Azole Moiety-containing Patents (Class 503/223)
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Patent number: 8545738Abstract: Provided are ink compositions, methods for making photochromic inks, and methods of using the photochromic inks for erasable media annotation. In accordance with various embodiments, there is an ink composition including a carrier medium and one or more photochromic species in the carrier medium, wherein each of the one or more photochromic species can be selected from the group consisting of monomeric photochromic molecules, photochromic oligomers, and photochromic polymers, and wherein each one of the one or more photochromic species exhibits a reversible transition from a colorless state to a colored state upon exposure to a radiant condition wherein the radiant condition can be selected from the group consisting of a radiant energy and a combination of a radiant energy and thermal energy.Type: GrantFiled: August 11, 2010Date of Patent: October 1, 2013Assignee: Xerox CorporationInventors: Peter M. Kazmaier, Gabriel Iftime, Kentaro Morimitsu, Adela Goredema
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Patent number: 8303858Abstract: The present disclosure relates to the process of making a photochromic composite having a photochromic polymer and a binder polymer. The photochromic polymer is made by solution polymerization of the photochromic monomer and two monomers in the presence of a base and the binder polymer is made by solution polymerization of the two monomers in the presence of a base.Type: GrantFiled: March 8, 2010Date of Patent: November 6, 2012Assignee: Xerox CorporationInventors: Kentaro Morimitsu, Adela Goredema, Gabriel Iftime, Peter M. Kazmaier, Roger E. Gaynor
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Publication number: 20120115719Abstract: A polymer composite material (10, 110, 210, 310) is described. The material includes a settable matrix material (12), a plurality of reinforcement members (14) and a plurality of capsule members (16). Each capsule member (16) includes a shell layer (22) encapsulating an indicator material (24). The polymer composite material comprises an initial condition in which each shell layer contains the indicator material, and a damaged condition in which at least one shell layer is ruptured, releasing indicator material. The polymer composite material is changed from the initial condition to the damaged condition by the application of a predetermined force to the polymer composite material.Type: ApplicationFiled: April 20, 2010Publication date: May 10, 2012Applicant: EPL Composite Solutions Ltd.Inventors: Matthew Richard Turner, David Anthony Johnson
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Publication number: 20100227760Abstract: The present disclosure provides a reusable and reimageable medium including a substrate coated with a photochromic polymer. The photochromic polymer has a glass transition temperature ranging from 30° C. to 150° C., such as from about 30° C. to about 100° C., and the coated substrate converts to a colored state when both UV light and temperatures ranging from 30° C. up to 100° C. are applied to the coated substrate. The present disclosure also provides a method for producing and using the reusable and reimageable medium.Type: ApplicationFiled: March 9, 2009Publication date: September 9, 2010Applicant: XEROX CORPORATIONInventors: Kentaro MORIMITSU, Tyler NORSTEN, Gabriel IFTIME, Peter M. KAZMAIER, Guerino SACRIPANTE
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Publication number: 20100041551Abstract: The presently disclosed embodiments are directed to image forming mediums useful for reimageable and transient documents. More particularly, the embodiments pertain to an image forming medium comprising thermally gated photochromic materials comprising diarylethene (DAE) photochromes which avoid problems with unwanted reduction in color contrast due to background coloration.Type: ApplicationFiled: August 12, 2008Publication date: February 18, 2010Applicant: XEROX CORPORATIONInventors: Kentaro Morimitsu, Tyler Norsten, Gabriel Iftime, Peter Kazmaier
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Patent number: 6900158Abstract: A high-molecular weight gel having a leuco dye represented by the formula (L-1) as defined herein, connected thereto by covalent bond or single bond, and a high-molecular weight gel represented by the formula (R-1) as defined herein.Type: GrantFiled: March 19, 2003Date of Patent: May 31, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Takashi Katoh, Akinori Fujita
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Patent number: 6432876Abstract: According to the present invention, a coloring property-improved novel leuco dye which can develop color by heat even with single molecule without requiring excess developer can be obtained, and an image recording medium having high sensitivity and excellent resolution effected by including the dye and a high sensitivity image recording medium further combined with an acid generator can also be obtained. Particularly, it relates to a leuco dye represented by a formula (1) (LD—(A—P1)n) and to an image recording medium which contains the leuco dye (wherein LD represents an acid-sensitive leuco dye mother nucleus, —A represents the residue of an acidic group (—AH) selected from —SO3H, —CO2H and —P(═O)(OH)xRy, R represents a hydrogen atom or a substituent group, x and y are x=1 and y=1 or x=2 and y=0, P1 represents a protecting group which can be removed by the action of light, heat or acid, and n is an integer of 1 or more).Type: GrantFiled: March 30, 2000Date of Patent: August 13, 2002Assignee: Fuji Photo Film Co., Ltd.Inventors: Tatsuhiko Obayashi, Atsuhiro Ohkawa
