JP2008150308A - Hair modifier, hair cosmetic comprising hair modifier ingredient and method for modifying hair - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a hair modifier essentially modifying damaged hair, improving coherency, moisture retaining properties and elasticity of hair and having excellent long-term persistence of effects, to provide a hair cosmetic comprising a hair modifier ingredient and to provide a method for modifying the hair using the hair cosmetic. <P>SOLUTION: The hair modifier comprises an ester compound of a 4-6C unsaturated dicarboxylic acid with a 12-24C linear or branched saturated or unsaturated alcohol. The hair cosmetic comprises the hair modifier ingredient. The method for modifying the hair comprises applying the hair cosmetic to the hair. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a hair modifier for reducing or repairing damage to the hair surface, or protecting the hair surface, a hair cosmetic containing a hair modifier component, and a method for modifying hair.

  In recent years, with the diversification of hairstyles, the effects of chemical treatments such as hair dyes, bleaches, permanent wave agents, hair straighteners, daily physical treatments such as excessive brushing and blowing, or ultraviolet rays, etc. Therefore, the hair tends to be damaged easily, particularly to the hair surface. When the lipid layer having a function as a protective layer on the hair surface is lost due to such damage, undesired phenomena such as so-called dryness, deterioration of finger passage and glossiness occur. Furthermore, interstitial substances inside the hair may flow out, resulting in a state of hair elasticity (relief, strain), reduced cohesiveness, and broken hair.

  Conventionally, hair modifiers have been used for the purpose of reducing or repairing damage to the hair surface or for enhancing the protection of the hair surface.

  As conventional hair modifiers, oils, polymer compounds capable of forming a film, or quaternary ammonium salts such as stearyltrimethylammonium chloride (STAC) are temporarily attached to the hair surface to improve the hair condition. Quality was the mainstream.

  For example, this STAC hydrophobizes the hair surface based on electrostatic interactions such as ionic bonds and physical phenomena such as adsorption to hair that has been damaged and has become hydrophilic and ionized. As a result, the frictional resistance of the hair surface is reduced as compared with damaged hair, and the surface modification of the hair is performed. Particularly, in recent years, the interaction between the hair surface and STAC has been strengthened. For this purpose, a hair modifier using diglucosyl gallic acid (DGA) has also been developed (for example, Non-Patent Document 1).

  In addition to the application of hair cosmetics containing protein hydrolysates and amino acids as hair damage repair ingredients to hair damage sites (for example, Patent Document 1), the purpose is not limited to hair modification. There is also a technique of introducing a long-chain alkyl group by a covalent bond for the purpose of modifying a keratin substance (for example, Patent Document 2).

  However, the hair modifier using the electrostatic interaction such as ionic bond and hydrogen bond as described above can obtain temporary effects, but STAC or DGA whose surface is covered by daily hair washing or the like. Hair modifiers such as are easily washed away. As a result, the hydrophilic part and ionic part of the hair surface are exposed again, and the hairiness, cohesiveness and deterioration of fingering are regenerated, so it cannot be said that it is a fundamental solution for modifying the hair surface. Moreover, it was also a problem from the viewpoint of the sustainability of the hair modification effect. Also, hair cosmetics in which protein hydrolyzate and amino acids are allowed to act on hair as hair damage repair ingredients are not satisfactory in terms of their sustainability, although hair elasticity and elasticity are obtained.

  Patent Document 2 specifically discloses a method for treating a keratin fiber that forms a covalent bond by an acylation reaction using an acid halide, but the acid halide is used for normal hair. In view of the stability of the compound in an aqueous solution, the sensitization to the human body, and the safety including mutagenicity, it was not easy to use.

  Because of these problems, it is desirable to develop a hair modifier that essentially modifies damaged hair, improves the cohesiveness, moisture retention, and elasticity of the hair, and has excellent durability. It was.

JOURNAL OF OLEO SCIENCE, Vol. 53, no. 6,295-304 (2004) Japanese Patent Application Laid-Open No. 11-139941 JP 2000-226763 A

  The present invention essentially modifies damaged hair, improves hair cohesiveness, moisture retention, elasticity, and has a long-lasting effect, and the hair modifying agent It aims at providing the hair cosmetics containing an ingredient, and the modification | reformation method of the hair using the hair cosmetics.

  As a result of intensive studies, the present inventors have found that an ester compound of an unsaturated dicarboxylic acid and a linear or branched saturated or unsaturated alcohol overcomes the drawbacks of conventional hair modifiers, Based on convenience and safety to the living body, the present inventors have found that the hair modifying agent has a remarkably excellent modifying effect on damaged hair, and completed the present invention.

That is, the present invention is as follows.
(1) A hair modifier containing an ester compound of an unsaturated dicarboxylic acid having 4 to 6 carbon atoms and a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms.
(2) The ester compound is a diester compound, and at least one carboxyl group of the unsaturated dicarboxylic acid forms an ester bond with a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms. The hair modifier according to (1).
(3) The diester compound according to (2), wherein the two carboxyl groups of the unsaturated dicarboxylic acid form an ester bond with a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms. Hair modifier.
(4) The hair modifier according to any one of (1) to (3), wherein the unsaturated dicarboxylic acid is maleic acid.
(5) The hair modifier according to any one of (1) to (4), wherein the alcohol is a linear or branched saturated alcohol having 18 to 22 carbon atoms.
(6) The hair modifier according to any one of (1) to (4), wherein the alcohol is a linear or branched unsaturated alcohol having 18 to 22 carbon atoms.
(7) The hair modifier according to (6), wherein the unsaturated alcohol is oleyl alcohol.
(8) The hair modifier according to (1), wherein the ester compound is dioleyl maleate.
(9) A hair cosmetic containing the hair modifying agent according to any one of (1) to (8).
(10) A method for modifying hair, wherein the hair cosmetic composition according to (9) is applied to hair.

