WO2020021798A1 - Hair protectant, hair treatment agent, and hair treatment method - Google Patents

Abstract

Provided are a novel hair protectant capable of achieving both suppression of hair damage and improvement of feel, and a hair treatment agent containing the same. The hair protectant of one embodiment of the present invention contains a perfluoropolyether.

Description

Hair protection agent, hair treatment agent and hair treatment method

(4) The present invention relates to a hair protecting agent, a hair treating agent containing the hair protecting agent, and a use of the hair treating agent.

Hair color treatment (also referred to as "hair dyeing treatment") and permanent wave treatment (also referred to simply as "perm treatment"), which are a type of hairdressing and beauty treatment, involve a chemical reaction to the hair, and may cause damage to the hair. Are known. These two types of processing have different operation steps. That is, while the hair color treatment decomposes the melanin pigment in the hair with hydrogen peroxide, the permanent wave treatment uses an oxidation / reduction reaction to cleave and recombine the disulfide bond of hair keratin (Non-Patent Document 1). See). As a result, the nature of the damage to the hair is different, such that the hair color treatment degrades the surface of the hair, while the permanent wave treatment degrades mainly inside the hair.

種 々 Various hair protection ingredients have been proposed as a technique for repairing and improving hair damaged by such treatment and irradiation with ultraviolet rays. For example, Patent Document 1 discloses (A) an N-acylamino acid condensate, (B) an organopolysiloxane containing no amino group and an amino-modified organopolysiloxane, and (C) a polyoxy resin having an ethylene oxide addition mole number of 60 or more. An oil-in-water emulsion composition for hair cosmetics comprising ethylene castor oil and / or polyoxyethylene hydrogenated castor oil, (D) water is disclosed. Patent Literature 2 discloses a hair protection component characterized by containing a protein having an average molecular weight measured by gel filtration column chromatography separated and purified from human hair of 11,000.

Japanese Unexamined Patent Publication "JP-A-2015-110538" Japanese Unexamined Patent Publication "JP-A-2004-286738"

However, it has been difficult for the conventional hair protecting ingredients as described above to achieve both suppression of hair damage and improvement of the feel. That is, silicone-based hair protectants have been mainly used to improve the feel of hair (for example, see Patent Document 1). However, while a silicone-based hair protectant has the effect of improving the feel of the hair surface, it cannot restore the strength of the hair. On the other hand, keratin-based hair protection agents have been mainly used to suppress hair damage (for example, see Patent Document 2). Although the keratin-based hair protective agent has the effect of increasing the strength of the hair, the stickiness peculiar to protein remains on the hair surface, and the feel of the hair does not improve but tends to deteriorate.

An object of one embodiment of the present invention is to provide a novel hair protection agent and a hair treatment agent containing the same, which can solve the above-mentioned problems.

As a result of intensive studies, the present inventors have found that it is effective to use perfluoropolyether as a hair protecting agent, and have completed the present invention.

That is, the present invention includes the following configurations.
<1> A hair protecting agent containing perfluoropolyether.
<2> The hair protection agent according to <1>, wherein the perfluoropolyether includes a perfluoropolyether represented by the following formula (1).
_{CF 3 - (CF 2) m} -O- (CF 2 CF 2 O) n - (CF 2 O) o - (CF (CF 3) CF 2 O) p - (CF (CF 3) O) q - ( _{CF 2 CF 2 CF 2 O)} r - (CF 2) s -CF 3 (1)
[In equation (1),
m + s represents a real number of 0 to 5,
n + o + p + q + r represents a real number of 1 to 50. ]
<3> The hair protection agent according to <1>, wherein the perfluoropolyether includes a perfluoropolyether represented by the following formula (2).
_{CF 3 - (CF 2) m} -O- (CF 2 CF 2 O) n - (CF 2 O) o - (CF (CF 3) CF 2 O) p - (CF (CF 3) O) q - ( _{CF 2 CF 2 CF 2 O)} r - (CF 2) s -CH 2 O-R1 (2)
[In equation (2),
R1 represents H, — [CH ₂ —CH (OH) CH ₂ O] _x —R3, or — (CH ₂ ) _y OH;
x represents a real number of 1 to 5, y represents a real number of 1 to 6,
R3 is H, _OH, a CH _3, C 6 _{H 5} or _C 6 _H 4 O-B,
B is a C1-C4 alkoxy group, amide group, or amino group;
m + s represents a real number of 1 to 5,
n + o + p + q + r represents a real number of 1 to 50. ]
<4> The hair protection agent according to <1>, wherein the perfluoropolyether includes a perfluoropolyether represented by the following formula (3).
_{R2-OCH 2 - (CF 2} ) m -O- (CF 2 CF 2 O) n - (CF 2 O) o - (CF (CF 3) CF 2 O) p - (CF (CF 3) O) q — (CF ₂ CF ₂ CF ₂ O) _r — (CF ₂ ) _s —CH ₂ O—R1 (3)
[In equation (3),
R1 and R2 each independently represent H, — [CH ₂ —CH (OH) CH ₂ O] _x —R3, or — (CH ₂ ) _y OH;
x represents a real number of 1 to 5, y represents a real number of 1 to 6,
R3 is H, _OH, a CH _3, C 6 _{H 5} or _C 6 _H 4 O-B,
B is a C1-C4 alkoxy group, amide group, or amino group;
m + s represents a real number of 1 to 5,
n + o + p + q + r represents a real number of 1 to 50. ]
<5> The hair protective agent according to any one of <1> to <4>, wherein the perfluoropolyether has a number average molecular weight of 100 to 10,000.
<6> A hair treatment agent comprising the hair protection agent according to any one of <1> to <6>.
<7> The hair treatment composition according to claim 6, wherein the content of the perfluoropolyether is 0.005 to 20% by mass.
<8> A hair treatment method using the hair treatment agent according to <6> or <7>.

According to one aspect of the present invention, there is provided a novel hair protection agent capable of achieving both suppression of hair damage and improvement in feel, and a hair treatment agent containing the same.

(A) is an SEM image showing the surface of healthy hair that has not been subjected to hair color treatment. (B) is an SEM image showing the surface of a hair sample that has been treated with a hair coloring agent to which D2N has been added as a hair protection agent. (C) is an SEM image showing the surface of a hair sample that has been treated with a hair coloring agent to which D2N has not been added. 3 is a graph showing the sulfur content of a hair sample treated with a hair coloring agent containing perfluoropolyether.

Hereinafter, an example of an embodiment of the present invention will be described in detail, but the present invention is not limited thereto. Unless otherwise specified in this specification, “A to B” representing a numerical range means “A or more and B or less”.

[1. Perfluoropolyether)
[Structure and physical properties of perfluoropolyether]
The hair protective agent according to one embodiment of the present invention contains perfluoropolyether.

