CN1153189A - Dye mixtures comprising methine and anthraquinone dyes - Google Patents
Dye mixtures comprising methine and anthraquinone dyes Download PDFInfo
- Publication number
- CN1153189A CN1153189A CN 96112611 CN96112611A CN1153189A CN 1153189 A CN1153189 A CN 1153189A CN 96112611 CN96112611 CN 96112611 CN 96112611 A CN96112611 A CN 96112611A CN 1153189 A CN1153189 A CN 1153189A
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- Prior art keywords
- alkyl
- phenyl
- group
- unsubstituted
- formula
- Prior art date
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- 239000000975 dye Substances 0.000 title claims abstract description 108
- 239000000203 mixture Substances 0.000 title claims abstract description 57
- 239000001000 anthraquinone dye Substances 0.000 title claims description 11
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 title description 2
- 238000012546 transfer Methods 0.000 claims abstract description 9
- -1 Phenyl Chemical group 0.000 claims description 131
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000001033 ether group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- IYCKMNAVTMOAKD-UHFFFAOYSA-N 1,2-thiazol-3-amine Chemical group NC=1C=CSN=1 IYCKMNAVTMOAKD-UHFFFAOYSA-N 0.000 claims description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical group NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 229950003476 aminothiazole Drugs 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 2
- 238000009792 diffusion process Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 238000010023 transfer printing Methods 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000004043 dyeing Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 238000007639 printing Methods 0.000 description 8
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
- 239000000976 ink Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 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 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 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 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VQLYBLABXAHUDN-UHFFFAOYSA-N bis(4-fluorophenyl)-methyl-(1,2,4-triazol-1-ylmethyl)silane;methyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1.C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 VQLYBLABXAHUDN-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine 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
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 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
- 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 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- 125000001402 nonanoyl group Chemical group O=C([*])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 2
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 2
- 125000005447 octyloxy 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])O* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JSLZUBLGGPEVQN-DIPNUNPCSA-N (2r)-4-methyl-2-propan-2-yl-2-[2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazin-1-yl]butoxy]phenyl]-1,4-benzothiazin-3-one Chemical compound COC1=C(OC)C(OC)=CC(CCN2CCN(CCCCOC=3C(=CC=CC=3)[C@@]3(C(N(C)C4=CC=CC=C4S3)=O)C(C)C)CC2)=C1 JSLZUBLGGPEVQN-DIPNUNPCSA-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
- 125000005976 1-phenylethyloxy group Chemical group 0.000 description 1
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[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
- 125000005924 2-methylpentyloxy group Chemical group 0.000 description 1
- HPEFYFPHOBNAST-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=[C]S1 HPEFYFPHOBNAST-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005975 2-phenylethyloxy group Chemical group 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- XXIMLNDEKXVCKR-UHFFFAOYSA-N C(C)(C)OC(C(C(OOCCC(C)C)(OCCCCC)OC(C)CC)(C)C)(OCC(C)C)OCCCC Chemical compound C(C)(C)OC(C(C(OOCCC(C)C)(OCCCCC)OC(C)CC)(C)C)(OCC(C)C)OCCCC XXIMLNDEKXVCKR-UHFFFAOYSA-N 0.000 description 1
- BTKLMGGKCQZDNC-UHFFFAOYSA-N CC(C)CCCCCCC[O] Chemical compound CC(C)CCCCCCC[O] BTKLMGGKCQZDNC-UHFFFAOYSA-N 0.000 description 1
- DGFQXXDHYHWWSP-UHFFFAOYSA-N CC(C)OC([O])=O Chemical compound CC(C)OC([O])=O DGFQXXDHYHWWSP-UHFFFAOYSA-N 0.000 description 1
- WZILWDLWRDLMNN-UHFFFAOYSA-N CCCOC([O])=O Chemical compound CCCOC([O])=O WZILWDLWRDLMNN-UHFFFAOYSA-N 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 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 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- GTZOZDOTOWNSJH-UHFFFAOYSA-N [O].CCCCCCC Chemical compound [O].CCCCCCC GTZOZDOTOWNSJH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
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- 150000001408 amides Chemical class 0.000 description 1
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- 230000008901 benefit Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
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- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229950001891 iprotiazem Drugs 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 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
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- RGLRXNKKBLIBQS-XNHQSDQCSA-N leuprolide acetate Chemical compound CC(O)=O.CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 RGLRXNKKBLIBQS-XNHQSDQCSA-N 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
- GPKUICFDWYEPTK-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=CC=C=C[CH]1 GPKUICFDWYEPTK-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 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
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])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
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Thermal Transfer Or Thermal Recording In General (AREA)
Abstract
Dye mixtures comprising one or more pyridine dyes of the formula, where M is a pyridine or triazolopyridone radical which is bonded to the thiazole ring via CH and the other radicals are each as defined in the description, and one or more dyes based on 1-aminoanthraquinone are useful for thermal transfer.
