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WO2018164164A1 - Hair treatment agent - Google Patents

Hair treatment agent Download PDF

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Publication number
WO2018164164A1
WO2018164164A1 PCT/JP2018/008693 JP2018008693W WO2018164164A1 WO 2018164164 A1 WO2018164164 A1 WO 2018164164A1 JP 2018008693 W JP2018008693 W JP 2018008693W WO 2018164164 A1 WO2018164164 A1 WO 2018164164A1
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WO
WIPO (PCT)
Prior art keywords
hair
treatment agent
hair treatment
alkyl ether
present
Prior art date
Application number
PCT/JP2018/008693
Other languages
French (fr)
Japanese (ja)
Inventor
宗一 亀田
菜保子 山本
Original Assignee
モアコスメティックス株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
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Application filed by モアコスメティックス株式会社 filed Critical モアコスメティックス株式会社
Priority to JP2019504627A priority Critical patent/JP6923955B2/en
Publication of WO2018164164A1 publication Critical patent/WO2018164164A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair

Definitions

  • the present invention relates to a hair treatment agent and a hair treatment method using the hair treatment agent.
  • General hair straighteners are mainly composed of a reducing agent and an oxidizing agent, and they suppress hair habits by their action.
  • a first agent containing a reducing agent thioglycolic acid or a salt thereof, cysteine or a salt thereof, thiolactic acid or a salt thereof, etc.
  • an alkaline agent ammonia water, ammonium hydrogen carbonate, monoethanolamine, etc.
  • a hair treatment agent that can suppress hairs and form a smooth hair surface and can correct curly hair without using a reducing agent and an oxidizing agent.
  • Patent Documents 1 and 2 propose using glyoxylic acid as a hair straightening component of a hair treatment agent that does not contain a reducing agent and an oxidizing agent.
  • Patent Document 1 discloses a step of applying a solution containing glyoxylic acid to the hair, a step of continuously contacting the substance with the hair for 15 to 120 minutes, a step of drying the hair, and about 200 ⁇ 50.
  • a hair straightening method is described which comprises the step of straightening the hair with a hair straightening iron at a temperature of 0C.
  • Patent Document 2 the step of applying a glyoxylic acid aqueous solution to the hair, the step of bringing the solution into contact with the hair for 30 to 120 minutes, the step of drying the hair using a hair dryer, and a temperature of about 200 ⁇ 30 ° C. are set.
  • a hair straightening method is described which includes the step of straightening hair using a straightening iron.
  • Patent Document 3 describes an approach for improving the hair straightening effect by mixing glyoxylic acid with other preparations.
  • the hair straightening effect achieved by these methods is weak and insufficient, and a method capable of obtaining a higher hair straightening effect is desired.
  • Patent Document 4 by using an alkyl ether carboxylic acid amino acid salt having a specific structure, which is an anionic surfactant, a liquid having low irritation and excellent usability and stability. It has been reported that cleaning compositions can be obtained.
  • the present invention provides a hair treatment agent that exhibits an excellent hair elongation action and is hypoallergenic without using a reducing agent and an oxidizing agent that can cause significant damage to hair, and a hair treatment method using the hair treatment agent.
  • the purpose is to provide.
  • the present inventors have used glyoxylic acid, which has been conventionally used as an active ingredient for hair straightening, in combination with an amino acid salt of an alkyl ether carboxylic acid.
  • glyoxylic acid which has been conventionally used as an active ingredient for hair straightening
  • an amino acid salt of an alkyl ether carboxylic acid in combination with an amino acid salt of an alkyl ether carboxylic acid.
  • the hair straightening effect can be realized significantly higher than when it is used alone, it has been found to be hypoallergenic.
  • the present invention has been completed through further studies based on these findings, and provides the following hair treatment agent and hair treatment method.
  • Item 1 Formula (I): R 1 -O- (CH 2 CH 2 O) n CH 2 COOM (I) (In the formula, R 1 represents a saturated or unsaturated hydrocarbon group, n represents a number of 1 to 10, and M represents lysine, histidine, or arginine.)
  • a hair treatment agent comprising an alkyl ether carboxylic acid amino acid salt represented by: and glyoxylic acid.
  • Item 2. Item 2. The hair treatment agent according to Item 1, wherein the pH is 1.0 to 2.5.
  • Item 3. Item 3.
  • the hair treatment agent according to Item 1 or 2 which is used for straightening hair.
  • a hair treatment method comprising a step of applying the hair treatment agent according to any one of Items 1 to 3 to all or part of the hair.
  • the hair treatment agent of the present invention exhibits an excellent hair elongation action without using a reducing agent and an oxidizing agent that can cause great damage to hair. Furthermore, since the hair treatment agent of the present invention contains an alkyl ether carboxylic acid amino acid salt that is known to be hypoallergenic, it is less irritating with less protein damage.
  • the hair treatment agent of the present invention can provide an excellent hair elongation action even if the hair is rinsed from the hair before the ironing treatment, thus facilitating the hair drying step before the ironing treatment.
  • amino acid means L-form, D-form or DL-form, preferably L-form.
  • the hair treatment agent for hair elongation of the present invention is represented by the general formula (I): R 1 -O- (CH 2 CH 2 O) n CH 2 COOM (I) (In the formula, R 1 represents a saturated or unsaturated hydrocarbon group, n represents a number of 1 to 10, and M represents lysine, histidine, or arginine.) It contains the alkyl ether carboxylic acid amino acid salt represented by these, and glyoxylic acid.
  • the alkyl ether carboxylic acid amino acid salt represented by the general formula (I) is a so-called anionic surfactant and has low protein irritation and low irritation as described in Patent Document 4.
  • Examples of the saturated or unsaturated hydrocarbon group represented by R 1 include aromatic hydrocarbons having 8 to 18 carbon atoms and linear or branched aliphatic hydrocarbons, of which aliphatic hydrocarbons (particularly, Alkyl groups and alkenyl groups) are preferred.
  • Examples of such aliphatic hydrocarbon groups include octyl, decyl, dodecyl, tridecyl, tetradecyl, hexadecyl, octadecyl, docosyl, 2-ethylhexyl, 2-hexyldecyl, 2- An octylundecyl group etc. are mentioned as a preferable example, and especially a dodecyl group, a tridecyl group, and a tetradecyl group are especially preferable.
