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

2-Aminobutanoic acid dialkyl ester derivatives Download PDF

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CS245134B1
CS245134B1 CS851038A CS103885A CS245134B1 CS 245134 B1 CS245134 B1 CS 245134B1 CS 851038 A CS851038 A CS 851038A CS 103885 A CS103885 A CS 103885A CS 245134 B1 CS245134 B1 CS 245134B1
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acid
acetic acid
acid dialkyl
derivatives
ester
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CS851038A
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Czech (cs)
Slovak (sk)
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CS103885A1 (en
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Stanislav Florovic
Juraj Forro
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Stanislav Florovic
Juraj Forro
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Abstract

Popisujú sa deriváty, dialkylesterov kyseliny 2-amínobutándiovej substituované na atóme dusíka obecného vzorca O O II II R1OOCHCH2COR2 NR3CH2CH2OH kde představuje Ri, R2 alkyl s 4 až 8 atómami uhlíka, R3 2-hydroxyletyl alebo atom vodíka a leh soli s kyselinou mraveou a octovou. Zlúčeniny sú vhodné na spracovanie skleněných vlákien a možno ich připravit pósobením monoetanolamínu alebo dietanolamínu na příslušné dialkylestery kyseliny buténdiovej.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) Deriváty dialkylesterov kyseliny 2-amínobutánovej(54) Derivatives of dialkyl esters of 2-aminobutanoic acid

Popisujú sa deriváty, dialkylesterov kyseliny 2-amínobutándiovej substituované na atóme dusíka obecného vzorcaDerivatives of dialkyl esters of 2-aminobutanedioic acid substituted on the nitrogen atom of the general formula are described

O OAbout About

II IIII II

R1OOCHCH2COR2R1OOCHCH2COR2

NR3CH2CH2OH kde představuje Ri, R2 alkyl s 4 až 8 atómami uhlíka, R3 2-hydroxyletyl alebo atom vodíka a leh soli s kyselinou mraveou a octovou. Zlúčeniny sú vhodné na spracovanie skleněných vlákien a možno ich připravit pósobením monoetanolamínu alebo dietanolamínu na příslušné dialkylestery kyseliny buténdiovej.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.

33

Vynález sa lýka derivátov dialkylesterov kyseliny 2-amínobutándiovej substituovaných na atome dusíka a ich solí, s kyselinou mravčou a octovou vhodných na úpravu a spracovanie skleněných a minerálnych vlákien.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.

Nové sposoby úpravy a spracovania skleněných vlákien sa odzrkadlili aj v širokej palete používaných látok, ktoré zlepšujú ich textilně vlastnosti a umožňujú ich spracovanie z vodných suspenzii na papiere, rohože, kartóny a iné plošné útvary. Zvlášť pre mokré technologie spracovania vlákien je požadované, aby používané prostriedky malí katlonlcký, připadne amfotérny charakter a nízku penivosť vodných kompozícií.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.

Z pohl'adu priemyselnej výroby takýchto prostredkov sú dané požiadavky dostupnosti surovin a nenáročnej technologie ich syntézy.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.

Pri aplikačnom výskume sme zistili, že týmto požiadavkám vyhovujú zlúčeniny podlá vynálezu. Vynález popisuje deriváty dialkylesterov kyseliny 2-amínobutándiovej substituované na atome dusíka obecného vzorcaDuring 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

O OAbout About

R1OCCHCH2COR2R1OCCHCH2COR2

NR3CH2CH2OH kde představujeNR3CH2CH2OH where represents

Ri, R2 alkyl s 4 až 8 atómaini uhlíka,R1, R2 alkyl with 4 to 8 carbon atoms,

R3 2-hydroxyetyl. alebo atom vodíka a ich soli s kyselinou mravčou a octovou.R3 2-hydroxyethyl. or a hydrogen atom and their formic and acetic acid salts.

Pripravu týchto zlúčenín je možné uskutočniť posobením monoetanolamínu alebo dietanolamínu na clialkylestery kyseliny buténdiovej, kde alkyl je s lineárnym alebo rozvětveným reťazcoin ako n-butyl, izobutyl,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-oktyl, 2-etylhexyl. Výhodou tohto postupu je, že suroviny sú bežne komerčně dostupné a syntéza je nenáročná na zariadenie. Z týchto dovodov je ich výroba realizovatelná aj v podnikoch, ktoré sa bezprostredne chemickou výrobou nezaoberajú.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.

