EA041597B1 - HAIR STRENGTHENING METHOD AND HAIR STRENGTHENING KIT CONTAINING AT LEAST TWO SEPARATE COMPOSITIONS - Google Patents

Description

Technical field

A hair strengthening method, hair strengthening composition and kit, including providing a composition capable of crosslinking functional amino acid groups of keratin fibers, as well as mixing such a crosslinking composition with commercially available hair dyes or hair bleaching compositions.

State of the art

The invention relates to hair treatment products that contain bifunctional active ingredients, wherein the active ingredients react with the amine groups and carboxyl groups of the hair and thereby improve the quality of the hair in various ways, and also significantly increase the durability of the perm. The present invention is also related to a method for improving the condition of the hair.

Constant bleaching, perming and coloring, and sometimes even frequent hair washing with degreasing surfactants or other active ingredients can damage the hair structure. Hair becomes brittle and loses its shine. In addition, combing the hair charges the hair electrostatically, and the rough surface of the hair leads to tangles. Combing thus becomes more difficult.

Hair treatment products with a nourishing effect on the hair, which can facilitate combing of the hair, have gained importance and relevance in the European patent application EP 234261. Such products are, for example, formulations in the form of a clear hair rinse solution or in the form of a so-called rinse cream emulsion, distributed over still damp hair after washing the hair, then after keeping the composition on the hair for a period of minutes to an hour, the hair is washed with water.

Hair treatments based on the aforementioned conditioning actives, however, show only a satisfactory result in the treatment of dry and weakened hair. When treating moderately oily hair, the products usually give a weak effect, in view of the fact that their use makes the hair more oily, while the resistance of the hair is reduced. Hairstyle durability is also known to depend on disulfide bonds, which are unstable and can be easily reduced to 2 sulfhydryl groups under reducing conditions. There have been many attempts to restore disulfide bonds by introducing oxidizing agents.

This technology is based on many agents that increase the resistance of perms. Also, a large number of patents and patent applications are directed to the reduction of disulfide bonds, these are applications such as US patent 9095518 B2, US patent applications 2015034119 A1, 201537270 A1, 201537271 A1 and WO 2015017768 A1. However, the hair treatments described in these documents have much room for improvement.

An attempt has also been made to use amino acids in the form of, for example, a weakly acid mixture containing various amino acids and vitamins (US-PS 4201235) as a hair conditioning component in order to avoid the disadvantages of known hair treatments. However, the manufacture of such a mixture of various vitamins and amino acids is troublesome and expensive.

In addition, the use of hydrolysed keratin and citric acid in the composition of a neutralizing shampoo is known from the article Cosmetics and Toileteries Vol. 98 (1983), S. 59-68. This shampoo, however, has a rather low hair care effect and leads to severe dehydration of the hair. For this reason, it is necessary to apply hair conditioning products one or more times after washing the hair.

It is also known from W. Fassbender, Parfumerie & Kosmetik, 39 (1), S. 11-16 (1958) that an amino acid solution containing 18 to 22 different amino acids can be used, for example, in the treatment of hair using weak acids. and hair care products. Obtaining such a solution of amino acids is carried out by fractionated hydrolysis of natural proteins, followed by purification of the obtained hydrolysates. As a result, it is difficult to guarantee a constant composition of the liquid, which in turn is important for the quality of the cosmetic product.

The aim of the invention is to provide a hair care product and a hair care method which are based on bifunctional organic acids as well as bifunctional Brønsted bases which overcome the disadvantages described above. In particular, the present invention provides a novel hair care agent and method for strengthening hair, which is suitable for the production of particularly durable hair styles.

Surprisingly, it has been found that a method that meets these requirements includes the steps

a) applying to the hair a first composition that contains at least a bifunctional Bronsted base of the general formula X-R-Y, where X and Y are independently selected from the groups amino, carboxylate, nitrate, hydrogen phosphate, phosphate, sulfate and carbonate, and R represents an organic group molecules with 1-20 carbon atoms, 0-5 oxygen atoms and 0-5 nitrogen atoms and is not aromatic or heteroaromatic, and X-R-Y has a molecular weight of less than 500 g/mol, and

b) applying to the hair a second composition containing at least a bifunctional organic acid capable of reacting with the amino groups of the hair,

- 1 041597 characterized in that at least the bifunctional Bronsted base of the general formula X-R-Y is a mixture of 4,7,10-trioxa-1,13-tridecanediamine, 4,9-dioxa-1,12-dodecanediamine and 1,11- diamino3,6,9-trioxaundecane, or at least a bifunctional Bronsted base of the general formula X-R-Y, is a mixture of 4,7,10-trioxa-1,13-tridecanediamine and 4,9-dioxa-1,12 dodecanediamine, or, according to at least the bifunctional Bronsted base of general formula X-R-Y is 4,7,10-trioxa-1,13-tridecanediamine, and at least the bifunctional organic acid is maleic acid, itaconic acid, or a mixture of maleic acid and itaconic acid, and the first the formulation has a pH of 7 to 12 and the second formulation has a pH of 1.5 to 7, and a reduction in hair breakage is achieved.

In one embodiment of the invention, in both of these 2 compositions, the bifunctional substances should have a concentration of 1-30 wt.%, respectively.

In general, compound (a) is applied before compound (b). However, it is also possible to apply composition (b) before composition (a).

The hair is dried in one embodiment of the invention between steps (a) and (b), and the drying time is from 1 to 60 minutes, while a dryer is used to dry the hair.

These compositions in one embodiment of the invention should be kept on the hair for 1-45 minutes. In one embodiment of the invention, the composition of step (a) is left on the hair for 1-45 minutes. In another embodiment of the invention, the composition of step (b) is left on the hair for 1-45 minutes.

The advantage is that the formulations of steps (a) and (b) are independently miscible with a cosmetically acceptable carrier, wherein the cosmetically acceptable carrier of the formulation of step (a) is either identical or non-identical to the cosmetically acceptable carrier of the formulation of step (b).

It is also an advantage that the composition of step (a) is mixed with commercially available hair coloring or bleaching agents before being applied to the hair. In turn, the composition of step (b) may be mixed with a commercially available hair coloring agent.

It is also recommended that before applying step (a) the hair is treated with a hair care composition containing thioglycolic acid for perming.

The essence of the invention

This document describes a method for strengthening and/or restoring hair, comprising the steps of: (a) applying to the hair a hair care composition that contains at least a bifunctional Bronsted base of the general formula X-R-Y, where X and Y are proton-withdrawing groups, and R is an organic substituent containing 1 to 20 carbon atoms, and 0 to 5 oxygen atoms, and 0 to 5 nitrogen atoms, and the molecular weight of X-R-Y is less than 500 g/mol, and leaving the alkaline hair strengthening composition in for 1 to 45 minutes, (b) if necessary, washing, shampooing and/or drying the hair, (c) applying to the hair a composition containing a cross-linking composition containing at least a bifunctional organic acid capable of reacting with amino groups of the hair, and leaving the alkaline composition to strengthen the hair for 1 to 45 minutes, (d) if necessary, rinsing, shampooing and/or drying the hair, characterized in that the composition of stage (a) has a pH of 7 to 12, and the composition of step (c) has a pH of 1.5 to 7. Optionally, the hair strengthening composition of step (a) may be mixed with commercially available hair coloring or bleaching agents prior to application. When applied without pre-mixing with either a commercially available hair dye or a bleaching composition, the hair strengthening composition may be modified such that the hair strengthening composition of step (c) is applied before the hair strengthening composition of step (a).

Detailed description of the invention

In this document, including all embodiments of all aspects of the present invention, the following definitions apply, unless specifically indicated otherwise. All percentages by weight of the total composition. All coefficients are weight coefficients. References to parts, for example, a mixture of 1 part X and 3 parts Y, is a ratio by weight. QS or QSP means sufficient for 100% or for 100 g. ± indicates the standard deviation. All ranges are quite wide and combinable. The number of significant digits is not limited either by the measurement limits of the quantities or by the accuracy of the measurements. It is understood that all numerical quantities are changed using the word about. All measurements mean measurement at 25°C and in ambient conditions where ambient conditions mean 1 atm pressure and 50% relative humidity. Relative humidity refers to the ratio (expressed as a percentage) of the moisture content of the air compared to the level of saturated moisture at the same temperature and pressure. Relative humidity can be measured with a hygrometer. Here min means minute or minutes, mole means mole; nanometer is abbreviated nm; g after the number means grams or grams. All weights that apply to ingredients listed are based on actual levels and do not include carriers or intermediates that may be contained in

- 2 041597 materials available on the market. Here containing means that other steps and other ingredients may be added. Containing encompasses the terms consisting of and consisting primarily of. The compositions, means, methods, uses, kits, and processes of the present invention may contain, consist of, and consist essentially of the elements and limitations described in the present invention, as well as any additional or optional ingredients, components, steps, or limitations described in the present invention. The embodiments and aspects described herein may include or be combined with elements, features, or components of other embodiments and/or aspects, although they cannot be clearly illustrated in combination unless incompatibility is indicated. In at least one embodiment, means that one or more embodiments, possibly all of the embodiments or a large subset of the embodiments of the present invention has/have the feature subsequently described. Where ranges of amounts are indicated, they should be understood as the total amount of the specified ingredient in the composition or, when more than one species falls under the definition of an ingredient, the total amount of all ingredients that meet this definition in the composition. For example, if a formulation contains from about 1 to about 5% fatty alcohol, then a formulation comprising 2% stearic alcohol and 1% cetyl alcohol would fall within the scope.

