JPH05229918A - Hair cosmetic - Google Patents

Abstract

PURPOSE:To provide a hair cosmetic capable of preventing the generation of sticky or dry hair and of giving good smoothness and tensible stiffness to the hair. CONSTITUTION:A hair cosmetic contains (A) a quaternary ammonium compound having an ether residue having an aliphatic group or aliphatic chain, an ester residue or acyl residue and a secondary or tertiary amino group, such as a compound of formula I [R<1> is 7-12C alkyl or alkenyl; R<2>-R<4> are 1-4C alkyl or hydroxyalkyl; M is -CONG- (G is H, 1-3C alkyl, hydroxyalkyl), O, COO; Y is G, group of formula II, but when G is alkyl or hydroxyalkyl, Y is not alkyl nor hydroxyalkyl ; X is H or OH; A is halogen ion, organic ion; (m) is 2,3; (n) is 0-5], and (B) fats and oils preferably in an A/B ratio of 0.05-10wt.%/0.05-20wt.%. The further addition of 0.1-10wt.% of a silicone derivative to the cosmetic can improve the touch of the cosmetic.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hair cosmetic such as a hair rinse, a hair conditioner, a hair treatment, a hair cream, etc., which imparts smoothness and firmness to the hair without making the hair sticky or dry.

[0002]

2. Description of the Related Art Conventionally, in order to improve the feel of hair, hair cosmetics have a mono- or di-linear long-chain alkyl quaternary ammonium salt or a mono- or di-branched long-chain alkyl quaternary ammonium salt. Cationic surfactants such as Further, in recent years, for the purpose of imparting suppleness and moisturizing feeling to hair, it has also been carried out to use fats and oils such as higher alcohols, glycerides, liquid paraffin and ester oils in combination with a cationic surfactant.

[0003]

However, this kind of hair cosmetics has insufficient smoothness and moist feeling at the time of finishing, and if the blending amount of the oil agent is increased to improve them, the residual amount of the oil agent remains. When applied to hair that has a feeling of feeling, that is, a greasy and sticky feeling, and is soft and firm and firm, there is a drawback that the feeling of volume is lost and a hairstyle as desired cannot be made.

Therefore, an object of the present invention is to obtain a hair cosmetic composition which is free from stickiness and dryness of the hair and can impart smoothness and firmness to the hair.

[0005]

Under the circumstances, the present inventors have conducted diligent studies to solve the above-mentioned problems, and as a result, when a specific quaternary ammonium type compound was used, the hair became greasy and dry. Found that a hair cosmetic that gives smoothness and firmness to hair can be obtained without
The present invention has been completed.

That is, the present invention provides the following components (A) and (B) (A) an ether residue, an ester residue or an acyl group having an aliphatic group or an aliphatic chain and a secondary or tertiary amino group. The present invention provides a hair cosmetic, which comprises a quaternary ammonium type compound (B).

The quaternary ammonium type compound of the component (A) used in the present invention has an ether residue, an ester residue or an acyl group having an aliphatic group or an aliphatic chain and a secondary or tertiary amino group. And examples thereof include compounds represented by the general formula (1).

[0008]

[Chemical 6]

[Wherein R ^{1 is a} linear or branched carbon number 7
21 represents an alkyl group or an alkenyl group. ^{R 2, R 3, R 4} : the same or different alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms. M: -CONG- (G is a hydrogen atom or a C1-C3 alkyl group or a hydroxyalkyl group), -O- or -COO- is shown. Y: hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, or a formula

[0010]

[Chemical 7]

A group represented by However, when G is an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group,
Y is not an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group. X: represents a hydrogen atom or a hydroxy group. A: Indicates a halogen ion or an organic anion. m: Indicates the number of 2 or 3. n: 0 or an integer of 1 to 5 is shown. However, when n = 1, X represents a hydrogen atom or a hydroxy group, and n = 0,
In the case of 2,3,4,5, X represents a hydrogen atom. ]

Of these, compounds represented by the general formula (2) are particularly preferable.

