GB685649A - A process for the preparation of polyesters, the polyesters so prepared and plastic compositions containing the polyesters - Google Patents

Abstract

Polyesters are prepared by heating a succinic acid having an open-chain hydrocarbon radical containing 18-26 carbon atoms substituted on one of its chain carbon atoms, or an anhydride thereof, with an organic compound containing two esterifiable hydroxyl groups. The remaining hydrogen atoms attached to the methylene groups of the succinic acid may be replaced by e.g. alkyl, alkenyl, halogen, acyl or alkoxy radicals. Specified substituted succinic acids and anhydrides are octadecyl, dioctadecyl, nonadecyl, eicosyl, docosyl, tricosyl, pentacosyl, 1-octadecenyl, 3-nonadecenyl, 3-eicosenyl, 2-heneicosenyl, tetracosenyl, 3,6-octadecadienyl, 9,12-octadecadienyl, 3,6-nonadecadienyl, 4,7 - heneicosdienyl, 3,8-tricosadienyl 3,5,7 - docosatrienyl, 4,6 - diisoamyldodecyl, 4 - isoamylheptadecyl, 6 - butyl-octadecyl, 2,5 - dibutyloctadecyl, 3,5 - diethyl-octadecenyl - 1, 3,5,7 - tripropyl - 2 - dodecenyl, 3,5,7 - tributyl - 2 - dodecenyl, 2 - ethyl - 4-eicosenyl, and tripropyl-2-dodecenyl. The compounds containing two hydroxy groups may be saturated or unsaturated, aliphatic, alicyclic or aromatic and may be substituted by halogen, alkoxy, sulphohydryl or carbalkoxy radicals. Specified are ethylene glycol, diethylene glycol, triethylene glycol, 3-ethyl hexanediol-1,3, glycerol monomethyl ether, glycerol monoethyl ether, glycerol monobutyl ether, 2,4-butadiene-1,4 diol, 1,2-pentanediol, 1,4-hexanediol, 2,8-dodecanediol, chlorethylene glycol, catechol, resorcinol, hydroquinone, glycerol monoacetate, glycerol monobutyrate, 2,5-dimethyl - 2,6 - heptanediol, 1,4 - butanediol, and 3-ethyl hexanediol-2,4. The reaction may be carried out in presence of catalysts, e.g. p-toluenesulphonic acid, zinc or stannic chloride; calcium, barium or zinc acetate; or hydrochloric acid; solvents, e.g. benzene, toluene, xylene, cyclohexane, chloroform, or carbon tetrachloride, and under a blanket of an inert gas, e.g. nitrogen, carbon dioxide, helium or ethane. Water is removed as formed, e.g. by azeotropic distillation with benzene or toluene. Specified modifying agents and fillers for the polyesters are cottonseed or castor oil fatty acids; castor oil; phenol- or urea-aldehyde resins; colophony, shellac, capol, camphor, naphthalene, alkyl and aryl phthalates, pitch, asphalt, sand or clay. The polyesters may be used to plasticize urea- or melamine-aldehyde-type resins such as those produced from urea, thiorea, 1,4-butylene diurea and formaldehyde, acetaldehyde or propionaldehyde or cellulose derivates and compositions of the polyester and cellulose derivates may contain fillers, e.g. whiting, clay, gum rosin, silica, oxides of bismuth barium oxides and plasticizers, e.g. dioctyl phthalate, dibutyl phthalate and tricresyl phosphate and solvents, e.g. methanol; butyl alcohol; acetone; methyl ethyl ketone; ethyl acetate; butyl acetate; ethylene glycol ethyl ether, toluene, low aromatic petroleum lacquer diluent or mixtures. In examples: (1) ethylene glycol and 1-octadecenyl succinic anhydride are reacted; (2) ethylene glycol and octadecylsuccinic anhydride are reacted; (3) diethylene glycol and 1-octadecenylsuccinic anhydride are reacted; (4) triethylene glycol and 3-eicosenylsuccinic anhydride are reacted; (5) ethylene glycol is reacted with (a) 4,6-diisoamyldodecylsuccinic acid; (b) dioctadecylsuccinic acid; (c) tricosylsuccinic acid and (d) 2,5-dibutyloctadecylsuccinic acid; (6) 1-octadecenylsuccinic acid is reacted with (a) 1,4-butanediol; (b) 3-ethyl hexanediol-2,4; (c) glycerol monoacetate; (d) glycerol monomethyl ether; (e) polyethylene glycol; (7) and (8), a coating composition consists of nitro-cellulose in a solvent comprising butyl acetate, ethyl acetate, butyl alcohol, toluene and petroleum lacquer and a plasticizer comprising (a) the polyester from ethylene glycol and 1-octadecenylsuccinic anhydride, and (b) the polyester from ethylene glycol and octadecyl-succinic anhydride; (9) a coating composition consists of cellulose acetate, methyl ethyl ketone, methanol and the polyester from diethylene glycol and 1-octadecenyl anhydride; (10) coating compositions comprise ethyl cellulose and the polyesters from (a) ethylene glycol and 1-octadecenylsuccinic acid; (b) triethylene glycol and 3-eicosenylsuccinic acid; (c) ethylene glycol and tricosylsuccinic acid, and (d) 1,4-butanediol and 1-octadecenylsuccinic acid. Specifications 464,276, 665,595 and 12778/48 (as open to inspection under Sect. 91) are referred to.