EP0235939B2 - Impression par transfert thermique - Google Patents

Impression par transfert thermique Download PDF

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Publication number
EP0235939B2
EP0235939B2 EP19870300841 EP87300841A EP0235939B2 EP 0235939 B2 EP0235939 B2 EP 0235939B2 EP 19870300841 EP19870300841 EP 19870300841 EP 87300841 A EP87300841 A EP 87300841A EP 0235939 B2 EP0235939 B2 EP 0235939B2
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Prior art keywords
alkyl
formula
dye
substrate
thermal transfer
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EP19870300841
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German (de)
English (en)
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EP0235939A2 (fr
EP0235939B1 (fr
EP0235939A3 (en
Inventor
Peter Gregory
Raymond Leslie White
Geoffrey Richard Rothwell
Roy Porter
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Syngenta Ltd
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Zeneca Ltd
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Priority claimed from GB868604993A external-priority patent/GB8604993D0/en
Priority claimed from GB868624696A external-priority patent/GB8624696D0/en
Application filed by Zeneca Ltd filed Critical Zeneca Ltd
Priority to AT87300841T priority Critical patent/ATE97063T1/de
Publication of EP0235939A2 publication Critical patent/EP0235939A2/fr
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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

  • This specification describes an invention relating to thermal transfer printing and more particularly to a thermal transfer printing sheet carrying a dye or a mixture of dyes and to a thermal transfer printing process in which dye is transferred from the transfer sheet to a receiver sheet by the application of heat.
  • EP-A-0001068 describes a thermal transfer printing sheet comprising certain azo dyes and a thermal transfer printing process suitable for printing textile materials. Under the process conditions described the sheet in heated to a temperature from 60°C to 260°C for a period from 0.5 to 75 seconds in order to cause the dye to sublime and thereby to be transferred non-selectively to the textile material.
  • GB-A-2159971 describes a transfer printing process and is concerned with the problem of preventing the dyes migrating from the receiver sheet after transfer by introducing a reactive group into the dye so that the dye is capable of reacting with a compound bound into the receiver.
  • 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, 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 the shape and density of which is in accordance with the pattern and intensity of heat applied to the transfer sheet.
  • a dye for TTP is its thermal properties, brightness of shade, fastness properties, such as light and heat fastness, and facility for application to the substrate in the preparation of the transfer sheet.
  • the dye should transfer evenly, in a predetermined relationship to the heat applied to the transfer sheet so that the depth of shade on the receiver sheet is smoothly related to the heat applied and a good density gradation can be achieved on the receiver sheet.
  • Brightness of shade is important in order to obtain as wide a range of shades with the three primary dye shades of yellow, cyan and magenta.
  • the dye must be sufficiently mobile to migrate from the transfer sheet to the receiver sheet at the temperatures employed, typically 150-400°C, more especially 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 alkanols.
  • aqueous or water-miscible media such as water and alkanols.
  • suitable dyes are also not readily soluble in the solvents which are commonly used in, and thus acceptable to, the printing industry, such as aromatic hydrocarbons, alkanols and alkyl-and cycloalkyl-ketones.
  • the dye can be applied as a dispersion in a suitable solvent, it has been found that brighter, glossier and smoother final prints can often be achieved on the receiver sheet if the dye is applied to the substrate from a solution.
  • the dye should be readily soluble in the ink medium, particularly if it has a relatively low extinction coefficient. 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.
  • phenyl group A optionally carries a C 1-4 -alkyl group, this preferably CH 3 , or C 1-4 -alkoxy, this is preferably -OCH 3 .
