EP0286116A2 - Matériau d'enregistrement thermosensible - Google Patents

Matériau d'enregistrement thermosensible Download PDF

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Publication number
EP0286116A2
EP0286116A2 EP88105625A EP88105625A EP0286116A2 EP 0286116 A2 EP0286116 A2 EP 0286116A2 EP 88105625 A EP88105625 A EP 88105625A EP 88105625 A EP88105625 A EP 88105625A EP 0286116 A2 EP0286116 A2 EP 0286116A2
Authority
EP
European Patent Office
Prior art keywords
heat
sensitive recording
recording material
parts
material according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP88105625A
Other languages
German (de)
English (en)
Other versions
EP0286116B1 (fr
EP0286116A3 (en
Inventor
Tochimi Central Research Laboratory Satake
Toshiaki Central Research Laboratory Minami
Tomoaki Central Research Laboratory Nagai
Fumio Central Research Laboratory Fujimura
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jujo Paper Co Ltd
Original Assignee
Jujo Paper Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jujo Paper Co Ltd filed Critical Jujo Paper Co Ltd
Publication of EP0286116A2 publication Critical patent/EP0286116A2/fr
Publication of EP0286116A3 publication Critical patent/EP0286116A3/de
Application granted granted Critical
Publication of EP0286116B1 publication Critical patent/EP0286116B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
    • G03C1/498—Photothermographic systems, e.g. dry silver
    • G03C1/4989—Photothermographic systems, e.g. dry silver characterised by a thermal imaging step, with or without exposure to light, e.g. with a thermal head, using a laser
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
    • B41M5/32—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers one component being a heavy metal compound, e.g. lead or iron
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
    • B41M5/323—Organic colour formers, e.g. leuco dyes
    • B41M5/327—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
    • B41M5/3275—Fluoran compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
    • B41M5/333—Colour developing components therefor, e.g. acidic compounds
    • B41M5/3333—Non-macromolecular compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
    • B41M5/333—Colour developing components therefor, e.g. acidic compounds
    • B41M5/3333—Non-macromolecular compounds
    • B41M5/3335—Compounds containing phenolic or carboxylic acid groups or metal salts thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
    • B41M5/333—Colour developing components therefor, e.g. acidic compounds
    • B41M5/3333—Non-macromolecular compounds
    • B41M5/3335—Compounds containing phenolic or carboxylic acid groups or metal salts thereof
    • B41M5/3336—Sulfur compounds, e.g. sulfones, sulfides, sulfonamides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/913—Material designed to be responsive to temperature, light, moisture
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/914—Transfer or decalcomania