  Although the reaction mechanism and binding state of the ester compound to the hair surface in the present invention are not clear, the unsaturated bond adjacent to the ester site has a high reaction activity, and thus easily and firmly covalently bonds to the hair surface. Alternatively, it is presumed that the adsorbability with the hair surface is increased.

(Hair modifier)
In the present specification, the term “hair modifier” means an agent capable of improving hair cohesiveness, moisture retention, elasticity, etc. by reducing or repairing hair damage or protecting the hair surface. To do.

(Hair cosmetics containing hair modifier components)
In the present specification, the term “hair cosmetic containing a hair modifier component” refers to any cosmetic that comes in contact with and / or comes into contact with keratin substances present in the human body including hair and body hair. Also means. Examples of hair cosmetics containing such a hair modifier component include hair care agents such as shampoos, rinses, and treatments, or styling agents such as gels, emulsions, mousses, and waxes, as well as hair dyes, hair manicures, Examples include topical cosmetic compositions that are blended as an additive component to hair dyes such as permanent agents and hair straighteners and drugs intended for wave / straight.

  The hair modifying agent of the present invention and the hair cosmetic containing the hair modifying component reduce or repair the damage to the hair surface, or protect the hair surface to modify the damaged hair, It effectively improves the cohesiveness, moisture retention and elasticity of the hair, and is excellent in long-lasting effect and feel after finishing.

The present invention will be specifically described below.
The hair modifying agent of the present invention and the hair cosmetic composition containing the hair modifying component include an unsaturated dicarboxylic acid having 4 to 6 carbon atoms and a linear or branched saturated or unsaturated carbon having 12 to 24 carbon atoms. It contains an ester compound with a saturated alcohol (hereinafter sometimes referred to as “hair modifier component”), and at least one of the two carboxyl groups in the unsaturated dicarboxylic acid has 12 carbon atoms. It is an ester compound which forms an ester bond with -24 linear or branched saturated or unsaturated alcohols.

  Examples of the ester compound include diester compounds in which two carboxyl groups of the unsaturated dicarboxylic acid form an ester bond with a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms, the two carboxyls A diester compound in which only one of the groups forms an ester bond with a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms, and the other carboxyl group forms an ester bond with another alcohol, Alternatively, a monoester compound in which only one of the two carboxyl groups forms an ester bond with a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms.

  Of these, the dicarboxyl compound in which the two carboxyl groups form an ester bond with a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms, or only one of the two carboxyl groups has a carbon number. A diester compound in which 12 to 24 linear or branched saturated or unsaturated alcohol forms an ester bond and the other carboxyl group forms an ester bond with another alcohol is preferable.

  These ester compounds in the hair cosmetic containing the hair modifier of the present invention and the hair modifier component may be any ester compound having the ester bond, and are produced from the corresponding dicarboxylic acid and alcohol. It is not limited at all.

  An ester compound in which two carboxyl groups in an unsaturated dicarboxylic acid form an ester bond with a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms is, for example, an unsaturated dicarboxylic acid or an unsaturated dicarboxylic acid. The acid anhydride and the corresponding long-chain alcohol compound can be obtained by adding a catalyst in a solvent capable of azeotropic dehydration such as toluene to form a dehydration ester, and then removing the solvent.

  In addition, one of two carboxyl groups in the unsaturated dicarboxylic acid forms an ester bond with a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms, and the other carboxyl group is an ester with another alcohol. For example, the ester compound forming the bond may be prepared by adding a catalyst in an azeotropic dehydration solvent such as toluene with unsaturated dicarboxylic acid or unsaturated dicarboxylic anhydride and two or more corresponding alcohol compounds. After dehydrating esterification, it can be obtained by distillation or separation and purification with a silica gel column using a suitable developing solvent.

  Examples of the unsaturated dicarboxylic acid having 4 to 6 carbon atoms include fumaric acid, maleic acid, acetylenedicarboxylic acid, itaconic acid, citraconic acid, trans-glutaconic acid, trans, trans-muconic acid, cis, cis-muconic acid and the like. Is mentioned. Of these, maleic acid is preferred.

  Examples of the linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms include lauryl alcohol, 1-tridecanol, myristyl alcohol, 1-pentadecanol, cetyl alcohol, 1-heptadecanol, Stearyl alcohol, 1-nonadecanol, arachin alcohol, 1-henicosanol, behenyl alcohol, 1-tricosanol, 1-tetracosanol, 2-dodecanol, 4-methyl-1-dodecanol, 2-tridecanol, 4-methyl-1-tridecanol, 2-tetradecanol, 4-methyl-1-tetradecanol, 2-pentadecanol, 2-hexadecanol, 7-methyl-1-hexadecanol, 4-heptadecanol, isostearyl alcohol, 2- Octadecanol, 2-nona Canol, 9-methyl-1-nonadecanol, 2-dodecen-1-ol, 8,10-dodecadien-1-ol, 7-dodecyn-1-ol, 2-tridecen-1-ol, 9-tetradecene-1- All, 9,12-tetradecadien-1-ol, oleyl alcohol, linoleyl alcohol, linolenyl alcohol, 11-icosen-1-ol, 5,8,11,14-icosatetraen-1-ol, 13- Docosen-1-ol, 2,6,10-trimethyl-5,9-undecadien-1-ol, 3,7,11,15-tetramethyl-2-hexadecen-1-ol, 3,7,11,15 -Tetramethyl-2,6,10,14-hexadecatetraen-1-ol and the like. Among these, a linear or branched saturated or unsaturated alcohol having 18 to 22 carbon atoms is preferable, and a linear or branched unsaturated alcohol having 18 to 22 carbon atoms is more preferable. These alcohols may be used alone or as a mixture of two or more.

