Patent GB-1094724-A (GB)
Title: N-vinyl-2-piperazinones and polymers thereof
IPC: C07D/
Filed: 1965-03-02
Abstract: Gasoline and lubricating oil compositions contain polymers or copolymers of N-vinyl-2-piperazinones of formula <FORM:1094724/C4-C5/1> in which R1 is hydrogen; C1-C18 alkyl; aralkyl or alkaralkyl each containing up to 18 carbon atoms, and in each of which each alkyl group contains up to 8 carbon atoms; dialkylaminoalkyl of up to 12 carbon atoms, and in which each alkyl group contains up to 8 carbon atoms; or furfuryl; R2 individually, is hydrogen or methyl; R3, individually, is hydrogen; C1-C18 alkyl; phenyl; naphthyl; alkyl-, chloro- or alkoxy-substituted phenyl or naphthyl each containing up to 18 alkyl carbon atoms; aralkyl or alkaralkyl of up to 18 carbon atoms; or 2-furyl; R2 and R3 collectively, represent an alkylene group containing up to 18 carbon atoms which together with the carbon atom to which it is attached forms a ring having 5 to 7 cyclic atoms; R4, individually, is hydrogen or C1-C4 alkyl; R, individually, is hydrogen or C1-C4 alkyl and R4 and R5, collectively, represent an alkylene group containing up to 18 carbon atoms which together with the carbon atom to which it is attached forms a ring having 5 to 7 cyclic carbon atoms, the terms "alkyl" and "alkoxy" in the definitions of R1, R3, R4 and R5 including cycloalkyl and cycloalkoxy respectively.ALSO:N-Vinyl-2- piperazinones of the following formula are homopolymerized or copolymerized <FORM:1094724/C3/1> in which R1 is hydrogen; C1-C18 alkyl; aralkyl or alkaralkyl each containing up to 18 carbon atoms, and in each of which each alkyl group contains up to 8 carbon atoms; dialkylaminoalkyl of up to 12 carbon atoms, and in which each alkyl group contains up to 8 carbon atoms; or furfuryl; R2 individually, is hydrogen or methyl; R3, individually, is hydrogen; C1-C18 alkyl; phenyl; naphthyl; alkyl-, chloro- or alkoxy-substituted phenyl or naphthyl each containing up to 18 alkyl carbon atoms; aralkyl or alkaralkyl of up to 18 carbon atoms; or 2-furyl; R2 and R3 collectively, represent an alkylene group containing up to 18 carbon atoms which together with the carbon atom to which it is attached forms a ring having 5 to 7 cyclic atoms; R4, individually, is hydrogen or C1-C4 alkyl; R, individually, is hydrogen or C1-C4 alkyl and R4 and R5, collectively, represent an alkylene group containing up to 18 carbon atoms which together with the carbon atom to which it is attached forms a ring having 5 to 7 cyclic carbon atoms, the terms "alkyl" and "alkoxy" in the definitions of R1, R3, R4 and R5 including cycloalkyl and cycloalkoxy respectively. Suitable comonomers include alkyl and aminoalkyl acrylic and methacrylic esters, acrylonitrile, methacrylonitrile, acrylamides, methacrylamides, styrenes, vinyl-benzenes, vinyl carboxylates, ethers, sulphides, and sulphones, N-vinyl lactams and alkyleneureas, olefines, fumaric, maleic and itaconic esters, and vinylpyridines. Polymerization may be effected in bulk solution, suspension or emulsion.  Conventional free radical catalysts may be used or high energy radiation.  Quaternary ammonium activators may be present. The polymers may be used in coating formulations, to form fibres, as gasoline and lubricant additives, to thicken starch-water mixtures for application to paper or cloth, as soil aggregants, as glossing agents for leather, as dye assistants, as corrosion inhibitors in acid pickling baths, to promote settling of clays from aqueous suspensions or as fungistatic or bacteriostatic agents.ALSO:The invention comprises compounds of formula <FORM:1094724/C2/1> in which R1 is hydrogen; C1- 18 alkyl; aralkyl or alkaralkyl each containing up to 18 carbon atoms, and in each of which each alkyl group contains up to 8 carbon atoms; dialkylaminoalkyl of up to 12 carbon atoms, and in which each alkyl group contains up to 8 carbon atoms; or furfuryl; R2 individually, is hydrogen or methyl; R3, individually, is hydrogen or methyl; R3, individually, is hydrogen; C1-C18 alkyl; phenyl; naphthyl; alkyl-, chloro- or alkoxy-substituted phenyl or naphthyl each containing up to 18 alkyl carbon atoms; aralkyl or alkaralkyl of up to 18 carbon atoms; or 2-furyl; R2 and R3 collectively, represent an alkylene group containing up to 18 carbon atoms which together with the carbon atom to which it is attached forms a ring having 5 to 7 cyclic atoms; R4, individually, is hydrogen or C1-C4 alkyl; R, individually, is hydrogen or C1-C4 alkyl and R4 and R5, collectively, represent an alkylene group containing up to 18 carbon atoms which together with the carbon atom to which it is attached forms a ring having 5 to 7 cyclic carbon atoms, the terms "alkyl" and "alkoxy" in the definitions of R1, R3, R4 and R5 including cycloalkyl and cycloalkoxy respectively.  They are prepared by vinylating the corresponding unsubstituted piperazinones with acetylene.