Patent GB-523506-A (GB)
Title: Polymeric material
IPC: C08G69/40
Filed: 1939-01-10
Abstract: 523,506. Polyamides. DU PONT DE NEMOURS & CO., E. I. Jan. 10, 1939, No. 787. Convention date, Jan. 14, 1938. [Class 2 (iii)] Bifunctional sulphonamides of the formula (in which A is an amide-forming group, R and R<SP>1</SP> are divalent hydrocarbon radicals having a chain length of at least three carbon atoms, R<SP>11</SP> is H or a univalent hydrocarbon radical and Q is NR<SP>11</SP>-CO or NR<SP>11</SP>-SO 2 ) are condensed with a bifunctional amide-forming reactant in which the amide-forming groups are complementary to those contained in the sulphonamide. The sulphonamides may be prepared by the condensation of a sulphonyl halide of the formula (in which Z is CO or SO and X halogen, preferably chlorine, R having a chain length of at least three carbon atoms) with a bifunctional compound of the formula (in which B is an amide-forming group or a univalent radical capable of yielding an amideforming group on hydrolysis, R<SP>1</SP> having a chain length of at least three carbon atoms). Suitable bifunctional sulphonamides include trimethylenedisulphonyl - bis - - e - aminocaproic acid (HOOC-(CH 2 ) 5 -NH-O 2 S-(CH 2 ) 3 -SO 2 -NH- (CH 2 ) 5 -COOH), hexamethylenedisulphonyl - bis - e - amino caproic acid (HOOC-(CH 2 ) 5 -NH-O 2 S-(CH 2 ) -SO 2 - NH-(CH 2 ) 5 -COOH), m-benzenedisulphonyl - bis - # - aminocaproic acid (HOOC-(CH 2 ) 5 -NH-O 2 S-(C 6 H) 4 -SO 2 -NH- (CH 2 ) 5 -COOH), tetramethylenedisulphonyl - bis - 6 - aminohexyl diamine (H 2 N-(CA 2 ) 6 -NH-O 2 S-(CH 2 ) 4 -SO 2 -NH- (CH 2 ) 6 -COOH) and compounds of the formulae H 3 COOC - (CH 2 ) 4  - NCH, - O 2 S - (CH 2 ) 4  - SO 2 -NCH 3 -(CH 2 ) 4 -COO-CH 3 , H 5 C 2  - OOC - (CH 2 ) 9  - NH - O 2 S - (CH 2 ) 2  - CHCH 3  - (CH 2 ) 3  - SO 2  - NH - (CH 2 ) 9  - COO - C 2 H 5 , HOOC - (CH 2 ) 5  - NH - 0  2 S - C 6 H 4  - C 6 H 4  - SO 2  - NH-(CH 2 ) 5 -COOH, HOOC - (CH 2 ) 2  - CHCH 3  - CH 2  - NH - O zS- (CH 2 ) 10  - SO 2  - NH - CH 2  - CHCH 3  - (CH 2 ) 2  - COOH, HOOC - (CH 2 ) 4  - NH - O 2 S -CH # CH-SO 2  -NH-(CH 2 ) 4 -COOH, HOOC - CH 2  - C 6 H 4  - CH, - NH - O 2 S - (CH 2 ) 6 - SO  2 -NR-CH 2 -C 6 H 4 -CH 2 -COOH, H 2 N - (CH 2 ) 6  - NH - O 2 S - (CH 2 ) 4  - SO 2  - NH - (CH 2 ) 6 -NH 2 , H 3 C - NH - (CH 2 ) 5  NH - O 2 S - (CH 2 ) 3  - SO, - NH-(CH 2 ) 5 -NH-CH 3 , H 2 N - (CH 2 ) 10  - NCH., - O 2 S - (CH 2 ) 5  - SO 2  - NCH 3 -(CH 2 ) 10 -NH 2 , H 2 N - CHCH 3  - (CH 2 ) 8  - CHCH 3  - NH - O 2 S - (CH 2 ) 5  - SO, - NH - CHCH 3  - (CH 2 ) 8  - CHCH 3  - NH 2 , HOOC - (CH 2 ) 5  - NH - CO - (CH 2 ) 3  - SO 2  - NH - (CH 2 ) 5 -COOH, HOOC - (CH 2 ) 9  - NH - CO - CH 2  - C 6 H 4  - SO, - NH-(CH,),-COOH, HOOC - (CH 2 ) 5  - NH - CO - (CH 2 ) 5  - SO 3  - NH - (CH 2 ) 5 -COOH, HOOC-(CH 2 ) - NH - CO - (CH 2 ) 3  - SO 2  - NH - (CH  2 ) 9 -COOH. The complementary diamines and dicarboxylic acids include bodies of the formulae H 2 N-(CH 2 ) 10 -NH 2 , H 2 N-(CH 2 ) 5 -NH 2 , H 2 N-(CH 2 ) 6 -NH 2 , H 2 N-(CH) 2 -CHCH 3 -(CH 2 ) 2 -NH 2 , H 3 C-NH-(CH 2 ) 6 - NH-CH 3 , H 2 N-CH 2 -C 6 H 4 -CH 2 -NH 2 , H 2 N-CHCH 3 -(CH 2 ) 8 -CHCH 3 -NH 2 , H  2 N-(CH 2 ) 3 -O-(CH 2 ) 3 -NH 2 , H  2 N-CH 2 -C 6 H 4 -CH 2 -NH 2 , HOOC-(CH 2 ) 4 -COOH, HOOC-(CH  2 ) 8 -COOH, H 5 C 2  - OOC - (CH 2 ) 2  - CHCH 3  - CH 2  - COO C 2 H 5 , C 6 H 5 -OOC-(CH 2 ) 7 -COO-C 6 H 5 , H 2 N-OC-(CH 2 ) 4 -CO-NH 2 , HOOC-CH 2 -C 6 H 4 -C 2 -COOH, H 3 C-OOO-(CH 2 ) 3 -CHCH 3 -(CH 2 ) 3 -COO-CH 3 , HOOC-CHCH 3 -(CH 2 ) 2 -CHOH 3 -COOH. In examples (1) trimethylene-, hexamethylene- or m-benzene-disulphonyl-bis-e-aminocaproic acid is reacted with hexamethylene diamine to obtain the salt which, after purification, is heated to obtain the polymer ; (4) tetramethylene disulphonyl-bis-6-aminohenyl diamine is reacted with adipic acid to obtain the salt which, after purification, is heated to obtain the polymer. Trimethylene-, hexamethylene- and m-benzenedisulphonyl-bis-#-aminocaproic acids are prepared by reacting trimethylene-, hexamethylene- and m-benzene-disulphonyl chlorides with maminocapronitrile to obtain the nitrile which is hydrolysed to the acid. Tetramethylenedisulphonyl - bis - 6 - aminohexyldiamine is prepared by reacting ethyl-6- aminohenylurethane hydrochloride with tetramethylene disulphonyl chloride followed by refluxing with concentrated hydrochloric acid.