JP5111947B2 - 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, particularly slipperiness and moist feeling after drying, even against 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 which is a cationic surfactant. When a hair composition containing a quaternary ammonium salt as a main component is used, the hair has excellent flexibility but may not have sufficient slipperiness and moist feeling after drying. Therefore, a method of blending silicone oil or the like to improve the slipperiness after drying is known, but when blending silicone oil or the like, the blending amount may affect the stability of the system, There may be restrictions on the amount.

  On the other hand, for the purpose of blending a cationic surfactant and imparting smoothness and flexibility, Patent Document 1 and Patent Document 2 include an ether type quaternary ammonium salt having an ether group obtained by adding ethylene oxide to a higher alcohol. Has been proposed. Further, Patent Document 3 and Patent Document 4 propose hair rinsing agents excellent in flexibility and smoothness using 2-hydroxyalkyl type quaternary ammonium salts having a hydroxyl group in the alkyl group. In the proposal of, sufficient satisfactory moist feeling and slipperiness are not obtained.

Furthermore, so-called damaged hair has been increasing due to the recent fashion of coloring, but the quaternary ammonium salt proposed in Patent Document 5 has improved the conditioning effect on healthy hair, but has improved on damaged hair. There was room for.
JP-A-6-107524 (page 1-7) Japanese Patent Laid-Open No. 6-178828 (page 1-4) JP 49-81550 A (page 1-3) JP-A-50-121443 (page 1-4) JP 2004-323496 A (page 1-12)

  Accordingly, the present invention relates to a hair composition, and more specifically, to develop a hair composition having a good conditioning effect, particularly slipperiness after drying and moist feeling even against damaged 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）

（Ｒは直鎖又は分岐した炭素数６〜３０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、Ｒ^４は炭素数１〜３のアルキル基、ヒドロキシアルキル基、又はベンジル基、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、Ｘ⁻は一価のアニオンを表す。）で表されるカチオン界面活性剤と（Ｂ）高級アルコールと（Ｃ）油性成分と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 having 6 to 30 carbon atoms, an alkenyl group or a hydroxyalkyl group), and the rest are alkyl groups having 1 to 3 carbon atoms, hydroxyalkyl groups, R ³ , R ⁴ represents an alkyl group having 1 to 3 carbon atoms, a hydroxyalkyl group, or a benzyl group, A represents an ethylene group and / or a propylene group, n represents an integer of 1 or more, and X ⁻ represents a monovalent anion. It was found that a hair composition satisfying the above requirements can be obtained by blending a cationic surfactant represented by (II) with (B) a higher alcohol and (C) an oil component.

  The preferable aspect of this invention is 0.1-10 mass% of (A) component, 1-10 mass% of (B) component, and 0.1-10 mass of (C) component in the hair composition whole quantity. %, And a good conditioning effect for damaged hair, in particular, good slipperiness and moist feeling after drying.

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

In the general formula (1), at least one or both of R ¹ and R ² is a group represented by the general formula (2). Here, R in the general formula (2) is a linear or branched alkyl group having 6 to 30 carbon atoms, preferably 12 to 24 carbon atoms, and more preferably 14 to 22 carbon atoms, an alkenyl group or a hydroxyalkyl group. In particular, an alkyl group is preferable, and the remainder is an alkyl group having 1 to 3 carbon atoms and a hydroxyalkyl group, preferably an alkyl group having 1 to 2 carbon atoms, and particularly preferably a methyl group.

R ³ and R ⁴ are an alkyl group having 1 to 3 carbon atoms, a hydroxyalkyl group, or a benzyl group, preferably an alkyl group having 1 to 2 carbon atoms, and particularly preferably a methyl 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. X ⁻ is a monovalent anion, and examples thereof include a halide ion and a methyl sulfate ion, and a chloride ion is particularly preferable.

（Ｒ、Ｒ^２、Ｒ^３、Ｒ^４、Ａ、ｎ、Ｘは前記の意味を表し、Ｒ’はＨ又はＣＨ_３を表す。） Although there is no limitation in particular as a manufacturing method of the cationic surfactant as (A) component used for this invention, Generally it can manufacture by the method shown by following Reaction formula (5)-(10).

