JP5117134B2 - Hair composition - Google Patents

Description

  The present invention relates to a hair composition, and more particularly to a hair composition having a good conditioning effect, especially slipperiness and flexibility even for damaged hair.

  Conventionally, for the purpose of removing hair stains, the hair is washed with a shampoo mainly composed of an anionic surfactant, but washing with the shampoo removes not only the hair stains but also the oil protecting the hair surface. As a result, the flexibility of the hair is lost, the hair becomes dull and uncomfortable, and the hair is easily damaged, split, and broken. Therefore, for the purpose of imparting a conditioning effect (flexibility, moist feeling, smooth feeling, slipperiness) to the hair, it is treated with a hair composition mainly composed of a quaternary ammonium salt that is a cationic surfactant, but is dried. There are cases where the slipperiness and flexibility afterwards are not sufficient, and a method of blending silicone oil or the like to improve the slipperiness after drying is known. However, when blending silicone oil or the like, the blending amount may affect the stability of the system and may be restricted by the blending amount.

  On the other hand, an amidoamine compound is blended in place of the quaternary ammonium salt, and it has excellent thickening properties (gel-forming properties) and stability over time. Patent Documents 1 and 2 propose a hair treatment composition to be applied. Further, a transparent conditioning composition comprising an amidoamine compound, an acid, a specific silicone derivative, and water is proposed in Patent Document 3, and in Patent Document 4, an amidoamine compound, an acid, a fatty alcohol, a fatty acid, or a derivative thereof Hair conditioning compositions containing oily substances and water have been proposed. Patent Document 5 proposes an amine compound having various binding species such as a hair composition containing an ester amine compound, a neutralizing agent, and a higher alcohol. However, these proposals provide a sufficiently satisfactory slip. And flexibility may not be obtained.

Furthermore, in recent years, so-called damaged hair, which has been chemically damaged by hair dyes, permanent agents and the like, and physically damaged by friction such as heat and brushing by a hair dryer after washing, has been increasing. Damaged hair has a hydrophilic surface and elutes internal proteins and lipids, giving it excellent slipperiness and flexibility from wet to dry, and after being fully satisfied It is more difficult than ever to obtain a hair composition that can provide a smooth, soft and moist feeling. For example, although the quaternary ammonium salt proposed in Patent Document 6 has improved the conditioning effect on normal hair, there is room for improvement on damaged hair.
Japanese Patent Application Laid-Open No. 5-271535 (page 1-9) Japanese Patent Application Laid-Open No. 5-271636 (page 1-9) JP-A-7-2629 (page 1-14) JP 2000-501430 (page 1-34) JP 2001-278751 A (page 1-8) JP 2004-323495 A (page 1-10)

  Therefore, the present invention is to develop a composition for hair that is excellent in slipperiness and flexibility after application to rinsing even after damaged hair, when wet until drying, and after drying.

（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）

（Ｒは直鎖又は分岐した炭素数６〜２４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）で表される基であり、残りは炭素数１〜３のアルキル基、ヒドロキシアルキル基、Ｒ^３は炭素数１〜３のアルキル基、ヒドロキシアルキル基、Ａはエチレン基および／又はプロピレン基、ｎは１以上の整数、ｍは１〜５の整数を表す。）で表される３級アミン化合物（Ａ）と（Ｂ）無機酸及び／又は有機酸を含有する毛髪用組成物が、上記要件を満たすことを見いだ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
(A) 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):

(R is a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 6 to 24 carbon atoms), the rest being an alkyl group having 1 to 3 carbon atoms, a hydroxyalkyl group, R ³ is A C1-C3 alkyl group, a hydroxyalkyl group, A represents an ethylene group and / or a propylene group, n represents an integer of 1 or more, and m represents an integer of 1 to 5. It was found that the composition for hair containing the tertiary amine compound (A) and (B) inorganic acid and / or organic acid represented by formula (1) satisfies the above requirements, and the present invention was completed.

  That is, according to the present invention, the hair composition containing the specific tertiary amine compound (A) and (B) inorganic acid and / or organic acid is rinsed from applied even to damaged hair, and is wet until dry. Gives slipperiness and flexibility after drying.

