JPS5951532B2 - Novel amine amide compound, method for producing the same, and surfactant containing the amine amide compound - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides novel amine amide compounds, specifically N-acyl-N-(2-hydroxyethyl)-N
', N-bis(carboxymethyl)ethylenediamine,
Alternatively, the present invention relates to salts thereof, a method for producing the same, and an amphoteric surfactant containing the amine amide compound.

In recent years, there has been a demand for surfactants used in detergents and the like to have excellent properties such as biodegradability, safety, and irritation to the eyes and skin in addition to surfactant ability.

Imidazoline type amphoteric surfactants are examples of surfactants that meet these demands. Imidazoline-type amphoteric surfactants are characterized by excellent foaming and cleaning power, as well as extremely low irritation to the eyes and skin. It is increasing. The method for producing imidazoline type amphoteric surfactants is disclosed in U.S. Patent Nos. 2,528,378 and 2,773.
It is described in the specification of No. 068.

One method for producing the compound described in US Pat. No. 2,528,378 is to dehydrate 1 mole of aminoethylethanolamine, which is equivalent in mole to the fatty acid, at 170°C, and then raise the temperature to 220°C. 1 mole of water is dehydrated to synthesize an imidazoline compound. Next, this imidazoline compound was added at room temperature to an aqueous solution of 1 mol sodium monochloroacetate and 2.25 mol sodium hydroxide, which had been prepared in advance at a temperature below 20°C, and an amphoteric reaction was carried out at a temperature of around 90°C, so that the pH was 13 From 8 to 8.
This is a method in which the reaction is terminated when the temperature reaches 5K to obtain an imidazoline type amphoteric surfactant. The compound obtained by the method is 2-alkyl-N-carboxymethyl-N-(2-hydroxyethyl)imidazolinium betaine having an imidazoline ring, as shown by the following general formula M. Says.

After that, Joseph, Nicholas, Masci and others
Publication No. 4762 mentions this substance.

Therein, it is stated that the compound of general formula (V) obtained by the method described in US Pat. No. 2,528,378 is a linear or branched chain compound and does not form an imidazoline ring. For example, what was thought to be an imidazoline compound represented by the structural formula (): obtained by the method of the above-mentioned U.S. patent was subsequently analyzed and found to be an N-
lauroyl-N'-sodium carboxymethyl-N'
It was found to be a mixture of -(2-hydroxyethyl)ethylenediamine and N-lauroyl-N'-(2-hydroxyethyl)ethylenediamine represented by the structural formula ().

The reason for this misidentification is the above-mentioned U.S. Patent No. 25283.
This is because, in the description of the production method in the specification of No. 78, it was overlooked that the imidazoline ring was hydrolyzed when carrying out the amphoteric reaction of the imidazoline compound using monochloroacetic acid and sodium hydroxide. The inventors also obtained the U.S. Patent No.
As a result of conducting additional tests on the compound described in No. 528378, results similar to those of Joseph, Nicholas, Masci et al. were obtained.

Further, US Pat. No. 2,773,068 describes the reaction of an imidazoline compound with 2 moles of a monohalogen carboxylic acid. One method for producing the compound described therein is to synthesize an imidazoline compound by reacting equimolar amounts of aminoethylethanolamine with a fatty acid in the same manner as described in U.S. Pat. No. 2,528,373. Next, add this imidazoline compound to 2
Add to 2 mol of monochloroacetic acid and 4.5 mol of sodium hydroxide aqueous solution adjusted at 0°C or below at room temperature to carry out an amphoteric reaction at 100°C, and the pH will change from 13 to 8.8 to 9.3.
In this method, the reaction is terminated at the point where the imidazoline type amphoteric surfactant is obtained. The compound obtained by this method is 2-alkyl-N-(carboxymethoxyethyl)-1N-carboxymethyl-imidazolinium petaine having 7 imidazoly rings, as shown by the following general formula (). It has said. However, as a result of the present inventors carrying out a follow-up test of the method described in US Pat. No. 2,773,068 and conducting a more detailed analysis of the product, a compound having an imidazoline ring of the general formula () could not be obtained. Moreover, the absence of ether groups was confirmed.

