JP2012077023A - Hair cosmetic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a hair cosmetic having ability for hydrophobizing the surface of the hair, imparting good feeling (smoothness, flexibility and nonsticky feeling) to the hair, and having effects for imparting moist feeling to the hair (especially damaged hair) by heightening the retentivity of water content.SOLUTION: The hair cosmetic contains (A) a cationic surfactant represented by general formula (1) (wherein, Ris 7-23C linear or branched alkyl, alkenyl or hydroxyalkyl; Ris 1-6C linear or branched alkyl, alkenyl or hydroxyalkyl; Rto Rare each 1-5C alkyl or hydroxyalkyl; n is an integer of 1-5; and Xis a monovalent anion).

Description

  The present invention relates to a hair cosmetic, and more particularly, has a hydrophobizing ability on the hair surface, gives the hair a good feel (smoothness, flexibility, no stickiness), and hair (particularly damaged hair). It is related with the hair cosmetics excellent in the effect which raises the water | moisture-content retention power and provides a moist feeling.

  In recent years, as coloring and perms have become commonplace, the hydrophobic film on the hair surface has been lost, resulting in hydrophilization, and the smoothness and flexibility of the hair has become insufficient, increasing the number of consumers who feel a sense of softness. There is a growing need to improve hair damage. In addition, even during shampooing, hair may be further damaged due to friction during use of the shampoo.

  Hair surface modification is effective for improving the feel of damaged hair, and the use of cationic surfactants and silicone compounds is known. Patent Document 1 discloses quaternary ammonium salts of hydroxylanolin fatty acids, non-hydroxylanolin. A cosmetic composition comprising a quaternary ammonium salt of a fatty acid, Patent Document 2 discloses a cosmetic composition containing a quaternary ammonium salt of a branched fatty acid as an essential component, and Patent Document 3 discloses L-theanine and quaternary ammonium. A hair cosmetic composition comprising an alkyl sulfate type cationic surfactant has been proposed. However, although these proposals are excellent in the repair effect of hair, the hair feel (smoothness, flexibility, lack of stickiness) is insufficient, and the effect of enhancing moisture retention of the hair and imparting a moisturizing effect is It was not satisfactory.

Further, although a bisamide cation (Patent Document 4) and a biscation (Patent Document 5) are blended as quaternary ammonium salts, a hair composition excellent in hair conditioning effects (slipperiness and smoothness) has also been proposed. In these proposals, it cannot be said that a sufficient touch (smoothness, flexibility, lack of stickiness) is given to hair after drying, and the hair surface repair effect is not mentioned.
JP-A-9-143135 (page 1-14) JP-A-10-139620 (page 1-15) JP 2006-104162 A (page 1-13) JP2003-113045 (page 1-7) JP 2006-199636 A (page 1-9)

  The present invention relates to a hair cosmetic, and more particularly, has a hydrophobizing ability on the hair surface, gives the hair a good feel (smoothness, flexibility, no stickiness), and hair (particularly damaged hair). It is in providing the hair cosmetics excellent in the effect which raises the water | moisture-content holding power and provides a moist feeling.

  As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that a hair cosmetic containing a specific cationic surfactant has a hydrophobizing ability on the hair surface and has a good feel (smoothness) on the hair. The present invention has been completed by finding that it imparts a moist feeling by giving the hair (particularly damaged hair) moisture retention and imparting a moist feeling.

（式中、Ｒ_１は炭素数７〜２３の直鎖又は分岐したアルキル基、アルケニル基もしくはヒドロキシアルキル基を示し、Ｒ_２は炭素数１〜６の直鎖又は分岐したアルキル基、アルケニル基もしくはヒドロキシアルキル基を示し、Ｒ_３〜Ｒ_６は炭素数１〜５のアルキル基、ヒドロキシアルキル基、ｎは１〜５の整数、Ｘ^-は一価のアニオンを示す。）で表されるカチオン界面活性剤を含有する毛髪化粧料に関する。 That is, the present invention provides (A) the following general formula (1)

(In the formula, R ₁ represents a linear or branched alkyl group having 7 to 23 carbon atoms, an alkenyl group or a hydroxyalkyl group, and R ₂ represents a linear or branched alkyl group having 1 to 6 carbon atoms, an alkenyl group or R represents a hydroxyalkyl group, R _{3 to} R ₆ represent an alkyl group having 1 to 5 carbon atoms, a hydroxyalkyl group, n represents an integer of 1 to 5, and X ⁻ represents a monovalent anion. The present invention relates to a hair cosmetic containing an active agent.

