WO2016008747A1

WO2016008747A1 - A use of isosorbide monooleate

Info

Publication number: WO2016008747A1
Application number: PCT/EP2015/065297
Authority: WO
Inventors: Claudia STOER; Claus Nieendick; Markus WEISSENEGGER; Daniela Prinz; Mirella WINZEK; Jennifer SCHOSS; Markus Dierker; Norbert Boyxen; Ute Griesbach; Werner Seipel; Werner Mauer
Original assignee: Basf Se
Priority date: 2014-07-16
Filing date: 2015-07-06
Publication date: 2016-01-21

Abstract

The present invention relates to the use of isosorbide monooleate in a cosmetic composition for improving the sensory impression brought about by the cosmetic composition when applied to human skin or hair, preferably when applied to human skin. Furthermore it relates to the use of isosorbide monooleate in a cosmetic composition for bringing about effects underlying or contributing to the improvement of the sensory impression, i. e. easy distributability of the cosmetic composition on human skin or hair, creamy foam obtained from the cosmetic composition, smooth skin or hair and/or skin or hair that is not dry.

Description

A Use of Isosorbide Monooleate

Cosmetic compositions, detergents and cleansers comprising isosorbide monooleate, i. e. the monoester of isosorbide and oleic acid, are known. Isosorbide monooleate has many advantageous properties which are the reason why isosorbide monooleate is used in cosmetic compositions, in detergents and in cleansers.

WO 2010/1 15565 (EP 2 239 315) discloses detergents and cleansers comprising isosorbide monoesters. In the example section a composition comprising 1 % by weight isosorbide monoester and 3 % by weight coco glucoside is disclosed.

WO 2013/041388 discloses cosmetic compositions comprising isosorbide monooleate, specifically disclosed is a composition comprising 1 % by weight isosorbide monooleate and 1.5 % by weight coco glucoside (Figure 4). This composition has good foaming performance.

European patent application no. 14154978 filed on February 13, 2014 (BASF internal file no. PF 75368) discloses a microemulsion comprising isosorbide monooleate and caprylyl/capryl glucoside and lauryl glucoside. It is disclosed that isosorbide monooleate which is used commercially is generally a mixture of monoester, diester, isosorbide and fatty acids, mainly oleic acid.

There is a constant need to improve the sensory impression brought about by a cosmetic composition when applied to human skin or hair, preferably when applied to human skin.

The problem underlying the present invention is therefore to improve the sensory impression brought about by a cosmetic composition when applied to human skin or hair, preferably when applied to human skin.

The improvement of the sensory impression brought about by a cosmetic composition when applied to human skin or hair, preferably when applied to human skin, is an objective effect that can be determined, e. g. by trained test persons (volunteers) in double blind studies, i. e. the improvement of the sensory impression is not a subjective notion that differs from one individual to another but a statistically relevant difference that can be determined reliably and objectively. The improvement of the sensory impression can comprise several aspects, e. g. easiness of distribution of the cosmetic composition on the skin or hair. Then, these aspects as such can also represent an effect which can be objectively determined independently from the overall improvement of the sensory impression. In the example chosen, easiness of distribution is an independent effect.

Improvement in the context of the present invention means an improvement achieved when adding isosorbide monooleate to a cosmetic formulation that apart from this addition stays essentially the same, preferably stays the same. Accordingly, relative terms like high, low, good and easy are to be understood in the context of the comparison of two products, one with and the other without isosorbide monooleate.

According to the present invention sensory impression means the perception of the whole product during application, wherein all sensory properties are taken into account, including visual and tactile evaluations.

A solution of the problem underlying the present invention and therefore a subject of the present invention is the use of isosorbide monooleate in a cosmetic composition for improving the sensory impression brought about by the cosmetic composition when applied to human skin or hair, preferably when applied to human skin. This use is called the use according to the present invention

One embodiment of the use according to the present invention is the use according to the present invention present invention, wherein the improvement of the sensory impression comprises easy distribution of the cosmetic composition on the skin or hair.

According to the present invention easy distribution means the spreading properties on the skin/hair during application. Easy distribution means that the force which is needed to disperse the shower gel or shampoo on the skin/hair is low, applying the product is easy. No dragging of the product on the skin/hair is necessary which would cause bad feeling, because this could hurt by stretching the skin or pulling on hair.

One embodiment of the use according to the present invention is the use according to the present invention present invention, wherein the improvement of the sensory impression comprises good creaminess and/or good acceptance of foam obtained from the cosmetic composition.

According to the present invention good creaminess of foam means that small bubbles and a cream-like foam, as preferred by consumers, is perceived by the test persons of a testing panel. The generated foam is compact and long lasting and feels like whipped cream. This soft foam is associated with an appreciative cover.