Below, the composition for hair of this invention is explained in full detail.
As the tertiary amine compound of the component (A) used in the present invention, in the general formula (1), at least one or both of R ¹ and R ² are the same in the general formula (2). Or a branched alkyl group having 6 to 24 carbon atoms, preferably 12 to 24 carbon atoms, more preferably 14 to 22 carbon atoms, an alkyl group, an alkenyl group or a hydroxyalkyl group. 3 alkyl group and hydroxyalkyl group, preferably an alkyl group having 1 to 3 carbon atoms, particularly preferably a methyl group and an ethyl group. R ³ is an alkyl group having 1 to ³ carbon atoms, preferably an alkyl group having 1 to 3 carbon atoms, particularly preferably a methyl group or an ethyl group. Furthermore, A is an ethylene group and / or a propylene group, particularly preferably an ethylene group. N is an integer of 1 or more, preferably 1 to 50, more preferably 1 to 20, and most preferably 1 to 5. m is an integer of 1-5, and 1-2 are especially preferable.

（Ｒ、Ｒ^３、Ａ、ｎは前記の意味を表し、Ｒ’は水素原子またはメチル基、Ｘはハロゲン原子である。） The method for producing the tertiary amine compound of the component (A) used in the present invention is not particularly limited, but an alkylene oxide is added to a higher alcohol (3), and an epihalohydrin is further reacted (4). The epoxy ring can be closed with an alkali (5) and reacted with a mono (di) alkylamine. (6) and (7).

(R, R ³ , A, and n are as defined above, R ′ is a hydrogen atom or a methyl group, and X is a halogen atom.)

  As a specific example of the formula (3), 0.5 to 1% KOH as a catalyst is added to a higher alcohol (1 mole) as a catalyst, dehydrated at 100 to 130 ° C., heated to 180 ° C., and 3 atm. While maintaining, ethylene oxide and / or propylene oxide (1 to 50 mol) is introduced to obtain the desired polyoxyalkylene (hereinafter abbreviated as POA) alkyl ether. Moreover, the obtained POA alkyl ether can be purified and used by distillation under reduced pressure. The POA alkyl ether can be produced by other methods, and the production method is not particularly limited.

As a specific example of the formula (4), a POA alkyl ether (1 mol) and a BF ₃ ether complex (BF ₃ pure alcohol higher alcohol to 0.5%) are charged, and epichlorohydrin 1 is heated and stirred at 50 to 90 ° C. ~ 1.5 mol) is added dropwise over 1 to 2 hours, and further aging is carried out at the same temperature for about 5 hours to obtain 1-chloro-3-POA alkoxy-2-hydroxypropane.
The obtained 1-chloro-3-POA alkoxy-2-hydroxypropane can also be purified by distillation under reduced pressure. Next, as a specific example of the formula (5), 1-chloro-3-POA alkoxy-2-hydroxypropane (1 mol) and 25% NaOH (1.5 to 2 mol) are charged at 50 to 90 ° C. Aging is carried out for 8 hours, and after stirring, the stirring is stopped and the two layers are separated. After the aqueous layer is cut, if necessary, it is further washed with warm water and dehydrated to obtain 1,2-epoxy-3-POA alkoxypropane. Further, the obtained 1,2-epoxy-3-POA alkoxypropane can be purified by distillation under reduced pressure.

  Next, as specific examples of the formulas (6) and (7), 1,2-epoxy-3-POA alkoxypropane (1 mol or 2 mol) to dialkylamine (1 to 1.5 mol) or monoalkyl An amine (0.8 to 1.2 mol) gas or aqueous solution is quickly added at room temperature to 120 ° C. and aged at the same temperature for 5 to 20 hours. In this reaction, a solvent such as a ketone such as acetone or a lower alcohol such as ethanol or isopropanol may be used. Furthermore, when excess dimethylamine or monomethylamine, a solvent, and water are used at the same temperature, they are distilled off under reduced pressure, and the desired tertiary amine compound (N- (3-POA alkoxy-2-hydroxypropyl)- N, N-dimethylamine or N, N-bis- (3-POAalkoxy-2-hydroxypropyl) -N-methylamine) is obtained. The obtained tertiary amine compound can also be purified and used by distillation under reduced pressure. The target tertiary amine compound can be produced by other methods, and the production method is not particularly limited.

