EP0567829A1 - Procédé pour le transfert de colorants anthraquinoniques - Google Patents
Procédé pour le transfert de colorants anthraquinoniques Download PDFInfo
- Publication number
- EP0567829A1 EP0567829A1 EP93105925A EP93105925A EP0567829A1 EP 0567829 A1 EP0567829 A1 EP 0567829A1 EP 93105925 A EP93105925 A EP 93105925A EP 93105925 A EP93105925 A EP 93105925A EP 0567829 A1 EP0567829 A1 EP 0567829A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- hydrogen
- alkoxy
- anthraquinone dyes
- cyano
- 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
Links
- 239000001000 anthraquinone dye Substances 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 239000004033 plastic Substances 0.000 claims abstract description 6
- 229920003023 plastic Polymers 0.000 claims abstract description 6
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims abstract description 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract description 5
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims abstract description 4
- 238000009792 diffusion process Methods 0.000 claims abstract description 4
- 238000000859 sublimation Methods 0.000 claims abstract description 4
- 230000008022 sublimation Effects 0.000 claims abstract description 4
- 239000000758 substrate Substances 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- -1 cyano, phenyl Chemical group 0.000 abstract description 9
- 150000002367 halogens Chemical group 0.000 abstract description 4
- 239000000975 dye Substances 0.000 description 21
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 239000011230 binding agent Substances 0.000 description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 238000010023 transfer printing Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000001045 blue dye Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 0 *C(c1c(*)c(*)c(C(C2C=CC=CC2C2=O)=O)c2c1*)=O Chemical compound *C(c1c(*)c(*)c(C(C2C=CC=CC2C2=O)=O)c2c1*)=O 0.000 description 1
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 1
- HPDVKZCKPOFXQA-UHFFFAOYSA-N 2-acetyl-1-aminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(C(=O)C)=CC=C3C(=O)C2=C1 HPDVKZCKPOFXQA-UHFFFAOYSA-N 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 229920000896 Ethulose Polymers 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241001295925 Gegenes Species 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012791 sliding layer Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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
- B41M5/3852—Anthraquinone or naphthoquinone dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/913—Material designed to be responsive to temperature, light, moisture
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/914—Transfer or decalcomania
Definitions
- the present invention relates to a new method for transferring anthraquinone dyes by diffusion or sublimation from a support to a plastic-coated substrate using an energy source.
- a transfer sheet which contains a thermally transferable dye in one or more binders, optionally together with suitable auxiliaries, on a support, with an energy source, e.g. with a heating head or a laser, heated by short heating impulses (duration: fractions of a second) from the back, whereby the dye migrates from the transfer sheet and diffuses into the surface coating of a recording medium, usually into the plastic layer of a coated paper.
- an energy source e.g. with a heating head or a laser
- short heating impulses duration: fractions of a second
- the color is recorded using the subtractive primary colors yellow, magenta, cyan (and possibly black).
- the invention was therefore based on the object of finding suitable blue dyes for thermal transfer printing processes which come closer to the required property profile than the dyes known hitherto.
- Suitable radicals R1, R2 or R3 are C1-C20 alkyl groups, C1-C12 alkyl groups are preferred and, in the case of R3, C1-C4 alkyl groups are particularly preferred.
- the following may be mentioned in detail: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, sec-pentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl , 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl and
- the alkyl groups can also be substituted by halogen, hydroxy or cyano; Examples include: - (CH2) 5-Cl, -CH (C4H9) - (CH2) 3-Cl and - (CH2) 4-CF3; - (CH2) 2-CH (CH3) -OH, - (CH2) 2-CH (C4H9) -OH and -CH (C2H5) - (CH2) 9-OH; - (CH2) 2-CN, - (CH2) 3-CN, -CH2-CH (CH3) -CH (C2H5) -CN, - (CH2) 6-CH (C2H5) -CN and - (CH2) 3-CH (CH3) - (CH2) 2-CH (CH3) -CN.
