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WO2008141769A1 - Compositions de parfum - Google Patents

Compositions de parfum Download PDF

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Publication number
WO2008141769A1
WO2008141769A1 PCT/EP2008/003940 EP2008003940W WO2008141769A1 WO 2008141769 A1 WO2008141769 A1 WO 2008141769A1 EP 2008003940 W EP2008003940 W EP 2008003940W WO 2008141769 A1 WO2008141769 A1 WO 2008141769A1
Authority
WO
WIPO (PCT)
Prior art keywords
perfume
malodour
perfume composition
phenoxyacetate
anisyl acetone
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2008/003940
Other languages
English (en)
Inventor
Cees Van Biezen
Keith Douglas Perring
Anne Churchill
Alan Forbes Provan
John Martin Behan
Gaetane Marie Wentzo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Givaudan Nederland Services BV
Original Assignee
Quest International Services BV
Givaudan Nederland Services BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Quest International Services BV, Givaudan Nederland Services BV filed Critical Quest International Services BV
Publication of WO2008141769A1 publication Critical patent/WO2008141769A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, 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
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring

Definitions

  • This invention relates to perfume compositions, to consumer products containing such perfume compositions, and to the use of such perfume compositions to provide malodour counteracting effects.
  • malodour is used here to refer to smells and odours generally regarded as undesirable or unpleasant in nature.
  • malodour counteraction is usually taken as any action that results in alleviation of the unpleasant perception of a malodour, and does not in itself indicate how such alleviation is brought about.
  • British Patent GB 1545561 similarly describes 1- cyclohexyl-1-alkyl alkanoates wherein neither the alkyl group nor the corresponding alkanoic acid contains no more than four carbon atoms; closely related alcohols are disclosed as malodour counteractants in US Patent 4,719,105. The ability of certain of these materials to cover specific base odours is disclosed in US Patent No. 6432891.
  • the present invention is based on the surprising discovery that anisyl acetone and 2-hydroxyethyl phenoxyacetate act synergistically in improving the malodour counteraction properties of perfumes.
  • the phenoxyacetate ester is a known low odour malodour counteractant (see for example US Patent No. 4,310,512).
  • Anisyl acetone (known more systematically as 4-[4-(methyloxy)phenyl]butan-2-one) is a common perfume ingredient that is not recognized as having particularly good malodour counteraction efficacy, an observation that has been borne out in the studies reported below.
  • this invention provides perfume compositions comprising by weight at least 5% of anisyl acetone and 2-hydroxyethyl phenoxyacetate in total, wherein the weight ratio of anisyl acetone to 2-hydroxyethyl phenoxyacetate is from 1:8 to 2: 1.
  • a perfume or fragrance composition is defined as a mixture of two or more odoriferous perfume ingredients, if desired mixed with or dissolved in a suitable solvent or solvents and/or mixed with a solid substrate, together with anisyl acetone and 2-hydroxyethylphenoxyacetate.
  • Perfume ingredients are well known to those skilled in the art, and include those mentioned, for example, in “Common Fragrance and Flavor Materials” by Bauer, Garbe and Surburg, VCH Publ., 3 rd edition (2001), “Perfume and Flavour Materials”, Steffen Arctander (Montclair, N.J., 1969) published in two volumes, “Perfume and Flavor Materials of Natural Origin”, S. Arctander (Elizabeth, N. J., 1960), and “Allured's Flavor and Fragrance Materials - 2001", Allured Publishing Co. Wheaton, 111. USA.
  • Perfume ingredients may include natural products such as extracts, essential oils, absolutes, resinoids, resins, concretes etc.
  • references herein to the percentage by weight of perfume ingredients means (unless specified otherwise) relative to the total weight of perfume ingredients in the perfume composition and includes materials that are used within perfumery as vehicles or solvents for other perfume ingredients, for example dipropylene glycol, isopropyl myristate, benzyl benzoate, diethyl phthalate, triacetin and triethyl citrate.
  • the invention also provides use of a mixture of 2-hydroxyethyl phenoxyacetate and anisyl acetone in a perfume composition for enhancing the malodour reduction properties of the composition.
  • the invention also includes in its scope a method of enhancing the malodour reduction properties of a perfume composition, comprising including in the composition a mixture of anisyl acetone and 2-hydroxyethyl phenoxyacetate.
  • the present invention is concerned with perfume compositions that reduce the perception of malodour s by sensory means not dependent upon the deployment of strong, or even overwhelming, perfume odour intensities.
  • the malodour counteractant 2-hydroxy ethyl phenoxy acetate also known as 2-hydroxy ethyl (phenyloxy)acetate, labelled for convenience as 2HEPA below
  • 2HEPA works against a wide variety of malodours, including both environmental (such as tobacco, fish, cooking smells, bathroom smells, etc) and body odours (such a sweat, urine, etc).
  • Perfumes of the invention comprise at least 5% by weight in total of anisyl acetone and 2HEPA in weight ratios in the range 1 :8 to 2: 1 (anisyl acetone to 2HEPA), more preferably in the range 1:4 to 1: 1. Because 2HEPA has a quite weak odour, the perfumer creating fragrances incorporating it has to strike a balance between enhancing malodour counteraction and enhancing hedonic properties, and this places a limit on how much of 2HEPA may usefully be incorporated. Preferably perfumes of the invention will contain no more than 25% w/w 2HEPA, more usually no more than 15%, most preferably no more than 10% .
  • Particularly preferred perfumes of the invention comprise 7.5% to 10% of 2HEPA in combination with anisyl acetone at a weight ratio of from 1:3 to 1: 1 (anisyl acetone to 2HEPA).
  • Preferred perfumes of the invention are more complex than simple accords and comprise at least 20 odoriferous perfume materials, more preferably at least 25.
  • the invention provides a perfumed consumer product comprising a perfume composition in accordance with the invention.
