CS245134B1 - Derivatives of 2-aminobutadiene acid's dialkyl esters - Google Patents

Abstract

Derivatives of dialkyl esters are described 2-aminobutanedio substituted at nitrogen atom of the formula O O II II R1OOCHCH2COR2 NR3CH2CH2OH wherein R 1, R 2 is alkyl of 4 to 8 atoms carbon, R3 is 2-hydroxyethyl or hydrogen and salts of formic and acetic acid. The compounds are suitable for processing glass fibers and can be prepared by the action of monoethanolamine or diethanolamine to the corresponding dialkyl esters butenedioic.

Description

(54) 2-Aminobutanoic acid dialkyl ester derivatives

Disclosed are derivatives of 2-aminobutanedioic acid dialkyl esters substituted on a nitrogen atom of the general formula

O O

II II

R1OOCHCH2COR2

NR 3 CH 2 CH 2 OH wherein R 1, R 2 is alkyl of 4 to 8 carbon atoms, R 3 is 2-hydroxylethyl or a hydrogen atom and light salts of formic and acetic acid. The compounds are suitable for processing glass fibers and can be prepared by reacting monoethanolamine or diethanolamine to the corresponding dialkylesters of butenedioic acid.

³

The present invention relates to nitrogen-substituted 2-aminobutanedioic acid derivatives of dialkyl esters and their salts, with formic and acetic acid, suitable for the treatment and processing of glass and mineral fibers.

New methods of glass fiber treatment and processing have also been reflected in the wide variety of substances used, which improve their textile properties and enable their processing from aqueous suspensions to papers, mats, cartons and other flat formations. Especially for wet fiber processing technologies, it is desirable that the compositions used be of a low cationic, possibly amphoteric nature and low foaming ability of the aqueous compositions.

From the point of view of industrial production of such devices, there are requirements for the availability of raw materials and unpretentious technology of their synthesis.

In our application research, we have found that the compounds of the invention meet these requirements. The present invention provides dialkyl 2-aminobutanedioic acid derivatives substituted at the nitrogen atom of the general formula

O O

R1OCCHCH2COR2

NR 3 CH 2 CH 2 OH wherein represents

R1, R2 alkyl of 4 to 8 carbon atoms,

R3 is 2-hydroxyethyl. or a hydrogen atom and salts thereof with formic and acetic acid.

The preparation of these compounds can be accomplished by coupling monoethanolamine or diethanolamine to the butylenedioic acid alkyl esters wherein the alkyl is a linear or branched chaincoin such as n-butyl, isobutyl,

3-pentyl, n-octyl, 2-ethylhexyl. The advantage of this process is that the raw materials are commercially available and the synthesis is low on equipment. From these imports, their production is also feasible in companies not directly involved in chemical production.

The invention is further illustrated by way of examples.

Example 1

Preparation of ester of formula

CH 3 (CH 2) 3 OOCCH (NHC 2 H 4 OH) CH 2 COO (C 1 H 3 CH 3)

A flask equipped with a stirrer and a thermometer was charged with 300 g (1.3 mol) of dibutyl maleate and 80.3 g (1.3 mol) of monoethanolamine. The exotherm set the batch temperature at 85 ° C for 1.5 hours. The prepared ester having a molecular weight of 289.37 had a viscosity at 20 ° C of 90 mPa. . s, specific gravity 1 060 kg. m ^-3 an _D ²⁰ = 1.4 551. Aqueous compositions of this water-insoluble ester were prepared by neutralizing 100 g ester, 25 g acetic acid, to form a salt on _n ²⁰ = 1.4 493. Effect of salt on reducing surface tension water at 20 ° C is shown in Table 1. Practically identical results are obtained using 20 g of inorganic acid instead of acetic acid, to give a salt on _D ²⁰ = 1.4 563.

