JPH09315946A - Hair-treating agent composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a hair-treating agent composition containing a specific amide compound having a penetration-stimulating action. SOLUTION: This hair-treating agent composition contains at least one kind among compounds of the formula R<1> R<2> NCOR<3> (R<1> -R<3> are each H, a 1-8C alkyl or alkenyl, an aryl) in an amount of 0.1-30wt.%. The compound of the formula includes pentanoamide, and N-butylformamide. The hair-treating agent composition can largely improve the penetration speed or penetration amount of a dye for dyeing hair, a polymer for conditioning hair, a perfume, a softener, an agent for imparting tension or nerve, an agent for enhancing a permanent wave effect, a damage-reducing agent, etc. When the hair-treating agent composition is especially compounded with the dye for dyeing hair, hair can well be dyed. The above compound has a more excellent penetration-stimulating action than benzyl alcohol as a conventional penetration-stimulating agent.

Description

Detailed Description of the Invention

[0001]

The present invention relates to various ingredients for hair, such as dyes for dyeing, conditioning polymers, fragrances, softeners, agents for imparting firmness and stiffness, agents for enhancing perming effects and agents for reducing damage. And a hair treatment composition having an improved penetration rate or penetration amount. In particular, the present invention relates to a hair treatment composition for dyeing containing a dye for dyeing hair.

[0002]

2. Description of the Related Art Hair treatment compositions intended for hair dyeing, perming or damage care are conventionally known. Most of these hair treatment compositions infiltrate certain ingredients into the hair in order to achieve their purpose.

For example, in the case of a hair treatment composition for dyeing hair, an acid dye which has relatively little effect on the scalp and hair and which can be easily dyed is incorporated and penetrated into the hair. It is dyed. In this case, since the acid dye alone does not have sufficient penetration speed and penetration amount into the hair, the hair treatment composition for hair dyeing contains benzyl alcohol as a penetration enhancer.

In addition, even in a hair treatment composition for performing a permanent treatment, a long-lasting hair setting, etc., it is necessary to penetrate the inside of the hair with a keratin reducing agent for cleaving a disulfide bond of keratin. And benzyl alcohol as a penetration promoter. Similarly, also in the case of a hair treatment composition containing a hair and hair conditioner, a hair softener, a hair damage reducing agent and the like, benzyl alcohol is blended as a penetration promoter.

[0005]

However, even when using benzyl alcohol as a penetration enhancer,
Within the good range of the handleability such as the concentration of the dye for hair dyeing and the hair treatment time, there is a problem that the dyeability of the hair treatment composition for hair dyeing is not sufficient.

Also in other hair treatment compositions,
Similarly, there is a problem that the penetration promoting effect is insufficient.

The present invention seeks to solve the problems of the prior art as described above, and comprises a hair treatment composition comprising a compound having a penetration promoting action superior to that of the conventional penetration promoting agent benzyl alcohol. It aims to provide goods.

[0008]

[Means for Solving the Problems] The present inventors have found that the above-mentioned object can be achieved by using a specific amide compound having a penetration promoting action in a specific compounding amount.
The present invention has been completed.

That is, the present invention relates to the formula (1)

[0010]

R ¹ R ² NCOR ³ (1) (wherein, R ¹ , R ² and R ³ are each independently (a)
Hydrogen atom, (b) linear, branched or cyclic alkyl group or alkenyl group having 1 to 8 carbon atoms, (c) aryl group or (d) aryl group, hydroxyl group, ether group, amide group, carbonyl group and carboxyl group It is a C1-C8 linear, branched or cyclic alkyl group or alkenyl group which has in the principal chain or a side chain at least 1 type of substituent selected from the group which consists of groups. A hair treatment composition comprising at least one of the compounds of the formula (1) in a proportion of 0.1 to 30% by weight.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below.

