# US 9,518,142 B2 · Process for preparing isocyanate homopolymers containing uretdione groups > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,518,142 B2 - Document ID: US9518142B2 - Status: Granted - Kind: B2 - Application number: 14/907,153 - Filed: 2014-03-03 - Published: 2016-06-09 - Granted: 2016-12-13 - Earliest claimed: 2013-11-26 - Assignees: Wanhua Chemical Group Co., Ltd. - Applicants: Wanhua Chemical (Ningbo) Co., Ltd.; Wanhua Chemical Group Co., Ltd. - Inventors: Lidong Sun - Web page: https://patentgrep.com/patent/US9518142B2 ## CPC - C08G 18/027: {the polymeric products containing urethodione groups} - C07F 9/5414: {substituted by B, Si, P or a metal} - C08G 18/168: {Organic compounds} - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) ## Abstract The present invention relates to a process for preparing isocyanate homopolymers containing uretdione groups, in which the phosphinoboron compound of formula (I) are used as catalysts to catalyze the homopolymerization reaction of raw isocyanates, thereby obtaining a solution of isocyanate homopolymers having uretdione groups, then separating the solution and thus obtaining the isocyanate homopolymers containing uretdione groups. The isocyanate homopolymers containing uretdione groups prepared by this process have a high amount of the uretdione groups, wherein the dependence of the amount on the conversion rate of raw isocyanates is significantly ameliorated, with low chromaticities. ## Claims ### Claim 1 A process for preparing isocyanate homopolymers containing uretdione groups comprising: in the presence of catalysts, homopolymerizing raw isocyanate monomers to prepare isocyanate homopolymers containing uretdione groups, wherein the catalysts comprise phosphinoboron compounds of the structure of formula (I): wherein R1, R2 and R3 are independently selected from linear or branched C1-C20 alkyl group, optionally substituted C3-C20 cycloalkyl group, optionally substituted C7-C15 aralkyl or optionally substituted C6-C12 aryl group. ### Claim 2 (depends on 1) The process according to claim 1, wherein the phosphinoboron compound catalysts of formula (I) are selected from the group consisting of: ### Claim 3 (depends on 1) The process according to claim 1, wherein the raw isocyanate monomer is selected from one of the following compounds: aliphatic isocyanate, cycloaliphatic isocyanate or aromatic isocyanate; wherein the isocyanate having a NCO functionality ≧2. ### Claim 4 (depends on 3) The process according to claim 3, wherein the isocyanates are selected from the following compounds: tetramethylene-1,4-diisocyanate, pentamethylene-1,5-diisocyanate, hexamethylene-1,6-diisocyanate, lysine diisocyanate, isophorone diisocyanate, trimethylhexamethylene diisocyanate, dicyclohexylmethane diisocyanate, norbornane dimethylene isocyanate, diphenylmethane diisocyanate, toluene diisocyanate or p-phenyl diisocyanate. ### Claim 5 (depends on 1) The process according to claim 1, wherein the amount of phosphinoboron compound catalysts of formula (I) is 0.1-4 mol %, based on the amount of raw isocyanate monomers. ### Claim 6 (depends on 5) The process according to claim 5, wherein the phosphinoboron compound catalysts of formula (I) are used solely or as a formulated solution, wherein the concentration of the solution is 0.5-5 mol/L. ### Claim 7 (depends on 6) The process according to claim 6, wherein the solvents used in formulating the solution from the phosphinoboron compound catalysts are free of an active hydrogen. ### Claim 8 (depends on 1) The process according to claim 1, wherein the temperature of homopolymerization reaction is 20-120° C. ### Claim 9 (depends on 1) The process according to claim 1, wherein, when the conversion rate of the raw isocyanate monomers in the homopolymerization reaction reaches 20%-60% based on the mass of raw isocyanate monomers, a catalyst poison is used to terminate the homopolymerization reaction. ### Claim 10 (depends on 9) The process according to claim 9, wherein the catalyst poisons are alkylating agents or phosphate esters, where a mole ratio of the catalyst poison to the phosphinoboron compound catalyst is 1:1-2:1. ### Claim 11 (depends on 1) The process according to claim 1, wherein R1, R2 and R3 are independently selected from methyl, linear or branched C3-C20 alkyl, alkyl-substituted C3-C20 cycloalkyl group, alkyl-substituted C7-C15 aralkyl group, alkyl-substituted C6-C12 aryl group or alkoxyl-substituted C6-C12 aryl group. ### Claim 12 (depends on 1) The process according to claim 1, wherein R1, R2 and R3 are independently selected from methyl, n-butyl, tert-butyl, cyclopropyl, cyclohexyl, phenyl or methoxyphenyl. ### Claim 13 (depends on 4) The process according to claim 4, wherein the isocyanate is selected from hexamethylene-1,6-diisocyanate or isophorone diisocyanate. ### Claim 14 (depends on 5) The process according to claim 5, wherein the amount of phosphinoboron compound catalysts of formula (I) is 0.5-2 mol %, based on the amount of raw isocyanate monomers. ### Claim 15 (depends on 6) The process according to claim 6, wherein the phosphinoboron compound catalysts of formula (I) are used solely or as a formulated solution, wherein the concentration of the solution is 2-4 mol/L. ### Claim 16 (depends on 7) The process according to claim 7, wherein the solvents used in formulating the solution from the phosphinoboron compound catalysts are selected from the group consisting of: halogenated hydrocarbons, aromatic hydrocarbons, ethers, and combinations thereof. ### Claim 17 (depends on 16) The process according to claim 16, wherein the solvents used in formulating the solution from the phosphinoboron compound catalysts are selected from the group consisting of: dichloromethane, tetrahydrofuran, methylbenzene, dimethylbenzene, chlorobenzene, and combinations thereof. ### Claim 18 (depends on 8) The process according to claim 8, wherein the temperature of homopolymerization reaction is 50-100° C. ### Claim 19 (depends on 10) The process according to claim 10, wherein the catalyst poisons are alkylating agents or phosphate esters, where a mole ratio of the catalyst poison to the phosphinoboron compound catalyst is 1:1-1.2:1.