EP0247737A1 - Impression par transfert thermique - Google Patents

Impression par transfert thermique Download PDF

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Publication number
EP0247737A1
EP0247737A1 EP87303831A EP87303831A EP0247737A1 EP 0247737 A1 EP0247737 A1 EP 0247737A1 EP 87303831 A EP87303831 A EP 87303831A EP 87303831 A EP87303831 A EP 87303831A EP 0247737 A1 EP0247737 A1 EP 0247737A1
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EP
European Patent Office
Prior art keywords
alkyl
dye
transfer printing
sheet
ring
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
EP87303831A
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German (de)
English (en)
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EP0247737B1 (fr
Inventor
Peter Gregory
Roy Bradbury
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to AT87303831T priority Critical patent/ATE55330T1/de
Publication of EP0247737A1 publication Critical patent/EP0247737A1/fr
Application granted granted Critical
Publication of EP0247737B1 publication Critical patent/EP0247737B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/388—Azo dyes

Definitions

  • TTP thermal transfer printing
  • a heat-transferable dye is applied to a sheet-like substrate in the form of an ink, usually containing a polymeric or resinous binder to bind the dye to the substrate, to form a transfer sheet.
  • This is then placed in contact with the material to be printed, (generally a film of polymeric material such as a polyester sheet) hereinafter called the receiver sheet and selectively heated in accordance with a pattern information signal whereby dye from the selectively heated regions of the transfer sheet is transferred to the receiver sheet and forms a pattern thereon in accordance with the pattern of heat applied to the transfer sheet.
  • a dye for TTP is its thermal properties, brightness of shade, fastness properties, such as light fastness, and facility for application to the substrate in the preparation of the transfer sheet.
  • the dye should transfer evenly, in proportion to the heat applied to the TTP sheet so that the depth of shade on the receiver sheet is proportional to the heat applied and a true grey scale of coloration can be achieved on the receiver sheet.
  • Brightness of shade is important in order to achieve as wide a range of shades with the three primary dye shades of yellow, magenta and cyan.
  • the dye As the dye must be sufficiently mobile to migrate from the transfer sheet to the receiver sheet at the temperatures employed, 300-400°C, it is generally free from ionic and water-solubilising groups, and is thus not readily soluble in aqueous or water-miscible media, such as water and ethanol.
  • aqueous or water-miscible media such as water and ethanol.
  • suitable dyes are also not readily soluble in the hydrocarbon solvents which are commonly used in, and thus acceptable to, the printing industry; for example, alcohols such as i-propanol, ketones such as methyl-ethylketone (MEK), methyl-i-butylketone (MIBK) and cyclohexanone and aromatic hydrocarbons such as toluene.
  • the dye can be applied as a dispersion in a suitable solvent, it has been found that brighter, glossier and smoother final prints can be achieved on the receiver sheet if the dye is applied to the substrate from a solution. In order to achieve the potential for a deep shade on the receiver sheet it is desirable that the dye should be readily soluble in the ink medium. It is also important that a dye which has been applied to a transfer sheet from a solution should be resistant to crystallisation so that it remains as an amorphous layer on the transfer sheet for a considerable time.
  • Stable dyesheets resistant to dye migration or crystallisation. Stable printed images on the receiver sheet (to heat and especially light).
  • CI Disperse Yellow 3 an azophenol dye, does not have the correct spectral characteristics (too red and dull), has poor solubility (precludes solution coated dyesheets), is tinctorially weak (gives low optical density on printing) and has poor light fastness.
  • CI Disperse Yellow 54 a quinophthalone dye which is probably the leading yellow dye for the conventional transfer printing of polyester textile materials, has very poor solubility which precludes its use for solution coated dyesheets.
  • thermo transfer printing sheet comprising a substrate having a coating comprising a dye of the formula: wherein
  • the coating preferably comprises a binder and one or more dyes of Formula I.
  • the ratio of binder to dye is preferably at least 1:1 and more preferably from 1.5:1 to 4:1 in order to provide good adhesion between the dye and the substrate and inhibit migration of the dye during storage.
