EP0251209A2 - Matériel pour l'enregistrement thermosensible - Google Patents

Matériel pour l'enregistrement thermosensible Download PDF

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Publication number
EP0251209A2
EP0251209A2 EP87109140A EP87109140A EP0251209A2 EP 0251209 A2 EP0251209 A2 EP 0251209A2 EP 87109140 A EP87109140 A EP 87109140A EP 87109140 A EP87109140 A EP 87109140A EP 0251209 A2 EP0251209 A2 EP 0251209A2
Authority
EP
European Patent Office
Prior art keywords
heat
sensitive recording
recording material
sensitive
group
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
EP87109140A
Other languages
German (de)
English (en)
Other versions
EP0251209A3 (en
EP0251209B1 (fr
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 EP0251209A2 publication Critical patent/EP0251209A2/fr
Publication of EP0251209A3 publication Critical patent/EP0251209A3/de
Application granted granted Critical
Publication of EP0251209B1 publication Critical patent/EP0251209B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • B41M5/337—Additives; Binders
    • B41M5/3377—Inorganic compounds, e.g. metal salts of organic acids
    • 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 heat-sensitive recording material which has superior resistance to the effects of light, climate and oils and better optical readability in the near infrared range.
  • a heat-sensitive recording sheet is generally prepared by applying to the surface of a support such as paper, synthetic paper, film, plastic, 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 them one Binder, filler, sensitizer, lubricant and other auxiliaries has been obtained. Under the influence of heat from the thermal spring, thermal head, thermal stamp, laser beam, etc., an instantaneous chemical conversion takes place, which leads to the recording.
  • heat-sensitive recording sheets include the use in technical recording devices, computer terminal printers, printers for facsimile machines, automatic ticket machines, printers for barcode notes and the like. Recently, much higher and more diverse requirements have been placed on recording devices, which is why high quality is required of the recording sheet required.
  • the heat-sensitive recording sheet is said to have a clear high-density recording image even at a low heat input, and to further superior resistance to the effects of light, climate and oils, i. H. good durability.
  • thermosensitive recording sheets are used for thermosensitive notes in which the color formation is limited in the visible area. Therefore, they were unsuitable for reading in the near infrared range, when using a semiconducting laser, bar code scanner, POS system, etc.
  • JO-LS 59-199757 and JO-LS 60-226871 propose heat-sensitive recording sheets with combined use of a known color developing agent (acid clay, phenolic resin, hydroxybenzoic acid ester, bisphenol-A) and a fluorene-fluorene leuco dye with superior color formation in the near infrared range been.
  • a known color developing agent as acid clay, phenolic resin, hydroxybenzoic acid ester, bisphenol-A
  • fluorene-fluorene leuco dye with superior color formation in the near infrared range been.
  • the image often discolors, or the image density decreases or the image is erased, and therefore, because of poor durability of the recording (poor resistance to light, climate and oils), the optical readability in the infrared range is significantly impaired if one leaves the leaves for a long time under environmental conditions with light, heat, moisture, etc.
  • the invention has for its object to provide a heat-sensitive recording material which is superior in the resistance to the action of light, climate and oils, and in the optical readability in the near infrared range, especially in bar code recordings.
