Fluoran Or Derivative Patents (Class 503/221)
  • Patent number: 5376617
    Abstract: 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: Grant
    Filed: May 2, 1994
    Date of Patent: December 27, 1994
    Assignee: Yamamoto Chemicals, Inc.
    Inventors: Yojiro Kumagae, Shigeo Fujita, Mansuke Matsumoto, Sayuri Wada, Shuuichi Hashimoto
  • Patent number: 5340537
    Abstract: Temperature indicating compositions of dispersions in an aqueous binder of a color changing electron donating compound having a melting point greater than about 300.degree. F. and a polymeric electron accepting resin reactive with the electron donating compound to produce a visible and permanent color change and having a T.sub.g and non-volatility effective to provide a color change to coatings containing the composition upon exposure to a predetermined heat history. Temperature indicating materials are also disclosed containing a support coated on at least one surface thereof with the temperature indicating composition to the present invention.
    Type: Grant
    Filed: April 16, 1993
    Date of Patent: August 23, 1994
    Assignee: Big Three Industries, Inc.
    Inventor: Richard B. Barrett
  • Patent number: 5324704
    Abstract: 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: Grant
    Filed: March 29, 1993
    Date of Patent: June 28, 1994
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
  • Patent number: 5318939
    Abstract: Compounds of formula ##STR1## wherein R, L, X and Y are as defined in claim 1, are very suitable for use as UV absorbers in pressure-sensitive or heat-sensitive recording materials.
    Type: Grant
    Filed: September 11, 1991
    Date of Patent: June 7, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Hugh S. Laver, Mario Slongo
  • Patent number: 5302571
    Abstract: 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: Grant
    Filed: June 14, 1993
    Date of Patent: April 12, 1994
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Atsuo Otsuji, Masakatsu Nakatsuka, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
  • Patent number: 5300473
    Abstract: Disclosed are a crystal of a fluoran compound having the formula 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: Grant
    Filed: March 8, 1993
    Date of Patent: April 5, 1994
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
  • Patent number: 5288688
    Abstract: Disclosed is a thermal recording material having, on a support, a heat-sensitive coloring layer containing an electron-donating colorless dye, an isocyanate compound and an amino compound. The storage stability of the raw stock material as well as the color image stability of the material are excellent.
    Type: Grant
    Filed: March 24, 1993
    Date of Patent: February 22, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hiroshi Kawakami, Chiyoshi Nozaki, Ken Iwakura
  • Patent number: 5286703
    Abstract: A heat-sensitive recording material comprising a support having thereon a color-developing layer and at least one UV-absorbing layer with a light-transmittance of 70% or less at 400 nm, 5% or less at 370 nm, and 70% or more for entire visible light range, is disclosed.
    Type: Grant
    Filed: November 21, 1991
    Date of Patent: February 15, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Naotaka Wachi, Ken Iwakura, Kensuke Ikeda, Katsuya Takemasa
  • Patent number: 5283222
    Abstract: 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: Grant
    Filed: September 24, 1992
    Date of Patent: February 1, 1994
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
  • Patent number: 5270281
    Abstract: 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: Grant
    Filed: June 22, 1992
    Date of Patent: December 14, 1993
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Atsuo Otsuji, Toshihiro Motoshima, Yoshimitsu Tanabe, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Masakatsu Nakatsuka, Akihiro Yamaguchi
  • Patent number: 5260252
    Abstract: Disclosed is a method and material for producing and developing thermal latent images. Upon imagewise thermal exposure of a heat sensitive recording material, the recording material selectively yields both a latent image and a visually readable image. The latent image may comprise confidential data or text, and may subsequently be rendered visually readable by an authorized recipient.
