JP6012395B2 - Damaged hair improving agent and hair cosmetic - Google Patents

Description

  The present invention relates to a damaged hair improving agent, and more particularly, a damaged hair improving agent for improving the elasticity and moisturizing property of hair damaged by daily physical and chemical action, and the damaged hair improving agent. The present invention relates to a hair cosmetic composition that has an effect of improving elasticity and moisture retention of hair and imparts good usability (harshness, firmness, smoothness, no stickiness) to hair.

  In recent years, with the diversification of hairstyles, the opportunity for hair to be treated with hair coloring agents, bleaching agents, permanent wave agents, hair straighteners and the like has increased. The chemical action of these chemicals and the physical action of hair care behavior such as daily dryer heat and brushing promote hair damage, losing the original elasticity, elasticity, firmness, smoothness and moisture of hair. It is a factor to make. Therefore, a method of supplying water and a method of coating oil have been used to improve such damaged hair, but this was only a temporary effect and did not lead to a fundamental improvement.

  Therefore, Patent Document 1 proposes a hair-healing agent that uses arginine, which is a basic amino acid, as an active ingredient, cures damaged hair when it reaches the core of the hair, and restores the original beauty and health of the hair. In addition, Patent Document 2 proposes a hair cosmetic or the like that can act from the inside of the hair and simultaneously perform hair repair and styling by using two types of amino acids, acidic amino acid and basic amino acid. The effect of improving the elasticity of the hair was insufficient only by using amino acids.

JP 2001-81013 A (page 1-14) JP 2004-346040 A (page 1-14)

  The present invention relates to a damaged hair improving agent, and more particularly, a damaged hair improving agent for improving the elasticity and moisturizing property of hair damaged by daily physical and chemical action, and the damaged hair improving agent. To provide a hair cosmetic that contains hair and has the effect of improving the elasticity and moisture retention of the hair and imparts good usability (harshness, firmness, smoothness, no stickiness) to the hair is there.

（式中、Ｒ^１は、下記一般式（２）で表される基、Ｒ^２は炭素数１〜３のアルキル基、アルケニル基もしくはヒドロキシアルキル基を表し、Ｍは水素原子、アルカリ金属、アルカリ土類金属、アンモニウム及び有機アミン類から選ばれる少なくとも１種を表す。）

（式中、Ｒ^３は直鎖又は分岐した炭素数１〜８のアルキル基、アルケニル基もしくはヒドロキシアルキル基）
で表されるタウリン誘導体からなる損傷毛髪改善剤が、優れた毛髪弾力性改善効果と毛髪保湿性改善効果を有することを見出し本発明を完成させた。 As a result of intensive studies to solve the above problems, the present inventors have
The following general formula (1)

(In the formula, R ¹ represents a group represented by the following general formula (2), R ² represents an alkyl group having 1 to 3 carbon atoms, an alkenyl group or a hydroxyalkyl group, and M represents a hydrogen atom, an alkali metal, an alkali. It represents at least one selected from earth metals, ammonium and organic amines.)

(Wherein R ³ is a linear or branched alkyl group having 1 to 8 carbon atoms, an alkenyl group or a hydroxyalkyl group)
The present invention was completed by finding that the damaged hair improving agent comprising a taurine derivative represented by the formula has excellent hair elasticity improving effect and hair moisturizing improving effect.

  That is, the damaged hair improving agent comprising the taurine derivative represented by the general formula (1) according to the present invention and the hair cosmetic containing the damaged hair improving agent improve the elasticity and moisture retention of the hair. It has an effect and can impart good usability (harshness, firmness, smoothness, no stickiness, moistness) to hair.

（式中、Ｒ^２、Ｒ^３、Ｍは前記と同じ。） Below, the damaged hair improving agent of this invention and the hair cosmetics containing this damaged hair improving agent are explained in full detail.
Although there is no limitation in particular as a manufacturing method of the taurine derivative which is a damaged hair improvement agent of this invention, it can manufacture with the method generally shown by the following Formula.

(Wherein R ² , R ³ and M are the same as above)

  As a specific method for producing the taurine derivative represented above, the active ingredient of the taurine derivative is 10 to 90% in an aqueous system and / or a solvent system or an aqueous solvent mixed system solvent (in the case of a mixed system solvent). Water: solvent = 5: 95 to 95: 5), N-alkyl taurine was neutralized with alkali to obtain an N-alkyl taurine salt solution, and 0.8 to 1.2 glycidyl ether at the same temperature to 95 ° C. Are added by a method such as batch or dropwise addition, and aged at 60 to 95 ° C. until the reaction is completed. Here, the glycidyl ether is more preferably 0.9 to 1 mol, an aging temperature of 70 to 90 ° C., and an aging time of 1 to 10 hours with respect to 1 mol of N-alkyltaurine.

