JPS604871B2 - Amidoamino acid surfactant composition and method for producing the same - Google Patents

Description

Detailed Description of the Invention The present invention provides an amphoteric surfactant composition containing an N-long chain carboxylic acid amide alkylene aminopropionic acid derivative (hereinafter simply referred to as an amide amino acid compound) and an acrylic acid polymer. and its manufacturing method.

Amidoamino acid compounds having amphoteric surfactant ability have conventionally been produced by the following method.

'1} A method in which N-long chain acyl-N'-(hydroxyalkyl)ethylenediamine (hereinafter abbreviated as amidoamine compound) or the like is reacted with a monohalocarboxylic acid such as monochloroacetic acid or monochloropropionic acid and sodium hydroxide.

[21 A method in which an amidoamine compound and an acrylic acid lower alcohol ester are reacted, and the ester is hydrolyzed with an alkali such as sodium hydroxide or an acid such as hydrochloric acid.

{3} A method of reacting an amidoamine compound and 8-propiolactone.

However, the method [1} above has the drawback that a large amount of inorganic salts such as sodium chloride, glycolates, etc. are produced as by-products after hydrolysis with the halocarboxylic acid used in stoichiometric excess.

In particular, when an amphoteric active agent containing an inorganic salt such as sodium chloride is applied to conditioning shampoos or heavy-duty liquid detergents, substances with conditioning effects (e.g. cationized cellulose) may be separated.
There are disadvantages such as precipitation, and the amount of inorganic salt builder added is limited, making it impossible to obtain a sufficient builder effect.
Furthermore, in the method (2), as described above, the ester must be hydrolyzed with an alkali or acid, and there is a risk that lower alcohols may be contained in the reaction product.

Generally speaking, in the method {3} above, it is necessary to maintain 8-propiolactone itself at a low temperature, which is disadvantageous in the manufacturing process.

As described above, conventional amide amino acid type surfactants contain factors that inhibit their ability as active agents.
An object of the present invention is to provide an amide amino acid type amphoteric surfactant composition that does not contain inorganic salts and has excellent performance as a detergent or thickener, and a method for producing the same.

The present inventors reacted an amidoamine compound with acrylic acid to obtain an amidoamino acid compound containing no inorganic salt, and then further polymerized the unreacted acrylic acid in the reaction product using a polymerization initiator. The present inventors have discovered that the above object can be achieved by an amide amino acid type amphoteric surfactant composition, and have completed the present invention.

That is, the amide amino acid type surfactant composition of the present invention has the following general formulas (b) and (m) [however, in the above formula, R is a saturated or unsaturated fat having 7 or 21 carbon atoms. represents a group hydrocarbon group, and R2 and R3 are each
represents a hydrogen atom or a hydroxyalkyl group having 1 to 4 carbon atoms, and R2 and R3 may be the same,
Alternatively, they may be different.

] At least one selected from the group consisting of amide amino acid compounds and water-soluble salts thereof, and at least one selected from the group consisting of polyacrylic acid and water-soluble salts thereof It is characterized by containing. Further, the method for producing the amidoamino acid type surfactant composition of the present invention can be carried out using the following general formula (1): [However, in the above formula, R is a saturated or unsaturated compound having 7 carbon atoms or 21 carbon atoms. represents a fatty acid hydrocarbon group, R2 and R3 each represent a hydrogen atom or a hydroxyalkyl group having 1 to 4 carbon atoms, and R2 and R3 may be the same or different. The amidoamine compound shown above is reacted with acrylic acid in an amount larger than the stoichiometric amount for the compound of the general formula (1), and one of the following general formulas (D) and (m): [However, in the above formula, , R, R2 and R3 are the same as defined above], and then adding a polymerization initiator to the reaction mixture to polymerize the remaining acrylic acid, The method is characterized in that it includes converting at least a part of the obtained mixture of the amide amino acid compound and polyacrylic acid into at least one kind of water-soluble salt.

The amidoamine compound serving as a starting material for obtaining the interfacial repellent agent of the present invention is a compound represented by the above general formula (1), and
The acyl group R, CO is caprylic acid, capric acid,
Lauric acid, myristic acid, palmitic acid, stearic acid, erucic acid, isostaric acid, oleic acid, linoleic acid, isoolefinic acid, coconut oil fatty acid, tallow fatty acid,
and at least one kind selected from residues of fatty acids such as bran fatty acids.

