JPH0656637A - First agent for permanent wave treatment - Google Patents

Abstract

PURPOSE:To provide a 1st agent for permanent wave treatment, capable of imparting excellent wave to the hair even in neutral region, to say nothing of alkaline region. CONSTITUTION:N-(2-mercaptoethyl)alkylamide expressed by the formula HSCH2 CH2NHCO-R (R is CH3 or CH3CH2) is used as a reducing agent of the 1st agent for permanent wave treatment. The amount of the compound in the 1st agent is 2-15wt.%. As necessary, the 1st agent is incorporated with hydrolyzed protein or its derivative.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION The present invention has less hair damage,
The present invention also relates to a first agent for permanent wave, which is capable of imparting a good wave to hair.

[0002]

2. Description of the Related Art A conventional permanent wave agent has a pH of 9.0 to 10 by adding a basic substance such as ammonia, monoethanolamine or triethanolamine to an aqueous solution containing a reducing agent such as thioglycolic acid or cysteine as a main component.
The first agent was adjusted to 9.5, and the second agent was an aqueous solution of an oxidizing agent such as sodium bromate and hydrogen peroxide [eg, Tetsusaku Ikeda, "Cosmetics," (1979).
Year), Nanzandou Co., Ltd., p323-324].

The mechanism of waving the hair with such a permanent waving agent is to fix the hair to a rod or the like to curl it, and to reduce and cleave the disulfide bond of cystine contained in the keratin of the hair with the first agent. To generate a mercapto group,
The agent is intended to oxidize the mercapto group to generate new disulfide bonds at different positions on the hair to immobilize the wave.

[0004]

However, thioglycolic acid and cysteine, which are used as the reducing agent for the first agent for permanent wave, exhibit a reducing action in the alkaline region, and therefore in the neutral region. When used, a sufficient wave effect was not obtained, so that the liquid property of the first agent had to be made alkaline.

As a result, the hair is swollen by alkali during the permanent wave treatment, a part of the keratin constituting the hair is dissolved, and the remaining part of the hair is also subjected to physical and chemical changes to make the hair dry. For example, the hair is greatly damaged, and the scalp and eyes are also strongly stimulated.

Further, since thioglycolic acid has an unpleasant odor, there is a problem that unpleasant odor remains not only during the permanent wave treatment but also on the hair after the permanent wave treatment.

On the other hand, although the cysteine-based first agent has less unpleasant odor and hair damage than the thioglycolic acid-based first agent, it has a problem that the wave effect is low.

[0008]

As a result of various investigations in view of the above problems, the present inventors have found that the first permanent wave
As a reducing agent for the agent, N- (2- represented by the following general formula (I) HSCH ₂ CH ₂ NHCO-R (I) (in the formula, R is a CH ₃ group or a CH ₃ CH ₂ group). When the mercaptoethyl) alkylamide is used and the N- (2-mercaptoethyl) alkylamide represented by the general formula (I) is contained in the first agent for permanent wave in an amount of 2 to 15% by weight, a neutral range is obtained. However, it has been found that a good wave can be imparted to hair, and damage to the hair and irritation to the scalp, eyes, etc. can be reduced, and the present invention has been completed.

That is, N represented by the above general formula (I)
Since-(2-mercaptoethyl) alkylamide can exert a reducing action even in the neutral region, it is possible to perform permanent wave treatment in the neutral region and prevent hair damage due to alkali. Further, N represented by the general formula (I)
-(2-Mercaptoethyl) alkylamide is -SH
Although it has a group, it has a very low unpleasant odor because it is non-volatile.

Therefore, the first agent for permanent wave using the N- (2-mercaptoethyl) alkylamide represented by the general formula (I) as a reducing agent has less unpleasant odor and is not only used during the permanent wave treatment. Also, the hair after the permanent wave treatment has very little unpleasant odor.

