EP0645259A1 - Transfert thermique de colorants infrarouges - Google Patents

Transfert thermique de colorants infrarouges Download PDF

Info

Publication number: EP0645259A1
Authority: EP; European Patent Office
Prior art keywords: formula; nickel; dyes; hydrogen; alkyl
Prior art date: 1993-09-24
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

EP94114502A

Other languages

German (de)

English (en)

Other versions

EP0645259B1 (fr

Inventor

Friedrich Closs

Juergen Dr. Kipper

Ruediger Dr. Sens

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.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

1993-09-24

Filing date

1994-09-15

Publication date

1995-03-29

1994-09-15 Application filed by BASF SE filed Critical BASF SE

1995-03-29 Publication of EP0645259A1 publication Critical patent/EP0645259A1/fr

1997-01-02 Application granted granted Critical

1997-01-02 Publication of EP0645259B1 publication Critical patent/EP0645259B1/fr

2014-09-15 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000012546 transfer Methods 0.000 title claims abstract description 13
239000000975 dye Substances 0.000 claims abstract description 32
238000000034 method Methods 0.000 claims abstract description 16
238000009792 diffusion process Methods 0.000 claims abstract description 3
239000011092 plastic-coated paper Substances 0.000 claims abstract description 3
238000000859 sublimation Methods 0.000 claims abstract description 3
230000008022 sublimation Effects 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 10
125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
125000001033 ether group Chemical group 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
229910052802 copper Inorganic materials 0.000 claims description 4
239000010949 copper Substances 0.000 claims description 4
229910052744 lithium Inorganic materials 0.000 claims description 4
239000011777 magnesium Substances 0.000 claims description 4
229910052749 magnesium Inorganic materials 0.000 claims description 4
229910052759 nickel Inorganic materials 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
239000011701 zinc Substances 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical compound N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 abstract description 2
-1 C1-C20 alkyl radicals Chemical class 0.000 description 54
239000000203 mixture Substances 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
239000011230 binding agent Substances 0.000 description 8
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
239000000976 ink Substances 0.000 description 6
238000007639 printing Methods 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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 3
239000001856 Ethyl cellulose Substances 0.000 description 3
229920001249 ethyl cellulose Polymers 0.000 description 3
235000019325 ethyl cellulose Nutrition 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229920000728 polyester Polymers 0.000 description 3
MJFITTKTVWJPNO-UHFFFAOYSA-N 3h-dithiole;nickel Chemical compound [Ni].C1SSC=C1 MJFITTKTVWJPNO-UHFFFAOYSA-N 0.000 description 2
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
238000010521 absorption reaction Methods 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
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 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
239000010410 layer Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000010023 transfer printing Methods 0.000 description 2
125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005976 1-phenylethyloxy group Chemical group 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000005975 2-phenylethyloxy group Chemical group 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
229920000896 Ethulose Polymers 0.000 description 1
239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241001295925 Gegenes Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
150000001298 alcohols 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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920006218 cellulose propionate Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
238000004891 communication Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 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
238000004043 dyeing Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 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
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 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
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([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
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920002037 poly(vinyl butyral) polymer Polymers 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
238000002360 preparation method Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000013557 residual solvent Substances 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
239000012791 sliding layer Substances 0.000 description 1
239000002904 solvent Substances 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
239000000758 substrate Substances 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
238000012360 testing method Methods 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

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
- B41M5/40—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography
- B41M5/46—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography characterised by the light-to-heat converting means; characterised by the heat or radiation filtering or absorbing means or layers
- B41M5/465—Infrared radiation-absorbing materials, e.g. dyes, metals, silicates, C black
- 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
- 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
- B41M5/39—Dyes containing one or more carbon-to-nitrogen double bonds, e.g. azomethine

