CN104334647A - 反应性染料、其制备及其用途 - Google Patents
反应性染料、其制备及其用途 Download PDFInfo
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- CN104334647A CN104334647A CN201380029732.7A CN201380029732A CN104334647A CN 104334647 A CN104334647 A CN 104334647A CN 201380029732 A CN201380029732 A CN 201380029732A CN 104334647 A CN104334647 A CN 104334647A
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- Prior art keywords
- formula
- group
- chemically
- alkyl
- following formula
- Prior art date
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- 239000000985 reactive dye Substances 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title description 6
- 238000004043 dyeing Methods 0.000 claims abstract description 43
- 239000000463 material Substances 0.000 claims abstract description 34
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 22
- 150000002367 halogens Chemical class 0.000 claims abstract description 21
- 239000000835 fiber Substances 0.000 claims abstract description 16
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 16
- 239000004952 Polyamide Substances 0.000 claims abstract description 12
- 229920002647 polyamide Polymers 0.000 claims abstract description 12
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 11
- 239000011651 chromium Substances 0.000 claims abstract description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000460 chlorine Substances 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 7
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 6
- 239000010941 cobalt Substances 0.000 claims abstract description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 239000011737 fluorine Substances 0.000 claims abstract description 6
- 229910052742 iron Inorganic materials 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 39
- 238000007639 printing Methods 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- -1 β-chloroethyl Chemical group 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000000123 paper Substances 0.000 claims description 16
- 238000009833 condensation Methods 0.000 claims description 14
- 230000005494 condensation Effects 0.000 claims description 14
- 239000002657 fibrous material Substances 0.000 claims description 10
- 239000000434 metal complex dye Substances 0.000 claims description 8
- 239000004753 textile Substances 0.000 claims description 8
