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NL2037620A - Fragrance compositions cross-reference to related application - Google Patents

Fragrance compositions cross-reference to related application Download PDF

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Publication number
NL2037620A
NL2037620A NL2037620A NL2037620A NL2037620A NL 2037620 A NL2037620 A NL 2037620A NL 2037620 A NL2037620 A NL 2037620A NL 2037620 A NL2037620 A NL 2037620A NL 2037620 A NL2037620 A NL 2037620A
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Prior art keywords
fragrance
fragrance composition
composition
methyl
dimethyl
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Application number
NL2037620A
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Dutch (nl)
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NL2037620B1 (en
Inventor
Vernaz Dominique
Timonet Laura
Saint-Paul Aurélien
Alexandra De Sousa Oliveira Maia Marta
Perrotta Enrica
Bellouard Claudie
Original Assignee
Coty Inc
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Priority claimed from NL2035897A external-priority patent/NL2035897B1/en
Application filed by Coty Inc filed Critical Coty Inc
Publication of NL2037620A publication Critical patent/NL2037620A/en
Application granted granted Critical
Publication of NL2037620B1 publication Critical patent/NL2037620B1/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18Magnoliophyta (angiosperms)
    • A61K36/185Magnoliopsida (dicotyledons)
    • A61K36/62Nymphaeaceae (Water-lily family)
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/345Alcohols containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/608Derivatives containing from 2 to 10 oxyalkylene groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/738Cyclodextrins
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783Angiosperms [Magnoliophyta]
    • A61K8/9789Magnoliopsida [dicotyledons]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00Formulations or additives for perfume preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00Anti-perspirants or body deodorants
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00Essential oils; Perfumes
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50Perfumes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/008Preparations for oily skin

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Mycology (AREA)
  • Wood Science & Technology (AREA)
  • Emergency Medicine (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Microbiology (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Medical Informatics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Fats And Perfumes (AREA)
  • Seasonings (AREA)
  • Cosmetics (AREA)

Abstract

Various embodiments disclosed relate to a fragrance composition. The fragrance composition includes a fragrance component and an extract solution. The extract solution includes nymphaea coerulea flower extract and nelumbo nucifera flower extract.

Description

380526.NL.02-967.475NL2
FRAGRANCE COMPOSITIONS
CROSS-REFERENCE TO RELATED APPLICATION
[1] This application claims the benefit of priority to U.S. Provisional Patent
Application Serial Nos. 63/500,388 filed May 5, 2023 entitled “Cosmetic Composition”; 63/500,382 filed May 5, 2023 entitled “Fragrance Compositions”; 63/614,226 filed December 22, 2023 entitled “Cosmetic Composition”; and NL 2035897 filed 27 Sep 2023 entitled “Fragrance
Compositions” the disclosure of which is incorporated herein in its entirety by reference.
BACKGROUND
Experimental and clmical studies have shown that fragrance oils can display varying evaporation profiles depending at least on the presence or absence of other components of the formula.. Fragrance oils can also act as prehaptens or prohaptens by forming allergens that are more potent than a parent substance by activation outside or in the skin, Activation occurs via abiotic, chemical and physical factors, or biotic activation, thus, increasing the risk of sensitization.
Some fragrance oils autoxidize on contact with air, forming potent sensitizers that can be an important source for contact allergy to fragrances and fragranced products. Some of them act as prohaptens and are activated in the skin as well.
SUMMARY OF THE INVENTION
[2] Various embodiments disclosed relate to a fragrance composition. The fragrance composition includes a fragrance component; optionally a modulator; and an extract solution capable of sebum reduction; sweat reduction; and/or acetylcholine release inhibition. The extract solution may include nymphaea coerulea flower extract and nelumbo nucifera flower extract. The synergistic effects of applying the modulator and extract solution prior to or simultaneously with application of a fragrance allergen to skin may result in decreased allergenicity.
[3] New ingredients for use as effective, active agents in compositions and formulations for application, preferably topical application, to the skin are advantageous to the industry and the consumer for a variety of uses in the areas of skin care treatment and therapy, and 1
380526.NL.02-967.475NL2 personal use products. Nelupure (INCI: Propanediol (and) Glycerin (and) Nymphaea Caerulea
Flower Extract (and) Nelumbo Nucifera Flower Extract, used interchangeably as trade name
Nelupure; INCI; “lotus flower extract”; and/or “lotus flower extract blend and/or constituents thereof” throughout) is a blended extract from two types of lotus flower, the Egyptian Lotus (Nymphaea caerulea) and the Sacred Lotus (Nelumbo nucifera). Tt has been speculated that
Nelupure (INCI: Propanediol (and) Glycerin (and) Nymphaea Caerulea Flower Extract (and)
Nelumbo Nucifera Flower Extract) acts via leptin-receptor inhibition to regulate the sebaceous glands, preventing the excess of sebum production and inflammatory processes that cause skin blemishes, and may also act to inhibit acetylcholine release.
[4] Unwind Sacred Lotus, marketed by the Naolys company, is a material consisting of active plant cells from Nelumbo nucifera whose action has been described as " modulating the skin’s neuro-system, Sacred Lotus cells have a relaxing effect that helps to restore the skin’s original balance.” https://www.unifect conv produects/anwind-sacred-lotus/
DETAILED DESCRIPTION OF THE INVENTION
[5] Reference will now be made in detail to certain aspects of the disclosed subject matter. While the disclosed subject matter will be described in conjunction with the enumerated claims, it will be understood that the exemplified subject matter is not intended to limit the claims to the disclosed subject matter.
[6] Throughout this document, values expressed in a range format should be interpreted in a flexible manner to include not only the numerical values explicitly recited as the limits of the range, but also to include all the individual numerical values or sub-ranges encompassed within that range as if each numerical value and sub-range is explicitly recited. For example, a range of “about 0.1% to about 5%” or “about 0.1% to 5%" should be interpreted to include not just about 0.1% to about 5%, but also the individual values (e.g., 1%, 2%, 3%, and 4%) and the sub-ranges (eg, 0.1% to 0.5%, 1.1% to 2.2%, 3.3% to 4.4%) within the indicated range. The statement “about
X to Y has the same meaning as “about X to about Y,” unless indicated otherwise. Likewise, the statement “about X, Y, or about Z” has the same meaning as “about X, about Y, or about Z,” unless indicated otherwise. 2
380526.NL.02-967.475NL2
[7] In this document, the terms “a,” “an,” or “the” are used to include one or more than one unless the context clearly dictates otherwise. The term “or” is used to refer to a nonexclusive “or” unless otherwise indicated. The statement “at least one of A and B” has the same meaning as “A, B, or A and B.” In addition, it is to be understood that the phraseology or terminology employed herein, and not otherwise defined, is for the purpose of description only and not of limitation. Any use of section headings is intended to aid reading of the document and is not to be interpreted as limiting; information that is relevant to a section heading may occur within or outside of that particular section.
[8] As used herein, the term “body splash” means a body care formulation that is applied to the body. Typically, the body splash 1s applied to the body after bathing and provides a subtle hint of scent to the body. Body splashes are commonly used by consumers who prefer less strong fragrance compositions. A body splash may comprise an ethanol-free composition according to the present invention which comprises from 0.2-8 wt%, relative to the total weight of the composition, of a fragrance component. The body splash may further comprise alkyl polyglucosides as non-ionic surfactants.
[9] As used herein, the term “body spray” means a formulation comprising fragrance materials intended to be applied to the body to prevent or mask body odor caused by the bacterial breakdown of perspiration on the body (e.g., armpits, feet, and other areas of the body). The body spray may also provide a fragrance expression to the a panel of experts or professional evaluators or individual experts or professional evaluators. Typically, body spray compositions are applied as an aerosol spray in an effective amount on the skin of a consumer.
[10] As used herein, the term “composition” includes a fine fragrance composition intended for application to a body surface, such as for example, skin or hair, e.g., to impart a pleasant odor thereto, or cover a malodour thereof. They are generally in the form of perfume concentrates, perfumes, eau de parfums, eau de toilettes, aftershaves, or colognes. The fine fragrance compositions may be an ethanol-based composition. The term “composition” may also include a cosmetic composition, which comprises a fragrance material for the purposes of delivering a pleasant smell to drive consumer acceptance of the cosmetic composition. The term “composition” may also include body splashes or body sprays. The term “composition” may also include cleaning compositions, such as fabric care composition or home care compositions, 3
380526.NL.02-967.475NL2 including air care compositions (e.g., air fresheners), for use on clothing or other substrates such as hard surfaces (e.g, dishes, floors, countertops). Additional non-limiting examples of “composition” may also include facial or body powder, deodorant, foundation, body/facial oil, mousse, creams (e.g., cold creams), waxes, sunscreens and blocks, bath and shower gels, lip balms, self-tanning compositions, masks and patches.
[11] As used herein, the term “consumer” means both the user of the composition and the observer nearby or around the user.
[12] As used herein, the term “fragrance material” and “fragrance materials” relates to a perfume raw material (“PRM”), or a mixture of perfume raw materials (“PRMs”), that are used to impart an overall pleasant odor or fragrance profile to a composition. “Fragrance materials” can encompass any suitable perfume raw materials for fragrance uses, including materials such as, for example, alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogenous or sulfurous heterocyclic compounds and essential oils. However, naturally occurring plant and animal oils and exudates comprising complex mixtures of various chemical components are also known for use as “fragrance materials”. The individual perfume raw materials which comprise a known natural oil can be found by reference to Journals commonly used by those skilled in the art such as “Perfume and Flavourist™ or “Journal of Essential Oil Research”, or listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969,
Montclair, New Jersey, USA and more recently re-published by Allured Publishing Corporation
Illinois (1994). Additionally, some perfume raw materials are supplied by the fragrance houses (Firmenich, International Flavors & Fragrances, Givaudan, Symrise) as mixtures in the form of proprietary specialty accords. Non-limiting examples of the fragrance materials useful herein include pro-fragrances such as acetal pro-fragrances, ketal pro-fragrances, ester pro-fragrances, hydrolyzable inorganic-organic pro-fragrances, and mixtures thereof. The fragrance materials may be released from the pro-fragrances in a number of ways. For example, the fragrance may be released as a result of simple hydrolysis, or by a shift in an equilibrium reaction, or by a pH-change, or by enzymatic release.
[13] As used herein, the term “fragrance profile” means the description of how the fragrance is perceived by the human nose at any moment in time. The fragrance profile may change over time. It is a result of the combination of the low, moderate and high volatile fragrance 4
380526.NL.02-967.475NL2 materials, if present, of a fragrance. A fragrance profile is composed of 2 characteristics: ‘intensity’ and ‘character’. The ‘intensity’ relates to the perceived strength whilst ‘character’ refers to the odor impression or quality of the perfume, e.g., fruity, floral, woody, etc.
[14] As used herein, the terms “modulator”, and “fragrance modulator” are used interchangeably to designate an agent having the capacity to affect the fragrance profile, such as for example, by impacting the fragrance materials’ evaporation rate. The modulator may mediate its effect by lowering the vapor pressure of the fragrance materials and increasing their adherence to the substrate (skin and/or hair) thus ensuring a longer-lasting impression of the fragrance. By incorporating the modulator, it is desired that the fragrance profile, preferably the fragrance components composition attributable to the high and moderate volatile fragrance materials, alone or individually, of the composition can be perceived by a panel of experts or professional evaluators or individual experts or professional evaluators, over a longer period of time, or the perceived harshness of overdosing of the fragrance material 1s mitigated or absent, as compared to the same perception in the absence of the modulator. As used herein “overdose” can include overdosing a moderate volatile component or high volatile component in aggregate (e.g., greater than 30 wt% of the fragrance component). The term “overdose” can further include overdosing an individual component of the moderate volatile component or the high volatile component (e.g., if the high volatile component includes three oils at least one of the oils may account for a greater wt% of the high volatile component than would be present in a traditional fragrance or a fragrance that is free of the modulators described herein). Suitable examples of the modulator are provided herein below.
[15] As used herein, “skin sensitizing potency” is defined as she relative ability of « chessicel je Induce sj sessiizaron, which i determined by the amount of chemical per unit area required for the acquisition of skin sensitization m a previously naive individual. For chemical safety assessment, it 1s of utmost importance to evaluate dose-effect relationships and to classify chermcals according to the strength of ther response. Skin sensitizing potency 18 measured by a
GARDskan dose response method. Figure 1 illustrates a summary of steps of the GARDskin dose response method. Figure 2 graphically illustrates application of the GARDskin dose response protocol in a titrated range of concentrations (n=6) starting from a determined top concentration. 5
380526.NL.02-967.475NL2
[16] As used herein, the term “substantially non-odorous” means an agent that does not impart an odor of its own when added into a composition of the present invention. For example, a “substantially non-odorous fragrance modulator” does not impart a new odor that alters the character of the fragrance profile of the composition to which it is added. The term “substantially non-odorous” also encompasses an agent that may impart a minimal or slight odor of its own when added into a composition of the present invention. However, the odor imparted by the “substantially non-odorous fragrance modulator” 1s generally undetectable or tends to not substantively alter the character of the fragrance profile of the composition to which it is added mitially or preferably over time. Furthermore, the term “substantially non-odorous” also includes materials that are perceivable only by a minority of people or those materials deemed “anosmic” to the majority of people. Furthermore, the term “substantially non-odorous” also includes materials that may, from particular suppliers, contain an odor due to impurities, such as when the materials contain the impurities at not more than about 5 wt%, preferably not more than 1 wt%, often even not more than 1 part per million (ppm). These impurities may be removed by purification techniques known 1n the art as required to make them suitable for use in fragrance compositions of the present invention.
[17] As used herein, the term “vapor pressure” means the partial pressure in air at a defined temperature (e.g., 25 °C) and standard atmospheric pressure (760 mmHg) for a given chemical species. It defines a chemical species’ desire to be in the gas phase rather than the liquid or solid state. The higher the vapor pressure the greater the proportion of the material that will, at equilibrium, be found in a closed headspace. It is also related to the rate of evaporation of a fragrance material which is defined in an open environment where material is leaving the system.
The vapor pressure is determined according to the reference program Advanced Chemistry
Development (ACD/Labs) Software Version 14.02, or preferably the latest version update).
[18] It is understood that the test methods that are disclosed in the Test Methods Section of the present application must be used to determine the respective values of the parameters of
Applicants’ inventions as described and claimed herein.
[19] In all embodiments of the present invention, all percentages are by weight of the total composition, as evident by the context, unless specifically stated otherwise. All ratios are 6
380526.NL.02-967.475NL2 weight ratios, unless specifically stated otherwise, and all measurements are made at 25 °C, unless otherwise designated.
[20] According to various aspects of the instant disclosure, a fragrance composition includes a fragrance component as well as an extract solution capable of reducing sebum production; sweat production; and / or acetylcholine release. The extract solution includes nymphaea coerulea flower extract and nelumbo nucifera flower extract. The solution is available as a product under the tradename NELUPURE (INCI: INCI: Propanediol (and) Glycerin (and)
Nymphaea Caerulea Flower Extract (and) Nelumbo Nucifera Flower Extract). The extract solution can be present in a range of from about 0.5 wt% to about 20 wt% of the fragrance composition, about 2 wt% to about 10 wt%, less than, equal to, or greater than, 0.5 wt%, 1, 1.5, 2, 25,3,35,4,45,5,55,6,65,7,75,8,85,9,10, 105,11, 11.5, 12, 12.5, 13, 13.5, 14, 14.5, 15, 15.5, 16, 16.5, 17, 17.5, 18, 18.5, 19, 19.5, or about 20 wt%.
[21] More specifically, the components (also referred to as active agents, constituents, ingredients, reagents, substances, or compounds herein) of this invention are extracts from the flower of one or more species of the lotus flowers, obtained from plants and the like, preferably of the Nelumbo family. These plant materials have been newly determined to be effective constituents in compositions and methods for treating, preventing, reducing, inhibiting, improving and/or eliminating wrinkles, fine lines, creases, folds, furrows, and other signs of dermatological aging due to chronological and/or hormonal aging, or due to sunlight exposure of the skin, as well for use in the treatment of hyperhidrosis; and may be useful (due to acetylcholine release inhibition and/or decreased sebum or sweat production leading to decreased inflammation) in lessening allergenic reaction to a fragrance composition applied to skin simultaneously with or subsequent to application of the lotus flower extract; and/or in modulating fragrance component evaporation when applied prior to or simultaneously with application of fragrance formulation components to the skin.
[22] According to the present invention, yet without wishing to be bound by theory, the extracts from the flower of one or more species of the lotus flower constituents exert their effects by their ability to inhibit, block, reduce, or prevent the release of acetylcholine at the neuromuscular junction (NMJ) of skeletal muscle cells and tissue, thereby relaxing muscles, for example, muscles associated with facial movement or expressions. Both nerve and muscle cells 7
380526.NL.02-967.475NL2 (skeletal muscle cells) are electrically excitable and the junctions between these types of cells are known as NMJ. It has been known for many years that the stimulation of a motor nerve innervating a skeletal muscle also causes the release of acetylcholine and that acetylcholine, in turn, stimulates the skeletal muscle to contract. Thus, acetylcholine has been identified as the neurotransmitter at the neuromuscular junction. (see, e.g., B. Alberts et al, 1989, Molecular Biology of the
Cell, 2"Ed., Chapter 19, The Nervous System, Garland Publishing, Inc., NY., pp. 1075 et seq.).
Provided by the present invention are extracts from the flower of one or more species of the lotus flower constituents which are newly described herein to inhibit, reduce, block, or prevent the release of acetylcholine at the NMJ of the skeletal muscle and thus relax the muscles, preferably those associated with facial expression or movement, particularly when employed in the compositions and methods of the invention. By being able to inhibit acetylcholine release, compositions and methods comprising the extracts from the flower of one or more species of the lotus flower constituents as described herein can reduce, treat, and/or prevent excessive sweating or perspiration.
[23] The ability of the extracts from the flower of one or more species of the lotus flower constituents to inhibit acetylcholine release by muscle cells results in a modulation of motor contraction so as to relax the muscle fibers.
[24] Thus, 1n one of its embodiments, the present invention encompasses compositions, formulations and methods containing components, preferably, extracts from the flower of one or more species of the lotus flower constituents, newly determined to be useful in the minimization of allergy elicitation associated with fragrance ingredient exposure and/or the inflammatory process.
[25] The plant-derived materials from the Lotus family may exert their effectiveness according to this invention by preferably working at the neuromuscular junctions (NMJ), such as in and around muscle and nerve cells and tissue at a site of application, e.g., the skin of face, neck, arms, feet, hands, or chest, or in the dermis layer of the skin where sweat glands are located. Prior to the present invention, these materials in combination were not previously known or recognized to inhibit acetylcholine release at NMJ of skeletal muscles.
[26] In general, for the purposes of the present invention, a substance, such as a extract from the flower of one or more species of the lotus flower constituent of the described 8
380526.NL.02-967.475NL2 compositions, is recognized as being a muscle relaxant when it elicits a relaxation effect on contracted muscle cells or on tissue, such as cutaneous or subcutaneous muscle tissue, and/or exhibits an inhibitory effect on acetylcholine release at the NMJ. Contracted muscle cells or tissue 1s associated with formation of wrinkles, fine lines, etc.
[27] It 1s another aspect of the present disclosure to provide compositions, formulations and methods utilizing materials that are newly determined to be useful in the reduction of sweating from the skin.
[28] The physiological act of sweating serves as the body's natural coolant, protecting it from overheating. When subjected to temperature increases, stress, or exercise, the body excretes sweat, a fluid comprising mostly water along with minerals, lactate and urea, to cool the body by evaporation of the water.
[29] Sweating can have adverse effects on the use of cosmetics, for example by adversely impacting the ability of foundation to maintain integrity on the skin. While occlusive agents have been uilized to decrease the amount of perspiration, such occlusive agents can also hinder the ski's ability to breathe and to release oils, which can result mm skin writation and comedogenic effects. {36} As used here, "sweating" refers to the excretion of perspiration from the pores of the skin, Sweating includes, but not houted to, non-pathological sweating, such as thermally mduced, exercise-induced, or stress-induced sweating, The mvention is useful in any area of the body where sweating occurs such as the hands, feet, face, head, torso, neck, arms, wrist, legs, or underarms {axiila}.
[31] It 15 an object of the present invention to provide a cosmetic composition that does not require the presence of an ahmmnum salt and/or an occlusive agent to debver a sweat management benefit.
[32] For use in the compositions of this invention, the extracts from the flower of one or more species of the lotus flower extracts can be chemically synthesized. Alternatively, these plant alkaloids may be extracted from plants. When extracted, they may be in a pure form, a semi- purified form, or may be a component of an unpurified plant extract. 9
380526.NL.02-967.475NL2
[33] The extracts from the flower of one or more species of the lotus flower plant materials contained in the compositions of the present invention can be chemically synthesized at industrial scale in large amounts. Alternatively, the materials may be extracted from natural raw materials from plants. Any and all methods of preparation may be used, including the use of cultured plant seed cells, as disclosed in commonly owned patent application U.S. Ser. No. 10/040,242, which is hereby incorporated by reference herein. For example, unpurified plant extracts may be employed in the present invention. Depending on the solubility of the particular plant extractin water or in organic solvent, the extraction process may differ. Two methods for extracting the materials from raw plant materials include organic solvent extraction, and aqueous- organic solvent extraction, as described in U.S. Pat. No. 6,372,239 to Wu et al. The organic extraction method involves a step of continuous washing and extracting the plant material against a stream of organic solvent. Examples of organic solvents include, but are not limited to methanol, ethanol, dichloromethane, chloroform, xylene, and petroleum ether. Alternatively, the alkaloid can be partially purified or completely purified. Chemical synthesis of the alkaloid obviates the need for extraction and purification.
[34] In accordance with this invention, the extracts from the flower of one or more species of the lotus flower constituents comprise compositions which include, without limitation, topically applied formulations, anti-oxidants, anti-inflammatories, sunscreens, cosmetics, including make-ups, anti-aging formulations, e.g., creams for fine lines and/or wrinkles, topicals, skin penetration enhancers, antiperspirants, deodorants, and the like. Also in accordance with this invention, the extracts from the flower of one or more species of the lotus flower constituents and additional ingredients comprising such compositions can be formulated in a variety of product forms. Preferably, the compositions are prepared in targeted delivery systems, e.g., transdermals, such as patches, and the like, particularly for topical administration. [BS] The present invention encompasses compositions comprising one or more extracts from the flower of one or more species of the lotus flower constituents, preferably in a pharmaceutically-acceptable cosmetic or dermatological formulation which is suitable for contact with living animal tissue, including human tissue, and for topical administration, with virtually no adverse physiological effect, e.g., irritation, to the user. Thus, the inventive compositions are especially suitable for sensitive skin. 10
380526.NL.02-967.475NL2
[36] The fragrance component can include one or more fragrant compounds. On the whole, the fragrance component present in an amount 1n a range of from about 0.04 wt% to about 40 wt% of the fragrance composition, about 0.5 wt% to about 30 wt%, less than, equal to, or greater than about 0.04 wt%, 0.5, 1,1.5,2,2.5,3,3.5,4,4.5,5,5.5,6,65,7,7.5,8,85,9,95, 10, 10.5, 11,11.5,12, 12.5, 13, 13.5, 14, 14.5, 15, 15.5, 16, 16.5, 17, 17.5, 18, 18.5, 19, 19.5, 20, 20.5, 21, 21.5,22,22.5,23,23.5, 24, 24.5, 25, 25.5, 26, 26.5, 27, 27.5, 28, 28.5, 29, 29.5, 30, 30.5, 31, 31.5, 32,32.5, 33, 33.5, 34, 34.5, 35, 35.5, 36, 36.5, 37, 37.5, 38, 38.5, 39, 39.5, or about 40 wt%.
