EP0287121B1 - Matériel d'enregistrement sensible à la chaleur et à la lumière et méthode d'enregistrement - Google Patents

Matériel d'enregistrement sensible à la chaleur et à la lumière et méthode d'enregistrement Download PDF

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Publication number
EP0287121B1
EP0287121B1 EP88106064A EP88106064A EP0287121B1 EP 0287121 B1 EP0287121 B1 EP 0287121B1 EP 88106064 A EP88106064 A EP 88106064A EP 88106064 A EP88106064 A EP 88106064A EP 0287121 B1 EP0287121 B1 EP 0287121B1
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Prior art keywords
heat
recording material
sensitive recording
group
parts
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.)
Expired - Lifetime
Application number
EP88106064A
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German (de)
English (en)
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EP0287121A3 (en
EP0287121A2 (fr
Inventor
Toshimi Satake
Toshiaki Minami
Tomoaki Nagai
Fumio Fujimura
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Jujo Paper Co Ltd
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Jujo Paper Co Ltd
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Publication date
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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
    • G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
    • G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic 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
    • B41M5/323—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
    • 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
    • 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
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/146—Laser beam

Definitions

  • the invention relates to a heat-sensitive and light-sensitive recording material which produces an image when heat and light energy are supplied, and to a recording method.
  • a heat-sensitive recording material is produced as follows: A coating composition is applied to the surface of a carrier such as paper, synthetic paper, film, plastic, etc., by finely grinding and dispersing a colorless chromogenic substance and a color development material, mixing the dispersions obtained with one another and adding a binder, filler, sensitizer, lubricant and other aids have been obtained. An instantaneous chemical occurs under the influence of heat from the thermal spring, thermal head, thermal stamp, laser beam, etc. Implementation that leads to the recording.
  • a carrier such as paper, synthetic paper, film, plastic, etc.
  • heat-sensitive recording method include the application in technical recording devices, terminal printers of computers, printers of facsimile machines, ticket machines, printers for barcode notes and the like.
  • the heat sensitive sheet must contain a basic colorless dye as an electron donating material. Both this dye and a Lewis acid are generally contained in the same layer, so that contamination due to inevitable color development may occur in the heat-sensitive recording sheet manufacturing process, storage or handling of the unused recording sheet.
  • the recording material according to the invention is a heat- and light-sensitive recording material which has a color formation layer on a support which contains an electron-donating compound but no electron-accepting compound, the electron-donating compound at least one fluoran dye of the following general formula (I) contains; 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 group or phenyl group; T3 and T4 can also be connected to an adjacent nitrogen atom to form a pyrrolidino, morpholino, piperidino or hexamethyleneimino group
  • 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 dyes of the following general formula (II) prefers.
  • 2-methyl-6-p- (p-dimethylaminophenyl) aminoanilinofluoran (melting point: 197-203 ° C.) of the following formula (III) and 2-chloro-3-methyl-6-p- (p-phenylaminophenyl) aminoanilinofluoran (melting point: 191.5-196 ° C) of the following formula (IV) is most preferred.
  • fluoranleuco dyes are not subject to any particular restrictions; the following can be used, for example: 2-methyl-6-p- (p-dimethylaminophenyl) aminoanilinofluoran, 2-methoxy-6-p- (p-dimethylaminophenyl) aminoanilinofluoran, 2-chloro-6-p- (p-dimethylaminophenyl) aminoanilinofluoran, p-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 fluoranleuco dyes of the general formula (I) according to the invention are used alone or in a mixture.
  • the color formation layer according to the invention contains the above basic colorless chromogenic dye, optionally a heat-fusible material, binder and other additives.
  • the heat-fusible material according to the invention does not contain an electron-accepting compound, but improves the color development sensitivity.