  • the substituents in phenyl group A are preferably in the ortho and/or para positions with respect to the azo link.
  • a preferred substituted phenyl group, A, in the dyes of Formula I, giving orange to violet shades, is of the formula: wherein
  • a preferred substituted phenyl group A in dyes of Formula I, giving blue shades, is of the formula: wherein
  • substituted phenyl group, A are: 2,4-dinitrophenyl, 2-cyano-4-nitrophenyl, 2,4-dicyanophenyl, 2-nitro-4-cyanophenyl, 3,4-dicyanophenyl 2,4-dinitro-6-cyanophenyl, 2,6-dicyano-4-nitrophenyl, 2-methylsulphonyl-4-nitrophenyl 2,6-dicyano-4-methylphenyl
  • the radical E is formed by loss of the H atom para to the amino group.
  • the radical E is formed by loss of the H atom in the 7-position on the tetrahydroquinoline nucleus.
  • the radical E is formed by loss the H-atom on the benzene ring situated in the para position to the N atom.
  • Suitable coupling components in accordance with Formulae V, VI and VII are: lilolidine julolidine N-benzylaniline N-ethyl-N-(2-acetoxyethyl)aniline N,N-diethylaniline N-ethyl-N-(2-phthalimidoethyl)aniline N,N-bis(2-acetoxyethyl)aniline N,N-bis(2-ethoxycarbonylethyl)aniline N-ethyl-N-(2-cyanoethyl)aniline N-ethyl-N-(n-butyl)aniline N,N-di(n-propyl)aniline N-ethyl-N-(2-ethoxyethyl)aniline N,N-bis (2-methoxycarbonylethyl)aniline N-ethyl-N-(2-ethoxycarbonylethyl) aniline N,N-bis(2-methoxycarbony
  • Preferred dyes of Formula I giving orange to violet shades, are of the formula: wherein
  • X 2 is NO 2 , CN or -SO 2 CH 3 .
  • An especially preferred class of dyes in accordance with Formula IX, giving a magenta shade, has the formula: wherein
  • Preferred dyes of Formula I giving a blue shade, are of the formula: wherein
  • Thermal transfer printing sheets carrying a compound of Formula I in which the coupling component is a substituted aniline of Formula V, wherein one or both of R 3 and R 4 is an alkyl group, especially ethyl or propyl, carrying an electron withdrawing group, especially CN, OCO-C 1-4 -alkyl or COO-C 1-4 -alkyl, are especially preferred species of the present invention because of their very good stability.
  • Stability of a dye on the transfer sheet is an important property because dyes with poor stability (i) tend to crystallise on the sheet and as a result do not transfer evenly onto the receiver sheet during the TTP process and/or (ii) tend to transfer under pressure alone so that (a) the receiver sheet becomes coloured in areas to which no heat is applied, while it is in contact, under pressure, with the transfer sheet during the TTP process and (b) dye is transfered from the front to the back of the transfer sheet when the transfer sheet is rolled up.
  • a dye of Formula I generally has good thermal properties giving rise to even prints on the receiver sheet, whose depth of shade is related to the quantity of applied heat so that a good gradation of colour density can be obtained.
  • a dye of Formula I also generally 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, such as alkanols, e.g. ethanol, isopropanol & 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, such as alkanols, e.g. ethanol, isopropanol & butanol, aromatic hydrocarbons, such as toluene and ketones such as MEK, MIBK and cyclohexanone.
  • the blue dye of Formula XII in which Y 1 & Y 2 are both CN, R 5 is H, R 12 is -NHCOCH 3 and R 14 & R 15 are both C 2 H 5 allows the achievement of a strong bright greenish-blue print on the receiver sheet of moderate lightfastness and high optical density.
  • the related dye in which Y 2 is NO 2 allows the achievement of a strong bright mid-blue shade print of good lightfastness and high optical density.
  • the dyes of Formula I give orange to blue shades.
  • another important shade in trichromatic printing is black and mixtures of the present dyes, especially of dyes giving orange shades and dyes giving reddish blue shades, can be used to give good strong black shades.
  • Preferred orange dyes for use in such mixtures are of the formula: wherein Z is H or -OCOCH 3 .
  • Preferred blue dyes for use in such mixtures are of the formula: wherein
  • the relative proportions of the blue dye of Formula XII or XIV and the orange dye of Formula XIII required to produce a mixture giving a black shade depend on the shade of black required and the relative strengths of the component dyes. However the relative proportions generally range from 90:10 to 10:90 and more preferably from 70:30 to 30:70.
