EP0460463A1 - Utilisation de colorants azoiques pour l'impression par transfert thermique - Google Patents

Utilisation de colorants azoiques pour l'impression par transfert thermique Download PDF

Info

Publication number: EP0460463A1
Authority: EP; European Patent Office
Prior art keywords: alkyl; ethyl; azo dyes; substituents; alkoxy
Prior art date: 1990-06-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

EP91108420A

Other languages

German (de)

English (en)

Other versions

EP0460463B1 (fr

Inventor

Ruediger Sens

Helmut Reichelt

Sabine Gruettner

Karl-Heinz Etzbach

Gunther Lamm

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-06-06

Filing date

1991-05-24

Publication date

1991-12-11

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6407854&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0460463(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1991-05-24 Application filed by BASF SE filed Critical BASF SE

1991-12-11 Publication of EP0460463A1 publication Critical patent/EP0460463A1/fr

1994-12-14 Application granted granted Critical

1994-12-14 Publication of EP0460463B1 publication Critical patent/EP0460463B1/fr

2011-05-24 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000987 azo dye Substances 0.000 title claims abstract description 20
238000010023 transfer printing Methods 0.000 title claims abstract description 14
125000001424 substituent group Chemical group 0.000 claims abstract description 21
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 12
239000000460 chlorine Substances 0.000 claims abstract description 11
229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052794 bromium Inorganic materials 0.000 claims abstract description 9
230000008878 coupling Effects 0.000 claims abstract description 8
238000010168 coupling process Methods 0.000 claims abstract description 8
238000005859 coupling reaction Methods 0.000 claims abstract description 8
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims abstract description 4
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 4
ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 claims abstract description 3
125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 claims abstract 2
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
238000000034 method Methods 0.000 claims description 10
229920003023 plastic Polymers 0.000 claims description 7
239000004033 plastic Substances 0.000 claims description 7
239000000758 substrate Substances 0.000 claims description 6
230000008569 process Effects 0.000 claims description 5
238000009792 diffusion process Methods 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 6
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 6
101000623895 Bos taurus Mucin-15 Proteins 0.000 abstract 1
-1 alkyl radicals Chemical class 0.000 description 146
239000000975 dye Substances 0.000 description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
239000011230 binding agent Substances 0.000 description 9
150000002431 hydrogen Chemical class 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
125000000217 alkyl group Chemical group 0.000 description 6
239000000123 paper Substances 0.000 description 6
150000003254 radicals Chemical group 0.000 description 5
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 4
101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
239000000203 mixture Substances 0.000 description 4
125000004430 oxygen atom Chemical group O* 0.000 description 4
238000007639 printing Methods 0.000 description 4
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 3
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
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
239000012876 carrier material Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
235000019325 ethyl cellulose Nutrition 0.000 description 3
229920001249 ethyl cellulose Polymers 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
125000005916 2-methylpentyl group Chemical group 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
229920000896 Ethulose Polymers 0.000 description 2
239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000002835 absorbance Methods 0.000 description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
229920002301 cellulose acetate Polymers 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
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 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 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
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 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 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
125000005394 methallyl group Chemical group 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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 2
150000003530 tetrahydroquinolines Chemical class 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
239000001043 yellow dye Substances 0.000 description 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 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
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical compound CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
229920002125 Sokalan® Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
244000297179 Syringa vulgaris Species 0.000 description 1
235000004338 Syringa vulgaris Nutrition 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction 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
125000004423 acyloxy group Chemical group 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
125000005236 alkanoylamino group Chemical group 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
125000005195 alkyl amino carbonyloxy group Chemical group 0.000 description 1
125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
125000005281 alkyl ureido 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
150000005010 aminoquinolines Chemical class 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
230000008901 benefit Effects 0.000 description 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
125000004802 cyanophenyl group Chemical group 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
150000002148 esters Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
239000010408 film Substances 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
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
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
DZFWNZJKBJOGFQ-UHFFFAOYSA-N julolidine Chemical class C1CCC2=CC=CC3=C2N1CCC3 DZFWNZJKBJOGFQ-UHFFFAOYSA-N 0.000 description 1
230000002045 lasting 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
238000004519 manufacturing process Methods 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
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
QGNBDSPDXGLEJP-UHFFFAOYSA-N n-fluoroacetamide Chemical compound CC(=O)NF QGNBDSPDXGLEJP-UHFFFAOYSA-N 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 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
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
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
239000001044 red dye Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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