Viscosity is measured at 25°C using a HAAKE Rotation Viscometer VT 550 with vessel cooling/heating and sensor systems according to DIN 53019 with a shear rate of 12.9 s ^-1 .

Water soluble refers to any material that is sufficiently soluble in water to form a clear solution under naked eye control at a concentration of 0.1% by weight of the material in water at 25°C. The term water insoluble refers to any material that is not water soluble.

Substantially free from or substantially free means less than 1%, or less than 0.8%, or less than 0.5%, or less than 0.3%, or about 0% of the total weight of the composition or composition.

Keratin fibers means a fibrous material composed of keratin. Hair means mammalian keratin fibers, including scalp hair, facial hair, eyelashes and body hair. The term hair also includes hair attached to a living object, as well as hair that has been removed from a living object, such as hair samples and hair on a doll/dummy. In at least one embodiment, hair means human hair. A hair shaft or hair fiber means a single strand of hair and can be used interchangeably with the term hair.

Cosmetically acceptable means that the compositions, formulations and described components are suitable for use in contact with human stratum corneum without undue toxicity, incompatibility, instability, allergic reaction, and the like. All compositions and compositions described herein, which are intended to be directly applied to keratin tissue, are limited in their use in that they must be cosmetically acceptable.

The term derivatives includes, but is not limited to, amides, ethers, esters, amino, carboxyl, acetyl derivatives, acids, salts and/or alcohol derivatives of these compounds. In at least one embodiment, derivatives means amides, esters, ethers, amino, carboxyl, acetyl derivatives, acids, salts, and alcohol derivatives.

Monomer means a discrete, unpolymerized chemical moiety capable of undergoing polymerization in the presence of an initiator or any suitable reaction that creates macromolecules, such as polycondensation, polyaddition, anionic or cationic polymerization reactions.

The unit means a monomer that has already been polymerized, ie. is part of the polymer.

Polymer means a chemical substance formed by the polymerization of two or more monomers. The term polymer includes all materials obtained by the polymerization of monomers, as well as natural polymers. Polymers made from only one type of monomer are called homopolymers. The polymer contains at least two monomers. Polymers made from two or more different types of monomers are called copolymers. The distribution of the various monomers may be random, variable or block (ie block copolymer). The term polymer as used herein includes any type of polymer, including homopolymers and copolymers.

A kit means a package containing a plurality of components. A set may be referred to as a composition-of-parts. An example of a kit is, for example, a first composition and a separately packaged second composition, and optionally an instruction for use.

The following describes the details of various aspects of the invention.

Description of individual aspects

This document describes a method for strengthening keratin fibers. The method makes it possible to achieve semi-permanent strengthening of the hair shaft either by treating the hair with such a hair strengthening composition or by mixing the hair strengthening composition with commercially available hair coloring or bleaching compositions. The method involves the use of two different formulations,

- 3 041597 one of which has a pH value of 7 to 12, and the second composition has a pH value of 1.5 to 7. The first composition is called alkaline, and the second composition is acidic. The hair strengthening effect is maintained after at least one shampooing. In addition, the inventors have found that this method increases the hair's resistance to water and moisture, increases styling comfort, and/or makes hair easier to handle after shampooing, and when mixed with commercially available hair coloring or bleaching formulations, the alkaline hair strengthening formulation does not have any effect. negative effects on the hair when dyeing or bleaching if the pH of the alkaline composition is chosen in the pH range from 9 to 11. Without reference to any theory, it is argued that the above advantages are due to the carried out process steps, their sequence, as well as the properties of specific components used including as an active agent. It is believed that selected active substances of the acid composition diffuse into the keratin fiber stem, interact with the amino groups in the keratin polypeptide and bind these functional groups in the keratin protein structure, providing sufficient cross-links to overcome the restoring force that prevents penetration into the keratin fiber structure. The acid composition cannot react with the potentially available sulfhydryl groups of the hair when the reaction conditions are acidic. The hypothetical reaction of potential hair sulfhydryl groups is such that deprotonation of such sulfhydryl groups is required. Since the selected protonating agents of the present invention are stronger acids than sulfhydryl groups, such a reaction cannot proceed. It is also believed that selected alkaline actives diffuse into the keratin fiber stem, react with carboxyl groups in the keratin polypeptide and bind these functional groups. This leads to an increase in the strength of the keratin fibers, for example, in the treatment of damaged hair.

The following describes the details of various aspects of the invention.

Description of the crosslinking composition

Cross-linking compositions of the present invention are significantly different from each other and work synergistically. The order in which they are applied does not matter for the results that will be achieved, however the order of addition is relevant when mixed with a commercially available hair coloring or bleaching product. Commercial hair coloring and bleaching products include a pH adjusting agent that creates an alkaline pH. In the case of oxidative hair coloring, a shift in pH >0.5 units can lead to a change in the final color of the hair. In the case of using a commercially available hair whitening preparation, a pH shift of >0.5 units reduces the bleaching power of such a commercially available hair whitening preparation. Therefore, if additives are added to commercially available hair coloring or bleaching products, it is important that these additives do not alter the pH of the hair coloring or bleaching mixture. Thus, commercially available hair coloring agents as well as hair bleaching agents have a pH of 8 to 12, and it is important that these agents are miscible with the alkaline composition of the present invention. When mixed with a commercially available hair coloring or bleaching agent, the blended formulation is applied first and then, secondarily, the unmixed hair strengthening formulation. The recommended holding time between application steps is 1-45 minutes. If desired, the hair is washed and dried between the first and second application steps. If desired, an interval of 1-45 minutes between the application of an acidic and alkaline composition to strengthen the hair is also applied.

The acidic hair strengthening composition [b] is usually applied after the alkaline hair strengthening composition [a] and contains at least difunctional Brønsted acids as crosslinkers. At the very least, bifunctional Brønsted acids are advantageous in the case of an acidic hair strengthening formulation in that the acids can form bonds between adjacent amino groups in the hair. Most Brønsted bifunctional acids are of natural origin, which is an advantage from the point of view of consumers in comparison with synthetic compounds. This is due not only to sensations and hypersensitivity, but also to considerations of compositional stability and environmental reasons, since natural compounds are destroyed naturally and quickly and do not require special methods of decomposition. In addition, they are also readily available and relatively inexpensive.

Since there is no desire to be bound by a rigorous theory, it is believed that the alkaline hair strengthening agent reacts with the carboxyl groups of the hair and further cross-links the hair proteins. Hair is composed of keratin polypeptides having functional groups of carboxylic acids [-COOH], hydroxyl [-OH], amino [-NH2], and possibly some sulfhydryl [-SH] groups. Various active agents may react preferentially with any of the functional groups. For example, at least difunctional Bronsted acids react with amino groups while at least difunctional proton acceptors react with carboxyl groups.

At least the bifunctional Brønsted acid as well as the bifunctional proton acceptor are in one embodiment of the invention present in a concentration of 1 to 30% by weight.

- 4 041597 of the total amount of acid or alkaline crosslinking composition, preferably from 2 to 25%, more preferably from 3 to 20%, even more preferably from 4 to 15% and most preferably from 5 to 10%. The molar ratio of at least the difunctional proton acceptor to the difunctional Bronsted acid in one embodiment is from about 1:1 to about 3:1, preferably from 1.5:1 to 2.5:1, but more preferably from about 2:1 to 2.5:1.

In at least one embodiment, the acidic as well as the alkaline crosslinker compositions individually comprise a cosmetically acceptable carrier. In at least one embodiment, the cosmetically acceptable carrier is any carrier suitable for formulating with the active agent a crosslinking formulation suitable for application to the hair. In at least one embodiment, the cosmetically acceptable carrier is selected from either an aqueous medium or a water-alcohol medium. In at least one embodiment, when the carrier is a water-alcohol carrier, the carrier contains water and alcohol. In at least one embodiment, the alcohol is selected from the group consisting of ethanol, isopropanol, propanol, and mixtures thereof. In at least one embodiment, when the carrier is an aqueous carrier, the carrier is comprised primarily of water and substantially free of alcohol. In at least one embodiment, the acidic as well as the alkaline crosslinking compositions individually constitute a safe and effective amount of a cosmetically acceptable carrier. In at least one embodiment, the acidic as well as the alkaline crosslinking compositions individually consist of about 0.1% to about 99%, or about 1% to about 98%, or about 10% to about 97%, or about 30% to about 95% water (relative to the weight of the crosslinker).

