CN104968732B - 不含金属的活性染料,及其制备方法和应用 - Google Patents
不含金属的活性染料,及其制备方法和应用 Download PDFInfo
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- CN104968732B CN104968732B CN201380032388.7A CN201380032388A CN104968732B CN 104968732 B CN104968732 B CN 104968732B CN 201380032388 A CN201380032388 A CN 201380032388A CN 104968732 B CN104968732 B CN 104968732B
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- Prior art keywords
- group
- halogen
- product
- alkoxy
- alkyl
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 239000000985 reactive dye Substances 0.000 title abstract description 6
- -1 formamido group Chemical group 0.000 claims abstract description 139
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 55
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 238000004043 dyeing Methods 0.000 claims abstract description 21
- 239000000463 material Substances 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 132
- 229910052736 halogen Inorganic materials 0.000 claims description 71
- 150000002367 halogens Chemical class 0.000 claims description 71
- 125000003545 alkoxy group Chemical group 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 63
- 125000002252 acyl group Chemical group 0.000 claims description 59
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000004423 acyloxy group Chemical group 0.000 claims description 51
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 50
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 50
- 125000001072 heteroaryl group Chemical group 0.000 claims description 49
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 48
- 125000003441 thioacyl group Chemical group 0.000 claims description 47
- 125000004685 alkoxythiocarbonyl group Chemical group 0.000 claims description 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 46
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 45
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 125000005333 aroyloxy group Chemical group 0.000 claims description 36
- 125000003435 aroyl group Chemical group 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 34
- 239000000835 fiber Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 238000005859 coupling reaction Methods 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000012954 diazonium Substances 0.000 claims description 9
- 150000001989 diazonium salts Chemical class 0.000 claims description 9
- 230000008878 coupling Effects 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 6
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 238000006193 diazotization reaction Methods 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Chemical group 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Chemical group 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 229920002994 synthetic fiber Polymers 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 150000002892 organic cations Chemical class 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 239000012209 synthetic fiber Substances 0.000 claims 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 58