According to the present invention good acceptance of foam means that the preference for this foam is very high, the volunteers like this foam best. One embodiment of the use according to the present invention is the use according to the present invention present invention, wherein the improvement of the sensory impression comprises high smoothness and/or little dryness of the skin or hair.

According to the present invention smoothness means that the skin/hair feels smooth, the fingers are gliding easily over the skin/hair.

According to the present invention dryness means that the skin/hair feels dry, the skin/hair is rough, strawy (hair). It is a feeling of tightness. The skin flakes.

One embodiment of the use according to the present invention is the use according to the present invention present invention, wherein the improvement of the sensory impression comprises good acceptance of the skinfeel.

According to the present invention good acceptance of the skinfeel means the reception of a nice skin feeling. The volunteers favor this product in comparison to another product tested.

A further subject of the present invention is the use of isosorbide monooleate in a cosmetic composition for bringing about easy distributability of the cosmetic composition on human skin or hair.

A further subject of the present invention is the use of isosorbide monooleate in a cosmetic composition for bringing about creamy foam obtained from the cosmetic composition.

A further subject of the present invention is the use of isosorbide monooleate in a cosmetic composition for bringing about smooth human skin or hair and/or for bringing about human skin or hair that is not dry.

One embodiment of the present invention is the use according to the present invention (i. e. according to any use which is a subject of the present invention or according to any of the embodiments described in the previous paragraphs), wherein the cosmetic composition comprises isosorbide monooleate in an amount of 0.2 to 3 % by weight, preferably 0.4 to 2.5 % by weight, more preferably 0.5 to 2 % by weight.

One embodiment of the present invention is the use according to the present invention (i. e. according to any use which is a subject of the present invention or according to any of the embodiments described in the previous paragraphs), wherein the cosmetic composition comprises a surfactant which is different from isosorbide monooleate selected from the group consisting of an anionic surfactant, a cationic surfactant, a nonionic surfactant an amphoteric or zwitterionic surfactant and mixtures thereof, preferably in an amount of 2 to 40 % by weight, more preferably 5 to 30 % by weight, more preferably 10 to 20 % by weight.

One embodiment of the present invention is the use according to the present invention (i. e. according to any use which is a subject of the present invention or according to any of the embodiments described in the previous paragraphs), wherein the cosmetic composition further comprises one or more cosmetically acceptable ingredients.

One embodiment of the present invention is the use according to the present invention (i. e. according to any use which is a subject of the present invention or according to any of the embodiments described in the previous paragraphs), wherein the cosmetic composition is selected from the group consisting of a shampoo, a shower gel, a body-wash composition and a skin or hair conditioner.

One embodiment of the present invention is the use according to the present invention (i. e. according to any use which is a subject of the present invention or according to any of the embodiments described in the previous paragraphs), wherein the isosorbide monooleate is a mixture comprising pure isosorbide monooleate in an amount of 65 - 95 % by weight, preferably 65 - 85 % by weight, more preferably 65 - 75 % by weight.

One embodiment of the present invention is the use according to the present invention (i. e. according to any use which is a subject of the present invention or according to any of the embodiments described in the previous paragraphs), wherein the fatty acid moieties in the pure isosorbide monooleate comprise more than 65 % by weight, preferably more than 70 % by weight, more preferably more than 75 % by weight, oleic acid moieties.

One embodiment of the present invention is the use according to the present invention (i. e. according to any use which is a subject of the present invention or according to any of the embodiments described in the previous paragraphs), wherein the use is realized in a process comprising contacting human skin or hair with a cosmetic composition comprising isosorbide monooleate and rinsing off the cosmetic composition comprising isosorbide monooleate with water.

Isosorbide monooleate can be made as disclosed in WO 2010/1 15565 or by other known esterification methods.

Cosmetic compositions comprising isosorbide monooleate can be made as disclosed in WO 2013/041388 or by other known methods for making cosmetic compositions.

Isosorbide monooleate according to the present invention generally is a mixture comprising (pure) isosorbide monooleate as major component and additionally isosorbide dioleate, oleic acid and isosorbide. In this mixture the oleic acid, which is generally obtained from plants, also is a mixture comprising oleic acid as major component and other fatty acids in minor amounts. The term pure isosorbide monooleate means the monoester of isosorbide with a fatty acid mixture comprising oleic acid as major component. Here, major component means more than 65 % by weight, preferably more than 70 % by weight, more preferably more than 75 % by weight, oleic acid. Therefore, in one embodiment of the present invention the isosorbide monooleate is a mixture comprising pure isosorbide monooleate in an amount of 65 - 95 % by weight, preferably 70 - 85 % by weight, more preferably 75 - 80 % by weight. The amounts in % by weight can be determined by gas chromatography (GC) with appropriate calibration. In this pure isosorbide monooleate the fatty acid moieties comprise more than 65 % by weight, preferably more than 70 % by weight, more preferably more than 75 % by weight, oleic acid moieties. The amounts in % by weight can be determined by gas chromatography (GC) with appropriate calibration.

