JP6877856B2 - Glyoxylic acid-containing hair composition - Google Patents

Description

The present invention relates to a composition for hair, and more particularly to a composition for hair containing glyoxylic acid, which has a high effect of preventing sagging on the scalp and the like when applied to hair and has an improved treatment effect on damaged hair.

Glyoxylic acid is one of the aldehyde carboxylic acids represented by the chemical formula CHOCOOH, and is also called glyoxylic acid. Since such glyoxylic acid can be used for straightening curly hair, curly hair, etc. when used in combination with a hair composition (hair cosmetic, hair treatment agent), various methods have been proposed in recent years.

For example, Patent Document 1 discloses a hair strengthening agent composed of glyoxylic acid, and Patent Document 2 describes (a) a step of applying a straightening composition to the hair and (b) the step of applying the straightening composition to the hair. The steps of leaving the composition for 1 to 120 minutes, (c) optionally rinsing the hair, (d) drying the hair, and (e) the surface temperature of the hair 130-250. One of (f) the step of treating the hair with an iron at ° C., (f) optionally the step of rinsing and / or shampooing the hair and drying it, and (g) the step of treating the hair with a cleaning composition and a conditioning composition. The straightening composition comprises a step of treating with or both, and the straightening composition has a pH of 4 or less and contains glyoxylic acid and / or a hydrate thereof and / or a salt thereof. One or more surfactants having a pH of 4 or less and selected from anionic surfactants, nonionic surfactants and amphoteric surfactants, and glyoxylic acid and / or hydrates thereof and / or salts thereof. The conditioning composition is characterized by having a pH of 4 or less and containing one or more conditioning components and glyoxylic acid and / or a hydrate thereof and / or a salt thereof. Processes for semi-permanent straightening and aftercare treatment are disclosed.

In addition, various methods have been proposed for techniques that combine organic acids and amidamines. Patent Document 3 discloses a hair cosmetic containing a specific amidamine and an aliphatic alcohol, and Patent Document 4 discloses a hair cosmetic containing a specific amidamine, a higher alcohol and an organic acid.

Japanese Unexamined Patent Publication No. 2019-26574 Japanese Patent No. 6244468 Japanese Unexamined Patent Publication No. 2005-298447 Japanese Unexamined Patent Publication No. 2013-253055

However, since the techniques described in Patent Documents 1 and 2 consider various cationic components, when glyoxylic acid is used as a hair cosmetic (hair treatment agent), it is applied to the scalp or the like when applied to the hair. In some cases, irritation due to sagging of the hair may occur. In particular, since glyoxylic acid is a substance that may cause serious damage to the eyes, it has been required to take all possible measures against sagging during application.

Further, since the techniques described in Patent Documents 3 and 4 use various organic acids, the treatment effect on damaged hair may not be sufficient, and moreover, irritation due to sagging on the scalp or the like may occur. There was, and improvement was desired.

Therefore, an object of the present invention is for hair, which solves the above-mentioned problems of the prior art, has a high effect of preventing sagging on the scalp and the like when applied to hair, and has an improved treatment effect on damaged hair. The purpose is to provide the composition.

As a result of diligent studies to solve the above problems, the present inventors have found that the above object can be achieved by combining a specific cation component and glyoxylic acid, and have completed the present invention. ..

（式（１）中、Ｒ^１は、直鎖又は分岐の炭素数２１の炭化水素基を表す）で表されるアミドアミンと、
（Ｂ）下記一般式（２）、

で表されるグリオキシル酸と、
（Ｃ）下記一般式（３）、

（式（３）中、Ｒ^２は、直鎖の割合が８０質量％以上の炭素数１８〜２４のアルキル基またはアルケニル基を表す）で表される高級アルコールと、を含有し、ゲル化したことを特徴とするものである。
That is, the hair composition of the present invention has (A) the following general formula (1),

(In the formula (1), R ¹ represents a linear or branched hydrocarbon group having 21 carbon atoms ) and amidoamine.
(B) The following general formula (2),

Glyoxylic acid represented by
(C) The following general formula (3),

(In the formula (3), R ² represents a higher alcohol represented by an alkyl group or an alkenyl group having 18 to 24 carbon atoms having a linear ratio of 80% by mass or more ) and gelled. It is characterized by that.

