# US 9,040,647 B2 · Photochromic material > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,040,647 B2 - Document ID: US9040647B2 - Status: Granted - Kind: B2 - Application number: 13/514,620 - Filed: 2010-11-30 - Published: 2012-09-27 - Granted: 2015-05-26 - Earliest claimed: 2009-12-11 - Assignees: Mitsubishi Gas Chemical Company, Inc.; Jiro Abe - Applicants: Jiro Abe; Atsuhiro Tokita; Takeru Horino; Toyoji Oshima; Atsushi Kimoto - Inventors: Jiro Abe; Atsuhiro Tokita; Takeru Horino; Toyoji Oshima; Atsushi Kimoto - Web page: https://patentgrep.com/patent/US9040647B2 ## CPC - G03C 1/73: containing organic compounds - C08F 20/02: Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof - C08F 20/34: Esters containing nitrogen {, e.g. N,N-dimethylaminoethyl (meth)acrylate} - C08F 20/36: containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate} - C09K 9/02: Organic tenebrescent materials - G03C: PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES (for photomechanical purposes G03F); PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY (photographic processes characterised by the use or manipulation of apparatus classifiable per se in subclass G03B, see G03B; photomechanical production of textured or patterned surfaces G03F; electrophotography, magnetography G03G) - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract Provided are: a method for controlling the decoloration reaction rate and color density of a fast light-modulating material to levels suitable for practical use; and a fast light-modulating material having a decoloration reaction rate and a color density which are suitable for practical use. A polymer obtained by polymerizing a paracyclophane-bridged hexaarylbisimidazole compound having a radical-polymerizable group, and a copolymer obtained by copolymerizing the compound with a (meth)acrylic acid compound or a sensitizer having a radical-polymerizable group can achieve controlled decoloration reaction rates, photosensitivity and color tones. ## Claims ### Claim 1 A homopolymer of a photochromic molecule represented by the following general formula (III): wherein, in the structural formula, A is a photochromic molecule having the above-mentioned structure, R1 is hydrogen or a methyl group, and n is an integer of 2 to 20, wherein R3 is a methoxy group and is bound to the para-position, and R4 to R7 are all methoxy groups and are bound to the meta-positions and para-positions. ### Claim 2 A block or random copolymer of a photochromic molecule represented by the following general formula (IV): wherein, in the structural formula, A is a photochromic molecule having the above-mentioned structure, R1, R1-2 and R1-3 are each independently hydrogen or a methyl group, R3 to R7 are each independently hydrogen or an alkoxy group, and n is an integer of 2 to 20. ### Claim 3 A block or random copolymer of a photochromic molecule represented by the following general formula (V): wherein, in the structural formula, A is a photochromic molecule having the above-mentioned structure, B is a photosensitizing compound having the above-mentioned structure, R1, R1-2, R1-3 and R1-4 are each independently hydrogen or a methyl group, R3 to R8 are each independently hydrogen or an alkoxy group, m is an integer of 2 to 20, and n is an integer of 2 to 20. ### Claim 4 A block or random copolymer of a photochromic molecule represented by the following general formula (VI): wherein, in the structural formula, A is a photochromic molecule having the above-mentioned structure, B is a photosensitizing compound having the above-mentioned structure, R1 and R1-2 are each independently hydrogen or a methyl group, R3 to R8 are each independently hydrogen or an alkoxy group, m is an integer of 2 to 20, and n is an integer of 2 to 20. ### Claim 5 A block or random copolymer of a photochromic molecule represented by the following general formula (VII): wherein, in the structural formula, A and A2 are photochromic molecules having the above-mentioned structures, R1 and R1-2 are each independently hydrogen or a methyl group, R3 and R9 are each independently hydrogen or an alkoxy group, R4 to R7 are hydrogens, R10 to R13 are alkoxy groups, m is an integer of 2 to 20, and n is an integer of 2 to 20. ### Claim 6 (depends on 2) The copolymer of a photochromic molecule according to claim 2, wherein R3 to R7 are each independently hydrogen or a methoxy group. ### Claim 7 (depends on 6) The copolymer of a photochromic molecule according to claim 6, wherein R3 is a methoxy group and is bound to the para-position, and R4 to R7 are all hydrogens. ### Claim 8 (depends on 6) The copolymer of a photochromic molecule according to claim 6, wherein R3 is a methoxy group and is bound to the para-position, and R4 to R7 are all methoxy groups and are bound to the meta-positions and para-positions. ### Claim 9 (depends on 3) The copolymer of a photochromic molecule according to claim 3, wherein R3 to R8 are each independently hydrogen or a methoxy group. ### Claim 10 (depends on 9) The copolymer of a photochromic molecule according to claim 9, wherein R3 and R8 are methoxy groups and are bound to the para-positions, and R4 to R7 are all hydrogens. ### Claim 11 (depends on 9) The copolymer of a photochromic molecule according to claim 9, wherein R3 and R8 are methoxy groups and are bound to the para-positions, and R4 to R7 are all methoxy groups and are bound to the meta-positions and para-positions. ### Claim 12 (depends on 4) The copolymer of a photochromic molecule according to claim 4, wherein R3 to R8 are each independently hydrogen or a methoxy group. ### Claim 13 (depends on 12) The copolymer of a photochromic molecule according to claim 12, wherein R3 and R8 are methoxy groups and are bound to the para-positions, and R4 to R7 are all hydrogens. ### Claim 14 (depends on 12) The copolymer of a photochromic molecule according to claim 12, wherein R3 and R8 are methoxy groups and are bound to the para-positions, and R4 to R7 are all methoxy groups and are bound to the meta-positions and para-positions. ### Claim 15 (depends on 5) The copolymer of a photochromic molecule according to claim 5, wherein R3 and R9 are methoxy groups and are bound to the para-positions, R4 to R7 are all hydrogens, and R10 to R13 are methoxy groups and are bound to the meta-positions and para-positions. ### Claim 16 (depends on 1) A method for decreasing the decoloration reaction rate of a photochromic material, comprising polymerizing a photochromic molecule to form the homopolymer according to claim 1. ### Claim 17 (depends on 5) A method for controlling the photosensitivity and color tone of a photochromic material, by changing the component ratio of the photochromic molecule having the structure A and the photochromic molecule having the structure A2 in the copolymer of photochromic molecules according to claim 5. ### Claim 18 (depends on 2) A method for decreasing the decoloration reaction rate of a photochromic material, comprising polymerizing a photochromic molecule to form the copolymer according to claim 2. ### Claim 19 (depends on 3) A method for decreasing the decoloration reaction rate of a photochromic material, comprising polymerizing a photochromic molecule to form the copolymer according to claim 3. ### Claim 20 (depends on 4) A method for decreasing the decoloration reaction rate of a photochromic material, comprising polymerizing a photochromic molecule to form the copolymer according to claim 4. ### Claim 21 (depends on 5) A method for decreasing the decoloration reaction rate of a photochromic material, comprising polymerizing a photochromic molecule to form the copolymer according to claim 5. ### Claim 22 (depends on 15) A method for controlling the photosensitivity and color tone of a photochromic material, by changing the component ratio of the photochromic molecule having the structure A and the photochromic molecule having the structure A2 in the copolymer of photochromic molecules according to claim 15.