EP0442360B1 - Procédé de transfert de colorants azoiques - Google Patents
Procédé de transfert de colorants azoiques Download PDFInfo
- Publication number
- EP0442360B1 EP0442360B1 EP91101564A EP91101564A EP0442360B1 EP 0442360 B1 EP0442360 B1 EP 0442360B1 EP 91101564 A EP91101564 A EP 91101564A EP 91101564 A EP91101564 A EP 91101564A EP 0442360 B1 EP0442360 B1 EP 0442360B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- radical
- alkoxy
- hydrogen
- transfer
- 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
- 238000012546 transfer Methods 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 15
- 239000000987 azo dye Substances 0.000 title claims description 13
- 230000008569 process Effects 0.000 title claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000009792 diffusion process Methods 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000011092 plastic-coated paper Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000000975 dye Substances 0.000 description 35
- -1 1,3-propylene Chemical group 0.000 description 28
- 239000011230 binding agent Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000001856 Ethyl cellulose Substances 0.000 description 4
- 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 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 229920001249 ethyl cellulose Polymers 0.000 description 4
- 235000019325 ethyl cellulose Nutrition 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 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
- 230000008033 biological extinction Effects 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 238000010023 transfer printing Methods 0.000 description 3
- 229920000896 Ethulose Polymers 0.000 description 2
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose 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
- 229920001577 copolymer Polymers 0.000 description 2
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 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
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 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
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-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
- 239000005977 Ethylene Substances 0.000 description 1
- 241001295925 Gegenes Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 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
- 230000008901 benefit Effects 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
- 230000005540 biological transmission Effects 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 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
- 125000006612 decyloxy group Chemical group 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 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
- 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000001050 lubricating effect Effects 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
- 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
- 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
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920003055 poly(ester-imide) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 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
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000004926 polymethyl methacrylate 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
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 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
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 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
- 238000012360 testing method Methods 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical class NC1=CC=CS1 GLQWRXYOTXRDNH-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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
Definitions
- the present invention relates to a new process for transferring azo dyes, which have a thiophene-based diazo component, from a support to paper coated with plastic with the aid of 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, 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.
- an energy source e.g. with a heating head
- short heating impulses duration: fractions of a second
- EP-A-216 483 or EP-A-258 856 describes azo dyes which have diazo components based on thiophene and coupling components based on aniline.
- disazo dyes based on thiophene and aniline are known from EP-A-218 397 for this purpose.
- EP-A-302 628 teaches the thermal transfer of azo dyes which are derived from 2-aminothiophenes which have a condensed carbonyl group in ring position 5.
- the object of the present invention was to provide a method for transferring azo dyes, the dyes being intended to meet the above-mentioned requirements as well as possible.
- Residues Y in formula I are e.g. Ethylene, 1,2- or 1,3-propylene, 1,2-, 1,3-, 1,4- or 2,3-butylene, pentamethylene, hexamethylene or 2-methylpentamethylene.
- Suitable radicals R1, R2, R3, R4, R5 and R7 in formula I are e.g. Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
- R1 and R4 are also, for example, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl or isodecyl.
- Residues R1 are furthermore, for example undecyl, dodecyl, tridecyl, isotridecyl (the designations isooctyl, isononyl, isodecyl and isotridecyl are trivial drawings and come from the alcohols obtained after oxosynthesis - cf.
- R4 and R5 are also, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy or sec-butoxy.
- Residues R4 are still e.g. Pentyloxy, isopentyloxy, neopentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy or decyloxy.
- Residues R5 are still e.g. Methylthio, ethylthio, propylthio, isopropylthio or butylthio.
- the dyes of the formula I are known from EP-A-201 896 or can be obtained by the methods mentioned there.
- the dyes transferred in the process according to the invention are generally distinguished by improved migration properties in the recording medium at room temperature, easier thermal transferability, higher photochemical stability, easier technical accessibility, better resistance to moisture and chemical substances, higher color strength , better solubility, higher color purity and higher thermal stability.
