Rhodamines Patents (Class 549/227)
  • Patent number: 5130446
    Abstract: Fluorescent linker moieties are provided which comprise a fluorescent compound such as fluorescein attached to a linker moiety such that a functional group of the linker is available for attachment to an affinity molecule such as a nucleic acid which has an N.sup.4 (substituted amino) cytosine moiety. Probes tagged with fluorescent derivatives such as fluorescein, tetramethyrhodamine or tetraethylrhodamine may be detected by fluorescence spectroscopic methods.
    Type: Grant
    Filed: March 14, 1989
    Date of Patent: July 14, 1992
    Assignee: Siska Diagnostics, Inc.
    Inventors: Gary F. Musso, Soumitra Ghosh, Leslie E. Orgel, Geoffrey M. Wahl, Emil T. Kaiser
  • Patent number: 5111472
    Abstract: A novel class of dye is disclosed which is particularly efficient and stable for dye laser applications, lasing between 540 and 570 nm.
    Type: Grant
    Filed: May 14, 1991
    Date of Patent: May 5, 1992
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Peter R. Hammond, James F. Feeman
  • Patent number: 5087706
    Abstract: 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: Grant
    Filed: September 18, 1990
    Date of Patent: February 11, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Atsuo Otsuji, Masakatsu Nakatsuka, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
  • Patent number: 5055594
    Abstract: A fluorogenic substrate for tryptophanase useful for identifying an unknown microorganism is a fluorescent dye linked to an amino acid by a carbamate or thiocarbamate group. In preferred substrates, the dye is fluorescein or 7-amino-4-methyl coumarin and the amino acid linked thereto is cysteine, threonine or serine.
    Type: Grant
    Filed: July 19, 1990
    Date of Patent: October 8, 1991
    Assignee: Becton, Dickinson and Company
    Inventor: Patrick D. Mize
  • Patent number: 5049673
    Abstract: The present invention discloses a new class of calcium specific fluorescent indicator dyes having visible excitation and emission wavelengths. The new fluorescent indicator dyes combine at least one tricyclic chromophore with a tetracarboxylate parent CA.sup.2+ chelating compound having the octacoordinate pattern of liganding groups characteristic of BAPTA to give a rhodamine-like or fluorescein-like fluorophore. Binding of calcium.sup.2+ increases the fluorescence of the new compounds by up to 40-fold. The calcium.sup.2+ dissociation constants are in the range 0.37-2.3 microM, so that the new indicators give better resolution of high [CA.sup.2+ ] levels than were previously obtainable with predecessor compounds such as quin-2 or fluo-2. The visible excitation wavelengths of the new compounds are more convenient for fluorescent microscopy and flow cytometry than the UV required by previous indicators.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: September 17, 1991
    Assignee: The Regents of the University of California
    Inventors: Roger Y. Tsien, Akwasi Minta
  • Patent number: 5047559
    Abstract: A novel class of dye is disclosed which is particularly efficient and stable for dye laser applications, lasing between 540 and 570 nm.
    Type: Grant
    Filed: January 22, 1991
    Date of Patent: September 10, 1991
    Assignee: United States Department of Energy
    Inventors: Peter R. Hammond, James F. Feeman
  • Patent number: 5013827
    Abstract: Triggerable dioxetanes with a fluorescent molecule containing group bonded or tethered in the dioxetane so as to produce fluorescence from the group are described. The compounds are useful in immunoassays and in probes using enzymes or other chemicals for triggering the dioxetanes to produce light from the fluorescent molecule in the group as a signal.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: May 7, 1991
    Assignee: Board of Governors of Wayne State University
    Inventor: Arthur P. Schaap
  • Patent number: 4992560
    Abstract: A novel class of dye is disclosed which is particularly efficient and stable for dye laser applications, lasing between 540 and 570 nm.
    Type: Grant
    Filed: May 18, 1990
    Date of Patent: February 12, 1991
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Peter R. Hammond, James F. Freeman
  • Patent number: 4977278
    Abstract: Salts of esterified rhodamine dyes are prepared in granular form by precipitating the rhodamine dyes with sodium chloride from an aqueous medium containing a water-miscible solvent by adding the sodium chloride at 80.degree.-100.degree. C., which precipitates the dyes in liquid form from the aqueous medium, then stirring the liquid dyes to convert them into a droplet form and then chilling the droplets by direct cooling to below 65.degree. C.
    Type: Grant
    Filed: September 8, 1989
    Date of Patent: December 11, 1990
    Assignee: BASF Aktiengesellschaft
    Inventor: Karl Schmeidl
  • Patent number: 4952707
    Abstract: Chemiluminescent 1,2-dioxetane compounds are disclosed in which the molecule is stabilized at the 3-position on the dioxetane ring against decomposition prior to the molecule's coming in contact with a labile group-removing substance (e.g., an enzyme that will cleave the labile group to cause the molecule to decompose to form at least one light-emitting fluorophore) and substituted at the 4-position on the dioxetane ring with a fused polycyclic ring-containing fluorophore moiety bearing a labile ring substituent whose point of attachment to the fused polycyclic ring, in relation to this ring's point(s) of attachment to the dioxetane ring, is such that the total number of ring atoms separating these points of attachment, including the ring atoms at the points of attachment, is an odd whole number. These odd pattern substituted compounds decompose to emit light of greater intensity and of a different wavelength than that emitted by the corresponding even pattern substituted isomers.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: August 28, 1990
  • Patent number: 4945176
    Abstract: A novel class of dye is disclosed which is particularly efficient and stable for dye layer applications, lasing between 540 and 570 nm.
    Type: Grant
    Filed: June 8, 1989
    Date of Patent: July 31, 1990
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Peter R. Hammond, James F. Feeman
  • Patent number: 4935059
    Abstract: Basic rhodamine dyes suitable for use in recording fluids for the ink jet process and for coloring paper stock have the formula ##STR1## where L is C.sub.2 -C.sub.10 -alkylene,R.sup.1, R.sup.2 and R.sup.3 are each independently of the others hydrogen, substituted or unsubstituted C.sub.1 -C.sub.10 -alkyl or C.sub.5 -C.sub.7 -cycloalkyl or R.sup.1 and R.sup.2 together with the nitrogen atom linking them together are a hetero cyclic radical,An.sup..crclbar. is one equivalent of an anion and m and n are each independently of the other 0 or 1.
    Type: Grant
    Filed: June 15, 1989
    Date of Patent: June 19, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Udo Mayer, Andreas Oberlinner
  • Patent number: 4921973
    Abstract: A (+)-charged dye transition metal complex, particularly a complex of platinum and a (+)-charged dye such as rhodamine 123. These products demonstrate antitumor and radio-sensitizing activity.
    Type: Grant
    Filed: April 26, 1988
    Date of Patent: May 1, 1990
    Assignee: Johnson Matthey Inc.
    Inventors: Beverly A. Teicher, Robert C. Richmond, Lan B. Chen
  • Patent number: 4906749
    Abstract: Novel chromophor derivatives of cyclic anhydrides are provided which have the ability to react with a variety of organic substrates forming adducts which are useful in analytical techniques for the detection and measurement of biological compounds.
    Type: Grant
    Filed: January 24, 1989
    Date of Patent: March 6, 1990
    Assignee: Viomedics Inc.
    Inventor: Spyros Theodoropulos
  • Patent number: 4895961
    Abstract: Completely esterified rhodamine dyes of the formula ##STR1## where R, R.sup.2 and R.sup.4 are independently of one another methyl or ethyl, R.sup.1 and R.sup.3 are independently of one another hydrogen, methyl or ethyl, R.sup.5 and R.sup.6 are independently of one another hydrogen or methyl and A.sup..crclbar. is an anion, are prepared from compounds of the formula II ##STR2## or from the corresponding water addition products by esterification with dialkyl sulfates in solvents by using .gamma.-butyrolactone, alkylene carbonates, dialkyl carbonates, methoxypropyl acetate or dialkyl phthalates as solvent and working in the presence of an excess of a base, based on dialkyl sulfate.
    Type: Grant
    Filed: March 11, 1988
    Date of Patent: January 23, 1990
    Assignee: BASF Aktiengesellschaft
    Inventor: Karl Schmeidl
  • Patent number: 4833256
    Abstract: A fluoran derivative useful for a heat-sensitive recording material, having the following general formula I; ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, stand for an alkyl group having 1 to 9 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl group or a phenyl group substituted by an alkyl group having 1 to 4 carbon atoms, and R.sub.3 and R.sub.4, which may be the same or different, stand for an alkyl group having 1 to 6 carbon atoms or a phenyl group or R.sub.3 and R.sub.4 may form a 5- to 8-membered cycloalkane together with the carbon atom to which they are bonded.
    Type: Grant
    Filed: October 8, 1986
    Date of Patent: May 23, 1989
    Assignee: Showa Denko Kabushiki Kaisha
    Inventors: Teijiro Kitao, Tetsuhiko Yamaguchi, Katsumi Murofushi, Masato Futagami, Nobuyuki Nagato, Kunio Imamura
  • Patent number: 4826976
    Abstract: This invention relates to a color-shifted dye compounds containing at least one thermally unstable carbamate moiety which are useful in thermal imaging. These compounds may be represented by the formula [M--(X).sub.q ].sub.p D wherein M is a carbamate moiety; X is --N.dbd., --SO.sub.2 -- or --CH.sub.2 --; D taken with X and M represents the radical of a color-shifted organic dye, said carbamate moiety M comprising a tert-alkoxycarbonyl group, ##STR1## wherein R' is halomethyl or alkyl.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: May 2, 1989
    Assignee: Polaroid Corporation
    Inventors: Alan L. Borror, Ernest W. Ellis, Donald A. McGowan
  • Patent number: 4749796
    Abstract: This invention relates to a xanthene derivative that develops color on oxidation, so that it is favorably used for a photoresist, a PS plate or a proofing agent. The xanthene derivative, which has the following structural formula (I), is produced by putting a fluoran derivative represented by the following structural formula (II) to an esterification reaction and then to a reduction reaction. ##STR1## In the above formulae R.sub.1 and R.sub.2 independently stand for hydrogen, an alkyl radical with 1 to 8 carbon atoms, a tetrahydrofurfuryl radical, a substitued or an unsubstituted phenyl radical, a substituted or an unsubstituted benzyl radical or a cyclic alkyl radical; in addition, R.sub.1 and R.sub.2 are able to form a ring in pairs. R.sub.3 and R.sub.6 independently stand for hydrogen, chlorine, fluorine, a lower alkyl radical or a lower alkoxy radical. R.sub.4 and R.sub.
    Type: Grant
    Filed: December 6, 1985
    Date of Patent: June 7, 1988
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Hideyuki Sensui, Michihiro Gonda, Toshio Obara
  • Patent number: 4727056
    Abstract: A recording material comprising at least one electron-donating colorless dye having, in a 95% acetic acid solution, a maximum absorption at a wavelength of from 400 to 550 nm in the spectral absorption range of from 400 to 700 nm, and at least one fluoran derivative represented by formula (I) ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 each represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, nitro, amino, cyano, acylamino, dialkylamino or a halogen atom.
    Type: Grant
    Filed: April 9, 1986
    Date of Patent: February 23, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shojiro Sano, Ken Iwakura
  • Patent number: 4721702
    Abstract: A pressure-sensitive recording material is described, comprising an electron-accepting compound, and at least one of electron-donating colorless dyes represented by formula (I) or formula (II) ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, and R.sub.8 each represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, or a halogen atom; and R.sub.9 and R.sub.10 each represents a hydrogen atom or a lower alkyl group, provided that at least one of R.sub.1, R.sub.2, R.sub.3, and R.sub.4 represents a lower alkyl group or a lower alkenyl group.
    Type: Grant
    Filed: March 20, 1986
    Date of Patent: January 26, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Ken Iwakura, Hiroyuki Kawasaki, Shojiro Sano
  • Patent number: 4710569
    Abstract: Dyestuffs of the formula ##STR1## wherein F stands for an organic chromophore andZ stands for radicals of the formulae ##STR2## wherein R.sub.1 -R.sub.2 denote hydrogen, alkyl, cycloalkyl, alkenyl, aryl, aralkyl or a heterocyclic structure orR.sub.2 and R.sub.3 represent an optionally substituted amino group or together form a ring orR.sub.1 with R.sub.2 and/or R.sub.3 with R.sub.4 form a ring,A.sup.(-) denotes an anion,Y denotes an anionic group,m denotes 0-2 andn denotes 1-6,and wherein the chromophore and said radicals can carry further substituents, provided that the total number of anionic substituents is smaller than the total number of quaternary and quaternizable amino groups, are used for dyeing cellulose fibres, in particular paper.
    Type: Grant
    Filed: September 10, 1985
    Date of Patent: December 1, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Franke, Dieter Ockelmann, Roderich Raue, Peter Wild
  • Patent number: 4557862
    Abstract: The present invention relates to a new class of novel Rhodamine derivatives. These derivatives which are bisamide substitution products are nonfluorescent. Whereas the monoamide substitution products exhibit high fluorescence. Cleavage of a single specified amide bond by bond-specific proteinases will therefore convert the nonfluorescent bisamide derivative into a highly fluorescent monoamide derivative.
    Type: Grant
    Filed: October 28, 1983
    Date of Patent: December 10, 1985
    Assignee: University Patents, Inc.
    Inventors: Walter F. Mangel, Stephen Leytus, L. Lee Melhado
  • Patent number: 4491662
    Abstract: Dyes of the formula ##STR1## where F is an (m+n)-valent radical of a quinophthalone, dioxazine, indigo, quinacridone, triphenylmethane or rhodamine dye, M.sup..sym. is H.sup..sym. or one equivalent of a metal cation, m is 0, 1 or 2 and n is 1, 2, 3 or 4, and their salts, are very useful for dyeing and printing paper. If they are used for wet-end dyeing, the waste water is virtually colorless. The colorations obtained exhibit good lightfastness and good bleeding fastness.
    Type: Grant
    Filed: April 20, 1982
    Date of Patent: January 1, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Patsch, Manfred Ruske
  • Patent number: 4473498
    Abstract: Novel organic, water-soluble compounds having fiber-reactive and fiber-finishing properties and containing, as a fiber-reactive group, one or two .beta.-chloroethylsulfonylmethyl-benzoic acid amide groups. These compounds can be prepared (1) by reacting novel .beta.-chloroethylsulfonylmethyl-benzoic acid halide compounds with an organic, water-soluble compound having fiber-finishing properties and containing one or two amino groups, or (2) analogously to known and usual procedures, from precursors containing the .beta.-chloroethylsulfonylmethyl-benzoic acid amide grouping. The novel fiber-finishing compounds are applied to and fixed on suitable fiber materials, especially cellulose fiber material and natural or synthetic polyamide fiber materials, by methods corresponding to those which are conventional for application and fixation of fiber-reactive compounds. The above-mentioned .beta.
    Type: Grant
    Filed: July 30, 1981
    Date of Patent: September 25, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ludwig Schlafer, Reinhard Hahnle
  • Patent number: 4436920
    Abstract: Recording members having excellent light resistance are obtained by using as a dye precursor specific diarylaminofluoran compounds.
    Type: Grant
    Filed: March 11, 1982
    Date of Patent: March 13, 1984
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kozo Sato, Ken Iwakura, Akira Igarashi
  • Patent number: 4433156
    Abstract: A process for preparing 3,6-bis-diarylaminofluoran derivatives which comprises reacting a 3,6-bis-arylaminofluoran derivative with an arylating agent.
    Type: Grant
    Filed: April 5, 1982
    Date of Patent: February 21, 1984
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Sadao Ishige, Kozo Sato, Ken Iwakura
  • Patent number: 4405788
    Abstract: There are described novel dye compounds which are represented by the formula ##STR1## wherein A is ##STR2## X is H, alkyl, aryl such as phenyl or naphthyl, or substituted aryl; W is H or alkyl; R is H or alkyl; Z and Y are each H or monovalent radicals; l and p are each 1 or 2 and m and n are each integers of from 2-6.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: September 20, 1983
    Assignee: Polaroid Corporation
    Inventors: Louis Locatell, Jr., Charles M. Zepp, Ronald F. Cieciuch