Description
The present invention relates to contain the new dye mixture of anthraquinone dye of the pyridone dyes of one or more formulas I and one or more formula IIIs and the method for these thermal dye transfer,
In the formula, M is the following formula group
Or
R
1And R
2Independent separately is C
1-C
10Alkyl can be by C
1-C
4Alkoxy carbonyl, C
1-C
4Alkoxyl group carbonyl oxygen base replaces, and its alkyl chain can be by 1 Sauerstoffatom at interval in ether functionality under each situation, or is replaced by phenyl, can be by 1-4 Sauerstoffatom interval in ether functionality; C
5-C
7Cycloalkyl; C
3-C
4Alkenyl; Unsubstituted or by C
1-C
4Alkyl, C
1-C
4The phenyl that alkoxyl group, halogen or nitro replace, perhaps the nitrogen-atoms that links to each other with them constitutes five yuan or hexa-atomic saturated heterocyclyl, other heteroatoms can be arranged, R
3When M is formula II
aGroup the time be the tertiary butyl or tert-pentyl; Or when M be formula II
bOr II
cGroup the time be C
3-C
10Alkyl, C
5-C
7Cycloalkyl, unsubstituted or by C
1-C
4Alkyl, C
1-C
4Phenyl or thienyl that alkoxyl group, halogen or nitro replace, R
4Be hydrogen, C
1-C
6Alkyl or unsubstituted or by C
1-C
4Alkane, C
1-C
4The phenyl that alkoxyl group, halogen or nitro replace, R
5Be cyano group, formamyl, one or two (C
1-C
8Alkyl) formamyl, carboxyl, C
1-C
8Alkoxy carbonyl or benzimidazolyl-, R
6Be C
1-C
10Alkyl can be replaced by phenyl, phenoxy group, cyclohexyloxy or pyrazolyl, and can be by 1-4 Sauerstoffatom at interval in ether functionality; C
5-C
7Cycloalkyl; Unsubstituted or by C
1-C
4Alkyl, C
1-C
4Phenyl or formula NB that alkoxyl group, halogen or nitro replace
1B
2Group, B wherein
1And B
2Independent separately is hydrogen, C
1-C
10Alkyl, unsubstituted or by C
1-C
4Alkyl, C
1-C
4The phenyl that alkoxyl group, halogen or nitro replace, C
1-C
9Alkyloyl, C
1-C
8Alkyl sulfide acyl group, unsubstituted or by C
1-C
4Alkyl, C
1-C
4The phenyl sulfonyl that alkoxyl group, halogen or nitro replace, the pyridyl sulfonyl, unsubstituted or by C
1-C
4Alkyl, C
1-C
4Benzoyl, pyridyl carbonyl or thienyl carbonyl that alkoxyl group, halogen or nitro replace, and in A or the E group one is nitrogen, and another is formula C-R
7Group, wherein R
7Be C
1-C
10Alkyl, can by phenyl, phenoxy group, encircle the oxygen base or pyrazolyl replaces and can be in ether functionality by 1-4 Sauerstoffatom interval); C
5-C
7Cycloalkyl or unsubstituted or by C
1-C
4Alkyl, C
1-C
4The phenyl that alkoxyl group, halogen or nitro replace,
L in the formula
1Be hydrogen, C
1-C
10Alkyl or unsubstituted or by C
1-C
4Alkyl, C
1-C
4The phenyl that alkoxyl group, halogen or nitro replace, L
2And L
3Be hydrogen independently of one another, unsubstituted or by phenyl or C
1-C
4The C that alkyl phenyl replaces
1-C
10Alkoxyl group, C unsubstituted or that replaced by phenyl
1-C
10Alkylthio, halogen, hydroxyphenyl, C
1-C
4The group of alkoxyl phenyl or following formula,
In the formula, G
1Be oxygen or sulphur, G
2Be hydrogen or C
1-C
8The monoalkyl sulfamyl, its alkyl chain can be by 1 or 2 Sauerstoffatoms at interval in ether functionality, and L
4Be amino, hydroxyl or C unsubstituted or that replaced by phenyl
1-C
10Alkylthio.
In the hot transfer printing method of printing and dyeing, be included in one or more tackiness agents can hot transfer printing the transfer printing thin plate energy of dyestuff (on carrier, suitable auxiliary can be arranged), the of short duration heating from the back side as heating head or laser (time: part second) makes dyestuff move and be diffused into the top coat of receiver media from the transfer printing thin plate.The major advantage of this method is to want the dye quantity (so gradation) of transfer printing to be easy to control by the energy of control energy emission.
Usually, the subtractive primaries with yellow, magenta and cyan (being with or without black) carries out the color record.
With homogencous dyes or to carry out the hot transfer printing method of printing and dyeing with dye mixture be known.But, have been found that used dyestuff usually still has some applied defects.
An object of the present invention is to provide in red color area, particularly at the new dye mixture in magenta district, these dye mixtures help hot transfer printing.
We have found that this purpose can reach with previously defined dye mixture.
That any alkyl that occurs in above-mentioned formula and alkenyl can be straight chain or side chain.
In any substituted alkyl that occurs in above-mentioned formula, substituent number is generally 1 or 2.
In the phenyl of any replacement that occurs in above-mentioned formula, pyridyl or the thienyl, substituent number is generally 1-3, preferred 1 or 2.
Here some groups have been enumerated for example.The listed group that also comprises among the following formula 1V.
B
1, B
2, L
1, R
1, R
2, R
4, R
6, R
7, W, Y
1, Y
2, Y
4, Y
5, Y
6, Y
7, Y
8, Z
2, Z
3, Z
4And Z
5For example all be methyl or ethyl.
R
3And Y
3And B
1, B
2, L
1, R
1, R
2, R
4, R
6, R
7, Y
1, Y
2, Y
4, Y
5, Y
6, Y
7, Y
8, Z
2, Z
3, Z
4And Z
5All be propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl, the tertiary butyl, amyl group, isopentyl, neo-pentyl, tert-pentyl, base or 2-methyl amyl.
B
1, B
2, L
1, R
1, R
2, R
4, R
6, R
7, W, Y
1, Y
2, Y
3, Y
4, Y
5, Y
6, Y
7And Y
8(iso-octyl, different nonyl and the name of hot decyl derive from being commonly called as of oxo alcohol method-referring to Ullmann ' s Encyclopedia of IndustrialChemistry for example also to can be heptyl, octyl group, 2-ethylhexyl, iso-octyl, nonyl, different nonyl, decyl or isodecyl, 5th Edition, Vol.A1, pages 290 to 293, and Vol. A10, pages284 and 285).
R
1, R
2, R
3, R
6, R
7, Y
1, Y
2, Y
3, Y
6And Y
7For example also can be cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl or suberyl.
R
1, R
2, R
6, R
7, W, Y
1, Y
2, Y
4, Y
6, Y
7And Y
8For example also can be the 2-methoxy ethyl, the 2-ethoxyethyl group, 2-propoxy-ethyl, 2-isopropoxy ethyl, the 2-butoxyethyl group, 2-or 3-methoxy-propyl, 2-or 3-ethoxycarbonyl propyl, 2-or 3-propoxy-propyl group, 2-or 3-butoxy propyl group, 2-or 4-methoxyl group butyl, 2-or 4-oxyethyl group butyl, 2-or 4-propoxy-butyl, 2-or 4-butoxy butyl, 3, the 6-dioxaheptyl, 3,6-two oxa-octyl groups, 4,8-two oxa-nonyls, 3,7-two oxa-octyl groups, 3,7-two oxa-nonyls, 4,7-two oxa-octyl groups, 4,7-two oxa-nonyls, 4,8-two oxa-decyls, 3,6,8-trioxa decyl, 3,6,9-trioxa undecyl, 3,6,9,12-four oxa-tridecyls or 3,6,9,12-four oxa-tetradecyls.
