Spiropyran Dye Or Dye Former Patents (Class 430/345)
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Patent number: 11519859Abstract: Provided are novel rhodol-based compounds, the preparation method thereof, and use thereof in Tl+ flux assays. The fluorescent thallium ion sensor compounds have a rhodol fluorophore attached to an amino dicarboxylic acid metal binding moiety. The compounds are prepared in the “pro-dye” form, with the rhodol oxygen and the carboxylic acids of the metal binding unit masked by protecting groups. The disclosed compounds may be used as more red-shifted and less pH-sensitive variants of Thallos.Type: GrantFiled: April 9, 2019Date of Patent: December 6, 2022Assignee: Vanderbilt UniversityInventors: Charles David Weaver, Brendan F. Dutter, Gary A. Sulikowski
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Patent number: 9748576Abstract: A polymer including a first repeating unit including at least one carboxyl group substituted with a cation and a second repeating unit including at least one carboxyl group substituted with a moiety containing a dihydroxyphenyl group.Type: GrantFiled: January 5, 2015Date of Patent: August 29, 2017Assignee: SAMSUNG ELECTRONICS CO., LTD.Inventors: Seungsik Hwang, Jaeman Choi, Yeonji Chung
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Patent number: 9494592Abstract: Reaction-based fluorescent probes are provided which detect, for example, biologically important sulfane sulfur species (persulfide, polysulfide, and elemental sulfur) in, for example, complex and living systems. The probes are high in selectivity and sensitivity to sulfane sulfurs. Moreover, probes are suitable for bioimaging sulfane sulfurs in living cells.Type: GrantFiled: April 11, 2014Date of Patent: November 15, 2016Assignee: Washington State UniversityInventors: Ming Xian, Wei Chen
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Patent number: 8343715Abstract: A method for producing a photochromic polyester, the method including: a) providing a reaction solution having at least one ester monomer, a photochromic compound having or functionalized to have at least one hydroxyl group, and a metal-free catalyst; b) reacting the at least one ester monomer and the photochromic compound using the metal-free catalyst to produce a polymeric product, where the polymeric product has a photochromic polyester; and c) separating the polymeric product from the reaction solution. A photochromic polyester includes a photochromic compound covalently linked to a polyester and the polyester is obtained by polymerizing a lactone.Type: GrantFiled: November 3, 2010Date of Patent: January 1, 2013Assignee: Xerox CorporationInventors: Santiago Faucher, Gabriel Iftime, Kentaro Morimitsu, Adela Goredema, Jordan H. Wosnick
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Patent number: 8076058Abstract: Compositions and methods for production of color images which are developable at desired wavelengths are disclosed and described. The color forming composition can include a color former which is a spiro dye. The color forming composition can include a radiation antenna admixed with or in thermal contact with the color former. The color forming composition can also be optimized for development using electromagnetic radiation having a selected development wavelength. The color forming compositions are useful in forming images on a wide variety of substrates such as optical disks.Type: GrantFiled: September 30, 2004Date of Patent: December 13, 2011Assignee: Hewlett-Packard Development Company, L.P.Inventor: Makarand P. Gore
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Patent number: 7498122Abstract: A solvent-less process for producing a transient document which is capable of self-erasing, wherein the solvent-less process includes a) heating and reacting a photochromic compound and a polymer to form a coating composition, and b) coating the coating composition onto an image-receiving side of a transient document substrate, and further an image forming method using the same solvent-less process and including (i) providing a reimageable medium of a substrate and a photochromic material, wherein the medium is capable of exhibiting a color contrast and an absence of the color contrast; (ii) exposing the medium to an imaging light corresponding to a predetermined image to result in an exposed region and a non-exposed region, wherein the color contrast is present between the exposed region and the non-exposed region to allow a temporary image corresponding to the predetermined image to be visible for a visible time; (iii) subjecting the temporary image to an indoor ambient condition for an image erasing time tType: GrantFiled: August 30, 2005Date of Patent: March 3, 2009Assignee: Xerox CorporationInventors: Gabriel Iftime, Peter M. Kazmaier, Naveen Chopra, San-Ming Yang, Raymond W. Wong
