JP2006265187A - Emulsified agent for hair treatment - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an agent for hair treatment improving stability of a specific cyclic mercapto compound in the agent even in the presence of water, preventing a reduction in the concentration of the cyclic mercapto compound in the agent with time, discoloring, formation of precipitates, etc., of the agent and maintaining stable performances and an excellent appearance over a long period. <P>SOLUTION: The agent for the hair treatment comprises the specific cyclic mercapto compound, a surfactant and water and is emulsified. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a hair treatment agent suitable for an emulsified hair treatment agent, in particular, a permanent wave treatment agent, and a hair permanent wave processing method using the same.

  It is known that a permanent wave is formed by two processes. That is, there are a step of reducing and cleaving the cystine (disulfide) bond of hair by the action of the reducing agent, and a subsequent neutralization or fixing step using an oxidizing agent, and the latter step restores the cystine (disulfide) bond.

  Conventionally, compounds generally used as keratin reducing substances such as thioglycolic acid, cysteine, acetylcysteine, and salts thereof have been used as compounds used in permanent processing of hair. Since these conventional compounds, which are also called keratin reducing substances, have practical performance under alkaline conditions for the permanent processing of hair, many permanent liquids are adjusted to be alkaline with a pH of about 9.5. However, it is known that perm liquid adjusted to alkaline causes damage to hair and scalp, and in order to solve these disadvantages, a neutral to slightly acidic pH range (pH: 3 to 7.5, 25). The development of keratin reducing substances that can be used at 0 ° C is underway.

For example, use of a monoglycerol ester of thioglycolic acid as a keratin reducing substance used in such a pH range has been studied (for example, Patent Document 1). In addition, the use of mercaptoglycolamide derivatives and mercaptolactic acid amide derivatives has also been studied for the purpose of solving skin disorders observed with thioglycolate esters (for example, Patent Document 2 and Patent Document 3). Furthermore, the use of cysteamine, which is considered to be effective with weak acidity, has also been studied. (For example, Patent Document 4)
Japanese Patent Application Laid-Open No. 08-291031 Special Table 2000-507272 Special table 2003-528901 gazette JP 03-271214 A

  However, the thioglycolic acid monoglycerol ester proposed in Patent Document 1 is in a liquid state and is excellent in terms of handleability and odor, but there is also a report of sensitization presumed to be derived from a hydroxyl group in the structure. It has not reached.

  The mercaptocarboxylic acid amide proposed in Patent Document 2 is already known to have skin irritation, and the same sensitization is also a concern with the mercaptocarboxylic acid amide derivative proposed in Patent Document 3, Furthermore, there is a problem that there is a concern about lack of purification, sensitization by raw material amine released during storage, and skin irritation.

The cysteamine proposed in Patent Document 4 does not have sufficient wave performance from weak acidity to acidity, and there are many problems such as the hair after perm treatment has a unique odor.
As described above, in the conventional keratin reducing substances, the desired permanent wave processing chemicals have not always been obtained.

As a solution to this problem, the present applicant has already proposed a permanent wave processing agent containing a cyclic mercapto compound represented by the formula (1) or the like as a keratin-reducing substance. This permanent waving agent has higher wave performance than known compounds in a neutral to weakly acidic pH range where there is little irritation to hair and skin, while reducing irritation to hair and skin. Wave processing can be reliably applied to the hair.

  However, the stability of the cyclic mercapto compound in an aqueous solution is not sufficient, and there is room for improvement. That is, since this specific cyclic mercapto compound decomposes with time in an aqueous solution, when the permanent waving agent contains water, the concentration of the cyclic mercapto compound in the agent decreases with time. There is a problem that coloring, precipitation, and the like occur along with the decomposition, deteriorating the appearance and reducing the commercial value.

  For this reason, the present invention improves the stability of the cyclic mercapto compound in a drug containing water, prevents the cyclic mercapto compound concentration in the drug from decreasing over time, prevents the coloring or precipitation of the drug, and the like. An object of the present invention is to provide a hair treatment agent having a stable performance and an excellent appearance.

  As a result of intensive research, the inventors of the present invention contain a specific cyclic mercapto compound, a surfactant, and water, and according to the emulsified hair treatment agent, the stability of the cyclic mercapto compound in the agent is stable. The inventors have found that the properties can be improved, and have completed the present invention.

That is, the present invention includes the following items (1) to (15), for example.
(1) A hair treatment agent comprising a compound represented by the following formula (1), a surfactant, and water and emulsifying;

(X represents a structure of any of —O—, —S—, —NH—, and —NR ¹ —. R ¹ represents an alkyl group having 1 to 6 carbon atoms. R ² represents a hydrogen atom or 1 carbon atom. Represents an alkyl group of ˜6, Y represents an oxygen atom or a sulfur atom, and R represents a divalent organic residue which may have a mercapto group.

X (2) Formula (1) is, -O -, - NH -, - NCH 3 - , or -S- hair treatment agent according to (1), characterized in that.
(3) The hair treatment agent according to (1) or (2) above, wherein Y in the formula (1) is an oxygen atom.

(4) The hair treatment agent according to any one of the above (1) to (3), wherein R in the formula (1) is an alkylene group.
(5) The permanent waving agent according to any one of (1) to (3) above, wherein R in the formula (1) is an alkylene group having one or more mercapto groups.

  (6) The compound represented by the formula (1) is 2-mercapto-4-butyrolactone, 2-mercapto-4-methyl-4-butyrolactone, 2-mercapto-4-ethyl-4-butyrolactone and 2-mercapto- The hair treatment agent according to (1) above, which is at least one selected from the group consisting of 6-hexanolactam.

  (7) The surfactant is at least selected from the group consisting of a nonionic surfactant, a cationic surfactant, an anionic surfactant, an amphoteric surfactant, a polymer surfactant, and a biosurfactant. The hair treatment agent according to any one of the above (1) to (6), wherein the hair treatment agent is one type.

  (8) The nonionic surfactant is at least one selected from the group consisting of polyoxyethylene alkyl ether, polyoxyethylene alkenyl ether, polyoxyethylene alkylphenyl ether having 10 to 100 polyoxyethylene addition moles. The hair treatment agent according to (7) above, wherein

(9) The hair treatment agent according to (7) above, wherein the nonionic surfactant is a silicone-based nonionic surfactant.
(10) The hair treatment agent according to (7), wherein the biosurfactant has a lipopeptide structure.

  (11) The compound represented by the formula (1) is contained in an amount of 0.2 to 30% as a reducing substance content (as thioglycolic acid). (10) The hair treatment agent according to any one of (10).

(12) The hair treatment agent according to any one of (1) to (11) above, wherein the surfactant is contained in an amount of 0.1 to 10% by mass.
(13) The hair treatment agent according to any one of (1) to (12) above, wherein the pH of the agent is 4.0 to 7.5.

