JPH0532996A - Detergent composition - Google Patents

Abstract

PURPOSE:To obtain a creamy detergent composition, containing a specific quater nary ammonium salt type compound and a cationic surfactant, having good foaming with low irritancy and excellent in conditioning properties. CONSTITUTION:The objective composition containing (A) 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 and preferably expressed by formula I [R<1> is 7-21C alkyl or alkenyl; R<2> to R<4> are 1-4C alkyl or hydroxyalkyl; M is -CONG(G is H, 1-3C alkyl or hydroxyalkyl), -O- or -COO-; Y is H, 1-3C alkyl or hydroxyalkyl] and (B) a cationic surfactant preferably expressed by the formula II [at least one of R<5> to R<8> is 8-28C (substituted) alkyl or alkenyl and the rest are benzyl, 1-5C alkyl, etc.; Z is halogen or organic anion].

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a detergent composition which is mild to skin and hair, and which is suitable for body shampoos, shampoos for hair and the like, and which has detergency, foaming and conditioning properties.

[0002]

2. Description of the Related Art In recent years,
A cleaning composition for body and hair is naturally required to have excellent surface activity (foaming property, detergency), as well as various physical properties such as safety and low irritation to eyes and skin. Excellent,
In addition, it is required to have a high conditioning effect. However, the cationic activator generally used for rinsing and the like has excellent conditioning properties, but adding an anionic activator to the detergent composition containing the detergent as the main component reduces the foaming property and stabilizes the composition. It has been considered difficult from the viewpoint of sex.

[0003]

[Means for Solving the Problems] Under such circumstances, the present inventors have conducted diligent research to solve the above problems, and as a result,
A detergent composition containing a specific quaternary ammonium salt-type compound as a cleansing active ingredient has low irritation to skin and hair, and has excellent foaming properties and cleansing properties, and moreover, as a conditioning component, a cationic interface. The present invention has been completed by finding that an activator can be added stably without lowering the foaming property. 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; ) A detergent composition comprising a cationic surfactant.

The detergent composition of the present invention containing the quaternary ammonium salt type compound of the above component (a) and the cationic surfactant of the component (b) is a hair / skin cleanser for infants and daily hair wash. Shampoos for people, and shampoos for people who have to contact professional shampoos for a long time,
It is suitable as a light detergent for fibers such as wool and a soft surface detergent for metals, tableware and the like.

The content of the quaternary ammonium salt type compound of the above-mentioned component (a) in the detergent composition of the present invention is 0.1 to 50% by weight in the case of a liquid detergent and 0.1 in the case of a paste-like detergent.
~ 80% by weight, or 50 for solid or powder cleaners
A range of up to 99% by weight is preferred. The amount of the cationic surfactant as the component (b) is 0.05 to 5% by weight in the case of a liquid detergent, 0.05 to 10% by weight in the case of a paste detergent, and in the case of a solid or powder detergent. The range of 0.05 to 10% by weight is preferred. As the quaternary ammonium salt type compound of the component (a) in the present invention, the compound represented by the general formula (1) is preferable.

[0006]

[Chemical 6]

[Wherein R ^{1 is a} straight or branched chain having 7 to 7 carbon atoms]
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: shows 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, in the case of 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 general formula (1), the compound represented by the general formula (2) is particularly preferable.

[0010]

[Chemical 8]

Further preferred as the quaternary ammonium salt type compound of 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. Further, 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). It is preferable that the detergent composition is desalted by electrodialysis or the like from the viewpoint of solubility and viscosity characteristics of the water-soluble polymer as a detergent composition. Manufacturing flow

[0015]

[Chemical 10]

(In the formula, R ¹ , R ² , R ³ , R ⁴ and A have the above-mentioned meanings.) As the cationic surfactant as the component (b) used in the present invention, for example, the following general formula Examples thereof include quaternary ammonium salts represented by (9) or (10).

[0017]

[Chemical 11]

(In the formula, at least one of R ⁵ , R ⁶ , R ⁷ and R ⁸ may be substituted with an alkoxy, alkenyloxy, alkanoylamino or alkenoylamino group having 8 to 28 carbon atoms in total. A good alkyl or alkenyl group, the rest is a benzyl group, an alkyl group having 1 to 5 carbon atoms or a hydroxyalkyl group, R ⁹ is an alkylene group having 2 to 3 carbon atoms, and Z is a halogen ion or an organic anion. And a is an integer of 1 to 20) Among such cationic surfactants, a quaternary ammonium salt represented by the general formula (9) is preferable, and a quaternary ammonium salt represented by the general formula (9) is further preferable. As preferable ammonium salts,
Examples include branched quaternary ammonium salts represented by the following general formulas (11) to (13).