  • the radical, A 1 , of the heteroaromatic amine, A 1 -NH 2 may be substituted by non-ionic groups, preferably those which are free from acidic hydrogen atoms, unless these are positioned so that they form intramolecular hydrogen bonds.
  • substituents are NO 2 ; CN; CNS; halogen, especially F, Cl & Br; CF 3 ; C 1-4 -alkyl; C 1-4 -alkoxy; C 1-4 -alkoxy-C 1-4 -alkyl; cyano-C 1-4 -alkyl; -SO 2 NH 2 ; -SO 2 F; -SO 2 Cl; -CONH 2 ; -COF; -COCl; C 1-4 -alkylthio; -SO 2 -C 1-4 -alkyl; -CON-(C 1-4 -alkyl) 2 ; -SO 2 N(C 1-4 -alkyl) 2 ; -COO-C 1-4 -alkyl and -CO-C 1-4 -alkyl.
  • heteroaromatic residues are: 2,3-dicyanoimidazol-5-yl, 1-ethyl-2,3-dicyanoimidazol-5-yl, 5-nitrothiazol-2-yl, 3-methyl-4-cyanoisothiazol-5-yl, 4-cyanoisothiazol-5-yl, 6-fluorosulphonylbenzothiazol-2-yl, 6-thiocyanobenzothiazol-2-yl, 6-methylsulphonylbenzothiazol-2-yl, 6-methoxybenzothiazol-2-yl, 5-nitro-2,1-benzoisothiazol-3-yl, 6-nitrobenzothiazol-2-yl, 1-ethyl-3,4-dicyanopyrazol-5-yl, 3,5-dicyanothiophen-1-yl, 3-cyanomethyl-4-cyanopyrazol-5-yl, 3,5-dinitrothiophen-1-yl, 6-cyanopyrid
  • the radical E present in the dye of Formula XV is preferably derived from a coupling component of Formula V.
  • Preferred dyes of Formula XV are the magenta dyes where A 1 is 3-methyl-4-cyanoisothiazol-5-yl, 4-cyanoisothiazol-5-yl and 1-cyanomethyl-3,4-dicyanopyrazol-5-yl, and where E is the radical of an aniline of Formula V where R 2 is H, Cl or C 1-4 -alkyl, especially CH 3 ; R 5 is H; and R 3 & R 4 are each independently selected from C 2 -C 4 -alkyl, optionally substituted by -OCO-C 1-4 -alkyl, and especially from C 2 H 5 , n -C 4 H 9 , and C 2 H 4 OCOCH 3 .
  • the preferred dyes of Formula XV are preferably used in admixture with the preferred dyes of Formula XI to prepare transfer sheets which have good storage stability and which give rise to magenta-shade prints of moderate lightfastness, of brighter shade than those derived from dyes of Formula XI and of significantly higher strength than is achievable with dyes of Formula XI alone.
  • the dyes of Formula XV are usually, but not necessarily, the minor components of the mixture.
  • 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 to 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 layer on which the dye is deposited.
  • Such laminates preferably comprise, in addition to the polyester, a backcoat of a heat-resistant material, such as a thermosetting resin, e.g. silicone or polyurethane, to separate the heat source from the polyester so that the latter is not melted.
  • a heat-resistant material such as a thermosetting resin, e.g. silicone or polyurethane
  • the thickness of the substrate may vary within wide limits depending upon its thermal characteristics but is preferably less than 50 ⁇ m and more preferably below 10 ⁇ m.
  • the coating preferably comprises a binder and one or more dyes of Formula I, optionally with one or more dyes of Formula XV.
  • 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 binder may be any resinous or polymeric material suitable for binding the dye to the substrate.
  • suitable binders are 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 copolymers derived from acrylates and acrylate derivatives, such as polyacrylic acid, polymethyl methacrylate and styrene-acrylate copolymers, polyester resins, polyamide resins, such as melamines; polyurea and polyurethane resins; organosilicones, such as polysiloxanes, epoxy resins and natural resins, such
  • 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.
  • 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 adjacent to the receiver sheet, and selectively heating an area of the transfer sheet whereby dye in the heated area 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 300°C to 400°C, for a period of from 0.5 to 30 msec, more preferably from 1 to 10 msec, while it is maintained 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, and temperature at, which the transfer sheet is heated while in contact with the receiver sheet.
  • the receiver sheet conveniently comprises a white polyester sheet material, especially of polyethylene terephthalate (PET).
  • PET polyethylene terephthalate
  • the dye of Formula I is known for the colouration of textile materials made from PET