In addition, N- (2 represented by the general formula (I)
-Mercaptoethyl) alkylamide has a high water solubility and has an amide bond, and therefore has a strong affinity with hair having a peptide bond, that is, an amide bond, and easily penetrates into the hair. Is superior to thioglycolic acid type and cysteine type. Also, the oxidized dimer produced as a by-product by the treatment with the second agent is a low-molecular-weight and water-soluble substance, and therefore does not remain on the hair
It has the feature of being easily washed away.

The N- (2-mercaptoethyl) alkylamide represented by the general formula (I) is a surfactant, a chelating agent, a pH adjusting agent, which is commonly used in the first agent for permanent wave. Can be used in combination with emulsifiers, thickeners, dyes, humectants, fragrances, etc., and by adding protein hydrolysates and their derivatives, cationic polymers, etc., further reduce damage to hair and impart a better wave to hair. be able to.

The first agent for permanent wave of the present invention is prepared, for example, as follows.

Basically, N- (2-mercaptoethyl) alkylamide represented by the general formula (I) is used as a reducing agent in place of the conventionally used thioglycolic acid type or cysteine type reducing agent. Other components include protein hydrolysates and their derivatives, cationic polymers, anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants and other various surfactants, and emulsifiers. , A thickener, a chelating agent, a dye, a pH adjusting agent, a wetting agent, a fragrance, etc. are appropriately added to water and mixed.

In the present invention, specific examples of the N- (2-mercaptoethyl) alkylamide represented by the general formula (I) include N- (2-mercaptoethyl) acetamide and N- (2-mercaptoethyl). Propionamide may be mentioned, and in the first agent for permanent wave,
The content of the N- (2-mercaptoethyl) alkylamide represented by the general formula (I) is 2 to 15% (% by weight, the same applies hereinafter), preferably 5 to 10%.

That is, N- represented by the general formula (I)
When the content of (2-mercaptoethyl) alkylamide in the first agent for permanent wave is less than 2%, the reducing action is not sufficiently exerted, so that the disulfide bond in the hair cannot be sufficiently cleaved. It is not possible to give sufficient permanent wave to hair. When the content of the N- (2-mercaptoethyl) alkylamide represented by the general formula (I) in the first agent for permanent waving is more than 15%, the waviness becomes excessively strong and the hair Individual differences of
Undesirable results may occur depending on the treatment temperature and treatment time.

The N- (2-mercaptoethyl) alkylamide represented by the general formula (I) is characterized in that it can exhibit a reducing action even in a neutral region. The represented N- (2-mercaptoethyl) alkylamide can exhibit a reducing action even in an alkaline region or a weakly acidic region.

Therefore, the first agent for permanent wave of the present invention can be used in a wide pH range of pH 4.5 to 10. However, the pH is preferably 6 to 8 in order to smoothly perform the permanent wave treatment while reducing damage to hair.

When the pH is adjusted to the alkaline range, the reducing action of the N- (2-mercaptoethyl) alkylamide represented by the general formula (I) becomes strong, and the conventional thioglycolic acid or cysteine-based compounds are used. When the reducing agent of is used, a stronger wave imparting action is exhibited.

Therefore, by adjusting the liquidity to an alkaline region, it is possible to prevent damage to the hair due to the permanent wave treatment by adding a protein hydrolyzate or a derivative thereof, and to impart a strong wave to the hair.

The reason why the addition of the protein hydrolyzate or its derivative makes it possible to further prevent the hair damage is as follows.

When the first agent for permanent wave of the present invention is used for hair, N- (2) represented by the general formula (I) is used.
-Mercaptoethyl) alkylamide penetrates into the hair and cleaves the disulfide bond (S-S bond) of cystine contained in the keratin of the hair to give a mercapto group (-S
H) is generated.

At this time, if the protein hydrolyzate or its derivative is added, they penetrate into the inside of the hair and are absorbed into the tissue of the hair.

