# US 12,180,335 B2 · Polycarbonate diol derived from ether diol of anhdrohexitol and preparation method thereof, and polyurethane prepared therefrom and adhesive comprising the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,180,335 B2 - Document ID: US12180335B2 - Status: Granted - Kind: B2 - Application number: 17/614,772 - Filed: 2020-05-28 - Published: 2022-07-21 - Granted: 2024-12-31 - Earliest claimed: 2019-05-31 - Assignees: Samyang Corporation - Applicants: Samyang Corporation - Inventors: Jun Seop Im; Seung Hyun Yoo; Hoon Ryu; Won Hyun Jeon - Web page: https://patentgrep.com/patent/US12180335B2 ## CPC - C08G 64/30: using carbonates - C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step - C08G 18/44: Polycarbonates - C08G 18/7671: {containing only one alkylene bisphenyl group} - C08G 64/02: Aliphatic polycarbonates - C08G 64/0208: {saturated} - C08G 64/305: {and alcohols} - C09D 175/06: from polyesters - C09J 175/06: from polyesters - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - 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 A polycarbonate diol is derived from ether diol of anhydrohexitol, a preparation method thereof, a polyurethane prepared therefrom, and adhesive, etc. including the same. More specifically, the polycarbonate diol includes repeated units derived from ether diol of anhydrohexitol; and carbonate diester; and optionally anhydrohexitol; and thereby showing better effect of improving color as compared with conventional polycarbonate diol, and being capable of providing polyurethane prepared therefrom with remarkably improved adhesion strength (T-peel strength or shear strength), preparation method thereof, polyurethane prepared therefrom, and adhesive, paint and coating agent including the same. ## Claims ### Claim 1 A polycarbonate diol comprising: (1) repeated units derived from ether diol of anhydrohexitol; and (2) repeated units derived from carbonate diester, wherein the polycarbonate diol is prepared by reacting a mixture comprising the ether diol of anhydrohexitol and the carbonate diester in the presence of a transesterification catalyst, and wherein the amount of the ether diol of anhydrohexitol in the mixture is 30 to 95% by weight, based on total 100% by weight of the mixture. ### Claim 2 A polycarbonate diol comprising: (1) repeated units derived from ether diol of anhydrohexitol; (2) repeated units derived from carbonate diester; and (3) repeated units derived from anhydrohexitol, wherein the polycarbonate diol is prepared by reacting a mixture comprising the ether diol of anhydrohexitol, the carbonate diester and the anhydrohexitol in the presence of a transesterification catalyst, and wherein the amount of the ether diol of anhydrohexitol in the mixture is 5 to 60% by weight and the amount of the anhydrohexitol in the mixture is 10 to 45% by weight, based on total 100% by weight of the mixture. ### Claim 3 (depends on 1) The polycarbonate diol of claim 1, wherein the anhydrohexitol is selected from isosorbide (1,4:3,6-dianhydrosorbitol), isomannide (1,4:3,6-dianhydromannitol), isoidide (1,4:3,6-dianhydroiditol) or mixtures thereof. ### Claim 4 (depends on 1) The polycarbonate diol of claim 1, wherein the ether diol of anhydrohexitol is a product obtained by reacting anhydrohexitol and alkylene oxide. ### Claim 5 (depends on 1) The polycarbonate diol of claim 1, wherein the ether diol of anhydrohexitol is a product obtained by reacting anhydrohexitol and ethylene carbonate. ### Claim 6 (depends on 1) The polycarbonate diol of claim 1, wherein the carbonate diester is selected from dialkyl carbonate, diaryl carbonate, alkylene carbonate or combinations thereof. ### Claim 7 (depends on 1) The polycarbonate diol of claim 1, further comprising repeated units derived from aliphatic diol. ### Claim 8 (depends on 1) The polycarbonate diol of claim 1, comprising repeated units having a structure of the following formula 1: wherein each of R1 and R2 is independently a linear or branched alkylene group having 2 to 20 carbons, and