WO2025224176A1

WO2025224176A1 - Conditioning composition for keratin fibers

Info

Publication number: WO2025224176A1
Application number: PCT/EP2025/061073
Authority: WO
Inventors: Sabine Schmid; Petra Lobmueller; Dorina SCHMUELLING
Original assignee: Kao Germany GmbH
Current assignee: Kao Germany GmbH
Priority date: 2024-04-24
Filing date: 2025-04-23
Publication date: 2025-10-30
Anticipated expiration: 2026-10-24

Abstract

An aqueous-alcoholic composition for keratin fibers especially for human hair characterized in that it comprises: a) one or more glyceryl ether(s), b) one or more polyol(s) other than the glyceryl ether, c) one or more amine and/or quaternary ammonium surfactant(s), d) one or more fatty alcohol(s), wherein the composition comprises water in the range of more than 10% by weight to 35% by weight or less, preferably in the range of 12.5% by weight to 25% by weight, more preferably in the range of 15% by weight to 25% by weight, calculated to the total weight of the composition, wherein the composition comprises one or more polyol(s) according to group b) at a concentration of at least 40% by weight, calculated to the total weight of the composition, wherein the one or more fatty alcohol according to group d) is selected from the compounds according to the following general structure R₁₁-OH, wherein R₁₁ is a saturated or unsaturated, branched, or straight alkyl chain with C₁₀-C₂₄ atoms.

Description

CONDITIONING COMPOSITION FOR KERATIN FIBERS

Field of the invention

The present invention relates to a care composition for keratin fibers, especially human hair, based on a low amount of water, polyols, cationic surfactants, fatty alcohols and an alkylglyceryl ether, which makes the hair instantly very soft when rinsed out, and significantly improves combability, hair feel and shine.

Background of the invention

Hair conditioning compositions have been known and used for ages. They are used for detangling the hair and providing further additional properties. They are usually aqueous compositions based on cationic surfactants and may additionally comprise oily substances, polymers and others. They may be emulsions which are usually rinsed off after application and processing on the hair, and solutions and/or dispersions which are usually left on the hair and not rinsed off. Since the compositions are generally aqueous compositions, they comprise only low amounts of care ingredients and therefore require relatively large amounts to be applied onto hair. This, furthermore, results in use of larger packaging materials mainly made of mixture of plastic materials which are often not recyclable and requires larger quantities to be transported which automatically means larger CO2 emission. These compositions may be seen in several aspects uneconomical and environmentally disadvantageous. As clearly pointed out there are many aspects which should definitively be overcome for the sake of environment and to reduce or keep the promises that the temperature increase will not exceed 1 ,5°C on average over time.

There have been efforts to overcome the above referred problems mainly by providing leave in compositions as detangling and further improvement of keratin fibers properties, which has not found a broad acceptance by the users because of mainly high loading on the hair, which results in volume reduction and makes hair in a way more covered and may as well be sticky.

Presence of cationic surfactants provide certain level of softening to the keratin fibers. It is quite important for the consumer feeling the softness during rinsing off the composition form hair and afterwards in towel dry and finally in dry state. Currently available conditioners have some drawback and therefore there is a need for further products. Summary of the invention

Therefore, the first object of the present invention is an aqueous-alcoholic composition for keratin fibers especially for human hair characterized in that it comprises: a) one or more glyceryl ether(s) according to the general structure wherein Ri is straight or branched, saturated or unsaturated alkyl chain with C4-C18 atoms, b) one or more polyol(s) other than the glyceryl ether, c) one or more amine and/or quaternary ammonium surfactant(s), d) one or more fatty alcohol(s), wherein the composition comprises water in the range of more than 10% by weight to 35% by weight or less, preferably in the range of 12.5% by weight to 25% by weight, more preferably in the range of 15% by weight to 25% by weight, calculated to the total weight of the composition, wherein the composition comprises one or more polyol(s) according to group b) at a concentration of at least 40% by weight, calculated to the total weight of the composition.