[37] The fragrance component can include a wide variety of fragrance materials. The fragrance materials can be grouped in terms of their volatility. Generally, the materials can be grouped as low volatile fragrance materials, moderate volatile fragrance materials, and high volatile fragrance materials. Each group of materials can be associated with various perceptions by a panel of experts or professional evaluators or individual experts or professional evaluators.
While not so limited, a high volatile fragrance may be associated with a citrus character; a moderate volatile fragrance may be associated with a spicy character; and a low volatile fragrance may be associated with a woody character. Each group of fragrance materials can include synthetic materials or natural materials. The volatility of the fragrance materials can be in reference to an individual fragrance material. Alternatively, in cases where a combination of materials produce a fragrance, for example a natural oil, the volatility may be in reference to that aggregation.
[38] As described herein, the “fragrance materials” or “fragrance components” have been classified as low, moderate or high volatile fragrance materials according to their volatility by their vapor pressure. This method of classifying fragrance materials by their vapor pressure avoids the problem of different classifications for the same fragrance material according to the traditional approach that relies on their subjective characteristic character. In the case that the fragrance materials are a natural oil, extract or absolute, which comprises a mixture of several compounds, the vapor pressure of the complete oil should be treated a mixture of the individual perfume raw material components using the reference program cited above. The individual components and their level, in any given natural oil or extract, can be determined by direct injection of the oil into a GC-MS column for analysis as known by one skilled in the art. In the scenario that the fragrance materials are a proprietary specialty accord, so called ‘bases’, the vapor pressure, 11
380526.NL.02-967.475NL2 using the reference program cited above, should preferably be obtained from the supplier.
However, it is understood by one skilled in the art that they can physically analyze the composition of a full fragrance oil available commercially to identity the fragrance raw materials and their levels using standard GC-MS techniques. This would be irrespective of whether they had been added to the fragrance oil as individual chemicals, as components of naturals or from proprietary bases. Although proprietary bases and naturals are included in our examples, when analyzing a commercially available fragrance via GC-MS one could simply identify the components of the base or natural oil as part of the overall fragrance mixture and their levels, without being able to identify which proprietary base or natural oil the fragrance had come from.
[39] A pH of the composition can be in a range of from about 4 to about 8, about 5 to about 7, less than, equal to, or greater than about 4, 5, 6, 7, or about 8. The ethanol concentration in any of the compositions described herein can be less than about 78 wt% ethanol, less than about 70 wt% ethanol, less than about 60 wt% ethanol, less than about 50 wt% ethanol, less than about 40 wt% ethanol, less than about 30 wt% ethanol, less than about 20 wt% ethanol, less than about 10 wt% ethanol, or free of ethanol. (1) Low Volatile Fragrance Materials
[40] The fragrance component may comprise at least one low volatile fragrance material. Individual low volatile fragrance materials or aggregate low volatile fragrance materials are those having a vapor pressure less than 0.001 Torr (0.000133 kPa) at 25 °C. According to some examples, the composition can include at least 3 low volatile fragrance materials, or at least 4 low volatile fragrance materials, or at least 5 low volatile fragrance materials, or at least 7 low volatile fragrance materials.
[41] If there are more than one low volatile fragrance materials, then the ranges provided hereinabove cover the total of all the low volatile fragrance materials. Examples of suitable low volatile fragrances materials are provided in Table 1A and 1B below.
[42] Preferably, the low volatile fragrance material is selected from at least 1 material, or at least 2 materials, or at least 3 materials, or at least 5 materials, at least 7, at least 8, at least 10, or at least 12 low volatile fragrance materials as disclosed in Table 1A. Natural fragrance 12
380526.NL.02-967.475NL2 materials or oils having an aggregrate vapour pressure less than 0.001 Torr (0.000133 kPa) at 25 °C are provided in Table 1B. Low Volatile Natural Oils.
Table 1A — Low Volatile Fragrance Materials
No. CAS Number | IUPAC Name Common Vapor a al at 25°C)* 3-0x0-2-(2Z)-2-penten-1- | jasmonate yl-, methyl ester, (1R,2R)- 2. 28219-60-5 2-Buten-l-ol, 2-methyl- | Hindinol 0.00096100 4-(2,2,3-trimethyl-3- cyclopenten-1-yl)- 3. 93-08-3 Ethanone, 1-(2- | Methyl beta- | 0.00095700 naphthalenyl)- naphthyl ketone 4. 67633-95-8 3-Decanone, 1-hydroxy- | Methyl 0.00095100
Lavender
Ketone 5. 198404-98-7 | Cyclopropanemethanol, | Javanol® 0.00090200 1-methyl-2-[(1,2,2- trimethylbicyclo[3.1.0]he x-3-yl)methyl]- 4-hydroxy- 7. 72403-67-9 3-Cyclohexene-1- Myraldylaceta | 0.00087900 methanol, 4-(4-methyl-3- | te penten-1-yl)-, 1-acetate
Ml [eee 3(4H)-one, 7-methyl- 139504-68-0 | 2-Butanol, 1-[[2-(1,1- | Amber core 0.00080300 dimethylethyl)cyclohexyl
Joxy]- 10. 502847-01-0 | Spiro[5.5]undec-8-en-1- | Spiro[5.5]und | 0.00073100 one, 2,2,7,9-tetramethyl- | ec-8-en-1-one, 2,2,7,9- tetramethyl- 11. 2570-03-8 Cyclopentaneacetic acid, | trans-Hedione | 0.00071000
EE ee ester, (1R,2R)-rel- 12. 24851-98-7 Cyclopentaneacetic acid, | Methyl 0.00071000 3-ox0-2-pentyl-, methyl | dihydrojasmo ester 13
380526.NL.02-967.475NL2
TT mt alternatives / 13. 101-86-0 Octanal, 2- | Hexyl 0.00069700
EL aldehyde 14. 365411-50-3 | Indeno[4,5-d]-1,3-dioxin, | Nebulone 0.00069200 4,4a,5,6,7,8,9,9b- octahydro-7,7,8,9,9- pentamethyl- 15. 37172-53-5 Cyclopentanecarboxylic | Dihydro Iso | 0.00067500 acid, 2-hexyl-3-oxo0-, | Jasmonate methyl ester 16. 65113-99-7 3-Cyclopentene-1- Sandalore® 0.00062500 butanol, 0,B,2,2,3- pentamethyl- 17. 68133-79-9 Cyclopentanone, 2-(3,7- | Apritone 0.00062000 dimethyl-2,6-octadien-1- yl)- 18. 7212-44-4 1,6,10-Dodecatrien-3-0l, | Nerolidol 0.00061600 ee [000 methyl-5-phenyl-, (27)- ethyl-o,a-dimethyl- 21. 77-53-2 1H-3a,7-Methanoazulen- | Cedrol Crude | 0.00056900
G-ol, octahydro-3,6,8,8- tetramethyl-, 3R,3aS,6R,7R 8aS)- 22. 68155-66-8 Ethanone, 1- | Iso Gamma | 0.00056500 (1,2,3,5,6,7,8,8a- Super octahydro-2,3,8,8- tetramethyl-2- naphthalenyl)- 23. 54464-57-2 Ethanone, 1- | Iso-E Super® | 0.00053800 (1,2,3,4,5,6,7,8- octahydro-2,3,8,8- tetramethyl-2- naphthalenyl)- tetrahydro-2- naphthalenyl)- 25. 141-92-4 2-Octanol, 8,8- | Hydroxycitro | 0.00052000 dimethoxy-2,6-dimethyl- | nellal
Dimethyl
Acetal 14
380526.NL.02-967.475NL2 26. 20665-85-4 Propanoic acid, 2-methyl- | Vanillin 0.00051200 , 4-formyl-2- | isobutyrate methoxyphenyl ester 27. 79-78-7 1,6-Heptadien-3-one, 1- | Hexalon 0.00049800 (2,6,6-trimethyl-2- cyclohexen-1-yl)- , hexyl ester Salicylate ester Benzoate 30. 153859-23-5 | Cyclohexanepropanol, Norlimbanol | 0.00046900 2,2.6-trimethyl-a-propyl- , (1R,65)- 2,2 6-trimethyl-a-propyl- | Norlimbanol 32. 68555-58-8 Benzoic acid, 2-hydroxy- | Prenyl 0.00045700 , 3-methyl-2-buten-1-yl | Salicylate ester 33. 950919-28-5 | 2H-1,5-Benzodioxepin- | Cascalone 0.00045500 3(4H)-one, 7-(1- methylethyl)- 34. 30168-23-1 Butanal, 4-(octahydro- | Dupical 0.00044100 4,7-methano-5H-inden-5- ylidene)- 35. 1222-05-5 Cyclopenta[g]-2- Galaxolide® | 0.00041400 benzopyran, 1,3,4,6,7.8- hexahydro-4,6,6,7,8,8- hexamethyl- 3,7,11-trimethyl- 37. 95962-14-4 Cyclopentanone, 2-[2-(4- | Nectaryl 0.00036700 methyl-3-cyclohexen-1- yl)propyl]- 38. 4674-50-4 2(3H)-Naphthalenone, Nootkatone 0.00035800 4,44,5,6,7,8-hexahydro- 4,4a-dimethyl-6-(1- methylethenyl)-, 4R 4aS,6R)- phenyl-, pentyl ester Cinnamate acetate Acetate hydroxy-2-methyl-
380526.NL.02-967.475NL2 42. 128119-70-0 | 1-Propanol, 2-methyl-3- | Bornafix 0.00033400 [(1,7,7- trimethylbicyclo[2.2.1]he pt-2-yloxy]- 43. 103614-86-4 | 1-Naphthalenol, Octalynol 0.00033200 octahydro-2,2,6,8- tetramethyl- 44. 7785-33-3 2-Butenoic acid, 2- | Geranyl 0.00033200 methyl-, (2E)-3,7- | Tiglate dimethyl-2,6-octadien-1 - yl ester, (2F)- 45. 117933-89-8 | 1,3-Dioxane, 2-(2,4- | Karanal 0.00033100 dimethyl-3-cyclohexen- 1-yl}-5-methyl-5-(1- methylpropyl)- 47. 67801-20-1 4-Penten-2-01, 3-methyl- | Ebanol 0.00028100 5-(2,2,3-trimethyl-3- cyclopenten-1-yl)- 48. 65416-14-0 Propanoic acid, 2-methyl- | Maltol 0.00028000 \ 2-methyl-4-ox0-4H- | Isobutyrate pyran-3-yl ester 49. 28219-61-6 2-Buten-1-0l, 2-ethyl-4- | Laevo 0.00028000 (2,2,3-trimethyl-3- Trisandol cyclopenten-1-yl)- 50. 5986-55-0 1,6-Methanonaphthalen- | Healingwood | 0.00027800 1(2H)-ol, octahydro- 4,84,9,9-tetramethyl-, (1R,4S,44S,6R, 8aS)- 51. 195251-91-3 |2H-1,5-Benzodioxepin- | Transluzone 0.00026500
Med ee dimethylethyl)- enone , (37)-3-hexen-1-yl ester | salicylate 3-hydroxy- methyl- , phenylmethyl ester salicylate 16
380526.NL.02-967.475NL2 57. 81783-01-9 6,8-Nonadien-3-one, Labienoxime | 0.00017300 pr ae oxime , cyclohexyl ester Salicylate 59. 91-87-2 Benzene, [2- | Amyl 0.00016300 (dimethoxymethyl)-1- Cinnamic hepten-1-yl]- Aldehyde
Dimethyl
Acetal 104864-90-6 | 3-Cyclopentene-1- Firsantol 0.00016000 butanol, B,2,2,3- tetramethyl-6-methylene- spiro[4.5]dec-7-en-7-yl- |e 62. 134-28-1 5-Azulenemethanol, Guaiyl 0.00013400 1,2,3,4,5,6,7,8- Acetate octahydro-a,0,3,8- tetramethyl-, 5-acetate, 3S,5R,8S)- 63. 236391-76-7 | Acetic acid, 2-(1- | Romandolide | 0.00012400 oxopropoxy)-, ~~ 1-(3,3-|® dimethylcyclohexyl)ethyl ester 64. 115-71-9 2-Penten-1-ol, S- | cis-alpha- 0.00011800 [(1R,3R,65)-2,3- Santalol dimethyltricyelo[2.2.1.02 ‚6]hept-3-y1]-2-methyl-, 7. 65. 107898-54-4 | 4-Penten-2-ol, 3,3- | Polysantol®™ 0.00011700 dimethyl-5-(2,2,3- trimethyl-3-cyclopenten- 1-yl)- 69486-14-2 5,8-Methano-2H-1- Florex® 0.00011000 id ethylideneoctahydro- 67. 84697-09-6 Heptanal, 2-[(4- | Acalea 0.00010100 methylphenyl)methylene]
Jr Joga ae [ro one, (4Z)- 32388-55-9 Ethanone, 1- | Vertofix® 0.00008490 [(3R,3aR,7R,8aS)- 2,3,4,7,8,8a-hexahydro- 3,6,8 8-tetramethyl-1H- 17
380526.NL.02-967.475NL2
DE yl]- 70. 131812-67-4 | 1,3-Dioxolane, 2,4- | Okoumal®™ 0.00007600 dimethyl-2-(5,6,7,8- tetrahydro-5,5,8,8- tetramethyl-2- naphthalenyl)- one 72. 141773-73-1 1-Propanol, ~~ 2-[1-(3,3- | Helvetolide® | 0.00005790 dimethylcyclohexyl)etho xy]-2-methyl-, 1- propanoate 73. 63314-79-4 5-Cyclopentadecen-1- Delta 0.00005650 pe i fo 74. 77-42-9 2-Penten-1-01, 2-methyl- | cis-beta- 0.00004810 5-[(15,2R,4R)-2-methyl- | Santalol 3- methylenebicyclo[2.2.1]h ept-2-yl]-, (22)- 75. 362467-67-2 | 2H-1,5-Benzodioxepin- | Azurone 0.00004770 3(4H)-one, 7-(3- methylbutyl)- 76. 28371-99-5 Ethanone, 1-(2,6,10- | Trimofix O 0.00004580 ee ome cyclododecatrien-1-yl)- 77. 16223-63-5 1H-3a,6- Khusimol 0.00004400
Methanoazulene-3- methanol, octahydro-7,7- dimethyl-8-methylene-, (3S,3aR,6R 8aS)- cyclohexylidene- 79. 90-17-5 Benzenemethanol, o- | Rosacetol 0.00004240 (trichloromethyl)-, 1- acetate 50607-64-2 Benzoic acid, 2-[(2- | Mevantraal 0.00004070
Ee e -, methyl ester dioxane phenylethyl ester Benzoate 18
380526.NL.02-967.475NL2 one 85. 66072-32-0 Cyclohexanol, 4-(1,7,7- | Iso Bornyl | 0.00003010 er Ee pt-2-y1)-
CT EEE carboxaldehyde, 4-(4- hydroxy-4- methylpentyl)- 87. 21145-77-7 Ethanone, 1-(5,6,7,8- | Musk Plus 0.00002860 tetrahydro-3,5,5,6,8,8- hexamethyl-2- naphthalenyl)- 88. 21145-77-7 Ethanone, 1-(5,6,7,8- | Fixolide 0.00002860 tetrahydro-3,5,5,6,8,8- hexamethyl-2- naphthalenyl)- one, 3-methyl- a all il one 91. 101-94-0 Benzeneacetic acid, 4-| Para Cresyl | 0.00002330 methylphenyl ester Phenyl
Acetate 92. 102-20-5 Benzeneacetic acid, 2- | Phenyl Ethyl | 0.00002300 phenylethyl ester Phenyl
Acetate
B-methyl- an 94. 103-41-3 2-Propenoic acid, 3- | Benzyl 0.00001050 ee Ea joe ester 95. 4707-47-5 Benzoic acid, 2.4- | Veramoss / | 0.00001050 dihydroxy-3,6-dimethyl-, | LRG201 / methyl ester Evernyl 6(7H)-one, 8,9-dihydro- 1,5,8-trimethyl-, (8R)- 97. 102-17-0 Benzeneacetic acid, (4-| Para Anisyl | 0.00000813
EAT ester Acetate 19
380526.NL.02-967.475NL2 120-11-6 Benzene, 2-methoxy-1- | Benzyl Iso | 0.00000676 le propen-1-yl)- 99. 102-22-7 Benzeneacetic acid, (2F)- | Geranyl 0.00000645 3,7-dimethyl-2,6- Phenylacetate octadien-1-yl ester 2-one, (12F)- 100% , 2-phenylethyl ester Salicylate 102. 78-37-5 2-Propenoic acid, 3- | Linalyl 0.00000174 phenyl-, 1-ethenyl-1,5- | Cinnamate dimethyl-4-hexen-1-yl ester 2-one 2-0ne, (8Z)- 105. | 3391-83-1 1,7- Musk RI 0.00000057
Dioxacycloheptadecan-8- one indol-1-yl)-2,6-dimethyl- 107. 89-43-0 Methyl 2-[(7-hydroxy- | Aurantinol 0.0000000100 3,7- dimethyloctylidene)amin o]benzoate
Dioxacyclohexadecane- 5,16-dione
Dioxacycloheptadecane- | Brassylate 5,17-dione 110. 3681-73-0 Hexadecanoic acid, (2F)- | Hexarose 0.00000000300 lll octadien-1-yl ester (benzoyloxy)-1-propen- | benzoate 1-y1]-2-methoxy- 112. | 144761-91-1 | Benzoic acid, 2-[(1- | Trifone DIPG | 0.00000000093 hydroxy-3- phenylbutyl)amino]-, methyl ester
380526.NL.02-967.475NL2 ! Non-limiting examples of alternative qualities from various suppliers can be purchased under the following tradenames: Kharismal® Super (IFF), Kharismal® (IFF), Hedione" (Firmenich),
Hedione® HC (Firmenich), Paradisone (Firmenich), Cepionate (Zenon), Super cepionate (Zenon),
Claigeon® (Zenon). * Vapor Pressures are acquired as described in the Test Methods Section. ** Origin: The low volatile fragrance materials may be obtained from one or more of the following companies: Firmenich (Geneva, Switzerland), Symrise AG (Holzminden, Germany), Givaudan (Argenteuil, France), IFF (Hazlet, New Jersey), Bedoukian (Danbury, Connecticut), Sigma
Aldrich (St. Louis, Missouri), Millennium Specialty Chemicals (Olympia Fields, Illinois),
Polarone International (Jersey City, New Jersey), and Aroma & Flavor Specialties (Danbury,
Connecticut).
Table 1B -Low Volatile Natural Oils. o [omc J ee [wt 21
380526.NL.02-967.475NL2
Suppliers:
Firmenich, Geneva, Switzerland
Global Essence Inc, New Jersey, USA
H. Reynaud & Fils, Montbrun-les-Bains, France
IFF, Hazlet, New Jersey, USA
Mane, Le Bar-sur-Loup, France
Robertet, Grasse, France
[43] Exemplary low volatile fragrance materials selected from the group of Tables 1A or IB Low Volatile Fragrance Materials are preferred. However, it is understood by one skilled in the art that other low volatile fragrance materials, not recited in Tables 1A or 1B, would also fall within the scope of the present invention, so long as they have a vapor pressure less than 0.001
Torr (0.000133 kPa) at 25 °C. (11) Moderate Volatile Fragrance Materials
[44] The fragrance component may include at least one moderate volatile fragrance material or aggregate of volatile fragrance materials having a vapor pressure in the range of 0.1
Torr to 0.001 Torr (0.0133 kPa to 0.000133 kPa) at 25 °C. In some examples, the composition according to the present disclosure can include at least 3 moderate volatile fragrance materials, or at least 5 moderate volatile fragrance materials, or at least 7 moderate volatile fragrance materials.
If there are more than one moderate volatile fragrance materials, then the ranges provided hereinabove cover the total of all of the moderate volatile fragrance materials. Suitable examples of moderate volatile fragrances materials are provided in Table 2A and 2B below.
[45] Preferable examples of moderate volatile fragrance materials having a vapor pressure in the range of 0.1 Torr to 0.001 Torr (0.0133 kPa to 0.000133 kPa) at 25 °C are provided in Table 2A and 2B. Preferably, the moderate volatile fragrance material 1s selected from at least 1 material, or at least 2 materials, or at least 3 materials, or at least 5 materials, or at least 7 moderate volatile fragrance materials as disclosed in Table 2A. Natural fragrance materials or oils having an 22
380526.NL.02-967.475NL2 aggregate vapor pressure between 0.1 Torr to 0.001 Torr (0.0133 kPa to 0.000133 kPa) at 25 °C are provided in Table 2B. Moderate Volatile Natural Oils.
