CN1157003A - 含氨基噻唑系列偶合组分的偶氨染料 - Google Patents
含氨基噻唑系列偶合组分的偶氨染料 Download PDFInfo
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- CN1157003A CN1157003A CN95194882A CN95194882A CN1157003A CN 1157003 A CN1157003 A CN 1157003A CN 95194882 A CN95194882 A CN 95194882A CN 95194882 A CN95194882 A CN 95194882A CN 1157003 A CN1157003 A CN 1157003A
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- China
- Prior art keywords
- phenyl
- unsubstituted
- group
- alkyl
- alkoxy carbonyl
- Prior art date
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- 239000000987 azo dye Substances 0.000 title abstract 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 title description 4
- 230000008878 coupling Effects 0.000 title description 4
- 238000010168 coupling process Methods 0.000 title description 4
- 238000005859 coupling reaction Methods 0.000 title description 4
- -1 aromatic heterocyclic amine Chemical class 0.000 claims abstract description 100
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 52
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 6
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 5
- 229920002994 synthetic fiber Polymers 0.000 claims abstract description 4
- 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 abstract description 4
- 239000000975 dye Substances 0.000 claims description 73
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 35
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 238000010023 transfer printing Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000004043 dyeing Methods 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 230000033228 biological regulation Effects 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- QRNATDQRFAUDKF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate Chemical compound NC(=S)SCCSC(N)=S QRNATDQRFAUDKF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000009792 diffusion process Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- 239000011092 plastic-coated paper Substances 0.000 claims description 2
- 150000003217 pyrazoles Chemical class 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- 150000004867 thiadiazoles Chemical class 0.000 claims description 2
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical class S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 claims description 2
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 claims 1
- 238000007639 printing Methods 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 13
- 229920000728 polyester Polymers 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000000976 ink Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 210000004209 hair Anatomy 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- VVYOMSIENMVPKA-UHFFFAOYSA-N n,n-dibutyl-4-tert-butyl-1,3-thiazol-2-amine Chemical class CCCCN(CCCC)C1=NC(C(C)(C)C)=CS1 VVYOMSIENMVPKA-UHFFFAOYSA-N 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
