WO2000001361A1

WO2000001361A1 - Perfume compositions

Info

Publication number: WO2000001361A1
Application number: PCT/GB1999/002164
Authority: WO
Inventors: Keith Douglas Perring; John Martin Behan
Original assignee: Quest International B.V.
Priority date: 1998-07-07
Filing date: 1999-07-06
Publication date: 2000-01-13
Also published as: GB9814655D0; EP1093358A1; AU4636999A

Abstract

A perfume composition contains at least 40 % by weight of at least three out of six defined perfume ingredient categories of hydroxylic materials, ketones, aldehydes, ethers, esters and nitriles. The perfume composition exhibits a deodorant effect, and is suitable for use in deodorant products, personal products and laundry treatment products.

Description

PERFUME COMPOSITIONS

This invention relates to perfume compositions, that is to say compositions of fragrance materials, to personal products and other products containing such perfume compositions, and to the use of such perfume compositions to give a deodorant effect.

EP-B-3172, EP-A-5618, US-A-4304679, US-A-4322308, US-A-4278658, US-A-4134838. US-A-4288341 , USA-4289641 and US 4 906 454 all describe perfume compositions which exhibit a deodorant action, (i.e. addresses the problem of human body odour, particularly that~ of the axillae) either when applied to human skin using a cosmetically acceptable vehicle or when included in a detergent product or fabric conditioning product used in laundering of textiles. EP-B-147191 and US-A-4663068 describes deodorant perfume compositions which are stable in the presence of bleaching materials.

A difficulty with the perfume compositions disclosed in these documents is that they generally include appreciable quantities of relatively high molecular weight perfume components which help to extend the effective lifetime of deodorant action following product application, but which tend to have less perfume impact and to exhibit odour characteristics which span a finite range. This limitation on perfume composition represents a compromise between long term deodorant efficacy and optimal hedonic performance.

We have now found that deodorant perfumes can be made by the use of materials from certain specified categories of perfume materials which makes it possible to obtain fragrances containing lower quantities of high boiling components while also obtaining good long term deodorant properties. Forms of this invention can deliver a deodorant performance which improves on that obtained from compositions exemplified in the prior documents above.

Accordingly, the present invention provides a perfume composition comprising at least 40% in total by weight of at least three of the following six categories of perfumery ingredients; a) at least 1.0%, preferably at least 5% and generally not more than 50% by weight of the perfume composition comprises one or more hydroxylic materials of general formula

ROH having an octanol-water partition coefficient within the range of 2.5 to 3.6 (in logarithmic form), and wherein the group R¹ is a hydrocarbyl radical containing no more than one olefinic double bond, and comprising aromatic or aliphatic groups, and mixtures thereof, and which may be cyclic or acyclic, straight chained or branched, and optionally substituted with other groups, b) at least 1.0%, preferably at least 5% and generally not more than 30% by weight of the perfume composition of one or more ketones selected from ketones of general formula rVCO R² having an octanol-water partition coefficient within the range of 3.0 to 4.1 (in logarithmic form), and wherein the groups R¹ and R² are independently hydrocarbyl radicals which may comprise aromatic or aliphatic groups, and mixtures thereof, and may be cyclic or acyclic, straight chained or branched, and optionally substituted with other groups, c) aldehydes of general formula

R¹CHO having an octanol-water partition coefficient within the range of 2.0 to 4.4 (in logarithmic form), and wherein the group R¹ is a hydrocarbyl radical which may comprise aromatic or aliphatic groups, and mixtures thereof, and which may be cyclic or acyclic, straight chained or branched, and optionally substituted with other groups, with the proviso that if no aromatic group is present then R¹ comprises an olefinic double bond, d) ethers of general formula

RO R² having an octanol-water partition coefficient within the range 3.0 to 4.0 (in logarithmic form), and wherein the groups R¹ and R² are independently hydrocarbyl radicals which may comprise aliphatic or aromatic groups, and mixtures thereof, and which may be straight chained or branched and optionally substituted with other groups, with the proviso that at least one of R¹ and R² comprises an olefinic double bond, e) esters of general formula

R'CO. R² having an octanol-water partition coefficient within the range 2.6 to 4.3 (in logarithmic form), and wherein the groups R¹ and R² are independently hydrocarbyl radicals which may comprise saturated aliphatic or aromatic groups, and mixtures thereof, and which may be straight chained or branched, cyclic or acyclic, and optionally substituted with other groups, and f) nitriles of general formula R¹CN having an octanol-water partition coefficient within the range 3.0 to 4.4 (in logarithmic form), and wherein the group R¹ is a hydrocarbyl radical comprising an olefinic double bond, which may comprise aliphatic or aromatic groups, and mixtures thereof, and which may be straight chained or branched, cyclic or acyclic and optionally substituted with other groups.