Other ingredients may be present in both the acidic and alkaline crosslinkers. In at least one embodiment, the acid as well as the alkaline crosslinkers contain antioxidants. Antioxidants are useful in that they provide long term stability to the crosslinker. In at least one embodiment, the acidic as well as alkaline crosslinkers contain a safe and effective amount of an antioxidant. In at least one embodiment, the acidic as well as alkaline crosslinking compositions include 0.001 to 5% or 0.5 to 1.0% of an antioxidant. In at least one embodiment, the antioxidant is selected from the group consisting of: ascorbic acid (vitamin C), ascorbyl esters of fatty acids, derivatives of ascorbic acid (for example, magnesium ascorbyl phosphate, sodium ascorbyl phosphate, ascorbyl sorbate), tocopherol (vitamin E), tocopherol sorbate, tocopherol acetate, other tocopherol esters, butyl-, hydroxy derivatives of benzoic acid and their salts, peroxides, including hydrogen peroxide, perborate, thioglycolates, persulfate salts, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (available sold under the brand name Trolox™), gallic acid and its alkyl esters, especially propyl gallate, uric acid and its salts and alkyl esters, ferulic acid and its salts and esters, sorbic acid and its salts, lipoic acid, amines (e.g., K,K-diethylhydroxyamine, aminoguanidine), sulfhydryl compounds (for example, glutathione), dihydrokeifumaric acid and its salts, glycine pyrrolidonecarboxylate, pidolate a rginine, nordihydroguaiaretic acid, bioflavonoids, curcumin, lysine, 1-methionine, proline, superoxide dismutase, silymarin, tea extracts, grape skin and/or grape seed extracts, melanin, rosemary extracts and mixtures thereof. In at least one embodiment, the antioxidant is tocopherol sorbate or tocopherol ester. In at least one embodiment, the antioxidant is sodium benzoate. In at least one embodiment, the antioxidant is ferulic acid. Ferulic acid has the advantage that it increases the oxidation stability of the final composition. In at least one embodiment, the acidic as well as the alkaline crosslinkers contain a safe and effective amount of ferulic acid. In at least one embodiment, the cross-linking composition is from 0.001 to 5% or from 0.5 to 1.0% ferulic acid.

In at least one embodiment, the acidic as well as alkaline crosslinking compositions contain a chelator or chelating agent. The terms chelator or chelating agent as used herein means an active agent capable of removing a metal ion from a system by forming a complex such that the metal ion is more difficult to participate in reactions or more difficult to catalyze chemical reactions. The inclusion of a chelating agent is particularly useful in providing protection against ultraviolet radiation, which can contribute to excessive changes in the structure or texture of the skin, and against other environmental components that can harm the skin, in turn, to reduce the local level of iron, which creates, as shown above, a pro-oxidant situation and pigmentation. The chelating agent is useful in that it provides long term stability to the crosslinker. In at least one embodiment, the acidic as well as alkaline crosslinking compositions contain a safe and effective amount of a chelator or chelating agent. In at least one embodiment, the acidic and also alkaline crosslinking compositions contain a chelating agent, wherein the chelating agent is selected from the group consisting of N-hydroxysuccinimide, EDTA, HTA, deferoxamine, hydroxamic acids and their salts, phytic acid, phytates, gluconic acid and its salts, transferrin, lactoferrin, as well as their mixtures. In at least one embodiment, acidic as well as alkaline crosslinkers

- 5 041597 contain a safe and effective amount of a chelating agent. In at least one embodiment, the acidic as well as alkaline crosslinking compositions are from 0.001 to about 10%, or from 0.01 to about 5%, or from 0.1 to about 5%, or from 0.5 to 1.0 % chelating agent. Examples of chelators that are useful here are disclosed in US Pat. No. 5,487,884 issued January 30, 1996 to Bisset et al.; in International Publication No. 91/16035 (Bush et al.), published October 31, 1995; and in International Publication No. 91/16034 (Bush et al.) published October 31, 1995. In at least one embodiment, the chelating agent is selected from the group consisting of N-hydroxysuccinimide, deferoxamine, lactoferrin, hydroxamic acids, gluconic acid, phytic acids, their derivatives and their mixtures.

In at least one embodiment, the acidic as well as the alkaline crosslinkers are present in a form suitable for application to the hair. In at least one embodiment, the crosslinking acidic as well as alkaline compositions are present in the form of an emulsion, solution, or slurry. In at least one embodiment, the crosslinking composition contains a surfactant. A surfactant can be used to create a stable emulsion. In at least one embodiment, at the time the emulsion is created, said emulsion may be a water-in-oil emulsion, an oil-in-water emulsion, or a multiple emulsion.

The emulsion provides an easy-to-apply mixture for the consumer using the hair formulation, and the emulsion also has aesthetic benefits. The acidic as well as the alkaline crosslinkers may be leave-on or rinse-off formulations. Acid as well as alkaline crosslinkers can be forms of a hair conditioning formulation. The crosslinking acid as well as alkaline formulations may also contain at least one cosmetic selected from styling polymers, conditioners, hair cleansers, or mixtures thereof. In at least one embodiment, the acidic as well as the alkaline crosslinking compositions comprise a styling polymer. In at least one embodiment, the styling polymer is selected from the group consisting of a nonionic polymer, an anionic polymer, a zwitterionic and/or amphoteric polymer, a cationic hair styling polymer, or mixtures thereof. Suitable styling polymers can be found in the CTFA International Cosmetics Ingredient Dictionary and Handbook, Hair Fixatives, 12th edition (2008). 19, line 1 of European patent application EP 08151246.9, filed February 11, 2008 and incorporated herein by reference.

In at least one embodiment, the acidic as well as alkaline crosslinking composition comprises 0.01 to 10% by weight, or 0.1 to 8%, or 0.1 to 5% by weight, hair styling polymer.

In at least one embodiment, the crosslinking composition comprises a non-ionic hair styling polymer. In at least one embodiment, the non-ionic hair styling polymer is a natural or synthetic polymer. In at least one embodiment, the non-ionic hair styling polymer is a polymer obtained by polymerization using at least one type of monomer selected from vinylpyrrolidone; vinylcaprolactam; vinyl esters; vinyl alcohol; vinyl acetate; (meth)acrylamide and/or derivatives thereof; (meth)acrylic acid, its salts and/or its derivatives; propylene and/or ethylene glycolic acid, crotonic acid or mixtures thereof. For example, such polymers are available under the trade names Luviskol® or Luviset Clear®.

In at least one embodiment, the crosslinking composition comprises an anionic hair styling polymer. In at least one embodiment, the anionic hair styling polymer is selected from the group consisting of an acrylic acid/α-kylacrylate/N-alkylacrylamide terpolymer, a vinyl acetate/crotonic acid copolymer; a C ₁ -C5α alkyl acrylate/(meth)acrylic acid copolymer; sodium polystyrenesulfonate; vinyl acetate/crotonic acid/vinyl alkanoate copolymer; vinyl acetate/crotonic acid/vinyl neodecanoate copolymer; aminomethylpropanol acrylate copolymer; vinylpyrrolidone/(meth)acrylic copolymer; a copolymer of methyl vinyl ether/monoalkyl esters of maleic acid; aminomethylpropanol salts of allyl methacrylate/(meth)acrylate copolymer; an ethyl acrylate/methacrylic acid copolymer; vinyl acetate/mono-nbutyl maleate/isobornyl acrylate copolymer; an octylacrylamide/(meth)acrylic acid copolymer; polyesters of diglycol, cyclohexanedimethanol, isophthalic acid and sulfoisophthalic acid and mixtures thereof.

In at least one embodiment, the acidic as well as the alkaline crosslinker comprises zwitterionic or amphoteric hair styling polymers. In at least one embodiment, the zwitterionic or amphoteric hair styling polymer is selected from the group consisting of alkylacrylamide/alkylaminoalkyl methacrylate/(meth)acrylic acid copolymers; copolymers that are formed from at least one monomer of the first group of monomers having a quaternary amine group in the structure and at least one monomer from the second group of monomers having an acidic group; copolymers of fatty alcohol acrylates, alkylamine oxide, methyl methacrylate and at least one monomer selected from acrylic acid and methacrylic acid; copolymers of methacrydoylethylbetaine/methacrylic acid and/or esters of this acid; polyquaternium-47; polyquaternium-43; oligomers or polymers derived from quaternary croton betaines or quaternary

- 6 041597 vertic croton betaine esters or mixtures thereof.