- the dyes are in a suitable organic solvent, for example chlorobenzene, isobutanol, methyl ethyl ketone, methylene chloride, toluene, tetrahydrofuran or their mixtures, processed with one or more binders, optionally with the addition of auxiliaries, to form a printing ink.
- a suitable organic solvent for example chlorobenzene, isobutanol, methyl ethyl ketone, methylene chloride, toluene, tetrahydrofuran or their mixtures
- binders optionally with the addition of auxiliaries
- binders All resins or polymer materials which are soluble in organic solvents and are capable of binding the dye to the inert support 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 in the form of a clear, transparent film, without any visible crystallization of the dye occurring.
- binders examples include cellulose derivatives, e.g. Methyl cellulose, ethyl cellulose, ethyl hydroxyethyl cellulose, hydroxypropyl cellulose, cellulose acetate or cellulose acetobutyrate, starch, alginates, alkyd resin, vinyl resin, polyvinyl alcohol, polyvinyl acetate, polyvinyl butyrate or polyvinyl pyrrolidone.
- Polymers and copolymers of acrylates or their derivatives, such as polyacrylic acid, polymethyl methacrylate or styrene-acrylate copolymers, polyester resin, polyamide resin, polyurethane resin or natural CH resin, such as gum arabic are also suitable as binders.
- Other suitable binders are e.g. in DE-A-3 524 519.
- Preferred binders are ethyl cellulose, ethyl hydroxyethyl cellulose or polyvinyl butyrate.
- the ratio of binder to dye preferably varies between 5: 1 and 1: 1.
- auxiliaries such as those specified in EP-A-227 092, EP-A-192 435 or the patent applications cited therein, are also suitable as auxiliaries, in addition, in particular organic additives which cause the transfer dyes to crystallize out during storage and when the ink ribbon is heated prevent, e.g. Cholesterol or vanillin.
- Inert carriers are e.g. Silk, blotting or glassine paper or plastic films with good heat resistance, e.g. optionally metal-coated polyester, polyamide or polyimide.
- the inert carrier is optionally additionally coated with a lubricating layer (slipping layer) in order to prevent the thermal head from sticking to the carrier material.
- a lubricating layer slipping layer
- Suitable lubricants are described, for example, in EP-A-216 483 or EP-A-227 095.
- 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 are suitable as the dye receiver layer. modified polycarbonate or polyester.
- Suitable formulations for the receiver layer composition are e.g. in EP-A-227 094, EP-A-133 012, EP-A-133 011, EP-A-111 004, JP-A-199 997/1986, JP-A-283 595/1986, JP- A-237 694/1986 or JP-A-127 392/1986 described in detail.
- the transmission takes place by means of an energy source, e.g. by means of a laser or by means of a thermal head which must 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 ms.
- the dye migrates from the transfer sheet and diffuses into the surface coating of the recording medium.
- the polyester film (donor) containing the dye to be tested in the coating composition front side was placed with the front side on commercially available Hitachi Color Video Print Paper (recipient) and pressed.
- the encoder / receiver was then wrapped with aluminum foil and heated between two heated plates at different temperatures T (in the temperature interval 70 ° C ⁇ T ⁇ 120 ° C).
- the dyes mentioned in the following tables were processed according to A) and the resulting dye-coated carrier according to B) was tested for the transfer behavior.
- the tables show the thermal transfer parameters T * and ⁇ E T , the absorption maxima of the dyes ⁇ max (measured in methylene chloride) and the binders used.
