DE1050540B - Process for the production of high molecular weight carboxylic acid esters and carboxylic acid amide group-containing polycondensation products - Google Patents

Description

C O 8 G 6 9 /

GERMAN // 7fi & m < PATENT OFFICE

kl 39 c 10

INTERNAT KL C 08 g

EXPLORATION PAPER 1050 540

REGISTRATION DAY

NOTICE
THE REGISTRATION G
AND ISSUE OF THE
EDITORIAL

F 10898 IVb / 39 c

JANUARY 23, 1953

FEBRUARY 12, 1959

It is known that the Oxazolinermg opposite inorganic acids under suitable conditions is unstable, with splitting of the ring at the Oxygen bridge occurs, mostly to the in / ^ position substituted N-alkyl acid amides thus becomes ζ Β by hydrolysis with dilute mineral acid that / 5-Oxyethylamide, with equimolar amounts of hydrogen bromide the / j-bromoethylamide obtained

The implementation \ on Oxazolmv onnectivity with oxy groups containing mono- and dicarboxylic acids at low temperatures and m the presence of water is known Furthermore, the reaction of Ox was azolmtn with Dicarbonsaureanhydnden to cyclic Imidoverbmdungen described have also already been oxazolines with monocarboxylic acids at temperatures above 100 ⁰ C reacted, although no long-chain products were obtained. The preparation of polymeric, resinous imidoesters by reacting bis-o \ azoones or bis-thiazones with a heteropolymeric compound of maleic anhydride and a polymerizable compound which still contains vinylhdene groups have also already been described, cyclic imido compounds were formed with splitting of the oxazole ring by the maleic anhydride groups

It has now been found that a splitting of the CKazolinnnges with the formation of carboxylic acid ester and carboxamide groups achieved when oxazolmverbindungen of formula

R-T-C =

-N

CH ₅

CH,

where R is an aliphatic, cycloaliphatic ^ araliphatic, aromatic or heterocyclic radical, which can also be substituted, and η is at least 2, with free polycarboxylic acids which contain only carbon and hydrogen in addition to the carboxyl groups, preferably converts dicarboxylic acids at polyamide-forming temperatures

The implementation is carried out with the exclusion of water carried out

Particularly valuable compounds are obtained if bis-oxazolmyl compounds of the formula

N - = C - R - C - = N

ELC

CH,

C H2 CH2

with free dicarboxylic acids. Process for the production

of high molecular weight carboxylic acid ester

and containing amide groups

Polycondensation products

Applicant:

Farbwerke Hoechst Aktiengesellschaft

formerly Master Lucius & Brunmg, Frankfurt / M., Bruningstr. 45

Dr Alfred Jaeger, Frankfurt / M -Unterliederbach, has been named as the inventor

Suitable oxazole compounds are in the 2-position by an organic radical substituted oxazolines of the formula

-C - = N

CH,

CH,

35

where R denotes an aliphatic, cycloaliphatic ^ araliphatic, aromatic or heterocyclic radical, which in turn can also be substituted, and η is at least 2 Examples may be mentioned

1,4-bis [oxazohnyl- (2)] benzene and 1,4-bis [oxazolmyl- (2)] butane

Free polycarboxylic acids can be used as carboxylic acids, provided they are in an anhydrous state Implementation

Above all are ahphatic and aromatic dicarboxylic acids, such as oxalic, succinic, malonic, glutaric, adipic acid, Terephthalic, Malic and Fumaric Acids, for the implementation Also suitable polycarboxylic acids such as \ conitic acid, can be used

Are ζ B dicarboxylic acids with bis-oxazole myr compounds implemented, one arrives in a simple manner in long-chain compounds which are more regular and alternating sequence containing the carboxylic acid ester and carboxamide group in the molecule

809 749/407

HOOC-R-COOH + -N = C- R '- C =

CH ₂ OO

CH ₂ HOOC R COOH + N = C ₇ -R'- C = - N

I ι

0 CH ₂

CH ₂ 0

CH ₉

CH,

CH,

CH ₂

HOOC-R-COOCH ₉ Ch ₉ NHCO- R'-CONH- CH, -CH, OCO -R CO-OCH, CH, NHCO R'-CONHCH, ...

The reaction of bis-oxazolines with free dicarboxylic acids carried out according to the present process in the absence of water at polyamide-forming temperatures leads in a smooth reaction to high molecular weight, linear products that are valuable raw materials for the manufacture of fibers and foils.

example

216 g of 4-bis [oxazolinyl- (2)] benzene and 150 g of adipic acid are ^{heated to 230 to 240 °} C. for 45 minutes with thorough stirring. The result is a polymer which is elastic even in the cold and has a softening point above 200 ^° C. and can be drawn out into long threads.

Claims (1)

Claim: draws that oxazoline ver compounds of the formula - C N CH, CH ₂ where R denotes an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical, which in turn can be substituted, and η is at least 2, with free polycarboxylic acids which contain only carbon and hydrogen in addition to the carboxyl groups, preferably dicarboxylic acids, with the exclusion of water polyamide-forming temperatures. Considered publications: Process for the preparation of high molecular weight 30 United States Patent Nos. 2402791, 2547494, 2580047, carboxylic acid ester and carboxamide group halves 2543602;
term polycondensation products, thereby identified- Chem. Abstracts, 1951, column 1114 i to 1115 b. © 809 749/407 2.