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Publication number: 20020016260Abstract: The present invention provides a method for forming an azo colorant by reaction of a diazo compound and a coupler. The coupler has a leaving group at the coupling position thereof, such that a coupling reaction rate is faster than it would be if the coupler did not have the leaving group. The coupling reaction rate constant k is preferably 0.1 (s−1) or more.Type: ApplicationFiled: April 18, 2001Publication date: February 7, 2002Inventors: Hisao Yamada, Mitsuyuki Tsurumi, Kazunori Nigorigawa
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Patent number: 5962691Abstract: Pyridone dyes of the formula I ##STR1## where X is nitrogen or CH,R.sup.1 is a 5-membered or 6-membered carbocyclic or heterocyclic radical,R.sup.2 is cyano, carbamoyl, C.sub.1 -C.sub.6 -alkoxycarbonyl or C.sub.1 -C.sub.4 -alkanoyl andR.sup.3 is unsubstituted or substituted C.sub.1 -C.sub.13 -alkyl, unsubstituted or substituted phenyl or unsubstituted or substituted amino,a method for their thermal transfer and a method for coloring or printing synthetic materials by means of the novel dyes.The invention concerns pyridone dyes of the formula (I) in which X is nitrogen or CH, R.sup.1 is a five-membered or six-membered carbocyclic or heterocyclic group, R.sup.2 is cyano, carbamoyl, C.sub.1 -C.sub.6 alkoxycarboyl or C.sub.1 -C.sub.4 alkanoyl and R.sup.3 is optionally substituted C.sub.1 -C.sub.13 alkyl, optionally substituted phenyl or optionally substituted amino.Type: GrantFiled: May 9, 1997Date of Patent: October 5, 1999Assignee: BASF AktiengesellschaftInventors: Andreas Johann Schmidt, Rudiger Sens, Karl-Heinz Etzbach
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Patent number: 5858583Abstract: Novel thermally imageable monochrome product compositions, elements, and processes are disclosed herein. These compositions and elements characteristically have high contrast and fast imaging speeds. The thermally imageable compositions of this invention comprise (a) at least one hexaarylbiimidazole (HABI) compound, (b) at least one leuco dye, (c) at least one acid-generating compound, (d) a polymeric binder, (e) optionally at least one UV stabilizer and/or at least one inhibitor of color formation, and, in certain embodiments, (f) at least one near IR-absorbing dye. These compositions have the propensity for affording, upon thermal imaging, highly colored images having high optical density values. At the same time, background color is low in preferred compositions even after extensive exposure to ambient light. These compositions can be imagewise heated to effect color formation (i.e.Type: GrantFiled: July 3, 1997Date of Patent: January 12, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Rolf Dessauer, Jonathan V. Caspar
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Patent number: 5739078Abstract: By using the fluoran compound represented by the following general formula (I); ##STR1## wherein R.sup.1 is alkyl containing 1 to 4 carbon atoms, R.sup.3 is alkyl containing 1 to 8 carbon atoms, R.sup.4 is hydrogen or alkyl containing 1 to 8 carbon atoms, or R.sup.3 and R.sup.4 may bond with each other to form a ring together with a N atom, R.sup.2 is alkyl containing 1 to 4 carbon atoms, and n denotes 0, 1 or 2, however, the substituents represented by R.sup.2 may be different with each other when n is 2, as a color former for color forming recording materials, recording materials which have excellent properties in whiteness of the background of the material under light and in photostability of color-formed images on the materials as well as in sufficient color forming capability of the material even after having exposed them to light, can be provided.Type: GrantFiled: August 22, 1996Date of Patent: April 14, 1998Assignee: Nippon Soda Co., Ltd.Inventors: Mitsuhiro Yanagita, Takehiro Sato, Shigemi Suga, Tomoya Hidaka, Toru Kawabe, Mamoru Aizawa, Shinichi Sato, Izuo Aoki
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Patent number: 5552365Abstract: Particularly advantageous and environmentally compatible recording material comprises, in microencapsulated form, at least one 3,1-benzoxazine color donor dissolved in a solvent, and is characterized in that the solvent consists of one or more natural oils and/or one or more esters of fatty acids on which natural oils are based, or comprises such oils and/or esters.Type: GrantFiled: March 10, 1995Date of Patent: September 3, 1996Assignee: Bayer AktiengesellschaftInventors: Horst Berneth, Gunter Klug, Jurgen Weisser
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Patent number: 5478793Abstract: A pressure sensitive recording material utilizing a color forming reaction between a colorless or light-colored basic dye and a color acceptor, and in which (1) a basic dye-containing layer and color acceptor-containing layer are formed on one surface of different substrates respectively, (2) a basic dye-containing layer and color acceptor-containing layer are formed on one surface and the other surface of a same substrate respectively, (3) a basic dye-containing layer and color acceptor-containing layer are superposed on one surface of a substrate or (4) a layer containing both basic dye and color acceptor is formed on one surface of a substrate, the pressure sensitive recording material being characterized in that the basic dye is at least one diarylmethane compound represented by the formula (1) given below, the basic dye being enclosed in synthetic high polymer microcapsules having a mean particle size of 3 to 15 .mu.m and an average film thickness of 0.1 to 0.7 .mu.Type: GrantFiled: September 9, 1993Date of Patent: December 26, 1995Assignee: Kanzaki Paper Manufacturing Co., Ltd.Inventors: Tetsuo Tsuchida, Yasuji Koga, Haruo Omura, Masato Tanaka, Nobuhisa Danou