  • the polymerization degree n of polyoxyethylene is an average polymerization degree, generally 1 to 5, preferably 2 to 4, and more preferably 3.
  • M is lysine, histidine or arginine.
  • alkyl ether carboxylic acid amino acid salt represented by the general formula (I) is as described above, it can be used alone or in admixture of two or more.
  • the blending amount of the alkyl ether carboxylic acid amino acid salt represented by the general formula (I) in the hair treatment agent of the present invention can be appropriately set.
  • 0.01 to 5% by mass, preferably 0.1 to 2% by weight can be mentioned.
  • the compound of the alkyl ether carboxylic acid amino acid salt represented by the general formula (I) to the hair treatment agent of the present invention can also be compounded by adding the alkyl ether carboxylic acid and the amino acid independently.
  • alkyl ether carboxylic acid amino acid salt represented by the general formula (I) promotes the penetration of glyoxylic acid into the hair in the hair treatment agent.
  • Glyoxylic acid can be used in a free state, a hydrate state, a salt state, and the like.
  • the glyoxylic acid in the present invention includes glyoxylic acid hydrates, glyoxylic acid salts and the like.
  • the salt include lithium salt, sodium salt, magnesium salt, calcium salt and the like.
  • Glyoxylic acid is recognized to have a pH adjusting action in addition to a hair straightening action, and is widely used in cosmetics and quasi drugs. *
  • the blending amount of glyoxylic acid in the hair treatment agent of the present invention can be appropriately set.
  • it is 5 to 25% by mass, preferably 10 to 25% by mass, more preferably 15 to 20% by mass.
  • it is 5 to 25% by mass, preferably 10 to 25% by mass, more preferably 15 to 20% by mass.
  • the hair treatment agent of the present invention can be blended with known components blended into the hair treatment agent.
  • known components blended into the hair treatment agent include water, anionic surfactants, Cationic surfactants, nonionic surfactants, amphoteric surfactants, silicones, waxes, higher alcohols, polyhydric alcohols, fatty acids, oil components, fats and oils, hydrocarbons, plant extracts, vitamins, proteins or Its hydrolysates, natural or synthetic polymers, amino acids, sequestering agents, wetting agents, UV absorbers, antioxidants, pH adjusting agents, coloring agents, anti-inflammatory agents, preservatives, fragrances, solvents, propellants, etc. Can be mentioned.
  • the pH of the hair treatment agent of the present invention is not particularly limited, and is usually pH 1.0 to 2.5.
  • the dosage form of the hair treatment agent of the present invention is not limited to a specific form, and examples thereof include forms such as cream, gel, foam, spray, mist, liquid, etc. using water as a medium.
  • the hair treatment agent of the present invention can be made into a one-part type that is used as it is, or a two-part type or a multi-part type that is used in combination with other agents as long as the effect of the hair treatment agent of the present invention is not impaired. .
  • the hair treatment agent can be prepared at the time of use by mixing with other agents immediately before use.
  • the hair treatment agent of the present invention can be used for straightening hair, suppressing hair loss, and the like.
  • the hair treatment agent of the present invention is used to correct curly hair, suppress peculiar hair, etc.
  • the straight state can be maintained semipermanently.
  • maintaining the semipermanently means that a straight state cannot be obtained by several hair washing operations, as in normal hair straightening and the like.
  • the hair treatment method of the present invention is characterized by including a step of applying the above-described hair treatment agent to all or part of the hair.
  • the hair treatment method of the present invention can perform curly hair correction, curly hair suppression, and the like.
  • the hair treatment agent in addition to the step of applying the above hair treatment agent to all or part of the hair, (B) leaving the hair in the applied state, the hair treatment agent is sufficiently applied to the hair. It is desirable to include a step of acting on the hair, (C) a step of washing the hair with water to wash away the hair treatment agent, (D) a step of drying the hair, and (E) a step of straightening the hair with a hairstyling iron.
  • step (A) the hair treatment agent can be applied to dry hair before shampooing, and since the hair treatment agent easily penetrates into the hair, wet hair that has been pre-washed with shampoo and drained moisture, It is also possible to apply to towel dry hair etc. from which the attached moisture has been removed with a towel.
  • step (B) after the hair treatment agent is applied, the hair treatment agent is allowed to act on the hair for 10 to 30 minutes, more preferably 15 to 20 minutes, at room temperature (about 25 ° C.). If the standing time is within this range, a sufficient elongation effect can be obtained.
  • step (C) the hair is rinsed with water or lukewarm water, and the hair treatment agent is washed away from the hair. By washing away the hair treatment agent from the hair, subsequent drying and handling of the hair is facilitated.
  • step (D) the hair is washed with water, wiped with a towel, and then dried with a hair dryer.
  • step (E) the hair is straightened while applying mechanical force and heat to the hair with a hairstyling iron heated to 140 to 200 ° C, preferably about 180 ° C.
  • the hair treatment method of the present invention it is possible to transform natural curly hairs or the like into straight hairs without cutting and rebinding SS bonds of proteins in the hair.
  • the hair treatment agent of the present invention can provide an excellent hair elongation effect without using a reducing agent and an oxidizing agent that can cause great damage to hair. Furthermore, since the hair treatment agent of the present invention contains an alkyl ether carboxylic acid amino acid salt that is known to be hypoallergenic, it is less irritating with less protein damage. In addition, since the hair treatment agent of the present invention can provide an excellent hair elongation effect even if the hair is rinsed from the hair before the ironing treatment, the hair drying step before the ironing treatment is facilitated.
  • the hair treatment method according to the present invention by applying a combination of glyoxylic acid and an alkyl ether carboxylic acid amino acid salt, compared to a conventional hair straightening method that applies a treatment containing glyoxylic acid alone. A hair elongation effect can be obtained.
  • alkyl ether carboxylic acid lysine, the alkyl ether carboxylic acid histidine, and the alkyl ether carboxylic acid arginine used in this example were prepared or obtained according to the following method.
