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EP0235939B1 - Impression par transfert thermique - Google Patents

Impression par transfert thermique Download PDF

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Publication number
EP0235939B1
EP0235939B1 EP19870300841 EP87300841A EP0235939B1 EP 0235939 B1 EP0235939 B1 EP 0235939B1 EP 19870300841 EP19870300841 EP 19870300841 EP 87300841 A EP87300841 A EP 87300841A EP 0235939 B1 EP0235939 B1 EP 0235939B1
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EP
European Patent Office
Prior art keywords
alkyl
formula
dye
thermal transfer
transfer printing
Prior art date
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Application number
EP19870300841
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German (de)
English (en)
Other versions
EP0235939A2 (fr
EP0235939A3 (en
EP0235939B2 (fr
Inventor
Peter Gregory
Raymond Leslie White
Geoffrey Richard Rothwell
Roy Porter
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.)
Syngenta Ltd
Original Assignee
Zeneca Ltd
Imperial Chemical Industries 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, Imperial Chemical Industries Ltd filed Critical Zeneca Ltd
Priority to AT87300841T priority Critical patent/ATE97063T1/de
Publication of EP0235939A2 publication Critical patent/EP0235939A2/fr
Publication of EP0235939A3 publication Critical patent/EP0235939A3/en
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Publication of EP0235939B1 publication Critical patent/EP0235939B1/fr
Publication of EP0235939B2 publication Critical patent/EP0235939B2/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.
  • thermo transfer printing sheet comprising a substrate having a coating comprising a dye of the formula: wherein
  • 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
  • X 1 is N0 2 , CN or -S0 2 CH 3 , gives strong magenta dyes of Formula I.
  • a preferred substituted phenyl group A in dyes of Formula I, giving blue shades, is of the formula: wherein
  • Y 1 & y2 are independently selected from CN, N0 2 provided that they are not both N0 2 In a dye of Formula IV, it is especially preferred that Y 1 and Y 2 are both CN or that Y 1 is CN and Y 2 is N0 2 .
  • 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 N0 2 , CN or -S0 2 CH 3 .
  • An especially preferred class of dyes in accordance with Formula IX, giving a magenta shade, has the formula: wherein
  • X 1 is CN
  • R 12 is methyl
  • R 14 is ethyl, n-propyl, n-butyl or -C 2 H 4 OCOCH 3
  • R 15 is -C 2 H 4 OCOCH 3 .
  • Preferred dyes of Formula I giving a blue shade, are of the formula: wherein
  • Y 1 and y2 are both CN or that Y 1 is CN and y2 is N0 2 and that R 5 is H, R 12 is -NHCOCH 3 and R 14 & R 15 are C 2 - 4 -alkyl.
  • 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 N0 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
  • Especially preferred blue dyes are those in which:
  • 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.
  • a suitable dye for use in admixture with one or more dyes of Formula I is one of the formula: wherein:
  • 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 N0 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; -S0 2 NH 2 ; -S0 2 F; -S0 2 CI; -CONH 2 ; -COF; -COCI; 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-Ci-4.-alkyl, and especially from C 2 Hs, 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 133011 A, 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 133,011 A & 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 /1 .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)

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
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Claims (9)

