Plural Nitrogens Bonded Directly To The Xanthene Ring System (e.g., 2,6 Diaminofluorans, Etc.) Patents (Class 549/226)
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Publication number: 20150110715Abstract: The present invention relates to a compound or a pharmaceutically acceptable salt thereof having a chemical structure comprising: (A) at least one motif specifically binding to cell membranes of neoplastic cells; (B) at least one chelator moiety of radiometals; and (C) at least one dye moiety; wherein said compound has a molecular weight of not more than 5 kDa. Further, the invention refers to a method for producing such compound and to the in vivo and in vitro uses thereof.Type: ApplicationFiled: July 18, 2014Publication date: April 23, 2015Applicants: RUPRECHT-KARLS-UNIVERSITAT HEIDELBERG, DEUTSCHES KREBSFORSCHUNGSZENTRUMInventors: Matthias Eder, Klaus Kopka, Martin Schaefer, Ulrike Bauder-Wuest, Uwe Haberkorn
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Patent number: 9006437Abstract: The present invention relates to fluorescent dyes in general. The present invention provides a wide range of fluorescent dyes and kits containing the same, which are applicable for labeling a variety of biomolecules, cells and microorganisms. The present invention also provides various methods of using the fluorescent dyes for research and development, forensic identification, environmental studies, diagnosis, prognosis, and/or treatment of disease conditions.Type: GrantFiled: April 9, 2013Date of Patent: April 14, 2015Assignee: Biotium, Inc.Inventors: Fei Mao, Wai-Yee Leung, Ching-Ying Cheung
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Patent number: 8940859Abstract: 1,3-Dipole-functional compounds (e.g., azide functional compounds) can be reacted with certain alkynes in a cyclization reaction to form heterocyclic compounds. Useful alkynes (e.g., strained, cyclic alkynes) and methods of making such alkynes are also disclosed. The reaction of 1,3-dipole-functional compounds with alkynes can be used for a wide variety of applications including the immobilization of biomolecules on a substrate.Type: GrantFiled: March 13, 2012Date of Patent: January 27, 2015Assignee: University of Georgia Research Foundation, Inc.Inventors: Geert-Jan Boons, Jun Guo, Xinghai Ning, Margaretha Wolfert
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Publication number: 20140011208Abstract: The present invention relates to fluorescent dyes in general. The present invention provides a wide range of fluorescent dyes and kits containing the same, which are applicable for labeling a variety of biomolecules, cells and microorganisms. The present invention also provides various methods of using the fluorescent dyes for research and development, forensic identification, environmental studies, diagnosis, prognosis, and/or treatment of disease conditions.Type: ApplicationFiled: April 9, 2013Publication date: January 9, 2014Inventors: Fei Mao, Wai-Yee Leung, Ching-Ying Cheung, Ching-Ying Cheung
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Publication number: 20130321521Abstract: There is provided a coloring composition containing a compound represented by Formula (1): wherein D represents a residue structure in which four hydrogen atoms are removed from the compound represented by Formula (2), R1 and R2 represent R1?R2?H or R1?R and R2=-L-CO2M, R represents a hydrogen atom or a monovalent substituent, and when a plurality of R is present, R's may be the same or different, L represents a divalent linking group, and when a plurality of L is present, L's may be the same or different, M represents a hydrogen atom or a counteraction, and when a plurality of M is present, M's may be the same or different, and n represents the number of 1 to 4, and m represents the number of 0 to 3, provided that m+n is 4.Type: ApplicationFiled: May 21, 2013Publication date: December 5, 2013Applicant: FUJIFILM CorporationInventors: Yoshihiko FUJIE, Keiichi TATEISHI, Clive Edwin FOSTER
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Patent number: 8586743Abstract: The present disclosure is directed to a reactive ester agent capable of conjugating a reporter molecule to a carrier molecule or solid support. The reactive ester agent has the general formula: wherein the variables are described throughout the application.Type: GrantFiled: January 30, 2008Date of Patent: November 19, 2013Assignee: Life Technologies CorporationInventors: Kyle Gee, Aleksey Rukavishnikov, Diane M. Witczak