(14) The hair treatment agent according to any one of (1) to (13) above, which is a permanent wave processing agent.
(15) A permanent wave processing method for hair, wherein the hair treatment agent according to any one of (1) to (13) is used as a permanent wave processing agent.

  According to the hair treatment drug of the present invention, even in the presence of water, the stability of a specific cyclic mercapto compound in the drug is improved, and the concentration of the cyclic mercapto compound in the drug is reduced over time. Coloring and precipitation can be prevented, and stable performance and excellent appearance can be maintained over a long period of time.

  That is, when the hair treatment agent of the present invention is used as a permanent wave processing agent, excellent permanent processing performance in a neutral to weakly acidic pH region can be exhibited without change even after long-term storage. In addition, appearance defects such as discoloration and precipitation can be suppressed, and the commercial value can be further increased.

  Therefore, the hair treatment agent of the present invention is suitable as a permanent wave processing agent, and is extremely useful for permanent processing of hair.

Hereinafter, the present invention will be specifically described.
The hair treatment agent of the present invention contains a compound represented by the following formula (1), a surfactant and water and is emulsified.

Cyclic Mercapto Compound The hair treatment agent of the present invention contains at least a cyclic mercapto compound represented by the following formula (1).

In the above formula (1), X is -O -, - S -, - NH -, - NR 1 - shows the structure of any of, R ¹ represents an alkyl group having 1 to 6 carbon atoms. R ² represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Y represents an oxygen atom or a sulfur atom. R represents a divalent organic residue which may have a mercapto group.

As R ¹ , a methyl group and an ethyl group are desirable from the viewpoint of improving the permeability to hair. More preferably, R ¹ is a methyl group.
X is —O—, —NH—, —NCH ₃ — or —S—, which has a relatively high solubility in an aqueous solution when preparing a hair treatment agent often used as an aqueous solution. From the viewpoint of liquid preparation.

In the formula (1), Y represents an oxygen atom or a sulfur atom, and an oxygen atom is more preferable from the viewpoint of industrial raw material availability and handleability.
Examples of R ² include a hydrogen atom, a methyl group, an ethyl group, and a propyl group. Among them, a hydrogen atom, a methyl group, and an ethyl group are preferable.

R represents a divalent organic residue which may have a mercapto group (-SH). R is not particularly limited as long as it is a divalent organic group, but is preferably an alkylene group. As the alkylene group, an alkylene group having 2 to 6 carbon atoms in the main chain is preferable. Moreover, you may have a branch and / or a side chain. Examples of the side chain include an alkyl group and an alkenyl group.

  Moreover, when R has a mercapto group, the mercapto group may be one or plural, but one or two is preferable. In particular, the divalent organic residue is preferably one having a mercapto group bonded to an alkylene group. Moreover, there is no restriction | limiting in particular in the position which a mercapto group couple | bonds with an alkylene group. The mercapto group may be directly bonded to the alkylene group, or may be further via an alkylene group (for example, a mercaptoethyl group).

Among these, preferable R includes an ethylene group and a propylene group in terms of industrial availability.
Specific examples of the compound represented by the formula (1) include 2-mercapto-3-propiolactone, 2-mercapto-2-methyl-3-propiolactone, 2-mercapto-3-methyl-
3-propiolactone, 2-mercapto-3-ethyl-3-propiolactone, 2-mercapto-2,3-dimethyl-3-propiolactone, 2-mercapto-3-propiolactam, 2-mercapto- 2-Methyl-3-propiolactam, 2-mercapto-3-methyl-3-propiolactam, 2-mercapto-3-ethyl-3-propiolactam, 2-mercapto-2,3-dimethyl-3- Propiolactam, 2-mercapto-3-propiothiolactone, 2-mercapto-2-methyl-3-propiothiolactone, 2-mercapto-3-methyl-3-propiothiolactone, 2-mercapto-3 -Ethyl-3-propiothiolactone, 2-mercapto-2,3-dimethyl-3-propiothiolactone, 2-mercapto-4-butyrolac 2-mercapto-2-methyl-4,4-dimethyl-4-butyrolactone, 2-mercapto-3- (2-propenyl) -4-butyrolactone, 2-mercapto-4-methyl-4-butyrolactone, 2- Mercapto-2-methyl-4-butyrolactone, 2-mercapto-3-methyl-4-butyrolactone, 2-mercapto-4-methyl-4-butyrolactone, 2-mercapto-3,4-dimethyl-4-butyrolactone, 2- Mercapto-2-ethyl-4-butyrolactone, 2-mercapto-3-ethyl-4-butyrolactone, 2-mercapto-4-ethyl-4-butyrolactone, 2-mercapto-4-butyrothiolactone, 2-mercapto-2 -Methyl-4-butyrothiolactone,

2-mercapto-3-methyl-4-butyrothiolactone, 2-mercapto-4-methyl-4-butyrothiolactone, 2-mercapto-3,4-dimethyl-4-butyrothiolactone, 2-mercapto 2-ethyl-4-butyrothiolactone, 2-mercapto-3-ethyl-4-butyrothiolactone, 2-mercapto-4-ethyl-4-butyrothiolactone, 2-mercapto-4-butyrolactam, 2-mercapto-2-methyl-4-butyrolactam, 2-mercapto-3-methyl-4-butyrolactam, 2-mercapto-4-methyl-4-butyrolactam, 2-mercapto-3,4-dimethyl-4-butyrolactam, 2-mercapto-2-ethyl-4-butyrolactam, 2-mercapto-3-ethyl-4-butyrolactam, 2-mercapto-4 Ethyl-4-butyrolactam, 2-mercapto-5-valerolactone, 2-mercapto-2-methyl-5-valerolactone, 2-mercapto-3-methyl-5-valerolactone, 2-mercapto-4-methyl-5 -Valerolactone, 2-mercapto-5-methyl-5-valerolactone, 2-mercapto-2-ethyl-5-valerolactone, 2-mercapto-3-ethyl-5-valerolactone, 2-mercapto-4-ethyl -5-valerolactone, 2-mercapto-5-ethyl-5-valerolactone, 2-mercapto-5-valerolactam, 2-mercapto-2-methyl-5-valerolactam,

2-mercapto-3-methyl-5-valerolactam, 2-mercapto-4-methyl-5-valerolactam, 2-mercapto-5-methyl-5-valerolactam, 2-mercapto-2-ethyl-5-valero Lactam, 2-mercapto-3-ethyl-5-valerolactam, 2-mercapto-4-ethyl-5-valerolactam, 2-mercapto-5-ethyl-5-valerolactam, 2-mercapto-5-valerothiolactone 2-mercapto-2-methyl-5-valerothiolactone, 2-mercapto-3-methyl-5-valerothiolactone, 2-mercapto-4-methyl-5-valerothiolactone, 2-mercapto-5-methyl -5-valerothiolactone, 2-mercapto-2-ethyl-5-valerothiolactone, 2-mercapto-3-ethyl-5 Valerothiolactone, 2-mercapto-4-ethyl-5-valerothiolactone, 2-mercapto-5-ethyl-5-valerothiolactone, 2-mercapto-6-hexanolactone, 2-mercapto-2-methyl- 6-hexanolactone,