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Patent number: 7432027Abstract: A reimageable medium including a transparent substrate having a first side and any opposing side, a protective layer and an imaging layer. The protective layer can be located on the first side of the transparent substrate and the imaging layer can be located on the opposing side of the transparent substrate.Type: GrantFiled: March 30, 2005Date of Patent: October 7, 2008Assignee: Xerox CorporationInventors: Naveen Chopra, Gabriel Iftime, Peter M. Kazmaier
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Patent number: 7410750Abstract: A multicolored display and process for forming such a display is provided. The multicolored display includes marking particles comprising a mixture of photochromic materials. The photochromic materials each exhibit a first “invisible” photochromic state at a first absorption spectrum and at least a second “visible” photochromic state at a second absorption spectrum. The second “visible” photochromic state of each photochromic material produces a different color relative to the other photochromic materials. In embodiments, the marking particles include a mixture of a spiropyran material and a dithienylethene material.Type: GrantFiled: June 30, 2004Date of Patent: August 12, 2008Assignee: Xerox CorporationInventors: Naveen Chopra, Daniel A. Foucher, Raj D. Patel
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Patent number: 7381506Abstract: An image forming medium includes a substrate and a mixture including a photochromic material and a solvent wherein the mixture is coated on the substrate, such that the photochromic material exhibits a reversible homogeneous-heterogeneous transition between a colorless state and a colored state in the solvent.Type: GrantFiled: September 8, 2005Date of Patent: June 3, 2008Assignee: Xerox CorporationInventors: Gabriel Iftime, Naveen Chopra, Peter M. Kazmaier
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Patent number: 7326526Abstract: In various aspects, the present invention provides substantially monolayer thick molecular films with photoresponsive wettability, the molecules of said films comprising a photochromic molecule coordinated to a metal atom, which is coordinated to an organic tethering molecule, surface coupling group, or both, having a group for attachment to a surface of a substrate. In various aspects, the present inventions also provide photochromic articles comprising said films, methods of forming said films, and methods of manufacturing photochromic articles using said films. In various embodiments, provided are molecular films where the photoconversion between configurations of the photochromic molecule is substantially reversible by irradiation with light. In various embodiments, provided are films where the photoconversion is substantially irreversible by irradiation with light.Type: GrantFiled: December 15, 2004Date of Patent: February 5, 2008Assignee: Worcester Polytechnic InstituteInventors: W. Grant McGimpsey, John C. MacDonald
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Patent number: 7316875Abstract: An image forming medium including at least a polymer and a photochromic compound such as spiropyran embedded in the polymer, wherein spiropyran molecules of the spiropyran compound are chelated by a cation.Type: GrantFiled: May 6, 2005Date of Patent: January 8, 2008Assignee: Xerox CorporationInventors: Gabriel Iftime, Peter M. Kazmaier
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Patent number: 7300727Abstract: An image forming method composed of: (a) providing a reimageable medium composed of a substrate and a photochromic material, wherein the medium is capable of exhibiting a color contrast and an absence of the color contrast; (b) exposing the medium to an imaging light corresponding to a predetermined image to result in an exposed region and a non-exposed region, wherein the color contrast is present between the exposed region and the non-exposed region to allow a temporary image corresponding to the predetermined image to be visible for a visible time; (c) subjecting the temporary image to an indoor ambient condition for an image erasing time to change the color contrast to the absence of the color contrast to erase the temporary image without using an image erasure device; and (d) optionally repeating procedures (b) and (c) a number of times to result in the medium undergoing a number of additional cycles of temporary image formation and temporary image erasure.Type: GrantFiled: April 29, 2004Date of Patent: November 27, 2007Assignee: Xerox CorporationInventors: Peter M. Kazmaier, Gabriel Iftime