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- WOZVHXUHUFLZGK-UHFFFAOYSA-N terephthalic acid dimethyl ester Natural products COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- 125000005976 1-phenylethyloxy group Chemical group 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- 125000005975 2-phenylethyloxy group Chemical group 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000000217 alkyl group Chemical group 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
- 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
- 238000006193 diazotization reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical class OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 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
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 235000011091 sodium acetates Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([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
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- 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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- BBAWTPDTGRXPDG-UHFFFAOYSA-N [1,3]thiazolo[4,5-b]pyridine Chemical compound C1=CC=C2SC=NC2=N1 BBAWTPDTGRXPDG-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229950003476 aminothiazole Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- OZPOKBYTBMPYGZ-UHFFFAOYSA-N hexylperoxymethylbenzene Chemical compound CCCCCCOOCC1=CC=CC=C1 OZPOKBYTBMPYGZ-UHFFFAOYSA-N 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 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
- 125000005932 isopentyloxycarbonyl group Chemical group 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
- 239000007788 liquid Substances 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
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Abstract
式(I)偶氮染料适用于热转印和合成材料的染色或印花式中:D是苯胺系列或芳族杂环胺系列的重氮组分的基团,R1与R2各自为可取代的C1-C10-烷基,C5-C7-环烷基、C3-C4-链烯基,取代的或未取代的苯基,或R1、R2与氮原子一起构成杂环基团,以及R3是叔丁基或叔戊基。
Description
EP-A-441208公开了以2-氨基噻唑为偶合组分的偶氮染料。
本发明的目的是为纺织材料的染色及印花提供具有优良应用性能的或是适于热染色转移用的新的偶氮染料。
我们已经发现,本发明目的可由本文开头定义的式I偶氮染料来实现。
需看重提出的是:式I偶氮染料中D是由苯胺系列的重氮基组分衍生的或由吡咯、噻吩、吡唑、噻唑、异噻唑、三唑、噻二唑、苯并噻吩、苯并噻唑、苯并异噻唑、吡啶并噻唑、嘧啶并噻吩或噻吩并噻吩系列的胺衍生的。
适用的D基符合下面所列各式式中:L1是硝基、氰基、C1-C6-烷酰基、苯甲酰基、C1-C6-烷氧基羰基、C1-C8烷基磺酰基,取代的或未取代的苯磺酰基或式-CH=T基团,其中T是羟基亚氨基、C1-C4-烷氧基亚氨基或酸式-CH化合物H2T的基团,L2是氢、C1-C6-烷基、卤素、羟基、巯基、未取代的或苯基或C1-C4-烷氧基取代的C1-C6-烷氧基、取代的或未取代的苯氧基、未取代的或苯基取代的C1-C8-烷基硫代、取代的或未取代的苯基硫代、C1-C8-烷基磺酰基或取代的或未取代的苯基磺酰基,L3是氰基、C1-C6-烷氧基羰基或硝基,L4是氢、C1-C6-烷基或苯基,L5是C1-C6-烷基或苯基,L6是氢、氰基、硝基、C1-C6-烷氧基羰基、C1-C6-烷酰基、氰硫基或卤素,L7是硝基、氰基、C1-C6-烷酰基、苯甲酰基、C1-C6-烷氧基羰基、C1-C8-烷基磺酰基、取代的或未取代的苯基磺酰基或式-CH=T基团,其中T定义同上。