  • the coating may also contain other additives, such as curing agents, preservatives, etc., these and other ingredients being described more fully in EP 133011A, EP 133012A and EP 111004A.
  • the binder may be any resinous or polymeric material suitable for binding the dye to the substrate which has acceptable solubility in the ink medium, i.e. the medium in which the dye and binder are applied to the transfer sheet.
  • binders include cellulose derivatives, such as ethylhydroxyethylcellulose (EHEC), hydroxypropylcellulose (HPC), ethylcellulose, methylcellulose, cellulose acetate and cellulose acetate butyrate; carbohydrate derivatives, such as starch; alginic acid derivatives; alkyd resins; vinyl resins and derivatives, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl butyral and polyvinyl pyrrolidone; polymers and co-polymers derived from acrylates and acrylate derivatives, such as polyacrylic acid, polymethyl methacrylate and styrene-acrylate copolymers, polyester resins, polyamide resins, such as melamines; polurea
  • binders of this type are EHEC, particularly the low and extra-low viscosity grades, and ethyl cellulose.
  • Formula I is written in the hydrazone tautomeric form because the dye is believed to exist in this form (see Lycka and Machacek, in Dyes and Pigments 1986, 171).
  • Ring A carries 1 or 2 substituents and that one of these groups is in the 4 position with respect to the azo link. Where there is a single substituent this is preferably in the 2 or 4 position, and where there are two substituents these are preferably in the 2 and the 4 positions.
  • X is fluorine and X is chlorine or fluorine.
  • R1 and R 2 are each independently selected from C 1-8 -alkyl, phenyl, C l-4 -alkylphenyl, methylene, and a chain of two or more alkyl groups, especially two or three C1-4-alkyl groups, carrying a total of up to 12 carbon atoms linked by -0- groups. Where R is alkylene, especially methylene, the substituent on A is preferably -CO.OCH 2 - and comprises a fused lactone ring attached to Ring A at the 3 and 4 positions with respect to the azo link.
  • substituents on Ring A are F; Cl; Br; -CF 3 ; -NO 2 ; -CN; -CO.O-C 1-4 -alkyl, especially -CO.OC 2 H 5 ; -CO.C 1-4 -alkyl, especially -CO.CH 3 ; -CO.H; -CO.Ph; -CO.SC 1-4 -alkyl, especially -CO.SC 2 H 5 ; -CO.OC 2 H 4 OCH3; -CO.OC 2 H 4 OC 2 H 4 OCH 3 , -CO.OCh; -CO-N(C 4 H 9 ) 2 , -OSO 2 .Ph, -SO 2 .OPh; -SO 2 .NH.C 8 H 17 , -OSO 2 .N(CH 3 ) 2 , -CO.OCH 2 -furyl and 4-(i-C 3 H 7 )PhCO-, in which Ph is phenyl and Ch
  • Ring A is 4-chloroPh, 2-chloroPh, 4-fluoroPh, 2-fluoroPh, 4-chloro-2-trifluoromethylPh, 4-nitroPh, 2-nitroPh, 4-cyanoPh, 2-cyanoPh, 4-formylPh, 4-acetylPh, 4-(ethylthiocarbonyl)Ph, 4-(methoxyethoxycarbonyl)Ph, 4-(methoxyethoxyethoxy- carbonyl)Ph, 2,4-dichloroPh, 4-(N-[2-ethylhexyl]aminosulphonyl)Ph, 3,4-dichloroPh, 3-(N,N-dimethylaminosulphonyloxy)Ph, 3-(phenyl- sulphonyloxy)Ph, 2-nitro-4-chloroPh, 4-(2-ethylhexylaminocarbonyl)Ph, 4-(phenoxysulphonyl)
  • the C 1-12 -alkyl group represented by Z is preferably not branched in the alpha- or beta-position and is more preferably unbranched. It is preferred that Z is C 1-4 -n-alkyl and, more especially, methyl.
  • the C 2 - 12 -alkyl group represented by R is preferably not branched in the alpha- or beta-position. It is preferred that R is C 2-6 -n-alkyl, especially C 3-5 -n-alkyl and more especially n-propyl or n-butyl. Where R represents an interrupted alkyl group this preferably comprises two or more alkyl groups, especially two or three C1-4-n-alkyl groups, carrying a total of up to 12 carbon atoms, linked by oxygen atoms.
  • interrupted alkyl represented by-R is C 1-4 -alkoxy-C 2-4 -n-alkyl, such as 2-methoxyethyl, 2-ethoxyethyl, 3-ethoxy-n-propyl and 3-n-butoxy-n-propyl.
  • R Specific examples of the group represented by R are ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-octyl, 2-ethyl- n-hexyl, 2-methoxyethyl, 2-ethoxyethyl, 3-methoxy-n-propyl, 3-n-butoxy-n-propyl, phenyl and 4-methylphenyl
  • free from hydrogen atoms capable of inter- molecular hydrogen bonding is meant that the group R is free of "acidic" hydrogen atoms such as are present in -OH and -NH- groups which are capable of forming inter-molecular hydrogen bonds. This restriction does not, however, exclude such groups if their position permits the formation of intra-molecular hydrogen bonds.
  • the dye of Formula I has particularly good thermal properties giving rise to even prints on the receiver sheet, whose depth of shade is accurately proportional to the quantity of applied heat so that a true grey scale of coloration can be attained.