  Examples of the alkali used for neutralizing the taurine derivative include alkali metals such as lithium, potassium and sodium, alkaline earth metals such as calcium and magnesium, and alkali metal hydroxides such as lithium hydroxide, potassium hydroxide and sodium hydroxide. And alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide can be preferably used. In addition, organic amines such as ammonia, monoethanolamine, diethanolamine, and triethanolamine can be preferably used.

  The glycidyl ether used for the production of the taurine derivative is a glycidyl ether having an alkyl group, alkenyl group or hydroxyalkyl group having 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms, specifically methyl glycidyl ether or ethyl glycidyl. Ether, n-propyl glycidyl ether, i-propyl glycidyl ether, n-butyl glycidyl ether, i-butyl glycidyl ether, n-pentyl glycidyl ether, 2-ethylhexyl-glycidyl ether, vinyl glycidyl ether, allyl glycidyl ether, 2-methyl Allyl glycidyl ether, butenyl glycidyl ether, octenyl glycidyl ether, 2-ethylhexenyl glycidyl ether and the like are listed. “Epogosei” series manufactured by Yokkaichi Synthesis Co., Ltd. , Has been commercially available as NOF Co., Ltd. "EPIOL" series, etc., but the present invention is not particularly limited to these.

  Taurine derivatives can be produced only in an aqueous system, but lower alcohols such as ethanol and 2-propanol, polyhydric alcohols such as propylene glycol, dipropylene glycol and 1,3-butylene glycol, acetone and the like. Production in a solvent such as ketones or an aqueous solvent mixed solvent is also possible, and among these, ethanol and 2-propanol are particularly preferably used. The active ingredient of the taurine derivative in the reaction system is 30 to 60%, in an aqueous system and / or a solvent system or an aqueous solvent mixed solvent (in the case of a mixed solvent, water: solvent = 20: 80 to 90:10), particularly in an aqueous system. Is more preferable.

  The obtained taurine derivative can be used as it is for the product of the present invention, but can also be purified and used by a conventional purification method such as column purification using an ion exchange resin, silica gel or the like. The taurine derivative of the present invention can be produced by other methods, and the production method is not particularly limited.

  The blending amount of the damaged hair improving agent of the present invention into the hair cosmetic is preferably 0.01 to 20% by weight, particularly preferably 0.05 to 10% by weight. If it is less than 0.01%, the effect of improving the elasticity and moisture retention of the hair is insufficient, and even if it is added in an amount of 20% or more, the usability becomes sticky.

  The hair cosmetic composition comprising the damaged hair improving agent of the present invention can be applied to any composition used for hair, and it can be applied from a dosage form such as a transparent liquid, gel, cream, emulsion, or mousse. Hair treatments such as shampoos, hair rinses, hair conditioners, hair treatments, hair packs, hair sprays, styling agents, hair coloring agents, bleaching agents, permanent wave agents, hair straighteners, etc. Agents and the like can be mentioned, and any of the usage forms such as those that are rinsed after applied to the hair and applied to the hair, and those that are not washed away are suitably used.

  The hair cosmetic composition containing the damaged hair improving agent of the present invention preferably contains a cationic surfactant, an oily component, a cationic polymer and the like in addition to the damaged hair improving agent.

  As the cationic surfactant, a quaternary ammonium salt and / or a tertiary amine can be used, and examples of the quaternary ammonium salt include alkyltrimethylammonium salt, alkylamidoamine, alkylhydroxyetheramine, and the like. Lauryltrimonium chloride, myristyltrimonium chloride, cetyltrimonium chloride, stearyltrimonium chloride, behentrimonium chloride, lauryltrimonium bromide, myristyltrimonium bromide, cetyltrimonium bromide, stearyltrimonium bromide, behenyltrimonium bromide, Lauryl PG trimonium chloride, myristyl PG trimonium chloride, cetyl PG trimonium chloride, stearyl PG trimonium chloride, Henyl PG trimonium chloride, lauryl PG trimonium bromide, myristyl PG trimonium bromide, cetyl PG trimonium bromide, stearyl PG trimonium bromide, behenyl PG trimonium bromide, dicetyl dimonium chloride, distearyl dimonium chloride, dicocodimomo Nitric chloride, etc .; tertiary amines such as lauryl dimethylamine, myristyl dimethylamine, cetyl dimethylamine, stearyl dimethylamine, oleyl dimethylamine, isostearyl dimethylamine, aralkyl dimethylamine, behenyl dimethylamine, lauramidopropyl dimethylamine, myrista Midopropyldimethylamine, palmitamidopropyldimethylamine, stearamidepropyldimethylamine, oleamido Pyrdimethylamine, isostearamidpropyldimethylamine, araquinamidepropyldimethylamine, behenamidepropyldimethylamine, stearamideethyldiethylamine, araquinamideethyldiethylamine, behenamideethyldiethylamine, laurylPGdimethylamine, myristylPGdimethyl Examples include amine, cetyl PG dimethylamine, stearyl PG dimethylamine, and behenyl PG dimethylamine. Among these, stearyl trimonium chloride and behentrimonium chloride are particularly preferably used.

