Hair styling and / or conditioning composition

Abstract

The present invention is directed to a ready-to-use hair treatment composition having a pH in the range of 7 to 12 comprising a) one or more dihydroxy phenolic compound according to general structure (I) wherein R1 is a straight or branched, saturated or unsaturated C2 to C6 alkyl chain, preferably a C2 to C4 alkyl chain, the alkyl chain being substituted with one or more hydroxyl, carboxyl, and / or amino groups, and more preferably R1 is selected from *CH2-CH2-OH, *CH-CH-COOH, *CH2-CH2-NH2, H2N-*CH-CH2-COOH, HO-*CH- CH2-NH2, HO-*CH-CH2-NH-CH3, HO-*CH-COOH, HO-*CH-CH2OH, and b) one or more polymers comprising a functional group having one or more reactive nucleophilic nitrogen(s).

Description

[0001] Hair Styling and / or Conditioning Composition

[0002] Field of the invention

[0003] The present invention relates to a ready-to-use hair treatment cosmetic composition having a pH of 7 to 12 and comprising one or more dihydroxy phenolic compounds, and one or more styling and / or care polymers having reactive nucleophilic nitrogen groups. The invention also relates to a method of treating human hair with said composition, and a kit for hair treatment.

[0004] Background of the invention

[0005] Hair conditioning compositions have been known and used for a long time. They are used for care, detangling, and styling the hair and for providing further additional properties. They are usually aqueous compositions based on cationic surfactants and may additionally comprise oily substances, polymers, and other ingredients. They may be emulsions, which are usually rinsed off after application and processing on the hair, or solutions and / or dispersions which are usually left on the hair and not rinsed off but blow dried. Since the compositions are generally aqueous compositions, they comprise low amounts of active ingredients and, therefore, require relatively large amounts to be applied onto hair. Furthermore, this results in use of larger packaging materials, mainly made of mixtures of plastic materials, which are often not recyclable and require larger quantities to be transported. This automatically means higher CO2emissions. These compositions may be viewed in several aspects as uneconomical and environmentally disadvantageous. As clearly pointed out, there are many aspects which should definitively be overcome for the sake of protecting the environment. There have been efforts to overcome the above referred problems, mainly by providing leave-in compositions for detangling and the further improvement of keratin fiber properties, which have not found broad acceptance by the users because of high loading on the hair resulting in volume reduction and making the hair in a way more covered and stickier as well.

[0006] Problems

[0007] Styling routines might take a long time and even have to be refreshed, e.g., due to the influence of weather, such as wind or rain. Also, most stylings only last until the next hair wash. After that, the whole styling procedure has to start from the beginning. Each refreshing styling procedure is, therefore, accompanied by time consumption, expenses, and material usage.

[0008] Similarly, most care ingredients or applications may also only last until the next hair wash or be removed after a couple of washes. People with damaged hair have to use a conditioner or hair mask with each hair washing to achieve easy hair combing.

[0009] WO2022233532 and WO2022233533 disclose inventions related to cosmetic agents for treating a keratin material, comprising amodimethicone / morpholinomethyl silsesquioxane copolymer or alpha-hydroxy ketone and hydroxytyrosol. The inventions also relate to a method in which the cosmetic agent is used.

[0010] WO2023110582 discloses aqueous compositions comprising ortho diphenols at alkaline pH, but is completely silent on polymers comprising a functional group having one or more nucleophilic nitrogens.

[0011] Several hair treatment compositions are known from the prior art, but none of them solve the above-mentioned problems satisfyingly.

[0012] Summary of the invention

[0013] The first object of the present invention is a ready-to-use hair treatment composition having a pH in the range of 7 to 12 comprising:

[0014] a) one or more dihydroxy phenolic compound according to general structure

[0015]

[0016] wherein R1is a straight or branched, saturated or unsaturated C2to C6alkyl chain, preferably a C2to C4alkyl chain, the alkyl chain being substituted with one or more hydroxyl, carboxyl, and / or amino groups, and more preferably R1is selected from *CH2-CH2-OH, *CH-CH-COOH, *CH2-CH2-NH2, H2N-*CH-CH2-COOH, HO-*CH-CH2-NH2, HO-*CH-CH2-NH-CH3, HO-*CH-COOH, HO-*CH-CH2OH,