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Patent number: 5476829Abstract: Pressure-sensitive copying material utilizes a blend of rapid- and slow-developing chromogenic materials in vegetable oil solvent and an acid clay or synthetic inorganic color developer. The surface pH of the color developer is not more than 8.7, which gives rise to enhanced image intensity and fade resistance compared with the use of conventional higher color developer surface pH values.Type: GrantFiled: July 1, 1994Date of Patent: December 19, 1995Assignee: The Wiggins Teape Group LimitedInventors: David J. Taylor, Margaret P. Templey, Ivan Sheiham
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Patent number: 5446011Abstract: A thermosensitive recording material capable of being imagewise colored when heated, having a support, and a thermosensitive recording layer formed thereon which contains an N-substituted indole or an aromatic polyhydroxy compound, a carbonyl compound, and an acid material.Type: GrantFiled: April 29, 1994Date of Patent: August 29, 1995Assignee: Ricoh Company, Ltd.Inventors: Kunio Hayakawa, Masafumi Torii
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Patent number: 5364830Abstract: Pressure or heat sensitive record materials with color-former sublimation problems reduced or eliminated whilst not reducing the color forming capability per unit weight of color former by providing what are in effect dimers of vinyl carbinols, with the vinyl carbinol residues, linked through the aryl groups of a diaryl amine.Type: GrantFiled: March 19, 1993Date of Patent: November 15, 1994Assignee: The Wiggins Teape Group LimitedInventors: Ivan Sheiham, Margaret P. Templey
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Patent number: 5329006Abstract: Chromogenic lactam compounds of the formula ##STR1## in which the ring A is an aromatic or heteroaromatic radical which has 6 ring atoms and may contain a fused aromatic ring, it being possible for both the ring A and the fused ring to be substituted;the ring B is an unsubstituted or substituted benzene ring;Z is ##STR2## R is hydrogen; unsubstituted or substituted C.sub.1 -C.sub.12 alkyl, cycloalkyl having 5 to 10 carbon atoms; unsubstituted or substituted aryl or aralkyl; C.sub.1 -C.sub.12 acyl; N-(lower alkyl)carbamoyl; or N-arylcarbamoyl which is unsubstituted or substituted on the ring;Q is C.sub.1 -C.sub.12 alkylene, aryl-C.sub.1 -C.sub.4 alkylene, 1,2-cycloalkylene, 1,2- or 1,8-arylene or aralkylene; andX.sub.1 and X.sub.2, independently of one another, are each hydrogen; unsubstituted or substituted alkyl having a maximum of 12 carbon atoms; acyl having 1 to 8 carbon atoms; cycloalkyl having 5 to 10 carbon atoms; or unsubstituted or ring-substituted aralkyl or aryl; or (X.sub.1 and X.sub.Type: GrantFiled: September 6, 1991Date of Patent: July 12, 1994Assignee: Ciba-Geigy CorporationInventors: Hans Baumann, Ian J. Fletcher
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Patent number: 5316852Abstract: A coated material comprising a substrate which is coated with a layer of a pyrrolopyrrole of formula I ##STR1## wherein R.sub.1 and R.sub.2 may be 4-pyridyl and X.sub.1 and X.sub.2 are O, said compound of formula I being at least partially in the form of a salt of a strong acid, is suitable for use as an optical recording material and, owing to its electrical conductivity and photoconductivity, as antistatically treated material, as sensor, photoreceptor and solar battery.Type: GrantFiled: August 18, 1992Date of Patent: May 31, 1994Assignee: Ciba-Geigy CorporationInventors: Jin Mizuguchi, Gerald Giller, Alain C. Rochat
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Patent number: 5270281Abstract: Heat-sensitive recording materials contain an electron-donating chromogenic compound and an electron-attracting compound. The recording materials also contain at least one compound represented by the following formula: ##STR1## wherein R.sub.1 and R.sub.3 mean a hydrogen atom or an alkyl, aralkyl or aryl group, R.sub.2 and R.sub.4 denote an alkyl, alkenyl, aralkyl or aryl group, X.sub.1, X.sub.2, Y.sub.1 and Y.sub.2 stand for an oxygen or a sulfur atom, and --Z.sub.1 -- and --Z.sub.2 -- are a specific aromatic group. Also provided are phenol compounds represented by the following formula: ##STR2## wherein R.sub.1, R.sub.2, X.sub.1 and Y.sub.1 have the same meanings as defined above; R.sub.5 and R.sub.6 are a hydrogen or halogen atom or an alkyl, alkoxy, aralkyl, aryl or hydroxyl group; p and q stand for an integer of 1-4; R.sub.5 and R.sub.6 may be either the same or different when p and q represent an integer of 2 or greater; and --Z.sub.3 -- means a specific divalent group.Type: GrantFiled: June 22, 1992Date of Patent: December 14, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Atsuo Otsuji, Toshihiro Motoshima, Yoshimitsu Tanabe, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Masakatsu Nakatsuka, Akihiro Yamaguchi