Table 2A — Moderate Volatile Fragrance Materials
Name** Pressure (Torr at 25 °C)* 24168-70-5 Pyrazine, 2- | Methoxyisobutylp | 0.09950000 ee methylpropyl)- 89-79-2 Cyclohexanol, 5- | Iso-Pulegol 0.09930000 2. methyl-2-(1- methylethenyl)-, 1R,25,5R)- 112-12-9 2-Undecanone Methyl Nonyl | 0.09780000 3. Ketone 103-05-9 Benzenepropanol, Phenyl Ethyl | 0.09770000 4. a,0-dimethyl- Dimethyl
Carbinol 125-12-2 Bicyclo[2.2.1]heptan | Iso Bornyl | 0.09590000 5. -2-ol, 1,7,7- | Acetate trimethyl-, 2-acetate, (1R,2R 4R)-rel- 78-70-6 1,6-Octadien-3-ol, Linalool 0.09050000 3,7-dimethyl- 101-97-3 Benzeneacetic acid, | Ethyl Phenyl | 0.08970000 7. ethyl ester Acetate 100-86-7 Benzeneethanol, q,0- | Dimethyl Benzyl | 0.08880000 re Em oT pe ylic acid, (3Z)-3- hexen-1-yl ester 67634-25-7 3-Cyclohexene-1- Floralate 0.08500000 re ER me dimethyl-, 1-acetate 112-44-7 Undecanal Undecyl 0.08320000 11. Aldehyde 23
380526.NL.02-967.475NL2 32669-00-4 Ethanone, 1-(3- | Tanaisone® 0.08150000 12. cycloocten-1-yl)- 98-53-3 Cyclohexanone, 4- | Patchi 0.07780000 13. (1, I-dimethylethyl)- 35854-86-5 6-Nonen-l-ol, (6Z)- | cis-6-None-1-0l 0.07770000 pes [ere meer fm 5331-14-6 Benzene, (2- | Butyl phenethyl | 0.07760000 15. butoxyethyl)- ether 80-57-9 Bicyclo[3.1.1]hept- | Verbenone 0.07730000 16. 3-en-2-one, 4,6,0- trimethyl- 22471-55-2 Cyclohexanecarboxy | Thesaron 0.07670000 17. lic acid, 2,2,6- trimethyl-, ethyl ester, (1R,65)-rel- 60-12-8 Benzeneethanol Phenethyl alcohol | 0.07410000 re me 106-26-3 2,6-Octadienal, 3,7- | Neral 0.07120000 19. dimethyl, (27)- 5392-40-5 2,6-Octadienal, 3,7- | Citral 0.07120000 20. dimethyl- 89-48-5 Cyclohexanol, 5- | Menthyl Acetate | 0.07070000 21. methyl-2-(1- methylethyl)-, 1- acetate, (1R,25,5R)- rel- 119-36-8 Benzoic acid, 2- | Methyl salicylate | 0.07000000 ee ee er ester
Ee 23. 104-46-1 methoxy-4-(1E)-1- propen-1-yl- 7549-37-3 2,6-Octadiene, 1,1-| Citral Dimethyl | 0.06780000
Be dimethyl- 25225-08-5 Cyclohexanemethan | Aphermate 0.06780000 1-formate 24
380526.NL.02-967.475NL2 = 3913-81-3 2-Decenal, (2E)- 0.06740000 26. 15373-31-6 3-Cyclopentene-1- Cantryl® 0.06700000 27. acetonitrile, 2,2.3- trimethyl- 6485-40-1 2-Cyclohexen-1-one, | Laevo carvone 0.06560000 28. 2-methyl-5-(1- methylethenyl)-, (SR) 16587-71-6 Cyclohexanone, 4- | Orivone 0.06490000 29. (1,1- dimethylpropyl)- 62406-73-9 6,10- Opalal CI 0.06290000 30. Dioxaspiro[4.5]deca ne, 8,8-dimethyl-7- 1-methylethy1)- 3720-16-9 2-Cyclohexen-1-one, | Livescone 0.06270000 31. 3-methyl-5-propyl- 13816-33-6 Benzonitrile, 4-(1- | Cumin Nitrile 0.06230000 32. methylethyl)- 67019-89-0 2,6-Nonadienenitrile | Violet Nitrile 0.06200000 33. 53398-85-9 Butanoic acid, 2- | cis-3-Hexenyl 0.06130000 34. methyl-, (3Z)-3- | Alpha Methyl hexen-1-yl ester Butyrate 208041-98-9 | n/a Jasmonitrile 0.05920000 35. 16510-27-3 Benzene, 1- | Toscanol 0.05870000 36. (cyclopropylmethyl) -4-methoxy- 111-80-8 2-Nonynoic acid, | Methyl Octine | 0.05680000 37. methyl ester Carbonate 103-45-7 Acetic acid, 2- | Phenyl Ethyl | 0.05640000 38. phenylethyl ester Acetate 2550-26-7 2-Butanone, 4- | Benzyl Acetone 0.05570000 39. phenyl-
380526.NL.02-967.475NL2 13491-79-7 Cyclohexanol, 2- | Verdol 0.05430000
EE
7786-44-9 2,6-Nonadien-1-01 2,6-Nonadien-1- | 0.05370000 41. ol 103-28-6 Propanoic acid, 2- | Benzyl Iso | 0.05130000
EE fe henylmethyl ester 104-62-1 Formic acid, 2- | Phenyl Ethyl | 0.05050000 43. phenylethyl ester Formate 28462-85-3 Bicyclo[2.2.1]heptan | Humus Ether 0.04870000 44. -2-01, 1,2,3,3- tetramethyl-,
LR,2R,4S)-rel- 122-03-2 Benzaldehyde, 4-(1- | Cuminic 0.04820000 45. methylethyl)- Aldehyde 358331-95-0 | 2,5-Octadien-4-one, | Pomarose 0.04810000
Ee 2F)- 562-74-3 3-Cyclohexen-1-ol, | Terpinenol-4 0.04780000 47. 4-methyl-1-(1- methylethyl)- 68527-77-5 3-Cyclohexene-1- Isocyclogeraniol | 0.04640000 48. methanol, 2,4,6- trimethyl- 35852-46-1 Pentanoic acid, (3Z)- | Cis-3-Hexenyl 0.04580000 49. 3-hexen-1-yl ester Valerate 2756-56-1 Bicyclo[2.2.1]heptan | Iso Bornyl | 0.04540000 50. -201, 1,7,7- | Propionate trimethyl-, 2- propanoate, 1R,2R,4R)-rel- 14374-92-6 Benzene, 1-methyl- | Verdoracine 0.04460000 51. 4-(1-methylethyl)-2- (1-propen-1-yl)- 6784-13-0 3-Cyclohexene-1- Limonenal 0.04380000
Ep dimethyl- 8000-41-7 2-(4-methyl-1- Alpha Terpineol | 0.04320000 enyl)propan-2-ol 26
380526.NL.02-967.475NL2 41884-28-0 1-Hexanol, 5- | Tetrahydro 0.04230000
Em methylethyl)-, (2R)- 22457-23-4 3-Heptanone, 5- | Stemone®™ 0.04140000 55. methyl-, oxime 104-50-7 2(3H)-Furanone, 5- | Gamma 0.04080000 56. butyldihydro- Octalactone 143-08-8 1-Nonanol Nonyl Alcohol 0.04070000 3613-30-7 Octanal, 7-methoxy- | Methoxycitronell | 0.04020000 58. 3,7-dimethyl- al 67634-00-8 Acetic acid, 2-(3- | Allyl Amyl | 0.04000000 59. methylbutoxy)-, 2- | Glycolate propen-1-yl ester 464-45-9 Bicyclo[2.2.1]heptan | 1-Borneol 0.03980000 60. -2-0l, 1,7,7- trimethyl-, 15,2R 4S5)- 124-76-5 Bicyclo[2.2.1]heptan | 1.7.7-Trimethyl- | 0.03980000 61. -2-ol, 1,7,7- | Bicyclo-1.2.2- trimethyl-, Heptanol-2 (LR, 2R AR)-rel- 67874-72-0 Cyclohexanol, 2- | Coniferan 0.03980000 62. (1,1- dimethylpropyl)-, 1- acetate 80-26-2 3-Cyclohexene-1- Terpinyl Acetate | 0.03920000 63. methanol, 0,0,4- trimethyl-, 1-acetate 498-81-7 Cyclohexanemethan | Dihydro 0.03920000
EE fe ee 112-45-8 10-Undecenal Undecylenic 0.03900000 65. aldehyde 35044-57-6 2,4-Cyclohexadiene- | Ethyl Safranate 0.03880000 l-carboxylic acid, 2,6,6-trimethyl-, ethyl ester ee oonene 67. dimethyl- 27
380526.NL.02-967.475NL2 84560-00-9 Cyclopentanol, 2- | Cyclopentol 0.03790000 pentyl- 82461-14-1 Furan, tetrahydro- | Rhubafuran® 0.03780000 69. 2,4-dimethyl-4- henyl- 56011-02-0 Benzene, [2-(3- | Phenyl Ethyl | 0.03690000 70. methylbutoxy)ethyl] | Isoamyl Ether 103-37-7 Butanoic acid, | Benzyl Butyrate | 0.03660000 71. phenylmethyl ester 6378-65-0 Hexyl hexanoate Hexyl hexanoate | 0.03490000 72. 118-61-6 Benzoic acid, 2- | Ethyl salicylate 0.03480000 73. hydroxy-, ethyl ester 98-52-2 Cyclohexanol, 4- | Patchon 0.03480000 74. (1,1-dimethylethyl)- 115-99-1 1,6-Octadien-3-ol, Linalyl Formate 0.03440000 75. 3,7-dimethyl-, 3- formate 112-54-9 Dodecanal Lauric Aldehyde | 0.03440000 76. 53046-97-2 3,6-Nonadien-1-0l, 3,6 Nonadien-1-o0l | 0.03360000 77. (3Z,6Z)- 76649-25-7 3,6-Nonadien-1-ol 3,6-Nonadien-1- | 0.03360000 78. ol 141-25-3 3,7-Dimethyloct-6- | Rhodinol 0.03290000 79. en-1-ol © ee 2216-51-5 Cyclohexanol, 5- | L-Menthol 0.03230000 81. methyl-2-(1- methylethyl)-, (1R,2S,5R)- 28
380526.NL.02-967.475NL2 3658-77-3 4-hydroxy-2,5- Pineapple Ketone | 0.03200000 82. dimethylfuran-3-one 103-93-5 Propanoic acid, 2- | Para Cresyl iso-| 0.03120000 83. methyl-, 4- | Butyrate methylphenyl ester 24717-86-0 Propanoic acid, 2- | Abierate 0.03110000 84. methyl-, (1R,2S,4R)- 1,7,7- trimethylbicyclo[2.2. 1]hept-2-yl ester, rel- 67845-46-9 Acetaldehyde, 2-(4- | Aldehyde XI 0.03090000 85. methylphenoxy)- 67883-79-8 2-Butenoic acid, 2- | Cis-3-Hexenyl 0.03060000 methyl-, (3Z)-3- | Tiglate hexen-1-yl ester, 2F)- 33885-51-7 Bicyclo[3.1.1]hept- | Pino 0.03040000 87. 2-ene-2-propanal, Acetaldehyde 6,6-dimethyl- 105-85-1 6-Octen-1-0l, 3,7- | Citronellyl 0.03000000 88. dimethyl-, I-formate | Formate 70214-77-6 2-Nonanol, 6,8- | Nonadyl 0.03010000 dimethyl- 215231-33-7 | Cyclohexanol, 1- | Rossitol 0.02990000 methyl-3-(2- methylpropyl)- 120-72-9 1H-Indole Indole 0.02980000 91. 2463-77-6 2-Undecenal 2-Undecene-1-al | 0.02970000 92. 675-09-2 2H-Pyran-2-0ne, Levistamel 0.02940000 93. 4,6-dimethyl- 98-55-5 3-Cyclohexene-1- Alpha-Terpineol | 0.02830000 94. methanol, 0,0,4- trimethyl- 81786-73-4 3-Hepten-2-one, Koavone 0.02750000 95. 3,4,5,6,6- pentamethyl-, (3Z)- 29
380526.NL.02-967.475NL2 122-97-4 Benzenepropanol Phenyl Propyl | 0.02710000 re JE ee pT RE [Sie De 97. butyldihydro-4- Octalactone methyl- 53767-93-4 7-Octen-2-ol, 2,6- | Dihydro Terpinyl | 0.02690000 dimethyl-, 2-acetate | Acetate 35044-59-8 1,3-Cyclohexadiene- | Ethyl Safranate 0.02660000 l-carboxylic acid, 2,6,6-trimethyl-, ethyl ester 104-55-2 2-Propenal, 3- | Cinnamic 0.02650000 100. phenyl- Aldehyde 144-39-8 1,6-Octadien-3-ol, Linalyl 0.02630000 101. 3,7-dimethyl-, 3- | Propionate propanoate 61931-80-4 1,6-Nonadien-3-ol, 3,7-Dimethyl-1,6- | 0.02630000 re i me acetate acetate 102-13-6 Benzeneacetic acid, | Iso Butyl | 0.02630000 103. 2-methylpropyl ester | Phenylacetate 65443-14-3 Cyclopentanone, Veloutone 0.02610000 104. 2,2, 5-trimethyl-5- pentyl- 141-12-8 2,6-Octadien-1-ol, Neryl Acetate 0.02560000 105. 3,7-dimethyl-, 1- acetate, (22)- 105-87-3 2,6-Octadien-1-ol, Geranyl acetate 0.02560000 er ee ree acetate, (2E)- on | ame na 107. dimethoxy-2- Acetaldehyde methyl- Dimethyl Acetal 2206-94-2 Benzenemethanol, a- | Indocolore 0.02550000 ree Ee BR me acetate 10528-67-3 Cyclohexanepropan | Cyclohexylmagno | 0.02550000 in | [Pres
I Fr ll 09 110. methoxy-
380526.NL.02-967.475NL2 57576-09-7 Cyclohexanol, 5- | Iso Pulegol | 0.02480000 111. methyl-2-(1- Acetate methylethenyl)-, 1- acetate, (1R,2.5,5R)- 51566-62-2 6-Octenenitrile, 3,7- | Citronellyl Nitrile | 0.02470000 112. dimethyl- 60335-71-9 2H-Pyran, 3,6- | Rosyrane Super 0.02470000 113. dihydro-4-methyl-2- phenyl- 30385-25-2 6-Octen-2-0l, 2,6- | Dihydromyrcenol | 0.02440000 114. dimethyl- 101-84-8 Benzene, 1,1’- | Diphenyl Oxide 0.02230000 115. oxybis- 136-60-7 Benzoic acid, butyl | Butyl Benzoate 0.02170000 116. ester 93939-86-7 5,8-Methano-2H-1- | Rhuboflor 0.02120000 117. benzopyran, 6- ethylideneoctahydro 83926-73-2 Cyclohexanepropan | Coranol 0.02100000 118. ol, a,a-dimethyl- 125109-85-5 | Benzenepropanal, B- | Florhydral 0.02070000 119. methyl-3-(1- methylethyl)- 104-21-2 Benzenemethanol, 4- | Anisyl Acetate 0.02050000 120. methoxy-, 1-acetate 1365-19-1 2-Furanmethanol, 5- | Linalool Oxide 0.02050000 121. ethenyltetrahydro- 0,0, 5-trimethyl- 137-03-1 Cyclopentanone, 2- | Frutalone 0.02040000 122. heptyl- 2563-07-7 Phenol, 2-ethoxy-4- | Ultravanil 0.02030000 123. methyl- 1128-08-1 2-Cyclopenten-1- Dihydrojasmone | 0.02020000 124. one, 3-methyl-2- entyl- 31
380526.NL.02-967.475NL2 7493-57-4 Benzene, [2-(1- | Acetaldehyde 0.01990000 125. propoxyethoxy)ethyl ]- 141-25-3 7-Octen-1-0l, 3,7- | Rhodinol 0.01970000 126. dimethyl- 216970-21-7 | Bicyclo[4.3.1]decan | 3-Methoxy-7,7- 0.01960000 127. e, 3-methoxy-7,7- | dimethyl-10- dimethyl-10- methylenebicyclo methylene- [4.3.1]decane 319002-92-1 | Propanoic acid, 2- | Sclareolate® 0.01960000 128. (1,1- dimethylpropoxy)-, propyl ester, (2S)- 85-91-6 Benzoic acid, 2- | Dimethyl 0.01930000 129. (methylamino)-, anthranilate methyl 13828-37-0 Cyclohexanemethan | Mayol 0.01920000 130. ol, 4-(1- methylethyl)-, cis- 26330-65-4 (E)-6-ethyl-3- Super Muguet 0.01850000 131. methyloct-6-en-1-ol 7540-51-4 6-Octen-1-0l, 3,7- | L-Citronellol 0.01830000 132. dimethyl-, (35)- 106-22-9 6-Octen-l-ol, 3.7- | Citronellol 0.01830000 133. dimethyl- 543-39-5 7-Octen-2-ol, 2- | Myrcenol 0.01820000 134. methyl-6-methylene- 7775-00-0 Benzenepropanal, 4- | Cyclemax 0.01820000 135. (1-methylethyl)- 18479-54-4 4,6-Octadien-3-ol, Muguol 0.01800000 136. 3,7-dimethyl- 29214-60-6 Octanoic acid, 2- | Gelsone 0.01790000 137. acetyl-, ethyl ester 1209-61-6 5- Tobacarol 0.01730000 138. Oxatricyclo[8.2.0.04 ,6]dodecane, 32
380526.NL.02-967.475NL2
TEE tetramethyl- 57934-97-1 2-Cyclohexene-1- Givescone 0.01710000 139. carboxylic acid, 2- ethyl-6,6-dimethyl-, ethyl ester 14901-07-6 3-Buten-2-0ne, 4- | Beta-Ionone 0.01690000 140. (2,6,6-trimethyl-1- cyclohexen-1-yl)-,
GE)- 64001-15-6 4,7-Methano-1H- Dihydro Cyclacet | 0.01630000 141. inden-5-ol, octahydro-, 5-acetate 95-41-0 2-Cyclopenten-1- Iso Jasmone T 0.01600000 142. one, 2-hexyl- 134-20-3 Benzoic acid, 2- | Methyl 0.01580000 143. amino-, methyl ester | Anthranilate 100-06-1 Ethanone, 1-(4- | Para Methoxy | 0.01550000 144. methoxyphenyl)- Acetophenone 105-86-2 2,6-Octadien-1-01, Geranyl Formate | 0.01540000 145. 3,7-dimethyl-, 1- formate, (2F)- 154171-77-4 | Spiro[1,3-dioxolane- | Ysamber K* 0.01470000 146. 2.8’ (5’H)-[2H- 2,4a]methanonaphth alene], hexahydro- 1’,1°,5°,5- tetramethyl-, (2°8,4°a8,8’as)- (9C1) 154171-76-3 | Spiro[1,3-dioxolane- | Ysamber 0.01470000 147. 2.8’ (5’H)-[2H- 2,4a|methanonaphth alene], 127-41-3 3-Buten-2-0ne, 4- | Alpha-Tonone 0.01440000 148. (2,6,6-trimethyl-2- cyclohexen-1-yl)-, (3E)- 151-05-3 Benzeneethanol, a,0- | Dimethyl Benzyl | 0.01390000 149. dimethyl-, 1-acetate | Carbinyl Acetate 33
380526.NL.02-967.475NL2 2500-83-6 4,7-Methano-1H- Flor Acetate 0.01370000 150. inden-5-0l, 3a,4,5,6,7,7a- hexahydro-, 5- acetate 150-84-5 6-Octen-1-ol, 3,7- | Citronellyl acetate | 0.01370000 151. dimethyl-, 1-acetate 30310-41-9 2H-Pyran, Pelargene 0.01350000 152. tetrahydro-2-methyl- 4-methylene-6- phenyl- 68845-00-1 Bicyclo[3.3.1]nonan | Boisiris 0.01350000 153. e, 2-ethoxy-2,6,6- trimethyl-9- methylene- 106-24-1 2,6-Octadien-1-0l, Geraniol 0.01330000 154. 3,7-dimethyl-, (2E)- 106-25-2 2,6-Octadien-1-o0l, Nerol 0.01330000 155. 3,7-dimethyl-, (2Z)- 75975-83-6 Bicyclo[7.2.0]undec | Vetyvenal 0.01280000 156. -4-ene, 4,11,11- trimethyl-8- methylene-, 1R,4E,9S)- 19870-74-7 1H-3a,7- Cedryl methyl | 0.01280000 157. Methanoazulene, ether octahydro-6- methoxy-3,6,8,8- tetramethyl-, (3R,3aS,6S, 7R,8aS)- 87-44-5 Bicyclo[7.2.0]undec | Caryophyllene 0.01280000 158. -4-ene, 4,11,11- | Extra trimethyl-8- methylene-,
LR 4L,98)- 54440-17-4 1H-Inden-1-one, 2,3- | Safraleine 0.01260000 159. dihydro-2,3,3- trimethyl- 110-98-5 2-Propanol, 1,1’- | Dipropylene 0.01250000 160. oxybis- Glycol 34
380526.NL.02-967.475NL2 41890-92-0 2-Octanol, 7- | Osyrol® 0.01250000 161. methoxy-3,7- dimethyl- 71077-31-1 4,9-Decadienal, 4,8- | Floral Super 0.01230000 162. dimethyl- 65-85-0 Benzoic Acid Benzoic Acid 0.01220000 163. 61444-38-0 3-Hexenoic acid, | cis-3-hexenyl-cis- | 0.01220000 164. (3Z)-3-hexen-1-yl 3-hexenoate ester, (3Z)- 116044-44-1 | Bicyclo[2.2.l]hept- | Herbanate 0.01210000 165. 5-ene-2-carboxylic acid, 3-(1- 104-54-1 2-Propen-1-ol, 3- | Cinnamic Alcohol | 0.01170000 166. phenyl- 78-35-3 Propanoic acid, 2- | Linalyl 0.01170000 167. methyl-, 1-ethenyl- | Isobutyrate 1,5-dimethyl-4- hexen-1-yl ester 23495-12-7 Ethanol, 2-phenoxy-, | Phenoxy Ethyl | 0.01130000 168. 1-propanoate Propionate 103-26-4 2-Propenoic acid, 3- | Methyl 0.01120000 169. phenyl-, methyl ester | Cinnamate 67634-14-4 Benzenepropanal, 2- | Florazon (ortho- | 0.01110000 170. ethyl-o,a-dimethyl- | isomer) 5454-19-3 Propanoic acid, | N-Decyl 0.01100000 171. decyl ester Propionate 93-16-3 Benzene, 1,2- | Methyl Iso | 0.01100000 172. dimethoxy-4-(1- Eugenol propen-1-yl)- 81782-77-6 3-Decen-5-ol, 4- | 4-Methyl-3- 0.01070000 173. methyl- decen-5-0l 67845-30-1 Bicyclo[2.2.2]oct-5- | Maceal 0.01060000 174. ene-2- carboxaldehyde, 6- methyl-8-(1- methylethyl)-