Definitions

the present invention relates to a new method for the thermal transfer of IR dyes, selected from the class consisting of naphthalocyanine derivatives and a nickel dithiolene complex.
IR dyes are those compounds that have their absorption maximum in the infrared (IR) range.
Printed barcodes which can be scanned and read with suitable light sources and detectors, serve as an example.
EP-A-553 614 discloses the use of such printing inks which contain IR dyes. It can be used to produce prints that are practically invisible to the human eye but can be read by suitable detectors.
a transfer sheet which contains a thermally transferable dye in one or more binders, possibly together with suitable auxiliaries, on a carrier, with an energy source, e.g. with a heating head or a laser, by means of short heating pulses (duration: fractions of a second ) heated from the back, whereby the dye migrates from the transfer sheet and diffuses into the surface coating of a recording medium.
an energy source e.g. with a heating head or a laser
the object of the present invention was to provide a new thermal transfer printing process in which special IR dyes are transferred to the substrate.
IR dyes from a support onto a plastic-coated paper by diffusion or sublimation using an energy source are selected from the class consisting of naphthalocyanines of the formula I.
Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 independently of one another are each hydrogen, hydroxy, C1-C20-alkyl or C1-C20-alkoxy, where the alkyl groups can each be interrupted by 1 to 4 oxygen atoms in ether function and optionally are substituted by phenyl, Y9, Y10, Y11 and Y12 independently of one another are each hydrogen, C1-C20-alkyl or C1-C20-alkoxy, where the alkyl groups can each be interrupted by 1 to 4 oxygen atoms in ether function, halogen, hydroxysulfonyl or C1-C4-dialkylsulfamoyl and Me means twice hydrogen, twice lithium, magnesium, zinc, copper, nickel, VO, TiO or AlCl, and the nickel-dithiolene complex of the formula II
the dyes of the formulas I and II have their absorption maximum in the range from 800 to 950 nm.
C1-C20 alkyl radicals which are optionally interrupted by 1 to 4 oxygen atoms in ether function, e.g. Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, Decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl, isotridecyl (the above terms isooctyl, isononyl, isodecyl and isotridecyl are trivial names and come from the alcohol
C1-C20 alkoxy radicals which are optionally interrupted by 1 to 4 oxygen atoms in ether function, for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, Pentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, isooctyloxy, nonyloxy, isononyloxy, decyloxy, isodecyloxy, undecyloxy, dodecyloxy, tridecyloxy, isotridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, methadecyloxy, methadecyloxy, methadecyloxy, methadecyloxy, methadecyloxy, methadecyloxy, heptadyloxy, Ethoxyethoxy, 2-propoxye
Halogen in formula I is e.g. Fluorine, chlorine or bromine.
Residues Y9 to Y12 in formula I are e.g. Dimethylsulfamoyl, diethylsulfamoyl, dipropylsulfamoyl, dibutylsulfamoyl or N-methyl-N-ethylsulfamoyl.
a procedure is preferred in which a carrier is used on which one or more naphthalocyanines of the formula Ia are in the Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 independently of one another are each hydrogen, hydroxy, C1-C4-alkyl or C1-C20-alkoxy and Me means twice hydrogen, twice lithium, magnesium, zinc, copper, nickel, VO or AlCl.
a carrier is used on which there are one or more naphthalocyanines of the formula Ia in which Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are each independently of one another hydroxy or C1-C20 -Alkoxy, in particular C1-C10 alkoxy.
the alkoxy radicals can be the same or different.
naphthalocyanines of the formula I are known per se and are described, for example, in GB-A-2 168 372 or GB-A-2 200 650 or can be prepared by methods known per se, such as are used in the preparation of phthalocyanines or naphthalocyanines like for example in FH Moser, A.L. Thomas “The Phthalocyanines", CRC Press, Boca Rota, Florida, 1983, or J. Am. Chem. Soc. Volume 106, pages 7404 to 7410, 1984.
the nickel-dithiolene complex of the formula II is also known per se and is described, for example, in DE-A-4 202 037.
the IR dyes of the formula I and / or II 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 suitable organic solvent or in mixtures of solvents with one or more binders if appropriate with the addition of auxiliaries.
This preferably contains the dyes in a molecularly dispersed form.
the printing ink can be applied to the inert support using a doctor blade and the dyeing can be dried in air.
Suitable organic solvents for the dye mixtures are, for example, those in which the solubility of the dye mixtures at a temperature of 20 ° C. is greater than 1% by weight, preferably greater than 5% by weight.
Examples include 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 which are capable of binding the dye mixtures to the inert carrier in an abrasion-resistant manner are suitable as binders. Preference is given to those binders which, after the printing ink has dried in air, absorb the dye mixture in the form of a clear, transparent film without any visible crystallization of the dye mixture.
Preferred binders are ethyl cellulose, ethyl hydroxyethyl cellulose, polyvinyl butyral, polyvinyl acetate, cellulose propionate or saturated linear polyesters.
the weight ratio of binder: IR dye is generally 1: 1 to 10: 1.
Suitable inert carriers are e.g. in US-A-5 132 438 or in the corresponding patent applications cited therein.
the thickness of the dye carrier is generally 3 to 30 microns, preferably 5 to 10 microns.
all temperature-stable plastic layers with affinity for the dyes to be transferred can be used as the dye-receiving layer, e.g. modified polycarbonate or polyester. Further details can e.g. can be found in US-A-S 132 438 or the corresponding patent applications cited therein.
the transfer takes place by means of an energy source, for example by means of a laser or a thermal head, the latter having to be heatable to a temperature of ⁇ 300 ° C. so that the dye transfer can take place in the time range t: 0 ⁇ t ⁇ 15 msec.
an energy source for example by means of a laser or a thermal head, the latter having to be heatable 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.