  • the dye of Formula I also has strong coloristic properties and good solubility in a wide range of solvents, especially those solvents which are widely used and accepted in the printing industry, for example, alkanols, such as i-propanol & butanol; aromatic hydrocarbons, such as toluene, and ketones such as MEK, MIBK and cyclohexanone.
  • solvents especially those solvents which are widely used and accepted in the printing industry, for example, alkanols, such as i-propanol & butanol; aromatic hydrocarbons, such as toluene, and ketones such as MEK, MIBK and cyclohexanone.
  • solvents especially those solvents which are widely used and accepted in the printing industry, for example, alkanols, such as i-propanol & butanol; aromatic hydrocarbons, such as toluene, and ketones such as MEK, MIBK and cyclohexanone.
  • the combination of strong coloristic properties and good solubility in the preferred solvents allows the achievement of deep, even shades on the receiver sheet.
  • the receiver sheets according to the present invention have bright, strong and even yellow shades which are fast to both light and heat.
  • the substrate may be any convenient sheet material capable of withstanding the temperatures involved in TTP, up to 400°C over a period of up to 20 milliseconds (msec) yet thin enough to transmit heat applied on one side through to the dye on the other side to effect transfer to a receiver sheet within such short periods, typically from 1-10 msec.
  • suitable materials are paper, especially high quality paper of even thickness, such as capacitor paper, polyester, polacrylate, polyamide, cellulosic and polyalkylene films, metallised forms thereof, including co-polymer and laminated films, especially laminates incorporating a polyester receptor layer on which the dye is deposited.
  • Such laminates preferably comprise, a backcoat, on the opposite side of the laminate from the receptor layer, of a heat resistant material, such as a thermoseting resin, e.g a silicone, acrylate or polyurethane resin, to separate the heat source from the polyester and prevent melting of the latter during the thermal transfer printing operation.
  • a heat resistant material such as a thermoseting resin, e.g a silicone, acrylate or polyurethane resin, to separate the heat source from the polyester and prevent melting of the latter during the thermal transfer printing operation.
  • the thickness of the substrate may vary within wide limits depending upon its thermal characteristics but is preferably less that 50 um and more preferably below 10 pm.
  • a transfer printing process which comprises contacting a transfer sheet coated with a dye of Formula I with a receiver sheet, so that the dye is in contact with the receiver sheet and selectively heating areas of the transfer sheet whereby dye in the heated areas of the transfer sheet may be selectively transferred to the receiver sheet.
  • the transfer sheet is preferably heated to a temperature from 250°C to 400°C, more preferably above 300°C and especially around 350°C, for a period of from 1 to 10 milliseconds while it is maintained with the coating in contact with the receiver sheet.
  • the depth of shade of print on any area of the receiver sheet will vary with the time period for which the transfer sheet is heated while in contact with that area of the receiver sheet.
  • the receiver sheet conveniently comprises a polyester sheet material, especially a white polyester film, preferably of polyethylene terephthalate (PET).
  • PET polyethylene terephthalate
  • some dyes of Formula I are known for the coloration of textile materials made from PET, the coloration of textile materials, by dyeing or printing is carried out under such conditions of time and temperature that the dye can penetrate into the PET and become fixed therein. In thermal transfer printing, the time period is so short that penetration of the PET is much less effective and the substrate is preferably provided with a receptive layer, on the side to which the dye is applied, into which the dye more readily diffuses to form a stable image.
  • Such a receptive layer which may be applied by co-extrusion or solution coating techniques, may comprise a thin layer of a modified polyester or a different polymeric material which is more permeable to the dye than the PET substrate. While the nature of the receptive layer will affect to some extent the depth of shade and quality of the print obtained it has been found that the dyes of Formula I give particularly strong and good quality prints (e.g. fast to light, heat and storage) on any specific transfer or receiver sheet, compared with other dyes of similar structure which have been proposed for thermal transfer printing. The design of receiver and transfer sheets is discussed further in EP 133,011 and EP 133012.