TABLE 1

gl ¹ ___ 0.5 ____ mN. m ^-1 50.5 48.5

Example 2

Preparation of ester of formula

CH 3 (CH ₂ ) 3 OOC'CHN (C ₂ H ₄ OH) 2

CH3 (CH2) 3OOGCH2

Into a flask equipped with a stirrer and a thermometer was charged 200 g (0.88 mol) of di 2 5 10

46.5 41.0 · 38.2 butyl maleate and 92 g (0.88 mol of diethanolamine) The batch was heated to 120 ° C and held for 3 hours. The prepared ester having a molecular weight of 333.43 has a viscosity at 20 ° C 483.5 mPa · s, specific gravity 1115 kg m ~ ³ an _D ²⁰ = 1.4 791. The ester is water-soluble and its effect on reducing the surface water tension is shown in Table 2.

TABLE 2 mN. m ^-1

50.5

48.0

44.5

41.0

38.0

gl ¹

0.5

Example 3 dialkyl maleate and equivalent amount of monoethanolamine. The shaft was heated at

Preparation of esters of formula 110 ° C for 2 hours.

50 g of the respective compound were introduced into the flask

TABLE 3

Dialkyl maleate R Amin g Mól. mass pentyl 12.0 317.42 n-hexyl 10.8 345.48 n-heptyl 9.8 373.53 n-octyl 9.0 401.58 2-ethylhexyl 9.0 401.59 Example 4

n _D ²⁰ Viscosity mPa. m / 20 ° Specific mass kg. m ^{3/20 c} 1,4 552 88 1 011 1,4 558 86 997 1,4 569 86 984 1,4 570 85 966 1,4 576 107 977 quarry environment. When solving this problem we found that more preferably, es-

Preparation of ester of formula

CH3 (CH2) 3CH (C2H5) CH2OOCCHN (C2H4OH) 2

CH 3 (CH 2) 5 CH (C 2 H 5) CH 2 OOCCH 2

50 g [0.15 mol) of di (2-ethylhexyl) maleate and 15.5 g (0.15 mol) of diethanolamine were charged to the flask and the batch was heated to 140 ° C for 2 hours. having a viscosity of 234 mPa · s, a specific gravity of 1015 kg · m ^{3 3} and a nD ²⁰ = 1.4.649. The salt can be prepared by mixing 10 g of the ester with 1.4 g of acetic acid and it has nn ²⁰ = 1.4 591 or a 1.1 g formic acid having n _u ²⁰ = 1.4 608. The prepared salts are insoluble in neutral water, so they can only be used in the compositions of the invention according to the invention to solubilize instead of acids using nonionic surfactants, which are a common component of lubricating compositions, oxyethylated fatty alcohols, alkylphenols and fatty acids can be used for this purpose, in addition to the exclusion of acids, compositions which can also be used at pH above 7 are prepared. proceeds so that non-ionic tension d, e.g.: nonylphenol oxyethylated with ethylene oxide in a 1: 9 molar ratio is mixed with the corresponding ester in a 1: 1 weight ratio and, after homogenization, dissolved in water to opalescent to clear solutions. The compositions prepared in this way can be used in the form of 0.1 to 0.5% solutions for the preparation of suspensions. of glass fibers, from which surface forms such as fiberglass paper and mats are made.

Claims (2)

SUBJECT CLAIMS 1. Derivatives of 2-aminobutanoic acid dialkyl esters substituted on a nitrogen atom of the general formula O O II I! R1OCCHCH2COR2 NR 3 GH 2 CH 2 OH wherein represents R1, R2 alkyl of 4 to 8 carbon atoms, YNÁLEZU R 2 is 2-hydroxyethyl or a hydrogen atom, and salts thereof with formic and acetic acid. 2. Sof 2-hydroxyethylaminobutanedioic acid dibutyl ester with acetic acid of the formula O O CH ₃ (CH 2 JOCOHCH 2 CO (CH ₂ J ₃ CH ₃ CH ₃ COO © NH2iCH ₂ CH ₂ OH) Correction to PVAO No. 245 134 (51) Int Cl. ⁴ C 07 C 101/22 Correct, the header name is: (54) 2-Aminobutanedioic acid dialkyl ester derivatives INVENTORY AND DISCOVERY OFFICE