380526.NL.02-967.475NL2 97-53-0 Phenol, 2-methoxy- | Eugenol 0.01040000 re ERE ee 120-57-0 1,3-Benzodioxole-5- | Heliotropin 0.01040000 176. carboxaldehyde 93-04-9 Naphthalene, 2- | Beta Naphthyl | 0.01040000 rm
Extra 99 20407-84-5 2-Dodecenal, (2F)- | Aldehyde 0.01020000 179. Mandarin 5462-06-6 Benzenepropanal, 4- | Canthoxal 0.01020000 oe Ee er 94-60-0 1,4- Dimethyl 1,4- | 0.01020000 181. Cyclohexanedicarbo | cyclohexanedicar xylic acid, 1,4- | boxylate dimethyl ester 57378-68-4 2-Buten-1-one, 1- | delta-Damascone | 0.01020000 182. (2,6,6-trimethyl-3- cyclohexen-1-yl)- 17283-81-7 2-Butanone, 4- | Dihydro Beta | 0.01020000 183. (2,6,6-trimethyl-1- Ionone cyclohexen-1-yl)- 1885-38-7 2-Propenenitrile, 3- | Cinnamalva 0.01010000 184. phenyl-, (2F)- 103-48-0 Propanoic acid, 2- | Phenyl Ethyl Iso | 0.00994000 oe phenylethyl ester me 186. one, 3-methyl-2- (2Z)-2-penten-1-yl- 7492-67-3 Acetaldehyde, 2- | Citronellyloxyace | 0.00967000 ee octen-1-yloxy]- 68683-20-5 1-Cyclohexene-1- Iso Bergamate 0.00965000 methylethyl)-, 1- formate 3025-30-7 2,4-Decadienoic Ethyl 2,4- | 0.00954000 189. acid, ethyl ester, | Decadienoate 2E,4Z)- 36
380526.NL.02-967.475NL2 103-54-8 2-Propen-1-ol, 3- | Cinnamyl Acetate | 0.00940000 190. phenyl-, 1-acetate on | ety ee 191. 1,1-dimethylethyl)- 3738-00-9 Naphtho[2,1- Ambrox® or | 0.00934000 192. b]furan, Cetalox* or dodecahydro- Synambran 3a,6,6,9a- tetramethyl- 51519-65-4 1,4- Tamisone 0.00932000 193. Methanonaphthalen- 5(1H)-one, 4,4a,6,7,8,8a- hexahydro- 148-05-1 Dodecanoic acid, 12- | Dodecalactone 0.00931000 194. hydroxy-, A-lactone 6CI,7CI); 1,12- 6790-58-5 (3aR,5a5,9a5,9bR)- | Ambronat* or | 0.00930000 195. 34,6,6,9a- Ambroxan® tetramethyl- 2,4,5,52,7,8,9,9b- octahydro-1H- benzo[e][ 1]benzofur an 86-26-0 1,1’-Biphenyl, 2- | Methyl Diphenyl | 0.00928000 196. methoxy- Ether 68738-94-3 2- Cyclomyral® 0.00920000 197. Naphthalenecarboxa
Idehyde, octahydro- 8,8-dimethyl on TEE Jae 198. oic acid, 2-propen-1- | Cyclohexane yl ester Propionate 7011-83-8 2(3H)-Furanone, 5- | Lactojasmone® 0.00885000 ul i methyl- an |" nei 200. Nonadienenitrile, 3,7-dimethyl- 692-86-4 10-Undecenoic acid, | Ethyl 0.00882000 201. ethyl ester Undecylenate 37
380526.NL.02-967.475NL2 103-95-7 Benzenepropanal, o- | Cymal 0.00881000 202. methyl-4-(1- methylethyl)- 13019-22-2 9-Decen-1-ol Rosalva 0.00879000 203. 94201-19-1 1- Methyl Laitone | 0.00872000 204. Oxaspiro[4.5]decan- | 10% TEC 2-one, 8-methyl- 104-61-0 2(3H)-Furanone, y-Nonalactone 0.00858000 205. dihydro-5-pentyl- 706-14-9 2(3H)-Furanone, 5- | y -Decalactone 0.00852000 206. hexyldihydro- 24720-09-0 2-Buten-1-one, 1- | a-Damascone 0.00830000 207. (2,6,6-trimethyl-2- cyclohexen-1-yl})-, 2F)- 39872-57-6 2-Buten-1-one, 1- | Isodamascone 0.00830000 208. (2,4,4-trimethyl-2- cyclohexen-1-yl)-, 2F)- 705-86-2 2H-Pyran-2-one, Decalactone 0.00825000 209. tetrahydro-6-pentyl- 67634-15-5 Benzenepropanal, 4- | Floralozone 0.00808000 210. ethyl-a,a-dimethyl- 40527-42-2 1,3-Benzodioxole, 5- | Heliotropin 0.00796000 211. (diethoxymethyl)- Diethyl Acetal 56973-85-4 4-Penten-1-one, 1- | Neobutenone a 0.00763000 212. (5,5-dimethyl-1- cyclohexen-1-yl)- 128-51-8 Bicyclo[3.1.1]hept- | Nopyl Acetate 0.00751000 213. 2-ene-2-ethanol, 6,6- dimethyl-, 2-acetate 103-36-6 2-Propenoic acid, 3- | Ethyl Cinnamate | 0.00729000 214. phenyl-, ethyl ester 5182-36-5 1,3-Dioxane, 2,4,6- | Floropal® 0.00709000 215. trimethyl-4-phenyl- 42604-12-6 Cyclododecane, Boisambrene 0.00686000 216. methoxymethoxy)- 38
380526.NL.02-967.475NL2 rr rr 0] 33885-52-8 Bicyclo[3.1.1]hept- | Pinyl Iso Butyrate | 0.00685000 217. 2-ene-2-propanal, Alpha 0,0,6,6-tetramethyl- 92015-65-1 2(3H)- Natactone 0.00680000 hexahydro-3,6- dimethyl- 63767-86-2 Cyclohexanemethan | Mugetanol 0.00678000 i re Ee methylethyl)- 3288-99-1 Benzeneacetonitrile, | Marenil CI 0.00665000 220. 4-(1,1- dimethylethyl)- 35044-68-9 2-Buten-1-one, 1- | beta-Damascone 0.00655000 221. (2,6,6-trimethyl-1- cyclohexen-1-yl)- 41724-19-0 1,4- Plicatone 0.00652000 6(2H)-one, octahydro-7-methyl 75147-23-8 Bicyclo[3.2.1]octan- | Buccoxime" 0.00647000 223. 8-one, 1,5-dimethyl-, oxime 25634-93-9 2-Methyl-5- Rosaphen® 0.00637000 224. phenylpentan-1-ol 600064 55066-48-3 3-Methyl-5- Phenyl Hexanol 0.00637000 225. phenylpentanol g 226. dimethyl-4-hexen-1- ylidene)-1-methyl- 2785-87-7 Phenol, 2-methoxy- | Dihydro Eugenol | 0.00624000 i rer EE ores an [Te Se MT 228. hydroxy-, 2- | Salicylate methylpropyl ester 4430-31-3 2H-1-Benzopyran-2- | Octahydro 0.00586000 229. one, octahydro- Coumarin 38462-22-5 Cyclohexanone, 2- | Ringonol 50 TEC | 0.00585000 ee ee ee 39
380526.NL.02-967.475NL2 mE methyl-
77-83-8 2-Oxiranecarboxylic | Ethyl Methyl 0.00571000 or Em phenyl-, ethyl ester
37677-14-8 3-Cyclohexene-1- Iso Hexenyl | 0.00565000 232. carboxaldehyde, 4- | Cyclohexenyl
(4-methyl-3-penten- | Carboxaldehyde 1-yl)-
103-60-6 Propanoic acid, 2- | Phenoxy Ethyl | 0.00562000 233. methyl-, 2- | 1so-Butyrate phenoxyethyl ester
18096-62-3 Indeno[1,2-d]-1,3- Indoflor® 0.00557000 234. dioxin, 4,44,5,9b-
tetrahydro-
63500-71-0 2H-Pyran-4-ol, Florosa Q/ Florol | 0.00557000 235. tetrahydro-4-methyl-
2-(2-methylpropyl)-
65405-84-7 Cyclohexanebutanal, | Cetonal® 0.00533000 236. 0,2,6,6-tetramethyl-
171102-41-3 | 4,7-Methano-1H- Flor Acetate 0.00530000 237. inden-6-ol,
34,4,5,6,7,7a- hexahydro-8,8- dimethyl-, 6-acetate
10339-55-6 1,6-Nonadien-3-ol, Ethyl linalool 0.00520000 238. 3,7-dimethyl-
23267-57-4 3-Buten-2-one, 4- | lonone Epoxide | 0.00520000 239. (2,2,6-trimethyl-7- Beta oxabicyclo[4.1.0]he pt-1-yl)-
97-54-1 Phenol, 2-methoxy- | Isoeugenol 0.00519000 re Rr me aa | lint TT 241. hexyldihydro-4-
methyl-
33885-52-8 Bicyclo[3.1.1]hept- | Pinyl Iso Butyrate | 0.00512000 ee Ep rg
0,0,6,6-tetramethyl-
23696-85-7 2-Buten-1-0ne, 1- | Damascenone 0.00503000 cyclohexadien-1-yl)-
380526.NL.02-967.475NL2 80-71-7 2-Cyclopenten-1- Maple Lactone 0.00484000
EE ner methyl- 67662-96-8 Propanoic acid, 2,2- | Pivarose Q 0.00484000 245. dimethyl-, 2- phenylethyl ester 2437-25-4 Dodecanenitrile Clonal 0.00480000 re [EE ee 141-14-0 6-Octen-1-o0l, 3,7- | Citronellyl 0.00469000 247. dimethyl-, 1- | Propionate propanoate 54992-90-4 3-Buten-2-one, 4- | Myrrhone 0.00460000 248. (2,2,3,6- tetramethylcyclohex yl)- 55066-49-4 Benzenepentanal, B- | Mefranal 0.00455000 i ree fm 7493-74-35 Acetic acid, 2-| Allyl Phenoxy | 0.00454000 250. phenoxy-, 2-propen- | Acetate 1-yl ester 80-54-6 Benzenepropanal, 4- | Lilial® 0.00444000 251. (1,1-dimethylethyl)- a-methyl- 86803-90-9 4,7-Methano-1H- Scentenal® 0.00439000 252. indene-2- carboxaldehyde, octahydro-5- methoxy- 68991-97-9 2- Melafleur 0.00436000 253. Naphthalenecarboxa dehyde, 1,2,3,4,5,6,7,8- octahydro-8,8- dimethyl- 18871-14-2 Pentitol, 1,5- | Jasmal 0.00434000 254. anhydro-2,4- dideoxy-2-pentyl-, 3-acetate 58567-11-6 Cyclododecane, Boisambren Forte | 0.00433000 255. (ethoxymethoxy)- so MM [nee 256. bJoxirene, 41
380526.NL.02-967.475NL2 1a,2,3,4,5,6,7,7a- octahydro- 1a,3,3,4,6,6- hexamethyl-, laR,4S,7aS-rel- oe 257. (2,5,6,6-tetramethyl- 2-cyclohexen-1-yl}- 65442-31-1 Quinoline, 6-(1- | Iso Butyl | 0.00408000 er EE we 87731-18-8 Carbonic acid, 4- | Violiff 0.00401000 259. cycloocten-1-yl methyl ester 173445-65-3 | 1H-Indene-5- Hivernal (A- | 0.00392000 260. propanal, 2,3- | isomer) dihydro-3,3- dimethyl- 23911-56-0 Ethanone, 1-(3- | Nerolione 0.00383000 261. methyl-2- benzofuranyl)- 52474-60-9 3-Cyclohexene-1- Precyclemone B | 0.00381000 262. carboxaldehyde, 1- methyl-3-(4-methyl- 3-penten-1-yl)- 139539-66-5 | 6-Oxabicyclo Cassifix 0.00381000 263. [3.2.1]octane, 5- methyl-1-(2,2,3- trimethyl-3- cyclopenten-1-yl)- 80858-47-5 Benzene, [2- | Phenafleur 0.00380000 264. (cyclohexyloxy)ethy 1]- 32764-98-0 2H-Pyran-2-0ne, Jasmolactone 0.00355000 re Ee ear ae penten-1-yl)- 78417-28-4 2,4,7-Decatrienoic Ethyl 2,4,7- | 0.00353000 266. acid, ethyl ester decatrienoate 140-26-1 Butanoic acid, 3- | Beta Phenyl Ethyl | 0.00347000
EN phenylethyl ester 105-90-8 2,6-Octadien-1-01, Geranyl 0.003360000 268. 3,7-dimethyl-, 1- | Propionate propanoate, (2£)- 42
380526.NL.02-967.475NL2 41816-03-9 Spiro[1,4- Rhubofix® 0.00332000 269. methanonaphthalene -2(1H),2’ -oxirane], 3.4,4a,5,8,8a- hexahydro-3’,7- dimethyl- 7070-15-7 Ethanol, 2- | Arbanol 0.00326000 270. [[(1R.2R,4R)-1,7,7- trimethylbicyclo[2.2.
L]hept-2-yl]oxy]-, rel- 93-29-8 Phenol, 2-methoxy- | Iso Eugenol | 0.00324000 271. 4-(1-propen-1-yl)-, | Acetate l-acetate 476332-65-7 | 2H-Indeno[4,5- Amber Xtreme | 0.00323000 272. b]furan, decahydro- | Compound 1 2,2,6,6,7,8,8- heptamethyl- 68901-15-5 Acetic acid, 2- | Cyclogalbanate 0.00323000 273. (cyclohexyloxy)-, 2- propen-1-yl ester 107-75-5 Octanal, 7-hydroxy- | Hydroxycitronella | 0.00318000 274. 3,7-dimethyl- 1 68611-23-4 Naphtho[2,1- Grisalva 0.00305000 275. b]furan, 9b- ethyldodecahydro- 34,7, 7-trimethyl- 313973-37-4 | 1,6-Heptadien-3- Pharaone 0.00298000 276. one, 2-cyclohexyl- 137-00-8 5-Thiazoleethanol, Sulfurol 0.00297000 or re er on [TS 278. (2,6,6-trimethyl-2- cyclohexen-1-yl)- 127-51-5 3-Buten-2-one, 3- | Isoraldeine Pure 0.00282000 279. methyl-4-(2,6,6- trimethyl-2- cyclohexen-1-yl)- 72903-27-6 1,4- Fructalate™ 0.00274000 280. Cyclohexanedicarbo xylic acid, 1,4- diethyl ester 43
380526.NL.02-967.475NL2 7388-22-9 3-Buten-2-0ne, 4- | Tonone Gamma | 0.00272000 ee methylenecyclohexy 1)-3-methyl- 104-67-6 2(3H)-Furanone, 5- | gamma- 0.00271000 282. heptyldihydro- Undecalactone racemic) 1205-17-0 1,3-Benzodioxole-5- | Helional 0.00270000 283. propanal, a-methyl- 33704-61-9 4H-Inden-4-one, Cashmeran 0.00269000 284. 1,2,3,5,6,7- hexahydro-1,1,2,3,3- pentamethyl- mr ee 285. (1-ethoxyethenyl)- 3.3,5,5-tetramethyl- 97384-48-0 Benzenepropanenitri | Citrowanil® B 0.00265000 286. le, a-ethenyl-a- methyl- 141-13-9 9-Undecenal, 2,6,10- | Adoxal 0.00257000 287. trimethyl- 2110-18-1 Pyridine, 2-(3- | Corps Racine VS | 0.00257000 288. phenylpropyl)- 27606-09-3 Indeno[1,2-d]-1,3- Magnolan 0.00251000 289. dioxin, 4,44,5,9b- tetrahydro-2,4- dimethyl- re [Je J acetate acetate 67634-20-2 Propanoic acid, 2- | Cyclabute 0.00244000 290. methyl-, 34,4,5,6,7,7a- hexahydro-4,7- methano-1H-mden- 5-yl ester 65405-72-3 1-Naphthalenol, Oxyoctaline 0.00236000 291. 1,2,3,4,44,7,8,8a- Formate octahydro-2,44,5,8a- tetramethyl-, 1- formate ao || mentee” | Aldus OO 292. (phenylmethylene)- | Aldehyde 44
380526.NL.02-967.475NL2 rr rr 0] 103694-68-4 | Benzenepropanol, Majantol® 0.00224000 293. B,B,3-trimethyl- 13215-88-8 2-Cyclohexen-1-one, | Tabanone Coeur | 0.00223000 ylidene)-3,5,5- trimethyl- 25152-85-6 3-Hexen-1-o0l, 1- | Cis-3-Hexenyl 0.00203000 295. benzoate, (3Z)- Benzoate 406488-30-0 | 2-Ethyl-N-methyl-N- | Paradisamide 0.00200000 296. (m-tolyl)butanamide 121-33-5 Benzaldehyde, 4- | Vanillin 0.00194000 297. hydroxy-3-methoxy- 77-54-3 1H-3a,7- Cedac 0.00192000 298. Methanoazulen-6-ol, octahydro-3,6,8,8- tetramethyl-, 6- acetate, (3R,3a5S,6R, 7R,8aS)- 76842-49-4 4,7-Methano-1H- Frutene 0.00184000 299. inden-6-ol, 34,4,5,6,7,7a- hexahydro-8,8- dimethyl-, 6- propanoate 121-39-1 2-Oxiranecarboxylic | Ethyl Phenyl | 0.00184000 300. acid, 3-phenyl-, ethyl | Glycidate ester 211299-54-6 | 4H-4a,9- Ambrocenide® 0.00182000 301. Methanoazuleno[5,6 -d]-1,3-dioxole, octahydro- 2,2,5,8,8,9a- hexamethyl-, (4aR,5R,7aS,9R)- 285977-85-7 | (2,5-Dimethyl-1,3- | Lilyflore 0.00180000 re EE )methanol 10094-34-5 Butanoic acid, 1,1- | Dimethyl Benzyl | 0.00168000 303. dimethyl-2- Carbinyl Butyrate phenylethyl ester
380526.NL.02-967.475NL2 40785-62-4 Cyclododeca[c] Muscogene 0.00163000 304. furan, 1,3,34,4,5,6,7, 8,9,10,11,13a- dodecahydro- 75490-39-0 Benzenebutanenitril | Khusinil 0.00162000 pe Ee 55418-52-5 2-Butanone, 4-(1,3- | Dulcinyl 0.00161000 306. benzodioxol-5-yl})- 3943-74-6 Benzoic acid, 4- | Carnaline 0.00157000 307. hydroxy-3-methoxy- , methyl ester 72089-08-8 3-Cyclopentene-1- | Brahmanol® 0.00154000 308. butanol, B,2,2,3- tetramethyl- 2-
Methyl-4-(2,2,3- trimethyl-3- cyclopenten-1- yl)butanol 3155-71-3 2-Butenal, 2-methyl- | Boronal 0.00147000 309. 4-(2,6,6-trimethyl-1- cyclohexen-1-yl)- 2050-08-0 Benzoic acid, 2- | Amyl Salicylate | 0.00144000 310. hydroxy-, pentyl ester 41199-20-6 2-Naphthalenol, Ambrinol 0.00140000 311. decahydro-2,5,5- trimethyl- 12262-03-2 ndecanoic acid, 3- | Iso Amyl | 0.00140000 312. methylbutyl ester Undecylenate 107-74-4 1,7-Octanediol, 3,7- | Hydroxyol 0.00139000 313. dimethyl- 91-64-5 2H-1-Benzopyran-2- | Coumarin 0.00130000 ee 68901-32-6 1,3-Dioxolane, 2-[6- | Glycolierral 0.00121000 315. methyl-8-(1- methylethyl)bicyclo[ 2.2.2]oct-5-en-2-yl]- 68039-44-1 Propanoic acid, 2,2- | Pivacyclene 0.00119000 316. dimethyl-, 34,4,5,6, 7,7a-hexahydro-4,7- 46
380526.NL.02-967.475NL2 methano-1H-inden- 6-yl ester 106-29-6 Butanoic acid, (2£)- | Geranyl Butyrate | 0.00116000 317. 3,7-dimethyl-2,6- octadien-1-yl ester 5471-51-2 2-Butanone, 4-(4- | Raspberry ketone | 0.00106000 318. hydroxyphenyl)- 109-42-2 10-Undecenoic acid, | Butyl 0.00104000 319. butyl ester Undecylenate 320. | 2785-89-9 4-Ethyl-2- 4-Ethylguaiacol 0.02000000 methoxyphenol 27538-10-9 2-ethyl-4-hydroxy- | Homofuronol 0.01210000
S-methylfuran-3-one * Vapor Pressures are acquired as described in the Test Methods Section. ** Origin: Same as for Table 1 hereinabove.
Table 2B--Moderate Volatile Natural Oils.
Cade Oil H. Reynaud & Fils
Clove Leaf Oil Rectified H. Reynaud & Fils
B Clove Stem Oil H. Reynaud & Fils
Li LC. 47
380526.NL.02-967.475NL2
Suppliers:
Citrus & Allied Essences, New York, USA
H. Reynaud & Fils, Montbrun-les-Bains, France
IFF, Hazlet, New Jersey, USA
Robertet, Grasse, France
[46] Moderate volatile fragrance materials can be selected from the group of Tables 2A or 2B. However, it is understood by one skilled in the art that other moderate volatile fragrance materials, not recited in Tables 2A or 2B, would also fall within the scope of the present invention, so long as they have a vapor pressure of 0.1 to 0.001 Torr at 25 °C. (i1) High Volatile Fragrance Materials
[47] The fragrance component may include at least one high volatile fragrance material having a vapor pressure greater than 0.1 Torr (0.0133 kPa) at 25 °C. In some examples, the high volatile fragrance material can include at least 2 high volatile fragrance materials, 3 high volatile fragrance materials, or at least 5 high volatile fragrance materials, or at least 7 high volatile fragrance materials. If there are more than one high volatile fragrance materials, then the ranges provided hereinabove cover the total of all of the high volatile fragrance materials. Suitable examples of high volatile fragrances materials are provided in Tables 3A and 3B below.