  • the colouration of textile materials by dyeing or printing, is carried out under such conditions of time and temperature that the dye can penetrate the PET and become fixed therein.
  • the time period is so short that penetration of the PET is less effective and the receiver sheet is preferably provided with a receptive layer on the side to which the dye is applied, into which the dye can more readily diffuse to form a stable image on the receiver sheet.
  • Such a receptive coating may comprise a thin layer, applied to the receiver sheet by co-extrusion or solution coating techniques, of a modified polyester or a different polymeric material which is more permeable to the dye than PET.
  • the nature of the receptive coating will affect to some extent the depth of shade and quality of the print obtained but it has been found that the present dyes give particularly strong and good quality prints compared with other dyes which have been previously proposed for thermal transfer printing on any specific receiver sheet.
  • the design of receiver sheets with receptive layers is discussed in EP 133,011A & EP 133,012A.
  • a further 25 inks were prepared by the same method as Ink 1 using each of the azo dyes or mixtures of azo dyes indicated in Table 1 below.
  • a thermal transfer sheet was prepared by forming a 24 ⁇ m coating of Ink 1 (using a Mayer bar) on the precleaned (with dichloromethane) surface of a sheet of PET film (6 ⁇ m, MELINEX) having a thermally protected back-coat layer (2 ⁇ m). The coating was dried in hot air stream.
  • the transfer sheet is hereinafter referred to as TS1.
  • a further 25 transfer sheets (TS2 to TS26) were prepared by the method of Example 1 using Inks 2 to 26 in place of Ink 1.
  • Transfer sheet TS1 was sandwiched with a composite receiver sheet comprising a white PET substrate and a receptive layer on the side in contact with the printed surface of TS1.
  • the sandwich was placed on the cylindrical drum of thermal transfer printing machine.
  • the sandwich passed over a matrix of closely spaced pixels which were selectively heated in accordance with a pattern information signal to a temperature of 350°C for periods from 1 to 10 msec, whereby a quantity of the dye, in proportion to the heating period, at the position on the transfer sheet in contact with a pixel while it was hot, was transferred from the transfer sheet to the receiver sheet.
  • the pattern information signal was formulated so that the heating period of the pixels was increased at regular intervals as the sandwiched passed over the matrix so that the printed pattern was in the form of a scale composed of bands of colour of increasing depth of shade. After passage over the array of pixels the transfer sheet was separated from the receiver sheet. Superficial dye which had not penetrated the receptor layer on the receiver sheet was removed by the application and removal of a strip of self-adhesive tape.
  • the printed receiver sheet is hereinafter referred to as RS1.
  • a further 25 receiver sheets (RS 2 to RS 26) were printed by the method of Example 27 using TS2 to TS 26 in place of TS1.
  • the reflectance optical density of the print on each receiver sheet was measured by examination of the band having the maximum depth of shade with a Sakura digital densitometer and the results of the measurements are given in Table 1. Magenta dyes were examined through a green filter and blue dyes were examined through a red filter.
  • Each of these mixtures was formed into an ink by the method for Ink 1 and the ink used to prepare a transfer sheet by the method of Example 1.
  • Each black mixture was transfered by the method of Example 27 to produce a receiver sheet having an even black shade.
  • An ink (Ink A) was made according to the procedure of Ink 1 using the same weight of 1-amino-2-phenoxy-4-hydroxyanthraquinone in place of Dye 1.
  • a transfer sheet (TSA) was prepared accoring to Example 1 using Ink A in place of Ink 1.
  • a printed receiver sheet (RSA) was prepared by the method of Example 27 using TSA in place of TS1.
  • the reflectance optical density of RSA was measured by examination of the band having maximum depth of shade with a Sakura digital densitometer under the same conditions as the asessment of receiver sheets RS1 to RS26. The result of the measurement is shown below in comparison with that of RS1 (taken from Example 27 in Table 1) Receiver Sheet Reflectance Optical Density RSA 0.63 RS1 1.08

