Patent GB-1115629-A (GB)
Title: Modified hydrocarbon polymers
IPC: C08F8/06
Filed: 1966-10-20
Abstract: Organic solvent soluble partially oxidized non-rubbery interpolymers of a polyunsaturated hydrocarbon, optionally substituted with halogen or oxygen-containing radicals, and at least one monoolefin, said interpolymer having prior to oxidation an essentially saturated carbon chain containing at least 20% of the total carbon atoms in the polymer molecule and at least 2 weight per cent of carbon atoms in ethylenic unsaturation, and containing after oxidation at least 0.5 weight per cent of added oxygen, may be prepared by oxidizing the interpolymers in bulk or in solution, preferably at elevated temperature.  The interpolymers may be derived from ethylene, propylene, 2-methylpropene, 2-propylhexene-1, butene-1, 4-methylpentene-1, pentene-1, hexene-1, octene-1,5-methylnonene-1, 5,6-trimethyldecene-1, dodecene-1, tetradecene-1, octadecene-1, styrene and vinyltoluene; and conjugated and non-conjugated polyenes, such as pentadiene-1,4, hexadiene-1,4, octadecadiene-1,9, 11-ethyl - 1,11 - tridecadiene, cyclopentadiene-1,3, 5 - methylcyclopentadiene - 1,3, tricyclopentadiene, 5 - methylcyclopentadiene - 1,3 - dimer, cyclohexadiene - 1,4, cyclooctadiene - 1,5, cyclododecatriene - 1,5,9, cyclooctatriene -1,4,6, 5 - (21 - butenyl) norbornene - 2, 5 - (11 - propenyl) norbornene - 2, 1,8(9) - p - menthadiene, divinyl benzene, 5 - vinylbicyclo-[2.2.1] heptene-2 and bicyclo-[4.3.0] nonadiene-3,7. Oxidation may be effected by oxygen, air, ozone or oxygen-releasing or containing substances, e.g. benzoyl peroxide, hydrogen peroxide, perbenzoic acid, peracetic acid and potassium permanganate; optionally in the presence of oxidation catalysts such as driers, e.g. cobalt and lead naphthenates, linoleates and resinates.  The products may be used, optionally with coreactive substances, e.g. drying and semi-drying oils, polycarboxylic acids and anhydrides, polyesters, aziridinyl compounds, polyisocyanates, polyepoxides, polymers of unsaturated carboxylic acid amides, aminoplast and phenolic resins and unsaturated hydrocarbon polymers, to give composition for forming curable coatings, e.g. on metals. Examples describe the oxidation of interpolymers of ethylene, propylene, dicyclopentadiene and bicycloheptadiene, and coating compositions comprising oxidized interpolymers and (1) hydrocarbon solvents and titanium dioxide, and (2) aromatic hydrocarbon solvents, magnesium and cobalt naphthenates and a butylated melamine/formaldehyde resin, butylated urea/formaldehyde resin or an epoxy ester reaction product of tall oil fatty acids and a bisphenol-A/epichlorohydrin condensate.ALSO:Substrates such as metals may be coated with compositions comprising organic solvent solutions of partially oxidised non-rubbery interpolymers of a polyunsaturated hydrocarbon, optionally substituted with halogen or oxygen-containing radicals, and at least one mono-olefin, said interpolymer having prior to oxidation an essentially saturated carbon chain containing at least 20 per cent of the total carbon atoms in the molecule and at least 2 weight per cent of carbon atoms in the ethylenic unsaturation, and containing after oxidation at least 0.5 weight per cent of added oxygen.  The compositions may also contain pigments and co-reactive substances, e.g. drying and semi-drying oils, polycarboxylic acids and anhydrides, polyesters, aziridinyl compounds, polyisocyanates, polyepoxides, polymers of unsaturated carboxylic acid amides, aminoplast and phenolic resins and unsaturated hydrocarbon polymers.  The oxidised interpolymer may be derived from ethylene, propylene, 2 - methylpropene, 2 - propylhexene-1, butene-1, 4-methylpentene-1, pentene-1, hexene-1, octene-1, 5-methylnonene-1, 5, 6, 6-trimethyldecene-1, dodecene-1, tetradecene-1, octadecene-1, styrene or vinyl toluene; and pentadiene-1, 4, hexadiene-1, 4, octadecadiene-1, 9, 11-ethyl-1, 11-tridecadiene, cyclopentadiene-1, 3, 5-methylcyclopentadiene-1, 3, tricyclopentadiene, 5-methylcyclopentadiene-1, 3-dimer, cyclohexadiene-1, 4, cyclooctadiene-1, 5, cyclododecatriene-1, 5, 9, cyclooctatriene-1, 4, 6, 5(2\sv-butenyl) norbornene-2, 5(1\sv-propenyl) norbornene-2, 1, 8 (9)-p-menthadiene, divinyl benzene, 5-vinylbicyclo [2, 2, 1] heptene-2 and bicyclo [4, 3, 0] nonadiene-3, 7.  In examples phosphated steel panels and electrolytic tin plate are coated by spraying with compositions comprising (1) oxidised ethylene/propylene/dicyclopentadiene / bicycloheptene interpolymers, titanium dioxide and hydrocarbon solvents; and are coated with drawn films of compositions comprising (2) the above oxidised interpolymer, hydrocarbon solvents, magnesium and cobalt naphthenates and a butylated melamine/formaldehyde resin, butylated urea/formaldehyde resin, or epoxy ester reaction product of tall oil fatty acids and a bisphenol A/epichlorohydrin condensate.