Patent GB-979401-A (GB)
Title: Improvements relating to glycols and their derivatives
IPC: C08G69/44
Filed: 1963-04-16
Abstract: The invention comprises glycols containing two cyclohexyl groups each substituted by a HOCH2-, any other constituents being ether oxygen or C1-8-saturated hydrocarbon groups, and esters of such glycols.  The glycols are produced by ring hydrogenating bibenzoic and or a bis (carboxyphenyl) alkane or ether corresponding to the required glycol and subsequently reducing the carboxyl groups to hydroxymethyl groups; the appropriate carboxy salts or esters may also be used. Numerous examples are given.  Geometrical isomers are isolated from the intermediate dodecahydro-bis (carboxyphenyl) acids or esters, prior to the final reduction step. The glycol products may be characterized as benzoates and phenylurethanes.ALSO:Solid linear polyesters contain in their structure at least 50% of units of a cyclic glycol containing two cyclohexyl groups each substituted by a HOCH2-, any other constituents of the glycol being ether oxygen or C1-8-saturated hydrocarbon groups. Preferred structural units have the formula -O-CH2-Q-(R)m-Q1-CH2-O-CO-(A)n-CO-wherein m and n are 0 or 1, Q and Q1 are 1,4-cyclohexylene, R is a C1-8-alkylene radical of which at most 4 carbon atoms are in the chain connecting Q and Q1 and A is the radical of a dicarboxylic acid. The dicarboxylic acid may be aliphatic, cycloaliphatic, heterocyclic, aromatic or halogenated aromatic. Up to 50% ml of the cyclic glycols may be replaced by aliphatic glycols (which may contain ether or sulphide linkages or may be fluorinated), other cycloaliphatic glycols, dihydric phenols or hydroxycarboxylic acids. Polyesteramides may be made by including a diamine, aminoalcohol or aminoacid in the reaction mixture. Copolyesters or polyesteramides may be made in segmented or random form. Examples (4)-(58) describe the manufacture of polyesters by reacting one of the cyclic glycols with dimethyl 4,41-tribenzoate (or a mixture thereof with sodium 3,5-di(carbomethoxy) benzene sulphonate), dimethyl 4,41-sulphonyl dibenzoate, dimethyl terephthalate (or a mixture thereof with dimethyl hexahydroterephthalate), dimethyl methylene-4,41-dibenzoate, 1,2-ethylene-4, 41-dibenzoate, dimethyl adamantane-1, 3-dicarboxylate, dimethyl decahydronaphthalene-2, 6-dicarboxylate, dimethyl dodecahydro-4, 41-bibenzoate, dimethyl 1, 3-propylene-4, 41-dibenzoate, dimethyl isopropylidene-4, 41-dibenzoate, 1, 2-bis (4-carbomethoxyphenoxy) ethane, dimethyl 2, 5-dimethylterephthalate and dimethyl glutarate. Examples (59)-(62) describe the manufacture of segmented polyesters by (59)-(60) heating a polyester from dimethyl azelate or dimethyl terephthalate and 2-methyl -2- ethyl-1:3-propane diol with a polyester from dimethyl 4, 41-bibenzoate and bis (4-hydroxymethylcyclohexyl); (61) heating a polyester from dimethyl 2, 5-dimethylterephthalate and ethylene glycol with a polyester from dimethyl 4,41-bibenzoate; (62) heating a polyester from dimethyl terephthalate and ethylene glycol with a polyester from dimethyl 2, 5-dimethylterephthalate and bis (4-hydroxymethylcyclohexyl). Examples (63)-(65) describe the manufacture of polyesteramide by heating (63) N,N1-bis (4-carbomethoxybenzoyl) hexamethylene diamine, dimethyl 4,41-bibenzoate and bis (4-hydroxymethylcyclohexyl); (64) N,N1-bis (4-carbomethoxybenzoyl) hexamethylene diamine and bis (4-hydroxymethylcyclohexyl); (65) dimethyl 4,41-bibenzoate, bis (4-hydroxymethylcyclohexyl) and hexamethylene diamine.