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Claims (9)

  1. Feuille d'impression par transfert thermique comprenant un substrat portant un revêtement comprenant un colorant de formule :

            A ― N = N ― E     I

    dans laquelle :
    A   représente un groupe phényle substitué avec deux ou trois groupes choisis entre des groupes NO2, CN et -SO2-(alkyle en C1 à C4), et facultativement avec un ou plusieurs groupes choisis entre des groupes alkyle en C1 à C4 et alkoxy en C1 à C4 ; et
    E   est choisi entre
    (i) un groupe anilino de formule :
    Figure imgb0076
    dans laquelle :
    R2   est choisi entre H, des groupes alkyle en C1 à C4, alkoxy en C1 à C4, alkylthio en C1 à C4, NH2-CO-NH-, HCONH-, phényl-CONH-, (alkyle en C1 à C4)-CO-NH-, (alkyle en C1 à C4)-SO2-NH-, CN, CF3 et halogéno ;
    R3 et R4   sont choisis indépendamment entre H, des groupes alkyle en C1 à C6 et cycloalkyle en C4 à C8, dont chacun est non substitué ou substitué avec un groupe choisi indépendamment entre des groupes halogéno, CN, phényle, hétéroaryle mono- ou bicyclique, -OCO-(alkyle en C1 à C4), -COO-(alkyle en C1 à C4), alcényle en C2 à C4 et alkoxy en C1 à C4 ; ou bien
    R3 et R4   conjointement avec l'atome d'azote auquel ils sont fixés, forment un noyau hétérocyclique, tel qu'un noyau morpholine, pipérazine ou thiomorpholine ; et
    R5   est choisi entre H, des groupes alkyle en C1 à C4 et alkoxy en C1 à C4 ;
    (ii) un groupe tétrahydroquinolinyle, de formule :
    Figure imgb0077
    dans laquelle :
    R3   est choisi entre H, des groupes alkyle en C1 à C6 et cycloalkyle en C4 à C8, dont chacun est indépendamment non substitué ou substitué avec un groupe choisi entre des groupes halogéno, CN, phényle, hétéroaryle mono- ou bicyclique, -OCO-(alkyle en C1 à C4), -COO-(alkyle en C1 à C4), alcényle en C2 à C4 et alkoxy en C1 à C4 ; et
    R6 à R9   sont choisis indépendamment entre H et un groupe alkyle en C1 à C4 ; et
    (iii) un groupe lilolidinyle ou julolidinyle, de formule :
    Figure imgb0078
    dans laquelle : n est égal à 2 (lilolidine) ou à 3 (julolidine), sous réserve que le substrat ne présente pas une bonne capacité de conduction de chaleur ou bien que le substrat ne consiste pas en papier.
  2. Feuille d'impression par transfert thermique suivant la revendication 1, dans laquelle A répond à la formule :
    Figure imgb0079
     dans laquelle :
    X1   représente un groupe NO2, CN ou -SO2CH3 ; et
    X2   représente un groupe NO2, CN ou -SO2CH3,
    sous réserve que le substrat ne présente pas une bonne capacité de conduction de chaleur ou bien que le substrat ne consiste pas en papier.
  3. Feuille d'impression par transfert thermique suivant la revendication 1, dans laquelle A répond à la formule :
    Figure imgb0080
     dans laquelle :
    X1   représente un groupe NO2, CN ou -SO2CH3,
    sous réserve que le substrat ne présente pas une bonne capacité de conduction de chaleur ou bien que le substrat ne consiste pas en papier.
  4. Feuille d'impression par transfert thermique suivant la revendication 1, dans laquelle A répond à la formule :
    Figure imgb0081
     dans laquelle :
    Y1 et Y2   sont choisis indépendamment entre des groupes CN et NO2,
    sous réserve qu'ils ne représentent l'un et l'autre un groupe NO2, sous réserve que le substrat ne présente pas une bonne capacité de conduction de chaleur.
  5. Feuille d'impression par transfert thermique suivant la revendication 1, dans laquelle le colorant répond à la formule :
    Figure imgb0082
     dans laquelle :
    X1   représente un groupe NO2 ou CN ;
    R12   est choisi entre H, un groupe CH3 et un groupe -NHCOCH3 ;
    R14 et R15   sont choisis chacun indépendamment entre des groupes alkyle en C2 à C4, (alkylène en C1 à C4)-OCO-(alkyle en C1 à C4) et C2H4CN,
    sous réserve que le substrat ne présente pas une bonne capacité de conduction de chaleur ou bien que le substrat ne consiste pas en papier.
  6. Feuille d'impression par transfert thermique suivant la revendication 1, dans laquelle le colorant répond à la formule :
    Figure imgb0083
     dans laquelle :
    Y1   représente un groupe NO2 ou CN ;
    Y2   représente un groupe CN ;
    R14 et R15   sont choisis chacun indépendamment entre des groupes alkyle en C2 à C4 et (alkylène en C1 à C4)-OCO-(alkyle en C1 à C4) ;
    R5   est choisi entre H, des groupes alkyle en C1 à C4 et alkoxy en C1 à C4 ; et
    R12   est choisi entre H, un groupe CH3 et un groupe -NHCOCH3,
    sous réserve que le substrat ne présente pas une bonne capacité de conduction de chaleur.
  7. Feuille d'impression par transfert thermique suivant la revendication 1, dans laquelle le revêtement comprend un colorant de formule :
    Figure imgb0084
     dans laquelle :
    Z   représente H ou un groupe -OCOCH3 ;
    en mélange avec un colorant de formule :
    Figure imgb0085
     dans laquelle :
    R   représente H ou un groupe -OCH3 ;
    Q   est choisi entre H, un groupe -OCOCH3 et un groupe -COOC2H4OCH3 ; et
    Q1   est choisi entre H, un groupe -C2H5 et un groupe -C2H4OCOCH3.
  8. Feuille d'impression par transfert thermique suivant la revendication 1, dans laquelle le revêtement comprend un colorant de formule :
    Figure imgb0086
     dans laquelle :
    X1   représente un groupe NO2 ou CN ;
    R12   est choisi entre H, un groupe CH3 et un groupe -NHCOCH3 ; et
    R14 et R15   sont choisis chacun indépendamment entre des groupes alkyle en C2 à C4, (alkylène en C1 à C4)-OCO-(alkyle en C1 à C4) et C2H4CN ;
    en mélange avec un colorant de formule :

