EP0287121A2 - 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
EP0287121A2
EP0287121A2 EP88106064A EP88106064A EP0287121A2 EP 0287121 A2 EP0287121 A2 EP 0287121A2 EP 88106064 A EP88106064 A EP 88106064A EP 88106064 A EP88106064 A EP 88106064A EP 0287121 A2 EP0287121 A2 EP 0287121A2
Authority
EP
European Patent Office
Prior art keywords
heat
light
recording material
dye
sensitive recording
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
EP88106064A
Other languages
German (de)
English (en)
Other versions
EP0287121B1 (fr
EP0287121A3 (en
Inventor
Toshimi Satake
Toshiaki Minami
Tomoaki Nagai
Fumio 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 EP0287121A2 publication Critical patent/EP0287121A2/fr
Publication of EP0287121A3 publication Critical patent/EP0287121A3/de
Application granted granted Critical
Publication of EP0287121B1 publication Critical patent/EP0287121B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/72Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
    • G03C1/73Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41MPRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/30Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
    • B41M5/323Organic colour formers, e.g. leuco dyes
    • B41M5/327Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
    • B41M5/3275Fluoran compounds
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00Stock material or miscellaneous articles
    • Y10S428/913Material designed to be responsive to temperature, light, moisture
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00Stock material or miscellaneous articles
    • Y10S428/914Transfer or decalcomania
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/146Laser beam

Definitions

  • the invention relates to a heat- and light-sensitive recording material which gives an image when heat and light energy is supplied and 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.
  • 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 having 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) aminoani linofluoran, 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 contains no 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
  • 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, methyl cellulose, carboxymethyl cellulose, styrene-maleic anhydride copolymers, styrene-butadiene copolymers, cellulose derivatives such as ethyl cellulose and acetyl cellulose, polyvinyl chloride, polyvinyl acetate, polyacrylamide, polyacrylic acid ester, polyvinyl butyral, polystyrene resin, polyamide resin, copolymers, the above, and coumarone resin.
  • These high molecular weight binders can be used after being dissolved in
  • 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.
  • Fillers both anor ganic as well as organic fillers used in the paper processing field are used.
  • 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 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 basic colorless chromogenic dye 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)
  • 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.
  • 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.
  • 3-diethylamino-6-methyl-7-anilinofluoran is a black colorant dye that 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)
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)

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

Family

ID=14114628

Family Applications (1)

Application Number Title Priority Date Filing Date
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)

Country Link
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
CA2009088C (fr) * 1989-02-03 1994-05-31 Toshimi Satake Support et methode d'enregistrement optique et dispositif d'enregistrement realisant cette methode
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
AU2005231979B2 (en) * 2004-04-07 2011-02-03 Basf Se Method of coloring a coating composition
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

Citations (5)

* 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
EP0089752A2 (fr) * 1982-02-24 1983-09-28 Kanzaki Paper Manufacturing Co., Ltd Dérivés de fluorane, procédé pour leur préparation et leur utilisation dans des systèmes d'enregistrement
JPS6274687A (ja) * 1985-09-30 1987-04-06 Shin Nisso Kako Co Ltd 発色性記録体
FR2602238A1 (fr) * 1986-07-31 1988-02-05 Shin Nisso Kako Co Ltd Composes du fluorane et matieres d'enregistrement chromogenes les utilisant
EP0286116A2 (fr) * 1987-04-09 1988-10-12 Jujo Paper Co., Ltd. Matériau d'enregistrement thermosensible

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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 (5)

* 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
EP0089752A2 (fr) * 1982-02-24 1983-09-28 Kanzaki Paper Manufacturing Co., Ltd Dérivés de fluorane, procédé pour leur préparation et leur utilisation dans des systèmes d'enregistrement
JPS6274687A (ja) * 1985-09-30 1987-04-06 Shin Nisso Kako Co Ltd 発色性記録体
FR2602238A1 (fr) * 1986-07-31 1988-02-05 Shin Nisso Kako Co Ltd Composes du fluorane et matieres d'enregistrement chromogenes les utilisant
EP0286116A2 (fr) * 1987-04-09 1988-10-12 Jujo Paper Co., Ltd. Matériau d'enregistrement thermosensible

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 11, no. 272 (M-622)(2719) 04 September 1987, & JP-A-62 074 687 (SHIN NISSO KAKO CO LTD) 06 April 1987 *
PATENT ABSTRACTS OF JAPAN vol. 7, no. 11 (C-145)(1156) 18 Januar 1983, & JP-A-57 169 484 (SHINNITSUSOU KAKOU K.K.) 19 Oktober 1982 *

Also Published As

Publication number Publication date
JPH066396B2 (ja) 1994-01-26
US4853361A (en) 1989-08-01
JPS63260483A (ja) 1988-10-27
EP0287121B1 (fr) 1993-08-04
DE3882779D1 (de) 1993-09-09
EP0287121A3 (en) 1990-07-11

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