JP7252153B2 - Aqueous perfume - Google Patents

Description

The present invention relates to an ethanol-free perfume composition suitable for leave-on cosmetics, which composition is clear, transparent and stable during storage. The present invention is also directed to ethanol-free perfume products obtainable by dilution of ethanol-free perfume formulations in water.

Historically, perfumes have been prepared by dissolving fragrance oils in volatile alcohols, primarily ethanol, or in mixtures of ethanol and water. The industrialization of surfactants and advances in colloid science have made it possible to solubilize fragrances in water by emulsification with surfactants. Emulsions are called microemulsions if they have a particle size of about 140 nm or less. The small size of these microemulsions containing fragrance oils results in clear or almost clear perfume products, not too different in appearance from traditional ethanol-based perfumes. Microemulsions contain physical structures that can be described as swollen micelles, inverse micelles or continuous bilayers. None of these structures are present in conventional ethanol-based perfume products.

A major advantage of water-based perfumes is the reduction of VOCs (volatile organic compounds). Another advantage is the direct perception of the inherent properties of fragrance oils due to the absence of ethanol or ethanol-like alcohols. However, microemulsion water-based products tend to be foamy, sticky, or even skin-irritating due to the presence of surfactants required to solubilize fragrances.

These drawbacks are magnified as the surfactant or perfume content increases. This content is determined by the inherent efficiency of the surfactant system chosen, the difficulty of solubilizing the fragrance oil itself, and the total content of fragrance oil in the final perfume product. In any case, T. J. Lin, Surfactants in Cosmetics, Surfactants Sci. Ser. It was stated that a ratio of surfactant solubilizer system to fragrance oil would be required. Therefore, it is necessary to make microemulsions with low concentrations of skin-compatible surfactants.

US Pat. No. 5,374,614 discloses low VOC microemulsions for perfumery applications with reduced surfactant content. Surfactant systems consist of a nonionic portion and an anionic portion and are also represented in other disclosures in the art such as US Pat. No. 7,655,613.

The nonionic portion in these documents is based on ethoxylated surfactants known for their excellent fragrance solubilizing properties. Both patents disclose long lists of ethoxylated compounds. However, ethoxylated interfaces based on fatty acids, fatty alcohols and even alkylphenols with molecular weights in the range of 400 to 1200 disclosed in US Pat. No. 5,374,614 and no longer used in consumer products. Active agents are known to disrupt stratum corneum lipids. While acceptable for use in many consumer and industrial products and may have functions in addition to fragrance solubilization, these surfactants are less suitable in perfumery products for application to skin or hair. . High molecular weight ethoxylated nonionic surfactants, such as the ethoxylated castor oil material disclosed in US Pat. No. 8,461,099, are very suitable for personal use perfumes.

The anionic surfactants disclosed in these patents are also known for use in many personal cleansing, household, laundry and detergent products in general. Anionic surfactants are known to interact negatively with the corneocytes of the skin, causing irritation, especially if left deposited on the skin, as in perfumery products for personal use. .

Thus, there remains a need for ethanol-free water-based perfume compositions that remain clear and stable over time, while being non-irritating to the skin.

U.S. Pat. No. 5,374,614 U.S. Pat. No. 7,655,613 U.S. Pat. No. 8,461,099

T. J. Lin, Surfactants in Cosmetics, Surfactants Sci. Ser. Vol. 16, (1985), 29-52

The present invention unexpectedly and advantageously addresses all of these needs by incorporating novel specific esters that completely replace the ethanol or anionic materials described as essential in the prior art. provide a solution. It is therefore an object of the present invention to provide novel leave-on ethanol-free water-based perfume compositions which are storage-stable, remain particularly clear and are non-irritating to the skin. .

The present invention is an ethanol-free perfume composition comprising water, a perfume, and an ester, wherein said ester comprises an ethoxylated glyceride derived from a carboxylic acid having 6 to 22 carbon atom moieties. about things.

The present invention also provides a method for the preparation of said ethanol-free perfume composition comprising the steps of:
a. preparing a solution of water and said ester under stirring and mixing until a clear and homogeneous solution is obtained;
b. adding perfume to said solution and mixing until a clear and homogeneous solution is obtained.

The present invention is also directed to the use of said perfume compositions for the preparation of fine perfume compositions or cosmetic or personal cleansing compositions.