  • a solution was prepared by stirring 47g of methyl ethyl ketone (MEK), 31g of cyclohexanone and 20g of a 20% solution of EHEC (extra low) in cyclohexanone until homogeneous (about 10 minutes). Then 2g of Dye 1 were added, the solution was again stirred until the dye had completely dissolved (about 20 minutes at ambient). The ink had a viscosity of 16 seconds (Zahn No 2 at 20°C).
  • MEK methyl ethyl ketone
  • EHEC extra low
  • Example 40 This was prepared by the method of Example 40 except that the Dye 1 was replaced by Dye 2.
  • the ink had the same viscosity as Ink 1'.
  • Inks 1C to 10C were prepared exactly as for Ink 1 except that in each ink the dye was replaced by a dye of the following formula: in which Q, T and Ring A are defined in Table 2.
  • each dye was virtually insoluble, even after heating to 40°C. Because the dyes are insoluble they are less desirable for use in TTP processes for the reasons given hereinbefore.
  • Dyes G, H & J three more comparative dyes of Formula II which fall outside the scope of Formula I, were soluble in the ink medium and inks comprising solutions of the dyes in the solvent could be prepared.
  • a solution was prepared by stirring 47g MEK,.31g of cyclohexanone and 20g of a 20% solution of EHEC (extra low) in cyclohexanone together until homogeneous (about 10 minutes). Then 2g of Dye A was added. The dye was almost completely out of solution, even after stirring for 30 minutes at 40°C.
  • a transfer sheet hereinafter called TS1
  • TS1 was prepared by applying Ink 1 to a 6 micron sheet of polyethylene terephthalate using a wire-wound metal Mayr-bar to produce a 2 micron layer of ink on the surface of the sheet.
  • the ink was dried with hot air.
  • transfer sheets TS1', TS2, TS2' and TS3 to TS39 were prepared according to the procedure of Example 1 using Ink 1, Ink 2, Ink 2' and Ink 3 to Ink 39, respectively, in place of Ink 1.
  • a further 11 comparative transfer sheets, transfer sheets TS1C to TS12C were prepared according to the procedure of Example 1 using Ink 1C to Ink 12C in place of Ink 1.
  • a sample of TS 1 was sandwiched with a receiver sheet, comprising a composite structure based on a white polyester base having a copolyester receptor surface with the receptor surface of the latter in contact with the printed surface of the former.
  • the sandwich was placed on the drum of a transfer printing machine and passed over a matrix of closely-spaced pixels which were selectively heated in accordance with a pattern information signal to a temperature of >300°C for a period of 2-10 msec, whereby the dye at the position on the transfer sheet in contact with a pixel while it is hot is is transferred from the transfer sheet to the receiver sheet. After passage over the array of pixels the transfer sheet was separated from the receiver sheet
  • the printed receiver sheet is hereinafter referred to as RS 1.
  • Example 1 The procedure of Example 1 was repeated using each of TS1', TS2, TS2' and TS3 to TS39 in place of TS 1 and the printed receiver sheets are hereinafter referred to as RSI', RSI' RS2' and RS3 to RS39.
  • Example 42 The procedure of Example 42 was repeated using each of TS IC to TS12C in place of TS 1 and the printed receiver sheets are hereinafter referred to as RS1C to RS12C.
  • the absorption maxima (WL max )and extinction coefficients (EC max ) ) of the dyes, the stability of the inks and the transfer sheets and the quality of the prints on the receiver sheets were assessed.
  • the inks were assessed by visual inspection, microscopy and viscosity; the dyesheets by visual inspection and microscopy both before and after temperature cycling tests to assess the presence of dye crystallisation and/or migration; and the printed impression on the receiver sheet was assessed in respect of reflection density of colour by means of a densitometer (Sakura Digital densitometer) and for light fastness by means of a xenon fadeometer, against blue scale standards 1-8; 1 indicating poor fastness and 8 indicating excellent fastness.
  • azopyridone dyes of Formula I are eminently suitable yellow dyes for TTP, but that not all azopyridone yellow dyes are suitable.
  • the comparative dyes, Dyes A to F have poor solvent solubility and therefore give poor inks (Inks IC to 6C, IIC and 12C).
  • the stabilities of the resulting transfer sheets (TS1C to TS6C, TS11C and TS12C) are generally poor and Dyes A to F have thermochemical profiles which generally result in lower optical densities of the printed impressions on the receiver sheets (RS1C to RS6C, RS11C and RS12C).