In the hair treatment composition of the present invention, at least one of the amide compounds of the formula (1) having a penetration promoting action is used. These compounds can accelerate the penetration speed and increase the penetration amount of various hair treatment ingredients to the hair, as compared with the conventional penetration enhancer benzyl alcohol.

In such a compound of the formula (1), preferred combinations of R ¹ , R ² and R ³ are each independently (a) a hydrogen atom or (b) a straight chain having 1 to 8 carbon atoms. In the case of a branched or cyclic alkyl group, a (c) aryl group or a linear, branched or cyclic alkyl group having at least one of an (d) aryl group, a hydroxyl group and an amido group, Examples include (a) a hydrogen atom or (b) a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms.

In the compound of formula (1), R ¹ ,
Examples of the (b) linear, branched or cyclic alkyl group or alkenyl group having 1 to 8 carbon atoms as R ² and R ³ include methyl, ethyl, n-propyl, n-butyl and n
-Pentyl group, n-hexyl group, n-heptyl group, n-
An octyl group, 2-ethylhexyl group, a cyclohexyl group etc. can be mentioned preferably. Moreover, as an (c) aryl group, a phenyl group, a furanyl group, etc. can be mentioned. (D) straight or branched chain having 1 to 8 carbon atoms having at least one substituent selected from the group consisting of aryl group, hydroxyl group, ether group, carbonyl group and carboxyl group in the main chain or in the side chain Alternatively, examples of the cyclic alkyl group or the alkenyl group preferably include a benzyl group, a pyridyl group, a hydroxyethyl group and a pyrrolidonyl group.

Specific examples of such compounds of the formula (1) are shown in Tables 1 and 2.

[0016]

[Table 1] Compound name of substituent group (1) R ¹ R ² R ³ Butyramide H H Propyl pentanoamide H H Butyl Hexanoamide H H Pentyl heptanoamide H H Hexyl Octanoamide H H Heptyl 2-Ethyl Hexanoamide H H 1-Ethylpentyl Cyclohexane Carboxa Amide H H cyclohexyl benzamide H H phenyl phenylacetamide H H benzyl N-propylformamide propyl H H N-butylformamide butyl H H N-pentylformamide pentyl H H N-hexylformamide hexyl H H N-heptylformamide heptyl H H N- Octylformamide octyl H H N 2-ethylhexylformamide 2-ethylhexyl H H N-cyclohexylformamide cyclohexyl H H - phenyl formamide phenyl H H N-benzyl formamide benzyl H H N, N-diethylformamide ethyl ethyl H N, N-dipropyl formamide propyl propyl H N, N-di-isophthalic ° Ropi Ruhorumuamito Bu isophthalic ° propyl isophthalic ° propyl H N, N-dipentyl formamide pentyl pentyl H N, N-Dihexylformamide hexyl hexyl H

[0017]

【Table 2】 Compound name of the substituent formula (1) R ¹ R ² R ³ N-propylacetamide propyl H methyl N-butylacetamide butyl H methyl N-pentylacetamide pentyl H methyl N-hexylacetamide hexyl H methyl N-heptylacetamide heptyl H methyl N-octylacetylamide octyl H methyl N-2-ethylhexyl acetoamide 2-ethylhexyl H methyl N-cyclohexyl acetamide cyclohexyl H methyl N-phenyl acetamide phenyl H methyl N-benzyl acetamide benzyl H methyl 5-pyrrole aminocarboxyl-2-pyrolidine H Propyl pyrrolidonyl 5-butylaminocarboyl-2-propylidene H-butyl pyrrolidonyl 5-pentylaminocarbonyl-propylolide H pentyl pyrrolidonyl 5-hexylaminocarbolyl-2-pyrrolidone H hexyl pyrrolidonyl 5-heptylaminocarboyl-2-propylidene H heptyl pyrrolidonyl 5-octylaminocarboyl-2-pyrolideone H octyl pyrrolidonyl 5- (2-ethylhexyl) aminocarbonyl-2 -Pyrrolidone H 2-ethylhexyl pyrrolidonyl N-methyl-N- (2-pyridine) formamide methyl pyridyl H

Particularly preferred among the compounds of the formula (1) listed in Tables 1 and 2 are pentanoamide, hexanoamide, heptanoamide, N-butylformamide, N-pentylformamide, N-hexylformamide, N-benzylformamide And N-cyclohexylformamide, 5-hexylaminocarbonyl-2-pyrrolidone and N-methyl-N- (2-pyridyl) formamide.