    Type: Grant
    Filed: July 24, 1990
    Date of Patent: November 9, 1993
    Assignee: Nashua Corporation
    Inventors: Frederick G. Frangie, Roberta R. Arbree
  • Patent number: 5250492
    Abstract: Carbonless coating compositions which can be printed onto one or more sheets of a business form or mailer to provide a visible image which is sharper and darker than previous coatings are provided. The compositions also find use on security documents and safety papers to provide a covert image on the document beneath information which may be subject to attempted alteration, such as the amount written on a check. The covert image becomes visible upon the application of pressure or solvent in the area coated to provide evidence of the attempted alteration. The self-contained composition includes an admixture of a color former, a color developer, and a plurality of pressure-rupturable microcapsules containing a solvent. Another solvent-sensitive composition includes an admixture of a color former and a color developer.
    Type: Grant
    Filed: March 7, 1991
    Date of Patent: October 5, 1993
    Assignee: The Standard Register Company
    Inventors: Mark D. Dotson, Frank V. Parenti
  • Patent number: 5250493
    Abstract: A thermosensitive recording material having a support and a thermosensitive coloring layer formed on the support, which thermosensitive coloring layer includes at least a first thermosensitive coloring layer containing at least one leuco dye having formula (I), (II) or (III) and a color developer capable of inducing color formation in the leuco dye under application of heat thereto, and a second thermosensitive coloring layer containing at least one leuco dye having formula (IV) and a color developer capable of inducing color formation in the leuco dye under application of heat thereto. The leuco dye for use in the first thermosensitive coloring layer has the absorption intensity in the near infrared region, and the leuco dye for use in the second thermosensitive coloring layer has the absorption intensity in the visible spectrum.
    Type: Grant
    Filed: November 22, 1991
    Date of Patent: October 5, 1993
    Assignee: Ricoh Company, Ltd.
    Inventors: Takashi Ueda, Yasuhiko Watanabe
  • Patent number: 5246905
    Abstract: A thermosensitive recording material which contains an aromatic isocyanate compound, an imino compound having at least one >C.dbd.
    Type: Grant
    Filed: December 24, 1991
    Date of Patent: September 21, 1993
    Assignee: Mitsubishi Paper Mills Limited
    Inventors: Mikiya Sekine, Hidetaka Tsukada
  • Patent number: 5242886
    Abstract: A pressure-sensitive recording sheet comprises a microencapsulated divinylphthalide compound represented by the following formula (I): ##STR1## wherein the microcapsules have the following particle size distribution:4.0 .mu.m.ltoreq.D.sub.50 .ltoreq.10.0 .mu.mD.sub.90 /D.sub.10 .ltoreq.2.0.
    Type: Grant
    Filed: July 15, 1992
    Date of Patent: September 7, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shojiro Sano, Masanobu Takashima
  • Patent number: 5231069
    Abstract: Heat-sensitive recording paper which employs as a chromogenic compound a novel fluoran compound represented by the formula: ##STR1## and prepared reacting a benzoic acid derivative of the formula: ##STR2## with a diphenylamine derivative of the formula: ##STR3## wherein R is a lower alkyl group have excellent stability.
    Type: Grant
    Filed: December 4, 1992
    Date of Patent: July 27, 1993
    Assignee: Mitsui Toatsu Chemicals Inc.
    Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
  • Patent number: 5220038
    Abstract: 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: Grant
    Filed: July 18, 1990
    Date of Patent: June 15, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
  • Patent number: 5210064
    Abstract: The addition, to a thermal imaging medium comprising a color-forming compound which undergoes a change of color upon heating above a color-forming temperature for a color-forming time, the color-forming compound being of the cyclic sulfonamide type described in U.S. Pat. Nos. 4,720,449 and 4,960,901, of a quinone or hydroquinone increases the sensitivity of the imaging medium and helps to prevent fading of images produced therefrom while the images are being projected.
    Type: Grant
    Filed: November 20, 1991
    Date of Patent: May 11, 1993
    Assignee: Polaroid Corporation
    Inventors: Rita S. Shon Baker, Larry C. Takiff
  • Patent number: 5208209
    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: December 19, 1991
    Date of Patent: May 4, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Atsuo Otsuji, Masakatsu Nakatsuka, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
  • Patent number: 5206208
    Abstract: The addition, to a thermal imaging medium comprising a color-forming compound which undergoes a change of color upon heating above a color-forming temperature for a color-forming time, the color-formingcompound being of the cyclic sulfonamide type described in U.S. Pat. Nos. 4,720,449 and 4,960,901,of a source of zinc, nickel, copper(II), cobalt(II) or aluminum(III) cations increases the sensitivity of the imaging medium and helps to prevent fading of images produced therefrom while the images are being projected.
