Patent GB-900150-A (GB)
Title: A process for the alkaline polymerisation of lactams
Inventor: DACHS KARL
IPC: C08G69/20
Filed: 1960-07-12
Abstract: A process for the polymerization of lactams having from 4 to 12 ring carbon atoms in the presence of an alkaline polymerization initiator and a polymerization activator comprises using as the activator a substituted urea, thiourea or guanidine, which is capable of being dissolved undecomposed in the lactams at the polymerization temperature, having the general formula <FORM:0900150/IV(a)/1> where R1, R2 and R3 are hydrogen atoms or monovalent hydrocarbon radicals having from 1 to 20 carbon atoms, or R1 and R2 together represent a divalent aryl radical of the general formula -CH-(CH2)n-CO- where n is an integer from 3 to 11, and in which said radicals R1, R2 and R3 may be substituted by fluorine or ether groups, X is oxygen, sulphur or the radical > N-R5 where R5 is a hydrogen atom or a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, and R4 is a monovalent hydrocarbon radical with from 1 to 20 carbon atoms or one of the radicals <FORM:0900150/IV(a)/2> and <FORM:0900150/IV(a)/3> wherein Y represents a divalent and Z a trivalent hydrocarbon radical with from 1 to 20 carbon atoms which may be substituted by fluorine or ether groups and X, R1, R2 and R3 have the same meanings as given above.  A large number of activators is specified.  Specified lactams are pyrrolidone, piperidone, S -caprolactam, oenanthic lactam, caprylic lactam and lauric lactam.  Specified initiators are the alkali and alkaline earth metals and alkaline reacting compounds thereof.  The examples describe the polymerization of caprylic lactam, S -caprolactam, lauric lactam and a -pyrrolidone in the presence of as activators 1,6-bis(N1-butylureids)hexane, 1,3-bis(N1-butylureids)benzene, 1,6-bis(caprolactam-N-carbamido)hexane, 1,6-bis(caprylic lactam-N-carbamido)-hexane, 1,6-bis(pyrrolidone-N-carbamido)-hexane, pyrrolidone N-carbonic acid anilide, 1,5-bis(caprolactam-N-carbamido)-naphthalene, N-phenyl-N1-butyl urea, N-phenyl-N1-stearyl urea, N-phenyl-N1-a -naphthyl urea, N-phenyl-N1-butyl thiourea, N-phenyl-N1-a -naphthyl thiourea, N-p-fluorphenyl-N1-phenyl urea, N-p-ethoxyphenyl-N1-phenyl urea, N-p-fluorphenyl-N1-p-methoxyphenyl urea, N,N1,N11-tricyclohexyl guanidine, morpholine-N-thiocarbonic acid anilide, 1,3-bis(N1-phenylthioureido)-4-methylbenzene, 1,3-bis-(N1-phenylureido)-4-methylbenzene, 1,3-bis-(N1,N11 - dicyclohexylguanido) - 4 - methylbenzene, 4,41-bis-(N1-phenylureido)-dicyclohexylmethane, 4,41-bis-(N1-phenylthioureido)-dicyclohexylmethane, 4,41-bis-(N1-phenylureido)-diphenyl ether, 4,41-bis-(N1-phenylureido)-diphenyl sulphone, 1,10-bis-(N1-phenylureido)-2-n-nonyldecane, 1,11-bis-(N1-phenylthioureido)-2-n-octylundecane, 4,41,411-tris-(N1-phenylureido) -tricyclohexylmethane, 4,41,411-tris-(N1-phenylthioureido) - 3,31 - dimethoxy - triphenylmethane, 3,31,311-tris-(N1-p-fluorphenylureido) -tri-n-propylamine, 3,31,311-tris-(N1-p-methoxyphenylureido) -tri-n-propylamine, pyrrolidone-N-carbonic acid anilide, pyrrolidone-N-carbonic acid p-fluoranilide, pyrrolidone-N-carbonic acid p-ethoxyanilide, caprylic lactam-N-carbonic acid stearylamine, 1,3-bis-(pyrrolidone-N-carbamido)-4-methylbenzene, 1,3-bis-(lauroylic lactam-N-carbamido)-4-methylbenzene, 1,5-bis-(pyrrolidone-N-carbamido)-naphthalene, 1,10-bis-(caprylic lactam-N-carbamido)-2-n-nonyl-decane, caprylic lactam-N-carbonic acid-N1,N11-dicyclohexylamidine, 4,41,411-tris-(caprylic lactam-N-carbamido)-triphenyl methane, 4,41,411-tris-(caprolactam-N-carbamido)-triphenyl methane, 6,61,611-tris-(caprylic lactam-N-carbamido)-tri-n-hexylamine and 2,4,41-tris-(caprylic lactam-N-carbamido)-biphenyl.