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Patent number: 7229740Abstract: An image forming medium includes a substrate and an imaging layer including a photochromic material and a polymer binder coated on the substrate, where the photochromic material exhibits a reversible homogeneous-heterogeneous transition between a colorless state and colored state in the polymer binder.Type: GrantFiled: September 8, 2005Date of Patent: June 12, 2007Assignee: Xerox CorporationInventors: Gabriel Iftime, Peter M. Kazmaier
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Patent number: 7214456Abstract: An reimageable medium composed of: a substrate; and a photochromic material, wherein the medium is capable of exhibiting a color contrast and an absence of the color contrast, wherein the medium has a characteristic that when the medium exhibits the absence of the color contrast and is then exposed to an imaging light corresponding to a predetermined image to result in an exposed region and a non-exposed region, the color contrast is present between the exposed region and the non-exposed region to form a temporary image corresponding to the predetermined image that is visible for a visible time, wherein the medium has a characteristic that when the temporary image is exposed to an indoor ambient condition for an image erasing time, the color contrast changes to the absence of the color contrast to erase the temporary image in all of the following: (i) when the indoor ambient condition includes darkness at ambient temperature, (ii) when the indoor ambient condition includes indoor ambient light at ambient tempType: GrantFiled: April 29, 2004Date of Patent: May 8, 2007Assignee: Xerox CorporationInventors: Gabriel Iftime, Naveen Chopra, Peter M. Kazmaier
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Patent number: 7166420Abstract: A protective, switchable layer adapted for use in transient imageable documents is disclosed. The protective layer can be disposed on an underlying photochromic layer and enables writing or imaging the underlying layer. The protective layer prevents unintentional writing on the photochromic layer, such as can otherwise occur from exposure to certain wavelengths of light.Type: GrantFiled: May 27, 2005Date of Patent: January 23, 2007Assignee: Xerox CorporationInventors: Naveen Chopra, Hadi Mahabadi, Peter M. Kazmaier, Gabriel Iftime
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Patent number: 6746830Abstract: A silver halide photosensitive material having a substrate, a heat-responsive-discolorable coloring layer and a photosensitive layer coated thereon and having a silver halide, dye-providing compound and a binder, the heat-responsive-discolorable coloring layer containing a heat-responsive-discolorable coloring composition, which is colored at a temperature lower than its discoloration initiation temperature (T) of 60 to 200° C.; which is substantially discolored at a temperature equal to or higher than T; and which does not recover its color once discolored, even when its temperature is lowered to a temperature lower than T again, and the heat-responsive-discolorable coloring composition containing a polymer having a glass transition temperature of 60 to 200° C.Type: GrantFiled: October 25, 2002Date of Patent: June 8, 2004Assignee: Fuji Photo Film Co., Ltd.Inventors: Jun Arakawa, Takahiro Ishizuka
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Publication number: 20030175612Abstract: A process for forming photosensitive microcapsules having discrete capsule walls comprising the steps of forming an emulsion of an oily core material in a continuous aqueous phase containing a carboxyvinyl polymer and enwrapping particles of the oily core material in an amine-formaldehyde condensation product produced by in situ condensation of an amine and formaldehyde wherein the carboxyvinyl polymer comprises a crosslinked polymer of acrylic acid is disclosed.Type: ApplicationFiled: March 15, 2002Publication date: September 18, 2003Inventors: Ibrahim Katampe, Alexander Y. Polykarpov, Joseph C. Camillus
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Publication number: 20030099910Abstract: The present invention relates to a photochromic spirobenzopyran compound of the formula (1) and its derivatives, a spirobenzopyran group having unsaturated terminal groups, a polymer prepared therefrom, a method for the production thereof, a composition comprising said spirobenzopyran or said spirobenzopyran group-containing polymer and a photochromic switch film using the same: 1Type: ApplicationFiled: August 24, 1999Publication date: May 29, 2003Inventors: EUN-KYOUNG KIM, YUN-KI CHOI, SAM-ROK KEUM
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Patent number: 6521753Abstract: The present invention provides indolinospiropyran compounds and methods for their manufacture, which compounds are useful as photochromic compounds. The compounds of the invention are substituted on the indole ring with succinimide, which substitution permits ring opening of the succinimide and modulation of the bulk and photochromic properties of the compounds. The compounds may be conveniently prepared using the solid phase organic synthesis of the invention.Type: GrantFiled: May 31, 2000Date of Patent: February 18, 2003Assignee: Johnson & Johnson Vision Care, Inc.Inventors: Erick M. Carreira, Weili Zhao
