# US 2014/0191168 A1 · Photochromic material > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0191168 A1 - Document ID: US20140191168A1 - Status: Published application - Kind: A1 - Application number: 13/629,975 - Filed: 2012-09-28 - Published: 2014-07-10 - Earliest claimed: 2010-01-06 - Assignees: Korea University Research and Business Foundation - Inventors: Dong Hoon CHOI - Web page: https://patentgrep.com/patent/US20140191168A1 ## CPC - C09B 19/00: Oxazine dyes - C09B 57/00: Other synthetic dyes of known constitution - C09K 9/02: Organic tenebrescent materials - G02B 5/23: Photochromic filters - C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS ## Abstract Photochromic dyes are disclosed. A photochromic dye can include a first photo-reactive group and a second photo-reactive group. A first photochromic reaction can be induced in the first photo-reactive group of the photochromic dye by radiation having a first wavelength, and a second photochromic reaction can be induced in the second photo-reactive group of the photochromic dye by radiation having a second wavelength. ## Claims ### Claim 1 A stable photochromic dye, comprising: at least two photo-reactive groups including: a first photo-reactive group configured to undergo a first reversible photochromic reaction in response to radiation having a first wavelength; and a second photo-reactive group configured to undergo a second reversible photochromic reaction in response to radiation having a second wavelength. ### Claim 2 (depends on 1) The photochromic dye of claim 1, wherein the at least two photo-reactive groups are coupled to one another by a non-conjugated linkage selected from the group consisting of C1-12 alkylene, C1-12 heteroalkylene, C1-12 alkoxy, C1-6 alkylenoxy, C1-6 alkylenedioxy, C1-6 phenyleneoxy, and C1-6 phenylenedioxy. ### Claim 3 (depends on 1) The photochromic dye of claim 1, wherein: the first photochromic reaction includes modification of a first conjugation system in the first photo-reactive group; and the second photochromic reaction includes modification of a second conjugation system in the second photo-reactive group. ### Claim 4 (depends on 1) The photochromic dye of claim 1, wherein the first photo-reactive group and the second photo-reactive group have different respective absorption maxima. ### Claim 5 (depends on 4) The photochromic dye of claim 4, wherein a difference of absorption maxima between the first photo-reactive group and the second photo-reactive group photochromic is greater than or equal to about 50 nm. ### Claim 6 (depends on 1) The photochromic dye of claim 1, wherein the at least two photo-reactive groups include at least one compound independently selected from the group consisting of a spiropyran compound, a spirooxazine compound, a diarylethene compound, and a fulgide compound. ### Claim 7 A stable photochromic dye, comprising: at least two photo-reactive groups including: a first photo-reactive group including a first conjugation system reversibly formed in response to radiation having a first wavelength, the first conjugation system exhibiting a first conjugation bond length; and a second photo-reactive group including a second conjugation system reversibly formed in response to radiation having a second wavelength, the second conjugation system exhibiting a second conjugation bond length that is longer than the first conjugation bond length. ### Claim 8 (depends on 7) The photochromic dye of claim 7, wherein the first photo-reactive group and the second photo-reactive group exhibit different respective absorption maxima. ### Claim 9 (depends on 7) The photochromic dye of claim 7, wherein the first photo-reactive group exhibits an absorption maximum of about 250 nm to about 350 nm, and the second photo-reactive group exhibits an absorption maximum of about 400 nm to about 500 nm. ### Claim 10 (depends on 7) The photochromic dye of claim 7, wherein the at least two photo-reactive groups include at least one independently selected from the group consisting of a spiropyran compound, a spirooxazine compound, a diarylethene compound and a fulgide compound. ### Claim 11 (depends on 7) The photochromic dye of claim 7, wherein the at least two photo-reactive groups include at least one member independently selected from the group consisting of thiophene perfluoropentenes, benzothiophene perfluoropentenes, benzothiophene maleicanhydrides, benzothiophene cyanoethenes, and benzothiophene sulfone perfluoropentenes. ### Claim 12 (depends on 7) The photochromic dye of claim 7, wherein the at least two photo-reactive groups include at least one member independently selected from the group consisting of 3-furyl, 3-thienyl fulgides, and fulgimides. ### Claim 13 A stable photochromic composition, comprising: at least one material selected from the group consisting of a polymer, an oligomer, and a monomer; and at least one photochromic dye incorporated into at least a portion of the at least one material, the at least one photochromic dye having at least two photo-reactive groups that are coupled to one another, wherein the at least one photochromic dye includes: a first photo-reactive group configured to undergo a first reversible photochromic reaction in response to radiation having a first wavelength; and a second photo-reactive group configured to undergo a second reversible photochromic reaction in response to radiation having a second wavelength. ### Claim 14 (depends on 13) The photochromic composition of claim 13, wherein the at least one material includes at least one polymer selected from the group consisting of polyacrylates, polymethacrylates, polyalkylmethacrylates, polyoxy(alkylene methacrylates), poly(alkoxylated phenol methacrylates), cellulose acetate, cellulose triacetate, cellulose acetate propionate, cellulose acetate butyrate, poly(vinyl acetate), poly(vinyl alcohol), poly(vinyl chloride), poly(vinylidene chloride), poly(vinylpyrrolidone), poly((meth)acrylamide), poly(dimethyl acrylamide), poly(hydroxyethyl methacrylate), poly((meth)acrylic acid), thermoplastic polycarbonates, polyesters, polyurethanes, polythiourethanes, poly(ethylene terephthalate), polystyrene, poly(alpha methylstyrene), copoly(styrene-methylmethacrylate), copoly(styrene-acrylonitrile), polyvinylbutyral, and polymers of members of the group consisting of polyol(allyl carbonate)monomers, mono-functional acrylate monomers, mono-functional methacrylate monomers, polyfunctional acrylate monomers, polyfunctional methacrylate monomers, diethylene glycol dimethacrylate monomers, diisopropenyl benzene monomers, alkoxylated polyhydric alcohol monomers, and diallylidene pentaerythritol monomers. ### Claim 15 (depends on 13) The photochromic composition of claim 13, wherein the at least one material includes at least a second material having a glass transition temperature less than about 0° C. ### Claim 16 (depends on 15) The photochromic composition of claim 15, wherein the at least one photochromic dye is coupled to the second material. ### Claim 17 (depends on 13) The photochromic composition of claim 13, wherein the at least one material includes at least one polysiloxane or at least one polyacrylate having a glass transition temperature less than about 0° C. ### Claim 18 (depends on 13) The photochromic composition of claim 13, wherein the first photo-reactive group and the second photo-reactive group are coupled to one another by a non-conjugated linkage selected from the group consisting of C1-12 alkylene, C1-12 heteroalkylene, C1-6 alkylenoxy, and C1-6 alkylenedioxy. ### Claim 19 (depends on 13) The photochromic composition of claim 13, wherein the at least two photo-reactive groups include at least one compound independently selected from the group consisting of a spiropyran compound, a spirooxazine compound, a diarylethene compound, and a fulgide compound. ### Claim 20 (depends on 7) The photochromic composition of claim 7, wherein the at least two photo-reactive groups include at least one member independently selected from the group consisting of thiophene perfluoropentenes, benzothiophene perfluoropentenes, benzothiophene maleicanhydrides, benzothiophene cyanoethenes, benzothiophene sulfone perfluoropentenes, 3-furyl, 3-thienyl fulgides, and fulgimides.