Further, hair compositions of the present invention is further selected from (D) preferably contains an aromatic alcohol, wherein (D) an aromatic alcohol, base down benzyl alcohol, the group consisting of benzyloxyethanol 1 Species or two or more species are preferred.

In addition, the hair composition of the present invention preferably further contains (E) a silicone compound.

According to the present invention, it is possible to provide a hair composition having a high effect of preventing sagging on the scalp and the like when applied to hair and having an improved treatment effect on damaged hair.

It is a photograph which shows the state of the gel of Example 2. It is a photograph which shows the state of the gel of the comparative example 3. It is a photograph which shows the state of the gel of the comparative example 6. It is a photograph showing the stability of the gel.

（式（１）中、Ｒ^１は、直鎖又は分岐の炭素数２１の炭化水素基を表す）で表されるアミドアミンと、
（Ｂ）下記一般式（２）、

で表されるグリオキシル酸と、
（Ｃ）下記一般式（３）、

（式（３）中、Ｒ^２は、直鎖の割合が８０質量％以上の炭素数１８〜２４のアルキル基またはアルケニル基を表す）で表される高級アルコールと、を含有し、ゲル化したことを特徴とするものである。これにより、毛髪に塗布したときに、頭皮等へのタレの防止効果の高く、しかも損傷した毛髪へのトリートメント効果が向上した毛髪用組成物を提供することができる。
Hereinafter, the hair composition of the present invention will be specifically described.
The composition for hair of the present invention is the composition for hair of the present invention (A) the following general formula (1),

(In the formula (1), R ¹ represents a linear or branched hydrocarbon group having 21 carbon atoms ) and amidoamine.
(B) The following general formula (2),

Glyoxylic acid represented by
(C) The following general formula (3),

(In the formula (3), R ² represents an alkyl group or an alkenyl group having 18 to 24 carbon atoms having a linear ratio of 80% by mass or more ) and gelled. It is characterized by that. This makes it possible to provide a hair composition having a high effect of preventing sagging on the scalp and the like when applied to hair and having an improved treatment effect on damaged hair.

（式（１）中、Ｒ^１は、直鎖又は分岐の炭素数２１の炭化水素基を表す）で表されるアミドアミンとしては、化粧料に使用できるものであれば特に限定されないが、例えば、ベヘナミドプロピルジメチルアミン、等を使用でき、具体的には、日光ケミカルズ株式会社製のＮＩＫＫＯＬ アミドアミン ＭＰＢ ＰＬＵＳ（商品名）等を使用できる。
In the present invention, (A) the following general formula (1),

The amide amine represented by (in the formula (1), R ¹ represents a linear or branched hydrocarbon group having 21 carbon atoms ) is not particularly limited as long as it can be used in cosmetics, but for example, Behenamide propyl dimethylamine , etc. can be used, and specifically, NIKKOL amidoamine MPB PLUS (trade name ) manufactured by Nikko Chemicals Co., Ltd. can be used.

で表されるグリオキシル酸は、グリオキシル酸だけでなく、その水和物またはその塩として使用することもできる。かかるグリオキシル酸としては、化粧料に使用できるものであれば特に限定されないが、グリオキザールフリー（５００ｐｐｍ以下）のものが好ましく、例えば、Ｗｅｙｌｃｈｅｍ Ｌａｍｏｔｔｅ社製のＧｌｙｏｘｏ Ｈｉｇｈ Ｐｕｒｅ ５０（商品名）等を挙げることができる。 Further, in the present invention, (B) the following general formula (2),

The glyoxylic acid represented by is not only glyoxylic acid but also can be used as a hydrate thereof or a salt thereof. The glyoxylic acid is not particularly limited as long as it can be used in cosmetics, but glyoxal-free (500 ppm or less) is preferable, and examples thereof include Glyoxo High Pure 50 (trade name) manufactured by Weylchem Lamotte. Can be done.

