JP2562405B2 - Keratin fiber treating agent composition - Google Patents

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a keratin fiber treating agent composition for chemically treating keratin fibers such as hair, wool, fibers for woolen fabrics, and more specifically imparting firmness and elasticity to the keratin fibers. Keratin for shaping and shaping, while enhancing the effect of shaping keratin fibers with curls, waves, straight perms, etc., and for maintaining the shape of shaped keratin fibers for a long time and sustaining them. The present invention relates to a fiber treatment composition.

[0002]

2. Description of the Related Art Heretofore, there have been reported many keratin fiber treating agents containing a polymer or a conditioning agent for imparting a firmness and elasticity to keratin fibers such as hair, wool, and fibers for woolen fabrics (Japanese Patent Laid-Open Publication No. Sho. 52-7449 and 58-216113). But these are
The effect is exhibited by the treatment agent adsorbing to the surface of the keratin fiber, which causes a feeling of dryness such as a dry feeling accompanying the application of the treatment agent, and the adsorbed treatment agent will fall off if washed, so it is always There was the annoyance that processing had to be performed. Further, in order to give the original shape of the keratin fiber to shaping such as curls and waves, a method of shaping with a temporary setting agent such as a blow agent for hair or a method of semipermanent chemical treatment with a perming agent etc. Are typical. However, among these methods, the keratin fiber shaped by the temporary setting agent loses its set shape due to an increase in humidity and getting wet with water. On the other hand, curls and waves produced by perm treatment cause shape loss due to repeated washing, and are not sufficient in the effect of sustaining a desired shape continuously, and in addition, straight curl hair straightening that straightens bent keratin fibers The perm treatment has a problem that the bending of the keratin fibers cannot be satisfactorily corrected.

In order to solve these problems, attempts have been made to penetrate a keratin fiber with a treating agent to continuously modify the fiber itself. For example, a treating agent containing an astringent (special feature: KAISHO 55-108812, 58-1
No. 09405, No. 60-87208), and a treating agent containing naphthalene sulfonic acids (J. Soc. Cosm).
et. Chem. , 36, 87-99 (1985)),
A treatment agent for forming a sparingly soluble salt in hair (Japanese Patent Laid-Open No. 1-22)
No. 33208) and a treating agent containing a divalent or higher valent metal salt (Japanese Patent Laid-Open No. 3-275614), but none of these effects were sufficiently satisfactory.

[0004]

SUMMARY OF THE INVENTION Therefore, the object of the present invention is to shape keratin fibers while maintaining their elasticity and elasticity without impairing the supple feel of keratin fibers, and to curl, wave or straight line by chemical treatment. The effect of shaping the shape is enhanced, and the shaped shape for a long time,
It is intended to provide a keratin fiber treating agent composition which imparts a sustained holding effect.

[0005]

In view of the above situation, the present inventor has conducted diligent research to solve the above problems, and as a result,
A treatment agent containing a naphthalene derivative represented by the general formula (1) or a salt thereof, which will be described later, effectively improves the elasticity of keratin fibers and does not impair the supple feel peculiar to keratin fibers, and the fibers are firm, It has been found that it can be shaped while giving it elasticity, it enhances the effect of shaping the fibers that have undergone chemical treatment such as perm, and is excellent in the effect of holding the shaped shape continuously for a long time. The present invention has been completed.

[0006]

That is, the present invention has the following general formula (1):

[0008]

Embedded image

[In the formula, A ¹ is PO ₄ H ₂ , PO ₃ H ₂ ,
COOH or CH ₂ COOH, A ² is H, OH, NO
₂ , COOH or an alkyl group having 1 to 10 carbon atoms is shown]
The present invention provides a keratin fiber treating agent composition characterized by containing a naphthalene derivative represented by: or a salt thereof.