- 238000007641 inkjet printing Methods 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000976 ink Substances 0.000 claims description 4
- 239000002985 plastic film Substances 0.000 claims description 4
- 229920006255 plastic film Polymers 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 8
- 125000001424 substituent group Chemical group 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000000975 dye Substances 0.000 description 43
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000006210 lotion Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 229940083608 sodium hydroxide Drugs 0.000 description 6
- 230000008719 thickening Effects 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 229920002302 Nylon 6,6 Polymers 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 4
- 229910021538 borax Inorganic materials 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000004328 sodium tetraborate Substances 0.000 description 4
- 235000010339 sodium tetraborate Nutrition 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229940072056 alginate Drugs 0.000 description 3
- 235000010443 alginic acid Nutrition 0.000 description 3
- 229920000615 alginic acid Polymers 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 3
- 238000009940 knitting Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- XGRZWVWRMKAQNU-UHFFFAOYSA-K 2-carboxyphenolate;chromium(3+) Chemical compound [Cr+3].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O XGRZWVWRMKAQNU-UHFFFAOYSA-K 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920002334 Spandex Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 2
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 238000010612 desalination reaction Methods 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000004698 iron complex Chemical class 0.000 description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 238000009980 pad dyeing Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 235000019832 sodium triphosphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- ZSRQMIJBMBDHIE-UHFFFAOYSA-N 2-ethylbutane-1,1-diamine Chemical compound CCC(CC)C(N)N ZSRQMIJBMBDHIE-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 206010013786 Dry skin Diseases 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