Since the protein hydrolyzate or its derivative absorbed into the hair tissue has a peptide bond similar to that of keratin which is a constituent protein of hair, both of them have acidic properties such as glutamic acid and aspartic acid. Hair due to ionic bonds between side chains of amino acids and basic amino acids such as arginine, lysine, and histidine, hydrogen bonds between peptide chains, and van der Waals forces between side chains of hydrophobic amino acids. A bond is formed between the tissue and the tissue and is not easily washed off even when washed with water.

The protein hydrolyzate or its derivative thus absorbed in the hair strengthens the hair and prevents damage to the hair caused by the permanent wave treatment.

The addition of the protein hydrolyzate or its derivative also improves the gloss, feel and combability of the hair.

The above protein hydrolyzate can be obtained, for example, by hydrolyzing collagen, keratin, silk, casein, elastin, conchiolin, soybean protein, egg protein such as egg white and egg yolk with an acid, an alkali or an enzyme. And as this protein hydrolyzate, what has an average molecular weight of 200-5000 is especially preferable.

Examples of the derivative of the protein hydrolyzate include an acylated product of the protein hydrolyzate or a salt thereof, a quaternary ammonium derivative of the protein hydrolyzate, an ester of the protein hydrolyzate, and the like.

Then, these protein hydrolysates or derivatives thereof were added in the amount of 0.1% in the first agent for permanent wave.
It is preferable to add 1 to 10%, particularly 0.5 to 5%.

By adding a cationic polymer to the first agent for permanent wave, the gloss, feel, combability and the like of hair can be improved.

As such a cationic polymer,
For example, cationized cellulose, cationized hydroxyethyl cellulose, poly (diallyldimethylammonium chloride), polyvinyl pyridine, polyethylene imine and the like are preferable.

As the anionic surfactant used in the present invention, for example, lauric sulfate, polyoxyethylene alkyl ether sulfate, alkylbenzene sulfonate, N-acyl amino acid salt and the like are preferable.

Examples of the cationic surfactant include distearyldimethylammonium, dipolyoxyethyleneoleylammonium chloride, stearyldimethylbenzylammonium chloride, stearyltrimethylammonium chloride, cetyltrimethylammonium chloride and tri (polyoxyethylene) chloride. Stearyl ammonium, lauryl trimethyl ammonium chloride and the like are preferable.

Examples of the nonionic surfactant used in the present invention include polyoxyethylene alkyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene oleyl ether, polyoxyethylene glyceryl oleate, polyoxyethylene stearyl ether and polyoxyethylene oleyl ether. Oxyethylene nonyl phenyl ether and polyoxyethylene lanolin are preferred.

Examples of the amphoteric surfactant include 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, undecylhydroxyethylimidazolium betaine, stearyldihydroxyethylbetaine, stearyldimethylaminoacetic acid betaine, Palm oil fatty acid amidopropyl betaine, palm oil alkyl-N-carboxyethyl-N-hydroxyethyl imidazolinium betaine and the like are preferable.

Examples of the thickener include isostearic acid diethanolamide, undecylenic acid monoethanolamide, oleic acid diethanolamide, beef fatty acid monoethanolamide, stearic acid diethanolamide,
Stearic acid diethylaminoethylamide, lauric acid ethanolamide and the like are preferable.

As the pH adjuster, for example, ammonia, ethanolamines, ammonium carbonate, sodium hydrogen carbonate, sodium carbonate, formic acid, acetic acid, hydrochloric acid, sulfuric acid and the like are preferable.

Preferred humectants are, for example, polysaccharides, propylene glycol, butylene glycol, ethylene glycol, glycerin, polyethylene glycol and the like.

In addition, an emulsifier, a chelating agent, a dye, a fragrance, etc. can be added to the first agent for permanent wave of the present invention, and these are conventionally used in the first agent for permanent wave. You can use one.