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Publication number: 20120322974Abstract: 1,3-Dipole-functional compounds (e.g., azide functional compounds) can be reacted with certain alkynes in a cyclization reaction to form heterocyclic compounds. Useful alkynes (e.g., strained, cyclic alkynes) and methods of making such alkynes are also disclosed. The reaction of 1,3-dipole-functional compounds with alkynes can be used for a wide variety of applications including the immobilization of biomolecules on a substrate.Type: ApplicationFiled: March 13, 2012Publication date: December 20, 2012Applicant: University of Georgia Research Foundation, Inc.Inventors: GEERT-JAN BOONS, Jun Guo, Xinghai Ning, Margaretha Wolfert
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Publication number: 20120172575Abstract: 1,3-Dipole-functional compounds (e.g., azide functional compounds) can be reacted with certain alkynes in a cyclization reaction to form heterocyclic compounds. Useful alkynes (e.g., strained, cyclic alkynes) and methods of making such alkynes are also disclosed. The reaction of 1,3-dipole-functional compounds with alkynes can be used for a wide variety of applications including the immobilization of biomolecules on a substrate.Type: ApplicationFiled: March 13, 2012Publication date: July 5, 2012Applicant: University of Georgia Research Foundation, Inc.Inventors: GEERT-JAN BOONS, Jun Guo, Xinghai Ning, Margaretha Wolfert
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Publication number: 20120149918Abstract: A process for the preparation of 3-dibutylamino-6-methyl-7-anilinofluoran and a heating- and pressure sensitive recording material are claimed.Type: ApplicationFiled: August 9, 2010Publication date: June 14, 2012Applicant: BASF SEInventor: Robert Montgomery O'Neil
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Patent number: 8114904Abstract: Provided herein are compounds or fluorogenic probes which can be used as reagents for measuring, detecting and/or screening ROS or RNS such as peroxynitrite or hypochlorite. Provided also herein are methods that can be used to measure, directly or indirectly, the amount of peroxynitrite or hypochlorite in chemical samples and biological samples such as cells and tissues in living organisms. Specifically, the methods include the steps of contacting the fluorogenic probes disclosed herein with the samples to form one or more fluorescent compounds, and measuring fluorescence properties of the fluorescent compounds. Provided also herein are high-throughput screening fluorescent methods for detecting or screening peroxynitrite or compounds that can increase or decrease the level of peroxynitrite or hypochlorite in chemical and biological samples.Type: GrantFiled: April 3, 2009Date of Patent: February 14, 2012Assignee: Versitech Limited & Morningside Ventures LimitedInventors: Dan Yang, Tao Peng
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Patent number: 7985865Abstract: A compound having the formula wherein R1, Z, and the carbonyl can be comprised by a common ring, wherein R1 comprises a chromophore that absorbs light from the visible wavelength range, and wherein n is an integer of at least 12. A solid phase change ink composition is also disclosed containing a colorant comprising a chromophore that absorbs light from the visible wavelength range and has the formula wherein R1, Z, and the carbonyl can be comprised by a common ring, and wherein n is an integer of at least 12. Also disclosed is a method of forming a colorant wherein a first compound having the formula is reacted with a second compound having the formula Z(CH2)nCH3 wherein n is an integer of at least 12 to form a third compound having the formula wherein the third compound comprises a chromophore that absorbs light from the visible wavelength range.Type: GrantFiled: December 14, 2007Date of Patent: July 26, 2011Assignee: Xerox CorporationInventors: Jeffrey H Banning, Michael B. Meinhardt, Donald R Titterington, Clifford R King
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Publication number: 20110166366Abstract: Provided are chalcogenoxanthylium compounds which can effectively be used as sensitizers in photodynamic therapy, virucides in photodynamic antimicrobial chemotherapy and reversal agents of Pgp function in cancer cells. Further provided is a general method for the preparation of chalcogenoxanthylium compounds.Type: ApplicationFiled: March 11, 2011Publication date: July 7, 2011Inventors: Michael R. Detty, David J. Donnelly, Stephen J. Wagner