R
1, R
2, Y
1, Y
2, Y
6And Y
7For example also can be 2-methoxyl group carbonyl ethyl, 2-oxyethyl group carbonyl ethyl, 2-propoxy-carbonyl ethyl, 2-isopropoxy carbonyl ethyl, 2-butoxy carbonyl ethyl, 2-or 3-methoxyl group carbonyl propyl group, 2-or 3-oxyethyl group carbonyl propyl group, 2-or 3-propoxy-carbonyl propyl group, 2-or 3-butoxy carbonyl propyl group, 2-or 4-methoxyl group carbonyl butyl, 2-or 4-oxyethyl group carbonyl butyl, 2-or 4-propoxy-carbonyl butyl, 2-or 4-butoxy carbonyl butyl, 2-methoxyl group carbonyl oxygen base ethyl, 2-oxyethyl group carbonyl oxygen base ethyl, 2-propoxy-carbonyl oxygen base ethyl, 2-isopropoxy carbonyl oxy ethyl, 2-butoxy carbonyl oxy ethyl, 2-or 3-methoxyl group carbonyl oxygen base propyl group, 2-or 3-oxyethyl group carbonyl oxygen base propyl group, 2-or 3-propoxy-carbonyl oxygen base propyl group, 2-or 3-butoxy carbonyl oxy propyl group, 2-or 4-methoxyl group carbonyl oxygen Ji Dingji, 2-or 4-oxyethyl group carbonyl oxygen Ji Dingji, 2-or 4-propoxy-carbonyl oxygen Ji Dingji, 2-or 4-butoxy carbonyl oxy butyl, third-1-alkene-3-base, but-2-ene-4-base or 2-methyl-prop-1-alkene-3-base.
R
6And R
7For example also can be 2-benzyloxy ethyl, 2-(pyrazol-1-yl) ethyl, 2-or 3-benzyloxy propyl group, 2-or 3-(pyrazol-1-yl) propyl group, 2-or 4-benzyloxy butyl, 2-or 4-(pyrazol-1-yl) butyl, 2-phenoxy group ethyl, 2-or 3-phenoxy propyl, 2-or 4-phenoxy group butyl, 2-cyclohexyloxy ethyl, 2-or 3-cyclohexyloxy propyl group or 2-or 4-cyclohexyloxy butyl.
R
1And R
2For example also can be base, 2-acetoxyl group ethyl, 2-or 3-acetoxyl group propyl group, 2-or 4-acetoxyl group butyl, 2-propionyloxy ethyl, 2-or 3-propionyloxy propyl group or 2-or 4-propionyloxy butyl under 2-cyano ethyl, 2-or 3-cyano group propyl group, 2-or 4-cyano group butyl, 2-hydroxyethyl, 2-or 3-hydroxypropyl, 2-or 4-hydroxybutyl, 2-chloroethyl, 2-or 3-chloropropyl, 2-or the 4-chlorine.
R
1, R
2, R
6, R
7, Y
1, Y
2, Y
6, Y
7And Z
2For example also can be benzyl or 1-or 2-phenylethyl.
B
1, B
2, L
1, R
1, R
2, R
3, R
4, R
6, R
7, Y
1, Y
2, Y
3, Y
6, Y
7And Z
2For example also can be phenyl, 2-, 3-or 4-aminomethyl phenyl, 2-, 3-or 4-ethylphenyl, 2-, 3-or 4-propyl group phenyl, 2-, 3-or 4-isopropyl phenyl, 2-, 3-or 4-butyl phenyl, 2,3-, 2,4-or 2,6-3,5-dimethylphenyl, 2-, 3-or 4-p-methoxy-phenyl, 2-, 3-or 4-ethoxyl phenenyl, 2,3-, 2,4-or 2,6-Dimethoxyphenyl, 2-, 3-or 4-fluorophenyl, 2-, 3-or 4-chloro-phenyl-, 2-, 3-or 4-bromophenyl or 2-, 3-or 4-nitrophenyl.
R
5For example be one or formyl-dimethylamino, one or diethylamino formyl radical, one or dipropyl formamyl, one or diisopropylaminoethyl formyl radical, one or dibutylamino formyl radical, one or diamyl formamyl, one or dihexyl formamyl, one or diheptyl formamyl, one or dioctyl formamyl, one or two (2-ethylhexyl) formamyl or N-methyl-N-ethylamino formyl radical.
L
2, L
3, L
4And Z
2For example also can be methylthio group, ethylmercapto group, rosickyite base, iprotiazem base, butylthio, isobutyl sulfenyl, penta sulfenyl, own sulfenyl, heptan sulfenyl, hot sulfenyl, different hot sulfenyl, the own sulfenyl of 2-ethyl, ninth of the ten Heavenly Stems sulfenyl, different ninth of the ten Heavenly Stems sulfenyl, last of the ten Heavenly stems sulfenyl, isodecyl sulfenyl, benzylthio-or 1-or 2-phenyl ethylmercapto group.
L
2, L
3, Y
4, Y
5, Z
2, Z
3, Z
4And Z
5For example also can be methoxyl group, oxyethyl group, propoxy-, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyl oxygen, uncle's pentyloxy, hexyloxy or 2-methyl pentyloxy.
L
2, L
3And Z
2For example also can be oxygen base in heptan, octyloxy, different octyloxy, 2-ethyl hexyl oxy, ninth of the ten Heavenly Stems oxygen base, different ninth of the ten Heavenly Stems oxygen base, last of the ten Heavenly stems oxygen base or isodecyl oxygen base.
L
2, L
3And Z
2For example also can be benzyloxy or 1-or 2-phenyl ethoxy.
L
2And L
3For example also can be 2-, 3-or 4-hydroxy phenyl, 2-, 3-or 4-p-methoxy-phenyl, 2-, 3-or 4-ethoxyl phenenyl, 2-, 3-or 4-propoxy-phenyl, 2-, 3-or 4-isopropyl phenyl or 2-, 3-or 4-butoxy phenyl.
Z
2And L
2, L
3, Z
3, Z
4And Z
5For example be fluorine, chlorine or bromine.
B
1, B
2, Z
3, Z
4And Z
5For example also can be methylsulfonyl group, ethyl sulfonyl, propylthio acyl group, sec.-propyl sulfonyl, butyl sulfonyl, isobutyl-sulfonyl, sec-butyl sulfonyl, amyl group sulfonyl, isopentyl sulfonyl, neo-pentyl sulfonyl, hexyl sulfonyl, heptyl sulfonyl, octyl group sulfonyl, 2-ethylhexyl sulfonyl, phenyl sulfonyl, 2-aminomethyl phenyl sulfonyl, 2-p-methoxy-phenyl sulfonyl or 2-chloro-phenyl-sulfonyl.