1. Feuille d'impression par transfert thermique qui comprend un substrat portant un revêtement comprenant un colorant de la formule :
Figure imgb0048
où
A est un radical phényle substitué par deux ou trois radicaux choisis parmi N02, CN et -SO2-C1-4- alcoyle et facultativement un ou plusieurs radicaux choisis parmi C1 -4-alcoyle et C1 -4-alcoxy, et
E est choisi parmi
(i) un radical anilino de formule :
Figure imgb0049
où
R2 est choisi parmi H, C1-4-alcoyle, C1-4-alcoxy, Ci-4-alcoylthio, NH2-CO-NH-, HCONH-, phényl-CONH-, C1-4-alcoyl-CO-NH-, C1-4-alcoyl-SO2-NH-, CN, CF3 et halogène;
R3 et R4 sont choisis indépendamment parmi H, c1-6-alcoyle et C4-g-cycloalcoyle, dont chacun est non substitué ou est substitué par un radical choisi indépendamment parmi halogène, CN, phényle, hétéroaryle mono- ou bicyclique, -OCO-C1-4-alcoyle, -COO-C1-4-alcoyle, C2-4-alcényle et Ci -4-alcoxy, ou
R3 et R4 conjointement avec l'atome d'azote auquel ils sont attachés forment un radical hétérocyclique, comme la morpholine, la pipérazine ou la thiomorpholine, et
R5 est choisi parmi H, c1-4-alcoyle et c1-4-alcoxy;
(ii) un radical tétrahydroquinolinyle de formule :
Figure imgb0050
où
R3 est choisi parmi H, C1-6-alcoyle et C4-8-cycloalcoyle dont chacun est indépendamment non substitué ou substitué par un radical choisi parmi halogène, CN, phényle, hétéroaryle mono- ou bicyclique, -OCO-C1-4-alcoyle, -COO-C1-4-alcoyle, C2-4-alcényle et C1-4-alcoxy, et
R6 à R9 sont choisis indépendamment parmi H et C1 -4-alcoyle, et
(iii) un radical lilolidinyle ou un radical julolidinyle de formule :
Figure imgb0051
où
n = 2 (lilolidine) ou 3 (julolidine).
2. Feuille d'impression par transfert thermique suivant la revendication 1, dans laquelle A est de formule :
Figure imgb0052
où
X1 est N02, CN ou -S02CH3, et
X2 est N02, CN, -S02CH3.
3. Feuille d'impression par transfert thermique suivant la revendication 1, dans laquelle A est de formule :
Figure imgb0053
où
X1 est N02, CN ou -S02CH3.
4. Feuille d'impression par transfert thermique suivant la revendication 1, dans laquelle A est de formule :
Figure imgb0054
où
Y1 et Y2 sont choisis indépendamment parmi CN, N02 avec la restriction qu'ils ne sont pas tous deux N02.
5. Feuille d'impression par transfert thermique suivant la revendication 1, dans laquelle le colorant est de la formule :
Figure imgb0055
où
X1 est N02 ou CN;
R12 est choisi parmi H, CH3 ou -NHCOCH3, et
R14 et R15 sont choisis chacun indépendamment parmi C2-4-alcoyle et C1-4-alcoylène-OCO-C1-4- alcoyle et -C2H4CN.
6. Feuille d'impression par transfert thermique suivant la revendication 1, dans laquelle le colorant est de formule :
Figure imgb0056
où
Y1 représente N02 ou CN;
Y2 représente CN, et
R14 et R15 sont choisis chacun indépendamment parmi C2-4-alcoyle et C1-4-alcoylène-OCO-C1-4- alcoyle;
R5 est H, C1 -4-alcoyle ou C1-4-alcoxy, et
R12 est H, CH3 ou -NHCOCH3.
7. Feuille d'impression par transfert thermique suivant la revendication 1, dans laquelle le revêtement comprend un colorant de formule :
Figure imgb0057
où
Z est H ou -OCOCH3; en mélange avec un colorant de formule :
Figure imgb0058
où
R est H ou -OCH3;
Q est choisi parmi H, -OCOCH3 et -COOC2H4OCH3, et
Q1 est choisi parmi H, -C2H5 et -C2H4OCOCH3.
8. Feuille d'impression par transfert thermique suivant la revendication 1, dans laquelle le revêtement comprend un colorant de formule :
Figure imgb0059
où
X1 est N02 ou CN;
R12 est choisi parmi H, CH3 ou -NHCOCH3, et
R14 et R15 sont choisis chacun indépendamment parmi C2-4-alcoyle et C1-4-alcoylène-OCO-C1-4- alcoyle et C2H4CN;
en mélange avec un colorant de formule :
Figure imgb0060
où
A1 est choisi parmi 3-méthyl-4-cyanoisothiazol-5-yle, 4-cyanoisothiazol-5-yle et 1-cyanométhyl-3,4- dicyanopyrazol-5-yle, et
E est de formule :
Figure imgb0061
où
R2 est choisi parmi H, chlore et C1 -4-alcoyle;
R3 et R4 sont chacun indépendamment C2-4-alcoylène-OCO-C1-4-alcoyle ou C2-4-alcoyle, et R5 est H.
9. Procédé d'impression par transfert thermique, qui comprend la mise en contact d'une feuille de transfert revêtue d'un colorant de formule I avec une feuille réceptrice de façon que le colorant soit adjacent à la feuille réceptrice et le chauffage sélectif d'une région de la feuille de transfert jusqu'à une température de 250 à 400 °C pendant une durée de 0,5 à 30 ms, de manière que le colorant de la région chauffée de la feuille de transfert soit transféré sélectivement sur la feuille réceptrice.
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
GB868604993A GB8604993D0 (en) 1986-02-28 1986-02-28 Thermal transfer printing
GB8604993 1986-02-28
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 true EP0235939B1 (fr) 1993-11-10
EP0235939B2 EP0235939B2 (fr) 1996-10-09

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EP19870300841 Expired - Lifetime EP0235939B2 (fr) 1986-02-28 1987-01-30 Impression par transfert thermique

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

Cited By (1)

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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

Also Published As

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EP0235939A2 (fr) 1987-09-09
EP0235939A3 (en) 1989-05-03
JPS62211190A (ja) 1987-09-17
DE3788072T3 (de) 1997-02-20
EP0235939B2 (fr) 1996-10-09
DE3788072D1 (de) 1993-12-16
JP2716434B2 (ja) 1998-02-18
DE3788072T2 (de) 1994-04-07

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