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Publication number: 20110053895Abstract: The invention relates to pharmacology and medicine, in particular to a class of mitochondrially-addressed compounds which can be used in the pharmaceutical compositions of medicinal agents (preparations) for preventing and treating cardiovascular diseases and diseases and pathological conditions caused by disturbed blood circulation or oxygen supply to tissues and organs.Type: ApplicationFiled: June 29, 2007Publication date: March 3, 2011Inventors: Maxim Vladimirovich Skulachev, Vladimir Petrovich Skulachev
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Patent number: 7704756Abstract: Fluorogenic or chromogenic dyes are useful as reporter molecules for detecting cell entry by a specific molecule.Type: GrantFiled: January 30, 2006Date of Patent: April 27, 2010Assignee: Novartis Vaccines and Diagnostics, Inc.Inventors: Daniel J. Suich, Ronald N. Zuckermann
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Patent number: 7615377Abstract: The present invention is directed, in part, to fluorescein-based ligands for detection of metal ions, and methods of making and using the same.Type: GrantFiled: August 27, 2004Date of Patent: November 10, 2009Assignee: Massachusetts Institute of TechnologyInventors: Stephen J. Lippard, Elizabeth Marie Nolan
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Patent number: 7399639Abstract: The present invention is directed, in part, to sensors for detecting metal ions, and methods of making and using the same.Type: GrantFiled: May 4, 2003Date of Patent: July 15, 2008Assignee: Massachusetts Institute of TechnologyInventors: Stephen J. Lippard, Carolyn Crystal Woodroofe
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Patent number: 6998493Abstract: Compounds of the formula wherein M is either (1) a metal ion having a positive charge of +p wherein p is an integer which is at least 2, said metal ion being capable of forming a compound with at least two chromogen moieties, or (2) a metal-containing moiety capable of forming a compound with at least two chromogen moieties, z is an integer representing the number of chromogen moieties associated with the metal and is at least 2, and R1, R2, R3, R4, R5, R6, R7, a, b, c, d, Y, Q?, A, and CA are as defined herein.Type: GrantFiled: June 26, 2003Date of Patent: February 14, 2006Assignee: Xerox CorporationInventors: Jeffery H. Banning, Bo Wu, James M. Duff, Wolfgang G. Wedler, Jule W. Thomas, Jr., Randall R. Bridgeman
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Patent number: 6916925Abstract: Dye labeled imidazonaphthyridine, imidazopyridine and imidazoquinoline compounds having immune response modulating activity are disclosed. The compounds arc useful, inter alia, for determining the binding and/or receptor sites of the molecules.Type: GrantFiled: July 22, 2003Date of Patent: July 12, 2005Assignee: 3M Innovative Properties Co.Inventors: Michael J. Rice, Mark A. Tomai, Ai-Ping Wei
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Patent number: 6635602Abstract: A process for the manufacture of mixtures of fluoran compounds by the reaction of keto acids of formula (II) with a compound of formula (III) in the presence of a dehydrating condensation agent, wherein R1 and R2 independently represent hydrogen; an alkyl of 1-18 carbon, a secondary alkyl with respect to the carbon atom bonded to the nitrogen atom of 3-13 carbon atoms, a cycloalkyl of 4-8 carbon atoms or a phenyl, both of which may be substituted by at least one substituted selected from the group consisting of halogen atoms and alkyls having 1-4 carbon atoms, an aralkyl of 7-10 carbon atoms; or R1 and R2, together with the adjacent nitrogen atom from a heterocyclic ring; R3 is hydrogen, an alkyl of 1-4 carbon atoms, an alkoxy of 1-4 carbon atoms, a phenyl; a substituted phenyl or a halogen; R4 is an alkyl group of 1-18 carbon atoms, a carboxyalkyl of 1-18 carbon atoms, a carboxycycloalkyl of 4-8 carbon atoms, an alkylamino of 1-18 carbon atoms, a cycloalkylamino of 4-8 carbon atoms, a dialkylamino or dicycloType: GrantFiled: February 26, 2001Date of Patent: October 21, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: James Philip Taylor, Michael Heneghan
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Patent number: 6630588Abstract: Dye labeled imidazonaphthyridine, imidazopyridine and imidazoquinoline compounds having immune response modulating activity are disclosed. The compounds are useful, inter alia, for determining the binding and/or receptor sites of the molecules.Type: GrantFiled: February 19, 2002Date of Patent: October 7, 2003Assignee: 3M Innovative Properties CompanyInventors: Michael J. Rice, Mark A. Tomai, Ai-Ping Wei