The compounding amount of the compound of the formula (1) in the hair treatment composition is 0.1 to 30% by weight, preferably 1 to 10.
It is 15% by weight. If it is less than 0.1% by weight, a sufficient penetration promoting effect can not be obtained, and if it exceeds 30% by weight, the solubility in water is reduced, and a uniform composition can not be obtained. Absent.

In the hair treatment composition of the present invention, in addition to the compound of the formula (1), various hair treatment ingredients are blended according to the purpose of use. In that case, as mentioned above, the penetration speed and penetration amount of the hair treatment components into the hair will be enhanced.

For example, the hair treatment composition may contain a dye for hair dyeing as a hair treatment component. This allows the hair to be fully dyed. Here, as the dye for dyeing, various dyes known as dyes for dyeing can be used, but an acid dye having a high penetration promoting effect on the hair by the compound of the formula (1) compared to other dyes It is preferred to use

Examples of such acid dyes include nitro dyes, azo dyes, nitroso dyes, triphenylmethane dyes, xanthene dyes, quinoline dyes, anthraquinone dyes, indigo dyes and the like. Specifically, red 2, red 3, red 102, red 104
No. 105 red, 106 red, 4 yellow, 5 yellow
No.3, Green No.1, Blue No.1, Blue No.2, Red No.201, Red No.227, Red No.220, Red No.230, Red No.231
No., Red No. 232, Orange No. 230, Orange No. 207, Orange No. 205, Yellow No. 202, Yellow No. 203, Green No. 201
, Green 204, Green 205, Blue 202, Blue 203, Blue 205, Brown 201, Red 401
, Red 502, Red 503, Red 504, Red 506, Orange 402, Yellow 402, Yellow 403
No. yellow 406, yellow 407, green 401, green 402, purple 401, black 401 and the like.

If the blending amount of these acid dyes in the hair treatment composition is too small, the dyeability will be insufficient, if it is too large, the solubility will decrease and further improvement in dyeability can not be expected. The content is made 0.0001 to 10% by weight, more preferably 0.01 to 1% by weight. In this case, the water content of the hair treatment composition for hair dyeing is preferably 10 to 97% by weight.

The pH of a hair treatment composition containing such an acid dye as a dye for dyeing is likely to damage the hair or scalp if it is too low, and the dyeability is preferably lowered if it is too high. It is adjusted to 2 to 6, more preferably 2 to 4. In this case, the pH can be adjusted by appropriately adding an organic acid such as lactic acid, tartaric acid, acetic acid, citric acid or oxalic acid, or an inorganic acid such as phosphoric acid or hydrochloric acid to the hair treatment composition.

In the hair treatment composition, a keratin reducing agent can be blended as a hair treatment component. This makes it possible to sufficiently cleave the disulfide bonds of keratins constituting the hair. Such a hair treatment composition can be preferably used as a permanent wave first agent.