    Type: Grant
    Filed: November 20, 1991
    Date of Patent: April 27, 1993
    Assignee: Polaroid Corporation
    Inventors: Rong C. Liang, William C. Schwarzel, Rita S. Shon Baker, Robert P. Short, Stephen R. Sofen, Michael A. Young
  • Patent number: 5206210
    Abstract: Disclosed is a heat-sensitive recording material comprising (A) a support and (B) a heat-sensitive recording layer formed on the support and containing a colorless or pale-colored basic dye and a color developing material which develops a color on contact with the dye, the recording material being characterized in that the color developing material comprises at least one member selected from the group consisting of o-naphthoic acid and polyvalent metal salts thereof.
    Type: Grant
    Filed: July 23, 1991
    Date of Patent: April 27, 1993
    Assignee: Kanzaki Paper Manufacturing Co., Ltd.
    Inventors: Tetsuo Tsuchida, Yukihiro Abe, Takehiro Minami, Naoto Arai
  • Patent number: 5206209
    Abstract: A heat-sensitive recording sheet of this invention comprises in a heat-sensitive color-developing layer both bis(4-hydroxyphenyl)butylacetate as an organic color-developing agent and a particular fluorane-leuco dye. This sheet provides an intense clear image less discoloration and superior heat-resistant preservability.
    Type: Grant
    Filed: April 10, 1991
    Date of Patent: April 27, 1993
    Assignee: Jujo Paper Co., Ltd.
    Inventors: Toshiaki Minami, Tadakazu Fukuchi, Toshio Kaneko
  • Patent number: 5206118
    Abstract: A color-change dosimeter film made of a halogen-containing polymer in which is dispersed an acid-sensitive leuco dye, which dye a) is substantially free from groups that are sensitive to high-energy radiation and b) becomes colored in acid. This color-change dosimeter film (1) remains substantially colorless upon exposure to artificial illumination, including fluorescent light, for at least several months, (2) becomes colored upon exposure to high-energy radiation and accurately indicates small changes in dosage by the intensity of its color, and (3) remains substantially unchanged in its intensity of that color after being stored for several months, whether or not exposed to artificial illumination. An article of either quantitative or qualitative determination of the extent of high-energy radiation exposure is also provided, displaying a colored message of words, codes, symbols, or patterns on a substrate after exposure to the high-energy radiation.
    Type: Grant
    Filed: June 19, 1991
    Date of Patent: April 27, 1993
    Assignee: Minnesota-Mining & Manufacturing Company
    Inventors: Lu Ann N. Sidney, Doreen C. Lynch, Peggy S. Willett
  • Patent number: 5196297
    Abstract: This invention relates to novel recording materials which employ color-forming di- and triarylmethane compounds possessing certain S-containing ring-closing moieties, namely, or thiolactone, dithiolactone or thioether ring-closing moiety and to a method of forming color by contacting these dye precursor compounds with a Lewis acid material capable of opening the thiolactone, dithiolactone or thioether ring-closing moiety whereby the compound is rendered colored, that is, converted to its chromophore color.
    Type: Grant
    Filed: December 5, 1986
    Date of Patent: March 23, 1993
    Assignee: Polaroid Corporation
    Inventors: Edward J. Dombrowski, Jr., James R. Freedman, Patrick F. King
  • Patent number: 5187143
    Abstract: The present invention provides a heat sensitive recording material having a recoridng layer formed on a substrate and containing a colorless or light-colored basic dye and a color developer, the heat sensitive recording material being characterized in that the color developer includes a zinc salt of terephthalaldehydic acid or a composite zinc salt of terephthalaldehydic acid and other aromatic carboxylic acid.