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Patent number: 6605731Abstract: Novel addition products of isocyanates with oxyalkylene-substituted aminophenol compounds as intermediates for the production of urethane-substituted xanthene colorants, particularly triphenylmethane derivatives such as rhodarnines, are provided. The xanthene colorants exhibit improved wax and/or oil solubility and high purity. The urethane-substituted xanthene, colorant features very good wax and/or oil solubility, and is believed to be relatively nontoxic. A method for producing this novel colorant is also provided.Type: GrantFiled: October 4, 2002Date of Patent: August 12, 2003Assignee: Milliken & CompanyInventors: Rajnish Batlaw, Patrick D. Moore
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Publication number: 20030096192Abstract: Optical data carrier comprising a preferably transparent substrate which may, if desired, have previously been coated with one or more reflection layers and to whose surface a light-writeable information layer, if desired one or more reflection layers and, if desired, a protective layer or a further substrate or a covering layer have been applied, which can be written on or read by means of blue or red light, preferably laser light, where the information layer comprises a light-absorbent compound and, if desired, a binder, characterized in that at least one xanthene dye which contains at least two anionic groups and has at least one cation containing at least one conjugated &pgr; system having at least 6 &pgr; electrons as counterion, where the cation must not be benzyltrimethylammonium, benzyltriethylammonium, tetraphenylphosphonium, butyltriphenylphosphonium or ethyltriphenylphosphonium, is used as light-absorbent compound.Type: ApplicationFiled: March 20, 2002Publication date: May 22, 2003Inventors: Horst Berneth, Friedrich-Karl Bruder, Wilfried Haese, Rainer Hagen, Karin Hassenruck, Serguei Kostromine, Peter Landenberger, Rafael Oser, Thomas Sommermann, Josef-Walter Stawitz, Thomas Bieringer
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Publication number: 20030068668Abstract: Systems, including compositions and methods, for measuring pH, particularly in cells, organelles, and other samples. The compositions include pH-sensitive fluorescent and fluorogenic 2′,7′-dialkylfluorescein derivatives and associated nonfluorescent precursor compounds. The compositions may permit ratiometric measurement in the excitation spectrum and the emission spectrum. The methods include adding a precursor compound to a sample cell, incubating the sample cell to release the free indicator, illuminating the sample cell, and detecting the fluorescence response of the free indicator.Type: ApplicationFiled: March 27, 2002Publication date: April 10, 2003Inventors: Zhenjun Diwu, Jesse J. Twu, Guoliang Yi, Luke D. Lavis, Yen-Wen Chen, Kelly J. Cassutt
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Publication number: 20030050481Abstract: Novel addition products of isocyanates with oxyalkylene-substituted aminophenol compounds as intermediates for the production of urethane-substituted xanthene colorants, particularly triphenylmethane derivatives such as rhodarnines, are provided. The xanthene colorants exhibit improved wax and/or oil solubility and high purity. The urethane-substituted xanthene, colorant features very good wax and/or oil solubility, and is believed to be relatively nontoxic. A method for producing this novel colorant is also provided.Type: ApplicationFiled: October 4, 2002Publication date: March 13, 2003Inventors: Rajnish Batlaw, Patrick D. Moore
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Patent number: 6452020Abstract: Novel addition products of isocyanates with oxyalkylene-substituted aminophenol compounds as intermediates for the production of urethane-substituted xanthene colorants, particularly triphenylmethane derivatives such as rhodamines, are provided. The xanthene colorants exhibit improved wax and/or oil solubility and high purity. The urethane-substituted xanthene colorant features very good wax and/or oil solubility, and is believed to be relatively nontoxic. A method for producing this novel colorant is also provided.Type: GrantFiled: April 10, 2001Date of Patent: September 17, 2002Assignee: Milliken & CompanyInventors: Rajnish Batlaw, Patrick D. Moore
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Patent number: 6376669Abstract: Dye labeled imidazonaphthyridine, imidazopyridine and imidazoquinoline compounds having immune response modulating activity are disclosed. The compounds are useful, inter alia, for determining the binding and/or receptor sites of the molecules.Type: GrantFiled: November 2, 2000Date of Patent: April 23, 2002Assignee: 3M Innovative Properties CompanyInventors: Michael J. Rice, Mark A. Tomai, Ai-Ping Wei
