JP4943980B2 - Hair composition - Google Patents

Description

  The present invention relates to a composition for hair, and more particularly, can impart good slipperiness and flexibility to a damaged hair from the time of being wet to the time of drying. It is related with the composition for hair excellent in a feeling.

  Washing the hair with shampoo removes not only the hair stains but also the oil that protects the hair surface, losing the flexibility of the hair, resulting in dull and uncomfortable hair, and damage to the hair , Split ends and cut hairs are likely to occur. Therefore, for the purpose of imparting conditioning effects (flexibility, slipperiness, smoothness, moistness) to the hair, it is treated with a hair composition mainly composed of a quaternary ammonium salt, which is a cationic surfactant, but is dried. There are cases where the slipperiness, flexibility and moist feeling 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.

Therefore, 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, giving the hair enough smoothness, moistness, flexibility, smoothness, and a light finish. 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 a hair composition containing an ester amine compound, a neutralizing agent and a higher alcohol, and Patent Document 6 contains a hydroxy ether amine compound, a neutralizing agent, a higher alcohol and an oily substance. Amine compounds having various binding species such as hair compositions have been proposed. However, with these proposals, it is possible to dry the hair from a sufficiently satisfactory wet condition for damaged hair caused by chemical damage such as hair dyes and permanents, and physical damage caused by friction such as heat or brushing after hair washing. A hair composition that imparts good slipperiness and flexibility until later and is excellent in slipperiness, flexibility, and feeling of unity after drying has not been obtained.
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)

  Damaged hair is more difficult than ever to obtain a hair composition that provides a sufficient conditioning effect because the hair surface is hydrophilized and internal proteins and lipids are eluted. The present invention is to develop a hair composition that imparts good slipperiness and flexibility to damaged hair from wet to after drying, and in particular, excellent slipperiness, flexibility, and feeling of tightness after drying. is there.

（Ｒは直鎖又は分岐した炭素数４〜２４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、Ｒ^１〜Ｒ^４は同一又は異なる炭素数１〜３のアルキル基、ヒドロキシアルキル基、ｎ、ｐは０又は１、ｍ、ｑは１〜５の整数を表す。）、（Ｂ）無機酸及び／又は有機酸を含有することにより、上記要件を満たす毛髪用組成物が得られることを見出し、本発明を完成させた。 As a result of intensive studies to solve the above problems, the present inventors have (A) any one or both of the tertiary amine compounds represented by the following general formulas (1) and (2).

(R is a linear or branched alkyl group having 4 to 24 carbon atoms, an alkenyl group, or a hydroxyalkyl group, and R ^{1 to} R ⁴ are the same or different alkyl groups having 1 to 3 carbon atoms, hydroxyalkyl groups, n , P represents 0 or 1, m, q represents an integer of 1 to 5.) (B) By containing an inorganic acid and / or an organic acid, a hair composition satisfying the above requirements can be obtained. The headline and the present invention were completed.

  That is, according to the present invention, the hair composition containing (A) the above-mentioned tertiary amine compound and (B) an organic acid and / or an inorganic acid is good for damaged hair from wet to dry. It can provide slipperiness and flexibility, and in particular, can provide slipperiness, flexibility, and feeling of grouping after drying.

  Below, the composition for hair of this invention is explained in full detail.

In the general formula (1) relating to the (A) tertiary amine compound used in the present invention, R is a linear or branched carbon number of 8 to 24, preferably 12 to 24, and more preferably carbon number. 14 to 22 alkyl group, alkenyl group or hydroxyalkyl group, R ^{1 to} R ⁴ are the same or different alkyl groups having 1 to 3 carbon atoms, hydroxyalkyl group, particularly preferably methyl group, hydroxyethyl group, n, p is 0 or 1, m, and q is an integer of 1 to 5, but 1 to 3 is particularly preferable.