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Patent number: 5244860Abstract: There is described a pressure-sensitive recording and transfer material containing in a first sheet a coating comprising one of the components (A) and (B) or a solvent for these components and in a second sheet the other or both of the components (A) and (B) and an electron-attracting and colour-developing material as component (C),(A) being a polycyclic compound of the formula ##STR1## where X is a monocyclic or polycyclic aromatic or heteroaromatic radical, Y is a substituent which is detachable as an anion, Q.sub.1 is --O--, --S--, ##STR2## Q.sub.2 is --CH.sub.2 --, --CO--, --CS-- or --SO.sub.2 --, R is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.10 cycloalkyl, aryl, such as phenyl, or aralkyl, such as benzyl, and the ring A, which may be substituted, is an aromatic or heterocyclic radical of 6 ring atoms with or without a fused aromatic ring which may likewise be substituted, and(B) being an organic condensation component.Type: GrantFiled: May 20, 1991Date of Patent: September 14, 1993Assignee: Ciba-Geigy CorporationInventors: Rene Graf, Werner Mischler, Peter Burri
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Patent number: 5240897Abstract: A heat-sensitive recording material which contains(A) a polycyclic compound of the formula ##STR1## in which X is a monocyclic or polycyclic aromatic or heteroaromatic radical,Y is a substituent detachable as an anion,Q.sub.1 is --O--, --S--, >N--R or >N--NH--R,Q.sub.2 is --CH.sub.2 --, --CO--, --CS-- or --SO.sub.2 -- andR is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.10 cycloalkyl, aryl such as phenyl or aralkyl such as benzyl, andring A is an aromatic or heterocyclic radical having 6 ring atoms, which can have an aromatic fused ring, it being possible for both ring A and the fused ring to be substituted, and(B) an organic condensable complex compound of a zinc salt.Type: GrantFiled: November 13, 1990Date of Patent: August 31, 1993Assignee: Ciba-Geigy CorporationInventors: Rosalinde Braun, Rudolf Zink
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Patent number: 5190909Abstract: Pressure- or heat-sensitive record material utilizes a chromogenic material of the formula (I) (Ia or Ib): ##STR1## in which: one of A.sub.1 and A.sub.3 is an optionally-substituted carbocyclic aryl group and the other of A.sub.1 and A.sub.3 is either an optionally-substituted aryl group which is the same as or different from A.sub.1, or an optionally-substituted nitrogen-containing aromatic heterocyclic group, with the proviso that if both A.sub.1 and A.sub.3 are aryl groups, then at least one of A.sub.1 and A.sub.3 has a substituted amino or -N-heterocyclic substituent in the 4- position (relative to the bond joining A.sub.1 or A.sub.3 respectively to the remainder of the molecule);A.sub.2 is hydrogen or an optionally-substituted aryl, alkyl or aralkyl group; andA.sub.4 is hydrogen or an optionally-substituted alkyl, aryl or aralkyl group.Type: GrantFiled: November 15, 1990Date of Patent: March 2, 1993Assignee: The Wiggins Teape Group LimitedInventors: Kenneth J. Shanton, Farid Azizian
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Patent number: 5157012Abstract: Pressure-sensitive and heat-sensitive record materials are described comprising a substrate, an acidic developer and chromogenic di-[bis-(indolyl) ethylenyl]tetrahalophthalides of the formula ##STR1## wherein each X.sup.1, S.sup.2, X.sup.3, and X.sup.4 is independently selected from chlorine or bromine;wherein each of R.sup.1 and R.sup.7 is independently selected from cycloalkyl, aralkyl, alkoxyalkyl, or aroxyalkyl;wherein each of R.sup.2 and R.sup.8 is independently selected from alkyl (C.sub.1 -C.sub.8) or aryl (substituted or unsubstituted);wherein each of R.sup.3, R.sup.4, R.sup.5, R.sup.6,R.sup.9, R.sup.10, R.sup.11, and R.sup.12 is independently selected from hydrogen alkyl (C.sub.1 -C.sub.8), cycloalkyl, aryl (substituted or unsubstituted), halogen, alkoxy (C.sub.1 -C.sub.8), aroxy, cycloalkoxy, dialkylamino including symmetrical and unsymmetrical alkyl (C.sub.1 -C.sub.Type: GrantFiled: July 24, 1990Date of Patent: October 20, 1992Assignee: Appleton Papers Inc.Inventors: Ponnampalam Mathiaparanam, Dean G. Dalebroux, Kenneth D. Glanz
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Patent number: 5155087Abstract: A recording material containing as a color forming system (a) a colorless or light-colored dye precursor, and (b) an isocyanate compound having aromaticity, and if necessary (c) a color developer is excellent in image retention rates in terms of light resistance and plasticizer resistance and has a large degree of freedom of hues.Type: GrantFiled: May 22, 1991Date of Patent: October 13, 1992Assignee: Mitsubishi Paper Mills, Ltd.Inventors: Toshihiko Matsushita, Shigetoshi Hiraishi, Sadao Morishita
