JPH0543433A - Shampoo composition - Google Patents

Abstract

PURPOSE:To obtain the subject composition, containing a specific quaternary ammonium salt type compound and a silicone derivative, having low irritancy to the skin and hair, excellent in high foaming properties, high washing properties and resistance to hard water and simultaneously capable of exhibiting excellent conditioning effects. CONSTITUTION:A shampoo composition containing a quaternary ammonium salt type compound having secondary or tertiary amino group and quaternary ammonium group in an aliphatic chain or an ether, an ester or an acyl compound having the aliphatic chain {preferably a compound expressed by formula I [R<1> is alkyl or alkenyl; R<2> to R<4> are alkyl or hydroxyalkyl; M is CONG (G is H, alkyl or hydroxyalkyl), O or COO; Y is H, alkyl, etc.; X is H or OH; A is halogen, etc.; m is 2 or 3; n is 0-5] (e.g. a compound expressed by formula II) and a silicone derivative (e.g. dimethylpolysiloxane). The composition is capable of imparting touch such as flexibility and smoothness and excellent combing properties to hair after washing.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a shampoo composition which is mildly irritating to skin and hair, has good foaming properties and cleansing properties, and has an excellent conditioning effect.

[0002]

2. Description of the Related Art In recent years,
Surfactants used as detergents are naturally required to have excellent surface activity (foamability / detergency), and are biodegradable, especially in the case of human detergents, they are safe. It is also required to have excellent physical properties such as low irritation to eyes and skin. Anionic surfactants (soap, linear alkylbenzene sulfonate (LAS), alkyl sulfate ester salt (AS), polyoxyethylene alkyl ether sulfate ester salt (AES), α
-Olefin sulfonate (AOS) etc. have good detergency and foamability, but on the other hand, they are irritating to eyes and skin. On the other hand, monoalkyl phosphates, N-acylglutamates, N-acyl-N-alkyl-β-alanine salts, and N-acyl-Ns which have been proposed as mild activators.
N-acyl amino acid salts such as -alkyl glycine salts are low in irritation but inferior in original properties of detergents such as hard water resistance, foaming property and detergency. Therefore, a shampoo that has a low irritation to hair and skin and is excellent in detergency, foamability, foam quality, and hard water resistance, and also has an excellent conditioning effect has been earnestly desired.

[0003]

Means for Solving the Problems As a result of earnest research in such an actual situation, the inventors of the present invention have a surfactant ability,
A novel quaternary ammonium salt-type compound having excellent foaming power and detergency and having low irritation was discovered, and a detergent composition containing such a specific quaternary ammonium salt-type compound is applied to skin and hair. It has been found that it is hypoallergenic and has washing properties, foaming properties and conditioning properties suitable for shampoo and the like, and has already filed a patent application (Japanese Patent Application No. 2-274860 and Japanese Patent Application No. 3-160296). The inventors of the present invention have further earnestly studied to solve the above problems, and as a result,
A shampoo composition containing a primary ammonium salt type compound and a silicone derivative is hypoallergenic to the skin and hair, has high foaming property, high detergency, is excellent in hard water resistance, and has an excellent conditioning effect. The present invention has been completed, and it was found that the hair has a good smoothness, smoothness to fingers, and good cohesion after drying. That is, the present invention provides (a) a quaternary ammonium salt-type compound having a secondary or tertiary amino group and a quaternary ammonium group in an aliphatic chain, or an ether, ester or acyl compound having an aliphatic chain, The present invention provides a shampoo composition containing a silicone derivative.

The shampoo composition of the present invention containing the quaternary ammonium salt type compound as the component (a) and the silicone derivative as the component (b) is a hair wash for infants, a shampoo for people who wash their hair daily, It is also suitable as a shampoo for those who have to contact the shampoo for a long time professionally. 4 of the component (a) in the shampoo composition of the present invention
The compounding amount of the primary ammonium salt type compound is 0.1 to 50% by weight for the liquid shampoo, 0.1 to 80% by weight for the paste shampoo, and 50 to 99% by weight for the solid or powdery shampoo. Is preferred.