（Ｒ、Ｒ^１〜Ｒ^４、ｎ、ｍ、ｐ、ｑは一般式（１）におけるものと同じの意味を表し、Ｘはハロゲン原子である。） The production method of the (A) tertiary amine compound used in the present invention is not particularly limited, but an alkyl produced by adding an epihalohydrin to a higher alcohol (3) and then ring-closing the epoxy with an alkali (4). Can be produced by the method shown in (5) or (6) using glycidyl ether (1 mol or 2 mol) or 1,2-epoxyalkane (1 mol or 2 mol) and reacting this with diamine. It is.

(R, R ^{1 to} R ⁴ , n, m, p, and q have the same meaning as in general formula (1), and X is a halogen atom.)

Formula (3) is prepared by adding higher alcohol (1 mole) and BF ₃ ether complex (BF ₃ pure alcohol to higher alcohol 0.5%) and heating and stirring at 50 to 90 ° C. with epichlorohydrin 1 to 1.5 mole). The solution is added dropwise over 1 to 2 hours, and further aged at the same temperature for about 5 hours to obtain 1-chloro-3-alkoxy-2-hydroxypropane. The obtained 1-chloro-3-alkoxy-2-hydroxypropane can also be purified by distillation under reduced pressure. Next, the formula (4) is prepared by charging 1-chloro-3-alkoxy-2-hydroxypropane (1 mol) and 25% NaOH (1.5-2 mol) and aging at 50-90 ° C. for 8 hours. After stirring is stopped, the two layers are separated, and after the water layer is cut, if necessary, it is further washed with warm water and dehydrated to obtain alkyl glycidyl ether. The obtained alkyl glycidyl ether can also be purified by distillation under reduced pressure.

  Next, the formulas (5) and (6) are diamines (1 to 10 mol in (5), 0.9 to 1.1 mol in (6)) to the alkyl glycidyl ether or 1,2-epoxyalkane (( In 5), 1 mol) and 2 mol in (6) are added at room temperature to 120 ° C. over 2 to 5 hours and aged at the same temperature for 5 to 20 hours. For this reaction, a solvent such as ketones such as acetone, a lower alcohol such as ethanol or isopropanol, or a water mixed solvent may be used. Furthermore, when excess diamine, solvent, and water are used at the same temperature, they are removed by distillation under reduced pressure or washing with water to obtain the desired tertiary amine compound. The resulting tertiary amine compound can be used as it is as a blending component of the product of the present invention, but can also be purified and used by a conventional purification method.

  Specific examples of the alkyl glycidyl ether used in this reaction include decyl glycidyl ether, dodecyl glycidyl ether, tetradecyl glycidyl obtained by reacting a saturated or unsaturated natural or synthetic higher alcohol with epichlorohydrin. Ether, stearyl glycidyl ether and the like can be mentioned, and a single composition or a mixture of two or more arbitrary ratios may be used. Industrially available alkyl glycidyl ethers include Epiol L-41 (decyl glycidyl ether), Epiol SK (stearyl glycidyl ether) manufactured by Nippon Oil & Fats Co., Ltd., Hexoxy manufactured by ACI Japan Limited. 8 (mixture with decyl glycidyl ether and tetradecyl glycidyl ether), Denacol EX-192 (mixture with dodecyl glycidyl ether and tetradecyl glycidyl ether) manufactured by Nagase Chemical Industries, Ltd., SY manufactured by Sakamoto Pharmaceutical Co., Ltd. -25L (a mixture with dodecyl glycidyl ether and dodecyl glycidyl ether) and the like are exemplified, but not particularly limited.

  Specific examples of 1,2-epoxyalkanes include “AOEX” series manufactured by Daicel Chemical Industries, Ltd., “Adeka Olefin Oxide” series manufactured by ADEKA Co., Ltd., etc. Absent.