[0013]

[Chemical 8]

[In the formula, G represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group. R ¹ , R ² , R ³ , R ⁴ and Y: have the same meaning as described above. ]
And more preferably a compound represented by the general formula (3)

[0015]

[Chemical 9]

[Wherein R ¹ , R ² , R ³ , R ⁴ and A: have the same meanings as described above. ] Is preferred.

These quaternary ammonium type compounds can be produced according to known methods, and of these, for example, the compound represented by the general formula (3) can be produced according to the following reaction formula.

[0018]

[Chemical 10]

That is, a fatty acid (R ¹ CO ₂ H) is reacted with aminoethylethanolamine represented by the general formula (4) to form an imidazoline derivative represented by the general formula (5), and this derivative is then treated with an alkali. After the treatment, the quaternary ammonium salt type compound represented by the general formula (3) is synthesized by reacting with the compound represented by the general formula (6) to quaternize. In addition, it is more preferable to use a salt that has been desalted by electrodialysis or the like.

These quaternary ammonium type compounds can be used alone or in combination of two or more kinds, and 0.01 to 20% by weight (hereinafter simply indicated by%), particularly 0.05, in the total composition. It is preferably blended in an amount of 10%.

The fats and oils as the component (B) used in the present invention are not particularly limited as long as they are generally used in hair cosmetics. For example, they have a linear or branched alkyl group or alkenyl group. Higher alcohols; hydrocarbons such as liquid paraffin, petrolatum and solid paraffin; lanolin derivatives such as liquid lanolin and lanolin fatty acid; higher fatty acid esters, higher fatty acids, oils and fats such as long-chain amidoamines having an alkyl group or an alkenyl group Kinds; animal and vegetable fats and oils such as mink oil and olive oil. Among these, monoglycerides derived from saturated or unsaturated linear or branched fatty acids having 12 to 24 carbon atoms, and higher alcohols and higher alcohols having linear or branched alkyl or alkenyl groups having 12 to 26 carbon atoms Fatty acids are particularly preferable, specifically, oleic acid monoglyceride, palmitic acid monoglyceride, behenic acid monoglyceride, fatty acid monoglyceride such as isostearic acid monoglyceride, cetyl alcohol, stearyl alcohol, araquin alcohol, behenyl alcohol,
Caranavir alcohol, higher alcohols such as ceryl alcohol, stearic acid, myristic acid, behenic acid,
Higher fatty acids such as isostearic acid, 18-methyleicosanoic acid and coconut oil fatty acid can be mentioned.

These oils and fats can be used alone or in combination of two or more, and 0.01 to 30% in the total composition,
It is particularly preferable to add 0.05 to 20%.

The hair cosmetic composition of the present invention may further contain a silicone derivative as the component (C) in order to improve the feel. As such a silicone derivative,
For example:

(A) Dimethylpolysiloxane represented by the formula (7): (CH ₃ ) ₃ SiO [(CH ₃ ) ₂ SiO] _n1 Si (CH ₃ ) ₃ (7) (wherein n ₁ is 3 or more. As the dimethylpolysiloxane represented by the general formula (7) (indicating an integer), for example, those commercially available from Shin-Etsu Chemical Co., Ltd. under the trade name of KF96 can be used.

(B) Methylphenyl polysiloxane represented by the formula (8)

[0026]

[Chemical 11]

(In the formula, a, b and c are numbers such that their sum is 1 or more. However, when b is 0, c is not 0 and when c is 0, b is not 0) Methylphenyl polysiloxane represented by the formula (8) is also widely known, and for example, those commercially available from Shin-Etsu Chemical Co., Ltd. under a trade name such as KF50 can be used.