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Patent number: 6398981Abstract: The present invention is concerned with photopolymer materials sensitive to infrared, near infrared, red and green light radiation for initiating polymerization and to applications of such photopolymer, like holographic polymer dispersed liquid crystal (H-PDLC) or reversible dye doped photopolymer (RDDP) materials, for making optical devices. The invention relates to holographic polymer dispersed liquid crystal and reversible dye materials having improved electrical and optical switching properties.Type: GrantFiled: February 14, 2000Date of Patent: June 4, 2002Assignee: Universite LavalInventors: Tigran Galstian, Amir Tork
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Publication number: 20020006589Abstract: Photochromatic compounds in the solid state belonging to the group of chromenes and spiro-pyrans, having general formula (I): 1Type: ApplicationFiled: March 6, 2001Publication date: January 17, 2002Inventors: Vincenzo Malatesta, Jonathan Hobley, William Giroldini, Maria Lucia Wis
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Patent number: 6162931Abstract: The family of dyes of the invention are fluoresceins and rhodols that are directly substituted on one or more aromatic carbons by fluorine. These fluorine-substituted fluorescent dyes possess greater photostability and have lower sensitivity to pH changes in the physiological range of 6-8 than do non-fluorinated dyes, exhibit less quenching when conjugated to a substance, and possess additional advantages. The dyes of the invention are useful as detectable tracers and for preparing conjugates of organic and inorganic substances.Type: GrantFiled: April 12, 1996Date of Patent: December 19, 2000Assignee: Molecular Probes, Inc.Inventors: Kyle R. Gee, Martin Poot, Dieter H. Klaubert, Wei-Chuan Sun, Richard P. Haugland, Fei Mao
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Patent number: 6071352Abstract: According to a first aspect of this invention, it is assumed that the recording is carried out on the recording medium by a non-catalyst-containing recording agent and a liquid-state catalyst is coated on the recording medium at the time of erasing processing and subsequently the heating and irradiation of near infrared rays are carried out as the erasing processing. Also, according to a second aspect of this invention, it is assumed that the recording is carried out on the recording medium by a catalyst-containing recording agent and, at the erasing processing time, the heating and irradiation of the recording agent are simultaneously carried out using a thermal emission and near IR irradiation source such as a halogen lamp.Type: GrantFiled: April 15, 1994Date of Patent: June 6, 2000Assignee: Fujitsu Isotec LimitedInventors: Masaru Sugie, Chiaki Sekioka, Yoshiaki Yanagida, Hisashi Uemura, Masayuki Kubota, Hirobumi Haga
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Patent number: 5811503Abstract: Describes polymerizable organic compositions of from about 30 to 95 weight percent of a first monomer component which is an alkoxylated diol, e.g., alkoxylated bisphenol, having acrylate or methacrylate groups, i.e., dimethacrylate of bisphenol A having an average of 1 to 4 ethoxy units, and from about 5 to 70 weight percent of a second monomer component which is an alkoxylated diol, e.g., alkoxylated bisphenol, having acrylate or methacrylate groups, i.e., dimethacrylate of bisphenol A having 25 to 70 ethoxy units. Optionally there may also be present from about 0 to 65 weight percent of at least one monomer component which is selected from: (i) a monoethylenically unsaturated monomer that is polymerizable by free radical initiation; (ii) a bis?(meth)acryloyl-terminated!polyethylene glycol monomer; and (iii) a monomer having at least three terminal ethylenically-unsaturated groups. Substantially completely cured polymerizates prepared from such compositions may be used to prepare photochromic articles, e.g.Type: GrantFiled: November 27, 1996Date of Patent: September 22, 1998Assignee: PPG Industries, Inc.Inventors: Robert D. Herold, Randy E. Daughenbaugh, Charles R. Wiedrich
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Patent number: 5782969Abstract: Present invention provides ionic spiropyran compounds having a C10-C22 alkyl group or groups at the 1'- and/or 8-positions of 3',3'-dimethyl-6-nitrospiro?2H-1-benzopyran-2',2'-indoline! and a composite material made by conjugating the said ionic spiropyrans with clay mineral, the said composite material being capable of forming a transparent thin film which is photo-interconvertible between the said spiropyrans and the corresponding merocyanines.Type: GrantFiled: March 19, 1996Date of Patent: July 21, 1998Assignee: Nissho Iwai Bentonite Co., Ltd.Inventor: Katsuhiko Takagi