  Tertiary amines are neutralized with inorganic acids and / or organic acids and used as salts. Specific examples of inorganic acids and / or organic acids include hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, lactic acid, glycolic acid, citric acid. An acid, glutamic acid, malic acid, succinic acid, etc. are mentioned, Among these, 1 type or 2 types can be used arbitrarily.

  In the present invention, one or more of these cationic surfactants can be arbitrarily used, and the blending amount in the hair cosmetic is preferably 0.1 to 20% by weight.

  Examples of the oil component include liquids and solids at room temperature, and include higher alcohols, higher fatty acids, ester oils, silicones, hydrocarbons, and the like, and suitable ones may be appropriately selected from these.

  Specific examples of the oil component include higher alcohols such as myristyl alcohol, cetyl alcohol, stearyl alcohol, cetostearyl alcohol, behenyl alcohol, batyl alcohol, and isostearyl alcohol; myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, isostearic acid Acids, higher fatty acids such as isopalmitic acid; isopropyl myristate, isopropyl palmitate, cetyl octoate, oleyl oleate, octyldodecyl myristate, hexyl laurate, cetyl lactate, propylene glycol monostearate, oleyl oleate, 2- Ester oil such as hexadecyl ethylhexanoate, isononyl isononanoate, tridecyl isononanoate, castor oil, cacao oil, mink oil, avocado oil, olive oil Ester oils such as glycerides such as buoy oil, waxes such as beeswax, spermaceti, lanolin and carnauba wax; chain polysiloxanes such as dimethicone, dimethiconol, methylphenylpolysiloxane, diphenylpolysiloxane, decamethylcyclopentasiloxane, dodeca Cyclic polysiloxanes such as methylcyclopentasiloxane, silicone resins having a three-dimensional network structure, silicone rubber, amino-modified silicone, fatty acid-modified polysiloxane, alcohol-modified silicone, aliphatic-modified polysiloxane, polyether-modified silicone, epoxy-modified silicone, Silicone such as fluorine-modified silicone and alkyl-modified silicone; and hydrocarbons such as liquid paraffin, squalane, squalene, paraffin, isoparaffin, petrolatum, etc. The present invention is not limited to.

  In this invention, 1 type (s) or 2 or more types can be arbitrarily used from these oil-based components, and the compounding quantity in hair cosmetics has preferable 0.01-20 weight%.

  Cationic polymers include cationized cellulose, cationized guar gum, cationized starch, cationized dextran, cationized galactomannan, homopolymer of diallyl quaternary ammonium salt, diallyl quaternary ammonium salt / acrylamide copolymer, quaternization. Polyvinyl pyrrolidone derivatives, polyglycol polyamine condensate, vinyl imidazolinium trichloride / vinyl pyrrolidone copolymer, hydroxyethyl cellulose / dimethyl diallylammonium chloride copolymer, vinyl pyrrolidone / quaternized dimethylaminoethyl methacrylate copolymer, polyvinyl pyrrolidone / Alkylaminoacrylate / vinylcaprolactam copolymer, vinylpyrrolidone / methacrylamidopropyl trimethylammonium chloride copolymer , Alkyl acrylamide / acrylate / alkylaminoalkyl acrylamide / polyethylene glycol methacrylate copolymers, although adipic acid / dimethyl amino hydroxypropyl diethylene triamine copolymers, and the like, but is not particularly limited.

  In this invention, 1 type (s) or 2 or more types can be used arbitrarily from these cationic polymers, and the compounding quantity in hair cosmetics has preferable 0.1 to 10 weight%.