Further, when R2 represents a hydroxyalkyl group, specific examples thereof include a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, and the like. This amidoamine compound is produced by known techniques. For example, the formula (1'-A) R, COOR (1'-A) (in the formula, R. is the same as the above definition, and R' is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms) represent.

) and the fatty acid ester represented by the general formula (1
'-B) (in the formula, R2 and R3 are the same as defined above.

) A method of condensing ethylenediamine or an ethylenediamine derivative represented by: (B' general formula (1'-C
) (In the formula, R and R3 are the same as defined above.

) A method of hydrolyzing the imidazoline compound shown in
etc. In obtaining the surfactant composition of the present invention, the acrylic acid used together with the amidoamine compound is used in an amount larger than the stoichiometric amount with respect to the amidoamine compound as the starting material, preferably 1 part of the stoichiometric amount. .3 None, 3. It is used in the amount of suffering.

If the amount of acrylic acid used is less than the stoichiometric amount for the amidoamine compound, a large amount of the starting material amidoamine will remain, which will not only reduce the yield of the amidoamino acid type surfactant, but also cause the residual amidoamine compound to be harmful to the skin and skin. This may irritate the eyes, be undesirable as a surfactant, or leave no acrylic acid to be subjected to polymerization. The reaction between amidoamine compound and acrylic acid is 70 None, 95
It is carried out at a temperature of qo. For example, an aqueous solution of an amidoamine compound is heated at 70° C. to 95° C., and acrylic acid is added dropwise to the solution over 1 hour while the solution is heated. When the temperature is maintained for an additional 2 hours for ripening, the reaction for producing the amidamino acid compound is completed. What is important in obtaining the surfactant of the present invention is that after the amidoamine compound and acrylic acid are reacted, a polymerization initiator is added to the reaction mixture to polymerize unreacted acrylic acid in the reaction mixture. The objective is to effectively utilize residual acrylic acid, which causes eye irritation, by converting it into an auxiliary substance that improves the performance of surfactants.

Examples of the polymerization initiator used at this time include azobisisobutyronitrile, dimethylazopisisobutyrate, azopisamidinopropane hydrochloride, azobisdimethylvaleronitrile, azobismethoxydimethyl/ereronitrile, and the like. System polymerization initiators, hydrogen peroxide, perboric acid, percarbonic acid, persulfuric acid, and their salts are used,
Generally, 0.4% of the total amount of acrylic acid used;
5. is used in an amount of % by weight. In addition, the polymerization reaction temperature of acrylic acid is 20 to 80 oo, preferably 35
None/70q0 will be adopted. If the polymerization reaction temperature is below 20°C, a large amount of acrylic acid remains, making it undesirable as a surfactant. If it exceeds 8 pi, the polymerization reaction will not proceed sufficiently and the resulting surfactant will become more colored, which is not preferable when producing a blended product of the surfactant. The amide amino acid compound which is the main component of the surfactant composition of the present invention is a compound represented by general formula (0) or (m).

However, in the formula, R,, R2 and R3 are the same as defined above.

At least a portion of the mixture of amidoamide/acid compound and polyacrylic acid is optionally at least one water-soluble salt, such as an alkali metal hydroxide, an ammonia lower alkanolamine, a basic amino acid, or a basic amino acid. It is metamorphosed into salts such as salt. As lower alkanolamines, monoethanolamine, diethanolamine, triethanolamine, etc. are used, as basic amino acids, lysine, alkynine, ornithine, etc. are used, and as basic amino acid salts, the above-mentioned basic amino acids are used. Alkali metal salts and the like are used.

In this salt modification, all of the carboxylic acid groups in the amidoamino compound of formula m may be modified into a salt, or only a portion thereof may be modified. The amide amino acid compounds contained in the composition of the present invention include the following formulas (W), (V
), (of), (skin) and (blood) compounds are preferred.

and However, R in the above formula is the same as defined above.