In other words, the compound that was thought to have the general formula 0X) is now the compound (
) has a similar structure to the branched chain compound shown in
It was confirmed that the compound is substantially the same as the compound given in US Pat. No. 2,528,378, and contains almost no unreacted substances as shown in compound ().
As described above, in the former method, unreacted substances are included, and in the latter method, a large amount of glycolate and common salt, which are decomposed monochloroacetic acid used in excess, coexist. Moreover, the resulting product has a high viscosity and is difficult to operate on an industrial scale. The present inventors conducted intensive research to obtain a substance with good amphoteric surface activity and fewer production difficulties as described above, and found that when reacting an imidazoline compound with a monohalogenated acetic acid, the pH of the reaction solution was lowered to 7. or 1.2
U.S. Patent No. 277 by adjusting the
The present invention was completed based on the discovery that, unlike the compound obtained in the specification of No. 3068, a novel compound having excellent viscosity properties and low irritation can be obtained as described below.

That is, the novel compound of the present invention has the general formula [wherein R represents a saturated or unsaturated aliphatic hydrocarbon group having 7 to 21 carbon atoms, and M represents a hydrogen atom, an alkali metal atom, ammonium or an alkanolamine atom] It is an amine amide compound represented by [ionic residue].

The compound of the present invention, ie, the compound of general formula (1), can be produced by two methods of the present invention.

That is, in the method 1 of the present invention, general formula (I[):
a fatty acid or fatty acid ester represented by [representing an alkyl group having 1 to 4 carbon atoms] and aminoethylethanolamine at a temperature of 80 to 170°C, and further reacted at a temperature of 180 to 220°C, As a condensation product, 2-alkyl-1-(2-hydroxyethyl)-2-imidazoline represented by the general formula (): [in the above formula, R is the same as defined above] was prepared, and this condensation product and monomer were prepared. The amine amide compound of the general formula (I) is prepared by reacting with halogenated acetic acid at pH 7 to 12, and if necessary, the amine amide compound is modified into its alkali metal salt, ammonium salt, or alkanolamine salt. .

In addition, in the method of the present invention (self), general formula QI): [
In the above formula, R represents an alkyl group having 1 to 4 carbon atoms as defined above] and aminoethylethanolamine are reacted at a temperature of 50 to 120°C in the presence of an alkali catalyst. Then, as a condensation product, N-acyl-N-(2-hydroxyethyl)ethylenediamine represented by the general formula H) [in the above formula, R is the same as defined above] was prepared, and this condensation product and monohalogen acetic acid at pH 7 to 12 to produce the above-mentioned -
An amine amide compound of general formula (I) is prepared, and if necessary, this amine amide compound is modified into its alkali metal salt, ammonium salt, or alkanolamine salt.

In method 0) of the present invention, a fatty acid or fatty acid ester of the general formula Q[) and aminoethylethanolamine are heated (stirred) at 80 to 170°C according to the method described in US Pat. while doing). At this time, it is not necessary to use a catalyst as described in the above US patent specification, or an acid or alkali may be used as a catalyst.
The reaction may be carried out under reduced pressure using an aqueous reaction solution, or
Alternatively, the reaction may be carried out under normal pressure using an organic solvent. The reaction time is generally 1 to 2 hours. The above reaction produces a condensation product while eliminating 1 mole of water or alcohol. This reaction mixture was further heated to 180-2
When heated to 20°C, an additional 1 mole of water is eliminated from the condensation product, resulting in a 2-alkyl- 1-(2-hydroxyethyl)-2-imidazoline (hereinafter simply referred to as an imidazoline compound) is obtained.

