JP4663540B2 - Hair treatment agent - Google Patents

Description

  The present invention relates to a hair treatment agent that can be used as a hair rinse, a hair conditioner, a hair treatment or the like.

Hair treatments such as shampoos, rinses, conditioners, treatments, hair dyes, and mousses have softness, smoothness, oiliness and dryness to the hair to improve hair protection and feel when used. There is a demand for imparting smoothness and good combing afterwards. Conventionally, quaternary ammonium salts and amine salts have been blended to meet these requirements. These counter ions include halogen ions such as Cl and Br, or short chain sulfate ions such as methyl sulfate and ethyl sulfate (Patent Document 1), acetic acid, tartaric acid, lactic acid, malic acid, succinic acid, and long chain alkyl. Organic acid ions such as carboxylic acid and sulfonic acid (Patent Documents 2 and 3) have been reported. However, they do not fully satisfy the feeling of use when applied to hair and after drying.
JP-A-6-9346 WO99 / 11226 pamphlet JP-A-9-118606

  An object of the present invention is to provide a hair treatment agent capable of imparting sufficient flexibility, smoothness, etc. at the time of application to hair and rinsing, and capable of imparting sufficient smoothness and good combing after drying. Is to provide.

  By using a specific organic acid as a counter ion of a quaternary ammonium salt or amine salt, the present invention can impart sufficient flexibility, smoothness, etc. at the time of application to hair and rinsing, It has been found that sufficient smoothness and good combing can be imparted even after drying.

That is, this invention provides the hair treatment agent containing the following (a) component and (b) component.
(A): Organic acid represented by general formula (1) (hereinafter referred to as organic acid (1)), or organic acid represented by general formula (2) (hereinafter referred to as organic acid (2)) and salts thereof At least one kind selected from.

[Wherein, R ¹ represents a linear or branched alkyl group or hydroxyalkyl group having 1 to 5 carbon atoms, and R ² represents H or a linear or branched alkyl group or hydroxyalkyl group having 1 to 5 carbon atoms. Show. ]
(B): At least one selected from quaternary ammonium salts, tertiary amines and salts thereof.

  The hair treatment agent of the present invention can impart sufficient flexibility, smoothness and oiliness when applied to hair, and can impart flexibility, smoothness and smoothness when rinsing, and can be dried. Later, sufficient smoothness and good combing can be imparted.

[(A) component]
The component (a) of the present invention is at least one selected from the organic acid (1), the organic acid (2), and salts thereof.

In the organic acid (1) and the organic acid (2), R ¹ represents a linear or branched alkyl group having 1 to 5 carbon atoms or a linear or branched hydroxyalkyl group having 1 to 5 carbon atoms, A linear or branched alkyl group having 1 to 4 carbon atoms or a linear or branched hydroxyalkyl group having 1 to 4 carbon atoms is preferable, and in particular, a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group. A hydroxyalkyl group having 2 to 3 carbon atoms is preferred. The hydroxyalkyl group having 2 to 3 carbon atoms is preferably a hydroxyethyl group, a 2,3-dihydroxypropyl group, a 1-methyl-2-hydroxyethyl group, or a 2-hydroxypropyl group.

In the organic acid (1) and the organic acid (2), R ² is selected from H, a linear or branched alkylene group having 1 to 5 carbon atoms, and a linear or branched hydroxyalkyl group having 1 to 5 carbon atoms. And a group selected from H, a linear or branched alkyl group having 1 to 4 carbon atoms, and a linear or branched hydroxyalkyl group having 1 to 4 carbon atoms, particularly H or a methyl group. , Ethyl group, propyl group, isopropyl group, tert-butyl group and hydroxyalkyl group having 2 to 3 carbon atoms are preferred. The hydroxyalkyl group having 2 to 3 carbon atoms is preferably a hydroxyethyl group, a 2,3-dihydroxypropyl group, a 1-methyl-2-hydroxyethyl group, or a 2-hydroxypropyl group.

  The method for synthesizing the organic acid (1) and the organic acid (2) is not particularly limited. For example, phosphoric anhydride, polyphosphoric acid, phosphoric acid, or the like is reacted with the corresponding alcohol using water or a solvent as necessary. In addition, if necessary, a method of extraction, crystallization, etc., or reaction of the corresponding alcohol with water, solvent, base, etc., if necessary, using phosphorus oxychloride, etc. There are methods for obtaining organic acid (1) by decomposition, extraction, crystallization, and the like. In addition, the reaction of phosphorus halides with organometallics, hydrogen phosphonates and olefins can be reacted with catalysts, solvents, etc. such as palladium, rhodium, and nickel as necessary, and extraction, distillation, etc. can be performed as necessary. And a method of obtaining the organic acid (2).