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Patent number: 5143891Abstract: A chromogenic compound for use in pressure- or heat-sensitive record material has the general formula (I):R.sub.1 --CH.dbd.CH--CR.sub.3 (OR.sub.4)--CH.dbd.CH--R.sub.2 (I)in which: R.sub.1 and R.sub.2 are the same or different and each is a group of one of the formula (II): ##STR1## in which the benzene ring of the group of formula (IIa) is optionally further substituted, and in which: R.sub.10 and R.sub.11 are each independently hydrogen or an optionally-substituted alkyl, aryl or aralkyl group, or R.sub.10 and R.sub.11 together with the nitrogen atom to which they are attached form an optionally-substituted heterocyclic ring, which may include one or more further hetero atoms; R.sub.12, and R.sub.13 and R.sub.14 are each independently hydrogen or an optionally-substituted alkyl, aryl or aralkyl group; R.sub.3 is an optionally-substituted aryl group; and R.sub.4 is hydrogen or an optionally-substituted alkyl, aryl or aralkyl group.Type: GrantFiled: November 15, 1990Date of Patent: September 1, 1992Assignee: The Wiggins Teape Group LimitedInventor: Kenneth J. Shanton
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Patent number: 5094688Abstract: Color-forming agents of the present formula ##STR1## wherein X denotes hydroxyl, alkoxy, alkenyloxy, aralkoxy, cycloalkoxy, aryloxy, acyloxy, alkylamino, dialkylamino, acylamino, aralkylamino or arylamino,R denotes alkyl, alkenyl or aralkyl,R.sub.1 denotes hydrogen, halogen or alkyl,R.sub.2 denotes alkoxy, aralkoxy, aryloxy or a radical of the formula ##STR2## Y.sub.1 and Y.sub.2 independently of one another denote alkyl, aryl, cycloalkyl or aralkyl or R.sub.2, with A in the o-position, forms a heterocyclic ring,a benzene ring can be fused onto the ring A, in the o-/m-position relative to R.sub.2, and the ring A and its fused-on rings and the cyclic and acyclic radicals can carry further non-ionic substitutents customary in dyestuffs chemistry,are used in thermoreactive papers and pressure-sensitive recording materials and for the preparation of highly concentrated solutions in organic solvents.Type: GrantFiled: August 12, 1988Date of Patent: March 10, 1992Assignee: Bayer AktiengesellschaftInventors: Udo Eckstein, Hubertus Psaar, Gert Jabs
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Patent number: 5024988Abstract: A pressure-sensitive or heat-sensitive recording material in which the color reactant system contains, as main components(A) a polycyclic compound of the formula ##STR1## in which X is a monocyclic or polycyclic aromatic or heteroaromatic radical,Y is a substituent detachable as an anion,Q.sub.1 is --O--, --S--, >N--R or >N--NH--R,Q.sub.2 is --CH.sub.2 --, --CO--, --CS-- or --SO.sub.2 -- andR is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.10 cycloalkyl, aryl such as phenyl or aralkyl such as benzyl, and ring A is an aromatic or heterocyclic radical having 6 ring atoms, which can have an aromatic fused ring, it being possible for both ring A and the fused ring to be substituted,(B) an organic condensation component capable of forming a chromogenic compound with component (A) and(C) an electron-withdrawing and a color-developing component.Type: GrantFiled: November 28, 1989Date of Patent: June 18, 1991Assignee: Ciba-Geigy CorporationInventors: Rudolf Zink, Rox Phaff
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Patent number: 5024987Abstract: Pressure-sensitive reactive recording material containinga) as the color-forming agent, a tetraindolylheptamethine ether or alcohol of the formulae I/1, I/2, I/3 or I/4 ##STR1## b) and, as the color developer, the salt of a polyvalent metal and an aromatic carboxylic acid having at least 10 carbon atoms, of the formula (II) ##STR2## wherein A, B, D and E denote ##STR3## and the other radicals have the meanings given in the description, produces light-stable copies which can also be read by machines (OCR).Type: GrantFiled: November 17, 1989Date of Patent: June 18, 1991Assignee: Bayer AktiengesellschaftInventors: Gunter Klug, Gert Jabs, Horst Berneth, Artur Botta
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Patent number: 5013707Abstract: Pressure-sensitive or heat-sensitive recording material in which the color reactant system contains, as essential components,(A) an electron-donating compound of the formula ##STR1## in which Y.sub.1 and Y.sub.2 are substituents which are detachable as anions and can be identical, different or bound to one another and Q.sub.1 is --O--, --S--, >N--R or >N--NH--R,Q.sub.2 is --CH.sub.2 --, --CO--, --CS-- or SO.sub.2 --,R is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.10 cycloalkyl, aryl or aralkyl and ring A is an aromatic radical which has 6 ring atoms and can contain an aromatic fused ring, it being possible not only for ring A but also for the fused ring to be substituted,(B) two organic condensation components which are identical to or different from one another and together are capable of forming a chromogenic compound with component (A) and(C) an electron-withdrawing and color-developing component.Type: GrantFiled: December 14, 1989Date of Patent: May 7, 1991Assignee: Ciba-Geigy CorporationInventors: Rox Phaff, Rudolf Zink
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Patent number: 5011811Abstract: In situ dye generation in a thermal transfer system is achieved by reacting an electrophile with a coupler compound to form an arylidene dye. The electrophile and/or the coupler compound are transferred from a donor element to a receiver element where they react to form a colored dye. The invention comprises a dye image recording element comprising a support bearing the electrophile which has the structure: ##STR1## wherein X is halogen, substituted or unsubstituted alkylsulfonyloxy, substituted or unsubstituted arylsulfonyloxy, or substituted or unsubstituted acyloxy;E.sup.1, E.sup.2, E.sup.3, and E.sup.4 are each independently hydrogen, substituted or unsubstituted alkyl or alkenyl having up to about six carbon atoms, substituted or unsubstituted aryl having up to about ten carbon atoms, halogen, cyano, benzoxazolyl, nitro, --CO.sub.2 R, --COR, --CONH.sub.2, --CONHR, --CONRR, or --SO.sub.Type: GrantFiled: March 7, 1990Date of Patent: April 30, 1991Assignee: Eastman Kodak CompanyInventors: Leslie Shuttleworth, Michael J. McManus
