Patent GB-760694-A (GB)
Title: Linear polyesters
Inventor: HOWLETT FRANK
IPC: C08G63/685
Filed: 1953-08-18
Abstract: Linear polyesters of improved dyeability contain at the ends of the polyester carbon chain and/or along the chain, benziminazole nuclei which may carry non-functional substituents (e.g. alkyl, aryl, alkoxy, aryloxy, aralkyl, halogen, or fused carbocyclic or heterocyclic rings).  The polyesters may be made by heating (1) a glycol and a dicarboxylic acid, or a hydroxy acid, or ester forming derivatives of these intermediates, or a polyester made from these intermediates or ester forming derivatives therof with (2a) a mono- or bi-functional benziminazole derivative or with (2b) o-phenylene diamine and formic acid which carry between them one or two additional functional substituents and optionally, non-functional substituents, or with (2c) o-phenylene diamine optionally carrying functional and/or non-functional substituents.  The functional groups are those capable of reacting with hydroxy or carboxy compounds, or ester-yielding functional derivatives of these compounds, so as to form ester, amide or other linkages, e.g. hydroxy, amino carboxyalkyl or carboxy groups.  Specified are: Glycols:-ethylene, trimethylene, decamethylene, hexamethylene, p-xylylene and propylene glycols. Dicarboxylic acids:-sebacic, adipic, diphenoxyethane-4,41-dicarboxylic, diphenyl-4,41-dicarboxylic, terephthalic and dimethyl furane-2,5-dicarboxylic acids.  Hydroxy acids:-9-hydroxycapric and omega-hydroxycaproic acids.  Benziminazole derivatives:-5-amino - 1 - N - methylbenziminazole - 2 - propionic acid, polyethylene 2-phenylbenziminazole - 5,41 - dicarboxylate, 5 - carboxy - 2 - hydroxynonylbenziminazole, methyl benziminazole - 2 - valerate, 5 - aminobenziminazole-2 - pelargonic acid, 5 - carboxybenziminazole - 2 - pelargonic acid, 5 - amino - 2 - omegaaminoamyl - benziminazole, 2 - epsilonhydroxyamyl - benziminazole - 5 - carboxy acid, 5 - carboxy - 2 - epsilon - aminoamylbenziminazole, 2 - gamma - carboxypropylbenziminazole - 5 - carboxy acid, 2 - omega carboxyoctyl - benziminazole, 2 - omega - aminoalkyl - benziminazole, 2 - phenylbenziminazole - 5,41 - dicarboxylate or its dimethyl ester, 2-omegacarboxy - butyl - benziminazole, 2 - p - carboxyphenyl - benziminazole, and 2 - (p - carbomethoxyphenyl) benziminazole, o-Phenylene diamine derivatives:-3,4-diaminotoluene, 2:3-diamino - 4 - carboxytoluene, 2:3 - diamino - 5 - carboxytoluene, 1 - methyl - 2,3 - diaminobenzene, 1,2 - diaminonaphthalene, N - ethyl - o - phenylene diamine, 3,4 - diaminomethyl benzoate, 1:2 - dimethyl - 4:5 - diaminobenzene and 1 - nitro - 3:4 - diaminobenzene.  In examples, polyesters containing benziminazole nuclei were made by heating together (a) 9-hydroxycapric acid and 5-carboxy-2-hydroxynonylbenziminazole, (b) sebacic acid, decamethylene glycol and 5-carboxy-benziminazole-2-pelargonic acid; (1) polyethylene adipate and o-phenylene diamine; (2), (4), (5)-(9) and (11)-(14) polyethylene terephthalate and p-phenylene diamine, 3,4-diaminotoluene, 2 - (p - carbomethoxyphenyl) benziminazole, 2 - phenyl - benziminazole - 5,41 - dicarboxylate, 3,4 - diaminomethyl benzoate, polyethylene 2-phenylbenziminazole - 5,41 - dicarboxylate and 5 - amino - benziminazole - 2 - pelargonic acid; (3) and (10) dimethyl terephthalate, ethylene glycol and methyl benziminazole-2-valerate or dimethyl - 2 - phenylbenziminazole - 5,41 - dicarboxylate; (15) dimethyl-2-phenylbenziminazole-5,41-dicarboxylate and ethylene glycol; (16) polyethylene terephthalate, adipic acid and o-phenylene diamine.  Specifications 578,079, 579,462 and 590,451, [all in Group IV], are referred to.