Further, in the first agent for permanent wave of the present invention, a reducing agent which has been conventionally used may be used as long as the effect of the N- (2-mercaptoethyl) alkylamide represented by the general formula (I) is not impaired. It can also be used partially.

Examples of such reducing agents include thioglycolic acid, ammonium thioglycolic acid, monoethanolamine thioglycolic acid, thioglycolic acid derivatives, cysteine, cysteine derivatives, cysteamine,
Examples include sulfites such as ammonium sulfite.

[0042]

EXAMPLES Next, the present invention will be described in more detail by way of examples. However, the present invention is not limited to the examples.

Example 1 A first agent for permanent wave was prepared with the following composition. In addition,% showing the blending amount is% by weight.

Reducing agent: N- (2-mercaptoethyl) acetamide 6.0% Sodium carbonate 2.0% Sodium ethylenediaminetetraacetate 0.1% Polyoxyethylene (15EO) nonylphenyl ether 0.2% pH adjuster ( Adjust to pH 7 with hydrochloric acid) Sterilized ion-exchanged water 100% total

(15EO) of the polyoxyethylene (15EO) nonylphenyl ether means that the number of added moles of ethione oxide is 15 moles.

Example 2 The same procedure as in Example 1 was repeated except that N- (2-mercaptoethyl) acetamide was replaced with N- (2-mercaptoethyl) propionamide as the reducing agent. One agent was prepared.

Comparative Example 1 A first agent for permanent wave was prepared in the same manner as in Example 1 except that ammonium thioglycolate was used instead of N- (2-mercaptoethyl) acetamide as the reducing agent.

Comparative Example 2 A first agent for permanent wave was prepared in the same manner as in Example 1 except that cysteine was used as the reducing agent instead of N- (2-mercaptoethyl) acetamide.

The first agent for permanent wave of Examples 1 and 2 and Comparative Examples 1 and 2 above was used, and the second agent for permanent wave was a 6% sodium bromate aqueous solution. According to 3, the first agent for permanent wave was evaluated.

<Test Example 1> The wave efficiency and wave retention of the first agents for permanent wave were compared by the following methods.

1-1 Preparation of Samples Women's hair (about 18 cm in length) that has never undergone permanent wave or hair dyeing is made into a bundle of 10 springs, and these bundles of polyoxyethylene are preliminarily used. It was washed with a 2% aqueous solution of nonylphenyl ether and naturally dried at room temperature to give a test hair bundle.

1-2 Test Operation and Measurement of Wave Efficiency and Wave Retention The test hair bundle obtained as described above was wrapped around a plastic rod having a diameter of 12 mm at a pitch of 10 mm, and the hair bundle was subjected to Example 1 described above. .About.2 and the first agent for permanent wave of Comparative Examples 1 and 2 were sufficiently applied, left at room temperature for 15 minutes, washed with water, and then thoroughly applied with the second agent for permanent wave, and then applied at room temperature for 10 minutes. After leaving for a minute, the hair bundle was removed from the rod, washed with water, and then naturally dried.

The hair bundles that have undergone the permanent wave treatment as described above are separated into individual hairs, and the hairs are placed in a natural state on a horizontal table. From the apex of the second wave on the left and right sides of the hair bundles. The length to the vertex of the penultimate wave and the number of waves were measured.

The measured length on the left side was L ₁ , the number of waves was n ₁ , the length on the right side was L ₂ , and the number of waves was n _2, and the average wave length L was calculated by the following equation.

Average wave length L (mm) = (L ₁ + L
₂ ) / (n ₁ + n ₂ )

Thus, the average wave length L of each hair was obtained, and the average value of 10 hairs was obtained for each treated hair, and the wave efficiency E ₁ was obtained by the following formula.

The pitch of the spiral groove of the rod is 10 m.
m, and if the wave is generated as wound around the spiral groove of the rod, the wave efficiency is 100%.