  • Alkyl ether carboxylic acid lysine was prepared by neutralizing polyoxyethylene lauryl ether acetic acid (manufactured by Sanyo Chemical Industries, Ltd., trade name “Bulite LCA-25NH”) in an aqueous lysine solution. .
  • Alkyl ether carboxylic acid histidine was prepared by neutralizing polyoxyethylene lauryl ether acetic acid (manufactured by Sanyo Chemical Industries, Ltd., trade name “Burelite LCA-25NH”) in an aqueous histidine solution. .
  • Arginine of alkyl ether carboxylate was prepared by neutralizing polyoxyethylene lauryl ether acetic acid (manufactured by Sanyo Chemical Industries, Ltd., trade name “Burelite LCA-25NH”) in an arginine aqueous solution. .
  • the hair treatment agents of Examples and Comparative Examples were prepared by stirring and mixing with the components and blending amounts shown in Table 1 below until each component was uniform in purified water. Potassium hydroxide was added to adjust the pH to 1.0 to 2.5.
  • the alkyl ether carboxylic acid amino acid salt was a mixture of the above three types.
  • the habit suppressing effect of the obtained hair treatment agent was evaluated by the following method. The evaluation results are shown in Table 1.
  • Natural curly hair Japanese black hair was trimmed to a length of 18 cm when stretched, and a hair bundle weighing 1 g was prepared. Next, after washing each hair bundle with a commercially available shampoo and rinsing with water, cut the moisture, measure the length a (cm) of the hair bundle when one end of the hair bundle is fixed and suspended vertically did.
  • the length b (cm) of the hair bundle when one end of the hair bundle was fixed again and suspended in the vertical direction was measured. Based on the measured values of a and b, the degree of elongation (%) was determined by the following formula, and the habit inhibiting effect was evaluated from the obtained degree of elongation according to the following evaluation criteria.

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Abstract

Disclosed are: a hair treatment agent containing a glyoxylic acid and an alkyl ether carboxylic acid amino acid salt represented by general formula (I): R1-O-(CH2CH2O)nCH2COOM (I) (in the formula, R1 represents a saturated or unsaturated hydrocarbon group, n represents number of 1-10, and M represents lysine, histidine, or arginine.); and a hair treatment method including a step of applying said hair treatment agent to the whole or a part of hair on the head.

Description

毛髪処理剤Hair treatment agent
　本発明は、毛髪処理剤、及び該毛髪処理剤を用いた毛髪処理方法に関する。 The present invention relates to a hair treatment agent and a hair treatment method using the hair treatment agent.
　一般的な縮毛矯正剤は、還元剤及び酸化剤を主成分としており、それらの作用により毛髪のクセを抑制する。具体的には、還元剤(チオグリコール酸又はその塩、システイン又はその塩、チオ乳酸又はその塩等)と、アルカリ剤(アンモニア水、炭酸水素アンモニウム、モノエタノールアミン等)とを含有する第１剤を毛髪に塗布することにより、毛髪内の構成タンパクに存在するジスルフィド結合を還元開裂して毛髪をストレート状に伸ばす。次に、酸化剤(臭素酸ナトリウム、過酸化水素等)を主成分とする第２剤で処理することで、新たな位置でジスルフィド基を再形成させて、毛髪の形状を固定化させる。 General hair straighteners are mainly composed of a reducing agent and an oxidizing agent, and they suppress hair habits by their action. Specifically, a first agent containing a reducing agent (thioglycolic acid or a salt thereof, cysteine or a salt thereof, thiolactic acid or a salt thereof, etc.) and an alkaline agent (ammonia water, ammonium hydrogen carbonate, monoethanolamine, etc.). By applying the agent to the hair, the disulfide bonds present in the constituent proteins in the hair are reductively cleaved to straighten the hair. Next, by treating with an oxidant (sodium bromate, hydrogen peroxide, etc.) as a main component, a disulfide group is re-formed at a new position to fix the shape of the hair.
　しかしながら、還元剤及び酸化剤の作用は毛髪にダメージを与えることが多いため、毛髪のなめらかさ、サラサラ感、指通りの良さ、うるおい感などが損なわれることで、処理後の毛髪の感触が悪くなる他、毛髪表面が荒れることにより、外観上の艶が失われ、毛髪の風合いが低下してしまう。このような酸化剤及び還元剤の髪に対する影響は消費者にも広く認識されているため、縮毛矯正を避ける大きな要因となっている。 However, the action of the reducing agent and the oxidizing agent often damages the hair, so that the smoothness, smoothness, good fingering, moisturization, etc. of the hair are impaired, resulting in poor touch of the hair after treatment. In addition, when the hair surface becomes rough, the gloss on the appearance is lost and the texture of the hair is lowered. Since the influence of such an oxidizing agent and a reducing agent on hair is widely recognized by consumers, it is a major factor for avoiding curly hair correction.
　そのため、還元剤及び酸化剤を使用せずに、クセ毛の抑制及び毛髪表面のなめらかさを形成すること、縮毛の矯正を行うことができる毛髪処理剤の開発が望まれている。 Therefore, it is desired to develop a hair treatment agent that can suppress hairs and form a smooth hair surface and can correct curly hair without using a reducing agent and an oxidizing agent.