  • a heat-sensitive recording material is produced by using at least one substance from the group of 4,4 als-dihydroxydiphenyl sulfone, 2-4 ⁇ -dihydroxydiphenyl sulfone and bis- (3-tert-butyl-4-hydroxy-6-methylphenyl) as the color developing agent in the heat-sensitive color development layer.
  • R1, R2, R3, R4, R5 and R6 are the same or different and each have a hydrogen atom, an alkyl radical having 1-18 carbon atoms, chloroalkyl radical having 3-7 carbon atoms , a lower alkoxy group, halogenated alkyl group, phenyl group, substituted phenyl group or benzyl group; R7, R8 and R9 are the same or different and each represents a hydrogen, halogen atom or a lower alkyl group; and wherein R1 and R2, or R3 and R4 optionally with the nitrogen atom (the amino group) a heterocyclic ring with 4-6 Can form carbon atoms (which can contain an oxygen, sulfur or a second nitrogen atom).
  • 4,4'-dihydroxydiphenyl sulfone bisphenol S
  • 2,4 ⁇ -dihydroxydiphenyl sulfone has a melting point of 181-183 ° C.
  • the two color developing agents are known.
  • bis (3-tert-butyl-4-hydroxy-6-methylphenyl) sulfone which was described in JP-OL 61-230983, is a new color developing agent with a melting point of 255-256 ° C.
  • the three color developing agents above have the following structures:
  • the three color developing agents above have the structural commonality that two phenol rings are connected by a sulfone group, this seems to be a reason for the effects according to the invention.
  • lower alkyl and alkoxy groups mean those having 1-5 carbon atoms, and these alkyl and alkoxy groups can be "linear or branched".
  • fluorene leuco dyes of the formulas (I) and (II) those compounds are preferred in which R1, R2, R3, R4, R5, R6, R7, R8 and R9 have the meaning given above.
  • 3,6,6 ⁇ -tris (dimethylamino) spiro (fluoren-9,3 ⁇ -phthalide) with the following structure (melting point of 244-246 ° C) is most preferred.
  • fluoran-leuco dyes which develop black color can also be used together with the dye according to the invention to supplement the color formation in the visible range.
  • fluoran dyes are as follows: 3-diethylamino-6-methyl-7-anilinofluoran, 3- (N-ethyl-p-toluidino) -6-methyl-7-anilinofluoran, 3- (N-ethyl-N-isoamyl) amino-6-methyl-7-anilinofluoran, 3-diethylamino-6-methyl-7- (p, p-dimethylanilino) fluoran, 3-pyrolidino-6-methyl-7-anilinofluoran, 3-piperidino-6-methyl-7-anilinofluoran, 3- (N-cyclohexyl-N-methylamino) -6-methyl-7-anilinofluoran, 3-diethylamino-7- (m-trifluoromethylanilino) fluor
  • the following substances can be used as sensitizers: Fatty acid amide such as stearic acid amide, palmitic acid amide; Ethylene bisamide; Montan wax; Polyethylene wax; Terephthalic acid dibenzyl ester; benzyl p-benzyloxybenzoate; Di-p-tolyl carbonate; p-benzylbiphenyl; Phenyl- ⁇ -naphthyl carbonate; 1,4-diethoxynaphthalene; 1-hydroxy-2- naphthalenecarboxylic acid phenyl ester; and the same.
  • Fatty acid amide such as stearic acid amide, palmitic acid amide
  • Ethylene bisamide Montan wax
  • Polyethylene wax Terephthalic acid dibenzyl ester
  • benzyl p-benzyloxybenzoate Di-p-tolyl carbonate
  • p-benzylbiphenyl Phenyl- ⁇ -naphthy
  • Halogen-substituted zinc benzoate derivatives for example, can be used as stabilizers and thus improve the invention.
  • Examples of zinc benzoate derivatives according to the invention are as follows:
  • the top of the color development layer and the back of the support can be coated with a thin transparent film such as polyester film, polypropylene film, etc.