    Type: Grant
    Filed: October 25, 1991
    Date of Patent: February 16, 1993
    Assignee: Kanzaki Paper Manufacturing Co., Ltd.
    Inventors: Kazuo Watanabe, Tosaku Okamoto
  • Patent number: 5178670
    Abstract: A color former for pressure- and heat-sensitive recording systems containinga) at least one 3,1-benzoxazine of the formula ##STR1## b) at least one fluoran of the formula ##STR2## c) at least one 3,1-benzoxazine of the formula ##STR3## and/or at least one lactone of the formula ##STR4## in which the substituents have the meanings given in the description, produces black colorations having good color intensity.
    Type: Grant
    Filed: March 25, 1991
    Date of Patent: January 12, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunther Klug, Horst Berneth, Gert Jabs
  • Patent number: 5164357
    Abstract: An improved heat-sensitive recording material is disclosed comprising a substrate, a binder, a chromogenic material, an electron-accepting color developer which reacts with said chromogenic material to form a color, and a color-stabilizing resin. The color stabilizing resin comprises an addition product of a diolefinic alkylated or alkenylated cyclic hydrocarbon or, an addition product of a phenol and a diolefinic alkylated or alkenylated cyclic hydrocarbon. The color-stabilizing resin, dye, and developer, have a weight percent resin phenolic group of about 5 or less. The heat-sensitive recording material has a fade index greater than 45. Imaged recording materials according to the invention resist fading when exposed to temperatures of 60.degree. C. for prolonged periods such as twenty-four hour oven tests.
    Type: Grant
    Filed: June 5, 1991
    Date of Patent: November 17, 1992
    Assignee: Appleton Papers Inc.
    Inventors: Gerald C. Bartman, Steven L. Vervacke, Peggy D. Sands
  • Patent number: 5157012
    Abstract: 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: Grant
    Filed: July 24, 1990
    Date of Patent: October 20, 1992
    Assignee: Appleton Papers Inc.
    Inventors: Ponnampalam Mathiaparanam, Dean G. Dalebroux, Kenneth D. Glanz
  • Patent number: 5155087
    Abstract: 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: Grant
    Filed: May 22, 1991
    Date of Patent: October 13, 1992
    Assignee: Mitsubishi Paper Mills, Ltd.
    Inventors: Toshihiko Matsushita, Shigetoshi Hiraishi, Sadao Morishita
  • Patent number: 5149689
    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 aralkylX.sub.3 and Y.sub.3 are hydrogen, unsubstituted or halogenhydroxyl-, 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: December 20, 1991
    Date of Patent: September 22, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Zink
  • Patent number: 5143890
    Abstract: The present invention provides a heat sensitive recording material, including a substrate and a heat sensitive recording layer thereon incorporating a colorless or light-colored basic dye and a color acceptor reactive with the dye to form a color when contacted therewith, the recording material also including 1-(4-methoxyphenoxy)-2-(2-methylphenoxy)ethane in the heat sensitive recording layer.
    Type: Grant
    Filed: November 21, 1990
    Date of Patent: September 1, 1992
    Assignees: Kanzaki Paper Manufacturing Co., Ltd., Sanko Kaihatsu Kagaku Kenkyusho Corporation
    Inventors: Tetsuo Tsuchida, Yukihiro Abe, Tomoyuki Okimoto, Toranosuke Saito
  • Patent number: 5132272
    Abstract: The present invention provides a heat sensitive recording material comprising a substrate and a recording layer thereon incorporating a colorless or light-colored basic dye and a color acceptor reactive with the dye to form a color when contacted therewith, the recording material being characterized in that, the basic dye comprises 1 at least one compound represented by the formula below [I] and 2 3-di-n-butylamino-6-methyl-7-anilinofluoran and/or 3-di-n-pentylamino-6-methyl-7-anilinofluoran, and the color acceptor comprises 4,4'-isopropylidenediphenol ##STR1## wherein R.sub.1, R.sub.2, a, b, c and d are as defined in the specification.
