JP2972372B2 - Surfactant composition and detergent composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

FIELD OF THE INVENTION The present invention relates to a surfactant composition comprising an amide amino acid type surfactant containing polyacrylic acid and a phosphite compound as essential components, and to containing the surfactant composition. The present invention relates to a cleaning composition characterized by the following.

[0002]

2. Description of the Related Art Recently, hair and scalp are mild and less irritating,
Amide amino acid-type amphoteric surfactants have been frequently used as bases for cleansing agents such as shampoos and facial cleansers with good foaming. However, since these amphoteric surfactants use monochloroacetic acid, monochloropropionic acid, or the like in the amphoteric reaction, there is a disadvantage that salt is by-produced. When salt is present, the compatibility with other surfactants and conditioning agents such as cationized cellulose deteriorates, which often causes inconvenience in formulation. As an amide amino acid type amphoteric surfactant containing no salt, there is a method of reacting acrylic acid with an amidoamine compound. (Sho 60-
No. 4871) However, the amido-amino acid type amphoteric surfactant produced by this method is mild and less irritating to the hair and scalp, has good foaming, and contains no salt, so that it can be blended with other surfactants. Although it has an advantage that it can be freely used, it has a drawback that it is colored over time, and there is a difficulty in blending it into a shampoo or the like. As a method of preventing this coloring with time, a method of adding sodium borohydride, a method of treating with activated carbon, and the like have been tried, but the former is only temporary decolorization, and the latter is micelles in which activated carbon is a surfactant. It cannot be separated by filtration and is not satisfactory as an industrial production method for improving defects.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to provide an amide amino acid type surfactant which is mild and less irritating to hair and scalp, has good foaming, has little coloring over time, and contains no salt. It is another object of the present invention to provide a composition and a detergent composition containing the surfactant composition as an essential component.

[0004]

That is, the present invention relates to the compounds represented by the general formulas (1) and (2):

Embedded image (1)

Embedded image (2) wherein R ¹ represents a saturated or unsaturated aliphatic hydrocarbon group having 7 to 21 carbon atoms, and R ² and R ³ represent a hydrogen atom or a C ¹ to C 4 Represents a hydroxyalkyl group and may be the same or different, and M represents one selected from a hydrogen atom, sodium, potassium and triethanolamine.) Or an amide amino acid type surfactant composition containing two or more kinds and polyacrylic acid or a water-soluble salt thereof, represented by the general formula (3):

Embedded image (3) (wherein, R ⁴ , R ⁵ , and R ⁶ represent a hydrogen atom, a sodium, potassium, or ammonium group, and may be the same or different.) A surfactant composition characterized by adding a seed, and a detergent composition characterized by comprising the following three components (A), (B) and (C) as essential components. (A) One or more amide amino acid type surfactants selected from amide amino acid compounds represented by the following general formulas (1) and (2).

Embedded image (1)

Embedded image (2) wherein R ¹ represents a saturated or unsaturated aliphatic hydrocarbon group having 7 to 21 carbon atoms, and R ² and R ³ represent a hydrogen atom or a C ¹ to C 4 Represents a hydroxyalkyl group and may be the same or different, and M represents one selected from a hydrogen atom, sodium, potassium and triethanolamine.) (B) Polyacrylic acid or its water solubility salt. (C) At least one phosphorous acid compound represented by the following general formula (3).

Embedded image (3) (In the formula, R ⁴ , R ⁵ , and R ⁶ represent a hydrogen atom, a sodium, potassium, or ammonium group, and may be the same or different.)

The amido-amino acid type amphoteric surfactant composition containing polyacrylic acid used in the present invention can be easily produced by the method described in JP-B-60-4871. That is, the following general formula (4)

Embedded image (4) (wherein, R ¹ represents a saturated or unsaturated aliphatic hydrocarbon group having 7 to 21 carbon atoms, and R ² and R ³ represent a hydrogen atom or a hydroxy having 1 to 4 carbon atoms. An alkylamine group, which may be the same or different.) And an equimolar amount or more of acrylic acid are reacted to obtain the following general formulas (1) and (2)

Embedded image (1)

Embedded image (2) (wherein R ¹ , R ² , and R ³ are the same as defined above), and then a polymerization initiator is added to the reaction mixture to remain. This is a method for producing an amide amino acid type surfactant composition for polymerizing acrylic acid.