The present invention also provides a carboxylic acid derived from a carboxylic acid having 6 to 22 carbon atom moieties for improving the solubility of perfume in water and/or imparting clarity to perfume compositions containing water and perfume. related to the use of esters containing ethoxylated glycerides.

The combination of certain esters, fragrances and water has made it possible to provide clear, transparent, shelf-stable, ethanol-free fragrance compositions that are completely non-irritating to the skin. It is to the benefit of the inventors that this discovery has been made.

In particular, within the meaning of the present invention, the pH of the composition remains stable over time (up to at least 3 weeks, preferably up to 12 weeks) during storage at 5°C or 45°C. Stability is understood to mean that the pH does not vary by more than 1 pH unit under the various storage conditions tested.

Ethanol-Free Compositions In the context of the present invention, ethanol-free perfume compositions are less than 5% by weight, preferably less than 4% by weight, more preferably less than 3% by weight, even more preferably less than 2% by weight, even more preferably less than 2% by weight. Preferred are compositions comprising less than 1% by weight of ethanol, and in a more preferred embodiment, said compositions do not contain ethanol.

Water The perfume composition of the present invention comprises at least 50% by weight water. In one embodiment, the composition comprises 5% to 75% by weight water. In a further embodiment, the composition comprises 10% to 50% water, preferably 15% to 30% water.

Perfume As mentioned above, the alcohol-free compositions of the present invention comprise at least one perfume.

In the context of the present specification, the term "perfume" is understood to mean one or a mixture of olfactory active materials currently used in perfume formulations that provide a pleasant odor. A mixture of perfumes can be referred to as a "perfumed composition". Perfumes can be of natural or synthetic origin. In general fashion, fragrances belong to diverse chemical classes such as terpene carbohydrates, acetate esters, alcohols, aldehydes, ketones, esters, ethers, nitriles, nitrogen or sulfur heterocycles and essential oils of natural or synthetic origin. It is a hydrophobic compound. A more detailed description is not required here, as one skilled in the art is familiar with the ingredients and can select them according to the nature of the flavored product and the desired olfactory effect.

The water solubility of a fragrance is inversely related to the theoretical octanol/water partition coefficient, usually expressed logarithmically as "log P octanol/water" or "log Pow". A lower log Pow value indicates a more water-soluble molecule, while a higher log Pow value indicates a more hydrophobic compound. However, log Pow characterizes fragrances in surfactant-free chemical environments. In the presence of surfactants, log Pow may only partially explain the fragrance intrinsic solubility, which is now dominated by the incorporation of fragrance ingredients into various locations of surfactant micelles. .

In one embodiment, the composition comprises between 1% and 40%, preferentially between 2% and 25% by weight of perfume relative to the total weight of the composition.

Polar Emollient Esters The perfume compositions of the present invention also contain polar emollient esters. Polar emollient esters are defined as amphiphilic polymers within the meaning of the invention. The term amphipathic defines a molecule that contains a water-soluble portion and an oil-soluble portion. Indeed, this class has a strong affinity and may be able to form chemical bonds to polar materials and thus to perfumes.

Accordingly, the present invention relates to ethanol-free perfume compositions, wherein said esters comprise ethoxylated glycerides derived from carboxylic acids having 6 to 22 carbon atom moieties.

In a preferred embodiment, ethoxylated glycerides derived from carboxylic acids having 6 to 22 carbon atoms are represented by formula (I)

［式中、
ｍ、ｎ、およびｌのそれぞれは独立して、０から４０の数字を表し、
ｍとｎとｌの合計は、８から２００、好ましくは９から３０、より好ましくは１５から２５の範囲内にあり、
Ｂ１、Ｂ２、およびＢ３は独立して、Ｈまたは６から２２個の炭素原子を有するアシル残基を表すが、但し、Ｂ１、Ｂ２、およびＢ３の少なくとも１つは、６から２２個の炭素原子を有するアシル残基である］
の化合物を含む。

[In the formula,
each of m, n, and l independently represents a number from 0 to 40;
the sum of m, n and l is in the range of 8 to 200, preferably 9 to 30, more preferably 15 to 25;
B1, B2, and B3 independently represent H or an acyl residue having from 6 to 22 carbon atoms, provided that at least one of B1, B2, and B3 has from 6 to 22 carbon atoms. is an acyl residue having]
containing compounds of