The above reaction is generally carried out for 1 to 2 hours. The imidazoline compound thus obtained has the general formula X-CH2CO
OH (in the formula, x represents a halogen atom) is added to a monohalogenated acetic acid aqueous solution, and then the pH thereof is 7 to 1.
2. Add an alkaline aqueous solution such as sodium hydroxide, potassium hydroxide, sodium carbonate, etc. while stirring until the temperature is preferably 7.5 to 10, and then reduce the temperature to 85±5℃.
raise it to react.

As the reaction progresses, the alkali is consumed and the pH decreases, so add additional alkaline aqueous solution dropwise to keep the pH at 7.
to 12, preferably 7.5 to 10. When the reaction is carried out in this manner for 1 to 5 hours, there is almost no change in pH and the reaction is completed. The compound thus obtained is the N-acyl-N-(2-hydroxyethyl)-N, gorbis (
carboxymethyl)ethylenediamine salt, in which the imidazoline ring is cleaved. In the method of the present invention (self), a fatty acid ester in the general formula (U) in which R represents an alkyl group having 1 to 4 carbon atoms;
Aminoethylethanolamine and U.S. Patent No. 2528
378, in the presence of an alkali catalyst such as sodium methoxide, sodium hydroxide, or sodium carbonate at a temperature of 50°C to 120°C to obtain the following general formula (IV): R is the same as the previous definition]
N-acyl-N-(2-hydroxyethyl) represented by
Ethylenediamine can be obtained.

The above reaction is generally carried out for 1 to 4 hours. Next, the amine amide compound of general formula (1) can be obtained by reacting the above condensation product with monohalogenated acetic acid in the same manner as described above. In this method, when a fatty acid-based raw material is used instead of the above-mentioned fatty acid ester, or when an acidic catalyst is used instead of the alkaline catalyst, the above-mentioned (I)
Compounds of formula V) are not obtained or are obtained only in small amounts. Therefore, this method is characterized by using a fatty acid ester as a raw material and using an alkali catalyst to obtain the compound of formula (IV). The amine amide compound of the present invention thus obtained, namely N-acyl-N-(2-
Hydroxyethyl)-N',N'-bis(carboxymethyl)ethylenediamine salt is a new substance and has excellent amphoteric surface activity. Examples of fatty acids and fatty acid esters of general formula (I[) used in the method of the present invention include hydrofuric acid, capric acid, lauric acid, myristic acid, valmitic acid, stearic acid, erucic acid,
Examples include isostearic acid, oleic acid, linoleic acid, isooleic acid, coconut oil fatty acid, beef tallow fatty acid, rice bran oil fatty acid, and esters thereof.

Furthermore, examples of the monohalogenated acetic acid include monochloroacetic acid, monobromoacetic acid, and the like. Further, the alkanolamine preferably has 2 to 4 carbon atoms, and for example, ethanolamine, propanolamine, butanolamine, etc. can be used.

Compounds according to the invention are disclosed in the aforementioned U.S. Pat. No. 2,528,378.
No. 2773068 and Special Publication No. 1973-
The fact that the compound and production method are essentially different from those described in 4762 will be explained in more detail.

In the method of reacting an imidazoline compound with monochloroacetic acid in a strongly alkaline environment according to US Pat. Reaction with monochloroacetic acid yields N-acyl-N-(2-hydroxyethyl)-N'-(carboxymethyl)ethylenediamine salt (Xl).

On the other hand, in the method of the present invention, the imidazoline compound and monochloroacetic acid are reacted under weak alkalinity with a pH of 7 to 12, preferably 7.5 to 10.
Under these conditions, the reaction according to the following reaction formula proceeds preferentially, so that the condensation product in the method of the present invention has the formula ([V
) compounds are produced.

