SU1139724A1 - Salts of monoalkylamidodimethyleneamino-n-(2,3-dihydroxypropyl)-n-acetic acid as foam generating agents - Google Patents

Abstract

Salts of monoalkylamide dimetyphenylHo-N- 2, 3-dihydroxypropyl) -Y-acetic acid of the general formula RCONH-CHjCHjN LSh, hw, h, OH where K is alcml with S; 12, M, 16 or 18 atoms of 14 and carbon} X - potassium, sodium or triethanolamine, as frothers.

Description

The invention relates to new chemical compounds, monoalkylamido dimethylene amino-K- (2,3-dihydroxypropyl) K-acetic acid salts of the general formula, CH. CHgCH-CHjOH where R is alkyl with 10, 12, -14, 16, or 18 carbon atoms | X is potassium, sodium, or trietano amine, as blowing agents. The closest to the proposed are the salts of alkylamido dimethylamino-N-hydroxyethyl-N-yccyclic acid of the formula: ccr Soan RCONH-CHzCH2-N. The disadvantages of these compounds are low surface activity and foaming ability. The purpose of the invention is the discovery of new derivatives in the range of acetic acid with improved foaming ability. This goal is achieved by new compounds - monoalkylamido dimethyleneamino-N- (2, 3-dihydroxypropyl) -N-acetic acid salts of formula (1) as blowing agents. The proposed compounds are prepared in two ways. In the first method, the reaction between the carboxylic acid chlorides and the salt of N-dimethylenedia HO-N- (2,3-dihydroxypropyl) -N-acetic acid is carried out. The reaction is carried out in aqueous solution of alkali at 40-60 ° C and lasts 2-3 hours. Then the reaction mixture is dried and extracted with a boiling mixture of solvents consisting of toluene and hexane. After distillation of the solvents, the desired product is obtained. In the second method, the reaction of carboxylic acid esters of lower aliphatic alcohols with the salts of H-dimethylenediamino-H- (2,3-dihydroxy-6-nx1) -n-acetic acid is carried out. The reaction is carried out in a medium of lower aliphatic alcohols at the boiling point of the solvent within 3–10 hours. The implementation of the method of obtaining new surfactants as foaming agents is illustrated by the following examples. P and not p 1. 24.8 g of capric acid chloride are added to 32.0 g of the potassium salt of N-dimethylenediamino-M- (2,3-dihydroxypropyl) -N-acetic acid, dissolved in 100 ml of water. At the same time, while stirring, to the mixture was added 8.0 g of KOH dissolved in 30 ml of water. The reaction mixture is heated for 2 hours at 45 ° C. At the end of the reaction, the mixture is dried and extracted with a boiling mixture of solvents consisting of 100 ml of toluene and 50 ml of hexane. After distilling off the solvents, the target product in the form of the potassium salt of monodecylamido dimethyleneimino-N- (2, 3-dihydroxypropyl) -N-acetic acid was obtained in an amount of 41.8 g, which corresponds to 80% of the theoretical yield. The gross formula of the target product: C H OjNgK. Example 2: To 47 g of sodium salt of H-dimethylenediamine 1M - (2,3-dihydroxypropyl) -N-acetic acid, dissolved in 130 ml of water, 46 g of lauric acid chloride are added with stirring. At the same time, 8.4 g of sodium hydroxide dissolved in 30 ml of water was added to the mixture. The reaction mixture is heated for 2 hours, then dried and extracted with a boiling mixture of solvents consisting of 130 ml of toluene and 70 i-m hexane. After distilling off the solvents, sodium dodecylamide dimethylene-amino-N- (2,3-dihydroxypropyl) -N-acetic acid is obtained in an amount of 65.5 g. The yield is 79% of the theoretical value. The gross formula of the target product; . Froze 24 g of methyl myristate, dissolved in 20 ml of methanol, are added to 22 g of sodium salt of K-dimethylenediamino-M - (2,3-dihydroxypropyl) -N-acetic acid, dissolved in 50 ml of methanol. The reaction mixture is boiled for 3 hours under reflux, then methanol is distilled off and the residue is washed with 200 ml of octane. Obtain 32 g of sodium salt monotetradecylamido dimethylaMHHo-N- (2,3-dihydroxypropyl) -N-acetic acid. The yield is 80% of theoretical. Gross formula of the target product:.

An example. 100 g of ethyl palmita, dissolved in 200 ml of ethanol, are dosed to 78 g of the triethanolamine salt of N-dimethylenediamino-M - (2,3-dihydroxypropyl) -Y-acetic acid, dissolved in 100 ml of ethanol. The reaction mixture is heated under reflux for 6 hours. Upon completion of the reaction, ethanol was distilled off, and unreacted ethyl palmitate was extracted with 150 ml of ether. 124 g of the triethanolamine salt of hexadecylamidodimethyleneamino-N- (2,3-dihydroxyprosh) -Y-acetic acid are obtained. The yield is 78% of the theoretical. The gross formula of the target product:

Example 5. 90 g of methyl stearate dissolved in 200 ml of methanol are dosed to 68.2 g of the triethanolamine salt of N-dimethylenediamino-N- (2,3-dihydroxypropyl) -Y-acetic acid, dissolved in 100 mp of methanol . The mixture was heated under reflux for 10 hours. After the completion of the reaction, the alcohol was distilled off, and the excess methyl stearate was extracted with 200 ml of ether. Obtain 102 g of the triethanolamine salt octadecylamidodimethyleneamino-H-- (2,3-dihydroxypropyl) -N-yK cus with hydrochloric acid or 84% of theory. Target gross formula

product: 0.1

The elemental composition of the proposed monoalkylamidodimethylenamino-N- (2,3-dihydroxypropyl) -N-acetic acid salts is given in Table 1.

Table 2 shows the surface activity of monoalkylamido dimethylenimio-L- (2,3-dihydroxypropsh1) -N-acetic acid salts (amidines) in comparison with the prototype (determined by the stalagleometric method at 20 ° C, the drop rate of 2 minutes).

Penoobrazukitsa ability salts monoalkilamndodimvtilenamino-N- (2,3-digidroksiproshSh) -N-acetic acid (amidines) and alkilamidodimetlenamino-N-gidpokcietil-N-ykcycnoy acid (prototype) by Ross Moyles with distilled water is given in Table 3.

As can be seen from Tables 2 and 3, the proposed compounds have better surface-active properties, as compared with the known ones of similar structure.

Table 1

Potassium80

-Yu

Sodium 79

-12

Sodium 80

four

Triethanolamine 78

Triethanol f8 amine 84

7.0 7.1 50.9 51.2 8.2 8.0 7.1, 6.9 57.6 57.4 9.3 9.5

6.6 6.4 59.0 58.2 9.6 9.7

7.9 8.0 56.5 56.3 11.2 11.4

6.9 6.8 61.3 60.9 10.7 11.0