Patent GB-1299446-A (GB)
Title: Improvements in or relating to dinorbornene compounds
Inventor: COLOMB HENRY OCTAVE JR
IPC: C08K5/00
Filed: 1969-10-10
Abstract: 1299446 Radiation cross-linkable polymers UNION CARBIDE CORP 10 Oct 1969 49988/69 Headings C3A C3P and C3R [Also in Divisions C2 and D1] Compositions cross-linkable by ionizing or non-ionizing radiation comprise (1) 0À01 to 80 weight per cent of a dinorbornene compound of one of formulµ where n is 0 or 1; y is 1 or 2; R is hydrogen, halogen, C 1-8  alkyl, C 2-8  alkenyl or C 6-16  aryl; X, X<SP>1</SP> and Y each represent C 1-8  alkylene, C 2-8  alkenylene, C 6-16  arylene, polyoxyalkylene having 2 to 5000 units each of 2 to 4 carbon atoms or poly(alkylene-carbonyloxy) having 5 to 5000 units each of 3 to 12 carbon atoms; G and G<SP>1</SP> are carbonyloxy, oxycarbonyl, oxydicarbonyl, carbonyl, carbonate, amido, imino, carbamyl, carbamoyloxy, ureylen iminodicarbonyl, thiocarbamyl, thio carbamoyloxy, glycyl, oxy, thio, sulphoxy, sulphonyl or sulphite; and (2) 20 to 99À99 weight per cent of a polymer other than (1). Specified polymers are polyolefins, olefin copolymers, vinyl and viriylidene polymers, acrylic polymers, polyesters, polyamides, siloxane polymers, polyethers, polyureas, polyurethanes, gutta percha, cellulose, methyl cellulose, starch, silk and wool. When cross-linking with non- ionizing radiation conventional photosensitizers may be present, and the compositions may be formed with the aid of inert solvents. Many suitable polymers and norbornene compounds are specified and examples describe the cross linking of compositions comprising pentacyclo- (8.2.1.1<SP>4,7</SP>.0<SP>2,9</SP>.0<SP>3,8</SP>)tetradeca - 5,11 - diene and (17) polycaprolactone and (18) polyethylene; [2.2.1]hept - 2 - en - 5 - yl methyl bicyclo- [2.2.1]hept - 2 - en - 5 - carboxylate and (19) polycaprolactone and (23) polyvinyl acetate; 5 - isocyanatomethyl bicyclo[2.2.1]hept - 2- ene/polycaprolactone diol condensates and (19) polycaprolactone, (20) polycaprolactone diol and barium/cadmium laurate stabilized polyvinyl chloride, (21) barium/cadmium laurate stabilized polyvinyl chloride, and (23) ethylene/ propylene/5 - ethylidene bicyclo[2.2.1] - hept- 2 - ene terpolymer; polyethylene oxide and (22) bicyclo[2.2.1]hept - 2 - en - 5 - ylmethyl bicyclo[2.2.1]hept - 2 - en - 5 - carboxylate and and (23) polypropylene and ethylene/norbornadiene copolymer and ethylene/acrylic acid copolymer and isocyanato bicycloheptene/polyethylene glycol condensate, ethylene/vinyl acetate copolymer and hexamethylene bis - (bicycloheptene carboxylate), ethylene/ethyl acrylate copolymer and di(bicyclo heptenylmethyl) terephthalate, polyvinylidene chloride and isocyanato bicycloheptene/hexamethylene diamine condensate, polyacrylic acid and polypentacyclo tetradeca - 5,11 - diene, polyacrolein and polyacrylonitrile and poly(isocyanatobicycloheptene/polycaprolactone condensate), polyethylene terephthalate and isocyanato bicycloheptene/hexamethylenediamine condensate, glycerol/ethylene oxide/propylene oxide condensate and poly(bicycloheptenylmethyl bicycloheptene carboxylate), polyurethane and poly(isocyanato bicycloheptene/polyethylene glycol condensate), and methyl cellulose and formyl bicycloheptene/hexamethylene diamine/ condensate. The preparation of dinorbornene polymeric materials is also described and exemplified by reacting 5-isocyanatomethylbicyclo- [2.2.1]hept-2-ene with (1 and 12) caprolactone diol, (4 and 5) polyethylene glycol and (6) polypropylene glycol; and by irradiation induced polymerization of (13) pentacyclo [8.2.1.1<SP>4,7</SP>.- 0<SP>2,9</SP>.0<SP>3,8</SP>] tetradeca - 5,11 - diene, (14) biycclo- [2.2.1]hept - 2 - en - 5 - ylmethyl biycclo- [2.2.1]hept - 2 - en - 5 - carboxylate, and reaction products of isocyanatomethyl bicyclohept-2-ene with (15) polycaprolactone diol and (16) polyethylene glycol.