EP0439200B1 - Procédé pour le transfert des colorants méthiniques bichromophores contenant des groupes cyanos - Google Patents
Procédé pour le transfert des colorants méthiniques bichromophores contenant des groupes cyanos Download PDFInfo
- Publication number
- EP0439200B1 EP0439200B1 EP91101566A EP91101566A EP0439200B1 EP 0439200 B1 EP0439200 B1 EP 0439200B1 EP 91101566 A EP91101566 A EP 91101566A EP 91101566 A EP91101566 A EP 91101566A EP 0439200 B1 EP0439200 B1 EP 0439200B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- cyano
- sulfyl
- dyes
- und
- 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
- 239000000975 dye Substances 0.000 title claims description 49
- 238000012546 transfer Methods 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 13
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 title claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 title claims description 10
- -1 monophenylcarbamoyl Chemical group 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 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 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 3
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
- 230000021615 conjugation Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical class 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000011092 plastic-coated paper Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 description 12
- 239000000123 paper Substances 0.000 description 10
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 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
- 230000008033 biological extinction Effects 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
- 239000003960 organic solvent Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- 0 *C(C#N)=C*I*C=C(*)C#N Chemical compound *C(C#N)=C*I*C=C(*)C#N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 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
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 229920000896 Ethulose Polymers 0.000 description 2
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 2
- 241001295925 Gegenes Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000010023 transfer printing Methods 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
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WICBZRCZQKMUTR-QDEBKDIKSA-N C/C=C(\C=Cc1c2cccc1)/N2[IH]C Chemical compound C/C=C(\C=Cc1c2cccc1)/N2[IH]C WICBZRCZQKMUTR-QDEBKDIKSA-N 0.000 description 1
- WGISLSXAUNRGSH-XCVCLJGOSA-N C/C=C1/Sc(cccc2)c2N1[IH]C Chemical compound C/C=C1/Sc(cccc2)c2N1[IH]C WGISLSXAUNRGSH-XCVCLJGOSA-N 0.000 description 1
- HRDPJAUEZZZPGA-UHFFFAOYSA-N COOC(CCC1)CC1OOC Chemical compound COOC(CCC1)CC1OOC HRDPJAUEZZZPGA-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- 230000006978 adaptation Effects 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 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
- 230000005540 biological transmission 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
- 125000004744 butyloxycarbonyl group Chemical group 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
- 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
- 239000008199 coating composition Substances 0.000 description 1
- 239000003086 colorant Substances 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
- 238000004043 dyeing Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 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
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- JIQNWFBLYKVZFY-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=C[C]=CC=C1 JIQNWFBLYKVZFY-UHFFFAOYSA-N 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
- 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
- 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
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- NFBAXHOPROOJAW-UHFFFAOYSA-N phenindione Chemical class O=C1C2=CC=CC=C2C(=O)C1C1=CC=CC=C1 NFBAXHOPROOJAW-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
- 229920000728 polyester 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
- 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
- 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
- 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
- 125000004742 propyloxycarbonyl 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
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch 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
- 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
- B41M5/3854—Dyes containing one or more acyclic carbon-to-carbon double bonds, e.g., di- or tri-cyanovinyl, methine
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/913—Material designed to be responsive to temperature, light, moisture
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/914—Transfer or decalcomania
Definitions
- the present invention relates to a new method for transferring bichromophoric cyano group-containing methine dyes, which have two individual chromophores which are connected to one another via a bridge member, 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
- Suitable radicals R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl , Hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl or isooctyl.
- R 1 and R 5 are, for example, nonyl, isononyl, decyl, isodecyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-butoxyethyl, 2-or 3-methoxypropyl, 2-or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2-or 3-butoxypropyl, 4-methoxybutyl, 4-ethoxybutyl, 4-butoxybutyl, 2-cyanoethyl, 3-cyanopropyl, 4-cyanobutyl, 2-hydroxyethyl,
- R 4 radicals are furthermore, for example, phenyl, 2-, 3- or 4-methylphenyl, 2- or 4-isopropylphenyl, 2-butylphenyl, 2-, 3- or 4-methoxyphenyl, 2-propoxyphenyl, 4-butoxyphenyl, 2- ( But-2-oxy) phenyl, benzyl, 2-, 3- or 4-methylbenzyl, 2-, 3- or 4-methoxybenzyl, fluorine, chlorine, bromine, thien-2-yl or thien-3-yl.
- R 2 and R 3 are furthermore methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy, hexyloxy, formylamino, acetylamino, propionylamino, butyrylamino, methylsulfonylamino, ethylsulfonylamino-isyl-sulfonamyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sul
- Residues X are e.g. Methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, 2-methoxyethoxycarbonyl, methylcarbamoyl, ethylcarbamoyl, 2-methoxyethylcarbamoyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cycloheptyloxycarbonyl, cyclopentylcarbamoyloyl cyclohexylcarbamylloyl cyclohexylcarbamoyl cyclohexylcarbamoyl, cyclohexylcarbamoyl, cyclohexylcarbamoyl, cyclohexylcarbamoyl, cyclohexylcarbamoyl, cyclohexylcarbamoy
- Residues E 1 and E 2 are, for example, methylene, 1,2-ethylene, ethylidene, 1,2- or 1,3-propylene or 1,4-, 1,3- or 2,3-butylene.
