Fluoran Or Derivative Patents (Class 503/221)
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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: 5340537Abstract: 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: GrantFiled: April 16, 1993Date of Patent: August 23, 1994Assignee: Big Three Industries, Inc.Inventor: Richard B. Barrett
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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: 5318939Abstract: 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: GrantFiled: September 11, 1991Date of Patent: June 7, 1994Assignee: Ciba-Geigy CorporationInventors: Hugh S. Laver, Mario Slongo
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Patent number: 5302571Abstract: 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: June 14, 1993Date of Patent: April 12, 1994Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Atsuo Otsuji, Masakatsu Nakatsuka, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
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Patent number: 5300473Abstract: 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: GrantFiled: March 8, 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: 5288688Abstract: 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: GrantFiled: March 24, 1993Date of Patent: February 22, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Hiroshi Kawakami, Chiyoshi Nozaki, Ken Iwakura
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Patent number: 5286703Abstract: 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: GrantFiled: November 21, 1991Date of Patent: February 15, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Naotaka Wachi, Ken Iwakura, Kensuke Ikeda, Katsuya Takemasa
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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: 5270281Abstract: 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: GrantFiled: June 22, 1992Date of Patent: December 14, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Atsuo Otsuji, Toshihiro Motoshima, Yoshimitsu Tanabe, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Masakatsu Nakatsuka, Akihiro Yamaguchi
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Patent number: 5260252Abstract: 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: GrantFiled: July 24, 1990Date of Patent: November 9, 1993Assignee: Nashua CorporationInventors: Frederick G. Frangie, Roberta R. Arbree
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Patent number: 5250492Abstract: 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: GrantFiled: March 7, 1991Date of Patent: October 5, 1993Assignee: The Standard Register CompanyInventors: Mark D. Dotson, Frank V. Parenti
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Patent number: 5250493Abstract: 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: GrantFiled: November 22, 1991Date of Patent: October 5, 1993Assignee: Ricoh Company, Ltd.Inventors: Takashi Ueda, Yasuhiko Watanabe
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Patent number: 5246905Abstract: A thermosensitive recording material which contains an aromatic isocyanate compound, an imino compound having at least one >C.dbd.Type: GrantFiled: December 24, 1991Date of Patent: September 21, 1993Assignee: Mitsubishi Paper Mills LimitedInventors: Mikiya Sekine, Hidetaka Tsukada
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Patent number: 5242886Abstract: 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: GrantFiled: July 15, 1992Date of Patent: September 7, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Shojiro Sano, Masanobu Takashima
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Patent number: 5231069Abstract: 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: GrantFiled: December 4, 1992Date of Patent: July 27, 1993Assignee: Mitsui Toatsu Chemicals Inc.Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, 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: 5210064Abstract: 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: GrantFiled: November 20, 1991Date of Patent: May 11, 1993Assignee: Polaroid CorporationInventors: Rita S. Shon Baker, Larry C. Takiff
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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: 5206208Abstract: 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: GrantFiled: November 20, 1991Date of Patent: April 27, 1993Assignee: Polaroid CorporationInventors: Rong C. Liang, William C. Schwarzel, Rita S. Shon Baker, Robert P. Short, Stephen R. Sofen, Michael A. Young
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Patent number: 5206210Abstract: 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: GrantFiled: July 23, 1991Date of Patent: April 27, 1993Assignee: Kanzaki Paper Manufacturing Co., Ltd.Inventors: Tetsuo Tsuchida, Yukihiro Abe, Takehiro Minami, Naoto Arai
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Patent number: 5206209Abstract: 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: GrantFiled: April 10, 1991Date of Patent: April 27, 1993Assignee: Jujo Paper Co., Ltd.Inventors: Toshiaki Minami, Tadakazu Fukuchi, Toshio Kaneko
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Patent number: 5206118Abstract: 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: GrantFiled: June 19, 1991Date of Patent: April 27, 1993Assignee: Minnesota-Mining & Manufacturing CompanyInventors: Lu Ann N. Sidney, Doreen C. Lynch, Peggy S. Willett
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Patent number: 5196297Abstract: 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: GrantFiled: December 5, 1986Date of Patent: March 23, 1993Assignee: Polaroid CorporationInventors: Edward J. Dombrowski, Jr., James R. Freedman, Patrick F. King
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Patent number: 5187143Abstract: 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: GrantFiled: October 25, 1991Date of Patent: February 16, 1993Assignee: Kanzaki Paper Manufacturing Co., Ltd.Inventors: Kazuo Watanabe, Tosaku Okamoto
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Patent number: 5178670Abstract: 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: GrantFiled: March 25, 1991Date of Patent: January 12, 1993Assignee: Bayer AktiengesellschaftInventors: Gunther Klug, Horst Berneth, Gert Jabs
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Patent number: 5164357Abstract: 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: GrantFiled: June 5, 1991Date of Patent: November 17, 1992Assignee: Appleton Papers Inc.Inventors: Gerald C. Bartman, Steven L. Vervacke, Peggy D. Sands
