JP5969293B2 - Hair composition - Google Patents

Description

  The present invention relates to a hair composition, and more particularly, good usability (easiness of spreading) even when applied to damaged hair, smoothness when rinsing, smoothness when wet, flexibility and drying. The present invention relates to a composition for hair that is excellent in imparting subsequent combing properties and feeling of unity.

  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 at the same time. 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 flexibility, smoothness and the like to the hair, it is treated with a hair composition such as a hair rinse or a hair treatment mainly composed of a quaternary ammonium salt which is a cationic surfactant. When a hair composition containing an ammonium salt as a main component is used, although there is an excellent flexibility with respect to hair, there are cases where the slipperiness and moist feeling are not sufficient. Therefore, a method of blending silicone oil or the like to improve the slipperiness after drying is also known, but when blending silicone oil or the like, the blending amount may affect the stability of the system. May be subject to volume constraints.

  On the other hand, an amidoamine compound is used in place of a cationic surfactant, and it has excellent thickening properties (gel-forming properties) and stability over time, giving the hair sufficient smoothness, moistness, flexibility, smoothness and light finish. Hair treatment agent compositions are proposed in Patent Document 1 and Patent Document 2, and in Patent Document 3, an esteramine compound is blended, and the hair conditioning effect is excellent, mild to the hair and scalp with low irritation, A hair composition having good biodegradability is disclosed in Patent Document 4, and a hair composition having a good hair conditioning effect, particularly slipperiness and moist feeling is disclosed in Patent Document 4 in which a hydroxy ether amine compound is blended. Contains an alkoxypropyldimethylamine, an amine having various binding species such as hair cosmetics that have excellent flexibility and slipperiness from application to drying. Although compounds have been proposed, spreadability ease at the time of application, smoothness during rinsing was insufficient.

  Patent Document 6 contains a hydroxy ether amine compound, a thickening polymer, and polyethylene glycol having an average molecular weight of 400,000 to 6 million, and has excellent elongation during application, familiarity, and smoothness during rinsing. Although cosmetics have been proposed, satisfactory usability (easiness of spreading and spreading) when applied sufficiently satisfactorily against damaged hair, smoothness when rinsed and when wet have 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 2001-278751 A (page 1-8) JP 2004-323495 A (page 1-10) JP 2004-2261 A (pages 1-25) JP 2008-001616 A (page 1-14)

  Therefore, the present invention has good usability (easiness of spreading) when applied to damaged hair, smoothness when rinsing, smoothness when wet, flexibility and combability after drying, feeling of unity It is an object of the present invention to provide a composition for hair that is excellent in imparting hair.

（式中、Ｒ^１は直鎖又は分岐の炭素数１６〜２４のアルキル基又はアルケニル基を表す。）で表されるヒドロキシエーテルアミンと（Ｂ）下記一般式（２）
Ｒ^２ＯＨ （２）
（式中、Ｒ^２は直鎖の割合が８０重量％以上の直鎖又は分岐の炭素数１２〜２４のアルキル基又はアルケニル基を表す。）で表される高級アルコールと（Ｃ）有機酸を配合することにより、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) The following general formula (1)

(Wherein R ¹ represents a linear or branched alkyl group or alkenyl group having 16 to 24 carbon atoms) and (B) the following general formula (2)
R ² OH (2)
(Wherein R ² represents a linear or branched alkyl group or alkenyl group having 12 to 24 carbon atoms in which the proportion of straight chain is 80% by weight or more) and (C) an organic acid. It has been found that a composition for hair satisfying the above requirements can be obtained by blending, and the present invention has been completed.

  That is, according to the present invention, (A) the above-mentioned specific hydroxy ether amine, and (B) the above-mentioned specific higher alcohol and an organic acid are blended into a damaged hair at the time of application. Good usability (easiness of spreading), smoothness at the time of rinsing, smoothness at the time of wetness, flexibility, combability after drying, and feeling of unity can be given.

Below, the composition for hair of this invention is explained in full detail.
Although there is no limitation in particular as a manufacturing method of the hydroxy ether amine compound of (A) component used for this invention, As a specific example, a higher alcohol (1 mol) and BF ₃ ether complex (BF ₃ pure high grade) 1 to 1.5 mol of epichlorohydrin) was added dropwise over 1 to 2 hours with heating and stirring at 50 to 90 ° C., followed by aging at the same temperature for about 5 hours. 1-chloro-3-alkoxy-2-hydroxypropane is obtained. The obtained 1-chloro-3-alkoxy-2-hydroxypropane can also be purified by distillation under reduced pressure.