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Patent number: 5001105Abstract: Novel bis-(indolyl)ethylenes, process for their production and record systems utilizing such bis-(indolyl)ethylene chromogens are described.Bis-(indolyl)ethylenes of the following general formula are prepared: ##STR1## wherein each L.sup.1 and L.sup.2 is the same or different and is each independently selected from indole moieties (J1) through (J4) (L.sup.1 need not be the same as L.sup.2), ##STR2## wherein Z is hydrogen, alkyl (C.sub.1 -C.sub.8), substituted or unsubstituted aryl, aralkyl, aroxyalkyl, alkoxyalkyl or halogen.Type: GrantFiled: August 25, 1990Date of Patent: March 19, 1991Assignee: Appleton Papers Inc.Inventor: Ponnampalam Mathiaparanam
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Patent number: 4997805Abstract: Chromogenic dicyanomethylenepyrazolinone for thermographic recording processes and the corresponding cyanomethylene dyes of the formula ##STR1## in which R is hydrogen, hydroxyl, amino, alkyl, cycloalkyl, aryl, aralkyl or a heterocyclic radical, T.sub.1 and T.sub.2, independently of one another, are each hydrogen, unsubstituted or halogen-, hydroxyl-, cyano- or lower alkoxy-substituted alkyl having a maximum of 12 carbon atoms, cycloalkyl having 5 to 10 carbon atoms or unsubstituted or halogen-, cyano-, lower alkyl- or lower alkoxy-(ring)substituted phenalkyl or phenyl, or T.sub.1 and T.sub.2 together with the nitrogen linking them are a five- or six-membered heterocyclic radical, and rings A and B, independently of one another, are unsubstituted or substituted by halogen, cyano, nitro, lower alkyl, lower alkoxy, (lower alkyl)carbonyl or (lower alkoxy)carbonyl.Type: GrantFiled: June 18, 1990Date of Patent: March 5, 1991Assignee: Ciba-Geigy CorporationInventors: Hans Junek, Manfred Klade
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Patent number: 4981833Abstract: A recording material comprising at least one thermodecoloring type dye represented by formula (I) or formula (II) ##STR1## wherein Ar.sup.1 and AR.sup.2 each represents an aryl group or heteroaryl group; R.sup.1 represents an alkyl group, alkenyl group, aralkyl group, aryl group, or heteroaryl group; A represents an atomic group forming a 5 to 6 member ring; and X.crclbar. represents a residue with an electric charge value of -1; or Ar.sup.1 and Ar.sup.2 bond together to form a ring.Type: GrantFiled: December 19, 1989Date of Patent: January 1, 1991Assignee: Fuji Photo Film Co., Ltd.Inventor: Kozo Sato
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Patent number: 4981836Abstract: A recording material is disclosed, which comprises a support having thereon a recording layer comprising at least one electron-donating colorless dye and at least one electron-accepting compound, wherein said electron-donating colorless dye is a fluorene derivative having a substituted amino group at the 3-position and the 5-position or a substituted amino group at the 2-position and the 6-position.The recording material gives colored portions having light absorption at near infrared region, has improved coloring property and shelf life, and gives colored images having improved stability.Type: GrantFiled: November 3, 1989Date of Patent: January 1, 1991Assignee: Fuji Photo Film Co., Ltd.Inventors: Naoto Yanagihara, Ken Iwakura, Hiroo Fukunaga, Akira Igarashi
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Patent number: 4959291Abstract: A light-sensitive material comprising a light-sensitive layer containing silver halide, a reducing agent, a polymerizable compound and a leuco dye provided on a support, characterized in that the leuco dye has the following formula (I): ##STR1## in which each of R.sup.1 and R.sup.2 independently is hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group, or R.sup.1 and R.sup.2 together with the neighboring nitrogen atom form a 5- or 6-membered ring; X is hydrogen, a halogen atom, an alkyl group, an alkoxy group, --NHCOR.sup.3 or --OCOR.sup.4 (each of R.sup.3 and R.sup.4 is an alkyl group or an aryl group) or --NR.sup.5 R.sup.6 (R.sup.5 and R.sup.6 have the same meanings as for R.sup.1 and R.sup.2); Y is an alkyl group or an aralkyl group; Z is hydrogen, an alkyl group or an aryl group; and each of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, X, Y, Z and the benzene ring A may have one or more substituent groups.Type: GrantFiled: August 8, 1989Date of Patent: September 25, 1990Assignee: Fuji Photo Film Co., Ltd.Inventors: Toru Harada, Toshiyuki Watanabe
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Patent number: 4918045Abstract: A recording material comprising a support, a microcapsule containing a substantially colorless electron-donating color former and a solvent, and an electron-accepting developer, wherein the color former is at least one selected from p-substituted aminophenylindolylphthalide derivatives, p-substituted aminophenylindolylazaphthalide derivatives and p-substituted aminophenylindolyldiazaphthalide derivatives, the solvent is a paraffin oil, and the amount of the solvent is at least 20% by weight based on the weight of the core substance.Type: GrantFiled: July 15, 1988Date of Patent: April 17, 1990Assignee: Fuji Photo Film Co., Ltd.Inventors: Katsumi Matsuoka, Masanobu Takashima, Ken Iwakura, Keiso Saeki
