EP0420036B1 - Utilisation de colorants azoiques pour l'impression par transfert thermique - Google Patents
Utilisation de colorants azoiques pour l'impression par transfert thermique Download PDFInfo
- Publication number
- EP0420036B1 EP0420036B1 EP90118082A EP90118082A EP0420036B1 EP 0420036 B1 EP0420036 B1 EP 0420036B1 EP 90118082 A EP90118082 A EP 90118082A EP 90118082 A EP90118082 A EP 90118082A EP 0420036 B1 EP0420036 B1 EP 0420036B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- hydrogen
- phenyl
- substituted
- azo dyes
- 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.)
- Expired - Lifetime
Links
- 239000000987 azo dye Substances 0.000 title claims description 17
- 238000010023 transfer printing Methods 0.000 title claims description 12
- -1 amino, hydroxyl Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229920003023 plastic Polymers 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 4
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000009792 diffusion process Methods 0.000 claims description 4
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 238000007651 thermal printing Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 31
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 22
- 239000000975 dye Substances 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- 239000011230 binding agent Substances 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- 238000007639 printing Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- 239000001856 Ethyl cellulose Substances 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229920001249 ethyl cellulose Polymers 0.000 description 3
- 235000019325 ethyl cellulose Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 239000001043 yellow dye Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 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
- 229920001577 copolymer Polymers 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 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
- 239000000314 lubricant Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 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
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 244000165918 Eucalyptus papuana Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 229920002301 cellulose acetate Polymers 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 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
- 150000002148 esters Chemical class 0.000 description 1
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000011086 glassine 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
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 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
- 230000002045 lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration 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
- 239000000025 natural resin Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 230000003287 optical effect Effects 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
- 239000011092 plastic-coated paper Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin 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
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 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
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
-
- 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
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31507—Of polycarbonate
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
Definitions
- thermal transfer printing In addition to the laser and IR lamp, a thermal head is used as the heat source, with which short heating pulses lasting a fraction of a second can be emitted.
- a transfer sheet which contains the dye to be transferred together with one or more binders, a carrier material and possibly other auxiliaries such as release agents or crystallization-inhibiting substances is heated from the rear by the thermal head.
- the dye diffuses from the transfer sheet into the surface coating of the substrate, e.g. into the plastic layer of a coated paper.
- the main advantage of this method is that the amount of ink transferred and thus the color gradation can be controlled in a targeted manner via the energy to be delivered to the thermal head.
- the azo dyes I themselves are known per se or can be obtained by known methods (EP-B-111 236).
- the invention was therefore based on the object of finding suitable yellow dyes for thermal transfer printing which come closer to the required property profile than the previously known dyes.
- a method for transferring azo dyes by diffusion from a support onto a plastic-coated substrate using a thermal head was found, which is characterized in that a support is used for this purpose, on which one or more of the azo dyes I defined at the outset are located.
- R 1 or R 2 are the alkyl groups methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, sec-pentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl , 2-ethylhexyl or the isomer mixture isooctyl, nonyl or decyl or their isomer mixtures isononyl and isodecyl and undecyl or dodecyl.
- tridecyl or its isomer mixture isotridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl or eicosyl are also suitable, for example
- the alkyl groups can also be substituted by phenyl;
- Ph phenyl
- Examples of further preferred groups II are: - (CH2) 3-O-CH3, - (CH2) 3-O-C2H5, - (CH2) 3-O-C3H7, - (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-C2H5, - [(CH2) 2-CH (CH3)
- alkanoyloxyalkyl, alkoxycarbonyloxyalkyl or alkoxycarbonylalkyl groups suitable as R1 or R2 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 or - (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 or - (CH2) 5-O-CO-O- (CH2) 5-CN; - (CH2) 2-CO-O-CH
- Phenyl or cyclohexyl radicals which may be present as R1 or R2 are, for example, the following: -Ph, -Ph-3-CH3, -Ph-4- (CH2) 10-CH3, -Ph-3- (CH2) 5-CH (CH3) -CH3, -PH-4-O-C4H9, -Ph-4- (CH2) 5-CH (C2H5) -CH3, -Ph-4-O-CH2-Ph or -Ph-4-Cl; -C6H10-4-CH3, -C6H10-4-C10H21, -C6H10-3-O-C4H9, -C6H10-3-O- (CH2) 4-CH (C2H5) -CH3 or -C6H10-4-Cl.