In this case, as the keratin reducing agent, preferably thioglycolic acid and its derivative, thiolactic acid and its derivative, cysteine and its derivative or a salt thereof, thioglyceryl alkyl ether of the formula (2) or a salt thereof

[0027]

Embedded image _{^{R 4 OCH 2 CH (OH)}} CH 2 SH (2) ( wherein, R ⁴ is a hydrogen atom, a lower alkyl group or a lower alkoxy-lower alkyl group.) Or mercaptoalkyl amides of formula (3) Or its salt

[0028]

Embedded image _{H- (CHOH) s - (CH} 2) p -CONH (CH 2) q -SH (3) ( wherein, s is a number from 0 to 5, p is a number from 0 to 3 Yes, q is a number from 2 to 5, where s and p are simultaneously 0
is not. Can be mentioned. More specifically,
Thioglycolic acid, thioglycollic acid glycerol ester, L-cysteine, D-cysteine, N-acetylcysteine, ammonium salts of these cysteines, ethanolamines such as monoethanolamine, diethanolamine, triethanolamine, ethoxyhydroxypropanethiol, Thioglyceryl alkyl ethers such as methoxyethoxyhydroxypropanethiol and isopropoxyethoxyhydroxypropanethiol, mercaptoethylpropanamide, mercaptoethyl gluconamide and the like can be mentioned.

It is preferable that the blending amount of these keratin reducing agents in the hair treatment agent composition is too small, because the reduction of keratin is insufficient, and excessive addition may cause damage to the skin and the hair. Is 1 to 20% by weight, more preferably 3 to 10% by weight. In this case, the pH of the hair treatment composition is preferably 3.0 to 9.5, more preferably 4.0 to inhibit damage to the skin and the hair.
It is assumed to be 9.0. Adjustment of pH can be performed using known pH adjusters.

Also, the first permanent wave mentioned above
In the hair treatment composition as a permanent wave second agent to be used in combination with the agent, an oxidizing agent for permanent such as bromate salts and perborate acids can be blended as a hair treatment component. This allows the disulfide bonds of cleaved keratin in the hair to be fully recombined.

In the hair treatment composition, as a hair treatment component, naphthalene sulfonic acid described in JP-A-5-43425, azulene sulfonic acid described in JP-A-5-43426, JP-A-5-286828 It is also possible to blend known hair and hair crumb imparting agents such as tetralin sulfonic acid described above, and aromatic sulfonic acid such as benzophenone sulfonic acid described in JP-A-5-286830 or a salt thereof. As a result, the hair is fully covered
It is possible to infiltrate the agent. Alternatively, the hair treatment composition may be blended with a known softener such as hydroxycarboxylic acid such as glycolic acid or a salt thereof as a hair treatment component, thereby providing the hair with good softness. be able to.

The hair treatment composition may also contain known damage reducing agents such as ethyl carbitol, ultraviolet light absorbers, lipids, surfactants, proteins or their derivatives as hair treatment components. And the damage reduction effect to hair can be provided. Alternatively, known conditioning treatments such as cationic polymers and amphoteric polymers such as cationic cellulose derivatives, cationic starches, cationic guar gum derivatives and quaternary polyvinylpyrrolidone derivatives as hair treatment components are added to the hair treatment composition. Agents can be formulated to
The hair can be provided with a long-lasting good conditioning effect. In addition, a perfume can be added to the hair treatment composition as a hair treatment component, whereby
It is possible to impart long lasting and strong odor to hair.

In the hair treatment composition of the present invention, additives such as lower alcohols, preservatives and chelating agents may be appropriately blended within the range in which the stability of the composition and the desired pH value can be maintained. it can.

The hair treatment composition of the present invention can be generally formulated into a cream, emulsion, gel, solution, mousse or foam.

The hair treatment composition in the form of cream, emulsion, gel or solution is a wetting agent (emulsifier), a solubilizer, a stabilizer, a touch improver which is usually used in the cosmetic field. , A hair setting base and the like can be added to the aqueous medium together with the compound of the formula (1) and manufactured according to a conventional method. Here, as the wetting agent (emulsifying agent), for example, anionic, amphoteric or alkylenic sulfonates such as alkyl benzene sulfonate, aliphatic alcohol sulfate, alkyl sulfonate, acylated amino acids, fatty acid alkanolamide, addition product of ethylene oxide and fatty alcohol, etc. Mention may be made of cationic surfactants. Further, examples of the touch improver or the hair setting base include silicone derivatives, higher alcohols, oil components such as various nonionic surfactants, and cationic surfactants.