- Residues D are, for example -O- (CH 2 ) 2 -O-, -O- (CH 2 ) 3 -O-, -O- (CH 2 ) 4 -O-, -O- (CH 2 ) 5 -O-, -O - (CH 2 ) 6 -O-, -O- (CH 2 ) 7 -O-, -O- (CH 2 ) 8 -O-, -O- (CH 2 ) 9 -O-, -O- ( CH 2 ) 10 -O-,
- bichromophoric methine dyes used in the process according to the invention are generally known and are e.g. in GB-A-1 201 925, US-A-3 553 245, DE-A-1 569 678, DE-A-2 519 592, DE-A-3 020 473, WO-A-86/04904 or WO-A-87/01121 described or can be obtained by the methods mentioned there.
- the dyes transferred in the process according to the invention are generally distinguished by improved fixation in the recording medium at room temperature, easier thermal transferability, higher lightfastness, higher stability to moisture and chemical substances, better solubility in organic solvents, higher Ribbon stability and higher color purity.
- the dyes of the formula I used in the new process are advantageously suitable for producing a trichromatic system required for the subtractive color mixture.
- the good transferability allows a large variation of the plastics used as a receiver and thus a very good adaptation of the dyes to the overall system (donor / receiver).
- the dyes are processed to a printing ink in a suitable organic solvent or in mixtures of solvents, with one or more binders, if appropriate with the addition of auxiliaries.
- a printing ink in a suitable organic solvent or in mixtures of solvents, with one or more binders, if appropriate with the addition of auxiliaries.
- the printing ink can be applied to the inert support using a doctor blade and the dyeing can be dried in air.
- Suitable organic solvents for the dyes I are, for example, those in which the solubility of the dyes I 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 are capable of binding the dye to the inert support in an abrasion-resistant manner are suitable as binders. Preference is given to binders which, after the printing ink has dried in air, absorb the dye in the form of a clear, transparent film without the dye crystallizing out visibly.
- 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, polyvinyl butyrate or polyvinyl acetate.
- the weight ratio of binder: dye is generally 1: 1 to 10: 1.
- Inert carriers are, for example, tissue paper, blotting paper or glassine paper or plastic films with good heat resistance, for example metal-coated polyester, polyamide or polyimide.
- the inert carrier is optionally additionally coated on the side facing the thermal head with a lubricating layer (slipping layer) in order to prevent the thermal head from sticking to the carrier material. 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 can be used as the dye-receiving layer, e.g. 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 dyes listed in the following tables were processed according to ⁇ ) and the resulting dye-coated supports were tested for transfer behavior according to ⁇ ).
- the tables show the thermal transfer parameters T * and ⁇ E T , the absorption maxima of the dyes ⁇ max (measured in methylene chloride), the binders used and the weight ratio of dye: binder: auxiliaries.
- the following methine dyes can be transferred in an analogous manner.
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Claims (2)
- Procédé de transfert de colorants méthiniques bichromophores entre un support et un papier revêtu de matière plastique 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 de formule IL est mis pour un maillon de pontage qui ne permet pas de conjugaison d'électrons π entre les restes Z et Y,X sont semblables ou différents et sont mis chacun pour un reste cyano, (alcoxy en C1-C6)carbonyle ou mono(alkyl en C1-C6)carbamoyle, les groupements alkyle pouvant être interrompus chacun par 1 ou 2 atomes d'oxygène, pour un reste (cycloalcoxy en C5-C7)carbonyle, mono(cycloalkyl en C5-C7)carbamoyle, phénoxycarbonyle ou monophénylcarbamoyle etZ et Y sont identiques ou différents et sont mis chacun, indépendamment l'un de l'autre, en combinaison avec le maillon de pontage L, pour un reste de formuleoùn est égal à 0 ou 1,R1 et R5 sont identiques ou différents et sont mis chacun, indépendamment l'un de l'autre, pour un reste alkyle, alcoxyalkyle, alcoxycarbonylalkyle ou alcanoyloxyalkyle, ces restes renfermant chacun jusqu'à 10 atomes de carbone et pouvant être éventuellement substitués par un groupement hydroxy ou cyano, pour un atome d'hydrogène ou pour un reste benzyle, cyclohexyle, phényle ou tolyle,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-C8, alcoxy en C1-C6, alcanoylamino en C1-C6 ou alkylsulfonylamino en C1-C6,R4 est mis pour un atome d'hydrogène, d'halogène ou pour un reste alkyle en C1-C8, phényle éventuellement substitué par un groupement alkyle en C1-C4 ou alcoxy en C1-C4, pour un reste benzyle éventuellement substitué par un groupement alkyle en C1-C4 ou alcoxy en C1-C4, pour un reste cyclohexyle, thiényle ou pour le reste -NHR1, R1 ayant la signification donnée ci-dessus, etR6 représente un atome d'hydrogène ou un reste alkyle en C1-C8.
