Plural Nitrogens Bonded Directly To The Xanthene Ring System (e.g., 2,6 Diaminofluorans, Etc.) Patents (Class 549/226)
  • Patent number: 5097044
    Abstract: Pyran-containing phthalides of the formula ##STR1## in which R is hydrogen, alkyl which has not more than 12 carbon atoms and is unsubstituted or substituted by halogen, cyano, hydroxyl or lower alkoxy, or is cycloalkyl, phenalkyl or phenyl each of which is unsubstituted or substituted, or an unsubstituted or substituted heterocyclic radical, R' is hydrogen, or R together with R' is C.sub.2 -C.sub.3 alkylene which is unsubstituted or substituted by methyl,X is hydrogen, alkyl having 1 to 12 carbon atoms or a monocyclic or polycyclic aromatic or heteroaromatic radical and the ring A is a benzene or naphthalene ring which is unsubstituted or monosubstituted or polysubstituted by halogen, lower alkyl, lower alkoxy or lower alkoxycarbonyl, and the ring B is an aromatic or heteroaromatic radical which has 6 ring atoms and which can contain an aromatic fused ring, it being possible for both the ring B and the fused ring to be substituted.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: March 17, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Rox Phaff
  • 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: 5071480
    Abstract: Fluoran color former mixtures which contain at least(a) a fluoran compound of the formula ##STR1## (b) a fluoran compound of the formula ##STR2## in which R.sub.1, R.sub.3 and R.sub.4 are hydrogen, halogen, lower alkyl or lower alkoxy,R.sub.2 is halogen, lower alkyl or lower alkoxy,X.sub.1, X.sub.2, Y.sub.1 and Y.sub.2 are hydrogen, unsubstituted or halogen, hydroxyl, cyano or (lower alkoxy)-substituted alkyl, cycloalkyl, aryl or aralkyl,X.sub.3 and Y.sub.3 are hydrogen, unsubstituted or halogen-hydroxyl-, cyano- or (lower alkoxy)-substituted alkyl, cycloalkyl, aryl or aralkyl,X.sub.4 and Y.sub.4 are unsubstituted or halogen-, hydroxyl-, cyano- or (lower alkoxy)-substituted alkyl, cycloalkyl or aralkyl or(X.sub.1 and X.sub.2), (X.sub.3 and X.sub.4), (Y.sub.1 and Y.sub.2) and Y.sub.3 and Y.sub.
    Type: Grant
    Filed: February 28, 1990
    Date of Patent: December 10, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Zink
  • Patent number: 5017710
    Abstract: Fluoran compounds represented by the general formula (I) ##STR1## (where R is an alkyl group having 9 to 12 carbon atoms) and coloring recording materials containing the said compounds as coloring components, and benzoic acid derivatives represented by the general formula (II) ##STR2## (where R is an alkyl group having 9 to 12 carbon atoms).
    Type: Grant
    Filed: October 24, 1989
    Date of Patent: May 21, 1991
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Tetsuo Igaki, Akio Kaneko, Sumio Manaka, Kimiaki Kinoshita
  • 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: 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: 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: 4837210
    Abstract: The invention relates to novel fluoran compounds of the general formula ##STR1## wherein R.sub.1 and R.sub.2, each independently of the other, are lower alkyl;A is ##STR2## or a pyrrolidinyl, piperidino, morpholino or piperazino radical; and R.sub.3 and R.sub.4, each independently of the other, are C.sub.1 -C.sub.12 alkyl, cycloalkyl, phenyl or phenyl substituted by lower alkyl or lower alkoxy.These compounds are particularly suitable for use as color formers in pressure-sensitive or heat-sensitive recording materials.
    Type: Grant
    Filed: January 27, 1987
    Date of Patent: June 6, 1989
    Assignee: Appleton Papers Inc.
    Inventors: Patricia Dwyer-Hallquist, William J. Becker, Robert E. Miller, Kenneth D. Glanz
  • 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: 4806657
    Abstract: A process for the preparation of fluoran compounds which are substituted by basic groups and have the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are each independently hydrogen, halogen or lower alkyl, or R.sub.1 and R.sub.2 together with the carbon atom to which they are attached are a fused benzene nucleus,X.sub.1 and X.sub.2 are each independently hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aryl or aralkyl, orX.sub.1 and X.sub.2 together with the nitrogen atom to which they are attached are a 5- or 6-membered heterocyclic radical, andY is unsubstituted or substituted alkyl, cycloalkyl, aryl or aralkyl, andthe ring A is unsubstituted or substituted, which process comprises reacting a ketonic acid of the formula ##STR2## with a substituted 4-formylaminophenol derivative of the formula ##STR3## wherein A, R.sub.1, R.sub.2, R.sub.3, X.sub.1, X.sub.
    Type: Grant
    Filed: May 5, 1986
    Date of Patent: February 21, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Zink
  • 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: 4727162
    Abstract: A molecular compound of a fluoran compound and a ketone useful as a color former for heat or pressure-sensitive color-developable recording material.
    Type: Grant
    Filed: November 25, 1986
    Date of Patent: February 23, 1988
    Assignee: Shin Nisso Kako Co., Ltd.
    Inventors: Masakichi Yahagi, Tetsuo Igaki
  • Patent number: 4695640
    Abstract: Addition compound of fluoran compound and ketone useful as color former for heat or pressure-sensitive color-developable recording material.
    Type: Grant
    Filed: October 21, 1985
    Date of Patent: September 22, 1987
    Assignee: Shin Nisso Kako Co., Ltd.
    Inventors: Masakichi Yahagi, Tetsuo Igaki, Shinji Yoshinaka, Kimiaki Kinoshita, Morikuni Saito, Toshiyuki Yamashita, Morio Nanbu
  • Patent number: 4694088
    Abstract: A fluoran compound represented by general formula (I): ##STR1## wherein R.sub.1 represents a straight or branched alkyl group having 1 to 8 carbon atoms, a cyclohexyl (C.sub.1 -C.sub.2) alkyl group, a cyclohexyl group, a phenyl group which may be substituted by chlorine, an alkoxyalkyl group, a benzyl group which may be substituted by chlorine, or a hydrogen atom;, R.sub.2 represents a hydrogen atom, a halogen atom, a lower alkyl group having 1 to 4 carbon atoms, a phenyl group which may be substituted by chlorine, a benzyl group which may be substituted by chlorine, a lower alkoxy group or a lower alkoxyalkyl group; R.sub.3 represents a hydrogen atom, a chlorine atom, a fluorine atom or a lower alkyl group having 1 to 4 carbon atoms; and n is 2.
    Type: Grant
    Filed: November 25, 1985
    Date of Patent: September 15, 1987
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Kazuo Kaneko, Susumu Suzuka, Michihiro Gonda, Mikiko Kanasugi
  • Patent number: 4665199
    Abstract: 3-N-isobutylethylamino-6-methyl-7-phenylamino fluoran of formula (I) ##STR1## is described.
    Type: Grant
    Filed: December 23, 1985
    Date of Patent: May 12, 1987
    Assignee: Shin Nisso Kako Co., Ltd.
    Inventors: Masakichi Yahagi, Tetsuo Igaki, Sinzi Yoshinaka, Kousaku Morita, Morikuni Saito, Kimiaki Kinoshita
  • Patent number: 4642357
    Abstract: A compound of the formula (I) ##STR1## wherein R is methyl or ethyl, useful in chromogenic recording materials, is described.
    Type: Grant
    Filed: May 20, 1986
    Date of Patent: February 10, 1987
    Assignee: Shin Nisso Kako Cp., Ltd.
    Inventors: Masakichi Yahagi, Tetsuo Igaki, Sinzi Yosinaka, Kousaku Morita, Morikuni Saito, Kimiaki Kinoshita
  • Patent number: 4629800
    Abstract: Fluoran compounds of the structural formula: ##STR1## wherein R.sub.1 is propyl or butyl, R.sub.2 is an alkyl of from one to four carbon atoms, R.sub.3 is methyl or ethyl, and R.sub.4 is hydrogen or methyl are particularly suitable for use in providing high quality pressure, heat or electrothermal sensitive recording sheets containing a color former in operative association with an electron-accepting substance.
    Type: Grant
    Filed: March 1, 1985
    Date of Patent: December 16, 1986
    Assignee: Kanzaki Paper Manufacturing Co., Ltd.
    Inventors: Naoki Yonese, Masayuki Omatsu, Mitsuru Kondo
  • Patent number: 4597795
    Abstract: A novel 6-tetrahydrofurfurylaminofluoran compound useful as a color former (precursory colorant) for a heat-sensitive recording sheet is of the formula (I): ##STR1## wherein R.sub.1 is H, C.sub.1-8 alkyl, tetrahydrofurfuryl, phenyl, alkyl(C.sub.1-5)phenyl, or C.sub.3-8 cyclic alkyl, R.sub.2 is H, Cl, F, C.sub.1-5 alkyl, C.sub.1-5 alkoxy, C.sub.2-10 alkoxyalkyl, phenyl or benzyl, and R.sub.3 is H, Cl, F, C.sub.1-5 alkyl and C.sub.2-7 acryl.
    Type: Grant
    Filed: January 22, 1985
    Date of Patent: July 1, 1986
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Hideyuki Sensui, Susumu Suzuka, Michihiro Gonda, Katsumasa Kikkawa
  • 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: 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: 4414399
    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)benzoid acids and substituted 4-hydroxyacetanilides or alkyl phenols which are esterified with alkyl halides or dialkyl sulfates.
    Type: Grant
    Filed: April 15, 1983
    Date of Patent: November 8, 1983
    Assignee: Sterling Drug Inc.
    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
  • Patent number: 4341403
    Abstract: A fluoran compound represented by the formula: ##STR1## wherein R.sub.1 and R.sub.2 each represents an alkyl group containing up to 18 carbon atoms, R.sub.3 represents an alkyl group, a halogenated alkyl group, or an alkoxyalkyl group containing up to 18 carbon atoms, and X represents a halogen atom, a process for preparing such fluoran compound and a pressure-or heat-sensitive recording sheet comprising such fluoran compound as a color former, which are capable of providing black images having excellent stability, e.g., with respect to light.
    Type: Grant
    Filed: April 18, 1980
    Date of Patent: July 27, 1982
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Akira Igarashi, Kozo Sato, Ken Iwakura
  • Patent number: 4330473
    Abstract: The present invention discloses novel fluoran compound useful as the lactone electron donative color-forming agents having the general formula: ##STR1## wherein, R.sub.1, R.sub.2 and R.sub.4 are respectively hydrogen, methyl or ethyl groups; R.sub.3 is hydrogen or a methyl group; and R.sub.5 is a phenyl group or a phenyl group substituted with from one to five methyl groups. The compound of the invention is soluble in aromatic solvents as well as in aromatic-aliphatic mixed solvents and also has excellent light fastness after developing color.
    Type: Grant
    Filed: November 26, 1980
    Date of Patent: May 18, 1982
    Assignee: Yamamoto Kagaku Gosei Kabushiki Kaisha
    Inventors: Yoshihiro Hatano, Kenji Yamamoto