# US 9,434,818 B2 · Polymerizable compositions, cured products obtained therewith, and use of these materials > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,434,818 B2 - Document ID: US9434818B2 - Status: Granted - Kind: B2 - Application number: 13/980,501 - Filed: 2011-01-21 - Published: 2014-02-20 - Granted: 2016-09-06 - Earliest claimed: 2011-01-21 - Assignees: Fraundhofer-Gesellschaft zur Foerderung der angewandter Forschung e.V.; Nissan Chemical Industries, Ltd. - Applicants: Michael Popall; Ruth Houbertz-Krauss; Sebastien Cochet; Herbert Wolter; Kentaro Ohmori; Tetsuo Sato - Inventors: Michael Popall; Ruth Houbertz-Krauss; Sebastien Cochet; Herbert Wolter; Kentaro Ohmori; Tetsuo Sato - Web page: https://patentgrep.com/patent/US9434818B2 ## CPC - C08G 77/80: {Siloxanes having aromatic substituents, e.g. phenyl side groups} - C08F 230/085: {the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes} - C08G 77/20: containing silicon bound to unsaturated aliphatic groups - C08L 83/04: Polysiloxanes - C08F 2/24: with the aid of emulsifying agents - C08L 43/04: Homopolymers or copolymers of monomers containing silicon - C09D 183/04: Polysiloxanes - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - 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) ## Abstract [Problem] To provide a polymerizable composition having an excellent transparency in near-infrared wavelength and excellent heat resistance, and a method for producing the same. [Means of Solving the Problem] A polymerizable composition includes: a reactive silicone compound obtained by polycondensing a diaryl silicic acid compound of Formula [1] below with a silane compound, selected under compounds of Formula [2] and Formula [2b] below in the presence of an acid or a base; and (b) a compound having at least one polymerizable group selected from the group consisting of alkenyl group and (meth)acryl group, wherein Ar1 and Ar2 are independently a phenyl group optionally substituted with a C1-C6 alkyl group, and X is a group which can undergo a hydrolytic condensation reaction, and wherein Ar3 is naphthyl or anthracyl substituted with at least one group having a polymerizable double bond, or wherein Ar3 is phenyl substituted with at least one group having a polymerizable double bond other than vinyl, or is phenyl substituted with at least two groups having a polymerizable double bond. ## Claims ### Claim 1 A polymerizable composition comprising: (a) a reactive silicone compound obtained by polycondensing a diaryl silicic acid compound of Formula [1] below with a silane compound, selected under compounds of Formula [2] and Formula [2b] below in the presence of an acid or a base; wherein Ar1 and Ar2 are independently a phenyl group optionally substituted with a C1-C6 alkyl group, and X is a group which can undergo a hydrolytic condensation reaction, and wherein Ar3 is naphthyl or anthracyl substituted with at least one group having a polymerizable double bond, or wherein Ar3 is phenyl substituted with at least one group having a polymerizable double bond other than vinyl, or is phenyl substituted with at least two groups having a polymerizable double bond, and (b) a compound having at least one polymerizable alkenyl group of Formula [3], wherein R1 is a hydrogen atom or methyl group, L is a hydrogen atom, a C1-20 aliphatic hydrocarbon residue having m-valence that is optionally substituted with a phenyl group, a C1-20 aliphatic hydrocarbon residue having m-valence that optionally contains an ether bond, or a C1-20 polyvalent alcohol residue optionally containing an ether bond, Ar4 is a monocyclic or bicyclic or tricyclic, in each case aromatic hydrocarbon residue with n+1 valences, m is 1 and n is 2; or wherein R1 is a hydrogen atom or methyl group, L is a single bond, an oxygen atom, a C1-20 aliphatic hydrocarbon residue having m-valence that is optionally substituted with a phenyl group, a C1-20 aliphatic hydrocarbon residue having m-valence that optionally contains an ether bond, or a C1-20 polyvalent alcohol residue optionally containing an ether bond, Ar4 is a monocyclic or bicyclic or tricyclic, in each case aromatic hydrocarbon residue with n+1 valences, m is 2 or 3 and each of n is independently 1 or 2; with the proviso that when L is a single bond or an oxygen atom, m is 2. ### Claim 2 (depends on 1) The composition according to claim 1, wherein X is an alkoxy group having 1 to 10 carbon atoms. ### Claim 3 (depends on 2) The composition according to claim 2, wherein X is methoxy or ethoxy. ### Claim 4 (depends on 1) The composition of claim 1, wherein Ar4 is a phenyl residue. ### Claim 5 (depends on 4) The composition according to claim 4, wherein in the formula [3], n is 2. ### Claim 6 (depends on 1) The composition according to claim 1, wherein in the formula [3], L is a hydrogen atom, m is 1, and n is 2. ### Claim 7 (depends on 1) The composition according to claim 1, further comprising inorganic fine particles. ### Claim 8 (depends on 1) The composition according to claim 1, further comprising a solvent. ### Claim 9 (depends on 1) The composition according to claim 1, further comprising a polymerization initiator. ### Claim 10 (depends on 1) A cured product obtained by reacting a polymerizable double bond in the reactive silicone compound with a polymerizable group in the compound having at least one polymerizable group, in the composition according to claim 1. ### Claim 11 (depends on 1) Use of a material comprising a composition according to claim 1, for the preparation of components of optical devices, such as optical adhesives, transparent sealers, or cores or claddings of optical signal transmission devices, wherein said preparation includes curing the composition by reacting a polymerizable double bond in the reactive silicone compound with a polymerizable group in the compound having at least one polymerizable group, in the presence of a photo-radical initiator or a thermal radical initiator by light irradiation or heating. ### Claim 12 (depends on 1) Use of a material according to claim 1, for the preparation of optical interconnections of printed wiring boards wherein the optical interconnection is preferably a chip-to-chip optical interconnection, wherein said preparation includes curing the composition by reacting a polymerizable double bond in the reactive silicone compound with a polymerizable group in the compound having at least one polymerizable group, in the presence of a photo-radical initiator or a thermal radical initiator by light irradiation or heating. ### Claim 13 (depends on 10) A cured product as claimed in claim 10 which is a component of optical devices, preferably an optical adhesive, transparent sealer, or core or cladding of optical signal transmission devices. ### Claim 14 (depends on 10) A cured product as claimed in claim 10 which is a component of an optical interconnection of printed wiring boards wherein the optical interconnection is preferably a chip-to-chip optical interconnection.