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Patent number: 5747225Abstract: The invention relates to a light sensing device comprising a spironaphthoxazine dispersed in a layer of gelatin on a base material.Type: GrantFiled: December 27, 1995Date of Patent: May 5, 1998Assignee: Eastman Kodak CompanyInventors: Joseph Anthony Manico, Richard Carroll Reem
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Patent number: 5576055Abstract: In a first form, photochromic material has anionic photochromic molecules and anionic polar molecules adsorbed between layers of anion-adsorptive inorganic layer-structured crystals. In a second form, photochromic material has neutral photochromic molecules and non-polar molecules adsorbed between layers of anion-adsorptive inorganic layer-structured crystals. The photochromic molecules are of anionic or neutral spiro-pyran compounds and the inorganic crystals are of hydrotalcite compounds. These photochromic materials in which anionic or neutral photochromic molecules remain thermally stable find application as optical recording material. In a third form, a photochromic thin film is available comprising a pyrolytically decomposed thin film of anion-adsorptive inorganic layer-structured crystals having anionic photochromic molecules and non-polar molecules adsorbed thereto. In a fourth form, a clay thin film is prepared by forming a thin film from an aqueous dispersion containing 0.Type: GrantFiled: June 6, 1995Date of Patent: November 19, 1996Assignee: TDK CorporationInventors: Hideyuki Tagaya, Tsuneo Kuwahara
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Patent number: 5512423Abstract: An optical information recording medium improved in storage stability and thermal stability, having a base and a recording layer, the recording layer containing a spiropyran compound and at least one carboxylic acid metallic complex expressed by general formulae I! and II!: ##STR1## where M represents a metallic element and each of R.sub.11 and R.sub.12 represents an alkylene group, an alkylidene group, an aromatic ring, an aliphatic ring, or a heterocyclic ring.Type: GrantFiled: February 4, 1994Date of Patent: April 30, 1996Assignee: Canon Kabushiki KaishaInventors: Teijiro Kitao, Hironori Oda
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Patent number: 5508145Abstract: Materials, films, methods, and systems are described which relate to infrared imaging using a polymeric semiconductor compound having an infrared absorption band crosslinked with a spiroypran capable of producing a visible absorption band. These materials, films, methods, and systems are adapted to produce a visible image when exposed to infrared radiation during use.Type: GrantFiled: May 22, 1995Date of Patent: April 16, 1996Assignee: Board of Regents, The University of Texas SystemInventor: Jean J. Robillard
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Patent number: 5501945Abstract: Several methods of using dyes within polymers and specifically in packaging materials are disclosed. These dyes respond to specific stimuli and indicate exposure to stimuli by a change or shift in the frequencies of light which they adsorb. The stimuli include temperature, radiation, chemicals (e.g. H.sub.2 O, CO.sub.2, NO.sub.2, ethylene, and SO.sub.2), and tensile or compressive stress. Within packaging materials (or affixed thereto as a label, decal or tag) these dyes could indicate spoilage or the possibility of spoilage, that the product has been irradiated, or that the product has been exposed to an undesirably high or low temperature. Many of the shifts in absorption frequencies result in visible color change which a consumer could quickly identify. The tensile or compressive stress sensitive dyes could indicate whether common opposing interlocking polymeric strips used to seal plastic bags have been effectively interlocked to seal the bags.Type: GrantFiled: August 30, 1994Date of Patent: March 26, 1996Assignee: The University of AkronInventor: Sebastian V. Kanakkanatt
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Patent number: 5451343Abstract: The present invention relates to a novel class of compounds which absorb light at wavelengths greater than 350 nm and are useful as fluorescers or as photoinitiators. The present invention provides compounds of the formulas (I) and (II) and their equivalents (the nomenclature of the compounds used herein is based on the numbering of positions as shown in formula (I)): ##STR1## where: when W is .dbd.O, W.sup.1 is hydrogen or --OR.sup.9 and when W is .dbd.NR.sup.+.sub.2, W is hydrogen or NR.sub.2.sup.+2, A is hydrogen, alkenyl, alkyl or an election withdrawing group, and the remaining groups are as defined in the disclosure.Type: GrantFiled: November 19, 1993Date of Patent: September 19, 1995Assignee: Spectra Group Limited, Inc.Inventors: Douglas C. Neckers, Jianmin Shi