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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: 6143904Abstract: The invention describes a color former mixture comprising(a) a compound of formula (1) and/or of formula (2) and/or of formula (3) and(b) a compound of formula (4),or a color former mixture comprising at least two compounds of component (b).The color former mixture is suitable for pressure- and particularly for heat-sensitive recording materials and has excellent storage ability and superior paper whiteness.Type: GrantFiled: June 17, 1997Date of Patent: November 7, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Rudolf Zink, Klaus Huber
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Patent number: 6130101Abstract: The present invention describes xanthene dyes, including rhodamines, rhodols and fluoresceins that are substituted one or more times by a sulfonic acid or a salt of a sulfonic acid. The dyes of the invention, including chemically reactive dyes and dye-conjugates are useful as fluorescent probes, particularly in biological samples.Type: GrantFiled: September 23, 1997Date of Patent: October 10, 2000Assignee: Molecular Probes, Inc.Inventors: Fei Mao, Wai-Yee Leung, Richard P. Haugland
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Patent number: 5376617Abstract: The improved .beta.-type crystal modification of 2-(3-methylanilino)-3-methyl-6-diethylaminofluoran has high solubility in inner-phase solvents. The compound is very useful as a color former for pressure-sensitive recording materials and thermal recording materials. Recording materials that use this compound as color former exhibit good performance in various characteristics such as whiteness of the background, its storage stability, color rendition, sensitivity for color formation and color fastness of image.Type: GrantFiled: May 2, 1994Date of Patent: December 27, 1994Assignee: Yamamoto Chemicals, Inc.Inventors: Yojiro Kumagae, Shigeo Fujita, Mansuke Matsumoto, Sayuri Wada, Shuuichi Hashimoto
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Patent number: 5342967Abstract: The improved two types of crystal modification of 2-n-toluidino-3-methyl-6-di-n-butylaminofluoran, as well as the crystalline toluene adduct thereof have high solubility in inner-phase solvent(s). Recording materials that use those compounds as electron donating color formers exhibit particularly good performance in various characteristics such as whiteness of the background, its storage stability, color rendition, sensitivity for color formation and image storage stability.Type: GrantFiled: July 31, 1992Date of Patent: August 30, 1994Assignee: Yamamoto Chemicals, Inc.Inventors: Shigeo Fujita, Mansuke Matsumoto, Yojiro Kumagae, Sayuri Wada, Shuichi Hashimoto
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Patent number: 5338866Abstract: The improved .beta.-type crystal modification of 2-(3-methylanilino)-3-methyl-6-diethylaminofluoran has high solubility in inner-phase solvents. The compound is very useful as a color former for pressure-sensitive recording materials and thermal recording materials. Recording materials that use this compound as color former exhibit good performance in various characteristics such as whiteness of the background, its storage stability, color rendition, sensitivity for color formation and color fastness of image.Type: GrantFiled: December 11, 1992Date of Patent: August 16, 1994Assignee: Yamamoto Chemicals, Inc.Inventors: Yojiro Kumagae, Shigeo Fujita, Mansuke Matsumoto, Sayuri Wada, Shuuichi Hashimoto
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Patent number: 5331097Abstract: A diamino-xanthene colorant is provided having the following structure: ##STR1## where Y is a poly(oxyalkylene) substituent having a straight or branched polymer chain of at least 3 monomer units selected from ethylene oxide, propylene oxide, butylene oxide and glycidol;R.sub.1 and R.sub.2 are independently selected from H, C1-C4 alkyl, C1-C4 alkoxy, Cl, Br and I;X is selected from H, SO.sub.3 --, CO.sub.2 -- and COOR.sub.3, where R.sub.3 is C1-C4 alkyl or aryl; andeach Z is independently selected from SO.sub.3 --, CO.sub.2 --, COOR.sub.4, Cl and OH, where R.sub.4 is C1-C4 alkyl or aryl, and n is 0, 1, or 2; the colorant is synthesized by condensing two moles of an N,N-bis(poly(oxyalkylene))-p-methoxyaniline and o-formylbenzene sulfonic acid.Type: GrantFiled: August 13, 1991Date of Patent: July 19, 1994Assignee: Milliken Research CorporationInventors: Timothy B. Gunnell, John B. Hines, Jr., Carey N. Barry, Jr.