　還元剤及び酸化剤を含まない毛髪処理剤の毛髪矯正成分として、特許文献１及び２では、グリオキシル酸を用いることが提案されている。具体的に、特許文献１には、グリオキシル酸を含む溶液を毛髪に塗布する段階と、物質を毛髪に15～120分間持続的に接触させる段階と、毛髪を乾燥させる段階と、約200±50℃の温度で毛髪矯正アイロンを用いて毛髪を矯正する段階とを有する毛髪矯正方法が記載されている。特許文献２には、グリオキシル酸水溶液を毛髪に塗布する段階、前記溶液を毛髪に30～120分間接触させる段階、ヘアドライヤーを用いて毛髪を乾燥する段階、約200±30℃の温度に設定された毛髪矯正アイロンを用いて毛髪を矯正する段階を含む毛髪矯正方法が記載されている。また、特許文献３にはグリオキシル酸と他の製剤を混ぜ合わせることで毛髪矯正効果を向上させる取り組みが記載されている。 Patent Documents 1 and 2 propose using glyoxylic acid as a hair straightening component of a hair treatment agent that does not contain a reducing agent and an oxidizing agent. Specifically, Patent Document 1 discloses a step of applying a solution containing glyoxylic acid to the hair, a step of continuously contacting the substance with the hair for 15 to 120 minutes, a step of drying the hair, and about 200 ± 50. A hair straightening method is described which comprises the step of straightening the hair with a hair straightening iron at a temperature of 0C. In Patent Document 2, the step of applying a glyoxylic acid aqueous solution to the hair, the step of bringing the solution into contact with the hair for 30 to 120 minutes, the step of drying the hair using a hair dryer, and a temperature of about 200 ± 30 ° C. are set. A hair straightening method is described which includes the step of straightening hair using a straightening iron. Patent Document 3 describes an approach for improving the hair straightening effect by mixing glyoxylic acid with other preparations.
　しかし、これらの方法で達成される毛髪矯正効果は弱くて不十分であり、より高い毛髪矯正効果が得られる方法が望まれている。 However, the hair straightening effect achieved by these methods is weak and insufficient, and a method capable of obtaining a higher hair straightening effect is desired.
　また、特許文献４及び非特許文献１では、アニオン性界面活性剤である、特定の構造を有するアルキルエーテルカルボン酸アミノ酸塩を使用することで、低刺激性で使用性及び安定性に優れた液体洗浄組成物が得られることが報告されている。 Further, in Patent Document 4 and Non-Patent Document 1, by using an alkyl ether carboxylic acid amino acid salt having a specific structure, which is an anionic surfactant, a liquid having low irritation and excellent usability and stability. It has been reported that cleaning compositions can be obtained.
日本国特表2013-520468号公報Japanese National Table 2013-520468 日本国特表2013-531046号公報Japan Special Table 2013-531046 日本国特許第5947340号公報Japanese Patent No. 5947340 日本国特許第5057337号公報Japanese Patent No. 5057337
　本発明は、毛髪に大きなダメージを与え得る還元剤及び酸化剤を用いずとも、優れた毛髪伸長作用を奏し、低刺激性である毛髪処理剤、及び該毛髪処理剤を用いた毛髪処理方法を提供することを目的とする。 The present invention provides a hair treatment agent that exhibits an excellent hair elongation action and is hypoallergenic without using a reducing agent and an oxidizing agent that can cause significant damage to hair, and a hair treatment method using the hair treatment agent. The purpose is to provide.
　本発明者等は、上記目的を達成すべく鋭意研究を重ねた結果、従来から毛髪矯正の有効成分として使用されているグリオキシル酸をアルキルエーテルカルボン酸アミノ酸塩と組み合わせて用いることにより、グリオキシル酸を単独で用いる場合と比べて格段に高い毛髪矯正効果を実現できる上に低刺激性となるという知見を得た。 As a result of intensive studies to achieve the above object, the present inventors have used glyoxylic acid, which has been conventionally used as an active ingredient for hair straightening, in combination with an amino acid salt of an alkyl ether carboxylic acid. In addition to the fact that the hair straightening effect can be realized significantly higher than when it is used alone, it has been found to be hypoallergenic.
　本発明は、これら知見に基づき、更に検討を重ねて完成されたものであり、次の毛髪処理剤及び毛髪処理方法を提供するものである。 The present invention has been completed through further studies based on these findings, and provides the following hair treatment agent and hair treatment method.
項１．一般式（Ｉ）：
R1-O-(CH2CH2O)nCH2COOM　　　　（Ｉ）
(式中、R1は飽和又は不飽和の炭化水素基を示し、nは1～10の数を示し、Mはリシン、ヒスチジン又はアルギニンを示す。)
で表されるアルキルエーテルカルボン酸アミノ酸塩及びグリオキシル酸を含む毛髪処理剤。
項２．pHが1.0～2.5である、項１に記載の毛髪処理剤。 
項３．縮毛矯正に用いられる、項１又は２に記載の毛髪処理剤。
項４．項１～３のいずれか一項に記載の毛髪処理剤を頭髪の全部又は一部に適用する工程を含む、毛髪処理方法。 Item 1. Formula (I):
R 1 -O- (CH 2 CH 2 O) n CH 2 COOM (I)
(In the formula, R 1 represents a saturated or unsaturated hydrocarbon group, n represents a number of 1 to 10, and M represents lysine, histidine, or arginine.)
A hair treatment agent comprising an alkyl ether carboxylic acid amino acid salt represented by: and glyoxylic acid.
Item 2. Item 2. The hair treatment agent according to Item 1, wherein the pH is 1.0 to 2.5.
Item 3. Item 3. The hair treatment agent according to Item 1 or 2, which is used for straightening hair.
Item 4. A hair treatment method comprising a step of applying the hair treatment agent according to any one of Items 1 to 3 to all or part of the hair.
　本発明の毛髪処理剤は、毛髪に大きなダメージを与え得る還元剤及び酸化剤を用いずとも、優れた毛髪伸長作用を奏する。さらに、本発明の毛髪処理剤は低刺激性であることが知られているアルキルエーテルカルボン酸アミノ酸塩を含むためタンパク質の損傷が少なく低刺激性である。 The hair treatment agent of the present invention exhibits an excellent hair elongation action without using a reducing agent and an oxidizing agent that can cause great damage to hair. Furthermore, since the hair treatment agent of the present invention contains an alkyl ether carboxylic acid amino acid salt that is known to be hypoallergenic, it is less irritating with less protein damage.
　その上、本発明の毛髪処理剤は、アイロン処理の前に毛髪からすすぎ流しても優れた毛髪伸長作用が得られるため、アイロン処理の前の毛髪乾燥工程が容易となる。 In addition, the hair treatment agent of the present invention can provide an excellent hair elongation action even if the hair is rinsed from the hair before the ironing treatment, thus facilitating the hair drying step before the ironing treatment.
　以下、本発明について詳細に説明する。 Hereinafter, the present invention will be described in detail.