[0010]

Specific examples of the naphthalene derivative represented by the above general formula (1) include 1-naphthylphosphoric acid and 2-
Naphthylphosphoric acid, 1-naphthol-2-phosphoric acid, 2-naphthol-1-phosphoric acid, 2-naphthol-3-phosphoric acid, 1-naphthylphosphonic acid, 2-naphthylphosphonic acid, 1-naphthoic acid, 2-naphthoic acid, 1 -Hydroxy-2-naphthoic acid, 2-hydroxy-1-naphthoic acid, 2-hydroxy-3-naphthoic acid, 2-hydroxy-6-naphthoic acid,
1-naphthyl acetic acid, 2-naphthyl acetic acid, 2,3-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid,
1,2-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid, 1,5-naphthalenedicarboxylic acid, 1,
8-naphthalenedicarboxylic acid, 1-nitro-2-naphthoic acid, 2-ethyl-6-naphthylphosphoric acid, 2-ethyl-6
-Naphthoic acid, and among these, 1-naphthylphosphoric acid, 2-naphthylphosphoric acid, 1-naphthylacetic acid, 2-naphthylacetic acid, 1-naphthoic acid, 2-naphthoic acid, 2-hydroxy-1-naphthoic acid, 1 -Hydroxy-2-naphthoic acid and 2-hydroxy-3-naphthoic acid are particularly preferred.

Examples of salts of these naphthalene derivatives include sodium salts, potassium salts, lithium salts, ammonium salts and organic quaternary ammonium salts.

The amount of the naphthalene derivative represented by the above general formula (1) or a salt thereof in the composition of the present invention is 0.1 to 1.
0% by weight (hereinafter, simply indicated by "%") is preferable, and 0.5 to 5% is particularly preferable. If it is less than 0.1%, the effect of treating keratin fibers cannot be sufficiently obtained, and if it exceeds 10%, the effect corresponding to the increased amount is not improved.

In the composition of the present invention, it is preferable to add a solvent in order to improve the solubility of the naphthalene derivative or a salt thereof, and the solvent is a compound represented by the following general formula (2):

[0015]

Embedded image

N-alkylpyrrolidone represented by the general formula (3):

[0017]

[Chemical 4]

[In the formula, R ³ represents a linear or branched alkyl group having 1 to 18 carbon atoms] and an alkylene carbonate having 1 to 4 carbon atoms.

Specific examples of these solvents include, for example, organic solvents such as ethanol, isopropanol, and n.
-Lower alcohols such as propanol, n-butanol and isobutanol; diols such as ethylene glycol, propylene glycol, 1,3-butanediol and glycerin, triols; benzyl alcohol, cinnamyl alcohol, phenethyl alcohol, p-anisyl alcohol, Aromatic alcohols such as p-methylbenzyl alcohol, phenoxyethanol, 2-benzyloxyethanol; polycarbylates such as methyl carbitol, ethyl carbitol, propyl carbitol, butyl carbitol, triethylene glycol monoethyl ether and triethylene glycol monobutyl ether. Oxyalkylene lower alkyl ether; N-alkylpyrrolidone such as N-methylpyrrolidone, N-octylpyrrolidone, N-laurylpyrrolidone, etc. It is below. The compounding amount of these organic solvents is 0.5 to 50%, particularly 2 to 30% in the composition of the present invention.
Is preferred.

Further, it is preferable that the composition of the present invention is further added with an acid or an alkali as a pH adjusting agent to adjust the total pH to a specific range. That is, by adjusting the pH to a specific region, the keratin fiber is sufficiently swollen and the penetration of the treatment agent into the fiber is further promoted. At this time, the pH of the composition is preferably adjusted to 2 to 5 when the acid is added, while the pH is preferably adjusted to 8 to 11 when the alkali is added. P of the composition
When H is less than 2 or exceeds 11, there is a risk of damaging keratin fibers.

Regarding the swelling of keratin fibers, especially hair by acid or alkali, the research report by Bat et al. {G. R.
Bhat et al. , J. et al. Soc. Cosmet.
Chem. , 32f, 393-405 (1981)}, and according to this, hydrochloric acid is used as the acid and sodium hydroxide is used as the alkali. In the composition of the present invention, an organic acid or phosphoric acid is used as the acid, and It is preferable to use ammonia or an organic amine.

Specific examples of the pH adjusting agent used in the composition of the present invention include citric acid, glycolic acid as an organic acid,
Succinic acid, tartaric acid, lactic acid, acetic acid, fumaric acid, malic acid,
Levulinic acid, butyric acid, valeric acid, oxalic acid, maleic acid, phthalic acid, mandelic acid and the like; organic amines such as monoethanolamine, diethanolamine, triethanolamine, morpholine, N-methylmorpholine, N-ethylmorpholine, morpholineethanol, Piperidine, piperidine ethanol, aminohydroxymethyl propanediol, 2-amino-2-methyl-1-propanol, 2
Examples thereof include basic amino acids such as -amino-2-methyl-1,3-propanediol and arginine.