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 240000008375 Hymenaea courbaril Species 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229920001410 Microfiber Polymers 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 229920000572 Nylon 6/12 Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 101710194948 Protein phosphatase PhpP Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
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- 229920004935 Trevira® Polymers 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 239000012928 buffer substance Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 1
- 239000011538 cleaning material Substances 0.000 description 1
- 150000004700 cobalt complex Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
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- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- ILRSCQWREDREME-UHFFFAOYSA-N lauric acid amide propyl betaine Natural products CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000009992 mercerising Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002939 oilproofing Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000933 poly (ε-caprolactam) Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 235000011091 sodium acetates Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000019830 sodium polyphosphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- NGSFWBMYFKHRBD-UHFFFAOYSA-N sodium;2-hydroxypropanoic acid Chemical compound [Na+].CC(O)C(O)=O NGSFWBMYFKHRBD-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009977 space dyeing Methods 0.000 description 1
- 239000004759 spandex Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000006886 vinylation reaction Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/095—Metal complex azo dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
- C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic Table compounds without a metal-carbon linkage
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
- C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
- C09B62/4411—Azo dyes
- C09B62/4416—Metal complex azo dyes
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- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
- D06P1/384—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes reactive group not directly attached to heterocyclic group
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/248—Polyamides; Polyurethanes using reactive dyes
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- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
