# US 10,370,570 B2 · Low-modulus silylated polyurethanes > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,370,570 B2 - Document ID: US10370570B2 - Status: Granted - Kind: B2 - Application number: 14/741,758 - Filed: 2015-06-17 - Published: 2015-10-08 - Granted: 2019-08-06 - Earliest claimed: 2012-12-17 - Assignees: Henkel AG & Co. KGaA - Applicants: Henkel AG & Co. KGAA - Inventors: Lars Zander; Helmut Loth; Marc Pascal Burmeister; Rolf Tenhaef; Johann Klein; Jan-Erik Damke - Web page: https://patentgrep.com/patent/US10370570B2 ## CPC - C09J 175/08: from polyethers - C08G 18/0852: {the solvents being organic} - C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step - C08G 18/12: using two or more compounds having active hydrogen in the first polymerisation step - C08K 5/0016: {Plasticisers} - C09K 3/1021: {Polyurethanes or derivatives thereof} - C08J 2375/08: from polyethers - 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) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) ## Abstract A method for producing a silylated polyurethane that comprises the following steps: (1) reacting at least one polyether polyol having a number average molecular weight of at least 2,000 g/mol with at least one polyisocyanate in the presence of at least one solvent; (2) reacting the reaction product of step (1) with at least one silane of formula (I) A-R—SiXYZ (I), where A means —NH2 or —NHB, wherein B stands for a branched or linear alkyl radical with 1-12 C atoms, possibly having functional groups, a cyclic alkyl radical having 5-8 C atoms, or an aryl radical, R is a divalent hydrocarbon radical having 1-12 C atoms, and X, Y, Z are substituents on the Si atom and are independently of each other C1-C8 alkyl, C1-C8 alkoxy or C1-C8 acyloxy groups, wherein at least one of radicals X, Y, Z is a C1-C8 alkoxy or C1-C8 acyloxy group, in the presence of at least one solvent. Further disclosed is a silylated polyurethane that can be produced by the method, a curable composition based thereon, and the use of such a composition as an adhesive, sealant and/or coating material. ## Claims ### Claim 1 Method for producing a silylated polyurethane, comprising the following steps: (1) mixing at least one polyether polyol having a number average molecular weight of 10,000 to 16,000 g/mol with at least one polyisocyanate and at least one solvent; (2) reacting the at least one polyether polyol having a number average molecular weight of 10,000 to 16,000 g/mol with the at least one polyisocyanate in the presence of the at least one solvent to form a reaction product, wherein the solvent includes an aromatic compound comprising a C10-C20 alkyl group; (3) reacting the reaction product from step (2) with at least one silane of formula (I) A-R—SiXYZ (I), wherein A means —NH2 or —NHB, where B stands for a branched or linear alkyl radical which contains 1-12 C atoms and optionally functional groups, or stands for a cyclic alkyl radical containing 5-8 C atoms, or an aryl radical, and R is a divalent hydrocarbon radical containing 1-12 C atoms, and X, Y, Z are substituents on the Si atom and independently stand for C1-C8 alkyl, C1-C8 alkoxy, or C1-C8 acyloxy groups, at least one of the radicals X, Y, Z standing for a C1-C8 alkoxy or C1-C8 acyloxy group, in the presence of at least one solvent, wherein the solvent includes an aromatic compound comprising a C10-C20 alkyl group. ### Claim 2 (depends on 1) Method according to claim 1, wherein the solvent is a C10-C20 alkyl-substituted benzene. ### Claim 3 (depends on 1) Method according to claim 1, wherein R in formula (I) is a methylene, ethylene, or n-propylene group. ### Claim 4 A curable composition consisting of the following components in the corresponding weight fractions: 10-40% by weight of silylated polyurethane produced by (1) reacting at least one polyether polyol having a number average molecular weight of at least 2,000 g/mol with at least one polyisocyanate in the presence of at least one solvent, wherein the solvent includes an aromatic compound comprising a C10-C20 alkyl group; (2) reacting the reaction product from step (1) with at least one silane of formula (I) A-R—SiXYZ (I), wherein A means —NH2 or —NHB, where B stands for a branched or linear alkyl radical which contains 1-12 C atoms and optionally functional groups, or stands for a cyclic alkyl radical containing 5-8 C atoms, or an aryl radical, and R is a divalent hydrocarbon radical containing 1-12 C atoms, and X, Y, Z are substituents on the Si atom and independently stand for C1-C8 alkyl, C1-C8 alkoxy, or C1-C8 acyloxy groups, at least two of the radicals X, Y, Z standing for a C1-C8 alkoxy or C1-C8 acyloxy group, in the presence of at least one solvent, wherein the solvent includes an aromatic compound comprising a C10-C20 alkyl group; 10-30% by weight solvent 10-80% by weight filler 0.01-1% by weight curing catalyst 0-10% by weight auxiliary substances where the weight fractions add up to 100% by weight, and are based on the total weight of the curable composition. ### Claim 5 (depends on 4) A curable composition according to claim 4, wherein the polyether polyol has a number average molecular weight of 7,000 g/mol to 16,000 g/mol. ### Claim 6 (depends on 4) A curable composition according to claim 4, wherein the filler is calcium carbonate. ### Claim 7 (depends on 4) The curable composition of claim 4 being an adhesive, sealant, and/or coating.