In at least one embodiment, the acidic as well as the alkaline crosslinker comprises a cationic hair styling polymer. In at least one embodiment, a cationic hair styling polymer is selected from the group consisting of homopolymers or copolymers in which quaternary nitrogen groups are present either in the polymer chain or as substituents on one or more cationic monomers. Monomers containing ammonium groups can enter into a copolymerization reaction with a cationic monomer. Suitable cationic monomers may be unsaturated, and free radical polymerizing compounds may have at least one cationic group in their structure, e.g. cationic nitrogen-containing groups such as pyridinium, imidazolinium, or quaternary pyrrolidones, for example alkylvinylimidazolinium, alkylvinylpyridinium or alkylvinylpyrrolidone salts. The alkyl groups of these monomers are preferably shorter alkyl groups such as, for example, C ₁ -C ₇ alkyl groups, particularly preferably C ₁ -C ₃ alkyl groups. Suitable non-cationic monomers may be selected from (meth)acrylamide, its derivatives; acrylate, its derivatives; vinylcaprolactone, vinylcaprolactam, vinylpyrrolidone, vinyl ethers, vinyl alcohol, propylene glycol or ethylene glycol. For example, suitable cationic styling polymers are available under the trade names Gafquat 755 N; Gafquat 734; Gafquat HS 100; Luviquat HM 550; Merquat Plus 3300; Gaffix VC 713; Aquaflex SF 40. In at least one embodiment, the crosslinking composition comprises a cationic hair styling polymer derived from a natural polymer. In at least one embodiment, the cationic hair styling polymer derived from a natural polymer is derived from a natural polymer selected from the group consisting of cationic polysaccharide derivatives such as cellulose, starch and/or guar gum; chitosan, its salts and/or its derivatives; or their mixtures. In at least one embodiment, the cationic hair styling polymers are selected from the group consisting of polyquaternium-4; polyquaternium-10, polyquaternium-24; guar hydroxypropyltrimonium chloride; chitosonium pyrrolidone carboxylate and mixtures thereof.

In at least one embodiment, the acidic as well as alkaline crosslinking composition comprises a hair conditioner or conditioner. The acidic as well as alkaline crosslinkers may contain any suitable and conventional hair conditioning agent. The term hair conditioning agent as used herein means any cosmetically acceptable compound that has a cosmetic effect on the hair, such as providing shine to the hair, making the hair more manageable, improving the feel of the hair, improving combability, and/or adding volume to the hair. Suitable hair conditioning agents can be found in the CTFA International Cosmetics Ingredient Dictionary and Handbook, Hair conditioning agents, 12th edition (2008). In at least one embodiment, a hair conditioning agent is selected from the group consisting of cationic surfactants, nonionic surfactants, silicone compounds, organic oily conditioning agents, and mixtures thereof. Suitable hair conditioning agents are, for example, the materials listed on page 19, line 3, page 27, line 33 of European patent application EP 08151246.9, filed February 11, 2008, which is incorporated herein by reference.

In at least one embodiment, the conditioner is a cationic surfactant. In at least one embodiment, the cationic surfactant contains amino or quaternary ammonium moieties. In at least one embodiment, the acidic as well as alkaline crosslinking compositions contain from about 0.05 to about 3.5%, or from about 0.1 to about 3.0%, or from about 0.5 to about 2.5 %, or from about 1.0 to about 2.0% cationic surfactant. In at least one embodiment, the cationic surfactant corresponds to formula II, wherein at least one of R ⁷¹ , R ⁷² , R ⁷³ and R ⁷⁴ is selected from an aliphatic residue containing from 8 to 30 carbon atoms; aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl groups having from 7 to 22 carbon atoms; while the groups R ⁷¹ , R ⁷² , R ⁷³ and R ⁷⁴ are selected individually from the group consisting of aliphatic groups containing from 1 to 22 carbon atoms; and aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl groups having up to 22 carbon atoms; wherein X is selected from the group consisting of halogen, acetate, citrate, lactate, glycolate, phosphate, nitrate, sulfonate, sulfate, alkyl sulfate, alkyl sulfonate radicals, and mixtures thereof. In at least one embodiment of the cationic surfactants according to formula II (see above), while at least one of R ⁷¹ ,

- 7 041597

R ⁷² , R ⁷³ and R ⁷⁴ is an aliphatic group having 16 to 24 carbon atoms; wherein the remaining substituents R ⁷¹ , R ⁷² , R ⁷³ and R ⁷⁴ are individually selected from the group consisting of an aliphatic residue having from 1 to 4 carbon atoms; wherein X is selected from the group consisting of chloride or sulfate. In at least one embodiment, the cationic surfactant is selected from the group consisting of behenyltrimethylammonium chloride, methyl sulfate, or ethyl sulfate; stearyltrimethylammonium chloride, methylsulfate or ethylsulfate; and mixtures thereof. The longer alkyl group is believed to provide improved smoothness and softness on wet and dry hair compared to cationic surfactants with a shorter alkyl group. It has also been verified that such cationic surfactants can provide less irritation to the scalp compared to a surfactant with a shorter alkyl group. In at least one embodiment, the cationic surfactant is didlnoalkyl-substituted quaternary ammonium salts selected from the group consisting of dialkyl (14-18 carbons) dimethylammonium chloride, ditallowalkyldimethylammonium chloride, di(hydrogenated tallow)alkyldimethylammonium chloride, distearyldimethylammonium chloride, dicetyldimethylammonium chloride and mixtures thereof. In at least one embodiment, the cationic surfactant is a tertiary amidoamine having an alkyl group containing from 12 to 22 carbon atoms. In at least one embodiment, the cationic surfactant is selected from the group consisting of cetyltrimethylammonium salt; behenyltrimethylammonium salt; ditallodimethylammonium salts; stearyl amidopropyldimethylamine; (di)esterquats; quaterniums - 8, 14, 15, 18, 22, 24, 26, 27, 30, 33, 37, 53, 60, 61, 72, 78, 80, 81, 82, 83, 84 and/or 91 or mixtures thereof .

In at least one embodiment, the conditioner is a non-ionic surfactant. Suitable non-ionic surfactants may be surfactants with an HLB of less than 8. Suitable non-ionic surfactants may be selected from glycerol esters; sugar esters; alkyl polyglucoside esters; oleyl- or isostearyl polyglucoside; polyoxyethylene (20) sorbitan monostearate or mixtures thereof.

In at least one embodiment, the conditioner is a silicone compound. In at least one embodiment, the silicone compound is a volatile or non-volatile and/or soluble or insoluble silicone. For example, suitable silicone conditioners are available under the brand names methylphenyl fluid SF 1075 (Electric company); liquid DC200, DC244, DC245, DC345, Dow 5-7113, DC556 cosmetic liquid, DC1248 (Dow Corning). In at least one embodiment, the acidic as well as the alkaline crosslinking compositions contain a conditioning agent, which is the reaction product of a) aminosilane; b) polysiloxane; and optionally c) polyester. In at least one embodiment, the acidic as well as the alkaline crosslinking compositions contain a conditioning agent, which is the reaction product of a) aminosilane; b) polysiloxane; and c) polyester. In at least one embodiment, the acidic as well as the alkaline crosslinking compositions contain a conditioning agent, wherein the conditioning agent is selected from the group consisting of epoxyaminosilane and polysiloxane/polyurea block copolymers and mixtures thereof. In at least one embodiment, the acidic as well as the alkaline crosslinking compositions contain a conditioning agent, which is the reaction product of a) aminosilane; b) polysiloxane; and c) polyester; and optionally d) an amine. In at least one embodiment, the polysiloxane is a polysiloxane containing unopened epoxy groups. In at least one embodiment, the polysiloxane may contain two epoxy or oxetane groups. In at least one embodiment, the polysiloxane contains from about 10 to about 450 silicon atoms, or from about 40 to about 400 silicon atoms, from about 75 to about 350 silicon atoms, from about 150 to about 250 silicon atoms. In at least one embodiment, the polysiloxane is a polysiloxane containing epoxy groups. In at least one embodiment, the polyester has the structure CH ₂ (O)CHCH ₂ O(CH ₂ (CH ₃ )CH ₂ O) _n CH ₂ CH(O)CH ₂ (on average), where n is an integer from 1 to 10. In at least one embodiment, the amine contains from 1 to 10 carbon atoms or from 2 to 5 carbon atoms. In at least one embodiment, the amine is an alkylamine having at least one alkyl group as a substituent. In at least one embodiment, the amine is selected from the group consisting of methylamine, ethylamine, propylamine, ethanolamine, isopropylamine, butylamine, isobutylamine. hexylamine, dodecylamine, oleylamine, aniline, aminopropyltrimethylsilane, aminopropylsilane, aminomorpholine, aminopropyldiethylamine, benzylamine, naphthylamine, 3-amino9-ethylcarbazole, 1-aminoheptafluorohexane, 2,2,3,3,4,4,5,5,6,6, 7,7,8,8,8-pentadecafluoro-1-octanamine and mixtures thereof. In at least one embodiment, the amine is selected from the group consisting of methylethylamine, methylhexylamine, methyloctadecylamine, diethanolamine, dibenzylamine, dihexylamine, dicyclohexylamine, piperidine, pyrrolidine, phthalimide, and mixtures thereof. In at least one embodiment, the conditioner is an epoxyaminosilane copolymer. In at least one embodiment, the conditioner is the reaction product of (a) an aminosilane; (b) a polysiloxane, where the polysiloxane contains from about 10 to about 450 silicon atoms, or from about 40 to about 400 silicon atoms; (c) a polyester; and (d) an amine, wherein the amine is an alkylamine substituted with at least one alkyl group.