[0017] b) one or more polymers comprising a functional group having one or more reactive nucleophilic nitrogen(s). The second object of the present invention is a hair treatment method comprising the following steps:

[0018] i) applying to hair the ready-to-use hair treatment composition as defined above, ii) leaving the ready-to-use hair treatment composition onto hair for a time period in the range of 1 min to 120 min, then

[0019] iii) applying heat to hair in a temperature range of 80°C to 230°C, then

[0020] iv) optionally shampooing and drying the hair.

[0021] The third object of the present invention is a hair treatment kit comprising the ready-to-use hair treatment composition as defined above and one further item selected from: - a hot tool,

[0022] - an oxidative composition comprising one or more persalt(s) and / or peroxy salt(s). Detailed description of the invention

[0023] The inventors of the present invention have surprisingly and unexpectedly found out that the invention set forth in the independent claims can be handled easily and results in prolonged care and / or styling effect lasting over several washes on hair. The present invention leads to prolonged intervals of refreshing hair styling procedures and thus to less time consumption, reduced expenses, and product use for the consumer, resulting in improved sustainability.

[0024] Ready-to-use composition

[0025] The present invention is directed to a ready-to-use hair treatment composition having a pH in the range of 7 to 12 comprising:

[0026] a) one or more dihydroxy phenolic compound according to general structure

[0027]

[0028] wherein R1is a straight or branched, saturated or unsaturated C2to C6alkyl chain, preferably a C2to C4alkyl chain, the alkyl chain being substituted with one or more hydroxyl, carboxyl, and / or amino groups, and more preferably R1is selected from *CH2-CH2-OH, *CH-CH-COOH, *CH2-CH2-NH2, H2N-*CH-CH2-COOH, HO-*CH-CH2-NH2, HO-*CH-CH2-NH-CH3, HO-*CH-COOH, HO-*CH-CH2OH,

[0029] b) one or more polymers comprising a functional group having one or more reactive nucleophilic nitrogen(s).

[0030] It is preferred from the viewpoint of durability of the styling and caring effect that the pH of the ready-to-use composition is in the range of 7.5 to 11, preferably in the range of 8 to 10.5, more preferably in the range of 8.5 to 10.

[0031] Preferably, the ready-to-use composition of the present invention is an aqueous composition. ‘Aqueous’ within the meaning of the present invention denotes a composition comprising water at 50% by weight or more, preferably at 60% by weight or more, more preferably at 75% by weight or more, calculated to the total weight of the ready-to-use composition.

[0032] The composition of the present invention comprises one or more dihydroxy phenolic compounds according to the general structure:

[0033]

[0034] wherein R1is a straight or branched, saturated or unsaturated C2to C6alkyl chain, preferably a C2to C4alkyl chain, the alkyl chain being substituted with one or more hydroxyl, carboxyl, and / or amino groups.

[0035] Preferably R1of the one or more dihydroxy phenolic compounds is selected from *CH2-CH2-OH, *CH-CH-COOH, H2-CH2-NH2, H2N- H-CH2-COOH, HO- H-CH2-NH2, HO- H-CH2-NH-CH3, HO-*CH-COOH, HO-*CH-CH2OH.

[0036] Suitable non-limiting examples for the one or more dihydroxy phenolic compounds are hydroxytyrosol, caffeic acid, dopamine, dihydroxyphenylalanine, noradrenaline, adrenaline, dihydroxyphenylglycol (DOPEG) and 3,4-dihydroxymandelicacid (DOMA). The preferred one or more dihydroxy phenolic compounds are hydroxytyrosol, caffeic acid, dopamine, dihydroxyphenylalanine. The most preferred dihydroxy phenolic compound is hydroxytyrosol.

[0037] It is preferred that the total concentration of the one or more dihydroxy phenolic compounds is in the range of 0.01% to 7.5% by weight, preferably in the range of 0.1% to 5% by weight, more preferably in the range of 0.25% to 5% by weight, calculated to the total weight of the ready-to-use composition.