  Next, 1-chloro-3-alkoxy-2-hydroxypropane (1 mol) and 25% NaOH (1.5-2 mol) are charged and aged at 50-90 ° C. for 8 hours. After aging, 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-alkoxypropane. The obtained 1,2-epoxy-3-alkoxypropane can also be purified by distillation under reduced pressure.

  Next, diethylamine (1 to 1.5 mol) is added to 1,2-epoxy-3-alkoxypropane (1 mol) 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, a lower alcohol such as ethanol or isopropanol, or a solvent / water mixture may be used. Further, when an excess of secondary amine and solvent at the same temperature and water are used, they are removed by washing with water or / and distillation under reduced pressure, etc., and N- (3-alkoxy-2-hydroxypropyl) -N, N-diethylamine is removed. Get. Further, the obtained N- (3-alkoxy-2-hydroxypropyl) -N, N-diethylamine 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 distillation under reduced pressure. The hydroxy ether amine compound can be produced by other methods, but the production method is not particularly limited.

R ¹ in the general formula (1) is a linear or branched alkyl group or alkenyl group having 16 to 24 carbon atoms, preferably a linear alkyl group or alkenyl group having 18 to 22 carbon atoms. A linear alkyl group having 18 to 22 carbon atoms is more preferable.

  The blending amount of the component (A) in the hair composition is preferably 0.01 to 10% by weight, more preferably 0.05 to 8% by weight, and still more preferably 0.1 to 5% by weight. If it is less than 0.01% by weight, a sufficient effect on the slipperiness when wet cannot be obtained, and if it exceeds 10% by weight, the conditioning effect is not improved, which is not preferable.

  The higher alcohol of the component (B) used in the present invention is a straight chain or branched alkyl group or alkenyl group having a straight chain ratio of 80% by weight or more, preferably a straight chain. A linear or branched alkyl group or alkenyl group having a carbon number of 90 to 90%, more preferably a linear alkyl group having 16 to 22 carbon atoms, specifically, cetyl alcohol, stearyl. Alcohol and behenyl alcohol are preferably used. In the present invention, one or more of these higher alcohols can be arbitrarily used.

  The blending amount of the component (B) in the hair composition is preferably 0.1 to 20% by weight, particularly preferably 3 to 8% by weight. If it is less than 0.1% by weight, the expected viscosity and slipperiness become insufficient, and even if it exceeds 20% by weight, the feeling after use is undesirably deteriorated.

  Specific examples of the organic acid (C) used in the present invention include acetic acid, lactic acid, glycolic acid, citric acid, glutamic acid, malic acid, succinic acid, and the like. Acid and malic acid are preferably used. In the present invention, one or more of these organic acids can be arbitrarily used.

  When the component (C) is blended in the hair composition of the present invention, the component (A) and the component (C) may be blended separately, or after the acid salt of the hydroxy ether amine compound is formed in advance. You may do it. The blending amount of the component (C) in the hair composition is preferably 0.3 to 10 moles, more preferably 0.5 to 5 moles, relative to the component (A).

  The hair composition of the present invention is used by partially or completely substituting it into a salt form by adjusting the pH, but preferably has a pH of 2-8, more preferably 3-6.

  The hair composition of the present invention can further contain an aromatic alcohol as component (D), specifically, phenoxyethanol, benzyl alcohol, benzyloxyethanol, cresol, p-chloro-m-xylenol, Examples include phenethyl alcohol, phenethylpropyl alcohol, p-tert-butylphenol, catechol, hydroxyquinone, phenylethyl alcohol, resorcinol, and phenol, and among these, phenoxyethanol, benzyl alcohol, and benzyloxyethanol are particularly preferably used. In the present invention, one or more of these aromatic alcohols can be arbitrarily used.

  The blending amount of the component (D) in the hair composition is preferably 0.01 to 10% by weight, more preferably 0.05 to 5% by weight, and particularly preferably 0.1 to 2% by weight. When the blending amount of the component (B) is too small, a sufficient conditioning effect on the hair and an antiseptic effect of the blended product cannot be obtained sufficiently.

  The hair composition of the present invention may further contain a component (E) silicone compound, specifically, dimethylpolysiloxane, methylphenylpolysiloxane, alcohol-modified silicone, alkyl-modified silicone, amino-modified silicone. , Polyether silicones, fatty acid-modified polysiloxanes, aliphatic alcohol-modified polysiloxanes, epoxy-modified silicones, fluorine-modified silicones, cyclic silicones, and the like. Examples include (a) to (g) below.