  Furthermore, one of the two carboxyl groups in the unsaturated dicarboxylic acid forms an ester bond with a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms, and the other carboxyl group is an ester with another alcohol. In the case of an ester compound forming a bond, the other alcohol is, for example, an alcohol having 1 to 11 carbon atoms, preferably an alcohol having 1 to 8 carbon atoms, specifically methyl alcohol, ethyl alcohol, isopropyl alcohol, Examples include octyl alcohol.

  Examples of ester compounds synthesized from these compounds in which two carboxyl groups in unsaturated dicarboxylic acid form an ester bond with a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms include: Examples of the ester compound of the unsaturated dicarboxylic acid and the alcohol include dilauryl maleate, dimyristyl maleate, dicetyl maleate, distearyl maleate, dibehenyl maleate, dioleyl maleate, dilinoleyl maleate, maleate. Dilinolenyl acid, di (11-icosenyl) maleate, diisostearyl maleate, di (3,7,11,15-tetramethyl-2-hexadecenyl) maleate, maleic acid (cetyl) (oleyl), maleic acid ( Oleyl) (stearyl), male Acid (linoleyl) (oleyl), maleic acid (icosenyl) (oleyl), maleic acid (linolenyl) (oleyl), maleic acid (linolenyl) (linoleyl), maleic acid (linoleyl) (stearyl), dilauryl fumarate, fumaric acid Dimyristyl, dicetyl fumarate, distearyl fumarate, dibehenyl fumarate, diisostearyl fumarate, dioleyl fumarate, dilinoleyl fumarate, dilinolenyl fumarate, di (11-icosenyl) fumarate, di (3,7, 11,15-tetramethyl-2-hexadecenyl), fumaric acid (cetyl) (oleyl), fumaric acid (oleyl) (stearyl), fumaric acid (linoleyl) (oleyl), fumaric acid (icosenyl) (oleyl), fumaric acid (Linolenyl) (oleyl), fumaric acid ( Norenyl) (linoleyl), fumaric acid (linoleyl) (stearyl), acetylenedicarboxylic acid distearyl, acetylenedicarboxylic acid dioleyl, itaconic acid distearyl, itaconic acid dioleyl, citraconic acid distearyl, citraconic acid dioleyl, trans-glutaconic acid distearyl , Trans-glutaconate dioleyl, trans, trans-muconate distearyl, trans, trans-muconate dioleyl, cis, cis-muconate distearyl, cis, cis-muconate dioleyl, and the like. Among them, considering the affinity and effect on the damaged part of the hair surface (feeling and coherence of hair), dilauryl maleate, dimyristyl maleate, dicetyl maleate, distearyl maleate, dibehenyl maleate, diiso maleate Stearyl, dioleyl maleate, dilinoleyl maleate, dilinolenyl maleate, di (11-icosenyl) maleate, di (3,7,11,15-tetramethyl-2-hexadecenyl) maleate, cetyl maleate (oleyl) ), Maleic acid (oleyl) (stearyl), maleic acid (linoleyl) (oleyl), maleic acid (icosenyl) (oleyl), maleic acid (linolenyl) (oleyl), maleic acid (linolenyl) (linoleyl), maleic acid ( Linoleil) (stearyl) Preferably diester compounds, distearyl maleate, dioleyl maleate are more preferred. Furthermore, in terms of saturated or unsaturated alcohols, diester compounds with unsaturated alcohols are preferred in terms of feel (hair unity, moist and soft).

  In addition, one of two carboxyl groups in the unsaturated dicarboxylic acid forms an ester bond with a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms, and the other carboxyl group is an ester with another alcohol. Examples of the ester compound forming a bond include maleic acid (ethyl) (oleyl), maleic acid (ethyl) (stearyl), maleic acid (ethyl) (isostearyl), maleic acid (ethyl) (cetyl), Examples thereof include maleic acid (octyl) (oleyl), maleic acid (octyl) (stearyl), maleic acid (octyl) (isostearyl) and the like.

  These hair modifier components in the hair cosmetic composition containing the hair modifier and the hair modifier component may be blended singly or in combination of two or more. The content of the hair modifier component is preferably from 0.01 to 20% by mass, more preferably from 0.05 to 20%, from the viewpoint that it can efficiently improve the moisture feeling and fingering property of the hair and give a preferable feel. It is 10 mass%, More preferably, it is 0.1-5 mass%.

  Furthermore, the hair modifying agent and the hair cosmetic containing the hair modifying component include, as other components, an oil component, a surfactant, a cationic polymer, an anionic polymer, an amphoteric polymer, a nonionic polymer, etc. Ingredients selected from these polymer compounds can be blended.