As used herein, “perfluoropolyether” refers to — (CF ₂ O) —, — (C ₂ F ₄ O) —, — (C ₃ F ₆ O) —, — (C ₄ F ₈ O) —. ,-(C ₅ F ₁₀ O)-, and-(C ₆ F ₁₂ O)-. The number of the repeating unit is preferably 1 to 50, and more preferably 1 to 20.

The repeating unit may be linear or branched. Preferably, it is linear. For example,-(C ₃ F ₆ O)-is-(CF ₂ CF ₂ CF ₂ O)-,-(CF (CF ₃ ) CF ₂ O)-,-(CF ₂ CF (CF ₃ ) O)-. And the like, but is preferably-(CF ₂ CF ₂ CF ₂ O)-. The same applies to other repeating units.

(4) The terminal of the perfluoropolyether may be modified with a functional group or may be unmodified. Here, “not modified with a functional group” means that the terminal is a perfluoroalkyl group. Examples of the functional group modifying the terminal include a hydroxyl group, a phosphazene group, an amino group, a carboxyl group, a phenyl group, a phenoxy group, a thiol group, an amide group, and an alkoxy group. The options of R1 and R2 in the formulas (2) and (3) described later are also examples of the functional group modifying the terminal.

限 り As long as the effects of the present invention are exerted, the perfluoropolyether may have a substituent or may contain an atom other than a carbon atom, a fluorine atom and an oxygen atom. Examples of such a substituent include a hydroxyl group, a phosphazene group, an amino group, a carboxyl group, a phenyl group, a phenoxy group, a thiol group, an amide group, and an alkoxy group. Examples of such atoms other than a carbon atom, a fluorine atom and an oxygen atom include a hydrogen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a halogen atom other than a fluorine atom.

In one embodiment, the perfluoropolyether has a structure represented by the following formula (1).
_{CF 3 - (CF 2) m} -O- (CF 2 CF 2 O) n - (CF 2 O) o - (CF (CF 3) CF 2 O) p - (CF (CF 3) O) q - ( _{CF 2 CF 2 CF 2 O)} r - (CF 2) s -CF 3 (1).

中 In the formula (1), m + s is a real number of 0 to 5, preferably a real number of 0 to 4. n + o + p + q + r is a real number of 1 to 50, preferably a real number of 1 to 20.

Formula (1) represents a perfluoropolyether in which both ends are not modified with functional groups. Such a perfluoropolyether can be prepared using, for example, Demnum (manufactured by Daikin Industries), Krytox (manufactured by DuPont Specialty Chemicals), and Fomblin (manufactured by Solvay) as starting materials (for example, a desired structure is obtained by chromatography. By separating the perfluoropolyether having). For example, when demnum is used as a starting material, perfluoropolyether in which demnum is a main chain and both ends are not modified with a functional group can be prepared. Such a perfluoropolyether is referred to herein as "D2N". Similarly, it is possible to prepare a perfluoropolyether having Krytox or Fomblin as a main chain and both ends not modified with a functional group. The latter is referred to as “Fomblin @ X” in this specification. Further, as another example of perfluoropolyether having Fomblin as a main chain and both ends not modified with a functional group, Fomblin @ HC / R (manufactured by Nikko Chemicals Co., Ltd.) can also be mentioned.

The structure of D2N is as follows.
CF ₃ CF ₂ CF ₂ (CF ₂ CF ₂ CF ₂ O) _m CF ₂ CF ₂ CF ₃ (m is a real number of 1 to 50, preferably 1 to 10).

The structure of Krytox is as follows.
CF ₃ CF ₂ CF ₂ O— (CF (CF ₃ ) CF ₂ O) _z —CF ₂ CF ₃ (z is a real number of 1 to 50, preferably 1 to 10).

The structure of Fomblin X is as follows.
CF ₃ CF ₂ O (CF ₂ CF ₂ O) _x (CF ₂ O) _y CF ₂ CF ₃ (x + y is a real number of 1 to 50, and preferably a real number of 1 to 10).

The structure of Fomblin HC / R is as follows.
CF ₃ O (CF ₂ O) _x (CF ₂ CF (CF ₃ ) O) _y CF ₃ (x + y is a real number of 1 to 50, preferably a real number of 1 to 10).

In one embodiment, the perfluoropolyether has a structure represented by the following formula (2).
_{CF 3 - (CF 2) m} -O- (CF 2 CF 2 O) n - (CF 2 O) o - (CF (CF 3) CF 2 O) p - (CF (CF 3) O) q - ( _{CF 2 CF 2 CF 2 O)} r - (CF 2) s -CH 2 O-R1 (2).

In the formula (2), R1 represents H, — [CH ₂ —CH (OH) CH ₂ O] _x —R3 or — (CH ₂ ) _y OH. Here, x is a real number of 1 to 5. y is a real number from 1 to 6. R3 is H, _OH, a CH _3, C 6 _{H 5} or _{C 6 H 4 O-B,} B is an alkoxy group of C1 ~ C4, the amide group, an amino group.

Here, C ₆ H ₅ and C ₆ H ₄ in R ₃ are a benzene ring. When R3 is C ₆ H ₄ OB, the positional relationship between the perfluoropolyether group and OB may be any of the ortho, meta and para positions.

Preferably, R1 _{is, H, CH 2 CH (OH} ) CH 2 OH, CH 2 CH (OH) CH 2 OCH 2 CH (OH) CH 2 OH, CH 2 CH (OH) CH 2 OCH 2 CH (OH) Selected from CH ₂ OCH ₂ CH (OH) CH ₂ OH or CH ₂ CH (OH) CH ₂ OCH ₂ CH (OH) CH ₂ OCH ₂ CH (OH) CH ₂ OCH ₂ CH (OH) CH ₂ OH .

中 In the formula (2), m + s is a real number of 1 to 5, preferably a real number of 2 to 4. n + o + p + q + r is a real number of 1 to 50, preferably a real number of 1 to 20.

Formula (2) represents a perfluoropolyether in which one end is not modified with a functional group. Such perfluoropolyethers can be prepared, for example, using Demnum (manufactured by Daikin Industries) and Fomblin (manufactured by Solvay) as starting materials (for example, separating perfluoropolyether having a desired structure by chromatography). by.). For example, when demnum is used as a starting material, perfluoropolyether having demnum as a main chain and one end not modified with a functional group can be prepared. Such a perfluoropolyether is referred to herein as "D2M". Similarly, a perfluoropolyether having Fomblin as the main chain and one end not modified with a functional group can be prepared. Such a perfluoropolyether is referred to herein as "Fomblin @ Y".

The structure of D2M is as follows.
CF ₃ CF ₂ CF ₂ (CF ₂ CF ₂ CF ₂ O) _m CF ₂ CF ₂ CH ₂ OH (m is a real number of 1 to 50, preferably a real number of 1 to 20).