- 8 041597

In at least one embodiment, the acidic as well as the alkaline conditioning agents are selected from the group consisting of epoxyaminosilane copolymers and polysiloxane/polyurea block copolymers, as well as mixtures thereof. In at least one embodiment, the conditioning agent is a polydimethylsiloxane derivative containing aminoalkyl groups and having an amine number of at least 0.1 meq/g polydimethylsiloxane. Such polydimethylsiloxane derivatives can be, for example, derivatives having terminal methoxy or hydroxy groups or mixtures thereof.

In at least one embodiment, the conditioner is an oily organic conditioning agent. In at least one embodiment, the organic oily conditioning agent is non-volatile, water-insoluble, oily, or fatty. Organic oil conditioners may be selected from hydrocarbon oils and fatty acid esters. In at least one embodiment, the conditioning agent is a fatty alcohol. In at least one embodiment, the fatty alcohol is a non-volatile fatty alcohol with a low melting point. In at least one embodiment, the conditioning agent is a fatty alcohol, and the fatty alcohols are selected from the group consisting of caprylic alcohol, lauryl alcohol, stearyl alcohol, cetyl alcohol, myristyl alcohol, and mixtures thereof.

The acidic as well as the alkaline crosslinking compositions may further comprise at least one direct hair dye. In at least one embodiment, the crosslinking composition comprises about 0.01% to about 15%, or about 0.1% to about 10%, or about 0.5% to about 8% direct hair dye.

The acidic as well as the alkaline crosslinking compositions may additionally contain at least one viscosity modifying agent. In at least one embodiment, the cross-linking composition contains from about 0.01 to about 20%, or from about 0.05 to about 10%, or from about 0.1 to about 5% of a viscosity modifying agent.

Acid as well as alkaline crosslinkers may additionally contain at least one emulsifier and/or surfactant. In at least one embodiment, the emulsifier and/or surfactant is selected from non-ionic surfactants; anionic surfactants; amphoteric surfactants or mixtures thereof. In at least one embodiment, the acidic as well as alkaline crosslinking compositions contain from about 0.01 to about 20%, or from about 0.05 to about 10%, or from about 0.1 to about 5% emulsifier and/or surface -active substance.

Acid as well as alkaline crosslinkers may additionally contain at least one pigment. In at least one embodiment, the pigment is selected from natural pigments; synthetic pigments or mixtures thereof. The pigments may be selected from organic pigment, inorganic pigment, or mixtures thereof. The pigments may be selected from colored pigments, pearlescent pigments or mixtures thereof. Said acidic as well as alkaline crosslinkers may contain from about 0.01% to 10%, or from about 1% to about 2% of the pigment (by weight of the total), contained in the mass of the product in undissolved form, both for acid and for alkaline crosslinking compositions. Acid as well as alkaline crosslinking compounds may include pigment materials such as inorganic, nitroso, monoazo, diazo compounds, carotenoids, derivatives of triphenylmethane, triarylmethane, xanthene, quinoline, oxazine, azine, anthraquinone, indigo dyes, thioindigo, quinacridone, phthalocyanine, as well as vegetable and other natural dyes, including water-soluble components, which are listed in C.I. Names.

In at least one embodiment, the acidic as well as the alkaline crosslinkers contain at least one solid. In at least one embodiment, the solid is selected from silica, silicates, aluminates, clay soils, mica, insoluble salts, substantially insoluble inorganic metal salts, metal oxides, mineral salts, insoluble polymer particles, or mixtures thereof. In at least one embodiment, the acidic as well as alkaline crosslinking compositions comprise from about 0.01% to about 10%, or from about 0.05% to about 5%, of at least one solid. In at least one embodiment, the acidic as well as the alkaline crosslinkers are substantially free of solid particles such as clay.

In at least one embodiment, the acidic as well as the alkaline crosslinkers contain at least one preservative. In at least one embodiment, the acidic as well as alkaline crosslinkers may contain from about 0.01% to about 5%, or from about 0.05% to about 1% by weight, of a preservative.

Various additional optional ingredients may be included in the acidic as well as alkaline crosslinking compositions of the present invention. An unlimited number of examples of such additional ingredients may be selected from preservatives; antioxidants; flavoring substances; reagents-stabilizers, solvents; fragrances and perfume substances; fillers; masking agents; odor absorbers; coloring matter; lipid vesicles; detergent surfactants; thickeners and suspending agents; viscosity modifiers, pearlescent agents; UV protective and sunscreens; means to combat free

- 9 041597 radicals; polyvinyl alcohol; pH-regulating agents; salts; dyes; polymeric plasticizers; direct dyes or their mixtures. Acid as well as alkaline crosslinkers may contain about 0% or about 0.1 to about 5% antimicrobials. In at least one embodiment, the acidic as well as alkaline crosslinking compositions contain an organic acid selected from the group consisting of: glycine, L-methionine, L-arginine, biotin, creatine, and mixtures thereof. In at least one embodiment, the acidic as well as the alkaline crosslinkers comprise panthenol. In at least one embodiment, the acidic as well as the alkaline crosslinkers comprise a waxy compound. In at least one embodiment, the acidic as well as the alkaline crosslinkers comprise beeswax.

In at least one embodiment, the acidic as well as the alkaline crosslinkers have a viscosity, measured at 25°C, of from about 0.1 to about 1,000,000 MPa-s, or from about 1 to about 80,000 MPa-s, or from about 5 to about 3500 MPa-s. Viscosity is measured with a HAAKE Rotation Viscometer VT 550 with vessel cooling/heating and sensor systems according to DIN 53019 (MVDIN, SV-DIN), shear rate is 12.9 s ^-1 .

In at least one embodiment, the acidic as well as the alkaline crosslinkers contain a buffering agent. In at least one embodiment, the buffering agent is a phosphate buffer. In at least one embodiment, the buffering agent is a borate buffer or a carbonate buffer. In at least one embodiment, the buffering agent is selected from the group consisting of glycine/sodium hydroxide; sodium carbonate/sodium hydrogen carbonate, sodium tetraborate/sodium hydroxide; sodium bicarbonate/sodium hydroxide; ammonium chloride / ammonia. The buffering agent aids in pH control, which helps to stabilize the crosslinking composition. In at least one embodiment, the acidic as well as alkaline crosslinking compositions contain an alkaline substance and/or a pH adjusting agent. Acid as well as alkaline crosslinkers may additionally contain a protonating agent. The protonating agent may be a monobasic or polybasic acid, a water-soluble or water-insoluble acid, and/or an organic or inorganic acid. In at least one embodiment, the protonating agent is selected from formic acid, acetic acid, sulfuric acid, hydrochloric acid, citric acid, and mixtures thereof.

Description of the method

Described herein is an embodiment of a method for strengthening hair and/or restoring hair, comprising: (a) applying an alkaline crosslinker to the hair and leaving the alkaline hair strengthening composition for 1 to 45 minutes; (b) if necessary, rinsing, shampooing and/or drying the hair; (c) applying the acidic crosslinking composition to the hair and leaving the acidic hair strengthening composition for 1 to 45 minutes; (d) if necessary, rinsing, shampooing and/or drying the hair. Before step (a), the hair strengthening composition may be mixed with commercially available hair coloring or bleaching compositions. When mixed with commercially available hair coloring or bleaching preparations, the process steps are in the following order: (a), then (b), then (c), then (d). If not mixed with a commercially available hair dye or bleaching formula, the process steps may be (c) then (d) then (a) then (b). In the method of the present invention, acidic as well as alkaline crosslinkers can be applied to wet hair and/or dry hair.

