Patent GB-1045869-A (GB)
Title: N-3-oxohydrocarbon-substituted acrylamides
Inventor: COLEMAN LESTER EARL
IPC: C10L1/236
Filed: 1964-11-04
Abstract: A lubricating composition comprises a mineral, vegetable, animal, silicone or synthetic polyester oil in admixture with a minor proportion of a homopolymer or copolymer of an N-3-oxohydrocarbon-substituted acrylamide of the formula R.CO.R1-NHCOC(R11)=CH2 wherein R and R11 represent hydrogen or C1- 10 alkyl or cycloalkyl radicals and R1 represents an ethylene radical or an ethylene radical substituted by a C1- 10 alkyl or cycloalkyl group, with the proviso that at least one such group is on the carbon atom attached to the nitrogen atom of the acrylamide group.  The composition may contain as additional ingredients sulphonates, thiophosphates, phosphites,amines, phenols, disulphides and chlorinated wax.ALSO:Novel N-3-oxohydrocarbon-substituted acrylamides of the formula R.CO.R1-NHCOC(R11) = CH2 wherein R and R11 represent hydrogen or C1- 10 alkyl or cycloalkyl radicals and R1 represents an ethylene radical or an ethylene radical substituted by a C1- 10 alkyl or cycloalkyl group, with the proviso that at least one such group is on the carbon atom attached to the nitrogen atom of the acrylamide group, are prepared by reacting at a temperature below 100 DEG  C. one mol. of an acrylonitrile of the formula CH2 = C(R11)-CN with either one mole of a beta-hydroxy oxohydrocarbon of the formula R.COC(R111)2.C(R111)2-OH or two moles of an aliphatic oxohydrocarbon of the formula R1.COCH(R2)2 in the presence of at least one mole of sulphuric acid, and subse hydrolysing the product, R111 representing hydrogen or a C1- 10 alkyl or cycloalkyl group, with the proviso that if any R111 represents a C1- 10 alkyl or cycloalkyl group at least one of the R111 radicals on the carbon atom adjacent the OH group represents a C1- 10 alkyl or cycloalkyl group, and each of R1 and R2 representing hydrogen or a C1- 10 alkyl or cycloalkyl radical, with the proviso that the sum of the carbon atoms in the two R2 groups does not exceed 9.ALSO:N - 3 - Oxohydrocarbon - substituted acrylamides of the formula R.CO.R1-NHCOC(R11)=CH2 wherein R and R11 represent hydrogen or C1- 10 alkyl or cycloalkyl radicals and R1 represents an ethylene radical or an ethylene radical substituted by a C1- 10 alkyl or cycloalkyl group, with the proviso that at least one such group is on the carbon atom attached to the nitrogen atom of the acrylamide group, are polymerized alone or in admixture with other ethylenically unsaturated compounds in the presence of azo, peroxide, sodium in ammonia, Ziegler, metal aryl or metal alkyl catalysts, or using heat or gamma ray irradiation.  Suitable comonomers include esters of unsaturated alcohols, polyols or unsaturated acids, vinyl cyclic compounds, vinyl halides and unsaturated ethers, ketones, amides, aliphatic hydrocarbons, acids, acid anhydrides, acid chlorides and nitriles.  Examples describe the preparation of homopolymers, copolymers and terpolymers using as comonomers decyl acrylate, vinyl acetate, mixtures of dialkyl fumarates, N-vinyl pyrrolidone, N-vinyloxazolidone, isoprene and acrylonitrile, and employing benzene/azobisisobutyronitrile or benzoyl peroxide, tetrahydrofuran/sodium naphthalene or sodium/liquid ammonia solvent/catalysts systems.