[48] Preferably, the high volatile fragrance material is selected from at least 1 material, or at least 2 materials, or at least 3 materials, or at least 5 materials, at least 7 materials, or at least 9 high volatile fragrance materials as disclosed in Table 3A. Natural fragrance materials or oils having an aggregate vapor pressure greater than 0.1 Torr (0.0133 kPa) at 25 °C are provided in
Table 3B. Moderate Volatile Natural Oils. 48
380526.NL.02-967.475NL2
Table 3A — High Volatile Fragrance Materials
No. CAS IUPAC Name Common Name** | Vapor
Number Pressure (Torr at 25 °C)* 107-31-3 Formic acid, | Methyl Formate 732.00000000 1. methyl ester 75-18-3 Methane, 1,1°- | Dimethyl Sulfide | 647.00000000 2. thiobis- 1.0% In DEP 141-78-6 Acetic acid ethyl | Ethyl Acetate 112.00000000 3. ester 105-37-3 Propanoic acid, | Ethyl Propionate 44.50000000 4. ethyl ester 110-19-0 Acetic acid, 2- | Isobutyl Acetate 18.00000000 5. methylpropyl ester 105-54-4 Butanoic acid, | Ethyl Butyrate 13.90000000 ethyl ester a 14765-30-1 Butyl Alcohol 8.52000000 7. 7452-79-1 Butanoic acid, 2- | Ethyl-2-Methyl 7.85000000 methyl-, ethyl | Butyrate ester 123-92-2 1-Butanol, 3- | Iso Amyl Acetate 5.68000000 9. methyl-, 1- acetate 66576-71-4 | Butanoic acid, 2- Iso Propyl 2- | 5.10000000 10. methyl-, 1- | Methylbutyrate methylethyl ester 110-43-0 2-Heptanone Methyl Amyl | 473000000 11. Ketone 6728-26-3 2-Hexenal, (2F)- | Trans-2 Hexenal 4.62000000 12. 123-51-3 1-Butanol, 3- | Isoamyl Alcohol 4.16000000 13. methyl- 49
380526.NL.02-967.475NL2 1191-16-8 2-Buten-l-ol, 3- | Prenyl acetate 3.99000000 14. methyl-, 1- acetate 57366-77-5 | 1,3-Dioxolane-2- | Methyl Dioxolan 3.88000000 15. methanamine, N- methyl- 7785-70-8 Bicyclo[3.1.1]he | Alpha Pinene 3.49000000 16. pt-2-ene, 2,6,6- trimethyl-, (1R,5R)- 79-92-5 Bicyeclo[2.2.1]he | Camphene 3.38000000 17. ptane, 2,2- dimethyl-3- methylene- 94087-83-9 | 2-Butanethiol, 4- | 4-Methoxy-2- 3.31000000 18. methoxy-2- Methyl-2- methyl- Butanenthiol 39255-32-8 | Pentanoic acid, | Manzanate 2.91000000 19. 2-methyl-, ethyl ester 3387-41-5 Bicyclo[3.1.0]he | Sabinene 2.63000000 20. xane, 4- methylene-1-(1- methylethyl)- 127-91-3 Bicyclo[3.1.1]he | Beta Pinene 2.40000000 21. ptane, 6,6- dimethyl-2- methylene- 105-68-0 1-Butanol, 3- | Amyl Propionate 2.36000000 22. methyl-, 1- propanoate 123-35-3 1,6-Octadiene, 7- | Myrcene 2.29000000 23. methyl-3- methylene- 124-13-0 Octanal Octyl Aldehyde 2.07000000 24. 7392-19-0 2H-Pyran, 2- | Limetol 1.90000000 25. ethenyltetrahydr 0-2,6,6- trimethyl- 111-13-7 2-Octanone Methyl Hexyl | 1.72000000 26. Ketone
380526.NL.02-967.475NL2 123-66-0 Hexanoic acid, | Ethyl Caproate 1.66000000 27. ethyl ester 470-82-6 2- Eucalyptol 1.65000000 28. Oxabicyclo[2.2.2
Joctane, 1,3,3- trimethyl- 99-87-6 Benzene, 1- | Para Cymene 1.65000000 29. methyl-4-(1- methylethyl)- 104-93-8 Benzene, 1- | Para Cresyl Methyl | 1.65000000 30. methoxy-4- Ether methyl- 13877-91-3 | 1,3,6-Octatriene, | Ocimene 1.56000000 31. 3,7-dimethyl- 138-86-3 Cyclohexene, 1- | dl-Limonene 1.54000000 32. methyl-4-(1- methylethenyl)- 5989-27-35 Cyclohexene, 1- | d-limonene 1.54000000 33. methyl-4-(1- methylethenyl)-, (4R)- 106-68-3 3-Octanone Ethyl Amyl Ketone | 1.50000000 34. 110-41-8 Undecanal, 2- | Methyl Nonyl | 1.43000000 35. methyl- Acetaldehyde 142-92-7 Acetic acid, | Hexyl acetate 1.39000000 36. hexyl ester 110-93-0 5-Hepten-2-one, | Methyl Heptenone | 1.28000000 37. 6-methyl- 81925-81-7 | 2-Hepten-4-one, | Filbertone 1% in | 1.25000000 38. 5-methyl- TEC 3681-71-8 3-Hexen-l-ol, 1- | cis-3-Hexenyl 1.22000000 39. acetate, (3Z)- acetate 97-64-3 Propanoic acid, | Ethyl Lactate 1.16000000 40. 2-hydroxy-, ethyl ester 51
380526.NL.02-967.475NL2 586-62-9 Cyclohexene, 1- | Terpineolene 1.13000000 41. methyl-4-(1- methylethylidene )- 51115-64-1 | Butanoic acid, 2- | Amyl butyrate 1.09000000 42. methylbutyl ester 106-27-4 Butanoic acid, 3- | Amyl Butyrate 1.09000000 43. methylbutyl ester 99-85-4 1,4- Gamma Terpinene | 1.08000000 44. Cyclohexadiene, 1-methyl-4-(1- methylethyl)- 18640-74-9 | Thiazole, 2-(2- | 2-Isobutylthiazole 1.07000000 45. methylpropyl)- 928-96-1 3-Hexen-1-ol, cis-3-Hexenol 1.04000000 46. (3Z)- 100-52-7 Benzaldehyde Benzaldehyde 0.97400000 47. 141-97-9 Butanoic acid, 3- | Ethyl Acetoacetate | 0.89000000 48. oxo-, ethyl ester 928-95-0 2-Hexen-1-ol, Trans-2-Hexenol 0.87300000 49. (2E)- 928-94-9 2-Hexen-1-ol, Beta Gamma | 0.87300000 50. (2Z)- Hexenol 24691-15-4 | Cyclohexane, 3- | Herbavert 0.85200000 51. ethoxy-1,1,5- trimethyl-, cis- 9CI 19872-52-7 | 2-Pentanone, 4- | 4-Methyl-4- 0.84300000 52. mercapto-4- Mercaptopentan-2- methyl- one ppm TEC 3016-19-1 2,4,6-Octatriene, | Allo-Ocimene 0.81600000 53. 2,6-dimethyl-, 4E,6E)- 69103-20-4 | Oxirane, 2,2- | Myroxide 0.80600000 54. dimethyl-3-(3- 52
380526.NL.02-967.475NL2
TEE, pentadien-1-yl)- 189440-77- | 4,7-Octadienoic | Anapear 0.77700000 re me ester, (4E)- 67633-96-9 | Carbonic acid, | Liffarome™ 0.72100000 56. (3Z)-3-hexen-1- yl methyl ester 123-68-2 Hexanoic acid, 2- | Allyl Caproate 0.67800000 57. propen-1-yl ester 106-72-9 S-Heptenal, 2,6- | Melonal 0.62200000 58. dimethyl- 106-30-9 Heptanoic acid, | Ethyl Oenanthate 0.60200000 59. ethyl ester
He li 1- carboxaldehyde, 2,4-dimethyl- o | ie, 61. dimethoxyethyl)- | Acetaldehyde
Dimethyl Acetal 16409-43-1 | 2H-Pyran, Rose Oxide 0.55100000 62. tetrahydro-4- methyl-2-(2- methyl-1- propen-1-yl)- 925-78-0 3-Nonanone Ethyl Hexyl Ketone | 0.55100000 63. 100-47-0 Benzonitrile Benzyl Nitrile 0.52400000 64. 589-98-0 3-Octanol Octanol-3 0.51200000 [ee 58430-94-7 | 1-Hexanol, Iso Nonyl Acetate | 0.47000000 66. 3,5,5-trimethyl-, 1-acetate 10250-45-0 | 4-Heptanol, 2,6- | Alicate 0.45400000 67. dimethyl-, 4- acetate 53
380526.NL.02-967.475NL2 105-79-3 Hexanoic acid, 2- | Iso Butyl Caproate | 0.41300000 oT Eee ester 2349-07-7 Propanoic acid, | Hexyl isobutyrate 0.41300000 69. 2-methyl-, hexyl ester 23250-42-2 | Cyclohexanecarb | Cyprissate 0.40500000 70. oxylic acid, 1,4- dimethyl-, methyl ester, trans- 122-78-1 Benzeneacetalde | Phenyl 0.36800000 71. hyde acetaldehyde 5405-41-4 Butanoic acid, 3- | Ethyl-3-Hydroxy 0.36200000 72. hydroxy-, ethyl | Butyrate ester 105-53-3 Propanedioic Diethyl Malonate 0.34400000 73. acid, 1,3-diethyl ester 93-58-3 Benzoic acid, | Methyl Benzoate 0.34000000 74. methyl ester 16356-11-9 | 1,3,5- Undecatriene 0.33600000 75. Undecatriene 65405-70-1 | 4-Decenal, (4E)- | Decenal (Trans-4) | 0.33100000 76. 54546-26-8 | 1,3-Dioxane, 2- | Herboxane 0.33000000 77. butyl-4,4,6- trimethyl- 13254-34-7 | 2-Heptanol, 2,6- | Dimethyl-2 6- | 0.33000000 78. dimethyl- Heptan-2-ol 98-86-2 Ethanone, 1- | Acetophenone 0.29900000
J
EE [ee hyde, a-methyl- | aldehyde 80118-06-5 | Propanoic acid, | Iso Pentyrate 0.28500000 81. 2-methyl-, 1,3- dimethyl-3- buten-1-yl ester 54
380526.NL.02-967.475NL2 557-48-2 2,6-Nonadienal, |E Z-2,6-Nonadien- | 0.28000000 ee Eee 24683-00-9 | Pyrazine, 2- | 2-Methoxy-3- 0.27300000 83. methoxy-3-(2- Isobutyl Pyrazine methylpropyl)- 104-57-4 Formic acid, | Benzyl Formate 0.27300000
Sal “alas ester 104-45-0 Benzene, 1- | Dihydroanethole 0.26600000 85. methoxy-4- propyl- 491-07-6 Cyclohexanone, | Iso Menthone 0.25600000 86. 5-methyl-2-(1- methylethyl)-, 2R,5R)-rel- 89-80-5 Cyclohexanone, | Menthone Racemic | 0.25600000 87. 5-methyl-2-(1- methylethyl)-, 2R,58)-rel- 2463-53-8 2-Nonenal 2 Nonen-1-al 0.25600000 88. 55739-89-4 | Cyclohexanone, | Thuyacetone 0.25000000 89. 2-ethyl-4,4- dimethyl- 150-78-7 Benzene, 1,4- | Hydroquinone 0.25000000 dimethoxy- Dimethyl Ether 64988-06-3 | Benzene, 1- | Rosacene 0.24600000 91. (ethoxymethyl)- 2-methoxy- wT 92. ptan-2-one, 1,7,7-trimethyl- 67674-46-8 | 2-Hexene, 6,6- | Methyl 0.21400000
Ee trimethyl- 112-31-2 Decanal Decyl Aldehyde 0.20700000 94. 16251-77-7 | Benzenepropanal | Trifernal 0.20600000 95. ‚ B-methyl-
380526.NL.02-967.475NL2 93-92-5 Benzenemethano | Methylphenylcarbi | 0.20300000
TE acetate or |" |e ee [970000 97. nonyl ester 122-00-9 Ethanone, 1-(4- | Para Methyl | 0.18700000 98. methylphenyl)- | Acetophenone 24237-00-1 | 2H-Pyran, 6- | Gyrane 0.18600000 99. butyl-3,6- dihydro-2,4- dimethyl- 41519-23-7 | Propanoic acid, | Hexenyl Isobutyrate | 0.18200000 100. 2-methyl-, (3Z)- 3-hexen-1-yl ester 93-89-0 Benzoic acid, | Ethyl Benzoate 0.18000000 101. ethyl ester 20780-48-7 | 3-Octanol, 3,7- | Tetrahydro Linalyl | 0.18000000
Ee acetate 101-41-7 Methyl 2- | Methylphenyl 0.17600000 103. phenylacetate acetate 40853-55-2 | 1-Hexanol, 5- | Tetrahydro 0.17300000 104. methyl-2-(1- Lavandulyl Acetate methylethyl)-, 1- acetate 933-48-2 Cyclohexanol, Trimethylcyclohexa | 0.17300000 105. 3.3,5-trimethyl-, | nol 1R,5R)-rel- 35158-25-9 | 2-Hexenal, 5- | Lactone of Cis | 0.17200000 106. methyl-2-(1- Jasmone methylethyl)- 18479-58-8 | 7-Octen-2-ol, Dihydromyrcenol 0.16600000 io [oe Eee 140-11-4 Acetic acid, | Benzyl acetate 0.16400000 108. phenylmethyl ester 14765-30-1 | Cyclohexanone, | 2-sec-Butyl Cyclo | 0.16300000 109. 2-(1- Hexanone methylpropyl)- 56
380526.NL.02-967.475NL2 20125-84-2 | 3-Octen-1-ol, Octenol 0.16000000 re 142-19-8 Heptanoic acid, | Allyl Heptoate 0.16000000 111. 2-propen-1-yl ester 100-51-6 Benzenemethano | Benzyl Alcohol 0.15800000 ee ee 10032-15-2 | Butanoic acid, 2- | Hexyl-2-Methyl 0.15800000 113. methyl-, hexyl | Butyrate ester 695-06-7 2(3H)-Furanone, | Gamma 0.15200000 114. S-ethyldihydro- | Hexalactone 21722-83-8 | Cyclohexaneetha | Cyclohexyl Ethyl | 0.15200000 115. nol, 1-acetate Acetate 111-79-5 2-Nonenoic acid, | Methyl-2- 0.14600000 116. methyl ester Nonenoate 16491-36-4 | Butanoic acid, | Cis 3 Hexenyl | 0.13500000 117. (3Z)-3-hexen-1- | Butyrate yl ester 111-12-6 2-Octynoic acid, | Methyl Heptine | 0.12500000 118. methyl ester Carbonate 59323-76-1 | 1,3-Oxathiane, 2- | Oxane 0.12300000 119. methyl-4-propyl- , (2R,4S)-rel- om [7 120. methoxy-2,6- dimethyl- 13851-11-1 | Bicyclo[2.2.1]he | Fenchyl Acetate 0.11700000 121. ptan-2-ol, 1,3,3- trimethyl-, 2- acetate 115-95-7 1,6-Octadien-3- | Lmalyl acetate 0.11600000 oe Te 3-acetate oo [EE er Re 123. dimethyl- Myrcenol 78-69-3 3,7- Tetra-Hydro 0.11500000 fe ol 57
380526.NL.02-967.475NL2 111-87-5 1-Octanol Octyl Alcohol 0.11400000 or ore oo [i 126. 1-methanethiol, mercaptan a, 0, 4-trimethyl- 80-25-1 Cyclohexanemet | Menthanyl Acetate | 0.10300000 127. hanol, o,o,4- trimethyl-, 1- acetate 88-41-5 Cyclohexanol, 2- | Verdox™ 0.10300000 128. (1,1- dimethylethyl)-, 1-acetate 32210-23-4 | Cyclohexanol, 4- | Vertenex 0.10300000 129. (1,1- dimethylethyl)-, 1-acetate 112-44-7 Undecanal n-Undecanal 0.10200000 130. 124-19-6 Nonanal Nonanal Aldehyde | 0.53200000 131. C-9 929253-05- | 6-methoxy-2,6- | 6-methoxy-2,6- 0.04020000 132. | 4 dimethyloctanal | dimethyl octanal 68039-47-4 | 2-propan-2- Phenethyl Isopropyl | 0.24900000 133. yloxyethylbenze | Ether ne 6413-10-1 ethyl 2-(2- | Apple Ketal 0.21900000 134. methyl-1,3- dioxolan-2- yl)acetate 106-23-0 3,7-dimethyloct- | citronellal 0.21500000 135. 6-enal
Pyrazine-2,3,5 23.5 * Vapor Pressures are acquired as described in the Test Methods Section. *% Origin: Same as for Table 1 hereinabove.
Table 3B— High Volatile Natural Materials 58
380526.NL.02-967.475NL2 a aen fe
Ke [wma 59
380526.NL.02-967.475NL2 25. Olibanum Oil Pyrogenous
Suppliers
Biolandes, Le Sen, France
Capua, Campo Calabro, Italy
Citrus & Allied Essences, New York, USA
Firmenich, Geneva, Switzerland
Global Essence Inc, New Jersey, USA
H. Reynaud & Fils, Montbrun-les-Bains, France
IFF, Hazlet, New Jersey, USA
Kerry, Co. Kerry, Ireland
Mane, Le Bar-sur-Loup, France
Misitano & Stracuzzi, Messina, Italy
Robertet, Grasse, France
Simone Gatto, San Pierre Niceto, Italy 60
380526.NL.02-967.475NL2
[49] Exemplary high volatile fragrance materials selected from the group of Tables 3A or 3B are preferred. However, it is understood by one skilled in the art that other high volatile fragrance materials, not recited in Tables 3A or 3B, would also fall within the scope of the present invention, so long as they have a vapor pressure of greater than 0.1 Torr (0.0133 kPa) at 25 °C.
[59] The individual fragrance materials can be present in various concentrations of the fragrance component. For example in a “diamond construction” the low volatile material can be present in a range of from about 0 wt% to about 30 wt% of the fragrance component, about 10 wt% to about 20 wt%, less than equal to or greater than about 0 wt%, 5, 10, 15, 20, 25, or 30 wt%; the moderate volatile component can be present in a range of from about 30 wt% to about 70 wt% of the fragrance component, about 40 wt% to about 60 wt%, less than, equal to, or greater than about 30 wt%, 35, 40, 45, 50, 55, 60, 65, or about 70 wt%; the high volatile fragrance component can be present in a 0 wt% to about 30 wt% of the fragrance component, about 10 wt% to about 20 wt%, less than equal to or greater than about 0 wt%, 5, 10, 15, 20, 25, or 30 wt%.
[51] The composition can further include at least one modulator as described herein below. Suitable examples of the fragrance modulators include: the compound according to Formula I:
OH
Aw
R' (1): a polymer including a repeating unit derived from the compound according to Formula II:
NT R4
R3 R® (TT); or a mixture thereof. RI. R?, R’, RY, and R5, are independently chosen from -H, -OH, or substituted or unsubstituted (Ci-Cao)hydrocarbyl. In some further embodiments, R!, R2, R3, R*, and R5, are independently chosen from (C1-C>o)alkyl, (C2-Cao)alkeneyl, (C:-C9)eycloalkyl, (Ci-
Can)alkoxyl, (Ci-Cao)aryl, or a combination thereof. In some specific embodiments, the modulator 61
380526.NL.02-967.475NL2 component includes pentylene glycol, polycitronellol, or a mixture thereof. In some embodiments, the polycitronellol can include 2-8 repeating units and can have a weight-average-molecular weight in a range of from about 460 g/mol to about 1500 g/mol. In some embodiments, the modulator component can include a mixture of pentylene glycol and polycitronellol and a molar ratio of pentylene glycol to polycitronellol is in a range of from about 5:1 to about 1:5, about 4:1 to about 1:4, about 3:1 to about 1:3, or about 2:1 to about 1:2, or about 1:1. In some embodiments, the modulator component can include at least some PPG-20 methyl glucose ether mixed with any of the aforementioned modulators. Alternativly, the modulator component can be free of (include 0 wt%) PPG-20 methyl glucose. If PPG-20 methyl glucose is present, it can be in range of from about 1 wt% to about 15 wt% of the modulator component, about 5 wt% to about 10 wt% of the modulator component, less than, equal to, or greater than about 1 wt%, 2,3, 4,5, 6, 7,8, 9, 10, 11, 12, 13, 14, or about 15 wt%.
[52] In some further examples, the modulator component can include other modulators included in addition to pentylene glycol, polycitronellol, or a mixture thereof. Examples of the additional modulators can include those listed herein below in Tables 4(a) and 4(b).
Tables 4(a) and 4(b) provide lists of suitable non-odorous fragrance modulators.
Table 4(a}): Substantially Non-Odorous Fragrance Modulators
Number 2.
PPG-20 Methyl Glucose Ether ’ | 61849-72-7
Ether *
Po eee fe 5. Undecyl Glucoside *< (France) 62
380526.NL.02-967.475NL2
Ashland (b) Isocetyl Alcohol * 36653-82-4 | Speciality
Ingredients (c) Neopentyl Glycol 28510-23-8 | Lubrizol
Diethylhexanoate ‘
Alfa
Sucrose Laurate 25339-99-5 | Chemicals
Ltd. (UK)
Alfa 10. Sucrose dilaurate 25915-57-5 | Chemicals (d) Ltd. (UK)
Mitsubishi 11. Sucrose Myristate 27216-47-3
Chemicals
Chemicals 13. Sucrose Stearate 25168-73-4
Ltd. (UK)
Mitsubishi 14. Sucrose Distearate 27195-16-0 | Chemicals (IP)
Mitsubishi 27923063- 15. Sucrose Tristearate 3 Chemicals (JP) (E)1-2.2.6-
Takasago 16. (e) trimethylcyclohexyl)oct-1-en-3- (Japan) one * 2-(1-menthoxy)ethane-1-ol * - , Takasago (f) 1-(1-menthoxy)propane-2-ol * - (Japan) 3-(1-menthoxy)propane-1-ol * - 63
380526.NL.02-967.475NL2 50 3-(1-menthoxy)propane-1,2- ' diol ” 2-methyl-3-(1- 21. . menthoxy)propane-1,2-diol ° 4-(1-menthoxy) butane-1-ol ° - 1,1,4,4-tetramethyl-6-acetyl-7- 23. formyl-1,2,3,4- /
Givaudan tetrahydronaphthalene (8) (Switzerland 1,1,2,4,4-pentamethyl-6-acetyl- ) 24. 7-formyl-1,2,3,4- tetrahydronaphthalene ’°
Hyaluronic acid disaccharide Sigma 25. 9004-61-9 (h) sodium salt 77 Aldrich
Sodium Hyaluronate ’/ 9067-32-7 | (UK) , Mono-o-(linalyl)-glucopyranose 27. i
Di-o-(linalyl)-glucopyranose *° -
Tri-o-(linalyl)-glucopyranose ** - . Tetra-o-(linalyl)-glucopyranose 30. D 3 Penta-o-(linalyl)-glucopyranose £2 Kanebo (1)
Mono-o-(cis-3-hexenyl)- (Japan) 32 glactopyranose ’? 3 Di-o-(cis-3-hexenyl)- glactopyranose *
Tri-o0-(cis-3-hexenyl)- 34. , glactopyranose 7
Tetra-o-(cis-3-hexenyl)- glactopyranose /2 64
380526.NL.02-967.475NL2 a | =e glactopyranose ee glucopyranose ’> ee glucopyranose ’? re glucopyranose ’* eere glucopyranose’?
Bis-0-(3,6-dioxaoctanyl)- are eee galactopyranose ’° galactopyranose’’ ra galactopyranose ’* pas xylopyranose * ice xylopyranose ** stome xylopyranose *
Bis-0-(3,6-dioxadodecanyl)- pl ee glucopyranose * 65
380526.NL.02-967.475NL2
Tetrakis-0-(3,6- 50. dioxadodecanyl)-glucopyranose 13
Pentakis-0-(3,6- 51. dioxadodecanyl)- glucopyranose’”
Hydroquinone beta-D-glycoside oo 52. (k) 4 497-76-7 Shiseido
Propylene Glycol Propyl Ether | 1569-01-3 | Sigma
Aldrich 54. Dicetyl Ether 4113-12-6 (UK)
Solvay 55. Polyglycerin-4 Ethers 25618-55-7
Chemicals
Isoceteth-10 69364-63-2 | Nihon 60. | Isoceteth-15 69364-63-2 | Company
Isoceteth-20 69364-63-2 | Ltd.
Isoceteth-30 69364-63-2
Disodium 64. —_— 68929-04-4 | Rhodia
Lauroamphodipropionate
Sigma
Hexaethylene glycol 65. 3055-96-7 | Aldrich monododecyl ether (UK)
Neopentyl Glycol } 27841-07-2 | Symrise (m) Diisononanoate ’° : (Germany)
Cetearyl Ethylhexnoate ‘° 90411-68-0 66
380526.NL.02-967.475NL2
Co Takasago 68. (n) 2-ethylhexyloxypropanediol ’” | 70455-33-9 (IP)
DSM
# Nutritional 69. Panthenol Ethyl Ether * 667-83-4
Products, (0)
Inc. (USA)
Roche Inc. 70. DL-Panthenol 16485-10-2 (USA)
Diisobutyl Adipate ** 141-04-8 Sigma (p) / ) Aldrich 72. Diisoamyl Adipate ’ 6624-70-0 (UK)
PPG-11 Stearyl Ether °° 25231-21-4 | Kao (JP)
N-hexadecyl n-nonanoate 7% 74. 72934-15-7 ©) (e.g., cetyl nonanoate) Symrise
T os Noctadecyl n-nonanoate 7 | 107647-13- | (Germany) (e.g., stearyl nonanoate) 2 16 methanone, (morphonyl) tricyclo[3.3.1.1%7]dec-1-yl- 79 77 methanone, (piperidinyl) tricyclo[3.3.1.1%"]dec-1-yl- ?/ 78 methanone, (pyrrolidinyl) tricyclo[3.3.1.1%"]dec-1-yl 77 methanone, (azetidinyl) Unilever 79. (s) 23 , tricyclo[3.3.1.1°"]dec-1-yl- ** (UK) methanone, (hexahydroazepinyl) tricyclo[3.3.1.13"]dec-1-y1-" methanone, (4-cyano- 81. piperidinyl)tricyclo[3.3.1.1%7]de c-1-yl- 67
380526.NL.02-967.475NL2 methanone, (4-amido-
82. piperidinyl}tricyclo[3.3.1.1°”]de c-I-yl- 2 methanone,
83. (Trieyclo[3.3.1. 1%7Jdecanyl)-N- tricyclo[3.3.1.1%?]dec-1-yl- +7 methanone,
84. (decahydroisoquinolinyl)tricycl o[3.3.1.1°’Jdec-1-yl- *7 methanone,
85. (decahydroisoquinolinyl)tricycl 0[3.3.1.1%"]dec-1-yl- 27 methanone,
86. (decahydroquinolinyl)tricyclo[3 3.1.1%7]dec-1-y1-20 methanone, (3,3-dimethyl-1-
87. piperidinyl)tricyclo[3.3.1.1%7] dec-1-yl- °° methanone, (2-methyl-1-
88. piperidinyl)tricyclo[3.3.1.1%7] dec-1-yl- *’ methanone, (4-methyl-1- piperidinyl)tricyclo[3.3.1.1°7] dec-1-yl- #* methanone, (3-methyl-1- piperidinyl)tricyclo[3.3.1.1%] dec-1-yl- °9 methanone, (3,5-dimethyl-1-
91. piperidinyl)tricyclo[3.3.1.1*7] dec-1-yl- *
68
380526.NL.02-967.475NL2 methanone, (4-methyl-4-ethy- 92. piperidinyl}trieyclo[3.3.1.1°7] dec-1-yl- 2 methanone, (3,3-diethyl-1- 93. pyrrolidinyl)tricyclo[3.3.1.1%7] dec-1-yl- 29 04 methanone, (VN, N-diisopropyl) tricyclo[3.3.1.1%"]dec-1-yl- 77 methanone, (3,3- 95. dimethylbutylaminyl) tricyclo[3.3.1.13"]dec-1-yl- #* methanone, (2,2- 96. dimethylpropylaminyl) tricyclo[3.3.1.1%"]dec-1-yl- ?/ methanone, (1,1-dimethyl-3,3- 97. dimethylbutylaminyl) tricyclo[3.3.1.1%"]dec-1-yl- °9 methanone, (1,3-dimethyl- butylaminyl) tricycle[3.3.1.1°7]dec-1-yl- 29
PolymerExp
Bis-methoxy PEG-13 PEG- 936645-35- | ert S.A. (1) 438/PPG-110 SMDI Copolymer 1 (Pessac,
France) propyl {4-[2-(diethylamino)-2-
Sigma 100. (u) oxoethoxy]-3- 61791-12-6 … Aldrich (US) methoxyphenyl}acetate “ 3-((2-ethylhexyl)oxy)propane- 101. (v) Co — 70445-33-9 1,2-diol © 69
380526.NL.02-967.475NL2 34 102. propylheptyl)oxy)propane-1,2- diol ” 1-amin0-3-({2- 103. 99509-00-9 emee ! available as GLUCAMTM P-20. ? available as Glucam™ E-20. * available as Plantacare® 810 UP. “available as Simulsol® SL 11W. “available as CERAPHYL" ICA. > available as Tegosoft™ APM. 9 available as Schercemol™ NGDO. 7 disclosed in U.S.