The structure of Fomblin Y is as follows.
CF ₃ CF ₂ O (CF ₂ CF ₂ O) _x (CF ₂ O) _y CF ₂ CH ₂ O—CH ₂ CH (OH) CH ₂ OH (x + y is a real number of 1 to 50 and a real number of 10 to 30 Is preferred).

In one embodiment, the perfluoropolyether has a structure represented by the following formula (3).
_{R2-OCH 2 - (CF 2} ) m -O- (CF 2 CF 2 O) n - (CF 2 O) o - (CF (CF 3) CF 2 O) p - (CF (CF 3) O) q — (CF ₂ CF ₂ CF ₂ O) _r — (CF ₂ ) _s —CH ₂ O—R1 (3).

In the formula (3), R1 and R2 each independently represent H, — [CH ₂ —CH (OH) CH ₂ O] _x —R3 or — (CH ₂ ) _y OH. Here, x is a real number of 1 to 5. y is a real number from 1 to 6. R3 is H, _OH, a CH _3, C 6 _{H 5} or _{C 6 H 4 O-B,} B is an alkoxy group of C1 ~ C4, the amide group, an amino group. C ₆ H ₅ and C ₆ H _{4 in} R ₃ are the same as described in the formula (2).

Preferably, R1 and R2 are each _{independently, H, CH 2 CH (OH} ) CH 2 OH, CH 2 CH (OH) CH 2 OCH 2 CH (OH) CH 2 OH, CH 2 CH (OH) CH 2 OCH ₂ CH (OH) CH ₂ OCH ₂ CH (OH) CH ₂ OH, or CH ₂ CH (OH) CH ₂ OCH ₂ CH (OH) CH ₂ OCH ₂ CH (OH) CH ₂ OCH ₂ CH (OH) CH ₂ OH.

中 In the formula (3), m + s is a real number of 1 to 5, preferably 2 to 5, and more preferably 3 to 5. n + o + p + q + r is a real number of 1 to 50, preferably a real number of 1 to 20.

Formula (3) represents a perfluoropolyether having both ends modified with functional groups. Such a perfluoropolyether can be prepared, for example, using Demnum (manufactured by Daikin Industries, Ltd.) as a starting material (for example, by separating a perfluoropolyether having a desired structure by chromatography). In this case, it is possible to prepare a perfluoropolyether in which demnum is a main chain and both ends are modified with functional groups. Such a perfluoropolyether is referred to herein as "D-4OH".

The structure of D-4OH is as follows.
HOCH ₂ CH (OH) CH ₂ OCH ₂ CF ₂ CF ₂ O (CF ₂ CF ₂ CF ₂ O) _m CF ₂ CF ₂ CH ₂ OCH ₂ CH (OH) CH ₂ OH (m is 1 to 50 and 1 ~ 20 is preferred).

パ ー Among the perfluoropolyethers represented by the formulas (1) to (3), those having a demnum main chain are more preferably used because they have a flat molecular chain and easily adhere to hair. That is, among the above-mentioned perfluoropolyethers, D2N, D2M and D-4OH are more preferably used.

In the hair protective agent according to one embodiment of the present invention, the number average molecular weight of the perfluoropolyether is preferably from 100 to 10,000, more preferably from 1,000 to 5,000, and still more preferably from 1,000 to 3,000. Here, the number average molecular weight can be measured, for example, by ¹⁹ F-NMR. Perfluoropolyether having a number average molecular weight of 100 to 10,000 is a by-product of perfluoropolyether for a lubricant. For this reason, it can be said that by-products, which have been poorly used in the past, can be used, and perfluoropolyether for hair protection agents can be provided at low cost, which is preferable.

[Method for producing perfluoropolyether]
The method for producing perfluoropolyether is a known technique (see, for example, WO 01/021630, WO 2009/066784, WO 2016/092900, etc.).

[2. Hair protection agent and hair treatment agent)
The hair protective agent according to one embodiment of the present invention contains a perfluoropolyether. The hair protecting agent may contain only one kind of the perfluoropolyether described in section [1], or may contain two or more kinds. The hair protection agent may include only perfluoropolyether, or may be a mixture of another substance and perfluoropolyether. Examples of other substances include nonpolar substances (silicones, olefins, halogenated alkanes, etc.). When another substance and perfluoropolyether are mixed, the content of the perfluoropolyether is, for example, 20% by mass or more, 50% by mass or more, 70% by mass or more, or 90% or more. Is also good.

毛 The hair treatment agent according to one embodiment of the present invention contains the hair protection agent according to one embodiment of the present invention. Here, “hair treatment agent” refers to an agent used for performing various treatments on hair. Specific examples of the hair treatment agent include, for example, a hair coloring agent for performing a hair color treatment; a permanent agent for performing a permanent wave treatment; a hair styling agent for performing hair styling (a hair wax, a gel, a foam, etc.); Shampoo for performing; rinsing, conditioner, treatment, etc. for maintaining good hair condition; hair oil for further improving hair condition, non-washing type treatment, etc.

The content of the perfluoropolyether in the hair treatment agent according to one embodiment of the present invention is not particularly limited, but is preferably 0.005 to 20% by mass, more preferably 0.01 to 15% by mass. And 0.1 to 10% by mass.

毛 The hair treatment agent according to one embodiment of the present invention may contain, in addition to the perfluoropolyether, ordinary components and / or additives contained in the hair treatment agent. Such components and / or additives include humectants, fats and oils, lanolins, higher alcohols, fluorine compounds, silicones, cationized polymers, surfactants (cationic surfactants, (Anionic surfactants, nonionic surfactants, amphoteric surfactants), thickeners / gelling agents, preservatives, chelating agents, pH adjusters / acids / alkalis, solvents, antioxidants Inflammatory agents, fragrances, pigments, antioxidants and the like can be mentioned.

Examples of humectants include polyhydric alcohols (1,3-butylene glycol, propylene glycol, glycerin, etc.), proteins and peptides (collagen, gelatin, elastin, collagen-degrading peptide, elastin-degrading peptide, keratin-degrading peptide, Silk proteolytic peptide, soybean proteolytic peptide, wheat proteolytic peptide, casein decomposing peptide, etc. and their derivatives, amino acids (arginine, serine, glycine, glutamic acid, trimethylglycine, etc.), plant extract components (aloe extract, hamamelis) Water, loofah water, chamomile extract, licorice extract, etc.), citrate, chondroitin sulfate, sodium lactate, sodium 2-pyrrolidone-5-carboxylate and the like.