L8是氢、C1-C6-烷基、取代或未取代的苯基、氰基、卤素、未取代的或苯基或C1-C4-烷氧基取代的C1-C8-烷氧基、未取代的或苯基取代的C1-C8-烷基硫代、取代的或未取代的苯基硫代、C1-C8-烷基磺酰基,取代或未取代的苯基磺酰基或C1-C6-烷氧基羰基,L9是氰基、未取代的或苯基或C1-C4-烷氧基取代的C1-C6-烷基、未取代的或苯基取代的C1-C8-烷氧基、未取代的或苯基取代的C1-C8-烷基硫代、取代的或未取代的苯基、噻吩基、C1-C4-烷基噻吩基、吡啶基或C1-C4-烷基吡啶基或与L6一起稠合的苯并基团,L10是苯基或吡啶基,L11是三氟代甲基、硝基、C1-C6-烷基、苯基、未取代的或苯基取代的C1-C8-烷基硫代或C1-C6-二烷基氨基,L12是未取代或乙酰氧基取代的C1-C6-烷基、苯基、未取代的或苯基取代的C1-C8烷基硫代、2-氰基乙基硫代或2-(C1-C6-烷氧基羰基)乙基硫代,L13是氢、硝基或卤素,L14是氢、氰基、C1-C6-烷氧基羰基、硝基或卤素,L15、L16及L17各自独立地是氢,C1-C6-烷基、C1-C6-烷氧基、卤素、硝基、氰基、未取代或苯基取代的C1-C6-烷氧基羰基、C1-C8-烷基磺酰基或取代的或未取代的苯基磺酰基、或L15与L16一起是式CO-NW-CO的基团,其中W是为醚官能中1个或2个氧原子隔开的或不隔开的并被羟基取代的或没有羟基取代的C1-C10-烷基,L18是氢、甲基或氯,以及L19是氰基或C1-C6-烷氧基羰基。
上式中任何取代的烷基或链烯基可以是直链或支链的。
上式任何取代的烷基中的取代基个数通常是1或2。
上式中任何取代的苯基可以有诸如C1-C6-烷基、C1-C8烷氧基、卤素(特别是氯或溴)或硝基取代基(另有说明的除外)。
上式任何取代的苯基、呋喃基、噻吩基中的取代基数通常为1-3,优选1或2。
L2、L4、L5、L8、L9、L11、L12、L15、L16、L17、R1、R2和W各自例如是甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、新戊基、叔戊基、己基或2-甲基戊基。
R1、R2、R6及W各自也可以例如是庚基、辛基、2-乙基己基、异辛基、壬基、异壬基、癸基、或异癸基(名称异辛基、异壬基及异癸基是由氧化合成法制的各类醇的衍生产物的俗名,参看“Ullmann的工业化学百科全书”(Encyclopedia of Industrial Chemistry),5thEdition,Vol.A.1,pages 290-293,及Vol.A 10 pages 284和285)。
R1、R2和R6各自也可以例如是环戊基、甲基环戊基、二甲基环戊基、环己基、甲基环己基或环庚基。
L9、R1、R2和W各自也可以例如是2-甲氧基乙基、2-乙氧基乙基、2-丙氧基乙基、2-异丙氧基乙基、2-丁氧基乙基、2-或3-甲氧基丙基、2-或3-乙氧基丙基、2-或3-丙氧基丙基、2-或3-丁氧基丙基、2-或4-甲氧基丁基、2-或4-乙氧基丁基、2-或4-丙氧基丁基或为2-或4-丁氧基丁基。
R1、R2和W各自也可以例如是3,6-二氧杂庚基、3,6-二氧杂辛基、4,8-二氧杂壬基、3,7-二氧杂辛基、3,7-二氧杂壬基、4,7-二氧杂辛基、4,7-二氧杂壬基或4,8-二氧杂癸基。
R1和R2各自也可以例如是3,6,8-三氧杂癸基、3,6,9-三氧杂十一烷基、3,6,9,12-四氧杂十三烷基、3,6,9,12-四氧杂十四烷基、2-氰基乙基、2-或3-氰基丙基、2-或4-氰基丁基、2-羟乙基、2-或3-羟丙基、2-或4-羟丁基、2-氯乙基、2-或3-氯丙基、2-或4-氯丁基、2-乙酰氧基乙基、2-或3-乙酰氧基丙基、2-或4-乙酰氧基丁基、2-丙酰氧基乙基、2-或3-丙酰氧基丙基、2-或4-丙酰氧基丁基、2-甲氧基羰基乙基、2-乙氧基羰基乙基、2-丙氧基羰基乙基、2-异丙氧基羰基乙基、2-丁氧基羰基乙基、2-或3-甲氧基羰基丙基、2-或3-乙氧基羰基丙基、2-或3-丙氧基羰基丙基、2-或3-丁氧基羰基丙基、2-或4-甲氧基羰基丁基、2-或4-乙氧基羰基丁基、2-或4-丙氧基羰基丁基、2-或4-丁氧基羰基丁基、2-甲氧基羰基氧乙基、2-乙氧基羰基氧乙基、2-丙氧基羰基氧乙基、2-异丙氧基羰基氧乙基、2-丁氧基羰基氧乙基、2-或3-甲氧基羰基氧丙基、2-或3-乙氧基羰基氧丙基、2-或3-丙氧基羰基氧丙基、2-或3-丁氧基羰基氧丙基、2-或4-甲氧基羰基氧丁基、2-或4-乙氧基羰基氧丁基、2-或4-丙氧基羰基氧丁基、2-或4-丁氧基羰基氧丁基、丙-1-烯-3-基、丁-2-烯-4-基或2-甲基丙-1-烯-3-基。
L9、R1和R2各自也可例如是苄基或1-或2-苯基乙基。
L12也可以例如是2-乙酰氧基乙基、2-或3-乙酰氧基丙基或为2-或4-乙酰氧基丁基。
L2、L8、L9和L11各自也可以例如是甲基硫代、乙基硫代、丙基硫代、异丙基硫代、丁基硫代、异丁基硫代、戊基硫代、己基硫代、庚基硫代、辛基硫代、2-乙基己基硫代、苄基硫代或为1-或2-苯基乙基硫代。
L2和L8各自也可以例如是苯基硫代、2-甲基苯基硫代、2-甲氧基苯基硫代或2-氯代苯基硫代。
L2、L8、L9、L15、 L16和L17各自也可以例如是甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基、戊氧基、异戊氧基、新戊氧基、叔戊氧基、己氧基或2-甲基戊氧基。
L9也可以例如是苄氧基或为1-或2-苯基乙氧基。
L6例如是氟、氯或溴、并且L2、L8、L13、L14、L15、L16及L17各自还可以是氟、氯或溴、
L7与L1每个及L2、L8、L15、L16与L17各自还可以例如是甲基磺酰基、乙基磺酰基、丙基磺酰基、异丙基磺酰基、丁基磺酰基、异丁基磺酰基、仲丁基磺酰基、戊基磺酰基、异戊基磺酰基、新戊基磺酰基、己基磺酰基、庚基磺酰基、辛基磺酰基、2-乙基己基磺酰基、苯基磺酰基、2-甲苯基磺酰基、2-甲氧基苯基磺酰基或2-氯代苯基磺酰基。
L3是及L1、L6、L7、L8、L14、L15、L16、L17与L19各自还可以例如是甲氧基羰基、乙氧基羰基、丙氧基羰基、异丙氧基羰基、丁氧基羰基、异丁氧基羰基、仲丁氧基羰基、戊氧基羰基、异戊氧基羰基、新戊氧基羰基或己氧基羰基。
L15、L16与L17各自也可以例如是2-苯氧基乙氧基羰基、2-或3-苯氧基丙氧基羰基或2-或4-苯氧基丁氧基羰基。
L2与L8各自也可以例如是2-甲氧乙氧基、2-乙氧基乙氧基、2-或3-甲氧基丙氧基、2-或3-乙氧基丙氧基、2-或4-甲氧基丁氧基、2-或4-乙氧基丁氧基、5-甲氧基戊氧基、5-乙氧基戊氧基,6-甲氧基己氧基、6-乙氧基己氧基、苄基氧基或1-或2-苯基乙氧基。