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 9
- 150000004696 coordination complex Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 description 23
- 239000005864 Sulphur Chemical group 0.000 description 16
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 16
- 239000000976 ink Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000007639 printing Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000004744 fabric Substances 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000219146 Gossypium Species 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 125000005518 carboxamido group Chemical group 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 2
- 229940015975 1,2-hexanediol Drugs 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- WKFQMDFSDQFAIC-UHFFFAOYSA-N 2,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CC(C)S(=O)(=O)C1 WKFQMDFSDQFAIC-UHFFFAOYSA-N 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 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
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- IIPYXGDZVMZOAP-UHFFFAOYSA-N lithium nitrate Chemical compound [Li+].[O-][N+]([O-])=O IIPYXGDZVMZOAP-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 229960004063 propylene glycol Drugs 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- HFIYIRIMGZMCPC-YOLJWEMLSA-J remazole black-GR Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(\N=N\C=3C=CC(=CC=3)S(=O)(=O)CCOS([O-])(=O)=O)C(O)=C2C(N)=C1\N=N\C1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 HFIYIRIMGZMCPC-YOLJWEMLSA-J 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- 239000004317 sodium nitrate Substances 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 239000004034 viscosity adjusting agent Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-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
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- 229940031723 1,2-octanediol Drugs 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- HGQSNMTUSGIWTJ-UHFFFAOYSA-N 1,3-bis(methoxymethyl)imidazolidine Chemical compound COCN1CCN(COC)C1 HGQSNMTUSGIWTJ-UHFFFAOYSA-N 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- WDQFELCEOPFLCZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrolidin-2-one Chemical compound OCCN1CCCC1=O WDQFELCEOPFLCZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0047—Mixtures of two or more reactive azo dyes
- C09B67/005—Mixtures of two or more reactive azo dyes all the reactive groups being not directly attached to a heterocyclic system