Below, the composition for hair of this invention is explained in full detail.
As the cationic surfactant of the component (A) used in the present invention, in the general formula (1), R ₁ represents a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 7 to 23 carbon atoms. An alkyl group or alkenyl group having 15 to 21 carbon atoms is preferred. R ₂ represents a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 1 to 6 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms. R _{3 to} R _{6 each} represent an alkyl group having 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms, a hydroxyalkyl group, more preferably a methyl group, and examples of X ⁻ include a halide ion and a sulfate ion. In particular, chloride ions are preferred.

  The cationic surfactant (target product) represented by the general formula (1) can be produced, for example, according to the following reaction formulas 1 to 4 after synthesizing an intermediate amidoamine compound.

＜反応式１＞

＜反応式２＞

＜反応式３＞

＜反応式４＞

（各反応式中のＲ_１〜Ｒ_６、Ｘ⁻は前記一般式（１）のものと同じ。） <Intermediate: Synthesis of Amidoamine>

<Reaction Formula 1>

<Reaction Formula 2>

<Reaction Formula 3>

<Reaction Formula 4>

(R _{1 to} R ₆ and X ^{− in} each reaction formula are the same as those in the general formula (1).)

  In the synthesis of the intermediate amidoamine, a derivative such as fatty acid or fatty acid lower alkyl ester and a dialkylaminoalkylamine (diamine) are subjected to a condensation reaction, and then unreacted diamine is distilled off by a method such as reduced pressure or nitrogen blowing. By doing so, fatty acid amide alkyldialkylamine (amidoamine) is obtained.

  As a specific method for synthesizing amidoamine, 0.9 to 2.0 mol of diamine is added dropwise at 80 to 220 ° C. with respect to 1 mol of fatty acid or a derivative thereof, and the same until the reaction is completed. Ripens at temperature. When the reaction is completed, excess diamine is distilled off under reduced pressure at the same temperature to obtain amidoamine. During the reaction, it is preferable to introduce an inert gas such as nitrogen and quickly distill the reaction distillate out of the system. When a fatty acid derivative is used, the reaction can proceed more rapidly by using an alkali catalyst such as sodium methylate.

  Examples of the diamine used here include dimethylaminoethylamine, dimethylaminopropylamine, diethylaminoethylamine, and diethylaminopropylamine. Among these, dimethylaminopropylamine and diethylaminoethylamine are particularly preferably used. The reaction molar ratio of diamine is more preferably 1.0 to 1.5 mol, and the reaction temperature is more preferably 150 to 200 ° C.

  Next, in order to obtain the target cationic surfactant, in the reaction formulas 1 and 2, a tertiary amine is used in a single solvent system or a mixed solvent system (hereinafter referred to as a reaction solvent) such as water and / or a lower alcohol or a polyhydric alcohol. Alternatively, an epihalohydrin is reacted with amidoamine, and a tertiary amine salt or an amidoamine salt (hereinafter referred to as a tertiary amine neutralized salt or amidoamine neutralized salt) obtained by neutralizing a tertiary amine with an organic acid or inorganic acid in a reaction solvent is added dropwise. To obtain the desired cationic surfactant. In the reaction formulas 3 and 4, the tertiary amine neutralized salt or the amidoamine neutralized salt in the reaction solvent is reacted with the epihalohydrin, and separately in the reaction solvent. A tertiary amine or amidoamine is dissolved and added by a method such as dropwise addition to obtain a target cationic surfactant.