The second object of the present invention is a method of conditioning keratin fibers especially human hair, comprising the following steps:

(i) Treating the keratin fibers with an aqueous composition, preferably a cleansing composition, and then, when the keratin fibers are wet,

(ii) Applying the composition onto the keratin fibers and leaving it for a time period in the range of 1 s to 10 min, then

(iii) Rinsing off the composition from the keratin fibers, and then (iv) Towel drying the keratin fibers.

The third object of the present invention is a kit for hair comprising two or more components wherein one of the first components is a composition as defined above.

Detailed description of the invention

The inventors of the present invention have surprisingly and unexpectedly found that the combination according to claim 1 makes the hair instantly very soft when rinsed out, and significantly improves combability, hair feel and shine. Additionally, the invention cares the hair very well with a minimum application amount and within very short application times.

Aqueous-alcoholic composition for keratin fibers

The present invention is directed to an aqueous-alcoholic composition for keratin fibers especially for human hair comprising: a) one or more glyceryl ether(s) according to the general structure wherein Ri is straight or branched, saturated or unsaturated alkyl chain with C4-C18 atoms, b) one or more polyol(s) other than the glyceryl ether, c) one or more amine and/or quaternary ammonium surfactant(s), d) one or more fatty alcohol(s), wherein the composition comprises water in the range of more than 10% by weight to 35% by weight or less, preferably in the range of 12.5% by weight to 25% by weight, more preferably in the range of 15% by weight to 25% by weight, calculated to the total weight of the composition, wherein the composition comprises one or more polyol(s) according to group b) at a concentration of at least 40% by weight, calculated to the total weight of the composition. Compound(s) according to group a) - Glyceryl ether(s)

The composition of the present invention comprises one or more glyceryl ether(s) as compound(s) according to group a) having the following general structure: wherein Ri is straight or branched, saturated or unsaturated alkyl chain with C4-C18 atoms.

Suitable examples for the one or more glyceryl ether(s) according to the general structure above are ethylhexyl glycerin, hexylglycerin, heptylglycerin, methylheptylglycerin, and/or mixtures thereof, preferably the one or more glyceryl ether according to the above general structure is ethylhexyl glycerin.

The total concentration of one or more compound(s) according to group a) in the composition of the present invention is in the range of 0.1 % by weight to 10% by weight, preferably in the range of 0.2% by weight to 7.5% by weight, more preferably in the range of 0.25% by weight to 5% by weight, calculated to the total weight of the composition.

Compound(s) according to group b) - Polyol(s)

The composition of the present invention comprises one or more polyol(s) as compound(s) according to the group b).

Preferably, said one or more polyol(s) are selected form glycerol, 1 ,2-propylene glycol, 1 ,3-propane diol, 1 ,3-butylene glycol, 1 ,2-pentylene glycol, sorbitol, panthenol, and mixtures thereof.

The most preferred one or more polyol(s) as compound(s) according to the group b) is glycerol.

The total concentration of the one or more compound(s) according to group b) in the composition of the present invention is at least 40% by weight, more preferably in the range of 40% by weight to 90% by weight, and more preferably in the range of 40% by weight to 85% by weight, still more preferably in the range of 50% by weight to 85% by weight, still more preferably in the range of 60% to 85% by weight, calculated to the total weight of the composition.

Compound(s) according to group c) - Amine and/or quaternary ammonium surfactant(s)

The composition of the present invention comprises one or more amine(s) and/or quaternary ammonium surfactant(s) as compounds according to group c).