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- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/30—Ink jet printing
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Abstract
式(1)的反应性染料,其中Me为铬、钴或铁,R1为氢或未取代或经取代的C1-C4烷基,E为式(1a)、(1b)或(1c)的二价基团,其中X表示氯或氟,T为式(2a)、(2b)、(2c)、(2d)、(2e)或(2f)的纤维反应性基团,(R3)0-2表示选自卤素、C1-C4烷基、C1-C4烷氧基和磺基的0至2个相同或不同的取代基,Z为乙烯基或-CH2-CH2-U基团,U为可在碱性条件下去除的基团,Q为-CH(Hal)-CH2-Hal或-C(Hal)=CH2基团,q为数值0或1,G为式(1d)或(1e)的二价基团,其中(R2)s表示选自卤素、硝基、未取代或卤素取代的C1-C4烷基、C2-C4烷酰氨基、C1-C4烷磺酰基、氨甲酰基、氨磺酰基、磺基和-E-T的s个相同或不同的取代基,其中E和T如上限定,s为数值0、1、2或3,A表示式(3a)、(3b)或(3c)的二价基团,其中R1、R2、X、T、q和s如上限定,R4和R7表示氢、C1-C4烷基、-COOH或-COO-C1-C4烷基,R5和R6分别相互独立表示选自羟基、卤素、硝基、未取代或卤素取代的C1-C4烷基、C1-C4烷氧基、C2-C4烷酰氨基、C1-C4烷磺酰基、氨甲酰基、氨磺酰基和磺基的相同或不同取代基,t和u分别相互独立为数值0、1、2或3,所述染料尤其适用于使合成聚酰胺纤维材料染色,并得到具有优良耐湿牢度性质的染色品或印刷品。
Description
本发明涉及新的藏青色反应性染料、其制备方法及其用于纺织纤维材料染色或印刷的用途。
近来,用反应性染料染色的实践导致对染色品品质和染色过程经济效率的更高需求。因此,仍需要尤其在其应用方面具有改善性质的新反应性染料。
现今,染色品需要具有足够直接性同时具有洗净未固定染料的良好便利性的反应性染料。它们也应具有良好的得色量和高反应性,目的是要尤其提供具有高固定度的染色品。已知染料并不在所有性质上满足这些要求。
至今只可用酸性染料得到在聚酰胺上的深色染色品,但这些染色品在高温不耐湿。可只用反应性染料得到同时永久耐湿的深色染色品。
因此,本发明的根本问题是对于纤维材料的染色和印刷寻找在很高程度上具有以上表征品质的新的改良反应性染料,尤其在用染料使合成聚酰胺纤维材料染色时。新染料应特征在于高固定率和高纤维-染料结合稳定性。染料尤其应产生具有优良的多方面牢度性质的染色品,例如,耐光牢度、耐湿牢度和耐氯牢度。
具体地讲,需要一种高亮反应性染料,所述染料适用于使合成聚酰胺微纤维染色,并提供具有高耐光牢度和耐湿牢度的染色品,尤其是藏青色。
已发现,通过以下限定的新染料,在很大程度上解决了所提出的问题。
因此,本发明涉及下式的反应性染料
其中Me为铬、钴或铁,
R1为氢或未取代或经取代的C1-C4烷基,
E为下式的二价基团
或
其中X表示氯或氟,
T为下式的纤维反应性基团
或
(R3)0-2表示选自卤素、C1-C4烷基、C1-C4烷氧基和磺基的0至2个相同或不同的取代基,
Z为乙烯基或-CH2-CH2-U基团,U为可在碱性条件下去除的基团,
Q为-CH(Hal)-CH2-Hal或-C(Hal)=CH2基团,
q为数值0或1,
G为下式的二价基团
或
其中(R2)s表示选自卤素、硝基、未取代或卤素取代的C1-C4烷基、C2-C4烷酰氨基、C1-C4烷磺酰基、氨甲酰基、氨磺酰基、磺基和-E-T的s个相同或不同的取代基,其中E和T如上限定,
s为数值0、1、2或3,
A表示下式的二价基团
或
其中R1、R2、X、T、m、n、q和s如上限定,
R4和R7表示氢、C1-C4烷基、-COOH或-COO-C1-C4烷基,
R5和R6分别相互独立表示选自羟基、卤素、硝基、未取代或卤素取代的C1-C4烷基、C1-C4烷氧基、C2-C4烷酰氨基、C1-C4烷磺酰基、氨甲酰基、氨磺酰基和磺基的相同或不同取代基,t和u分别相互独立为数值0、1、2或3。
在式(2c)的基团中,Me为甲基,Et为乙基。除了氢外,所述基团还适合作为氮原子上的取代基。
对于R1至R7,所考虑的C1-C4烷基分别相互独立为例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基或异丁基,优选甲基或乙基,尤其甲基。在R1的情况下,所述烷基未被取代或被例如羟基、磺基、硫酸基、氰基、羧基、C1-C4烷氧基或被苯基取代,优选被羟基、硫酸基、C1-C4烷氧基或被苯基取代。对于R1,相应的未取代基团是优选的。
对于R2、R5和R6,所考虑的C1-C4烷基为例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基或异丁基,优选甲基或乙基,尤其甲基。所述烷基未被取代或被卤素单取代或多取代,例如,被氟、氯或溴取代,优选被氟或氯取代。
对于R3,所考虑的C1-C4烷氧基为例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基或异丁氧基,优选甲氧基或乙氧基,尤其甲氧基。
对于R2、R3、R5和R6,所考虑的卤素分别相互独立为例如氟、氯或溴,优选氯。
对于R2,所考虑的C2-C4烷酰氨基为例如乙酰氨基或丙酰氨基,优选乙酰氨基。
对于R2、R5和R6,所考虑的C1-C4烷磺酰基为例如甲磺酰基、乙磺酰基、正丙磺酰基、异丙磺酰基或正丁磺酰基,优选甲磺酰基或乙磺酰基。