  As a specific method for synthesizing the cationic surfactant (A), a mixed solvent of water / lower alcohol or polyhydric alcohol = 10 to 90 / 90-10 so that the active ingredient of the cationic surfactant is 10 to 90%. (Reaction Formula 1) Tertiary amine or (Reaction Formula 2) Amidoamine or (Reaction Formula 3) Tertiary amine neutralized salt or (Reaction Formula 4) 1 mol of amidoamine neutralized salt is dissolved at 30 to 95 ° C. Then, 1 to 2 mol of epihalohydrin is added dropwise, and the mixture is aged at the same temperature until the reaction is completed. Next, (reaction formula 1) amidoamine neutralized salt or (reaction formula 2) tertiary amine neutralized salt, or (reaction formula 3) amidoamine or (reaction formula 4) tertiary amine 1 adjusted in a reaction solvent. It can be added by a method such as dropwise addition of 2 mol, and ripened at the same temperature until the reaction is completed to obtain the desired cationic surfactant. Here, epihalohydrin and (reaction formula 1) amidoamine neutralization salt or (reaction equation 2) tertiary amine neutralization salt, or (reaction equation 3) amidoamine or (reaction equation 4) tertiary amine added later are 1 to 1.2 moles per 1 mole of 1) tertiary amine or (reaction formula 2) amidoamine, or (reaction formula 3) tertiary amine neutralization salt or (reaction formula 4) amidoamine neutralization salt A temperature of 50 to 85 ° C. and an aging time of 5 to 20 hours are more preferable.

In addition, when R ₂ , R ₅ , and R ₆ are all methyl groups in Reaction Formula 1 or Reaction Formula 3, commercially available (Reaction Formula 1) glycidyltrimethylammonium chloride (GTA / “Cation Master G” manufactured by Yokkaichi Chemical Co., Ltd.) “SY-GTA80” manufactured by Sakamoto Yakuhin Co., Ltd.) or (Reaction Formula 3) 3-chloro-2-hydroxypropyltrimethylammonium chloride (CTA / “Cation Master C” manufactured by Yokkaichi Chemical Co., Ltd.) can also be used ( Reaction method 1) Amidoamine neutralized salt, or (Reaction equation 3) (Reaction equation 1) GTA or (Reaction equation 3) CTA 1-2 mol is added dropwise at 30-95 ° C. Cationic surfactants can also be obtained, GTA (Reaction Formula 1), or CTA (Reaction Formula 3) is an amidoamine neutralized salt (Reaction Formula 1), There are 1 to 1.2 moles to amidoamine (Scheme 3), dropwise, aging temperature 50 to 85 ° C., the aging time from 5 to 20 hours is more preferable.

  Examples of the lower alcohol or polyhydric alcohol used as the reaction solvent include ethanol, 2-propanol, propylene glycol, dipropylene glycol, 1,3-butylene glycol and the like. Among these, ethanol, 2-propanol, propylene glycol Dipropylene glycol is particularly preferably used. The active ingredient of the cationic surfactant in the reaction system is preferably 40 to 60%, and the mixing ratio of water / reaction solvent is more preferably water / reaction solvent = 20-80 / 80-20.

  The cationic surfactant obtained by each method can be used as it is as a compounding component of the product of the present invention, but can also be purified and used by a conventional purification method such as column purification using silica gel or the like. The cationic surfactant of the present invention can be produced by other methods, and the production method is not particularly limited.

  (A) 0.01-20 mass% is preferable, as for the compounding quantity in the hair cosmetics of a component, 0.1-10 mass% is more preferable, and 0.5-5 mass% is especially preferable. If the blending amount of the component (A) is too small, sufficient hair surface hydrophobicity and hair feel (smoothness, flexibility, moisturizing feeling with increased moisture retention) cannot be obtained. It may be sticky or heavy, which is not preferable.

  The hair cosmetic composition of the present invention may further contain an oil component (B). Examples of the oil component include higher alcohols, ester oils, silicones, hydrocarbons and the like, and suitable ones may be appropriately selected from these.

  The higher alcohol is a higher alcohol having a linear or branched alkyl group or alkenyl group, preferably a higher alcohol having a linear or branched alkyl group or alkenyl group having 12 to 26 carbon atoms. Examples include myristyl alcohol, cetyl alcohol, stearyl alcohol, cetostearyl alcohol, behenyl alcohol, batyl alcohol, and isostearyl alcohol. Among these, cetyl alcohol, stearyl alcohol, and behenyl alcohol are particularly preferably used. In the present invention, one or more of these higher alcohols can be arbitrarily used.