The invention also provides a deodorant product comprising a perfume composition as defined above.

The invention further provides the use, as a deodorant, of a perfume composition and a deodorant product as defined above. The term 'perfume material (or ingredient)' is herein taken to represent materials which may be acceptably employed within fragrances to provide an odour contribution to the overall hedonic performance of the fragrance. Typically, such materials will be generally recognised as possessing odours in their own right, and will be relatively volatile, and characterised by molecular weights within the range of around 100 to 300 amu.

The concentration of perfume materials or ingredients referred to herein is relative to the total concentration of perfume components present in the composition, ie excludes, for example, the presence of any optional diluent.

The octanol-water partition coefficient (or its common logarithm to base 10, 'logP') is well known in the literature as an indicator of hydrophobicity and water solubility (see Hansch and Leo, Chemical Reviews, 526 to 616, (1971 ), 71; Hansch, Quinlan and Lawrence, J.Organic Chemistry, 347 to 350 (1968), 33). Where such values are not available in the literature they may be measured directly, or approximately estimated using mathematical algorithms. Software providing such estimations are available commercially, for example 'LogP' from Advanced Chemistry Design lnc.(ACD). For the purposes of the present invention the results obtained using ACD software are preferred.'

A perfume composition according to the present invention has the following preferred features, either singly or in any combination;

(i) hydroxylic materials of category (a) which are one or more of Citronellol

Dimethylheptanol

4-(4'-hydroxy-4'-methylpentyl)cyclohex-3-enecarbaldehyde 3-(4'-hydroxy-4'-methylpentyl)cyclohex-3-enecarbaldehyde Tetrahydrolinalol, (ii) aldehydes of category (c) which comprise less than two hydrogen atoms in the position directly adjacent to the formyl functional group, (iii) ethers of category (d) in which R¹ comprises an alicyclic or aromatic ring, and (iv) esters of category (e) in which R¹ or R² comprises an alicyclic or aromatic ring.

In certain instances, it may be that materials are capable of classification into more than one category, for example, 4-(4'-hydroxy-4'-methylpentyl)cyclohex-3-enecarbaldehyde comprises both hydroxyl and formyl functional groups and hence could be a member of category (c) as well as (a). In such cases the material is deemed to be within the first named category, that is, in (a) before (b), in (d) before (e) and so forth. Acetals are considered herein as ethers. With regard to the essential oils, synthetic oils and complex mixtures common within the perfumery business, the above rules must be applied to their individual constituents. Preferred perfumes comprise at least 50%, more preferably at least 60%, and particularly at least 75% by weight of perfume ingredients as described herein. The perfume composition preferably comprises at least 4, more preferably at least 5, and particularly all 6 classes of perfumery ingredients as described herein.

The invention is directed to perfume compositions and to consumer products which provide a deodorant action when applied to the body within a cosmetically acceptable vehicle. Suitable deodorant products include, but are not limited to, deodorants and antiperspirants including different physical forms such as roll ons, gels, sticks, and aerosols, other personal products such as deocolognes, talcum powders, hand creams, lotions , skin and hair conditioners, sunscreens, soaps, shampoos, and shower gels .

The perfumes described herein may also be usefully employed for deodorant properties in other product areas, for example in detergent and household products such as laundry powders, laundry liquids, rinse conditioners, and household cleaning compositions. Perfumes of the inventions may also be incorporated into textiles directly during manufacture using techniques known in the art, to provide long lasting deodorant protection. It is also known in the art to carry or encapsulate perfumes within other materials such as porous solids or polymeric matrices, in order to provide extended lifetimes, and to provide the possibility of triggered release, for example, during perspiration. Such techniques are applicable within the scope of the present invention.

The invention is illustrate by the following examples.

EXAMPLES

Table 1 presents a representative list of perfume materials falling within the above categories, together with comparative examples of commonly used perfume ingredients which do not fall within the categories.

Table 2 presents a perfume composition 'A' failing within the scope of the invention, together with a comparative example 'B' comprising deodorant perfume constructed from the knowledge in the prior documents above, and comprising significant quantities of high boiling low impact perfume materials.

Tables 3 to 5 illustrate the use of perfumes of the invention within deodorant products. Their preparation is well known to those skilled in the art.

Perfumes A and B were tested for long term deodorant action in the underarm roll-on product whose composition is given in Table 5, using an Odour Reduction Value test as generally described in US-A-4278658. The results of this 24 hour deodorant test are given in Table 6, and demonstrate that perfume 'A' provides at least as effective long term deodorancy as the perfume B built on musks and other substantive ingredients.

Table 1

Examples of Ingredient Categorisation

Note: 'ex' = excluded from classification

Table 2

Compositions of perfumes A and B

Note: materials marked 'Q' are available from Quest International.