R1 and R2 may be the same or different from each other. ### Claim 9 (depends on 2) The polycarbonate diol of claim 2, comprising repeated units having a structure of the following formula 1; and repeated units having a structure of the following formula 2: wherein each of R1 and R2 is independently a linear or branched alkylene group having 2 to 20 carbons, and R1 and R2 may be the same or different from each other; ### Claim 10 (depends on 7) The polycarbonate diol of claim 7, comprising repeated units having a structure of the following formula 3: wherein R3 is a linear or branched alkylene group having 2 to 10 carbons. ### Claim 11 A method for preparing a polycarbonate diol, comprising a step of reacting a mixture comprising (i) ether diol of anhydrohexitol and (ii) carbonate diester, in the presence of a transesterification catalyst, wherein the amount of the ether diol of anhydrohexitol in the mixture is 30 to 95% by weight, based on total 100% by weight of the mixture. ### Claim 12 A method for preparing a polycarbonate diol, comprising a step of reacting a mixture comprising (i) ether diol of anhydrohexitol, (ii) carbonate diester and (iii) anhydrohexitol, in the presence of a transesterification catalyst, wherein the amount of the ether diol of anhydrohexitol in the mixture is 5 to 60% by weight and the amount of the anhydrohexitol in the mixture is 10 to 45% by weight, based on total 100% by weight of the mixture. ### Claim 13 (depends on 11) The method for preparing a polycarbonate diol of claim 11, wherein the mixture further comprises aliphatic diol. ### Claim 14 (depends on 1) A polyurethane comprising repeated units derived from the polycarbonate diol of claim 1. ### Claim 15 (depends on 1) A method for preparing a polyurethane, comprising the steps of: reacting a polyol component and a polyisocyanate component to prepare a prepolymer; and reacting the prepolymer with a chain extender; the method being characterized in that the polyol component comprises the polycarbonate diol of claim 1. ### Claim 16 (depends on 14) An adhesive comprising the polyurethane of claim 14. ### Claim 17 (depends on 14) A paint comprising the polyurethane of claim 14. ### Claim 18 (depends on 14) A coating agent comprising the polyurethane of claim 14. ### Claim 19 (depends on 2) The polycarbonate diol of claim 2, comprising repeated units having a structure of the following formula 3: wherein R3 is a linear or branched alkylene group having 2 to 10 carbons. ### Claim 20 (depends on 2) The polycarbonate diol of claim 2, wherein the anhydrohexitol is selected from isosorbide (1,4:3,6-dianhydrosorbitol), isomannide (1,4:3,6-dianhydromannitol), isoidide (1,4:3,6-dianhydroiditol) or mixtures thereof. ### Claim 21 (depends on 2) The polycarbonate diol of claim 2, wherein the ether diol of anhydrohexitol is a product obtained by reacting anhydrohexitol and alkylene oxide. ### Claim 22 (depends on 2) The polycarbonate diol of claim 2, wherein the ether diol of anhydrohexitol is a product obtained by reacting anhydrohexitol and ethylene carbonate. ### Claim 23 (depends on 2) The polycarbonate diol of claim 2, further comprising repeated units derived from aliphatic diol. ### Claim 24 (depends on 12) The method for preparing a polycarbonate diol of claim 12, wherein the mixture further comprises aliphatic diol. ### Claim 25 (depends on 2) A polyurethane comprising repeated units derived from the polycarbonate diol of claim 2. ### Claim 26 (depends on 2) A method for preparing a polyurethane, comprising the steps of: reacting a polyol component and a polyisocyanate component to prepare a prepolymer; and reacting the prepolymer with a chain extender; the method being characterized in that the polyol component comprises the polycarbonate diol of claim 2. ### Claim 27 (depends on 25) An adhesive comprising the polyurethane of claim 25. ### Claim 28 (depends on 25) A paint comprising the polyurethane of claim 25. ### Claim 29 (depends on 25) A coating agent comprising the polyurethane of claim 25.