This amide compound (IV) is a very unstable intermediate, and it was found that when it was heated alone or made strongly alkaline, the amide rearranged to form compound (X). Compound wax I) according to the present invention can be obtained in good yield by reacting this compound (IV) with monochloroacetic acid. According to experiments conducted by the present inventors, as shown in Table 4 of Example 1 below, imidazoline and monochloroacetic acid were reacted with the pH controlled at 7 to 12. Compared to what is said to be an imidazoline-type amphoteric surfactant compound synthesized by the method described in Patent No. 2773068 (hereinafter simply referred to as the control product (1)), it has a lower viscosity and is easier to handle. be.

In addition, the compound of the present invention is less irritating to the eyes and skin than the control product (1), has low toxicity, is highly biodegradable, produces very stable foam, has excellent foaming properties, and has excellent foaming properties. It has characteristics such as not causing precipitation in the area, good compatibility with other surfactants, and excellent hard water resistance. For example, the foaming power of the compound obtained in Example 3,
The surface tension and penetration power are as shown in Table 1, and it can be seen that it has excellent surface activity in acidic, alkaline, and neutral conditions. Furthermore, in an ocular mucosal irritation test conducted using white rabbits, the compound of Example 2 was compared with the control product (1) in terms of the total score of irritation of the cornea, conjunctiva, and iris obtained by the tracing method. Table 2 shows that the compound of the present invention is less irritating to the eyes than the control product (1).

Furthermore, Table 3 shows the results of a patch test conducted on 47 male adults to determine whether the compound of Example 2 caused irritation to human skin.

This result also shows that the compounds of the present invention are better than the control products (1) and (2).
) shows less skin irritation.

As described above, the compound according to the present invention is even less irritating than the conventional imidazoline type amphoteric surfactants, which have been used for a long time as being less irritating to the skin and eyes.
Amine amide compounds of the present invention, i.e. N-acyl-N
-(2-hydroxyethyl)-N',N'-bis(carboxymethyl)ethylenediamine salt itself alone,
or other surfactants, such as fatty acids, higher alkyl ether sulfates, higher alkyl sulfates, higher alkylbenzene sulfonic acids, higher alcohol phosphates, etc. and their salts as anionic surfactants; higher alcohols as nonionic surfactants; Higher alkyl phenols, polyhydric alcohols, alkylene oxide adducts such as fatty acid alkylolamides, fatty acid alkylolamides, etc. Cationic surfactants such as higher alkyldimethylpendyl ammonium salts, higher alkyl amines, higher alkyl trimethyl ammonium salts, etc. It can be used as a surfactant in appropriate combination with one or more amphoteric surfactants such as alkylaminopropionate and alkyldimethylpetaine.

This surfactant is effective for cleaning and can be used in applications such as Jump 1, Heavy Jump 1, kitchen detergent, Pet Jump 1, bubble bath cleaning agent, and acidic Jump 1. The present invention will be specifically explained with reference to Examples, but the scope of the present invention is not limited thereto.

Example 1 N-cocoyl-N-(2-hydroxyethyl)-ga,N
Production of '-bis(sodium carboxymethyl)ethylenediamine 225 t of coconut oil fatty acid methyl ester and 104 t of aminoethylethanolamine were reacted with 1 t of sodium methoxide as a catalyst at 85 DEG C. for 1 hour under reduced pressure with stirring.

Thereafter, 4f of phosphoric acid was added as a catalyst to the reaction mixture, and the mixture was treated under reduced pressure at 190±10°C for 2 hours to eliminate 1 mol of water from the reaction product. 1-(2-hydroxyethyl)-2-imidazoline was obtained. The reaction mixture was cooled to room temperature, and added to a solution of separately prepared monochloroacetic acid 189f dissolved in 200 mt of water, and while stirring, a portion of an aqueous solution of sodium hydroxide 160f dissolved in 320 wt of water was added. The pH was set to 7.6. Next, the temperature of the reaction mixture was raised, and the reaction was carried out at 85±5° C. while additional sodium hydroxide aqueous solution was added dropwise so that the pH of the reaction solution was maintained between 7 and 8. The dropwise addition of the aqueous sodium hydroxide solution was completed in 4 hours.