Wave efficiency E ₁ (%) = (10 / L) × 100

After measuring the wave efficiency as described above, 10 hairs each were suspended, a weight of 3.2 g was attached to each hair and left for 12 hours, then the weight was removed from the hair and the wave efficiency was measured. The same measurement as the measurement was performed, the wave efficiency E ₂ of the reproduced wave was calculated, and the wave retention rate was calculated by the following equation.

Wave retention rate (%) = (E ₂ / E ₁ ) × 100

The wave efficiency (provided that the wave efficiency E ₁ ) and the wave retention rate obtained as described above are shown in Table 1.
Shown in.

[0062]

[Table 1]

As shown in Table 1, when the first agent for permanent wave of Examples 1 and 2 was used, the first agent for permanent wave of Comparative Example 1 using ammonium thioglycolate as a reducing agent and cysteine were used. Compared to the case where the first agent for permanent wave of Comparative Example 2 used as the reducing agent was used, the wave efficiency and the wave retention rate were large, and N-
It can be seen that (2-mercaptoethyl) alkylamide has an excellent wave imparting effect on hair as compared with ammonium thioglycolate and cysteine.

<Test Example 2> The degree of damage to hair was evaluated by quantitatively determining cysteic acid in the hair by the following amino acid analysis. The production of cysteic acid in hair is associated with hair damage, and the higher the amount of cysteic acid in hair, the greater the damage to hair due to permanent wave treatment.

That is, using the first agent for permanent wave of Examples 1 and 2 and Comparative Example 1, hydrochloric acid was added to each hair subjected to the permanent wave treatment in the same manner as in Test Example 1, and the mixture was vacuum-sealed at 110. After hydrolyzing at ℃ for 24 hours, further dried under reduced pressure to remove hydrochloric acid, diluted with sodium citrate buffer, filtered, and the amount of cysteic acid was measured by an amino acid analyzer. The results are shown in Table 2.

[0066]

[Table 2]

As shown in Table 2, when the first agent for permanent wave of Examples 1 and 2 was used, the cysteine in the hair was larger than that when the first agent for permanent wave of Comparative Example 1 was used. It can be seen that less acid is produced and N- (2-mercaptoethyl) alkylamide does less damage to the hair than ammonium thioglycolate.

<Test Example 3> Examples 1 and 2 and Comparative Example 1
Using the first agent for permanent wave of No. 1, the permanent wave treatment was carried out in the same manner as in Test Example 1, the feel of the hair after the permanent wave treatment, and the residual odor in a wet state after the permanent wave treatment (unpleasant odor based on mercapto group) The sensory evaluation of the residual odor in a dry state was carried out by a panel of 5 persons. The results are shown in Table 3.

[0069]

[Table 3]

Evaluation Criteria for Feeling of Hair ◯: Good Δ: Normal ×: Poor

Evaluation Criteria for Residual Odor ○: Almost not felt Δ: Slightly felt ×: Strongly felt

Table 3 shows the evaluation with the largest number of people as the evaluation result. As shown in Table 3, Example 1
When using the first agent for permanent wave of ~ 2,
Compared with the case where the first agent for permanent wave of Comparative Example 1 was used, the feel of the hair after the permanent wave treatment was good, and the residual odor was small, and N- (2-mercaptoethyl) alkylamide was thioglycol. It can be seen that, compared with ammonium acidate, it gives a good feel to hair and has less unpleasant odor.

Example 3 A first agent for permanent wave was prepared with the following composition,
Using it, a permanent wave treatment and a test were conducted in the same manner as in Example 1 above. The test results are shown in Table 4.

N- (2-mercaptoethyl) acetamide 6.0% Cetyltrimethylammonium chloride 0.3% Trimethyl quaternary ammonium derivative of keratin peptide 0.5% (trade name: Promois WK-HQ, Seiwa Co., Ltd. Kasei) Sodium ethylenediaminetetraacetate 0.1% Ammonia water (adjusted to pH 7) Sterilized ion-exchanged water Total 100%

Example 4 Instead of the trimethyl quaternary ammonium derivative of keratin peptide, keratin peptide (trade name: Promois W)
KH, manufactured by Seiwa Kasei Co., Ltd.) was used in the same manner as in Example 3, except that the first agent for permanent wave was prepared, and the permanent wave treatment and permanent wave treatment were performed in the same manner as in Example 1. The test was conducted. The test results are shown in Table 4.