-
- 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
- C09B62/44—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
- C09B62/4415—Disazo or polyazo dyes
-
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
活性染料及其金属配合物,及制备方法和应用本发明涉及式(I)所示染料及其混合物
Description
本发明涉及活性染料技术领域,所述活性染料用于包含羟基,氨基,和/或甲酰氨基的材料的染色和印花。
不含金属的活性染料是现有技术已知的,并可作为着色剂在不同应用中使用,参见例子US005817779A,CH695613A5。
然而,在包含羟基,氨基和/或甲酰氨基材料的染色和印花的背景技术中,现有的不含金属的染料具有许多技术缺陷,比如耐光性不佳,以及特别是在实现深色调中的限制,所述深色调如深褐色,紫色,海军蓝和黑色。
令人惊奇的是,现已发现如下所述的式(I)所示的染料与已知染料相比,显示出极为优越的性能。这些三偶氮或四偶氮染料可以提升在上述材料及其混纺物上的深色调,同时所述深色调具有优异的耐光性和良好的总体染色牢度性能。最为重要的是,式(I)所示的染料是不含金属的,因此具有优异的生态性能并提供了均染度非常好的染色。本发明不包括双偶氮染料。
本发明涉及式(I)所示染料及其混合物
其中,
A和C,各自独立为,通式(1a)所示的基团
其中,
R3~R5,各自独立为,氢,卤素,烷基,N-酰氨基,烷氧基,硫代烷氧基,羟基,氰基,硝基,烷氧基羰基,烷氧基硫代羰基,酰基,硫代酰基,芳酰基,三氟甲基,酰氧基,芳酰氧基,环烷基,芳基,杂芳基,杂环烷基,N-肉桂酰氨基,SO3M或COOM;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
或为SO2-X,其中X是乙烯基或基团–CH2CH2-Y,并且Y是在碱性条件下可离去的基团,如OSO3M,SSO3M,OCOCH3,OPO3M或卤素;
或为通式(2a),(2b)或(2c)所示的基团
其中,
R6和R9,各自独立为,氢,卤素,烷基,N-酰氨基,烷氧基,硫代烷氧基,羟基,氰基,烷氧基羰基,烷氧基硫代羰基,酰基,硫代酰基,芳酰基,三氟甲基,酰氧基,芳酰氧基,环烷基,芳基,杂芳基,杂环烷基,SO3M或COOM;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N-酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基或芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N-酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基或芳酰氧基;
R7,R8,R10和R14,各自独立为,氢,烷基,环烷基或芳基;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N-酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基或芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N-酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基或芳酰氧基;
R11~R13,各自独立为,氢,卤素,烷基,烷氧基或SO3M;
c是0~6的整数;
d是1~6的整数;
当c和d,各自独立为≥2的整数时,R6和R9可以在上述所定义的相同的基团含义范围内,具有不同的含义;
e是0或1;
RG是通式(3a),(3b)或(3c)所示的活性锚;
其中,
R16~R21,各自独立为,卤素;
另外,R16可以是式(4a)所示的基团
其中,
R22是氢,卤素,烷基,烷氧基,硫代烷氧基,羟基,环烷基,芳基,杂芳基,杂环烷基,SO3M或COOM;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N-酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基或芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N-酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基或芳酰氧基;
R15选自通式(5a)或(5b)所示基团之一;
其中,
R23,R24和R26,各自独立为,氢,烷基,环烷基或芳基;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N-酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基或芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N-酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基或芳酰氧基;
R25,R27和R28,各自独立为,氢,卤素,烷基,N-酰氨基,烷氧基,硫代烷氧基,羟基,氰基,烷氧基羰基,烷氧基硫代羰基,酰基,硫代酰基,芳酰基,氨基磺酰基,三氟甲基,酰氧基,芳酰氧基,环烷基,芳基,杂芳基,杂环烷基,SO3M或COOM;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N-酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基或芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N-酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基或芳酰氧基;
另外,R24可以是–CH2CH2-SO2-X,其中X是乙烯基或基团–CH2CH2-Y,其中Y是在碱性条件下可离去的基团,如OSO3M,SSO3M,OCOCH3,OPO3M或卤素;
另外,R28可以是-SO2-X,其中X与上述所定义的相同;
B和D,各自独立为,通式(6a)所示的基团