    Type: Grant
    Filed: January 30, 1991
    Date of Patent: July 21, 1992
    Assignee: Kanzaki Paper Manufacturing Co., Ltd.
    Inventors: Katsuaki Yoshizawa, Ritsuo Mandoh, Yukio Takayama
  • Patent number: 5116802
    Abstract: The invention provides a heat-sensitive recording material comprising (a) a base sheet and (b) a heat-sensitive recording layer formed on the base sheet and comprising a colorless or pale-colored basic dye, a color developing material which develops a color on contact with the dye, and a heat-fusible material, the recording material being characterized in that the basic dye comprises 3-di(n-butyl)amino-6-methyl-7-phenylaminofluoran, and that the heat-fusible material comprises di(p-methylbenzyl) oxalate.
    Type: Grant
    Filed: January 23, 1991
    Date of Patent: May 26, 1992
    Assignee: Kanzaki Paper Manufacturing Co., Ltd.
    Inventors: Naoto Arai, Kazuo Watanabe
  • Patent number: 5110848
    Abstract: A process for dispersing particles of an organic commpound in water is disclosed, which comprises dispersing the organic compound in water using (1) a water-soluble high molecular weight compound having a molecular weight of at least 10,000 and (2) a copolymer formed from a monomer represented by the following formula (I) and a monomer represented by the following formula (II), said copolymer having a molecular weight of not more than 10,000: ##STR1## wherein M.sub.1 and M.sub.2 each represents an alkali metal atom or an ammonium group; R.sub.1 represents a hydrogen atom, a methyl group, or an ethyl group; and R.sub.2 represents an alkyl group having from 2 to 18 carbon atoms.
    Type: Grant
    Filed: February 1, 1989
    Date of Patent: May 5, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Akira Igarashi
  • Patent number: 5110786
    Abstract: A heat-sensitive recording material comprises a recording layer formed on a base sheet where the recording layer comprises a colorless or pale colored basic chromogenic material, a color developing material which develops a color by contacting with said chromogenic material, and a stabilizer.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: May 5, 1992
    Assignee: Kanzaki Paper Manufacturing Co., Ltd.
    Inventors: Naoto Arai, Nobuo Kanda, Masaharu Nojima
  • Patent number: 5102858
    Abstract: In a process of producing high purity bis(4-hydroxyphenyl) sulfides which comprises reacting phenols with sulfur dichloride in organic solvents, the improvement comprising: reacting the phenols with sulfur dichloride in nonpolar organic solvents; removing partly or wholly the nonpolar organic solvents after the reaction; adding polar organic solvents to the reaction mixture to dissolve the reaction mixture therein at elevated temperatures; and crystallizing out the high purity bis(4-hydroxyphenyl)sulfides.There is further provided a high performance heat-sensitive recording material which comprises high purity bis(4-hydroxy-3-methylphenyl)sulfide thus prepared and having a melting point in the range of from 123.9.degree. C. to 124.9.degree. C. as a developer and a fluoran compound as a color former.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: April 7, 1992
    Assignee: Seitetsu Kagaku Co., Ltd.
    Inventors: Akira Onoe, Masao Kawamura, Kunioki Kato, Tomiharu Amitani, Makoto Sato, Tsuyoshi Morishita
  • Patent number: 5098882
    Abstract: A heat-sensitive recording medium comprising, on a support, a heat-sensitive color-developing layer containing a colorless or light-colored leuco dye (or an electron-donating dye precursor) and a color-developing agent (or an electron-accepting substance) reacting with the leuco dye to develop color as main constituents, said leuco dye being a compound represented by the formula (I): ##STR1## wherein X represents CH.sub.3 --(CH.sub.2).sub.3 --CH.sub.2 or CH.sub.3 --CH.sub.2 --CH.sub.2 and Y represents CH.sub.3 --(CH.sub.2).sub.3 --Ch.sub.2 or CH.sub.3, and said heat-sensitive color-developing layer containing at least one of the compounds represented by the general formula (II) and (III): ##STR2## where R.sub.1, R.sub.1 ' are respectively any one of H, Cl, and CH.sub.3, and may be the same with or different from each other: ##STR3## where R.sub.2, R.sub.2 ' are respectively any one of H and CH.sub.3, and may be the same with or different from each other.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: March 24, 1992
    Assignee: Daio Paper Corporation
    Inventors: Hiroshige Teraji, Yasunori Shimada, Motokazu Aono, Hisashi Yamamoto
  • Patent number: 5096873
    Abstract: A thermosensitive recording sheet comprising a support and a thermosensitive color developer layer thereon containing a basic leuco dye and an organic color developer, said layer containing a bis-phenyl sulfone compound selected from bis-(3-phenyl-4-hydroxyphenyl)sulfone and bis-(2-methyl-4-hydroxy-5-cyclohexylphenyl)sulfone as the organic color developer.