The main amide amino acid compounds include, for example, N-cocoyl-N'-(2-hydroxyethyl)-N'-(hydroxyethyl)ethylenediamine, N-lauroyl-N'-(2-hydroxyethyl)-N' −(
hydroxyethyl) ethylenediamine, N-cabroyl-N'-(2-hydroxyethyl)-N'-(carboxyethyl)ethylenediamine, N-stearoyl-N'
-(2-Hydroxyethyl)-N'-(hydroxyethyl)ethylenediamine, N-cocoyl-N-(2-hydroxyethyl)-N'・N'-bis(hydroxyethyl)ethylenediamine, N-lauroyl-N-(2- Hydroxyethyl)-N'・N'-bis(hydroxyethyl)ethylenediamine, N-stearoyl-N-(2-hydroxyethyl)-N'・N'-pis(hydroxyethyl)ethylenediamine, N-cocoyl-N-(2-hydroxyethyl) ethyl)-N'-(hydroxyethyl)ethylenediamine, N-lauroyl-N-(2-hydroxyethyl)-N'-(hydroxyethyl)ethylenediamine,
N-caproyl N-(2-hydroxyethyl)-N'
1-(hydroxyethyl)ethylenediamine, N-lauroyl-N'・N'-bis(hydroxyethyl)ethylenediamine, N-lauroyl-N'-(2-hydroxyethyl)ethylenediamine, N-lauroyl-N-(2-hydroxyethyl)-N' Examples include 1-(2-hydroxyethyl)-N'-(carpoxyethyl)ethylenediamine. The content of polyacrylic acid or its salt in the composition of the present invention may be in the range of 3.5% to 4.5% based on the total weight of the amidoamide/acid compound and polyacrylic acid. preferable. The surfactant of the present invention can be used with other surfactants such as fatty acids, higher alkyl ether sulfates, higher alkyl sulfates, higher alkylbenzene sulfonic acids, higher alcohol phosphates, N-acyl amide/
Anionic surfactants such as acids and their salts, higher alcohols, higher fatty acids, higher alkylphenols, polyhydric alcohols, alkylene oxide adducts such as fatty acid alkylolamides, nonionic surfactants such as fatty acid alkylolamides, high Enteric ionic surfactants such as alkyl dimethylbenzylammonium salts, higher alkyl amines, higher alkyl trimethyl ammonium salts, amphoteric surfactants such as alkyl amide/propionates, alkyl dimethyl betaines, and optionally commonly used in detergents. A cleaning composition can be prepared by appropriately selecting and blending additives such as builders, brightening agents, brightening agents, fragrances, and pigments.

Conventional amide amino acid type surfactants have the disadvantage that they cannot fully demonstrate their abilities because they contain inorganic salts and lower alcohols. However, the composition of the present invention does not contain any inorganic salt, and moreover, the acrylic acid remaining in the first stage reaction when producing the surfactant of the present invention is removed from the second stage.
By polymerizing in the step reaction, acrylic acid polymer not only eliminates factors that adversely affect the skin and eyes, but also converts into a substance that acts as a powerful auxiliary agent for the surfactant ability of the amide amino acid compound, which is the main component. This includes merging. For these reasons, the surfactant of the present invention can fully bring out its ability as an amide amino acid type surfactant, and when the surfactant of the present invention is used in a cleaning agent, It gives fineness and appropriate hardness to the foam, and has a high conditioning effect, especially when added to shampoo, making it easier to rinse the hair after washing, giving shine and suppleness to the hair, and making it easy to pass through. , has the effect of giving a moist texture.

The amphoteric surfactant composition containing the amide amino acid compound of the present invention as a main component is effective for cleaning, such as shampoo, conditioner shampoo, baby shampoo, kitchen detergent, pet shampoo, baffle bath cleaning agent, and acid shampoo. It is used in applications such as laundry detergents, dry cleaning detergents, household detergents, and metal surface detergents, and is also useful as a thickener and seawater foaming agent.

The present invention will be specifically explained below using examples.

Example 1 Preparation of N-cocoyl-N'-(2-hydroxyethyl)-N'-(sodium carpoxyethyl)ethylenediamine N-cocoyl-N-(2-hydroxyethyl)ethylenediamine 305 (1.0 mol) and water 6
After mixing 11 minutes and heating to 85 degrees, add 93 degrees of acrylic acid.
7 moles (1.3 mol) was added dropwise over 1 hour.

After further aging at the same temperature for 2 hours, the reaction solution was cooled to 3,000 ml of N-cocoyl-N'-(2-hydroxyethyl)-N'
An aqueous solution of -(ruboxethyl)ethylenediamine was obtained. Next, add 3.32% of 35% hydrogen oxide water per week to this aqueous solution.
The mixture was heated at 55°C and 60°C for 1 hour to polymerize unreacted acrylic acid. Then, a mixed solution of 48% sodium hydroxide aqueous solution (108%) and water (303%) was added to neutralize the mixture to obtain an aqueous solution (1381%) of the title compound.
The nitrogen content in all components of this product is 2.00%, and it is gask. Quantitative analysis by matography revealed that the content of acrylic acid monomer was 0.35%. In addition, the polyacrylic acid content per solid content in the composition is 8.9%.
Met. Example 2 Production of N-lauroyl-N'-bis(hydroxyethyl)ethylenediamine N-lauroylethylenediamine 2
After mixing 422 (1.0 mol) and 839 mol of water and heating to 85°C, 216.2 mol (3.0 mol) of acrylic acid was mixed.
Dripped between vowels.