Definitions

  • the invention relates to a thermosensitive recording material which has superior optical readability in the near ultra-red range.
  • Heat-sensitive recording sheets in which a color reaction between a colorless or slightly colored or chromogenic substance and a phenolic substance or an organic acid takes place due to the action of heat or heat include in Japanese Patent Publications No. 4160/1968 and 14039/1970 and in JP-OLS No. 27736/1973. They are used in many different ways in practice.
  • a heat-sensitive recording sheet is generally prepared by applying to the surface of a support such as paper, film, etc., a coating composition which is obtained by finely grinding and dispersing a colorless chromogenic substance and a color developing material, mixing the dispersions obtained with one another and adding a binder, filler, Sensitizer, lubricant and other aids has been obtained. When exposed to heat or heat, the coating immediately undergoes a chemical reaction with color formation.
  • heat-sensitive recording sheets include use in medical and technical recording devices, terminal printers for computers and information systems, printers for facsimile or copying machines and electronic calculating machines, ticket machines and the like.
  • the heat sensitive recording sheets containing a leuco dye and a coloring agent are used as thermal labels in the field of POS systems.
  • the color development occurs in the visible range, so that the color development when a semiconductor laser beam is used in the near ultra-red range cannot be read by the bar code scanner.
  • Metal chelate color development type heat sensitive recording sheets are used as heat sensitive sheets for POS systems, etc., but have the disadvantage that the legibility is insufficient when using a semiconductor laser beam operating in the near-red range as a bar code measuring point scanner.
  • the invention has for its object to provide a heat-sensitive recording sheet which has superior optical readability in the near ultraviolet range in color development with chelating agents using metal compounds.
  • a near-infrared absorbing fluoran dye of the following general formula (I) is used in a heat-sensitive recording material which has a heat-sensitive recording layer of a chelating agent type on a support: wherein at least one of the radicals R1, R2, R3, R4, R5, R6, R7, R8, and R9 is a group of the general formula: means wherein T1, T2 and T3 are the same or different and each represents a hydrogen atom, a C1-C8 alkyl, C3-C9 alkenyl or C3-C9 alkynyl group; T4 represents a hydrogen atom, a C1-C8 alkyl, C3-C9 alkenyl, C3-C9 alkynyl or phenyl group; T3 and T4 may also be connected to an adjacent nitrogen atom to form a morpholino, pyrrolidino, piperidino or hexamethyleneimino group; and the radical
  • the alkyl groups preferably have 1 to 6 carbon atoms
  • the cycloalkyl groups preferably have 3 to 6 carbon atoms
  • the substitution of the amino groups preferably consists of a mono- or di-C1-C6-alkyl substitution
  • the aryl groups are preferably phenyl radicals.
  • the choice of the electron acceptor according to the invention is not subject to any particular restrictions; the known electron acceptors, preferably the metal double salts of the higher fatty acids, can be used.
  • the metal double salts of higher fatty acids according to the invention are double salts which have at least two types of metal atoms per molecule. They therefore differ significantly in their physicochemical properties from the previous metal salts of higher fatty acids, which only contain one type of metal atom in their molecule.
  • These metal double salts of the higher fatty acids are prepared by reacting at least two inorganic metal salts with an alkali metal salt or ammonium salt of the selected higher fatty acid.
  • the type and the mixing ratio of the metal atoms of the at least two inorganic metal salts can be easily adjusted and controlled in this way.
  • the zinc-iron double salt of behenic acid with iron and zinc in a ratio of 2: 1 can be prepared by reacting sodium behenate with an aqueous solution of ferrichloride and zinc chloride in a molar ratio of 2: 1.
  • Suitable metals for the double salt formation of the higher fatty acids are polyvalent metals, for example iron, zinc, calcium, magnesium, aluminum, barium, lead, manganese, tin, nickel, cobalt, copper, silver, mercury, etc .; preferably iron, zinc, calcium, aluminum, magnesium and silver.
  • Suitable fatty acids for the double salt formation are saturated and / or unsaturated aliphatic fatty acids with 16 to 35 carbon atoms.
  • the electron donors according to the invention which are used with the metal double salt of a higher fatty acid, are preferably polyvalent aromatic hydroxyl compounds, diphenylcarbazide, diphenylcarbazone, hexamethylenetetramine, spirobenzopyran and 1-formyl-4-phenylsemicarbazide; most preferred are the polyvalent aromatic hydroxyl compounds of the general formula (I): in the R an alkyl group with 18 to 35 (wherein R1 represents an alkyl group having 18 to 35 carbon atoms); n represents an integer from 2 to 3; and "-X-" for ⁇ CH2 ⁇ , ⁇ CO2 ⁇ , ⁇ CO ⁇ , ⁇ O ⁇ , ⁇ CONH ⁇ , -C - (wherein R ⁇ is an alkyl group having 5 to 30 carbon atoms), -SO2-, -SO3- or -SO2NH-.
  • the heat-sensitive recording layer according to the invention which contains an electron acceptor and an electron donor, also contains a near-infrared absorbing fluoran dye of the general formula (I).