  • Binders according to the invention are e.g. B. fully saponified polyvinyl alcohol, degree of polymerization: 200-1900, partially 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-vinyl chloride, cellulose-acrylate, cellulose-acrylate, cellulose , Polyvinyl butyral, polystyrene, copolymers of the above compounds, polyamide resin, silicone resin, petroleum resin, terpene resin, ketone resin and coumarone resin.
  • These high molecular weight binders can be used after being dissolved in a solvent such as water, alcohol, ketone, ester
  • the type and amount of the organic color developing agent of the present invention, the basic colorless chromogenic dye, the other additives, which are determined 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 organic color developing agent according to the invention and 1 to 20 parts by weight of filler, based on 1 part of the basic colorless chromogenic dye, and 10 to 25 parts by weight of binder, based on the total solids content.
  • the heat-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.
  • the above organic color developing agent according to the present invention, iron salt of a saturated higher fatty acid, the above basic colorless chromogenic dye, optionally the other additives are mixed by means of a grinding device such as ball mill, attrition mill, sand grinder, etc., or by means of a suitable emulsifying machine to a particle size of several microns or grind smaller.
  • a grinding device such as ball mill, attrition mill, sand grinder, etc.
  • a suitable emulsifying machine to a particle size of several microns or grind smaller.
  • additives are added to this.
  • the additives that can be used according to the invention are e.g. B.
  • Inorganic or organic fillers such as silicon dioxide, calcium carbonate, kaolin, baked kaolin, diatomaceous earth, talc, titanium dioxide, Aluminum hydroxide, etc .
  • Release agents such as metal salts of fatty acids
  • Lubricants such as waxes
  • UV absorbers of the benzophenone and triazole series waterproofing agents such as glyoxal, etc .
  • Dispersants Antifoam and so on.
  • the reason for the superior optical readability of the heat-sensitive recording sheet according to the invention in the near infrared range is perhaps the following:
  • the colored image of the recording sheet takes - when using the previous electron-donating color developing agents, e.g. Fluoran dyes - no light in the near infrared range.
  • the particular fluorene leuco dyes according to the invention effectively absorb the light in the near infrared range (particularly the range from 700-1000 nm) during color development in the heat-melt reaction with an electron acceptor (color developing agent).
  • a heat-sensitive recording sheet consists of a basic colorless dye as an electron donor and an organic acidic substance, e.g., a phenolic compound, aromatic carboxylic acid, organic sulfonic acid, etc.
  • the heat-melting reaction is a kind of acid-base reaction based on electron donation and uptake, thereby forming a metastable electron moving complex, which leads to the colored image.
  • 4,4 ⁇ -dihydroxydiphenyl sulfone, 2,4 ⁇ -dihydroxydiphenyl sulfone and bis- (3-tert-butyl-4-hydroxy-6-methylphenyl) sulfone have a structure with two phenol rings connected by a sulfone group.
  • the chemical bonding force between one of the above special colorless fluorene leuco dyes and 4,4'-dihydroxydiphenyl sulfone, 2,4 ⁇ -dihydroxydiphenyl sulfone and / or bis (3-tert-butyl-4-hydroxy-6- 6- methylphenyl) sulfone much stronger than that between one of the basic colorless fluorene leuco dyes and a previous color developing agent, for example acid clay, phenolic resins, hydroxybenzoic acid esters, bisphenol A and p-hydroxybenzoic acid benzyl esters. Therefore, it is believed that the chemical bond is not released for a long time even under the influence of light, heat, moisture, etc., so that the recording image is very stable, and the optical readability in the near infrared range is not reduced.