As fats and oils, vegetable fats (castor oil, coconut oil, palm oil, palm kernel oil, safflower oil, olives, avocado oil, sesame oil, evening primrose oil, wheat germ oil, macadamia nut oil, hazelnut oil, rosehip oil, Meadowfoam oil, tea tree oil, peppermint oil, corn oil, rapeseed oil, sunflower oil, cottonseed oil, soybean oil, peanut oil, rice bran oil, liquid shea butter, jojoba oil, etc.), hydrocarbons (liquid paraffin, squalane, light) Liquid isoparaffin, ceresin, paraffin wax, polyethylene, microcrystalline wax, petrolatum, etc.), esters (di-2-ethylhexyl succinate, isopropyl palmitate, etc.), waxes (bee wax, candelilla wax, carnauba wax, rice wax, whale wax) , Shellac, cotton wax, mokuro, hydrogenated e Ba oil, etc.) and the like.

Lanolins include liquid lanolin, reduced lanolin, adsorption purified lanolin and the like.

As higher alcohols, straight-chain alcohols (lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, cetostearyl alcohol, etc.), branched chain alcohols (monostearyl glycerin ether (bacyl alcohol), Decyltetradecinol, lanolin alcohol, cholesterol, phytosterol, hexyldecanol, isostearyl alcohol, octyldodecanol, etc.).

Examples of the fluorine-based compounds include fluorine-based compounds and derivatives thereof (polyperfluoroethoxymethoxydifluorohydroxyethyl, polyperfluoroethoxymethoxydifluoromethyldistearylamide, polyperfluoroethoxymethoxydifluoroethyl polyethylene glycol phosphoric acid, and the like). Can be

Silicones include low-viscosity dimethylpolysiloxane, high-viscosity dimethylpolysiloxane, cyclic dimethylsiloxane (decamethylcyclopentasiloxane), methylphenylpolysiloxane, diphenylpolysiloxane, silicone resin, silicone rubber, amino-modified polysiloxane, and cation-modified Examples thereof include polysiloxane, polyether-modified polysiloxane, and fluorine-modified polysiloxane.

Examples of the cationized polymers include cationized cellulose derivatives, cationized starch, cationized guar gum, diallyl quaternary ammonium polymers or copolymers, and quaternized polyvinylpyrrolidone derivatives.

Examples of the cationic surfactants include cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, behenyltrimethylammonium chloride, alkyltrimethylammonium chloride, distearyldimethylammonium chloride, and aminopropylethyldimethylammonium fatty acid lanolin fatty acid ethyl sulfate.

Examples of the anionic surfactants include fatty acid salts, alkyl sulfate salts, polyoxyethylene alkyl sulfate salts, polyoxyethylene fatty amine sulfate salts, acyl N-methyl taurine salts, alkyl ether phosphate salts, N-acyl amino acids. And the like.

Examples of the nonionic surfactants include polyhydric alcohol fatty acid partial esters, polyglycerin fatty acid esters, alkyldimethylamine oxides, alkylpolyglycosides, and alkylglucosides.

と し て Examples of the amphoteric surfactants include betaine alkyldimethylaminoacetate, betaine alkylamidodimethylaminoacetate, and 2-alkyl-N-carboxy-N-hydroxyimidazolinium betaine.

Examples of thickening and gelling agents include cetostearyl glucoside, guar gum, xanthan gum, carrageenan, alginic acid, tragacanth, starch derivatives, sodium carboxymethylcellulose, carboxyvinyl polymer, meadowfoam oil fatty acid dimethicone copolyol, acrylic acid and methacrylic acid ester. Polymer, N, N-dimethylaminoethyl methacrylate diethyl sulfate, N, N-dimethylacrylamide / dimethacrylate, acrylic acid / alkyl methacrylate copolymer, polyvinyl alcohol, acrylic resin alkanolamine liquid, etc. .

Examples of preservatives include p-hydroxybenzoates, benzoates, phenoxyethanol, and quaternary ammonium salts.

Examples of the chelating agent include edetates, phosphonic acids, polyamino acids and the like.

pH adjusters, acids and alkalis include phosphoric acid, malic acid, tartaric acid, carbonic acid, fumaric acid, citric acid, lactic acid, glycolic acid, succinic acid, hydrochloric acid, sulfuric acid, nitric acid, hydroxyethanediphosphonic acid and salts thereof , Sodium hydroxide, potassium hydroxide, disodium hydrogen phosphate, monoethanolamine, diethanolamine, triethanolamine, arginine, aqueous ammonia, aminomethylpropanol, and salts thereof.

Examples of the solvent include water, ethanol, decamethylcyclopentasiloxane, and lower alcohols (such as 2-propanol).

Anti-inflammatory agents include licorice derivatives (glycyrrhizic acid, disodium carbenoxolone, etc.), allantoin, guaiazulene, aloe, α-bisabolol and the like.

防止 Examples of the antioxidant include sodium ascorbate, sodium sulfite and the like.

毛 The hair treatment agent according to one embodiment of the present invention may include a component used for a permanent wave treatment or a hair straightening treatment. Examples of such components include a reducing agent, an oxidizing agent, an alkali agent, a reaction regulator and the like.

As the reducing agent, ammonium thioglycolate, monoethanolamine thioglycolate, L-cysteine, DL-cysteine, L-cysteine hydrochloride, DL-cysteine hydrochloride, acetylcysteine, cysteamine, cysteamine hydrochloride, thiolactic acid, thioapple Acid, glyceryl thioglycolate, thioglycerin, butyrolactone thiol and the like. The reducing agent can be contained in the hair treatment agent within an allowable range (for example, the total content of all reducing agents in terms of thioglycolic acid is less than 2% by mass).

Examples of the oxidizing agent include sodium bromate and hydrogen peroxide.

Examples of the alkaline agent include ammonia water, monoethanolamine, triethanolamine, ammonium carbonate, sodium carbonate, sodium bicarbonate, sodium hydroxide, arginine and the like.

Examples of the reaction modifier include dithiodiglycolic acid and dithiodiglycolate.

毛 A hair treatment agent can be prepared using the above-mentioned components according to a conventional method.

剤 Examples of the dosage form of the hair treatment agent according to one embodiment of the present invention include creams, gels, emulsions, solutions, mist, foams, and the like.

[3. Use of hair treatment agent)
One embodiment of the present invention also includes a method (hair treatment method) of treating the hair of a subject using the above-described hair treatment agent according to one embodiment of the present invention.

に お い て In the present specification, the “subject” is not limited to a human. The hair treatment agent according to one embodiment of the present invention can also treat hair of a non-human mammal. Examples of non-human mammals include artiodactyls (cows, wild boars, pigs, sheep, goats, etc.), odd ungulates (horses, etc.), rodents (mouse, rat, hamster, squirrel, etc.), lagomorphs (rabbits) Etc.), meat (dogs, cats, ferrets, etc.) and the like. The above-mentioned non-human mammals include wild animals in addition to domestic animals or companion animals.

に お い て In the present specification, “hair” means “hair growing on a subject”. When the subject is a human, examples of hair include head hair, beard, eyebrows, eyelashes, nose hair, ear hair, armpit hair, pubic hair, and body hair. When the subject is a human, the hair treatment agent according to one embodiment of the present invention is preferably used for hair.

