# US 10,370,498 B2 · Curable polysilsesquioxane compound, production method thereof, curable composition, cured product and use method of curable composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,370,498 B2 - Document ID: US10370498B2 - Status: Granted - Kind: B2 - Application number: 15/309,052 - Filed: 2015-05-07 - Published: 2017-03-16 - Granted: 2019-08-06 - Earliest claimed: 2014-05-07 - Assignees: Lintec Corporation - Applicants: Lintec Corporation - Inventors: Masami Matsui; Mikihiro Kashio - Web page: https://patentgrep.com/patent/US10370498B2 ## CPC - C08G 77/26: nitrogen-containing groups - C08G 77/045: {containing less than 25 silicon atoms} - C08G 77/06: Preparatory processes - C08G 77/08: characterised by the catalysts used - C08K 5/54: Silicon-containing compounds {(C08K5/0091 takes precedence)} - C08K 5/5435: containing oxygen in a ring - C08K 5/5455: containing at least one [IMAGE cpc-sch-C08K-1012.gif] group - C08L 83/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen - C09J 11/06: organic - H10H 20/854: characterised by their material, e.g. epoxy or silicone resins - H10W 74/10: characterised by their shape or disposition - H10W 74/40: characterised by their materials - H10W 74/476: {Organic materials comprising silicon} - C08G 77/80: {Siloxanes having aromatic substituents, e.g. phenyl side groups} - 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) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - 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) - H10H: INORGANIC LIGHT-EMITTING SEMICONDUCTOR DEVICES HAVING POTENTIAL BARRIERS - H10W: GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10 ## Abstract The present invention is a curable polysilsesquioxane compound comprising at least one structural unit represented by CHR1X0-D-SiO3/2, the curable polysilsesquioxane compound having a 29Si nuclear magnetic resonance spectrum that has a first peak top within a range of −73 ppm or more and less than −65 ppm, has a second peak top within a range of −82 ppm or more and less than −73 ppm, and substantially does not have a peak within a range of −65 ppm or more and less than −55 ppm, and a method for producing the curable polysilsesquioxane compound, and a curable composition comprising the curable polysilsesquioxane compound and a silane coupling agent, and a cured product obtained by heating the curable composition, and a method for using the curable polysilsesquioxane compound or the curable composition, as an optical device-securing material. ## Claims ### Claim 1 A curable polysilsesquioxane compound comprising at least one structural unit represented by CHR1X0-D-SiO3/2, wherein R1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, X0 is a cyano group, or a group represented by OG (wherein G is a protecting group for a hydroxyl group), and D is a single bond, or a substituted or unsubstituted divalent organic group having 1 to 20 carbon atoms, the curable polysilsesquioxane compound having a 29Si nuclear magnetic resonance spectrum that has a first peak top within a range of −73 ppm or more and less than −65 ppm, has a second peak top within a range of −82 ppm or more and less than −73 ppm, and substantially does not have a peak within a range of −65 ppm or more and less than −55 ppm. ### Claim 2 (depends on 1) The curable polysilsesquioxane compound according to claim 1, further comprising at least one structural unit represented by R2SiO3/2, wherein R2 is an alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group. ### Claim 3 (depends on 1) The curable polysilsesquioxane compound according to claim 1, the curable polysilsesquioxane compound having the 29Si nuclear magnetic resonance spectrum in which a ratio of an integral value (P2) of a peak within the range of −82 ppm or more and less than −73 ppm to an integral value (P1) of a peak within the range of −73 ppm or more and less than −65 ppm is 60 to 90%. ### Claim 4 (depends on 1) The curable polysilsesquioxane compound according to claim 1, the curable polysilsesquioxane compound being a compound having a mass average molecular weight of 800 to 5,000. ### Claim 5 (depends on 1) A method for producing the curable polysilsesquioxane compound according to claim 1, the method comprising a step (I) that subjects at least one compound represented by a formula (1) to polycondensation in the presence of a polycondensation catalyst, CHR1X0-D-Si(OR3)3 (1) wherein R1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, X0 is a cyano group, or a group represented by OG (wherein G is a protecting group for a hydroxyl group), D is a single bond, or a substituted or unsubstituted divalent organic group having 1 to 20 carbon atoms, and R3 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, provided that a plurality of R3 are either identical to or different from each other. ### Claim 6 (depends on 2) A method for producing the curable polysilsesquioxane compound according to claim 2, the method comprising a step (I) that subjects a mixture that comprises at least one compound represented by a formula (1) and at least one compound represented by a formula (2) to polycondensation in the presence of a polycondensation catalyst, CHR1X0-D-Si(OR3)3 (1) wherein R1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, X0 is a cyano group, or a