Definitions

the main heat source used is a thermal head with which short heating impulses 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 color transferred and thus the color gradation can be specifically controlled via the energy to be delivered to the thermal head.
Thermal transfer printing generally uses the three subtractive primary colors yellow, magenta and cyan, possibly also black, whereby the dyes used for optimum color recording must have the following properties: easy thermal transferability, low tendency to migrate within or from the surface coating of the recording medium at room temperature , high thermal and photochemical stability as well as resistance to moisture and chemicals, no tendency to crystallize when storing the transfer sheet, a suitable color for the subtractive color mixture, a high molar absorption coefficient and easy technical accessibility.
the azo dyes I themselves are known from the earlier German patent applications P 38 10 643.4 and P 38 16 698.4 or can be obtained by the methods mentioned there.
the invention was therefore based on the object, suitable for thermal transfer printing red and To find yellow dyes that 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.
Suitable alkyl radicals R 1 or R 2 are especially methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl.
Alkyl radicals R 1 can also be pentyl, isopentyl, neopentyl, tert-pentyl, hexyl and 2-methylpentyl.
alkoxy radicals R 2 are methoxy, ethoxy, propoxy, isopropoxy, butoxy and isobutoxy.
radical R 1 is a phenyl group bearing substituents, the following may be mentioned, for example: methyl, ethyl, methoxy, ethoxy, chlorine, bromine and cyanophenyl, the substituents of which are each in the 2, 3 or 4 position to sit.
Suitable alkyl radicals R 3, R 3 ' , R 4, R 4 ', R S , R 6 , R 7 or R 8 are especially methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert.- Butyl.
Alkyl radicals R 3 , R 3 ', R 4 , R 4 ', R 7 or R 8 are also, for example, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl and 2-ethylhexyl, R 3 , R 3 ', R 4 or R 4 ' additionally, for example, nonyl and decyl.
the C chain of the alkyl radicals R 3 , R 3 ', R 4 ' or R 4 ' is interrupted by one to three oxygen atoms
the following groups may be mentioned, for example: 2-methoxy, 2-ethoxy, 2-propoxy , 2-butoxyethyl, 2- and 3-methoxypropyl, 1-methoxyprop-2-yl, 2-ethoxypropyl, 2-propoxypropyl, 4,7-dioxaoctyl, 4,7-dioxanonyl, 4,8-dioxadecyl, 4,7, 10-trioxaundecyl and 4,7,10-trioxadodecyl.
Suitable alkoxy radicals R 5 or R 6 are, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy and isobutoxy.
Preferred azo dyes I can be found in the examples.
the dyes I to be used according to the invention are distinguished from the red and yellow dyes previously used for thermal transfer printing by the following properties: easier thermal transferability despite 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 production of the printing ink, higher color strength and easier technical accessibility.
the azo dyes show a significantly better color purity, especially in dye mixtures, and result in improved black prints.
the transfer sheets required as dye donors for the thermal transfer printing process according to the invention are prepared as follows:
the azo dyes I are dissolved in an organic solvent, e.g. Isobutanol, methyl ethyl ketone, methylene chloride, chlorobenzene, toluene, tetrahydrofuran or mixtures thereof, processed with one or more binders and possibly other auxiliaries such as release agents or crystallization inhibitors to give a printing ink which preferably contains the dyes in molecularly dispersed solution.
the printing ink is then applied to an inert support and dried.
Suitable binders for the use according to the invention of the azo dyes I are all materials which are soluble in organic solvents and are known to serve for thermal transfer printing, for example cellulose derivatives such as methyl cellulose, hydroxypropyl cellulose, cellulose acetate or cellulose acetobutyrate, especially ethyl cellulose and ethyl hydroxyethyl cellulose, starch, alginates, alkynyl alcohol and alkyd alcohol or polyvinylpyrrolidone and especially polyvinyl acetate and polyvinyl butyrate.
cellulose derivatives such as methyl cellulose, hydroxypropyl cellulose, cellulose acetate or cellulose acetobutyrate, especially ethyl cellulose and ethyl hydroxyethyl cellulose, starch, alginates, alkynyl alcohol and alkyd alcohol or polyvinylpyrrolidone and especially polyvinyl acetate and polyvinyl butyrate.
polymers and copolymers of acrylates or their derivatives such as polyacrylic acid, polymethyl methacrylate or styrene acrylate copolymers, polyester resins, polyamide resins, polyurethane resins or natural resins such as gum arabic.
binders are often recommended, e.g. those made of ethyl cellulose and polyvinyl butyrate in a weight ratio of 2: 1.
the weight ratio of binder to dye is usually 8: 1 to 1: 1, preferably 5: 1 to 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 also 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 are described in EP-A-216 483.
the thickness of the dye carrier is generally 3 to 30 microns, preferably 5 to 10 microns.
the substrate to be printed e.g. Paper
a binder that absorbs the dye during the printing process.
Polymeric materials whose glass transition temperature Tg is between 50 and 100 ° C., i.e. e.g. Polycarbonates and polyester. 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.
a thermal head which can be heated to temperatures above 300 ° C., so that the dye transfer takes place in a maximum of 15 msec.
transfer sheets were produced in a conventional manner from 8 ⁇ m thick polyester film, which was provided with an approx. 5 ⁇ m thick transfer layer made from 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 substrate to be printed consisted of paper approximately 120 ⁇ m thick, which was coated with an 8 ⁇ m thick plastic layer (Hitachi Color Video Print Paper).
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 temperature T * at which the absorbance reaches the value 2 can also be taken from the application, ie the transmitted light intensity is one hundredth of the incident light intensity.
the smaller the temperature T * the better the thermal transferability of the investigated dye.
Tables 1a to 9a list the azo dyes I tested for their thermal transfer behavior and their color.