に お い て In this specification, “treating hair” means performing hair color treatment, permanent wave treatment, hair styling, hair care treatment (hair washing, treatment, etc.). The hair treatment method according to one embodiment of the present invention uses the hair treatment agent according to one embodiment of the present invention. That is, a hair treatment agent containing the hair protection agent according to one embodiment of the present invention is used. Therefore, according to the hair treatment agent according to one embodiment of the present invention, suppression of damage to hair (suppression of damage to the surface of hair, suppression of damage to inside of hair, etc.), improvement in hand (suppression of puffiness, and feeling of unity) Improvement, etc.) and effects such as suppression of static electricity generation can be obtained simultaneously or by the same treatment.

[4. Advantages of hair protecting agent according to one embodiment of the present invention]
Hereinafter, advantages that the hair protective agent according to one embodiment of the present invention may have will be described. However, it is not necessary that certain embodiments of the present invention meet some or all of the advantages described below.

[Simultaneous control of damage and improvement of touch feeling]
As described in the problem column and the effect column, the hair protection agent according to one embodiment of the present invention is a novel hair protection agent that can achieve both suppression of hair damage and improvement in feel.

[Control of external and internal damage to hair]
The main causes of hair damage include hair color treatment and permanent wave treatment. In the hair color treatment, the melanin pigment in the hair is decomposed by the aqueous hydrogen peroxide, and at the same time, the color is formed by the action of the oxidation dye with the hydrogen peroxide. Therefore, the hair coloring process degrades the surface of the hair. On the other hand, the permanent wave treatment cleaves disulfide bonds in hair with an alkaline solution containing a reducing agent, and forms new disulfide bonds with an oxidizing agent. Therefore, the permanent wave treatment mainly degrades the inside of the hair.

The hair protectant according to one embodiment of the present invention has the effect of suppressing damage to the hair and improving the feel to the touch, both for hair damage due to the hair color treatment and for hair damage due to the permanent wave treatment. To play. That is, the hair protection agent according to one embodiment of the present invention reduces external damage and internal damage of hair.

[Effective use of by-products]
Perfluoropolyether having a specific structure is used industrially as a lubricating oil. However, in the process of producing perfluoropolyether for lubricating oil, perfluoropolyether as a by-product different from the desired structure is generated. At present, such a by-product perfluoropolyether is disposed at a high cost.

の 一 In one embodiment of the present invention, perfluoropolyether which is the above-mentioned by-product can be used for the hair protecting agent and the hair treating agent of the present invention. Therefore, it is possible to reduce industrial waste, and it can be said that the present invention is useful also from the viewpoint of using by-products. In addition, the production cost of a fluorine-containing compound such as perfluoropolyether is usually high, but if perfluoropolyether which is a by-product is used as in one embodiment of the present invention, the cost is relatively low. It can be said that it is possible to provide a hair protection agent and a hair treatment agent containing perfluoropolyether.

Examples of such a perfluoropolyether which is a by-product of the perfluoropolyether for a lubricating oil include, for example, the perfluoropolyethers represented by the above formulas (1) to (3) and a number average molecular weight of 100 Perfluoropolyethers up to 10,000. In particular, perfluoropolyethers whose both terminals are not modified with functional groups (such as the perfluoropolyether represented by the formula (1)) have not been found to have remarkable industrial uses. The effect of using as a by-product is great.

[Example 1]
The effect of the hair protectant according to one embodiment of the present invention on the damage that the hair coloring agent gives to the hair was examined. Specifically, a hair sample treated with a hair coloring agent was prepared, and the breaking strength and the friction coefficient of the hair sample were measured.

[Method of preparing hair sample]
The method of preparing the hair sample is as follows.
1. A hair switch that had not undergone any chemical treatment was prepared.
2. The first agent and the second agent were mixed at a weight ratio of 1: 2 to prepare a hair coloring agent. The composition of the first agent and the second agent will be described later.
The hair coloring agent prepared in 3.2 was applied to a hair switch. The amount of application was such that the hairpiece: hair coloring agent = 1: 1 (weight ratio).
4. The hair switch was allowed to stand at 30 ° C. for 30 minutes.
5. The hair switch was washed with a 10% by mass aqueous solution of SDS (aqueous sodium dodecyl sulfate) and then dried.

(Composition of the first agent and the second agent)
The basic composition of the first agent and the second agent is as follows. When the content of the hair protecting agent was changed, the content was adjusted by changing the amount of water (see Examples 1-9 to 1-13 and Comparative Example 1-1). The purpose of the present embodiment is to compare the damage of the hair caused by the hair color treatment. Therefore, the coloring agent for hair dye normally contained in the hair coloring agent was not contained in the first agent used in this example.
● First agent: Cetyl alcohol (higher alcohol): 10% by mass
・ Polyoxyethylene cetyl ether (surfactant): 4% by mass
・ Sodium cetostearyl sulfate (surfactant): 1% by mass
・ Sodium ascorbate (antioxidant): 0.5% by mass
・ Sodium sulfite (antioxidant): 0.5% by mass
・ 25% ammonium water: 10% by mass
・ Sodium bicarbonate: 2% by mass
・ Hair protectant: 0.5% by mass
・ Water: 71.5% by mass
● 2nd agent ・ cetyl alcohol (higher alcohol): 3% by mass
・ Isopropyl palmitate (oil): 0.3%
・ Polyoxyethylene cetyl ether (surfactant): 1% by mass
・ Phosphoric acid (pH adjusting agent): 0.1% by mass
・ Hydroxyethane diphosphonic acid (pH adjuster): 0.3% by mass
-Disodium hydrogen phosphate (pH adjuster): 0.1% by mass
・ 35% hydrogen peroxide: 17% by mass
-Water: 78.2% by mass.

[Method of measuring breaking strength]
Twelve hairs were arbitrarily selected from the hair pieces treated with the hair coloring agent as described above. The major axis and the minor axis of the hair were measured by a hair diameter measuring system (manufactured by Kato Tech Co., Ltd.). From the obtained values, the cross-sectional area was determined by the following equation.
Cross-sectional area (mm ² ) = (π / 4) × major axis (mm) × minor axis (mm).

Next, the tensile breaking value (cN) of the hair was measured using a table type material testing machine Tensilon STA-1150 (manufactured by Orientec Co., Ltd.). The measurements were made in water to prevent the effects of hydrogen bonding.

Finally, the breaking strength per cross-sectional area was calculated based on the following equation.
Breaking strength (cN / mm ² ) = tensile breaking value (cN) / cross-sectional area (mm ² ).

