JP6209401B2 - Hair elasticity improver - Google Patents

Description

  The present invention relates to a hair elasticity improving agent, and more particularly, a hair elasticity improving agent for improving the elasticity of hair damaged by daily physical and chemical action, and the hair elasticity improving agent. The present invention relates to a hair cosmetic composition that has an effect of improving the elasticity 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 and cause the loss of elasticity, elasticity, firmness and smoothness of the hair. It has become. 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. In addition, Patent Document 3 proposes a hair cosmetic that gives an excellent oily feeling to hair by using an arginine derivative as an active ingredient, but the feeling of use such as stickiness is not sufficient.

JP 2001-81013 A (page 1-14) JP 2004-346040 A (page 1-14) JP-A-2-764 (page 1-8)

  The present invention relates to a hair elasticity improver, and more particularly a hair elasticity improver for improving the elasticity of hair damaged by daily physical and chemical action, and a hair elasticity improver. It is an object of the present invention to provide a hair cosmetic that contains an effect of improving the elasticity of hair and imparts good usability (harshness, firmness, smoothness, no stickiness) to hair.

（式中、Ｒ_１、Ｒ_２の少なくとも一方／又は両方は、下記一般式（２）で表され、残りは水素原子を表す。）

（式中、Ｒは直鎖又は分岐した炭素数１〜４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す。）
で表されるアルギニン誘導体からなる毛髪弾力性向上剤に優れた毛髪弾力性改善効果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, at least one or both of R ₁ and R ₂ are represented by the following general formula (2), and the remainder represents a hydrogen atom.)

(In the formula, R represents a linear or branched alkyl group having 1 to 4 carbon atoms, an alkenyl group, or a hydroxyalkyl group.)
The present invention was completed by finding an excellent hair elasticity improving effect for a hair elasticity improving agent comprising an arginine derivative represented by the formula:

  That is, the present invention has the effect that the hair elasticity improver comprising the arginine derivative represented by the general formula (1) and the hair cosmetic containing the hair elasticity improver improve the elasticity of the hair. In addition, the hair can be given good usability (harshness, firmness, smoothness, no stickiness).

（式中、Ｒは直鎖又は分岐した炭素数１〜４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す。） Below, the hair elasticity improving agent of this invention and the hair cosmetics containing this hair elasticity improving agent are explained in full detail.
Although there is no limitation in particular as a manufacturing method of the arginine derivative which is a hair elasticity improving agent of this invention, it can manufacture by making arginine and glycidyl ether react generally as shown by the following Formula.

(In the formula, R represents a linear or branched alkyl group having 1 to 4 carbon atoms, an alkenyl group, or a hydroxyalkyl group.)

  As a specific production method of the arginine derivative represented above, in an aqueous system and / or a solvent system or an aqueous solvent mixed system solvent (in the case of a mixed system solvent) so that the active ingredient of the arginine derivative is 10 to 90%. Is dissolved in water: solvent = 5: 95 to 95: 5) and 1 mol of arginine is dissolved at room temperature to 95 ° C., or 0.8 to 1.2 or 1.8 to 2.2 mol of glycidyl ether is added all at once or dropwise. Etc., and matured at 50 to 95 ° C. until the reaction is completed. Glycidyl ether is more preferably 0.9 to 1 or 1.9 to 2 mol, an aging temperature of 50 to 90 ° C., and an aging time of 1 to 10 hours with respect to 1 mol of arginine.

  As the glycidyl ether used in the production of the arginine derivative, a glycidyl ether having an alkyl group having 1 to 4 carbon atoms, an alkenyl group, or a hydroxyalkyl group, specifically, methyl glycidyl ether, ethyl glycidyl ether, n-propyl glycidyl ether, Examples thereof include i-propyl glycidyl ether, n-butyl glycidyl ether, and i-butyl glycidyl ether, which are commercially available as “Epogosei” series manufactured by Yokkaichi Gosei Co., Ltd., “Epiol” series manufactured by NOF Corporation. Moreover, although allyl glycidyl ether, hydroxybutyl glycidyl ether, etc. are mentioned, it does not specifically limit to these.

  Arginine 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 arginine derivative in the reaction system is 20 to 50%, in an aqueous system and / or a solvent system or an aqueous solvent mixed system 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 arginine 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 arginine derivative of the present invention can be produced by other methods, and the production method is not particularly limited.

  The blending amount of the hair elasticity 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 the blending is less than 0.01%, the effect of improving hair elasticity is insufficient, and even if blending more than 20%, the usability becomes sticky, which is not preferable.

  The hair cosmetic composition containing the hair elasticity improving agent of the present invention is applicable to any composition used for hair, and is in the form of a transparent liquid, gel, cream, on milk, mousse, etc. Hair such as shampoos, hair rinses, hair conditioners, hair treatments, hair packs, hair sprays, styling agents, hair color agents, bleach agents, permanent wave agents, hair straighteners, etc. A treatment agent and the like can be mentioned, and any of the usage forms such as those which are applied to the hair and applied to the hair and then rinsed and those which are not washed off are suitably used.

  In the hair cosmetic composition containing the hair elasticity improver of the present invention, in addition to the hair elasticity improver, a cationic surfactant, an oil component, a cationic polymer and the like can be blended as necessary.