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Patent number: 5157012Abstract: 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: GrantFiled: July 24, 1990Date of Patent: October 20, 1992Assignee: Appleton Papers Inc.Inventors: Ponnampalam Mathiaparanam, Dean G. Dalebroux, Kenneth D. Glanz
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Patent number: 5155087Abstract: 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: GrantFiled: May 22, 1991Date of Patent: October 13, 1992Assignee: Mitsubishi Paper Mills, Ltd.Inventors: Toshihiko Matsushita, Shigetoshi Hiraishi, Sadao Morishita
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Patent number: 5149689Abstract: 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: GrantFiled: December 20, 1991Date of Patent: September 22, 1992Assignee: Ciba-Geigy CorporationInventor: Rudolf Zink
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Patent number: 5143890Abstract: 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: GrantFiled: November 21, 1990Date of Patent: September 1, 1992Assignees: Kanzaki Paper Manufacturing Co., Ltd., Sanko Kaihatsu Kagaku Kenkyusho CorporationInventors: Tetsuo Tsuchida, Yukihiro Abe, Tomoyuki Okimoto, Toranosuke Saito
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Patent number: 5132272Abstract: 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: GrantFiled: January 30, 1991Date of Patent: July 21, 1992Assignee: Kanzaki Paper Manufacturing Co., Ltd.Inventors: Katsuaki Yoshizawa, Ritsuo Mandoh, Yukio Takayama
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Patent number: 5116802Abstract: 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: GrantFiled: January 23, 1991Date of Patent: May 26, 1992Assignee: Kanzaki Paper Manufacturing Co., Ltd.Inventors: Naoto Arai, Kazuo Watanabe
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Patent number: 5110848Abstract: 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: GrantFiled: February 1, 1989Date of Patent: May 5, 1992Assignee: Fuji Photo Film Co., Ltd.Inventor: Akira Igarashi
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Patent number: 5110786Abstract: 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: GrantFiled: April 12, 1990Date of Patent: May 5, 1992Assignee: Kanzaki Paper Manufacturing Co., Ltd.Inventors: Naoto Arai, Nobuo Kanda, Masaharu Nojima
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Patent number: 5102858Abstract: 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: GrantFiled: June 12, 1989Date of Patent: April 7, 1992Assignee: Seitetsu Kagaku Co., Ltd.Inventors: Akira Onoe, Masao Kawamura, Kunioki Kato, Tomiharu Amitani, Makoto Sato, Tsuyoshi Morishita
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Patent number: 5098882Abstract: 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: GrantFiled: August 20, 1990Date of Patent: March 24, 1992Assignee: Daio Paper CorporationInventors: Hiroshige Teraji, Yasunori Shimada, Motokazu Aono, Hisashi Yamamoto
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Patent number: 5096873Abstract: 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: GrantFiled: April 4, 1990Date of Patent: March 17, 1992Assignees: Jujo Paper Co., Ltd., Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Toshiaki Minami, Tadakazu Fukuchi, Toshio Kaneko, Fumio Fujimura, Kazuto Tsukinuki, Kazumi Saeki, Akira Shimada
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Patent number: 5092925Abstract: 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: GrantFiled: December 6, 1989Date of Patent: March 3, 1992Assignee: Bayer AktiengesellschaftInventors: Horst Berneth, Gunter Klug, Gert Jabs
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Patent number: 5079211Abstract: 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: GrantFiled: October 11, 1989Date of Patent: January 7, 1992Assignee: Mitsubishi Paper Mills LimitedInventors: Yutaka Shimura, Toshimitsu Nakajima, Shigetoshi Hiraishi
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Patent number: 5075279Abstract: 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: GrantFiled: June 15, 1989Date of Patent: December 24, 1991Assignee: Fuji Photo Film Co., Ltd.Inventor: Shojiro Sano
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Patent number: 5071480Abstract: 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: GrantFiled: February 28, 1990Date of Patent: December 10, 1991Assignee: Ciba-Geigy CorporationInventor: Rudolf Zink
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Patent number: 5066633Abstract: 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: GrantFiled: February 9, 1990Date of Patent: November 19, 1991Assignee: Graphic Controls CorporationInventors: Tomoo Shibata, John Semler, George Gaesser
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Patent number: 5066634Abstract: 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: GrantFiled: September 27, 1990Date of Patent: November 19, 1991Assignee: Jujo Paper Co., Ltd.Inventors: Toshiaki Minami, Tadakazu Fukuchi, Reiji Ohashi, Toshio Kaneko
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Patent number: 5055595Abstract: 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: GrantFiled: November 14, 1989Date of Patent: October 8, 1991Assignee: Ciba-Geigy CorporationInventor: Bernhard Wietfeld
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Patent number: 5017710Abstract: 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: GrantFiled: October 24, 1989Date of Patent: May 21, 1991Assignee: Nippon Soda Co., Ltd.Inventors: Tetsuo Igaki, Akio Kaneko, Sumio Manaka, Kimiaki Kinoshita
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Patent number: 4999332Abstract: 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: GrantFiled: September 8, 1988Date of Patent: March 12, 1991Assignee: Mitsubishi Paper Mills, LimitedInventors: Fumio Okumura, Akinori Okada, Kazuyoshi Kondo
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Patent number: 4999333Abstract: 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: GrantFiled: October 3, 1988Date of Patent: March 12, 1991Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshimasa Usami, Seiji Hatakeyama, Akihiro Shimomura, Ken Iwakura
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Patent number: 4997741Abstract: 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: GrantFiled: May 27, 1988Date of Patent: March 5, 1991Assignee: Fuji Photo Film CompanyInventor: Toshiyuki Watanabe
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Patent number: RE33815Abstract: A heat sensitive record sheet which comprises a coated layer comprising 2-anilino-3-methyl-6-dibutylaminofluoran.Type: GrantFiled: June 27, 1988Date of Patent: February 4, 1992Assignee: Hodogaya Chemical Co., Ltd.Inventors: Masahiko Yamaguchi, Michihiro Gonda, Yutaka Satoh, Mikiko Kanasugi