Patent GB-734632-A (GB)
Title: A stabilized fuel oil composition
IPC: C10L1/236
Filed: 1953-04-07
Abstract: Compositions comprise a fuel oil having incorporated therein at least 0.001 per cent of an oil-soluble basic copolymer containing 0.1 to 3.5 per cent of amino nitrogen of a plurality of polymerizable ethylenically unsaturated compounds, at least one of which is amino nitrogen free, and at least one of which contains a hydrocarbon chain of at least 8 carbon atoms, such as 2-ethylhexyl and decyl acrylates, n-octyl, sec.-capryl, 3,5,5-trimethyl hexyl, technical lauryl, tridecyl, cetyl, octadecyl, technical octadecenyl, N-tert.-octylaminoethyl, and octylphenyl methacrylates, vinyl laurate and stearate, lauryl fumarate, vinyl lauryl ether, n-octyl and tert.-octyl acrylamides, and dodecyl styrene.  The amino nitrogen may be introduced into the copolymers by means of monomers containing amino nitrogen such as beta-methylaminoethyl and beta, beta-dido-decylaminoethyl acrylates, dimethylaminoethyl, diethylaminoethyl, dimethylaminopropyl, diisopropylaminoethyl, N,N - di - 2 - ethylhexyl-aminoethyl, tert. - octylaminoethyl, 2,3 - dimethyl - 3 - dimethylaminopropyl, methylbenzylamino, and 4 - diethylaminocyclohexyl methacrylates, bis - (diethylaminoethyl) maleate, N - (beta - dimethylaminoethyl) acrylamide, dimethylaminomethyl styrene, aminoethyl and diethylaminoethyl vinyl ethers, 4-vinyl pyridine, 2-vinyl-5-ethyl pyridine, and diallylamine; alternatively there may be used in copolymerization monomers which contain groups which are reacted to form amino groups, for example copolymers derived from vinyl chloroacetate, glycidyl acrylate and methacrylate, or glycidyl vinyl ether may be reacted with ammonia or amines, such as diamylamine, or a copolymer made from N-(betavinyloxyethyl formamide) may be hydrolysed with hydrochloric acid and then converted with sodium hydroxide to the free base containing monomer units of beta-vinyloxyethyl amine.  Additional monomers which may be present in the copolymers are ethylene, propylene, isobutylene, styrene, vinyl toluene, cyclohexyl styrene, butadiene, isoprene, vinyl and allyl formates, acetates, propionates and butyrates, acrylic acid, methyl methacrylate, acrylonitrile, methacrylamide, N-tert.-butylacrylamide, acrylanilide and methacrylanilide, ethyl vinyl ether, butyl vinyl ether, and glycidyl allyl ether.  The fuel oil compositions may also contain conventional metal deactivators such as di - (2 - hydroxybenzal) - 1,2 - propylenediamine.  The copolymers may be made by bulk, solution, or dispersion methods employing catalysts such as benzoyl peroxide and alpha-alpha-azo diisobutyronitrile.  Suitable polymerization solvents are mineral oil, white oil, kerosene, and benzene.  Specifications 719,648 and 722,258 are referred to.ALSO:Branched chain dodecyl styrene is prepared by the acetylation of a commercial mixture of branched chain dodecylbenzenes with acetyl chloride in the presence of aluminium chloride, selective hydrogenation of the resulting ketone with a nickel catalyst, followed by dehydration of the carbinol thus produced by refluxing with xylene containing iodine. Specifications 719,648 and 722,258, [both in Group IV (a)], are referred to.ALSO:Compositions comprise a fuel oil having incorporated therein at least 0.001 per cent of an oil-soluble basic copolymer containing 0.1 to 3.5 per cent of amino nitrogen of a plurality of polymerizable ethylenically unsaturated compounds, at least one of which is amino nitrogen free, and at least one of which contains a hydrocarbon chain of at least 8 carbon atoms, such as 2-ethylhexyl and decyl acrylates, n-octyl, sec.-capryl, 3,5,5-trimethylhexyl, technical lauryl, tridecyl, cetyl, octadecyl, technical octadecenyl, octylphenyl, and N-tert.-octylaminoethyl methacrylates, vinyl laurate and stearate, lauryl fumarate, vinyl lauryl ether, n-octyl and tert.-octyl acrylamides, and dodecyl styrene.  The amino nitrogen may be introduced into the copolymers by means of monomers containing amino nitrogen, such as methylaminoethyl and didodecylaminoethyl acrylates, dimethylaminoethyl, diethylaminoethyl, dimethylaminopropyl, diisopropylaminoethyl, N,N - di - 2 - ethylhexylaminoethyl, tert. - octylaminoethyl, 2,3 - dimethyl - 3 - dimethylaminopropyl, methylbenzylamino, and 4 - diethylaminoacrylates, bis - (diethylaminoethyl) maleate, N - (beta - dimethylaminomethyl) acrylamide, dimethylaminomethyl styrene, aminoethyl and diethylaminoethyl ethers, 4-vinyl pyridine, 2 - vinyl - 5 - ethyl pyridine, and diallylamine; alternatively there may be used in copolymerization monomers which contain groups which are reacted to form amino groups, for example copolymers derived from vinyl chloroacetate, glycidyl acrylate and methacrylate, glycidyl vinyl ether, and N-(beta-vinyloxyethylformamide).  Additional monomers which may be present in the copolymers are ethylene, propylene, isobutylene, styrene, vinyl toluene, cyclohexyl styrene, butadiene, isoprene, vinyl and allyl formates, acetates, propionates, and butyrates, acrylic acid, methyl methacrylate, acrylonitrile, methacrylamide, N-tert.-butyl-acrylamide, acrylanilide, methacrylanilide, ethyl vinyl ether, butyl vinyl ether, and glycidyl allyl ether.  The fuel oil compositions may also contain conventional metal deactivators, such as di - (2 - hydroxybenzal) - 1,2 - propylenediamine.  Specifications 719,648 and 722,258, [Group IV (a)], are referred to.