　なお、本明細書において「含む(comprise)」とは、「本質的にからなる(essentially consist of)」という意味と、「のみからなる(consist of)」という意味をも包含する。 In the present specification, “comprise” also includes the meaning of “essentially“ consist ”of” and the meaning of “consistent of”.
　本明細書においてアミノ酸は、L体、D体又はDL体を意味し、好ましくはL体である。 In the present specification, amino acid means L-form, D-form or DL-form, preferably L-form.
　本発明の毛髪伸長における毛髪処理剤は、一般式（Ｉ）：
R1-O-(CH2CH2O)nCH2COOM　　　　（Ｉ）
(式中、R1は飽和又は不飽和の炭化水素基を示し、nは1～10の数を示し、Mはリシン、ヒスチジン又はアルギニンを示す。)
で表されるアルキルエーテルカルボン酸アミノ酸塩及びグリオキシル酸を含むことを特徴とする。 The hair treatment agent for hair elongation of the present invention is represented by the general formula (I):
R 1 -O- (CH 2 CH 2 O) n CH 2 COOM (I)
(In the formula, R 1 represents a saturated or unsaturated hydrocarbon group, n represents a number of 1 to 10, and M represents lysine, histidine, or arginine.)
It contains the alkyl ether carboxylic acid amino acid salt represented by these, and glyoxylic acid.
　一般式（Ｉ）で表されるアルキルエーテルカルボン酸アミノ酸塩は、いわゆるアニオン性界面活性剤であり、特許文献４に記載されているようにタンパク質の損傷が少なく低刺激性である。 The alkyl ether carboxylic acid amino acid salt represented by the general formula (I) is a so-called anionic surfactant and has low protein irritation and low irritation as described in Patent Document 4.
　R1で示される飽和又は不飽和の炭化水素基としては、例えば、炭素数8～18の芳香族炭化水素及び直鎖状又は分岐状脂肪炭化水素が例示され、そのうち、脂肪族炭化水素(特にアルキル基、アルケニル基)が好ましい。このような脂肪族炭化水素基としては、例えば、オクチル基、デシル基、ドデシル基、トリデシル基、テトラデシル基、ヘキサデシル基、オクタデシル基、ドコシル基、２－エチルヘキシル基、２－ヘキシルデシル基、２－オクチルウンデシル基等が好ましい例として挙げられ、中でもドデシル基、トリデシル基及びテトラデシル基が特に好ましい。 Examples of the saturated or unsaturated hydrocarbon group represented by R 1 include aromatic hydrocarbons having 8 to 18 carbon atoms and linear or branched aliphatic hydrocarbons, of which aliphatic hydrocarbons (particularly, Alkyl groups and alkenyl groups) are preferred. Examples of such aliphatic hydrocarbon groups include octyl, decyl, dodecyl, tridecyl, tetradecyl, hexadecyl, octadecyl, docosyl, 2-ethylhexyl, 2-hexyldecyl, 2- An octylundecyl group etc. are mentioned as a preferable example, and especially a dodecyl group, a tridecyl group, and a tetradecyl group are especially preferable.
　ポリオキシエチレンの重合度nは平均重合度であり、一般に1～5であり、2～4が好ましく、3がより好ましい。 The polymerization degree n of polyoxyethylene is an average polymerization degree, generally 1 to 5, preferably 2 to 4, and more preferably 3.
　Mは、リシン、ヒスチジン又はアルギニンである。かかる塩基性アミノ酸の塩とすることにより、細胞に対する刺激が低減される。 M is lysine, histidine or arginine. By using such a basic amino acid salt, stimulation to cells is reduced.
　一般式（Ｉ）で表されるアルキルエーテルカルボン酸アミノ酸塩は、上記のものであれば単独で又は2種以上を混合して用いることができる。 As long as the alkyl ether carboxylic acid amino acid salt represented by the general formula (I) is as described above, it can be used alone or in admixture of two or more.
　本発明の毛髪処理剤中の一般式（Ｉ）で表されるアルキルエーテルカルボン酸アミノ酸塩の配合量は、適宜設定することができるものであり、例えば、0.01～5質量%、好ましくは0.1～2質量%を挙げることができる。 The blending amount of the alkyl ether carboxylic acid amino acid salt represented by the general formula (I) in the hair treatment agent of the present invention can be appropriately set. For example, 0.01 to 5% by mass, preferably 0.1 to 2% by weight can be mentioned.
　本発明の毛髪処理剤への一般式（Ｉ）で表されるアルキルエーテルカルボン酸アミノ酸塩の配合は、アルキルエーテルカルボン酸とアミノ酸とをそれぞれ単独で添加する形で配合することもできる。 The compound of the alkyl ether carboxylic acid amino acid salt represented by the general formula (I) to the hair treatment agent of the present invention can also be compounded by adding the alkyl ether carboxylic acid and the amino acid independently.
　一般式（I）で表されるアルキルエーテルカルボン酸アミノ酸塩は、毛髪処理剤中においてグリオキシル酸の毛髪への浸透を促進させていると考えられる。 It is considered that the alkyl ether carboxylic acid amino acid salt represented by the general formula (I) promotes the penetration of glyoxylic acid into the hair in the hair treatment agent.
　グリオキシル酸は、フリーの状態、水和物の状態、塩の状態等で使用することができる。本発明におけるグリオキシル酸には、グリオキシル酸の水和物、グリオキシル酸の塩等も包含される。塩としては、リチウム塩、ナトリウム塩、マグネシウム塩、カルシウム塩等が挙げられる。グリオキシル酸は、毛髪矯正作用の他、pH調整作用等を有することが認められており、化粧品及び医薬部外品に広く用いられている。　 Glyoxylic acid can be used in a free state, a hydrate state, a salt state, and the like. The glyoxylic acid in the present invention includes glyoxylic acid hydrates, glyoxylic acid salts and the like. Examples of the salt include lithium salt, sodium salt, magnesium salt, calcium salt and the like. Glyoxylic acid is recognized to have a pH adjusting action in addition to a hair straightening action, and is widely used in cosmetics and quasi drugs. *
　本発明の毛髪処理剤中のグリオキシル酸の配合量は、適宜設定することができるものであり、例えば、5～25質量%、好ましくは10～25質量%、より好ましくは15～20質量%を挙げることができる。 The blending amount of glyoxylic acid in the hair treatment agent of the present invention can be appropriately set. For example, it is 5 to 25% by mass, preferably 10 to 25% by mass, more preferably 15 to 20% by mass. Can be mentioned.