  • Typical examples of the heat-fusible materials according to the invention are: fatty acid amides such as stearinamide, palmitinamide, etc .; Ethylene bisamide; Montan wax; Polyethylene wax; Dimethyl terephthalate; benzyl p-benzyloxybenzoate; Dibenzyl terephthalate; ⁇ -naphthyl benzoate; N-acetyldiphenylamine; p-nitrobenzoic acid methyl ester; Diphenyl carbonate; methyl p-benzyloxybenzoate; p-nitrobenzaldehyde; Fluorene; Phenanthrene; ⁇ -naphthoquinone; 4 ⁇ -t-butylbenzyl 4- (4 ⁇ -t-butylbenzyloxy) benzoate; 4,4 ⁇ -n-butoxydiphenyl sulfone; p-tolyl carbonate; m-tolyl carbonate; o-tolyl carbon
  • the type and amount of the basic colorless chromogenic dye according to the invention, the heat-fusible material, the other additives, which are selected depending on the desired effect and the suitability for recording purposes, are not particularly limited. In general, it is advantageous to use 1 to 8 parts by weight of the heat-fusible material, 1 to 20 parts by weight of filler and 10 to 25 parts by weight of binder for binding the dye, based on 1 part by weight of the basic colorless chromogenic dye to use.
  • the heat and light sensitive material according to the invention is produced by applying the coating composition to a base material such as paper, synthetic paper, film, plastic, etc.
  • a base material such as paper, synthetic paper, film, plastic, etc.
  • the above basic colorless chromogenic dye according to the invention and optionally the other additives are ground to a particle size of several microns or smaller by means of a grinding device such as a ball mill, attritor, sand grinder, etc., or by means of a suitable emulsifying machine. Various additives are added to this.
  • the additives which can be used according to the invention are, for example, the following: Fillers; Release agents for preventing sheet sticking such as metal salts of fatty acids; Mottling prevention lubricants such as fatty acid amides, ethylene bisamide, montan wax, polyethylene wax, etc .; Dispersants such as sodium dioctylsulfosuccinic acid, sodium dodecylbenzenesulfonate, sodium auryl alcohol sulfate, sodium alginate, etc .; UV absorbers of the benzophenone and triazole series; Anti-foaming agents; waterproofing agents, etc. Both inorganic and as well as organic fillers used in the paper processing field.
  • 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.
  • a recording material having a color formation layer is used.
  • the recording process consists of two steps: (1) First, a latent image is thermally formed in the color formation layer. (2) Then the latent image is made a visible image by light irradiation.
  • the thermal pattern is generated using a thermal spring, a thermal head, laser beams, etc.
  • the light irradiation is carried out with a black light lamp, xenon lamp, carbon arc lamp, etc., UV light being the most suitable.
  • the exposure time is very short see you shortly. It is at most a few minutes.
  • the time interval between the end of the thermal recording and the exposure depends on the conditions of the recording method according to the invention. This means that the exposure can take place immediately, a few months (storage) or a few years (storage) after the thermal recording.
  • the recording image obtained absorbs light from the visible range to the near infrared range, ie light from 370-2000 nm.
  • the fluoranleuco dye according to the invention has the following structural component, in which two benzene nuclei are bonded to the fluorine skeleton in the molecule by three nitrogen atoms:
  • This part of the structure is photochemically active during exposure and forms an absorption point that absorbs light in the near infrared range.
  • the thermal recording and the exposure do not produce a colored image by themselves, one can assume the following: When heat energy is supplied, the basic colorless chromogenic dye is activated with melting, and when light energy is supplied, the above photochemical reaction occurs, so that color formation occurs.
  • Dispersion A (dye dispersion) Basic colorless dye (See Table 1.) 2.0 parts 10% aqueous solution of polyvinyl alcohol 4.6 parts water 2.6 parts
  • Dispersion A (dye dispersion) 9.2 parts Kaolin clay dispersion (50% dispersion) 12 parts
  • the 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 achieve a smoothness of 200-600 seconds.
  • a heat and light sensitive recording sheet was obtained.
  • Dispersion B (dispersion of thermofusible material) Heat fusible material (see table 1.) 6.0 parts 10% aqueous solution of polyvinyl alcohol 18.7 parts water 11.3 parts
  • Dispersion A (dye dispersion) 9.2 parts
  • Dispersion B (dispersion of thermofusible material) 36 parts Kaolin clay (50% dispersion) 12 parts
  • a heat and light sensitive recording sheet was obtained in the same manner as in Example 1 using this coating composition.
  • a heat and light sensitive recording sheet was obtained in the same manner as in Example 1, but using the following dispersion C instead of dispersion A.
  • Dispersion C Basic colorless dye See Table 1.
  • 3-diethylamino-6-methyl-7-anilinofluoran is a black colorant dye which is commonly used and is 3,6,6 ⁇ -tris (dimethylamino) spiro [fluorene-9,3 ⁇ -phthalide] a dye in which the superior optical legibility of the colored image was found in the near infrared range.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)