Vynález je ďalej objasněný formou príkladov.The invention is further clarified by way of examples.

Příklad 1Example 1

Příprava esteru vzorcaPreparation of an ester of the formula

CHs (CH2) 3OOCCH (NHC2H4OH ] CH2COO (CIh ] 3CH3CHs(CH2)3OOCCH(NHC2H4OH]CH2COO(CIh]3CH3

Do banky opatrenej miešadlom a teplomerom sa předložilo 300 g (1,3 molu) dibutylmaleinátu a 80,3 g (1,3 molu) monoetanolamínu. Exotermom teplota násady vystňpila na 85 °C, na ktorej sa udržovaly 1,5 hod. Připravený ester o molekulovej hmotnosti 289,37 má viskozitu při 20 °C 90 mPa . . s, mernú hmotnost 1 060 kg . m-3 a nD 20 = = 1,4 551. Vodné kompozície tohoto vo vodě nerozpustného esteru sa připravili neutralizáciou 100 g esteru, 25 g kyseliny octovej, za vzniku soli o nn 20 = 1,4 493. Vplyv soli na zníženie povrchového napatia vody pri 20 °C je uvedený v tabufke 1. Prakticky zhodné výsledky sa dosiahnu pri použití namiesto kyseliny octovej 20 g kyseliny inravčej, za vzniku soli o nD 20 = 1,4 563.300 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.

TABULKA 1TABLE 1

g.l1___0,5____ mN. m_1 50,5 48,5gl 1 ___0.5____ mN. m _1 50.5 48.5

Příklad 2Example 2

Příprava esteru vzorcaPreparation of an ester of the formula

CHs (CH2 )3OOC'CHN (C2H4OH )2CHs (CH 2 ) 3 OOC'CHN (C 2 H 4 OH ) 2

CH3(CH2)3OOGCH2CH3(CH2)3OOGCH2

Do banky opatrenej miešadlom a teplomerom sa předložilo 200 g (0,88 molu) di2 5 10200 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 butylmaleinátu a 92 g (0,88 móluj dietanolamínu. Násada sa vyhriala na 120 °C, na ktorej sa udržovala 3 hod. Připravený ester o molekulovej hmotnosti 333,43 má viskozitu pri 20 °C 483,5 mPa . s, mernú hmotnost 1115 kg. m~3 a nD 20 = 1,4 791. Ester je rozpustný vo vodě a jeho vplyv na zníženie povrchového napátia vody je uvedený v tabufke 2.46.5 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.

TABULKA 2 mN . m-1 TABLE 2 mN.m -1

50,550.5

48,048.0

44,544.5

41,041.0

38,038.0

g.l1 gl 1

0,50.5

Přiklad 3 dialkylmaleinatu a ekvivalentně množstvo monoetanolamínu. Násada sa zahrievala přiExample 3 dialkyl maleate and an equivalent amount of monoethanolamine. The batch was heated at

Příprava esterov vzorca 110 °C 2 hod. Množstvo aminu a vlastnosti jednotlivých esterov sú uvedené v tabul'ROOCCHfNHCzHdOHjCHzCOOR ke 3.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.

Do banky sa předložilo 50 g příslušného50 g of the relevant substance was submitted to the bank.

TABULKA 3TABLE 3

Dialkylmaleinát R Dialkyl maleate R Amin g Amen g Mól. hmotnost Molecular weight pentyl pentyl 12,0 12.0 317,42 317.42 n-hexyl n-hexyl 10,8 10.8 345,48 345.48 n-heptyl n-heptyl 9,8 9.8 373,53 373.53 n-oktyl n-octyl 9,0 9.0 401,58 401.58 2-etylhexyl 2-ethylhexyl 9,0 9.0 401,59 401.59 Příklad 4 Example 4

nD 20 nD 20 Viskožita mPa . m/20° Viscosity mPa . m/20° Měrná hmot. kg . m 3/20c Specific gravity kg . m 3 /20 c 1,4 552 1.4 552 88 88 1 011 1,011 1,4 558 1.4 558 86 86 997 997 1,4 569 1.4 569 86 86 984 984 1,4 570 1.4 570 85 85 966 966 1,4 576 1.4 576 107 107 977 977 lom prostředí. environmental damage. Pri riešení When solving tohto problému this problem sme zistili, že we found out that podstatné výhodnejšie je es- significantly more advantageous is es-