- the substituents X and Y are preferably hydrogen and nitro, and also chlorine and bromine. Further substituents X are methyl, methyloxy, ethyloxy, propyloxy, butyloxy, phenoxy, tolyloxy or dimethylphenyloxy.
- the cyano group is particularly preferred as the substituent Z, and hydrogen, acetyl and carbamoyl are also suitable.
- the dyes I to be used according to the invention are distinguished from the yellow dyes previously used for thermal transfer printing by the following properties: easier thermal transferability in spite of the relatively high molecular weight, improved migration properties in the recording medium at room temperature, significantly higher lightfastness, better resistance to moisture and chemicals, better solubility in the manufacture of the printing ink, higher color strength and easier technical accessibility.
- binders are often recommended, e.g. those made of ethyl cellulose and polyvinyl butyrate in a weight ratio of 2: 1.
- Inert carrier materials are, for example, tissue paper, blotting paper or glassine paper and films made of heat-resistant plastics such as polyesters, polyamides or polyimides, these films also being able to be metal-coated.
- the inert carrier can additionally be coated with a lubricant on the side facing the thermal head in order to prevent the thermal head from sticking to the carrier material.
- Suitable lubricants are, for example, silicones or polyurethanes, as described in EP-A-216 483.
- the substrate to be printed for example paper, must in turn be coated with a binder which absorbs the dye during the printing process.
- a binder which absorbs the dye during the printing process.
- Polymeric materials whose glass transition temperature T g is between 50 and 100 ° C., for example polycarbonates and polyester, are preferably used for this purpose. Further details can be found in EP-A-227 094, EP-A-133 012, EP-A-133 011, JP-A-199 997/1986 or JP-A 283 595/1986.
- transfer sheets were made in a conventional manner from 8 ⁇ m thick polyester film, which was provided with an approximately 5 ⁇ m thick transfer layer made of a binder B, each of which contained 0.25 g of azo dye I.
- the weight ratio of binder to dye was 4: 1 in each case.
- the coated side of the encoder and slave was placed on top of one another, wrapped with aluminum foil and heated to a temperature between 70 and 80 ° C. for two minutes between two heating plates. With similar samples, this process was repeated three times at a higher temperature between 80 and 120 ° C.
- the amount of dye diffused into the plastic layer of the receiver is proportional to the optical density, which was determined as absorbance A photometrically after the respective heating to the temperatures given above.
- the azo dyes I used are divided into groups in the following tables; the variable P indicates the position of the oxadiazole residue on the phenyl nucleus of the diazo component in relation to the azo group (o: ortho, m: meta, p: para).
- binder B used in each case.