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Claims (3)
- Procédé de transfert de colorants azoïques sur un papier revêtu de matière plastique à partir d'un support, par diffusion à l'aide d'une source d'énergie, caractérisé en ce que l'on utilise un support sur lequel se trouvent un ou plusieurs colorants azoïques de formule I
X représente un atome d'azote ou le reste C-CN,Z représente un atome d'oxygène ou le reste -CH(R⁷)-, R⁷ étant mis pour un atome d'hydrogène ou pour un groupement alkyle en C₁-C₄,R¹ représente un reste alkyle, alcanoyloxyalkyle, alcoxycarbonyloxyalkyle ou alcoxycarbonylalkyle, ces restes renfermant chacun jusqu'à 15 atomes de carbone et pouvant être substitués par des groupements phényle, (alkyl en C₁-C₄)phényle, (alcoxy en C₁-C₄)-phényle, halogénophényie, benzyloxy, (alkyl en C₁-C₄)benzyloxy, (alcoxy en C₁-C₄)benzyloxy, par un atome d'halogéne ou par un groupement hydroxy ou cyano, un atome d'hydrogène, un reste phényle éventuellement substitué par un groupement alkyle en C₁-C₁₅, alcoxy en C₁-C₁₅ ou par un atome d'halogéne, ou un reste de formule II
[-Y-O]m-R⁸ (II)
dans laquelleY est mis pour un reste alkylène en C₂-C₆,m est mis pour 1, 2, 3, 4, 5 ou 6 etR⁸ est mis pour un reste alkyle en C₁-C₄ ou pour un reste phényle eventuellement substitué par un groupement alkyle en C₁-C₄ ou alcoxy en C₁-C₄,R² et R³ sont identiques ou différents et représentent chacun, indépendamment l'un de l'autre, un atome d'hydrogène ou un reste alkyle en C₁-C₄,R⁴ représente un atome d'hydrogène, un reste alkyle en C₁-C₁₀, alcoxy en C₁-C₁₀ ou le reste -NH-COR² ou -NHSO₂R⁸, R² et R⁸ ayant chacun la signification donnée ci-dessus,R⁵ représente un atome d'hydrogène, de chlore, un reste alkyle en C₁-C₄, alcoxy en C₁-C₄, alkylthio en C₁-C₄ ou phényle éventuellement substitue par un groupement alkyle en C₁-C₄, alcoxy en C₁-C₄ ou par un atome d'halogène, etR⁶ représente un groupement cyano ou le reste -CO-OR¹, -CO-NHR¹ ou -CO-N(R¹)₂, R¹ ayant chaque fois la signification donnée ci-dessus. - Procédé selon la revendication 1, caractérisé en ce qu'il se trouve, sur le support, un ou plusieurs colorants azoïques de formule I dans laquelleR¹ représente un reste alkyle, alcanoyloxyalkyle ou alkyloxycarbonylalkyle, ces restes renfermant chacun jusqu'à 12 atomes de carbone et pouvant être substitués par des groupements hydroxy ou cyano, ou un reste de formule II
[-Y-O]m-R⁸ (II)
dans laquelleY est mis pour un reste alkylène en C₂-C₄,m est mis pour 1, 2, 3 ou 4 etR⁸ est mis pour un reste alkyle en C₁-C₄ ou pour un reste phényle éventuellement substitué par un groupement alkyle en C₁-C₄ ou alcoxy en C₁-C₄,R⁴ représente un atome d'hydrogène, un reste alkyle en C₁-C₆, alcoxy en C₁-C₆ ou le reste -NH-COR² ou -NHSO₂R⁸, R² et R⁸ ayant chacun la signification donnée dans la revendication 1,R⁵ représente un atome d'hydrogène, de chlore, un reste alkyle en C₁-C₄, alcoxy en C₁-C₄ ou phényle, etR⁶ représente un groupement cyano ou le reste -CO-OR¹, -CO-NHR¹ ou -CO-N(R¹)₂, R¹ ayant chaque fois la signification donnée ci-dessus. - Procédé selon la revendication 1, caractérisé en ce qu'il se trouve, sur le support, un ou plusieurs colorants azoïques de formule Ia