Patent No. 6,737,396B2 (Firmenich), column 1, lines 43-47. * diclosed as compound 1°i in U.S.
Patent No. 6,440,400B1 (Takasago Int.
Corp.), col. 5. 34 diclosed in U.S.
Patent No. 4,313,855 (Dragoco Gerberding & Co.
GmbH), col. 1, lines 12-13. ? disclosed in U.S.
Patent No. 7,538,081B2 (Takasago Int.
Corp.), column 7, lines 50-53. 19 disclosed in U.S.
Patent No. 6,147,049 (Givaudan Roure), col. 5, line 24, to col. 6, line 17. 17 disclosed in PCT Publication No.
WO85/04803 (Diagnostic), pg. 2, line 1 to pg. 4, line 2. 15’? disclosed in JP Patent No. 61-083114 (Kanebo). 13 disclosed in JP Patent No. 61-063612 (Kanebo). 1 disclosed in JP Patent No. 62-084010 (Shiseido). 1 available as: Laureth-6. disclosed in U.S.
Patent Publication No. 2011/0104089A1 (Symrise), para. [0001]. 79 available as PCL-Liquid® 100. 7 disclosed in U.S.
Patent No. 7,196,052 (Takasago Int.
Corp.). col. 4, lines 34-35. 1% disclosed in EP Patent Publication No. 616800A2 (Givaudan), pg. 2, lines 12-25. 9 disclosed in U.S.
Patent No. 4,110,626 (Shiseido), column 3, lines 54-56. 4 disclosed in PCT Publication No.
WO2014/155019 (LVMH). 1% disclosed in U.S.
Patent No. 9,050,261 (Symrise). 70
380526.NL.02-967.475NL2 79 disclosed as compounds C1-C22 in WO2014/139952 (Unilever).
I available as Expert Gel® EGS6. 2? available as Kolliphor® EL. 73 disclosed in U.S. Patent No. 9,050,261 (Symrise).
Further examples of non-odorous fragrance modulator is selected from the group of materials disclosed in Table 4(b).
Table 4(b): Substantially Non-Odorous Fragrance Modulators
No. Chemical or INCI
Trade Name CAS Number | Supplier
Name
Tergitol® 15-S- Sigma Aldrich 1. C12-14 Sec-Pareth-3 68131-40-8 7 (UK)
Poly(ethylene glycol- ‚ | Iycol) PPG-7-Buteth- 0038.95.3 Sigma Aldrich 2 ran-propylene glyco -95- (UK) monobutyl ether
PPG-4-Ceteth-10 Nikkel PBC-33 | 37311-01-6 Chemical Navi
Ethox Chemicals, 4. Deceth-4 Ethal DA-4 5703-94-6
Inc.
A & E Connock
AEC PPG-5- 5. PPG-5-Ceteth-20 9087-53-0 (Perfumery &
Ceteth-20
Cosmetics) Ltd.
Neodol 45-7
Shell Chemical
C14-15 Pareth-7 alcohol 68951-67-7
Company ethoxylate
Linear alcohol (C12-15)
Stephan Company 7. Pareth-3ethoxylate, Bio-soft N25-7 | 68131-39-5 (USA)
POE-7 71
380526.NL.02-967.475NL2
Linear alcohol (C12-13) | __
Bio-soft N23-
Pareth-3ethoxylated, 65 66455-14-9
POE-6.5)
Polyethylene glycol 9. 1100 Cremophor® A Sigma Aldrich 68439-49-6 mono(hexadecyl/octade | 25 (UK) cyl) ether
Linear alcohol (C9-11)
Stephan Company 10. ethoxylated POE -8 | Bio-soft N91-8 | 68439-46-3 (USA)
Pareth-3
Coceth-10 or . Sigma Aldrich 11. Polyoxyethylene (10) | Genapol® C-100 | 61791-13-7 (UK) dodecyl ether
Alcohols, C12-14, | Rhodasurf® LA | Solvay Solutions 12. 68439-50-9 ethoxylated 30 Italia S.p.A.
Poly(ethylene
Poly(ethylene glycol) Sigma Aldrich 13. glycol) methyl | 9004-74-4 methyl ether (UK) ether
N Shell Chemical 14. C10-16 Pareth-1 Neodol* PC 110 | 68002-97-1
Company
ArlamolTM 15. PPG-11 Stearyl Ether 25231-21-4 Croda (UK)
PSIIE en Sigma Aldrich 16. Steareth-100 Brij» S100 9005-00-9 (UK)
Polyethylene glycol . Sigma Aldrich
Brij® C-58 9004-95-9 17. hexadecyl ether (UK) 72
380526.NL.02-967.475NL2 ‚ oe Sigma Aldrich 18. Pluronic” F-127 Pluronic® F-127 | 9003-11-6 (UK)
Linear Alcohol (Cl1)| _ Stepan Canada
Bio-soft N1-5 34398-01-1 19. Ethoxylate, POE-5 Inc.
Intrasol FA Evonik Industries 20. Laureth-10 6540-99-4 12/18/10 AG
Polyoxyethylen
Decaethylene glycol Sigma Aldrich 21. e (10) lauryl | 9002-92-0 mono-dodecyl ether (UK) ether
Ethylene glycol | 2- Sigma Aldrich 22. 109-86-4 monomethyl ether Methoxyethanol (UK)
Grau Aromatics
Homulgator 920 23. Myreth-4 G 27306-79-2 GmbH &
Company KG
Oleth-16 Alkoxylated Toho Chemical 24. Pegnol O-16A | 25190-05-0
Alcohols Industry Co., Ltd.
Nihon Emulsion 25. Isosteareth-5 Emalex 1805 52292-17-8
Company, Ltd.
Arlamol™ 26. PPG-10 Cetyl Ether 9035-85-2 Croda (UK)
PC10
Polyoxy(ethylene Poly(ethylene
Sigma-Aldrich 27. glycol) (18) tridecyl | glycol) (18) | 24938-91-8 (UK)
K ether tridecyl ether 73
380526.NL.02-967.475NL2
Poly(oxy-1,2- ©
ALFONIC® 10- Sasol Chemicals 28. ethanediyl), a-decyl-w- 26183-52-8 8 Ethoxylate (USA) LLC hydroxy-
Mackam™ 29. Laureth- 1 4536-30-5 Rhodia (DE) 2LSF
PEG-5 Hydrogenated Ethox Chemicals, 30. Ethox HTAM-5 | 61791-26-2
Tallow Amine Inc.
Nikkol Nikko Chemicals 31. PEG-15 Oleamine 26635-93-8
TAMNO-15 Co. Ltd.
Polyoxyethylene (20) ~ Sigma Aldrich 32. Brij® 020-SS 9004-98-2 oleyl ether (UK)
Cetoleth-10 Bri® CO10 8065-81-4
Sanyo Chemical 34. Talloweth-7 Emulmin 70 61791-28-4
Industries Ltd.
Isobutoxypropanol Isobutoxypropa 35. 34150-35-1 MolPort
Alcohols nol
Isobutoxypropanol Isobutoxypropa AKos Consulting 36. YPrOp YPIoP 23436-19-3
Alcohols nol & Solutions
Diethylene Glycol Twincide EDG | 111-46-6 74
380526.NL.02-967.475NL2
Toho Chemical 38. Methoxyethanol Hisolve MC 109-86-4
Industry Co., Ltd.
Ethoxyethanol 2- Sigma-Aldrich 39. 110-80-5
Alcohols Ethoxyethanol (UK)
The Dow
Methoxyisopropanol 40. Dowanol™ PM | 107-98-2 Chemical
Alcohols
Company
Toho Chemical 41. Methoxyethanol Hisolve MC 32718-54-0
Industry Co., Ltd.
Methylal Dimethoxymeth Sigma-Aldrich 42. 109-87-5
Ethers ane (UK)
Hans
Methoxybutano 43. 3-Methoxybutanol | 2517-43-3 Schwarzkopf
GmbH / Co. KG
Shell Chemical 44. Butoxyethanol Butyl OXITOL | 111-76-2
Company
The Dow
Propylene Glycol n- 5131-66- 45. Dowanol™ PnB Chemical
Butyl Ether 8/29387-86-8
Company
Propylene
Propylene Glycol Butyl Sigma Aldrich 46. Glycol Butyl | 15821-83-7
Ether (UK)
Ether
Diethylene / / 2-(2- Sigma Aldrich 47. glycol butyl | 112-34-5 butoxyethoxy ethanol (UK) ether 75
380526.NL.02-967.475NL2
CrodafosTM 48. Deceth-4 Phosphate 52019-36-0 Croda, Inc.
D4A
Ethylene glycol 2- © Sigma-Aldrich 49. | monohexadecyl | 2136-71-2 (Hexadecyloxy)ethanol (UK) ether
Poly(propylene
Poly(propylene glycol) Sigma-Aldrich 50. glycol) 9003-13-8 monobutyl ether (UK) monobutyl ether
The Dow
Propylene Glycol 51. DowanolTM PnP | 30136-13-1 Chemical
Propyl Ether
Company
The Dow
Propylene Glycol n- 29387-86- 52. Dowanol™ PnB Chemical
Butyl Ether 8/5131-66-8
Company
Di(propylene 53. Dipropylene lycol | glycol) methyl Sigma Aldrich propy gly glycol, | y 34590-94-8 monomethyl ether ether, mixture of (UK) isomers
Di 1 Glycol | Proglyde™ The bow ipropylene ycol | Proglyde 54. 111109-77-4 | Chemical
Dimethyl Ether DMM
Company
The Dow
Dowanol™ 55. PPG-2 Methyl Ether 13429-07-7 Chemical
DPM
Company
Methoxydiglycol OriStar 56. 111-77-3 Orient Stars LLC
Ethers DEGME 76
380526.NL.02-967.475NL2
Di(ethylene
Diethylene glycol ethyl Sigma Aldrich 57. glycol) ethyl | 111-90-0 ether (UK) ether
Dimethoxydiglycol Dimethyldiglyc 58. 111-96-6 H&V Chemicals
Ethers ol
The Dow
DowanolTM 59. PPG-3 Methyl Ether 37286-64-9 Chemical
TPM
Company 224286
Methyl Morpholine | ALDRICH
Sigma-Aldrich
Oxide 4- 7529-22-8 oo | (UK)
Amine Oxides Methylmorpholi ne N-oxide . Croda Europe, 61. Oleth-3 Brij“ O3 5274-66-8
Ltd.
Tri(propylene glycol) n- | DowanolTM Sigma-Aldrich 62. (pray yen) 55934-93-5 = butyl ether TPnB (UK)
Tripropylene Sigma-Aldrich 63. Tripropylene Glycol 24800-44-0
Glycol (UK)
The Dow
PPG-3 Methyl Ether Dowanol™ 64. 25498-49-1 Chemical
Alkoxylated Alcohols | TPM
Company
Sigma Aldrich 65. Triethylene glycol Triglycol 112-27-6 (UK) 77
380526.NL.02-967.475NL2
Toho Chemical
PEG-3 Methyl Ether HymolTM 112-35-6
Industry Co., Ltd.
A & E Connock 67. Laureth-3 AEC Laureth-3 | 3055-94-5 (Perfumery &
Cosmetics) Ltd. “ Ethylhexylglycerin AG-G-75008 70445-33-9 Angene Chemical
Tetraethylene Sigma Aldrich
Tetra(ethylene glycol) 112-60-7 glycol (UK) or oe
Nihon Emulsion 71. Ceteth-3 Emalex 103 4484-59-7
Company, Ltd.
Myreth-3 26826-30-2 Vevy Europe SpA
Alfonic® TDA- Sasol North 73. Trideceth-3 3 Ethoxylate America, Inc.
Co Croda Europe, 74. Ceteth-2 Brij* C2 5274-61-3
Ltd. or 78
380526.NL.02-967.475NL2
Cetoleth-10 Brij* CO10 8065-81-4
Trimethyl
Trimethyl Pentanol 78. Pentanol
Hydroxyethyl Ether 68959-25-1 Angene Chemical
Hydroxyethyl
Alcohols
Ether
Steareth-10 Allyl Ether | Salcare® SC80 | 109292-17-3 | BASF material ID-
TEA-Lauryl Ether 1733-93-3 Angene Chemical
AG-J-99109
Polyglyceryl-2 Oleyl 81. ú Chimexane NB | 71032-90-1 Chimex
Ether
B402 | Sigma-Aldrich 82. Batyl Alcohol 544-62-7
ALDRICH (UK) 15879 Sigma-Aldrich 83. Octaethylene Glycol 5117-19-1
ALDRICH (UK)
Triglycerol 84. ~ CithrolTM 66082-42-6 Croda (UK) diisostearate
Sakamoto 85. Diglycerin Diglycerin 801 | 59113-36-9 Yakuhin Kogyo
Co., Ltd. 79
380526.NL.02-967.475NL2
Sakamoto
Polyglycerin
Polyglycerin #310 4310 25618-55-7 Yakuhin Kogyo
Co. Ltd.
Sasol Germany 87. Distearyl Ether Cosmacol® SE | 6297-03-6
GmbH
Caprylyl AKos Consulting 88. Caprylyl Glyceryl Ether 10438-94-5
Glyceryl Ether & Solutions
Nikko Chemicals
Chimyl Alcohol Chimyl Alcohol | 506-03-6
Co. Ltd.
Dipentaerythrityl .
Liponate® DPC- Lipo Chemicals, 90. Hexacaprylate/Hexacap 68130-24-5 6 Inc. rate 394467 Sigma-Aldrich 91. Morpholine 110-91-8
ALDRICH (UK)
The Dow 92. Dimethyl Oxazolidine | OXABAN™ -A | 51200-87-4 Chemical
Company 4-
Ethyl Hydroxymethyl 93. | Oxazolemethan | 68140-98-7 Angene Chemical
Oleyl Oxazoline ol
Methyl Hydroxymethyl | Adeka Nol GE- Adeka 94. | 14408-42-5
Oleyl Oxazoline RF Corporation
Pramoxine HCI OriStar PMHCL | 637-58-1 Orient Stars LLC 80
380526.NL.02-967.475NL2
Allantoin 96. Allantoin Ascorbate 57448-83-6 ABI Chem
Ascorbate
Stearamidopropyl Mackalene™ 97. 55852-14-7 Rhodia Inc.
Morpholine Lactate 326 — Lambiotte & CIE
Dioxolane Elcotal DX 646-06-0
S.A.
Sigma Aldrich
Glycerol Formal Glycerol Formal | 5464-28-8 (UK)
Stearamidopropyl 100. Mackine 321 55852-13-6 Rhodia Inc.
Morpholine
Poly(melamine- 2,4,6- 101. oo co- Sigma-Aldrich
Tris[bis(methoxymethy 68002-20-0 oo formaldehyde) (UK)
Damino]-1,3,5-triazine methylated
Poloxamine 1307 Pluracare* 1307 | 11111-34-5 BASF
Nonoxynol-8 Igepal® CO-610 | 27177-05-5 Rhodia Inc.
Nonoxynol-10 Igepal® CO-710 | 27177-08-8 Rhodia Inc.
Nikko Chemicals
Octoxynol-10 Nikkol OP-10 2315-66-4 105. Co., Ltd. 81
380526.NL.02-967.475NL2
Nonoxynol-9 Igepal® CO-630 | 68987-90-6 Rhodia Inc.
Nonoxynol-9 107. | Nonoxynol-9 Iodine oo 94349-40-3 Angene Chemical iodine
Octylphenoxy 108. | poly(ethyleneoxy)ethan | Igepal® CA-630 | 68987-90-6 Rhodia Inc. ol, branched
The Dow
Sodium Octoxynol-2 109. Triton™ X-200 | 55837-16-6 Chemical
Ethane Sulfonate
Company
Lanxess 110. | Benzylhemiformal Preventol D2 14548-60-8
Corporation
Nonoxynol-2 Igepal® CO-210 | 27176-93-8 Rhodia Inc.
The Dow 112. | Octoxynol-3 Igepal* CA-420 | 2315-62-0 Chemical
Company
Sasol Germany 113. | Nonoxynol-3 Marlophen NP 3 | 27176-95-0
GmbH
Alkoxylated Alcohols | Alkasurf NP-4 | 7311-27-5 Rhodia Inc.
Triethylene Santa Cruz
Nonoxynol-3 51437-95-7 115. Glycol Mono(p- Biotechnology 82
380526.NL.02-967.475NL2 nonylphenyl)
Ether
Jos. H. 116. | Nonoxynol-7 Lowenol 2689 | 27177-03-3 Lowenstein &
Sons, Inc.
Nonoxynol-6 Igepal* CO-530 | 27177-01-1
Igepal* CO-520 | 20636-48-0 Rhodia Inc.
Nonoxynol-5 Igepal® CO-520 | 26264-02-8 Rhodia Inc.
Nonoxynol-4 Alkasurf NP-4 | 27176-97-2
Polyglyceryl-10 Nikkol Nikko Chemicals 121. | 102051-00-3
Trioleate Decaglyn 3-OV Co., Ltd.
Polyglyceryl-10 Nikkol Nikko Chemicals 122. 33940-99-7
Dioleate Decaglyn 2-0 Co. Ltd.
Polyglyceryl-10 Abitec 123. Caprol 10G40 | 34424-98-1
Tetraoleate Corporation
Nikkol
Polyglyceryl-10 Nikko Chemicals 124. Decaglyn 1-SV | 79777-30-3
Stearate Co., Ltd.
EX
83
380526.NL.02-967.475NL2
Sakamoto
S-Face O-1001 125. | Polyglyceryl-10 Oleate p 79665-93-3 Yakuhin Kogyo
Co. Ltd.
Nikkol
Polyglyceryl-10 Nikko Chemicals 126. | Decaglyn 1-MV | 87390-32-7
Myristate Co., Ltd.
EX
Rn Dermofeel® G oo 127. | Dermofeel* G10L (OL 34406-66-1 Dr. Straetmans
NIKKOL
128. | Polyglyceryl-6 Laurate 51033-38-6 Chemical Navi
Hexaglyn I-L
Sakamoto
Polyglyceryl-6 129. S-Face IS-601 P | 126928-07-2 | Yakuhin Kogyo
Isostearate
Co. Ltd. == Nihon Emulsion 130. | Choleth-10 Emalex CS-10 | 27321-96-6
Company, Ltd.
Steareth-10 Allyl 131. | Ether/Acrylates Salcare* SC80 | 109292-17-3 | BASF
Copolymer
Phoenix 132. | Polyvinyl Stearyl Ether | Giovarez®1800 | 9003-96-7
Chemical, Inc.
Cosmacol Ether Sasol Germany 133. | Dicetyl Ether 16 GmbH
Pola Chemical 134. | PPG-23-Steareth-34 Unisafe 345-23 | 9038-43-1
Industries, Inc. 84
380526.NL.02-967.475NL2
Stearoxypropyl Farmin DM E- 135. 17517-01-0 Kao Corp.
Dimethylamine 80
Sasol Germany 136. | Distearyl Ether Cosmacol SE 6297-03-6
GmbH
AEC A & E Connock 137. | Polyquaternium-10 Polyquaternium | 55353-19-0 (Perfumery & -10 Cosmetics) Ltd.
Sigma Adlrich 138. | Octyl ether Dioctyl ether 629-82-3 (UK)
Ethyl Ether Diethyl Ether EMD Chemicals
Methyl Hexyl Ether methyl hexyl 140. 4747-07-3 TCI AMERICA
Ethers ether
Nihon Emulsion 141. | Ceteth-12 Emalex 112 94159-75-8
Company, Ltd.
Ceteth-10 or cetyl 142. Jeecol CA-10 14529-40-9 Jeen International alcohol POE-10
Steareth-10 Jeecol SA-10 13149-86-5
Nonaethylene glycol | Nonaethylene Sigma Aldrich 144. 3055-99-0 monododecyl ether glycol (UK) 85
380526.NL.02-967.475NL2 monododecyl ether
Oleth-10 Brij* O10 71976-00-6
Oleth-10 Brij* 010 24871-34-9
The Dow
Carbowax™ 147. PEG-12 6790-09-6 Chemical
PEG 600
Company
PEG-9 Sabopeg 400 3386-18-3
DECAETHYL
149. PEG-10 5579-66-8 MolPort
ENE GLYCOL
The Dow
CarbowaxTM 150. | PEG-6 2615-15-8 Chemical
PEG 300
Company
Glycerol | Sigma Aldrich 151. | Glycerol propoxylate 25791-96-2 propoxylate (UK)
Glycerol Sigma Aldrich 152. | Glycerol ethoxylate 31694-55-0 ethoxylate (UK)
A & E Connock 153. | Laureth-8 AEC Laureth-8 | 3055-98-9 (Perfumery &
Cosmetics) Ltd. 86
380526.NL.02-967.475NL2
Nihon Emulsion 154. | Oleth-8 Emalex 508 27040-03-5
Company, Ltd.
Alfonic
Sasol North 155. | Laureth-7 1216CO-7 3055-97-8
America, Inc.
Ethoxylate
Polyoxyethylen 156. | Steareth-7 e (7) stearyl | 66146-84-7 Sigma Aldrich ether
Alfonic 1012- Sasol North 157. | Deceth-6 5168-89-8 6.0 Ethoxylate America, Inc.
Nihon Emulsion 158. Steareth-6 Emalex 606 2420-29-3
Company, Ltd.
Hexaethylene 159. | Hexaethylene lycol | glycol Sigma-Aldrich y = Sy 3055-96-7 monododecyl ether monododecyl (UK) ether
Hexaethylene 160. | Hexaethylene slycol | glycol Sigma-Aldrich y Sy Sy 5168-91-2 monohexadecyl ether monohexadecyl (UK) ether
Nikko Chemicals 161. | Beheneth-5 Nikkol BB-5 136207-49-3
Co., Ltd.
Myreth-5 92669-01-7 Vevy Europe SpA 87
380526. NL.02-967.475NL2
Jeen International 163. | Steareth-5 Jeecol SA-5 71093-13-5
Corporation
Nihon Emulsion 164. Ceteth-5 Emalex 105 4478-97-1
Company, Ltd.
Safol® 23E5 Sasol North 166. Laureth-5 3055-95-6
Ethoxylate America, Inc.
Jeen International 167. | Steareth-4 Jeecol SA-4 59970-10-4
Corporation vr or
Grau Aromatics
Homulgator 920 169. Myreth-4 G 39034-24-7 GmbH &
Company KG
Protameen 170. | Ceteth-4 Procol CA-4 5274-63-5
Chemicals
Oleth-4 Chemal OA-4 5353-26-4
Oleth-4 Chemal OA-4 103622-85-1 88
380526.NL.02-967.475NL2 en Aquaflex™ XL- 173. | Polyimide-1 20 497926-97-3 | Chemwill
Polymethoxy Bicyclic | Caswell No. 174. - 56709-13-8 Angene Chemical
Oxazolidine 494CA
Hydroxymethyl Angus Chemical 175. | | ZoldineTM ZT 6542-37-6 7
Dioxoazabicyclooctane Company 5-Ethyl-1-aza-
Dihydro-7a- 176. 3,7- Sigma Aldrich ethyloxazolo[3,4- 7747-35-5 dioxabicyclo[3. (UK) cloxazole 3.0]octane m oe Roquette 177. | Dibenzylidene Sorbitol | Disorbene* 32647-67-9
America, Inc.
