# US 10,308,750 B2 · Polymerizable composition containing reactive silsesquioxane compound > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,308,750 B2 - Document ID: US10308750B2 - Status: Granted - Kind: B2 - Application number: 15/122,308 - Filed: 2015-02-26 - Published: 2016-12-22 - Granted: 2019-06-04 - Earliest claimed: 2014-02-28 - Assignees: Nissan Chemical Industries, Ltd. - Applicants: Nissan Chemical Industries, Ltd. - Inventors: Kentaro Ohmori; Takehiro Nagasawa - Web page: https://patentgrep.com/patent/US10308750B2 ## CPC - C08F 290/068: {Polysiloxanes} - C08F 230/08: containing silicon - C08G 77/20: containing silicon bound to unsaturated aliphatic groups - C08L 83/04: Polysiloxanes - C08L 83/10: Block- or graft-copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C08L51/08, C08L53/00) - G02B 1/041: {Lenses} - C08G 77/442: containing vinyl polymer sequences - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS ## Abstract A polymerizable composition that is suitable to produce a molded product that can suppress cracking and dimensional change caused by a high-temperature heat history with a high refractive index of a cured product maintained. A polymerizable composition including (a) 100 parts by mass of the specific reactive silsesquioxane compound, (b) 10 to 500 parts by mass of the specific fluorene compound, a cured product obtained by the polymerizable composition and a material for a high-refractive index resin lens including the polymerizable composition. ## Claims ### Claim 1 A polymerizable composition comprising a chain transfer agent in an amount of from 0.01 to 20 parts by mass, relative to a total amount of 100 parts by mass of polymerizable components in the polymerizable composition, the polymerizable components including: (a) 100 parts by mass of reactive silsesquioxane compound obtained by polycondensation of an alkoxy silicon compound A of Formula [1] with an alkoxy silicon compound B of Formula [2] in the presence of an acid or a base, and (b) 10 to 500 parts by mass of a fluorene compound of Formula [3], where the Formulae [1], [2] and [3] are as follows: Ar1—Si(OR1)3 [1] wherein Ar1 is a phenyl group having at least one group having a polymerizable double bond or a naphthyl group having at least one group having a polymerizable double bond, and R1 is a methyl group or an ethyl group; Ar2—Si(OR2)3 [2] wherein Ar2 is a phenyl group optionally substituted by a C1-6 alkyl group, or a naphthyl group optionally substituted by a C1-6 alkyl group, and R2 is a methyl group or an ethyl group; and wherein R3 and R4 are each independently a hydrogen atom or a methyl group, L1 and L2 are each independently a phenylene group optionally having a substituent, L3 and L4 are each independently a C1-6 alkylene group, and m and n are 0 or a positive integer such that m+n is 0 to 40. ### Claim 2 (depends on 1) The polymerizable composition according to claim 1, further comprising 10 to 100 parts by mass of (c) (meth)acrylate compound that is different from the fluorene compound. ### Claim 3 (depends on 2) The polymerizable composition according to claim 2, wherein the (c) (meth)acrylate compound is a mono(meth)acrylate compound having an aromatic group. ### Claim 4 (depends on 1) The polymerizable composition according to claim 1, wherein the (a) reactive silsesquioxane compound is a reactive silsesquioxane compound obtained by polycondensation of a compound of Formula [1a] with a compound of Formula [2a] in the presence of an acid or a base, where the Formulae [1a] and [2a] are as follows: wherein R1 has the same meaning as described above; and wherein R2 has the same meaning as described above. ### Claim 5 (depends on 1) The polymerizable composition according to claim 1, wherein a cured product obtained from the composition has an Abbe number of 32 or less. ### Claim 6 (depends on 1) A cured product obtained by polymerization of the polymerizable composition according to claim 1. ### Claim 7 (depends on 1) A material for a high-refractive index resin lens that comprises the polymerizable composition according to claim 1. ### Claim 8 A method for producing a molded body comprising the steps of: charging a space between a support and a mold with a polymerizable composition; exposing the charged composition to light resulting in photopolymerization; releasing a photopolymerized product on the support from the mold; and heating the photopolymerized product together with the support; wherein the polymerizable composition comprises: (a) 100 parts by mass of reactive silsesquioxane compound obtained by polycondensation of an alkoxy silicon compound A of Formula [1] with an alkoxy silicon compound B of Formula [2] in the presence of an acid or a base, and (b) 10 to 500 parts by mass of a fluorene compound of Formula [3], where the Formulae [1], [2] and [3] are as follows: Ar1—Si(OR1)3 [1] wherein Ar1 is a phenyl group having at least one group having a polymerizable double bond or a naphthyl group having at least one group having a polymerizable double bond, and R1 is a methyl group or an ethyl group; Ar2—Si(OR2)3 [2] wherein Ar2 is a phenyl group optionally substituted by a C1-6 alkyl group, or a naphthyl group optionally substituted by a C1-6 alkyl group, and R2 is a methyl group or an ethyl group; and wherein R3 and R4 are each independently a hydrogen atom or a methyl group, L1 and L2 are each independently a phenylene group optionally having a substituent, L3 and L4 are each independently a C1-6 alkylene group, and m and n are 0 or a positive integer such that m+n is 0 to 40. ### Claim 9 (depends on 8) The method according to claim 8, wherein the molded body is a lens for a camera module. ### Claim 10 A polymerizable composition comprising (a) 100 parts by mass of reactive silsesquioxane compound, the 100 parts by mass of reactive silsesquioxane compound obtained by a reaction consisting of a polycondensation of an alkoxy silicon compound A of Formula [1] with an alkoxy silicon compound B of Formula [2] in the presence of an acid or a base, and optionally a solvent, and (b) 10 to 500 parts by mass of a fluorene compound of Formula [3], where the Formulae [1], [2] and [3] are as follows: Ar1—Si(OR1)3 [1] wherein Ar1 is a phenyl group having at least one group having a polymerizable double bond or a naphthyl group having at least one group having a polymerizable double bond, and R1 is a methyl group or an ethyl group; Ar2—Si(OR2)3 [2] wherein Ar2 is a phenyl group optionally substituted by a C1-6 alkyl group, or a naphthyl group optionally substituted by a C1-6 alkyl group, and R2 is a methyl group or an ethyl group; and wherein R3 and R4 are each independently a hydrogen atom or a methyl group, L1 and L2 are each independently a phenylene group optionally having a substituent, L3 and L4 are each independently a C1-6 alkylene group, and m and n are 0 or a positive integer such that m+n is 0 to 40. ### Claim 11 (depends on 10) The polymerizable composition according to claim 10, further comprising 10 to 100 parts by mass of (c) (meth)acrylate compound that is different from the fluorene compound. ### Claim 12 (depends on 11) The polymerizable composition according to claim 11, wherein the (c) (meth)acrylate compound is a mono(meth)acrylate compound having an aromatic group. ### Claim 13 (depends on 10) The polymerizable composition according to claim 10, wherein the (a) reactive silsesquioxane compound is a reactive silsesquioxane compound obtained by polycondensation of a compound of Formula [1a] with a compound of Formula [2a] in the presence of an acid or a base, where the Formulae [1a] and [2a] are as follows: wherein R1 has the same meaning as described above; and wherein R2 has the same meaning as described above. ### Claim 14 (depends on 10) The polymerizable composition according to claim 10, wherein a cured product obtained from the composition has an Abbe number of 32 or less. ### Claim 15 (depends on 10) A cured product obtained by polymerization of the polymerizable composition according to claim 10. ### Claim 16 (depends on 10) A material for a high-refractive index resin lens that comprises the polymerizable composition according to claim 10.