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Patent number: 5434032Abstract: Materials, films, methods, and systems are described which relate to infrared imaging using a polymeric semiconductor compound having an infrared absorption band crosslinked with a spiroypran capable of producing a visible absorption band. These materials, films, methods, and systems are adapted to produce a visible image when exposed to infrared radiation during use.Type: GrantFiled: November 6, 1992Date of Patent: July 18, 1995Assignee: Board of Regents, The University of Texas SystemInventor: Jean J. Robillard
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Patent number: 5432048Abstract: A rewritable photochromic optical disc which comprises a photochromic recording layer made of a diaryl ethene derivative capable of assuming first to third states, the first state with a first absorption band transforming into the second state with a second absorption band in response to light of a first wavelength, the second state transforming into the first state in response to light of a second wavelength in said second absorption band, the fist state transforming into the third state with a third absorption band in response to light of a third wavelength, and the third state transforming into the first state in response to light of a fourth wavelength in said third absorption band.Type: GrantFiled: September 28, 1990Date of Patent: July 11, 1995Assignee: Pioneer Electronic CorporationInventors: Hitoshi Taniguchi, Fumio Matsui
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Patent number: 5426018Abstract: The present invention provides a novel photochromic material which is capable of forming two kinds of aggregates, each having a sharp absorption peak at a different wavelength. The photochromic material comprises a spiropyran compound represented by the following general formula: ##STR1## wherein R.sup.1 and R.sup.2 are independently alkyl groups each containing 1 to 30 carbon atoms, and R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are independently selected from the group consisting of hydrogen, an amino group, an alkoxy group with 1 to 5 carbon atoms, and an alkylamino group with 1 to 5 carbon atoms with the proviso that at least one of R.sup.3, R.sup.4, R.sup.5, and R.sup.6 is an amino group, an alkoxy group or an alkylamino group.Type: GrantFiled: November 15, 1993Date of Patent: June 20, 1995Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Junichi Hibino, Kumiko Moriyama, Yoshio Kishimoto
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Patent number: 5403702Abstract: The object of the invention is to provide a novel compound suited for use as a thermochromic and photochromic material.The invention relates to an indolinospirobenzopyran derivative of the general formula ##STR1## [wherein R.sup.1 stands for C.sub.1-20 alkyl, aralkyl, methacryloxymethyl or methacryloxyethyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 may for example be hydrogen; R.sup.8 may for example be hydrogen or methacryloxymethyl; Y may for example be oxygen or sulfur] and a process for producing the derivative.Type: GrantFiled: April 20, 1994Date of Patent: April 4, 1995Assignee: Otsuka Kagaku Kabushiki KaishaInventor: Akira Miyashita
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Patent number: 5399451Abstract: An optical recording medium contains a fluorescent material and a photo-reactive bistable quencher. Information is digitally recorded by utilizing the bistable isomers of the photo-reactive bistable quencher by irradiating the medium with a light in the wavelength to be absorbed by the fluorescent material, whereby energy is transferred from the fluorescent material to the photo-reactive bistable quencher. Reading is made by irradiating the medium with a weaker light and detecting the fluorescence emitted by the fluorescent material.Type: GrantFiled: April 9, 1993Date of Patent: March 21, 1995Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Takashi Hashida, Yoshio Kishimoto
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Patent number: 5360699Abstract: The present invention provides a photochromic material which comprises a spiropyran compound of formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently alkyl groups each containing 1 to 30 carbon atoms and Y is a halogen.The photochromic material possesses absorption sensitivity at wavelengths in the length region of about 700 nm which is the oscillation range of a semi-conductor laser device, and possesses higher stability compared with conventional one when it becomes a colored form.Type: GrantFiled: April 23, 1993Date of Patent: November 1, 1994Assignee: Matsushita Electric Industrial Co. Ltd.Inventors: Junichi Hibino, Eiji Ando