  • a consumer product comprises a solid, liquid, gel or soft solid formulation for use in or on a substrate such as skin, hair, clothing or hard surface.
  • a substrate such as skin, hair, clothing or hard surface.
  • Examples of such products include bathroom and kitchen cleaners, carpet cleaners, polishes, personal body refreshers and deodorants, pet deodorants, in a variety of formats such as liquids (particularly as delivered by trigger sprays or aerosols), gels and powders, all of which are well known in the art.
  • perfume compositions are used as an olfactory component of a consumer composition, such as a solid or liquid anionic, cationic, nonionic or zwitterionic detergent or a cosmetic powder or a deodorant stick, as little as 0.1 % by weight of the fragrance composition in the perfumed article will suffice. In space odorant applications, on the other hand, as much as 99% of the combined carrier perfume substance and fragrance composition(s) can be present.
  • consumer compositions may contain in the range of from about 0.1 % up to about 99% of a composition of matter consisting essentially of perfume composition(s) of this invention.
  • perfumed product excluding packaging and other matter extraneous to the perfumed solid, liquid, gel or soft solid formulation.
  • the perfumes of the invention compounds may be applied in a variety of consumer products that have malodour control as a primary or secondary function. Such products may be used to exert a malodour control effect on air containing malodour either directly, for instance in a conventional room freshener (or deodorant) composition such as an aerosol or other spray, a wick or other liquid system, or a solid, for instance a wax base as in pomanders and plastics, powders as in sachets or dry sprays or gels, as in solid gel sticks, or they may be applied to the air indirectly.
  • a conventional room freshener (or deodorant) composition such as an aerosol or other spray, a wick or other liquid system, or a solid, for instance a wax base as in pomanders and plastics, powders as in sachets or dry sprays or gels, as in solid gel sticks, or they may be applied to the air indirectly.
  • clothes deodorants may be included in clothes deodorants as applied by washing machine applications such as in detergents, powders, liquids, whiteners or fabric softeners or by other applications such as closet blocks, closet aerosol sprays, or clothes storage areas or in dry cleaning to overcome residual solvent notes on clothes; in bathroom accessories such as paper towels, bathroom tissues, sanitary napkins, towellets, disposable wash cloths, disposable diapers, and diaper pail deodorants; in cleansers such as disinfectants and toilet bowl cleaners; in cosmetic products such as antiperspirant and underarm deodorants, general body deodorants in the form of powders, aerosols, liquids or solid, or hair care products such as hair sprays, conditioners, rinses, hair colours and dyes, permanent waves, depilatories, hair straighteners, hair groom applications such as pomade, creams and lotions, shampoos, or foot care products such as foot powders, liquids or colognes, after shaves and body lotions, or soaps and synthetic detergents such as bars, liquids, foams or
  • the sensory panel consists of a pool of between 25 and 35 members, who are all screened and then trained over a period of 6 months. Training includes learning to identify individual odour characters in complex mixtures, and to score their perceived intensity using a ratio scoring technique (Magnitude Estimation). The level of efficiency of the panel is continuously monitored to ensure a high level of accuracy and reproducibility.
  • the perfume material and malodour are placed alongside each other in a 500ml glass vessel: 3ml of malodour in a squat 15ml jar alongside a perfume material (1ml in a 15ml upright jar).
  • Equivalent jars containing diethyl phthalate (odourless solvent) in place of malodour were prepared using the same process. The vessel is closed and allowed to equilibrate for half an hour before assessment.
  • Each panel member assesses each sample for the intensity of malodour and perfume material that can be perceived in the headspace of the glass vessel using a line scale anchored at the extremes (0-100).
  • the malodour control is used as a standard (perceived intensity 75) against which all other perceived intensities are scaled.
  • perfume only controls detailed above hidden blanks (malodour but no perfume) were included as further internal controls.
  • the scores for each of the panellists are normalised and averaged to give a consensus score across the whole panel.
  • Typical malodour examples are well known in the art e.g. as disclosed in GB 1545561.
  • a typical bathroom malodour composition was prepared (example 36 in GB 1545561) and used in testing (see example 2 herein) as a 0.5% dilution in diethyl phthalate (DEP).
  • DEP diethyl phthalate
  • Perfume Composition 2.1 detailed in Table 1 was created following the guidelines of the present invention.
  • Formulations 2.2, and 2.3 are comparatives that fall outside these guidelines.
  • Table 4 details further examples of perfumes according to the invention whose performance is enhanced by the combination of anisyl acetone and 2-hydroxyethyl phenoxyacetate in the correct levels and ratios.
  • Lily aldehyde 3-[4-(l , l-dimethylethyl)phenyl]-2-methylpropanal
  • APPLINAL (G)TM is ethyl (2-methyl-l,3-dioxolan-2-yl)acetate
  • BANGALOL (G) TM is 2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-l-yl)but-2-en-l-ol
  • BOURGEONAL (G) TM is 3-[4-(l,l-dimethylethyl)phenyl]propanal
  • ETHYL SAFRANATE (G) TM is ethyl 2,6,6-trimethylcyclohexa-l,3-diene-l-carboxylate
  • FLOROCYCLENETM is tricyclo[5.2.1.0 ⁇ ⁇ 2,6 ⁇ ]dec-3-en-8-yl propanoate
  • ISOAMBOIS (G) TM is a mixture of a) l-(2,3,8,8-tetramethyl-l,2,3,5,6,7,8,8 a-octahydronaphthalen-2-yl)ethanone b)l-(2,3,8,8-tetramethyl-l,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethanone JADENOL (G) TM is 4-methyldec-3-en-5-ol
  • JASMACYCLENE TM is tricyclo[5.2.1.0 ⁇ ⁇ 2,6 ⁇ ]dec-4-en-8-yl acetate
  • JASMOPYRANE FORTE (G) TM is 3-pentyltetrahydro-2H-pyran-4-yl acetate
  • LIGUSTRAL (G) TM is 2,4-dimethylcyclohex-3-ene-l-carbaldehyde
  • MEFROSOL (G) TM is 3-methyl-5-phenylpentan-l-ol
  • OCTAHYDROCOUMARIN (G) is octahydro-2H-chromen-2-one
  • ORTHOLATE (G) TM is 2-(l,l-dimethylethyl)cyclohexyl acetate
  • SILVANONE (G) TM is mixture of : a) cyclohexadecanolide; b) cyclopentadecanone;c) isopropyl myristate