In particular, ethoxylated glycerides are
(i) compounds of formula (I) wherein each of B1, B2, and B3 independently represents an acyl group having from 6 to 22 carbon atoms;
(ii) compounds of formula (I) wherein two of B1, B2 and B3 independently represent an acyl group having from 6 to 22 carbon atoms and the remainder represent H;
(iii) compounds of formula (I) wherein one of B1, B2 and B3 represents an acyl group having from 6 to 22 carbon atoms and the remainder represent H;
(iv) compounds of formula (I), wherein each of B1, B2, and B3 represents H, wherein the weight ratio of compounds (i)/(ii)/(iii) is from 46 to 90/9 to 35/ It is preferably used as a mixture of compounds of formula (I) above which are 1 to 15.

These compounds are preferably prepared by the reaction between triglycerides and glycerides and ethylene oxide.

Acyl groups having 6 to 22 carbon atoms, preferably 12 to 18 carbon atoms, are preferably derived from natural fats or oils or synthetic glycerides. Preferred fats and oils (oils) include vegetable palm kernel oil, sunflower oil, rapeseed oil, castor oil, olive oil, soybean oil, and animal fats such as tallow, bone oil, fish oil, hydrogenated oils and semi-solids thereof. Hydrogenated oils, as well as mixtures thereof. Particularly preferred are acyl groups derived from tallow such as coconut oil, palm oil and beef tallow.

Preferred ethoxylated glycerides are available from Kao S.T. A. Glycereth-17 cocoate marketed under the trade name LEVENOL C-201B by the Company. This is the compound of formula (I) above wherein the sum of m, n and l is 17 and either one or two groups of B1 and B2 are acyl groups derived from coconut oil. or the ester comprises glycereth-20 cocoate, wherein the sum of m and n and l is 20 and either one or two groups of B1 and B2 are derived from coconut oil A mixture of compounds of formula (I), which are acyl groups.

Another preferred ethoxylated glyceride is glycereth-20 cocoate. This is a mixture of compounds of formula (I) above wherein the sum of m, n and p is 20 and either one or two groups of B1 and B2 are acyl groups derived from coconut oil. is.

In one embodiment, the perfume to ester weight ratio is comprised between 1:1.1 and 1:16 (including 1:1.1 and 1:16).

In one embodiment, the weight ratio of ester to water is comprised between 3:1 and 0.33:1 (including 3:1 and 0.33:1).

In a preferred embodiment, the amount of perfume in the composition ranges from 2% to 40% and the amount of ester ranges from 20% to 60% by weight, relative to the total weight of the composition. and the amount of water ranges from 15% to 75% by weight.

In certain embodiments of the invention, the composition may preferably consist of water, perfume, and esters including ethoxylated glycerides derived from carboxylic acids having 6 to 22 carbon atom moieties.

Alkane-1,2-diol The alcohol-free perfume composition of the present invention optionally further comprises an alkane-1,2-, preferably having 3 to 10 carbon atoms, preferably 3 to 6 carbon atoms. It may contain a diol.

A preferred 1,2-alkanediol is pentylene glycol (INCI name), sold under the name HYDROLITE® 5GREEN by Symrise.

Another preferred 1,2-alkanediol is caprylyl glycol (INCI name), sold under the name HYDROLITE® CG by Symrise.

Alkanediols such as glycols provide cosmetic compositions with improved volatilization properties by thinning the composition.

The 1,2-alkanediols may be present in the composition in amounts ranging from 0.1% to 20% by weight relative to the total weight of the composition.

Additional Ingredients According to certain embodiments of the present invention, alcohol-free perfume compositions provide certain additional benefits, such as colorants, pigments, preservatives and/or bactericidal agents. One or more additional ingredients may optionally be further included. Such additional ingredients are compounds known to those skilled in the art. Such additional ingredients may be synthetic or natural.

Method of Preparation of Perfume Compositions Perfume compositions according to the present invention are prepared by mixing water and esters of the present invention, for example by simple mixing of all ingredients, for example by manual stirring or the use of a mechanical stirrer if desired. It can be prepared by forming a clear, homogeneous solution, and finally, adding perfume to the solution and mixing to form a clear, homogeneous solution.