2-mercapto-3-methyl-6-hexanolactone, 2-mercapto-4-methyl-6-hexanolactone, 2-mercapto-5-methyl-6-hexanolactone, 2-mercapto-6-methyl- 6-hexanolactone, 2-mercapto-6-hexanolactam, 2-mercapto-2-methyl-6-hexanolactam, 2-mercapto-3-methyl-6
Hexanolactam, 2-mercapto-4-methyl-6-hexanolactam, 2-mercapto-5-methyl-6-hexanolactam, 2-mercapto-6-methyl-6-hexanolactam, 2-mercapto- 6-hexanothiolactone, 2-mercapto-2-methyl-6-hexanothiolactone, 2-mercapto-3-methyl-6-hexanothiolactone, 2-mercapto-4-methyl-6-hexanothiolactone, 2- Mercapto-5-methyl-6-hexanothiolactone, 2-mercapto-6-methyl-6-hexanothiolactone, 2-mercapto-7-heptanolactone, 2-mercapto-7-heptanothiolactone, 2-mercapto- 7-heptanolactam, 2-mercapto-8-octanolactone, 2-mercapto-8-octanochi Lactone, 2-mercapto-8-octanolactam, 2-mercapto-9-nonalactone, 2-mercapto-9-nonathiolactone, 2-mercapto-9-nonalactam, and N-methyl or N- of these lactams Examples thereof include ethyl derivatives.

  Among these, 2-mercapto-4-butyrolactone (2-mercapto-4-butanolide), 2-mercapto-4-butyrothiolactone, 2-mercapto-4-butyrolactam, 2-mercapto-4-methyl-4- Butyrolactone, 2-mercapto-4-ethyl-4-butyrolactone, 2-mercapto-5-valerolactone, 2-mercapto-5-valerolactam, 2-mercapto-6-hexanolactam have permanent performance, hair straightening From the viewpoint of hair straightening performance such as curling and industrial production.

  These compounds can be produced according to known methods. For example, it can be synthesized by introducing a mercapto group after using a lactone compound or a lactam compound as a halogenated compound.

  Specifically, mercaptolactone and mercaptothiolactone are commercially available using a commercially available lactone or thiolactone. Am. Chem. Soc. 1945,. 67. 2218-2220, a halogen compound synthesized by the method described in 67.2218-2220, or a commercially available halogen compound, is further used in Ann. A lactone derivative can be synthesized by reacting according to the method described in 1960, 639.146-56.

  Mercaplactams are described in J. Org. Am. Chem. Soc. 1958.80.6233-6237, using a halogen compound synthesized according to the method described in Ann. A lactam derivative can be synthesized by reacting according to the method described in 1960, 639.146-56.

  When such a mercapto compound is used as the main component of a hair treatment agent, it acts at a low pH that does not affect the hair, and exhibits a good permanent wave effect. Is also effective and has little effect on the skin. Although the reason for this is not clear, having the structure of the compound increases lipophilicity compared to conventional reducing agents, improves hair permeability, and has a heterocyclic ring to oxidize mercapto compounds. In particular, it is likely to be neutral and weakly acidic and more easily oxidized. As a result, unlike mercapto compounds that have been used conventionally, it is considered that they function as a reducing agent without being alkaline.

However, such a mercapto compound tends to undergo a decomposition reaction over time in the presence of water.
Surfactants, the hair processing agents of the water present invention, in addition to the above cyclic mercapto compound includes a surfactant and water. In the present invention, since the surfactant is contained in addition to the cyclic mercapto compound, the cyclic mercapto compound can be stably maintained in an emulsified state in the presence of water.

  The surfactant that can be used for the hair treatment agent of the present invention is not particularly limited as long as it can sufficiently emulsify the cyclic mercapto compound in the presence of water. Preferable examples include at least one selected from the group consisting of a cationic surfactant, an anionic surfactant, an amphoteric surfactant, a polymer surfactant, and a biosurfactant.

Non-ionic surfactants include
Polyoxyethylene (2) lauryl ether, polyoxyethylene (4.2) lauryl ether, polyoxyethylene (9) lauryl ether, polyoxyethylene (21) lauryl ether, polyoxyethylene (23) lauryl ether, polyoxyethylene (25) Lauryl ether, polyoxyethylene (2) cetyl ether, polyoxyethylene (5,5) cetyl ether, polyoxyethylene (7) cetyl ether, polyoxyethylene (10) cetyl ether, polyoxyethylene (15) Cetyl ether, polyoxyethylene (20) cetyl ether, polyoxyethylene (23) cetyl ether, polyoxyethylene (25) cetyl ether, polyoxyethylene (30) cetyl ether, polyoxyethylene (40) Ether, polyoxyethylene (2) stearyl ether, polyoxyethylene (4) stearyl ether, polyoxyethylene (20) stearyl ether, polyoxyethylene (5) behenyl ether, polyoxyethylene (10) behenyl ether, polyoxyethylene (20) polyoxyethylene alkyl ethers such as behenyl ether, polyoxyethylene (30) behenyl ether, polyoxyethylene (2) alkyl ether, polyoxyethylene (4) alkyl ether, polyoxyethylene (10) alkyl ether;
Polyoxyethylene alkylphenyl ethers such as polyoxyethylene (16) nonylphenyl ether;

Polyoxyethylene alkenyl such as polyoxyethylene (7) oleyl ether, polyoxyethylene (10) oleyl ether, polyoxyethylene (15) oleyl ether, polyoxyethylene (20) oleyl ether, polyoxyethylene (50) oleyl ether ether;
Polyoxyethylene poly, such as polyoxyethylene (1) polyoxypropylene (4) cetyl ether, polyoxyethylene (10) polyoxypropylene (4) cetyl ether, polyoxyethylene (1) polyoxypropylene (8) cetyl ether Oxypropylene alkyl ether;
Polyoxyethylene alkyl alcohols such as polyoxyethylene (5) lanolin alcohol, polyoxyethylene (10) lanolin alcohol, polyoxyethylene (20) lanolin alcohol;
Polyoxyethylene polyoxypropylene glycol; polyoxyethylene polyoxypropylene alkyl glycol;
Polyoxyethylene glyceryl such as polyoxyethylene (5) glyceryl monooleate, polyoxyethylene (15) glyceryl monooleate;