- alkanoyloxyalkyl, alkoxycarbonyloxyalkyl and alkoxycarbonylalkyl groups suitable as R1, R2 or R3 are: - (CH2) 2-O-CO-CH3, - (CH2) 3-O-CO- (CH2) 7-CH3, - (CH2) 2-O-CO- (CH2) 3-Ph-2-O-CH3, -CH (CH2-Ph-3-CH3) -O-CO-C4H9 and - (CH2) 4-O-CO- (CH2) 4-CH (C2H5) -OH; - (CH2) 2-O-CO-O-CH3, - (CH2) 3-O-CO-O- (CH2) 7-CH3, -CH (C2H5) -CH2-O-CO-O-C4H9, -CH2) 4-O-CO-O- (CH2) 2-CH (CH3) -O-Ph-3-CH3 and - (CH2) 5-O-CO-O- (CH2) 5-CN; - (CH2) 2-CO-O-
- radicals R 1, R 2 or R 3 are groupings of the formula II
- suitable alkylene groups W are, for example, 1,2-, 1,3-, 1,4- or 2,3-butylene, pentamethylene, hexamethylene, 2- Methyl pentamethylene, especially 1,2- and 1,3-propylene and especially ethylene and radicals R4 preferably methyl, ethyl, propyl, isopropyl, butyl and phenyl, for example by methyl (oxy), ethyl (oxy), propyl (oxy) or butyl (oxy) may be substituted, but is preferably unsubstituted.
- Examples of further preferred groups II are: - (CH2) 3-O-CH3, - (CH2) 3-O-C2H5, - (CH2) 3-O-C3H7, - (CH2) 3-O-CH (CH3) 2, - (CH2) 3-O-C4H9, - (CH2) 3-O-Ph, -CH2-CH (CH3) -O-CH3, -CH2-CH (CH3) -O-C2H5, -CH2-CH (CH3) -O-C3H7, -CH2-CH (CH3) -O-C4H9, -CH2-CH (CH3) -O-Ph, - (CH2) 4-O-CH3, - (CH2) 4-O-C2H5, - (CH2) 4-O-C4H9, - (CH2) 4-O-Ph, - (CH2) 4-O-CH2-Ph-2-O-C2H5, - (CH2) 4-O-C6H10-2-C2H5, - [(CH2) 4-O] 2-C
- Suitable radicals R1, R2 or R3 are also benzyl and especially phenyl groups, which can carry up to three C1-C1,, preferably C1-C4 alkyl or alkoxy radicals, but are preferably substituted twice or once or unsubstituted.
- R1 is particularly preferably hydrogen
- R2 is phenyl, which can be substituted by C1-C4-alkyl or alkoxy
- R3 is C1-C4-alkyl, in particular methyl
- X in addition to cyano is especially hydrogen.
- the anthraquinone dyes I are known per se or can be prepared by known methods.
- the anthraquinones I which have an acetyl group in the 2-position are e.g. Expediently from 1-amino-2-acetylanthraquinone (Houben-Weyl, Vol. 7 / 3c, p. 251), which can then be reacted with the desired amines in the usual way after bromination in the sense of a Ullmann reaction.
- the dyes I used are generally distinguished by improved migration properties in the recording medium at room temperature, easier thermal transferability, higher thermal and photochemical stability, easier technical accessibility, better resistance to moisture and chemicals, higher color strength, better solubility or better suitability for subtractive color mixing (higher color purity, more favorable form of the absorption band, higher transparency in the green spectral range).
- the dyes are processed to a printing ink in a suitable organic solvent or in mixtures of solvents with one or more binders, if appropriate with the addition of auxiliaries.
- a printing ink in a suitable organic solvent or in mixtures of solvents with one or more binders, if appropriate with the addition of auxiliaries.
- the printing ink can be applied to the inert carrier using a doctor blade. The resulting color is then air dried.
- Suitable organic solvents are those in which the solubility of the dyes I generally at a temperature of 20 ° C. is greater than 1% by weight, preferably greater than 5% by weight.
- ethanol for example, ethanol, propanol, isobutanol, tetrahydrofuran, methylene chloride, methyl ethyl ketone, cyclopentanone, cyclohexanone, toluene, chlorobenzene or mixtures thereof.
- binders All resins or polymer materials which are soluble in organic solvents and bind the dye to the inert support in an abrasion-resistant manner are suitable as binders capital. Preference is given to those binders which, after the printing ink has dried in air, absorb the dye in the form of a clear, transparent film without the dye crystallizing out visibly.
- Preferred binders are especially ethyl cellulose, ethyl hydroxyethyl cellulose, polyvinyl butyrate, polyvinyl acetate, cellulose propionate and saturated linear polyesters.
- the weight ratio of binder: dye is generally 1: 1 to 10: 1.
- Suitable inert carriers are also described in EP-A-441 282 and in the patent applications cited therein.
- the thickness of the dye carrier is generally 3 to 30 microns, preferably 5 to 10 microns.
- thermostable plastic layers with affinity for the dyes to be transferred can be used as the dye-receiving layer, e.g. modified polycarbonates or polyester. Further details can be found in EP-A-441 282 or the patent applications cited therein.
- the dye is transferred using an energy source, such as a laser or, above all, a thermal head, the latter having to be able to be heated to a temperature of ⁇ 300 ° C. so that the dye transfer can take place in the time range t: 0 ⁇ t ⁇ 15 msec.