Preferably, said one or more compounds according to group c) is/are selected from the compounds according to the general structures A, B, or C,

Structure A Structure B

Structure C wherein R2 is a saturated or unsaturated, branched, or straight alkyl chain with C8-C24 atoms or wherein Re is saturated or unsaturated, branched, or straight alkyl chain with C7-C21 atoms and n has value of 1 - 4, or o c (CH₂)_n R7 o wherein R7 is saturated or unsaturated, branched, or straight alkyl chain with C7-C21 atoms and n has value of 1 - 4, Rs and R4 are hydrogen or unsaturated or saturated, and straight or branched alkyl chain with C1-C4 atoms, and

Rs, Rs and R9 are unsaturated or saturated, branched, or straight alkyl chains with C1-C4 atoms, wherein R10 is a straight alkyl chain with C1-C4 atoms, wherein the term unsaturated or saturated refers to C2-C4 alkyl chain and branched alkyl chain refers to C3-C4 alkyl chain.

Preferably, the one or more amine or quaternary ammonium surfactant is selected from stearyl amine, stearoylethyl amine, stearamidopropyldimethylamine, behenamidopropyl dimethyl amine, stearyl amine, palmamine, oleamine, palmitamine, stearoxypropyl dimethylamine, a halogen salt of cetrimonium, steartrimonium, behentrimonium, preferably said surfactant is selected from halogen salts of behentrimonium and cetrimonium such as behentrimonium chloride or bromide or cetrimonium chloride or bromide, and/or their mixtures.

The total concentration of the one or more compound(s) according to group c) is in the composition of the present invention is in the range of 0.1 % by weight to 10% by weight, preferably in the range of 0.2% by weight to 7.5% by weight, more preferably in the range of 0.25% by weight to 5% by weight, calculated to the total weight of the composition.

Compound(s) according to group d) - Fatty alcohol(s)

The composition of the present invention comprises one or more fatty alcohol(s) as compound(s) according to group d).

Preferably, said compound(s) is/are selected from the compounds according to the following general structure R11-OH, wherein R11 is a saturated or unsaturated, branched, or straight alkyl chain with C10-C24 atoms and preferably selected from cetyl alcohol, stearyl alcohol, cetearyl alcohol, behenyl alcohol, arachidyl alcohol, myristyl alcohol, isocetly alcohol and oleyl alcohol, and mixures thereof.

The most preferred fatty alcohol according to group d) is myristyl alcohol. It is preferred that the composition as described above comprises one or more fatty alcohols at a concentration in the range of 0.1 % by weight to 10% by weight, preferably in the range 0.2% by weight to 7.5% by weight, more preferably in the range 0.25% by weight to 5% by weight, calculated to the total weight of the composition. pH of the inventive composition

It is preferred that the pH of the present invention is in the range of 3.0 to 6.0, preferably 3.5 to 5.5 and more preferably 3.5 to 5.0, when diluted 1 :3 by weight with water and at 20°C.

The pH can be measured with a calibrated glass electrode.

Preferably the pH is adjusted with one or more organic acids.

Preferably said organic acid(s) is/are selected from citric acid, malic acid, lactic acid, glycolic acid, tartaric acid, formic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, maleic acid, and fumaric acid, and/or mixtures thereof.

It is preferred that the total concentration of the one or more organic acid(s) is in the range of 0.01 % by weight to 2% by weight, calculated to the total weight of the composition as described above.

Mono-alcohols

The composition as described above can additionally comprise one or more linear and/or saturated mono-alcohol(s) having 2 to 6 carbon atoms.

Preferably, said alcohol(s) is/are selected from ethanol, butanol, propanol, pentanol, hexanol, the most preferred mono-alcohol is ethanol.

It is preferred that the total concentration of said alcohol(s) is in the range of 1 % by weight to 30% by weight, more preferably in the range of 2% by weight to 25% by weight, still more preferably in the range of 5% by weight to 25% by weight, calculated to the total weight of the composition. Thickening polymer(s)

The composition as described above may comprise one or more thickening polymer(s), preferably selected from cellulose ethers.

Suitable cellulose ethers are carboxymethylcellulose, methylcellulose and derivatives such as hydroxypropyl methylcellulose and hydroxyethyl methylcellulose, hydroxyethylcellulose and derivatives such as ethyl hydroxyethylcellulose and methyl ethyl hydroxyethylcellulose, hydroxypropyl cellulose, and ethylcellulose, more preferably the thickening polymer(s) is hydroxyethyl cellulose.