So-called "fine perfumery" is defined as the art of creating fragrances resulting from the combination of various essences, natural or artificial. The goal is to design pleasant and unpleasant odors.

The following examples are used to illustrate the invention without in any way indicating a limiting character. In these examples, component amounts are given as weight percentages relative to the total weight of the composition.

[Example 1]
- 60% esters,
- 20% perfume, and - 20% water
A series of ethanol-free perfume compositions were prepared, comprising:

The 14 solutions are esters containing ethoxylated glycerides derived from carboxylic acids having 6 to 22 carbon atom moieties according to the invention or esters exhibiting similar chemical structures but outside the scope of the invention. prepared using either

As can be seen from the results shown in the table above, the compositions of the present invention containing esters with ethoxylated glycerides derived from carboxylic acids having 6 to 22 carbon atom moieties are clear and transparent solutions. while comparative compositions containing various esters gave opaque solutions.

[Example 2]
Two additional ethanol-free perfume compositions according to the invention (compositions 15 and 16) were prepared having the following compositions.

Compositions 2, 15, and 16 are all transparent.

In addition, the long-term stability of these three compositions according to the invention was also evaluated by measuring the pH of the compositions after storage.

The pH of the composition according to the invention remains stable over time during storage. The variations in pH under the various storage conditions tested never exceed 1 pH unit.

[Example 3]
Two additional ethanol-free perfume compositions according to the invention (compositions 17 and 18) were prepared having the following compositions.

Compositions 17 and 18 are both transparent.

[Example 4]
One further ethanol-free perfume composition according to the invention (Composition 19) was prepared having the following composition.

［式中、
ｍ、ｎ、およびｌのそれぞれは独立して、０から４０の数字を表し、
ｍとｎとｌの合計は、８から２００、好ましくは９から３０、より好ましくは１５から２５の範囲内にあり、
Ｂ１、Ｂ２、およびＢ３は独立して、Ｈまたは６から２２個の炭素原子を有するアシル残基を表すが、但し、Ｂ１、Ｂ２、およびＢ３の少なくとも１つは、６から２２個の炭素原子を有するアシル残基である］
の化合物を含む、前記［１］に記載の組成物。
［３］前記エトキシル化グリセリドが、
（ｉ）Ｂ１、Ｂ２、およびＢ３のそれぞれが独立して、６から２２個の炭素原子を有するアシル基を表す、式（Ｉ）の化合物、
（ｉｉ）Ｂ１、Ｂ２、およびＢ３の２つが独立して、６から２２個の炭素原子を有するアシル基を表し、残りがＨを表す、式（Ｉ）の化合物、
（ｉｉｉ）Ｂ１、Ｂ２、およびＢ３の１つが、６から２２個の炭素原子を有するアシル基を表し、残りがＨを表す、式（Ｉ）の化合物、
（ｉｖ）Ｂ１、Ｂ２、およびＢ３のそれぞれがＨを表す、式（Ｉ）の化合物
を含み、化合物（ｉ）／（ｉｉ）／（ｉｉｉ）の重量比が、４６から９０／９から３５／１から１５である、前記式（Ｉ）の化合物の混合物である、前記［２］に記載の組成物。
［４］６から２２個の炭素原子、好ましくは１２から１８個の炭素原子を有する前記アシル基が、天然の脂肪もしくは油または合成グリセリド、好ましくはココナッツ油から誘導される、前記［１］から［３］のいずれか一項に記載の組成物。
［５］前記エステルが、ｍとｎとｌの合計が１７であり、Ｂ１およびＢ２の１つの基または２つの基のいずれかが、ココナッツ油から誘導されるアシル基である式（Ｉ）の化合物の混合物であるグリセレス－１７ココエートを含み、または前記エステルが、ｍとｎとｌの合計が２０であり、Ｂ１およびＢ２の１つの基または２つの基のいずれかが、ココナッツ油から誘導されるアシル基である式（Ｉ）の化合物の混合物であるグリセレス－２０ココエートを含む、前記［１］から［４］のいずれか一項に記載の組成物。
［６］前記エステル対前記水の重量比が、３：１から０．３３：１の範囲である、前記［１］から［５］のいずれかに記載の組成物。
［７］３から１０個の炭素原子、好ましくは３から６個の炭素原子を有するアルカン－１，２－ジオールを含む、前記［１］から［６］のいずれか一項に記載の組成物。
［８］前記組成物の総重量に対して、１重量％から４０重量％、好ましくは２重量％から２５重量％の香料を含む、前記［１］から［７］のいずれか一項に記載の組成物。
［９］香料対エステルの重量比が、１：１．１から１：１６の範囲にある、前記［１］から［８］のいずれか一項に記載の組成物。
［１０］前記組成物の総重量に対して、香料の量が２重量％から４０重量％の範囲にあり、エステルの量が２０重量％から６０重量％の範囲にあり、水の量が１５重量％から７５重量％の範囲にある、前記［１］から［９］のいずれか一項に記載の組成物。
［１１］５重量％未満、好ましくは４重量％未満、より好ましくは３重量％未満、さらにより好ましくは２重量％未満、さらにより好ましくは１重量％未満のエタノールを含み、より好ましい実施形態において、エタノールを含有しない、前記［１］から［１０］のいずれか一項に記載の組成物。
［１２］着色剤、顔料、保存剤および／または殺菌剤を含む、前記［１］から［１１］のいずれか一項に記載の組成物。
［１３］水、香料および６から２２個の炭素原子部分を有するカルボン酸から誘導されるエトキシル化グリセリドを含むエステルからなる、前記［１］から［１２］のいずれか一項に記載の組成物。
［１４］前記［１］から［１３］のいずれか一項に記載のエタノール非含有香料組成物の調製のための方法であって、以下のステップ：
ａ．攪拌下、水および前記エステルの溶液を調製し、明澄で均一な溶液が得られるまで混合するステップと、
ｂ．前記溶液に前記香料を加え、明澄で均一な溶液が得られるまで混合するステップと
を含む、方法。
［１５］ファインパフューム組成物、または化粧料組成物またはパーソナルクレンジング組成物の調製のための、前記［１］から［１３］に記載の香料組成物の使用。
［１６］水への香料の溶解度を改善するための、ならびに／または水および香料を含む香料組成物に透明性を与えるための、６から２２個の炭素原子部分を有するカルボン酸から誘導されるエトキシル化グリセリドを含むエステルの使用。 Composition 19 is transparent and exhibits improved volatilization.
It should be noted that the present invention includes the following embodiments.
[1] An ethanol-free perfume composition comprising water, a perfume, and an ester, wherein said ester comprises an ethoxylated glyceride derived from a carboxylic acid having 6 to 22 carbon atom moieties. .
[2] said ethoxylated glyceride derived from a carboxylic acid having 6 to 22 carbon atoms is represented by formula (I)