Cosmetic compositions are to be understood here as meaning all compositions which are exclusively or primarily intended to be used externally on the human body or in its oral cavity for cleaning, care, protection, maintaining a good condition, perfuming, changing the appearance or for the purposes of influencing body odor.

The cosmetic compositions according to the invention can be in particular formulations for bodycare, e.g. a body milk, creams, lotions, sprayable emulsions, products for eliminating body odor etc. They can be surfactant-containing formulations such as e.g. foam and shower baths, hair shampoos and care rinses. Depending on the intended application, the cosmetic formulations can comprise a series of further auxiliaries and additives, for example surfactants, oil bodies, emulsifiers, pearlescent waxes, consistency regulators, thickeners, superfatting agents, stabilizers, polymers, fats, waxes, lecithins, phospholipids, biogenic active ingredients, UV light protection factors, antioxidants, deodorants, antiperspirants, antidandruff agents, film formers, swelling agents, insect repellents, self-tanning agents, tyrosine inhibitors (depigmentation agents), hydrotropes, solubilizers, preservatives, perfume oils, dyes etc., which are listed below by way of example.

Surfactants Surface-active substances which may be present are anionic, nonionic, cationic and/or amphoteric or zwitterionic surfactants. In surfactant-containing cosmetic preparations, for example shower gels, foam baths, shampoos etc., preferably at least one anionic surfactant is present. The fraction of surfactants here is usually about 1 to 30, preferably 5 to 25 and in particular 10 to 20% by weight.

Typical examples of anionic surfactants are soaps, alkylbenzenesulfonat.es, alkanesulfonates, olefinsulfonates, alkyl ether sulfonates, glycerol ether sulfonates, a-methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and salts thereof, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, N-acylamino acids, such as, for example, acyl lactylates, acyl tartrates, acyl glutamates and acyl aspartates, alkyl oligoglycoside sulfates, protein fatty acid condensates (in particular wheat-based vegetable products) and alkyl (ether) phosphates. If the anionic surfactants contain polyglycol ether chains, these can have a conventional homolog distribution, but preferably have a narrowed homolog distribution. Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers and mixed formals, optionally partially oxidized alk(en)yl oligoglycosides and glucuronic acid derivatives, fatty acid N-alkylglucamides, protein hydrolyzates (in particular wheat-based vegetable products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, these can have a conventional homolog distribution, but preferably have a narrowed homolog distribution. Typical examples of cationic surfactants are quaternary ammonium compounds, such as, for example, dimethyldistearylammonium chloride, and ester quats, in particular quaternized fatty acid trialkanolamine ester salts. Typical examples of amphoteric or zwitterionic surfactants are alkylbetaines, alkylamidobetaines, aminopropionates, aminoglycinates, imidazoliniumbetaines and sulfobetaines. Said surfactants are exclusively known compounds. As regards structure and preparation of these substances, reference may be made to relevant review works in this field. Typical examples of particularly suitable mild, i.e. particularly skin-compatible, surfacatants are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and/or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid glutamates, a-olefinsulfonates, ether carboxylic acids, alkyl oligoglucosides, fatty acid glucamides, alkylamidobetaines, amphoacetals and/or protein fatty acid condensates, the latter preferably based on wheat proteins.

Oil bodies: Bodycare compositions, such as creams, lotions and milks, usually comprise oil bodies and emollients. Suitable oil bodies and emollients are disclosed in WO 2013/041388.

Fats and waxes: Fats and waxes are added to bodycare products as care substances and also in order to increase the consistency of the cosmetics. Suitable fats and waxes are disclosed in WO 2013/041388.

Suitable thickeners are disclosed in WO 2013/041388.

UV light protection factors are to be understood as meaning, for example, organic substances (light protection filters) that are present in liquid or crystalline form at room temperature and which are able to absorb ultraviolet rays and release the absorbed energy again in the form of longer-wave radiation, e.g. heat. Suitable UV light protection factors are disclosed in WO 2013/041388.

Biogenic active ingredients are to be understood as meaning, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, (deoxy)ribonucleic acid and fragmentation products thereof, β-glucans, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts, such as e.g. prune extract, bambara nut extract and vitamin complexes.

Deodorizing active ingredients counteract, mask or eliminate body odors. Suitable deodorizing active ingredients are disclosed in WO 2013/041388.