It is preferred that the total concentration the one or more thickening polymer(s) is in the range of 0.01 % by weight to 5% by weight, preferably in the range of 0.1 % by weight to 5% by weight, calculated to the total weight of the composition.

The present invention is also directed to a composition comprising: a) ethylhexyl glycerin at a total concentration in the range of 0.1 % by weight to 10% by weight, calculated to the total weight of the composition, b) glycerol at a total concentration in the range of 40% by weight to 85% by weight, calculated to the total weight of the composition, c) a halogen salt of behentrimonium or cetrimonium, and/or their mixtures, at a total concentration in the range of 0.1 % by weight to 10% by weight, calculated to the total weight of the composition, d) myristyl alcohol at a total concentration in the range of 0.1 % by weight to 10% by weight, calculated to the total weight of the composition, wherein the composition comprises water in the range of more than 10% by weight to 35% by weight or less, preferably in the range of 12.5% by weight to 25% by weight, more preferably in the range of 15% by weight to 25% by weight, calculated to the total weight of the composition.

Method of conditioning keratin fibers

Another aspect of the present invention is a method of conditioning keratin fibers especially human hair, comprising the following steps: (i) Treating the keratin fibers with an aqueous composition, preferably a cleansing composition, and then, when the keratin fibers are wet,

(ii) Applying the composition as described above onto the keratin fibers and leaving it for a time period in the range of 1 s to 10 min, then

(iii) Rinsing off the composition from the keratin fibers, and then

(iv) Towel drying the keratin fibers.

It is further preferred from the viewpoint of hair smoothness that the leave-on time in step ii) is in the range of 10 s to 10 min, preferably in the range of 30 s to 10 min.

Kit for hair

Still another aspect of the present invention is a kit for hair comprising two or more components wherein one of the components is the composition as described above.

Preferably, the second component of the kit may be shampoo or blow dryer.

The following examples are to illustrate the invention, but not to limit it.

EXAMPLES

Table 1 : Formulation(s) of the present invention juxtaposed to comparative example.

The values of the combing force measurements are represented in mN.

Discussion of results

The formulations were applied onto the hair and their effect was evaluated by measuring the combing force. The inventive examples 1 , 2, and 3 (s. Table 1 , above) showed similar results at different water concentrations. Increasing the water concentration (and/or decreasing glycerol concentration) to 80 wt.-%, significantly increased the combing force. The data show clearly that the inventive formulations considerably alleviated the combing procedure by significantly decreasing the force which needed to be applied for hair combing. The less force is applied during combing the easier the hair is combed.

Furthermore, sensory effects of the inventive formulations (Inv. ex. 1 to 3) were observed and confirmed by an expert panel. All inventive examples showed superior results juxtaposed to the comparative example (s. Table 1). Methods

0.5 g of each of the compositions from above was applied onto wet human hair fibers (25 cm long, 2 g per bundle) and left for 5 s. The hair was then rinsed off with water. Combing force was measured according to the protocol below after blow-drying the hair. The panel test as detailed below was conducted on wet and dry hair with level 9 damage.

Combing force measurement

Sample tresses, of approximately 25 cm in length, were treated with the different compositions from above. The combing force was determined with a tensile testing machine from Zwick-Roell (Ulm, Germany) fitted with a combing attachment and using a nominal force of 20N. The combing rate was 15 seconds per 20 cm streak.

Hair tresses to be tested were stored in a climate-controlled atmosphere of 20°C and 60% relative humidity for 16 hours prior to testing. After that the measurements were performed three times per tress and the average force was calculated.

Expert Panel

Sensory effects were observed and confirmed by an expert panel. The “in vivo" sensory evaluation by hairdressers is a well-established method used since about 50 years in the test salon at Kao Germany GmbH. This type of sensory evaluation is an industry standard method for testing the properties of professional hair care products on human hair.