The mousse-like or foam-like hair-treating agent composition may be prepared by mixing the compound of the formula (1) and a conventional nonionic surfactant, anionic surfactant or cationic surfactant in an amount of 1% by weight or less. A solution obtained by dissolving or dispersing active agents or their mixed surfactants and 0.5 to 1% by weight of a thickener in an aqueous medium is filled in an aerosol can together with liquefied petroleum gas (propellant) and used at the time of use It may be injected in the form of a mousse or foam.

As a usage mode of the hair treatment composition of the present invention, it is used by a method according to the hair treatment component to be blended therein and the purpose of use. For example, when used as a hair dye composition for dyeing keratinous fibers of the hair, the hair treatment composition is allowed to act on the keratinous fibers at a temperature of 15 to 50 ° C. for 10 to 30 minutes, and then washed You can dry it.

[0038]

EXAMPLES The present invention will be described in detail by way of examples.

Examples 1 to 5 and Comparative Examples 1 to 2 A hair treatment composition for hair dyeing having the composition of Table 3 was prepared according to a conventional method.

[0040]

[Table 3]

(Evaluation) In order to evaluate the effect of the penetration enhancer contained in the hair treatment composition for hair dyeing obtained, the human as described below using each hair treatment composition The dyeability test on the hair was carried out to evaluate its dyeability.

Dyeability Test The hair treatment composition was applied to a gray, human hair and left in a room at 30 ° C. for 15 minutes. after that,
The hair was washed with a conventional shampoo, rinsed thoroughly with water and then dried, and its dyeability was evaluated according to the following evaluation criteria. The results are shown in Table 4.

Stainability evaluation criteria Rank Condition 5: In the case of significantly better dyeability than in the case of using benzyl alcohol 4: in the case of better dyeability than in the case of using benzyl alcohol 3: equivalent to the case of using benzyl alcohol In the case of a degree of stainability 2: In the case of inferior dyeability than in the case of using benzyl alcohol 1: In the case of considerably inferior dyeability in the case of using benzyl alcohol

[0044]

[Table 4]

It is apparent from Table 4 that the hair treatment composition for hair dyeing of Examples 1 to 5 has the dyeability remarkably improved as compared with the conventional hair treatment composition for hair dyeing (Comparative Example 1). , It can be seen that the penetration promoting effect is greatly improved.

In the case of Comparative Example 2 in which the compound having a penetration enhancing action was not used, it showed only a very insufficient staining.

Example 6 A hair treatment composition for black hair dyeing having the composition shown in Table 5 was prepared according to a conventional method.

[0048]

[Table 5] Component name Compounding amount (% by weight) Black No. 401 0.1 Purple No. 401 0.1 Ethanol 20 Xanthan gum 1.0 N-benzylformamide 10.0 lactic acid / citric acid buffer (required for pH 3 Amount) Flavoring amount Appropriate amount of water balance

The dyeability of the obtained hair treatment composition was evaluated in the same manner as in Example 1. As a result, the same excellent dyeability as in Example 1 was exhibited.

Example 7 A hair treatment composition for brown hair dyeing having the composition shown in Table 6 was prepared according to a conventional method.

[0051]

[Table 6] Component name Compounding amount (% by weight) Purple No. 401 0.07 Orange No. 205 0.2 Red No. 204 0.01 Black No. 401 0.03 Ethanol 10 1,3-butanediol 10 Xanthan gum 1.0 N -Pentyl formamide 10 citric acid and sodium citrate buffer (amount required to reach pH 3.3) perfume appropriate amount water balance amount

The dyeability of the obtained hair treatment composition was evaluated in the same manner as in Example 1. As a result, the same excellent dyeability as in Example 1 was exhibited.

EXAMPLE 8 A keratin reducing agent-containing hair treatment composition was prepared by uniformly mixing the ingredients listed in Table 7.