[In the formula,
each of m, n, and l independently represents a number from 0 to 40;
the sum of m, n and l is in the range of 8 to 200, preferably 9 to 30, more preferably 15 to 25;
B1, B2, and B3 independently represent H or an acyl residue having from 6 to 22 carbon atoms, provided that at least one of B1, B2, and B3 has from 6 to 22 carbon atoms. is an acyl residue having]
The composition according to [1] above, comprising the compound of
[3] The ethoxylated glyceride is
(i) compounds of formula (I) wherein each of B1, B2, and B3 independently represents an acyl group having from 6 to 22 carbon atoms;
(ii) compounds of formula (I) wherein two of B1, B2 and B3 independently represent an acyl group having from 6 to 22 carbon atoms and the remainder represent H;
(iii) compounds of formula (I) wherein one of B1, B2 and B3 represents an acyl group having from 6 to 22 carbon atoms and the remainder represent H;
(iv) compounds of formula (I), wherein each of B1, B2, and B3 represents H;
wherein the weight ratio of compounds (i)/(ii)/(iii) is from 46 to 90/9 to 35/1 to 15, wherein the mixture of compounds of formula (I) [2] The composition according to .
[4] from [1] above, wherein said acyl group having 6 to 22 carbon atoms, preferably 12 to 18 carbon atoms, is derived from a natural fat or oil or a synthetic glyceride, preferably coconut oil; The composition according to any one of [3].
[5] the ester of formula (I) wherein the sum of m, n and l is 17 and either one or two groups of B1 and B2 are acyl groups derived from coconut oil; Glycereth-17 cocoate, which is a mixture of compounds, or said ester wherein the sum of m and n and l is 20 and either one or two groups of B1 and B2 are derived from coconut oil The composition according to any one of [1] to [4] above, comprising glycereth-20 cocoate, which is a mixture of compounds of formula (I) that are acyl groups.
[6] The composition of any one of [1] to [5], wherein the weight ratio of said ester to said water ranges from 3:1 to 0.33:1.
[7] The composition according to any one of [1] to [6] above, comprising an alkane-1,2-diol having 3 to 10 carbon atoms, preferably 3 to 6 carbon atoms. .
[8] Any one of the above [1] to [7], comprising 1% to 40% by weight, preferably 2% to 25% by weight of perfume relative to the total weight of the composition. composition.
[9] The composition of any one of [1] to [8], wherein the weight ratio of perfume to ester is in the range of 1:1.1 to 1:16.
[10] Based on the total weight of the composition, the amount of perfume is in the range of 2% to 40% by weight, the amount of ester is in the range of 20% to 60% by weight, and the amount of water is 15% by weight. The composition according to any one of the above [1] to [9], which is in the range of weight % to 75 weight %.
[11] In a more preferred embodiment, comprising less than 5 wt%, preferably less than 4 wt%, more preferably less than 3 wt%, even more preferably less than 2 wt%, even more preferably less than 1 wt% ethanol , The composition according to any one of the above [1] to [10], which does not contain ethanol.
[12] The composition according to any one of [1] to [11] above, which contains a coloring agent, a pigment, a preservative and/or a bactericide.
[13] The composition according to any one of the above [1] to [12], consisting of water, perfume and an ester comprising an ethoxylated glyceride derived from a carboxylic acid having 6 to 22 carbon atom moieties. .
[14] A method for preparing the ethanol-free perfume composition of any one of [1] to [13] above, comprising the steps of:
a. preparing a solution of water and said ester under stirring and mixing until a clear and homogeneous solution is obtained;
b. adding said perfume to said solution and mixing until a clear and homogeneous solution is obtained;
A method, including
[15] Use of the perfume composition according to the above [1] to [13] for preparing a fine perfume composition, a cosmetic composition or a personal cleansing composition.
[16] derived from a carboxylic acid having 6 to 22 carbon atom moieties for improving the solubility of the perfume in water and/or imparting clarity to a perfume composition comprising water and perfume Use of esters containing ethoxylated glycerides.