group represented by OG (wherein G is a protecting group for a hydroxyl group), D is a single bond, or a substituted or unsubstituted divalent organic group having 1 to 20 carbon atoms, and R3 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, provided that a plurality of R3 are either identical to or different from each other, R2Si(OR4)3 (2) wherein R2 is an alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group, and R4 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, provided that a plurality of R4 are either identical to or different from each other. ### Claim 7 (depends on 1) A curable composition comprising the curable polysilsesquioxane compound according to claim 1, and a silane coupling agent. ### Claim 8 (depends on 1) An optical device-securing material comprising: the curable polysilsesquioxane compound according to claim 1. ### Claim 9 (depends on 7) An optical device-securing material comprising: the curable composition according to claim 7. ### Claim 10 (depends on 1) The curable polysilsesquioxane compound according to claim 1, the divalent organic group is divalent hydrocarbon group. ### Claim 11 A curable polysilsesquioxane compound comprising at least one structural unit represented by CHR1X0-D-SiO3/2, wherein R1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, X0 is a cyano group, or a group represented by OG (wherein G is a protecting group for a hydroxyl group), and D is a single bond, or a substituted or unsubstituted divalent organic group having 1 to 20 carbon atoms, the curable polysilsesquioxane compound having a 29Si nuclear magnetic resonance spectrum that has a first peak top within a range of −73 ppm or more and less than −65 ppm, has a second peak top within a range of −82 ppm or more and less than −73 ppm, and a peak is not observed within the range of −65 ppm or more and less than −55 ppm, or, a ratio of the integral value of the peak within the range of −65 ppm or more and less than −55 ppm to the integral value of the peak within the range of −73 ppm or more and less than −65 ppm is less than 0.5% in the 29Si nuclear magnetic resonance spectrum. ### Claim 12 (depends on 11) The curable polysilsesquioxane compound according to claim 11, further comprising at least one structural unit represented by R2SiO3/2, wherein R2 is an alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group. ### Claim 13 (depends on 11) The curable polysilsesquioxane compound according to claim 11, the curable polysilsesquioxane compound having the 29Si nuclear magnetic resonance spectrum in which a ratio of an integral value (P2) of a peak within the range of −82 ppm or more and less than −73 ppm to an integral value (P1) of a peak within the range of −73 ppm or more and less than −65 ppm is 60 to 90%. ### Claim 14 (depends on 11) The curable polysilsesquioxane compound according to claim 11, the curable polysilsesquioxane compound being a compound having a mass average molecular weight of 800 to 5,000. ### Claim 15 (depends on 11) A method for producing the curable polysilsesquioxane compound according to claim 11, the method comprising a step (I) that subjects at least one compound represented by a formula (1) to polycondensation in the presence of a polycondensation catalyst, CHR1X0-D-Si(OR3)3 (1) wherein R1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, X0 is a cyano group, or a group represented by OG, wherein G is a protecting group for a hydroxyl group, D is a single bond, or a substituted or unsubstituted divalent organic group having 1 to 20 carbon atoms, and R3 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, provided that a plurality of R3 are either identical to or different from each other. ### Claim 16 (depends on 12) A method for producing the curable polysilsesquioxane compound according to claim 12, the method comprising a step (I) that subjects a mixture that comprises at least one compound represented by a formula (1) and at least one compound represented by a formula (2) to polycondensation in the presence of a polycondensation catalyst, CHR1X0-D-Si(OR3)3 (1) wherein R1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, X0 is a cyano group, or a group represented by OG (wherein G is a protecting group for a hydroxyl group), D is a single bond, or a substituted or unsubstituted divalent organic group having 1 to 20 carbon atoms, and R3 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, provided that a plurality of R3 are either identical to or different from each other, R2Si(OR4)3 (2) wherein R2 is an alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group, and R4 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, provided that a plurality of R4 are either identical to or different from each other. ### Claim 17 (depends on 11) A curable composition comprising the curable polysilsesquioxane compound according to claim 11, and a silane coupling agent. ### Claim 18 (depends on 11) An optical device-securing material comprising: the curable polysilsesquioxane compound according to claim 11. ### Claim 19 (depends on 17) An optical device-securing material comprising: the curable composition according to claim 17. ### Claim 20 (depends on 11) The curable polysilsesquioxane compound according to claim 11, the divalent organic group is divalent hydrocarbon group.