其中,
R29~R31,各自独立为,氢,卤素,烷基,N-酰氨基,烷氧基,硫代烷氧基,羟基,氰基,硝基,烷氧基羰基,烷氧基硫代羰基,酰基,硫代酰基,芳酰基,三氟甲基,酰氧基,芳酰氧基,环烷基,芳基,杂芳基,杂环烷基,N-肉桂酰氨基,SO3M或COOM;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
或为SO2-X,其中X是乙烯基或基团–CH2CH2-Y,并且Y是在碱性条件下可离去的基团,如OSO3M,SSO3M,OCOCH3,OPO3M或卤素;
或为如上述所定义的通式(2a)或(2b)所示的基团;
a和b,各自独立为整数0或1,一般情况下,a+b不为0,并且通式(I)所示染料包含至少一个活性锚
M是氢,锂,钠,钾,铵或单,二,三或四-(C1-C4)-烷基铵,一个当量的碱土金属,或者一价有机阳离子。
本发明涉及式(I)所示染料所有类型的互变异构体和几何异构体。
出现在本申请中的烷基可以是直链的或支链的,并且是(C1-C12)-烷基,优选(C1-C8)-烷基,例如正丁基,异丁基,正戊基,异戊基,正己基,2-乙基己基,仲丁基,叔丁基和甲基丁基。
相同的逻辑适于烷氧基,据此,所述烷氧基优选(C1-C8)-烷氧基,例如甲氧基和乙氧基,也适于硫代烷氧基,所述硫代烷氧基优选(C1-C8)-硫代烷氧基,例如-SCH3或-SC2H5。
环烷基优选(C3-C8)-环烷基,特别优选环戊基和环己基。根据本发明宗旨,术语环烷基包括取代环烷基以及不饱和环烷基。此类型优选环戊烯基。优选的取代基是烷基,羟烷基,卤素,羟基,烷氧基,酰基,氰基,硝基,氨基,单烷基氨基,二烷基氨基,单(羟烷基)氨基,二(羟烷基)氨基,单烷基-单(羟烷基)氨基,氨基甲酰基,氨基磺酰基,酰氨基,脲基,氨基磺酰基氨基,烷氧基羰基和酰氧基。
出现在本申请中的芳基优选苯基或萘基。术语苯基和萘包括未取代的以及取代的苯基和萘基。优选的取代基是烷基,环烷基,杂环烷基,羟烷基,卤素,羟基,烷氧基,烷硫基,酰基,硝基,氰基,氨基,单烷基氨基,二烷基氨基,单(羟烷基)氨基,二(羟烷基)氨基,单烷基-单(羟烷基)氨基,氨基甲酰基,氨基磺酰基,酰氨基,脲基,氨基磺酰基氨基,烷氧基羰基或酰氧基。
出现在本申请中的杂芳基优选吡啶,嘧啶,哒嗪,吡嗪,吡咯,咪唑,吡唑,1,2,4-噻二唑,1,2,4-三唑,四唑,噻吩,噻唑,异噻唑,苯并噻唑,苯并异噻唑,1,3,4-噻二唑,呋喃,恶唑,苯并恶唑或异恶唑。术语杂芳基包括未取代的以及取代形式的上述基团。优选的取代基是烷基,羟烷基,卤素,羟基,烷氧基,烷硫基,酰基,硝基,氰基,氨基,单烷基氨基,二烷基氨基,单(羟烷基)氨基,二(羟烷基)氨基,单烷基-单(羟烷基)氨基,氨基甲酰基,氨基磺酰基,酰氨基,脲基,氨基磺酰基氨基,烷氧基羰基和酰氧基。
杂环烷基优选吡咯烷,哌啶,吗啉,四氢呋喃或哌嗪。术语杂环烷基包括未取代的以及取代形式的上述基团。优选的取代基是烷基,羟烷基,卤素,羟基,烷氧基,烷硫基,酰基,硝基,氰基,氨基,单烷基氨基,二烷基氨基,单(羟烷基)氨基,二(羟烷基)氨基,单烷基-单(羟烷基)氨基,氨基甲酰基,氨基磺酰基,酰氨基,氨基羰基氨基,氨基磺酰基氨基,烷氧基羰基和酰氧基。
卤素优选氯,溴或氟。
M优选氢,锂,钠,或钾
在碱性条件下可离去的基团(Y)为,在碱性条件下将离开分子以得到乙烯基砜官能团的基团。此类基团的例子是OSO3M,SSO3M,OCOCH3,OPO3M,和卤素。
本发明特别优选的染料是式(Ia)所示的染料及其混合物。
其中,
R34~R43,各自独立为,氢,卤素,烷基,N-酰氨基,烷氧基,硫代烷氧基,羟基,氰基,硝基,烷氧基羰基,烷氧基硫代羰基,酰基,硫代酰基,芳酰基,三氟甲基,酰氧基,芳酰氧基,环烷基,芳基,杂芳基,杂环烷基,N-肉桂酰氨基,SO3M或COOM;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
X和M与上述所定义的相同
g和h,各自独立为0或1,一般情况下,g+h不为0。
在特别优选的通式(Ia)所示的染料中,
R34~R43,各自独立为,氢,(C1-C4)烷基,(C1-C4)烷氧基,卤素,酰基,N-酰氨基或SO3M。
本发明进一步优选的染料是通式(Ib)所示的染料及其混合物:
其中,
R47~R56,各自独立为,氢,卤素,烷基,N-酰氨基,烷氧基,硫代烷氧基,羟基,氰基,硝基,烷氧基羰基,烷氧基硫代羰基,酰基,硫代酰基,芳酰基,三氟甲基,酰氧基,芳酰氧基,环烷基,芳基,杂芳基,杂环烷基,N-肉桂酰氨基,SO3M或COOM;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
T是通式(2a)或(2b)所示的基团,其中,(2a)和(2b)与上述所定义的相同;
或为通式(9a)所示的基团
其中,
R57~R59,各自独立为,氢,卤素,烷基,烷氧基或SO3M;
R60是氢,烷基,环烷基或芳基;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N-酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基或芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N-酰氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基或芳酰氧基;
RG与上述所定义的相同,
X和M与上述所定义的相同
i和f,各自独立为整数0或1,一般情况下,i+f不为0。
在特别优选的通式(Ib)所示的染料中,
R47~R56,各自独立为,氢,(C1-C4)烷基,(C1-C4)烷氧基,卤素,酰基,N-酰氨基或SO3M。
T是–NH-RG,其中RG与上述所定义的相同;
或为–(CH2)j-NH-RG,其中j是1~3的整数,并且RG与上述所定义的相同;
或为通式(9a)所示的基团,其中R57~R59,各自独立为,氢,烷基或SO3M,R60是氢或烷基。
本发明进一步优选的染料是通式(Ic)所示的染料及其混合物:
其中,
R61~R69,各自独立为,氢,卤素,烷基,N-酰氨基,烷氧基,硫代烷氧基,羟基,氰基,硝基,烷氧基羰基,烷氧基硫代羰基,酰基,硫代酰基,芳酰基,三氟甲基,酰氧基,芳酰氧基,环烷基,芳基,杂芳基,杂环烷基,N-肉桂酰氨基,SO3M或COOM;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基。
