Patent GB-913735-A (GB)
Title: Optically brightened macromolecular organic substances
Inventor: STILZ WALTER
IPC: C07C63/66
Filed: 1960-06-23
Abstract: A macromolecular organic substance contains for the homogeneous optical brightening thereof at least one compound of the 1,4-bis-styryl benzene series having the general formula <FORM:0913735/IV(a)/1> in which R1 and R11 denote carboxyl groups carboxylic acid ester or amide groups or nitrile groups, R2 and R3 denote hydrogen, halogens, alkyl groups, aralkyl groups or alkoxy groups, and in which R1 and R11 may be identical or different and symmetrically or unsymmetrically attached to the benzene rings, and R2 and R3 may be identical or different.  Specified macromolecular substances are polyamides, polyesters, aminoplasts, rubbers, regenerated cellulose, polymers and copolymers of styrene, vinyl chloride, vinylidene chloride, butadiene, acrylamide and acrylonitrile, polyethylene, polypropylene, polyisobutylene and polyformaldehyde.  In the Examples:- (1) a mixture of caprolactam and hexamethylene diammonium adipate is polymerized in the presence of 1,4-bis-(p-carbomethoxystyryl)-benzene; (2) caprolactam is polymerized in the presence of titanium dioxide and 1,4-bis-(p-cyanostyryl)-benzene; (3) hexamethylene diammonium adipate is polymerized in the presence of 1,4-bis-(m-carbomethoxystyryl) benzene; (4) sebacic acid and hexamethylene diamine are polymerized in the presence of 1,4-bis-(p-carbomethoxystyryl)-benzene; (5) polycaprolactam is mixed with 1,4-bis-(p-cyanostyryl)-benzene and ditertiary-butyl-p-cresol; (6) polypropylene is mixed with 1,4-bis-(p-cyanostyryl)-benzene; (7) dimethyl terephthalate and ethylene glycol are polymerized in the presence of zinc acetate, antimony trioxide and 1,4-bis-(p-carbomethoxystyryl)-benzene; (8) polypropylene is mixed with titanium dioxide and 1,4-bis-(p-carbomethoxystyryl)-benzene; (9) dimethyl terephthalate and ethylene glycol are polymerized in the presence of antimony trioxide, zinc acetate and 1,4-bis-(p-cyanostyryl)-benzene and (10) polyformaldehyde impregnated with a solution of a polyamide made from hexamethylene diammonium adipate, p-diamino-dicyclohexylmethane adipate, caprolactam and 2,21-methylene-bis-(4-ethyl-6-t-butyl phenol) is mixed with (a) 1,4-bis-(41-carbomethoxystyryl)-benzene, (b) bis-(41-cyanostyryl)-benzene.  Specification 813,539 is referred toALSO:1,4-bis-styrylbenzenes of the formula:  <FORM:0913735/IV (b)/1> wherein R1 and R11 are identical or different and may be carboxyl groups, esterified carboxyl groups, nitrile groups, or carboxylic amide groups are made by reacting a m or p-benzyl halide derivative of the formula <FORM:0913735/IV (b)/2> with a triarylphosphine to form triaryl-cyano benzylphosphonium chloride, 2 mols of which are reacted in the presence of an alkaline condensing agent with one mol of a terephthaldehyde of the general formula <FORM:0913735/IV (b)/3> where R2 and R3 which may be the same or different are hydrogen, halogens, alkyl groups, aralkyl groups or alkoxy groups. Examples describe the preparation of 1,4-bis-(p-carbomethoxystyryl)benzene; 1,4-bis-(p-cyanostyryl) benzene; 1,4-bis(m-cyanostyryl)benzene; and 1,4 - bis(m-carbomethoxystyryl)benzene.  Specification 813,539 is referred to.