- EC ethyl cellulose
- PVB polyvinyl butyrate
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Claims (4)
- Utilisation, pour l'impression par transfert thermique, de colorants azoïques de formule générale I
R¹, R² atomes d'hydrogène;
groupements alkyle, alcoxyalkyle, alcanoyloxyalkyle, alcoxycarbonyloxyalkyle, alcoxycarbonylalkyle, halogénoalkyle, hydroxyalkyle ou cyanoalkyle, qui peuvent être substitués chacun par des restes phényle, (alkyl en C₁-C₄)phényle, (alcoxy en C₁-C₄)phényle, halogénophényle, benzyloxy, (alkyl en C₁-C₄)benzyloxy, (alcoxy en C₁-C₄)benzyloxy, halogénobenzyloxy, halogéno, hydroxy ou cyano;
groupements phényle ou cyclohexyle, qui peuvent être substitués par des restes alkyle en C₁-C₁₅, alcoxy en C₁-C₁₅, halogéno ou benzyloxy;
un reste de formule générale II
[-W-O]n-R⁴ II
dans laquelleW représente des groupements alkylène en C₂-C₆ identiques ou différents,n est un nombre de 1 à 6 etR⁴ est mis pour un groupement alkyle en C₁-C₄ ou phényle, qui peut être substitué par un radical alkyle en C₁-C₄ ou alcoxy en C₁-C₄;R³ atome d'hydrogène, groupement amino, hydroxy ou alkyle;X atome d'hydrogène, de chlore, de brome, groupement nitro, méthyle, phénoxy, tolyloxy, diméthylphényloxy, chlorophénoxy ou alcoxy en C₁-C₄;Y atome d'hydrogène, de chlore ou de brome; etZ atome d'hydrogène, groupement acétyle, carbamoyle ou cyano. - Procédé de transfert de colorants azoïques par diffusion entre un support et un substrat enduit d'une couche de matière plastique à l'aide d'une tête thermique, caractérisé en ce qu'on utilise à cet effet un support sur lequel se trouvent un ou plusieurs colorants azoïques de formule I selon la revendication 1.
- Procédé selon la revendication 2, caractérisé en ce qu'on utilise à cette fin un colorant azoïque de formule Ia
- Procédé selon la revendication 2, caractérisé en ce qu'on utilise à cette fin un colorant azoïque de formule Ib
R1', R2' atomes d'hydrogène;
groupements alkyle, alcoxyalkyle, alcanoyloxy ou alcoxycarbonylalkyle, qui peuvent contenir chacun jusqu'à 15 atomes de carbone et peuvent être substitués par des restes phényle, (alkyl en C₁-C₄)phényle, (alcoxy en C₁-C₄)phényle, hydroxy ou cyano;
un reste de formule générale III
[-(CH₂)₃-O]p-⁅-(CH₂)₂-O]q-R4'
dans laquelle p est mis pour 0 ou 1 et q pour un nombre de 1 à 4, et R4' représente un groupement alkyle en C₁-C₄ ou phényle.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3932523A DE3932523A1 (de) | 1989-09-29 | 1989-09-29 | Verwendung von azofarbstoffen fuer den thermotransferdruck |
| DE3932523 | 1989-09-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0420036A1 EP0420036A1 (fr) | 1991-04-03 |
| EP0420036B1 true EP0420036B1 (fr) | 1994-05-18 |
Family
ID=6390467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90118082A Expired - Lifetime EP0420036B1 (fr) | 1989-09-29 | 1990-09-20 | Utilisation de colorants azoiques pour l'impression par transfert thermique |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5093308A (fr) |
| EP (1) | EP0420036B1 (fr) |
| JP (1) | JPH03126591A (fr) |
| DE (2) | DE3932523A1 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010025338A1 (fr) | 2008-08-29 | 2010-03-04 | Corindus Ltd. | Système de commande de cathéter et interface utilisateur graphique |