In one embodiment, depending on the first step of the method, which can be either step (a) or step (c), the hair is washed with a shampoo, such as a clarifying shampoo. Alternatively, either step (b) or step (d) follows at the end of the treatment cycle, depending on whether the method started from step (a) or step (c), while the hair is treated with a conditioning agent containing a conditioner. Conditioning agents are disclosed here and are suitable for this option. There is an option where the hair is dried with a hair dryer and a brush.

In one embodiment, the method relates to a method for strengthening hair and/or restoring hair, comprising: (a) applying an alkaline hair care composition to the hair, wherein the hair care composition contains at least a bifunctional Bronsted base of the general formula X-R-Y where X and Y are proton-withdrawing groups and R is an organic bridge containing 1 to 20 carbon atoms and 0 to 5 oxygen atoms and 0 to 5 nitrogen atoms, and X-R-Y has a molecular weight of less than 500 g /mol, and leaving the alkaline hair strengthening composition for 1 to 45 minutes, and at least the bifunctional Bronsted base of the general formula X-RY is a mixture of 4,7,10-trioxa-1,13-tridecanediamine, 4 ,9-dioxa-1,12-dodecanediamine and 1,11-diamino-3,6,9-trioxaundecane, or at least a bifunctional Bronsted base of the general formula X-R-Y is a mixture of 4,7,10-trioxa-1, 13-tridecanediamine and 4,9-dioxa1,12-dodecanediamine, or at least least, the bifunctional Bronsted base of the general formula X-R-Y is 4,7,10-trioxa-1,13-tridecanediamine, (b) washing or drying the hair, if necessary, (c) applying to the hair an acidic composition, including a cross-linking composition containing, at least bifunctional organic acids capable of reacting with the amino groups of the hair, and leaving the acid composition to strengthen the hair for 1 to 45 minutes, at least

- 10 041597 the bifunctional organic acid is maleic acid, itaconic acid or a mixture of maleic acid and itaconic acid, (d) if necessary, washing, shampooing and / or drying the hair, characterized in that the composition of stage (a) has a pH value from 7 to 12, and the composition of step (c) has a pH value of 1.5 to 7. Optionally, the hair strengthening composition of step (a) can be mixed with commercially available hair coloring or bleaching agents before application. When used without pre-mixing with a commercially available hair coloring or bleaching agent, the hair strengthening method may be changed such that the hair strengthening composition of step (c) is applied before the hair strengthening composition of step (a).

Applying a hair care product

The present invention relates to a method for strengthening and/or restoring hair, comprising: (a) applying an alkaline hair care composition to the hair, which contains. at least a bifunctional Bronsted base of general formula X-R-Y, wherein X and Y are proton acceptor groups and R is an organic bridge containing 1 to 20 carbon atoms and 0 to 5 oxygen atoms and 0 to 5 atoms nitrogen, and X-R-Y has a molecular weight of less than 500 g/mol, while at least the bifunctional Brönsted base of the general formula X-R-Y is a mixture of 4,7,10-trioxa-1,13-tridecanediamine, 4,9-dioxa-1 ,12-dodecanediamine and 1,11-diamino-3,6,9-trioxaundecane, or at least a bifunctional Bronsted base of general formula X-R-Y is a mixture of 4,7,10-trioxa-1,13-tridecanediamine and 4, 9-dioxa1,12-dodecanediamine, or at least a bifunctional Brönsted base of the general formula X-R-Y is 4,7,10-trioxa-1,13-tridecanediamine, and (c) applying to the hair an acid composition containing a crosslinking composition, containing at least a bifunctional organic acid capable of p react with the amino groups of the hair, and at the same time, at least the bifunctional organic acid is maleic acid, itaconic acid or a mixture of maleic acid and itaconic acid, while about 0.01 to about 5 g of these compositions are applied to the hair per 1 g hair. In one embodiment, the acidic as well as the alkaline formulations are left on the hair for at least 1 minute, or about 5 to about 45 minutes, or about 10 to about 40 minutes, or about 20 to about 35 minutes, before performing the remaining step ( a) or (c), depending on whether the method starts from step (a) or (c).

Hair drying

The method for straightening and/or relaxing the hair may include drying the hair in steps (b) and/or (d). In an embodiment, the hair is dried with a hair dryer. In one embodiment, the hair is dried for about 1 to about 45 minutes, or about 2 to 20 minutes, or about 5 to 15 minutes. In general, after drying the hair, the hair may still be damp, but a reasonable, for example, 75%, drying of the scalp hair fibers must be achieved. Some residual moisture in the hair is acceptable. In one embodiment, the drying of the hair is carried out with an exhaust device. In one embodiment, drying the hair is done by wiping the hair with a towel and/or wringing the hair out by hand.

The distance between the hair dryer or dryer and the head is usually about 10 cm. Hair dryers direct hot air through a nozzle for combing or treating hair. The hair dryer is usually used in such a way that there is some distance to the hair (for example, 20, or 30, or 40 cm) and is often used with a comb or brush. In one embodiment, drying of the hair is carried out with a hair dryer at a temperature of from about 50 to about 100°C. In the variant, hair drying is carried out with a hair dryer at temperatures up to 130°C. Hair drying is also carried out using a hair dryer with a brush in order to assist in hair styling.

In one embodiment, the method for strengthening and/or restoring hair includes, in addition to steps (a), (b), (c), (d), also the step of straightening the hair (e). The hair straightening step (e) includes the use of a hair straightening device composed of metal or ceramic plates. In an embodiment, the metal or ceramic plates are held at a temperature of from about 100 to about 280°C. In an embodiment, the metal or ceramic plates are held at 110 to about 250°C, or about 120 to 240°C, or about 140 to 230°C, or about 160 to about 220°C, or about 180 to about 210°C, or from about 190 to about 200°C.

Also in an embodiment, the straightening of the hair with the appliance is carried out for a period of time from about 1 to about 45 minutes, or from about 2 to 20 minutes, or from about 5 to 15 minutes. In an embodiment, mechanical hair straightening with the help of the device is carried out for at least 10 minutes or at least 12 minutes.

In one embodiment, method (a)-(d) is repeated 2 to 4 times a month on an ongoing basis to strengthen the hair and reduce hair damage.

In an embodiment, the alkaline crosslinker may contain first, second, and third crosslinkers. The first crosslinker may be 4,7,10-trioxa-1,13-tridecanediamine, the second may be 4,9-dioxa-1,12-dodecanediamine, and the third crosslinker may be 1,11-diamino-3,6, 9trioxaundecane.

Also, in an embodiment, the crosslinking composition may include

- 11 041597 from about 3 to about 24% 4,7,10-trioxa-1,13-tridecanediamine, 4,9-dioxa-1,12-dodecanediamine and

1,11-diamino-3,6,9-trioxaundecane present in a weight ratio of 1:1:1, 2:1:1 or 4:1:1;

optionally, a buffer agent;

a cosmetically acceptable carrier;

conditioning agent, which is the reaction product of (a) aminosilane; (b) polysiloxane and optionally (c) polyester;

and wherein the composition has a pH of from about pH 7 to about pH 12.

In one embodiment, the composition includes from about 0.1 to about 15%, or from about 1 to about 10%, or from about 2 to about 5% of conditioning agents, which are products of reaction (a) aminosilane; (b) a polysiloxane; and optionally (c) a polyester. In an embodiment of the invention, the conditioning agent is the reaction product of (a) an aminosilane; (b) polysiloxane; (c) polyester.

In one embodiment, the kit may include: (i) an alkaline crosslinker; (ii) an acidic crosslinker; (iii) conditioning composition. In an embodiment, the kit may serve to strengthen and repair damaged hair. In an embodiment, the kit may serve to facilitate the hair styling process.

The present invention also relates to a hair strengthening kit containing at least two separate compositions, where the first composition contains at least a bifunctional Bronsted base of the general formula X-R-Y, where X and Y are independently selected from the groups amino, carboxylate, nitrate, hydrogen phosphate, phosphate, sulfate, carbonate, and R is an organic molecule group with 1-20 carbon atoms, 0-5 oxygen atoms and 0-5 nitrogen atoms and is not an aromatic or heteroaromatic compound, X-R-Y has a molecular weight of less than 500g /mol, and the second composition contains at least a bifunctional organic acid that can react with the amino groups of the hair, characterized in that at least the bifunctional Brönsted base of the general formula X-R-Y is a mixture of 4,7,10-trioxa-1, 13-tridecanediamine, 4,9-dioxa-1,12-dodecanediamine and 1,11-diamino3,6,9-trioxaundecane, or at least a bifunctional Brønsted base about of general formula X-R-Y is a mixture of 4,7,10-trioxa-1,13-tridecanediamine and 4,9-dioxa-1,12 dodecanediamine, or at least a bifunctional Brønsted base of general formula X-R-Y is 4,7,10- trioxa-1,13-tridecanediamine, and at least the bifunctional organic acid is maleic acid, itaconic acid, or a mixture of maleic acid and itaconic acid, and the first composition has a pH value of 7 to 12, and the second composition has a pH value of 1 .5 to 7, and a reduction in hair breakage is achieved.