（式（３）中、Ｒ^２は、直鎖の割合が８０質量％以上の炭素数１８〜２４のアルキル基またはアルケニル基を表す）で表される高級アルコールとしては、化粧料に使用できるものであれば特に限定されないが、例えば、ステアリルアルコール、オレイルアルコール、ベヘニルアルコール、イソステアリルアルコール、ヘキシルデカノール、オクチルドデカノール、デシルテトラデカノール、オレイルアルコール、アラキルアルコール、ベヘニルアルコール等を挙げることができる。 Further, in the present invention, (C) the following general formula (3),

(In the formula (3), R ² represents an alkyl group or an alkenyl group having 18 to 24 carbon atoms having a linear ratio of 80% by mass or more) and can be used in cosmetics as a higher alcohol. is not particularly limited as long as, for example, it may be mentioned stearyl alcohol, oleyl alcohol, behenyl alcohol, isostearyl alcohol, hexyl decanol, octyl dodecanol, decyl tetradecanol, oleyl alcohol, arachidyl alcohol, behenyl alcohol and the like.

In addition, the hair composition of the present invention preferably further contains (D) an aromatic alcohol. The aromatic alcohol (D) is not particularly limited as long as it can be used in cosmetics, but it is preferably one or more selected from the group consisting of phenoxyethanol, benzyl alcohol, and benzyloxyethanol.

In addition, the hair composition of the present invention preferably further contains (E) a silicone compound. The silicone compound (E) is not particularly limited as long as it can be used for cosmetics, and for example, dimethicone (dimethylpolysiloxane), highly polymerized dimethicone (highly polymerized dimethylpolysiloxane), cyclomethicone (cyclic dimethylsiloxane, etc.) Decamethylcyclopentasiloxane), phenyltrimethicone, diphenyldimethicone, phenyldimethicone, stearoxypropyldimethylamine, (aminoethylaminopropylmethicone / dimethicone) copolymer, dimethiconol, dimethiconol crosspolymer, silicone resin, silicone rubber, aminopropyldimethicone and Amino-modified silicones such as amodimethicone, cationic-modified silicones, polyether-modified silicones such as dimethicone copolyol, polyglycerin-modified silicones, sugar-modified silicones, carboxylic acid-modified silicones, phosphate-modified silicones, sulfate-modified silicones, alkyl-modified silicones, fatty acids Modified silicone, alkyl ether modified silicone, amino acid modified silicone, peptide modified silicone, fluorine modified silicone, cationic modified and polyether modified silicone, amino modified and polyether modified silicone, alkyl modified and polyether modified silicone, polysiloxane / oxyalkylene A polymer can be mentioned.

Further, in the present invention, the amount of the amidamine represented by (A) the general formula (1) is not limited as long as the effect of the present invention is obtained, but is 0.1 to 5.0% by mass. Is preferable, and 1.0 to 3.0% by mass is more preferable. Within such a range, when applied to hair, the effect of preventing sagging on the scalp and the like can be further improved, and the treatment effect on damaged hair can be further improved.

Further, in the present invention, the amount of glyoxylic acid represented by (B) the general formula (2) is not limited as long as the effect of the present invention is obtained, but may be 5.0 to 40% by mass. preferable. Within such a range, when applied to hair, the effect of preventing sagging on the scalp and the like can be further improved, and the treatment effect on damaged hair can be further improved.

Furthermore, in the present invention, the amount of the higher alcohol compounded by (C) the general formula (3) is not limited as long as the effect of the present invention is obtained, but is 1.0 to 10.0% by mass. It is preferably 2.0 to 5.0% by mass, and more preferably 2.0 to 5.0% by mass. Within such a range, when applied to hair, the effect of preventing sagging on the scalp and the like can be further improved, and the treatment effect on damaged hair can be further improved.