After that, it was aged at the same temperature for 1 hour, and N-cocoyl-N-(2
-Hydroxyethyl)-N',N'-bis(sodium carboxymethyl)ethylenediamine as a main component, an amine amide compound 1148f was obtained. This product was a pale yellow transparent liquid, and its viscosity at 25°C was 220 cP (measured with a B-type rotational viscometer manufactured by Tokyo Keiki Co., Ltd.; all viscosities below were measured with this viscometer). . Examples 2 to 5 The same operations as in Example 1 were performed.

However, when reacting the imidazoline compound with monochloroacetic acid, instead of pH 7 to 8, pH 8 to 9 (Example 2), 9 to 10 (Example 3), 10 to 11 (Example 4), 11 to 12 ( The reaction was carried out at the pH of Example 5). At this time, the dropping times of the aqueous sodium hydroxide solution were 1.5 hours, 1 hour, 40 minutes, and 30 minutes, respectively. In this way, N-cocoyl-N-(2-hydroxyethyl)-N,N-bis(sodium carboxymethyl)ethylenediamine was obtained. Compounds of Examples 2-5 and a control product prepared by the method of U.S. Pat. No. 2,528,378 (
The properties of 1) are shown in Table 4.

Example 6 N-lauroyl-N-(2-hydroxyethyl)-N'
, N-Bis(sodium carboxymethyl)ethylenediamine 200 tons of lauric acid and 104 tons of aminoethylethanolamine were heated and stirred under reduced pressure at 170° C. for 1 hour to react, thereby liberating 1 mole of water.

Thereafter, the reaction mixture was further heated to 220°C and stirred for 2 hours to liberate an additional 1 mol of water from the reaction product.
-undecyl-1-(2-hydroxyethyl)-
268t of 2-imidazoline was obtained. Next, this reaction mixture was cooled to room temperature, and 189 t of monochloroacetic acid was added to 189 t of water.
PH8.
A portion of an aqueous sodium hydroxide solution prepared by dissolving 160 t of sodium hydroxide in 320 ml of water was added until the amount of N-lauroyl-N-(
2-Hydroxyethyl)-N',d-bis(sodium carboxymethyl)ethylenediamine 1126f was obtained as a pale yellow transparent liquid. The viscosity of this product is 245cP
(25°C). Example 7N-caproyl-N-
Production of (2-hydroxyethyl)-N',N-bis(sodium carboxymethyl)ethylenediamine 172 tons of caffrylic acid and 104 tons of aminoethylethanolamine
was reacted in the same manner as in Example 6 using 2-nonyl-
1-(2-hydroxyethyl)-2-imidazoline 240V was obtained.

Next, the imidazoline compound was added to a solution of 189 V of monochloroacetic acid dissolved in 161 V of water, and then a portion of an aqueous solution of 160 T of sodium hydroxide dissolved in 320 V of water was added to adjust the pH of the reaction mixture to 9. It was set as 2. Thereafter, the temperature was raised to 85±5° C., and a reaction was carried out while gradually adding an aqueous sodium hydroxide solution to maintain the pH between 9 and 10. The dropwise addition of the sodium hydroxide aqueous solution was completed in about 1 hour. Thereafter, it was aged for 2 hours at the same temperature, and N-caproyl-N-(2-hydroxyethyl)-N',N'-bis(sodium carboxymethyl)ethylenediamine 1070
I got t. This product was a pale yellow transparent liquid with a viscosity of 35 cP at 25°C. Example 8 N-stearoyl-N-(2-hydroxyethyl)-N',N'-bis(
Preparation of sodium carboxymethyl) ethylenediamine 284f of stearic acid and 104t of aminoethylethanolamine were reacted according to Example 6 to obtain 352f1 of 2-heptadecyl-1-(2-hydroxyethyl)-2-imidazoline.