The amidoamine compound represented by the general formula (4) can be produced by a method of condensing a fatty acid or a fatty acid ester with an ethylenediamine derivative or a method of hydrolyzing an imidazoline compound.

Specific examples of the amide amino acid compounds represented by the general formulas (1) and (2) include N-cocoyl-N '-(2-hydroxyethyl) -N'-(carboxyethyl) ethylenediamine, -Lauroyl-N'-
(2-hydroxyethyl) -N '-(carboxyethyl) ethylenediamine, N-caproyl-N'-(2-
(Hydroxyethyl) -N '-(carboxyethyl) ethylenediamine, N-stearoyl-N'-(2-hydroxyethyl) -N '-(carboxyethyl) ethylenediamine, N-cocoyl-N- (2-hydroxyethyl)
-N ', N'-bis (carboxyethyl) ethylenediamine, N-lauroyl-N- (2-hydroxyethyl)
-N ', N'-bis (carboxyethyl) ethylenediamine, N-stearoyl-N- (2-hydroxyethyl) -N', N'-bis (carboxyethyl) ethylenediamine, N-cocoyl-N- (2-hydroxy Ethyl) -N ′-(carboxyethyl) ethylenediamine,
N-lauroyl-N- (2-hydroxyethyl) -N '
-(Carboxyethyl) ethylenediamine, N-caproyl-N- (2-hydroxyethyl) -N '-(carboxyethyl) ethylenediamine, N-lauroyl-
N ', N'-bis (carboxyethyl) ethylenediamine, N-lauroyl-N'-(carboxyethyl) ethylenediamine, N-lauroyl-N- (2-hydroxyethyl) -N '-(2-hydroxyethyl) -N '-(Carboxyethyl) ethylenediamine and sodium, potassium and triethanolamine salts of these compounds.

The content of polyacrylic acid or a water-soluble salt thereof in the amide amino acid type surfactant composition is in the range of 3.5 to 45% based on the total amount (active ingredient) of the amide amino acid compound and polyacrylic acid. It is preferably within.

The phosphite compound represented by the general formula (3), which is the other component of the present invention, is specifically exemplified by phosphorous acid, sodium phosphite, sodium hydrogen phosphite, phosphorus phosphite Potassium acid, potassium hydrogen phosphite, ammonium phosphite, ammonium hydrogen phosphite and the like can be mentioned. The compounding amount of the phosphite compound is 0.0 to the active ingredient of the amide amino acid type surfactant composition.
3-15%, preferably 0.1-10% is good. 0.
If it is less than 03%, the effect of preventing coloring is small, and if it is more than 15%, it is unnecessary.

[0010] The surfactant composition of the present invention can be applied to shampoos, body shampoos, baby shampoos, pet shampoos, facial cleansers, kitchen detergents and the like. When incorporated into these detergent compositions, the following components can be used in combination with the surfactant composition of the present invention as long as their performance is not reduced. That is, fatty acid soap, higher alcohol sulfate, polyoxyethylene higher alcohol sulfate, higher alcohol phosphate, polyoxyethylene higher alcohol phosphate, sulfosuccinate, α-olefin sulfonate, Anionic surfactants such as alkyl phosphate ester salts, acylmethyl taurine salts, acyl isethionate salts, amphoteric surfactants such as alkyl imidazolinium betaine type and amidopropyl betaine type, fatty acid diethanolamide, fatty acid monoethanolamide, alkylamine Examples thereof include nonionic surfactants such as oxides and polyoxyethylene higher alcohol ethers, and cationic surfactants such as quaternary ammonium salt type cationic surfactants.

If necessary, a solubilizing agent such as glycols, an emollient such as ester oil, a preservative such as hyaluronic acid, chitin, chitosan, a cell activator such as aloe extract, placenta extract, and allantoin And anti-inflammatory agents such as glycyrrhizinate, anti-dandruff agents such as zinc pyrithione and pyrocton olamine, fragrances, dyes and the like.