Further, in the present invention, a cationic surfactant can be added in addition to (A) the amidamine represented by the general formula (1), and the cationic surfactant can be usually used in cosmetics. The above is not particularly limited, but for example, stearyltrimethylammonium chloride, hydroxystearyltrimethylammonium chloride, capryltrimethylammonium chloride, myristyltrimethylammonium chloride, cetyltrimethylammonium chloride, cetiltriethylammonium bromide, behenyltrimethylammonium chloride, lauryltrimethylammonium chloride. , Trioleyl Methylammonium Chloride, Dioleyl Monostearyl Methyl Ammonium Chloride, Dioleyl Monobehenyl Methyl Ammonium Chloride, Distearyl Dimethyl Ammonium Chloride, DiCured Beef Alkyl Dimethyl Ammonium Chloride, Di Beef Alkyl Dimethyl Ammonium Bromide, Dioleil Dimethyl Ammonium Chloride, Dipalmitylmethylhydroxyethylammonium metosulfate, distearyldimethylammonium chloride, diisostearyldimethylammonium metosulfate, tristearylmethylammonium metosulfate, N-stearyl-N, N, N-tri (polyoxyethylene) ammonium chloride ( Quaternary cationic surfactants such as di [(2-dodecanoylamino) ethyl] dimethylammonium chloride, di[(2-stearoylamino) propyl] dimethylammonium etosulfate, cetylbenzyldimethylammonium chloride) , Each of which may be used alone or in combination of two or more.

Further, in the present invention, the hair composition is not particularly limited as long as it can be used for human hair, and is mainly a cosmetic product, but does not exclude uses such as quasi-drugs and pharmaceutical products. In particular, it is a hair cosmetic used for hair treatment and hair treatment.

Further, in the present invention, other components and the like can be appropriately added as long as the effects of the present invention are not impaired. Any ingredient other than the above can be blended within the qualitative and quantitative range, and ingredients normally blended in cosmetics, such as surfactants, oily ingredients, moisturizers, antioxidants, fragrances, and various vitamins. , Chelating agent, coloring agent, ultraviolet absorber, medicinal ingredient, inorganic salts and the like can be blended.

Examples of components that can be blended include monofatty acid polyglyceryl, polyfatty acid polyglyceryl, polyoxyethylene glycerin fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbit fatty acid ester, and polyoxyethylene propylene. Glycol fatty acid ester, polyoxyethylene castor oil derivative, polyoxyethylene hydrogenated castor oil derivative, polyoxyethylene sterol, polyoxyethylene hydrogenated sterol, polyethylene glycol fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene polyoxypropylene alkyl ether , Sucrose fatty acid ester and the like.

As amphoteric surfactants, for example, 2-undecyl-N, N, N- (hydroxyethylcarboxymethyl) -2-imidazoline sodium, 2-cocoyl-2-imidazolinium hydroxide-1-carboxyethyloxy 2-sodium Imidazoline-based amphoteric surfactants such as salts, 2-heptadecyl-N-carboxymethyl-N-hydroxyethyl imidazolinium betaine, lauryldimethylaminoacetic acid betaine, alkylbetaine, amide betaine, sulfobetaine and other betaine-based surfactants. And so on.

Examples of polyhydric alcohols include glycerin, 1,3-butylene glycol, propylene glycol, propanediol, 1,2-hexanediol, pentylene glycol, pentaerythritol, hexylene glycol, diglycerin, polyglycerin, diethylene glycol and polyethylene. Examples thereof include glycol, dipropylene glycol, polypropylene glycol, ethylene glycol / propylene glycol copolymer, and one or more selected from the group consisting of these polymers.

Polymer components include, for example, xanthan gum, gellan gum, gum arabic, tragacanth gum, galactan, guar gum, carrageenan, pectin, agar, quince seed, dextran, purulan, casein, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl methyl cellulose, gelatin methyl cellulose, sodium alginate. , Cardovinyl polymer and the like.