  Examples of the salt of the organic acid (1) or the organic acid (2) include alkali metal salts such as Na and K, substituted or unsubstituted ammonium salts, and the like.

[Component (b)]
The component (b) of the present invention is at least one selected from quaternary ammonium salts, tertiary amines and salts thereof.

  The component (b) is not particularly limited as long as it forms a salt with the organic acid (1) or the organic acid (2) and becomes a cationic surfactant, but is preferably represented by the general formula (3). A quaternary ammonium salt, a tertiary amine represented by the general formula (4) or a salt thereof, and it is preferable that the component (b) contains at least a tertiary amine represented by the general formula (4).

[Where:
R ³ is a linear or branched alkyl group having 8 to 30 carbon atoms or a linear or branched alkenyl group having 8 to 30 carbon atoms, which may be interrupted by an ester group, an amide group or an ether group,
R ⁴ is a linear or branched alkyl group having 8 to 30 carbon atoms or a linear or branched alkenyl group having 8 to 30 carbon atoms, which may be interrupted by an ester group, an amide group or an ether group, Or a linear or branched alkyl group having 1 to 3 carbon atoms, or a linear or branched hydroxyalkyl group having 1 to 3 carbon atoms,
R ⁵ and R ⁶ are a linear or branched alkyl group having 1 to 3 carbon atoms or a linear or branched hydroxyalkyl group having 1 to 3 carbon atoms,
X represents an anion].

[Where:
R ⁷ is a linear or branched alkyl group having 8 to 30 carbon atoms or a linear or branched alkenyl group having 8 to 30 carbon atoms, which may be interrupted by an ester group, an amide group or an ether group,
R ⁸ is a linear or branched alkyl group having 8 to 30 carbon atoms or a linear or branched alkenyl group having 8 to 30 carbon atoms, which may be interrupted by an ester group, an amide group or an ether group, Or a linear or branched alkyl group having 1 to 3 carbon atoms, or a linear or branched hydroxyalkyl group having 1 to 3 carbon atoms,
R ⁹ represents a linear or branched alkyl group having 1 to 3 carbon atoms or a linear or branched hydroxyalkyl group having 1 to 3 carbon atoms].

In general formula (3), R ³ is preferably a linear or branched alkyl group having 10 to 28 carbon atoms which may be interrupted by an ester group, an amide group or an ether group, and in particular, an ester group, an amide group or A linear or branched alkyl group having 14 to 24 carbon atoms which may be separated by an ether group is preferred.

In the general formula (3), R ⁴ is a linear or branched alkyl group having 14 to 24 carbon atoms or a linear chain having 1 to 3 carbon atoms, which may be interrupted by an ester group, an amide group or an ether group. Alternatively, a branched alkyl group or a linear or branched hydroxyalkyl group having 1 to 3 carbon atoms is preferable, a linear or branched alkyl group having 1 to 3 carbon atoms is more preferable, and a methyl group or an ethyl group is particularly preferable. preferable.

In the general formula (3), R ⁵ and R ⁶ are preferably a methyl group or an ethyl group. Examples of the anion represented by X include halogen ions such as Cl ⁻ and Br ⁻ , short chain alkyl sulfate ions such as methyl sulfate ion and ethyl sulfate ion, organic acid ions such as acetic acid, tartaric acid, lactic acid, malic acid and succinic acid, Examples thereof include OH ⁻ and carbonate ions, and halogen ions, short-chain alkyl sulfate ions, OH ⁻ and carbonate ions are preferable.

In the general formula (4), R ⁷ is preferably a linear or branched alkyl group having 10 to 28 carbon atoms which may be separated by an ester group, an amide group or an ether group, and in particular, an ester group, an amide group or A linear or branched alkyl group having 14 to 24 carbon atoms which may be separated by an ether group is preferred.

In the general formula (4), R ⁸ is a linear or branched alkyl group having 14 to 24 carbon atoms or a linear chain having 1 to 3 carbon atoms, which may be interrupted by an ester group, an amide group or an ether group. Alternatively, a branched alkyl group or a linear or branched hydroxyalkyl group having 1 to 3 carbon atoms is preferable, a linear or branched alkyl group having 1 to 3 carbon atoms, or a linear or branched group having 1 to 3 carbon atoms. More preferred are chain hydroxyalkyl groups.

In the general formula (4), R ⁹ is preferably a methyl group, an ethyl group or a hydroxyalkyl group, more preferably a methyl group or an ethyl group.

  Examples of the tertiary amine salt represented by the general formula (4) include salts of inorganic acids such as hydrochloric acid, sulfuric acid and phosphoric acid, and salts of organic acids such as acetic acid, tartaric acid, lactic acid, malic acid and succinic acid. .