R
5, Z
3, Z
4And Z
5For example also can be methoxycarbonyl, ethoxy carbonyl, propoxycarbonyl, isopropoxy carbonyl, butoxy carbonyl, isobutoxy carbonyl, sec-butoxy carbonyl, pentyloxy carbonyl, isopentyloxy carbonyl, sec-butoxy carbonyl, pentyloxy carbonyl, isopentyloxy carbonyl, neopentyl oxygen carbonyl, hexyloxy carbonyl, heptan oxygen base carbonyl, carbonyl octyloxy, different carbonyl octyloxy or 2-ethyl hexyl oxy carbonyl.
Z
3, Z
4And Z
5For example also can be 2-phenoxy group ethoxy carbonyl, 2-or 3-phenoxy group propoxycarbonyl or 2-or 4-phenoxy group butoxy carbonyl.
Z
2For example also can be 2-or 3 methyl thiophene base or 2-, 3-or 4-picolyl.
B
1, B
2And Z
1For example also can be formyl radical, ethanoyl, propionyl, butyryl radicals, pentanoyl or caproyl.
B
1And B
2Also can be oenanthyl, capryloyl, 2-ethyl hexanoyl base, different capryloyl, nonanoyl, different nonanoyl, benzoyl, 2-, 3-or 4-methyl benzoyl or 2-, 3-or 4-anisoyl.
Y
4For example also can be acetylamino; propionyl amino; the methoxyl group acetylamino; benzoyl-amido; methoxycarbonyl amino; ethoxy carbonyl amino; methylsulfonyl group amino; ethyl sulfonyl amino; the propylthio acyl amino; sec.-propyl sulfonyl amino; butyl sulfonyl amino; one or dimethylamino sulfonyl amino; one or diethylamino sulfonyl amino; one or the amino sulfonyl amino of dipropyl; one or diisopropylaminoethyl sulfonyl amino; one or the dibutylamino sulfonyl is amino or (N-methyl-N-ethylamino sulfonyl) amino.
G
2It for example is the methyl sulfamyl; the ethyl sulfamyl; the propyl group sulfamyl; the sec.-propyl sulfamyl; the butyl sulfamyl; the amyl group sulfamyl; the hexyl sulfamyl; the heptyl sulfamyl; the octyl group sulfamyl; 2-ethyl sulfamyl; 2-methoxy ethyl sulfamyl; 2-oxyethyl group base sulfamyl; 3; 6-dioxaheptyl sulfamyl; 3; 6-two oxa-octyl group sulfamyl; 4; 8-two oxa-nonyl alkylsulfonyls; 3; 7-two oxa-octyl group sulfamyl; 3; 7-two oxa-nonyl alkylsulfonyls; 4; 7-two oxa-octyl group sulfamyl; 4; 7-two oxa-nonyl amino-sulfonyls or 4,8-two oxa-decyl amino-sulfonyls.
R
1And R
2, Y
1And Y
2Or Y
6And Y
7Can constitute five yuan or hexa-atomic saturated heterocyclic group (also other heteroatoms can be arranged) with the nitrogen-atoms that they link to each other, for example pyrrolidyl, piperidyl, morpholinyl, the assorted morpholinyl of sulfo-, thio-morpholinyl-S, S-dioxide, piperazinyl or N-(C
1-C
4Alkyl) piperazinyl such as N-methyl-or N-ethyl-piperazinyl.
R in formula I
1And R
2All be C
1-C
10Alkyl or work as R
1And R
2In one be C
1-C
10Alkyl, and another is C
5-C
7During cycloalkyl, preferred such pyridone dyes in dye mixture is wherein at R
1And R
2The sum of the carbon atom that exists in the base is at least 7, preferably is at least 8.
M in formula I is formula II
bOr II
cGroup the time, preferred such pyridone dyes in dye mixture, wherein E is a nitrogen, A is formula C-R
7Group, R wherein
7As above definition.
Also preferred such dye mixture, they contain the pyridone dyes of one or more formulas I, and wherein M is formula II
aOr II
cGroup.
Also preferred such dye mixture, they contain the pyridone dyes of one or more formulas I, wherein R
4Be methyl.
Also preferred such dye mixture, they contain the pyridone dyes of one or more formulas I, wherein R
5Be cyano group.
Also preferred such dye mixture, they contain the pyridone dyes of one or more formulas I, wherein R
3Be C
3-C
10Alkyl, preferred side chain C
3-C
10Alkyl, particularly C
3-C
8Alkyl), phenyl or thienyl.
Also preferred such dye mixture, they contain-kind or the pyridone dyes of multiple formula I, wherein R
6Be C
1-C
8Alkyl, cyclopentyl, cyclohexyl or unsubstituted or C
1-C
4Alkyl or by C
1-C
4The phenyl that alkoxyl group replaces.
Also preferred such dye mixture, they contain the pyridone dyes of one or more formulas I, wherein R
7Be C
1-C
10Alkyl or unsubstituted or by C
1-C
4Alkyl or C
1-C
4The phenyl that alkoxyl group replaces.
Also preferred such dye mixture, they contain the pyridone dyes of one or more formulas I, wherein R
1And R
2Independent separately is C
1-C
8Alkyl (can be by C
1-C
4Alkoxyl group, C
1-C
4Alkoxy carbonyl or phenyl replace), cyclopentyl, cyclohexyl or third-1-alkene-3-base.
Preferred especially such dye mixture, they contain the pyridone dyes of one or more formulas I, wherein R
3C for side chain
3-C
6Alkyl, particularly sec.-propyl, isobutyl-or the tertiary butyl.The tertiary butyl is particularly suitable.
Preferred especially such dye mixture, they contain the pyridone dyes of one or more formulas I, wherein R
6Be C
4-C
8Alkyl or cyclohexyl.
Also preferred especially such dye mixture, they contain the pyridone dyes of one or more formulas I, wherein R
7Be C
1-C
10Alkyl.
Also preferred especially such dye mixture, they contain the pyridone dyes of one or more formulas I, wherein R
1And R
2Be C
1-C
8Alkyl, C
1-C
4Alkoxy-C
2-C
4Alkyl, C
1-C
4Alkoxyl group-carbonyl-C
2-C
4Alkyl, benzyl or third-1-alkene-3-base or R
1And R
2In one be C
1-C
4Alkyl, and another is a cyclohexyl.