[Method of measuring friction coefficient]
The hair switch treated with the hair coloring agent as described above was conditioned for at least 24 hours at 20 ° C. and 60% humidity. A hair sample having an equivalent ellipticity was stuck to a slide glass except for those having an extreme cross-sectional area ellipticity from the hair samples (12 or more per slide glass). The friction coefficient was measured using a friction tester KES-SE (manufactured by Kato Tech Co., Ltd.). The measurement sensitivity was H, the static friction load was 50 gf, and the sensor used was a silicon type. The scanning direction of the sensor was a direction from the root of the hair to the tip of the hair. The average value of five slide glasses 10 times per sample was defined as the average friction coefficient (MIU), and the value obtained by multiplying the average friction coefficient by 0.1 was defined as the friction coefficient (μ).

[Example 1-1]
D2N (PFPE not modified with a functional group at both ends) was used as a hair protectant. The structure of D2N is as follows. Table 1 shows the measurement results of the hair samples.
_{CF 3 CF 2 CF 2 (CF} 2 CF 2 CF 2 O) m CF 2 CF 2 CF 3 (m = 4.28).

[Example 1-2]
D2M (PFPE whose one end was not modified with a functional group) was used as a hair protectant. The structure of D2M is as follows. Table 1 shows the measurement results of the hair samples.
_{CF 3 CF 2 CF 2 (CF} 2 CF 2 CF 2 O) m CF 2 CF 2 CH 2 OH (m = 12).

[Example 1-3]
As a hair protectant, a mixture of D2N and D2M was used (the same as that used in Examples 1-1 and 1-2). The 1-2 mixing ratio was D2N: D2M = 1: 1 (mass ratio). Table 1 shows the measurement results of the hair samples.

[Example 1-4]
Krytox (PFPE whose both ends were not modified with a functional group) was used as a hair protectant. The structure of Krytox is as follows. Table 1 shows the measurement results of the hair samples.
_{CF 3 CF 2 CF 2 O- (} CF (CF 3) CF 2 O) z -CF 2 CF 3 (z = 6.5).

[Example 1-5]
D-4OH (polar PFPE modified at both ends with a functional group) was used as a hair protectant. The structure of D-4OH is as follows. Table 1 shows the measurement results of the hair samples.
_{HOCH 2 CH (OH) CH 2} OCH 2 CF 2 CF 2 O (CF 2 CF 2 CF 2 O) m CF 2 CF 2 CH 2 OCH 2 CH (OH) CH 2 OH (m = 11).

[Example 1-6]
Fomblin X (PFPE not modified with a functional group at both ends) was used as a hair protectant. The structure of Fomblin X is as follows. Table 1 shows the measurement results of the hair samples.
_{CF 3 CF 2 O (CF 2} CF 2 O) x (CF 2 O) y CF 2 CF 3 (x = 4.10, y = 4.18).

[Example 1-7]
Fomblin Y (PFPE whose one end was not modified with a functional group) was used as a hair protectant. The structure of Fomblin Y is as follows. Table 1 shows the measurement results of the hair samples.
CF ₃ CF ₂ O (CF ₂ CF ₂ O) _x (CF ₂ O) _y CF ₂ CH ₂ O—CH ₂ CH (OH) CH ₂ OH (x = 10, y = 10).

[Example 1-8]
Fomblin HC / R was used as a hair protectant. The structure of Fomblin HC / R is as follows, with an average molecular weight of 6,250. Table 1 shows the measurement results of the hair samples.
CF ₃ O (CF ₂ O) _x (CF ₂ CF (CF ₃ ) O) _y CF ₃ (y / x = 20 to 40).

[Comparative Example 1-1]
The experiment was performed without adding a hair protectant and changing the water content to 71.5% by mass. Table 1 shows the measurement results of the hair samples.

[Comparative Example 1-2]
As a hair protective agent, silicone-based raw material KF-8015 (dimethylpolysiloxane with aminopropyl group added; manufactured by Shin-Etsu Chemical Co., Ltd.) was used. Table 1 shows the measurement results of the hair samples.

[Comparative Example 1-3]
As a hair protectant, KF-9021 (a mixture of 50% trimethylsiloxysilicic acid and 50% cyclopentasiloxane; manufactured by Shin-Etsu Chemical Co., Ltd.) as a silicone-based material was used. Table 1 shows the measurement results of the hair samples.

[Comparative Example 1-4]
As a hair protecting agent, Promois WK (hydrolytic peptide derived from wool; Seiwa Kasei Co., Ltd.), a protein-based material, was used. Table 1 shows the measurement results of the hair samples.

[Comparative Example 1-5]
Proteinic raw material Proticute H gamma (hydrolyzed peptide derived from wool; manufactured by Ichimaru Falcos Co., Ltd.) was used as a hair protectant. Table 1 shows the measurement results of the hair samples.

[Example 1-9]
The experiment was performed using D2N as the hair protectant (same as that used in Example 1-1), changing the content of the hair protectant to 0.01% by mass and the content of water to 71.99% by mass. went. Table 2 shows the measurement results of the hair samples.

[Example 1-10]
The experiment was performed using D2N as the hair protectant (same as that used in Example 1-1), changing the content of the hair protectant to 0.1% by mass and the content of water to 71.9% by mass. went. Table 2 shows the measurement results of the hair samples.

[Example 1-11]
The experiment was performed using D2N as the hair protectant (same as that used in Example 1-1), changing the content of the hair protectant to 1.0% by mass and the content of water to 71% by mass. . Table 2 shows the measurement results of the hair samples.

[Example 1-12]
The experiment was performed using D2N as the hair protectant (the same as that used in Example 1-1), changing the content of the hair protectant to 5.0% by mass and the content of water to 67% by mass. . Table 2 shows the measurement results of the hair samples.

[Example 1-13]
The experiment was performed using D2N as the hair protectant (same as that used in Example 1-1), changing the content of the hair protectant to 10.0% by mass and the content of water to 62% by mass. . Table 2 shows the measurement results of the hair samples.

(result)
According to Table 1, in the case of a hair coloring agent using perfluoropolyether as a hair protecting agent, an improvement in hair breaking strength and a decrease in friction coefficient are observed (see Examples and Comparative Examples 1-1 for comparison). ). On the other hand, when the silicone-based hair protective agent was used, the coefficient of friction was reduced, but the hair breaking strength was not improved (see Comparative Examples 1-2 and 1-3). Further, when the protein-based hair protectant was used, the hair breaking strength was improved, but the coefficient of friction was rather increased (see Comparative Examples 1-4 and 1-5).

Further, according to Table 2, when the content of D2N was in the range of 0.01 to 10.00% by mass, improvement in hair breaking strength and reduction in friction coefficient were observed. Of these, the maximum hair breaking strength was when the D2N content was 1.00% by mass, and the coefficient of friction was minimum when the D2N content was 0.5% by mass. there were.

From these results, it can be said that the hair protectant according to one embodiment of the present invention is effective in suppressing hair damage due to hair color treatment and improving the feel. That is, it is suggested that the hair protective agent according to one embodiment of the present invention can suppress damage to the hair surface and further improve the feel.