[0019]

[Chemical 12]

The branched quaternary ammonium salt represented by the general formula (11) is usually synthesized by using, for example, an oxo alcohol having 8 to 16 carbon atoms as a raw material, and an example thereof is an alkyl derived from oxo alcohol. Examples thereof include a dialkyldimethylammonium salt having a group, a dialkylmethylhydroxyethylammonium salt, and a dialkylmethylbenzylammonium salt.

In the present invention, the branching ratio of R ^{10 in} the formula (11) is
Usually, 10 to 100% is used, but 10 to 50% is particularly preferable. Further, those having a total carbon number of R ¹⁰ of 8 to 16 are used, but those having a constant distribution are preferable, and those having the distribution shown below are particularly preferable. C ₈ ~C _11: 5% or less _{C 12: 10~35% C 13:} 15~40% C 14: 20~45% C 15: 5~30% C 16: 5% or less such branched quaternary ammonium Specific examples of the salt include dialkyldimethylammonium chloride having an alkyl group having 8 to 16 carbon atoms and a branching rate of 10 to 50%.
The branched quaternary ammonium salt represented by the general formula (12) is usually a Guerbet alcohol having 8 to 28 carbon atoms.

[0022]

[Chemical 13]

It is synthesized using as a raw material. Preferable examples of the branched quaternary ammonium salt include alkyl trimethyl ammonium salt having an alkyl group derived from Guerbet alcohol, alkyl dimethyl benzyl ammonium salt, dialkyl dimethyl ammonium salt,
Examples thereof include dialkylmethylhydroxyethylammonium salt and dialkylmethylbenzylammonium salt. Furthermore, among these, particularly preferred specific examples are:
Examples thereof include 2-decyltetradecyltrimethylammonium chloride, 2-dodecylhexadecyltrimethylammonium chloride, di-2-hexyldecyldimethylammonium chloride and di-2-octyldodecyldimethylammonium chloride.

A preferred example of the methyl-branched quaternary ammonium salt represented by the general formula (13) is one in which the sum of s and t is 15. In addition, the general formula (9), (10), (11), (1
Specific examples of Z, which is a counter ion of the quaternary ammonium salt represented by 2) and (13), include halogen ions such as chlorine, iodine, and bromine; methosulfate, ethosulfate, metphosphate, etophosphate, etc. The organic anions of

Further, in the detergent composition of the present invention, the above-mentioned (a) component quaternary ammonium salt type compound and (b) component cationic surfactant and other conventional amphoteric surfactants or Foaming is even further enhanced by the use in combination with nonionic activators. Examples of amphoteric activators include amidobetaine, carbobetaine, sulfobetaine, phosphobetaine, hydroxysulfobetaine and the like. Examples of nonionic activators include amine oxides, sugar-based nonionic activators such as alkyl glucosides, mono- and dialkanolamides, and the like.

The detergent composition of the present invention includes the above (a)
In addition to the quaternary ammonium salt-type compound as the component and the above-mentioned activator, various polymers such as water-soluble polymers such as carboxymethyl cellulose, anionic polymers such as acrylic acid-based polymers or water-dispersible silicone derivatives are blended as a conditioning component. In addition, higher alcohols can be added in the same manner. In addition, if necessary, fragrances, pigments, preservatives, antioxidants, thickeners and anti-dandruff agents, bactericides, antiphlogistics, vitamins and other medicinal ingredients, and others, Encyclopedia of Shampoo Ingredients (Micelle p
Ress, 1985) can be added.

[0027]

EFFECTS OF THE INVENTION The detergent composition of the present invention is creamy, has good foaming properties, is mild, and has excellent conditioning properties. Therefore, various detergents, particularly body shampoos, hair shampoos, and fine fabrics are washed. It can be suitably used as an agent.

[0028]

EXAMPLES The present invention will be described in more detail with reference to test examples and examples, but the present invention is not limited to these examples.