  Specific examples of the diamine used in this reaction include diamines such as diethylaminoethylamine, dimethylaminopropylamine, and diethylaminopropylamine, but are 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 (B) inorganic acid 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, citric acid, glutamic acid, malic acid, and succinic acid. Examples of the acid include lactic acid and malic acid. 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 0.1 to 10 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 (C) higher alcohol used in the present invention include myristyl alcohol, cetyl alcohol, stearyl alcohol, cetostearyl alcohol, behenyl alcohol, batyl alcohol, isostearyl alcohol, etc. 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 20% 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.

  Furthermore, (D) 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.

  (D) 0.01-10 mass% is preferable and the compounding quantity in the composition for hair of component (D) has more preferable 0.5-3 mass%. If the blending amount of the component (D) is too small, the expected effect becomes insufficient, and if it is too large, the sticky feeling such as stickiness is deteriorated.

  Furthermore, (E) silicone and / or a silicone derivative can be mix | blended with the composition for hair of this invention. Specifically, chain polysiloxanes such as dimethicone, dimethiconol, methylphenylpolysiloxane, diphenylpolysiloxane, cyclic polysiloxanes such as decamethylcyclopentasiloxane and dodecamethylcyclopentasiloxane, silicone resins having a three-dimensional network structure, Modified silicone derivatives such as silicone rubber, amino-modified silicone, fatty acid-modified polysiloxane, alcohol-modified silicone, aliphatic-modified polysiloxane, polyether-modified silicone, epoxy-modified silicone, fluorine-modified silicone, alkyl-modified silicone, etc. are particularly limited. Is not to be done.

  (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.

  Specific examples of the aromatic alcohol (F) used in the present invention include phenoxyethanol, benzyl alcohol, benzyloxyethanol, cresol, p-chloro-m-xylenol, phenethyl alcohol, phenethylpropyl alcohol, and p-tert-butylphenol. , Catechol, hydroxyquinone, phenylethyl alcohol, resorcinol, phenol and the like, among which phenoxyethanol, benzyl alcohol and benzyloxyethanol are particularly preferably used. In the present invention, one or more of these aromatic alcohols can be arbitrarily used.

  (F) 0.01-10 mass% is preferable, the compounding quantity in the composition for hair of a component has more preferable 0.05-5 mass%, and its 0.1-2 mass% is especially preferable. When the blending amount of the component (F) is too small, a sufficient conditioning effect for the hair and a preservative effect of the blended product cannot be obtained sufficiently, and an excessive amount is not preferable because the effect is not improved.

  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 normally used in cosmetics, etc., and is appropriately selected depending on the purpose of use and required function, for example, hydrocarbons such as liquid paraffin, petrolatum, squalane, isopropyl palmitate, cetyl octanoate, Nonionic surfactants such as ester oils such as oleic oleate, polyoxyethylene stearyl ether, glyceryl trioctanoate, polyglycerin fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, camellia oil, olive oil, avocado oil And animal and vegetable fats and oils such as jojoba oil, cation-modified water-soluble polymers such as cationized cellulose, cationized guar gum and diallyldimethylammonium polymers, and fragrances.

  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.

  Next, the present invention will be described in more detail with reference to production examples and examples, but the present invention is not limited to the examples and production examples. The tertiary amine compounds used for comparison are shown in Table 1. Moreover, Examples 1-12 and Comparative Examples 1-4 were prepared by a conventional method, the effect was measured, and the result was shown to Tables 2-5. Content is mass%.

Production Example 1
Into a 2 L four-necked round bottom flask, 928 g (8 mol) of diethylaminoethylamine was added, and 193.6 g (0.8 mol) of dodecylglycidyl ether was cooled as necessary while maintaining at 90 ° C. or lower for 5 hours. The mixture was added dropwise and stirred for another 10 hours. After confirming the disappearance of glycidyl ether by gas chromatography, washing was performed by adding water at the same temperature, and the washing operation was repeated until excess amine could be removed, followed by dehydration under reduced pressure at 110 ° C. to obtain a crude amine. . The crude amine was purified by column chromatography (filler; Wakosil C-200 (Wako Pure Chemical Industries, Ltd.), eluent: chloroform / methanol = 7/3 (v / v)), and 224 g of tertiary amine ( Yield 20.0%). The obtained tertiary amine was confirmed to be a single substance by liquid high performance chromatography (column; TSKgel G1000HHR, eluent: THF).