  The oil component is preferably blended from the viewpoint of imparting a moist feeling to the hair and improving fingering properties. Specific components include oils and fats, waxes, higher alcohols, higher fatty acids, alkyl glyceryl ethers, Examples include esters, hydrocarbons, and silicones.

  As fats and oils, olive oil, camellia oil, shea fat, almond oil, tea seed oil, sasanqua oil, safflower oil, sunflower oil, soybean oil, cottonseed oil, sesame oil, beef fat, cacao butter, corn oil, peanut oil, rapeseed oil, Examples include rice bran oil, rice germ oil, wheat germ oil, pearl barley oil, grape seed oil, avocado oil, carrot oil, macadamia nut oil, castor oil, flaxseed oil, coconut oil, mink oil, egg yolk oil and the like. Examples of waxes include beeswax, candelilla wax, carnauba wax, jojoba oil, and lanolin.

  Higher alcohols include lauryl alcohol, myristyl alcohol, cetyl alcohol (cetanol), stearyl alcohol, cetostearyl alcohol, arachin alcohol, behenyl alcohol, 2-hexyldecanol, isostearyl alcohol, 2-octyldodecanol, decyltetradecanol, oleyl alcohol Linoleyl alcohol, linolenyl alcohol, lanolin alcohol and the like. Examples of higher fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, isostearic acid, hydroxystearic acid, oleic acid, undecylenic acid, linoleic acid, ricinoleic acid, and lanolin fatty acid.

  Examples of the alkyl glyceryl ether include batyl alcohol (monostearyl glyceryl ether), chimyl alcohol (monocetyl glyceryl ether), selachyl alcohol (monooleyl glyceryl ether), and isostearyl glyceryl ether.

  Esters include diisopropyl adipate, diisobutyl adipate, dioctyl adipate, 2-hexyldecyl adipate, diisostearyl adipate, isopropyl myristate, cetyl octanoate, cetyl isooctanoate, isononyl isononanoate, isodecyl isononanoate , Isotridecyl isononanoate, diisopropyl sebacate, octyldodecyl myristate, isopropyl palmitate, butyl stearate, stearyl stearate, hexyl laurate, myristyl myristate, decyl oleate, hexyl decyl dimethyloctanoate, triisodecyl myristate, myristic acid Isostearyl, 2-ethylhexyl palmitate, octyldodecyl ricinoleate, fatty acid (C10-30) (choleste Lanylyl), lauryl lactate, cetyl lactate, myristyl lactate, octyldodecyl lactate, lanolin acetate, isocetyl stearate, isocetyl isostearate, cholesteryl 12-hydroxystearate, ethylene glycol di-2-ethylhexanoate, dipentaerythritol fatty acid Examples thereof include esters, N-alkyl glycol monoisostearate, cetyl caprate, glyceryl tricaprylate, neopentyl glycol dicaprate, diisostearyl malate, and lanolin derivatives.

  Examples of the hydrocarbon include α-olefin oligomer, light isoparaffin, light liquid isoparaffin, liquid isoparaffin, liquid paraffin, squalane, polybutene, paraffin, polyethylene powder, microcrystalline wax, petrolatum and the like.

  Examples of silicones include dimethyl silicone, methyl phenyl silicone, cyclic dimethyl silicone, cyclic silicone, methyl hydrogen silicone, amino modified silicone, ammonium modified silicone, terminal hydroxyl group modified dimethyl polysiloxane, alcohol modified silicone, aliphatic alcohol modified silicone, alkyl modified. Examples thereof include silicone, polyether-modified silicone, epoxy-modified silicone, and fluorine-modified silicone. Specifically, octamethylcyclotetrasiloxane, octamethyltrisiloxane, methylpolysiloxane (dimethicone), dimethylsiloxane / methylstearoxysiloxane copolymer, dimethylsiloxane / methylcetyloxysiloxane copolymer, stearoxytrimethylsilane, Stearoxymethyl polysiloxane, decamethylcyclopentasiloxane, decamethyltetrasiloxane, tetradecamethylcycloheptasiloxane, tetradecamethylhexasiloxane, tetrahydrotetramethylcyclotetrasiloxane, dodecamethylcyclohexasiloxane, tris (tributoxysiloxy) Methylsilane, trimethylsiloxysilicic acid, bisphenyldodecamethylhexasiloxane, hexadecylmethylcyclopolysiloxane, Samethylcyclotrisiloxane, hexamethyldisiloxane, poly (oxyethylene / oxypropylene) methylpolysiloxane copolymer, polyoxyethylene / methylpolysiloxane copolymer, polyoxypropylene / methylpolysiloxane copolymer, polymethacryl Methyl / dimethylpolysiloxane graft copolymer, methylcyclopolysiloxane, methylhydrogenpolysiloxane, methylphenylpolysiloxane, methylpolysiloxane / cetylmethylpolysiloxane / poly (oxyethylene / oxypropylene) methylpolysiloxane copolymer And poly (oxyethylene / oxypropylene) / butylene / methylpolysiloxane copolymer.

  Among these silicone derivatives, it is preferable to be at least one selected from dimethyl silicone, polyether-modified silicone, and amino-modified silicone because it can improve the finger-penetrating property of hair.