    Type: Grant
    Filed: April 4, 1990
    Date of Patent: March 17, 1992
    Assignees: Jujo Paper Co., Ltd., Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Toshiaki Minami, Tadakazu Fukuchi, Toshio Kaneko, Fumio Fujimura, Kazuto Tsukinuki, Kazumi Saeki, Akira Shimada
  • Patent number: 5092925
    Abstract: The invention relates to mixtures of a) at least one 3,1-benzoxazine of the formula ##STR1## and b) at least one fluorane of the formula ##STR2## wherein the radicals of the abovementioned formulae have the meaning given in the description, and their use as color-forming agents for pressure- and heat-sensitive recording materials and to such recording materials.
    Type: Grant
    Filed: December 6, 1989
    Date of Patent: March 3, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Berneth, Gunter Klug, Gert Jabs
  • Patent number: 5079211
    Abstract: The present invention provides a heat sensitive recording material which is less in fog in background area and has superior color toning effect with high image storage stability which contain a fluoran compound represented by the following formula in addition to an aromatic isocyanate compound and an imino compound having at least one >C.dbd.NH group which forms color upon application of heat: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 each represents a hydrogen atom, a lower alkyl group, a cyclohexyl group or an allyl group and R.sub.4 and R.sub.5 each represents a hydrogen atom, a lower alkyl group, a phenyl group, a cyclohexyl group or an aralkyl group. This heat sensitive recording material may further contain a heat fusible substance and/or a phenol compound to further improve heat responsivity or anti-fogging properties of background portion.
    Type: Grant
    Filed: October 11, 1989
    Date of Patent: January 7, 1992
    Assignee: Mitsubishi Paper Mills Limited
    Inventors: Yutaka Shimura, Toshimitsu Nakajima, Shigetoshi Hiraishi
  • Patent number: 5075279
    Abstract: A method for the manufacture of microcapsules for use in pressure-sensitive recording sheets is disclosed, which comprises after dispersing and emulsifying in a hydrophilic liquid a solution obtained by dissolving (a) a polyisocyanate, (b) an alkyleneoxide adduct of an amine and (c) an electron-donating color former in a hydrophobic liquid, adding a polyamine to the emulsified dispersion and forming microcapsules of poly(urethane urea) around the liquid droplets containing the color former.
    Type: Grant
    Filed: June 15, 1989
    Date of Patent: December 24, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Shojiro Sano
  • 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: 5066633
    Abstract: A heat sensitive coating has a colorless or light colored leuco dye precursor, preferably having a five-membered spirol lactone ring at one end of the molecule, and a tertiary amino group at another end of the molecule, and a developer. Sensitizers which increase the heat sensitivity of these dye precursors, and compositions of sensitized dye/developer systems are disclosed. The sensitizers are .gamma.-substituted lactones, 3-naphthylmethylidenephthalide, and derivatives of benzalphthalide.
    Type: Grant
    Filed: February 9, 1990
    Date of Patent: November 19, 1991
    Assignee: Graphic Controls Corporation
    Inventors: Tomoo Shibata, John Semler, George Gaesser
  • Patent number: 5066634
    Abstract: A heat-sensitive recording sheet of this invention comprises in a heat-sensitive color-developing layer both 4-hydroxy-4'-n-propoxydiphenylsulfone as an organic color-developing agent and a particular fluorane-leuco dye. This sheet provides an intense, clear image, less discoloration, and stable brightness.