  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 Midpropyldimethylamine, palmitamidopropyldimethylamine, stearamidepropyldimethylamine, oleamide Lopyldimethylamine, isostearamidpropyldimethylamine, araquinamidepropyldimethylamine, behenamidopropyldimethylamine, stearamideethyldiethylamine, araquinamidoethyldiethylamine, behenamidoethyldiethylamine, laurylPGdimethylamine, myristyl PG Examples include dimethylamine, 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 octanoate, 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 hair elasticity improvers 1 to 4 synthesized by the method described in this specification. Table 2 shows the results (test method 1) of the results of measuring the hair elasticity of the hair elasticity improvers (Examples 1 to 4 and Comparative Examples 1 to 4). Hair cosmetics (Examples 5 to 13 and Comparative Examples 5 to 9) and test results thereof, and Table 4 show hair cosmetics for in-baths (Examples 14 to 19 and Comparative Examples 10 to 15) and test results thereof. The hair elasticity improving agent and the measurement of the hair elasticity improving effect of the hair cosmetic (test methods 1 and 2) were confirmed using a hair tension tester, and the friction reducing effect of the hair cosmetic (test method 3, smooth hair) ) And wear reduction effect (Test Method 4, evaluation of prevention of hair breakage due to friction such as brushing) was confirmed using an NRF type friction coefficient meter, and the sense of firmness and firmness from sensory evaluation (Test Method 5) The results of sensory evaluation of 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 hair elasticity improving agent)
Commercially available healthy black hair or bleached hair (both manufactured by Beaulux) was immersed in a pH 5 citrate buffer solution for 1 hour, dried overnight (20 ° C., 40% RH), and then a hair tension tester (KES manufactured by Kato Tech Co., Ltd.). The measurement value of healthy black hair when the hair breakage measurement (N = 10) was performed with -G1-SH) was A, and the measurement value of bleached hair was B. Moreover, after immersing a commercially available bleach hair in the solutions shown in Examples 1 to 4 and Comparative Examples 1 to 4 for 1 hour, the hair was dried overnight (20 ° C., 40% RH), and the hair breakage measurement was similarly performed (N = 10). The measured value when the hair was taken was defined as C, and the degree of improvement in hair elasticity was calculated according to 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 40% or more ○: Hair elasticity improvement degree is 25% or more and less than 40% △: Hair elasticity improvement degree is 10% or more and less than 25% ×: 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. In addition, the hair cosmetics for out bath shown in Examples 5 to 13 and Comparative Examples 5 to 9 are sprayed on a commercially available bleached hair (Bulux Co., Ltd., 20 cm × 20 g) with an atomizer, dried overnight, or Examples 14-19, 1 g of hair cosmetic for invasion shown in Comparative Examples 10-15 was applied to the same bleached hair, rinsed, dried overnight (same conditions as described above), and then a hair tension tester (KES-Tech, manufactured by Kato Tech Co., Ltd.). The measured value when the hair breakage was measured with G1-SH) (N = 10) was defined as D, and the degree of improvement in hair elasticity was calculated according to the following equation.
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 wear reduction effect of hair cosmetics / Evaluation of hair breakage prevention)
Until the above-mentioned test method 3 (measurement of hair friction reducing effect of hair cosmetics) is performed using a NRF friction coefficient meter (manufactured by Rheological Instruments) to break the bleached hair treated under the load conditions of a load of 100 g and a rotation speed of 200 rpm. Was measured (N = 10), and the effect of reducing hair wear (prevention of hair breakage due to friction such as brushing) was evaluated. The evaluation criteria are as follows.
◎: Break time 600 seconds or more ○: Break time 480 seconds or more and less than 600 seconds Δ: Break time 360 seconds or more and less than 480 seconds X: Break time 360 seconds or less

Test Method 5 (Evaluation of Usability of Hair Cosmetics (No firmness, firmness, smoothness, stickiness))
Test method 3 (Measurement of hair friction reduction effect of hair cosmetics) Sensitive evaluation of bleached hairs treated in the same manner as above by 10 expert panelists for “feeling of firmness, smoothness and smoothness” went. 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 19 and Comparative Examples 1 to 15, the hair cosmetic containing the arginine derivative of the present invention has a hair elasticity improving effect, a friction reducing effect (smooth hair evaluation), and a wear reducing effect. (Evaluation of preventing hair breakage due to friction such as brushing) and usability (sensory evaluation: firmness, firmness, smoothness, no stickiness) showed excellent performance.

  As described above, the hair elasticity improver of the present invention and the hair cosmetic containing the hair elasticity improver are excellent in improving elasticity to hair damaged by daily physical and chemical actions. It is clear that it gives good usability (harshness, firmness, smoothness, no stickiness).

Claims (3)

A hair elasticity improving agent comprising an arginine derivative represented by the following general formula (1).

(In the formula, at least one or both of R ₁ and R ₂ are represented by the following general formula (2), and the remainder represents a hydrogen atom.)

(In the formula, R represents a linear or branched alkyl group having 1 to 4 carbon atoms.) A hair cosmetic containing the hair elasticity improving agent according to claim 1. The hair cosmetic composition according to claim 2, which has an effect of restoring the elasticity of the hair.