Patent GB-1012261-A (GB)
IPC: C08F263/00
Abstract: 1,012,261. Synthetic resins. CIBA Ltd. April 24, 1964 [May 3, 1963], No. 17132/64. Heading C3P. [Also in Division B5] Curable synthetic resin masses comprise a prepolymer or telomer of a poly-(2-chloroallyl) ester of a polycarboxylic acid and a substance capable of inhibiting the elimination of hydrogen chloride selected from calcium, strontium, barium, cadmium and lead salts of C 12-18  fatty acids, basic lead and cadmium salts and epoxides. Specified polycarboxylic acids are oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, sebacic, maleic, fumaric, itaconic, aconitic, allylsuccinic, dodecenylsuccinic, butane-1,2,4-tri-carboxylic, butane tetracarboxylic hexahydrophthalic, tetrahydrophthalic, endomethylene tetrahydrophthalic, isophthalic, terephthalic, pyromellitic and orthophthalic acids. The prepolymers and telomers may contain units of other monomers, e.g. olefins and halogen-substituted olefins, vinyl ethers, vinyl aromatic compounds and α-substitution products thereof, esters and nitriles of acrylic, methacrylic, α-halo-acrylic, maleic and fumaric acids, allyl esters, and 2- chloroallyl esters of monocarboxylic acids. The polymerization may be effected in bulk or preferably in a solvent, e.g. alcohols and acetone. Specified telogens are benzyl alcohol, ethylene chloride, heptachloropropane, trichloropropane and 2,3-dichloropropene-1. Regulators, e.g. dodecyl mercaptans, and epoxy compounds, e.g. butanediol diglycidyl ether or 3,4 - epoxycyclohexane dimethanol - 1,1- acrolein acetal. Polymerization catalysts specifled are hydrazine derivatives, azo compounds and inorganic and organic peroxy compounds. Specified inhibitors of hydrogen chloride elimination are metal soaps, optionally together with with fatty acid monoglycerides, basic lead salts and mono- and polyepoxy compounds. The compositions may also comprise lubricants, e.g. fatty acids and waxes; fillers; reinforcing means; dyestuffs and pigment; flame inhibitors and plasticizers. Examples describe the preparation of curable prepolymers in which bis-(2-chloroallyl) phthalate is (I) propolymerized, (II) prepolymerized in the presence of isopropanol, (III) telomerized in the presence of acetone, (IV) telomerized in the presence of 2,3-dichloropropene or benzyl alcohol, (V) telomerized in the presence of 1,2-dichlorethane and 3,4-epoxycyclohexane-1,1-dimethanol acrolein acetal or butene-2-diol-1,4-diglycidyl ether, (VI) copolymerized with diallyl phthalate, (VII) copolymerized with styrene, (VIII) copolymerized with 2-chloroallyl acetate, copolymerized with (IX) methyl methacrylate, (X) 2-chloroallylcrotonate and (XI) bis-(2- chloroallyl) adipate in the presence of 2,3- dichloropropene, and telomerized in the presence (XIV) heptachloropropane, (XV) acetone and (XVI) methyl ethyl ketone, and in which (XII) bis-(2-chloroallyl) isophthalate, and (XIII) bis-(2-chloroallyl) succinate are telomerized in the presence of 2,3-dichloropropene. The products may be compounded to give moulding and laminating compositions. Examples describe moulding compositions comprising (1) product I, diallyl phthalate, 1,2-dichlorethane, calcium stearate, titanium dioxide, kaolin, chalk and t.-butyl perbenzoate; (2) product IV, bis-(2-chloroallyl) phthalate, calcium stearate, red azo pigment, clay and t.-butyl perbenzoate; (3) product IV, bis-(2-chloroallyl) phthalate, chalk, clay, calcium stearate, barium/cadmium laurate, pigment and t.-butyl perbenzoate; (4) prodoct IV, bis-(2-chloroallyl) phthalate, chalk, calcium stearate, barium/cadmium laurate, copper phthalocyanine, glass fibres and t.-butyl perbenzoate; (5) product IV, bis-(2- chloroallyl) phthalate, chalk, pigment, calcium stearate, barium/cadmium laurate, nylon fibres and t.-butyl perbenzoate; (6) product IV, bis- (2-chloroallyl) phthalate, chalk, clay, calcium stearate, red pigment, barium/cadmium laurate and t.-butyl perbenzoate; (7 to 10) product IV, diallyl phthalate prepolymer, bis-(2-chloroallyl) phthalate, chalk, clay, calcium stearate, barium/cadmium laurate, red pigment and t.-butyl perbenzoate; (12) product VII, bis- (2-chloroallyl) phthalate, chalk, clay, calcium stearate, barium/cadmium laurate, red pigment and t.-butyl perbenzoate; (13) product VIII, chalk, clay, lead stearate red pigment and t.-butyl perbenzoate; (14) product VI, diallyl phthalate, chalk, clay, calcium stearate, red pigment and t.-butyl perbenzoate; (15) product X, bis-(2-chloroallyl) phthalate, chalk, clay, red pigment, calcium stearate and t.- butyl perbenzoate; (16) product VIII and (17) product IX with clay, lead stearate, 3,4- epoxy cyclohexane-1,1-dimethanol acrolein acetal and t.-butyl perbenzoate; (18) product IV, bis-(2-chloroallyl) succinate, kaolin, titanium dioxide, 3,4-epoxy cyclohexane-1,1-dimethanol acrolein acetal and t.-butyl perbenzoate; as (18) where the succinate is replaced by (19) the adipate and (20) the itaconate; (21) product IV, chloroallyl methacrylate, chalk, clay, calcium stearate, chlorinated copper phthalocyanine and t.-butyl perbenzoate; and as (21) where the methacrylate is replaced by (22) chloroallyl crotonate and (23) bis-(2-chloroallyl) itaconate; in Example (24) glass fabrics are impregnated with compositions comprising product XVI, a condensate of epichlorhydrin with bis-(4-hydroxyphenyl) dimethyl methane; dimethyl phthalate and t.-butyl perbenzoate, and laminated under heat and pressure.