Suitable insect repellents, self-tanning agents, tyrosine inhibitors, preservatives, perfumes, pearlescent waxes, superfatting agents, stabilizers, hydrotropes, which can be present in the composition according to the present invention are disclosed in WO 2013/041388.

Examples

A shower gel formulation containing isosorbide monooleate (formulation B) was compared to a so-called placebo formulation (formulation A) in a sensory assessment by trained volunteers. Both formulations were compared directly using well defined criteria in a double blind test. The test procedure, the same as described in the experimental section of WO 2013/007473, was the following.

The two formulations were tested in a forearm test by test subjects. A comparison was carried out between Formulation A and B. For this, the formulations were dripped onto the wetted forearm of the test subjects in a concentration of 10 g/l and left there for 30 seconds. The arm was then rinsed with water for 5 seconds. The test subjects were asked to assess their impressions for the areas "easiness of distribution", "good creaminess of foam", "good acceptance of foam", "smoothness (after 8 min after rinse-off)", "dryness (after 8 min after rinse-off)" and "acceptance of the skinfeel". The two formulations were tested against one another.

To calculate the statistical significance of the pair-wise comparison the Wilcoxon test was used. A scale was applied from -1 (worse), -0.5 (slightly worse), 0 (equal), + 0.5 (slightly better) to + 1 (better). Only statistically significant differences are mentioned. The following formulations were used.

Formulation B showed several significant advantages versus formulation A:

^■ easier distribution: + 0.5

^■ better creaminess of foam: + 0.5

^■ better acceptance of foam: + 0.5

^■ more smoothness (after 8 min after rinse-off): + 0.5

^■ less dryness (after 8 min after rinse-off): + 0.5

^■ higher acceptance of the skinfeel: + 0.5 It could be shown that isosorbide monooleate improves the skin feeling with respect to the various aspects tested, which means that in improves the sensory impression, when used in a cosmetic formulation.

Claims

1. The use of isosorbide monooleate in a cosmetic composition for improving the sensory impression brought about by the cosmetic composition when applied to human skin or hair, preferably when applied to human skin.

2. The use according to claim 1 , wherein the improvement of the sensory impression comprises easy distribution of the cosmetic composition on the skin or hair.

3. The use according to claim 1 , wherein the improvement of the sensory impression comprises good creaminess and/or good acceptance of foam obtained from the cosmetic composition.

4. The use according to claim 1 , wherein the improvement of the sensory impression comprises high smoothness and/or little dryness of the skin or hair.

5. The use according to claim 1 , wherein the improvement of the sensory impression comprises good acceptance of the skinfeel.

6. The use of isosorbide monooleate in a cosmetic composition for bringing about easy distributability of the cosmetic composition on human skin or hair.

7. The use of isosorbide monooleate in a cosmetic composition for bringing about creamy foam obtained from the cosmetic composition.

8. The use of isosorbide monooleate in a cosmetic composition for bringing about smooth human skin or hair and/or for bringing about human skin or hair that is not dry.

9. The use according to any of claims 1 to 8, wherein the cosmetic composition comprises isosorbide monooleate in an amount of 0.2 to 3 % by weight, preferably 0.4 to 2.5 % by weight, more preferably 0.5 to 2 % by weight.

10. The use according to any of claims 1 to 9, wherein the cosmetic composition comprises a surfactant which is different from isosorbide monooleate selected from the group consisting of an anionic surfactant, a cationic surfactant, a nonionic surfactant an amphoteric or zwitterionic surfactant and mixtures thereof, preferably in an amount of 2 to 40 % by weight, more preferably 5 to 30 % by weight, more preferably 10 to 20 % by weight.

1 1. The use according to any of claims 1 to 10, wherein the cosmetic composition further comprises one or more cosmetically acceptable ingredients.

12. The use according to any of claims 1 to 1 1 , wherein the cosmetic composition is selected from the group consisting of a shampoo, a shower gel, a body-wash composition and a skin or hair conditioner.

13. The use according to any of claims 1 to 12, wherein the isosorbide monooleate is a mixture comprising pure isosorbide monooleate in an amount of 65 - 95 % by weight, preferably 65 - 85 % by weight, more preferably 65 - 75 % by weight.

14. The use according to claim 13, wherein the fatty acid moieties in the pure isosorbide monooleate comprise more than 65 % by weight, preferably more than 70 % by weight, more preferably more than 75 % by weight, oleic acid moieties.

15. The use according to any of claims 1 to 14, wherein the use is realized in a process comprising

contacting human skin or hair with a cosmetic composition comprising isosorbide monooleate and

rinsing off the cosmetic composition comprising isosorbide monooleate with water.