Polyoxyethylene (3) castor oil, polyoxyethylene (10) castor oil, polyoxyethylene (20) castor oil, polyoxyethylene (40) castor oil, polyoxyethylene (50) castor oil, polyoxyethylene (60 ) Castor oil, polyoxyethylene (5) hydrogenated castor oil, polyoxyethylene (10) hydrogenated castor oil, polyoxyethylene (20) hydrogenated castor oil, polyoxyethylene (30) hydrogenated castor oil, polyoxyethylene (40) Polyoxyethylenated castor oil, such as hydrogenated castor oil, polyoxyethylene (50) hydrogenated castor oil, polyoxyethylene (60) hydrogenated castor oil, polyoxyethylene (80) hydrogenated castor oil;
Polyoxyethylene (6) sorbitol monolaurate, polyoxyethylene (20) sorbitan monolaurate, polyoxyethylene (20) sorbitan monopalmitate, polyoxyethylene (6) sorbitan monostearate, polyoxyethylene monostearate (20 ) Sorbitan, polyoxyethylene monoisostearate (20) sorbitan, polyoxyethylene tristearate (20) sorbitan, polyoxyethylene monooleate (6) sorbitan, polyoxyethylene monooleate (20) sorbitan, trioleic acid Polyoxyethylene (20) sorbitan, polyoxyethylene (20) palm oil fatty acid sorbitan, polyoxyethylene (10-80) sorbitan monolaurate, polyoxyethylene tristearate Sorbitan, polyoxyethylene (20) sorbitan isostearate, polyoxyethylene (150) sorbitan tristearate, polyoxyethylene (6) sorbitol tetraoleate, polyoxyethylene (30) sorbitol tetraoleate, polytetraoleate poly Polyoxyethylene sorbitan fatty acid esters such as oxyethylene (40) sorbit, polyoxyethylene tetraoleate (60) sorbit;

Sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monoisostearate, sorbitan monooleate, sorbitan sesquistearate, sorbitan sesquiisostearate, sorbitan sesquioleate, sorbitan tristearate, sorbitan trioleate, coconut Sorbitan fatty acid esters such as oil fatty acid sorbitan, sorbitan isostearate, sorbitan sesquiisostearate, sorbitan distearate;
Polyhydric alcohol fatty acid partial ester; Polyoxyethylene polyhydric alcohol fatty acid partial ester; Polyoxyethylene fatty acid mono (di) ester; Polyglycerin fatty acid ester;
Polyoxyethylene fatty acid amides such as polyoxyethylene (5) oleic acid amide; fatty acid diethanolamide; polyoxyethylene alkylamine; triethanolamine fatty acid partial ester; trialkylamine oxide;
Examples thereof include silicone-based nonionic surfactants such as polyoxyethylene / methylpolysiloxane copolymer (dimethicone copolyol) and aminoethylaminopropylsiloxane / dimethylsiloxane copolymer (amodimethicone).

These can be used alone or in combination of two or more.
Among these, from the viewpoint of the strength of emulsification and the ease of handling, it is composed of polyoxyethylene alkyl ether, polyoxyethylene alkenyl ether, polyoxyethylene alkylphenyl ether having a polyoxyethylene addition mole number of 10 to 100. Preferred is at least one selected from the group. In addition, silicone-based nonionic surfactants are also preferably used from the viewpoint of expecting slipping to hair and imparting an antistatic effect. The silicone-based nonionic surfactant is known as a polyether-modified silicone oil, an amino-modified silicone oil, etc., but exhibits a behavior as a nonionic surfactant. Classify as an agent. Examples of commercially available products include SH3771M (Toray Dow Corning Silicone Co., Ltd.), SM8704C (Toray Dow Corning Silicone Co., Ltd.), and the like.

As a cationic surfactant,
Cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, lauryltrimethylammonium chloride, behenyltrimethylammonium chloride, distearyldimethylammonium chloride, dicocoyldimethylammonium chloride, dimethyldiallylammonium chloride-acrylic acid copolymer, dimethyldiallylammonium chloride-acrylic acid Acrylamide terpolymer, benzalkonium chloride, cetylpyridinium chloride, benzethonium chloride, lanolin-derived quaternary ammonium, amidoamines, dimethylaminopropylamide stearate, diethylaminoethylamide stearate, JP2004-176070
And silicone-based cationic surfactants (silanes or siloxanes having a quaternary ammonium group in the molecule) described in Japanese Patent Publication No. JP-A No. 2004-26883.

Examples of anionic surfactants include fatty acid salts; polyoxyethylene alkyl ether methyl carboxylates; alkylbenzene sulfonates; alkyl naphthalene sulfonates; alkyl sulfonates; α-olefin sulfonates; Condensate; Dialkylsulfosuccinic acid ester salt such as dioctyl sodium sulfosuccinate; Disodium alkylamidoethyl sulfosuccinic acid ester; α-sulfonated aliphatic alkyl ester salt; Sodium alkyl isethinate; Petroleum sulfonate; Sodium lauryl sulfate, etc. Alkyl sulfates; alkyl ether sulfates such as ammonium lauryl ether sulfate; sulfated oils and fats; polyoxyethylene alkyl sulfates such as polyoxyethylene (2,5) sodium lauryl sulfate Polyoxyethylene alkyl ether sulfate; polyoxyethylene alkyl phenyl ether sulfate; polyoxyethylene styrenated phenyl ether sulfate; alkyl phosphate; polyoxyethylene alkyl ether phosphate; polyoxyethylene alkyl phenyl ether phosphate Salts; N-acyl-N-methyl taurine salts such as sodium N-methyl-N-oleyl taurine and the like.

Amphoteric surfactants include N, N-dimethyl-N-alkyl-N-carboxymethylammoniobetaine, N, N, N-trimethyl-N-alkyleneammoniocarboxybetaine, lauryldimethylaminoacetic acid betaine, coconut oil fatty acid Carboxybetaines such as amidopropyldimethylaminoacetic acid betaine;
Sulfobetaines such as N-acylamidopropyl-N ′, N′-dimethyl-N′-β-hydroxypropylene ammoniosulfobetaine;
N, N-dialkyl-N, N-bis (polyoxyethylene sulfate) ammoniobetaine;
Imidazolinium betaines such as 2-alkyl-1-hydroxyethyl-1-carboxymethylimidazolium betaine;
N-coconut oil fatty acid acyl-N-carboxymethyl-N-hydroxyethylethylenediamine sodium, N-coconut oil fatty acid acyl-N-carboxymethyl-N-hydroxyethylethylenediamine, sodium lauryl sulfate and the like can be mentioned.

Examples of the polymer surfactant include acrylic acid / methacrylic acid copolymer, polyacrylamide, and sodium polyacrylate.
Examples of the biosurfactant include lecithin, hydrogenated lecithin, saponin, surfactins and / or salts thereof. Here, the biosurfactant means a substance having a surfactant-like property that a prokaryote synthesizes during its life activity. Among these, surfactins are compounds having a lipopeptide structure represented by the following formula (2) and / or related compounds thereof, or compositions containing two or more of these compounds.

