WO2008141769A1 - Perfume compositions based on anisylacetone and 2-hydroxyethyl phenoxyacetate - Google Patents

Abstract

The invention relates to perfume compositions comprising at least 5% by weight 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, which have been found to possess surprising malodour counteractancy properties.

Description

PERFUME COMPOSITIONS BASED ON ANISYLACETONE AND 2-HYDROXYETHYL PHENOXYACETATE

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.

It is clearly desirable to be able to reduce malodour s in many circumstances, for example in domestic environments where common malodours include kitchen, bathroom (lavatory) and malodours in carpets and other furnishings eg. mould, pets odours. Other common malodours include body odours and malodours on clothes e.g. perspiration, smoke, cooking and other environmental odours. The term "malodour" is used here to refer to smells and odours generally regarded as undesirable or unpleasant in nature. The term "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.

Many routes have been taken to address malodour problems, including routes based around delivering perfume into air containing malodour. It is well known to incorporate perfume materials in a wide range of products such as kitchen and bathroom cleaners, air fresheners, carpet and fabric cleaners, laundry products, and personal hygiene products, with a view to reducing such malodours.

A large number of perfumes have high odour intensities and may act by smothering malodours so as to mask them from being perceived. However, this form of malodour counteraction may require the use of overwhelming perfume intensities, and such intensity levels are often regarded as not desirable, and it useful to be able to create perfumes that can exhibit high efficacy in combatting malodours without providing excessive odour intensities in use. A variety of mechanisms have been proposed to explain how high efficacy may be achieved. For example, some materials are considered to remove malodours at least in part by chemical reaction (see for example US Patents Nos. 3,077,457, 3,074,892 and 3,250,724). US 6,610,648 discloses mixtures of materials that have low odour and comprise activated esters (esters with alpha, beta-unsaturation).

Other high performance materials and mixtures thereof have been described as 'true' malodour counter actants that work via sensory mechanisms such as odour blocking, perhaps by impeding access to olfactory receptors (though definitive research output on this is generally not available). Fragrance compositions that comprise high efficiency malodour counteractants that work via sensory means have been available for some time, such as those sold under the tradename Veilex(tm). For example US Patent No. 4,310,512 describes hydroxyalkyl aryloxyacetates and aryloxypropionates that are effective in counteracting malodours in air. 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.

In spite of the above, there remains a need to provide more cost-effective malodour counteraction solutions. 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.

In one aspect, 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. For the purposes of this invention 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. , and also synthetic substances such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ketals, nitriles, etc. , including saturated and unsaturated compounds, aliphatic, macrocyclic and heterocyclic compounds.

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.

In a further aspect, 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. We have found that the malodour counteractant 2-hydroxy ethyl phenoxy acetate (also known as 2-hydroxy ethyl (phenyloxy)acetate, labelled for convenience as 2HEPA below) is one of the most effective materials disclosed in the prior art as a malodour counter actant. 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). It has surprisingly been discovered that its malodour counteraction efficacy is enhanced when it is incorporated in perfumes also containing anisyl acetone. Anisyl acetone has been used in perfume compositions for many years. It is described by Arctander in "Perfume and Flavour Materials" (op.cit.) in monograph 248. No teachings exist as to its use for malodour counteraction enhancement in combination with 2HEPA nor with analogues or similar materials to 2HEPA.

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.

In a further aspect, the invention provides a perfumed consumer product comprising a perfume composition in accordance with the invention. For the purposes of this 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. 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.

When 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. Thus, 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.

However, typical levels of perfume would be in the range 0.01 % to 15% by weight, more usually 0.1 % to 10% by weight based on the 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. For instance they 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 powders; in car fresheners; in pet care products such as deodorants, shampoo or cleaning agents, or animal litter material and in large scale closed air systems such as auditoria, and subways and transport systems.

The performance of perfume compositions in reducing malodour was measured experimentally by assessing for their effectiveness in reducing (counteracting) a standard bathroom malodour in small scale headspace assessments carried out by trained sensory assessors.