(R, R ² , R ³ , R ⁴ , A, n, X represent the above meaning, and R ′ represents H or CH _3. )

  Specific examples of the formulas (5) and (6) include 1,2-epoxyalkane (1 mol or 2 mol) to dimethylamine (1 to 1.5 mol) or monomethylamine (0.8 to 1.2). Mol) gas or aqueous solution is rapidly added at room temperature to 120 ° C., and aged at 50 to 120 ° C. for 5 to 20 hours. In this reaction, a solvent capable of dissolving 1,2-epoxyalkane 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 to obtain the desired hydroxyalkylamine compound (N, N-dimethyl-N- (2-hydroxyalkyl) amine. Alternatively, N, N-bis- (2-hydroxyalkyl) -N-methylamine) is obtained. The obtained tertiary amine compound can also be purified and used by distillation under reduced pressure. The tertiary amine compound can be produced by other methods, and the production method is not particularly limited.

  As specific examples of the formulas (7) and (8), a tertiary amine compound is added to the resulting tertiary amine compound as a catalyst in an amount of 0.5 to 1% KOH, dehydrated at 100 to 130 ° C., 180 While maintaining 3 atm by raising the temperature to 0 ° C., ethylene oxide and / or propylene oxide (1 to 20 mol) was introduced, and the target polyoxyalkylene (hereinafter abbreviated as POA) alkylamine compound (N, N-dimethyl-N -(2-POA alkyl) amine or N, N-bis- (2-POA alkyl) -N-methylamine). The obtained tertiary amine compound can also be purified and used by distillation under reduced pressure. The tertiary amine-POA adduct can be produced by other methods, and the production method is not particularly limited.

  Further, in the formulas (9) and (10), a lower alcohol such as ethanol or isopropanol or water or a lower alcohol / water mixed solution is added to a hydroxyalkylamine compound or POA alkylamine compound, and methyl chloride or the like is added at 70 to 100 ° C. A quaternizing agent is added over 5 to 10 hours to obtain the desired cationic surfactant. The obtained cationic surfactant 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 an ordinary purification method. The cationic surfactant of the present invention can be produced by other methods, but 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 higher alcohol (B) 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.

  (B) As for the compounding quantity in the composition for hair of a component, 1-10 mass% is preferable, and 3-8 mass% is more preferable. If the blending amount of the component (B) is too small, the expected effect is insufficient, and if it is too large, the feeling after use is unfavorable.

  Specific examples of the oily substance (C) used in the present invention include hydrocarbons such as liquid paraffin, petrolatum 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.

  0.1-10 mass% is preferable and the compounding quantity in the composition for hair of (C) component has more preferable 0.5-3 mass%. If the blending amount of the component (C) is too small, the expected effect becomes insufficient, and if it is too large, the stickiness such as stickiness is deteriorated.

  Furthermore, the hair composition of the present invention can be blended with silicone oil as component (D). 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.

  (D) As for the compounding quantity in the composition for hair of a component, 0.1-10 mass% is preferable, and 0.5-3 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 stability deteriorates, which is not preferable.

  Furthermore, (E) 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.

  (E) 0.1-10 mass% is preferable, and, as for the compounding quantity in the composition for hair of a component, 0.5-3 mass% is more preferable. If the blending amount of the component (E) is too small, the expected effect becomes insufficient, and if it is too large, the stickiness such as stickiness is deteriorated.

（式中、Ｒ^５、Ｒ^６の少なくとも一方／又は両方は、下記一般式（４）

（Ｒは直鎖又は分岐した炭素数６〜３０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^７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以上の整数を表す。） The hair composition of the present invention may contain (F) a tertiary amine compound represented by the following general formula (3).

(In the formula, at least one or both of R ⁵ and R ⁶ are represented by the following general formula (4):

(R is a linear or branched alkyl group having 6 to 30 carbon atoms, an alkenyl group, or a hydroxyalkyl group), and the remainder is an alkyl group having 1 to 3 carbon atoms, a hydroxyalkyl group, and R ⁷ is An alkyl group having 1 to 3 carbon atoms, a hydroxyalkyl group, A represents an ethylene group and / or a propylene group, and n represents an integer of 1 or more. )

As the tertiary amine compound of the component (F), in the general formula (3), at least one or both of R ⁵ and R ⁶ are the same as those in the general formula (4), where R is linear or branched carbon number 6. To 24, preferably an alkyl group having 12 to 24 carbon atoms, more preferably an alkyl group having 14 to 22 carbon atoms, an alkenyl group or a hydroxyalkyl group, particularly preferably an alkyl group, and the remainder being an alkyl group having 1 to 3 carbon atoms, a hydroxy group An alkyl group, preferably an alkyl group having 1 to 3 carbon atoms, particularly preferably a methyl group or an ethyl group. R ⁷ 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.