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Coloring (AREA)
  • Cosmetics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
EP87303831A 1986-05-27 1987-04-29 Impression par transfert thermique Expired - Lifetime EP0247737B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT87303831T ATE55330T1 (de) 1986-05-27 1987-04-29 Thermouebertragungsdruck.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB868612778A GB8612778D0 (en) 1986-05-27 1986-05-27 Thermal transfer printing
GB8612778 1986-05-27

Publications (2)

Publication Number Publication Date
EP0247737A1 true EP0247737A1 (fr) 1987-12-02
EP0247737B1 EP0247737B1 (fr) 1990-08-08

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EP87303831A Expired - Lifetime EP0247737B1 (fr) 1986-05-27 1987-04-29 Impression par transfert thermique

Country Status (7)

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EP (1) EP0247737B1 (fr)
JP (1) JP2572767B2 (fr)
AT (1) ATE55330T1 (fr)
DE (1) DE3764183D1 (fr)
ES (1) ES2016356B3 (fr)
GB (1) GB8612778D0 (fr)
GR (1) GR3000700T3 (fr)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0302627A2 (fr) * 1987-08-04 1989-02-08 Imperial Chemical Industries Plc L'impression par transfert thermique
EP0319234A2 (fr) * 1987-12-03 1989-06-07 MITSUI TOATSU CHEMICALS, Inc. Méthode de coloration utilisant un nouveau colorant jaune et un matériau de transfer à utiliser pour le transfert thermique selon cette méthode
EP0389101A1 (fr) * 1989-03-23 1990-09-26 Zeneca Limited Impression par transfert thermique
EP0423796A1 (fr) * 1989-10-18 1991-04-24 Fuji Photo Film Co., Ltd. Matériaux donneurs de colorants pour le transfert thermique
EP0462447A1 (fr) * 1990-06-19 1991-12-27 BASF Aktiengesellschaft Utilisation de colorants azoiques pour l'impression par transfert thermique
US5093308A (en) * 1989-09-29 1992-03-03 Basf Aktiengesellschaft Oxadiazolyl-benzene azo hydroxy-pyridone dyes for thermal transfer printing a yellow print
EP0483792A1 (fr) * 1990-10-31 1992-05-06 Eastman Kodak Company Elément donneur de colorant de type pyridoneindoaniline pour utilisation dans le transfert thermique de colorant
US5262377A (en) * 1989-10-18 1993-11-16 Fuji Photo Film Co., Ltd. Thermal transfer dye donating materials
EP0701907A1 (fr) 1994-09-13 1996-03-20 Agfa-Gevaert N.V. Elément donneur de colorant pour utilisation dans un procédé de transfert thermique de colorant
EP0733487A2 (fr) 1995-01-30 1996-09-25 Agfa-Gevaert N.V. Procédé pour la fabrication de plaques lithographiques ne nécessitant pas de traitement liquide
EP0792757A1 (fr) 1996-02-27 1997-09-03 Agfa-Gevaert N.V. Elément donneur de colorant pour utilisation dans un procédé pour l'impression par le transfert thermique
WO2002094581A1 (fr) 2001-05-22 2002-11-28 Micyte Limited Appareil et procede de transfert d'image
US6576748B1 (en) 2002-06-27 2003-06-10 Xerox Corporation Method for making dimeric azo pyridone colorants
US6576747B1 (en) 2002-06-27 2003-06-10 Xerox Corporation Processes for preparing dianthranilate compounds and diazopyridone colorants
US6590082B1 (en) 2002-06-27 2003-07-08 Xerox Corporation Azo pyridone colorants
US6646111B1 (en) 2002-06-27 2003-11-11 Xerox Corporation Dimeric azo pyridone colorants
US6663703B1 (en) 2002-06-27 2003-12-16 Xerox Corporation Phase change inks containing dimeric azo pyridone colorants
EP1375599A1 (fr) * 2002-06-27 2004-01-02 Xerox Corporation Colorants pyridone azoiques sous forme du dimere
US6673139B1 (en) 2002-06-27 2004-01-06 Xerox Corporation Phase change inks containing dimeric azo pyridone colorants
US6696552B2 (en) 2002-06-27 2004-02-24 Xerox Corporation Process for preparing substituted pyridone compounds
US6755902B2 (en) 2002-06-27 2004-06-29 Xerox Corporation Phase change inks containing azo pyridone colorants
CN103525126A (zh) * 2013-10-23 2014-01-22 江苏德旺化工工业有限公司 一种分散深蓝色染料
CN103525122A (zh) * 2013-09-25 2014-01-22 江苏德旺化工工业有限公司 一种分散染料组合物及其制品和应用

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7381253B2 (en) 2004-12-03 2008-06-03 Xerox Corporation Multi-chromophoric azo pyridone colorants

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GB2159971A (en) * 1984-06-06 1985-12-11 Mitsubishi Chem Ind Transfer recording method

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DE2930481A1 (de) * 1979-07-27 1981-02-12 Bayer Ag Anthrachinonazo-verbindungen, verfahren zu ihrer herstellung sowie ihre verwendung als pigmente
JPS6027594A (ja) * 1983-07-27 1985-02-12 Mitsubishi Chem Ind Ltd ピリドンアゾ系感熱転写記録用色素
JPS6112393A (ja) * 1984-06-29 1986-01-20 Mitsui Toatsu Chem Inc 黄色系熱転写用色材

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Publication number Priority date Publication date Assignee Title
GB2159971A (en) * 1984-06-06 1985-12-11 Mitsubishi Chem Ind Transfer recording method

Non-Patent Citations (1)

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PATENT ABSTRACTS OF JAPAN, vol. 9, no. 152 (M-391)[1875], 27th June 1985; & JP-A-60 27 594 (MITSUBISHI KASEI KOGYO K.K.) 12-02-1985 *

