Patent GB-1024905-A (GB)
Title: Copolymers of specific heterocyclic compounds
IPC: C07D487/04
Filed: 1963-05-17
Abstract: A lubricating oil, gasoline or fuel oil additive comprises a copolymer of (A) at least one nitrogenous monomer of the formula <FORM:1024905/C4-C5/1> where R1 represents hydrogen or a C1-C5 alkyl group and R2 and R3 each represents hydrogen or a hydrocarbon group free of nonaromatic unsaturation with the proviso that one of the pairs R1, R2 or R2 R3 may be formed together to form a hydrocarbon group having a ring of 5 or 6 carbon atoms which may contain an endomethylene group; and Q represents a divalent hydrocarbon group which (a) is free of non-aromatic unsaturation, (b) is attached to each nitrogen atom through a carbon atom which is itself attached to not more than two other carbons, and (c) provides a chain than two other carbons, and (c) provides a chain of two or three carbon atoms between the two nitrogen atoms, and (B) at least one other ethylenically unsaturated free radically polymerizable comonomer.ALSO:A copolymer of (A) at least one nitrogenous monomer of the formula <FORM:1024905/C3/1> where R1 represents hydrogen or a C1-C5 alkyl group and R2 and R3 each represent hydrogen or a hydrocarbon group free of non-aromatic unsaturation, with the proviso that one of the pairs R1, R2 or R2R3 may be formed together to form a hydrocarbon group having a ring of 5 or 6 carbon atoms which may contain an endomethylene group; and Q represents a divalent hydrocarbon group which (a) is free of non-aromatic unsaturation, (b) is attached to each nitrogen atom through a carbon atom which is itself attached to not more than two other carbons, and (c) provides a chain of two or three carbon atoms between the two nitrogen atoms and (B) at least one other ethylenically unsaturated free radically polymerizable comonomer.  Exemplified comonomers are methyl methacrylate, acrylonitrile, dimethyl fumarate, diethyl fumarate; diisobutyl fumarate, diethyl maleate, styrene with or without the addition of divinyl benzene, vinyl acetate and diethyl fumarate, vinylidene cyanide, acrylamide, cetyl methacrylate and hexyl acrylate, sec-butyl methacrylate and 2-N-tert.-butyl amino ethyl methacrylate, vinyl stearate and diethyl fumarate and N-vinyl pyrrolidinone, N - (2 - vinoxyethyl) urea.ALSO:Compounds of the formula <FORM:1024905/C2/1> in which R1 represents hydrogen or a C1-C5 alkyl group and R2 and R3 each represents hydrogen or a hydrocarbon group free of non-aromatic unsaturation, with the proviso that one of the pairs R1, R2 or R2, R3 may be joined together to form a hydrocarbon group having a ring of 5 or 6 carbon atoms which may contain an endomethylene group and Q represents a divalent hydrocarbon group which (a) is free of non-aromatic unsaturation, (b) is attached to each nitrogen atom through a carbon atom which is itself attached to not more than two other carbons and (c) provides a chain of two or three carbon atoms between the two nitrogen atoms, are obtained by reacting ketonitriles having the formula <FORM:1024905/C2/2> with diprimary amines NH2 QNH2 under conditions whereby ammonia and water are split out and removed.  The reaction is generally carried out in the presence of an inert solvent that forms an azeotrope with water, and the water is removed as the reaction progresses, usually at a temperature of 40 DEG  to 250 DEG  C. Alternatively, if the amine reactant is high boiling, a solvent is not used and the combination of reactants are heated together at 80 DEG  to 150 DEG  C. while water and ammonia are withdrawn. The product may be isolated by distillation under reduced pressure or recrystallized form a solvent.