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Patent number: 5324704Abstract: Disclosed are novel fluoran compounds represented by the formula (I): ##STR1## wherein R.sub.1 and R.sub.2 are different groups selected from cyclohexyl, n-butyl and isobutyl, e.g., in the form of crystals characterized by a specific X-ray diffraction diagram; crystalline toluene adducts thereof; and recording materials containing these fluoran compounds.Type: GrantFiled: March 29, 1993Date of Patent: June 28, 1994Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
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Patent number: 5315015Abstract: Compounds of the formula ##STR1## wherein F is a fluorescing compound; Y is --NH-- or a single covalent bond; Z is a straight or branched alkylene chain of 2 to 10 carbon atoms which is substituted by at least one hydrophilic group; Q is oxygen or sulfur; and X is a ligand-analog, the ligand-analog capable of being recognized by an antibody specific to the corresponding ligand. These compounds have improved properties in fluorescence polarization immunoassays by possessing either a better intensity and/or a larger span.Type: GrantFiled: November 10, 1992Date of Patent: May 24, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Raymond A. Hui, Kathryn S. Schwenzer
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Patent number: 5300661Abstract: Disclosed are novel crystal of the fluoran compound represented by the formula (I) ##STR1## ,characterized by a specific X-ray diffraction diagram; preparation process thereof; and recording materials comprising the crystal.Type: GrantFiled: July 21, 1993Date of Patent: April 5, 1994Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
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Patent number: 5283222Abstract: Disclosed are novel crystal of the fluoran compound represented by the formula (I) ##STR1## , characterized by a specific X-ray diffraction diagram; preparation process thereof; and recording materials comprising the crystal.Type: GrantFiled: September 24, 1992Date of Patent: February 1, 1994Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
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Patent number: 5274155Abstract: A process for the preparation of compounds of formula ##STR1## and pharmaceutically acceptable salts thereof; wherein X is --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or --CH.sub.2 O-- (where O is linked to Z); Z is a hydrophobic anchor R.sub.1 is hydrogen, alkyl, cycloalkyl or aryl; comprising the steps of:(A) reacting a compound of formula ##STR2## with a compound of formula ##STR3## or a compound of formula ##STR4## in the presence of an amine base or an alkali metal hydride in an organic solvent to form a compound having the formula ##STR5## (B) heating the compound of formula IX at a temperature of from about 100.degree. C. to about 200.degree. C., to form a compound of formula ##STR6## and (C) quenching the compounds of formula VIII with an acid provides the compounds of formula I.Type: GrantFiled: December 7, 1992Date of Patent: December 28, 1993Assignee: E. R. Squibb & Sons, Inc.Inventors: John K. Thottathil, David Kronenthal
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Patent number: 5250708Abstract: A poly(oxyalkylene) substituted xanthene colorant is providing having the following structure: ##STR1## where Y is a poly(oxyalkylene) substituent having a straight or branched polymer chain of from 3 to 400 monomer units selected from ethylene oxide, propylene oxide, butylene oxide and glycidol;R.sub.1 and R.sub.2 are independently selected from H, C1-C8 alkyl, aryl and Y, provided that if either R.sub.1 or R.sub.2 are Y, the other is not H;R.sub.3 and R.sub.4 are independently selected from H, C1-C4 alkyl, C1-C4 alkoxy, Cl, Br and I;X is selected from H, SO.sub.3 --, CO.sub.2 -- and COOR.sub.5, where R.sub.5 is C1-C4 alkyl or aryl; andeach Z is independently selected from SO.sub.3 --, CO.sub.2 --, COOR.sub.6, Cl, and OH, where R.sub.6 is C1-C4 alkyl or aryl, and n is 0, 1, 2 or 3.The colorant is synthesized using a novel poly(oxyalkylene) substituted aminophenol intermediate.Type: GrantFiled: August 13, 1991Date of Patent: October 5, 1993Assignee: Milliken Research CorporationInventor: Carey N. Barry, Jr.