表示氨甲酰基的R2、R5和R6相当于式-CONH2的基团。
表示氨磺酰基的R2、R5和R6相当于式-SO2NH2的基团。
R1优选为氢。
优选(R2)s表示选自卤素、硝基、C2-C4烷酰氨基和磺基的相同或不同取代基,尤其硝基和磺基,更尤其硝基。
优选(R3)0-2表示选自C1-C4烷基、C1-C4烷氧基和磺基的0至2个相同或不同的取代基,尤其甲基、甲氧基和磺基。
尤其优选式(2c)不含取代基R3。
T优选为式(2c)、(2d)、(2e)或(2f)的基团,尤其式(2c)或(2d)的基团,更尤其式(2c)的基团。
式(2f)的纤维反应性基团中的Hal优选为氯或溴,尤其溴。
所考虑的离去基团U为例如-Cl、-Br、-F、-OSO3H、-SSO3H、-OCO-CH3、-OPO3H2、-OCO-C6H5、-OSO2-C1-C4烷基或-OSO2-N(C1-C4烷基)2。优选U为式-Cl、-OSO3H、-SSO3H、-OCO-CH3、-OCO-C6H5或-OPO3H2的基团,尤其-Cl或-OSO3H。
因此,适合基团Z的实例为乙烯基、β-溴-或β-氯乙基、β-乙酰氧基乙基、β-苯甲酰基氧基乙基、β-磷酸根合乙基、β-硫酸根合乙基和β-硫代硫酸根合乙基。Z优选为乙烯基、β-氯乙基或β-硫酸根合乙基,尤其乙烯基。
s优选为数值0、1或2,尤其是数值0或1,更尤其是数值0。
q优选为数值0。
Me优选为铬。
E优选为下式的二价基团
或
特别是式(1a1)的基团。
式(2c)的基团优选为下式的基团
或
。
A优选表示下式的二价基团
或
。
在式(1)中,取代基-NR1-ET优选在萘基的8-位,其中氧原子结合到1-位。
在式(1)中,第二磺基取代基优选在萘基的5-位或6-位,最优选在6-位,其中氧原子结合到1-位。
本发明还涉及制备以上限定的式(1)的反应性染料的方法,其中E为式(1a)的基团,所述方法包括
(i)从下式的化合物
和
使用适合的铬、钴或铁化合物,制备下式的1:2金属络合物染料
和
(ii)在第一缩合步骤,使根据(i)得到的式(6)的1:2金属络合物染料与下式的氰尿酰卤缩合
和
(iii)在第二缩合步骤,使根据(ii)得到的下式的初步缩合产物
与下式的化合物缩合
或者
(iv)使根据(i)得到的式(6)的1:2金属络合物染料与下式的化合物缩合
R1、Me、X、T、A、G和q分别具有以上所给的定义。
式(6)的适合氰尿酰卤为氰尿酰氯。
式(10)的化合物已知或者可类似于已知方法制备,例如通过式(6)的氰尿酰卤与式(9)的化合物缩合,其中T具有以上所给的定义和优选意义。
式(6)的1:2铬络合物染料已知,或者可类似于已知化合物制备,例如,通过使下式的1:1铬络合物
与式(5)的偶氮化合物反应,A、G、T、R1和q分别具有以上所给的定义和优选意义。
式(11)的1:1铬络合物与式(5)的偶氮化合物的反应在含水介质中进行,在例如40至130℃的温度,尤其70至100℃,在例如8至14的pH值,尤其在10至13的pH值。反应更有利地在无机酸中和介质或碱性介质存在下进行,例如,在碱金属碳酸盐、碱金属乙酸盐或碱金属氢氧化物存在下,优选的碱金属为钠。
如果A不是对称基团,则根据(i)制备的式(6)的1:2金属络合物通常包括两个配位异构体。
除了本发明上下文中以化学式(例如式(1)、(6)和(8))形式公开的金属络合物外,应认为本公开也包括相应的配位异构体。
式(4)、(5)、(9)和(11)的化合物已知,或者可类似于已知方法得到。
例如,可根据常规铬化方法得到式(11)的1:1铬络合物,其中与铬盐的反应可例如在含水介质中进行,任选在压力下,在例如90至130℃的温度。适合的铬盐为例如乙酸铬(III)、硝酸铬(III)、氯化铬(III)、水杨酸铬(III)和硫酸铬(III)。
式(4)和(5)的化合物可根据常用重氮化和偶联反应得到。重氮化一般通过亚硝酸的作用来进行,在含水无机酸溶液中在低温下例如0至20℃;偶联有利地在碱性pH值进行,例如在8至12的pH值。
式(4)和(5)的偶氮化合物的1:2钴或铁络合物染料已知,或者可类似于已知方法得到。
1:2铬或1:2钴络合物染料可例如类似于GB-A-716 753、GB-A-719 274、GB-A-745 641和GB-A-851 861中所述的方法得到。1:2铁络合物染料可例如类似于US 5 376 151中所述的方法得到。
缩合反应通常在水溶液中在例如0至50℃的温度和例如2至10的pH值下以本身已知的方式进行。
式(6)的1:2金属络合物染料与式(7)的氰尿酰卤根据(ii)的缩合优选在0至5℃温度和3至6的pH值下进行。式(8)的初步缩合产物与式(9)的化合物根据(iii)的缩合优选在0至30℃的温度和4至7的pH值下进行。式(5)的1:2金属络合物染料与式(10)的化合物根据(iv)的缩合优选在20至50℃的温度和4至6的pH值下进行。
应了解,式(1)包括在多阶段合成期间产生的所有不同配位异构体。
另外,应了解,式(1)包括可由质子迁移产生的互变异构体。
另外,可任选使最终产物经受转化反应。这种转化反应为例如可乙烯基化反应性基团T(Z或Q)通过用稀氢氧化钠溶液处理转化成其乙烯基形式,例如,诸如β-硫酸根合乙基磺酰基或β-氯乙基磺酰基转化成乙烯基磺酰基,或者α,β-二卤丙酰氨基转化成α-卤丙烯酰氨基。这些反应本身是已知的。转化反应一般在中性至碱性介质中在例如20至70℃的温度在例如6至14的pH值下进行。
可以类似方式制备其中E为式(1b)或(1c)的基团的式(1)的反应性染料。
式(1)的反应性染料包含磺基,这些磺基分别为游离磺酸的形式,或者优选为其盐的形式,例如钠、锂、钾或铵盐,或者有机胺盐,例如三乙醇铵盐。
式(1)的反应性染料可包含其它添加剂,例如氯化钠或糊精。
本发明的式(1)的反应性染料可任选包含例如改善处理或提高储存稳定性的其它辅助剂,例如诸如缓冲剂、分散剂或防尘剂。这些辅助剂为本领域的技术人员所熟悉。
本发明的反应性染料例如适用于含羟基或含氮纤维材料染色或印刷。可提及的实例为丝绸、羊毛、各种纤维素纤维材料和聚氨酯及聚酰胺纤维。纤维素纤维材料为例如天然纤维素纤维(例如棉、亚麻和大麻)和纤维素及再生纤维素。本发明的反应性染料也适用于在混纺织物中存在的含羟基纤维染色或印刷,例如,棉与聚酯纤维或聚酰胺纤维的混纺物。
优选对天然或合成聚酰胺纤维材料染色或印刷,尤其合成聚酰胺纤维材料,例如诸如聚酰胺6(聚ε-己内酰胺)、聚酰胺6,6(聚己二酰己二胺)、聚酰胺7、聚酰胺6,12(聚十二烷酰己二胺)、聚酰胺11或聚酰胺12;与聚酰胺6,6或聚酰胺6的共聚酰胺,例如诸如己二胺、ε-己内酰胺和己二酸的聚合物,和己二酸、己二胺和间苯二甲酸的聚合物,或己二酸、己二胺和2-甲基戊二胺或2-乙基丁二胺的聚合物。本发明的式(1)的反应性染料还适用于对合成聚酰胺和羊毛的混纺织物或纱染色或印刷。
本发明的方法也有利地适用于对合成聚酰胺的微纤维染色或印刷。应了解,微纤维是指由具有小于1旦(1.1 dTex)单丝细度的丝制成的纤维材料。这些微纤维已知,通常通过熔纺制备。
所述纺织材料可以采用很多种加工形式,例如采用纤维、纱、机织织物或针织织物的形式和毡毯形式。
式(1)的反应性染料可根据常用染色和印刷方法用于染色或印刷。除了包含水和染料外,染色液体或印刷糊还可包含其它添加剂,例如湿润剂、防沫剂、匀染剂或影响纺织材料性质的剂(例如软化剂、用于阻燃整理的添加剂或防污剂、防水剂和防油剂)以及水软化剂和天然或合成增稠剂(例如藻酸盐和纤维素醚)。
在织毯材料的情况下,印刷方法是重要的,例如置换印刷或间隔染色。
优选尤其根据尽染方法进行的染色,在毯染色的情况下,也可根据连续方法进行。
染色优选在2至7的pH值进行,尤其2.5至5.5,更尤其3至4.5。液体比可在宽范围选择,例如1:5至1:50,优选1:5至1:30。染色优选在80至130℃温度进行,尤其85至120℃。
式(1)的反应性染料得到具有优良的多方面性质的均匀染色品,例如,优良的耐氯牢度、耐摩擦牢度、耐湿牢度、耐湿-摩擦牢度、耐洗牢度、耐水牢度、耐海水牢度和耐汗牢度及优良的耐光牢度。它们特征还在于均匀的颜色积累、优良的亲合性、高反应性、优良的固定能力和极佳的积累能力。本发明的染料具有优良的水溶解性,并且可容易与其它染料组合。
本发明的式(1)的染料也适合作为记录系统使用的着色剂。此类记录系统为例如用于纸或纺织品印刷的市售喷墨印刷机或书写工具,例如钢笔或圆珠笔,尤其是喷墨印刷机。对于该用途,首先使本发明的染料形成适用于记录系统的形式。适合的形式为例如包含本发明的染料作为着色剂的水性油墨。通过单独组分在所需量的水中一起混合,可以通常方式制备油墨。
所考虑的基材为上述含羟基或含氮纤维材料,尤其天然或合成聚酰胺纤维材料。纤维材料优选为纺织纤维材料。
所考虑的基材也可为纸和塑料膜。
可提及的纸的实例为市售可得的喷墨纸(ink-jet paper)、相纸、光泽纸、塑料涂覆纸,例如Epson喷墨纸、Epson相纸、Epson光泽纸、Epon光泽膜、HP特种喷墨纸、Encad光泽相纸和Ilford相纸。塑料膜例如透明或模糊/不透明。适合的塑料膜为例如3M透明膜。
根据用途特性,例如,纺织品印刷或纸印刷,可能有必要例如相应改变油墨的粘度或其它物理性质,尤其对所讨论的基材的亲合性有影响的性质。
在水性油墨中使用的染料应优选具有低盐含量,即,它们应具有基于染料重量小于0.5%重量的总盐含量。例如,通过膜分离过程,例如超滤、反渗透或渗析,可使由于其制备和/或由于随后加入稀释剂而具有相对高盐含量的染料脱盐。
油墨优选具有基于油墨总重量1至35%重量的总染料含量,尤其1至30%重量,优选1至20%重量。在此情况下,优选的下限为1.5%重量,优选2%重量,尤其3%重量。
油墨可包含水混溶性有机溶剂,例如C1-C4醇,例如,甲醇、乙醇、正丙醇、异丙醇、正丁醇、仲丁醇、叔丁醇或异丁醇;酰胺,例如,二甲基甲酰胺或二甲基乙酰胺;酮或酮醇,例如丙酮或双丙酮醇;醚,例如四氢呋喃或二氧杂环己烷;含氮杂环化合物,例如N-甲基-2-吡咯烷酮或1,3-二甲基-2-咪唑烷酮;聚烷二醇,例如聚乙二醇或聚丙二醇;C2-C6烷二醇和硫代二醇,例如乙二醇、丙二醇、丁二醇、二缩三乙二醇、硫代二甘醇、己二醇和一缩二乙二醇;其它多元醇,例如甘油或1,2,6-己三醇;和多元醇的C1-C4烷基醚,例如,2-甲氧基-乙醇、2-(2-甲氧基乙氧基)乙醇、2-(2-乙氧基乙氧基)乙醇、2-[2-(2-甲氧基乙氧基)-乙氧基]乙醇或2-[2-(2-乙氧基乙氧基)乙氧基]乙醇;优选N-甲基-2-吡咯烷酮、一缩二乙二醇、甘油或尤其1,2-丙二醇,通常为基于油墨总重量2至30%重量,尤其5至30%重量,优选10至25%重量的量。
另外,油墨也可包含增溶剂,例如ε-己内酰胺。
油墨可包含天然或合成来源的增稠剂,尤其用于调节粘度。
可提及的增稠剂的实例包括市售可得的藻酸盐增稠剂、淀粉醚或刺槐豆粉醚,尤其藻酸钠本身或其与改性纤维素的混合物,改性纤维素如甲基纤维素、乙基纤维素、羧甲基纤维素、羟乙基纤维素、甲基羟乙基纤维素、羟丙基纤维素或羟丙基甲基纤维素,尤其优选与20至25%重量羧甲基纤维素混合。也可提及的合成增稠剂为例如基于聚(甲基)丙烯酸或聚(甲基)丙烯酰胺和具有例如2000至20000分子量的聚烷二醇的那些增稠剂,聚烷二醇例如诸如聚乙二醇或聚丙二醇或环氧乙烷和环氧丙烷的混合聚烷二醇。
油墨包含例如基于油墨总重量0.01至2%重量的这些增稠剂,尤其0.01至1%重量,优选0.01至0.5%重量。