[0038] The ready-to-use composition of present invention comprises one or more polymers comprising a functional group having one or more reactive nucleophilic nitrogen(s). Preferably, the one or more reactive nucleophilic nitrogen(s) of the polymer is / are one or more primary amino groups, one or more secondary amino groups, one or more tertiary amino groups, one or more imidazole groups.

[0039] Suitable examples are styling and / or care polymers, preferably selected from Polyquaternium-68 (PQ-68), carbohydrate modified amino silicones such as CHT-BeauSil RE-AMO 919 (INCI name: Gluconamido amodimethicone (and) Coco-Glucoside), Amodimethicone and grafted aminated Amodimethicone derivatives (e.g., aminopropyl dimethicone, sold under the tradename X-52-2265; Dowsil 969; Belsil ADM 6057 E), VP / Methacrylamide / Vinyl Imidazole Copolymer (Luviset Clear E), Chitosan, and / or their salt(s), and / or their mixtures.

[0040] The most preferred polymers are Polyquaternium-68, and / or amodimethicone, and / or their salt(s), and / or their mixtures.

[0041] Preferably, the total concentration of the polymers is in the range of 0.01% to 10% by weight, preferably 0.1% to 6% by weight, more preferably 0.5% to 5% by weight, still more preferably 1 % to 5% by weight, calculated to the total weight of the ready-to-use composition.

[0042] It is further preferred from the viewpoint of alkalinity that the ready-to-use composition of the present invention further comprises one or more alkalizing agents, preferably said alkalizing agents are one or more alkali metal hydroxides or alkaline earth hydroxides, ammonia and / or its salts, alkyl and / or alkanolamines according to the general structure

[0043]

[0044] R2wherein R2, R3, R4are the same or different from H, and R2, R3, R4are selected from C1to C4, C3to C4unsaturated alkyl, C3to C4branched alkyl, C1to C4hydroxyl alkyl, C3to C4unsaturated hydroxyl alkyl, C3to C4branched hydroxyl alkyl, with the condition that at least one of R2, R3, or R4is different from H, and / or their salt(s), and / or their mixtures, more preferably said alkyl or alkanolamines is / are monoethanolamine, diethanolamine, triethanolamine, monomethylamine, dimethylamine, trimethylamine, monoethylamine, diethylamine, tris-(hydroxymethyl)-aminomethane, and 2-aminomethyl propanol, and / or their mixtures, and / or their salt(s), still more preferably said alkalizing agents are selected from ammonia and / or its salt(s), sodium hydroxide, potassium hydroxide, monoethanolamine, 2-amino-2-methylpropanol, tris-(hydroxymethyl)-aminomethane, and / or its / their salt(s).

[0045] It is further preferred that the total concentration of the one or more alkalizing agents in the ready-to-use composition is in the range of 0.1 % to 50% by weight, preferably in the range 0.5% to 45% by weight, more preferably in the range of 1 % to 40% by weight, calculated to the total weight the ready-to-use composition.

[0046] It is further preferred that the ready-to-use composition comprises oxidizing agents at 1% by weight or less, preferably said ready-to-use composition comprises oxidizing agents at 0.1% by weight or less, more preferably said ready-to-use composition is free of oxidizing agents.

[0047] It is further preferred that the ready-to-use composition comprises reducing agents at 1% by weight or less, preferably said ready-to-use composition comprises reducing agents at 0.1% by weight or less, more preferably said ready-to-use composition is free of reducing agents.

[0048] In another aspect of the present invention, the ready-to-use composition comprises one or more persalt(s) and / or peroxy salt(s), and / or their mixtures, and preferably the one or more persalt(s) and / or peroxy salt(s) are sodium persulfate, potassium persulfate, ammonium persulfate, and / or their mixtures.

[0049] For this aspect, it is preferred that the total concentration of the one or more persalt(s) and / or peroxy salt(s), still more preferably the total concentration of sodium persulfate, potassium persulfate, ammonium persulfate, and / or their mixtures, is in the range of 0.1% to 10% by weight, more preferably in the range of 0.25% to 7.5% by weight, still more preferably in the range of 0.5% to 5% by weight, calculated to the total weight of the composition.