Claims (8)

  1. Matériau pour l'enregistrement thermosensible et photosensible, caractérisé par une couche révélatrice de couleur, sur un support, contenant un composé donneur d'électrons, mais pas de composé accepteur d'électrons, un composé donneur d'électrons étant au moins un colorant à base de fluoranne de la formule générale suivante (I):
    Figure imgb0014
     dans laquelle au moins l'un des restes R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈ et R₉ représente un groupe de la formule générale
    Figure imgb0015
     dans laquelle T₁, T₂ et T₃ sont identiques ou différents et représentent, chacun, un atome d'hydrogène, un groupe C₁-C₈ alcoyle, C₃-C₉ alcényle ou C₃-C₉ alcinyle,
    T₄ réprésente un atome d'hydrogène, un groupe C₁-C₈ alcoyle, C₃-C₉ alcényle ou C₃-C₉ alcinyle ou un groupe phenyle, de plus T₃ et T₄ peuvent former ensemble un groupe pyrrolidino-, morpholino, piperidino ou hexaméthylène imino par fixation sur un atome d'azote voisin et
    les restes R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈ et R₉ sont identiques ou différents et représentent, chacun, un atome d'hydrogène ou d'halogène, un groupe alcoyle, alcoxy, cyclo-alcoyle, nitro, hydroxy, amino, amino substitué, aralkyle, aralkyle substitué, aryle ou aryle substitué et n représente un nombre entier de 0 à 4.
  2. Matériau pour l'enregistrement suivant la revendication 1, caractérisé en ce que le leucocolorant à base de fluoranne de formule générale (I) est le 2-chloro-3-méthyl-6-p-(p-phénylaminophényl)aminoanilinofluoranne ou le 2-méthyl-6-p-(p-diméthylaminophényl)aminoanilinofluoranne.
  3. Matériau pour l'enregistrement thermosensible suivant l'une des revendications 1 ou 2, caractérisé en ce que la couche révélatrice de couleur contient de 1 à 8 parties en poids d'un matériau thermofusible, de 1 à 20 parties en poids de charge et de 10 à 25 parties en poids de liant pour une partie en poids du colorant à base de fluoranne (= colorant chromogène incolore basique).
  4. Matériau pour l'enregistrement thermosensible suivant l'une des revendications 1 ou 3, caractérisé en ce que le support est un papier, un papier synthétique, un film ou une matière plastique.
  5. Procédé d'enregistrement thermosensible et photosensible, caractérisé en ce que sur un matériau thermosensible et photosensible suivant l'une des revendications 1 à 4 est produite, par enregistrement thermique, une image latente et que celle-ci est ensuite convertie, par exposition, en une image visible.
  6. Procédé d'enregistrement suivant la revendication 5, caractérisé en ce que l'enregistrement thermique est produite par une plume thermique, une tête thermique ou des rayons laser.
  7. Procédé d'enregistrement suivant la revendication 5, caractérisé en ce que l'exposition se fait à l'aide d'une lampe à lumière noire, d'une lampe au xénon ou d'une lampe à arc.
  8. Procédé d'enregistrement suivant l'une des revendications 5 ou 7, caractérisé en ce que l'exposition se fait par rayonnement UV.
EP88106064A 1987-04-17 1988-04-15 Matériel d'enregistrement sensible à la chaleur et à la lumière et méthode d'enregistrement Expired - Lifetime EP0287121B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP94595/87 1987-04-17
JP62094595A JPH066396B2 (ja) 1987-04-17 1987-04-17 感熱感光記録材料及びその記録方法

Publications (3)

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EP0287121A2 EP0287121A2 (fr) 1988-10-19
EP0287121A3 EP0287121A3 (en) 1990-07-11
EP0287121B1 true EP0287121B1 (fr) 1993-08-04

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EP88106064A Expired - Lifetime EP0287121B1 (fr) 1987-04-17 1988-04-15 Matériel d'enregistrement sensible à la chaleur et à la lumière et méthode d'enregistrement

Country Status (4)

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US (1) US4853361A (fr)
EP (1) EP0287121B1 (fr)
JP (1) JPH066396B2 (fr)
DE (1) DE3882779D1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0381492B1 (fr) * 1989-02-03 1998-04-15 Nippon Paper Industries Co., Ltd. Matériau pour l'enregistrement optique, méthode pour l'enregistrement optique, et dispositif pour l'enregistrement optique utilisé dans cette méthode
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
US5260252A (en) * 1990-07-24 1993-11-09 Nashua Corporation Thermal latent image material and method of producing and developing the same
US5494768A (en) * 1992-10-01 1996-02-27 Nashua Corporation Toner composition containing ethylene bisamide compounds
US5441418A (en) * 1993-05-20 1995-08-15 Binney & Smith Inc. Thermochromic drawing device
US5514635A (en) * 1993-12-29 1996-05-07 Optum Corporation Thermal writing surface and method for making the same
CN1938370B (zh) * 2004-04-07 2011-01-26 西巴特殊化学品控股有限公司 涂料组合物显色方法
US20060093958A1 (en) * 2004-10-28 2006-05-04 Vladek Kasperchik Color forming compositions and associated methods
US7505058B2 (en) * 2005-12-07 2009-03-17 Dell Product L.P. Single head receipt printer
US7892619B2 (en) * 2006-12-16 2011-02-22 Hewlett-Packard Development Company, L.P. Coating for optical recording

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57169484A (en) * 1981-04-14 1982-10-19 Shin Nisso Kako Co Ltd Novel fluoran compound
US4524373A (en) * 1982-02-24 1985-06-18 Kanzaki Paper Manufacturing Co., Ltd. Fluoran derivatives as new compounds, process for preparing the same and recording system utilizing the same as colorless chromogenic material
JPS6274687A (ja) * 1985-09-30 1987-04-06 Shin Nisso Kako Co Ltd 発色性記録体
US4826806A (en) * 1986-07-31 1989-05-02 Shin Nisso Kako Co., Ltd. Fluoran compounds and color forming recording materials using same
JPH066392B2 (ja) * 1987-04-09 1994-01-26 日本製紙株式会社 感熱記録体
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

Also Published As

Publication number Publication date
JPS63260483A (ja) 1988-10-27
DE3882779D1 (de) 1993-09-09
JPH066396B2 (ja) 1994-01-26
EP0287121A3 (en) 1990-07-11
EP0287121A2 (fr) 1988-10-19
US4853361A (en) 1989-08-01

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