CS245134B1 - 2-Aminobutanoic acid dialkyl ester derivatives - Google Patents

Abstract

Derivatives of 2-aminobutanedioic acid dialkyl esters substituted on the nitrogen atom of the general formula O O II II R1OOCHCH2COR2 NR3CH2CH2OH where R1, R2 represent alkyl with 4 to 8 carbon atoms, R3 represents 2-hydroxyethyl or a hydrogen atom and their salts with formic and acetic acid are described. The compounds are suitable for the processing of glass fibers and can be prepared by the action of monoethanolamine or diethanolamine on the corresponding dialkyl esters of butanedioic acid.

Description

(54) Derivatives of dialkyl esters of 2-aminobutanoic acid

Derivatives of dialkyl esters of 2-aminobutanedioic acid substituted on the nitrogen atom of the general formula are described

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II II

R1OOCHCH2COR2

NR3CH2CH2OH where represents Ri, R2 alkyl with 4 to 8 carbon atoms, R3 2-hydroxylethyl or a hydrogen atom and a salt with formic and acetic acid. The compounds are suitable for the processing of glass fibers and can be prepared by treating monoethanolamine or diethanolamine with the respective dialkylesters of butenedioic acid.

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

New methods of treatment and processing of glass fibers were also reflected in the wide range of substances used, which improve their textile properties and enable their processing from aqueous suspensions to paper, mats, cardboard and other surface structures. Especially for wet fiber processing technologies, it is required that the agents used have a low catholic, possibly amphoteric character and low foaming of aqueous compositions.

From the point of view of the industrial production of such means, the requirements for the availability of raw materials and the undemanding technology of their synthesis are given.

During applied research, we found that the compounds according to the invention meet these requirements. The invention describes derivatives of dialkyl esters of 2-aminobutanedioic acid substituted on the nitrogen atom of the general formula

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R1OCCHCH2COR2

NR3CH2CH2OH where represents

R1, R2 alkyl with 4 to 8 carbon atoms,

R3 2-hydroxyethyl. or a hydrogen atom and their formic and acetic acid salts.

The preparation of these compounds can be carried out by converting monoethanolamine or diethanolamine into clialkylesters of butenedioic acid, where the alkyl is linear or branched, such as n-butyl, isobutyl,

3-pentyl, n-octyl, 2-ethylhexyl. The advantage of this procedure is that the raw materials are usually commercially available and the synthesis is easy on the equipment. For these reasons, their production is feasible even in companies that are not directly involved in chemical production.

The invention is further clarified by way of examples.

Example 1

Preparation of an ester of the formula

CHs(CH2)3OOCCH(NHC2H4OH]CH2COO(CIh]3CH3

300 g (1.3 mol) of dibutyl maleate and 80.3 g (1.3 mol) of monoethanolamine were placed in a flask equipped with a stirrer and a thermometer. By exotherm, the temperature of the mixture rose to 85 °C, where it was maintained for 1.5 hours. The prepared ester with a molecular weight of 289.37 has a viscosity of 90 mPa at 20 °C. . s, specific weight 1,060 kg. m ^-3 an _D ²⁰ = = 1.4 551. Aqueous compositions of this water-insoluble ester were prepared by neutralizing 100 g of the ester, 25 g of acetic acid, forming a salt on _n ²⁰ = 1.4 493. The effect of salt on reducing the surface tension of water at 20 °C is shown in table 1. Practically identical results are achieved when 20 g of acetic acid is used instead of acetic acid inravčej, to form a salt he _D ²⁰ = 1.4 563.

TABLE 1

gl ¹ ___0.5____ mN. m ^_1 50.5 48.5

Example 2

Preparation of an ester of the formula

CHs (CH ₂ ) 3 OOC'CHN (C 2 H 4 OH ) 2

CH3(CH2)3OOGCH2

200 g (0.88 mol) of di2 5 10 was placed in a flask equipped with a stirrer and a thermometer

46.5 41.0· 38.2 butyl maleate and 92 g (0.88 moles of diethanolamine. The mixture was heated to 120 °C, where it was maintained for 3 hours. The prepared ester with a molecular weight of 333.43 has a viscosity at 20 °C of 483.5 mPa . s, a specific gravity of 1115 kg. m~ ³ an _D ²⁰ = 1.4 791. The ester is soluble in water and its effect on reducing the surface tension of water 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 an equivalent amount of monoethanolamine. The batch was heated at

Preparation of esters of the formula 110 °C 2 hours. The amount of amine and the properties of individual esters are listed in table 3. ROOCCHfNHCzHdOHjCHzCOOR.

50 g of the relevant substance was submitted to the bank.

TABLE 3

Dialkyl maleate R Amen g Molecular weight 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

_nD ²⁰ Viscosity mPa . m/20° Specific gravity 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 environmental damage. When solving this problem we found out that significantly more advantageous is es-

Preparation of an ester of the formula

CH3(CH2 ) 3CH ( C2TI5 ) CH2OOCCHN (C2H4OH )2

CH s (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 introduced into the flask. The batch was heated to 140 °C, where it was maintained for 2 hours. The prepared ester with a molecular weight of 445.65 has a viscosity of 234 mPa.s at 20 °C, a specific gravity of 1015 kg. m~ ³ and nD ²⁰ = = 1.4 649. The salt can be prepared by mixing 10 g of ester with 1.4 g of acetic acid and has nn ²⁰ = 1.4 591 or a 1.1 g of formic acid, which has n _u ²⁰ = 1.4 608. The prepared salts are insoluble in neutral water, so they can only be used in compositions ikysters according to the invention can be solubilized instead of using acids nonionic surfactants, which are a common component of lubricating compositions. For this purpose, it is possible to use oxyethylated fatty alcohols, alkylphenols and fatty acids. In addition to excluding acids, compositions can be prepared in this way, which can also be used at a pH above 7. The preparation is carried out in such a way that a nonionic surfactant, e.g. nonylphenol oxyethylated with ethylene oxide in a molar ratio of 1:9 is mixed with the appropriate ester in a mass ratio of 1:1 and after homogenization is dissolved in water to form opalescent to clear solutions. Compositions prepared in this way can be used in the form of 0.1 to 0.5% solutions to prepare suspensions! of glass filaments, from which flat structures such as fiberglass paper and mats are produced.

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