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

EP91108420A 1990-06-06 1991-05-24 Utilisation de colorants azoiques pour l'impression par transfert thermique Expired - Lifetime EP0460463B1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4018067		1990-06-06
DE4018067A DE4018067A1 (de)	1990-06-06	1990-06-06	Verwendung von azofarbstoffen fuer den thermotransferdruck

Publications (2)

Publication Number	Publication Date
EP0460463A1 true EP0460463A1 (fr)	1991-12-11
EP0460463B1 EP0460463B1 (fr)	1994-12-14

Family

ID=6407854

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP91108420A Expired - Lifetime EP0460463B1 (fr)	1990-06-06	1991-05-24	Utilisation de colorants azoiques pour l'impression par transfert thermique

Country Status (4)

Country	Link
US (1)	US5200386A (fr)
EP (1)	EP0460463B1 (fr)
JP (1)	JPH04232093A (fr)
DE (2)	DE4018067A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5256624A (en) *	1991-04-18	1993-10-26	Basf Aktiengesellschaft	Transfer of methine dyes
WO1995028287A1 (fr) *	1994-04-18	1995-10-26	Zeneca Limited	Impression par transfert thermique a diffusion de colorants
EP0544301B1 (fr) *	1991-11-28	1997-05-14	Sony Corporation	Système de transfert par terminal, papier d'impression et ruban encreur pour le système de transfert thermique
US5693766A (en) *	1994-04-18	1997-12-02	Zeneca Limited	Dye diffusion thermal transfer printing
EP2868702A1 (fr) *	2013-10-29	2015-05-06	DyStar Colours Distribution GmbH	Colorants dispersives, leur préparation et utilisation

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9806810D0 (en) *	1998-03-31	1998-05-27	Zeneca Ltd	Compositions
JP4512053B2 (ja) *	2006-02-28	2010-07-28	富士フイルム株式会社	感熱転写方式を用いた画像形成方法
CN105820596B (zh) *	2016-04-22	2017-12-22	深圳市国华光电科技有限公司	一种四氢喹啉类染料、油墨和电润湿显示器
WO2025070630A1 (fr) *	2023-09-29	2025-04-03	富士フイルム株式会社	Composition, filtre d'absorption de lumière, filtre optique et son procédé de fabrication, dispositif d'affichage électroluminescent organique, dispositif d'affichage électroluminescent inorganique, dispositif d'affichage à cristaux liquides, et composé

Citations (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0216483A1 (fr) *	1985-08-27	1987-04-01	Zeneca Limited	Impression par transfert thermique
EP0227095A2 (fr) *	1985-12-24	1987-07-01	EASTMAN KODAK COMPANY (a New Jersey corporation)	Elément donneur de colorant magenta utilisé pour le transfert de colorant par la chaleur
EP0258856A2 (fr) *	1986-09-05	1988-03-09	BASF Aktiengesellschaft	Méthode de transfert de colorant
EP0335234A2 (fr) *	1988-03-29	1989-10-04	BASF Aktiengesellschaft	Colorants azo isothiazole
EP0344487A2 (fr) *	1988-05-17	1989-12-06	BASF Aktiengesellschaft	Colorants azoiques de la série des 5-aminoisothiazoles
EP0346729A2 (fr) *	1988-06-15	1989-12-20	BASF Aktiengesellschaft	Procédé de transfert de colorants azoiques avec un composant de couplage pyridine