Hereinafter, the present invention will be described in more detail with reference to examples.

EXAMPLES Production Example-1 N-cocoyl-N '-(2-hydroxyethyl) -N'
-Of (sodium carboxyethyl) ethylenediamine
Production 305 g (1.0 mol) of N-cocoyl-N ′-(2-hydroxyethyl) ethylenediamine and 611 g of water were mixed, heated to 85 ° C., and then 93.7 g (1.3 mol) of acrylic acid was added dropwise for 1 hour. did. After further aging at the same temperature for 2 hours, the reaction solution was cooled to 30 ° C. to obtain an aqueous solution of N-cocoyl-N ′-(2-hydroxyethyl) -N ′-(carboxyethyl) ethylenediamine. Next, 35
3.32 g of an aqueous hydrogen peroxide solution was added, and the mixture was kept at 55 to 60 ° C. for 12 hours to polymerize unreacted acrylic acid. Then, 411 g of a 12.6% aqueous sodium hydroxide solution
And neutralized to obtain 1390 g of an aqueous solution of the title compound. The active ingredient was 30.1%, and polyacrylic acid was 8.7% of the active ingredient.

Production Example-2N-lauroyl-N'-bis (sodium carboxyl
Chill) Production of ethylenediamine  242 g of N-lauroylethylenediamine (1.0 m
And 839 g of water and heated to 85 ° C.
216.2 g (3.0 mol) of the acid were added dropwise over 1.5 hours.
Was. Aged at 85 or 90 ° C for 2 hours
Thereafter, the reaction solution was cooled to 30 ° C. Next, 3
Add 16.1 g of 5% hydrogen peroxide solution,
For 15 hours to polymerize unreacted acrylic acid and react
After that, the mixture was neutralized by adding an alkali, and N-lauroyl-N'-bi
(Sodium carboxyethyl) ethylenediamine
1270 g of an aqueous solution of polyacrylic acid was obtained. This one
The active ingredient is 30.2%, and polyacrylic acid is
34.7%.

Production Example 3 N-cocoyl-N '-(2-hydroxyethyl) -N'
-With (sodium carboxyethyl) ethylenediamine
N-cocoyl-N- (2-hydroxyethyl) -N'-
Mixture of (sodium carboxyethyl) ethylenediamine
Preparation of compound 2-cocoalkyl-N- (2-hydroxyethyl) -2
-A mixture of N-cocoyl-N '-(2-hydroxyethyl) ethylenediamine, N-cocoyl-N- (2-hydroxyethyl) ethylenediamine and water obtained by hydrolyzing 43 g (0.15 mol) of imidazoline 163
g to 80 ° C., and then 32.4 g of acrylic acid (0.45 g).
Mol) was added dropwise over 1 hour. After further aging the reaction solution at 80 to 90 ° C. for 2 hours, the reaction solution was cooled to 30 ° C.
0.78 g of aqueous hydrogen peroxide solution was added, and the mixture was kept at 50 to 60 ° C. for 15 hours to polymerize unreacted acrylic acid. After the reaction, alkali was added for neutralization, and N-cocoyl-N ′-(2-
192 g of an aqueous solution of a mixture of hydroxyethyl) -N ′-(sodium carboxyethyl) ethylenediamine, N-cocoyl-N- (2-hydroxyethyl) -N ′-(sodium carboxyethyl) ethylenediamine and polyacrylic acid were obtained. Its active ingredient is 30.4
%, Polyacrylic acid was 30.8% with respect to the active ingredient.

Examples 1 to 19 and Comparative Examples 1 to 4 To 100 g of the amide amino acid type surfactant composition obtained in Production Examples 1 to 3 were added a phosphite compound or the like to give 50%.
A test was performed in which the test was left at 10 ° C. for 10 days, and the change in color before and after the test was measured. The hue was measured by the Gardner method specified in the standard fat and oil analysis method. Table 1 shows the test conditions and test results. In the table, the number in parentheses next to the amount of the phosphite compound added indicates the rate of addition of the phosphite compound to the active ingredient of the amide amino acid surfactant composition.

