# US 9,006,381 B2 · Impact-resistant polyamide composition and process for production of same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,006,381 B2 - Document ID: US9006381B2 - Status: Granted - Kind: B2 - Application number: 13/806,055 - Filed: 2011-06-23 - Published: 2013-07-25 - Granted: 2015-04-14 - Earliest claimed: 2010-06-23 - Assignees: Nagase Chemtex Corporation - Applicants: Tokizane Imanishi; Hirofumi Nishida - Inventors: Tokizane Imanishi; Hirofumi Nishida - Web page: https://patentgrep.com/patent/US9006381B2 ## CPC - C08G 69/14: Lactams - C08G 69/18: Anionic polymerisation - C08G 69/20: characterised by the catalysts used - C08L 77/02: Polyamides derived from omega-amino carboxylic acids or from lactams thereof (C08L77/10 takes precedence) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract Provided are: an impact-resistant polyamide composition which exhibits improved toughness and improved impact strength and which can be easily polymerized in-situ in a molding stage; and a novel process for the production of the same. The novel process comprises initiating the anionic polymerization of ε-caprolactam in the presence of (A) an anionic polymerization catalyst, (B) an anionic polymerization activator, (C) 2.0 to 30% by weight (relative to the ε-caprolactam) of an N,N-disubstituted vinylbenzylamine, and (D) a radical polymerization initiator, and subjecting the resulting system to reaction under conditions comprising a reaction temperature of the reaction system of 120 to 180° C. and a reaction time of 10 seconds to 120 minutes. Since radical polymerization in the process is conducted without hindering the anionic polymerization, an alloyed polyamide composed of both polycaprolactam and poly (N,N-disubstituted vinylbenzylamine) can be obtained. ## Claims ### Claim 1 A polymerizable composition, comprising: (A) an anionic polymerization catalyst; (B) an anionic polymerization activator; (C) 2.0 to 30% by weight, based on the weight of ε-caprolactam, of an N,N-disubstituted vinylbenzylamine represented by general formula (I): wherein R1 and R2 are the same or different and each are a straight-chain or branched-chain saturated hydrocarbon group having 2 to 15 carbon atoms, wherein the saturated hydrocarbon group may have one —O— bond between two carbon atoms when the number of carbon atoms is 2, and one or two —O— bonds between two carbon atoms when the number of carbon atoms is 3 or more; (D) a radical polymerization initiator; and (E) ε-caprolactam. ### Claim 2 (depends on 1) The polymerizable composition according to claim 1, wherein the N,N-disubstituted vinylbenzylamine (C) is one in which R1 and R2 in general formula (I) are the same or different and each are a straight-chain or branched-chain alkyl group having 2 to 12 carbon atoms. ### Claim 3 (depends on 1) The polymerizable composition according to claim 1, wherein the N,N-disubstituted vinylbenzylamine (C) is one in which R1 and R2 in general formula (I) are the same or different and each are a straight-chain or branched-chain saturated hydrocarbon group having 2 to 12 carbon atoms wherein the saturated hydrocarbon group has one —O— bond between two carbon atoms. ### Claim 4 (depends on 3) The polymerizable composition according to claim 3, wherein the N,N-disubstituted vinylbenzylamine (C) is one in which R1 and R2 in general formula (I) are the same and each are a group represented by —(CH2)m—O—(CH2)n—CH3 wherein n=0, 1, 2, 3 or 4, and m=1 or 2. ### Claim 5 (depends on 1) The polymerizable composition according to claim 1, wherein the N,N-disubstituted vinylbenzylamine (C) is at least one selected from the group consisting of