　本発明の毛髪処理剤には、上記の成分以外にも、毛髪処理剤に配合される公知の成分を配合することができ、そのような成分としては、例えば、水、アニオン性界面活性剤、カチオン性界面活性剤、ノニオン性界面活性剤、両性界面活性剤、シリコーン類、ロウ類、高級アルコール、多価アルコール、脂肪酸、油性成分、油脂類、炭化水素、植物抽出物、ビタミン類、タンパク質又はその加水分解物、天然又は合成高分子、アミノ酸、金属封鎖剤、湿潤剤、紫外線吸収剤、酸化防止剤、pH調整剤、着色剤、抗炎症剤、防腐剤、香料、溶剤、噴射剤などが挙げられる。 In addition to the above components, the hair treatment agent of the present invention can be blended with known components blended into the hair treatment agent. Examples of such components include water, anionic surfactants, Cationic surfactants, nonionic surfactants, amphoteric surfactants, silicones, waxes, higher alcohols, polyhydric alcohols, fatty acids, oil components, fats and oils, hydrocarbons, plant extracts, vitamins, proteins or Its hydrolysates, natural or synthetic polymers, amino acids, sequestering agents, wetting agents, UV absorbers, antioxidants, pH adjusting agents, coloring agents, anti-inflammatory agents, preservatives, fragrances, solvents, propellants, etc. Can be mentioned.
　本発明の毛髪処理剤のpHとしては、特に限定されるものではなく、通常pH1.0～2.5である。 The pH of the hair treatment agent of the present invention is not particularly limited, and is usually pH 1.0 to 2.5.
　本発明の毛髪処理剤の剤型としては、特定のものに限定されるものではなく、例えば、水を媒体とする、クリーム、ジェル、フォーム、スプレー、ミスト、液状等の形態が挙げられる。 The dosage form of the hair treatment agent of the present invention is not limited to a specific form, and examples thereof include forms such as cream, gel, foam, spray, mist, liquid, etc. using water as a medium.
　本発明の毛髪処理剤は、そのまま使用する１剤式、又は本発明の毛髪処理剤の効果を損なわなければ、更に他の剤と組合せて使用する２剤式若しくは多剤式とすることができる。同様に本発明の毛髪処理剤の効果を損なわなければ、該毛髪処理剤が他の剤と使用直前に混合する用時調製式とすることができる。 The hair treatment agent of the present invention can be made into a one-part type that is used as it is, or a two-part type or a multi-part type that is used in combination with other agents as long as the effect of the hair treatment agent of the present invention is not impaired. . Similarly, as long as the effect of the hair treatment agent of the present invention is not impaired, the hair treatment agent can be prepared at the time of use by mixing with other agents immediately before use.
　本発明の毛髪処理剤は、縮毛矯正、クセ毛抑制等のために使用することができる。本発明の毛髪処理剤を使用して縮毛矯正、クセ毛抑制等を行った場合、ストレート状態を半永久的に持続させることができる。なお、前記半永久的に持続させるとは、通常の縮毛矯正等と同等に、数回の洗髪操作ではストレート状態が取れないことを意味する。 The hair treatment agent of the present invention can be used for straightening hair, suppressing hair loss, and the like. When the hair treatment agent of the present invention is used to correct curly hair, suppress peculiar hair, etc., the straight state can be maintained semipermanently. In addition, maintaining the semipermanently means that a straight state cannot be obtained by several hair washing operations, as in normal hair straightening and the like.
　本発明の毛髪処理方法は、上記の毛髪処理剤を頭髪の全部又は一部に適用する工程を含むことを特徴とする。 The hair treatment method of the present invention is characterized by including a step of applying the above-described hair treatment agent to all or part of the hair.
　本発明の毛髪処理方法により、縮毛矯正、クセ毛抑制等を行うことができる。 The hair treatment method of the present invention can perform curly hair correction, curly hair suppression, and the like.
　本発明の毛髪処理方法は、(A)上記の毛髪処理剤を頭髪の全部又は一部に適用する工程に加えて、(B)適用した状態で毛髪を放置して毛髪処理剤を毛髪に十分に作用させる工程、(C)毛髪を水洗して毛髪処理剤を洗い流す工程、(D)毛髪を乾燥させる工程、及び(E)整髪用アイロンで毛髪を矯正する工程を含むことが望ましい。 In the hair treatment method of the present invention, (A) in addition to the step of applying the above hair treatment agent to all or part of the hair, (B) leaving the hair in the applied state, the hair treatment agent is sufficiently applied to the hair. It is desirable to include a step of acting on the hair, (C) a step of washing the hair with water to wash away the hair treatment agent, (D) a step of drying the hair, and (E) a step of straightening the hair with a hairstyling iron.
　(A)工程では、毛髪処理剤は、シャンプー前のドライ毛に適用することが可能であり、また、毛髪処理剤が毛髪に浸透し易いため、シャンプーで予め洗浄し水分を切ったウェット毛、付着した水分をタオルで取り除いたタオルドライ毛などに適用することも可能である。 In step (A), the hair treatment agent can be applied to dry hair before shampooing, and since the hair treatment agent easily penetrates into the hair, wet hair that has been pre-washed with shampoo and drained moisture, It is also possible to apply to towel dry hair etc. from which the attached moisture has been removed with a towel.
　(B)工程では、毛髪処理剤を適用後、室温(約25℃)にて10～30分間、より好ましくは15～20分間放置し、毛髪処理剤を毛髪に作用させる。放置時間がこの範囲であれば、十分な伸長効果が得られる。 In step (B), after the hair treatment agent is applied, the hair treatment agent is allowed to act on the hair for 10 to 30 minutes, more preferably 15 to 20 minutes, at room temperature (about 25 ° C.). If the standing time is within this range, a sufficient elongation effect can be obtained.