  As the tertiary amine compound of component (F), N, N-dimethyl-N- (2-hydroxypalmityl) amine, N, N-dimethyl-N- (2-hydroxystearyl) amine, N, N-diethyl N, N-dialkyl-N- (2-hydroxyalkyl) amines such as N- (2-hydroxypalmityl) amine and N, N-diethyl-N- (2-hydroxystearyl) amine, N, N-bis -(2-hydroxypalmityl) -N-methylamine, N, N-bis- (2-hydroxystearyl) -N-methylamine, N, N-bis- (2-hydroxypalmityl) -N-ethylamine, N, N-bis- (2-hydroxystearyl) -N-ethylamine and the like, N, N-bis- (2-hydroxyalkyl) -N-alkylamine), N, N-dihydroxye N, N-dihydroxyalkyl-N- (2-hydroxyalkyl) amine, such as ru-N- (2-hydroxypalmityl) amine, N, N-dihydroxyethyl-N- (2-hydroxystearyl) amine, N, N, N-bis- (2-hydroxyalkyl) -N such as N-bis- (2-hydroxypalmityl) -N-hydroxyethylamine, N, N-bis- (2-hydroxystearyl) -N-hydroxyethylamine -Hydroxyalkylamine and the like.

Further, N, N-, which is obtained by adding ethylene oxide and / or propylene oxide to the N, N-dialkyl-N- (2-hydroxyalkyl) amine or N, N-dialkyl-N- (2-hydroxyalkyl) amine. N, N-dialkyl-N- (2-polyoxyalkylenealkyl) amines such as dimethyl-N- (2-polyoxyethylene and / or propylene stearyl) amine, N, N-bis- (2-polyoxyethylene and And / or N, N-bis- (2-polyoxyalkylenealkyl) -N-methylamine such as propylene stearyl) -N-methylamine. Among these, N, N-dimethyl-N- (2-hydroxypalmityl) amine, N, N-dimethyl-N- (2-hydroxystearyl) amine, N, N-bis- (2-hydroxypalmityl)- N-methylamine and N, N-bis- (2-hydroxystearyl) -N-methylamine are particularly preferably used. In the present invention, one or more of these tertiary amine compounds can be arbitrarily used.

  The content of the component (F) in the hair composition is 0.01 to 10% by mass, preferably 0.5 to 5% by mass, and more preferably 1 to 3% by mass.

  Furthermore, (G) inorganic acid and / or organic acid can be mix | blended with the composition for hair of this invention. Specific examples of the inorganic acid include hydrochloric acid, sulfuric acid, and phosphoric acid, and examples of the organic acid include acetic acid, lactic acid, glycolic acid, citric acid, glutamic acid, malic acid, and succinic acid. In particular, lactic acid and citric acid can be 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 (G) in the hair composition is preferably 0.3 to 5 mol times, particularly preferably 0.5 to 3 mol times with respect to 1 mol of the component (F). 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.

  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 required function. For example, cation-modified water such as cationized cellulose, cationized guar gum, diallyldimethylammonium polymer, etc. Polymers, polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, 1,3-butylene glycol and glycerin, 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.

  EXAMPLES Next, although an Example demonstrates this invention still in detail, this invention is not limited to an Example. Tables 1 and 2 show the cationic surfactants 1 to 4 of the present invention synthesized by the method described in this specification. (In the table, A is an abbreviation when EO is an ethylene group, and PO is an abbreviation when it is a propylene group.) Using these cationic surfactants, dynamic friction coefficient measurement (smoothness) is measured, and measurement of a comparative cationic surfactant is performed. The results are shown in Table 4, and the cationic surfactant used for comparison is shown in Table 3. 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 5-9. Content is mass%.