  The blending amount of the higher alcohol in the hair cosmetic composition is preferably 1 to 10% by weight, particularly 3 to 8% by weight. If it is less than 1% by weight, the expected effect is insufficient, and even if it exceeds 10% by weight, the feeling after use is unfavorable.

  Examples of ester oils include ester oils having a total carbon number of 8 to 48, specifically isopropyl myristate, isopropyl palmitate, cetyl octoate, oleyl oleate, etc., and isopropyl myristate and isopropyl palmitate are particularly preferred. Although used, it is not particularly limited to these.

  As silicone, dimethylpolysiloxane, methylphenylpolysiloxane, amino-modified silicone, fatty acid-modified polysiloxane, alcohol-modified silicone, aliphatic alcohol-modified polysiloxane, polyether-modified silicone, epoxy-modified silicone, fluorine-modified silicone, cyclic silicone, alkyl Although modified silicone etc. are mentioned, it is not specifically limited to these.

  Examples of hydrocarbons include liquid paraffin, squalane, squalene, paraffin, isoparaffin, petrolatum and the like, but are not particularly limited thereto.

  In the hair cosmetic composition of the present invention, a cationic surfactant other than the cationic surfactant of the present invention can be blended within a range that does not impair the effects of the present invention. Examples of such cationic surfactants include quaternary ammonium salts and tertiary amine salts. Specifically, cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, aralkyltrimethylammonium chloride, behenyltrimethyl chloride. Quaternary ammonium salts such as ammonium; palmitamidopropyldimethylamine, stearamidepropyldimethylamine, araquinamidepropyldimethylamine, behenamidopropyldimethylamine, stearamideethyldiethylamine, araquinamidoethyldiethylamine, behenamide Examples include organic acid salts of amidoamines such as ethyldiethylamine.

  The hair cosmetic composition of the present invention can also contain a hair repair component. Examples of such components include amino acids or amino acid derivatives, vitamins, sphingosines, ceramides, and the like. Specifically, arginine, lysine, histidine, proline, cysteine, methionine, serine, threonine, tyrosine, glutamine Amino acid derivatives such as trimethylglycine, acylated amino acids, acylalkylamino acids, peptides such as dipeptides and tripeptides; tocopherol acetate, ascorbic acid, vitamin B1, vitamin B5, vitamin D, vitamin A, nicotinic acid Vitamins such as amide, panthenol, pantothenyl ethyl ether; sphingosines such as sphingomyelin, cerebroside, ganglioside; ceramide 1, ceramide 2, ceramide 3, ceramide 4, cerami 5, ceramide such as pseudoceramides manufactured by natural ceramides and chemical synthesis of ceramide 6, and the like.

  In addition to the oil component, the hair cosmetic of the present invention further includes polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,3-butylene glycol, glycerin, polyoxyethylene stearyl ether, glyceryl trioctanoate, Usually used for non-ionic surfactants such as polyglycerin fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, animal and vegetable oils such as camellia oil, olive oil, avocado oil, jojoba oil, etc. Surfactants, medicinal agents, anti-inflammatory agents, bactericides, preservatives, ultraviolet absorbers, antioxidants, organic and inorganic powders, viscosity modifiers, pigments, etc. can be blended as necessary. . Moreover, a solid oil part and a semi-solid oil part can be added in the range which does not impair the effect of invention. Specifically, it may be one that is usually used in cosmetics and the like, and is appropriately selected depending on the purpose of use and required function. For example, humectant, polysaccharide cationized cellulose, cationized guar gum, diallyldimethylammonium polymer, etc. Cationic polymers, fragrances, pH adjusters, and the like.

  The hair cosmetic composition of the present invention can be applied to any composition used for hair, and is a hair treatment agent such as a shampoo or other hair cleaning agent, hair rinse, hair conditioner, hair treatment, hair pack, hair spray, styling agent, or the like. The hair composition of the present invention is a hair rinse that is used after rinsing after application. It is particularly suitable for hair conditioners and hair treatments.