[0050] Optionally, the ready-to-use composition of the present invention may comprise one or more additional hair conditioning compounds selected from synthetic oils, natural oils, cationic surfactants, anionic surfactants, or non-ionic surfactants.

[0051] Method for treating hair

[0052] The present invention is also directed to a hair treatment method comprising the following steps:

[0053] i) applying to hair the ready-to-use hair treatment composition as defined above, ii) leaving the ready-to-use hair treatment composition onto hair for a time period in the range of 1 min to 120 min, then

[0054] iii) applying heat to hair in a temperature range of 80°C to 230°C, then

[0055] iv) optionally shampooing and drying the hair.

[0056] Preferably, the time period for step ii) is in the range of 2 min to 90 min, more preferably in the range of 5 min to 60 min, still more preferably in the range of 10 min to 45 min. Furthermore, preferably the temperature range in step iii) is from 80°C to 220°C, more preferably in the range of 120°C to 210°C. From the viewpoint of user convenience, it is preferred that heat is applied to the hair with a hot tool, more preferably with a hair iron, still more preferably with a round iron or flatiron.

[0057] Hair treatment kit

[0058] The present invention is also directed to a hair treatment kit comprising the ready-to-use hair treatment composition as defined above and one further item selected from: - a hot tool, - an oxidative composition comprising one or more persalt(s) and / or peroxy salt(s). Suitable one or more persalt(s) and / or peroxy salt(s) of the oxidative composition are sodium persulfate, potassium persulfate, ammonium persulfate, and / or their mixtures. Suitable concentrations of the one or more persalt(s) and / or peroxy salt(s) in the oxidative composition are in the range of 1 % to 80% by weight, preferably in the range of 2% to 75% by weight, still more preferably in the range of 5% to 70% by weight, calculated to the total weight of the oxidative composition.

[0059] Such hot tools include, but are not limited to, hair irons such as round irons or flatirons. Preferably, the hot tool is a flatiron.

[0060] The following examples are to illustrate the present invention, but not to limit it. A- 16 / 24

[0061] EXAMPLES

[0062] Table 1

[0063] Com. 1 Com. 2 Com. 3 Inv. 1 Ingredients

[0064] [% by weight]

[0065] a) Hydroxytyrosol - 1.5 - 1.5 b) Amodimethicone* - - 0.6 0.6 - NH4Cl / NH3Ad pH 9.5

[0066] - Water Ad 100.0

[0067] Evaluation [Combing force, mN]

[0068] Washing 1x wash 59.5 47.5 36.9 34.6 cycles 7x wash 69.9 52.5 45.1 35.3

[0069]

[0070] *X-52-2265 from ShinEtsu Corp.

[0071] A lower combing force value [mN] indicates a better care effect. The inventive example 1 showed the highest durability of the reduction in combing force. A- 16 / 24

[0072] Table 2

[0073] Comp. 4 Comp. 5 Comp. 6 Inv. 2 Ingredients

[0074] [% by weight]

[0075] a) Hydroxytyrosol - 1.5 - 1.5 b) Polyquaternium-68 - - 2.4 2.4 - NH4Cl / NH3Ad pH 9.5

[0076] - Water Ad 100.0

[0077] Evaluation [Bending force, mN] unwashed 126 160 608 808 Washing

[0078] 1x wash 121 127 303 780 cycles

[0079] 8x wash 119 114 156 307

[0080]

[0081] A higher bending force [mN] indicates a better styling hold. The inventive example 2 showed the highest durability of the styling hold. A- 16 / 24

[0082] Table 3

[0083] Comp. 7 Inv. 3 Ingredients

[0084] [% by weight]

[0085] a) Hydroxytyrosol - 1.5

[0086] b) Polyquaternium-68 2.0 2.0

[0087] - Sodium persulfate 1.5 1.5

[0088] - NH4CI / NH3 Ad pH 9.5

[0089] - Water Ad 100.0

[0090] Evaluation [Bending

[0091] force, mN]

[0092] Washing unwashed 4150 7060 cycles

[0093] 7x wash 92 1540

[0094]

[0095] A higher bending force [mN] indicates a better styling hold. The inventive example 3 showed the highest durability of the styling hold. A- 16 / 24

[0096] Methods

[0097] Chinese white hair was used to measure the styling effect (bending force), and European coarse hair level 7 was used to measure the care effect (combing force). The hair was immersed in a one of the compositions as disclosed above for 15 min at room temperature. After the application time of 15 min, the hair was taken out of the solution and blow dried. For the examples of tables 1 and 2, the hair streaks were treated with a hair iron set to a temperature of 210°C. No heat was applied for the examples of table 3.