Most preferably such dye mixture, they contain the pyridone dyes of one or more formulas I, wherein R
1And R
2Independent separately is C
1-C
8Alkyl, benzyl or third-1-alkene-3-base.
Also preferred such dye mixture, they contain the anthraquinone dye of one or more formula IIIs, wherein L
1Be hydrogen, L
4Be hydroxyl, and L
2And L
3Define the same.
Also preferred such dye mixture, they contain the anthraquinone dye of one or more formula IIIs, wherein L
2And/or L
3Group for following formula
In the formula, G
1And G
2Define the same.
Also preferred especially such dye mixture, they contain one or more formula IIIs
aAnthraquinone dye
In the formula, G
1And G
2Define the same.
Also preferred such dye mixture, they also contain one or more azoic dyestuffs except that the anthraquinone dye of the pyridone dyes of formula I and formula III, and its azo component is selected from aminoisothiazoles and aniline; And its coupling component is selected from aminothiazole, aniline and tetrahydroquinoline.
Particularly suitable is the azoic dyestuff of formula IV
D-N=N-K (IV), in the formula, D is the group of following formula
In the formula, Z
1Be hydrogen, cyano group, C
1-C
8Alkoxy carbonyl, C
1-C
6Alkyloyl, thiocyano, halogen or nitro, Z
2Be cyano group, the C that unsubstituted or phenyl replaces
1-C
6Alkyl, the C that unsubstituted or phenyl replaces
1-C
10Alkoxyl group, the C that unsubstituted or phenyl replaces
1-C
10Alkylthio, unsubstituted or by C
1-C
4Alkyl, C
1-C
4The phenyl that alkoxyl group, halogen or nitro replace, thienyl, C
1-C
4The alkylthrophene base, pyridyl or C
1-C
4Alkylpyridyl, and Z
3, Z
4And Z
5Independent separately is hydrogen, C
1-C
6Alkyl, C
1-C
6Alkoxyl group, halogen, nitro, cyano group, the C that unsubstituted or phenoxy group replaces
1-C
8Alkoxy carbonyl, C
1-C
8Alkyl sulfide acyl group or unsubstituted or by C
1-C
4Alkyl, C
1-C
4The phenyl sulfonyl that alkoxyl group, halogen or nitro replace, perhaps Z
3And Z
4The group of constitutional formula CO-NW-CO together, wherein W is C
1-C
10Alkyl (in ether functionality, can and can be replaced) by 1 or 2 Sauerstoffatom interval by hydroxyl, and K is the group of following formula
In the formula,
Y
1And Y
2Independent separately is C
1-C
10Alkyl can be by cyano group, hydroxyl, halogen, C
1-C
4Alkanoyloxy, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkoxyl group carbonyl oxygen base replaces, and in ether functionality, its alkyl chain can be by a Sauerstoffatom at interval under each situation, or be substituted in by phenyl can be by 1-4 Sauerstoffatom interval in the ether functionality; C
5-C
7Cycloalkyl; C
3-C
4Alkenyl; Unsubstituted or by C
1-C
4Alkyl, C
1-C
4The phenyl that alkoxyl group, halogen or nitro replace; Perhaps the nitrogen-atoms that links to each other with them constitutes five yuan or hexa-atomic saturated heterocyclyl (other heteroatoms can be arranged).
Y
3Be C
3-C
10Alkyl, C
5-C
7Cycloalkyl, unsubstituted or by C
1-C
4Alkyl, C
1-C
4Phenyl or thienyl that alkoxyl group, halogen or nitro replace.
Y
4Be hydrogen; C
1-C
10Alkyl can be by 1-4 Sauerstoffatom at interval in ether functionality; Hydroxyl; C
1-C
6Alkoxyl group (particularly methoxy or ethoxy); C
1-C
4The alkyl sulfide acyl amino; One or two (C
1-C
8Alkyl) sulfonyl amino or-NHCOY
8Or-NHCO
2Y
8Group, Y wherein
8Be phenyl, benzyl, tolyl or C
1-C
10Alkyl (in ether functionality can at interval) by 1-4 Sauerstoffatom,
Y
5Be hydrogen, C
1-C
6Alkyl or C
1-C
6Alkoxyl group, and
Y
6And Y
7Independent separately is hydrogen; C
1-C
10Alkyl (can be by cyano group, hydroxyl, halogen, C
1-C
4Alkanoyloxy, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkoxyl group carbonyl oxygen base replaces, and its alkyl chain all can be by-individual Sauerstoffatom at interval in ether functionality under each situation, and perhaps being substituted in the ether functionality by phenyl can be by 1-4 Sauerstoffatom interval), C
5-C
7Cycloalkyl; C
3-C
4Alkenyl; Unsubstituted or by C
1-C
4Alkyl, C
1-C
4The phenyl that alkoxyl group, halogen or nitre replace; Perhaps the nitrogen-atoms that links to each other with them constitutes five yuan or hexa-atomic saturated heterocyclyl (other heteroatoms can be arranged).
Particularly preferably be in the azoic dyestuff of formula IV, wherein
Z
1Be cyano group or nitro,
Z
2Be C unsubstituted or that phenyl replaces
1-C
6Alkyl, the C that unsubstituted or phenyl replaces
1-C
6Alkylthio or unsubstituted or C
1-C
4Alkyl, C
1-C
4Phenyl or thienyl that alkoxyl group, halogen or nitro replace,
Z
3, Z
4And Z
5Independent separately is hydrogen, C
1-C
6Alkyl, C
1-C
6Alkoxyl group, nitro, cyano group or C unsubstituted or that phenoxy group replaces
1-C
6Alkoxy carbonyl, perhaps Z
3And Z
4Be the group of formula CO-NW-CO together, wherein the W definition is the same.Y
1, Y
2, Y
6And Y
7Independent separately is C
1-C
6Alkyl (can be by hydroxyl, C
1-C
4Alkanoyloxy, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkoxyl group carbonyl oxygen base or phenyl replace and can be by 1 or 2 Sauerstoffatoms at interval in ether functionality), Y
3C for side chain
3-C
10Alkyl, and Y
4Be hydrogen, C
1-C
4Alkyl, methoxyl group, oxyethyl group or C
1-C
6Alkanoylamino.
In addition, preferred such dye mixture, wherein various in the single substituting group of setting up branch jointly be selected from the combination of above-mentioned listed preferred substituents.