Test Example 1 A quaternary ammonium salt type compound shown in Table 1, a cationic surfactant and other active agents were blended in the composition shown in Table 1,
The foamability, skin irritation, detergency and conditioning were evaluated by the following test methods. The results are shown in Table 1.

<Test method> ・ Foaming test method 4 ° DH so that the final concentration of the active ingredient of the surfactant is 2%.
It diluted with hard water and measured by the inversion stirring method. The measurement was carried out at 40 ° C. with the addition of 0.3% lanolin, and the results are shown in terms of foam volume (ml). The foam quality was evaluated according to the following criteria. ◯: Creamy Δ: Slightly rough X: Coarse / Skin irritation test method As a skin irritation test method, a 24-hour closed patch test for humans was performed. That is, 20 test subjects were patched with a bandage plaster for batch test impregnated with 0.1 ml of an aqueous solution containing 0.2% of a surfactant as an active ingredient for 24 hours, and after the patch was removed.
Irritation was determined 24 hours later. Judgment results were made positive by showing clear erythema, and indicated by the positive rate.

Detergency test 5 cm x 5 cm wool muslin cloth with 2% carbon black
Stain with almost the same composition as scalp oil containing (paraffin 12%, wax ester 21%, triglyceride 26%, higher fatty acid
32%, cholesterol 5%, monoglyceride 2%) are evenly applied and dried. This contaminated cloth has an active agent content of 0.
About 1000 containing 500 ml of 6%, pH 7.0, 4 ° DH detergent solution
It is placed in a stainless steel cylinder of ml, shaken for 6 minutes in a constant temperature bath of 40 ° C., the contaminated cloth is rinsed well in running water, dried, and then the reflectance is measured. The cleaning rate is calculated by the following formula.

[0032]

[Equation 1]

Conditioning test To 20 g of a hair bundle (15 cm) of a Japanese woman, 1 g of a 20% aqueous solution of the active ingredient was applied, whipped and rinsed with running water at 40 ° C.,
After drying with a drier, the conditioning properties were evaluated by 5 expert panelists. ◯: Excellent conditionability Δ: Slightly insufficient conditionability ×: Poor conditionability

[0034]

[Table 1]

Example 1 A shampoo having the following composition was prepared. The obtained shampoo was excellent in detergency and foamability, and was excellent in texture and had no squeak during washing and rinsing.

[0036]

[Chemical 14]

Lauryldimethylamine oxide 3% by weight 2-dodecylhexadecyltrimethylammonium chloride 3 Carboxymethyl cellulose (No. 1310 manufactured by Daicel) 0.5 Hydroxyethyl cellulose (SE-850K manufactured by Daicel) 0.1 Sodium benzoate 0.3 Chromium Suitable amount Fragrance Proper amount Citric acid Proper amount Water Total 100 pH 6.5 Example 2 A shampoo having the following composition was prepared. The obtained shampoo was excellent in detergency and foamability, and was excellent in texture and had no squeak during washing and rinsing.

[0038]

[Chemical 15]

Polyoxyethylene (3) lauryl glucoside 3% by weight 2-dodecylhexadecyltrimethylammonium chloride 3 carboxymethylcellulose (manufactured by Daicel, No. 1310)
0.5 Hydroxyethyl cellulose (SE-850K manufactured by Daicel) 0.1 Sodium benzoate 0.3 Chromatic dye proper amount Fragrance proper amount Citric acid proper amount water 100 pH 6.5 Example 3 A body shampoo having the following composition was prepared. The obtained body shampoo was excellent in detergency and foamability and had a moist and good feeling after washing.

[0040]

[Chemical 16]

[0041]   Lauryl dimethylamine oxide 3% by weight   Cetyltrimethylammonium chloride 3   Polyoxyethylene (3) lauryl glucoside 5   Glycerin 5   Sucrose fatty acid ester 1   Methylparaben 0.3   Color element   Perfume suitable amount   Citric acid   Water 100                                             pH 7.5

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Office reference number FI technical display location C11D 1:38)

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, (b) A detergent composition comprising a cationic surfactant. 2. The cleaning 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 hydroxyalkyl group of ~ 3. X: shows 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, in the case of 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 cleaning 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 1 carbon atom.
It is not an alkyl group or hydroxyalkyl group of ~ 3. X: shows 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, in the case of 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 cleaning 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, and 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.)