Patent GB-536017-A (GB)
Title: Polymeric quaternary ammonium salts from ditertiary diamines and dihalides
IPC: C08G73/02
Filed: 1939-08-29
Abstract: 536,017. Polymeric quaternary compounds. DU PONT DE NEMOURS & CO., E. I. Aug. 29, 1939, No. 24771. Convention date, Aug. 30, 1938. [Class 2 (iii)] Linear polymeric quaternary ammonium compounds are prepared by heating a dihalide, preferably a di-primary dihalide, with a ditertiary diamine. Dihalides, wherein the halogen atoms are attached to singly-bonded carbon atoms, include aliphatic or aromatic, cyclic or acyclic, straight or branched chain, saturated or unsaturated, unsubstituted or substituted diiodides, di-bromides or di-chlorides such as triglycol dichloride, dichlordipropyl ether, methylene dibromide, 1:3-dichloropropane, iso-butylene dibromide, trimethylethylene dibromide, 1:4- dibromopentane, p-xylylene dibromide, 1:4- cyclohexylenedichloride, methylenediiodide, 1-bromo-10-chlorodecane, octamethylenediiodide, 2:6-dibromo-n-heptane, tetramethylenedichloride, 2:3-dibromobutane, dodecamethylenedibromide, decamethylene dibromide and ethylene dichloride ; other radicals that may occur in the dihalide and which do not interfere in the reaction include ether, hydroxyl, keto, nitro, thiol, sulphide, carboxyl and ester groups. Diamines, wherein each nitrogen atom must be attached to at least two saturated radicals, include aliphatic, aromatic, cyclic, acyclic, homocyclic, heterocyclic, saturated, unsaturated substituted or unsubstituted diamines such as N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethyltriethyleneglycoldiamine N:N:N<SP>1</SP>:N<SP>1</SP>-tetraethyl- 1: 4-diaminocyclohexane, 1:10-bis-(diethylaminomethoxy)-decane, N:N<SP>1</SP>- bis-(2-hydroxyethyl)-piperazine, bis-(4-morpholine)-dodecane, bis-(1-piperidyl)-octane, 1:6-bis- (dimethylamino)-2:5-dimethylhexane, N:N:N<SP>1</SP>: N<SP>1</SP>-tetramethyl-p-phenylenediamine, N-N-N<SP>1</SP>N<SP>1</SP>- tetramethyl -1:6- diamino - 3 - hexene, N - allyl- N: N<SP>1</SP> : N<SP>1</SP>- trimethyloctadecamethylenediamine, N:N:N<SP>1</SP>:N<SP>1</SP>-diethylene - 1:2 - ethylenediamine, N:N: N<SP>1</SP>: N<SP>1</SP>- tetramethyldecamethylenediamine, N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethylethylene diamine, N:N: N<SP>1</SP>:N<SP>1</SP>-tetramethyl-p-p<SP>1</SP>-diamino diphenylmethane, and N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethylhexamethylenediamine ; other radicals that may occur in the diamine and do not interfere with the reaction include ether, sulphide, ketone, nitro, amide, hydroxyl and thiol groups. The amino and its halide must be so selected that their combined radical length exceeds seven. The products may be used as photographic chemicals, leather-treating chemicals, mold inhibitors, bactericides, pour-point depressors, pigment dispersion control agents, surface-active agents, modifying-agents for viscose or cellulose acetate, or as adhesives. In examples, solutions in methanol of decamethylene dibromide and (1) N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethylhexamethylenediaamine, (2 )N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethyldecamethylenediamine, (3) N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethylethylenediamine, or (4) N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethyl-p-p<SP>1</SP>- diaminodiphenylmethane are heated to yield polymers ; (5) ethylene dichloride is heated with N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethylhexamethylenediamine.