Nitrogen Bonded Directly To The Xanthene Ring System (e.g., Rhodols, Aminofluorans, Etc.) Patents (Class 549/225)
  • Patent number: 4954631
    Abstract: 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, 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: Grant
    Filed: February 2, 1989
    Date of Patent: September 4, 1990
    Assignee: Shin Nisso Kako Co., Ltd.
    Inventors: Takeo Obitsu, Yutaka Ohnishi, Shinji Yoshinaka, Minoru Koguchi, Mitsuhiro Yanagita, Nobuyuki Hirai
  • 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: 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: 4894348
    Abstract: A method for conducting assays for an analyte, usually in a biological sample, utilizes reagents which contain biological ligands linked to fluorescein or a derivative of fluorescein through a linkage to the fluorescein nucleus selected from acetamido and thioacetamido. In these reagents, the fluorescence efficiency is improved over that obtained in the commonly used FITC-labeled reagents.
    Type: Grant
    Filed: July 1, 1987
    Date of Patent: January 16, 1990
    Inventors: Ronald Robert C., Phuc H. Nguyen, Gerald L. Rowley
  • 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: 4822878
    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: May 27, 1988
    Date of Patent: April 18, 1989
    Assignee: Viomedics, Inc.
    Inventor: Spyros Theodoropulos
  • Patent number: 4789742
    Abstract: Novel Isomaleimido and isophthalimido derivatives of chromophoric compounds are provided which are useful in analytic techniques for the detection and measurement of biological compounds such as bacteria, enzymes, hormones and the like.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: December 6, 1988
    Inventor: Spyros Theodoropulos
  • Patent number: 4780535
    Abstract: Conjugates of isomaleimides and isophthalimides and organic chromophoric compounds exhibiting fluorescence, luminescence, chemiluminescence or absorption of analytical value having the structural formula I and II ##STR1## wherein R is an organic aromatic molecule which may be substituted, heteroaromatic which may be substituted, aliphatic having 1 to 50 carbon atoms and which may be substituted or an organic chromophoric molecule exhibiting fluorescence, luminescence, chemiluminiescence or absorption of analytical value. R' is an organic chromophoric molecule exhibiting fluorescence, luminescence, chemiluminescence, or absorption of analytical value; R.sub.1 is hydrogen, halogen, carboxylic, alkyl, aryl, hydroxyl, amino group which may be substituted, nitro or sulfonic group. R.sub.2, R.sub.3 and R.sub.4 have the same meaning as R.sub.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: October 25, 1988
    Inventor: Spyros Theodoropulos
  • 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: 4728633
    Abstract: A recording material comprising a fluoran derivative represented by formula (I): ##STR1## wherein X.sub.1 represents a group derived from an amine, or a hydrogen atom; Y.sub.1 represents an alkyl group, an alkoxy group, an aryl group, a halogen atom, a group derived from an amine, an aralkyl group, or a hydrogen atom; Z.sub.1 represents a group derived from an amine residue; R.sub.1 represents a halogen atom, a lower alkyl group having 6 or less carbon atoms, or a hydrogen atom; and either R.sub.2 or R.sub.3 represents an alkoxy group or an aryloxy group, and either R.sub.2 or R.sub.3 which does not represent an alkoxy group or an aryloxy group represents an alkyl group, a halogen atom, or a hydrogen atom.
    Type: Grant
    Filed: July 29, 1986
    Date of Patent: March 1, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Masato Satomura, Ken Iwakura, Akira Igarashi
  • Patent number: 4687862
    Abstract: The fluoran compounds of the formula (I) are new red color forming chromogenic dyes. ##STR1## wherein R represents an isobutyl or isopentyl group, R.sub.1 represents a hydrogen or halogen atom or an alkyl group, R.sub.2 represents a hydrogen or halogen atom or an alkyl group, R.sub.3 represents a hydrogen atom, and R.sub.4 represents a hydrogen atom, or R.sub.4 and R.sub.1 as well as R.sub.2 and R.sub.3 taken together with the carbon atoms to which they are attached may form a benzene ring which may be substituted with a halogen atom. They are used, together with an acidic developer, in chromogenic recording materials for use in pressure sensitive copying paper, heat-sensitive recording paper and thermo-sensitive, reversible color changing composition.
    Type: Grant
    Filed: October 14, 1986
    Date of Patent: August 18, 1987
    Assignee: Shin Nisso Kako Co., Ltd.
    Inventors: Takeo Obitsu, Tetsuo Igaki, Kimiaki Kinoshita, Morio Nanbu, Shinichi Satoh
  • Patent number: 4668967
    Abstract: 3-N-isobutyl-ethylamino-7-phenylaminofluoran is a new green color former. It is used, together with an acidic substance, in color forming record materials for use in pressure sensitive copying paper, heat-sensitive recording paper and the like.