(A) Dimethylpolysiloxane: A polymer having a methylsiloxane structure and a viscosity of 6 to 100,000 mPa · s at 25 ° C.
(B) Cyclic silicone: A silicone oil having a cyclic methylpolysiloxane structure, such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, and cyclic silicone resin.
(C) Highly polymerized dimethylpolysiloxane: one having a methylsiloxane structure and a viscosity at 25 ° C. of 50,000 to 20,000,000 mPa · s. When blended in, it may be blended by dissolving in liquid oil, or an aqueous emulsion prepared in an aqueous solution of a nonionic surfactant such as a cationic surfactant or polyoxyethylene alkyl ether may be blended. preferable. Examples of the liquid oil include dimethylpolysiloxane, cyclic silicone, and isoparaffinic hydrocarbon.
(D) Amino-modified silicone: A silicone oil having an N- (2-aminoethyl) aminopropyl group or N- (2-aminoethyl) aminoisobutyl group, and the amino-modified silicone is blended in the hair cosmetic composition of the present invention. In this case, it is preferable to mix in a liquid oil or mix an aqueous emulsion prepared in an aqueous solution of a nonionic surfactant such as a cationic surfactant or polyoxyethylene alkyl ether. When used as an aqueous emulsion, the amount of amino-modified silicone contained in the aqueous emulsion is preferably 20 to 60%, more preferably 30 to 50%. Examples of the liquid oil include dimethylpolysiloxane, cyclic silicone, and isoparaffinic hydrocarbon.
(E) Polyether-modified silicone: dimethylsiloxane / methyl (polyoxyethylene) siloxane / methyl (polyoxypropylene) siloxane copolymer, dimethylsiloxane / methyl (polyoxyethylene) siloxane copolymer, dimethylsiloxane / methyl (polyol) Xypropylene) siloxane copolymer and the like.
(F) Alcohol-modified silicone: has a structure in which part of the methyl group of dimethylpolysiloxane is replaced with an alkoxy group, and examples thereof include stearoxymethyl polysiloxane and cetoxymethyl polysiloxane.
(G) Alkyl-modified silicone: A structure in which a part of the methyl group of dimethylpolysiloxane is replaced with a long-chain alkyl group, and has a liquid to waxy property depending on the substitution rate and size of the alkyl group. It is done.
(H) Aminophenyl-modified silicone: A silicone oil having an N- (2-aminoethyl) aminopropyl group or N- (2-aminoethyl) aminoisobutyl group and a phenyl group. When blended in cosmetics, dissolve in liquid oil or blend an aqueous emulsion prepared in a nonionic surfactant solution such as a cationic surfactant or polyoxyethylene alkyl ether. It is preferable. Examples of the liquid oil include dimethylpolysiloxane, cyclic silicone, and isoparaffinic hydrocarbon.

  Among these silicone derivatives, (a) dimethylpolysiloxane, (c) highly polymerized dimethylpolysiloxane, (d) amino-modified silicone and (h) aminophenyl-modified silicone are particularly preferable. These silicone derivatives can be used alone or in combination of two or more, and the blending amount is 0.01 to 20%, more preferably 0.05 to 3%, based on the entire composition. This blending amount is preferable because it can give the hair a supple and moist finish without feeling sticky or heavy.

  The blending amount of the silicone compound in the hair composition is preferably 0.01 to 25% by weight and 0.05 to 3% by weight. If it is less than 0.01% by weight, the expected effect becomes insufficient, and even if it exceeds 25% by weight, the stability is deteriorated, which is not preferable.