Dimethyldibenzylidene a Milliken 178. | Millad® 3988 135861-56-2
Sorbitol Chemicals
Alfonic
Sasol North 179. | Laureth-2 1216CO-2 3055-93-4
America, Inc.
Ethoxylate 2{2-
Piperonyl | Sigma-Aldrich 180. | Butoxyethoxy)ethyl (6- 51-03-6
Butoxide (UK) propylpiperonyl) ether
Menthone Glycerin | Frescolat® 181. 63187-91-7 Symrise
Acetal MGA
Propylene Glycol | Mackaderm 68332-79-6 Rhodia Inc. 182. | Caprylate PGC 89
380526.NL.02-967.475NL2
LL
Takasago
Alcohols
Corporation 2-Diphenylmethoxy- 185. | N,N- Diphenhydrami Sigma-Aldrich dimethylethylamine ne HCI 147240 (UK) hydrochloride 34(2- 186. | ethylhexyl)oxy)propan 70445-33-9 e-1,2-diol 342 187. | propylheptyl)oxy)propa ne-1,2-diol l-amino-3-((2- 188. | ethylhexyljoxy)propan- 99509-00-9 2-01 1-{1-Methyl-2- Di(propylene 189. | propoxyethoxy)-2- glycol) propyl | 29911-27-1 Sigma Aldnen propanol ether (Uk)
[53] According to some examples, the modulator(s) can be characterized as being “low odor”, “substantially non-odorous”, or non-odorous. In some examples, if the modulator is present at | wt% or less, no odor may be detected from the modulator.
[54] In some examples, the fragrance modulator is biodegradable. This can make the fragrance composition to which it is included a “green” or environmentally friendly fragrance composition. Additionally, the stability of a fragrance composition that includes the substantially 90
380526.NL.02-967.475NL2 non-odorus fragrance modulator can be increased. The increase in stability can be shown by observing that the composition undergoes undesirable color formation (e.g., yellowing) at a slower rate.
[55] The fragrance modulator component can be present in an amount of from about 0.1 wt% to about 27 wt% relative to the total weight of the composition of the composition, about 0.5 wt% to about 18 wt%, about 2.5 wt% to about 15 wt%, or less than, equal to, or greater than about 0.1 wt%, 0.5,1,1.5,2,25,3,35,4,45,5,55,6,65,7,75,8,85,9,95,10,10.5, 11, 11.5, 12, 12.5, 13, 13.5, 14, 14.5, 15, 15.5, 16, 16.5, 17, 17.5, 18, 18.5, 19, 19.5, 20 wt%. If there are more than one fragrance modulators, then the ranges provided hereinabove cover the total of all of the fragrance modulators.
[56] The fragrance modulator can be a liquid at temperatures lower than 100 °C, such as at ambient temperature. The fragrance modulators may be fully miscible with the fragrance materials to form a single phase liquid. However, if the fragrance materials are not entirely miscible, or are immiscible, then co-solvents (e.g., dipropylene glycol (DPG), triethyl citrate, or others well known to those skilled in the art) can be added to aid in the solubility of the fragrance materials.
[57] According to various examples, the effect of the fragrance modulator on the fragrance profile, particularly the characters of the fragrance profile which is attributable to the high and moderate volatile fragrance materials, can be improved. By “improved” it is meant that the fragrance profile of the composition, particular the components contributed by at least one of the high and moderate volatile fragrance materials, can be perceived by a panel of experts or professional evaluators or individual experts or professional evaluators at later time points such as, for example, 15 mins, 30 mins, 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 10 hours, and possibly all the way up to 30 hrs after application as compared to controls, eg, lacking any of the disclosed non-odorous fragrance modulators such as pentylene glycol, polycitronellol or an equivalent traditional fragrance construction.
[58] Alternatively, by “improved” it can mean that the perception, by a panel of experts or professional evaluators or individual experts or professional evaluators, of the fidelity of the fragrance profile contributed by the high and moderate volatile fragrance materials is markedly increased or enhanced as compared to the controls. “Increased” or “enhanced” means that a panel 91
380526.NL.02-967.475NL2 of experts or professional evaluators or individual experts or professional evaluators perceives the fragrance profile, preferably the characters attributable to the high and/or moderate volatile fragrance materials, of a composition as not changing from its initial impression or the changes are minimal from when the composition was first applied to when it dissipates. In other words, the fidelity of the perceived fragrance profile of the composition is maintained over time. In contrast the composition lacking any of the disclosed non-odorous fragrance modulators or an equivalent traditional fragrance construction will undergo a rapid loss of the characters attributable to the high and/or moderate volatile fragrance materials.
[59] Such a solution as presented herein provides enhanced or improved fidelity and/or longevity of the fragrance profile, particularly amongst those composition formulated from volatile fragrance materials having moderate to high vapor pressure ranges (greater than or equal to 0.001
Torr (0.000133 kPa) at 25 °C), without having to rely on the presence or significant amounts of the low volatile fragrance materials, which has a tendency to overpower and alter the overall fragrance profile, particularly over time. As a result, the present disclosure provides the perfumer options to formulate compositions having new fragrance profiles not possible before.
[60] Specific modulators that can be useful include pentylene glycol, polycitronellol,
PPG-20 methyl glucose ether, methyl glucoside polyol, ethyl glucoside polyol, propyl glucoside polyol, or a mixture thereof.
[61] In some aspects, the fragrance composition can include a carrier. The carrier can be an aqueous carrier, organic carrier, or a mixture thereof. The organic carrier can be ethanol, dipropylene glycol, benzyl benzoate, diethyl phthalate, isopropyl myristate, (C1-C>0)alkyl, (Ci-
Cao)alkenyl, (C1-Cao)alkynyl, (C1-C20)hydroxyl, or mixtures thereof. Additionally, the carrier can be any of, solutions, aerosols, emulsions (including oil-in-water or water-in-oil), gels, and liposomes.
[62] The fragrance composition can include an active component. The active component is in a range of from about0.0001 wt% to about 35 wt% of the cosmetic formula, about 20 wt% to about 30 wt%, less than, equal to, or greater than 15 wt%, 16, 171, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, or about 35 wt%. The active component can include any component or mixture of components to achieve a desired result. Examples of active components include lactic acid, a hyaluronic acid, vitamin E, saccharomyces/xylinum/black tea ferment, 92
380526.NL.02-967.475NL2 diglucosyl gallic acid, adenosine, panthenol, dimethylmethoxy chromanol, alpha-glucan oligosaccharide, thermus thermophilus ferment, hydrolyzed hyaluronic acid, caffeine, acetyl di- peptide-1 cetyl ester, glycerin, niacinamide, swertia chirata extract, creatine, or a mixture thereof.
The mixture of gels described and surfactant(s) herein above, allow for the relatively high amount of active component. The ability of the formulation to have a high amount of active component can enhance the formulation’s effectiveness.
[63] In some examples, the formulation can include a chelant or a mixture of two or more chelants. Examples of suitable chelants can include tetrasodium glutamate diacetate (GLDA), ethylenediaminetetraacetic acid (EDTA), ethylenediamine-N, N’-disuccinic acid (EDDS), NTA, EDDS, IDS, methylglycinediacetic acid (MGDA), L-glutamic acid N,N-diacetic acid (GLDA), ethylenediamine-N,N-diglutaric acid (EDDG), ethylenediamine-N,N’-dimalonic acid (EDDM), 3-hydroxy-2,2-iminodisuccinic acid (HIDS), 2-hydroxyethyliminodiacetic acid (HEIDA), methylglycine N,N-diacetic acid trisodium salt (MGDA), sodium gluconate, or a mixture thereof.
[64] The formulas herein can contain a variety of other optional components suitable for rendering such compositions more cosmetically or aesthetically acceptable or to provide them with additional usage benefits. Such conventional optional ingredients are well-known to those skilled in the art. These include any cosmetically acceptable ingredients such as those found in the CTFA
International Cosmetic Ingredient Dictionary and Handbook, 7th edition, edited by Wenninger and
McEwen, (The Cosmetic, Toiletry, and Fragrance Association, Inc., Washington, D.C., 1997). As used herein “cosmetically acceptable” means a material (e.g., compound or composition) which is suitable for use in contact with skin, hair or other suitable substrate.
The fragrance composition can include a cyclodextrin, a film former or a mixture thereof.
According to some examples, the film former comprises anionic compounds or polymers, non- ionic compounds or polymers, amphoteric compounds or polymers, zwitterionic compounds or polymers, cationic compounds or polymers, proteins, viscosity modifiers, polyacrylates, polymethacrylates, polyacrylate copolymers, polymethacrylate copolymers, polyamides, polyaminoamides, polyesters, polysaccharides, polyacrylamides, starches, gums, or a mixture thereof. The cyclodextrin can include, but is not limited to, a-cyclodextrin, B-cyclodextrin, gamma-cyclodextrin, methyl-a-cyclodextrin, methyl-B-cyclodextrin, hydroxypropyl-o- 93
380526.NL.02-967.475NL2 cyclodextrin hydroxypropyl-B-cyclodextrin, and mixtures thereof . Most preferred examples of cyclic oligosaccharides for use herein are methyl-a-cyclodextrin and methyl-B-cyclodextrin. These are available from Wacker-Chemie GmbH Hanns-Seidel-Platz 4, Munchen, DE under the tradename Alpha W6 M and Beta W7 M respectively.
[65] There are many benefits associated with various fragrance compositions associated with the instant disclosure. For example, it is suspected that the fragrance component is detectable for an amount of time longer than a corresponding fragrance composition that free of the extract solution. That is the fragrance materials can be perceived for a long amount of time and thus a user may not have to constantly apply the fragrance composition.
[66] Additionally, according to various aspects, it 1s suspected that a user will perceive that the fragrance composition is more comfortable than a corresponding fragrance composition that free of the extract solution. For example, a user may perceive the fragrance composition as not feeling too oily, greasy, or dry.
[67] Additionally, according to various aspects, it 1s suspected that the fragrance composition will be more effective at reducing or eliminating malodor (e.g., of an odor that is unpleasant or offensive to the human nose) than a corresponding composition that 1s free of the extract solution.
[68] Additionally, according to various aspects, it is suspected that modulation of the fragrance composition is increased relative to a corresponding composition that is free of the extract solution and comprises a cyclodextrin, PPG 20 methyl glucose ether, a chelator, or a mixture thereof. That 1s the extract can help to increase the intensity of the fragrance materials.
[69] Additionally, according to various aspects, it 1s suspected that the fragrance composition can be effective for decreasing skin sensitizing potency of the fragrance component.
That 1s if the fragrance composition includes the extract solution and it is possible that a user’s tendency to be sensitized to the fragrance component can be decreased. The fragrance composition may also prevent irritation or allergy inducement when applied to an intimate area. According to various aspects, the use of a combination of methyl glucose ether and an extract solution comprising nymphaea coerulea flower extract; and nelumbo nucifera flower extract may decrease fragrance sensitization likelihood and/or severity. Any portion of the aforementioned constitutes can be combined in any desirable manner to produce many different types of cosmetic 94
380526.NL.02-967.475NL2 compositions. The cosmetic compositions can be applied to the epithelial layer of a user’s skin.
For example the cosmetic composition can be a pretreatment formulation, make-up formulation, a foundation, a sunscreen, or any other cosmetic applied to a user’s epithelial tissue. Additionally, any portion of the aforementioned constituents can be combined to create a cosmetic formulation that can be applied to a keratinous tissue of a user. For example, the cosmetic formulation can be a mascara, hair dye, nail polish, lip gloss, lipstick or other pigmented/colored cosmetic formulation intended to be a long-wear formulation.
Examples
[70] Various embodiments of the present invention can be better understood by reference to the following Examples which are offered by way of illustration. The present invention 1s not limited to the Examples given herein.
[71] EVALUATIONS:
[72] Evaluations are performed on skin, with a 50uL application of product (one reference and one tested sample). The sample to evaluate and the reference sample are applied on the same wearer. Evaluators are asked to smell the 2 samples randomly and blind. Then they are asked to rate the tested sample versus the reference according to the following scales and following the evaluation protocol:
[73] Evaluated at 3 different time points: Fresh; 2h 6h (Note: exception of the water- resistant test. Which is evaluated at Fresh and 2h.
[74] Character evaluation following the “Odor Grading Scale” presented below: 5 ->
Perfume unchanged. 4 -> Slight perfume character change. 3 -> Moderate perfume change but similar character . Not consumer noticeable. 2 > Large difference in perfume change, consumer noticeable (unacceptable). 1 -> Total difference in perfume character (unacceptable)
[75] Intensity evaluation following “Intensity scale” +2 -> Very Strong (tested sample is much more intense than the reference); +1 -> Strong; 0 -> Same intensity (reference); -1 ->
Weaker; -2 -> Very weak (tested sample is much less intense than the reference)
[76] A minimum of 3 expert panelists and 8 panelists in total are participating in each evaluation, to obtain conclusive results. 95
380526.NL.02-967.475NL2
[77] The averages of the character and intensity difference are calculated. The conclusions are based on the following:
[78] The character result values above 3 are considered as: no character change
[79] The intensity result values from -0.3 to +0.3 are considered as: no significant difference between the tested sample and the references
[80] We tested 4 fragrance accords (Accord 1 (fruity), Accord 2 (citrus), Accord 3 (fougere), Accord 4 (floral) in the patent) covering 4 of the biggest olfactive fragrances families.
Full fine fragrances were tested as well.
[81] NELUPURE Formulas and Skin evaluation results:
[82] Alcoholic chassis (EAT):
[83] Nelupure is added in the water and then mixed with the ethanol / fragrance oil. Full formula here below: [Reece [Tested spe
Alcohol - EtOH 55-70 50-70
Fragrance Accord *
[84] Results of the evaluations as per the protocol described above. i . . Ch t Intensit
Fragrance oil/accord change er pa Technology effect
No character change,
Accord 1 Fresh 3.50 0.5 more intense
No character change, no 2h 3.63 0.1 significant difference in intensity oh 3.25 08 Neo character change, less intense
No character change, no
Accord 2 Fresh 3.75 -0.1 significant difference in intensity 96
380526.NL.02-967.475NL2
No character change, no 2h 3.63 -0.3 significant difference in intensity 6h 395 05 No character change, less intense
No character change, no
Accord 3 Fresh 3.63 0.0 significant difference in intensity oh 3.88 04 No character change, less intense 6h 338 04 No character change, less intense
No character change, no
Accord 4 Fresh 3.25 -0.1 significant difference in intensity
No character change, no 2h 3.25 0.3 significant difference in intensity
No character change, no 6h 3.38 -0.3 significant difference in intensity
Fresh 330 04 Neo character change, less intense
No character change, no 2h 3.30 -0.3 significant difference in intensity
No character change, no 6h 3.30 0.3 significant difference in intensity
No character change, no
Perfume 2 Fresh 3.70 -0.1 significant difference in intensity oh 3.80 0.5 No character change, more intense 6h 3.50 05 No character change, less intense
No character change, no
Perfume 3 Fresh 4.00 -0.3 significant difference in intensity 97
380526.NL.02-967.475NL2
No character change, no 2h 4.00 0.2 significant difference in intensity
No character change, no 6h 4.00 -0.1 significant difference in intensity
[85] Alcoholic chassis with Cyclodextrin
Nelupure is added in the water and then mixed with the ethanol / fragrance oil/cyclodextrin solution. Full formula here below:
EE
Alcohol “EOF 50
Nede
Fragrance Accord *
Min SSP 100 Nia 3 GSP 100
Cavasol (Methyl Cyclodextrin and | 0.5 - 25 05-25 water and alcohol)
GLDA solution 0.0005 - 0.003 0,0005 — 0.003
[87] The samples were activated with water afterwards.
Fragrance Charact Intenst 5 Time point er | v Technology effect oil/accord difference change
No ch: 7 chang
Fresh 3.43 0.7 No € aracter change, more intense oo No ct ter ch: [ 2h pre activation 3.86 0.6 “9 character change, more intense oo No cl ter change, 2h post activation | 3.00 -0.7 (0 chatactel change, fess mntense
No character change, no 6h pre activation 3.86 0.3 significant difference in intensity
CL No character ch: 1 6h post activation 3.29 -1.3 ‚ © character change, less intense 98
380526.NL.02-967.475NL2
No character change, no
Perfume 4 Fresh 3.86 0.1 significant difference in intensity
Character change, no 2h pre activation 2.86 -0.3 significant difference in intensity 2h post activation | 3.29 -0.4 No character change, less intense 6h pre activation 3.57 -0.4 No character change, less intense
No character change, no 6h post activation | 3.14 -0.3 significant difference mn intensity [Reese [TewdSampe
Nope Jo orm]
Cavasol (Methyl Cyclodextrin and 0,5-25 rio ME
Intensit r change .
Perfume 3 No character change, no (Nelupure vs | Fresh 4.11 -0.1 significant difference in
No character change, no oe 2h 4.11 0.1 significant difference in intensity
CL No character change, 6h pre activation 4.00 0.4 : more intense 6hpostactivation |288 16 Crater change, more intense
Alcoholic chassis with Glucam: 99
380526.NL.02-967.475NL2
[88] Nelupure is added in the water and then mixed with the ethanol / fragrance oil/glucam solution. Full formula here below:
Ree [TowdSample
Newpwe Jo Term
PPG-20 Methyl Glucose Ether 0,5-25 (Guam
Character Intensity Technology effect change difference
No character change, no
Perfume 5 Fresh 3.78 -0.1 significant difference in oh 400 04 No character change, less intense 6h 413 08 No character change, less intense
No character change, no
Perfume 6 Fresh 3.67 0.3 significant difference in ==
No character change, no 2h 3.78 0.1 significant difference in intensity
No character change, no 6h 3.75 -0.1 significant difference in intensity
Alcoholic chassis with Dermacryl 79/Acrylates/Octylacrylamide Copolymer:
[90] Nelupure is added in the water and then mixed with the ethanol / fragrance oil/cyclodextrin solution. Full formula here below: 100
380526.NL.02-967.475NL2
Alcohol - EtOH 65-80 65- 80
Fragrance Accord *
Min 2 GSF 100 in ZGSF 100
Dermaeryl 7 . . . Cl t Intensit
Fragrance oil/accord | Time point iaracter n ensity Technology effect change difference
No character cl 1
Fresh 3.63 08 No character change, less mtense
No character change, no 2h 3.86 -0.3 significant difference in intensity 6h 3.63 06 Neo character change, less intense
[91] Water-base fine fragrance:
[92] Nelupure is added in the water base fine fragrance and mixed together with the Fragrance oil added afterwards. Full formula here below:
I
Tested Sample
Neue 0 [01-53
Fragrance Accord
GSP [sei
[93] Results of the evaluations as per the protocol described above. : : Cl t Intensi
Fragrance oil/accord te Technology effect
Fresh 3 86 04 No character change, less intense 101
380526.NL.02-967.475NL2 oh 3.57 07 No character change, less intense oh 3.43 0.9 Ne character change, less
Intense
No character change, no
Accord 2 Fresh 3.86 0.1 significant difference in intensity
No character change, no 2h 3.86 -0.1 significant difference in intensity 6h 3.29 04 No character change, more mtense
Fresh 3 57 0.7 No character change, more
Intense oh 371 06 No character change, more intense 6h 357 07 No character change, more intense
No character change, no
Accord 4 Fresh 4.14 0.3 significant difference in intensity
No character change, no 2h 3.71 0.0 significant difference mn intensity
No character change, no 6h 3.71 0.0 significant difference In intensity
No character change, no
Perfume 1 Fresh 3.50 0.3 significant difference mn intensity
No character change, no 2h 3.70 -0.2 significant difference in intensity
No character change, no 6h 3.80 0.0 significant difference in intensity
Fresh 330 07 No character change, less
Intense 102
380526.NL.02-967.475NL2 oh 3.70 04 No character change, less intense oh 4.00 0.5 Neo character change, less intense
No character change, no
Perfume 4 3.25 0.1 significant difference mn intensity 3.43 04 Ne character change, less tense
No character change, no 3.38 0.1 significant difference in intensity
[94] Waterproof evaluation Process:
[95] "The following test is carried out to demonstrate the improved or enhanced retention of a fragrance of a composition of the present invention In particular, the test measures the film forming and fixative effect on fragrance materials of a composition apphed to an mm-vitro substrate {e.g., glass slide). The properties are triggered after exposure fo water. The amount of fragrance materials left on the substrate 1s evaluated by an expert panel”
[96] A test composition comprising ethanol, water, one or more fragrances and Nelupue.
A control composition to the test composition is made with ethanol, water, and the same one of mare fragrances used in the test composition.
A hotplate 18 set to a temperature of 32 °C. A glass shide, with dimensions of about 76X26 mum, is placed on the hotplate. SOuL of the test or control composition is dispensed on a test area of the glass slide using a mucropipeite. The time at whuch this takes place is deternuned to be time zero (Le, T=10}
The solution is left to evaporate on the glass slide at 32°C for 10min from T=0. The glass shde is then onmersed in water having 4 teraperature around 20-27°C for 4 minutes, The excess water is dabbed carefully avoiding the test area, and the glass slide is left to further dry for at 32°C ona hotplate for 2h
After Zh, the glass slide 1s again tomersed 10 water having a temperature around 20-27°C for 4 nunutes. The excess water 1s dabbed carefully avoiding the test area, and the glass shde is left to further dry until given to the expert panel for evaluation,
The procedure 13 repeated for the "Fresh" tene point. In thus case, samples are given to the expert panel after the first UTunersion In water, [Ree [Towne]
Nee Jo Jor 103
380526.NL.02-967.475NL2
Fragrance Accord? i . . Ch t Intensit
Fragrance oil/accord change et i oro Technology effect
N haract h: more tense on 400 03 No character change, more intense
Unperfumed water base used as a primer
[98] Nelupure is added in unperfumed water base used as a primer, meaning it is first applied on skin and then a standard EDT 1s sprayed on top of the primer.
Full formula here below:
Tee Tvhwes
Tested Sample
GSF 100
Nelpue Jo [01-10
[84] Malodour is evaluated at the following times — note comments are directed towards a EDT solution with 5% Nelupure versus a EDT solution without Nelupure:
Tested Technology | tested Evaluated time sample % accord point Evaluators comment
NeluPur .
Accord 1 | Fresh Less plastic 2h 6h
Accord 2 | Fresh 104
380526.NL.02-967.475NL2 oh Less fatty sweaty note a fatty sweaty note 6h
Accord 3 | Fresh Less mossy plastic 2h Less mossy plastic
[85] Indicia indicating malodour include: plastic; fatty / sweaty; mossy plastic notes.
Example 3: Sensitizing potency using GARDskin
[86] In addition to a longevity of a fragrance, users are concerned with skin sensitization potency of cosmetic fragrance formulations. Skin sensitization potency, i.e. Adverse Outcome
Pathway, is measured herein with a GARDskin Dose-Response assay. This assay 1s a modification of the validated GARDskin protocol , OECD TGP 4.106, that incorporates dose response analysis.
[87] The GARDskin assay employs a gene expression biomarker to identify skin sensitizers in a human myeloid dendritic-like cell line. The GARDskin Dose-Response investigates the GARDSKIN response values in a titrated range of multiple concentrations in a dose-response manner to find a concentration threshold required to induce a positive decision value. The concentration threshold is used to estimate the inherent sensitizing potency of a chemical. A low value indicates a high inherent skin sensitizing potency and a high value indicates a low inherent skin sensitizing potency. The readout is a cDVO value, describing the lowest concentration required to generate a positive classification. This value correlates with potency and can be used to rank test items by their relative sensitizing potency. This assay allows to evaluate mixtures and delivers continuous potency predictions, crucial point for comparing the modulator’s effect on the formulations’ skin sensitizing potency. One description of the method is described in this article: Quantitative assessment of sensitizing potency using a dose-response adaptation of
GARDskin, R. Gradin et al., Scientific Reports, 18904 (2021).