L11也可以例如是二甲基氨基、二乙基氨基、二丙基氨基、二异丙基氨基、二丁基氨基、二戊基氨基、二己基氨基或N-甲基-N-乙基氨基。
L12也可以例如是2-甲氧基羰基乙基硫代或2-乙氧基羰基乙基硫代。
L8、L9、R1与R2各自也可以例如是苯基、2-、3-或4-甲基苯基、2,4-二甲基苯基、2-、3-或4-甲氧基苯基、2-、3-或4-氯代苯基或2-、3-或4-硝基苯基。
L9可以例如是2-或3-甲基噻吩基或为2-、3-、或4-甲基吡啶基。
L1、L6与L7各自也可以例如是甲酰基、乙酰基、丙酰基、丁酰基、异丁酰基、戊酰基或己酰基。
在-CH=T(L1或L7)基中,T是由酸式-CH化合物H2T衍生的,所述酸式CH化合物H2T是一种诸如下式的化合物:式中:Z1是氰基、硝基、C1-C4-烷酰基、取代的或未取代的苯甲酰基、C1-C4-烷基磺酰基、取代的或未取代的苯基磺酰基、C1-C4-烷氧基羰基、C3-C4-链烯氧基羰基、苯氧基羰基、氨基甲酰基、单-或二(C1-C4-烷基)氨基甲酰基、取代的或未取代的苯基氨基甲酰基、取代的或未取代的苯基、2-苯并噻唑基、2-苯并咪唑基、5-苯基-1,3,4-噻二唑-2-基或2-羟基-3-喹喔啉基,Z2是C1-C4-烷基、C1-C4-烷氧基或C3-C4链烯氧基,Z3是C1-C4-烷氧基羰基、C3-C4链烯氧基羰基、苯基氨基甲酰基或2-苯并咪唑基,Z4是氰基、C1-C4-烷氧基羰基或C3-C4-链烯氧基羰基,Z5是氢或C1-C6烷基,Z6是氢,C1-C4-烷基或苯基,以及Z7是C1-C4-烷基。
应注意由式IIIa、IIIb、或IIIc化合物衍生的基团,式中Z1是氰基、C1-C4-烷酰基、C1-C4-烷氧基羰基或C3-C4-链烯氧基羰基,Z2是C1-C4-烷基、C1-C4-烷氧基或C3-C4链烯氧基,Z3是C1-C4-烷氧基羰基或C3-C4链烯氧基羰基及Z4是氰基。
特别应注意由式IIIa、IIIb、或IIIc化合物衍生的基团,式中Z1是氰基、C1-C4-烷氧基羰基或C3-C4-链烯氧基羰基,Z2是C1-C4-烷氧基或C2-C4-链烯氧基,Z3是C1-C4-烷氧基羰基或C3-C4链烯氧基羰基及Z4是氰基。
R1及R1与氮原子结合在一起构成五元或六元饱和的杂环(还可含或不含别的杂原子)基,例如吡咯烷基、哌啶基、吗啉基、硫代码啉基、硫代吗啉基S,S-二氧化物,哌嗪基或N-(C1-C4-烷基)哌嗪基如N-甲基-或N-乙基哌嗪基。
式I偶氮染料中R1与R2各自独立地为C1-C8烷基,如C1-C4-烷氧基、C1-C4-烷氧基羰基或取代的苯基、环戊基、环己基或丙-1-烯-3-基是优选的
式I偶氮染料中D是式IIb、IId、IIe、IIh或IIq基也是优选。
式I偶氮染料中R1与R2各自独立地为被苯基取代的或未取代的C1-C6烷基是特别优选的。
式I偶氮染料中R3是叔丁基也是特别优选的。
式I偶氮染料中D是式IIb、IId、IIe、IIh或IIq也是特别优选的,其中:L1是硝基、氰基、甲酰基或式-CH=T基团,其中T是酸式-CH化合物H2T的基团,L2是C1-C6-烷基或卤素,L3是氰基、C1-C6-烷氧基羰基或硝基,L6是氰基,L7是硝基、氰基、甲酰基、C1-C6-烷氧基羰基或式-CH=T的基,其中T规定同上,L8是C1-C6-烷基、取代的或未取代的苯基、氰基、卤素或C1-C6-烷氧基羰基,L9是未取代的或苯基取代的C1-C6-烷基、未取代的或苯基取代的C1-C6-烷基硫代或取代的或未取代的苯基,L12是未取代的或苯基取代的C1-C8-烷基硫代,以及L15、L16与L17各自独立地是氢,C1-C6-烷基、C1-C6-烷氧基、硝基、氰基或未取代的或苯氧基取代的C1-C6-烷氧基羰基,或L15与L16一起是式CO-NW-CO的基团,其中W定义同上。
可按常规方法制得新的式I偶氮染料,例如对式IV的重氮基组分进行常规重氮化
D-NH2 (IV),式中D定义同上,并将得到的重氮化盐与式V的氨基噻唑偶合式中R1、R2和R3各自定义同上。
本发明还提供借助能源通过染料的扩散或升华使染料从转印载体转印到塑料涂布纸上的方法,该方法包括采用一种其上有一种或多种式I偶氮染料的转印载体。
为制造供本发明方法所需的转印载体,将式I偶氮染料与一种或多种胶粘剂掺混在一种适用的有机溶剂或混合溶剂中,在有或没有辅助组分存在下以形成印刷油墨。该印刷油墨中优选含分子分散形式的染料,即溶解状态的染料。可借助医用刮刀将该印刷油墨涂敷在惰性载体上后经风干。适用于式I偶氮染料的有机溶剂包括如在温度为20℃、染料的溶解度大于1%(重量)、优选大于5%(重量)的那些溶剂。
溶剂的实例是乙醇、丙醇、异丁醇、四氢呋喃、二氯乙烷、甲基乙基酮、环戊酮、环己酮、甲苯、氯苯或它们的混合物。
适用的胶粘剂包括所有能溶于有机溶剂中并能将偶氮染料牢固地粘结在惰性载体上以防止擦去的树脂或聚合物材料。优选的胶粘剂是那些在印刷油墨经风干后,在呈清沏、透明膜中的染料不存在任何可见的染料结晶的胶粘剂。
这类胶粘剂已在如US-A-5132438或其中所引用的有关专利申请中提到。饱和的线型聚酯也是适用的。
优选的胶粘剂包括乙基纤维素、乙基羟乙基纤维素、聚乙烯缩丁醛、聚乙酸乙烯酯、丙酸纤维素酯或饱和线型聚酯。
胶粘剂与偶氮染料的重量比通常为1∶2-4∶1之间。
适用的辅助组分包括如在US-A-5132438或其中所引用的有关专利申请中提到的脱模剂。特别是防止转移染料在贮存期间或色带加热时结晶析出的有机添加剂,如胆甾醇或香草醛也是适用的。
适用的惰性载体已在如US-A-5132438或其中所列举有关专利申请中公开。载体的厚度通常在3-30微米,优选5-10微米之间。
适用的染料接受层原则上包括所有与被转移染料有亲和力的、热稳定的塑料层,如改性聚碳酸酯或聚酯层。更详细的说明可在如US-A-5132438或其中所列举的有关专利申请中找到。
可借助能源,例如借助激光或热转印印刷头来实现染料的转移,后者必须可加热至温度≥300℃,以使染料能在时间t:0<t<15毫秒范围内发生转移。染料从片状转移载体迁移出并扩散进入涂布有接受介质的表面上。
本发明式I偶氮染料在应用性能方面的优点是值得注意的。这些染料在色带中具有高的溶解度(与胶粘剂有好的相容性)、在印刷油墨中具有高度稳定性,好的转移性以及高的图象稳定性(即好的耐光牢度及对环境因素如湿度、温度或化学品有好的稳定性),并具有灵活多变的色彩可适应减色法三原色配色中最佳三原色(染料混合物)的要求。
该新的染料也适用作为黑色混合物的组分。