Production Example 2
The raw material amine was replaced with 816 g (8 mol) of dimethylaminopropylamine, and 326 g (1 mol) of octadecylglycidyl ether was reacted and purified in the same manner as in Production Example 1 to obtain 217 g of tertiary amine (yield 19.0%). .

Production Example 3
The raw material amine was replaced with diethylaminopropylamine 159.3 g (1.23 mol), and 1,2-epoxyoctadecane (ADEKA ADEKA olefin oxide C18) 920 g (2.5 mol) was reacted in the same manner as in Production Example 1 for purification. 259 g of amine (yield 22.0%) was obtained.

Production Example 4
The raw material amine was replaced with 249.9 g (2.45 mol) of dimethylaminopropylamine, and 984 g (5 mol) of C12, C14 epoxy (AOEX-24 manufactured by Daicel Chemical Industries) was reacted in the same manner as in Production Example 1 to obtain 183 g of purified amine ( Yield 17.1%).

  The test methods used in this example are as follows.

(Flexibility, slipperiness, sense of group and comprehensive evaluation)
20 g (length 20 cm) of healthy black hair (healthy hair) not subjected to bleaching treatment 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, and softness after drying, slipperiness, and feeling of grouping by 10 expert panelists, and compared the following criteria It was evaluated with. The same treatment is applied to a damaged hair bundle (20 g × 20 cm) that has been bleached for 30 minutes for healthy black hair, and the flexibility, slipperiness, and drying at the time of application to (drying) to towel drying. The same evaluation was performed by 10 expert panelists on the later flexibility, slipperiness and sense of grouping.
◎: 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.
A: 13 points or more
○: 9 to 12 points
Δ: 5-8 points
×: 4 points or less

  As is clear from Examples 1 to 12 and Comparative Examples 1 to 4, the hair composition of the present invention was applied to the hair, rinsed from the hair, slipped when wet until drying, flexibility, and slip after drying. All showed excellent performance in terms of performance, flexibility, sense of packing, and comprehensive evaluation.

In addition, as described above, the hair composition of the present invention imparts good slipperiness and flexibility from wet to dryness even for damaged hair, and in particular, slipperiness, flexibility, and feeling of unity after drying. Can be given.

Claims (7)

(A) one or both of the tertiary amine compounds represented by the following general formulas (1) and (2)

(R represents a linear or branched alkyl group having 4 to 24 carbon atoms, an alkenyl group or a hydroxyalkyl group, and R ^{1 to} R ⁴ are the same or different alkyl groups having 1 to 3 carbon atoms, hydroxyalkyl group, n, p represents 0 or 1, m, and q represents an integer of 1 to 5.) (B) A hair composition containing an inorganic acid and / or an organic acid. 2. The hair composition as a whole, comprising 0.1 to 10% by mass of component (A) and 0.3 to 10 moles of component (B) relative to 1 mole of component (A). The composition for hair described. Furthermore, the hair composition of Claim 1 or 2 formed by mix | blending 0.1-20 mass% of (C) higher alcohol. Furthermore, the composition for hair of any one of Claims 1-3 formed by mix | blending 0.01-10 mass% of (D) polyhydric alcohol. Furthermore, (E) The composition for hair of any one of Claims 1-4 formed by mix | blending 0.1-10 mass% of silicone and / or a silicone derivative. Furthermore, the composition for hair of any one of Claims 1-5 formed by mix | blending 0.01-10 mass% of (F) aromatic alcohol. The hair composition according to any one of claims 1 to 6, wherein the aromatic alcohol of component (F) is one or more selected from phenoxyethanol, benzyl alcohol, and benzyloxyethanol.