Claims (9)

An ethanol-free perfume composition comprising water, a perfume, and an ester,
said ester comprises glycereth-17 cocoate or glycereth-20 cocoate;
The amount of ethanol is less than 5% by weight, the amount of perfume is in the range of 1% to 40% by weight, and the amount of esters is in the range of 20% to 60% by weight, relative to the total weight of the composition. , wherein the amount of water ranges from 15% to 75% by weight. 2. The composition of claim 1, wherein the weight ratio of said ester to said water ranges from 3:1 to 0.33:1. A composition according to claim 1 or 2, comprising an alkane-1,2-diol having 3 to 10 carbon atoms. 4. A composition according to any preceding claim, wherein the weight ratio of perfume to ester ranges from 1:1.1 to 1:16. 5. The composition according to any one of claims 1 to 4, comprising coloring agents, pigments, preservatives and/or bactericides. An ethanol-free perfume composition comprising water, a perfume, and an ester,
said ester comprises glycereth-17 cocoate or glycereth-20 cocoate;
The amount of ethanol is less than 5% by weight, the amount of perfume is in the range of 1% to 40% by weight, and the amount of esters is in the range of 20% to 60% by weight, relative to the total weight of the composition. , wherein the amount of water ranges from 15% to 75% by weight . 7. A method for the preparation of an ethanol-free perfume composition according to any one of claims 1 to 6, comprising the steps of:
a. preparing a solution of water and said ester under stirring and mixing until a clear and homogeneous solution is obtained;
b. adding said perfume to said solution and mixing until a clear and homogeneous solution is obtained. 7. Use of a perfume composition according to any one of claims 1 to 6 for the preparation of fine perfume compositions or cosmetic or personal cleansing compositions. Ethanol-free perfume composition according to any one of claims 1 to 6 for improving the solubility of perfume in water and/or for imparting clarity to a perfume composition comprising water and perfume Use of an ester comprising glycereth-17 cocoate or glycereth-20 cocoate in