| JP5634019B2 (ja) * | 2008-10-14 | 2014-12-03 | キヤノン株式会社 | 色素化合物並びに該色素化合物を含有するインク |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4505975A (en) * | 1981-07-25 | 1985-03-19 | Sony Corporation | Thermal transfer printing method and printing paper therefor |
| DE3244960A1 (de) * | 1982-12-04 | 1984-06-07 | Basf Ag, 6700 Ludwigshafen | Pyridonfarbstoffe |
| US4555427A (en) * | 1983-07-25 | 1985-11-26 | Dai Nippon Insatsu Kabushiki Kaisha | Heat transferable sheet |
| US4927666A (en) * | 1983-07-25 | 1990-05-22 | Dai Nippon Insatsu Kabushiki Kaisha | Image-receiving sheet |
| EP0133011B1 (fr) * | 1983-07-25 | 1990-03-14 | Dai Nippon Insatsu Kabushiki Kaisha | Feuille pour utilisation en impression par thermotransfer |
| JPS60152563A (ja) * | 1984-01-20 | 1985-08-10 | Mitsubishi Chem Ind Ltd | ピリドン系感熱転写記録用色素及び感熱転写シート |
| JPS6112392A (ja) * | 1984-06-29 | 1986-01-20 | Mitsui Toatsu Chem Inc | 赤色系熱転写用色材 |
| JPS6112393A (ja) * | 1984-06-29 | 1986-01-20 | Mitsui Toatsu Chem Inc | 黄色系熱転写用色材 |
| JPS6131293A (ja) * | 1984-07-24 | 1986-02-13 | Sharp Corp | 感熱記録方法 |
| JPH0741746B2 (ja) * | 1985-02-28 | 1995-05-10 | 大日本印刷株式会社 | 熱転写受像シート |
| JPS61244595A (ja) * | 1985-04-24 | 1986-10-30 | Mitsubishi Chem Ind Ltd | 感熱転写記録用ピリドンアゾ系色素 |
| JPS61262191A (ja) * | 1985-05-16 | 1986-11-20 | Sumitomo Chem Co Ltd | 昇華転写体 |
| JPH0764123B2 (ja) * | 1985-05-23 | 1995-07-12 | 大日本印刷株式会社 | 熱転写シ−ト |
| JPH0714665B2 (ja) * | 1985-06-10 | 1995-02-22 | 大日本印刷株式会社 | 被熱転写シ−ト |
| GB8518572D0 (en) * | 1985-07-23 | 1985-08-29 | Ici Plc | Anthraquinone dye |
| GB8521327D0 (en) * | 1985-08-27 | 1985-10-02 | Ici Plc | Thermal transfer printing |
| US4695286A (en) * | 1985-12-24 | 1987-09-22 | Eastman Kodak Company | High molecular weight polycarbonate receiving layer used in thermal dye transfer |
| GB8612668D0 (en) * | 1986-05-23 | 1986-07-02 | Turnright Controls | Electronic time switch |
| GB8612778D0 (en) * | 1986-05-27 | 1986-07-02 | Ici Plc | Thermal transfer printing |
| EP0301752B1 (fr) * | 1987-07-30 | 1993-12-29 | Zeneca Limited | Impression par transfert thermique |
| JP2966849B2 (ja) * | 1987-12-03 | 1999-10-25 | 三井化学株式会社 | 黄色系昇華転写用色材 |
| US4985396A (en) * | 1987-12-29 | 1991-01-15 | Matsushita Electric Industrial Co., Ltd | Dye transfer type thermal printing sheets |
| US4985397A (en) * | 1988-10-03 | 1991-01-15 | Ricoh Company, Ltd. | Thermal image transfer recording system |
| GB8826455D0 (en) * | 1988-11-11 | 1988-12-14 | Ici Plc | Dyesheet |
| EP0384040B1 (fr) * | 1989-02-24 | 1994-01-26 | Agfa-Gevaert N.V. | Elément donateur de colorant pour le transfert thermique de colorant par sublimation |
-
1989
- 1989-09-29 DE DE3932523A patent/DE3932523A1/de not_active Withdrawn
-
1990
- 1990-09-20 DE DE59005730T patent/DE59005730D1/de not_active Expired - Lifetime
- 1990-09-20 EP EP90118082A patent/EP0420036B1/fr not_active Expired - Lifetime
- 1990-09-28 US US07/590,130 patent/US5093308A/en not_active Expired - Fee Related
- 1990-09-28 JP JP2257626A patent/JPH03126591A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE59005730D1 (de) | 1994-06-23 |
| EP0420036A1 (fr) | 1991-04-03 |
| JPH03126591A (ja) | 1991-05-29 |
| US5093308A (en) | 1992-03-03 |
| DE3932523A1 (de) | 1991-04-11 |
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