油墨也可包含缓冲物质,例如硼砂、硼酸盐、磷酸盐、多磷酸盐或柠檬酸盐。可提及的实例包括硼砂、硼酸钠、四硼酸钠、磷酸二氢钠、磷酸氢二钠、三聚磷酸钠、五聚磷酸钠和柠檬酸钠。为了确立例如4至9的pH值,尤其5至8.5,它们尤其以基于油墨总重量0.1至3%重量的量使用,优选0.1至1%重量。
油墨可包含表面活性剂或湿润剂作为另外的添加剂。
适合的表面活性剂包括市售可得的阴离子或非离子表面活性剂。所考虑的本发明油墨中的湿润剂为例如尿素或乳酸钠(有利地采用50%至60%水溶液形式)和优选0.1至30%重量(尤其2至30%重量)量的甘油和/或丙二醇的混合物。
优选油墨具有1至40mPa·s粘度,尤其1至20mPa·s,更尤其1至10mPa·s。
另外,油墨还可额外包含常用添加剂,例如防沫剂或尤其抑制真菌和/或细菌生长的防腐剂。此类添加剂通常以基于油墨总重量0.01至1%重量的量使用。
所考虑的防腐剂为甲醛产生剂,例如,低聚甲醛和三氧杂环己烷,尤其约30至40%重量甲醛水溶液;咪唑化合物,例如2-(4-噻唑基)-苯并咪唑;噻唑化合物,例如1,2-苯并异噻唑啉-3-酮或2-正辛基-异噻唑啉-3-酮;碘化合物、腈、酚、卤代烷基硫基化合物或吡啶衍生物,尤其1,2-苯并异噻唑啉-3-酮或2-正辛基-异噻唑啉-3-酮。适合的防腐剂为例如一缩二丙二醇中1,2-苯并异噻唑啉-3-酮的20%重量溶液(Proxel® GXL)。
油墨也可包含基于油墨总重量例如0.01至1%重量的其它添加剂,例如氟化聚合物或调聚物,例如聚乙氧基全氟醇(Forafac®或Zonyl®产品)。
在喷墨印刷方法的情况下,将单独油墨滴从喷嘴以控制方式喷到基材上。用于该用途的主要是连续喷墨方法和按需喷墨方法。在连续喷墨方法的情况下,液滴连续产生,印刷操作不需要的液滴排入贮器并再循环。另一方面,在按需喷墨方法的情况下,液滴按需要产生并用于印刷,即,只在印刷操作需要时产生液滴。例如,通过压电喷墨头或热能(泡压喷墨)实现液滴产生。优选通过压电喷墨头印刷和根据连续喷墨方法印刷。
因此,本发明也涉及包含本发明的式(1)的染料的水性油墨,和此类油墨在喷墨印刷方法中用于印刷多种基材(尤其纺织纤维材料)的用途,以上所示定义和优选项适用于染料、油墨和基材。
以下实施例用于说明本发明。除非另外指明,否则温度以摄氏度给出,份数为重量份数,百分数是指%重量。重量份数是指以千克与升的比率计的体积份。
实施例
1
:
(a)将26.4份游离酸形式的对应于下式的化合物
搅拌入100份水中。浆料通过加入约50份冰冷却到0℃,用氢氧化钠水溶液调节至pH 3,温度通过用冰冷却保持在0℃。所得溶液缓慢送入18.2份氰尿酰氯在20份水中的浆料、约80份冰和0.2份Na2HPO4·12H2O中,pH通过加入氢氧化钠水溶液保持在3,温度通过加冰保持在0℃。得到悬浮液,悬浮液包含本文指示为游离酸形式的下式的化合物
。
(b)将39份游离酸形式的对应于下式的化合物
与550份水、15份甲酸和6.8份乙酸铬(III)制成浆料,并在100至105℃温度下在压热器中加热20小时。压力为约3bar。在冷却到室温后,将沉淀的产物滤出,用水洗涤,并在真空中在50℃温度干燥。得到游离酸形式的对应于下式的1:1络合物
。
(c)将42.2份游离酸形式的对应于下式且已根据通常方法从重氮化2-氨基苯酚和1-氨基-8-萘酚-3,6-二磺酸制备的单偶氮染料
与600份水中的根据(b)得到的47份铬络合物一起搅拌至均匀,并加热到70℃。确立8.0至8.5的pH值,并通过加入2N氢氧化钠溶液保持。然后在以上温度搅拌,直到在所得澄清溶液中不能检测到两种起始化合物的任一种。得到游离酸形式的对应于下式的异构配位化合物
和 。
(d)使澄清溶液冷却到50℃,通过加入含水盐酸将pH调节到约5的值,缓慢加入根据(a)得到的悬浮液,pH通过加入氢氧化钠水溶液保持在5的值。为了完成反应,进行搅拌另外两小时。随后,在室温用pH值为10-11的氢氧化钠处理该溶液约两小时。得到的溶液通过在pH 6至7渗析除盐,并通过蒸发浓缩至干。得到游离酸形式的染料,对应于下式的化合物及其配位异构体(λmax=586nm)
,
并得到在含氨基的纤维上具有极佳多方面牢度性质的藏青色染色品或印刷品。
实施例
2
至
12
可以类似于实施例1中所述的方式得到下式的染料
(除了以化学式形式公开的式(102)至(112)的染料外,应认为本公开也包括相应的配位异构体)。
染色程序
1
:
使10份聚酰胺6,6纤维材料(Helanca
tricot)在用乙酸调节至pH 3的500份含水液体中染色。实施例1的染料比例为基于纤维重量的2%。在98℃温度的染色时间为30至90分钟。然后移出经染色的纤维材料,用水清洗,并在20至30分钟过程中在pH 10至11.5和70至90℃的纯碱洗涤液中清除未固定的染料。再次用水清洗并在乙酸浴液中酸化至pH 4后,使纤维材料干燥。得到具有卓越的耐光牢度和耐湿牢度性质的藏青色染色品。
染色程序
2
:
用含3g甲酸、0.4g润湿剂和0.7g匀染剂的1.5升液体,将由72%聚酰胺微纤维和28%弹性纤维(elastane)组成的70g混纺织物在染色装置中在40℃处理10分钟。液体的pH为2.9。然后加入预先溶于少量水的3.8g实施例1的染料。将要染色的材料在40℃在染色液体中处理5分钟,然后加热到100℃,并在该温度干燥20分钟。随后加入14g氯化钙,然后进行染色40分钟。染色后,将材料在70至90℃用含2g 1,6-己二胺的1.5升后处理浴液处理20分钟。然后清洗材料,并以常规方式整理。得到具有极佳牢度性质的深度匀染染色品(耐洗牢度根据AATCC 16E:注解5).