After further aging at 85%, 9% and 0% for 2 hours,
The reaction solution was cooled to 3000 ml. Then add 35% to this solution.
Add 16.1% hydrogen peroxide solution and hold at 70°C for 1 hour to polymerize unreacted acrylic acid to form an aqueous solution of N-lauroyl-N'-bis(hydroxyethyl)ethylenediamine and polyacrylic acid. I got the evening. The yield of this product was 96.5%, the nitrogen content was 2.11%, the acrylic acid monomer content was 0.38%, and the neutralization value was 130. Further, the content of polyacrylic acid per solid content in the composition was 34.9%. Examples 3 and 4N-cocoyl-N'-(2-hydroxyethyl)-N'-(
Production of N-cocoylN-(2-hydroxyethyl)-N'-(hydroxyethyl)ethylenediamine In Example 3, 2
-Shasialkyl-N-(2-hydroxyethyl)-2-
Mixture 163 of N-cocoyl-N'-(2-hydroxyethyl)ethylenediamine obtained by hydrolyzing imidazoline (0.15 mol), N-cocoyl-N-(2-hydroxyethyl)ethylenediamine, and water. After heating to 8000℃, acrylic acid 32.4℃ (0.45℃)
mol) was added dropwise over 1 hour.

Further, the reaction solution was heated to 80% hydrogen peroxide, kept at 90qC for 2 hours, cooled to 300qC, and added with 35% hydrogen peroxide aqueous solution 0.78 qC.
The acrylic acid was polymerized at 50 to 60 mil for 15 hours to obtain the title compound 191.
The nitrogen content of this product was 2.10%, the acrylic acid monomer content was 0.34%, and the neutralization value was 130. In addition, the content of polyacrylic acid per solid content in the composition is 31
．． It was 0%. Next, in Example 4, in place of hydrogen peroxide in the reaction, azobisisobutyronitrile 1
When a similar reaction was carried out using
I got 90 nights. The nitrogen content of this product is 2.15%, the acrylic acid monomer content is 0.38%, and the neutralization value is 127.
Met. Further, the content of polyacrylic acid per solid content in the composition was 29.5%. Example 5 Skin irritation test using amphoteric surfactant on white rabbits The compound obtained in Example 1 and the compound obtained in Example 1 in which hydrogen peroxide was not added and acrylic acid was not polymerized (hereinafter compared) Example 1
) was adjusted to pH 7.0 with dilute hydrochloric acid.
A closed patch test was conducted on white rabbits using a % aqueous solution.

The cloth piece was removed 4 hours after applying the sample, and the presence or absence of deformation was observed after 1 hour, 2 hours, and 7 hours. As a result, amide amino acid compounds containing acrylic acid polymers are more effective than those containing acrylic acid monomers.
It was found that there is little skin irritation. The results are shown in Table 1. Table 1 Judgment Criteria No reaction - Erythema and eruption 10 Suspicious positive Erythema, eruption and blisters + 10 Erythema 10 Visible floating spots and blisters 10 days 10 Examples 6 Conducting a closed patch test on the cortex of the human body As a result of Example 5, it was found that the composition of Example 1 did not cause any skin irritation to white rabbits. Therefore, a patch test was conducted on the composition of Example 1 with 48 adult males to determine its irritation to human skin. A comparison was made with a midazolinium betaine type surfactant (Control Product 1) and sodium dodecyl sulfate (Control Product 2).

As a result, the composition of Example 1 was found to be equivalent to the imidazolinium betaine type surfactant (Control Product 1) and lower than sodium dodecyl sulfate (Control Product 2) in terms of skin irritation. Table 2 shows the results. Table 2 Note 1 Measurement method Two drops of the sample solution were dropped onto a patch test patch and applied to the back of the test subject for 4 hours.

Approximately 2 hours after the small wound is removed, the condition of the skin is observed and judged. Example 7 Sensory test on hair The compositions obtained in Examples 1 to 4 were adjusted to 7.0 using hydrochloric acid or sodium hydroxide, and the concentration was adjusted to 30%.
Approximately 40 qo of these samples were given to 10 people (5 men, 5 women).
Wash your hair with warm water, and after shampooing, your hair will become shiny and
Comparisons were made with commercially available imidazolinium betaine surfactants in terms of flexibility and shearability.