  These oil components in the hair cosmetic composition containing the hair modifier and the hair modifier component may be blended singly or in combination of two or more. The content of the oil component is preferably 0.01 to 30% by mass, more preferably 0.05 to 20% by mass, from the viewpoint of efficiently improving the moisture feeling of the hair, fingering property and preventing stickiness of the hair. %, More preferably 0.1 to 10% by mass.

  In the hair modifying agent of the present invention and the hair cosmetic containing the hair modifying component, a surfactant is added from the viewpoint of improving the stability of the system including solubilization, dispersibility and the like of the solvent. It can be included. As the surfactant, any of a nonionic surfactant, a cationic surfactant, an anionic surfactant and an amphoteric surfactant can be used.

  Specific examples of the nonionic surfactant include polyoxyethylene (hereinafter referred to as POE) alkyl ethers, POE alkylphenyl ethers, POE / polyoxypropylene alkyl ethers, POE sorbitan fatty acid esters, POE propylene glycol fatty acid. Examples thereof include esters and aliphatic alkanolamides.

  Cationic surfactants include lauryl trimethyl ammonium chloride, cetyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, alkyl trimethyl ammonium chloride, distearyl dimethyl ammonium chloride, cetyl trimethyl ammonium bromide, stearyl trimethyl ammonium bromide, ethyl lanolin sulfate fatty acid Examples thereof include aminopropylethyldimethylammonium, stearyltrimethylammonium saccharin, cetyltrimethylammonium saccharin, and methyl behenyltrimethylammonium sulfate.

  Examples of anionic surfactants include alkyl sulfates such as sodium lauryl sulfate, POE alkyl sulfates such as POE lauryl ether sodium sulfate, alkyl sulfate esters such as lauryl sulfate triethanolamine, stearoylmethyl taurine sodium, dodecylbenzenesulfonic acid Examples include triethanolamine, sodium tetradecenesulfonate, POE lauryl ether phosphate and salts thereof, N-lauroyl glutamates, N-lauroylmethyl-β-alanine salts, carboxymethyldextran and carboxymethylchitin.

  Examples of amphoteric surfactants include 2-undecyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine sodium, cocoamidopropyl betaine, lauryldimethylaminoacetic acid betaine.

  Cationic polymers, anionic polymers, amphoteric polymers, and nonionic polymers are generally known as polymer compounds, and specific compounds include the following.

  The cationic polymer contains an amino group or an ammonium group bonded to a polymer chain, or is water-soluble having at least dimethyldiallylammonium halide as a structural unit, such as a cationized cellulose derivative, a cationic starch, or a cationized guar gum. Derivatives, diallyl quaternary ammonium salt polymers, diallyl quaternary ammonium salt / acrylamide copolymers, quaternized polyvinylpyrrolidone derivatives, and the like.

  Commercially available products of cationized cellulose derivatives include “Leocard G” and “GP” from Lion Corporation, and polymers “JR-125”, “JR-400” and “JR-30M” from Union Carbide. , “LR-400”, “LR-30M”, and the like. Examples of other cationized cellulose derivatives include hydroxyethyl cellulose dimethyl diallylammonium chloride, and examples of commercially available products include trade names “Cellcoat H-100” and “L-200” of National Starch and Chemical Co., Ltd. Examples of the cationized guar gum derivatives include, for example, trade names “Jaguar C-13S”, “-14S”, “-17”, “-210”, “-162”, “-162”, “HI-” of RHONE-POULNC®. CARE1000 "is commercially available. Examples of the diallyl quaternary ammonium salt polymer include commercially available product name “MARCOAT 100” manufactured by Ondeo Nalco. Examples of the cationic diallyl quaternary ammonium salt / acrylamide copolymer include commercially available product names “Marcote 2200” and “550” of Ondeo Nalco. As the quaternized polyvinyl pyrrolidone derivative, those having a molecular weight of 10,000 to 2,000,000 are preferable, and as commercial products, trade names “Guff Coat 734”, “755”, “755 N”, etc. of IP Japan Co., Ltd. Is mentioned.

  Other useful cationic polymers include methacrylic acid chloride polymers, specifically 2-methacryloyloxyethyl phosphorylcholine polymer, 2-methacryloyloxyethyl phosphorylcholine polymer, 2-methacryloyloxyethyl phosphorylcholine, Examples include butyl methacrylate copolymer, 2-methacryloyloxyethyl phosphorylcholine · 2-hydroxy-3-methacryloyloxypropyltrimethylammonium chloride copolymer, and chlorocholine methacrylate polymer. Commercially available products containing chloromethacrylic acid ester polymers include “Salcare SC95” and “SC96” manufactured by Ciba Specialty Chemicals, “Lipidure HM” and “Same PMB” manufactured by NOF Corporation. “Same C” and the like. These cationized polymers may be blended singly or in combination of two or more.

  Examples of the anionic polymer include acrylic acid / acrylic acid amide / ethyl acrylate copolymer, acrylic acid / acrylic acid amide / ethyl acrylate copolymer potassium salt solution, acrylic acid alkyl ester / methacrylic acid alkyl ester Acetone acrylamide / methacrylic acid copolymer liquid, acrylic acid / alkyl methacrylate copolymer, acrylic resin alkanolamine liquid, carboxyvinyl polymer, hydroxypropyl acrylate, butylaminoethyl methacrylate, octylamide acrylate copolymer, acetic acid Vinyl / crotonic acid copolymer, vinyl acetate / crotonic acid / vinyl neodecanoate copolymer, vinyl acetate / crotonic acid / vinyl propionate copolymer, methyl vinyl ether / maleic acid monobutyl ester copolymer, etc. It is below.