  • the dyes of the following general formula (II) prefers.
  • the fluorine leuco dyes according to the invention are not subject to any particular restrictions; the following can be used, for example: 2-methyl-6-p- (p-dimethylaminophenyl) aminoani linofluoran, 2-methoxy-6-p- (p-dimethylaminophenyl) aminoanilinofluoran, 2-chloro-6-p- (p-dimethylaminophenyl) aminoanilinofluoran, ⁇ -nitro-6-p- (p-di ethylaminophenyl) aminoanilinofluoran, 2- Amino-6-p- (p-dimethylaminophenyl) aminoanilinofluoran, 2-diethylamino-6-p- (p-dimethylaminophenyl) aminoanilinofluoran, 2-phenyl-6-p- (p-phenylaminophenyl) aminoanilinofluoran, 2-benzyl-6-p - (
  • the fluorantypleuco dyes of the general formula (I) according to the invention are used alone or in a mixture.
  • Binders according to the invention are, for example, completely saponified polyvinyl alcohol, degree of polymerization: 200-1900, partly saponified polyvinyl alcohol, carboxylated polyvinyl alcohol, amide-modified polyvinyl alcohol, sulfonic acid-modified polyvinyl alcohol, butyral-modified polyvinyl alcohol, other modified polyvinyl alcohols, hydroxyethyl cellulose styrene, methyl malolymethyl copolymer, methyl cellulose, methyl cellulose, methyl cellulose, methyl cellulose, methyl cellulose, methyl cellulose, methyl cellulose, methylcellulose, methylcellulose Copolymers, cellulose derivatives such as ethyl cellulose and acetyl cellulose, polyvinyl chloride, polyvinyl acetate, polyacrylamide, polyacrylic acid ester, polyvinyl butyral, polystyrene, copoly mers of the above compounds, polyamide resin, silicone resin, petroleum resin
  • the type and amount of the electron acceptor according to the invention such as the metal double salt of the saturated higher fatty acid, the electron donor such as the polyhydric phenol, the near-infrared absorbing leuco dye, the binder and the other additives, which are chosen depending on the desired effect and suitability for recording purposes, are not particularly limited.
  • the heat sensitive material of the present invention made by applying the coating composition to a base material such as paper, synthetic paper, film, plastic, etc.
  • the electron acceptor according to the invention, the electron donor according to the invention and the basic colorless chromogenic dye according to the invention are ground to a particle size of several microns or smaller by means of a grinding device, such as a ball mill, attrition mill, sand grinder, etc., or by means of a suitable emulsifying machine: binders are added, if appropriate , various additives to produce the coating composition of the invention.
  • the additives which can be used according to the invention are, for example, the following: Fillers; Anti-sticking releasing agents such as metal salts of fatty acids; Mottling prevention lubricants such as fatty acid amide, ethylene bisamide, montan wax, polyethylene wax, etc .; Dispersants such as sodium dioctyl sulfosuccinic acid, sodium dodecyl benzene sulfonate, sodium lauryl alcohol sulfate, sodium alginate, etc .; UV absorbers of the benzophenone and triazole series; Anti-foaming agents; water mooring agents, etc.
  • fillers according to the invention are alumina, talc, silicon dioxide, magnesium carbonate, aluminum hydroxide, magnesium hydroxide, barium sulfate, kaolin, titanium dioxide, zinc oxide, calcium carbonate, aluminum oxide, urea-formaldehyde resin, polystyrene resin, phenolic resin, etc.
  • the reason for the superior optical legibility in the near-red range of the heat-sensitive recording sheet according to the invention is based on the fact that during color development with complex formation by melting reaction between a metal double salt as an electron acceptor and an electron donor such as polyvalent phenol derivative, a colored image in the visible and near-red range (wavelength range 700 -1500 nm) arises.
  • the fluoranleuco dye of the present invention is added to this combination, which can more effectively absorb the near-ultraviolet rays in the melting reaction with an electron donor such as phenolic derivatives. In this way, a thermosensitive recording sheet is obtained which has superior optical readability in the near ultraviolet range.
  • Double metal salt of a higher fatty acid See Table 1.
  • Solution C (dispersion of a near-infrared absorbing leuco dye)
  • Leuco dye See Table 1.
  • Solution A 25.0 parts
  • Solution B 29.5 parts
  • Solution C 2.5 parts Kaolin clay (5% aqueous dispersion) 12.0 parts
  • the above coating composition was applied in a coating amount of 6.0 g / m2 on a base paper with a weight of 50 g / m2, dried and supercalendered to set a smoothness of 200-600 seconds.
  • a heat sensitive recording sheet was obtained.
  • Metal double salt of a higher fatty acid See Table 1.
  • Solution D 25.0 parts
  • Solution F 29.5 parts Kaolin clay (50% aqueous dispersion) 12.0 parts
  • a heat-sensitive recording sheet was obtained in the same manner as in Example 1.
  • the recording material of the present invention has superior optical readability in the near ultra-red range.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Optics & Photonics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
EP88105625A 1987-04-09 1988-04-08 Matériau d'enregistrement thermosensible Expired - Lifetime EP0286116B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP62087503A JPH066392B2 (ja) 1987-04-09 1987-04-09 感熱記録体
JP87503/87 1987-04-09

