Patent GB-948304-A (GB)
Title: í¡í¡
IPC: C07D263/20
Filed: 1960-03-29
Abstract: The invention comprises an N:N-disubstituted arylamide of the formula: <FORM:0948304/C2/1> where R1 is an aliphatic or cycloaliphatic hydrocarbon group free of acetylenic unsaturation or an epoxidised olefinically unsaturated aliphatic or cycloaliphatic hydrocarbon group free of acetylenic unsaturation, R2 is an aliphatic or cycloaliphatic group free of acetylenic unsaturation, an epoxidised olefinically unsaturated aliphatic or cycloaliphatic hydrocarbon group free of acetylenic unsaturation or a group R 1CO-, where R1 is as defined above and R3 is hydrogen or an organic group as defined for R 1; with the proviso that at least one of the groups R 1 and R2 and/or at least one of the groups R 3 is an epoxidised group as defined, said arylamide containing a total of from 24 to 72 carbon atoms. Such compounds are employed as plasticizers for polyvinyl halide resins (see Division C3). The invention also comprises a mixture of N, N-disubstituted arylamides of the formula: <FORM:0948304/C2/2> where R 1 is an aliphatic or cycloaliphatic hydrocarbon group free of acetylenic unsaturation, R2 is an aliphatic or cycloaliphatic hydrocarbon group free of acetylenic unsaturation or a group R 1CO-, R 1 being as defined above the R 3 groups are hydrogen or aliphatic or cycloaliphatic hydrocarbon groups free of acetylenic unsaturation said arylamides each containing a total of from 24-72 carbon atoms and wherein, in said mixture, one or more of said arylamides contains as an R 1 and/or R 2 and/or R 3 substituent an olefinically unsaturated group, said olefinically unsaturated group or groups being at least partially epoxidised. Such compounds are prepared by subjecting an unsaturated N-arylamide to treatment with an epoxidising per acid which may be preformed or formed in situ using hydrogen peroxide. Various known epoxidation procedures are mentioned.  The examples relate to the preparation of N-phenyl -N- isodecyl-9, 10-epoxystearamide and N-(9, 10-epoxyoctadecyl)-N-phenylbutyramide. Among the many additional products mentioned are N-tetradecyl-N-phenyl-9, 10-epoxystearamide, N-tetradecyl-N-phenyl -9, 10, 12, 13-diepoxystearamide, N-decyl-N-phenyl-9, 10, 12, 13, 15, 16-triepoxy-stearamide, N-tetradecyl-N-phenylamide of epoxidised tall oil fatty acids and N-isodecyl-N-phenylamide of epoxidised soybean oil fatty acids.ALSO:Vinyl halide polymers are plasticized with one or more disubstituted arylamides of the formula: <FORM:0948304/C3/1> where R1 is an alphatic or cycloaliphatic hydrocarbon group free of acetylenic unsaturated or an epoxidised olefinically unsaturated aliphatic or cycloaliphatic hydrocarbon group free of acetylene unsaturation, R2 is an aliphatic or cycloaliphatic hydrocarbon group free of acetylenic unsaturation an epoxidised olefinically unsaturated aliphatic or cyclo-aliphatic hydrocarbon group free of acetylenic unsaturation or a group R1CO- where R1 is as defined above and the R3 groups, which may be the same or different, are hydrogen or organic groups as defined for R1; with the proviso that at least one of the groups R1 and R2 and/or at least one of the R3 groups is an epoxidised group as defined said acrylamides containing a total of from 24 to 72 carbon atoms (see Division C2). The term "vinyl halide polymers" is intended to include homopolymers of vinyl halides and copolymers. Materials which may be copolymerised with vinyl halides include vinylidene chloride, vinyl chloracetate, chlorstyrene and chlorobutadienes. Copolymers specified include copolymers of vinyl chloride with vinylidene chloride, vinyl esters of carboxylic acids e.g. the acetate, propionate, butyrate and benzoate, esters of unsaturated acid e.g. from methyl to butyl acrylate, allyl acrylate and the corresponding methacrylates, styrene, esters of a , b -unsaturated carboxylic acids e.g. of maleic, crotonic, itaconic and fumaric acids.  Optionally conventional plasticizers may be included in the compositions e.g. alkyl phthalates and phosphates. The plasticizers are normally incorporated by mixing the powdered resin wtih liquid plasticizer and curing the mixture. Compositions are described prepared from polyvinyl chloride and barium cadmium laurate together with N-tetradecyl-N-phenyl -9,10,12,13- diepoxystearamide and -9,10 - epoxystearamide, N - isodecyl - N - phenyl - and N - ethyl - N - phenyl -9,10 - epoxystearamide. In further compositions described the polyvinyl chloride is replaced by copolymers of vinyl chloride and vinyl acetate, vinylidene chloride, methylacrylate or vinyl isobutyl ether. Many additional acrylamides are specified.