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1223154A (fr) *	1983-07-25	1987-06-23	Sadanobu Kawasaki	Feuille de thermodecalcomanie
GB8504518D0 (en) *	1985-02-21	1985-03-27	Ici Plc	Thermal transfer dyesheet
US4740496A (en) *	1985-12-24	1988-04-26	Eastman Kodak Company	Release agent for thermal dye transfer
US4695286A (en) *	1985-12-24	1987-09-22	Eastman Kodak Company	High molecular weight polycarbonate receiving layer used in thermal dye transfer

1990
- 1990-06-06 DE DE4018067A patent/DE4018067A1/de not_active Withdrawn
1991
- 1991-05-24 EP EP91108420A patent/EP0460463B1/fr not_active Expired - Lifetime
- 1991-05-24 DE DE59103852T patent/DE59103852D1/de not_active Expired - Lifetime
- 1991-05-31 US US07/708,371 patent/US5200386A/en not_active Expired - Fee Related
- 1991-05-31 JP JP3128943A patent/JPH04232093A/ja not_active Withdrawn

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0216483A1 (fr) *	1985-08-27	1987-04-01	Zeneca Limited	Impression par transfert thermique
EP0227095A2 (fr) *	1985-12-24	1987-07-01	EASTMAN KODAK COMPANY (a New Jersey corporation)	Elément donneur de colorant magenta utilisé pour le transfert de colorant par la chaleur
EP0258856A2 (fr) *	1986-09-05	1988-03-09	BASF Aktiengesellschaft	Méthode de transfert de colorant
EP0335234A2 (fr) *	1988-03-29	1989-10-04	BASF Aktiengesellschaft	Colorants azo isothiazole
EP0344487A2 (fr) *	1988-05-17	1989-12-06	BASF Aktiengesellschaft	Colorants azoiques de la série des 5-aminoisothiazoles
EP0346729A2 (fr) *	1988-06-15	1989-12-20	BASF Aktiengesellschaft	Procédé de transfert de colorants azoiques avec un composant de couplage pyridine

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5256624A (en) *	1991-04-18	1993-10-26	Basf Aktiengesellschaft	Transfer of methine dyes
EP0544301B1 (fr) *	1991-11-28	1997-05-14	Sony Corporation	Système de transfert par terminal, papier d'impression et ruban encreur pour le système de transfert thermique
WO1995028287A1 (fr) *	1994-04-18	1995-10-26	Zeneca Limited	Impression par transfert thermique a diffusion de colorants
US5693766A (en) *	1994-04-18	1997-12-02	Zeneca Limited	Dye diffusion thermal transfer printing
EP2868702A1 (fr) *	2013-10-29	2015-05-06	DyStar Colours Distribution GmbH	Colorants dispersives, leur préparation et utilisation

Also Published As

Publication number	Publication date
EP0460463B1 (fr)	1994-12-14
US5200386A (en)	1993-04-06
DE59103852D1 (de)	1995-01-26
JPH04232093A (ja)	1992-08-20
DE4018067A1 (de)	1991-12-12

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Publication	Publication Date	Title
EP0416434B1 (fr)	1994-05-25	Colorants triazolopyridiniques ainsi qu'un procédé de transfert thermique de colorants méthiniques
EP0346729B1 (fr)	1993-10-20	Procédé de transfert de colorants azoiques avec un composant de couplage pyridine
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EP0490225B1 (fr)	1993-09-15	Utilisation de colorants anthraquinoniques pour l'impression par transfert thermique
EP0480278B1 (fr)	1993-09-08	Utilisation de colorants d'anthraquinones pour l'impression par transfert thermique
EP0420036B1 (fr)	1994-05-18	Utilisation de colorants azoiques pour l'impression par transfert thermique
EP0449109B1 (fr)	1995-07-12	Colorants d'indonaphtol et un procédé pour leur transfert thermique
EP0509302B1 (fr)	1997-01-29	Procédé pour le transfert de colorants méthiniques
EP0479068B1 (fr)	1997-03-05	Colorants de type quinoléine méthine et procédé pour leur transformation thermique
DE69603952T2 (de)	2000-01-05	Thermischer farbstoffdiffusionsübertragungsdruck

EP0460463A1 - Utilisation de colorants azoiques pour l'impression par transfert thermique - Google Patents

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ID=6407854

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Cited By (5)

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Citations (6)

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