Příprava esteru vzorcaPreparation of an ester of the formula

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

CHs (CH2 )5CH( C2H5) CH2OOCCH2CH s (CH 2 ) 5 CH( C 2 H 5 ) CH 2 OOCCH 2

Do banky sa předložilo 50 g [0,15 molu) di( 2-etylhexyl jmaleinátu a 15,5 g (0,15 molu) dietanolamínu. Násada sa vyhriala na 140 °C, na ktorej sa udržovala 2 hod. Připravený ester o molekulovej hmotnosti 445,65 má pri 20 °C viskozitu 234 mPa . s, mernú hmotnost 1015 kg. m~3 a nD20 = = 1,4 649. Sol' je možné připravit zmiešaním 10 g esteru s 1,4 g kyseliny octovej a má nn20 = 1,4 591 alebo a 1,1 g kyseliny mravčej, ktorá má nu 20 = 1,4 608. Připravené soli sú v neútrálnej vodě nerozpustné, preto je ich možné používat do· kompozícií len v ikystery podta vynálezu solubilizovať namiesto kyselin použitím neiónových tenzidov, ktoré sú běžnou zložkou lubrikačných kompozícií. K tomuto účelu je možné použit oxyetylované mastné alkoholy, alkylfenoly a mastné kyseliny. Týmto spósobom okrem vylúčenia kyselin sa pripravia kompozície, ktoré je možné používat aj pri pH nad 7. Pri přípravě sa postupuje tak, že neiónový tenzid, napr.: nonylfenol oxyetylovaný etylénoxidom v molárnom pomere 1 : 9 sa zmieša s příslušným esterom v hmotnostnom pomere 1 : 1 a po homogenizácii sa rozpúšťa vo vodě na opalescentné až číře roztoky. Týmto spósobom připravené kompozície je možné používat vo formě 0,1 až 0,5 % roztokov k príprave suspenzi! skleněných vláfcien, z ktorých sa vyrábajú plošné útvary ako sklovláknitý papier a rohože.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)

PREDMETSUBJECT 1. Deriváty dialkylesterov kyseliny 2-amínobutánovej substituované na atome dusíka obecného vzorcaCLAIMS 1. Derivatives of 2-aminobutanoic acid dialkyl esters substituted on a nitrogen atom of the general formula O OO O II I!II I! R1OCCHCH2COR2R1OCCHCH2COR2 NR3GH2CH2OH kde představujeNR 3 GH 2 CH 2 OH wherein represents Ri, R2 alkyl s 4 až 8 atómami uhlíka,R1, R2 alkyl of 4 to 8 carbon atoms, YNÁLEZUYNÁLEZU Rs 2-hydroxyetyl alebo atom vodíka, a ich soli s kyselinou mravčou a octovou.R 2 is 2-hydroxyethyl or a hydrogen atom, and salts thereof with formic and acetic acid. 2. Sof dibutylesteru kyseliny 2-hydroxyetylamínobutándiovej s kyselinou octovou vzorca2. Sof 2-hydroxyethylaminobutanedioic acid dibutyl ester with acetic acid of the formula O OO O CH3 (CH2 jjOCOHCHzCO (CH2 J3CH3 CH3COO©©NH2iCH2CHzOHCH 3 (CH 2 JOCOHCH 2 CO (CH 2 J 3 CH 3 CH 3 COO © NH2iCH 2 CH 2 OH) OPRAVA k PVAO č. 245 134 (51) Int Cl.4 C 07 C 101/22Correction to PVAO No. 245 134 (51) Int Cl. 4 C 07 C 101/22 Správný, název záhlaví je:Correct, the header name is: (54) Deriváty dialkylesterov kyseliny 2-amínobutándiovej(54) 2-Aminobutanedioic acid dialkyl ester derivatives ÚŘAD PRO VYNÁLEZY A OBJEVYINVENTORY AND DISCOVERY OFFICE
CS851038A 1985-02-14 1985-02-14 2-Aminobutanoic acid dialkyl ester derivatives CS245134B1 (en)

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