In the above formula (2), X is leucine, isoleucine, valine, glycine, serine, alanine, threonine, asparagine, glutamine, aspartic acid, glutamic acid, lysine, arginine, cysteine, methionine, phenylalanine, tyrosine, tryptophan, histidine, proline. Represents an amino acid residue selected from the group consisting of 4-hydroxyproline and homoserine. Of these, preferred X is leucine, isoleucine or valine.

R is a normal alkyl group having 8 to 14 carbon atoms, an isoalkyl group having 8 to 14 carbon atoms, or an anteisoalkyl group having 8 to 14 carbon atoms. The normal alkyl group is a linear alkyl group, the isoalkyl group is usually a group consisting of (CH ₃ ) ₂ CH— (CH ₂ ) _n —, and the anteisoalkyl group is usually CH ₃ —CH ₂ —CH (CH ₃ ) —. A group consisting of (CH ₂ ) _n —.

  The related compound refers to a compound in which a part of the amino acid of the formula (2) is replaced with another amino acid. Specific examples include, but are not limited to, those in which the second L-leucine, the fourth L-valine, the sixth D-leucine and the like are replaced with other amino acids.

  Surfactins are normally produced by prokaryotes, but other production methods such as those obtained by chemical synthesis can be used as well. As prokaryotes, Bacillus subtilis IAM 1213 strain, IAM 1069 strain, IAM 1259 strain, IAM 1260 strain, IFO 3035 strain, ATCC 21332 strain, and other microorganisms belonging to the genus Bacillus are generally used.

  Surfactin salts include alkali metal salts such as sodium, potassium and lithium, alkaline earth metal salts such as calcium and magnesium, trimethylamine, triethylamine, tributylamine, monoethanolamine, diethanolamine, triethanolamine, lysine and arginine. And organic salts such as choline. Among these, as surfactin sodium salts, those sold under the trade name of Aminofect (R) (registered trademark of Showa Denko KK) from Showa Denko as Surfactin Sodium can be used. .

The water that can be used for the hair treatment agent of the present invention is not particularly limited, but water that has undergone a purification step such as ion-exchanged water, distilled water, or purified water is preferred.
Hair Treatment Agent The hair treatment agent of the present invention contains at least a cyclic mercapto compound represented by the above formula (1), a surfactant, and water and is emulsified.

  Preferred examples of the hair treatment agent include permanent wave processing agents and hair straighteners. Hair straighteners are mainly used to improve hair curling, curl stretching, so-called sleepiness, and curling, as well as bromates commonly used in permanent wave processing agents. No oxidation treatment with hydrogen peroxide is required.

  The use of the hair straightener is not particularly limited, and for example, it is used as a shampoo, rinse, conditioner, hair treatment, hair water, hair wax, hair mousse, hair gel, and the like. Among these, it is preferably used as any hair cosmetic selected from the group consisting of shampoos, rinses, conditioners, hair treatments, hair waters, or hair mousses.

When the hair treatment agent of the present invention is used as a permanent wave processing agent, the cyclic mercapto compound represented by the above formula (1) is preferably a content of reducing substance (as thioglycolic acid), preferably 0.2 to It is contained in an amount of 30%, more preferably 1 to 15%. If the content of the cyclic mercapto compound is within this range, there is no damage to the hair and skin,
Wave efficiency can be kept high.

  When the content of the reducing substance is less than 0.2%, the performance as a permanent wave processing chemical may not be obtained at all. On the other hand, if it exceeds 30%, in the case of a Mongoloid race, hair damage may increase by promoting extreme curly hair and partial peeling of the cuticle.

The content of reducing substances (as thioglycolic acid), also referred to as thioglycolic acid reducing power conversion, is a notation of the concentration of keratin reducing substances determined for each treatment in the permanent wave quality standards for quasi-drugs. This is a concentration measured according to the following methods (I) to (III).

  (I) Take 10 mL of a sample in a 100 mL volumetric flask and add purified water (hereinafter simply referred to as “water”) that conforms to cosmetic raw material standards to make the total volume 100 mL, which is used as a test solution.

  (II) Take exactly 20 mL of the test solution, add 50 mL of water and 5 mL of 30% sulfuric acid, gently heat and boil for 5 minutes. After cooling, titrate with 0.1N iodine solution, and the amount of consumption is AmL (indicator: starch sample solution 3 mL).

(III) The obtained titration result is calculated as a thioglycolic acid content by the following formula.
Reducing substance content (as thioglycolic acid) (%) = 0.4606 × A
In addition, the permanent wave agent (curling agent) for cosmetics classification has a self-regulated value set by the Permanent Wave Industry Association, and the amount used is regulated by the same measurement method.

  Moreover, when using the hair treatment chemical | medical agent of this invention as a hair straightener, the cyclic mercapto compound represented by the said Formula (1) is 0.01-15 mass% normally, More preferably, it is 0.1-10 mass%. More preferably, it is contained in an amount of 1 to 5% by mass. If the content of the cyclic mercapto compound is within this range, the expected hair straightening effect can be sufficiently exhibited.

  On the other hand, if the content of the cyclic mercapto compound is less than the above lower limit value, the hair straightening effect may be hardly exhibited, and if the content exceeds the above upper limit value, the odor becomes strong and may not be practical. When used as a hair straightener in this way, after application to the hair, it is possible to straighten the hair and curl in a relatively short time from combing or shampooing, and the hair softness is improved. The reason for this is not clear, but the use of the cyclic mercapto compound represented by the above formula (1) increases the lipophilicity of the agent and improves the permeability to hair, so that the effect appears in a short time. Further, as described later, since it is used in a weakly acidic to neutral region as described later, it is considered that there is no hair damage and a soft feeling can be obtained.

  Further, the surfactant for hair treatment of the present invention preferably contains the surfactant in an amount of 0.02 to 15% by mass, more preferably 0.1 to 10% by mass. By blending the surfactant in such an amount, the cyclic mercapto compound can be sufficiently emulsified even in the presence of water, and a hair treatment agent such as a permanent waving agent or a hair straightener. It is possible to suppress degradation of the cyclic mercapto compound in the medium over time. Moreover, since the said cyclic mercapto compound exists in the lipophilic area | region in a micelle in the emulsified chemical | medical agent, it also has an effect which masks the odor of a cyclic mercapto compound.

The method for preparing the hair treatment agent of the present invention is not particularly limited as long as the specific cyclic mercapto compound represented by the formula (1) can be emulsified in water as a solvent using the surfactant. The mixing method, mixing order, mixing conditions, etc. are not particularly limited.

  The agent for treating hair of the present invention includes a cyclic mercapto compound represented by the above formula (1), a surfactant, and water, and as long as it is emulsified, its form is not particularly limited. , Gel, cream, paste and the like. And according to the form, it can be used as various types of drugs such as liquid type, spray type, aerosol type, cream type and gel type.