These acids or alkalis can be used alone or in combination, and the compounding amount is preferably 0.3 to 50%, more preferably 0.5 to 30%. When the content of the pH adjuster is less than 0.3%,
The swelling effect is small due to the ion exchange capacity of the keratin fiber, and the effect cannot be increased even if the content exceeds 50%.

The keratin fiber treating agent composition of the present invention preferably contains a sodium salt, potassium salt, ammonium salt or the like of an organic acid to form a buffer system.

In the composition of the present invention, the rest of the components other than the naphthalene derivative represented by the general formula (1) or the salt thereof, the solvent and the pH adjusting agent is usually water, but the effect of the present invention is not impaired. In the range, if necessary, a thickener such as hydroxyethyl cellulose, a surfactant, a fragrance, a pearling agent,
Dyes, ultraviolet absorbers, antioxidants, preservatives and the like may be added. In addition, in order to improve the feel of keratin fibers, cationic polymers such as cationized cellulose,
Silicone derivatives such as dimethylpolysiloxane and amino-modified silicone can also be blended.

Further, the composition of the present invention comprises thioglycolic acid, cysteine, acetyl cysteine, glutathione,
Perming fluid 1 containing a reducing agent such as thioglycolamide
It can be used as an agent (reducing agent) or as a perm liquid 2 agent (oxidizing agent) containing an oxidizing agent such as sodium bromate, potassium bromate and sodium perborate.

As a method of using the composition of the present invention, the keratin fiber may be in a dry state or in a wet state after washing,
Specifically, keratin fibers are dipped in the keratin fiber treatment agent of the present invention and left for a certain period of time, preferably 5 to 30 minutes, and then washed off, or left without washing, or applied for several hours during sleep. Examples of the method include leaving after being left in the state and then rinsing, or leaving without rinsing. Further, when left for immersion or after application, it may be heated to an appropriate temperature, preferably 30 to 50 ° C. Further, when the composition of the present invention is used immediately after the perming or straight perming treatment of the hair or between the 1st and 2nd perming liquids, the effect can be further enhanced. Further, it is sufficiently effective to use it as one perm solution or two perm solution.

[0028]

EFFECTS OF THE INVENTION The keratin fiber treating agent composition of the present invention can be shaped while imparting elasticity and elasticity to the fiber without impairing the supple feel of the keratin fiber, and by curling, waving, straight perm, etc. It is excellent in enhancing the effect of shaping and maintaining the shape of keratin fibers that have undergone chemical treatment such as perm or straight perm.

[0029]

EXAMPLES The present invention will now be described by way of examples, which should not be construed as limiting the invention thereto.

Examples 1 to 4, Comparative Example 1: Effect of imparting a firmness and firmness to the keratin fiber The effect of imparting a firmness and firmness to the keratin fibers was tested by the following method. As the test method, the hair of a Japanese woman, which had not been subjected to cosmetic treatment such as cold perm or bleach as keratin fiber by the time of the test, was used, and the hair was dipped in the treatment agent shown in Table 1 at 40 ° C. for 30 minutes. Then, it is washed with ion-exchanged water and dried, and its tensile elasticity is measured under a relative humidity of 50%, and the tensile elasticity of untreated hair measured under the same conditions is set to 1.00 and treated. The tensile elasticity of the hair was calculated relatively. The results are shown in Table 1.

[0031]

[Table 1]

From the results of tensile elasticity in Table 1, it is understood that Examples 1 to 4 using the composition of the present invention have remarkably improved elasticity of keratin fibers as compared with Comparative Example 1.

Examples 5 to 8: Sensory evaluation of firmness and firmness

A keratin fiber treating agent having the composition shown in Table 3 was prepared, and hair bundles of 10 g of hair of a Japanese woman who had not been subjected to cosmetic treatment such as cold perm or bleach as keratin fibers by the time of the test were prepared. After the bundle was treated in the same manner as in Example 1, five panelists performed sensory evaluation of firmness and firmness. As the evaluation criteria, the criteria shown in Table 2 were followed.

[0035]

[Table 2] Firmness and firmness were remarkably improved over untreated hair: ◎ Firmness and firmness were improved over untreated hair: ○ Firmness and firmness were almost unchanged from untreated hair: ×

[0036]

[Table 3]

From the evaluation of the firmness and firmness in Table 3, it was found that Examples 5 to 8 using the composition of the present invention significantly improved the firmness and firmness as compared with untreated hair.