    Type: Grant
    Filed: May 28, 1986
    Date of Patent: May 26, 1987
    Assignee: Shin Nisso Kako Co., Ltd.
    Inventors: Masakichi Yahagi, Takeo Obitsu, Tetsuo Igaki, Kazuyuki Horisawa, Morio Nanbu, Kimiaki Kinoshita, Sumio Manaka
  • Patent number: 4612558
    Abstract: A fluoran compound having the formula: ##STR1## wherein each of R.sub.1 and R.sub.2 is a hydrogen atom, a straight chain or branched alkyl group having from 1 to 8 carbon atoms, a cyclohexyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted benzyl group, Q is ##STR2## (wherein X is a hydrogen atom, a halogen atom, or a straight chain or branched alkyl group having from 1 to 8 carbon atoms), ##STR3## (wherein X is as defined above), or --(CH.sub.2).sub.n OR.sub.4 (wherein R.sub.4 is a straight chain or branched alkyl group having from 1 to 8 carbon atoms, a cycloalkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted benzyl group, and n is an integer of from 1 to 8), and R.sub.3 is a hydrogen atom, a halogen atom, a lower fluoroalkyl group, an acyl group, an alkoxy group, an alkoxyalkyl group, or a straight chain or branched alkyl group having from 1 to 8 carbon atoms.
    Type: Grant
    Filed: March 12, 1985
    Date of Patent: September 16, 1986
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Mitsutoshi Anzai, Masahiko Yamaguchi, Kazuyuki Wakasugi, Susumu Suzuka, Michihiro Gonda, Toshiyuki Abe, Katsumasa Kikkawa, Mikiko Kanasugi
  • Patent number: 4585862
    Abstract: This disclosure relates to a method and reagents for determining ligands in biological fluids such as serum, plasma, spinal fluid, amnionic fluid and urine. In particular, this disclosure relates to a fluorescence polarization immunoassay procedure and to a novel class of tracer compounds employed as reagents in such procedures. The procedure disclosed combines the specificity of an immunoassay with the speed and convenience of fluorescence polarization techniques to provide a means for determining the amount of the specific ligand present in a sample.
    Type: Grant
    Filed: February 8, 1984
    Date of Patent: April 29, 1986
    Assignee: Abbott Laboratories
    Inventors: Chao-Huei J. Wang, Stephen D. Stroupe, Michael E. Jolley
  • Patent number: 4536220
    Abstract: A new fluoran derivative useful as a colorless chromogenic material has the following formula: ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, X and Y have the same meaning as defined hereinbefore.
    Type: Grant
    Filed: December 19, 1983
    Date of Patent: August 20, 1985
    Assignee: Kanzaki Paper Manufacturing Co., Ltd.
    Inventors: Mitsuru Kondo, Hiroshi Iwasaki, Haruo Omura, Nobuo Kanda
  • Patent number: 4515971
    Abstract: Dialkylamino-substituted 2-anilino-5'/6'-carboxyfluorans, 2-amino and substituted amino-5'/6'-carboxyfluorans, 1,3-dialkyl-5'/6'-carboxyfluorans, esterified dialkylamino-substituted 2-anilino-5'/6'-carboxyfluorans, 2-amino and substituted amino-5'/6'-carboxyfluorans, 1,3-dialkyl-5'/6'-carboxyfluorans and 3,3-(corresponding-substituted-diaryl)-5/6-carboxyphthalides useful as color formers, particularly in carbonless duplicating and thermal marking systems, are prepared by the interaction of 4/5-carboxy-2-(4-dialkylamino-substituted-2-hydroxybenzoyl)benzoic acids and substituted diphenylamines to produce the phthalides which are then subjected to ring closure to produce the carboxyfluorans and by the interaction of 4/5-carboxy-2-(4-dialkylamino-substituted-2-hydroxybenzoyl)benzoic acids and substituted 4-hydroxyacetanilides or alkyl phenols which are esterified with alkyl halides or dialkyl sulfates.
    Type: Grant
    Filed: July 6, 1981
    Date of Patent: May 7, 1985
    Assignee: Hilton-Davis Chemical Co.
    Inventors: Paul J. Schmidt, William M. Hung
  • Patent number: 4410708
    Abstract: Certain 3-substituted amino-7-substituted fluoran derivatives useful as color recording materials.
    Type: Grant
    Filed: February 3, 1976
    Date of Patent: October 18, 1983
    Assignee: Shin Nisso Kako Co., Ltd.
    Inventors: Masakichi Yahagi, Shoichi Horiuchi, Takahumi Toyama, Akio Kashiwagi, Teruo Suzuki, Tetsuo Igaki, Kazuyuki Horisawa, Mituhiro Shoji