[Example 2]
The effect of the hair protective agent according to one embodiment of the present invention on the damage to the hair caused by the perm agent was examined. Specifically, a hair sample treated with a perm agent was prepared, and the breaking strength and friction coefficient of the hair sample were measured.

[Method of preparing hair sample]
The method of preparing the hair sample is as follows.
1. A hair switch that had not undergone any chemical treatment was prepared.
2. The first part was applied to the hair switch. Hair switch: Perm agent = 1: 1 (weight ratio). The composition of the first agent will be described later.
3. The hair switch was allowed to stand at 30 ° C. for 30 minutes, and then washed with water.
4. The second part was applied to the hair switch. The amount of application was such that the hairpiece: hair coloring agent = 1: 1 (weight ratio). The composition of the second agent will be described later.
5. The hair switch was allowed to stand at 30 ° C. for 30 minutes.
6. The hair switch was washed with a 10% by mass aqueous solution of SDS (aqueous sodium dodecyl sulfate) and then dried.

In this example, in order to measure only the effect of the perming agent on the hair, a process of winding the hairpiece around the hair rod was not performed.

(Composition of the first agent and the second agent)
The basic composition of the first agent and the second agent is as follows. When the content of the hair protecting agent was changed, the content was adjusted by changing the amount of water (see Examples 2-3 to 2-6 and Comparative Example 2-5).
● First agent: 50% ammonium thioglycolate (reducing agent): 12% by mass
・ Monoethanolamine (alkali agent): 2% by mass
・ Triethanolamine (alkali agent): 3% by mass
・ Sodium ascorbate (antioxidant): 0.5% by mass
・ Hair protectant: 0.5% by mass
・ Water: 82% by mass
● Second agent: sodium bromate (oxidizing agent): 8% by mass
-Water: 92 mass%.

(4) The method for measuring the breaking strength and the method for measuring the friction coefficient are the same as those in Example 1, and the description thereof will not be repeated.

[Example 2-1]
D2N was used as a hair protectant (the same as that used in Example 1-1). Table 3 shows the measurement results of the hair samples.

[Example 2-2]
D2M was used as a hair protectant (same as used in Example 1-2). Table 3 shows the measurement results of the hair samples.

[Comparative Example 2-1]
As a hair protecting agent, KF-8015, a silicone-based raw material, was used (the same as that used in Comparative Example 1-2). Table 3 shows the measurement results of the hair samples.

[Comparative Example 2-2]
As a hair protecting agent, KF-9021 as a silicone raw material was used (the same as that used in Comparative Example 1-3). Table 3 shows the measurement results of the hair samples.

[Comparative Example 2-3]
Promois WK, a protein-based material, was used as a hair protectant (same as that used in Comparative Examples 1-4). Table 3 shows the measurement results of the hair samples.

[Comparative Example 2-4]
Proteinic raw material Proticute H gamma was used as the hair protectant (same as that used in Comparative Examples 1-5). Table 3 shows the measurement results of the hair samples.

[Comparative Example 2-5]
The experiment was carried out without adding a hair protecting agent and changing the water content to 82.5% by mass. Table 3 shows the measurement results of the hair samples.

[Example 2-3]
The experiment was carried out using D2N as the hair protectant (same as that used in Example 1-1), changing the content of the hair protectant to 0.01% by mass and the content of water to 82.49% by mass. Was. Table 4 shows the measurement results of the hair samples.

[Example 2-4]
The experiment was performed using D2N as the hair protectant (same as that used in Example 1-1), changing the content of the hair protectant to 0.1% by mass and the content of water to 82.4% by mass. went. Table 4 shows the measurement results of the hair samples.

[Example 2-5]
Using D2N as the hair protectant (same as that used in Example 1-1), the experiment was performed by changing the content of the hair protectant to 5.0% by mass and the content of water to 77.5% by mass. went. Table 4 shows the measurement results of the hair samples.

[Example 2-6]
Using D2N as the hair protectant (same as that used in Example 1-1), the experiment was performed by changing the content of the hair protectant to 10.0% by mass and the content of water to 72.5% by mass. went. Table 4 shows the measurement results of the hair samples.

(result)
According to Table 3, in the permanent waving agent using perfluoropolyether as a hair protecting agent, improvement in hair breaking strength and reduction in friction coefficient can be seen (see Examples and Comparative Examples 2-5 for comparison). ). On the other hand, when the silicone-based hair protectant was used, the coefficient of friction was reduced, but the hair breaking strength was not improved (see Comparative Examples 2-1 and 2-2). When the protein-based hair protectant was used, the hair breaking strength was improved, but the friction coefficient was not reduced (see Comparative Examples 2-3 and 2-4).

Further, according to Table 4, when the content of D2N was in the range of 0.01 to 10.00% by mass, an improvement in hair breaking strength and a decrease in friction coefficient were observed. Of these, the maximum hair breaking strength was at a D2N content of 5.00%, and the minimum friction coefficient was at a D2N content of 10.00%. .

From these results, it can be said that the hair protectant according to one embodiment is effective in suppressing hair damage due to permanent wave treatment and improving the feel. That is, it is suggested that the hair protecting agent according to one embodiment of the present invention can suppress damage inside the hair and further improve the feel.

[Example 3]
The effect of the hair protective agent according to one embodiment of the present invention on the damage that the hair coloring agent causes to the hair surface was confirmed. Specifically, a hair sample treated with a hair coloring agent was prepared, and the surface of the hair sample was observed using a scanning electron microscope (SEM). The method for preparing the hair sample and the composition of the hair coloring agent were the same as in Example 1-1, and D2N was used as the hair protective agent (the same as that used in Example 1-1). The results are as shown in FIG.

(result)
FIG. 1A shows the surface of healthy hair that has not been subjected to hair color treatment. (B) is the surface of the hair that has been treated with a hair coloring agent to which D2N has been added as a hair protecting agent. (C) is the surface of the hair that has been treated with the hair coloring agent to which D2N is not added. When D2N was not added to the hair coloring agent, peeling was observed on the cuticle on the hair surface (FIG. 1 (c)). On the other hand, when D2N was added to the hair coloring agent, cuticle peeling was suppressed.

From these results, it was shown that the hair protective agent according to one embodiment of the present invention has an effect of suppressing damage to the hair surface in hair color treatment. Therefore, the surface of the hair can be kept smooth, and the effect of improving the feel of the hair is also expected.

[Example 4]
The effect of the hair protective agent according to one embodiment of the present invention on the outflow of protein from the hair due to the hair color treatment was examined. Specifically, a hair sample that had been subjected to hair color treatment once or three times was prepared, and the sulfur content of the hair sample was measured by SEM-EDX. For comparison, the sulfur content of hair treated with a hair coloring agent without the addition of D2N was also measured. The method of preparing the hair sample and the composition of the hair coloring agent were the same as those in Example 1 (for the hair sample on which the hair coloring treatment was performed three times, steps 3 to 5 in Example 1 were repeated a total of three times). The method for measuring the sulfur content is as described below.