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Patent number: 5346931Abstract: Color former preparations comprisingA) a core of solid particles of a color former,B) a first envelope of a water-soluble nonionic polymer, andC) a second envelope of a crosslinked polymer,are useful for producing heat- and pressure-sensitive recording materials.Type: GrantFiled: January 24, 1992Date of Patent: September 13, 1994Assignee: BASF AktiengesellschaftInventor: Dietrich Hoffmann
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Patent number: 5330864Abstract: Phothermographic material capable of producing a high density cyan image upon image-wise exposure and thermal development at a relatively low temperature and for a short period of time. The photothermographic material of the invention comprise coated on a support base at least one light-sensitive emulsion layer containing: (a) a binder; (b) a silver source material; (c) a light sensitive silver halide in catalytic proximity to said silver source material, wherein said emulsion layer or an adjacent layer thereto comprises a chromogenic cyan leuco dye.The photothermographic material of the invention may be used to obtain good cyan image of suitable density in single color or multicolor photothermographic articles. At the same time the chromogenic leuco dye is stable enough not to be oxidized by oxygen of the air or by simple heating and to limit the fog formation after development.Type: GrantFiled: September 2, 1992Date of Patent: July 19, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Raffaella Biavasco, Cristina Soncini
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Patent number: 5322945Abstract: A method of making a photochromic polysiloxane includes the steps of forming a photochromic spironaphthooxazine monomer including an alkene terminated side and, by addition reaction, covalently bonding the alkene carbon to [SiH] moieties of a siloxane polymer. Novel spironaphthooxazine monomers and photochromic polysiloxanes are disclosed.Type: GrantFiled: February 19, 1993Date of Patent: June 21, 1994Assignee: Yeda Research and Development Co. Ltd.Inventors: Valeri Krongauz, Frida Buchhultz, Alexander Zelichenok, Shlomo Yitzchaik
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Patent number: 5294522Abstract: A novel photochromic compound as a photoreactive material making use of photochromism is provided, which compound is expressed by the following formula (1) or (2)): ##STR1## wherein R is alkyl, alkoxy, perfluoroalkyl or cyano; X.sub.1, X.sub.2, X.sub.3, X.sub.4, X.sub.5 and X.sub.6 are each H, halogen, alkyl, alkoxy, cyano, alkanoyloxy or alkyloxycarbonyl, or a substituted or unsubstituted benzene ring is formed by condensation between at adjacent groups among X.sub.1 to X.sub.6 ; Y is Y.sub.1 C=CY.sub.2, O, S, SO, SO.sub.2 or NY.sub.3 wherein Y.sub.1 and Y.sub.2 are each as defined in the case of the above X.sub.1 to X.sub.6 and Y.sub.3 is H, alkyl, alkanoyl, alkyloxycarbonyl or aryl; and the symbol refers to occurrence of E- or Z-isomer, and which compound is useful as rewritable optical memory element or photo-display element and also as solar energy-storage material, duplicating material, masking material, optical filter, toys, etc.Type: GrantFiled: March 2, 1993Date of Patent: March 15, 1994Assignee: Chisso CorporationInventors: Manabu Uchida, Masahiro Irie
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Patent number: 5288592Abstract: The object of the invention is to provide a novel compound exhibiting stable photochromism.The invention is directed to a transition metal-spirobenzothiopyran complex of the general formula ##STR1## wherein R.sup.1 for example be C.sub.1-20 alkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently may mean hydrogen; Y means O or S; M may for example be Cr, and a process for producing the complex.Type: GrantFiled: November 12, 1992Date of Patent: February 22, 1994Assignee: Otsuka Kagaku Kabushiki KaishaInventor: Akira Miyashita
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Patent number: 5266447Abstract: Disclosed is a photochromic composition comprising an organic photochromic compound and a specific tertiary amine compound which are dissolved or dispersed in a high-molecular compound. Also disclosed are a photochromic film composed of the above photochromic composition and a photochromic laminate having a photochromic layer composed of the above photochromic composition on a surface of a substrate.Type: GrantFiled: February 20, 1991Date of Patent: November 30, 1993Assignee: Lintec CorporationInventors: Kazuhiro Takahashi, Yasukazu Nakada, Shigenobu Maruoka, Ichiro Tsuchida, Takanori Saito