Examples 9-13:

A keratin fiber treating agent having the composition shown in Table 4 was prepared, treated in the same manner as in Example 5, and subjected to a sensory evaluation of firmness and firmness.

[0040]

[Table 4]

In Examples 9 to 13 in which the composition of the present invention was used, it was confirmed that the firmness and stiffness of the hair were improved as compared with untreated hair.

Examples 14 to 17 and Comparative Example 2: Sustained shaping effect on keratin fibers

A keratin fiber treating agent composition having the composition shown in Table 5 was prepared, and the sustained shaping effect of the treating agent on hair was tested by the following method. As a test method, the hair of a Japanese man who has not undergone cosmetic treatment such as cold perm or bleach as keratin fiber by the time of the test and has a habit of constant curvature (so-called habit hair) is used. Treatment agent 40 shown in Table 5 fixed in a straight line with a Teflon rod.
After immersing at 30 ° C. for 30 minutes and washing with ion-exchanged water, the hair was removed from the rod and dried under a relative humidity of 50%, and then the curvature of the hair was measured. From these measured values, the effect of shaping keratin fibers was evaluated. After that, the hair was washed 20 times with shampoo, dried again under relative humidity of 50%, the curvature of the hair was measured, and the curvature before and after shampoo was compared to evaluate the duration of effect.

[0044]

[Table 5]

Results In Examples 14 to 17 in which the composition of the present invention was used, the curvature was lower than in Comparative Example 2, and the keratin fibers were linearly shaped, and the rate of change in the curvature was high even after repeated washing. It was low. That is, it was confirmed that the composition of the present invention is excellent in the effect of shaping keratin fibers and its durability.

Examples 18 to 21, Comparative Example 3: Effect of sustaining the shape of chemically treated keratin fibers

To prepare a keratin fiber treating agent composition having the composition shown in Table 6 and imparting curls or waves to hair,
The effect of sustaining the shape of the keratin fiber chemically treated with perm was tested by the following method. As a test method, the hair of a Japanese woman who had not been subjected to cosmetic treatment such as cold perm or bleach as keratin fiber by the time of the test was used, and this hair was wrapped around a Teflon rod having a diameter of 1 cm to be permed. Then, the hair was immersed in the treatment agent shown in Table 6 at 40 ° C. for 10 minutes, washed with ion-exchanged water, the hair was removed from the rod, and the hair was dried under a relative humidity of 50%, and the curl diameter of the hair was measured. After that, this hair was washed 20 times with shampoo, dried again under relative humidity of 50%, the curl diameter of the hair was measured, and the curl diameter before and after shampoo was compared to maintain the shaping of the treatment agent continuously. The effect of doing was evaluated.

[0048]

[Table 6]

Results Examples 18 to 2 using the treating agent comprising the composition of the present invention
1 has a lower rate of change in curl diameter after repeated washing as compared with Comparative Example 3, and it was confirmed that the composition of the present invention is excellent in the effect of sustaining the shaped curl continuously.

Examples 22 to 25, Comparative Example 4: Effect of continuously correcting the habit remaining in the keratin fibers subjected to the straight perm treatment.

A keratin fiber treating agent composition having the composition shown in Table 7 was prepared, and the effect of continuously correcting the habit remaining on the straight-permed hair was tested by the following method. As a test method, the hair of a Japanese man who has not undergone cosmetic treatment such as cold perm or bleach as keratin fiber by the time of the test and has a habit of constant curvature (so-called habit hair) is used. After fixing in a straight line with a Teflon rod and performing straight perm treatment, see Table 7
After immersing in the treatment agent shown in 40 ° C. for 30 minutes and washing with ion-exchanged water, the hair is removed from the rod and the relative humidity is adjusted to 50
The curvature of the hair was measured after drying under%. From these measured values, the effect of correcting the habit remaining in the straight permed keratin fibers was evaluated. After that, this hair was washed 20 times with shampoo, dried again under relative humidity of 50%, the curvature of the hair was measured, and the curvature before and after shampoo was compared to maintain the effect of correcting the habit of the treatment agent. The sex was evaluated.