This imidazoline compound was added to a separately prepared solution of 189 t of monochloroacetic acid dissolved in 188 t of water, and then 160 f of sodium hydroxide was added to 320 ml of water. A portion of an aqueous solution dissolved in water was added until the pH reached 9.6. Next, the temperature of this reaction mixture was raised, and the reaction was carried out at 85±5° C. while adding the sodium hydroxide aqueous solution dropwise so that the pH was maintained between 9 and 10. Dripping of the entire amount of sodium hydroxide was completed in one hour.

Thereafter, it was aged for 2 hours at the same temperature, and N-stearoyl-N-(2-hydroxyethyl)-N',N'-bis(sodium carboxymethyl)ethylenediamine 2588
I got t. This material was a white paste. Example 9 N-lauroyl-N-(2-hydroxyethyl)-go,
Production of N'-bis(sodium carboxymethyl)ethylenediamine 1 t of sodium methoxide was added as a catalyst to 214f of lauric acid methyl ester and 125f of aminoethylethanolamine, and the mixture was reacted under reduced pressure at 80°C for 2 hours.

During the reaction, 1 mole of methanol was liberated. Excess aminoethylethanolamine was then removed under reduced pressure and N-
286t of a gel-like condensate containing lauroyl-N-(2-hydroxyethyl)ethylenediamine as a main component was obtained.
Next, this product was cooled to room temperature and added to a separately prepared solution consisting of 189 f of monochloroacetic acid and 189 g of water.
Furthermore, a portion of an aqueous solution prepared by dissolving 160 f of sodium hydroxide in 320 g of water was added to this solution until the pH reached 8.5. Next, the temperature of this reaction mixture was raised, and the reaction was carried out at 85±5° C. while adding the sodium hydroxide aqueous solution dropwise so that the pH was maintained between 8 and 9. 1.
The dropwise addition of the sodium hydroxide aqueous solution was completed in 5 hours.

After that, it was aged for 2 hours at the same temperature and N-lauroyl-N-(2
-Hydroxyethyl)-N'-bis(sodium carboxymethyl)ethylenediamine (1166 ft) was obtained. The viscosity of this product was 210 cP at 25°C. Example 10 N-oleoyl-N-(2-hydroxyethyl,-N'
,N'-pis(sodium carboxymethyl)ethylenediamine 276f of oleic acid methyl ester and 125r of aminoethylethanolamine were added with 5f of sodium carbonate as a catalyst, and reacted under reduced pressure at 90°C for 3 hours.

During the reaction, 1 mole of methanol was liberated. Next, excess aminoethylethanolamine was removed under reduced pressure to obtain 371t of a gel-like substance containing N-heptadecenyl-N-(2-hydroxyethyl)ethylenediamine as a main component. After cooling this gel-like material to room temperature, it was reacted with monochloroacetic acid at a pH of 8 to 9 in the same manner as in Example 9.
Oleoyl-N-(2-hydroxyethyl)-N',N
'-Bis(sodium carboxymethyl)ethylenediamine 1326f was obtained. This material has a viscosity of 230 cP (2
It was an orange-yellow liquid at a temperature of 5°C. Example 11 N-cocoyl-N-(2-hydroxyethyl)-N',
N'-bis(triethanolaminecarboxymethyl)
Manufacture of ethylenediamine Palm fatty acid methyl ester 22
5f and aminoethylethanolamine 104f1 were reacted under reduced pressure at 85° C. for 1 hour using sodium methoxide 1f as a catalyst, and 1 mole of methanol was eliminated.