为了进一步改善牢度性质,可增加常规固定后步骤或碱性后处理。对于碱性后处理,将染色品在60至80℃在含2g/l纯碱且具有pH 9.2的新浴液中处理20分钟。
染色程序
3
:
将染料浴液用于聚酰胺6,6织毯材料的连续染色,每1000份染料浴液包含3份实施例1的染料和1份市售可得的增稠剂、1份非离子润湿剂及产生pH 5.0的染料浴液所需的柠檬酸量。然后使织毯材料在蒸汽中在100℃固定5分钟,洗涤并以通常方式干燥。织毯材料特征在于具有优良牢度性质的均匀藏青色染色品。
染色程序
4
:
将10份羊毛针织纱在30℃搅入染料浴液,所述染料浴液每100份水包含1.6份实施例1的染料、0.5份硫酸钠和2份乙酸钠,且已用乙酸(80%)调节到pH值4.5。在45分钟过程中使液体沸腾,并在沸腾温度保持另外45至70分钟。然后移出经染色材料,彻底用冷水清洗,并干燥。得到具有极佳牢度性质的藏青色染色品。
印刷程序
I
(a)将丝光棉缎用含30g/l碳酸钠和50g/l尿素的液体轧染(70%液体轧染率),并干燥。
(b)使用按需喷墨喷墨头(泡压喷墨),将根据步骤(a)预处理的棉缎用水性油墨印刷,所述水性油墨包含
- 15%重量实施例1的式(101)的反应性染料,
-
15%重量1,2-丙二醇,和
-
70%重量水。
使印刷品完全干燥,并在饱和蒸汽中在102℃固定8分钟,冷清洗,在沸腾下洗净,再次清洗,并干燥。
Claims (13)
1. 一种下式的反应性染料
其中Me为铬、钴或铁,
R1为氢或未取代或经取代的C1-C4烷基,
E为下式的二价基团
或,
其中X表示氯或氟,
T为下式的纤维反应性基团
或
(R3)0-2表示选自卤素、C1-C4烷基、C1-C4烷氧基和磺基的0至2个相同或不同的取代基,
Z为乙烯基或-CH2-CH2-U基团,U为可在碱性条件下去除的基团,
Q为-CH(Hal)-CH2-Hal或-C(Hal)=CH2基团,
q为0或1,
G为下式的二价基团
或
其中(R2)s表示选自卤素、硝基、未取代或卤素取代的C1-C4烷基、C2-C4烷酰氨基、C1-C4烷磺酰基、氨甲酰基、氨磺酰基、磺基和-E-T的s个相同或不同的取代基,其中E和T如上限定,s为数值0、1、2或3,
A表示下式的二价基团
或
其中R1、R2、X、T、q和s如上限定,
R4和R7表示氢、C1-C4烷基、-COOH或-COO-C1-C4烷基,
R5和R6分别相互独立表示选自羟基、卤素、硝基、未取代或卤素取代的C1-C4烷基、C1-C4烷氧基、C2-C4烷酰氨基、C1-C4烷磺酰基、氨甲酰基、氨磺酰基和磺基的相同或不同取代基,t和u分别相互独立为数值0、1、2或3。
2. 权利要求1的式(1)的反应性染料,其中R1为氢。
3. 权利要求1或2的式(1)的反应性染料,其中Z为乙烯基、β-氯乙基或β-硫酸根合乙基。
4. 权利要求1至3中任一项的式(1)的反应性染料,其中T为下式的纤维反应性基团
或
。
5. 权利要求1至4中任一项的式(1)的反应性染料,其中q为数值0。
6. 权利要求1至5中任一项的式(1)的反应性染料,其中s为数值0。
7. 权利要求1至6中任一项的式(1)的反应性染料,其中A表示下式的二价基团
或
。
8. 权利要求1至6中任一项的式(1)的反应性染料,其中G表示式(1d)的二价基团,其中s为数值0。
9. 一种制备权利要求1的式(1)的反应性染料的方法,其中E为式(1a)的基团,所述方法包括
(i)从下式的化合物
和
使用适合的铬、钴或铁化合物,制备下式的1:2金属络合物染料
和
(ii)在第一缩合步骤,使根据(i)得到的式(6)的1:2金属络合物染料与下式的氰尿酰卤缩合
和
(iii)在第二缩合步骤,使根据(ii)得到的下式的初步缩合产物
与下式的化合物缩合
T-H (9),
或
(iv)使根据(i)得到的式(6)的1:2金属络合物染料与下式的化合物缩合
R1、Me、X、T、A、G和q分别具有权利要求1所给的定义。
10. 权利要求1至8中任一项的反应性染料或根据权利要求9制备的反应性染料用于含羟基或含氮纤维材料的染色或印刷的用途。
11. 权利要求10的用途,其中对天然或合成聚酰胺纤维材料尤其是合成聚酰胺纤维材料染色或印刷。
12. 一种水性油墨,所述水性油墨包含权利要求1的式(1)的反应性染料。
13. 一种根据喷墨印刷方法印刷纺织纤维材料、纸或塑料膜的方法,所述方法包括使用权利要求12的水性油墨。
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CN105647238A (zh) * | 2016-03-17 | 2016-06-08 | 浙江瑞华化工有限公司 | 一种灰色活性染料组合物及其制备方法和用途 |
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RU2014146197A (ru) | 2016-07-27 |
JP2015529690A (ja) | 2015-10-08 |
ES2639092T3 (es) | 2017-10-25 |
IN2014DN07971A (zh) | 2015-05-01 |
PT2855597T (pt) | 2017-09-14 |
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KR102055110B1 (ko) | 2019-12-13 |
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Effective date of registration: 20230407 Address after: Basel, SUI Patentee after: Huntsman Textile Dyeing (Switzerland) Co.,Ltd. Address before: Basel, SUI Patentee before: HUNTSMAN ADVANCED MATERIALS (SWITZERLAND) GmbH |