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention porte sur des compositions de parfum comprenant au moins 5 % en poids d'acétone anisique et de phénoxyacétate de 2-hydroxyéthyle au total, le rapport en poids de l'acétone anisique au phénoxyacétate de 2-hydroxyéthyle étant de 1:8 à 2:1. On a découvert que ces compositions de parfum possèdent des propriétés surprenantes d'action contre les mauvaises odeurs.
PCT/EP2008/003940 2007-05-23 2008-05-16 Compositions de parfum Ceased WO2008141769A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0709885A GB0709885D0 (en) 2007-05-23 2007-05-23 Perfume compositions
GB0709885.8 2007-05-23

Publications (1)

Publication Number Publication Date
WO2008141769A1 true WO2008141769A1 (fr) 2008-11-27

Family

ID=38265218

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2008/003940 Ceased WO2008141769A1 (fr) 2007-05-23 2008-05-16 Compositions de parfum

Country Status (2)

Country Link
GB (1) GB0709885D0 (fr)
WO (1) WO2008141769A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4310512A (en) * 1977-08-29 1982-01-12 Bush Boake Allen Inc. Derivatives of acetic and propionic acids, compositions containing same and use as malodor counteractants
US6432891B1 (en) * 2000-06-23 2002-08-13 Bush Boake Allen Inc., Malodor counteractant compositions and methods for preparing and using same
JP2005272378A (ja) * 2004-03-25 2005-10-06 Kao Corp 毛髪化粧料

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4310512A (en) * 1977-08-29 1982-01-12 Bush Boake Allen Inc. Derivatives of acetic and propionic acids, compositions containing same and use as malodor counteractants
US6432891B1 (en) * 2000-06-23 2002-08-13 Bush Boake Allen Inc., Malodor counteractant compositions and methods for preparing and using same
JP2005272378A (ja) * 2004-03-25 2005-10-06 Kao Corp 毛髪化粧料

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 200576, Derwent World Patents Index; AN 2005-737588, XP002498901 *

Also Published As

Publication number Publication date
GB0709885D0 (en) 2007-07-04

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