            A1 ― N = N ― E

    dans laquelle :
    A1   est choisi entre les groupes 3-méthyl-4-cyanoisothiazole-5-yle, 4-cyanoisothiazole-5-yle et 1-cyanométhyl-3,4-dicyanopyrazole-5-yle ; et
    E   répond à la formule :
    Figure imgb0087
    dans laquelle :
    R2   est choisi entre H, le chlore et un groupe alkyle en C1 à C4 ;
    R3 et R4   représentent chacun indépendamment un groupe (alkylène en C2 à C4)-OCO-(alkyle en C1 à C4) ;
    R5   représente H.
  9. Procédé d'impression par transfert thermique, qui comprend la mise en contact d'une feuille de transfert suivant la revendication 1 revêtue d'un colorant de formule I avec une feuille réceptrice, de telle sorte que le colorant soit adjacent à la feuille réceptrice, et le chauffage sélectif d'une zone de la feuille de transfert à une température de 250°C à 400°C pendant un temps de 0,5 à 30 ms, ce qui provoque le transfert sélectif à la feuille réceptrice du colorant présent dans la zone chauffée de la feuille de transfert.
EP19870300841 1986-02-28 1987-01-30 Impression par transfert thermique Expired - Lifetime EP0235939B2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT87300841T ATE97063T1 (de) 1986-02-28 1987-01-30 Thermouebertragungsdruck.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB8604993 1986-02-28
GB868604993A GB8604993D0 (en) 1986-02-28 1986-02-28 Thermal transfer printing
GB868624696A GB8624696D0 (en) 1986-10-15 1986-10-15 Thermal transfer printing
GB8624696 1986-10-15

Publications (4)

Publication Number Publication Date
EP0235939A2 EP0235939A2 (fr) 1987-09-09
EP0235939A3 EP0235939A3 (en) 1989-05-03
EP0235939B1 EP0235939B1 (fr) 1993-11-10
EP0235939B2 true EP0235939B2 (fr) 1996-10-09

Family

ID=26290417

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19870300841 Expired - Lifetime EP0235939B2 (fr) 1986-02-28 1987-01-30 Impression par transfert thermique

Country Status (3)