The evaluation method is to compare with the commercial product and give an evaluation score of ○ if it is equivalent to the commercial product, 11 if it is better, and -1 if it is inferior, and then give the total score of the 10 people's evaluation. It was determined that The results are shown in Table 3. Score Judgment -10Y-6 × -5 Y.

1 to 5 ○ 6YIO ◎ Table 3 Example 8 (increase *indicator) 20 of the composition obtained in Example 1 adjusted to pH 7.0
% aqueous solution and 20% sodium lauryl sulfate or 20% sodium lauryl ether sulfate aqueous solution adjusted to pH 7.0, and a B-type viscometer (Tokyo Keiki K.K.
The compound viscosity was measured using a commercially available imidalinium betaine surfactant, and the compound viscosity of the active agent was compared with the compound of Comparative Example 1 and a commercially available imidalinium betaine type surfactant.

As a result, it was found that the surfactant of the present invention had a much greater thickening effect than Comparative Example 1 and commercially available imidalinium betaine. The results are shown in FIGS. 1 and 2. Example 9 Foaming agent in seawater (blood with a hardness of 600) The compositions of Examples 1 to 4 and the imidazolinium betaine type surfactant (control product) were treated with 0.0% of the active ingredient.
Prepare a 25% aqueous solution and measure the foaming power at 40°C by JI
It was measured according to the method of SK-3362.

The results are shown in Table 4. Examples 10 to 15 below in Table 4 show examples in which the surfactant of the present invention was used in a cleaning agent.

Example 10 Weakly Acidic Shampoo Sodium Salt of the Composition of Example 1 (Water Content 70%)
41.7% Polyoxyethylene (3 mol) Sodium Lauryl Sulfate Wam
10.0 Lauric acid jetanolamide 5.0 Flavoring appropriate amount Hydrochloric acid Amount to make water = 6.5 Citric acid - Amount to make pH = 6.0 Water
After lowering the pH to 6.5 or higher with 100 rubs of hydrochloric acid, a transparent weakly acidic shampoo is obtained by adjusting the pH to 6.0 with citric acid.

This product lathered well, gave shine to the hair, and was easy to comb. Example 11 Gel shampoo Sodium salt of the composition of Example 1 (water content 70%)
20.8% Sodium lauryl sulfate 15.0 Lauric acid jetanolamide 2.5 Hydrochloric acid
Amount of salt to adjust to wind = 7.0
2.0% water
Heat the above mixture in an amount to make the total volume 100%,
Adjust the pH to 7.0 with hydrochloric acid and cool to obtain a transparent gel shampoo.

It was found that the present detergent composition foams well, is easy to rinse after hair washing, and gives shine to the hair. Example 1
2 Rinse shampoo Sodium salt of the composition of Example 1 (water content 70%)
Spots. 0% Lauric Jetanolamide 4.0 Lanolin Fatty Acid Polyethylene Glycol Ester 3.0 Cationic Cell.

-su conductor 0.2 hydrochloric acid
Amount of water to make pH=6.0
When the total amount is 100% and treated in the same manner as in Example 11 and adjusted to pH=6.0 with hydrochloric acid, a transparent liquid shampoo is obtained. This detergent composition was found to foam well and give gloss and suppleness to the hair, as well as a moist texture. Example 13 Sodium salt of the composition of yarn detergent Example 1 (70% water content)
83.3% Stearyltrimethylammonium chloride 3.0 Lauric acid jetanolamide 2.0 Hydrochloric acid
Amount of water to make pH=7.0
The total amount is 100% The present detergent composition foamed well and had good cleaning properties, and was found to impart softness and suppleness to woolen products after drying.

Example 14 Potassium salt of the composition of facial cleanser Example 3 (60% water content)
25.0% myristic acid 24.0 rawalic acid
5.0 stearic acid
4.0 Potassium hydroxide (25
%) 19.4 polyoxyethylene (1
0 mol) coconut fatty acid monoethanolamide
7.0 Lauric acid monoethanolamide 1.0 Ethylene glycol distearate
3.0 glycerin
20 polyethylene glycol #200
3.0 water 6.
6 Perfume Appropriate amount A mixture of the above composition was mixed under heating and then cooled to obtain a facial cleansing cream with pearlescent luster.