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0302627A3 (en) * 1987-08-04 1990-04-18 Imperial Chemical Industries Plc Thermal transfer printing
US4968657A (en) * 1987-08-04 1990-11-06 Imperial Chemical Industries Plc Thermal transfer printing
EP0302627A2 (fr) * 1987-08-04 1989-02-08 Imperial Chemical Industries Plc L'impression par transfert thermique
EP0319234A2 (fr) * 1987-12-03 1989-06-07 MITSUI TOATSU CHEMICALS, Inc. Méthode de coloration utilisant un nouveau colorant jaune et un matériau de transfer à utiliser pour le transfert thermique selon cette méthode
EP0319234A3 (en) * 1987-12-03 1990-06-27 Mitsui Toatsu Chemicals, Inc. Coloring method by use of new yellow dyestuff and coloring base for thermal transfer for use in this method
EP0389101A1 (fr) * 1989-03-23 1990-09-26 Zeneca Limited Impression par transfert thermique
US5093308A (en) * 1989-09-29 1992-03-03 Basf Aktiengesellschaft Oxadiazolyl-benzene azo hydroxy-pyridone dyes for thermal transfer printing a yellow print
EP0423796A1 (fr) * 1989-10-18 1991-04-24 Fuji Photo Film Co., Ltd. Matériaux donneurs de colorants pour le transfert thermique
US5262377A (en) * 1989-10-18 1993-11-16 Fuji Photo Film Co., Ltd. Thermal transfer dye donating materials
US5403811A (en) * 1989-10-18 1995-04-04 Fuji Photo Film Co., Ltd. Thermal transfer dye donating materials
EP0462447A1 (fr) * 1990-06-19 1991-12-27 BASF Aktiengesellschaft Utilisation de colorants azoiques pour l'impression par transfert thermique
US5204312A (en) * 1990-06-19 1993-04-20 Basf Aktiengesellschaft Azo dyes for thermal transfer printing
EP0483792A1 (fr) * 1990-10-31 1992-05-06 Eastman Kodak Company Elément donneur de colorant de type pyridoneindoaniline pour utilisation dans le transfert thermique de colorant
EP0701907A1 (fr) 1994-09-13 1996-03-20 Agfa-Gevaert N.V. Elément donneur de colorant pour utilisation dans un procédé de transfert thermique de colorant
EP0733487A2 (fr) 1995-01-30 1996-09-25 Agfa-Gevaert N.V. Procédé pour la fabrication de plaques lithographiques ne nécessitant pas de traitement liquide
EP0792757A1 (fr) 1996-02-27 1997-09-03 Agfa-Gevaert N.V. Elément donneur de colorant pour utilisation dans un procédé pour l'impression par le transfert thermique
WO2002094581A1 (fr) 2001-05-22 2002-11-28 Micyte Limited Appareil et procede de transfert d'image
US6663703B1 (en) 2002-06-27 2003-12-16 Xerox Corporation Phase change inks containing dimeric azo pyridone colorants
US6576747B1 (en) 2002-06-27 2003-06-10 Xerox Corporation Processes for preparing dianthranilate compounds and diazopyridone colorants
US6590082B1 (en) 2002-06-27 2003-07-08 Xerox Corporation Azo pyridone colorants
US6646111B1 (en) 2002-06-27 2003-11-11 Xerox Corporation Dimeric azo pyridone colorants
US6576748B1 (en) 2002-06-27 2003-06-10 Xerox Corporation Method for making dimeric azo pyridone colorants
EP1375599A1 (fr) * 2002-06-27 2004-01-02 Xerox Corporation Colorants pyridone azoiques sous forme du dimere
US6673139B1 (en) 2002-06-27 2004-01-06 Xerox Corporation Phase change inks containing dimeric azo pyridone colorants
US6696552B2 (en) 2002-06-27 2004-02-24 Xerox Corporation Process for preparing substituted pyridone compounds
US6755902B2 (en) 2002-06-27 2004-06-29 Xerox Corporation Phase change inks containing azo pyridone colorants
CN103525122A (zh) * 2013-09-25 2014-01-22 江苏德旺化工工业有限公司 一种分散染料组合物及其制品和应用
CN103525126A (zh) * 2013-10-23 2014-01-22 江苏德旺化工工业有限公司 一种分散深蓝色染料

Also Published As

Publication number Publication date
EP0247737B1 (fr) 1990-08-08
ES2016356B3 (es) 1990-11-01
DE3764183D1 (de) 1990-09-13
ATE55330T1 (de) 1990-08-15
JPS62290583A (ja) 1987-12-17
GB8612778D0 (en) 1986-07-02
JP2572767B2 (ja) 1997-01-16
GR3000700T3 (en) 1991-09-27

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