  In addition to the components described above, the hair cosmetic of the present invention includes additives usually used in the production of cosmetics, such as emulsifiers such as surfactants, viscosity modifiers, pH adjusters, chelating agents, dispersion media, and softeners. , Powders, oily ingredients, oily substances, polymers, preservatives, fragrances, stabilizers, colorants, UV absorbers, antioxidants, moisturizers, antidandruff agents, vitamins, bactericides, anti-inflammatory agents, etc. In addition, plant extracts and the like can be appropriately blended and produced according to a conventional method. The pH at that time is preferably adjusted to pH 2 to 10, particularly pH 3 to 8.

  EXAMPLES Next, although an Example demonstrates this invention still in detail, this invention is not limited to an Example. Table 1 shows damaged hair improving agents 1 to 3 synthesized by the method described in this specification. Table 2 shows the results of measurement of the hair elasticity improving effect of the damaged hair improving agent (Test Method 1) and the measurement of the effect of improving hair moisture retention (Test Method 4) in Examples 1 to 3 and Comparative Examples 1 to 4. Table 3 shows the hair cosmetics for out baths prepared in a conventional manner in Examples 4 to 9 and Comparative Examples 5 to 9, and Table 4 shows the hair cosmetics for in baths in Examples 10 to 13 and Comparative Examples 10 to 15. It was. The hair elasticity improving effect of the damaged hair improving agent and the hair cosmetic (test methods 1 and 2) was measured using a hair tension tester, and the friction reducing effect of the hair cosmetic (test method 3, evaluation of the smoothness of the hair) ) Was measured using an NRF type coefficient of friction meter, and the effect of improving hair moisture retention (test methods 4 and 5) was confirmed using a Karl Fischer moisture meter with a moisture evaporation device. The results of sensory evaluation (test method 6) of sensory evaluation of elasticity, smoothness, and no stickiness were shown. The content is% by weight.

  The test methods used in this example are as follows.

Test Method 1 (Measurement of hair elasticity improving effect of damaged hair improving agent)
A commercially available healthy black hair or bleach hair (both manufactured by Beaulux) was immersed in a pH 5 citrate buffer solution for 1 hour, and the hair tensile strength in a conditioned state was measured by a hair tension tester (KES-G1-SH manufactured by Kato Tech Co., Ltd.). ) (N = 10), and the tensile strength load value at which the hair elongation was 20% (specifically, 5 cm of hair was elongated to 6 cm) was measured. At this time, the measured value of healthy black hair is A, the measured value of bleached hair is B, and commercially available bleached hair is immersed in the solutions shown in Examples 1 to 3 and Comparative Examples 1 to 4 for 1 hour. The measurement value at the time of measurement (N = 10) was set as C, and the degree of improvement in hair elasticity was calculated by the following formula.
Increase in hair elasticity (%) = [(CB) / (AB)] × 100
The evaluation criteria for the effect of improving hair elasticity are as follows.
(Evaluation criteria)
◎: Hair elasticity improvement degree is 60% or more ○: Hair elasticity improvement degree is 30% or more and less than 60% △: Hair elasticity improvement degree is 10% or more and less than 30% ×: Hair elasticity improvement degree is less than 10%

Test Method 2 (Measurement of hair elasticity improvement effect of hair cosmetics)
Similarly to the above test method 1 (measurement of the hair elasticity improving effect of the hair elasticity improving agent), the measurement value of healthy black hair was A, and the measurement value of bleached hair was B. Further, the hair cosmetics for out bath shown in Examples 4 to 9 and Comparative Examples 5 to 9 are sprayed on a commercially available bleached hair (Bulux Co., Ltd., 20 cm × 20 g) with an atomizer and dried overnight (20 ° C., 40%). RH) or after applying 1 g of hair cosmetics for invasion shown in Examples 10-13 and Comparative Examples 10-15 to the same bleached hair, rinsing and drying overnight (same conditions as above), then a hair tension tester The measured value when the hair breakage was measured (N = 10) with KES-G1-SH (Kato Tech Co., Ltd.) was defined as D, and the degree of improvement in hair elasticity was calculated according to the following formula.
Increase in hair elasticity (%) = [(D−B) / (A−B)] × 100
The evaluation criteria for the effect of improving hair elasticity are as follows.
◎: Hair elasticity improvement is 50% or more ○: Hair elasticity improvement is 30% or more and less than 50% △: Hair elasticity improvement is 10% or more and less than 30% ×: Hair elasticity improvement is less than 10%