  Examples of amphoteric polymers include N-methacryloylethyl N, N-dimethylammonium α-N-methylcarboxybetaine / butyl methacrylate copolymer (commercial name “Yukaformer AM-75”; manufactured by Mitsubishi Chemical Corporation), hydroxypropyl acrylate.・ Butylaminoethyl methacrylate / octylamide acrylate copolymer (commercial name “Amphomer 28-4910”; manufactured by National Starch Co., Ltd.), dimethyldiallylammonium chloride / acrylic acid copolymer (commercial name “Mercoat 280”, “same 295 "; manufactured by Ondeo Nalco Co., Ltd.), terpolymer of dimethyldiallylammonium chloride, acrylamide, and acrylic acid (commercial names" Mercoat Plus 3330 "and" 3331 "; manufactured by Ondeo Nalco Co., Ltd.), acrylic acid, methyl acrylate, METACl Le amidopropyl trimethylammonium copolymer (trade name "Merquat 2001"; ONDEO Nalco Co.) and the like.

  Although the kind of nonionic polymer is not limited, For example, the thing of a natural system, a semisynthetic system, and a synthetic system is mentioned. Examples of natural nonionic polymers include cellulose, guar gum, agar, starch, hydrolyzed starch, and dextrin. Examples of the semisynthetic nonionic polymer include methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, and hydroxypropyl methylcellulose. Further, synthetic nonionic polymers include polyethyl acrylate, polyacrylic amide, polyethylene glycol, polypropylene glycol, polyoxyethylene (hereinafter referred to as POE) polyoxypropylene (hereinafter referred to as POP) copolymer, POE. -POP butyl ether, POE / POP hexylene glycol ether, POP butyl ether, polyvinyl pyrrolidone, POE monostearate, POE distearate and the like.

  In addition to the above-described components, the hair modifier containing the hair modifier of the present invention and the hair modifier component can be appropriately blended with components used in normal hair cosmetics depending on the purpose. Examples of such components include solvents, antidandruff agents, vitamin agents, antiseptics, anti-inflammatory agents, chelating agents, coloring agents such as dyes and pigments, viscosity modifiers such as carboxyvinyl polymer, xanthan gum, and clay minerals, PH adjusters such as citric acid, 2-amino-2-methyl-1-propanol, sodium hydroxide, hydrolyzed PPTs and amino acids and their derivatives, reducing agents, oxidizing agents, extracts extracted from plants, animals and microorganisms And pearlizing agents, fragrances, pigments, ultraviolet absorbers, antioxidants, propellants and the like. Specific examples of these ingredients include cosmetic raw material standards, cosmetic ingredient-specific formulation standards, legal dye handbooks, Japan Cosmetic Industry Association ingredient display name lists, INCI dictionary (The International Cosmetic Ingredient Dictionary and Handbook), quasi-drugs, etc. Ingredients listed in the raw material standards, the quasi-drug raw material standards 2006, the Japanese Pharmacopoeia, the pharmaceutical additives standards, the official standards for food additives, and the like.

  The pH of the hair modifying agent and the hair cosmetic is adjusted to pH 3 to 10, more preferably pH 4 by using one kind of pH adjusting agent, or by using a pH buffering agent using an organic acid or inorganic acid having a buffering action and a salt thereof. It is preferable to adjust between 5 and 8.5. In particular, it is more preferable to adjust the pH between 6.0 and 8.0. Examples of the organic acid used as the pH buffer include citric acid, glycolic acid, succinic acid, tartaric acid, lactic acid, fumaric acid, malic acid, levulinic acid, and the like. Examples of inorganic acids include phosphoric acid, sulfuric acid, and the like. And nitric acid. Examples of these acid salts include alkali metal salts such as sodium salts and potassium salts, and alkanolamine salts such as ammonium salts and triethanolamine salts.

  Hair modifiers and hair cosmetics containing hair modifier components are liquids, water-in-oil emulsions, oil-in-water emulsions, complex emulsions, microemulsions, sprays, gels, foams, granules, lotions, creams Or the like. This hair modifying agent and hair cosmetic can also be used directly as a hair care agent such as shampoo, rinse and treatment, or as a styling agent such as gel, emulsion, mousse and wax. In addition, it can also be added as a component added to hair dyes such as hair dyes, hair manicures, wave / straights such as permanent agents and hair straighteners, and drugs intended for hair growth.

  The hair modifying agent and the hair cosmetic composition containing the hair modifying component may be used after being applied to the hair and washed off with water or warm water. The same composition adhering to the hair is washed away with water or warm water. You may use without. Alternatively, by applying the hair modifying agent or hair cosmetic of the present invention to the hair and then heating it, the reactivity of the component on the hair surface and the penetration into the hair can be promoted. For heating, there is no problem even if it is left warming with a warming device (dryer, warmer, steamer, high-temperature hair-styling iron, warming lot, self-heating device, etc.), and the standing time is 1-30. Minutes are appropriate. In addition, when heating is performed using a high-temperature hair-styling iron, the contact time with the hair per part is suitably about 2 seconds to 1 minute.

  This hair modifier and a hair cosmetic containing a hair modifier component are hair treatments such as oxidative hair dyes and acidic hair dyes, hair treatments such as bleaching agents, permanent wave agents, and hair straighteners. In addition to being applied to hair treated with an agent, the effect can be exerted even when applied to hair damaged by factors other than the hair treatment agent, such as ultraviolet rays.

  EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

Examples 1-6, Comparative Examples 1-2 and Reference Example 1 (hair treatment)
Hair treatments (Examples 1 to 6, Comparative Examples 1 and 2 and Reference Example 1) having the compositions shown in Table 1 were prepared by the following methods, and “smoothness” of the hair surface, “elasticity” of the hair, and “collection” Tests were conducted to evaluate “ability”, “feel (smoothness, moistness, softness, oiliness)” and “sustainability” thereof, and “damage reduction effect” of hair. In addition, the hair treatment which does not mix | blend the said component (reference example 1) is made into a comparison object, The test result is put together in Table 3, and is shown. Moreover, the numerical value in Table 1 shows the mass%.

<Preparation method>
1) In a 300 mL beaker, components other than purified water, a pH adjuster, and “silicone SM8704C” were added in a required amount to give a final production amount of 200 g and heated to 80 ° C. to dissolve uniformly.
2) A required amount of 200 g of purified water was added to a 200 mL beaker, heated to 80 ° C., added to the mixture obtained in 1), and emulsified. Thereafter, the mixture was cooled with stirring.
3) After cooling to 40 ° C. or lower, a pH adjuster, “Silicone SM8704C” and purified water were added to prepare a hair treatment with a final production amount of 200 g.

(Evaluation methods)
Evaluation of “smoothness” 1) Evaluation hair bundle Using hair of a Japanese woman who has not been subjected to chemical treatment such as perm and hair color, a hair bundle of 15 cm in length and 2.0 g in weight is made and bleached ( Houyu Co., Ltd., using Promaster LT) was performed twice to obtain evaluation hair bundles.

2) Treatment of hair bundles After shampooing the evaluation hair bundle (manufactured by Hoyu Co., Ltd., using Promaster Color Care Shampoo), towel drying, hair treatments of Examples, Comparative Examples or Reference Examples (hereinafter referred to as “treatment agents”) 0. 2 g was uniformly applied and left in a thermostatic bath at 50 ° C. for 10 minutes. Thereafter, the treatment agent was washed thoroughly with water, and the hair bundle was dried with a dryer.

3) Evaluation method Using a friction tester manufactured by Kato Tech, the dynamic friction coefficient of the hair surface was measured, and “smoothness” was judged based on the MIU value and MMD value obtained by the measurement. The hair surface change was measured before and after treatment with the same evaluation hair bundle. Using Reference Example 1 as a control, the evaluation was made in five levels: very good (◎), good (◯), equivalent to Reference Example 1 (Δ), slightly defective (X), and defective (XX).

Evaluation of “elasticity”, “cohesiveness”, “feel (smoothness, moistness, softness, oiliness)” and “sustainability” 1) Evaluation hair bundles No chemical treatment such as perm, hair color, etc. Using a Japanese woman's hair, a hair bundle of 25 cm in length and 10 g in weight was made and subjected to bleach treatment (manufactured by Hoyu Co., Ltd., using Promaster LT, twice treatment), and further to this bleach treated hair. A hair bundle subjected to perm treatment (manufactured by Hoyu Co., Ltd., using Fit Me Wave 45) is defined as an evaluation hair bundle.

2) Treatment of hair bundles After shampooing the evaluation hair bundle (made by Hoyu Co., Ltd., using Promaster Color Care Shampoo) and towel drying, hair treatments of Examples, Comparative Examples or Reference Examples (hereinafter referred to as “treatment agents”) 0 g was uniformly applied and left in a thermostatic bath at 50 ° C. for 10 minutes. Thereafter, the treatment agent was washed thoroughly with water, and the hair bundle was dried with a dryer.

3) Evaluation Criteria Sensory evaluation was performed according to the criteria shown in Table 2 by five expert panelists, and the average value of the evaluation points is shown in Table 3.

4) Evaluation of sustainability Thereafter, shampoo (manufactured by Hoyu Co., Ltd., using Promaster Color Care Shampoo) and dryer drying were repeated 20 times using the evaluation hair bundle which was subjected to the first evaluation. Again, sensory evaluation was performed by five identical professional panelists according to the criteria shown in Table 2 to evaluate the sustainability of the effect. Using Reference Example 1 as a control, the evaluation was made in five levels: very good (◎), good (◯), equivalent to Reference Example 1 (Δ), slightly defective (X), and defective (XX).

Evaluation of “damage reduction effect” 1) Evaluation hair bundle Using hair of a Japanese woman who has not been subjected to chemical treatment such as perm, hair color, etc., a hair bundle of 15 cm in length and 2.0 g in weight is made and bleached. (Used by Hoyu Co., Ltd., using Promaster LT) was performed twice to obtain evaluation hair bundles.

2) Treatment of hair bundles After shampooing the evaluation hair bundle (manufactured by Hoyu Co., Ltd., using Promaster Color Care Shampoo), towel drying, hair treatments of Examples, Comparative Examples or Reference Examples (hereinafter referred to as “treatment agents”) 0. 2 g was uniformly applied and left in a thermostatic bath at 50 ° C. for 10 minutes. Thereafter, the treatment agent was washed thoroughly with water, and the hair bundle was dried with a dryer.