In an embodiment, the kit further comprises a hair conditioner.

In an embodiment of the kit, the concentration of at least the bifunctional Bronsted base in the first formulation is 1-30%.

In an embodiment of the kit, the concentration of at least the difunctional organic acid in the second composition is 1-30%.

In an embodiment of the kit, the first and second formulations further comprise at least a viscosity modifying agent.

In an embodiment of the kit, the first and second formulations further comprise at least one emulsifier and/or surfactant.

In an embodiment of the kit, the first and second formulations further comprise at least one particulate material.

In an embodiment of the kit, the first and second formulations further comprise at least one preservative.

In an embodiment of the kit, the first and second formulations are independently mixed with cosmetically acceptable substrates, and the cosmetically acceptable substrate of the first formulation is either identical to or different from the cosmetically acceptable substrate of the second formulation.

In an embodiment, the crosslinker may be used to strengthen hair and/or repair damaged hair. In an embodiment, alkaline as well as acidic crosslinkers can be used to facilitate the hair styling process.

Examples

The following examples further describe and demonstrate embodiments of the method within the scope of the present invention. The examples are for illustrative purposes only and should not be construed as limiting the present invention, as many variations are possible without departing from its scope.

Composition example for an alkaline crosslinker (total weight 100 g).

Liquid A: 10 g 4,7,10-trioxa-1,13-tridecanediamine, 5 g 4,9-dioxa-1,12-dodecanediamine, 5 g 1,11-diamino-3,6,9-trioxaundecane, 2 g epoxyaminosilane copolymer, QSP water.

Liquid B: 25 g 4,7,10-trioxa-1,13-tridecanediamine, QSP water.

- 12 041597

Liquid C: 12 g 4,7,10-trioxa-1,13-tridecanediamine, 3 g 4,9-dioxa-1,12-dodecandiamine, 3 g

1,11-diamino-3,6,9-trioxaundecane, 2 g epoxyaminosilane copolymer, QSP water.

Rinse conditioner A: 16 g 4,7,10-trioxa-1,13-tridecanediamine, 8 g 4,9-dioxa-1,12 dodecanediamine, 1.00 g cetyltrimethylammonium chloride, 1.00 g polymethylphenylsiloxane, 0.40 g phenoxyethanol , 0.20 g PHB-methyl ester, 1.00 g Dow Corning 949 Cationic Emulsion®, 5.00 g isododecane, 0.40 g perfume oil, QSP water.

Rinse-off conditioner B: 18 g 4,7,10-trioxa-1,13-tridecanediamine, 1.00 g cetyltrimethylammonium chloride, 1.00 g polymethylphenylsiloxane, 0.40 g phenoxyethanol, 0.20 g PHB-methyl ether, 8, 00 g Dow Corning 57113 Cationic Emulsion®, 5.00 g isododecane, 0.40 g perfume oil, QSP water.

Leave-in conditioner A: 6 g 4,7,10-trioxa-1,13-tridecanediamine, 3 g 4,9-dioxa-1,12 dodecanediamine, 1.00 g cetyltrimethyl chloride 1.00 g polymethylphenylsiloxane, 0.40 g phenoxyethanol, 0 .20 g PHB-methyl ester, 8.00 g Momentive™ Cationic Emulsion®, 5.00 g isododecane, 0.40 g perfume oil, QSP water.

Leave-in conditioner B: 10 g 4,7,10-trioxa-1,13-tridecanediamine, 5 g 1,11-diamino-3,6,9 trioxadecane, 0.10 g vitamin E-acetate, 0.50 g polymethylphenylsiloxane, 10 0.00 g propylene glycol, 0.50 g behenyltrimethylammonium chloride, 0.05 g sodium chloride, 0.30 g D-panthenol, 0.30 g PHB propyl ether, 2.00 g isododecane, 0.20 g perfume oil, QSP water.

Composition example for an acidic crosslinker (total weight 100 g).

Liquid A': 25 g maleic acid, QSP water.

Liquid B': 25 g itaconic acid, QSP water.

Liquid C': 12 g maleic acid, 12 g itaconic acid, 3 g 1,11-diamino-3,6,9 trioxaundecane, 2 g epoxyaminosilane copolymer, QSP water.

Rinse conditioner A': 12 g maleic acid, 1.00 g ammonium cetyltrimethyl chloride, 1.00 g polymethylphenylsiloxane, 0.40 g phenoxyethanol, 0.20 g PHB-methyl ester, 1.00 g Dow Corning 949 Cationic Emulsion®, 5 .00 g isododecane, 0.40 g perfume oil, QSP water.

Rinse conditioner B': 6 g maleic acid, 6 g itaconic acid, 1.00 g ammonium cetyltrimethyl chloride, 1.00 g polymethylphenylsiloxane, 0.40 g phenoxyethanol, 0.20 g PHB-methyl ester, 8.00 g Dow Corning 57113 Cationic Emulsion®, 5.00 g isododecane, 0.40 g perfume oil, QSP water.

Leave-in conditioner A': 3g maleic acid, 1.00g cetyltrimethylammonium chloride, 1.00g polymethylphenylsiloxane, 0.40g phenoxyethanol, 0.20g PHB-methyl ester, 8.00g Momentive™ Cationic Emulsion®, 5, 0 g isododecane, 0.40 g perfume oil, QSP water.

Leave-in conditioner B': 3 g maleic acid, 3 g itaconic acid, 0.10 g vitamin Eacetate, 0.50 g polymethylphenylsiloxane, 10.00 g propylene glycol, 0.50 g behenyltrimethylammonium chloride, 0.05 g sodium chloride, 0, 30 g D-panthenol, 0.30 g PHB-propyl ether, 2.00 g isododecane, 0.20 g perfume oil, QSP water.

Data

The effectiveness of strengthening hair tested on alkaline as well as acidic cross-linking compositions of the present invention. Used brushes from short natural hair. They are washed with K-RAK Shampoo to ensure that the hair is in a clean condition without residues of substances that can affect the final result. The brushes are then rinsed. Excess water is removed from the hair by squeezing the brushes. The brushes are treated with a crosslinker that consists of the active agents as listed in the table, QSP water buffered to pH 10 for alkaline crosslinkers and QSP water buffered to pH 4 for acid crosslinkers. These ingredients are mixed on a rotary mixer for 15 minutes. 0.5 g of cross-linking composition per 1 g of hair is used. The cross-linking composition remains on the hair for 30 minutes. After this time, the hair is dried with a hairdryer and combed with a standard metal comb up to 500 movements. Fortified hair and damaged hair are redistributed based on the number of damaged hair fibers collected by the comb and normalized depending on the volume of hair brushes. 5 brushes of hair in the experiment were processed and combed, the results were averaged. When the first and second treatments were applied, the hair tassels were first treated with the alkaline hair strengthening composition as described above without the hair drying step, followed by the treatment with the acid hair strengthening composition as described above, including drying the hair.

- 13 041597

Hair breakage results after n brushings

Treatment 50 combs 250 combs 500 combs Reference: Unprocessed hair 5.0% 8.1% 9.7% 25% maleic acid 2.8% 4.1% 6.3% 25% itaconic acid 2.5% 3.9% 6.4% 12% maleic + 12% itaconic acid 2.5% 4.4% 5.9% 15% 4,7,10-trioxa-1,13- tridecanediamine 2.9% 4.4% 6.8% 15% 4,9-dioxa-1,12- dodecanediamine 3.1% 3.9% 5.9% 15% 1,11-diamino-3,6,9- trioxaundecana 3.1% 4.2% 6.2% first: 25% maleic acid second: 15% 4,7,10-trioxa-1,13- tridecanediamine 0.8% 2.1% 3.3% first: 25% maleic acid second: 15% 4,9-dioxa-1,12- dodecanediamine 1.1% 2.3% 3.2% first: 25% maleic acid second: 1,11-diamino-3,6,9- trioxaundecana 1.0% 1.9% 3.4% first: 25% itaconic acid second: 5% 4,7,10-trioxa-1,13- tridecanediamine + 5% 4,9-dioxa- 1,12 dodecanediamine + 5% 1,11- diamino-3,6,9-trioxaundecane 1.2% 2.5% 3.1%

When averaged over five experimental results, the relative standard deviation is less than 15%. As can be seen from the table, sequential use of the alkaline hair strengthening composition of the present invention with the acidic hair strengthening composition of the present invention significantly reduces hair breakage. The same results in reducing hair breakage were achieved when an alkaline hair strengthening compound was first mixed with a commercially available hair coloring agent, then left on the hair brush for the time specified by the dye manufacturer's instructions, followed by an acidic hair strengthening compound according to instructions for use, followed by hair drying.