The amino-modified silicone represented by formula (iii) below _{^{(9) (R 5 d B}} (3-d)) -Si- (OSi (B) 2) n2 - [OSi (B e R 5 (2-e ₎ )] _n3 -OSi (R ⁵ _d B _(3-d) ) (9) [In the formula, B is a hydrogen atom, a phenyl group, a hydroxyl group, or a carbon number 1
Selected from the group consisting of alkyl groups of ~ 8, d is 0 or an integer of 1 to 3, e is 0 or 1, n ₂
Is 0 or an integer of 1 to 1999, and n ₃ is 1 to 2
000 is an integer, n ₂ + n ₃ is an integer of 1 to 2000, R ⁵ is a group —C _f H _2f L [where f is an integer of 2 to 8 and L is a formula]

[0029]

[Chemical 12]

(In the formula, Z is selected from the group consisting of a hydrogen atom, a phenyl group, a benzyl group and an alkyl group having 1 to 20 carbon atoms, and D ⁻ represents Cl ⁻ , Br ⁻ , I ⁻ or F ⁻ . )
Examples of the amino-modified silicone represented by the general formula (9) include those commercially available from Toray Dow Corning Silicone Co., Ltd. under trade names such as SF8417 and DC536, and aminoalkyl silicone emulsions. SM8702C (manufactured by Toray Dow Corning Silicone Co., Ltd.) or the like can be used.

(D) Fatty acid-modified polysiloxane represented by the formula (10)

[0032]

[Chemical 13]

[In the formula (10), g, h and i are 1 to 35
0 is a number, j is a number from 0 to 10, and R ⁶ is a carbon number from 9 to
21 represents an alkyl group]

(E) Formula (11-a) or formula (11-b)
Alcohol-modified silicone represented by

[0035]

[Chemical 14]

[In the formula, k and l represent a number of 1 to 500 (preferably 1 to 200), and R ⁷ and R ^{7 ′} represent C _n4 H
_2n4 (n ₄ is a number of 0 to 4) shows a]

(F) Aliphatic alcohol-modified silicone represented by the formula (12)

[0038]

[Chemical 15]

[In the formula (12), m ₁ , o and q ₁ are a total of ₁ to 300, and r is a number of 0 to 5,
R ⁸ represents C _n5 H _{2n5 + 1} (n ₅ represents a number of 4 to 22)]

(G) Polyether-modified silicone represented by the following formulas (13) to (16)

[0041]

[Chemical 16]

A ₁ : an alkyl group having 1 to 12 carbon atoms or a hydrogen atom x ₁ : 0 to 50 z ₁ : 0 to 10 m ₂ : 1 to 2000 n ₆ : 1 to 1000 y ₁ : 0 to 50 (x ₁ + Y ₁ ≧ 1)]

(H) Epoxy-modified silicone represented by the formula (17)

[0044]

[Chemical 17]

[In the formula (17), α is a number of 1 to 500 (preferably 1-250) and β is a number of 1 to 50 (preferably 1).
To 30), and R ¹⁰ represents an alkylene group having 1 to 3 carbon atoms]

(B) Fluorine-modified silicone represented by the formula (18)

[0047]

[Chemical 18]

[In the formula (18), γ represents a number of 1 to 400 (preferably 1 to 250)]

(N) Cyclic silicone represented by the formula (19)

[0050]

[Chemical 19]

[In the formula (19), δ represents a number of 3 to 8,
R ¹¹ represents an alkyl group having 1 to 3 carbon atoms]

(L) Formula (20-a) or Formula (20-b)
Alkyl-modified silicone represented by

[0053]

[Chemical 20]

[In the formula (20-a), ε and η are 1 to 5 respectively.
00 (preferably 1 to 200), R ¹² is an alkyl group having 2 to 18 carbon atoms, R ¹³ is C _n7 H _2n7 (n ₇ is 0 to 0).
4)]

[0055]

[Chemical 21]

[In the formula (20-b), θ and κ are 1 to 5 respectively.
00 (preferably 1 to 200) and R ¹⁴ represents an alkyl group having 10 to 16 carbon atoms]

Any of these silicone derivatives can sufficiently exert the effects of the present invention, but from the viewpoint of improving the smoothness and firmness and firmness of hair, (i) dimethyl is particularly preferable. It is preferable to use polysiloxane, (c) amino-modified silicone, and (to) polyether-modified silicone.