  Furthermore, you may mix | blend various additives with the chemical | medical agent for hair treatment of this invention according to the objective and the usage form which improve the processing performance of hair. As additives, swelling agents, penetration enhancers, buffers, oil agents, thickeners, hair protecting agents, wetting agents, pH adjusting agents, fragrances, dyes, stabilizers, odor masking agents and the like can be used.

  As swelling agents and penetration enhancers, ethanol, propanol, isopropanol, 1,2-propylene glycol, 1,3-butanediol, glycerin, ethyl carbitol, benzyl alcohol, benzyloxyethanol, urea, benzylamine, 2-methyl Examples include pyrrolidone.

Examples of the buffer include inorganic buffers and buffers containing basic amino acids such as arginine and lysine.
Examples of the oil include paraffin, liquid paraffin, beeswax, squalane, jojoba oil, olive oil, ester oil, triglyceride, petrolatum, lanolin and the like.

  Thickeners include carboxymethylcellulose, carboxyvinyl polymer, hydroxyethylcellulose, hydroxypropylcellulose, xanthan gum, carrageenan, alginate, pectin, tragacanth gum, lauryl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, behenyl alcohol, etc. Examples include higher alcohols, kaolin, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, undecyl acid, isostearic acid and other fatty acids, petrolatum, and the like.

Examples of the hair protecting component include hydrolysates such as collagen and keratin, and derivatives thereof.
Examples of the wetting agent include glycerin, diglycerin, propylene glycol, dipropylene glycol, 1,3-butanediol, sorbitol, plant extract, vitamins, hyaluronate, chondroitin sulfate, and the like.

  Examples of pH adjusters include inorganic acids such as hydrochloric acid and phosphoric acid, or inorganic acid salts such as disodium hydrogen phosphate and sodium dihydrogen phosphate; organic acids such as citric acid, malic acid, lactic acid, succinic acid, and oxalic acid. Or an alkali agent such as ammonia, diethanolamine, triethanolamine, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, or the like.

Examples of the stabilizer include dithiodiglycolic acid and the like in addition to the disulfide of the reducing compound for the purpose of preventing excessive reduction.
Examples of other additives include edetic acid and its metal salt, glutamic acid 4 acetic acid and its metal salt, aspartic acid 4 acetic acid and its metal salt, propyldiamine tetraacetic acid and its metal salt as chelating agents.

  In addition, the hair treatment agent of the present invention is an amount within the range not impairing the effects of the present invention, and conventionally known keratin reducing substances such as sulfite and bisulfite, thioglycolic acid and The monoglycerol ester, thiolactic acid, cysteine, acetylcysteine, cysteamine, acylcysteamine and salts thereof may be used in combination.

  When the hair treatment agent of the present invention is used as a permanent wave processing agent, its pH is not particularly limited, and it may be used with an alkalinity of about pH 9, preferably pH 2.5 to 8.7, It is desirable to use in the range of preferably pH 3.5 to 8.0, most preferably pH 4.0 to 7.5.

  That is, when the hair treatment agent of the present invention is used as a permanent wave processing agent, the permanent wave processing agent has a permanent wave processing effect even if it is alkaline, but the effect becomes more neutral and weakly acidic. Becomes larger.

  When the pH of the drug is in the above range, there is little skin irritation and it does not cause damage to hair and scalp. Moreover, the chemical | medical agent concerning this invention can exhibit the practical performance of a permanent process even if it uses pH within the said range. In addition, what is necessary is just to add the said pH adjuster to a chemical | medical agent, etc., in order to control the pH of a chemical | medical agent within the said range.

  In the present invention, since the cyclic mercapto compound described above is contained, the hair is excellent in the permanent wave processing performance in a neutral to weakly acidic pH range with little irritation to the skin.

  In addition, when the hair treatment agent of the present invention is used as the hair straightener, it goes without saying that it can be used on the alkaline side, but it is lower than the pH used in conventional hair treatment agents, from weakly acidic to neutral. It can be used in an area, and rather shows a better hair straightening effect in the pH area. Although there is no restriction | limiting in particular about pH to be used, Preferably it is pH 2.5-9.0, More preferably, it is pH 3.5-8.0, Most preferably, it is pH 4.0-7.5. When the pH is in the above range, there is little skin irritation and it is difficult to cause damage to hair.

Permanent wave processing method The permanent wave processing method of the present invention is not particularly limited as long as the above-described hair treatment agent is used as a permanent wave processing agent. For example, permanent wave treatment for hair is performed. Examples of the method include methods having the following steps (1) to (4). The permanent wave process includes a permanent wave forming process, a wave spreading process using a permanent wave process, and a hair straightening process.
(1) A permanent waving agent is moistened on the hair and wound with a rod for shaping the hair. Note that a rod is not used for straightening hair. Alternatively, the permanent waving agent may be moistened after fixing the hair with a water roll or the like.
(2) After the drug is wetted, it is left at room temperature. In that case, it is preferable to heat to about 30 to 40 degreeC.
(3) The cyclic mercapto compound is oxidized with a composition containing an oxidizing agent to fix the hair.
(4) Remove the rod from the fixed hair, wash the hair, shampoo and dry.

In addition, as an oxidizing agent used by (3), about 3-8 mass% aqueous solution of sodium bromate generally used, and dilution liquids, such as hydrogen peroxide and sodium perborate, can be used.
According to the present invention, since the above-mentioned permanent waving agent is used, there is little influence on the skin, sensitization is weak, and the wave efficiency of the hair is excellent.

  EXAMPLES Hereinafter, although this invention is demonstrated further more concretely based on an Example, this invention is not limited to these Examples.

[Synthesis Example 1]
Manufacture of 2-mercapto-4-butyrolactone 70% sodium hydrosulfide (49 g, 0.6 mmol, manufactured by Junsei Chemical Co., Ltd.) and methyl alcohol (500 g, Junsei Chemical Co., Ltd., special grade) and purified water (ion exchange filter after distillation) Water, 500 g). The dissolved liquid was cooled to 10 ° C. or lower under ice cooling while stirring. To the cooled solution, 2-bromo-4-butyrolactone (100 g, 0.6 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise over about 30 minutes. After the completion of the dropwise addition, the liquid was stirred for 10 minutes, and then the reaction liquid was concentrated to about half volume under reduced pressure. To the concentrated liquid, ethyl acetate (500 mL, manufactured by Junsei Chemical Co., Ltd., special grade) was added for extraction. The resulting aqueous phase was re-extracted with ethyl acetate (500 mL). These extracted organic phases were combined, concentrated under reduced pressure, and purified by distillation to obtain 2-mercapto-4-butyrolactone (23 g, bp. 94 ° C./0.3 kPa, yield 32%).