  (A) As for the compounding quantity in the composition for hair in a component, 0.1-10 mass% is preferable, 0.5-8 mass% is more preferable, 1-5 mass% is especially preferable. If the blending amount of the component (A) is too small, a sufficient conditioning effect on the hair cannot be obtained, and if too large, the effect is not improved, which is not preferable.

  Specific examples of the inorganic acid and / or organic acid (B) used in the present invention include hydrochloric acid, sulfuric acid, phosphoric acid and the like, and examples of the organic acid include acetic acid, lactic acid, glycolic acid, and citric acid. , Glutamic acid, malic acid, succinic acid and the like, among which lactic acid and malic acid are particularly preferably used. In the present invention, one or more of these inorganic acids / organic acids can be arbitrarily used.

  The blending amount of the component (B) in the hair composition is preferably 0.3 to 5 moles, more preferably 0.5 to 3 moles per mole of the component (A). The hair composition is preferably adjusted to pH 2-8, particularly 3-6, from the feel of the hair and the stability of the product.

  Specific examples of the higher alcohol (C) used in the present invention include myristyl alcohol, cetyl alcohol, stearyl alcohol, cetostearyl alcohol, behenyl alcohol, batyl alcohol, and isostearyl alcohol. Among these, Cetostearyl alcohol and stearyl 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 component (C) in the hair composition is preferably 0.1 to 10% by mass, and more preferably 3 to 8% by mass. If the blending amount of the component (C) is too small, the expected effect is insufficient, and if it is too large, the feeling after use is undesirably deteriorated.

  Specific examples of the oily substance (D) used in the present invention include hydrocarbons such as liquid paraffin, petroleum jelly and squalane, ester oils such as isopropyl palmitate, cetyl octanoate and oleyl oleate, poly Nonionic surfactants such as oxyethylene stearyl ether, glyceryl trioctanoate, 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. However, it is not limited to these.

  (D) As for the compounding quantity in the composition for hair of a component, 0.1-10 mass% is preferable, and 1-3 mass% is more preferable. If the blending amount of the component (D) is too small, the expected effect becomes insufficient, and if it is too large, the stickiness such as stickiness is deteriorated.

  Furthermore, silicone oil as component (E) can be blended in the hair composition of the present invention. Specifically, methylpolysiloxane, methylphenylpolysiloxane, amino-modified silicone, fatty acid-modified polysiloxane, alcohol-modified silicone, aliphatic-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.

  (E) The compounding quantity in the composition for hair of a component is 0.1-10 mass%, Preferably it is 0.5-3 mass%. If the blending amount of the component (E) is too small, the expected effect becomes insufficient, and if it is too large, the stability deteriorates, which is not preferable.

  Furthermore, (F) polyhydric alcohol can be mix | blended with the composition for hair of this invention. Specific examples include ethylene glycol, diethylene glycol, propylene glycol, 1,3-butylene glycol, and glycerin, but are not particularly limited.

  The blending amount of the component (F) in the total amount of the hair composition is preferably 0.1 to 10% by mass, and more preferably 0.5 to 3% by mass. If the blending amount of the component (F) is too small, the expected effect becomes insufficient, and if it is too large, the stickiness such as stickiness is deteriorated.

  This invention is manufactured by mixing the above each component with a specific compounding composition. The blending composition can be determined by a blending test usually performed by a developer.

  The hair composition of the present invention further includes surfactants, medicinal agents, anti-inflammatory agents, bactericides, preservatives, ultraviolet absorbers, antioxidants, organic and inorganic powders commonly used in cosmetics, pharmaceuticals and the like. A body, a viscosity modifier, a pigment | dye, etc. can be mix | blended as needed. 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, etc., and is appropriately selected depending on the purpose of use and the required function. Polymers, fragrances and the like.