[0054]

[Table 7] Component name Weight% Keratin reducing agent Thioglycollic acid 4.5 Ammonium hydrogen carbonate 2.0 N-methyl-N- (2-pyridine) formamide 3.0 monoethanolamine 0.9 ethanol 15.0 water balance

The hair treatment composition of this example was evaluated for curling ability in permanent wave treatment and showed excellent curling ability.

Example 9 A hair treatment composition for firming and firming was prepared by uniformly mixing the ingredients shown in Table 8.

[0057]

[Table 8] Ingredient name Weight and weight imparting agent for hair 2,7-Naphthalenedisulfonic acid disodium 3.0 hexanoamide 10.0 ethanol 25.0 sodium citrate 0.1 citric acid 0.5 lactic acid 5.0 Water balance

When the hair was treated with the hair treatment composition of this example, it was possible to impart a sufficiently high degree of gloss to the hair even after shampooing for a long time.

Example 10 A hair treatment composition for a hair conditioner was prepared by uniformly mixing the ingredients listed in Table 9.

[0060]

Component name : % by weight softener glycolic acid 1.5 sodium glycolate 1.5 propylene glycol 25.0 xanthan gum 0.5 stearyltrimethylammonium chloride 1.0 N-cyclohexylformamide 5.0 water balance

After the hair was treated with the hair treatment composition of this example, it exhibited sufficient flexibility when washed and dried as well as after 24 hours of hair washing.

[0062]

The hair treatment composition of the present invention exhibits a greatly improved penetration rate and penetration of hair treatment ingredients into the hair. Therefore, for example, when a dye for hair dyeing is blended as a hair treatment component, the hair can be dyed well.

 ── ── ── ── ──続 き 続 き Continuation of the front page (72) Inventor Akira Kiyomine 2606 Akabori-kai, Haga-gun, Tochigi Pref.

Claims (9)

[Claim of claim] 1. A compound according to claim 1, wherein R ¹ R ² NCOR ³ (1) wherein R ¹ , R ² and R ³ are each independently (a)
Hydrogen atom, (b) linear, branched or cyclic alkyl group or alkenyl group having 1 to 8 carbon atoms, (c) aryl group, or (d) aryl group, hydroxyl group, ether group, amide group, carbonyl group, It is a C1-C8 linear, branched or cyclic alkyl group or alkenyl group which has in a principal chain or a side chain at least 1 type of substituent selected from the group which consists of carboxyl groups. A hair treatment composition comprising 0.1 to 30% by weight of at least one of the compounds represented by 1.). 2. R ¹ , R ² and R ³ in the formula (1) each independently represent (a) a hydrogen atom, (b) a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms The hair treatment composition according to claim 1, which is a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms and at least one of (c) aryl group or (d) aryl group, hydroxyl group and amide group. . ^3. Each of R ¹ , R ² and R ³ in the formula (1) independently represents (a) a hydrogen atom or (b) 1 to 8 carbon atoms
The hair treatment composition according to claim 2, which is a linear, branched or cyclic alkyl group of 4. The compound of formula (1) is pentanoamide,
Hexanoamide, heptanoamide, N-butylformamide, N-pentylformamide, N-hexylformamide, N-benzylformamide, N-cyclohexylformamide, 5-hexylaminocarbonyl-2-
The hair treatment composition according to claim 1, which is at least one selected from the group consisting of pyrrolidone and N-methyl-N- (2-pyridyl) formamide. 5. The hair treatment composition according to any one of claims 1 to 4, which contains a dye for dyeing hair. 6. The hair treatment composition according to claim 5, wherein the hair dye is an acid dye. 7. A keratin reducing agent according to any one of claims 1 to 4.
The hair treatment composition according to any one of the above. 8. A hair treatment composition as claimed in any one of claims 1 to 4 which contains a hair and hair conditioner. 9. A softener for hair according to claim 1.
The hair treatment composition in any one of -4.