    Type: Grant
    Filed: September 27, 1990
    Date of Patent: November 19, 1991
    Assignee: Jujo Paper Co., Ltd.
    Inventors: Toshiaki Minami, Tadakazu Fukuchi, Reiji Ohashi, Toshio Kaneko
  • Patent number: 5055595
    Abstract: Etherified fluorescein compounds of the general formula ##STR1## in which X.sub.1 is alkyl having 4 to 12 carbon atoms or cycloalkyl and X.sub.2 is alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or cycloalkyl, the rings A and B, independently of one another, are unsubstituted or substituted by halogen, lower alkyl or lower alkoxy, and the ring D is unsubstituted or substituted by halogen, nitro, lower alkyl, lower alkoxy, lower alkylthio, lower alkoxycarbonyl, amino, mono-lower alkylamino or di-lower alkylamino, with the exception that X.sub.1 and X.sub.2 are not at the same time n-butyl.These novel lactone compounds are particularly suitable for use a color formers in pressure-sensitive or heat-sensitive recording materials and they produce intense yellow, orange or rose-pink colorations.
    Type: Grant
    Filed: November 14, 1989
    Date of Patent: October 8, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Bernhard Wietfeld
  • 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: 4999332
    Abstract: A heat-sensitive recording material comprising a dye precursor which is colorless or light-colored in the usual state and a color developing agent capable of reacting with said dye precursor upon heating to develop a color which is a combination of compounds of the following chemical formulas (I) and (II).
    Type: Grant
    Filed: September 8, 1988
    Date of Patent: March 12, 1991
    Assignee: Mitsubishi Paper Mills, Limited
    Inventors: Fumio Okumura, Akinori Okada, Kazuyoshi Kondo
  • Patent number: 4999333
    Abstract: A heat sensitive recording material which is comprised of a support having thereon at least a transparent heat sensitive layer excellent in freshness-keeping property is disclosed. The transparent heat sensitive layer is obtained by coating a solution obtained by mixing a microcapsule containing a colorless or light colored electron donating dye precursor with an emulsion prepared by dispersing a color developer dissolved in an organic solvent, which is slightly soluble or insoluble in water, into an aqueous solution containing both of a surface active agent and water soluble polymer. The stabilities of emulsion and heat sensitive layer are improved by using a partially saponified polyvinyl alcohol as the water soluble polymer and/or adding a metal salts of a salicylic acid derivatives into the coolor developer. A heat sensitivity of the heat sensitive recording material is improved by using a organic solvent having a boiling point lower than 150.degree. C.
    Type: Grant
    Filed: October 3, 1988
    Date of Patent: March 12, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshimasa Usami, Seiji Hatakeyama, Akihiro Shimomura, Ken Iwakura
  • Patent number: 4997741
    Abstract: A color image forming method comprises bringing a developer into contact with a recording material comprising a support and a recording layer containing at least two kinds of leuco dyes being capable of forming colors different in hue from each other on contact with the developer. The leuco dyes are a yellow color forming leuco dye, a magenta color forming leuco dye and/or a cyan color forming leuco dye. The equilibrium constants of the reactions between these dyes contained in the recording layer and the developer are not lower than 0.05.
    Type: Grant
    Filed: May 27, 1988
    Date of Patent: March 5, 1991
    Assignee: Fuji Photo Film Company
    Inventor: Toshiyuki Watanabe
  • Patent number: RE33815
    Abstract: A heat sensitive record sheet which comprises a coated layer comprising 2-anilino-3-methyl-6-dibutylaminofluoran.
    Type: Grant
    Filed: June 27, 1988
    Date of Patent: February 4, 1992
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Masahiko Yamaguchi, Michihiro Gonda, Yutaka Satoh, Mikiko Kanasugi