This product was found to foam well and give a refreshing feel to the skin. Example 15 Hard Surface Detergent (for Vinyl Leather) Composition of Example 4 Sodium Salt (70% Moisture Content)
5.0% Sodium metacitrate 10.0 Silicone oil (water soluble) 1.0 Water
84.0 This product was found to have good cleaning properties and to give gloss to hard surfaces.

[Brief explanation of drawings]

FIG. 1 shows the composition of Example 1, the composition of Comparative Example 1, and a commercially available imidazolinium betaine type amphoteric surfactant at pH 7. It is a graph showing changes in viscosity depending on the mixing ratio of the two when each aqueous solution was adjusted to an aqueous solution with a u concentration of 20% and mixed with an aqueous sodium lauryl sulfate solution adjusted to a pH of 7.0 and a concentration of 20%. . FIG. 2 shows each of the above aqueous solutions and pH 7. It is a graph showing the change in viscosity depending on the mixing ratio of both when mixed with a sodium lauryl ether sulfate aqueous solution adjusted to a final concentration of 20%. Figure 1 Figure 2

Claims (1)

[Claims] 1 The following general formulas (II) and (III) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [However, in the above formula, R^1 is a carbon atom represents a saturated or unsaturated aliphatic hydrocarbon group having 7 to 21 atoms; R_2 and R_3 each represent a hydrogen atom or a hydroxyalkyl group having 1 to 4 carbon atoms;
2 and R_3 may be the same or different. At least one selected from the group consisting of the amidoamic acid compound shown in ] and its water-soluble salt; and at least one selected from the group consisting of polyacrylic acid and its water-soluble salt. An amide amino acid type surfactant composition comprising. 2 In the general formulas (II) and (III), the R_1CO group is caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, erucic acid, isostearic acid, oleic acid, linoleic acid, isooleic acid, linoleic acid. The composition according to claim 1, which is a residue of a fatty acid selected from the group consisting of acids, coconut oil fatty acids, beef tallow fatty acids and bran fatty acids. 3. The amide amino acid compound has the following formula (IV): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, in the above formula, R_1 is the same as the above definition],
A composition according to claim 1. 4. The composition according to claim 1, wherein the amide amino acid compound has the following formula (V): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, in the above formula, R_1 is the same as defined above] . 5. The composition according to claim 1, wherein the amide amino acid compound has the following formula (V): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, in the above formula, R_1 is the same as defined above] . 6 The content of the polyacrylic acid is 3 to the total weight of the amide amino acid compound and the polyacrylic acid.
．． Claim 1 within the range of 5 to 45%
Compositions as described in Section. 7. Each water-soluble salt of the amide amino acid compound and polyacrylic acid is a one-member salt selected from the group consisting of an alkali metal hydroxide, ammonia, a lower alkanolamine, a basic amino acid, and a basic amino acid salt. , the composition according to claim 1. 8 The following general formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, in the above formula, R_1 represents a saturated or unsaturated fatty acid hydrocarbon group having 7 to 21 carbon atoms, and R_2 and R_3 each represents a hydrogen atom or a hydroxyalkyl group having 1 to 4 carbon atoms, and R_2
and R_3 may be the same or different] and acrylic acid in an amount larger than the stoichiometric amount for the compound of general formula (I), - The following general formulas (II) and (III): ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [However, in the above formula, R_1R_2 and R_3 are the same as the above provisions]. Both produce one type of amide amino acid compound, and then add a polymerization initiator to this reaction mixture,
An amide amino acid type surfactant comprising polymerizing the remaining acrylic acid and optionally converting at least a part of the obtained mixture of the amide amino acid compound and polyacrylic acid into at least one water-soluble salt. Method for producing a drug composition. 9. The method according to claim 8, wherein the acrylic acid is used in an amount of 1.3 to 3 times the stoichiometric amount for the amidoamine compound of general formula (I). 10. The method according to claim 8, wherein the reaction between the amidoamine compound of general formula (I) and acrylic acid is carried out at a temperature of 70 to 95°C. 11. The method of claim 8, wherein the polymerization of acrylic acid is carried out at a temperature of 20 to 80°C. 12 The polymerization initiator is azobisisobutyronitrile,
selected from dimethylazobisisobutyrate, azobisamidinopropane hydrochloride, azobisdimethylvaleronitrile, azobismethoxydimethylvaleronitrile, hydrogen peroxide, and perboric acid, percarbonic acid, persulfuric acid and salts of said acids. The method according to claim 8. 13. The method according to claim 8, wherein the polymerization initiator is used in an amount of 0.4 to 5% based on the total amount of acrylic acid used.