[Hair treatment agent]
The content of the component (a) in the hair treatment agent of the present invention provides the hair with a good feel and suppresses product separation, solidification, etc. On the other hand, it is preferably 0.05 to 20 mol times, more preferably 0.2 to 10 mol times, and particularly preferably 0.3 to 5 mol times.

  The content of the component (b) in the hair treatment agent of the present invention is preferably 0.1 to 20% by weight, more preferably 0.2 to 15% by weight, and particularly preferably 0.5 to 10% by weight.

  The hair treatment agent of the present invention preferably further contains an oily component. Examples of the oily component of the present invention include higher alcohols, ester oils, silicones, hydrocarbons and the like, and preferably oil agents such as higher alcohols and ester oils and / or silicones, particularly higher alcohols and / or silicones.

  As the higher alcohol, a linear or branched alkyl group having 10 to 30 carbon atoms or a higher alcohol having a linear or branched alkenyl group having 10 to 30 carbon atoms, preferably a linear chain having 12 to 26 carbon atoms. Or a higher alcohol having a branched alkyl group or a linear or branched alkenyl group having 12 to 26 carbon atoms, more preferably cetanol, cetyl alcohol, stearyl alcohol, aralkyl alcohol, behenyl alcohol, caranavir alcohol, ceryl Alcohol etc. are mentioned.

  As ester oils, esters of a fatty acid having 8 to 40 carbon atoms and a linear or branched alcohol having 1 to 4 carbon atoms, preferably a fatty acid having 10 to 24 carbon atoms and a linear chain having 1 to 3 carbon atoms, or Esters with branched chain alcohols, more preferably esters of fatty acids having 12 to 22 carbon atoms with propyl alcohol or isopropyl alcohol.

  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 Examples include modified silicone.

  The content of the oily component in the hair treatment agent of the present invention is preferably from 0.1 to 30% by weight, preferably from 0.5 to 25% by weight from the viewpoint of good hair feel and emulsification / dispersion stability of the oily component. Further preferred is 1 to 20% by weight.

  The hair treatment agent of the present invention may further contain an organic acid (a) other than the organic acid (1), the organic acid (2), and salts thereof. Examples of the other organic acids include, but are not limited to, for example, lactic acid, hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, malonic acid, succinic acid, glutaric acid, adipic acid, maleic acid, fumaric acid, glycolic acid, Hydroxyacrylic acid, glyceric acid, malic acid, tartaric acid, citric acid, polyglutamic acid, glutamic acid, aspartic acid and the like can be mentioned. However, the organic acid used as a pH adjuster is not included in the organic acid used in combination with the component (a).

  The content of the organic acid other than the component (a) is preferably equal to or less than that of the component (a), and is preferably 0 to 10 mol times, more preferably 0 to 5 mol relative to the component (b). Double, particularly 0 to 3 times is preferable.

  The hair treatment agent of the present invention includes other anionic surfactants, nonionic surfactants, surfactants such as amphoteric surfactants, lanolin derivatives, higher fatty acid esters, higher fatty acids, fats and oils, glycerin, Amino acids, humectants, cationic polymers, polysaccharides, polypeptides, pearlizing agents, solvents, liquid crystal forming agents, inorganic acids, dyes, fragrances, UV absorbers, antioxidants, propellants, chelating agents, pH adjusters, Preservatives, antidandruff agents, and the like can be appropriately blended within a range not impairing the object of the present invention.

  The hair treatment agent of the present invention can be made into a desired dosage form such as an aqueous solution, an ethanol solution, an emulsion, a suspension, a gel, a liquid crystal, and an aerosol.

  The pH of the hair treatment agent of the present invention is preferably 2 to 12, more preferably 3 to 11 for imparting conditioning effects, and particularly preferably 3 to 6 from the viewpoint of good hair feel and product stability.

  The hair treatment agent of the present invention can be used for hair rinse, hair conditioner, hair treatment, hair pack, hair cream, conditioning mousse, hair mousse, hair spray, leave on treatment, shampoo, hair lotion shampoo, hair dye and the like.

  Hereinafter, “%” in the examples is “% by weight” unless otherwise specified. The components (a) used in the following examples are collectively shown in Table 1, and the components (b) are collectively shown in Table 2.

Examples 1-7 and Comparative Examples 1-3
(A) Organic hairs A to G as components, or lactic acid, L-glutamic acid, hydrochloric acid as comparative acids, (b-1) as components (b), and hair rinse agents having the compositions shown in Table 3 were prepared by conventional methods. did. About these hair rinse agents, the following method evaluated the performance at the time of application to hair, at the time of rinsing, and after drying. The results are shown in Table 3.