  • Solution A (dye dispersion): 3,6,6 ⁇ -tris (dimethylamino) spiro (fluorene-9,3 ⁇ -phthalide) 2.0 parts 10% aqueous solution of polyvinyl alcohol 4.6 parts Water 2.6 parts
  • Solution B color developer dispersion: 4,4'-dihydroxydiphenyl sulfone 6.0 parts 10% aqueous solution of polyvinyl alcohol 18.8 parts Water 11.2 parts
  • This 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 sensitive recording sheet was obtained.
  • Solution C (sensitizer dispersion): p-Benzylbiphenyl 4.0 parts 10% aqueous solution of polyvinyl alcohol 12.5 parts Water 7.5 parts
  • the solution C was individually in a attritor until Grind particle size of 3 microns.
  • This coating composition was treated in the same manner as in Example 1. A heat sensitive recording sheet was obtained.
  • Solution D stabilizer dispersion: Z-salt of p-chlorobenzoic acid 4.0 parts 10% aqueous solution of polyvinyl alcohol 12.5 parts Water 7.5 parts
  • a heat-sensitive recording sheet was obtained in the same manner as in Example 2, except that Solution D was used instead of Solution C.
  • Solution E color developer dispersion: 2,4'-dihydroxydiphenyl sulfone 6.0 parts 10% aqueous solution of polyvinyl alcohol 18.8 parts Water 11.2 parts
  • Solution E was ground and dispersed as in Example 1.
  • a heat-sensitive recording sheet was obtained in the same manner as in Example 1, except that Solution E was used instead of Solution B.
  • a heat-sensitive recording sheet was obtained in the same manner as in Example 2, except that Solution E was used instead of Solution B.
  • a heat-sensitive recording sheet was obtained in the same manner as in Example 3, except that Solution E was used instead of Solution B.
  • Solution F color developer dispersion: Bis (3-tert-butyl-4-hydroxy-6-methylphenyl) sulfone 6.0 parts 10% aqueous solution of polyvinyl alcohol 18.8 parts Water 11.2 parts
  • Solution G (dye dispersion): 3,6-bis (diethylamino) fluorenspiro (9,3 ⁇ ) phthalide (a compound XIV given above) 2.0 parts 10% aqueous solution of polyvinyl alcohol 4.6 parts Water 2.6 parts
  • Solution G (dye dispersion) 9.2 parts
  • Solution F (color developing agent dispersion) 36.0 parts Kaolin clay (50% aqueous dispersion) 12.0 parts
  • This 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 sensitive recording sheet was obtained.
  • a heat-sensitive recording sheet was obtained in the same manner as in Example 2, except that Solution F was used instead of Solution B and Solution G was used instead of Solution A.
  • a heat-sensitive recording sheet was obtained in the same manner as in Example 3, except that Solution F was used instead of Solution B and Solution G was used instead of Solution A.
  • Solution A (dye dispersion): 3,6,6 ⁇ -tris (dimethylamino) spiro (fluorene-9,3 ⁇ -phthalide) 2.0 parts 10% aqueous solution of polyvinyl alcohol 4.6 parts Water 2.6 parts
  • Solution B Color developer dispersion: Color developing agent (see Table 1) 6.0 parts 10% aqueous solution of polyvinyl alcohol 18.8 parts Water 11.2 parts
  • This 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. You got one heat sensitive recording sheet.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Inorganic Chemistry (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Color Printing (AREA)
EP87109140A 1986-06-25 1987-06-25 Matériel pour l'enregistrement thermosensible Expired - Lifetime EP0251209B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP61149196A JPS634990A (ja) 1986-06-25 1986-06-25 感熱記録材料
JP149196/86 1986-06-25