In (a) dimethylpolysiloxane, n ₁ in the formula (7) is 3 to 900 depending on the finished feeling.
Although it can be selected up to 0, it is 1000 or more, particularly 2000 to 70, in order to sufficiently impart a firmness and elasticity to the hair.
About 00 is preferable. (C) Amino-modified silicones are those in which d = 0, e = 1, f = 3 in formula (9), B is a hydroxyl group and a methyl group, and L is —NHCH ₂ CH ₂ NH _2, that is, USA. The one represented by the name of amodimethicone in the CTFA dictionary is particularly preferably used. (G) As the polyether-modified silicone, the polyoxyalkylene group in the molecule is 3 to 30%, particularly 5 to
Those containing 25% are preferably used.

These silicone derivatives can be used singly or in combination of two or more kinds.
It is preferable to add 1 to 20%, particularly 0.1 to 10%.

Further, the hair cosmetic composition of the present invention may contain, if necessary, components that are usually added to cosmetics, pharmaceuticals, foods, etc., such as anti-dandruff agents such as Zpt, bactericides, vitamins and the like. Medicinal agents; preservatives such as parabens; humectants such as propylene glycol, glycerin, diethylene glycol monoethyl ether, sorbitol, panthenol, glycine betaine; thickeners such as water-soluble polymers; coloring agents such as dyes and pigments; Conditioning agents such as fluoropolyethers and cationic polymers; pearling agents such as glycol esters; chitosan derivatives such as hydroxypropyl chitosan; hair setting polymers such as acrylic resin liquids;
Various fragrances; Other Encyclopedia of Conditioning Rinse Ingredients [EN
CYCLOPEDIA OF CONDITIONIN
G RINSE INGREDIENTS (MICEL
The components listed in LE PRESS 1987)] may be appropriately blended within a range that does not impair the effects of the present invention.

The hair cosmetics of the present invention refer to all cosmetics excluding detergents applied to the hair, for example, pre-shampoo agents, hair conditioners, hair conditioners, hair treatments, set lotions, blow styling. Lotion, hair spray, foam styling agent, gel styling agent, hair liquid, hair tonic, hair cream, permanent wave first agent,
Includes permanent wave second agent, permanent hair dye, temporary hair dye, and the like. Further, the dosage form may be in various forms such as an aqueous solution, an ethanol solution, an emulsion, a suspension, a gel, a liquid crystal, a solid, a foam, an aerosol, etc., depending on its use.

The hair cosmetic composition of the present invention is prepared by adding the above-mentioned component (A) and component (B), and optionally component (C) and optional component to heated water according to a conventional method, and stirring the mixture. It can be manufactured by a cooling method. On this occasion,
It is also possible to use solvents such as alcohol, propylene glycol and glycerin. Further, in this case, when the hair cosmetic is hair rinse or the like, if necessary, an organic acid such as citric acid or lactic acid is added so that the pH of the 5% aqueous solution thereof becomes 3 to 8 which is the same as that of the usual hair rinse agent. It is preferable to adjust with inorganic acids such as phosphoric acid and hydrochloric acid; inorganic alkalis such as caustic soda; organic alkalis such as triethanolamine.

Table 1 shows particularly preferable composition ranges including the optional components of the hair cosmetic composition of the present invention.

[0064]

[Table 1]

In the case of aerosols such as mousses and hair sprays, in addition to the above composition (stock solution), propellants such as fluorocarbon, liquefied petroleum gas and dimethyl ether have an internal pressure of 2.0.
~ 6.0 kg / cm ² G, that is, 1 to 1 in the total composition
It is preferable to use 20%.

[0066]

EFFECTS OF THE INVENTION The hair cosmetic composition of the present invention is particularly soft because it can impart smoothness and elasticity to the hair without causing tackiness and dryness of the hair.
It is suitable for hair without tension.