在某些情况下,由于染料在光谱的兰色和红色区域的高度透明性而出现高亮度也是值得注意的。
本发明式I偶氮染料也完全适于合成材料如聚酯、聚酰胺或聚碳酸酯的染色或印花。尤其适宜于纺织材料,如聚酯、改性聚酯(如阴离子改性聚酯)或聚酯与纤维素、棉花、粘胶或羊毛混纺的纤维、纱、线、针织品、织造织物或无纺织物的染色或印花。染色和印花条件本质上是已知的。根据本发明的染料也可用于角蛋白纤维,如毛发或毛皮的染色。
新的式I偶氮染料对制造如EP-A-399473所述的滤色器也是特别适用的。
最后,这类染料也可有效地作为电子照相调色剂用染料。
下列实施例是本发明的说明。
A)制备
实施例1
将22.2克3-甲基-4-氰基-5-氨基异噻唑悬浮在150毫升7∶3V/V冰醋酸/丙酸混合液中,添加6毫升浓硫酸,随后在0-5℃滴加48克亚硝基硫酸。接着在0-5℃下搅拌该混合物3小时。然后将所得重氮盐溶液滴加到0-5℃的52克2-二丁氨基-4-叔丁基噻唑(82.9%重量浓度)的100毫升N,N-二甲基甲酰胺溶液中。继之以用20克乙酸钠进行缓冲,在室温下继续搅拌,然后抽滤法滤出沉淀,用甲醇和水洗涤并干燥,得到55.8克(理论值的83.5%)下式染料熔点:202℃;λmax(在四氢呋喃中):527nm
实施例2
将5.2克2,5-二氯-4-硝基苯胺悬浮在20-30℃10克96%(重量浓度)硫酸中,然后在15-20℃与13克亚硝基硫酸混合。将所得的溶液加到50毫升水和100克冰中,其后搅拌15分钟并过滤。于0-5℃将滤液滴加到9.3g 2-二丁氨基-4-叔丁基噻唑溶于100毫升甲醇的溶液中。在室温下搅拌过夜,用抽滤法滤出沉淀,用甲醇和水洗涤并干燥,得到9.58克(理论值的78.8%)下式染料熔点:164℃;λmax(在四氢呋喃中):522nm
实施例3
将5.2克2-氨基对苯二甲酸二甲酯悬浮在25毫升冰醋酸和10毫升浓盐酸中,并于0-5℃与8毫升23%(重量浓度)亚硝酸钠水溶液混合。接着在0-5℃搅拌1小时,然后在0-5℃将反应溶液加到9.2克2-二丁氨基-4-叔丁基噻唑溶于200毫升甲醇的溶液中。用10克乙酸钠缓冲后,搅拌并过滤,用甲醇和水洗涤过滤的沉淀物并干燥,得到6.23克(理论值的51%)下式染料熔点:74℃;λmax(在四氢呋喃中):462nm
能用同样方法制得的染料列于表1中。
B)在热转移印花中的用途
热转移印花方法
a).将10克染料置于100克10%(重量浓度)粘合剂的甲乙酮/甲苯/环己酮(4.5∶2∶2 V/V/V)溶液中搅拌(如果需要可短暂加热到80-90℃)。
用医用6微米刮刀将上述混合物涂敷在6微米厚、背面已有适宜增滑层的聚酯薄膜上,并用电吹发器于1分钟内将其吹干。因为残留溶剂可能会损害转印工艺,所以色带在能用于转印前还必须风干至少24小时。
b).在装有市售热转印印刷头的实验用计算机控制装置上将色带转印到市售彩色图象印刷纸(Hitachi)上。
可改变电压来控制热转印印刷头发射的能量,脉冲宽度已设定在7毫秒,并每次只发射一个脉冲。发射的能量大小范围在0.7-2.0毫焦/点。
因为色浓度正比于供给的能量,利用色楔进行光谱的评价是可能的。
以色浓度对每一加热单元供给的能量作图可用来确定Q*值(=吸收值为1时的能量,毫焦)和梯度m,l/毫焦。
得到的结果与λmax值(在图象打印纸上测定的)一起列于下表2中。
每种染料所用的粘合剂都是以饱和线型聚酯和以聚乙烯缩丁醛为主要成分的产物。表中每一实施例的Q*和m值中第一个数据是由聚酯作粘合剂测量的,第二个数据是以聚乙烯缩丁醛作粘合剂测量的。表2
染料 | Q*[mJ/Dot] | m[l/mJ] | λmax[nm] |
1 | 0.870.93 | 3.002.40 | 534 |
4 | 1.051.07 | 2.172.31 | 582 |
5 | 1.201.32 | 1.751.06 | 637 |
7 | 0.891.02 | 2.861.78 | 531 |
8 | 1.381.84 | 1.380.82 | 528 |
9 | 0.890.95 | 2.862.30 | 540 |
10 | 1.000.99 | 1.222.11 | 518 |
11 | 1.001.10 | 1.971.69 | 492 |
12 | 0.991.07 | 2.051.85 | 485 |
13 | 0.990.97 | 2.022.08 | 540 |
14 | 0.860.94 | 2.702.40 | 520 |
15 | 0.780.84 | 2.803.56 | 515 |
16 | 1.011.13 | 2.011.74 | 515 |
染料 | Q*[mJ/Dot] | m[l/mJ] | λmax[nm] |
17 | 0.891.01 | 3.702.63 | 523 |
18 | 0.910.98 | 3.292.60 | 502 |
19 | 0.921.01 | 3.122.50 | 515 |
20 | 0.920.98 | 2.802.50 | 530 |
21 | 0.891.13 | 2.141.71 | 527 |
23 | 0.860.87 | 3.123.12 | 534 |
24 | 0.961.07 | 2.201.95 | 537 |
25 | 0.870.92 | 3.032.59 | 537 |
26 | 0.920.99 | 2.242.32 | 537 |
27 | 0.860.85 | 2.852.79 | 535 |
28 | 0.850.90 | 3.343.21 | 531 |
29 | 0.850.90 | 3.143.04 | 532 |
30 | 0.871.01 | 2.852.04 | 549 |
染料 | Q*[mJ/Dot] | m[l/mJ] | λmax[nm] |
31 | 0.91 | 3.00 | 531 |
32 | 0.79 | 2.74 | 518 |
33 | 0.83 | 3.63 | 554 |
34 | 1.02 | 2.06 | 458 |
35 | 0.900.89 | 2.562.42 | 536 |
36 | 0.880.92 | 2.872.50 | 535 |
37 | 0.920.92 | 2.562.20 | 540 |
38 | 0.900.90 | 2.682.71 | 536 |
39 | 0.880.95 | 2.342.28 | 537 |
40 | 1.101.07 | 1.611.66 | 518 |
