# US 10,246,545 B2 · Bismuth-containing catalyst for polyurethane compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,246,545 B2 - Document ID: US10246545B2 - Status: Granted - Kind: B2 - Application number: 14/359,666 - Filed: 2012-12-12 - Published: 2014-11-20 - Granted: 2019-04-02 - Earliest claimed: 2011-12-12 - Assignees: Sika Technology AG - Applicants: Sika Technology AG - Inventors: Urs Burckhardt; Rita Cannas - Web page: https://patentgrep.com/patent/US10246545B2 ## CPC - C08G 18/227: {of antimony, bismuth or arsenic} - C07C 235/74: of a saturated carbon skeleton - C07F 9/94: Bismuth compounds - C08G 18/4812: {Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups} - C08G 18/4829: {Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)} - C08G 18/7671: {containing only one alkylene bisphenyl group} - C09D 175/08: from polyethers - C09J 175/08: from polyethers - C08G 2190/00: Compositions for sealing or packing joints - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) ## Abstract Invention relates to bismuth-containing catalysts, obtainable by reacting at least one bismuth(III) salt or bismuth(III) complex with at least one 1,3-ketoamide with the formula (I). Such complex compounds are suited in particular as catalysts for one- and two-component polyurethane compositions. The invention further relates to two-component polyurethane compositions, including at least one polyisocyanate as the first component, at least one polyol as the second component, and at least one such bismuth-containing catalyst. The invention further relates one-component polyurethane compositions, including at least one polyurethane prepolymer having isocyanate groups, produced from at least one polyisocyanate with at least one polyol, and one such bismuth-containing catalyst. The invention also relates to various uses of the aforementioned polyurethane compositions. ## Claims ### Claim 1 A bismuth-containing catalyst, obtained by reacting at least one bismuth(III) salt or bismuth(III) complex with at least one 1,3-ketoamide with the formula (I), where R1 and R2 independently of one another are a hydrogen group, a monovalent saturated or unsaturated hydrocarbon group having 1 to 10 carbon atoms, or together are a bivalent alkylene group having 3 to 6 carbon atoms, and R3 and R4 independently of one another are a hydrogen group, a monovalent saturated hydrocarbon group, which optionally includes heteroatoms, having 1 to 12 carbon atoms, or together are a bivalent alkylene group, which optionally includes heteroatoms, having 3 to 6 carbon atoms. ### Claim 2 (depends on 1) The bismuth-containing catalyst according to claim 1, wherein the bismuth-containing catalyst has the formula Bi(L)x(Y)3-x, in which x is 1, 2 or 3, Y is a singly negative ligand, and L is a ligand with the formula (I). ### Claim 3 (depends on 1) The bismuth-containing catalyst according to claim 1, wherein R1 is an alkyl group having 1 to 4 carbon atoms, a phenyl group, or together with R2 is a bivalent alkylene group having 3 to 4 carbon atoms. ### Claim 4 (depends on 1) The bismuth-containing catalyst according to claim 1, wherein R2 is a hydrogen group. ### Claim 5 (depends on 1) The bismuth-containing catalyst according to claim 1, wherein R3 is a hydrogen group, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 6 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkyl ether group having 1 to 4 carbon atoms, or together with R4 is a divalent alkylene group with the formula —(CH2)n—X—(CH2)n— with X=O, NR, where R is a monovalent alkyl group having 1 to 4 carbon atoms, or S and n=2 to 6. ### Claim 6 (depends on 1) The bismuth-containing catalyst according to claim 1, wherein R4 is a hydrogen group, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 6 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms or an alkyl ether group having 1 to 4 carbon atoms. ### Claim 7 (depends on 1) The bismuth-containing catalyst according to claim 1, wherein the stoichiometric ratio between the bismuth(III) salt or the bismuth(III) complex and the 1,3-ketoamide with the formula (I) ranges between approximately 1:0.5 and 1:20. ### Claim 8 (depends on 1) A method for producing the bismuth-containing catalyst according to claim 1, wherein at least one bismuth(III) salt or one bismuth(III) complex is reacted with at least one 1,3-ketoamide with the formula (I), where R1, R2, R3 and R4 are as defined above. ### Claim 9 (depends on 8) The method according to claim 8, wherein a bismuth(III) carboxylate is used as the bismuth(III) salt or bismuth(III) complex. ### Claim 10 (depends on 1) A method comprising: catalyzing curable compounds with the bismuth-containing catalyst according to claim 1. ### Claim 11 (depends on 1) A two-component polyurethane composition, comprising: as a first component: at least one polyol; and at least one bismuth-containing catalyst according to claim 1; and as a second component: at least one polyisocyanate, wherein the first and second components are stored in separate containers. ### Claim 12 (depends on 11) The two-component polyurethane composition according to claim 11, wherein the polyol is a polyether polyol and the polyisocyanate is a diisocyanate. ### Claim 13 (depends on 11) The two-component polyurethane composition according to claim 11, wherein the bismuth-containing catalyst accounts for 0.001 to 5 mmol-equivalent bismuth based on 100 g of the composition. ### Claim 14 (depends on 1) A one-component polyurethane composition, comprising at least one polyurethane prepolymer having isocyanate groups, produced from at least one polyisocyanate with at least one polyol, and at least one bismuth-containing catalyst according to claim 1. ### Claim 15 (depends on 11) A method comprising: applying the two-component polyurethane composition according to claim 11 as a casting compound, sealant, adhesive, covering, coating, paint, subcoating, molding, or elastomer for building and industrial applications. ### Claim 16 (depends on 1) The bismuth-containing catalyst according to claim 1, wherein R1 is butyl, R2 is H, R3 is butyl and R4 is butyl.