Transferring dyes for thermal printing: tri-cyano-vinyl aniline dyes

Information

  • Patent Grant
  • 4999026
  • Patent Number
    4,999,026
  • Date Filed
    Monday, July 24, 1989
    35 years ago
  • Date Issued
    Tuesday, March 12, 1991
    33 years ago
Abstract
Dyes are transferred from a carrier by sublimation/vaporization to plastic-coated papers by a process in which the dyes used are of the general formula (I) ##STR1## where A is D--N.dbd.N-- or ##STR2## R.sup.1 and R.sup.2 are each hydrogen, alkyl, alkoxy, alkylthio or halogen and R.sup.1 and R together may furthermore form a 5-membered or 6-membered heterocyclic ring, and R and R' independently of one another are each hydrogen, phenyl which is unsubstituted or substituted by methyl or methoxy, or C.sub.5 - or C.sub.6 -cycloalkyl or C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.2 -C.sub.5 -alkanoyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyloxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -or C.sub.3 -alkoxycarbonyloxy, hydroxyl, cyano, halogen, phenyl or C.sub.5 - or C.sub.6 -cycloalkyl, or ##STR3## is a 5-membered or 6-membered saturated heterocyclic ring where D is a radical of a diazo component of the thiophene, thiazole, isothiazole or 1,2,4-thiadiazole series and R.sup.3 is hydrogen or CN.In the process, the dyes (I) give strong dyeings which have good light fastness and are resistant to chemical substances.
Description
Claims
  • 1. A process for transferring a dye from a carrier by sublimation/vaporization with the aid of a thermal printing head to a plastic-coated paper, said carrier employing a dye of the formula:
  • wherein R.sup.1 is C.sub.1 -C.sub.4 -alkoxy, and R.sup.1 is phenyl which is unsubstituted or substituted by methyl or methoxy, or is C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.2 -C.sub.5 -alkanoyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyloxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 - or C.sub.3 -alkoxycarbonyl, hydroxyl or cyano.
  • 2. The process as claimed in claim 1, wherein R.sup.2 is C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by hydroxyl or cyano, or R.sup.2 is C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxycarbonyloxy-C.sub.2 -C.sub.4 -alkyl.
  • 3. The process as claimed in claim 1, wherein R.sup.1 is methoxy.
  • 4. The process as claimed in claim 2, wherein R.sup.1 is methoxy.
  • 5. The process as claimed in claim 1, wherein R.sup.2 is C.sub.1 -C.sub.4 -alkyl, cyanoethyl, hydroxyethyl, C.sub.1 -C.sub.2 -alkoxyethy, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.2 -C.sub.3 -alkyl or methylphenyl.
  • 6. The process as claimed in claim 3, wherein R.sup.2 is C.sub.1 -C.sub.4 -alkyl, cyanoethyl, hydroxyethyl, C.sub.1 -C.sub.2 -alkoxyethyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.2 -C.sub.3 -alkyl or methylphenyl.
Priority Claims (1)
Number Date Country Kind
3630279 Sep 1986 DEX
Parent Case Info

This application is a continuation of application Ser. No. 07/228,874, filed on Aug. 5, 1988, now abandoned, which is a continuation of application Ser. No. 07/089,542, filed on Aug. 26, 1987, now abandoned. In the sublimation transfer process, a transfer sheet which contains a sublimable dye with or without a binder on a carrier is heated from the rear by short heat pulses (lasting fractions of a second) using a thermal printing head, the dye being sublimed or vaporized and transferred to a receiving medium. The essential advantage of this process is that the amount of dye to be transferred (and hence the color gradation) can readily be controlled by adjusting the energy to be supplied to the thermal printing head. In general, the color image is produced using the three subtractive primary colors, yellow, magenta and cyan (and if necessary black). In order to permit an optimum color image to be produced, the dyes must have the following properties: (i) readily sublimable or vaporizable; in general, this requirement is most difficult to meet in the case of the cyan dyes; (ii) high thermal and photochemical stability and resistance to moisture and chemical substances; (iii) suitable hues for subtractive color mixing; (iv) a high molecular absorption coefficient; (v) readily obtainable industrially. Most of the known dyes used for thermal transfer printing do not adequately meet these requirements. The prior art discloses dyes for this purpose. JP-A 159091/1985 describes dyes of the formula ##STR4## where R is alkyl, aralkyl, aryl or a 5-membered or 6-membered carbocyclic ring, for this purpose. JP-A 30392/1985 discloses dyes of the formula ##STR5## where R, R.sup.1 and R.sup.2 are each allyl, alkyl or alkoxyalkyl and X is H or methyl. JP-A 229786/1985 describes dyes of the formula ##STR6## where R and R.sup.1 are each methyl, ethyl, propyl or butyl and X is H or methyl, for this application. In JP-A 239292/1985, dyes of the formula ##STR7## are described for the transfer process. In the formula, R.sup.1 is C.sub.1 -C.sub.8 -alkyl, R.sup.2 is H or methyl and D is ##STR8## Quinone derivatives of the formula ##STR9## where R and R.sup.1 are each methyl, ethyl, propyl or butyl, are described for this application in JP-A 229 786/1985. Furthermore, the use of indoaniline dyes of the general formula ##STR10## is described for this purpose in DE-A 35 24 519. It is an object of the present invention to provide dyes which are readily sublimable or vaporizable under the conditions produced by a thermal printing head, do not undergo thermal or photochemical decomposition, can be processed to give printing inks and meet the color requirements. The dyes should also be readily obtainable industrially. We have found that this object is achieved by a process for transferring dyes from a carrier by sublimation/vaporization with the aid of a thermal printing head to a plastic-coated paper, wherein a carrier is used on which dyes of the general formula ##STR11## where A is D--N.dbd.N-- or ##STR12## R.sup.1 and R.sup.2 independently of one another are each hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or halogen and R.sup.1 together with R may form a 5-membered or 6-membered heterocyclic ring, and R and R' independently of one another are each hydrogen, phenyl which is unsubstituted or substituted by methyl or methoxy, or C.sub.5 - or C.sub.6 -cycloalkyl or C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.2 -C.sub.5 -alkanoyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyloxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 - or C.sub.3 -alkoxycarbonyloxy, hydroxyl, cyano, halogen, phenyl or C.sub.5 - or C.sub.6 -cycloalkyl, or ##STR13## is a 5-membered or 6-membered heterocyclic ring, D is ##STR14## R.sup.3 is hydrogen or CN, R.sup.4 is C.sub.1 -C.sub.4 -alkyl, phenyl, benzyl or CN, R.sup.5 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkoxy, C.sub.5 - or C.sub.6 -cycloalkyl, benzyl, C.sub.5 - or C.sub.6 -cycloalkylthio, C.sub.5 - or C.sub.6 -cycloalkoxy, benzyloxy or benzylthio, R.sup.6 is CN or --CHO, R.sup.7 is C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or chlorine and R.sup.8 is --CHO, CN or nitro, and R.sup.1 and R.sup.2 must not be hydrogen when A is and R.sup.5 is alkylthio or when A is ##STR15## Compared with the dyes used in the conventional processes, those employed in the novel process possess better sublimability and in some cases greater lightfastness and greater resistance to chemical substances.

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Entry
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Continuations (2)
Number Date Country
Parent 228874 Aug 1988
Parent 89542 Aug 1987