To dye human hair using oxidation dye technology, it is generally necessary to treat the hair with a mixture of suitable oxidation dyes and at least one dye oxidant. Hydrogen peroxide is the most commonly used dye oxidizing agent. However, in addition to oxidizing the color, treating the hair with hydrogen peroxide can also solubilize the color component of melanin in the hair and can lead to undesirable qualities of the hair, such as poor condition associated with increased brittleness and damage to the hair. These undesirable properties are explained by the conditions of conventional peroxide treatment, which is part of the hair coloring process, which requires high pH (pH > 9), long exposure (10 to 60 minutes) and relatively high concentration of oxidizing solutions (up to 20% oxygen volume) for effective dyeing. oxidation. Thus, there is a need for hair coloring agents that can oxidize dyes and color hair effectively and at the same time strengthen the hair to prevent damage to the hair.

The hair bleaching process is very similar to the hair coloring process. Bleaching is basically the process of removing the natural color from the hair. Due to the virtually unlimited color variations of hair color, bleaching as such usually does not create the shape or aesthetic appeal of the color in the hair, bleaching only emphasizes the tone of the color inherent in the original hair. For these reasons, hair that has been bleached is then treated with a hair tonic, a composition containing a hair dye that imparts the desired final color to bleached hair. The degree to which the natural color should be bleached in the hair is primarily determined by the desired end color. Toners do not lighten hair to a significant extent, they bring the color tone of pre-lightened hair to the desired basic shade of blond, for example, a pastel blond color shade leads to a pale blond color after processing pre-bleached hair, when processing unbleached hair, it leads only to a blond color hair.

Used as such in admixture with commercially available hair coloring or bleaching agents, followed by the use of acidic hair strengthening formulations, the alkaline as well as acidic hair strengthening formulations of the present invention improve hair quality, reduce hair breakage, and reduce hair damage. 14 041597 improves hair shine and shine, facilitates hair styling and improves moisture resistance of hair.

The dimensions and values given in this document should not be construed as being strictly limited to precise numerical values. Instead, unless otherwise indicated, each such value denotes both the value itself and a functionally equivalent range surrounding that value. For example, a value shown as 10% should mean about 10%.

Each document cited herein, including any cross-references or related patents or patent publications, is hereby incorporated by reference in its entirety unless expressly excluded or otherwise limited. The citation of any document is not an admission that it is prior art with respect to any document disclosed or claimed herein, or that it, by itself or in any combination with any other reference or references, teaches, suggests or discloses any such embodiment. In addition, to the extent that any meaning or definition of a term in this document conflicts with any meaning or definition of the same term in a document incorporated by reference, the meaning or definition given to that term in this document shall control.

While specific variations have been illustrated and described herein, it should be understood that various other changes and modifications may be made without departing from the spirit and scope of the claimed subject matter. In addition, although various aspects of the claimed subject matter have been described here, such aspects should not be used in combination. Therefore, the appended claims are intended to cover all such changes and modifications that fall within the scope of the claimed subject matter.

Claims (22)

CLAIM 1. A method for strengthening hair, including the steps: a) applying to the hair a first composition that contains at least a bifunctional Bronsted base of the general formula X-R-Y, where X and Y are independently selected from the groups amino, carboxylate, nitrate, hydrogen phosphate, phosphate, sulfate and carbonate, and R represents an organic molecules with 1-20 carbon atoms, 0-5 oxygen atoms and 0-5 nitrogen atoms and is not aromatic or heteroaromatic, and X-R-Y has a molecular weight of less than 500 g/mol, and b) application to the hair of a second composition containing at least a bifunctional organic acid capable of reacting with the amino groups of the hair, characterized in that at least the bifunctional Bronsted base of the general formula X-R-Y is a mixture of 4,7,10-trioxa-1 ,13-tridecanediamine, 4,9-dioxa-1,12-dodecanediamine and 1,11-diamino3,6,9-trioxaundecane, or at least a bifunctional Bronsted base of the general formula X-R-Y is a mixture of 4,7,10- trioxa-1,13-tridecanediamine and 4,9-dioxa-1,12 dodecanediamine, or at least a bifunctional Bronsted base of general formula X-R-Y is 4,7,10-trioxa-1,13-tridecanediamine, and at least , the bifunctional organic acid is maleic acid, itaconic acid, or a mixture of maleic acid and itaconic acid, and the first composition has a pH of 7 to 12, and the second composition has a pH of 1.5 to 7, and hair breakage reduction is achieved. 2. The method according to claim 1, wherein the concentration of at least the bifunctional Bronsted base in step (a) is 1-30%. 3. The method according to any one of the preceding claims, wherein the concentration of at least the difunctional organic acid in step (b) is 1-30%. 4. A method according to any one of the preceding claims, wherein step (a) is performed before step (b). 5. A method according to any one of the preceding claims, wherein step (b) is performed before step (a). 6. The method according to any one of the preceding claims, wherein the hair is dried between steps (a) and (b) and the drying time is from 1 to 60 minutes. 7. The method of claim 6 wherein a dryer is used to dry the hair. 8. A method according to any one of the preceding claims, wherein the composition of step (a) is left on the hair for 1-45 minutes. 9. A method according to any one of the preceding claims, wherein the composition of step (b) is left on the hair for 1-45 minutes. 10. The method according to any one of the preceding claims, wherein between the execution of steps (a) and (b) or (b) and (a) there is a waiting time of 1 to 60 minutes. 11. The method according to any of the preceding claims, wherein the formulations of steps (a) and (b) are independently admixed with a cosmetically acceptable carrier, and wherein the cosmetically acceptable carrier of the formulation of step (a) is either identical or non-identical to the cosmetically acceptable carrier of the formulation of step (b). ). 12. The method according to any of the previous paragraphs, in which the composition of stage (a) is mixed with commercial - 15 041597 a commercially available composition for coloring hair or for bleaching hair prior to application to the hair. 13. The method according to any one of the preceding claims, wherein the hair is treated with a hair care composition containing thioglycolic acid before performing step (a). 14. A set for strengthening hair, containing at least two separate compositions, where the first composition contains at least a bifunctional Brönsted base of the general formula X-R-Y, where X and Y are selected independently from each other from the groups amino, carboxylate, nitrate, hydrogen phosphate, phosphate, sulfate, carbonate, and R is an organic molecule group with 1-20 carbon atoms, 0-5 oxygen atoms, and 0-5 nitrogen atoms and is not an aromatic or heteroaromatic compound, X-R-Y has a molecular weight of less than 500 g/mol, and the second composition contains at least a bifunctional organic acid that can react with the amino groups of the hair, characterized in that at least the bifunctional Bronsted base of the general formula X-R-Y is a mixture of 4,7,10-trioxa-1,13-tridecanediamine, 4,9-dioxa-1,12-dodecanediamine and 1,11-diamino3,6,9-trioxaundecane, or at least a bifunctional Bronsted base of the general formula X-R-Y is a mixture 4,7,10-trioxa-1,13-tridecanediamine and 4,9-dioxa-1,12 dodecanediamine, or at least a bifunctional Bronsted base of the general formula X-R-Y is 4,7,10-trioxa-1,13- tridecanediamine, and at least the bifunctional organic acid is maleic acid, itaconic acid, or a mixture of maleic acid and itaconic acid, and the first composition has a pH value of 7 to 12, and the second composition has a pH value of 1.5 to 7, and hair breakage is reduced. 15. The hair strengthening kit of claim 14, wherein the kit further comprises a hair conditioner. 16. A hair strengthening kit according to any one of claims 14 or 15, wherein the concentration of at least the bifunctional Bronsted base in the first composition is 1-30%. 17. A hair strengthening kit according to any one of claims 14-16, wherein the concentration of at least the bifunctional organic acid in the second composition is 1-30%. 18. A hair strengthening kit according to any one of claims 14 to 17, wherein the first and second formulations further comprise at least a viscosity modifying agent. 19. A hair strengthening kit according to any one of claims 14 to 18, wherein the first and second formulations further comprise at least one emulsifier and/or surfactant. 20. A hair strengthening kit according to any one of claims 14 to 19, wherein the first and second formulations further comprise at least one particulate material. 21. Set for strengthening hair according to any one of paragraphs. 14-20, wherein the first and second formulations further comprise at least one preservative. 22. A hair strengthening kit according to any one of claims 14 to 21, wherein the first and second formulations are independently mixed with cosmetically acceptable substrates, and wherein the cosmetically acceptable substrate of the first formulation is either identical to or different from the cosmetically acceptable substrate of the second formulation. .