Country Link
EP (1) EP0235939B2 (fr)
JP (1) JP2716434B2 (fr)
DE (1) DE3788072T3 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3810726A1 (de) * 1988-03-30 1989-10-12 Cassella Ag Mischungen von monoazofarbstoffen
JP2684183B2 (ja) * 1988-02-05 1997-12-03 富士写真フイルム株式会社 感熱転写材料
DE3905527A1 (de) * 1989-02-23 1990-09-06 Cassella Ag Verwendung von farbstoffen fuer das sublimations-transferverfahren
US4988665A (en) * 1989-05-18 1991-01-29 Eastman Kodak Company Arylazoaniline blue dyes for color filter array element
US4975410A (en) * 1989-05-26 1990-12-04 Eastman Kodak Company Thermally-transferred color filter array element and process for preparing
EP0432314B1 (fr) * 1989-12-12 1995-05-17 Agfa-Gevaert N.V. Méthode de transfert thermique de colorants par sublimation
DE4004600A1 (de) * 1990-02-15 1991-08-22 Basf Ag Verfahren zur uebertragung von azofarbstoffen
DE4005939A1 (de) * 1990-02-26 1991-08-29 Cassella Ag Verwendung von farbstoffen fuer das sublimations-transferverfahren
EP0453020B1 (fr) * 1990-04-20 1995-01-18 Agfa-Gevaert N.V. Elément donateur noir pour la sublimation thermique de colorants par transfert
EP0485665B1 (fr) * 1990-11-14 1996-02-07 Agfa-Gevaert N.V. Colorants pour transfert thermique de colorant
US5350731A (en) * 1993-12-07 1994-09-27 Minnesota Mining And Manufacturing Company Thermally transferable fluorine-containing AZO dyes
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
EP0733487B1 (fr) 1995-01-30 2000-05-24 Agfa-Gevaert N.V. Procédé pour la fabrication de plaques lithographiques ne nécessitant pas de traitement liquide
DE69613208T2 (de) 1996-02-27 2002-04-25 Agfa Gevaert Nv Farbstoffdonorelement zum Gebrauch in einem thermischen Übertragungsdruckverfahren
DE19611351A1 (de) 1996-03-22 1997-09-25 Basf Ag Farbstoffmischungen, enthaltend Thienyl- und/oder Thiazolazofarbstoffe
CN106928748B (zh) * 2017-03-10 2019-03-15 绍兴金祥惠纺织印染有限公司 一种分散染料

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Publication number Priority date Publication date Assignee Title
JPS5932319B2 (ja) * 1974-03-22 1984-08-08 富士写真フイルム株式会社 記録材料
FR2334721A1 (fr) * 1975-12-11 1977-07-08 Toms River Chemical Corp Colorants azoiques et leur application dans l'impression par transfert sublimation
AU3887978A (en) * 1977-08-23 1980-02-21 Fromson H A Lithographic printing plate
GB2036809B (en) * 1978-12-08 1982-08-25 Kodak Ltd Transfer printing
US4614521A (en) * 1984-06-06 1986-09-30 Mitsubishi Chemical Industries Limited Transfer recording method using reactive sublimable dyes
JPS60260391A (ja) * 1984-06-07 1985-12-23 Mitsubishi Chem Ind Ltd 感熱記録用シ−ト・セツト
JPS61227092A (ja) * 1985-04-01 1986-10-09 Mitsubishi Chem Ind Ltd 感熱転写記録用アゾ色素及び感熱転写シート
JPH0764123B2 (ja) * 1985-05-23 1995-07-12 大日本印刷株式会社 熱転写シ−ト
GB8521327D0 (en) * 1985-08-27 1985-10-02 Ici Plc Thermal transfer printing
JPH0798426B2 (ja) * 1985-09-18 1995-10-25 大日本印刷株式会社 熱転写シ−ト
JPS6299195A (ja) * 1985-10-28 1987-05-08 Mitsui Toatsu Chem Inc 感熱昇華転写記録用マゼンタ色色素
JPH0667673B2 (ja) * 1985-12-05 1994-08-31 三井東圧化学株式会社 感熱昇華転写記録用シアン色色素

Also Published As

Publication number Publication date
JP2716434B2 (ja) 1998-02-18
DE3788072T2 (de) 1994-04-07
EP0235939A2 (fr) 1987-09-09
DE3788072D1 (de) 1993-12-16
JPS62211190A (ja) 1987-09-17
EP0235939B1 (fr) 1993-11-10
DE3788072T3 (de) 1997-02-20
EP0235939A3 (en) 1989-05-03

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