X représente un atome d'azote ou le reste C-CN,R¹ représente un reste alkyle en C₁-C₆ ou un reste de formule III
[-CH₂-CH₂-O]n-R⁸ (III)
dans laquellen est mis pour 1 ou 2 etR⁸ est mis pour un reste alkyle en C₁-C₄,R⁴ représente un atome d'hydrogène ou un reste méthyle, méthoxy ou (alcanoyl en C₂-C₅)amino etR⁶ représente un groupement cyano ou le reste -CO-OR¹, R¹ ayant la signification donnée ci-dessus.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4004600 | 1990-02-15 | ||
| DE4004600A DE4004600A1 (de) | 1990-02-15 | 1990-02-15 | Verfahren zur uebertragung von azofarbstoffen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0442360A1 EP0442360A1 (fr) | 1991-08-21 |
| EP0442360B1 true EP0442360B1 (fr) | 1995-11-22 |
Family
ID=6400157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP91101564A Expired - Lifetime EP0442360B1 (fr) | 1990-02-15 | 1991-02-06 | Procédé de transfert de colorants azoiques |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5145828A (fr) |
| EP (1) | EP0442360B1 (fr) |
| JP (1) | JPH05584A (fr) |
| DE (2) | DE4004600A1 (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0581342B1 (fr) * | 1992-07-14 | 1997-01-02 | Agfa-Gevaert N.V. | Elément donneur de colorant pour le transfert thermique de colorants par sublimation |
| ATE146135T1 (de) * | 1992-07-14 | 1996-12-15 | Agfa Gevaert Nv | Thiazolylazoanilinfarbstoffe zur anwendung in der thermischen farbstoffsublimationsübertragung |
| DE69307042T2 (de) * | 1992-07-14 | 1997-06-26 | Agfa Gevaert Nv | Farbstoffdonorelement zur Anwendung in der thermischen Farbstoffsublimationsübertragung |
| US5571765A (en) * | 1994-01-31 | 1996-11-05 | Agfa-Gevaert N.V. | Thermal dye transfer image with improved light-fastness |
| EP0665117A1 (fr) * | 1994-01-31 | 1995-08-02 | Agfa-Gevaert N.V. | Image produite par transfert thermique de colorant, ayant une stabilité à la lumière améliorée |
| GB9506117D0 (en) * | 1995-03-25 | 1995-05-10 | Ici Plc | Dye diffusion thermal transfer printing |
| JP5829648B2 (ja) | 2013-06-11 | 2015-12-09 | 株式会社中部コーポレーション | 食材カッター |
| CN109574880B (zh) * | 2017-09-29 | 2022-06-17 | 纳莹(上海)生物科技有限公司 | 一种荧光探针及其制备方法和用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8521327D0 (en) * | 1985-08-27 | 1985-10-02 | Ici Plc | Thermal transfer printing |
| DE3788072T3 (de) * | 1986-02-28 | 1997-02-20 | Ici Plc | Thermoübertragungsdruck. |
| DE3630279A1 (de) * | 1986-09-05 | 1988-03-17 | Basf Ag | Verfahren zur uebertragung von farbstoffen |
| DE3818404A1 (de) * | 1988-05-31 | 1989-12-07 | Basf Ag | Verfahren zur uebertragung von azofarbstoffen |
| GB8817220D0 (en) * | 1988-07-20 | 1988-08-24 | Ici Plc | Thermal transfer printing |
-
1990
- 1990-02-15 DE DE4004600A patent/DE4004600A1/de not_active Withdrawn
-
1991
- 1991-02-05 US US07/651,455 patent/US5145828A/en not_active Expired - Fee Related
- 1991-02-06 EP EP91101564A patent/EP0442360B1/fr not_active Expired - Lifetime
- 1991-02-06 DE DE59106925T patent/DE59106925D1/de not_active Expired - Lifetime
- 1991-02-12 JP JP3018818A patent/JPH05584A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP0442360A1 (fr) | 1991-08-21 |
| JPH05584A (ja) | 1993-01-08 |
| DE4004600A1 (de) | 1991-08-22 |
| US5145828A (en) | 1992-09-08 |
| DE59106925D1 (de) | 1996-01-04 |
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