[Table 1]

Example 20 Body Shampoo 5.0% by weight Lauric acid Composition of Preparation Example 10.0 10.0 Phosphorous acid 0.2 (6.2%) Amidopropyl dimethylamino laurate betaine acetate 5.0 Laurin Acid diethanolamide 3.0 Potassium hydroxide Amount to pH 8 Glycerin 3.0 Methyl paraben 0.1 Purified water Remaining This body shampoo has good lather and is mild on the skin,
There was no coloring over time.

Example 21 Hair shampoo polyoxyethylene (3) lauryl ether-sodium sulfate 10.0% by weight Composition of Preparation Example 1 40.0 Phosphorous acid 1.0 (7.7%) lauroylmethyl-β -Sodium alanine 2.0 sodium lauroylmethyltaurine 2.0 coconut oil fatty acid diethanolamide 1.0 cationized cellulose 0.5 citric acid pH 7 amount disodium edetate 0.1 methyl paraben 0.1 purified water residue This hair shampoo Had good foaming, was mild on hair and skin, and had no coloring with time.

Example 22 Facial cleanser Myristic acid 24.0% by weight Lauric acid 5.0 Stearic acid 4.0 Composition of Production example-1 5.0 Sodium hydrogen phosphite 0.1 (9.1%) Water Potassium oxide 4.8 Polyoxyethylene (5) coconut oil fatty acid-monoethanol amide 7.0 Ethylene glycol distearate 3.0 Glycerin 4.0 Polyethylene glycol 400 3.0 Hyaluronic acid 0.5 Methyl paraben 0.1 Purified water Residue This facial cleanser had good lathering, gave a mild and moist feeling to the skin, and was not colored over time.

Example 23 Composition of Kitchen Detergent Preparation Example 1 50.0% by weight Phosphorous acid 1.0 (6.2%) Potassium phosphite 0.2 (1.2%) α-olefin sulfonic acid Soda 5.0 Laurylamine oxide 3.0 Methyl paraben 0.2 Purified water residue This kitchen detergent foams, has good detergency, is mild on the skin,
There was no coloring over time.

[0020]

According to the present invention, foaming and detergency are excellent,
An amide amino acid type surfactant composition which is mild to the skin and hair, has no coloring over time, and does not contain salt, has a high degree of freedom of formulation, and a detergent composition containing the surfactant composition as an essential component. Can be manufactured.

Claims (2)

(57) [Claims] 1. General formulas (1) and (2) (1) (2) wherein R ¹ represents a saturated or unsaturated aliphatic hydrocarbon group having 7 to 21 carbon atoms, and R ² and R ³ represent a hydrogen atom or a C ¹ to C 4 Represents a hydroxyalkyl group and may be the same or different, and M represents one selected from a hydrogen atom, sodium, potassium and triethanolamine.) An amidoamino acid type surfactant composition containing one or more kinds and polyacrylic acid or a water-soluble salt thereof is represented by a general formula (3): (3) (wherein, R ⁴ , R ⁵ , and R ⁶ represent a hydrogen atom, a sodium, potassium, or ammonium group and may be the same or different.) A surfactant composition, wherein one type is added. 2. A cleaning composition comprising the following three components (A), (B) and (C) as essential components. (A) One or more amide amino acid type surfactants selected from amide amino acid compounds represented by the following general formulas (1) and (2). Embedded image (1) (2) wherein R ¹ represents a saturated or unsaturated aliphatic hydrocarbon group having 7 to 21 carbon atoms, and R ² and R ³ represent a hydrogen atom or a C ¹ to C 4 Represents a hydroxyalkyl group, which may be the same or different, and M represents a kind obtained from a hydrogen atom, sodium, potassium and triethanolamine.) (B) Polyacrylic acid or its aqueous solution Sex salt. (C) At least one phosphorous acid compound represented by the following general formula (3). Embedded image (3) (In the formula, R ⁴ , R ⁵ , and R ⁶ represent a hydrogen atom, a sodium, potassium, or ammonium group, and may be the same or different.)