The compound represented by the general formula (1) is preferable as the quaternary ammonium salt type compound of the component (a) in the present invention.

[0006]

[Chemical 6]

[Wherein R ^{1 is a} linear or branched carbon number of 7 to
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 H or an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group), -O- or -COO-. Y: H, an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, or a formula

[0008]

[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: H or a hydroxy group. A: Halogen ion or OH, an organic anion such as an alkylsulfate group having 1 to 4 carbon atoms. m: Indicates the number of 2 or 3. n: 0 or an integer of 1 to 5 is shown. However, when n = 1, X = H or a hydroxy group is shown, and n = 0, 2, 3,
In the case of 4 and 5, X = H is shown. Among the quaternary ammonium salt type compounds represented by the above general formula (1), particularly the general formula
The compound represented by (2) is preferable.

[0010]

[Chemical 8]

Further preferred as the quaternary ammonium salt type compound as the component (a) are compounds represented by the general formula (3), and among these compounds, the following general formula (4) and
The compound represented by (5) may be contained as a by-product.

[0012]

[Chemical 9]

Among the quaternary ammonium salt type compounds represented by the above general formula (3), it is particularly desirable that R ₁ is a linear or branched alkyl group or alkenyl group having 11 to 17 carbon atoms. Furthermore, it is more preferable that the group represented by R ¹ CO— is a lauroyl or myristoyl group, and R ² , R ³ and R ⁴ are all methyl groups.

The quaternary ammonium salt type compound represented by the above general formula (3) used in the present invention is produced by the following method. That is, as shown in the following production flow, a fatty acid (R ¹ CO ₂ H) is reacted with aminoethylethanolamine represented by the following general formula (6) to produce an imidazoline derivative represented by the following general formula (7). Then, the derivative is treated with an alkali and then reacted with a compound represented by the general formula (8) to quaternize to synthesize a quaternary ammonium salt type compound represented by the general formula (3). Manufacturing flow

[0015]

[Chemical 10]

(In the formula, R ¹ , R ² , R ³ , R ⁴ and A have the above-mentioned meanings.) The silicone derivative of the component (b) used in the present invention has the following 1) to 9). What is shown is illustrated. 1) Dimethyl polysiloxane

[0017]

[Chemical 11]

2) Methylphenyl polysiloxane

[0019]

[Chemical formula 12]

3) Polyether modified silicone

[0021]

[Chemical 13]

4) Epoxy-modified silicone

[0023]

[Chemical 14]

X ₂ is 1 to 500 (preferably 1 to 250),
y ₂ represents a number of 1 to 50 (preferably 1 to 30), and R ⁵ represents an alkylene group having 1 to 3 carbon atoms. 5) Fluorine modified silicone

[0025]

[Chemical 15]

Where x ₃ is 1 to 400 (preferably 1 to 250)
Represents the number of. 6) Alcohol-modified silicone

[0027]

[Chemical 16]

Where x ₄ and y ₄ are each 1 to 500 (preferably 1
Represents the number of ~200), R ⁶ represents _{C n "H 2n" (n} "= 0~4). 7) alkyl-modified silicone

[0029]

[Chemical 17]

Where x ₅ and y ₅ are each 1 to 500 (preferably 1
~ 200), R ⁷ is an alkyl group having 2 to 18 carbon atoms, R ⁸
Is C _{n "} H _2n" (n "= 0-4), and R ⁹ is an alkyl group having 10 to 16 carbon atoms. 8) Alkoxy-modified silicone

[0031]

[Chemical 18]

Here, R ¹⁰ represents a methyl group or a phenyl group, l ₁ represents an integer of ₁ to 3000, m ₂ and n ₂ represent m ₂ + n ₂ = 1 to
Represents an integer of 500, R ¹¹ represents an alkyl group having 1 to 28 carbon atoms (preferably 12 to 22 carbon atoms), and k represents an integer of 0 to 6. 9) Amino-modified silicone

[0033]

[Chemical 19]

Of these, a particularly preferred amino-modified silicone is represented by the following general formula.