After that, 4t of phosphoric acid was added as a catalyst, and 190±1% was added under reduced pressure.
The reaction was carried out at 0°C for 2 hours, 1 mol of water was eliminated, and 2-(coconut fatty acid alkyl)-1-(2-hydroxyethyl) was produced.
-2-imidazoline was obtained and cooled to room temperature. The imidazoline compound was added to a separately prepared solution of 189f monochloroacetic acid dissolved in 200mt of water, and while stirring, 160t of sodium hydroxide was added to 33mt of water.
Add a portion of the aqueous solution dissolved in 20 yoke to adjust the pH to 8.2.
And so. The reaction mixture was then heated to a pH of 8.
The reaction was carried out at 85±5° C. while the sodium hydroxide aqueous solution was added dropwise so as to maintain the temperature between 85° C. and 9° C. 1
．． The dropwise addition of the sodium hydroxide aqueous solution was completed in 5 hours.

After that, it was aged at the same temperature for 1 hour, then cooled to a temperature of 50℃, and 208f of hydrochloric acid (purity 35 (L)) was added for 10 minutes.
Heat and stir at ±5°C, then triethanolamine 2
98 t and 108 f of water were added, and the mixture was heated and stirred at the same temperature for 30 minutes to obtain 1762 t of N-cocoyl-N-(2-hydroxyethyl)-go,N'-bis(triethanolaminecarboxymethyl)ethylenediamine. This product was a pale yellow transparent liquid with a viscosity of 8.2 cP at 25°C. Example 12 Preparation of N-cocoyl-N-(2-hydroxyethyl)-N',N'-bis(ammoniumcarboxymethyl)ethylenediamine The same procedure as in Example 11 was carried out.

However, instead of triethanolamine, 250f of ammonium hydroxide aqueous solution (purity 28%) was added to prepare N-cocoyl-N-(2-hydroxyethyl)-N,N-bis(
ammonium carboxymethyl)ethylenediamine 16
06t was obtained.

This is a pale yellow transparent liquid with a viscosity of 11.
It was 7cP. Example 13 A hypoallergenic jump product was prepared by mixing the following ingredients.

Claims (1)