The standard sensory evaluation is executed on real hair models by well-trained hairdresser experts, which are specialized in specific product segments e.g., color, perm, styling, and care products to ensure the reliability and reproducibility of the tests. The evaluation of the formulations (s. Table 1 ) was conducted as monadic comparison on 5 clients. Every head was analyzed by the hairdressers for each property (s. Table 1 ) on the scale between 1 and 5, wherein 1 stands for “not at all satisfied”, 2 stands for “little satisfied”, 3 stands for “satisfied”, 4 stands for “well satisfied”, and 5 stands for “very well satisfied” performance. Each client head was evaluated by 10 stylists and a mean value was calculated (s. Table 1 ).

Claims

1 . An aqueous-alcoholic composition for keratin fibers especially for human hair characterized in that it comprises: a) one or more glyceryl ether(s) according to the general structure wherein Ri is straight or branched, saturated or unsaturated alkyl chain with C4-C18 atoms, b) one or more polyol(s) other than the glyceryl ether, c) one or more amine and/or quaternary ammonium surfactant(s), d) one or more fatty alcohol(s), wherein the composition comprises water in the range of more than 10% by weight to 35% by weight or less, preferably in the range of 12.5% by weight to 25% by weight, more preferably in the range of 15% by weight to 25% by weight, calculated to the total weight of the composition, wherein the composition comprises one or more polyol(s) according to group b) at a concentration of at least 40% by weight, calculated to the total weight of the composition, wherein the one or more fatty alcohol according to group d) is selected from the compounds according to the following general structure

R11-OH, wherein R11 is a saturated or unsaturated, branched, or straight alkyl chain with C10-C24 atoms.

2. The composition according to claim 1 characterized in that the one or more glyceryl ether(s) according to the above general structure is selected from ethylhexyl glycerin, hexylglycerin, heptylglycerin, methylheptylglycerin, and/or mixtures thereof, preferably the one or more glyceryl ether according to the above general structure is ethylhexyl glycerin.

3. The composition according to any of the preceding claims characterized in that the composition comprises one or more glyceryl ether according to the above general structure at a total concentration in the range of 0.1 % to 10% by weight, preferably 0.2% to 7.5% by weight, more preferably 0.25% to 5% by weight, calculated to the total weight of the composition.

4. The composition according to any of the preceding claims characterized in that the composition comprises one or more polyol(s) according to group b) at a total concentration in the range of 40% by weight to 85% by weight, preferably in the range of 50% by weight to 85% by weight, still more preferably in the range of 60% to 85% by weight, calculated to the total weight of the composition.

5. The composition according to any of the preceding claims characterized in that one or more polyol is selected form glycerol, 1 ,2-propylene glycol, 1 ,3-propane diol, 1 ,3-butylene glycol, 1 ,2-pentylene glycol, sorbitol, panthenol, and mixtures thereof.

6. The composition according to any of the preceding claims characterized in that the one or more amine(s) and/or quaternary ammonium surfactant(s) is/are selected from the compounds according to the general structures A, B, or C, Structure A Structure B Structure C wherein R2 is a saturated or unsaturated, branched, or straight alkyl chain with C8-C24 atoms or wherein Re is saturated or unsaturated, branched, or straight alkyl chain with C7-C21 atoms and n has value of 1 - 4, or wherein R7 is saturated or unsaturated, branched, or straight alkyl chain with C7-C21 atoms and n has value of 1 - 4,

R3 and R4 are hydrogen or unsaturated or saturated, and straight or branched alkyl chain with C1-C4 atoms, and

7. The composition according to any of the preceding claims characterized in that the one or more amine or quaternary ammonium surfactant is selected from stearyl amine, stearoylethyl amine, stearamidopropyldimethylamine, behenamidopropyl dimethyl amine, stearyl amine, palmamine, oleamine, palmitamine, stearoxypropyl dimethylamine, a halogen salt of cetrimonium, steartrimonium, behentrimonium, preferably said surfactant is selected from a halogen salt of behentrimonium and cetrimonium.