[0035]

[Chemical 20]

(In the formula, R ¹⁴ , m ₃ and n ₃ have the above-mentioned meanings.) A typical amino-modified silicone in the present invention is represented by the following general formula and has an average molecular weight of about 3 , 00
It is from 0 to 100,000, which is called CTFA dictionary (American, Cosmetics) under the name of Amodimethicone.
Ingredient Dictionary) 3rd edition.

[0037]

[Chemical 21]

(In the formula, m ₃ and n ₃ have the above meanings.) The above amino-modified silicone is preferably used as an aqueous emulsion, and the aqueous emulsion is, for example,
According to the method described in JP-B-56-38609, cyclic diorganopolysiloxane and an organodialkoxysilane having an aminoalkyl group and a hydroxy group, a hydroxyalkyl group, an oxyalkylene group, or a polyoxyalkylene group, Obtained by emulsion polymerization in the presence of a quaternary ammonium salt surfactant and water. When the amino-modified silicone is used as an aqueous emulsion, the amount of the amino-modified silicone contained in the aqueous emulsion is usually 20 to 60% by weight, preferably 30 to
It is 50% by weight. Commercially available preferred amino-modified silicone aqueous emulsions are SM 8702C (manufactured by Toray Silicone Co., Ltd.) and DC 929 (manufactured by Dow Corning Co., Ltd.).
Etc.

The above-mentioned silicone derivative of the component (b) can be used alone or in combination of two or more kinds, and is preferably 0.01 to 0.01 in the shampoo composition of the present invention.
2% by weight, and more preferably 0.1 to 0.8% by weight.

Further, in the detergent composition of the present invention, the use of a nonionic activator or an amphoteric activator, which has been widely used in the past, in combination with the above-mentioned quaternary ammonium salt type compound and silicone derivative results in further foaming. To be enhanced. Examples of amphoteric activators include amidobetaine, alkyltaurine, carbobetaine, hydroxysulfobetaine, phosphobetaine and the like. However, the effect is enhanced especially by combination with a sugar-based nonionic activator such as alkyl polyglucoside or amine oxide. In addition to the above quaternary ammonium salt type compound, the silicone derivative and the above-mentioned activator, various polymers, for example, water-soluble polymers such as carboxymethyl cellulose are blended as a conditioning component in the detergent composition of the present invention. Similarly, cationic activators, higher alcohols and the like can be added. Also, if necessary, fragrances, pigments, preservatives, antioxidants, thickeners and anti-dandruff agents, bactericides, antiphlogistics, vitamins and other medicinal agents, and others, Encyclopedia of Shampoo Ingredients (Mi-cellep
The components listed in ress, 1985) can also be added.

[0041]

EXAMPLES The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. Example 1 Various shampoos having the following formulations were prepared and their performance was evaluated according to the following evaluation criteria. The results are shown in Table 1.

<Formulation Example> Comparative product 1 Polyoxyethylene (3) lauryl sulfate triethanolamine salt 17% by weight Lauric acid diethanolamide 3 Sodium benzoate 0.3 Fragrance Colorant Appropriate amount Water balance (pH 7.0) Comparative product 2 Polyoxyethylene (3) Lauryl sulphate triethanolamine salt 17% by weight Lauric acid diethanolamide 3 Polyether-modified silicone (KF-352A manufactured by Shin-Etsu Chemical Co., Ltd.) 0.5 Sodium benzoate 0.3 Perfume proper amount Colorant proper amount Water balance (pH 7 0.0) Reference product 1

[0043]

[Chemical formula 22]

Lauryl dimethylamine oxide 5% by weight Carboxymethyl cellulose (No. 1330 manufactured by Daicel) 0.3 Sodium benzoate 0.3 Amount of flavor Amount of colorant Amount of water balance (pH 7.0) Product 1 of the present invention

[0045]

[Chemical formula 23]