41 | 0.890.96 | 2.652.08 | 514 |
42 | 0.850.92 | 2.882.85 | 529 |
43 | 0.860.86 | 3.393.36 | 531 |
染料 | Q*[mJ/Dot] | m[l/mJ] | λmax[nm] |
44 | 0.910.96 | 2.262.34 | 516 |
45 | 0.901.02 | 2.442.01 | 520 |
46 | 0.950.99 | 2.442.31 | 514 |
47 | 0.870.93 | 3.432.75 | 531 |
48 | 0.950.92 | 2.382.65 | 534 |
49 | 0.900.96 | 2.982.45 | 534 |
50 | 0.860.88 | 3.143.04 | 515 |
51 | 0.920.96 | 2.482.61 | 527 |
52 | 1.041.15 | 1.881.66 | 531 |
53 | 0.830.90 | 3.252.93 | 530 |
54 | 0.810.88 | 4.303.07 | 531 |
55 | 0.961.04 | 2.352.09 | 476 |
56 | 0.880.97 | 2.712.40 | 446 |
染料 | Q*[mJ/Dot] | m[l/mJ] | λmax[nm] |
57 | 1.17 | 1.45 | 654 |
58 | 0.911.00 | 2.482.09 | 477 |
59 | 1.051.12 | 1.661.46 | 445 |
60 | 1.041.08 | 1.541.70 | 459 |
61 | 1.141.17 | 1.531.66 | 440 |
62 | 1.311.37 | 1.301.13 | 441 |
63 | 0.91 | 3.11 | 550 |
64 | 0.860.94 | 3.092.63 | 508 |
65 | 0.860.94 | 2.872.42 | 489 |
66 | 0.820.83 | 3.613.11 | 494 |
67 | 0.870.94 | 3.142.66 | 546 |
68 | 0.871.01 | 2.852.04 | 549 |
69 | 0.94 | 2.38 | 545 |
染料 | Q*[mJ/Dot] | m[l/mJ] | λmax[nm] |
70 | 0.890.95 | 2.862.30 | 540 |
71 | 0.891.02 | 2.861.78 | 531 |
72 | 0.790.89 | 3.332.77 | 552 |
73 | 0.840.91 | 2.922.28 | 524 |
74 | 0.860.94 | 2.542.49 | 563 |
75 | 0.820.87 | 4.012.98 | 582 |
76 | 0.86 | 3.40 |
c).在染色中的应用
将10克聚酯织物置于50℃、200毫升含X%(以纤维重量计)染料的染液中,用乙酸调节染液的pH至4.5。5分钟后,将染液的温度于30分钟内升至130℃,保温60分钟,然后于20分钟内将温度降至60℃。
然后将染过色的聚酯织物用65℃的200毫升含5毫升/升32%(重量浓度)的氢氧化钠溶液、3克/升连二亚硫酸钠以及1克/升的由48摩尔环氧乙烷与1摩尔蓖麻油的加成产物的液体进行还原清洗15分钟。最后,对织物进行漂洗,用稀乙酸中和,再漂洗一次并进行干燥。
染料1和染料20给出下列结果:
染料1染料量(X): 0.26%(重量)HGD: 358.9色度: 54耐光牢度: 6-7染料20染料量(X): 0.29%(重量)HGD: 351.7色度: 54.9耐光牢度: 6-7
Claims (10)
2.根据权利要求1的偶氮染料,其中D是由苯胺系列的重氮基组分衍生的或由吡咯、噻吩、吡唑、噻唑、异噻唑、三唑、噻二唑、苯并噻吩、苯并噻唑、苯并异噻唑、吡啶并噻吩、嘧啶并噻吩或噻吩并噻吩系列的胺衍生的。
3.根据权利要求1的偶氮染料,其中D是下列各式的基团:式中:L1是硝基、氰基、C1-C6-烷酰基、苯甲酰基、C1-C6-烷氧基羰基、C1-C8-烷基磺酰基,取代或未取代的苯磺酰基或式-CH=T的基团,其中T是羟基亚氨基、C1-C4-烷氧基亚氨基或酸式-CH化合物H2T的基团,L2是氢、C1-C6-烷基、卤素、羟基、巯基、未取代的或苯基或C1-C4-烷氧基取代的C1-C6-烷氧基、取代的或未取代的苯氧基、未取代的或苯基取代的C1-C8-烷基硫代、取代的或未取代的苯基硫代、C1-C8-烷基磺酰基或取代的或未取代的苯基磺酰基,L3是氰基、C1-C6-烷氧基羰基或硝基,L4是氢、C1-C6-烷基或苯基,L5是C1-C6-烷基或苯基,L6是氢、氰基、硝基、C1-C6-烷氧基羰基、C1-C6-烷酰基、氰硫基或卤素,L7是硝基、氰基、C1-C6-烷酰基、苯甲酰基、C1-C6-烷氧基羰基、C1-C8-烷基磺酰基、取代的或未取代的苯基磺酰基或式-CH=T基团,其中T规定同上,L8是氢、C1-C6-烷基、取代或未取代的苯基、氰基、卤素、未取代的或苯基或C1-C4-烷氧基取代的C1-C6-烷氧基、未取代的或苯基取代的C1-C8-烷基硫代、取代的或未取代的苯基硫代、C1-C8-烷基磺酰基,取代或未取代的苯基磺酰基或C1-C6-烷氧基羰基,L9是氰基、未取代的或苯基或C1-C4-烷氧基取代的C1-C6-烷基、未取代的或苯基取代的C1-C8-烷氧基、未取代的或苯基取代的C1-C8烷基硫代、取代的或未取代的苯基、噻吩基、C1-C4-烷基噻吩基、吡啶基或C1-C4-烷基吡啶基,L10是苯基或吡啶基,L11是三氟代甲基、硝基、C1-C6-烷基、苯基、未取代的或苯基取代的C1-C8-烷基硫代或C1-C6-二烷基氨基,L12是未取代或乙酰氧基取代的C1-C6-烷基、苯基、未取代的或苯基取代的C1-C8烷基硫代、2-氰基乙基硫代或2-(C1-C6-烷氧基羰基)乙基硫代,L13是氢、硝基或卤素,L14是氢、氰基、C1-C6-烷氧基羰基、硝基或卤素,L15、L16及L17各自独立地为氢,C1-C6-烷基、C1-C6-烷氧基、卤素、硝基、氰基、未取代或苯氧基取代的C1-C6-烷氧基羰基、C1-C8-烷基磺酰基或取代或未取代的苯基磺酰基、或L15与L16一起是式CO-NW-CO的基团,其中W是为醚官能中1个或2个氧原子隔开的或不隔开的、并被羟基取代的或没有羟基取代的C1-C10-烷基,L18是氢、甲基或氯,以及L19是氰基或C1-C6-烷氧基羰基。