Extract components include, for example, chamomile extract, parsley extract, watermelon extract, rice extract, rice bran extract, hop extract, sardine extract, yokuinin extract, senburi extract, melilot extract, birch extract, kanzo extract, shakuyaku extract, sabonsou extract, and hechima extract. , Togarashi extract, lemon extract, gentiana extract, perilla extract, aloe extract, rosemary extract, sage extract, thyme extract, eucalyptus extract, tea extract, seaweed extract, cucumber extract, chowji extract, carrot extract, marronnier extract, hamamelis extract, quail extract , Chinpi extract, pecan nut extract, grapefruit extract, shikuwasa extract, passion fruit extract, biwa extract, grape extract, rose fruit extract, clara extract, peppermint extract and the like.

Examples of the moisturizing component include xylitol, sorbitol, maltitol, chondroitin sodium sulfate, elastin, glucosamine, hyaluronic acid, cyclodextrin, collagen, bile acid salt and the like.

As medicinal ingredients, for example, vitamins such as vitamin A, vitamin B, vitamin C, vitamin D, vitamin E and their derivatives, glycyrrhizinic acid and derivatives, glycyrrhetinic acid and derivatives, various salts such as urea, creatinine, CoQ10 , Astaxanthin, polyphenol, ceramide and other components.

Examples of the ultraviolet absorber include benzophenone derivatives such as 2-hydroxy-4-methoxybenzophenone, paraaminobenzoic acid derivatives such as paraaminobenzoic acid, methoxycinnamic acid derivatives such as octyl paramethoxycinnamic acid, and salicylic acid derivatives such as octyl salicylate and phenyl salicylate. , Urocannamic acid, ethyl urocanate, 4-tert-butyl-4'methoxydibenzoylmethane, benzotriazole and the like.

Further, in the present invention, as a method for producing a composition for hair, a method for producing a composition for hair can be produced by an ordinary method for producing a cosmetic, a method for producing by heating an oil phase component and an aqueous phase component, a D phase emulsification method, and the like. Can be used.

Furthermore, as a method for treating hair using the composition for hair of the present invention, it can be used in the usual method for using the composition for hair.

Further, in the present invention, the method of applying the hair composition to the hair is not particularly limited as long as the hair composition can be applied to the hair, and the hair composition may be applied directly to the hair by hand or in a container. You may apply it directly from the above.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples. The numbers in the table for the following prescriptions indicate mass%.

(Examples 1 to 3 and Comparative Examples 1 to 6)
Hair compositions of Examples 1 to 3 and Comparative Examples 1 to 6 were prepared according to the formulations shown in Table 1 below. In addition, the appearance of the hair composition was observed by the following evaluation method, and the results are also shown in Table 1.

(Evaluation of gel condition)
The gel state was visually confirmed and evaluated according to the following criteria.
Evaluation criteria for gel state ◎: Gel state is maintained slightly, but gel state is maintained: Visual ○: Gel state elimination, viscous fluid liquid: viscosity 500 mPas or more Δ: Gel state elimination, low viscosity fluid liquid: viscosity 100 mPas or more Viscosity less than 500 mPas ×: Gel state elimination, non-viscous fluid liquid: Viscosity less than 100 mPas * Viscosity was measured using a B-type viscometer.

(Evaluation of gel stability)
2 g of a sample of the hair composition was measured on a spatula spoon, and the speed at which the gel flowed was confirmed and evaluated using the inclination of the beaker's mouth.

FIG. 1 is a photograph showing the state of the gel of Example 2, FIG. 2 is a photograph showing the state of the gel of Comparative Example 3, and FIG. 3 is a photograph showing the state of the gel of Comparative Example 6. .. From the results of Table 1 and FIGS. 1 to 3, the hair compositions of Examples 1 to 3 were in a good gel state. On the other hand, the hair compositions of Comparative Examples 1 to 6 had a good gel state in the hair compositions of Comparative Examples 3 and 6, but the other hair compositions could sufficiently maintain the gel state. It wasn't a thing. The hair compositions of Example 2 and Comparative Example 3 formed a glossy and clean gel, but the hair composition of Comparative Example 6 was a gel having a low gloss and a light white color. Further, FIG. 4 is a photograph showing the stability of the gel. From this result, Example 2 was more stable than Comparative Examples 3 and 6.