Example 1 : Experimental testing procedure

Techniques have been developed for the accurate measurement of the performance of perfume materials and compositions against standard malodours utilising small scale headspace assessments carried out by a sensory panel of trained sensory assessors.

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.

During testing all variables other than those actually under test are controlled as carefully as possible. Samples are always prepared so that they are, as far as possible, identical apart from their differences in odour. When presented to panellists they are presented in random order and given random 3-figure codes. A minimum of 30 assessments were collated for each sample. All assessments reported in the examples were carried out in a purpose built panel suite. The suite is designed so that all external distractions (ie. odour, noise, movement) are eliminated, and the panellists are not distracted during testing.

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. As well as 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.

Standard statistical techniques were employed to compare the performance of each sample against the malodour and the statistical significance of any differences detected.

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).

Example 2. Perfume Compositions

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 1 Perfume Compositions (% w/w)

(G) = Trademark material of Givaudan

(S) = Solvent

* (3-(4-isopropylphenyl)-2-methylpropanal)

Following the methods outlined previously, the above examples give results detailed in Tables 2 and 3.

Table 2. Results from assessment of samples with malodour

Table 3. Results from assessment of samples in absence of malodour

Note: The samples with the same character (a) alongside are NOT significantly different (p = 0.90)

The results (Table 2) show that Perfume Composition 2.1 is significantly better at reducing the malodour compared to compositions 2.2 and 2.3. Table 3 indicates that there is no significant difference in perfume intensity between the three compositions when assessed separately.

Example 4: Perfume compositions

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.

Table 4 Perfume Compositions w/w%

INGREDIENT 3.1 3.2 3.3

2-HYDROXYETHYL PHENOXYACETATE 11 4.5 8 ANISYL ACETONE 4.9 1.5 2.8

ALLYL AMYL GLYCOLATE 0 0 0.5 ANISIC ALDEHYDE 1.8 O 0 APPLINAL (G)™ O 0.5 2 BANGALOL (G) ™ 0.4 0.5 0 BENZYL ACETATE O 3 6.5 BERGAMOT OIL O 5.8 0 BOURGEONAL (G) ™ 1 0.7 0 CIS-3-HEXEN0L O O 1 CIS-3-HEXENYL ACETATE O O 0.6 CITRONELLOL O 4.9 1.5 CITRONELLYL ACETATE O 2 1.3 DAMASCONE, ALPHA- O O 0.1 DECALACTONE, GAMMA- 0.2 0.5 0 DIHYDROMYRCENOL O O 6.5 DIMETHYL BENZYL CARBINYL O 0.7 2.7 BUTYRATE

DIPROPYLENE GLYCOL 41 21 26.7 ETHYL 2-METHYLBUTYRATE O O 0.2 ETHYL MALTOL 1 % IN DPG 2 O 0 ETHYL METHYL PHENYLGLYCIDATE 0.4 O 0 ETHYL SAFRANATE (G) ™ O 0.6 0 ETHYLENE BRASSYLATE 6 O 0 EUGENOL O 0.3 0 FLOROCYCLENE™ 0.5 O 1.2 GERANIOL O 2 0 GERANYL ACETATE 0.4 2 0.3 HELIOTROPIN 1.2 O 0 HEXYL ACETATE 0.3 O 4 HEXYL CINNAMIC ALDEHYDE O 2 0 HEXYL SALICYLATE O 2 0 IONONE, ALPHA- 2 O 0 IONONE, BETA- O 3 1.2 ISO EUGENYL ACETATE O 0.3 0 ISOAMBOIS (G) ™ 3.5 0.75 0 JADENOL (G) ™ O 0 0.4 JASMACYCLENE ™ O 1.4 1 JASMOPYRANE FORTE (G) ™ O 0.4 0 LEMON ITALIAN OIL O 0 0.5 LIGUSTRAL (G) ™ O 0 0.5 LILY ALDEHYDE O 3.6 0 LINALOL O 3 2