4.根据权利要求1-3任何一项的偶氮染料,其中R1和R2各自独立地是被C1-C4-烷氧基,C1-C4-烷氧基羰基或苯基取代的C1-C8-烷基,环戊基,环己基或丙-1-烯-3-基。
5.根据权利要求1-3任何一项偶氮染料,其中D是式IIb、IId、IIe、IIh或IIq的基团。
6.根据权利要求1的偶氮染料,其中R1与R2各自独立地为苯基取代的或未取代的C1-C6-烷基。
7.根据权利要求1的偶氮染料,其中R3是叔丁基。
8.根据权利要求1-3任何一项偶氮染料,其中D是式IIb、IId、IIe、IIh或IIq的基团,式中:L1是硝基、氰基、甲酰基或式-CH=T基,其中T是酸式-CH化合物H2T的基团,L2是C1-C6-烷基或卤素,L3是氰基、C1-C6-烷氧基羰基或硝基,L6是氰基,L7是硝基、氰基、甲酰基、C1-C6-烷氧基羰基或式-CH=T基团,其中T规定同上,L8是C1-C6-烷基、取代的或未取代的苯基、氰基、卤素或C1-C6-烷氧基羰基,L9是未取代的或苯基取代的C1-C6-烷基,未取代的或苯基取代的C1-C6-烷基硫代或取代或未取代的苯基,L12是未取代的或苯基取代的C1-C8-烷基硫代,以及L15、L16与L17各自独立地是氢、C1-C6-烷基、C1-C6-烷氧基、硝基、氰基或未取代的或苯氧基取代的C1-C6-烷氧基羰基,或L15与L16一起是式CO-NW-CO的基团,其中W规定同权利要求3。
9.借助能源通过染料的扩散或升华而使染料从转印载体转印到塑料涂布纸上的方法,该方法包括采用一种其上有一种或多种权利要求1规定的偶氮染料的转印载体。
10.权利要求1偶氮染料在合成材料的染色或印花中的用途。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4426023A DE4426023A1 (de) | 1994-07-22 | 1994-07-22 | Azofarbstoffe mit einer Kupplungskomponente aus der Aminothiazolreihe |
DEP4426023.7 | 1994-07-22 |
Publications (1)
Publication Number | Publication Date |
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CN1157003A true CN1157003A (zh) | 1997-08-13 |
Family
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CN95194882A Pending CN1157003A (zh) | 1994-07-22 | 1995-07-20 | 含氨基噻唑系列偶合组分的偶氨染料 |
Country Status (6)
Country | Link |
---|---|
US (1) | US5789560A (zh) |
EP (1) | EP0773976B1 (zh) |
KR (1) | KR970704834A (zh) |
CN (1) | CN1157003A (zh) |
DE (2) | DE4426023A1 (zh) |
WO (1) | WO1996003462A1 (zh) |
Cited By (1)
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WO2016134556A1 (zh) * | 2015-02-28 | 2016-09-01 | 苏州帅马金属制品有限公司 | 板材表面图案制作工艺及其所制板材和家具 |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19533026A1 (de) * | 1995-09-07 | 1997-03-13 | Basf Ag | Farbstoffmischungen, enthaltend Methin- und Anthrachinonfarbstoffe |
DE19611351A1 (de) * | 1996-03-22 | 1997-09-25 | Basf Ag | Farbstoffmischungen, enthaltend Thienyl- und/oder Thiazolazofarbstoffe |
CN1531724A (zh) * | 2001-03-28 | 2004-09-22 | 在信息层中含有作为吸光性化合物的杂环偶氮染料的光学数据存储介质 | |
US7960175B2 (en) | 2003-06-16 | 2011-06-14 | Kyushu University, National University Corporation | Process for producing human-origin immunocompetent cell |
EP1975204B1 (en) * | 2007-03-27 | 2013-10-02 | FUJIFILM Corporation | Azo dye and azo compound |
JP4668228B2 (ja) * | 2007-03-30 | 2011-04-13 | 富士フイルム株式会社 | 感熱転写記録用インクシートおよび感熱転写記録方法 |
TWI481954B (zh) * | 2009-06-10 | 2015-04-21 | Fujifilm Corp | 著色硬化組成物、彩色光阻、噴墨印墨、彩色濾光片及其製造方法、固態攝影裝置、影像顯示裝置、液晶顯示器、有機電致發光顯示器及著色劑化合物以及其互變異構物 |
US11351106B2 (en) | 2020-09-14 | 2022-06-07 | Milliken & Company | Oxidative hair cream composition containing thiophene azo colorant |
US11344492B2 (en) | 2020-09-14 | 2022-05-31 | Milliken & Company | Oxidative hair cream composition containing polymeric colorant |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
