Patent GB-717841-A (GB)
Title: Plasticised compositions
Inventor: DILKE MAX HENRY
IPC: C08K5/11
Filed: 1951-08-23
Abstract: The invention comprises plasticized compositions comprising a polymeric resin containing at least 10 per cent. by weight of vinylidene chloride units in its molecular structure and as a plasticizer therefor a di-ester of alpha-methylbenzyl alcohol with a dibasic acid from the group consisting of benzene dicarboxylic acids, naphthalene dicarboxylic acids and nuclear chloro substituted derivatives thereof, carbonic acid, oxalic acid, saturated straight-chain alpha-omega dicarboxylic acids of formula HOCC.(CH2)nCOOH in which n has values 2-8, maleic acid and fumaric acid.  The term "vinylidene chloride unit" means the group -CH2-CCl2- present in polymers and copolymers of vinylidene chloride.  Suitable polymeric resins are polyvinylidene chloride and copolymers of vinylidene chloride with one or more copolymerizable compounds such as vinyl chloride, methyl acrylate, ethyl acrylate, methylmethacrylate, dimethyl maleate, diethyl maleate, vinyl acetate and acrylonitrile.  In general the plasticizer is used in amounts of 5 to 50 per cent. by weight of the resin.  The plasticized compositions are suitable for the production of fibres or filaments. The plasticizer may be mixed with the polymeric resin in any suitable way, e.g. the plasticizer may be added quickly to the finely-powdered resin and mixing effected by mechanical means or the plasticizer may be dissolved in a volatile organic solvent, such as acetone or benzene, the solution thoroughly mixed with the powdered resin and the solvent removed by drying.  Compositions in which the plasticizers are incorporated may contain light stabilizers, lubricants, pigments and dyes.  In the examples (1) the copolymer obtained from 85 per cent. vinylidene chloride and 15 per cent. vinyl chloride is mixed with the di-alpha-methyl benzyl ester of (a) phthalic acid, (b) tetrachlorophthalic acid, (c) naphthalic acid, (d) succinic acid, (e) oxalic acid, (f) maleic acid, (g) fumaric acid, (h) sebacic acid, (i) carbonic acid, (j) adipic acid, (k) terephthalic acid; (2) the copolymer obtained from 85 per cent. vinylidene chloride and 15 per cent. vinyl chloride is mixed with 2 per cent. by weight of 5-chloro-2-hydroxy-benzophenone as light stabilizer and 10 per cent. of the di-alphamethylbenzyl ester of (a) phthalic acid, (b) succinic acid, (c) sebacic acid, (d) carbonic acid, (e) adipic acid, and (f) terephthalic acid.ALSO:The invention comprises the di-esters of a -methylbenzyl alcohol with the following dibasic acids: benzene dicarboxylic acids, naphthalene dicarboxylic acids and nuclear chloro-substituted derivatives thereof, carbonic acid, oxalic acid, saturated straight-chain a -o  dicarboxylic acids of formula HOOC(CH2)nCOOH in which n has values from 2 to 6, maleic acid and fumaric acid.  These esters are plasticizers for use with vinylidine chloride polymers and copolymers.  The esters are preferably prepared by (a) the reaction of a -methyl benzyl alcohol with the chloride of the dibasic acid in the presence of a tertiary base such as dimethylaniline, pyridine or quinoline; or (b) ester interchange between a -methylbenzyl alcohol and the dimethyl or diethyl ester of the dibasic acid in the presence of a metal alkoxide as catalyst.  In the examples (a) di-alpha-methyl benzyl phthalate is prepared by mixing a -methyl benzyl alcohol with dimethyl phthalate and benzene, adding sodium methoxide and steam distilling the resultant mixture; (b) di-alpha-methyl benzyl succinate is prepared by ester interchange from alpha-methyl-benzyl alcohol and diethyl succinate using sodium ethoxide as catalyst and toluene as reaction medium; (c) di-alpha methyl benzyl sebacate is prepared from alpha-methyl benzyl alcohol using sodium methoxide as catalyst and benzene as reaction medium; (d) di-alpha methyl benzyl carbonate is prepared from alpha methyl benzyl alcohol and diethyl carbonate using sodium ethoxide as catalyst; (e) di-alpha methyl benzyl adipate is prepared from alpha methyl benzyl alcohol and dimethyl adipate, using sodium methoxide as catalyst and benzene as reaction medium; and (f) di-alpha-methyl benzyl terephthalate is prepared by reacting terephthaloyl chloride dissolved in trichlorethylene with a mixture of alpha-methyl benzyl alcohol and pyridine dissolved in trichlorethylene.