  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 a surfactant, a moisturizer, a medicinal agent, an anti-inflammatory agent, a bactericidal agent, an antiseptic agent, an ultraviolet absorber, an antioxidant, an organic agent usually used in cosmetics, pharmaceuticals and the like. Inorganic powders, viscosity modifiers, pigments, pearlizing agents, solvents, liquid crystal forming agents, chelating agents, preservatives, colorants, fragrances and the like 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, etc., and is appropriately selected depending on the purpose of use and required function. For example, a cationic interface such as behenyltrimethylammonium chloride, stearyltrimethylammonium chloride, cetyltrimethylammonium chloride, etc. Activators, liquid paraffin, squalane, squalene, paraffin, isoparaffin, petrolatum and other hydrocarbons, polyoxyethylene stearyl ether, glyceryl trioctanoate, polyglycerin fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, etc. Multivalents such as nonionic surfactants, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,3-butylene glycol, glycerin, diglycerin Animal and vegetable oils and fats such as lecoles, camellia oil, olive oil, avocado oil and jojoba oil, cation-modified water-soluble polymers such as cationized cellulose, cationized guar gum and diallyldimethylammonium polymers, fragrance, linseed oil and camellia oil , Macadamia nut oil, corn oil, mink oil, olive oil, avocado oil, sasanqua oil, castor oil, sunflower oil, jojoba oil, sunflower oil, almond oil, rapeseed oil, sesame oil, soybean oil, peanut oil, triglycerin, trioctane Liquid oils such as glyceryl acid, glyceryl triisopalmitate, higher fatty acids such as stearic acid, behenic acid, oleic acid; isopropyl myristate, cetyl octanoate, hexyl laurate, isopropyl myristate, isopropyl palmitate, octyl palmitate, Isocetyl tearate, isopropyl isostearate, octyl isopalmitate, isodecyl oleate, oleyl oleate, pentaerythritol tetra-2-ethylhexanoate, 2-ethylhexyl succinate, diethyl sebacate, etc., zinc pyrithione, benzil chloride An anti-dandruff agent such as luconium is included.

  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. Table 1 shows hydroxy ether amines 1 to 3 synthesized by the method described in this specification. Moreover, Examples 1-8 and Comparative Examples 1-6 were prepared by a conventional method, the effect was measured, and the results are shown in Tables 2 and 3. The content is% by weight.

  The test methods used in this example are as follows.

Test method 1 (dynamic friction coefficient measurement: smoothness when wet and after drying)
<Pretreatment>
Commercially available bleached hair (Burex 10 g × 20 cm) is bundled, the oil is removed with ethanol, washed with 10% polyoxyethylene (2) sodium lauryl ether sulfate solution at 40 ° C., rinsed, and dried (20 ° C. , 40% RH, overnight), dipped in a solution of hair composition diluted 20 times with water (40 ° C., 10 minutes), rinsed with running water at 40 ° C. for 3 minutes, and then dried (20 ° C., 40% The test was performed using RH (overnight) hair. The wet evaluation was performed in the same manner after soaking the treated hair in water and drying the towel.
<Dynamic friction coefficient measurement>
The dynamic friction coefficient was measured using an NRF type friction coefficient meter (manufactured by Rheology Instruments Co., Ltd.), measuring at a load of 20 g and 5 revolutions per minute, and obtaining an average value of 20 hairs. Moreover, the reduction rate from the blank measured simultaneously as the result of the dynamic friction coefficient measurement was calculated below.
In addition, a measurement result shows that smoothness is so favorable that a numerical value is large.
Reduction rate = (B−S) / B × 100
B: Blank measurement value S: Sample measurement value

Test method 2 (sensory evaluation)
Bundling commercially available bleached hair (Burex 10 g × 20 cm), removing oil with ethanol, washing with 10% polyoxyethylene (2) sodium lauryl ether sulfate solution, and uniformly dispersing hair composition (1 g) Apply, rinse with running water at 40 ° C, dry easily after drying with towel drier, spread easily when applied, no squeaking feeling when rinsing, no squeaking feeling after towel drying (when wet), and drying The feeling of moistness and cohesion later were compared sensorially with 10 professional panelists and evaluated according to the following criteria.
◎: 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 8 and Comparative Examples 1 to 6, the hair composition of the present invention can be applied to damaged hair at the time of application, rinsing, wetting and drying. Excellent performance.

As described above, the hair composition of the present invention has good usability (easiness of spreading) when applied to damaged hair, smoothness when rinsing, smoothness when wet, flexibility and drying. It is clear that it gives a feeling of unity and unity later.

Claims (4)

(A) a hydroxy ether amine represented by the following general formula (1):

(In the formula, R ¹ represents a linear or branched alkyl group or alkenyl group having 16 to 24 carbon atoms.)
(B) Higher alcohol R ² OH represented by the following general formula (2) (2)
(In the formula, R ² represents a linear or branched alkyl group or alkenyl group having 12 to 24 carbon atoms in which the linear ratio is 80% by weight or more.)
And (C) a hair composition containing a hydroxy acid . The hair composition according to claim 1, further comprising (D) an aromatic alcohol. Component (D), phenoxyethanol, benzyl alcohol, one or more at which claim 2 hair compositions according selected from benzyloxy ethanol. Furthermore, the composition for hair in any one of Claims 1-3 containing (E) silicone compound.