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

EP94114502A 1993-09-24 1994-09-15 Transfert thermique de colorants infrarouges Expired - Lifetime EP0645259B1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4332552		1993-09-24
DE4332552A DE4332552A1 (de)	1993-09-24	1993-09-24	Thermische Übertragung von IR-Farbstoffen

Publications (2)

Publication Number	Publication Date
EP0645259A1 true EP0645259A1 (fr)	1995-03-29
EP0645259B1 EP0645259B1 (fr)	1997-01-02

Family

ID=6498530

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP94114502A Expired - Lifetime EP0645259B1 (fr)	1993-09-24	1994-09-15	Transfert thermique de colorants infrarouges

Country Status (3)

Country	Link
EP (1)	EP0645259B1 (fr)
JP (1)	JPH07149060A (fr)
DE (2)	DE4332552A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4753923A (en) *	1987-11-20	1988-06-28	Eastman Kodak Company	Thermally-transferred near-infrared absorbing dyes
JPH05169838A (ja) *	1991-12-19	1993-07-09	Mitsubishi Kasei Corp	赤外線加熱型感熱転写記録用シート
EP0553614A1 (fr) *	1992-01-25	1993-08-04	BASF Aktiengesellschaft	Utilisation comme encre d'impression d'un liquide contenant un colorant infrarouge

1993
- 1993-09-24 DE DE4332552A patent/DE4332552A1/de not_active Withdrawn
1994
- 1994-09-15 DE DE59401456T patent/DE59401456D1/de not_active Expired - Lifetime
- 1994-09-15 EP EP94114502A patent/EP0645259B1/fr not_active Expired - Lifetime
- 1994-09-20 JP JP6225350A patent/JPH07149060A/ja not_active Withdrawn

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4753923A (en) *	1987-11-20	1988-06-28	Eastman Kodak Company	Thermally-transferred near-infrared absorbing dyes
EP0316928A2 (fr) *	1987-11-20	1989-05-24	EASTMAN KODAK COMPANY (a New Jersey corporation)	Colorants pour transfert thermique absorbant des rayons du proche infrarouge
JPH05169838A (ja) *	1991-12-19	1993-07-09	Mitsubishi Kasei Corp	赤外線加熱型感熱転写記録用シート
EP0553614A1 (fr) *	1992-01-25	1993-08-04	BASF Aktiengesellschaft	Utilisation comme encre d'impression d'un liquide contenant un colorant infrarouge

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
& US-A-4 753 923 *

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Publication number	Publication date
DE59401456D1 (de)	1997-02-13
JPH07149060A (ja)	1995-06-13
DE4332552A1 (de)	1995-03-30
EP0645259B1 (fr)	1997-01-02

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