[Examples 1 to 15]
85 g of purified water (water passed through an ion exchange filter after distillation) was weighed into a 300 mL tall beaker made of glass, and 3 g of propylene glycol, 0.2 g of monosodium dihydrogen phosphate and disodium hydrogen phosphate were listed in Table 1. The amount was added at room temperature and stirred to dissolve completely.

  2 g of the surfactants listed in Table 1 were added to the obtained solution and stirred so as to be almost uniform. While stirring this solution vigorously with a homomixer, 2.6 g of 2-mercapto-4-butyrolactone synthesized in Synthesis Example 1 was added little by little. After completion of the addition, the mixture was stirred with a homomixer for 5 minutes. Thereafter, purified water was added so that the liquid weight would be 100 g, and the mixture was stirred again with a homomixer to obtain a test liquid.

The appearance of the obtained test solution was a colorless and transparent liquid or a milky white to slightly yellow emulsion.
The content of 2-mercapto-4-butyrolactone in the test solution thus obtained is
It corresponds to 2% in terms of thioglycolic acid reducing power.

  Immediately after the preparation, this test solution was put in a 100 mL lidded sample bottle to remove the odor, and the odor improvement was evaluated according to the following evaluation criteria based on the odor immediately after the preparation of the test solution of Comparative Example 1 described later. Thereafter, the lid of the sample bottle was closed and left in a constant temperature bath at 40 ° C.

  On the 10th day after standing, the concentration change of 2-mercapto-4-butyrolactone in the test solution was analyzed by high performance liquid chromatography under the following analytical conditions to calculate the decomposition rate of 2-mercapto-4-butyrolactone. did. Furthermore, the color change of the test liquid on the 10th day after the standing was visually evaluated as compared with the test liquid immediately after preparation.

These results and the pH of the test solution are shown in Table 1.
Analytical conditions for high performance liquid chromatography
Column: Shodex RSpak NN-814 (Column Size: 8.0mmφ × 250mm)
Eluent: 0.008mM-KH ₂ PO ₄ + 0.1% H ₃ PO ₄
Flow Rate: 1.0mL / min
Detector: UV (210nm), RI
Column temp .: 40 ℃
Inj. Vol .: 20μL
Odor evaluation criteria ◎; significant reduction in odor compared to non-surfactant added solution.

O: The odor is reduced compared to the surfactant-free solution.
Δ: Slightly improved as compared with the surfactant-free solution.
×: Equivalent to a surfactant-free solution.

[Comparative Example 1]
90 g of purified water was weighed into a glass 300 mL tall beaker, and 3 g of propylene glycol, 0.2 g of monosodium dihydrogen phosphate and 0.6 g of disodium hydrogen phosphate were added at room temperature, and the mixture was completely dissolved by stirring.

  To the resulting solution, 2.6 g of 2-mercapto-4-butyrolactone synthesized in Synthesis Example 1 was added little by little while stirring with a homomixer. After completion of the addition, the mixture was stirred with a homomixer for 5 minutes. Thereafter, purified water was added so that the liquid weight would be 100 g, and the mixture was stirred again with a homomixer to obtain a test liquid.

The appearance of the obtained test solution was a colorless and transparent solution.
The content of 2-mercapto-4-butyrolactone in the test solution thus obtained is
It corresponds to 2% in terms of thioglycolic acid reducing power.

  Immediately after the preparation, this test solution was put in a 100 mL lidded sample bottle to remove the odor, and the odor was used as a comparative odor sample (odor of a surfactant-free solution) based on the above odor evaluation criteria. Thereafter, the lid of the sample bottle was closed and left in a constant temperature bath at 40 ° C.

  On the 10th day after standing, the change in the concentration of 2-mercapto-4-butyrolactone in the test solution was analyzed by high performance liquid chromatography under the same conditions as in Examples 1 to 15 above, and 2-mercapto-4-butyrolactone was analyzed. The degradation rate was calculated. Furthermore, the color change of the test liquid on the 10th day after the standing was visually evaluated as compared with the test liquid immediately after preparation.

  These results and the pH of the test solution are shown in Table 1.

  From Table 1, compared with the test solution of Comparative Example 1, the test solutions of Examples 1 to 15 suppressed the decomposition of 2-mercapto-4-butyrolactone and prevented coloring even after 10 days at 40 ° C. In addition, it can be seen that the odor is improved.

[Examples 16 to 30]
In a glass 300 mL tall beaker, 65 g of purified water is weighed, and 3 g of propylene glycol, 0.3 g of monosodium dihydrogen phosphate and disodium hydrogen phosphate are added in the amounts shown in Table 2 at room temperature and stirred. And completely dissolved. 4 g of the surfactant listed in Table 2 was added to the solution and stirred so as to be almost uniform. While stirring this solution vigorously with a homomixer, 2.6 g of 2-mercapto-4-butyrolactone synthesized in Synthesis Example 1 was added little by little. After completion of the addition, the mixture was stirred with a homomixer for 5 minutes. Thereafter, purified water was added so that the liquid weight would be 100 g, and the mixture was stirred again with a homomixer to obtain a test liquid.

The content of 2-mercapto-4-butyrolactone in the test solution thus obtained is
It corresponds to 12.7% in terms of thioglycolic acid reducing power.
The appearance of the obtained test solution was a colorless and transparent liquid or a milky white to slightly yellow emulsion.

  Immediately after the preparation, the test solution was put in a 100 mL lidded sample bottle to remove the odor, and the improvement in odor was evaluated according to the evaluation criteria based on the odor immediately after the preparation of the test solution of Comparative Example 2 described later. Thereafter, the lid of the sample bottle was closed and left in a constant temperature bath at 40 ° C.

  On the 10th day after standing, the change in the concentration of 2-mercapto-4-butyrolactone in the test solution was analyzed by high performance liquid chromatography under the same conditions as in Examples 1 to 15 above, and 2-mercapto-4-butyrolactone was analyzed. The degradation rate was calculated. Furthermore, the color change of the test liquid on the 10th day after the standing was visually evaluated as compared with the test liquid immediately after preparation.

These results and the pH of the test solution are shown in Table 2.
[Comparative Example 2]
70 g of purified water was weighed into a glass 300 mL tall beaker, and 3 g of propylene glycol, 0.3 g of monosodium dihydrogen phosphate and 0.8 g of disodium hydrogen phosphate were added at room temperature, and the mixture was stirred and completely dissolved. To the obtained solution, 15 g of 2-mercapto-4-butyrolactone synthesized in Synthesis Example 1 was added little by little while stirring with a homomixer. After completion of the addition, the mixture was stirred with a homomixer for 5 minutes. Thereafter, purified water was added so that the liquid weight would be 100 g, and the mixture was stirred again with a homomixer to obtain a test liquid.

The appearance of the obtained test solution was a colorless liquid, but a slightly oily substance remained undissolved.
The content of 2-mercapto-4-butyrolactone in the test solution thus obtained is
It corresponds to 12.7% in terms of thioglycolic acid reducing power.