[88] The potential of a lotus flower extract to reduce the skin sensitizing potency of fragrance formulations containing different concentrations of fragrance oils was investigated using the GARDskin protocol.
[89] The GARDskin Dose-Response assay is based on the validated protocols of
GARDskin (OECD TG 442E) and incorporates dose-response measurements to derive continuous potency predictions. The readout of the assay corresponds to the lowest concentration required to 105
380526.NL.02-967 475NL2 exceed the binary classification threshold in GARDskin (DV= 0), referred to as the cDVO value.
This concentration is inversely correlated to skin sensitizing potency and can be used to predict a corresponding LLNA EC3/human NESIL value in, for instance, micrograms per square centimeter, or be directly interpreted on its own to compare differences in skin sensitizing potency between investigated samples.
[90] In this study, fragrance formulations with and without 2% Nelupure will be evaluated. The purpose of the study will be to investigate Nelupure’s efficacy for reducing skin sensitization. Table I: TESTED SAMPLES:
IE I
Perfume 1 EDT WITHOUT GLUCAM Negative control
Perfume 1 EDT + 2% NELUPURE Nelupure alone
Results are shown below, with the sample containing Nelupure designated as MP23008, indicating a lower inherent skin sensitizing potency for a sample containing Nelupure. testen Opel Moon | Su tiove | Le | EN 3 sob Hem # JD Epe) | £3 OY 3% £3 BYE Cp) | Category | NOEL fend)
PORR ENE 1d § : ì ) ; A : | ; Esha 3
MSR es SA 1 RAID MT sne, DCN
GARDskin DOSE RESPONSE METHOD:
[91] The ability of each sample tested to modulate the sensitization potency will be measured using a GARDskin dose response method. The GARDskin dose response method 1s an in vitro test based on human dendritic-like cell cline, SenzaCell, a set of 200 genes known as the
GARD Prediction Signature and a prediction model developed with machine learning technology.
A summary of the GARDskin method is shown in FIG. 1. A test sample that includes at least one test substance is prepared and different concentrations of the test sample are grown in cells obtained from SenzaGen AB. A determination is made of the concentration of the test substance where cells react and 90 percent of cells survive. Then, a fresh batch of quality controlled cells are exposed to the determined concentration wherein cells react and 90% survive. 106
380526.NL.02-967.475NL2
[92] After exposure to the test sample, total RNA will be isolated from SenzaCells.
Gene expression will be quantified and analyzed by pattern recognition using a machine learning algorithm based on a fixed set of reference samples. The genes that will be measured are well characterized and are related to several skin sensitization methanistic events. The resulting classification is that of a sensitizer or non-sensitizer. Additional information about the method can be found in a Nature article, “Quantitative assessment of sensitizing potency using a dose-response adaptation of GARDskin,” Nature, article no. 18904 (2021).
[93] It 1s hypothesized that the lowest concentration required to exceed the binary classification threshold (DV > 0} and generate a positive classification, referred to as the cDVy concentration, would be mformative of sensitizing potency. As such, the proposed dose response measurements would also be aligned with common toxicological principles for potency assessments, where the response value {DV}, the binary threshold (BV 20}, and the derved cDVo concentrations may be viewed as an analogue to the response value (stimulation index {SI}, the binary threshold (812 3}, and the EC3 concentrations m the LLNA assay, respectively.
Exemplary Embodiments.
[94] The following exemplary embodiments are provided, the numbering of which is not to be construed as designating levels of importance:
[95] Aspect 1 provides a fragrance composition comprising; a fragrance component; and an extract solution comprising: nymphaea coerulea flower extract; and nelumbo nucifera flower extract.
[96] Aspect 2 provides the fragrance composition of Aspect 1, wherein the fragrance component present in an amount in a range of from about 0.04 wt% to about 40 wt% of the fragrance composition.
[97] Aspect 3 provides the fragrance composition of any of Aspects | or 2, wherein the fragrance component present in an amount in a range of from about 0.5 wt% to about 30 wt% of the fragrance composition.
[98] Aspect 4 provides the fragrance composition of any of Aspects 1-3, wherien the extract solution is present in an amount of at least 2 wt% of the fragrance composition. 107
380526.NL.02-967.475NL2
[99] Aspect 5 provides the fragrance composition of any of Aspects 1-4, further comprising a modulator component.
[100] Aspect 6 provides the fragrance composition of Aspect 5, wherein the modulator component is present in an amount in a range of from about 0.04 wt% to about 40 wt% of the fragrance composition.
[101] Aspect 7 provides the fragrance composition of any of Aspects 5 or 6, wherein the modulator component 1s present in a range of from about 0.1 wt% to about 27 wt%.
[102] Aspect 8 provides the fragrance composition of any of Aspects 5-7, wherien the modulator component comprises: the compound according to Formula I:
OH
A
R' (I): a repeating unit derived from the compound according to Formula II:
NTN Re
R3 R® (IT); or a mixture thereof, wherein
R!, R% RY R* and R®, are independently chosen from -H, -OH, or substituted or unsubstituted (C-
Cap)hydrocarbyl.
[103] Aspect 9 provides the fragrance composition of any of Aspects 5-8, wherien the modulator component comprises pentylene glycol, polycitronellol, PPG-20 methyl glucose ether, methyl glucoside polyol, ethyl glucoside polyol, propyl glucoside polyol, or a mixture thereof. 108
380526.NL.02-967.475NL2
[104] Aspect 10 provides the fragrance composition of any of Aspects 5-9, wherien the modulator component is substantially non-odorous.
[105] Aspect 11 provides the fragrance composition of any of Aspects 1-10, wherein the fragrance component comprises at least of: at least one low volatile fragrance material having a vapor pressure less than 0.001 Torr (0.000133 kPa) at 25 °C; at least one moderate volatile fragrance material having a vapor pressure in the range of 0.1 Torr to 0.001 Torr (0.0133 kPa to 0.000133 kPa) at 25 °C; and at least one high volatile fragrance material having a vapor pressure greater than 0.1 Torr (0.0133 kPa) at 25 °C.
[106] Aspect 12 provides the fragrance composition of Aspect 11, wherein the at least one low volatile fragrance material is present in a range of from about 0 wt% to about 30 wt% of the fragrance component; the at least one moderate volatile fragrance material 1s present in a range of from about 30 wt% to about 70 wt% of the fragrance component; and the at least one high volatile fragrance material is present in a range of from about 0 wt% to about 30 wt% of the fragrance component.
[107] Aspect 13 provides the fragrance composition of any of Aspects 11 or 12, wherein the at least one low volatile fragrance material 1s present in a range of from about 30 wt% to about 70 wt% of the fragrance component; the at least one moderate volatile fragrance material is present at greater than about 30 wt% of the fragrance component; and the at least one high volatile fragrance material is present in a range of from about 0.1 wt% to about 30 wt% of the fragrance component.
[108] Aspect 14 provides the fragrance composition of any of Aspects 11-13, wherein the at least one low volatile fragrance material is present in a range of from about 0.1 wt% to about 30 wt% of the fragrance component; the at least one moderate volatile fragrance material is present in a range of from about 30 wt% to about 70 wt% of the fragrance component; and 109
380526.NL.02-967.475NL2 the at least one high volatile fragrance material is present at greater than about 30 wt% of the fragrance component.
[109] Aspect 15 provides the fragrance composition of any of Aspects 11-14, wherein the at least one low volatile fragrance material is present in a range of from about 30 wt% to about 35 wt% of the fragrance component; the at least one moderate volatile fragrance material 1s present in a range of from about 30 wt% to about 35 wt% of the fragrance component; and the at least one high volatile fragrance material 1s present in a range of from about 30 wt% to about 35 wt% of the fragrance component.
[110] Aspect 16 provides the fragrance composition of any of Aspects 11-15, wherein the at least one low volatile fragrance material is present in a range of from about 0 wt% to about 35 wt% of the fragrance component; the at least one moderate volatile fragrance material is present in a range of from about 40 wt% to about 60 wt% of the fragrance component; and the at least one high volatile fragrance material is present in a range of from about 0 wt% to about 30 wt% of the fragrance component.
[111] Aspect 17 provides the fragrance composition of any of Aspects 11-16, wherein the at least one low volatile fragrance material is present in a range of from about 25 wt% to about 50 wt% of the fragrance component; the at least one moderate volatile fragrance material 1s present in a range of from about 0 wt% to about 35 wt% of the fragrance component; and the at least one high volatile fragrance material is present in a range of from about 0.1 wt% to about 35 wt% of the fragrance component.
[112] Aspect 18 provides the fragrance composition of any of Aspects 11-17, wherein the at least one low volatile fragrance material is present in a range of from about 25 wt% to about 60 wt% of the fragrance component; the at least one moderate volatile fragrance material is present in a range of from about 0 wt% to about 35 wt% of the fragrance component; and the at least one high volatile fragrance material is present in a range of from about 25 wt% to about 60 wt% of the fragrance component. 110
380526.NL.02-967.475NL2
[113] Aspect 19 provides the fragrance composition of any of Aspects 11-18, wherein the at least one low volatile fragrance material is present in a range of from about 25 wt% to about 60 wt% of the fragrance component; the at least one moderate volatile fragrance material 1s present in a range of from about 25 wt% to about 60 wt% of the fragrance component; and the at least one high volatile fragrance material 1s present in a range of from about 25 wt to about 60 wt% of the fragrance component
[114] Aspect 20 provides the fragrance composition of any of Aspects 11-19, wherein the high volatile fragrance material is chosen from any of the materials or combinations of materials listed in any of Tables 3A and 3B; the low volatile fragrance material is chosen from chosen from any of the materials or combinations of materials listed in any of Tables 1A and 1B; and the moderate volatile fragrance material is chosen from chosen from any of the materials or combinations of materials listed in any of Tables 2A and 2B.
[115] Aspect 21 provides the fragrance composition of any of Aspects 1-20, further comprising a carrier.
[116] Aspect 22 provides the fragrance composition of Aspect 21, wherein the carrier is an aqueous carrier, an organic carrier, or a mixture thereof.
[117] Aspect 23 provides the fragrance composition of any of Aspects 21 or 22, wherein the organic carrier is ethanol, dipropylene glycol, benzyl benzoate, diethyl phthalate, isopropyl myristate, (Ci-Cao)alkyl, (Ci-Cao)alkenyl, (C1-C29)alkynyl, (Ci-Cao)hydroxyl, or mixtures thereof.
[118] Aspect 24 provides the fragrance composition of any of Aspects 1-23, wherien the fragrance component is detectable for an amount of time longer than a corresponding fragrance composition that free of the extract solution.
[119] Aspect 25 provides the fragrance composition of any of Aspects 1-24, wherien the fragrance component 1s more comfortable than a corresponding fragrance composition that free of the extract solution.
[120] Aspect 26 provides the fragrance composition of any of Aspects 1-25, further comprising lactic acid, a hyaluronic acid, vitamin E, saccharomyces/xylinum/black tea ferment, 111
380526.NL.02-967.475NL2 diglucosyl gallic acid, adenosine, panthenol, dimethylmethoxy chromanol, alpha-glucan oligosaccharide, thermus thermophilus ferment, hydrolyzed hyaluronic acid, caffeine, acetyl di- peptide-1 cetyl ester, glycerin, niacinamide, swertia chirata extract, creatine, or a mixture thereof
[121] Aspect 27 provides the fragrance composition of any of Aspects 1-26, further comprising niacinamide.
[122] Aspect 28 provides the fragrance composition of any of Aspects 1-27, further comprising a chelant.
[123] Aspect 29 provides the fragrance composition of Aspect 28, wherein the chelant comprises tetrasodium glutamate diacetate (GLDA), ethylenediaminetetraacetic acid (EDTA), ethylenediamine-N, N’-disuccinic acid (EDDS), NTA, EDDS, IDS, methylglycinediacetic acid (MGDA), L-glutamic acid N,N-diacetic acid (GLDA), ethylenediamine-N,N-diglutaric acid (EDDG), ethylenediamine-N,N’-dimalonic acid (EDDM), 3-hydroxy-2,2-iminodisuccinic acid (HIDS), 2-hydroxyethyliminodiacetic acid (HEIDA), methylglycine N‚N-diacetic acid trisodium salt (MGDA), sodium gluconate, or a mixture thereof.
[124] Aspect 30 provides the fragrance composition of any of Aspects 1-29, wherein the fragrance composition is more effective at reducing or eliminating malodor than a corresponding composition that is free of the extract solution.
[125] Aspect 31 provides the fragrance composition of any one of Aspects 1-30, wherien modulation of the fragrance composition is increased relative to a corresponding composition that is free of the extract solution and comprises a cyclodextrin, PPG 20 methyl glucose ether, a chelator, or a mixture thereof.
[126] Aspect 32 provides the fragrance composition of any one of Aspects 1-31, further comprising a cyclodextrin, a film former, or a mixture thereof.
[127] Aspect 33 provides the fragrance composition of Aspect 32, wherein the at least one film former is chosen from anionic compounds or polymers, non-ionic compounds or polymers, amphoteric compounds or polymers, zwitterionic compounds or polymers, cationic compounds or polymers, protems, viscosity modifiers, polyacrylates, polymethacrylates, polyacrylate copolymers, polymethacrylate copolymers, polyurethanes, polyamides, 112
380526.NL.02-967.475NL2 polyaminoamides, polyesters, polysaccharides, polyacrylamides, starches, gums, or mixtures thereof.
[128] Aspect 34 provides the fragrance composition of any one of Aspects 32 or 33, wherien the cyclodexrin comprises an a-cyclodextrin, a B-cyclodextrmn a gamma-cyclodextrin, or mixtures thereof.
[129] Aspect 35 provides a formulation for decreasing skin sensitizing potency of the fragrance, comprising one or more: fragrance components;
PPG 20 methyl glucose ether and ethanol; and an extract solution comprising: nymphaea coerulea flower extract; and nelumbo nucifera flower extract,
[130] Aspect 36 provides a method comprising: applying a sebum reducing composition comprising a topically acceptable vehicle and the fragrance composition of any of Aspects 1-35.
[131] Aspect 37 provides a method of treating skin with a component effective for functioning in a fragrance composition of Aspects 1-36, wherein the effectiveness of the component is determined by an assay for determining the levels of sebum, leptin, acetylcholine, or a mixture thereof in a sample that has been contacted with the extract or a composition including the extract.
[132] Aspect 38 provides a method of inhibiting acetylcholinesterase, the method comprising contacting the fragrance composition of any of Aspects 1-37, with a keratinous tissue.
[133] Aspect 39 provides a method of inhibiting a cholinergic receptor, the method comprising contacting the fragrance composition of any of Aspects 1-38, with a keratinous tissue. 113

Claims (24)

CONLCUSIES Wat wordt geclaimd is:CONLCUSIONS What is claimed is: 1. Een geursamenstelling die bestaat uit: Een oplosmiddel; een geurstof; en een extractoplossing bestaande uit: nymphaea coerulea bloemextract; en nelumbo nucifera bloemextract.1. A fragrance composition comprising: A solvent; a fragrance; and an extract solution comprising: nymphaea coerulea flower extract; and nelumbo nucifera flower extract. 2. De geurcompositie van claim 1, waarin het oplosmiddel water en/of ethanol bevat.2. The fragrance composition of claim 1, wherein the solvent contains water and/or ethanol. 3. De geurcompositie van bewering 2, waarin water aanwezig is in een verhouding van ten minste 1:1 met de extractoplossing van de geurcompositie.3. The fragrance composition of claim 2, wherein water is present in a ratio of at least 1:1 with the extract solution of the fragrance composition. 4. De geurcompositie van bewering 1, waarin de verhouding tussen geurstof en extractoplossing tussen 1:2 en 5:1 ligt.4. The fragrance composition of claim 1, in which the ratio of fragrance to extract solution is between 1:2 and 5:1. 5. De geurcompositie van claim 1, waarin de extractoplossing aanwezig is in een concentratie van ten minste 5% en het geurmateriaal bestaat uit een fougére-akkoord, De geurcompositie vertoont een grotere intensiteit in vergelijking met een geurcompositie die identiek is met uitzondering van de aanwezigheid van de extractoplossing bij het aanbrengen op de menselijke huid; 2 uur na het aanbrengen op de menselijke huid; en 6 uur na het aanbrengen op de menselijke huid.5. The fragrance composition of claim 1, wherein the extract solution is present in a concentration of at least 5% and the fragrance material consists of a fougere accord, The fragrance composition exhibits a greater intensity compared to a fragrance composition that is identical except for the presence of the extract solution upon application to human skin; 2 hours after application to human skin; and 6 hours after application to human skin. 6. De geurcompositie van claim 1, waarin wanneer de extractoplossing aanwezig is in een concentratie van minstens 5% en het geurmateriaal bestaat uit een citrusakkoord, De geurcompositie vertoont een grotere intensiteit in vergelijking met een geurcompositie die identiek is met uitzondering van de aanwezigheid van de extractoplossing 6 uur na aanbrengen op de menselijke huid. 1146. The fragrance composition of claim 1, wherein when the extract solution is present in a concentration of at least 5% and the fragrance material consists of a citrus accord, The fragrance composition exhibits a greater intensity compared to a fragrance composition that is identical except for the presence of the extract solution 6 hours after application to human skin. 114 7. De geurcompasitie van claim 1, waarin het geurmateriaal aanwezig is in een hoeveelheid van ongeveer 0,04 wt% tot ongeveer 40 wt% van de geurcompositie.7. The fragrance composition of claim 1, wherein the fragrance material is present in an amount of from about 0.04 wt% to about 40 wt% of the fragrance composition. 8. De geurcompositie van claim 1, waarin de compositie een groter behoud van geurcapaciteit vertoont bij blootstelling aan water in vergelijking met een equivalente formule die alleen verschilt in de aanwezigheid van Nelupure.8. The fragrance composition of claim 1, wherein the composition exhibits greater retention of fragrance capacity upon exposure to water compared to an equivalent formulation differing only in the presence of Nelupure. 9. De geurcompositie van claim 1, waarin het geurmateriaal aanwezig is in een hoeveelheid van ongeveer 0,5 wt% tot ongeveer 30 wi% van de geurcompositie.9. The fragrance composition of claim 1, wherein the fragrance material is present in an amount of from about 0.5 wt% to about 30 wt% of the fragrance composition. 10. De geurcompositie van claim 1, waarin het geurmateriaal aanwezig is in een hoeveelheid van ongeveer 20% tot ongeveer 40% van de geurcompositie.10. The fragrance composition of claim 1, wherein the fragrance material is present in an amount of from about 20% to about 40% of the fragrance composition. 11. De geurcompositie van claim 1, waarin de extractoplossing aanwezig is in een hoeveelheid van ten minste 4 wt% van de geurcompositie.11. The fragrance composition of claim 1, wherein the extract solution is present in an amount of at least 4 wt% of the fragrance composition. 12. De geurcompositie van claim 1 bevat verder een modulatorcomponent.12. The fragrance composition of claim 1 further contains a modulator component. 13. De geurcompositie van claim 12, waarin de modulatorcomponent aanwezig is in een hoeveelheid van ongeveer 0,04 wt% tot ongeveer 40 wt% van de geurcompositie.13. The fragrance composition of claim 12, wherein the modulator component is present in an amount of from about 0.04 wt% to about 40 wt% of the fragrance composition. 14. De geurcompositie van claim 12, waarin de modulatorcomponent aanwezig is in een bereik van ongeveer 0,1 wt% tot ongeveer 27 wt%.14. The fragrance composition of claim 12, wherein the modulator component is present in a range of about 0.1 wt% to about 27 wt%. 15. De geursamenstelling van claim 13, waarbij de modulatorcomponent bestaat uit: de verbinding volgens Formule |: OH 1 R 0; een repeterende eenheid afgeleid van de verbinding volgens formule II: 11515. The fragrance composition of claim 13, wherein the modulator component consists of: the compound of Formula |: OH 1 R 0; a repeating unit derived from the compound of Formula II: 115 NT Re? R3 R® (11); or een mengsel daarvan, waarin R1, R2, R3, R4 en R5 onafhankelijk gekozen worden uit -H, -OH, of gesubstitueerde of niet- gesubstitueerde (C1-C20)hydrocarbyl.NT Re? R3 R® (11); or a mixture thereof, wherein R1, R2, R3, R4 and R5 are independently selected from -H, -OH, or substituted or unsubstituted (C1-C20)hydrocarbyl. 16. De geurcompositie van claim 12, waarbij de modulatorcomponent bestaat uit pentylene glycol, polycitronellol, PPG-20 methylglucose-ether, methylglucosidepolyol, ethylglucosidepolyol, propylglucosidepolyol of een mengsel daarvan.16. The fragrance composition of claim 12, wherein the modulator component consists of pentylene glycol, polycitronellol, PPG-20 methyl glucose ether, methyl glucoside polyol, ethyl glucoside polyol, propyl glucoside polyol or a mixture thereof. 17. De geurcompositie van claim 1, bevat verder een organische draagstof bestaande uit ethanol, dipropyleenglycol, benzylbenzoaat, diethylftalaat, isopropylmyristaat, (C1-C20}alkyl, (C1-C20)alkenyl, (C1-C20)alkynyl, (C1-C20)hydroxyl, of mengsels daarvan in een bereik van meer dan 10% van de geurcompositie.17. The fragrance composition of claim 1 further comprises an organic carrier consisting of ethanol, dipropylene glycol, benzyl benzoate, diethyl phthalate, isopropyl myristate, (C1-C20)alkyl, (C1-C20)alkenyl, (C1-C20)alkynyl, (C1-C20)hydroxyl, or mixtures thereof in a range of more than 10% of the fragrance composition. 18.. De geurcompositie van claim 1, waarin de geurcomponent langer detecteerbaar is dan een overeenkomstige geurcompositie zonder extractoplossing.18.. The fragrance composition of claim 1, wherein the fragrance component is detectable for a longer period than a corresponding fragrance composition without extract solution. 19. De geurcompositie van claim 12, verder bestaande uit een chelant.19. The fragrance composition of claim 12, further consisting of a chelant. 20. De geurcompositie van claim 1, verder bestaande uit een filmvormer.20. The fragrance composition of claim 1, further comprising a film former. 21. Een primersamenstelling bestaande uit: Een oplosmiddel bestaande uit water of ethanol en water; en een extractoplossing bestaande uit nymphaea coerulea bloemextract; en nelumbo nucifera bloemextract; Met dien verstande dat de primersamenstelling geen geurstoffen bevat.21. A primer composition consisting of: A solvent consisting of water or ethanol and water; and an extract solution consisting of nymphaea coerulea flower extract; and nelumbo nucifera flower extract; Provided that the primer composition does not contain any fragrances. 22. De geursamenstelling van claim 1, waarin de geursamenstelling effectiever is in het verminderen of elimineren van onwelriekende geur dan een overeenkomstige samenstelling die geen extractoplossing bevat. 11622. The fragrance composition of claim 1, wherein the fragrance composition is more effective in reducing or eliminating malodor than a corresponding composition not containing the extract solution. 116 23. De geurcompositie van claim 22, waarbij de modulatie van de geurcompositie is verhoogd ten opzichte van een overeenkomstige samenstelling die vrij is van de extractoplossing en een cyclodextrine, PPG 20 methylglucose-ether, een chelator of een mengsel daarvan bevat.23. The fragrance composition of claim 22, wherein the modulation of the fragrance composition is increased relative to a corresponding composition free of the extract solution and containing a cyclodextrin, PPG 20 methyl glucose ether, a chelating agent or a mixture thereof. 24. De geurcompositie van claim 23 bevat verder een cyclodextrine, een filmvormer of een mengsel daarvan. 11724. The fragrance composition of claim 23 further contains a cyclodextrin, a film former or a mixture thereof. 117
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