- the dye migrates from the transfer sheet and diffuses into the surface coating of the recording medium.
- the printing ink obtained was knife-coated onto a 6 ⁇ m-thick polyester film with a sliding layer on the back using a 6 ⁇ m doctor blade.
- the ink ribbons were then first blown dry with a hair dryer and then air-dried for at least 24 hours in order to remove residual amounts of solvent.
- the ribbons were then printed on Hitachi VY-S video print paper on a computer-controlled experimental set-up with a commercially available thermal head.
- the energy emitted by the thermal head is controlled by changing the voltage, the set pulse duration being 7 ms and only one pulse being emitted.
- the energy delivered is between 0.71 and 1.06 mJ per dot.
- the following table shows the transferred anthraquinone dyes I, their absorption maximum ⁇ max [nm] measured in methylene chloride, their half-value values HWB [cm ⁇ 1] and their transfer data Q * [mJ / Dot] and m [1 / mJ].
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4214175 | 1992-04-30 | ||
| DE4214175A DE4214175A1 (de) | 1992-04-30 | 1992-04-30 | Verfahren zur uebertragung von anthrachinonfarbstoffen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0567829A1 true EP0567829A1 (fr) | 1993-11-03 |
| EP0567829B1 EP0567829B1 (fr) | 1997-01-22 |
Family
ID=6457784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP93105925A Expired - Lifetime EP0567829B1 (fr) | 1992-04-30 | 1993-04-13 | Procédé pour le transfert de colorants anthraquinoniques |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5302577A (fr) |
| EP (1) | EP0567829B1 (fr) |
| JP (1) | JPH0624158A (fr) |
| DE (2) | DE4214175A1 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5491045A (en) * | 1994-12-16 | 1996-02-13 | Eastman Kodak Company | Image dye combination for laser ablative recording element |
| DE19716811A1 (de) † | 1997-04-22 | 1998-10-29 | Grob Gmbh & Co Kg | Transferstraße |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3617173A (en) * | 1968-06-24 | 1971-11-02 | Toms River Chemical Corp | 2-benzoylanthraquinone dyes for polyester fibers |
| GB1456957A (en) * | 1974-07-05 | 1976-12-01 | Bayer Ag | Transfer printing process |
| US4940692A (en) * | 1988-04-12 | 1990-07-10 | Basf Aktiengesellschaft | Transfer of dyes |
| JPH03158294A (ja) * | 1989-11-16 | 1991-07-08 | Mitsui Toatsu Chem Inc | シアン色系感熱昇華転写シート |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4004612A1 (de) * | 1990-02-15 | 1991-08-22 | Basf Ag | Neue bichromophore methin- und azamethinfarbstoffe und ein verfahren zu ihrer uebertragung |
| DE4031984A1 (de) * | 1990-10-09 | 1992-04-16 | Basf Ag | Verwendung von anthrachinonfarbstoffen fuer den thermotransferdruck |
| DE4039923A1 (de) * | 1990-12-14 | 1992-06-17 | Basf Ag | Verwendung von anthrachinonfarbstoffen fuer den thermotransferdruck |
-
1992
- 1992-04-30 DE DE4214175A patent/DE4214175A1/de not_active Withdrawn
-
1993
- 1993-03-29 US US08/038,867 patent/US5302577A/en not_active Expired - Fee Related
- 1993-04-13 DE DE59305197T patent/DE59305197D1/de not_active Expired - Lifetime
- 1993-04-13 EP EP93105925A patent/EP0567829B1/fr not_active Expired - Lifetime
- 1993-04-27 JP JP5100633A patent/JPH0624158A/ja not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3617173A (en) * | 1968-06-24 | 1971-11-02 | Toms River Chemical Corp | 2-benzoylanthraquinone dyes for polyester fibers |
| GB1456957A (en) * | 1974-07-05 | 1976-12-01 | Bayer Ag | Transfer printing process |
| US4940692A (en) * | 1988-04-12 | 1990-07-10 | Basf Aktiengesellschaft | Transfer of dyes |
| JPH03158294A (ja) * | 1989-11-16 | 1991-07-08 | Mitsui Toatsu Chem Inc | シアン色系感熱昇華転写シート |
Also Published As
| Publication number | Publication date |
|---|---|
| DE4214175A1 (de) | 1993-11-04 |
| JPH0624158A (ja) | 1994-02-01 |
| DE59305197D1 (de) | 1997-03-06 |
| EP0567829B1 (fr) | 1997-01-22 |
| US5302577A (en) | 1994-04-12 |
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