Publications (3)

Publication Number Publication Date
EP0251209A2 true EP0251209A2 (fr) 1988-01-07
EP0251209A3 EP0251209A3 (en) 1989-09-06
EP0251209B1 EP0251209B1 (fr) 1992-04-15

Family

ID=15469917

Family Applications (1)

Application Number Title Priority Date Filing Date
EP87109140A Expired - Lifetime EP0251209B1 (fr) 1986-06-25 1987-06-25 Matériel pour l'enregistrement thermosensible

Country Status (5)

Country Link
US (1) US4868151A (fr)
EP (1) EP0251209B1 (fr)
JP (1) JPS634990A (fr)
CA (1) CA1264549A (fr)
DE (1) DE3778222D1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0410721A3 (en) * 1989-07-26 1991-06-05 Jujo Paper Co., Ltd. Heat-sensitive recording material
US5348930A (en) * 1993-03-31 1994-09-20 Nicca Chemical Co., Ltd. Heat sensitive recording material
EP0616897A3 (fr) * 1993-03-24 1994-12-14 Nicca Chemical Co Matériau d'enregistrement sensible à la chaleur.
FR2713991A1 (fr) * 1993-12-16 1995-06-23 Ricoh Kk Matériau d'impression thermique.

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6692525B2 (en) 1992-02-28 2004-02-17 Advanced Medical Optics, Inc. Intraocular lens
US5233007A (en) * 1992-04-14 1993-08-03 Allergan, Inc. Polysiloxanes, methods of making same and high refractive index silicones made from same
US5512609A (en) * 1992-04-14 1996-04-30 Allergan, Inc. Reinforced compositions and lens bodies made from same
US5278258A (en) * 1992-05-18 1994-01-11 Allergan, Inc. Cross-linked silicone polymers, fast curing silicone precursor compositions, and injectable intraocular lenses
US5391590A (en) * 1993-01-12 1995-02-21 Allergan, Inc. Injectable intraocular lens compositions and precursors thereof
US5326677A (en) * 1993-02-19 1994-07-05 Eastman Kodak Company Optical retrieval apparatus using a tellurium (IV) leuco dye
US5340537A (en) * 1993-04-16 1994-08-23 Big Three Industries, Inc. Temperature indicating compositions
US6468306B1 (en) 1998-05-29 2002-10-22 Advanced Medical Optics, Inc IOL for inhibiting cell growth and reducing glare
US7249885B2 (en) * 2002-10-16 2007-07-31 Clyde Bergemann Gmbh Heat flux measuring device for pressure pipes, method for producing a measuring device, method for monitoring an operating state of a heat exchanger, heat exchanger and method for measuring a heat flux

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3560229A (en) * 1961-08-31 1971-02-02 Burroughs Corp Colorforming compositions and methods for preparing and controlling same
US3344189A (en) * 1963-06-24 1967-09-26 Davis Chester Amino-fluorene-compounds and process for the preparation thereof
DE2145027A1 (de) * 1971-09-09 1973-03-15 Basf Ag Verfahren zur herstellung von aminofluorenverbindungen
JPS57203590A (en) * 1981-06-09 1982-12-13 Honshu Paper Co Ltd Heat-sensitive recording medium
JPS59199757A (ja) * 1983-04-28 1984-11-12 Yamamoto Kagaku Gosei Kk フルオレン化合物、その製造法およびそれを用いる記録材料
JPS6061289A (ja) * 1983-09-16 1985-04-09 Jujo Paper Co Ltd 感熱記録紙
JPS60226871A (ja) * 1984-04-25 1985-11-12 Yamamoto Kagaku Gosei Kk フルオレン化合物、その製造法および該化合物を用いる記録材料
US4721701A (en) * 1985-01-09 1988-01-26 Jujo Paper Co., Ltd. Thermosensitive recording sheet
DE3601645A1 (de) * 1985-01-31 1986-08-07 Mitsubishi Paper Mills, Ltd., Tokio/Tokyo Waermeempfindliches aufzeichnungsmaterial
US4658276A (en) * 1985-06-22 1987-04-14 Kanzaki Paper Manufacturing Co., Ltd. Phthalide derivatives and recording system utilizing the same
JPH0815813B2 (ja) * 1986-06-09 1996-02-21 山田化学工業株式会社 感熱記録材料
JPH01172791A (ja) * 1987-12-28 1989-07-07 Hitachi Ltd 放射線検出素子
JPH115255A (ja) * 1997-06-17 1999-01-12 Ricoh Co Ltd 三次元物体形成方法、三次元物体形成装置及び三次元物体

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0410721A3 (en) * 1989-07-26 1991-06-05 Jujo Paper Co., Ltd. Heat-sensitive recording material
EP0616897A3 (fr) * 1993-03-24 1994-12-14 Nicca Chemical Co Matériau d'enregistrement sensible à la chaleur.
US5348930A (en) * 1993-03-31 1994-09-20 Nicca Chemical Co., Ltd. Heat sensitive recording material
EP0618082A1 (fr) * 1993-03-31 1994-10-05 NICCA CHEMICAL CO., Ltd. Matériau d'enregistrement sensible à la chaleur
FR2713991A1 (fr) * 1993-12-16 1995-06-23 Ricoh Kk Matériau d'impression thermique.
US5536697A (en) * 1993-12-16 1996-07-16 Ricoh Company, Ltd. Thermal printing material for providing improved image reliabilities

Also Published As

Publication number Publication date
EP0251209A3 (en) 1989-09-06
CA1264549A (fr) 1990-01-23
DE3778222D1 (de) 1992-05-21
US4868151A (en) 1989-09-19
EP0251209B1 (fr) 1992-04-15
JPS634990A (ja) 1988-01-09

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