# US 5,346,984 A · Star-shaped nylons, methods for their preparation, tetrasubstituted carboxylic acids and methods for their preparation > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,346,984 A - Document ID: US5346984A - Status: Granted - Kind: A - Application number: 08/046,837 - Filed: 1993-04-14 - Granted: 1994-09-13 - Earliest claimed: 1992-04-14 - Assignees: Kabushiki Kaisha Toyota Chuo Kenkyusho - Inventors: Naoki Hasegawa; Arimitsu Usuki; Akane Okada; Toshio Kurauchi - Web page: https://patentgrep.com/patent/US5346984A ## CPC - C08G 69/02: Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids - C07C 63/331: with all carboxyl groups bound to non-condensed rings - C08G 69/26: derived from polyamines and polycarboxylic acids - C08G 69/48: Polymers modified by chemical after-treatment - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract Star-shaped nylons with low melt viscosities and excellent mechanical properties, methods for their preparation, a novel tetrasubstituted carboxylic acid for use as a polymerization core therefor and methods for its preparation are provided. A star-shaped nylon has polymer chains emanating from 3 or more polymerization initiation groups which are substituents bonded to every other or more separated carbon atoms on an aromatic ring of an aromatic compound. The star-shaped nylon is produced by homogeneously mixing the aromatic compound with molten nylon monomer and polymerizing the nylon monomer with the respective polymerization initiation groups as the starting points. A novel tetrasubstituted carboxylic acid having a structure of 3,5,3',5'-biphenyltetracarboxylic acid is useful as a polymerization core for star-shaped nylons. ## Claims ### Claim 1 A star-shaped nylon with polymer chains emanating from 3 or more polymerization initiation groups which are substituents bonded to every other or more separated carbon atoms on an aromatic ring of an aromatic compound. ### Claim 2 (depends on 1) The star-shaped nylon of claim 1 wherein the aromatic ring of an aromatic compound is one selected from the group consisting of benzene ring, naphthalene ring, anthracene ring, pyridine ring, pyrrole ring, indole ring, furane ring, thiophene ring, purine ring, quinoline ring, phenanthrene ring, porphyrin ring, phthalocyanine ring and naphthalocyanine ring. ### Claim 3 (depends on 1) The star-shaped nylon of claim 1 wherein the aromatic ring of an aromatic compound is composed of at least two rings selected from the group consisting of benzene ring, naphthalene ring, anthracene ring, pyridine ring, pyrrole ring, indole ring, furane ring, thiophene ring, purine ring, quinoline ring, phenanthrene ring, porphyrin ring, phthalocyanine ring and naphthalocyanine ring, said at least two rings being combined together, with or without condensation. ### Claim 4 (depends on 1) The star-shaped nylon of claim 1 wherein the aromatic compound is selected from the group consisting of 1,3,5-benzenetricarboxylic acid (trimesic acid); 3,5,3',5'-biphenyltetracarboxylic acid; 2,4,6-pyridinetricarboxylic acid; 3,5,3',5'-bipyridyltetracarboxylic acid; 1,3,5,7-naphthalenetetracarboxylic acid; 1,3,6,8-acridinetetracarboxylic acid; 3,5,3',5+-benzophenonetetracarboxylic acid; ### Claim 5 (depends on 1) The star-shaped nylon of claim 1 wherein the aromatic compound is a porphyrin selected from the group consisting of tetracarboxyphenylporphyrin, aluminum tetracarboxyporphyrin, titanium tetracarboxyporphyrin, nickel tetracarboxyporphyrin and rhodium tetracarboxyporphyrin. ### Claim 6 (depends on 1) The star-shaped nylon of claim 1 wherein the aromatic compound is a phthalocyanine selected from the group consisting of tetracarboxyphthalocyanine, chloro(tetracarboxyphthalocyaninate)aluminum, (tetracarboxyphthalocyaninate)cobalt, (tetracarboxyphthalocyaninate)copper, (tetracarboxyphthalocyaninate)nickel , (tetracarboxyphthalocyaninate)iron, (tetracarboxyphthalocyaninate)oxovanadium, (tetracarboxyphthalocyaninate)lead, (tetracarboxyphthalocyaninate)magnesium, (tetracarboxyphthalocyaninate)tin, and (tetracarboxyphthalocyaninate)zinc. ### Claim 7 (depends on 1) The star-shaped nylon of claim 1 wherein the aromatic compound is a naphthalocyanine selected from the group consisting of tetracarboxynaphthalocyanines and metallic tetracarboxynaphthalocyanines. ### Claim 8 (depends on 1) The star-shaped nylon of claim 1 wherein a monomer for the polymer chains of the nylon is a monomer selected from the group consisting of valerolactam, caprolactam, 2-azacyclododecanone, 2-azacyclotridecanone and 1,8-diazacyclotetradecane-2,7-dione, ### Claim 9 (depends on 1) The star-shaped nylon of claim 1 wherein the polymerization initiation group is a carboxyl group. ### Claim 10 (depends on 1) The star-shaped nylon of claim 1 having a number average molecular weight in the range of 5,000-50,000. ### Claim 11 (depends on 1) The star-shaped nylon of claim 1 having a number average molecular weight in the range of 10,000-30,000. ### Claim 12 A method for the preparation of a star-shaped nylon, which comprises preparing an aromatic compound substituted with 3 or more polymerization initiation groups for initiating polymerization of nylon monomers, which are bonded to every other or more separated carbon atoms on an aromatic ring of the aromatic compound, homogeneously mixing the aromatic compound with lactam monomer under a condition where other polymerization initiators for nylon monomers are excluded, and polymerizing the nylon monomer starting at the respective polymerization initiation groups of the aromatic compound as the polymerization starting points. ### Claim 13 (depends on 12) The method of claim 12, comprising polymerizing under vacuum. ### Claim 14 (depends on 12) The method of claim 12, comprising polymerizing in a sealed tube. ### Claim 15 (depends on 1) The star-shaped nylon of claim 1 wherein the polymer chains are directly bonded to every other or more separated carbon atoms on an aromatic ring of an aromatic compound. ### Claim 16 (depends on 1) The star-shaped nylon of claim 1 wherein the aromatic compound is selected from the group consisting of 1,3,5-triaminobenzene; 1,3,5-tri(aminomethyl)benzene; 3,5,3',5'-tetraaminobiphenyl; 2. 4,6-triaminopyridine; 3,5,3',5'-tetraaminobipyridine; 1,3,5,7-tetraaminonaphthalene; 1,3,6,8-tetraaminoacridine; and 3,5,3',5'-tetraaminobenzophenon. ### Claim 17 (depends on 1) The star-shaped nylon of claim 1 wherein the polymerization initiation group is an amino group.