Table 3 Deodorant stick

Table 4 Deodorant aerosol

Table 5 Roll-ons

Table 6

Results of 24 hr underarm deodorant efficacy test

Average panel score perfume A 1.85

Average panel score perfume B 1.89

Control panel score 2.41

Odour Reduction Value perfume A 0.56

Odour Reduction Value perfume B 0.52

Odour Reduction Value as percentage of control score - perfume A 23.2%

Odour Reduction Value as percentage of control score - perfume B 21.6%

Difference for significance @95% 0.18

The results show that perfume A yields excellent deodorancy effect, whilst having improved hedonic properties.

Claims

1. A perfume composition comprising at least 40% in total by weight of at least three of the following six categories of perfumery ingredients; a) at least 1.0%, preferably at least 5% and generally not more than 50% by weight of the perfume composition comprises one or more hydroxylic materials of general formula

ROH having an octanol-water partition coefficient within the range of 2.5 to 3.6 (in logarithmic form), and wherein the group R¹ is a hydrocarbyl radical containing no more than one olefinic double bond, and comprising aromatic or aliphatic groups, and mixtures thereof, and which may be cyclic or acyclic, straight chained or branched, and optionally substituted with other groups, b) at least 1.0%, preferably at least 5% and generally not more than 30% by weight of the perfume composition of one or more ketones selected from ketones of general formula

R'CO R² having an octanol-water partition coefficient within the range of 3.0 to 4.1 (in logarithmic form), and wherein the groups R¹ and R² are independently hydrocarbyl radicals which may comprise aromatic or aliphatic groups, and mixtures thereof, and may be cyclic or acyclic, straight chained or branched, and optionally substituted with other groups, c) aldehydes of general formula

R'CHO having an octanol-water partition coefficient within the range of 2.0 to 4.4 (in logarithmic form), and wherein the group R is a hydrocarbyl radical which may comprise aromatic or aliphatic groups, and mixtures thereof, and which may be cyclic or acyclic, straight chained or branched, and optionally substituted with other groups, with the proviso that if no aromatic group is present then R¹ comprises an olefinic double bond, d) ethers of general formula

RO R² having an octanol-water partition coefficient within the range 3.0 to 4.0 (in logarithmic form), and wherein the groups R¹ and R² are independently hydrocarbyl radicals which may comprise aliphatic or aromatic groups, and mixtures thereof, and which may be straight chained or branched and optionally substituted with other groups, with the proviso that at least one of R and R² comprises an olefinic double bond, e) esters of general formula

R'C0₂ R² having an octanol-water partition coefficient within the range 2.6 to 4.3 (in logarithmic form), and wherein the groups R¹ and R² are independently hydrocarbyl radicals which may comprise saturated aliphatic or aromatic groups, and mixtures thereof, and which may be straight chained or branched, cyclic or acyclic, and optionally substituted with other groups, and f) nitriles of general formula 5 R¹CN having an octanol-water partition coefficient within the range 3.0 to 4.4 (in logarithmic form), and wherein the group R¹ is a hydrocarbyl radical comprising an olefinic double bond, which may comprise aliphatic or aromatic groups, and mixtures thereof, and ~ which may be straight chained or branched, cyclic or acyclic and optionally substituted 0 with other groups.

2. A perfume composition according to claim 1 wherein the hydroxylic materials of category (a) comprise one or more of the following materials

Citronellol Dimethylheptanol 5 4-(4'-hydroxy-4'-methylpentyl)cyclohex-3-enecarbaldehyde

3-(4'-hydroxy-4'-methylpentyl)cyclohex-3-enecarbaldehyde Tetrahydrolinalol.

3. A perfume composition according to either one of claims 1 and 2 wherein the aldehydes of category (c) comprise less than two hydrogen atoms attached to the carbon 0 atom adjacent to the carbonyl function.

4. A perfume composition according to any one of the preceding claims wherein the ethers of category (d) comprise an alicyclic or aromatic ring within R¹.

5. A perfume composition according to any one of the preceding claims wherein the esters of category (e) comprise an alicyclic or aromatic ring within R¹ or R². 5

6. A perfume composition according to any one of the preceding claims comprising at least 50% by weight of specified ingredients.

7. A perfume composition according to any one of the preceding claims comprising at least 60% by weight of specified ingredients.

8. A perfume composition according to any one of the preceding claims comprising at 30 least 75% by weight of specified ingredients.

9. A deodorant product comprising a perfume composition defined in any one of the preceding claims.

10. A deodorant product according to claim 9 wherein the product is a personal product including shampoos, creams, lotions, conditioners, soaps and talcs.

35 11. A deodorant product according to claim 9 wherein the product is a laundry treatment product including detergents and rinse conditoners.

12. The use, as a deodorant, of a perfume composition defined in any one of claims 1 to 8, and of a deodorant product defined in any one of claims 9 to 11.