[Claims] 1 General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the above formula,
R represents a saturated or unsaturated aliphatic hydrocarbon group having 7 to 21 carbon atoms, M is a hydrogen atom, an alkali metal atom,
An amine amide compound represented by a cationic residue of an ammonium group or an alkanolamine. 2 The amine amide compound is N-cocoyl-N-(2
2. The compound according to claim 1, which is -hydroxyethyl)-N',N'-bis(sodium carboxymethyl)ethylenediamine. 3 The amine amide compound is N-lauroyl-N-(
2-Hydroxyethyl)-N',N'-bis(sodium carboxymethyl)ethylenediamine. 4 The amine amide compound is N-caproyl-N-(
2-Hydroxyethyl)-N',N'-bis(sodium carboxymethyl)ethylenediamine. 5 The amine amide compound is N-stearoyl-N-
The compound according to claim 1, which is (2-hydroxyethyl)-N',N'-bis(sodium carboxymethyl)ethylenediamine. 6 The amine amide compound is N-oleoyl-N-(
2-Hydroxyethyl)-N',N'-bis(sodium carboxymethyl)ethylenediamine. 7 The amine amide compound is N-cocoyl-N-(2
2. The compound according to claim 1, which is (hydroxyethyl)-N',N'-bis(triethanolaminecarboxymethyl)ethylenediamine. 8 The amine amide compound is N-cocoyl-N-(2
2. The compound according to claim 1, which is -hydroxyethyl)-N',N'-bis(ammonium carboxymethyl)ethylenediamine. 9. The compound according to claim 1, wherein the cationic residue of the alkanolamine has 2 to 4 carbon atoms. 10 General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [R in the above formula
represents a saturated or unsaturated aliphatic hydrocarbon group having 7 to 21 carbon atoms, and M represents a hydrogen atom, an alkali metal atom, an ammonium group, or a cationic residue of an alkanolamine. Therefore, general formula (II): ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (II) ]
The fatty acid or fatty acid ester represented by the formula (III) and aminoethylethanolamine are reacted at a temperature of 80 to 170°C, and further reacted at a temperature of 180 to 220°C to form a condensation product of the general formula (III): ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (III) [In the above formula, R is the same as defined above] 2-alkyl-1-(2-hydroxyethyl)-2-imidazoline represented by is prepared, and the condensation product is and monohalogenated acetic acid at pH 7 to 12,
An amine amide of the general formula (I), which is characterized in that the amine amide compound of the general formula (I) is prepared and, if necessary, the amine amide compound is modified into an alkali metal salt, an ammonium salt, or an alkanolamine salt thereof. Method of manufacturing the compound. 11 The compound of general formula (II) is caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, erucic acid, isostearic acid, oleic acid, linoleic acid, isooleic acid, coconut oil fatty acid, bovine oil 11. The method according to claim 10, which is an oil fatty acid, a rice bran oil fatty acid, or an alkyl ester thereof having 1 to 4 carbon atoms. 12. The method according to claim 10, wherein the monohalogenated acetic acid is monochloroacetic acid or monobromoacetic acid. 13. The method of claim 10, wherein the alkanolamine has 2 to 4 carbon atoms. 14 General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [R in the above formula
represents a saturated or unsaturated aliphatic hydrocarbon group having 7 to 21 carbon atoms, and M represents a hydrogen atom, an alkali metal atom, an ammonium group, or a cationic residue of an alkanolamine. Therefore, the general formula (II)': ▲ Numerical formulas, chemical formulas, tables, etc. are available. The expressed fatty acid ester and aminoethylethanolamine are reacted at a temperature of 50 to 120°C in the presence of an alkali catalyst, and the condensation product is produced by the general formula (IV): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (IV) [In the above formula, R is the same as defined above] N-acyl-N-(2-hydroxyethyl)ethylenediamine is prepared, and this condensation product and monohalogenated acetic acid are mixed at pH 7 to 12. to prepare the amine amide compound of the general formula (I), and if necessary, convert the amine amide compound into its alkali metal salt, ammonium salt, or alkanolamine salt. A method for producing an amine amide compound of formula (I).15 The compound of general formula (II)' is caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid,
Claim 14, which is an alkyl ester having 1 to 4 carbon atoms of stearic acid, erucic acid, isostearic acid, oleic acid, linoleic acid, isooleic acid, coconut oil fatty acid, beef oil fatty acid, or bran oil fatty acid. Method. 16. The method according to claim 14, wherein the monohalogenated acetic acid is monochloroacetic acid or monobromoacetic acid. 17. The method of claim 14, wherein the alkanolamine has 2 to 4 carbon atoms. 18 General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [R in the above formula
represents a saturated or unsaturated aliphatic hydrocarbon group having 7 to 21 carbon atoms, and M represents a hydrogen atom, an alkali metal atom, an ammonium group or an organic ammonium group. 19 N-cocoyl-N-(2-hydroxyethyl)-
19. The surfactant of claim 18 comprising N',N'-bis(sodium carboxymethyl)ethylenediamine. 20 N-lauroyl-N-(2-hydroxyethyl)
19. The surfactant of claim 18, comprising -N',N'-bis(sodium carboxymethyl)ethylenediamine. 21 N-caproyl-N-(2-hydroxyethyl)
19. The surfactant of claim 18, comprising -N',N'-bis(sodium carboxymethyl)ethylenediamine. 22 N-stearoyl-N-(2-hydroxyethyl)-N',N'-bis(sodium carboxymethyl)
The surfactant according to claim 18, which contains ethylenediamine. 23 N-oleoyl-N-(2-hydroxyethyl)
19. The surfactant of claim 18, comprising -N',N'-bis(sodium carboxymethyl)ethylenediamine. 24 N-cocoyl-N-(2-hydroxyethyl)-
19. The surfactant of claim 18 comprising N',N'-bis(triethanolaminecarboxymethyl)ethylenediamine. 25 N-cocoyl-N-(2-hydroxyethyl)-
19. The surfactant of claim 18 comprising N',N'-bis(ammoniumcarboxymethyl)ethylenediamine.