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Patent number: 5248791Abstract: A fluorescence polarization immunoassay (FPIA) for detecting the presence of one or more amphetamine-class analytes in a test sample is provided. The immunoassay uses competition between the analyte and a fluorescently labeled tracer for the binding site on an antibody specific for phenethylamine derivatives. The concentration of amphetamine-class analyte in the sample determines the amount of tracer that binds to the antibody. The amount of tracer/antibody complex formed can be quantitatively measured and is inversely proportional to the quantity of analyte in the test sample. The invention relates to tracers, to immunogens used to elicit antibodies for use as assay reagents, and to assay kits incorporating these tracers and assay reagents.Type: GrantFiled: January 14, 1992Date of Patent: September 28, 1993Assignee: Abbott LaboratoriesInventors: Paul J. Brynes, Donald D. Johnson, Cynthia M. Molina, Charles A. Flentge, Patrick F. Jonas
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Patent number: 5244769Abstract: A light-sensitive image-forming material is disclosed, comprising a support having thereon a recording layer containing a leuco dye which forms color upon oxidative development, a photo-oxidizing agent and a reducing agent, wherein the leuco dye is an xanthene compound having a cyclic amino group at the 2-position. The light-sensitive image-forming material of the present invention provides an image having satisfactory color density and stability to light after imagewise exposure and fixation.Type: GrantFiled: March 7, 1991Date of Patent: September 14, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Naoto Yanagihara, Akihiko Takeda, Akira Igarashi
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Patent number: 5245049Abstract: Disclosed are a crystal and crystalline solvate of a fluoran compound represented by the formula ##STR1## wherein R.sub.1 is ##STR2## and which are useful as chromogenic compounds in recording materials such as pressure-sensitive and heat-sensitive recording materials, a process for preparation of said crystal and said crystalline solvate, and recording materials comprising said crystal or said crystalline solvate.Type: GrantFiled: July 12, 1991Date of Patent: September 14, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Atsuo Otsuji, Masakatsu Nakatsuka, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
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Patent number: 5220038Abstract: Disclosed are novel fluoran compounds represented by the formula (I): ##STR1## wherein R.sub.1 and R.sub.2 are different groups selected from cyclohexyl, n-butyl and isobutyl, e.g., in the form of crystals characterized by a specific X-ray diffraction diagram; crystalline toluene adducts thereof; and recording materials containing these fluoran compounds.Type: GrantFiled: July 18, 1990Date of Patent: June 15, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
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Patent number: 5210221Abstract: Disclosed are a crystal of a fluoran compound having the formula (I) comprising exhibiting high peaks at diffraction angles (2.theta.) of 7.5.degree. and 17.0.degree. and relatively high peaks at diffraction angles (2.theta.) of 15.1.degree., 19.1.degree., 21.5.degree. and 25.3.degree. in an X-ray diffraction diagram by the Cu-K.alpha. beam and a crystal of a fluoran compound having the formula (II) comprising exhibiting high peaks at diffraction angles (2.theta.) of 5.5.degree. and 19.2.degree. in an X-ray diffraction diagram by the Cu-K.alpha. beam, which is useful as a color forming compound in recording materials.Type: GrantFiled: September 10, 1991Date of Patent: May 11, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
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Patent number: 5208209Abstract: Novel fluoran compounds represented by the formula (I): ##STR1## wherein R.sup.1 is an alkyl group having from 1 to 4 carbon atoms, preparation process of the fluoran compounds, and a heat-sensitive and a pressure-sensitive recording material comprising the fluoran compound, are disclosed.Type: GrantFiled: December 19, 1991Date of Patent: May 4, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Atsuo Otsuji, Masakatsu Nakatsuka, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