  Immediately after the preparation, this test solution was put in a 100 mL lidded sample bottle to remove the odor, and the odor was used as a comparative odor sample (odor of a surfactant-free solution) based on the above odor evaluation criteria. Thereafter, the lid of the sample bottle was closed and left in a constant temperature bath at 40 ° C.

  On the 10th day after standing, the change in the concentration of 2-mercapto-4-butyrolactone in the test solution was analyzed by high performance liquid chromatography under the same conditions as in Examples 1 to 15 above, and 2-mercapto-4-butyrolactone was analyzed. The degradation rate was calculated. Furthermore, the color change of the test liquid on the 10th day after the standing was visually evaluated as compared with the test liquid immediately after preparation.

  These results and the pH of the test solution are shown in Table 2.

  From Table 2, even when the compounding amount of 2-mercapto-4-butyrolactone was increased, the test solutions of Examples 16 to 30 were compared with the test solution of Comparative Example 2 even after 10 days at 40 ° C. It can be seen that the decomposition of 2-mercapto-4-butyrolactone is suppressed, coloring is prevented, and odor is also improved.

[Examples 31 to 34]
Using the test solution after the decomposition rate test of Examples 1, 6, 9, and 10 as the first liquid for permanent wave, and further using the second liquid for permanent wave as described below, permanent wave treatment was performed by the following method. The effect on performance was confirmed.
First liquid for permanent wave The test liquid after the decomposition rate test of Examples 1, 6, 9, and 10 shown in Table 1 was used as the first liquid for permanent wave.
Preparation of second liquid for permanent wave 5 g of sodium bromate and 95 g of purified water were mixed to obtain a second liquid for permanent wave.
Permanent wave treatment wave efficiency was evaluated by the Kilby method according to the method described in the special issue of fragrance journal (1984, No. 5, page 442).

  First, Chinese hair (about 20 cm in length) was fixed to a Kilby instrument. The hair fixed in the first liquid for permanent wave heated to 33 ° C. was soaked for 20 minutes. After the treatment, the hair taken out from the first liquid was wiped lightly to such an extent that the liquid did not drip.

  The second liquid for permanent wave was moistened on the hair and allowed to stand at 25 ° C. for 10 minutes. After the above-described treatment with the second liquid was completed, the hair was washed with running water, the hair was removed from the kilbies, and the hair was dried. The dry hair thus obtained was measured, and the wave efficiency was calculated by the following wave efficiency calculation formula.

Wave efficiency (%) = 100− [100 × (B−A)] ÷ (C−A)
A: Distance between the first and sixth rods of the kirby apparatus (actual measurement of the center point of the rods) (mm)
B: Length of 6 piles of curled hair (mm)
C: Length of 6 mountains when curled hair is straightened (mm)
The result of the wave efficiency obtained in this way was defined as X2 (using the test solution after the decomposition rate test in Examples 1, 6, 9, and 10 above). Further, the wave efficiencies were determined in the same manner except that the test solutions immediately after preparation of Examples 1, 6, 9, and 10 were used, and the result was designated as X1.

From the above X1 and X2, the reduction rate of the wave efficiency was calculated using the following formula. The calculated results are shown in Table 3.
Decrease rate of wave efficiency (%) = [(X1−X2) / X1] × 100
[Comparative Example 3]
Permanent wave treatment was performed in the same manner as in Examples 31 to 34 except that the test liquid after the decomposition rate test used in Comparative Example 1 was used as the first liquid for permanent wave, and the wave efficiency X2 was calculated. Further, the wave efficiency was determined in the same manner except that the test solution immediately after preparation of Comparative Example 1 was used, and the result was designated as X1.

  Using these X1 and X2, the rate of decrease in wave efficiency was calculated in the same manner as in Examples 31-34. The results are shown in Table 3.

  From Table 3, according to the test liquids of Examples 31 to 34, the degradation of 2-mercapto-4-butyrolactone was suppressed even after aging, so that even when compared with the test liquid immediately after the preparation, the wave efficiency of the hair was improved. It can be seen that the rate of decline is low. Therefore, these test solutions can be used longer as permanent waving agents than the test solution of Comparative Example 3.

Claims (15)

A hair treatment agent comprising a compound represented by the following formula (1), a surfactant, and water and emulsified;

(X represents a structure of any of —O—, —S—, —NH—, and —NR ¹ —. R ¹ represents an alkyl group having 1 to 6 carbon atoms. R ² represents a hydrogen atom or 1 carbon atom. Represents an alkyl group of ˜6, Y represents an oxygen atom or a sulfur atom, and R represents a divalent organic residue which may have a mercapto group. The hair treatment agent according to claim 1, wherein X in the formula (1) is —O—, —NH—, —NCH ₃ — or —S—.   The agent for hair treatment according to claim 1 or 2, wherein Y in the formula (1) is an oxygen atom.   The hair treatment agent according to any one of claims 1 to 3, wherein R in the formula (1) is an alkylene group.   The hair treatment agent according to any one of claims 1 to 3, wherein R in the formula (1) is an alkylene group having one or more mercapto groups. The compound represented by the formula (1) is
At least one selected from the group consisting of 2-mercapto-4-butyrolactone, 2-mercapto-4-methyl-4-butyrolactone, 2-mercapto-4-ethyl-4-butyrolactone and 2-mercapto-6-hexanolactam The hair treatment agent according to claim 1, wherein   The surfactant is at least one selected from the group consisting of a nonionic surfactant, a cationic surfactant, an anionic surfactant, an amphoteric surfactant, a polymer surfactant, and a biosurfactant. The hair treatment agent according to claim 1, wherein the agent is for hair treatment.   The nonionic surfactant is at least one selected from the group consisting of polyoxyethylene alkyl ether, polyoxyethylene alkenyl ether, polyoxyethylene alkylphenyl ether having a polyoxyethylene addition mole number of 10 to 100. The hair treatment agent according to claim 7.   The said nonionic surfactant is a silicone type nonionic surfactant, The agent for hair treatment of Claim 7 characterized by the above-mentioned.   8. The hair treatment agent according to claim 7, wherein the biosurfactant has a lipopeptide structure.   11. The compound represented by the formula (1) is contained in an amount of 0.2 to 30% in terms of a reducing substance content (as thioglycolic acid). The agent for hair treatment described in 1.   The said surface active agent is contained in the quantity of 0.1-10 mass%, The chemical | medical agent for hair treatment in any one of Claims 1-11 characterized by the above-mentioned.   The drug for hair treatment according to any one of claims 1 to 12, wherein the pH of the drug is 4.0 to 7.5.   The hair treatment agent according to any one of claims 1 to 13, which is a permanent wave processing agent.   A method for permanent waving hair, wherein the hair treating agent according to any one of claims 1 to 13 is used as a permanent waving agent.