　(C)工程では、毛髪を水又はぬるま湯ですすぎ、毛髪処理剤を毛髪から洗い流す。毛髪から毛髪処理剤を洗い流すことで、その後の毛髪の乾燥及び取り扱いが容易になる。 In step (C), the hair is rinsed with water or lukewarm water, and the hair treatment agent is washed away from the hair. By washing away the hair treatment agent from the hair, subsequent drying and handling of the hair is facilitated.
　(D)工程では、毛髪を水洗後、水分をタオルで拭き取った後に、ヘアドライヤーで乾燥させる。 In step (D), the hair is washed with water, wiped with a towel, and then dried with a hair dryer.
　(E)工程では、140～200℃、好ましくは約180℃に熱した整髪用アイロンで毛髪に機械力及び熱を加えながら毛髪をストレート状に伸ばす。 In step (E), the hair is straightened while applying mechanical force and heat to the hair with a hairstyling iron heated to 140 to 200 ° C, preferably about 180 ° C.
　本発明の毛髪処理方法では、毛髪内のタンパク質のSS結合の切断及び再結合によらずに、天然の縮れ毛等を直毛状に変形することが可能である。 In the hair treatment method of the present invention, it is possible to transform natural curly hairs or the like into straight hairs without cutting and rebinding SS bonds of proteins in the hair.
　本発明の毛髪処理剤は、毛髪に大きなダメージを与え得る還元剤及び酸化剤を用いずとも、優れた毛髪伸長作用が得られる。さらに、本発明の毛髪処理剤は低刺激性であることが知られているアルキルエーテルカルボン酸アミノ酸塩を含むためタンパク質の損傷が少なく低刺激性である。その上、本発明の毛髪処理剤は、アイロン処理の前に毛髪からすすぎ流しても優れた毛髪伸長作用が得られるため、アイロン処理の前の毛髪乾燥工程が容易となる。 The hair treatment agent of the present invention can provide an excellent hair elongation effect without using a reducing agent and an oxidizing agent that can cause great damage to hair. Furthermore, since the hair treatment agent of the present invention contains an alkyl ether carboxylic acid amino acid salt that is known to be hypoallergenic, it is less irritating with less protein damage. In addition, since the hair treatment agent of the present invention can provide an excellent hair elongation effect even if the hair is rinsed from the hair before the ironing treatment, the hair drying step before the ironing treatment is facilitated.
　本発明に係る毛髪処理方法によれば、グリオキシル酸とアルキルエーテルカルボン酸アミノ酸塩とを組み合わせて適用することにより、グリオキシル酸を単独で含む処理剤を適用する従来の毛髪矯正方法と比べて、高い毛髪伸長効果を得ることができる。 According to the hair treatment method according to the present invention, by applying a combination of glyoxylic acid and an alkyl ether carboxylic acid amino acid salt, compared to a conventional hair straightening method that applies a treatment containing glyoxylic acid alone. A hair elongation effect can be obtained.
　以下、本発明を更に詳しく説明するため実施例を挙げる。しかし、本発明はこれら実施例等になんら限定されるものではない。 Hereinafter, examples will be given to explain the present invention in more detail. However, the present invention is not limited to these examples.
　サンプルの調製及び入手
　本実施例で使用したアルキルエーテルカルボン酸リシン、アルキルエーテルカルボン酸ヒスチジン、及びアルキルエーテルカルボン酸アルギニンは、以下の方法に従い調製乃至入手した。 Sample Preparation and Acquisition The alkyl ether carboxylic acid lysine, the alkyl ether carboxylic acid histidine, and the alkyl ether carboxylic acid arginine used in this example were prepared or obtained according to the following method.
　・アルキルエーテルカルボン酸リシンの調製
　アルキルエーテルカルボン酸リシンは、ポリオキシエチレンラウリルエーテル酢酸(三洋化成工業株式会社製、商品名「ビューライトLCA-25NH」)をリシン水溶液中で中和して調製した。 ・ Preparation of alkyl ether carboxylic acid lysine Alkyl ether carboxylic acid lysine was prepared by neutralizing polyoxyethylene lauryl ether acetic acid (manufactured by Sanyo Chemical Industries, Ltd., trade name “Bulite LCA-25NH”) in an aqueous lysine solution. .
　・アルキルエーテルカルボン酸ヒスチジンの調製
　アルキルエーテルカルボン酸ヒスチジンは、ポリオキシエチレンラウリルエーテル酢酸(三洋化成工業株式会社製、商品名「ビューライトLCA-25NH」)をヒスチジン水溶液中で中和して調製した。 Preparation of alkyl ether carboxylic acid histidine Alkyl ether carboxylic acid histidine was prepared by neutralizing polyoxyethylene lauryl ether acetic acid (manufactured by Sanyo Chemical Industries, Ltd., trade name “Burelite LCA-25NH”) in an aqueous histidine solution. .
　・アルキルエーテルカルボン酸アルギニンの調製
　アルキルエーテルカルボン酸アルギニンは、ポリオキシエチレンラウリルエーテル酢酸(三洋化成工業株式会社製、商品名「ビューライトLCA-25NH」)をアルギニン水溶液中で中和して調製した。 Preparation of arginine of alkyl ether carboxylate Arginine of alkyl ether carboxylate was prepared by neutralizing polyoxyethylene lauryl ether acetic acid (manufactured by Sanyo Chemical Industries, Ltd., trade name “Burelite LCA-25NH”) in an arginine aqueous solution. .
　下記の表１に示した成分及び配合量で、各成分が精製水に均一になるまで撹拌混合することにより実施例及び比較例の毛髪処理剤を調製した。pHが1.0～2.5となるように水酸化カリウムを添加して調節した。なお、アルキルエーテルカルボン酸アミノ酸塩は上記3種の混合物を使用した。 The hair treatment agents of Examples and Comparative Examples were prepared by stirring and mixing with the components and blending amounts shown in Table 1 below until each component was uniform in purified water. Potassium hydroxide was added to adjust the pH to 1.0 to 2.5. The alkyl ether carboxylic acid amino acid salt was a mixture of the above three types.