<Evaluation method>
20 g of hair (length 20 cm, average diameter 60 μm) of a Japanese woman who had not been chemically treated such as cold perm was bundled and washed with 5 g of shampoo. This shampoo composition is 15% polyoxyethylene alkyl (carbon number 12) ether ether sulfate (ethylene oxide average addition mole number 2.5) 15%, diethanolamide 3%, the balance is water.

Thereafter, 2.0 g of the hair rinse agent was evenly applied and rinsed with running water at about 40 ° C. for 30 seconds. About the softness at the time of application, smoothness, oiliness, softness at the time of rinsing, smoothness, persistence of smoothness, smoothness after drying, and feeling of combing, 5 panelists specialized in the following criteria evaluated.
◎; Responding that 4 or more people are effective ○; Responding that 3 people are effective △; Responding that 2 people are effective ×;

Examples 8-11
Using the acid shown in Table 4 and the component (b), a hair rinse agent having the composition shown in Table 4 was prepared by a conventional method. About these hair rinse agents, it carried out similarly to Example 1, and evaluated the performance at the time of the application to hair, the time of rinsing, and drying. The results are shown in Table 4.

Example 12
A hair conditioner having the following composition was produced. This hair conditioner had flexibility and smoothness at the time of application and rinsing, a feeling of oiliness, sufficient smoothness after drying, and good combing.

Organic acid A 0.6%
(Molar ratio of component (b) = 1.3)
(B-2) 1.6%
Stearyl alcohol ^{* 1} 4.0%
Glycerin 1.0%
Benzyloxyethanol 0.3%
Silicone ^{* 2} 2.0%
Amino-modified silicone-polyoxyalkylene block copolymer ^{* 3} 0.5%
Dipentaerythritol fatty acid ester ^{* 4} 0.2%
Hydroxyethyl cellulose ^{* 5} 0.2%
Highly polymerized polyethylene glycol ^{* 6} 0.05%
Tocopherol acetate 0.1%
Fragrance, methylparaben appropriate amount Purified water remaining (pH 4.5)
* 1: Calcoal 8098 manufactured by Kao Corporation
* 2: BY00-003 manufactured by Toray Dow Corning Silicone
* 3: Nippon Unicar FZ-3789
* 4: Nisshin Oil Co., Ltd. Cosmall 168AR
* 5: SE-850 manufactured by Daicel Chemical Industries, Ltd.
* 6: Union Carbide Polyox WSRN-60K
Example 13
A hair treatment agent having the following composition was produced. This hair treatment had flexibility and smoothness at the time of application and rinsing, a feeling of oiliness, sufficient smoothness after drying, and good combing.

Organic acid C 1.1% (to component (b) molar ratio = 1.2)
(B-3) 2.5%
Stearyl alcohol 4.5%
Behenyl alcohol ^{* 1} 1.5%
Isononyl isononanoate ^{* 2} 0.5%
Silicone ^{* 3} 1.0%
Amino-modified silicone ^{* 4} 0.5%
Malic acid 0.1%
Dipropylene glycol 3.0%
Benzyl alcohol 0.3%
Arginine 0.2%
Pantothenyl ethyl ether 0.1%
Fragrance, methylparaben appropriate amount Purified water remaining (pH 4.0)
* 1 Calcoal 22080 manufactured by Kao Corporation
* 2 Salacos 99 manufactured by Nisshin Oil Co., Ltd.
* 3 SH200C-5000cs manufactured by Toray Dow Corning Silicone Co., Ltd.
* 4 SM8704C manufactured by Toray Dow Corning Co., Ltd.

Claims (5)

The hair treatment agent containing the following (a) component and (b) component.
(A): At least one selected from organic acids represented by general formula (1), organic acids represented by general formula (2), and salts thereof.

[Wherein, R ¹ represents a linear or branched alkyl group or hydroxyalkyl group having 1 to 5 carbon atoms, and R ² represents H or a linear or branched alkyl group or hydroxyalkyl group having 1 to 5 carbon atoms. Show. ]
(B): At least one selected from quaternary ammonium salts, tertiary amines and salts thereof.   The content of the organic acid (a) is 0.05 to 20 mol times the component (b), and the content of the component (b) is 0.1 to 20% by weight. Hair treatment agent. 3. The general formula (1) or the general formula (2), wherein R ¹ and R ² are a linear or branched alkyl group having 1 to 4 carbon atoms or a hydroxyalkyl group having 2 to 3 carbon atoms. The hair treatment agent described.   Furthermore, the hair treatment agent in any one of Claims 1-3 containing an oily component.   The hair treatment agent according to any one of claims 1 to 4, wherein at least one of the components (b) is a tertiary amine or a salt thereof.