[0067]

EXAMPLES Next, the present invention will be further described with reference to examples, but the present invention is not limited to these examples.
The test method used in this example is as follows. (1) Sensory evaluation 25 g (15 cm in length, 60 μm in average diameter) of Japanese women's hair that has not been subjected to chemical treatment such as cold perm is bundled, and 2.5 g is added to this hair bundle for rinsing type hair cosmetics. The agent was evenly applied, rinsed with running water for 30 seconds, towel-dried and then dried with a dryer. Further, with respect to the hair cosmetics of the soot-free type, a predetermined amount of the agent was applied to this hair bundle and then air-dried.
The hair bundle was evaluated for its smoothness, firmness, stiffness and stickiness according to the following criteria. (Smoothness) ◎: Very smooth. ○: Smooth. Δ: Neither can be said. X: Not smooth (Silience and elasticity) ◎: Very good. ○: Yes. Δ: Neither can be said. X: None (Stickiness) A: Very little. ○: Little. Δ: Neither can be said. X: Many.

Example 1 A hair rinse agent having the composition shown in Table 2 was prepared and its rinse performance was examined. The results are shown in Table 2.

[0069]

[Table 2]

Example 2 A hair rinse composition having the following composition was prepared and permed.
Comparison of rinsing performance using 10 panelists
It was evaluated by the method. The comparison standard is +2 if it is very good,
The good case was set to +1. The results are shown in Table 3. Invention product 3: (%) (1) 2-hydroxy-3-[(2-hydroxyethyl) [2-[(1-oxotetradecyl) amino] ethyl] amino] propyl-N, N, N-trimethyl Ammonium chloride 1.0 (2) Cetyl alcohol 3.0 (3) Amino-modified silicone ^{* 1} 1.0 (4) Propylene glycol 3.0 (5) Hydroxyethyl cellulose 0.5 (6) Water 91.1 (7) Perfume 0.4 * 1: Toray Dow Corning Silicone Co., Ltd. aminoalkyl silicone emulsion SM8702C Comparative product 3: (%) (1) Stearyl trimethyl ammonium chloride 1.0 (2) Cetyl alcohol 3.0 (3) Propylene glycol 3.0 (4) Hydroxyethyl cellulose 0.5 (5) Water 92.1 ( 6) Fragrance 0.4

[0071]

[Table 3]

Example 3 Hair rinse composition: A hair rinse composition having the composition shown in Table 4 was produced by a conventional method.

[0073]

[Table 4]

Example 4 Hair Treatment Composition: A hair treatment composition having the composition shown in Table 5 was produced by a conventional method.

[0075]

[Table 5]

Example 5 Styling lotion composition: A styling lotion composition (invention product 10) having the following composition was produced by a conventional method. (%) (1) 2-hydroxy-3-[(2-hydroxyethyl) [2-[(1-oxohexadecyl) amino] ethyl] amino] propyl-N, N, N-trimethylammonium chloride 0 .5 (2) polyethylene glycol 0.5 (3) acrylic resin alkanolamine liquid 5.0 (4) propylene glycol 1.0 (5) methacrylic ester polymer 1.0 (6) ethanol 20.0 (7) fragrance 0.4 (8) Water balance 100.0

Example 6 Conditioning Foam Composition: A conditioning foam composition having the following composition (Product 11 of the present invention) was produced by a conventional method. (%) (1) 2-hydroxy-3-[(2-hydroxyethyl) [2-[(1-oxododecyl) amino] ethyl] amino] propyl-N-hydroxyethyl-N, N-trimethylammonium Chloride 0.5 (2) Octyldodecyl myristate 1.0 (3) Dipropylene glycol 1.0 (4) Glycerin 2.5 (5) Liquid paraffin 2.5 (6) Polyoxyethylene sorbitan monostearate 0. 2 (7) Ethanol 5.0 (8) Methylparaben 0.1 (9) Perfume 0.1 (10) Propellant (LPG) 10.0 (11) Water balance 100.0