[0098] Bending force measurement

[0099] To quantify the styling effect of the composition on the hair, the bending force was measured in mN. The tresses treated with the different compositions from above, were subjected to a three-point bending test (Zwick / Roell Z0.5, ZwickRoell GmbH & Co. KG, Ulm, Germany) using a bending rate of 200 mm min’1, and the maximum force required to deform the tresses by 20 mm was measured.

[0100] Hair tresses to be tested were stored in a climate-controlled atmosphere of 20°C and 65% relative humidity for 16 hours prior to testing. After that, the measurements were performed three times per tress and the average force was calculated.

[0101] The hair tresses were then washed by hand and the maximum force of deformation was remeasured, as above, after a number of washing steps. Each washing step consisted of prewetting the hair with warm water, followed by the application of ca. 2 g of 3.5% SLES solution onto the tress and rubbing for ca. 30 sec, followed by rubbing the hair tress under a stream of warm water for a further 30 sec. The hair tresses were then blow-dried for 30 min.

[0102] Combing force measurement

[0103] Sample tresses 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. A- 16 / 24

[0104] Hair tresses to be tested were stored in a climate-controlled atmosphere of 20 °C and 65% relative humidity for 16 hours prior to testing. After that the measurements were performed ten times per tress and the average force calculated.

[0105] The hair tresses were then washed by hand and the maximum force of deformation was remeasured, as above, after a number of washing steps. Each washing step consisted of prewetting the hair with warm water, followed by the application of ca. 2 g of 3.5% SLES solution onto the tress and drubbing for ca. 30 sec, followed by rubbing the hair tress under a stream of warm water for a further 30 sec. The hair tresses were then blow-dried for 30 min.

Claims

Claims1. A ready-to-use hair treatment composition having a pH in the range of 7 to 12 comprising:a) one or more dihydroxy phenolic compound according to general structurewherein R1is a straight or branched, saturated or unsaturated C2to C6alkyl chain, preferably a C2to C4alkyl chain, the alkyl chain being substituted with one or more hydroxyl, carboxyl, and / or amino groups, and more preferably R1is selected from *CH2-CH2-OH, *CH-CH-COOH, *CH2-CH2-NH2, H2N-*CH-CH2-COOH, HO-*CH-CH2-NH2, HO-*CH-CH2-NH-CH3, HO-*CH-COOH, HO-*CH-CH2OH,b) one or more polymers comprising a functional group having one or more reactive nucleophilic nitrogen(s).

2. The composition according to claim 1 characterized in that the one or more dihydroxy phenolic compound(s) according to group a) are selected from hydroxytyrosol, caffeic acid, dopamine, dihydroxyphenylalanine, noradrenaline, adrenaline, dihydroxymandelic acid and dihydroxyphenylglycol, more preferably it is hydroxytyrosol.

3. The composition according to any of the claims 1 and / or 2 characterized in that the total concentration of the one or more dihydroxy phenolic compound is in the range of 0.01% to 7.5% by weight, preferably in the range of 0.1% to 5% by weight, more preferably in the range of 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 functional group of polymers comprising reactive nucleophilic nitrogen(s) as compound(s) according to group b) of the aqueous composition is one or more primary amino groups, one or more secondary amino groups, one or more tertiary amino groups, and / or one or more imidazole groups, preferably said polymers according togroup b) are selected from Polyquaternium-68, Gluconamido amodimethicone, Polysilicone-29, Amodimethicone, Chitosan, and / or their salt(s), and / or their mixtures, still more preferably said polymers are Polyquaternium-68 and / or Amodimethicone, and / or their salt(s), and / or their mixture(s).