Dye mixture of the present invention is by the weight of dye mixture, usually contain 5-95% (weight) (preferred 20-80% (weight), preferred especially 40-60% (weight)) anthraquinone dye of one or more formula IIIs of the pyridone dyes of one or more formulas I and 5-95% (weight) (preferred 20-80% (weight), preferred especially 40-60% (weight)).
By the weight of pyridone dyes and anthraquinone dye, dye mixture also contains 40-60% (weight) azoic dyestuff usually.
The new dye mixture can make with traditional method, for example each homogencous dyes is pressed above-mentioned weight ratio blending.
The pyridone dyes of formula I itself is known, for example US-A-5079365, WO-A-95/17470, WO-A-95/22581 or before Europe patent application No.96 101637.5 in disclosed, the perhaps available method of being mentioned here makes.Open among for example former patent application EP-A-680834 of the hot transfer printing of these dyestuffs.
The anthraquinone dye of formula III itself also is known, for example at K.Venkataraman " TheChemistry of Synthetic Dyes ", and Vol.111, pages 391 to 413, AcademicPress, New York, London, 1970 describe.
The azoic dyestuff of formula IV itself also is known, and is open among for example former patent application WO-A-9603462.These have, and disclosed method makes among the also available method of mentioning here of azoic dyestuff of aniline series coupling component or the US-A-5283326.
Dye mixture of the present invention has fabulous application performance.They have high solvability (good intermiscibility being arranged with tackiness agent) in ink-stick, high stability is arranged in printing and dyeing, good transfer printing, high image stabilization (be good light fastness and to the good stability of environmental activity (as steam, temperature or chemical)) and guarantee other subtractive primariess color-match is flexibly produced the high quality colour gamut.In addition, dye mixture of the present invention makes the good black dyes of generation become possibility.
What pay special attention to is that single component spectra evenly loses lustre when irradiation, just, has the single dyestuff of low light fastness preferentially not lose lustre usually.
The present invention also provides a kind of makes dyestuff be transferred to method on the paper that is coated with plastics from transfer device by the method for the energy by diffusion or distillation, and this method comprises the transfer device that uses the dye mixture that contains above-detailed.
In order to make the required transfer plate of the inventive method, dye mixture is added in the suitable organic solvent or solvent mixture, form the seal China ink, one or more tackiness agents are arranged in the solvent, also various auxiliarys can be arranged.This seal China ink preferably contains the dyestuff of molecular dispersion, promptly dissolves the dyestuff of form.Available scraper plate will print China ink and be coated on the inert support, and use dry air.Mixing the organic solvent that is fit to for this dyestuff for example is such solvent, greater than 1% (weight), is preferably greater than 5% (weight) in the solubleness of 20 ℃ of following dye mixtures in this solvent.
The example of solvent is ethanol, propyl alcohol, isopropylcarbinol, tetrahydrofuran (THF), methylene dichloride, methylethylketone, cyclopentanone, pimelinketone, toluene, chlorobenzene or its mixture.
The tackiness agent that is fit to comprises resin or the polymkeric substance that all are such, and they are soluble in organic solvent, and they can fall enough firm being adhered on the inert support of dye mixture to prevent stranding.Preferred such tackiness agent, after the black dry air of seal, this tackiness agent is contained in the clean transparent film dye mixture, and without any the crystallization of visible dye mixture.
Such tackiness agent is for example mentioned in the relevant patent application that draw US-A-5132438 or it.The saturated straight chain polyester also is fit to.
Preferred adhesive comprises ethyl cellulose, ethyl hydroxylated cellulose, polyvinyl butyrate, polyvinyl acetate, cellulose propionate or saturated straight chain polyester.
Tackiness agent: the weight ratio of dye mixture is generally 1: 1 to 10: 1.
The auxiliary that is fit to for example comprises releasing agent, as what mention in the US-A-5132438 and the relevant patent application of being drawn thereof.Can prevent in storage process or organic additive that the crystallization of ink-stick when heating dye transfer is separated out also is particularly suitable, as cholesterol or Vanillin.
The inert support that is fit to is for example disclosed in the relevant patent application that US-A-5132438 or its drew.The thickness of carrier is generally 3-30 μ m, preferred 5-10 μ m.
The dyestuff receiving layer that is fit to comprises that in principle all have the heat-stabilised poly compound layer of affinity, for example polycarbonate of modification or polyester to the dyestuff of wanting transfer printing.More detailed content for example can find in the relevant patent application that US-A-5132438 or its drew.
Carry out transfer printing with the energy, for example with laser or heating head, for this reason, heating head must be able to be heated to 〉=and 300 ℃, can in time range t:0＜t＜15ms, take place with the transfer printing that causes dyestuff.Dye migration goes out the transfer printing thin plate, and is diffused on the top coat of receiver media.
Dye mixture of the present invention is also very suitable to dye synthetic materials or printing and dyeing (comprising ink jet method), as polyester, polymeric amide or polycarbonate.Particularly suitable is textile material, as fiber, yarn, line, knitted fabrics, yarn fabric or the nonwoven fabric of being made up of polyester, modified poly ester (as anion-modified polyester) or polyester and Mierocrystalline cellulose, cotton, viscose fiber or woolen union yarn.Dyestuff and printing and dyeing condition itself are known, as have been included in the dyeing in the critical carbon dioxide.Dyestuff of the present invention also can be used for dyeing keratinous fibres, as dyeing hair or dye fur.
The new dye mixture also can be used for making the colour filter that is described among the EP-A-399473 for example preferably.
At last, they also can be used as tinting material, are used to produce the toning agent of photoelectric photometer.
Following embodiment is used for illustrating the present invention.
Following table 1-4 lists each the single dyestuff as blending compound.
Table 1
| Dyestuff | ???????NR 1R 2 | ????R 3 | ??????R 6 |
| ????1 | N(C 4H 9) 2 | C(CH 3) 3 | CH 3 |
| ????2 | N(C 4H 9) 2 | C(CH 3) 3 | C 4H 9 |
| ????3 | N(C 4H 9) 2 | C(CH 3) 3 | C 2H 4OCH 3 |
| ????4 | N(C 4H 9) 2 | C(CH 3) 3 | C 3H 6OCH 3 |
| ????5 | N[CH(CH 3)C 2H 5] 2 | C(CH 3) 3 | CH 3 |
| ????6 | N[CH(CH 3)C 2H 5] 2 | C(CH 3) 3 | C 4H 9 |
| ????7 | N(C 2H 5) 2 | C(CH 3) 3 | CH(CH 3)C 2H 5 |
| ????8 | N(C 2H 5) 2 | C(CH 3) 3 | CH 3 |
Table 2
Table 3
| Dyestuff | ???G 1 | ???????G 2 | ????L 3 |
| ????11 | ???O | SO 2NHC 3H 6OC 2H 5 | ????H |
| ????12 | ???O | ???????H | ????H |
| ????13 | ???S | SO 2NHC 3H 6OC 2H 5 | ????H |
| ????14 | ???O | ???????H | ???OC 6H 5 |
Table 4
D-N＝N-K
Hot transfer step
A) 10g dye mixture (then of short duration if desired the 80-90 of being heated to ℃) is dug mix in the solution of tackiness agent of 1 00g 10% (weight) polyethylene butyraldehyde for the basis, its methylethylketone/toluene/pimelinketone volume ratio is 4.5: 2: 2.