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Patent number: 5252437Abstract: A photochromic material having a thin film of an ion complex of a photochromic substance having an anionic group and a cationic surface active agent is described. Since the surface active agent is used, a uniform film with good photochromism can be obtained. A method for fabricating the photochromic material is also described.Type: GrantFiled: August 2, 1990Date of Patent: October 12, 1993Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Masaaki Suzuki, Kumiko Moriyama, Eiji Ando
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Patent number: 5234799Abstract: A photochromic material containing a copolymer of a spirobenzothiopyran derivative prepolymer and a liquid crystal prepolymer. In addition, a rewritable optical recording medium using the photochromic material. A rewritable optical recording medium obtained by coating a dispersed material, which is obtained by uniformly dispersing a spirobenzothiopyran derivative compound in a thermoplastic resin, on a substrate. A photochromic material capable of controlling a colored state and a decolorized state in a photon mode or a heat mode using an ultraviolet light source and a near-infrared light source. A rewritable optical recording medium capable of rewriting an information in a photon mode using a semiconductor laser.Type: GrantFiled: March 25, 1992Date of Patent: August 10, 1993Assignee: Mitsubishi Denki Kabushiki KaishaInventors: Suguru Nagae, Sei Tsuroda, Kenji Nomura, Kazuhiko Tsutsumi, Yoshiyuki Nakaki
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Patent number: 5230986Abstract: A Photohardenable composition consisting essentially of a free radical polymerizable compound, an electron donating coinitiator, and a benzospiropyran, wherein the benzospiropyran undergoes ring opening to form a merocyanine upon exposure to a actinic radiation or heat and exposure to a second 296 radiation causes the composition to harden.Type: GrantFiled: February 1, 1991Date of Patent: July 27, 1993Assignee: StereoGraphics Limited PartnershipInventor: Douglas C. Neckers
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Patent number: 5208132Abstract: The photochromic material of the invention is such that a composition having an organic photochromic compound dissolved or dispersed in a hindered amine-type compound is microencapsulated. The photochromic material of the invention is not deteriorated in photochromic properties and can be used for a wide range of applications even when coloring or decolorizing repeatedly occurs on intermittent irradiation in air or when it is continuously irradiated with light for a long term.Type: GrantFiled: February 10, 1992Date of Patent: May 4, 1993Assignee: Matsui Shikiso Chemical Co., Ltd.Inventors: Masayasu Kamada, Shozo Suefuku
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Patent number: 5192644Abstract: An improved optical memory device comprising a substrate and a plurality of optical memory layers made of a photochromic material and formed over the substrate, the plurality of optical memory layers being laminated to each other through a heat conductive transparent film, which is adaptable for high density and/or high capacity recording of information.Type: GrantFiled: October 29, 1990Date of Patent: March 9, 1993Assignee: Sharp Kabushiki KaishaInventors: Kenji Ohta, Kazuo Van
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Patent number: 5164287Abstract: A photochromic material containing a copolymer of a spirobenzothiopyran derivative prepolymer and a liquid crystal prepolymer. In addition, a rewritable optical recording medium using the photochromic material. A rewritable optical recording medium obtained by coating a dispersed material, which is obtained by uniformly dispersing a spirobenzothiopyran derivative compound in a thermoplastic resin, on a substrate. A photochromic material capable of controlling a colored state and a decolorized state in a photon mode or a heat mode using an ultraviolet light source and a near-infrared light source. A rewritable optical recording medium capable of rewriting an information in a photon mode using a semiconductor laser.Type: GrantFiled: February 14, 1991Date of Patent: November 17, 1992Assignee: Mitsubishi Denki Kabushiki KaishaInventors: Suguru Nagae, Sei Tsunoda, Kenji Nomura, Kazuhiko Tsutsumi, Yoshiyuki Nakaki
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Patent number: 5118586Abstract: In accordance with the present invention, there are provided photo-recording media comprising photochromic compounds having been dispersed or dissolved in stretched films or nematic liquid crystals, the transition moment of light absorption of said photochromic compounds being orientated in a definite direction. In the photo-recording media as provided, an information recorded in the photochromic compounds can be read out without destroying the same.Type: GrantFiled: March 20, 1989Date of Patent: June 2, 1992Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Yukari Hattori, Junichi Yoshitake, Tooru Yamanaka