N,N-bis(ethyl)-4-vinylbenzylamine, N,N-bis(n-propyl)-4-vinylbenzylamine, N,N-bis(n-butyl)-4-vinylbenzylamine, N,N-bis(n-amyl)-4-vinylbenzylamine, N,N-bis(n-hexyl)-4-vinylbenzylamine, N,N-bis(n-octyl)-4-vinylbenzylamine, N,N-bis(n-decyl)-4-vinylbenzylamine, N,N-bis(n-dodecyl)-4-vinylbenzylamine, N,N-bis(2-methoxyethyl)-4-vinylbenzylamine, N,N-bis(2-ethoxyethyl)-4-vinylbenzylamine and N,N-di-2-ethylhexyl-4-vinylbenzylamine. ### Claim 6 (depends on 5) The polymerizable composition according to claim 5, wherein the radical polymerization initiator (D) is tetraphenylethanediol. ### Claim 7 (depends on 1) The polymerizable composition according to claim 1, wherein the polymerizable composition contains 0.01 to 20% by weight of the radical polymerization initiator (D) based on the weight of the N,N-disubstituted vinylbenzylamine (C). ### Claim 8 (depends on 1) A polymer composition obtained by polymerizing the polymerizable composition according to claim 1. ### Claim 9 A process for producing a polyamide composition, comprising: initiating anionic polymerization of ε-caprolactam in the presence of (A) an anionic polymerization catalyst; (B) an anionic polymerization activator; (C) 2.0 to 30% by weight, based on the weight of ε-caprolactam, of an N,N-disubstituted vinylbenzylamine represented by general formula (I): wherein R1 and R2 are the same or different and each are a straight-chain or branched-chain saturated hydrocarbon group having 2 to 15 carbon atoms, wherein the saturated hydrocarbon group may have one —O— bond between two carbon atoms when the number of carbon atoms is 2, and one or two —O— bonds between two carbon atoms when the number of carbon atoms is 3 or more; and (D) a radical polymerization initiator, and subjecting the resulting system to reaction under conditions of a reaction temperature of the reaction system of 120 to 180° C. and a reaction time of 10 seconds to 120 minutes. ### Claim 10 (depends on 9) The process according to claim 9, wherein the N,N-disubstituted vinylbenzylamine (C) is one in which R1 and R2 in general formula (I) are the same or different and each are a straight-chain or branched-chain alkyl group having 2 to 12 carbon atoms. ### Claim 11 (depends on 9) The process according to claim 9, wherein the N,N-disubstituted vinylbenzylamine (C) is one in which R1 and R2 in general formula (I) are the same or different and each are a straight-chain or branched-chain saturated hydrocarbon group having 2 to 12 carbon atoms wherein the saturated hydrocarbon group has one —O— bond between two carbon atoms. ### Claim 12 (depends on 11) The process according to claim 11, wherein the N,N-disubstituted vinylbenzylamine (C) is one in which R1 and R2 in general formula (I) are the same and each are a group represented by -(CH2)m—O—(CH2)n—CH3 wherein n=0, 1, 2, 3 or 4, and m=1 or 2. ### Claim 13 (depends on 9) The process according to claim 9, wherein the N,N-disubstituted vinylbenzylamine (C) is at least one selected from the group consisting of N,N-bis(ethyl)-4-vinylbenzylamine, N,N-bis(n-propyl)-4-vinylbenzylamine, N,N-bis(n-butyl)-4-vinylbenzylamine, N,N-bis(n-amyl)-4-vinylbenzylamine, N,N-bis(n-hexyl)-4-vinylbenzylamine, N,N-bis(n-octyl)-4-vinylbenzylamine, N,N-bis(n-decyl)-4-vinylbenzylamine, N,N-bis(n-dodecyl)-4-vinylbenzylamine, N,N-bis(2-methoxyethyl)-4-vinylbenzylamine, N,N-bis(2-ethoxyethyl)-4-vinylbenzylamine and N,N-di-2-ethylhexyl-4-vinylbenzylamine. ### Claim 14 (depends on 9) The process according to claim 9, wherein the radical polymerization initiator (D) is tetraphenylethanediol. ### Claim 15 (depends on 9) The process according to claim 9, wherein the radical polymerization initiator (D) is present in an amount of 0.01 to 20% by weight based on the weight of the N,N-disubstituted vinylbenzylamine (C).