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Patent number: 4904637Abstract: Compounds of the formula ##STR1## wherein Z.sup.1 denotes hydrogen, alkyl, cycloalkyl or ##STR2## R.sup.1 denotes hydrogen, alkyl, cycloalkyl, aralkyl, aryl, heteroalkyl or heteryl,X.sup.1, X.sup.2 and X.sup.3 denote hydrogen, halogen, alkyl, cycloalkyl, aryl, alkanoylamino, aroylamino or heteryl, and at least one of these radicals denotes NH.sup.1 Y.sup.2, OY.sup.3 or SY.sup.3,Y.sup.1, Y.sup.2 and Y.sup.3 denote hydrogen, alkyl, cycloalkyl, aralkyl, aryl or heteryl andY.sup.1 +Y.sup.2 denote the remaining members of a 5-membered or 6-membered ring which optionally contains further hetero-atoms,are outstanding suitable as color-forming agents for pressure-sensitive, heat-sensitive and electrosensitive recording materials with an acid developer. Deep copies which are fast to light are obtained.Type: GrantFiled: February 14, 1989Date of Patent: February 27, 1990Assignee: Bayer AktiengesellschaftInventor: Horst Berneth
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Patent number: 4880762Abstract: Coloring phthalide compounds having general formula [I], a method of producing the phthalide compounds and a recording material comprising as a coloring component any of the coloring phthalide compounds are disclosed, ##STR1## wherein R.sup.1 and R.sup.2 each represent a straight chain or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group, or a benzyl group, and R.sup.1 and R.sup.2 in combination may form a ring; R.sup.3 represents an alkyl group having 1 to 4 carbon atoms; R.sup.4 represents a dialkylamino group having 1 to 6 carbon atoms, a cyclic amino group or halogen, l is an integer of 0 to 4; A represents ##STR2## wherein R.sup.5 and R.sup.6 each represent a straight chain or branched alkyl group having 1 to 8 carbon atoms, a cycloalkyl group, or a benzyl group, R.sup.5 and R.sup.6 in combination may form a ring; and B is the same as A, or represents a phenyl group which may have a substituent.Type: GrantFiled: November 20, 1987Date of Patent: November 14, 1989Assignee: Ricoh Company, Ltd.Inventors: Kiyotaka Iiyama, Kunio Hayakawa
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Patent number: 4870050Abstract: Bis{[1-(2-A-2-B)ethenyl]}[2-R.sup.2 -4-X-phenyl-or 1-(2-R.sup.2 -4-X-phenyl) ethenyl]methanes useful as color formers, particularly in transfer imaging, pressure sensitive and thermal-responsive carbonless duplicating systems, are prepared by the interaction of two molecular proportions of the corresponding 1-A-1-B-ethene with the appropriate 2-R.sup.2 -4-X-phenyl-(CH.dbd.CH).sub.n --CHO presence of an acidic catalyst.Type: GrantFiled: March 11, 1988Date of Patent: September 26, 1989Assignee: Hilton Davis Co.Inventor: William M. Hung
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Patent number: 4861748Abstract: A recording material containing the combination of at least one electron-donating colorless dye containing a p-substituted aminophenylindolyl azaphthalide and at least one electron-accepting compound containing an organic acid having at least one phenolic hydroxyl group. The material provides colored images having improved stability.Type: GrantFiled: July 9, 1987Date of Patent: August 29, 1989Assignee: Fuji Photo Film Co., Ltd.Inventors: Keiso Saeki, Masanobu Takashima, Ken Iwakura
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Patent number: 4855282Abstract: A recording material is disclosed, which comprises a support having thereon a recording layer containing an at least one electron-donating colorless dye and at least one electron-accepting compound, wherein said electron-donating colorless dye is a copolymer of at least one polymerizable colorless dye monomer and at least one comonomer. The recording material has improved color forming property, shelf life, and stability of colored images.Type: GrantFiled: September 22, 1987Date of Patent: August 8, 1989Assignee: Fuji Photo Film Co., Ltd.Inventors: Masato Satomura, Ken Iwakura, Masanobu Takashima, Akira Igarashi
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Patent number: 4853363Abstract: A heat-sensitive recording material has a substrate and a color-developing layer which comprises a near infrared-absorbing fluorantype leuco dye.This heat-sensitive recording material provides a superior optical readability in near infrared region.Type: GrantFiled: April 6, 1988Date of Patent: August 1, 1989Assignee: Jujo Paper Co., Ltd.Inventors: Toshimi Satake, Toshiaki Minami, Tomoaki Nagai, Fumio Fujimura
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Patent number: 4853362Abstract: A heat-sensitive recording material has a support and a color-developing layer which comprises both as a colorless basic chromogenic dye at least one of a particular fluorane-type leuco dye and a particular divinyl compound and as a stabilizer a particular halogen-substituted zinc benzoate derivative.This heat-sensitive recording material is superior in light resistance, weather resistance, oil resistance and optical readability in the near infrared region.Type: GrantFiled: August 19, 1988Date of Patent: August 1, 1989Assignee: Jujo Paper Co., Ltd.Inventors: Toshimi Satake, Tadakazu Fukuchi, Toshiaki Minami, Tomoaki Nagai, Toshio Kaneko, Fumio Fujimura