With 10 μ m scraper plates mixture is painted the thick polyester film of 6 μ m, it has suitable smooth layer overleaf, dries up 1min with blower.Before ink-stick can be printed and dyed, it is dry air 24h at least also, because residual solvent can damage dyeing process.
B) on the industrial color printing paper of on the laboratory computer operating device that industry heating printing head is housed ink-stick being printed and dyed (Hita-chi).
Change voltage and control the energy that the heating printing head is launched, chong channel length is decided to be 7ms, only launches a pulse at every turn.The energy of emission is 0.5-2.0mJ/dot.
Because color depth directly is proportional to the energy that is applied, it is possible producing the tonal wedge (color wedge) that is used for spectral assessment.
The energy mapping that color depth applies each heating unit is to determine Q
*Value (being the energy mJ of 1l absorption value) and gradient m (l/mJ).
Result who obtains and λ
MaxValue (measuring on colour seal paper) is listed following table 5 together in.
Table 5
| Dye mixture | Weight ratio | ???λ max????[nm] | ?????Q *??[mJ/dot] | ??????m *????[l/mJ] |
| ????1/11 | ??????3∶1 | ????536 | ????0.80 | ????3.04 |
| ????1/11 | ??????2∶1 | ????536 | ????0.81 | ????2.96 |
| ????1/11 | ??????1∶1 | ????536 | ????0.87 | ????2.53 |
| ???1/11/13 | ?????1∶1∶1 | ????537 | ????0.98 | ????2.18 |
| ????2/11 | ??????3∶1 | ????537 | ????0.91 | ????2.46 |
| ????2/11 | ??????2∶1 | ????537 | ????0.86 | ????2.91 |
| ????2/11 | ??????1∶1 | ????537 | ????0.89 | ????2.58 |
| ????2/12 | ??????1∶1 | ????537 | ????0.82 | ????3.41 |
| ????2/13 | ??????1∶1 | ????536 | ????0.95 | ????2.86 |
| ???3/11/13 | ?????1∶1∶1 | ????537 | ????0.99 | ????2.24 |
| ????4/12 | ??????1∶1 | ????537 | ????0.81 | ????3.36 |
| ???4/11/13 | ?????1∶1∶1 | ????537 | ????1.06 | ????1.91 |
| ???5/11/13 | ?????1∶1∶1 | ????537 | ????1.07 | ????2.01 |
| ???6/11/13 | ?????1∶1∶1 | ????538 | ????1.06 | ????1.78 |
| ???7/11/13 | ?????1∶1∶1 | ????534 | ????1.04 | ????1.75 |
| ????8/12 | ??????1∶1 | ????537 | ????0.84 | ????3.31 |
| ????8/13 | ??????1∶1 | ????536 | ????0.91 | ????2.62 |
| ???9/11/13 | ????1.5∶1∶1.5 | ????569 | ????1.32 | ????1.39 |
| ???10/12/14 | ?????1∶1∶1 | ????0.92 | ????2.56 |
Also obtain good result with following table 6 listed dye mixtures.
Table 6
| Dye mixture | Weight ratio | ????Q *??[mJ/dot] | ??????m *????[l/mJ] |
| ????1/12/14 | ????1∶1∶1 | ????1.10 | ????[l/mJ] |
| ????2/14/16 | ????1∶1∶1 | ????0.87 | ????2.60 |
| ????2/14/17 | ????1∶1∶1 | ????0.88 | ????2.81 |
| ????6/12/18 | ????1∶1∶1 | ????0.86 | ????2.76 |
| ????10/12/17 | ????1∶1∶0.5 | ????0.90 | ????2.99 |
Claims (8)
1. the dye mixture that contains the anthraquinone dye of the pyridone dyes of one or more formulas I and one or more formula IIIs
In the formula, M is the group of following formula
Or
R
1And R
2Independent separately is C
1-C
10Alkyl can be by C
1-C
4Alkoxy carbonyl, C
1-C
4Alkoxyl group carbonyl oxygen base replaces, and its alkyl chain can be by 1 Sauerstoffatom at interval in ether functionality under each situation, or is replaced by phenyl, can be by 1-4 Sauerstoffatom interval in ether functionality; C
5-C
7Cycloalkyl; C
3-C
4Alkenyl; Unsubstituted or by C
1-C
4Alkyl, C
1-C
4The phenyl that alkoxyl group, halogen or nitro replace, perhaps the nitrogen-atoms that links to each other with them constitutes five yuan or hexa-atomic saturated heterocyclyl, other heteroatoms can be arranged, R
3When M is formula II
aGroup the time be the tertiary butyl or tert-pentyl; Or when M be formula II
bOr II
cGroup the time be C
3-C
10Alkyl, C
5-C
7Cycloalkyl, unsubstituted or by C
1-C
4Alkyl, C
1-C
4Phenyl or thienyl that alkoxyl group, halogen or nitro replace, R
4Be hydrogen, C
1-C
6Alkyl or unsubstituted or by C
1-C
4Alkane, C
1-C
4The phenyl that alkoxyl group, halogen or nitro replace, R
5Be cyano group, formamyl, one or two (C
1-C
8Alkyl) formamyl, carboxyl, C
1-C
8Alkoxy carbonyl or benzimidazolyl-, R
6Be C
1-C
10Alkyl can be replaced by phenyl, phenoxy group, cyclohexyloxy or pyrazolyl, and can be by 1-4 Sauerstoffatom at interval in ether functionality; C
5-C
7Cycloalkyl; Unsubstituted or by C
1-C
4Alkyl, C
1-C
4Phenyl or formula NB that alkoxyl group, halogen or nitro replace
1B
2Group, B wherein
1And B
2Independent separately is hydrogen, C
1-C
10Alkyl, unsubstituted or by C
1-C
4Alkyl, C
1-C
4The phenyl that alkoxyl group, halogen or nitro replace, C
1-C
9Alkyloyl, C
1-C
8Alkyl sulfide acyl group, unsubstituted or by C
1-C
4Alkyl, C
1-C
4The phenyl sulfonyl that alkoxyl group, halogen or nitro replace, the pyridyl sulfonyl, unsubstituted or by C
1-C
4Alkyl, C
1-C
4Benzoyl, pyridyl carbonyl or thienyl carbonyl that alkoxyl group, halogen or nitro replace, and in A or the E group one is nitrogen, and another is formula C-R
7Group, wherein R
7Be C
