Patent GB-544649-A (GB)
Title: Manufacture of polymeric materials
IPC: C08G69/02
Filed: 1940-10-18
Abstract: 544,649. Polyamides. DU PONT DE NEMOURS & CO., E. I. Oct. 18, 1940, No. 15423. Convention date, Oct. 18, 1939. [Classes 2 (iii) and 15 (ii)] Improved fibre-forming polyamides of the type described in Specifications 461,236, 461,237, and U.S.A. Specifications 2,071,253 and 2,130,948 are obtained from mixtures of diamines and dibasic acids or from monoamino mono carboxylic acids by the employment of at least one of the above re-actants having a lateral substituent comprising or containing a hydroxyl group which is removed by at least five atoms from any carboxyl group and by at least three atoms from any amino group in the molecule. The polymerization is effected by heating to 300 C. in an open or closed vessel and under normal, increased or reduced pressure and in the presence of inert solvents, e.g. phenols, cresols, xylenols, hydroxy diphenyls or non-solvents, e.g. white medicinal oil. There are specified- (1) Hydroxyl substituted dibasic acids. 6 : 6 bis and 6-(p-hydroxyphenyl) - hendecanedioic acid, 6 : 6 bis and 6 - (4<SP>1</SP> - hydroxynaphthyl) hendecanedioic acid, 6 - hydroxyhendecanedioic acid, # (p - hydroxyphenyl) adipic acid, 4 : 4 bis and 4 - (4<SP>1</SP> - hydroxynaphthyl) - pimelic acid, phenol 2 : 4 - dibutyric acid, phenol - 2 : 4 - dicaproic acid, # - (4 - bydroxy - cyclohexyl) adipic acid. (2) Hydroxy substituted diamines. 3 - (41 - hydroxyphenyl) hexamethylenediamine, 3 - (41- hydroxycyclohexyl) bexamethylenediamine, 6 - hydroxyhendecamethylenediamine, 2 - 4<SP>1</SP> - hydroxyphenyl - tetramethylenediamine, 5 - bydroxynonamethylenediamine, 4 - hydroxyoctamethylenediamine, 4 - hydroxyheptamethylenediamine, 3 - (4<SP>1</SP> - hydroxyphenyl) pentamethylenediamine, 3 - (hydroxymethyl) hexamethylenediamine, phenol - - 2 : 4 - bis (6<SP>1</SP> - hexylamine) ; phenol - 2 : 4 - bis (2<SP>1</SP> - ethylamine). (3) Hydroxy substituted aminomonocarboxylic acids. # - (4 - hydroxyphenyl) - e - amino - caproic acid, 11 - amino - 6 - hydroxyhendecanoic acid, # - (4 - hydroxycyclohexyl) - e - aminocaproic acid. The hydroxyl group increases the solubility of the polymer and facilitates pressing of fabrics made therefrom ; while the solubility may be decreased by reacting the hydroxyl groups with a diisocyanate, or dimethylolurea or long chain acylethenone. Hydroxyl groups coupled with aromatic groups may be coupled with diazonium compounds, e.g. benzene diazonium chloride to give coloured derivatives. In examples (4) the salt of hexamethylenediamine and #-(p-hydroxyphenyl) adipic acid was prepared by mixing equivalent alcoholic solutions of the two compounds. 10 per cent. of this salt and 90 per cent. of the salt of hexamethylenediamine and adipic acid together with 1.25 mol. per cent. of acetic acid as viscosity stabilizer were heated together at 250 C. for 2 hours in a sealed tube filled with nitrogen and then at 268 C. for 2 hours at atmospheric pressure. A hard tough interpolyamide was obtained which could be spun into long filaments easily cold drawn. #-(p-hydroxyphenyl) adipic acid is obtained by nitrating #-phenyladipic acid, hydro-' genating the nitro compound in presence of platinum, and diazotizing the hydrogenated compound.