　得られた毛髪処理剤のクセ抑制効果を、以下の方法により評価した。その評価結果を、表１に示す。 The habit suppressing effect of the obtained hair treatment agent was evaluated by the following method. The evaluation results are shown in Table 1.
　＜クセ抑制効果の評価＞
　天然カーリーヘア(日本人黒毛)を伸長時の長さが18 cmになるように切りそろえ、重さ1 gの毛束を作製した。次に、各毛束を市販のシャンプーにて洗浄し水ですすいだ後に、水分を切り、毛束の一端を固定して垂直方向に吊したときの毛束の長さa (cm)を測定した。 <Evaluation of habit suppression effect>
Natural curly hair (Japanese black hair) was trimmed to a length of 18 cm when stretched, and a hair bundle weighing 1 g was prepared. Next, after washing each hair bundle with a commercially available shampoo and rinsing with water, cut the moisture, measure the length a (cm) of the hair bundle when one end of the hair bundle is fixed and suspended vertically did.
　この毛束に、調製した毛髪処理剤を1 g塗布し、25℃で15分間放置した。その後、水ですすいで毛髪処理剤を洗い流した。タオルで拭き取ってからドライヤーで乾燥させ、180℃に熱した整髪用アイロンを2秒間押し当てて毛髪を伸長した。 1 g of the prepared hair treatment agent was applied to this hair bundle and left at 25 ° C. for 15 minutes. Then, the hair treatment agent was rinsed off with water. After wiping with a towel, the hair was dried with a dryer and the hair was stretched by pressing a hairstyling iron heated to 180 ° C. for 2 seconds.
　この毛束の一端を再度固定して垂直方向に吊したときの毛束の長さb (cm)を測定した。測定したa及びbの値をもとに下記の式により伸長度(%)を求め、得られた伸長度から下記の評価基準によりクセ抑制効果を評価した。 The length b (cm) of the hair bundle when one end of the hair bundle was fixed again and suspended in the vertical direction was measured. Based on the measured values of a and b, the degree of elongation (%) was determined by the following formula, and the habit inhibiting effect was evaluated from the obtained degree of elongation according to the following evaluation criteria.
Figure JPOXMLDOC01-appb-M000001
Figure JPOXMLDOC01-appb-M000001
＜評価基準＞
A：伸長度が85～100%
B：伸長度が70～85%
C：伸長度が30～70%
D：伸長度が0～30% <Evaluation criteria>
A: Degree of elongation is 85-100%
B: Elongation is 70-85%
C: Degree of elongation is 30-70%
D: Degree of elongation is 0-30%
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002
　表１の結果から、グリオキシル酸をアルキルエーテルカルボン酸アミノ酸塩と組み合わせた場合に、著しく高いクセ抑制効果が得られた。これに対し、アルキルエーテルカルボン酸アミノ酸塩を含まない場合には、クセ抑制効果は不十分であった。 From the results shown in Table 1, when glyoxylic acid was combined with an alkyl ether carboxylic acid amino acid salt, a remarkably high addictive effect was obtained. On the other hand, when the alkyl ether carboxylic acid amino acid salt is not included, the habit suppressing effect is insufficient.
　処方例
　以下、本発明の毛髪処理剤の処方例を挙げる。なお、配合量は全て毛髪処理剤全量に対する質量%で表す。 Formulation Examples Hereinafter, formulation examples of the hair treatment agent of the present invention will be given. In addition, all compounding quantities are represented by the mass% with respect to the hair treatment agent whole quantity.
　・処方例１
毛髪処理剤(pH1.7) ・ Prescription example 1
Hair treatment agent (pH1.7)
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000003

Claims (4)

  1. 　一般式（Ｉ）：
    R1-O-(CH2CH2O)nCH2COOM　　　　（Ｉ）
    (式中、R1は飽和又は不飽和の炭化水素基を示し、nは1～10の数を示し、Mはリシン、ヒスチジン又はアルギニンを示す。)
    で表されるアルキルエーテルカルボン酸アミノ酸塩及びグリオキシル酸を含む毛髪処理剤。     Formula (I):
    R 1 -O- (CH 2 CH 2 O) n CH 2 COOM (I)
    (In the formula, R 1 represents a saturated or unsaturated hydrocarbon group, n represents a number of 1 to 10, and M represents lysine, histidine, or arginine.)
    A hair treatment agent comprising an alkyl ether carboxylic acid amino acid salt represented by: and glyoxylic acid.
  2. 　pHが1.0～2.5である、請求項１に記載の毛髪処理剤。  2. The hair treatment agent according to claim 1, having a pH of 1.0 to 2.5.
  3. 　縮毛矯正に用いられる、請求項１又は２に記載の毛髪処理剤。 The hair treatment agent according to claim 1 or 2, which is used for straightening hair.
  4. 　請求項１～３のいずれか一項に記載の毛髪処理剤を頭髪の全部又は一部に適用する工程を含む、毛髪処理方法。 A hair treatment method comprising a step of applying the hair treatment agent according to any one of claims 1 to 3 to all or a part of hair.
PCT/JP2018/008693 2017-03-08 2018-03-07 Hair treatment agent WO2018164164A1 (en)

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EP4382173A1 (en) * 2022-12-07 2024-06-12 Kao Germany GmbH Aqueous composition for semi-permanent straightening keratin fibers especially human hair
JP7560912B1 (en) 2024-03-06 2024-10-03 株式会社Very Very Hair treatment products

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JPH01110611A (en) * 1987-10-22 1989-04-27 Shiseido Co Ltd Agent for permanent wave treatment
JP5057337B2 (en) * 2008-04-08 2012-10-24 モアコスメティックス株式会社 Hypoallergenic liquid cleaning composition
JP2011225467A (en) * 2010-04-16 2011-11-10 Kao Corp Skin detergent composition
JP2013227232A (en) * 2012-04-24 2013-11-07 Kracie Home Products Ltd Foamy aerosol composition
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Publication number Priority date Publication date Assignee Title
EP4382173A1 (en) * 2022-12-07 2024-06-12 Kao Germany GmbH Aqueous composition for semi-permanent straightening keratin fibers especially human hair
JP7560912B1 (en) 2024-03-06 2024-10-03 株式会社Very Very Hair treatment products

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