LINALYL ACETATE O 0 0.5 MEFROSOL (G) ™ O 3.5 0 METHYL CEDRYL KETONE O 3.25 0 METHYL DIHYDROJASMONATE 9.1 3.5 6 METHYL IONONE, ALPHA-ISO- O 1 2 MOSS OAKMOSS SYNTHETIC O 0.4 0 OCTAHYDROCOUMARIN (G) 0.5 0 0 ORANGE OIL O 0 10.4 ORTHOLATE (G) ™ 2.2 3 2 PHENYL ACETIC ACID 10% IN DPG O 0.5 0 PHENYL ETHYL ALCOHOL O 9 6 PHENYLETHYL PHENYLACETATE O 3 0 PHENYLETHYL ISO-BUTYRATE O 0 0.2 RASPBERRY KETONE 0.4 0.8 0 ROSACETONE O 1.8 0 SILVANONE (G) ™ O 2 0 TERPINEOL O 0 1

TETRAHYDROLINALOL 7.5 0 0 UNDECALACTONE, GAMMA- 2.2 1.3 0.4 VANILLIN 10% IN DPG 1.5 0 0

TOTAL % 100 100 100

TOTAL AA AND 2HEPA = 15.9 6 10.8

RATIO 2HEPA:AA = 2.24 3.00 2.86

Key to Table 4

(G): available from Givaudan

DPG: dipropylene glycol

Roseacetone: 2,2,2-trichloro-l-phenylethyl acetate

Lily aldehyde: 3-[4-(l , l-dimethylethyl)phenyl]-2-methylpropanal

Raspberry ketone: 4-[4-(methyloxy)phenyl]butan-2-one

APPLINAL (G)™ is ethyl (2-methyl-l,3-dioxolan-2-yl)acetate BANGALOL (G) ™ is 2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-l-yl)but-2-en-l-ol

BOURGEONAL (G) ™ is 3-[4-(l,l-dimethylethyl)phenyl]propanal ETHYL SAFRANATE (G) ™ is ethyl 2,6,6-trimethylcyclohexa-l,3-diene-l-carboxylate

FLOROCYCLENE™ is tricyclo[5.2.1.0^Λ{2,6}]dec-3-en-8-yl propanoate

ISOAMBOIS (G) ™ 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) ™ is 4-methyldec-3-en-5-ol

JASMACYCLENE ™ is tricyclo[5.2.1.0^Λ{2,6}]dec-4-en-8-yl acetate JASMOPYRANE FORTE (G) ™ is 3-pentyltetrahydro-2H-pyran-4-yl acetate LIGUSTRAL (G) ™ is 2,4-dimethylcyclohex-3-ene-l-carbaldehyde

MEFROSOL (G) ™ is 3-methyl-5-phenylpentan-l-ol OCTAHYDROCOUMARIN (G) is octahydro-2H-chromen-2-one

ORTHOLATE (G) ™ is 2-(l,l-dimethylethyl)cyclohexyl acetate

SILVANONE (G) ™ is mixture of : a) cyclohexadecanolide; b) cyclopentadecanone;c) isopropyl myristate

Claims

4013Claims

1. A perfume composition comprising at least 5% by weight of anisyl acetone and 2-hydroxy ethyl phenoxyacetate in total, wherein the weight ratio of anisyl acetone to 2-hydroxy ethyl phenoxyacetate is froml:8 to 2: 1.

2. A perfume composition according to claim 1, wherein the weight ratio of anisyl acetone to 2-hydroxy ethyl phenoxyacetate is from 1:4 to 1: 1.

3. A perfume composition according to claim 1 or claim 2, comprising at least 10% by weight of anisyl acetone and 2-hydroxy ethyl phenoxyacetate.

4. A perfume composition according to any one of the preceding claims comprising at least twenty perfume ingredients.

5. A consumer product comprising a perfume composition according to any one of the preceding claims.

6. A method of counteracting malodour perception comprising exposing an air space to a perfume composition according to any one of claims 1 to 4 or a product according to claim 5.

7. A method of counteracting malodour perception comprising treating a surface with a perfume composition according to any one of claims 1 to 4 or a product according to claim 5.

8. Use of a mixture of 2-hydroxy ethyl phenoxyacetate and anisyl acetone in a perfume composition to enhance its malodour counteraction properties.