2-Dodecylhexadecyltrimethylammonium chloride 1% by weight Polyoxyethylene (3) lauryl glucoside 5 dimethylpolysiloxane (KF-96 manufactured by Shin-Etsu Chemical Co., Ltd., viscosity 200cs) 0.5 Xanthan gum (Echo Gum T manufactured by Dainippon Pharmaceutical Co., Ltd.) 0.3 Sodium benzoate 0.3 Perfume Appropriate amount Colorant Appropriate amount Water balance (pH 7.0) Inventive product 2

[0047]

[Chemical formula 24]

5% by weight of betaine lauric acid amidopropyldimethylaminoacetate Polyether-modified silicone (KF-352A manufactured by Shin-Etsu Chemical Co., Ltd.) 0.5 Carboxymethyl cellulose (No1330 manufactured by Daicel) 0.3 Sodium benzoate 0.3 Percentage of fragrance Colorant of appropriate amount Water balance ( pH 7.0) Invention product 3

[0049]

[Chemical 25]

Lauryl dimethylamine oxide 5% by weight Amino-modified silicone emulsion (Toray Silicone SM8702C) 0.5 Xanthan gum (Echogum T manufactured by Dainippon Pharmaceutical Co., Ltd.) 0.3 Sodium benzoate 0.3 Fragrance Appropriate amount Colorant Appropriate amount Water balance (pH 7.0) <Evaluation criteria ＞ Feeling of hair when washing hair: ◎ Soft and smooth with very good finger passage ○ Smooth and with good finger passage △ Hair does not slip, finger passage is not good × Squeaky and tangled hair Finger passage characteristics: ◎ Squeaky There is no scratches and the fingers are very good. ○ The squeak is weak and the fingers are good. △ The squeak is slightly strong and the fingers are difficult to pass. × The squeak is strong and the fingers are not sticky .: Sticky and slightly sticky △ Somewhat sticky × With stickiness Cohesiveness: ◎ Very cohesive ○ Natural cohesion △ Slightly cohesive Poor × Lots of messy hair and poorly organized Combability: ◎ Very good combability and smoothness ○ Good combability and smoothness △ Slightly snags through comb × Poor combing, such as hair tips Skin irritation: ○ No stimulation to slight stimulation △ Weak stimulation × Medium to strong stimulation

[0051]

[Table 1]

[0052]

EFFECTS OF THE INVENTION The shampoo composition of the present invention exhibits creamy and good foaming, has an excellent moisturizing feel at the time of washing and rinsing, and has suppleness, smoothness and the like on the hair after washing and has a smooth combing effect. Since it can impart excellent conditioning effects such as goodness and is mild and hypoallergenic to the skin and hair, it can be suitably used especially for hair shampoo.

Claims (4)

[Claims] 1. A quaternary ammonium salt type compound having a secondary or tertiary amino group and a quaternary ammonium group in an aliphatic chain or an ether, ester or acyl compound having an aliphatic chain, and (b) A shampoo composition comprising a silicone derivative. 2. The shampoo composition according to claim 1, wherein the quaternary ammonium salt type compound as 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 H or an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group), -O- or -COO-. Y: H, 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 a hydroxyalkyl group of ~ 3. X: H 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 = H or a hydroxy group is shown, and n = 0, 2, 3,
In the case of 4 and 5, X = H is shown. ] 3. The shampoo composition according to claim 1, wherein the quaternary ammonium salt type compound as 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: H or an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group. Y: H, 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 not an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group. X: H 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 = H or a hydroxy group is shown, and n = 0, 2, 3,
In the case of 4 and 5, X = H is shown. ] 4. The shampoo composition according to claim 1, wherein the quaternary ammonium salt type compound as the component (a) is a compound represented by the general formula (3). [Chemical 5] (In the formula, R ¹ is a linear or branched alkyl group or alkenyl group having 7 to 21 carbon atoms, R ² , R ³ and R ⁴ are the same or different and each is an alkyl group having 1 to 4 carbon atoms or hydroxyalkyl. The group, A represents a halogen ion or an organic anion.)