5. The composition according to any of the preceding claims characterized in that the total concentration of the polymers according to group b) is in the range of 0.01% to 10% by weight, preferably 0.1% to 6% by weight, more preferably 0.5% to 5% by weight, still more preferably 1% to 5% by weight, calculated to the total weight of the composition.

6. The composition according to any of the preceding claims characterized in that the composition further comprises one or more alkalizing agent(s), preferably said alkalizing agent(s) are alkali metal hydroxides or alkaline earth hydroxides, ammonia and / or its salt(s), alkyl and / or alkanolamines according to the general structurewherein R2, R3, R4 are the same or different from H, and R2, R3, R4 are selected from Ci to C4, C3 to C4 unsaturated alkyl, C3 to C4 branched alkyl, Ci to C4 hydroxyl alkyl, C3 to C4 unsaturated hydroxyl alkyl, C3 to C4 branched hydroxyl alkyl, with the condition that at least one of R2, R3, or R4is different from H, and / or their salt(s), and / or their mixtures, more preferably said alkyl or alkanolamines is / are monoethanolamine, diethanolamine, triethanolamine, monomethylamine, dimethylamine, trimethylamine, monoethylamine, diethylamine, tris-(hydroxymethyl)-aminomethane, and 2-aminomethyl propanol, and / or their mixtures, and / or their salt(s), most preferably said alkalizing agent sodium or potassium hydroxide, ammonia, monoethanolamine, and / or their salt(s), and / or their mixtures, and further preferably the total concentration of one or more alkalizing agents in the composition is in the range of 0.1 % to 50% by weight, preferably in the range 0.5% to 45% by weight, more preferably in the range of 1% to 40% by weight, calculated to the total weight of the composition.

7. The composition according to any of the preceding claims characterized in that the pH of the composition is in the range of 7.5 to 11, preferably in the range of 8 to 10.5, more preferably in the range of 8.5 to 10.

8. The composition according to any of the preceding claims characterized in that the composition comprises oxidizing agents at 1% by weight or less, preferably said composition comprises oxidizing agents at 0.1% by weight or less, more preferably said composition is free of oxidizing agents.

9. The composition according to any of the preceding claims characterized in that the composition comprises reducing agents at 1% by weight or less, preferably said composition comprises reducing agents at 0.1% by weight or less, more preferably said composition is free of reducing agents.

10. The composition according to any of the claims 1 to 7 and / or 9 characterized in that the composition further comprises one or more persalt(s) and / or peroxy salt(s), and / or their mixtures, and preferably the one or more persalt(s) and / or peroxy salt(s) are sodium persulfate, potassium persulfate, ammonium persulfate, and / or their mixtures, and more preferably the total concentration of the one or more persalt(s) and / or peroxy salt(s), still more preferably the total concentration of sodium persulfate, potassium persulfate, ammonium persulfate, and / or their mixtures, is in the range of 0.1% to 10% by weight, more preferably in the range of 0.25% to 7.5% by weight, still more preferably in the range of 0.5% 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 is an aqueous composition and comprises water at 50% by weight or more, preferably at 60% by weight or more, more preferably at 75% by weight or more, calculated to the total weight of the composition.

12. A hair treatment method comprising the following steps:i) applying to hair the ready-to-use hair treatment composition as defined in any of the claims 1 to 11,ii) leaving the ready-to-use hair treatment composition onto hair for a time period in the range of 1 min to 120 min, theniii) applying heat to hair in a temperature range of 80°C to 230°C, theniv) optionally shampooing and drying the hair.

13. The method according to claim 12 characterized in that the composition in step ii) is left on the hair for a time period in the range of 2 min to 90 min, preferably in the range of 5 min to 60 min, more preferably in the range of 10 min to 45 min.

14. The method according to any of the claims 12 and / or 13 characterized in that the temperature in step iii) is in the range of 80°C to 220°C, preferably in the range of 120°C to 210°C.

15. A hair treatment kit comprising the ready-to-use hair treatment composition according to any of the claims 1 to 7, and / or 9 and / or 11 and one further item selected from:- a hot tool,- an oxidative composition comprising one or more persalt(s) and / or peroxy salt(s).

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