The hair compositions of Examples 1 to 3 and Comparative Examples 1 to 6 were subjected to sensory evaluation of the hair compositions by the following evaluation methods, and the results are also shown in Table 2.

(sensory evaluation)
Bundle commercially available bleached hair, remove oil with ethanol, wash with 10% polyoxyethylene (2) sodium lauryl ether sulfate solution, apply hair composition (1 g) evenly, and run water at 40 ° C. Too much, easy to spread and spread when applied when dried with a dryer after towel drying, no squeaky feeling when rinsing, no squeaky feeling after towel drying (when wet), moist feeling after drying, cohesive feeling Ten professional panelists made a sensual comparison and evaluated according to the following criteria.
◎: When 9 or more people answered good ○: When 6 to 8 people answered good △: When 3 to 5 people answered good ×: 2 people answered good For less than one person

From the results in Table 2, the hair compositions of Examples 1 to 3 showed excellent performance for damaged hair in terms of usability during application, rinsing, wetting, and drying. On the other hand, the hair compositions of Comparative Examples 1 to 6 were compared with the hair compositions of Examples 1 to 3 in terms of usability during application, rinsing, wetting and drying even for damaged hair. It was inferior. From this, the hair composition of the present invention has good usability when applied to damaged hair (easiness to spread and spread), smoothness when rinsing, smoothness when wet, flexibility and after drying. I was able to give a feeling of cohesiveness and combability.

The hair compositions of Examples 1 and 2 and Comparative Examples 3 and 6 were subjected to sensory evaluation by the following evaluation method by actual use of the hair composition, and the results are also shown in Table 3.

(Sensory evaluation by actual use)
As a normal hair treatment after washing hair, 20 professional panelists apply the hair composition evenly, rinse it with running water at 40 ° C, towel dry it, and then dry it with a dryer. The lack of squeaky feeling at the time, the lack of squeaky feeling after towel drying (when wet), and the moist feeling and cohesiveness after drying were sensually compared and evaluated according to the following criteria.
◎: When 9 or more people answered good ○: When 6 to 8 people answered good △: When 3 to 5 people answered good ×: 2 people answered good For less than one person

From the results in Table 3, the hair compositions of Examples 1 and 2 showed excellent performance for damaged hair in terms of usability during application, rinsing, wetting, and drying. On the other hand, the hair compositions of Comparative Examples 3 and 6 were compared with the hair compositions of Examples 1 and 2 in terms of usability during application, rinsing, wetting and drying even for damaged hair. It was inferior. From this, the hair composition of the present invention has good usability when applied to damaged hair (easiness to spread and spread), smoothness when rinsing, smoothness when wet, flexibility and after drying. I was able to give a feeling of cohesiveness and combability.

Claims (4)

(A) The following general formula (1),

(In the formula (1), R ¹ represents a linear or branched hydrocarbon group having 21 carbon atoms ) and amidoamine.
(B) The following general formula (2),

Glyoxylic acid represented by
(C) The following general formula (3),

(In the formula (3), R ² represents a higher alcohol represented by an alkyl group or an alkenyl group having 18 to 24 carbon atoms having a linear ratio of 80% by mass or more ) and gelled. A composition for hair, characterized in that. The hair composition according to claim 1, further comprising (D) an aromatic alcohol. Wherein (D) an aromatic alcohol, benzyl alcohol, one or more at which claim 2 hair compositions according selected from the group consisting of benzyloxy ethanol. The hair composition according to any one of claims 1 to 3, further comprising (E) a silicone compound.

Images