Publications (3)

Publication Number Publication Date
EP0286116A2 true EP0286116A2 (fr) 1988-10-12
EP0286116A3 EP0286116A3 (en) 1989-04-12
EP0286116B1 EP0286116B1 (fr) 1991-12-11

Family

ID=13916784

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88105625A Expired - Lifetime EP0286116B1 (fr) 1987-04-09 1988-04-08 Matériau d'enregistrement thermosensible

Country Status (4)

Country Link
US (1) US4853363A (fr)
EP (1) EP0286116B1 (fr)
JP (1) JPH066392B2 (fr)
DE (1) DE3866752D1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0287121A2 (fr) * 1987-04-17 1988-10-19 Jujo Paper Co., Ltd. Matériel d'enregistrement sensible à la chaleur et à la lumière et méthode d'enregistrement
EP0307836A2 (fr) * 1987-09-14 1989-03-22 Jujo Paper Co., Ltd. Matériau d'enregistrement thermosensible
EP0574879A1 (fr) * 1992-06-17 1993-12-22 Mitsubishi Paper Mills, Ltd. Matériau d'enregistrement thermosensible et réversible
EP0599580A1 (fr) * 1992-11-20 1994-06-01 Nippon Paper Industries Co., Ltd. Feuille pour l'enregistrement thermique

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69032232T2 (de) * 1989-02-03 1998-08-06 Jujo Paper Co Ltd Optisches Aufzeichnungsmaterial, optisches Aufzeichnungsverfahren und optische Aufzeichnungsvorrichtung für dieses Verfahren
US5200947A (en) * 1989-02-03 1993-04-06 Jujo Paper Co., Ltd. Optical recording medium, optical recording method, and optical recording device used in method
JP2536917B2 (ja) * 1989-02-06 1996-09-25 日本製紙株式会社 光記録体
JP4090154B2 (ja) * 1999-07-23 2008-05-28 富士フイルム株式会社 平版印刷版の製造方法
JP2012220883A (ja) * 2011-04-13 2012-11-12 Casio Electronics Co Ltd 負帯電性消色型電子写真トナーおよびその製造方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4004065A (en) * 1974-12-13 1977-01-18 General Company, Ltd. Coated heat sensitive recording member
JPS5993387A (ja) * 1982-11-19 1984-05-29 Ricoh Co Ltd 感熱記録材料

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0713195B2 (ja) * 1986-07-31 1995-02-15 日本曹達株式会社 フルオラン化合物およびそれを使用した発色性記録体
JP2778701B2 (ja) * 1988-09-12 1998-07-23 マナック株式会社 ブリーチ加工用脱色促進剤

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4004065A (en) * 1974-12-13 1977-01-18 General Company, Ltd. Coated heat sensitive recording member
JPS5993387A (ja) * 1982-11-19 1984-05-29 Ricoh Co Ltd 感熱記録材料

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN, Band 8, Nr. 203 (M-326)[1640], 18. September 1984; & JP-A-59 093 387 (RICOH K.K.) 29-05-1984 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0287121A2 (fr) * 1987-04-17 1988-10-19 Jujo Paper Co., Ltd. Matériel d'enregistrement sensible à la chaleur et à la lumière et méthode d'enregistrement
EP0287121A3 (en) * 1987-04-17 1990-07-11 Jujo Paper Co., Ltd. Heat and light-sensitive recording material and recording method
EP0307836A2 (fr) * 1987-09-14 1989-03-22 Jujo Paper Co., Ltd. Matériau d'enregistrement thermosensible
EP0307836A3 (en) * 1987-09-14 1990-09-19 Jujo Paper Co., Ltd. Heat-sensitive recording material
EP0574879A1 (fr) * 1992-06-17 1993-12-22 Mitsubishi Paper Mills, Ltd. Matériau d'enregistrement thermosensible et réversible
US5395815A (en) * 1992-06-17 1995-03-07 Mitsubishi Paper Mills Limited Reversible heat-sensitive recording material
EP0599580A1 (fr) * 1992-11-20 1994-06-01 Nippon Paper Industries Co., Ltd. Feuille pour l'enregistrement thermique
US5446009A (en) * 1992-11-20 1995-08-29 Nippon Paper Industries Co., Ltd. Thermal recording sheet

Also Published As

Publication number Publication date
EP0286116B1 (fr) 1991-12-11
DE3866752D1 (de) 1992-01-23
EP0286116A3 (en) 1989-04-12
JPS63252784A (ja) 1988-10-19
JPH066392B2 (ja) 1994-01-26
US4853363A (en) 1989-08-01

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