1-C
10Alkyl, can by phenyl, phenoxy group, encircle the oxygen base or pyrazolyl replaces and can be in ether functionality by 1-4 Sauerstoffatom interval); C
5-C
7Cycloalkyl or unsubstituted or by C
1-C
4Alkyl, C
1-C
4The phenyl that alkoxyl group, halogen or nitro replace,
L in the formula
1Be hydrogen, C
1-C
10Alkyl or unsubstituted or by C
1-C
4Alkyl, C
1-C
4The phenyl that alkoxyl group, halogen or nitro replace, L
2And L
3For being hydrogen independently of one another, unsubstituted or by phenyl or C
1-C
4The C that alkyl phenyl replaces
1-C
10Alkoxyl group, C unsubstituted or that replaced by phenyl
1-C
10Alkylthio, halogen, hydroxyphenyl, C
1-C
4The group of alkoxyl phenyl or following formula,
In the formula, G
1Be oxygen or sulphur, G
2Be hydrogen or C
1-C
8The monoalkyl sulfamyl, its alkyl chain can be by 1 or 2 Sauerstoffatoms at interval in ether functionality, and L
4Be amino, hydroxyl or C unsubstituted or that replaced by phenyl
1-C
10Alkylthio.
2. according to the dye mixture of claim 1, R wherein
4Be methyl.
3. according to the dye mixture of claim 1, R wherein
3Be C
3-C
10Alkyl, phenyl or thienyl.
4. according to the dye mixture of claim 1, R wherein
6Be C
1-C
8Alkyl, cyclopentyl, cyclohexyl or unsubstituted or by C
1-C
4Alkyl or C
1-C
4The phenyl that alkoxyl group replaces.
5. according to the dye mixture of claim 1, R wherein
7Be C
1-C
10Alkyl or unsubstituted or by C
1-C
4Alkyl or C
1-C
4The phenyl that alkoxyl group replaces.
6. according to the dye mixture of claim 1, L wherein
1Be hydrogen, L
4Be hydroxyl and L
2And L
3Definition is with claim 1.
7. according to the dye mixture of claim 1, wherein also contain one or more azoic dyestuffs, its azo component is selected from aminoisothiazoles and aniline, and its coupling component is selected from aminothiazole, aniline and tetrahydroquinoline.
8. one kind from transfer device is transferred to the method paper that is coated with plastics on by diffusion or distillation with dyestuff by the energy, and this method comprises the transfer device that uses the dye mixture that contains claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 96112611 CN1153189A (en) | 1995-09-07 | 1996-09-06 | Dye mixtures comprising methine and anthraquinone dyes |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19533026.9 | 1995-09-07 | ||
| CN 96112611 CN1153189A (en) | 1995-09-07 | 1996-09-06 | Dye mixtures comprising methine and anthraquinone dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1153189A true CN1153189A (en) | 1997-07-02 |
Family
ID=5121522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 96112611 Pending CN1153189A (en) | 1995-09-07 | 1996-09-06 | Dye mixtures comprising methine and anthraquinone dyes |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1153189A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1100832C (en) * | 1999-02-11 | 2003-02-05 | 中国科学院化学研究所 | Organic photoconductive composite and its preparation method |
| CN100384944C (en) * | 2006-04-04 | 2008-04-30 | 大连理工大学 | Tetrahydro quinoline functional dye containing thiophene bridge chain |
| CN101984000A (en) * | 2010-07-30 | 2011-03-09 | 江苏亚邦染料股份有限公司 | Bright red disperse dye capable of being used for direct printing of polyester fiber |
| CN102964611A (en) * | 2007-09-18 | 2013-03-13 | 朗盛德国有限责任公司 | Red paint mixture |
| CN101392102B (en) * | 2007-09-18 | 2014-03-12 | 朗盛德国有限责任公司 | Red dye mixture |
| CN103874584A (en) * | 2011-09-27 | 2014-06-18 | 凸版印刷株式会社 | Heat-sensitive transfer recording medium |
| CN108603041A (en) * | 2015-12-10 | 2018-09-28 | 德司达染料分销有限公司 | High humidity fastness disperse brilliant blue mixture |
-
1996
- 1996-09-06 CN CN 96112611 patent/CN1153189A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1100832C (en) * | 1999-02-11 | 2003-02-05 | 中国科学院化学研究所 | Organic photoconductive composite and its preparation method |
| CN100384944C (en) * | 2006-04-04 | 2008-04-30 | 大连理工大学 | Tetrahydro quinoline functional dye containing thiophene bridge chain |
| CN102964611A (en) * | 2007-09-18 | 2013-03-13 | 朗盛德国有限责任公司 | Red paint mixture |
| CN101392102B (en) * | 2007-09-18 | 2014-03-12 | 朗盛德国有限责任公司 | Red dye mixture |
| CN102964611B (en) * | 2007-09-18 | 2016-03-09 | 朗盛德国有限责任公司 | Red dye mixture |
| CN101984000A (en) * | 2010-07-30 | 2011-03-09 | 江苏亚邦染料股份有限公司 | Bright red disperse dye capable of being used for direct printing of polyester fiber |
| CN103874584A (en) * | 2011-09-27 | 2014-06-18 | 凸版印刷株式会社 | Heat-sensitive transfer recording medium |
| CN103874584B (en) * | 2011-09-27 | 2015-08-19 | 凸版印刷株式会社 | Heat-sensitive transfer recording medium |
| CN108603041A (en) * | 2015-12-10 | 2018-09-28 | 德司达染料分销有限公司 | High humidity fastness disperse brilliant blue mixture |
| CN108603041B (en) * | 2015-12-10 | 2020-09-04 | 德司达染料分销有限公司 | High wet fastness disperse brilliant blue mixture |
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