[0076]

[Table 4]

As shown in Table 4, when the first agent for permanent wave of Examples 3 to 4 was used, the amount of cysteic acid was less than that in Example 1, and a keratin peptide or a derivative of keratin peptide was added. Therefore, it can be seen that hair damage can be further reduced.

Regarding the wave effect and the wave holding ratio, the first permanent wave wave of Examples 3 to 4 was used.
The agent was almost the same as the first agent for the permanent wave of Example 1, and no significant decrease in the wave imparting effect due to the addition of the keratin peptide or the derivative of the keratin peptide was observed.

Example 5 Reducing agent: N- (2-mercaptoethyl) acetamide 6.0% Monoethanolamine 1.0% Ethylenediaminetetraacetic acid disodium 0.1% Polyoxyethylene (15EO) nonylphenyl ether 0.2 % PH adjuster (pH adjusted to 9 with hydrochloric acid) Sterilized ion-exchanged water 100% total

Comparative Example 3 A first agent for permanent wave was prepared in the same manner as in Example 5 except that ammonium thioglycolate was used as the reducing agent instead of N- (2-mercaptoethyl) acetamide.

Using the first agent for permanent wave of Example 5 and Comparative Example 3 above, a permanent wave treatment and a test were carried out in the same manner as in Example 1.

Table 5 shows the measurement results of wave efficiency, wave retention rate and cysteic acid. Table 6 shows the results of a sensory test on the feel of the hair after the permanent wave treatment, the residual odor in the wet state after the permanent wave treatment, and the residual odor in the dry state. The evaluation criteria for the feel of the hair and the residual odor in Table 6 are the same as those in Table 3.

[0083]

[Table 5]

[0084]

[Table 6]

First Example for Permanent Wave of Example 5
PH of both agents and the first agent for permanent wave of Comparative Example 3
Was adjusted to 9, but as shown in Table 5 and Table 6, when the first agent for permanent wave of Example 5 was used, when the first agent for permanent wave of Comparative Example 3 was used Compared with the above, the wave efficiency and the wave retention rate were large, the amount of cysteic acid was small, the feel of the hair after the permanent wave treatment was good, and the residual odor was small.

The first agent for permanent wave of Comparative Example 3 corresponds to the conventional first agent for permanent wave, but N- (2-mercaptoethyl) is used as a reducing agent.
When acetamide was used to adjust the pH to 9, compared to the case where the conventional permanent wave first agent was used,
It can be seen that a strong wave can be imparted to the hair, the hair is less damaged, the hair feels good after the permanent wave treatment, and the residual odor is small.

[0087]

As described above, in the present invention, by using N- (2-mercaptoethyl) alkylamide represented by the general formula (I) as a reducing agent, good hair is obtained even in the neutral region. It was possible to provide the first agent for permanent wave, which can be imparted with waves and which causes less damage to the hair due to the permanent wave treatment.

Front page continuation (72) Inventor Takashi Adachi 1-2-14, Nunoichi-cho, Higashiosaka-shi, Osaka Prefecture Seiwa Kasei Co., Ltd.

Claims (2)

[Claims] 1. N- (2-mercapto) represented by the following general formula (I) HSCH ₂ CH ₂ NHCO-R (I) (wherein R is a CH ₃ group or a CH ₃ CH ₂ group). A first agent for permanent wave, which comprises 2 to 15% by weight of ethyl) alkylamide as a reducing agent. 2. The first agent for permanent wave according to claim 1, wherein a protein hydrolyzate or a derivative thereof is added.