Test Method 3 (Measurement of Hair Friction Reduction Effect of Hair Cosmetic / Evaluation of Smoothness)
Test method 2 (Measurement of hair elasticity improvement effect of cosmetics for hair) Similarly, commercially available bleached hairs were treated with the hair cosmetics for out baths or in baths shown in Examples and Comparative Examples, and NRF type friction coefficient meter (Measured when untreated commercial bleached hair was measured with E as the measured value when the dynamic friction coefficient was measured (N = 10) with a load of 40 g, a rotational speed of 3 rpm, and a measurement time of 5 minutes using Rheological Instruments) Assuming that the value is F, the dynamic friction coefficient reduction rate was calculated by the following equation.
Dynamic friction coefficient reduction rate = E / F
The evaluation criteria for the effect of reducing hair friction (smoothness of hair) are as follows.
◎: Dynamic friction coefficient reduction rate is 0.85 or less ○: Dynamic friction coefficient reduction rate is 0.85 or more and less than 0.95 Δ: Dynamic friction coefficient reduction rate is 0.95 or more and less than 1.0 ×: Dynamic friction coefficient reduction rate is 1. 0 or more

Test Method 4 (Measurement of hair moisturizing effect of damaged hair improving agent / Evaluation of water retention ability)
Commercially available bleached hair (1 g, manufactured by Beaulux) was dipped in the solutions shown in Examples 1-3 and Comparative Examples 1-4 for 1 hour and dried overnight (20 ° C., 40% RH) to evaporate moisture. The hair moisture content was measured with a Karl Fischer moisture meter with a device (MKL-510N (KF device), ADP-511S (moisture vaporizer) manufactured by Kyoto Electronics Industry). Moreover, the evaluation criteria of the hair moisturizing improvement effect are as follows. The moisture content of untreated hair was 5.0%.
◎: Hair moisture amount is 6.0% or more ○: Hair moisture amount is 5.7% or more and less than 6.0% Δ: Hair moisture amount is 5.4% or more and less than 5.7% ×: Hair moisture amount is 5 Less than 4%

Test Method 5 (Measurement of hair moisturizing effect of hair cosmetics / Evaluation of moisture retention)
Test method 2 (Measurement of effect of improving hair elasticity of hair cosmetics) Similarly, commercially available bleached hairs were treated with the hair cosmetics for out baths or in baths shown in the examples and comparative examples, and curled with a moisture evaporation device. The moisture content of the hair was measured with a Fisher moisture meter (same as above). Moreover, the evaluation criteria of the hair moisturizing improvement effect are as follows.
◎: Hair moisture amount is 6.2% or more ○: Hair moisture amount is 5.8% or more and less than 6.2% Δ: Hair moisture amount is 5.4% or more and less than 5.8% ×: Hair moisture amount is 5 Less than 4%

Test method 6 (Evaluation of usability of hair cosmetics (no firmness, firmness, smoothness, stickiness))
Test method 3 (Measurement of hair friction reduction effect of cosmetics for hair) 10 expert panelists evaluated the "no firmness, smoothness, and stickiness" evaluation by 10 expert panelists. Went to. The evaluation criteria are as follows.
◎: When there are more than 9 people who answered good ○: When there are 6-8 people who answered good △: When there are 3-5 people who answered good ×: 2 people who answered good For people below

  As is clear from Examples 1 to 13 and Comparative Examples 1 to 15, the taurine derivative of the present invention and the hair cosmetic containing the taurine derivative have an effect of improving hair elasticity, an effect of reducing friction (evaluation of smoothness of hair), Excellent performance in moisturizing effect (evaluation of water retention) and usability (sensory evaluation: firmness, firmness, smoothness, no stickiness).

As described above, the damaged hair improving agent of the present invention and the hair cosmetic containing the damaged hair improving agent are excellent in improving elasticity and moisturizing excellent in hair damaged by daily physical and chemical actions. It is clear that the effect of improving the properties and good usability (no firmness, smoothness, and stickiness) are provided.

Claims (3)

The following general formula (1)

(In the formula, R ¹ represents a group represented by the following general formula (2), R ² represents an alkyl group having 1 to 3 carbon atoms, an alkenyl group, or a hydroxyalkyl group, and M represents a hydrogen atom, an alkali metal, or an alkaline earth. metalloid, representing at least one selected ammonium and organic Amin or al.)

(Wherein R ³ is a linear or branched alkyl group having 1 to 8 carbon atoms, an alkenyl group or a hydroxyalkyl group)
A damaged hair improving agent comprising a taurine derivative represented by: A hair cosmetic comprising the damaged hair improving agent according to claim 1. The hair cosmetic composition according to claim 2, which aims to restore the elasticity and / or moisture retention of the hair.