- Procédé selon la revendication 1, caractérisé en ce que X représente un reste cyano.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4004614A DE4004614A1 (de) | 1990-02-15 | 1990-02-15 | Verfahren zur uebertragung von bichromophoren cyanogruppen enthaltenden methinfarbstoffen |
DE4004614 | 1990-02-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0439200A1 EP0439200A1 (fr) | 1991-07-31 |
EP0439200B1 true EP0439200B1 (fr) | 1996-08-14 |
Family
ID=6400164
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP91101566A Expired - Lifetime EP0439200B1 (fr) | 1990-02-15 | 1991-02-06 | Procédé pour le transfert des colorants méthiniques bichromophores contenant des groupes cyanos |
Country Status (4)
Country | Link |
---|---|
US (1) | US5139997A (fr) |
EP (1) | EP0439200B1 (fr) |
JP (1) | JPH05318938A (fr) |
DE (2) | DE4004614A1 (fr) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4105197A1 (de) * | 1991-02-20 | 1992-08-27 | Basf Ag | Bichromophore methinfarbstoffe |
PL348193A1 (en) | 1998-12-11 | 2002-05-06 | Pharmasolutions | Self-emulsifying compositions for drugs poorly soluble in water |
US6057289A (en) * | 1999-04-30 | 2000-05-02 | Pharmasolutions, Inc. | Pharmaceutical composition comprising cyclosporin in association with a carrier in a self-emulsifying drug delivery system |
DE10009580A1 (de) * | 2000-02-29 | 2001-08-30 | Bayer Ag | Verfahren zum Massefärben von Kunststoffen |
US6841514B2 (en) * | 2002-12-26 | 2005-01-11 | Eastman Kodak Company | Thermal transfer imaging element containing infrared bichromophoric colorant |
US6831163B2 (en) * | 2002-12-26 | 2004-12-14 | Eastman Kodak Company | Bichromophoric molecules |
US7288121B2 (en) * | 2004-02-27 | 2007-10-30 | L'oreal S.A. | Composition comprising at least one mixed dye comprising at least one chromophore chosen from compounds of the methine family and/or the carbonyl family, dyeing process and kit, and mixed dyes |
US7303591B2 (en) * | 2004-02-27 | 2007-12-04 | L'oreal S.A. | Composition comprising at least one mixed dye comprising at least two chromophores of (hetero) aromatic nitro or cyclic azine type, dyeing process, and mixed dyes |
FR2879927A1 (fr) * | 2004-02-27 | 2006-06-30 | Oreal | Composition comprenant un colorant mixte a base d'au moins un chromophore de type nitre (hetero) aromatique,procede de coloration et colorants mixtes. |
FR2866808A1 (fr) * | 2004-02-27 | 2005-09-02 | Oreal | Composition comprenant un colorant mixte a base d'au moins un chromophore de type nitre(herero)aromatique ou azine cyclique, procede de coloration et colorants mixtes |
FR2866803B1 (fr) * | 2004-02-27 | 2007-06-29 | Oreal | Composition comprenant un colorant mixte a base d'au moins un chromophore de type nitre (hetero) aromatique ou azine cyclique, procede de coloration et colorants mixtes |
FR2889954B1 (fr) * | 2005-08-26 | 2007-10-19 | Oreal | Colorants mixtes cationiques comprenant un chromophore anthraquinone et leur utilisation en colorant capillaire |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3846069A (en) * | 1968-07-26 | 1974-11-05 | Ciba Geigy Ag | Sublimation transfer dyeing with styryl dyes |
CH1123568A4 (de) * | 1968-07-26 | 1972-02-29 | Ciba Geigy Ag | Transferdruckverfahren auf Textilmaterialien |
US4018810A (en) * | 1972-10-25 | 1977-04-19 | Minnesota Mining And Manufacturing Company | Organic dye having fluoroaliphatic substituent |
US4748149A (en) * | 1987-02-13 | 1988-05-31 | Eastman Kodak Company | Thermal print element comprising a yellow merocyanine dye stabilized with a cyan indoaniline dye |
US4833123A (en) * | 1987-10-08 | 1989-05-23 | Sumitomo Chemical Company Limited | Yellow dye-donor element used in thermal transfer and thermal transfer and thermal transfer sheet using it |
-
1990
- 1990-02-15 DE DE4004614A patent/DE4004614A1/de not_active Withdrawn
-
1991
- 1991-02-04 US US07/650,430 patent/US5139997A/en not_active Expired - Fee Related
- 1991-02-06 EP EP91101566A patent/EP0439200B1/fr not_active Expired - Lifetime
- 1991-02-06 DE DE59108061T patent/DE59108061D1/de not_active Expired - Lifetime
- 1991-02-13 JP JP3019981A patent/JPH05318938A/ja not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
DE4004614A1 (de) | 1991-08-22 |
JPH05318938A (ja) | 1993-12-03 |
US5139997A (en) | 1992-08-18 |
EP0439200A1 (fr) | 1991-07-31 |
DE59108061D1 (de) | 1996-09-19 |
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