The test methods used in this example are as follows.
(Dynamic friction coefficient measurement)
Healthy hair was washed with 10% polyoxyethylene (3) sodium lauryl ether sulfate aqueous solution, rinsed and then immersed in various cationic surfactant aqueous solutions shown in Table 4 adjusted to 0.5%, respectively, at 40 ° C. for 5 minutes. After rinsing, it was dried. After drying, the hair was fixed on a preparation, and the coefficient of dynamic friction (MIU) was measured with a friction tester (KES-SE manufactured by Kato Tech Co., Ltd.) under the following conditions.
Measurement weight: 50g
Number of measurements: 10 times The rate of decrease from the simultaneously measured blank was calculated as follows.
Reduction rate _{= (M B -M S) /} M B × 100
M _B : Blank MIU value M _S : MIU value of cationic surfactant The criteria for evaluation were set as follows.
〇 ・ ・ ・ Decrease rate 20% or more
△ ・ ・ ・ Decrease rate 10% or more and less than 20%
× ・ ・ ・ Decrease rate less than 10%

(Flexibility, moist feeling, smooth feeling, slipperiness and comprehensive evaluation)
The prepared composition was sensorially compared with the following criteria by 10 panelists, and the hair flexibility, hair moistness, hair smoothness and hair slipperiness were compared.
◎: 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 and 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 1-15 and Comparative Examples 1-10,
The hair composition of the present invention exhibited excellent performance in terms of hair flexibility, hair moistness, hair smoothness, hair slipperiness and comprehensive evaluation.

(Flexibility, moist, smooth, slipperiness and comprehensive evaluation of bleached hair)
A damaged hair bundle (10 g × 30 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. After drying, it was evaluated by the following criteria by sensory comparison of the flexibility of the hair, the moist feeling of the hair, the smoothness of the hair, and the slipperiness of the hair by a professional panel of five women.
◎: If there are 4 or more people who answered good
○: When three people answered good
△: When two people answered good
×: When the number of people who answered good is 1 or less, and for comprehensive evaluation, the result of sensory evaluation 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 described above, it is clear that the hair composition of the present invention gives a conditioning effect to damaged hair, in particular, slipperiness after drying and a moist feeling.

Claims (7)

(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 having 6 to 30 carbon atoms, an alkenyl group or a hydroxyalkyl group), and the rest are alkyl groups having 1 to 3 carbon atoms, hydroxyalkyl groups, R ³ , R ⁴ represents an alkyl group having 1 to 3 carbon atoms, a hydroxyalkyl group, or a benzyl group, A represents an ethylene group and / or a propylene group, n represents an integer of 1 to 20 , and X ⁻ represents a monovalent anion. The composition for hair containing the cationic surfactant represented by (B), (B) higher alcohol, and (C) oil-based component. Claims (A) 0.1 to 10% by mass, (B) component 1 to 10% by mass, and (C) component 0.1 to 10% by mass in the total amount of the hair composition. 2. A composition for hair according to 1. Furthermore, the hair composition of Claim 1 or 2 formed by mix | blending 0.1-10 mass% of (D) silicone oil in the hair composition whole quantity. Furthermore, the composition for hair of any one of Claims 1-3 formed by mix | blending (E) polyhydric alcohol 0.1-10 mass% in the composition for hair. Furthermore, (F) the following general formula (3)

(In the formula, at least one or both of R ⁵ and R ⁶ are represented by the following general formula (4):

(R is a linear or branched alkyl group having 6 to 30 carbon atoms, an alkenyl group, or a hydroxyalkyl group), and the remainder is an alkyl group having 1 to 3 carbon atoms, a hydroxyalkyl group, and R ⁷ is An alkyl group having 1 to 3 carbon atoms, a hydroxyalkyl group, A represents an ethylene group and / or a propylene group, and n represents an integer of 1 or more. The composition for hair of any one of Claims 1-5 containing the tertiary amine compound represented by this. The hair composition according to claim 5, wherein 0.01 to 10% by mass of the component (F) is blended in the total amount of the hair composition. Furthermore, (G) inorganic acid and / or organic acid are contained, and pH is 2-8, The composition for hair of any one of Claims 1-6.