  EXAMPLES Next, although an Example demonstrates this invention still in detail, this invention is not limited to an Example. Table 1 shows cationic surfactants 1 to 6 synthesized by the method described in this specification, and Table 2 shows cationic surfactants 1 to 3 used for comparison. Moreover, the hair cosmetics of Examples 1-9 and Comparative Examples 1-6 were prepared by the conventional method. The effect of applying hair cosmetics is determined by checking the presence or absence of an improvement in the moisture retention capacity of the hair by measuring the moisture content of the hair (Test Method 1) and by measuring the contact angle of the hair surface (Test Method 2). The presence or absence of improved chemical ability was confirmed and used as an index of damage repair effect. Moreover, smoothness, a softness | flexibility, the absence of a sticky feeling, and a moist feeling were evaluated from sensory evaluation (test method 3), and the result was shown to Tables 3-4. Content is mass%.

  The test methods used in this example are as follows.

Test Method 1 (Measurement of hair moisture)
<Pretreatment>
After applying the hair cosmetic (0.1 g) prepared on commercial bleached hair (1 g) washed with 10% LES aqueous solution, rinsing with running water, and drying the hair overnight (20 ° C., 40% RH) Tests were performed.
<Moisture measurement>
The moisture measurement was performed by measuring the moisture content of the hair with a Karl Fischer moisture meter with a moisture evaporation device (KF device: MKL-510N, moisture vaporizer: ADP-511S) manufactured by Kyoto Electronics Industry. In addition, a measurement result shows the relative value when the moisture content of the hair at the time of un-processing is set to 1, and shows that there is so much moisture content that a numerical value is large.

Test method 2 (contact angle measurement)
<Pretreatment>
Hair subjected to the same treatment as in Test Method 1 (measurement of water content of hair) was used.
<Contact angle measurement>
The contact angle was measured using a portable contact angle meter (PG-3) manufactured by Matsubo, and 2 μl of water droplets were dropped on the treated hair to measure the contact angle. Untreated bleached hair was 94 ° and healthy hair was 156 °. The judgment criteria are as follows.
A: Contact angle is 150 ° or more
○: Contact angle of 135 to less than 150 °
Δ: Contact angle of 120 or more and less than 135 °
×: Contact angle is less than 120 °

Test method 3 (sensory evaluation)
<Pretreatment>
The hair cosmetic (1 g) prepared was applied to commercially available bleached hair (10 g) washed with a 10% LES aqueous solution, rinsed with running water, and then tested using hair sufficiently dried with a dryer.
<Sensory test>
The evaluation of “smoothness”, “flexibility”, “no stickiness”, and “moistness” were sensuously evaluated by 20 expert panelists. The judgment criteria are as follows.
◎: When more than 16 test subjects answered good
○: When there are 11 to 15 test subjects who answered good
△: When 6 to 10 test subjects answered good
×: When the number of test subjects who answered good is 5 or less

  As is clear from Examples 1 to 9 and Comparative Examples 1 to 6, the hair cosmetic composition of the present invention has an effect of improving the hydrophobizing ability and moisture retention of the hair surface, and has a good feel (smoothness, The performance was excellent in the effect of imparting flexibility, no stickiness, and moist feeling.

As described above, the hair cosmetic composition of the present invention has the ability to hydrophobize the surface of the hair, gives the hair a good feel (smoothness, flexibility, no stickiness), and hair (particularly damaged hair). It is clear that the moisture retention power of the water is increased to give a moist feeling.

Claims (3)

(A) The following general formula (1)

(In the formula, R ₁ represents a linear or branched alkyl group having 7 to 23 carbon atoms, an alkenyl group or a hydroxyalkyl group, and R ₂ represents a linear or branched alkyl group having 1 to 6 carbon atoms, an alkenyl group or R represents a hydroxyalkyl group, R _{3 to} R ₆ represent an alkyl group having 1 to 5 carbon atoms, a hydroxyalkyl group, n represents an integer of 1 to 5, and X ⁻ represents a monovalent anion. Hair cosmetic containing an active agent. The hair cosmetic according to claim 1, further comprising (B) an oily component. The hair cosmetic composition according to claim 2, wherein the oil component (B) is one or more selected from higher alcohols, silicones and / or silicone derivatives, and ester oils.