[Measurement of sulfur content]
Hair tips for 12 prepared hair samples were cut out. The reason why the hair tips were cut out is that the hair tips are portions where the hair is more damaged by the hair color treatment. Next, the sulfur content of the cut hair samples was measured by SEM-EDX. The ratio (atomic%) of the sulfur atoms in the hair was calculated from the average of the intensity of the K-line (SK) of the sulfur atoms detected for the twelve samples. The results are shown in FIG.

(result)
According to FIG. 2, when D2N was added to the hair coloring agent, the decrease in the sulfur content due to the hair coloring treatment of the hair was suppressed as compared with the case where D2N was not added. In particular, in the hair sample that was subjected to the hair color treatment once, the decrease in the sulfur content of the hair was strongly suppressed.

か ら From the results, it is considered that the hair protecting agent according to one embodiment of the present invention suppresses the outflow of proteins from hair. Therefore, it is suggested that the hair protective agent according to one embodiment of the present invention has an effect of suppressing hair damage due to hair color treatment.

[Example 5]
The effect of the hair protective agent according to one embodiment of the present invention on hair puffiness was studied. Specifically, a sample in which D2N was added to a commercially available non-washable treatment was applied to a 30 cm long hair switch. Then, the amount of static electricity of the hair switch was measured. Specifically, it is as follows.
1. Glamorous curl cream essence (manufactured by Nakano Pharmaceutical Co., Ltd.) was used as a commercially available non-washable treatment. The amount of D2N added was 1.0% by mass. 2. A hairdressing agent was applied to the hair switch. The amount of application was such that the treatment of hair switch: non-washing type was 1: 1 (weight ratio).
3. The hair switch was rubbed 30 times with hands wearing vinyl gloves to generate static electricity.
4. The amount of generated static electricity was measured using an electrostatic meter (Digital Electro Static Meter Model [KDS-0303]: manufactured by Kasuga Electric Co., Ltd.). Table 5 shows the results. As a comparison, the amount of static electricity of a hair sample treated with a non-rinsing type treatment to which D2N was not added was also measured.

(result)
By applying a non-washable treatment to which D2N was added, a decrease in the amount of static electricity was observed. From these results, it is confirmed that the hair protective agent according to one embodiment of the present invention has an effect of suppressing the generation of static electricity in hair. That is, it can be said that the hair protective agent according to one embodiment of the present invention has an effect of suppressing hair puffiness.

[Example 6]
The effect of the hair protective agent according to one embodiment of the present invention on the feel of hair was sensory evaluated. Specifically, the wig was treated with a non-washing type treatment to which D2N was added, and nine panelists were evaluated for the feeling of touch (moistness and unity). More specifically, the following procedure was performed.
1. 2.1 g of a commercially available non-washable treatment to which D2N was added (the same as in Example 5) was applied to a wig (manufactured by Bureaux Corporation). After application, the mixture was well mixed with a comb.
2. The wig was sequentially washed with water, dried with a towel, and dried. The feel of the wig after completion of each stage was compared to that of a wig treated with a non-flushable treatment without D2N. Table 6 shows the results.

(result)
When a treatment sample of a non-washable type to which D2N is added is applied, the touch tends to be improved after washing with water, after drying with a towel, and after drying. In particular, after drying, all panelists reported improved touch, and 4 out of 9 panelists evaluated that the touch was further improved.

From these results, it is considered that the hair protecting agent according to one embodiment of the present invention has an effect of improving the feel of hair.

The present invention can be used in industries dealing with various hair treatment agents such as hair color treatment and permanent wave treatment.

Claims (8)

1. 毛 A hair protective agent containing perfluoropolyether.
2. The hair protection agent according to claim 1, wherein the perfluoropolyether includes a perfluoropolyether represented by the following formula (1).
   _{CF 3 - (CF 2) m} -O- (CF 2 CF 2 O) n - (CF 2 O) o - (CF (CF 3) CF 2 O) p - (CF (CF 3) O) q - ( _{CF 2 CF 2 CF 2 O)} r - (CF 2) s -CF 3 (1)
   [In equation (1),
   m + s represents a real number of 0 to 5,
   n + o + p + q + r represents a real number of 1 to 50. ]
3. The hair protection agent according to claim 1, wherein the perfluoropolyether includes a perfluoropolyether represented by the following formula (2).
   _{CF 3 - (CF 2) m} -O- (CF 2 CF 2 O) n - (CF 2 O) o - (CF (CF 3) CF 2 O) p - (CF (CF 3) O) q - ( _{CF 2 CF 2 CF 2 O)} r - (CF 2) s -CH 2 O-R1 (2)
   [In equation (2),
   R1 represents H, — [CH ₂ —CH (OH) CH ₂ O] _x —R3, or — (CH ₂ ) _y OH;
   x represents a real number of 1 to 5, y represents a real number of 1 to 6,
   R3 is H, _OH, a CH _3, C 6 _{H 5} or _C 6 _H 4 O-B,
   B is a C1-C4 alkoxy group, amide group, or amino group;
   m + s represents a real number of 1 to 5,
   n + o + p + q + r represents a real number of 1 to 50. ]
4. The hair protecting agent according to claim 1, wherein the perfluoropolyether includes a perfluoropolyether represented by the following formula (3).
   _{R2-OCH 2 - (CF 2} ) m -O- (CF 2 CF 2 O) n - (CF 2 O) o - (CF (CF 3) CF 2 O) p - (CF (CF 3) O) q — (CF ₂ CF ₂ CF ₂ O) _r — (CF ₂ ) _s —CH ₂ O—R1 (3)
   [In equation (3),
   R1 and R2 each independently represent H, — [CH ₂ —CH (OH) CH ₂ O] _x —R3, or — (CH ₂ ) _y OH;
   x represents a real number of 1 to 5, y represents a real number of 1 to 6,
   R3 is H, _OH, a CH _3, C 6 _{H 5} or _C 6 _H 4 O-B,
   B is a C1-C4 alkoxy group, amide group, or amino group;
   m + s represents a real number of 1 to 5,
   n + o + p + q + r represents a real number of 1 to 50. ]
5. The hair protective agent according to any one of claims 1 to 4, wherein the perfluoropolyether has a number average molecular weight of 100 to 10,000.
6. 毛 A hair treatment agent comprising the hair protection agent according to any one of claims 1 to 5.
7. 7. The hair treatment composition according to claim 6, wherein the content of the perfluoropolyether is 0.005 to 20% by mass.
8. 方法 A hair treatment method using the hair treatment agent according to claim 6 or 7.

Images