Example 7 Hair Cream Composition: A hair cream composition having the following composition (product 12 of the present invention) was produced by a conventional method. (%) (1) 2-hydroxy-3-[(2-hydroxyethyl) [2-[(1-oxododecyl) amino] ethyl] amino] propyl-N, N, N-trimethylammonium chloride 2.0 (2) Cetyl trimethyl ammonium chloride 1.0 (3) Polyoxyethylene sorbitan monostearate (EO = 20) 0.5 (4) Cetyl alcohol 5.0 (5) Dipropylene glycol 6.0 (6) Glycerin 10 .0 (7) Liquid paraffin 3.0 (8) Amino-modified silicone ^{* 5} 2.0 (9) Fragrance 0.4 (10) Water balance 100.0 * 5: Amino manufactured by Toray Dow Corning Silicone Co., Ltd. Alkyl silicone emulsion SM8702C

[Procedure amendment]

[Submission date] June 5, 1992

[Procedure Amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0028

[Correction method] Change

[Correction content]

[0028] (c) amino-modified silicone represented by formula ^{_{(9) (R 5 d)}} (B 3-d) SiO- [Si (B 2) O] n2 - [Si (B e) (R 5 2- ^{_{e) 0] n3 -Si (R}} 5 d) (B 3-d) (9) wherein, B represents a hydrogen atom, a phenyl group, a hydroxyl group, C 1 -C
Selected from the group consisting of alkyl groups of 8 to 8, d is an integer of 0 to 3 , e is 0 or 1, and n ₂ is 0 to 19
Shows an integer of 99 , n ₃ shows an integer of 1 to 2000,
n ₂ + _{n 3} represents an integer of 1 - 2000, ^{R 5} is a group -C
_f H _2f L [where f is an integer of 2 to 8 and L
Is an expression

Claims (5)

[Claims] 1. The following components (A) and (B) (A) Quaternary ammonium having an aliphatic group or an ether residue having an aliphatic chain, an ester residue or an acyl group and a secondary or tertiary amino group. A hair cosmetic comprising a type compound (B) an oil or fat. 2. The hair cosmetic composition according to claim 1, wherein the component (A) is a compound represented by the general formula (1). [Chemical 1] [In the formula, R ^{1 represents a} linear or branched alkyl group or alkenyl group having 7 to 21 carbon atoms. ^{R 2, R 3, R 4} : the same or different alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms. M: -CONG- (G is a hydrogen atom or a C1-C3 alkyl group or a hydroxyalkyl group), -O- or -COO- is shown. Y: a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, or a compound represented by the formula: Represents a group represented by. However, when G is an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, Y is 1 carbon atom.
It is not an alkyl group or hydroxyalkyl group of ~ 3. X: represents a hydrogen atom or a hydroxy group. A: Indicates a halogen ion or an organic anion. m: Indicates the number of 2 or 3. n: 0 or an integer of 1 to 5 is shown. However, when n = 1, X represents a hydrogen atom or a hydroxy group, and n = 0,
In the case of 2,3,4,5, X represents a hydrogen atom. ] 3. The hair cosmetic composition according to claim 1, wherein the component (A) is a compound represented by the general formula (2). [Chemical 3] [In the formula, R ^{1 represents a} linear or branched alkyl group or alkenyl group having 7 to 21 carbon atoms. ^{R 2, R 3, R 4} : the same or different alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms. G: A hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group is shown. Y: a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, or a compound represented by the formula: Represents a group represented by. However, when G is an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, Y is 1 carbon atom.
It is not an alkyl group or hydroxyalkyl group of ~ 3. X: represents a hydrogen atom or a hydroxy group. A: Indicates a halogen ion or an organic anion. m: Indicates the number of 2 or 3. n: 0 or an integer of 1 to 5 is shown. However, when n = 1, X represents a hydrogen atom or a hydroxy group, and n = 0,
In the case of 2,3,4,5, X represents a hydrogen atom. ] 4. The hair cosmetic composition according to claim 1, wherein the component (A) is a compound represented by the general formula (3). [Chemical 5] [In the formula, R ^{1 represents a} linear or branched alkyl group or alkenyl group having 7 to 21 carbon atoms. ^{R 2, R 3, R 4} : the same or different alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms. A: Indicates a halogen ion or an organic anion. ] 5. The hair cosmetic composition according to claim 1, which further comprises (C) a silicone derivative.