[0052]

[Table 7]

Results Examples 22 to 25 using the composition of the present invention have a lower curvature than the comparative example 4 and the habit remaining in the keratin fibers subjected to the straight perm treatment is corrected, and after repeated washing. However, the rate of change in the curvature was low, and it was confirmed that the composition of the present invention was excellent in the effect of maintaining the correction effect.

Examples 26 to 27, Comparative Example 5: Effect of sustaining the shape of keratin fibers chemically treated with a perm solution in which the composition of the present invention is added to the reducing agent side of a two-part perm solution.

A reducing agent for a two-part perm solution having the composition shown in Table 8 was prepared, and the shape of the keratin fiber chemically treated with the perm solution was continuously applied to impart curl or wave to hair. The retaining effect was tested by the following method.
As the test method, the hair of a Japanese woman who had not been subjected to a cosmetic treatment such as cold perm or bleach as keratin fiber by the time of the test was used, and the hair was wrapped around a Teflon rod with a diameter of 1 cm and the perm shown in Table 8 was used. Immerse in liquid 1 agent (reduction treatment agent) at 30 ° C for 10 minutes, and then perm solution 2
Agent (oxidizing agent: 8% sodium bromate aqueous solution) 30
After dipping at 10 ° C for 10 minutes for perm, the hair was washed with ion-exchanged water, removed from the rod, and dried under relative humidity of 50%, and then the curl diameter of the hair was measured. After that, this hair was washed 20 times with shampoo, dried again under relative humidity of 50%, the curl diameter of the hair was measured, the curl diameter before and after shampoo was compared, and the curl diameter before and after the composition of the present invention was used. It was evaluated whether or not the shape of the keratin fiber subjected to the perm treatment was retained continuously.

[0056]

[Table 8]

Results Compared to the keratin fibers treated with the perm solution of Examples 26 to 27 containing the composition of the present invention, the rate of change in curl diameter was low even after repeated washing, When the composition of the present invention was added to the perm solution, it was confirmed that the curl lasted a long time.

Examples 28 to 29, Comparative Example 6: The habit of keratin fibers that have been subjected to straight perm treatment with a perm solution containing the composition of the present invention on the reducing agent side of a two-part perm solution is continuously corrected. Effect

A reducing treatment agent side of a two-pack type perm solution having the composition shown in Table 9 was prepared, and a straight perm was applied with this perm solution to test the effect of continuously correcting the habit of keratin fibers by the following method. did. As a test method, the hair of a Japanese man who has not undergone a cosmetic treatment such as cold perm or bleach as keratin fiber by the time of the test and has a certain curvature (so-called habit hair) is used. Permanent liquid 1 shown in Table 9 after being fixed linearly to the rod made of
After being dipped in the agent (reduction treatment agent) at 30 ° C for 10 minutes and then dipped in 2 agents of perm liquid (oxidation treatment agent: 8% sodium bromate aqueous solution) at 30 ° C for 10 minutes to give a straight perm, After washing the hair with ion-exchanged water, removing the hair from the rod, and drying under relative humidity of 50%,
The curvature of the hair was measured. Then, this hair was washed 20 times with shampoo, dried again under relative humidity of 50%, the curvature of the hair was measured, the curvature before and after shampoo was compared, and the hair was straightened with a perm solution containing the composition of the present invention. -Evaluation of the effect of continuously correcting the habit of keratin fibers subjected to perm treatment.

[0060]

[Table 9]

Results Example 28 using a perm solution containing the composition of the present invention
The keratin fiber treated with the perm solution of ~ 29 has a lower curvature than the one treated in Comparative Example 6, and the habit remaining in the keratin fiber subjected to the straight perm treatment is corrected, and even after repeated washing, Curvature change rate is low,
It has been found that the perm solution comprising the composition of the present invention is excellent in the effect of correcting the habit of keratin fibers, and the correction effect is persistent.

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Kaoru Tsujii 1-11-23 Yoto, Utsunomiya City, Tochigi Prefecture Naoi Heights 405

Claims (2)

(57) [Claims] 1. The following general formula (1): Wherein, ^{A 1} is a _{PO 4 H 2, PO 3 H} 2, COOH or _CH 2 ^COOH, A 2 is H, _OH, NO 2, COOH
Or a naphthalene derivative represented by C1-10 alkyl group] or a salt thereof is contained. 2. A keratin fiber treating agent composition comprising a compound represented by the general formula (1) according to claim 1 and a reducing agent or an oxidizing agent.