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Patent number: 5194632Abstract: Disclosed are a novel fluoran compound represented by the formula (I): ##STR1## and a heat-sensitive recording paper which is obtained by using the fluoran compound as a chromogenic compound and is excellent in preserving stability.Type: GrantFiled: July 31, 1990Date of Patent: March 16, 1993Assignee: Mitsui Toatsu Chemicals Inc.Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
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Patent number: 5185453Abstract: Disclosed are novel crystal of the fluoran compound represented by the formula ##STR1## , characterized by a specific X-ray diffraction diagram; preparation process thereof; and recording materials comprising the crystal.Type: GrantFiled: June 19, 1991Date of Patent: February 9, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
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Patent number: 5166350Abstract: A process for the preparation of a fluoran compound of the formula ##STR1## wherein R, R.sub.1, R.sub.2 and R.sub.4 are each independently hydrogen, halogen, lower alkyl or lower alkoxy,R.sub.3 is hydrogen, halogen, lower alkyl, lower alkoxy or --NX.sub.3 X.sub.4, or (R.sub.1 and R.sub.2) or (R.sub.3 and R.sub.4) each pair together with the carbon atoms to which they are attached, form a fused benzene nucleus,X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are each independently hydrogen, alkyl containing not more than 12 carbon atoms which is unsubstituted or substituted by cyano, halogen, hydroxy, tetrahydrofuryl or lower alkoxy, or are cycloalkyl, aryl or aralkyl or (X.sub.1 and X.sub.2) or (X.sub.3 and X.sub.Type: GrantFiled: September 30, 1991Date of Patent: November 24, 1992Assignee: Ciba-Geigy CorporationInventors: Davor Bedekovic, Jerry L. Pool, Brian J. Williams, Robert Garner, John B. Henshall
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Patent number: 5149830Abstract: Substituted xanthene compounds are described which are capable of functioning as absorbers in high intensity light protective compositions and in materials used to prevent the transmission of high intensity light at selected wavelengths. Also described are high intensity light protective compositions containing an effective amount of a substituted xanthene compound and a polymeric compound and a material which prevents transmission of high intensity light at wavelengths between about 482 to about 556 nanometers. The material of this invention can be used to make protective eyewear, optical filters, shields for protecting a persons body from high intensity light, or shields for protecting components of an optical instrument from high intensity light.Type: GrantFiled: February 23, 1990Date of Patent: September 22, 1992Assignee: Steadfast, Inc.Inventors: Louis Locatell, Kenneth Norland, F. Donald Roberts, Charles Zepp
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Patent number: 5110952Abstract: A method of producing a high melting point 3-dibutyl amino-6-methyl-7-anilinofluoran characterized by peaks at diffraction angle (2 .theta.) of 6.9.degree., 11.0.degree., 18.5.degree. and 18.9.degree. in X-ray diffractiometry using Cu-K .alpha. ray and having a melting point in the range of 179.degree.-186.degree. C., which comprises: condensing 2-(4-dibutylamino-2-hydroxy-benzoyl) benzoic acid with 4-methoxy-2-methyldiphenylamine in the presence of concentrated sulfuric acid to provide a phthalide at a temperature in the range of 0.degree.-50.degree. C., neutralizing the phthalide, and then subjecting the phthalide to ring closure reaction using an alkali in an amount of 0.5-15 mols per mol of the compound used in smaller amounts of 2-(4-dibutylamino-2-hydroxy-benzoyl) benzoic acid and 4-methoxy-2-methyldiphenylamine at a temperature of not less than 50.degree. C. in the presence or absence of an organic solvent.Type: GrantFiled: December 20, 1990Date of Patent: May 5, 1992Assignee: Yamamoto Chemicals, Inc.Inventors: Hiroaki Harada, Yasuhisa Iwasaki