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Patent number: 4853361Abstract: A heat- and light-sensitive recording material has a substrate and a color-forming layer which comprises a particular fluoran-type leuco dye.This heat- and light-sensitive recording material provides a clear image a superior contamination-resistance and an excellent readability in visible and near infrared range.Type: GrantFiled: April 14, 1988Date of Patent: August 1, 1989Assignee: Jujo Paper Co., Ltd.Inventors: Toshimi Satake, Toshiaki Minami, Tomoaki Nagai, Fumio Fujimura
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Patent number: 4849397Abstract: A pressure-sensitive recording medium producing a colored image utilizing the reaction between a substantially colorless electron donating dye precursor and an electron accepting developer is disclosed. This recording sheet is characterized in that the electron accepting developer layer contains an aromatic carboxylic acid metal salt and the electron donating dye precursor layer contains (a) an indolylazaphthalide compound and (b) Crystal Violet lactone.Type: GrantFiled: October 21, 1988Date of Patent: July 18, 1989Assignee: Fuji Photo Film Co., Ltd.Inventors: Shojiro Sano, Keiso Saeki
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Patent number: 4845072Abstract: A thermosensitive recording material is disclosed, which comprises a support material and a thermosensitive coloring layer formed thereon comprising a leuco dye, a color developer capable of inducing color formation in the leuco dye upon application of heat thereto, and a vinyl ether compound having the general formula, ##STR1## which serves as thermosensitivity improvement agent.Type: GrantFiled: November 20, 1987Date of Patent: July 4, 1989Assignee: Ricoh Company, Ltd.Inventors: Hiromi Furuya, Kiyotaka Iiyama
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Patent number: 4839332Abstract: A heat-sensitive recording material is disclosed. The material is comprised of a support having thereon a heat-sensitive color forming layer comprising at least one electron-donating colorless dye and at least one electron-accepting compound, wherein the electron-donating colorless dye is a fluorene derivative having at least one substituted amino group and the electron-accepting compound has an acid group and a solubility in ethanol of 10 or less at 25.degree. C.The material exhibits improved color developability, improved preservability before recording, improved image stability, and improved chemical resistance.Type: GrantFiled: January 15, 1988Date of Patent: June 13, 1989Assignee: Fuji Photo Film Co., Ltd.Inventors: Kensuke Ikeda, Naoto Yanagihara, Ken Iwakura
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Patent number: 4839335Abstract: A heat responsive recording element having a recording layer containing a colorless di- or tri-aryl methane compound having a closed ring moiety incorporating the meso carbon atom and containing a nitrogen atom directly bonded to the meso carbon. The nitrogen atom is also bonded to a heterocyclic or carbocyclic ring substituted with an alkylating group. Upon heating the recording layer imagewise the alkylating group effects intramolecular alkylation of the nitrogen atom with irreversible breaking of the meso carbon atom-nitrogen atom bond rendering the compound colored in the imagewise heating pattern.Type: GrantFiled: September 28, 1987Date of Patent: June 13, 1989Assignee: Polaroid CorporationInventor: Ernest W. Ellis
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Patent number: 4835291Abstract: Disclosed herein are novel divinyl compounds represented by the formula (I): ##STR1## and a recording-material prepared by utilizing the divinyl compounds. The divinyl compound is in itself almost colorless, extremely stable in the atmosphere and develops rapidly blackish color by a developer. The color image given by the divinyl compound is excellent in light-resistance and moisture-resistance and the letters developed can be read by an optical letter-reading apparatus or a barcord reading apparatus.Type: GrantFiled: April 13, 1987Date of Patent: May 30, 1989Assignee: Yamada Chemical Co., Ltd.Inventors: Hajime Kawai, Yoshiharu Fujino, Youji Shimizu, Seiichi Nieda, Kazuhiko Gendai, Katsuhiko Tsunemitsu
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Patent number: 4826806Abstract: Fluoran compounds are disclosed of formula (I) ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently represent hydrogen, halogen, lower alkoxy, C.sub.1 -C.sub.9 -alkyl, C.sub.5 or C.sub.6 -cycloalkyl, benzyl or phenyl, said benzyl or phenyl being optionally substituted by halogen, lower alkyl or lower alkoxy, and further R.sub.1 and R.sub.2 as well as R.sub.3 and R.sub.4 taken together with Ring A, may form a naphthalene ring optionally substituted by halogen, lower alkyl or lower alkoxy, R.sub.5, R.sub.6 and R.sub.7 independently represent halogen, lower alkyl or lower alkoxy, B.sub.1 and B.sub.2 independently represent hydrogen, C.sub.1 -C.sub.8 -alkyl, benzyl or phenyl, said benzyl or phenyl being optionally substituted by halogen, lower alkyl, lower alkoxy, or alkyl-substituted amino, X represents hydrogen atom or --NR.sub.8 R.sub.9 wherein R.sub.8 and R.sub.9 independently represent hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.5 or C.sub.Type: GrantFiled: July 29, 1987Date of Patent: May 2, 1989Assignee: Shin Nisso Kako Co., Ltd.Inventors: Takeo Obitsu, Yutaka Ohnishi, Shinji Yoshinaka, Minoru Koguchi, Mitsuhiro Yanagita, Nobuyuki Hirai