8. The composition according to any of the preceding claims characterized in that the composition comprises one or more amine or quaternary ammonium surfactant at a total concentration in the range of 0.1 % by weight to 10% by weight, preferably in the range of 0.2% by weight to 7.5% by weight, more preferably in the range of 0.25% by weight to 5% by weight, calculated to the total weight of the composition.

9. The composition according to any of the preceding claims characterized in that one or more fatty alcohol is selected from the compounds according to the following general structure

R11-OH, wherein R11 is a saturated or unsaturated, branched, or straight alkyl chain with C10-C24 atoms and preferably selected from cetyl alcohol, stearyl alcohol, cetearyl alcohol, behenyl alcohol, arachidyl alcohol, myristyl alcohol, isocetyl alcohol and oleyl alcohol, and mixtures thereof.

10. The composition according to any of the preceding claims characterized in that the composition comprises one or more fatty alcohols at a concentration in the range of 0.1 % by weight to 10% by weight, preferably in the range of 0.2% by weight to 7.5% by weight, more preferably in the range of 0.25% by weight to 5% by weight, calculated to the total weight of the composition.

11 .The composition according to any of the preceding claims characterized in that the composition has a pH in the range of 3.0 to 6.0, preferably 3.5 to 5.5 and more preferably 3.5 to 5.0, when diluted 1 :3 by weight with water and at 20°C, preferably the pH is adjusted with one or more organic acids, preferably said organic acids are selected from citric acid, malic acid, lactic acid, glycolic acid, tartaric acid, formic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, maleic acid, and fumaric acid, further preferably the total concentration of the one or more organic acids is in the range of 0.01% by weight to 2% by weight, calculated to the total weight of the composition.

12. The composition according to any of the preceding claims characterized in that it comprises one or more linear and saturated mono-alcohol having 2 to 6 carbon atoms, preferably said alcohol is selected from ethanol, butanol, propanol, pentanol, hexanol, and more preferably the total concentration of said alcohols is in the range of 1 % by weight to 30% by weight, more preferably in the range of 2% by weight to 25% by weight, still more preferably in the range of 5% by weight to 25% by weight, calculated to the total weight of the composition.

13. The composition according to any of the preceding claims characterized in that it comprises one or more thickening polymer(s), preferably selected from cellulose ethers, more preferably said thickening polymer(s) is hydroxyethyl cellulose, and further preferably the total concentration of the thickening polymer(s) is in the range of 0.01 % by weight to 5% by weight, calculated to the total weight of the composition.

14. The composition according to any of the claims 1 to 13 characterized in that the composition comprises: a) ethylhexyl glycerin at a total concentration in the range of 0.1 % by weight to 10% by weight, calculated to the total weight of the composition, b) glycerol at a total concentration in the range of 40% by weight to 85% by weight, calculated to the total weight of the composition, c) a halogen salt of behentrimonium or cetrimonium, and/or their mixtures, at a total concentration in the range of 0.1 % by weight to 10% by weight, calculated to the total weight of the composition, d) myristyl alcohol at a total concentration in the range of 0.1 % by weight to 10% by weight, calculated to the total weight of the composition, wherein the composition comprises water in the range of more than 10% by weight to 35% by weight or less, preferably in the range of 12.5% by weight to 25% by weight, more preferably in the range of 15% by weight to 25% by weight, calculated to the total weight of the composition.

15. A method of conditioning keratin fibers especially human hair, comprising the following steps:

(ii) Applying the composition according to any of the claims 1 to 14 onto the keratin fibers and leaving it for a time period in the range of 1 s to 10 min, then

(iii) Rinsing off the composition from the keratin fibers, and then

(iv) Towel drying the keratin fibers.