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DE3400364A1 (de) * | 1984-01-07 | 1985-07-18 | Basf Ag, 6700 Ludwigshafen | Isothiazolazofarbstoffe |
DE3427201A1 (de) * | 1984-07-24 | 1986-01-30 | Basf Ag, 6700 Ludwigshafen | Heterocyclische azofarbstoffe |
DE3810643A1 (de) * | 1988-03-29 | 1989-10-12 | Basf Ag | Isothiazolazofarbstoffe |
DE3833442A1 (de) * | 1988-10-01 | 1990-04-12 | Basf Ag | Thiophenazofarbstoffe mit einer kupplungskomponente aus der thiazolreihe |
US5216139A (en) * | 1988-10-01 | 1993-06-01 | Basf Aktiengesellschaft | Thiopheneazo dye based on a coupling component of the thiazole series |
DE3910408A1 (de) * | 1989-03-31 | 1990-10-04 | Basf Ag | Azofarbstoffe, deren diazo- und kupplungskomponente aus der thiazolreihe stammt |
US4975410A (en) * | 1989-05-26 | 1990-12-04 | Eastman Kodak Company | Thermally-transferred color filter array element and process for preparing |
DE3917455A1 (de) * | 1989-05-30 | 1990-12-06 | Basf Ag | Benzisothiazolazofarbstoffe mit einer kupplungskomponente aus der thiazol- oder pyridinreihe |
US4933226A (en) * | 1989-12-11 | 1990-06-12 | Eastman Kodak Company | Thermal print element comprising a magenta 3-aryl-2-arylazo-5-aminothiazole or aminothiophene dye stabilized with a cyan indoaniline dye |
DE4003780A1 (de) * | 1990-02-08 | 1991-08-14 | Basf Ag | Verwendung von azofarbstoffen fuer den thermotransferdruck |
DE4004612A1 (de) * | 1990-02-15 | 1991-08-22 | Basf Ag | Neue bichromophore methin- und azamethinfarbstoffe und ein verfahren zu ihrer uebertragung |
DE4215495A1 (de) * | 1992-05-12 | 1993-11-18 | Basf Ag | Azofarbstoffe mit einer acetalisierten Diazokomponente aus der Thiophen- oder Thiazolreihe |
-
1994
- 1994-07-22 DE DE4426023A patent/DE4426023A1/de not_active Withdrawn
-
1995
- 1995-07-20 US US08/765,442 patent/US5789560A/en not_active Expired - Fee Related
- 1995-07-20 WO PCT/EP1995/002866 patent/WO1996003462A1/de not_active Application Discontinuation
- 1995-07-20 KR KR1019970700523A patent/KR970704834A/ko not_active Application Discontinuation
- 1995-07-20 EP EP95927678A patent/EP0773976B1/de not_active Expired - Lifetime
- 1995-07-20 DE DE59502608T patent/DE59502608D1/de not_active Expired - Lifetime
- 1995-07-20 CN CN95194882A patent/CN1157003A/zh active Pending
Cited By (1)
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---|---|---|---|---|
WO2016134556A1 (zh) * | 2015-02-28 | 2016-09-01 | 苏州帅马金属制品有限公司 | 板材表面图案制作工艺及其所制板材和家具 |
Also Published As
Publication number | Publication date |
---|---|
EP0773976B1 (de) | 1998-06-17 |
US5789560A (en) | 1998-08-04 |
EP0773976A1 (de) | 1997-05-21 |
DE4426023A1 (de) | 1996-01-25 |
DE59502608D1 (de) | 1998-07-23 |
KR970704834A (ko) | 1997-09-06 |
WO1996003462A1 (de) | 1996-02-08 |
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