  The composition for hair of the present invention can be applied to any composition used for hair, and is a hair treatment such as a hair cleansing agent such as shampoo, hair rinse, hair conditioner, hair treatment, hair pack, hair spray, styling agent and 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. Tables 1 and 2 show tertiary amine compounds 1 to 4 synthesized by the method described in this specification (in the table, A is an abbreviation for EO when A is an ethylene group, and PO for a propylene group). Table 3 shows the quaternary ammonium salts, amidoamine compounds and esteramine compounds used. Moreover, Examples 1-15 and Comparative Examples 1-10 were prepared by a conventional method, the effect was measured, and the results are shown in Tables 5-8. Content is mass%.

  The test methods used in this example are as follows.

(Flexibility, slipperiness and comprehensive evaluation)
20 g of hair (20 cm in length) was bundled and washed with a commercially available shampoo mainly composed of an anionic surfactant. A hair rinse agent 1.0 g was uniformly applied and rinsed with running water at 40 ° C. for 30 seconds. From the time of application to (in the case of rinsing) to the wetness from towel drying to softness, slipperiness, softness after drying, and slipperiness were sensorially compared by 10 professional panelists and evaluated according to the following criteria. .
◎: If there are more than 9 people who answered good
○: When there are 6-8 people who answered good
△: 3 to 5 people answered good
×: When there are 2 or less people who answered that it is good For comprehensive evaluation, the sensory evaluation result is point system (◎: 3 points, ○: 2 points, △: 1 point, ×: 0 points) From the total, the following criteria were evaluated.
: 10 points or more
○: 7-9 points
Δ: 4-6 points
×: 3 points or less

  As is clear from Examples 1 to 13 and Comparative Examples 1 to 3, the hair composition of the present invention was rinsed from the hair to the hair, slipped, wet and soft after drying. In the evaluation, all showed excellent performance.

(Flexibility, slipperiness and comprehensive evaluation of bleached hair)
A damaged hair bundle (20 g × 20 cm) obtained by bleaching healthy black hair for 30 minutes was washed with a commercially available shampoo mainly composed of an anionic surfactant. Thereafter, 1 g of hair rinse agent was uniformly applied and rinsed with running water at 40 ° C. for 30 seconds. From the time of application to (in the case of rinsing) to the wetness from towel drying to softness, slipperiness, softness after drying, and slipperiness were sensorially compared by 10 professional panelists and evaluated according to the following criteria. .
◎: If there are more than 9 people who answered good
○: When there are 6-8 people who answered good
△: 3 to 5 people answered good
×: When two or less people answered that it was good

Moreover, about the comprehensive evaluation, the result of sensory evaluation was made into a point system ((double-circle): 3 point, (circle): 2 point, (triangle | delta): 1 point, x: 0 point), and it evaluated by the following reference | standard from the sum total.
: 10 points or more
○: 7-9 points
Δ: 4-6 points
×: 3 points or less

As described above, it is clear that the hair composition of the present invention has an excellent conditioning effect even on damaged hair, and particularly provides slipperiness and flexibility when wet and after drying.

Claims (5)

(A) 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):

(R is a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 6 to 24 carbon atoms), the rest being an alkyl group having 1 to 3 carbon atoms, a hydroxyalkyl group, R ³ is A C1-C3 alkyl group, a hydroxyalkyl group, A represents an ethylene group and / or a propylene group, n represents an integer of 1 or more, and m represents an integer of 1 to 5. The composition for hair containing the tertiary amine compound represented by this, and (B) inorganic acid and / or organic acid. 2. A composition comprising 0.1 to 10% by mass of component (A) and 0.3 to 5 moles of component (B) relative to 1 mol of component (A) in the total amount of the hair composition. The composition for hair described in 1. Furthermore, the composition for hair of Claim 1 or 2 formed by mix | blending 0.1-10 mass% of (C) higher alcohol and 0.1-10 mass% of (D) oil-based components. Furthermore, the composition for hair of any one of Claims 1-3 formed by mix | blending 0.1-10 mass% of (E) silicone oil. Furthermore, the composition for hair of any one of Claims 1-4 formed by mix | blending 0.1-10 mass% of (F) polyhydric alcohol.