3) Evaluation method (moisture absorption rate of hair)
About the hair | bristle bundle after performing each process, the moisture content which a fixed amount of hair absorbs was measured. When the damage to the hair increased, the water absorption rate increased in proportion to the damage, and the degree of damage was compared. Conversely, if the moisture absorption rate decreases, it is judged that there is a damage reduction effect, and the damage reduction effect on hair is classified from the degree of moisture absorption rate with reference to Reference Example 1, which is very good (◎), good (◯), which was the same as Reference Example 1 (Δ), and was evaluated in five stages: slightly defective (×) and defective (XX).

  From the above results, the product of the present invention substantially improves the damaged hair by reducing the damage on the hair surface or protecting the hair surface, and improves the cohesiveness, moisture retention and elasticity of the hair. In addition, it was confirmed that the effect was long-lasting and excellent in touch after finishing.

Example 7 (Shampoo)
(mass%)
Dioleyl maleate 2.0
POE (3) sodium lauryl ether sulfate 15.0
Palm oil fatty acid amidopropyl betaine 2.5
Diglycerin 1.0
Dimethylpolysiloxane 0.5
Polyethylene glycol distearate 1.5
O- [2-hydroxy-3- (trimethylammonio) propyl] hydroxyethylcellulose chloride 0.3
Edetate tetrasodium 0.2
Taurine 0.5
Fragrance 0.05
Water remaining amount Citric acid (pH adjuster) Adjusted to pH 5.5

  The shampoo prepared by mixing the above components by a conventional method was excellent in smoothness during rinsing, cohesiveness after drying, and moisture retention.

Example 8 (Treatment without washing off)
(mass%)
Diisooleyl maleate 4.0
Cetanol 0.8
Glycerin 1.0
Decamethylcyclopentasiloxane 2.5
Highly polymerized methylpolysiloxane 1.5
Alkyltrimethylammonium chloride 0.5
Isopropylmethylphenol 0.3
Hydrolyzed silk 0.2
Fragrance 0.05
Water remaining amount Tartaric acid (pH adjuster) Adjusted to pH 6.0

  A non-washing treatment prepared by mixing the above components by a conventional method has an appropriate oily feeling when finished, but has a reduced stickiness and is excellent in hair cohesion and moisture retention.

Example 9 (styling agent)
(mass%)
Distearyl maleate 5.0
Microcrystalline wax 3.5
Tetraisostearic acid pentaerythrit 1.0
Stearic acid 2.0
Highly polymerized methylpolysiloxane 0.5
Dipropylene glycol 0.5
Carboxyvinyl polymer 0.1
Hydrolyzed oat protein 0.5
Fragrance 0.05
Water remaining Aminomethylpropanol (pH adjuster) Adjusted to pH 6.5

  The styling agent prepared by mixing and adjusting the above components by a conventional method had an appropriate setting force when finished, and was excellent in hair cohesiveness and elasticity.

Example 10 (hair dye)
(1 agent) (mass%)
Toluene-2,5-diamine 1.5
p-aminophenol 1.0
m-aminophenol 0.3
Resorcin 0.4
p-Amino-o-cresol 0.2
28% ammonia water 4.0
Ascorbic acid 0.5
Oleyl alcohol 2.0
Propylene glycol 4.0
Benzyl alcohol 8.0
Polyoxyethylene (25) behenyl ether 12.0
Polyoxyethylene (10) oleyl ether 8.0
Stearyltrimethylammonium chloride 1.0
Amodimethicone 0.3
Sodium sulfite 0.1
EDTA disodium 0.1
Water remaining amount (2 agents) (mass%)
Diisostearyl maleate 1.5
Stearyl alcohol 1.5
Polyoxyethylene (2) cetyl ether 0.3
Polyoxyethylene (30) cetyl ether 0.3
Stearyltrimethylammonium chloride 0.3
Glycerin 2.5
Sodium stannate 0.1
35% hydrogen peroxide solution 16.6
Water remaining Phosphoric acid (pH adjuster) Adjusted to pH 4.5

  When the above ingredients are mixed in a conventional manner, and the prepared hair dyes 1 and 2 are mixed at a ratio of 1: 1 and dyed, a natural hair can be obtained, and the finished state is moderately smooth and glossy. And the hair was excellent in unity.

Claims (10)

  A hair modifier containing an ester compound of an unsaturated dicarboxylic acid having 4 to 6 carbon atoms and a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms.   The ester compound is a diester compound, and at least one carboxyl group of the unsaturated dicarboxylic acid forms an ester bond with a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms. The hair modifying agent described.   The hair modifying agent according to claim 2, wherein the diester compound is such that two carboxyl groups of the unsaturated dicarboxylic acid form an ester bond with a linear or branched saturated or unsaturated alcohol having 12 to 24 carbon atoms. .   The hair modifier according to any one of claims 1 to 3, wherein the unsaturated dicarboxylic acid is maleic acid.   The hair modifier according to any one of claims 1 to 4, wherein the alcohol is a linear or branched saturated alcohol having 18 to 22 carbon atoms.   The hair modifier according to any one of claims 1 to 4, wherein the alcohol is a linear or branched unsaturated alcohol having 18 to 22 carbon atoms.   The hair modifying agent according to claim 6, wherein the unsaturated alcohol is oleyl alcohol.   The hair modifier according to claim 1, wherein the ester compound is dioleyl maleate.   A hair cosmetic containing the hair modifying agent according to any one of claims 1 to 8.   A method for modifying hair, wherein the hair cosmetic composition according to claim 9 is applied to hair.