T是通式(2a)或(2b)所示的基团,其中(2a)和(2b)与上述所定义的相同。
X与上述所定义的相同。
k和m,各自独立为整数0或1,一般情况下,k+m不为0。
在特别优选的通式(Ic)所示的染料中,
R61~R69,各自独立为,氢,(C1-C4)烷基,(C1-C4)烷氧基,卤素,酰基,N-酰氨基或SO3M。
T是–NH-RG,其中RG与上述所定义的相同;
或为–(CH2)n-NH-RG,其中n是1~3的整数,并且RG与上述所定义的相同。
本发明进一步优选的染料是通式(Id)所示的染料及其混合物:
其中,
R70~R79,各自独立为,氢,卤素,烷基,N-酰氨基,烷氧基,硫代烷氧基,羟基,氰基,硝基,烷氧基羰基,烷氧基硫代羰基,酰基,硫代酰基,芳酰基,三氟甲基,酰氧基,芳酰氧基,环烷基,芳基,杂芳基,杂环烷基,N-肉桂酰氨基,SO3M或COOM;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基。
T是通式(2a),(2b)或(9a)所示的基团,其中(2a),(2b)和(9a)与上述所定义的相同,
M与上述所定义的相同。
o和p,各自独立为整数0或1,一般情况下,o+p不为0。
在特别优选的通式(Id)所示的染料中,
R70~R79,各自独立为,氢,(C1-C4)烷基,(C1-C4)烷氧基,卤素,酰基,N-酰氨基或SO3M。
T是–NH-RG,其中RG与上述所定义的相同;
或为–(CH2)q-NH-RG,其中q是1~3的整数,并且RG与上述所定义的相同;
或为通式(9a)所示的基团,其中R57~R59,各自独立为,氢,烷基或SO3M,R60是氢或烷基。
本发明进一步优选的染料是通式(Ie)或(If)所示的染料及其混合物:
其中,
R80~R99,各自独立为,氢,卤素,烷基,N-酰氨基,烷氧基,硫代烷氧基,羟基,氰基,硝基,烷氧基羰基,烷氧基硫代羰基,酰基,硫代酰基,芳酰基,三氟甲基,酰氧基,芳酰氧基,环烷基,芳基,杂芳基,杂环烷基,N-肉桂酰氨基,SO3M或COOM;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
另外,R87~R89和R97~R99,可以各自独立为通式(8a)所示的基团
其中,
R44~R46,各自独立为,氢,卤素,烷基,烷氧基或SO3M,
T是通式(2a)或(2b)所示的基团,其中(2a)和(2b)与上述所定义的相同,
X和M与上述所定义的相同
r,s,t和u,各自独立为整数0或1,一般情况下,r+s不为0,t+u不为0。
在特别优选的通式(Ie)或(If)所示的染料中,
R80~R99,各自独立为,氢,(C1-C4)烷基,(C1-C4)烷氧基,卤素,酰基,N-酰氨基或SO3M。
T是–NH-RG,其中RG与上述所定义的相同;
或为–(CH2)v-NH-RG,其中v是1~3的整数,并且RG与上述所定义的相同;
本发明进一步优选的染料是通式(Ig)所示的染料及其混合物:
其中,
R100~R109,各自独立为,氢,卤素,烷基,N-酰氨基,烷氧基,硫代烷氧基,羟基,氰基,硝基,烷氧基羰基,烷氧基硫代羰基,酰基,硫代酰基,芳酰基,三氟甲基,酰氧基,芳酰氧基,环烷基,芳基,杂芳基,杂环烷基,N-肉桂酰氨基,SO3M或COOM;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
另外,R100~R102和R107~R109,可以各自独立为通式(8a)所示的基团,其中8a与上述所定义的相同,
T是通式(2a)或(2b)所示的基团,其中(2a)和(2b)与上述所定义的相同,
M与上述所定义的相同
w和x,各自独立为整数0或1,一般情况下,w+x不为0。
在特别优选的通式(Ig)所示的染料中,
R100~R109,各自独立为,氢,(C1-C4)烷基,(C1-C4)烷氧基,卤素,酰基,N-酰氨基或SO3M。
T是–NH-RG,其中RG与上述所定义的相同;
或为–(CH2)y-NH-RG,其中y是1~3的整数,并且RG与上述所定义的相同;
本发明进一步优选的染料是通式(Ih)所示的染料及其混合物:
其中,
R110~R118,各自独立为,氢,卤素,烷基,N-酰氨基,烷氧基,硫代烷氧基,羟基,氰基,硝基,烷氧基羰基,烷氧基硫代羰基,酰基,硫代酰基,芳酰基,三氟甲基,酰氧基,芳酰氧基,环烷基,芳基,杂芳基,杂环烷基,N-肉桂酰氨基,SO3M或COOM;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
另外,R116~R118,可以各自独立为通式(8a)所示的基团,其中8a与上述所定义的相同,
X和M与上述所定义的相同
T是通式(2a)或(2b)所示的基团,其中(2a)和(2b)与上述所定义的相同,
在特别优选的通式(Ih)所示的染料中,
R110~R118,各自独立为,氢,(C1-C4)烷基,(C1-C4)烷氧基,卤素,酰基,N-酰氨基或SO3M,
T是–NH-RG,其中RG与上述所定义的相同;
或为–(CH2)z-NH-RG,其中z是1~3的整数,并且RG与上述所定义的相同;
本发明进一步优选的染料是通式(Ii)所示的染料及其混合物:
其中,
R119~R126,各自独立为,氢,卤素,烷基,N-酰氨基,烷氧基,硫代烷氧基,羟基,氰基,硝基,烷氧基羰基,烷氧基硫代羰基,酰基,硫代酰基,芳酰基,三氟甲基,酰氧基,芳酰氧基,环烷基,芳基,杂芳基,杂环烷基,N-肉桂酰氨基,SO3M或COOM;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
或为被一个或多个杂原子如氧或硫中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
X和M与上述所定义的相同
T是通式(2a)或(2b)所示的基团,其中(2a)和(2b)与上述所定义的相同,
在特别优选的通式(Ii)所示的染料中,
R119~R126,各自独立为,氢,(C1-C4)烷基,(C1-C4)烷氧基,卤素,酰基,N-酰氨基或SO3M,
T是–NH-RG,其中RG与上述所定义的相同;
或为–(CH2)a’-NH-RG,其中a’是1~3的整数,并且RG与上述所定义的相同;
优选的式(Ia)~(Ii)所示的染料的例子是下面表1中所列的化合物I1~I159,并且具有通式(I’)所示的结构。
本发明还提供了式(I)所示染料的制备方法。该方法包括式A-NH2所示化合物的重氮化,其中A与上述所定义的相同,以及当a为0时,重氮化产物与式(II)所示化合物的偶联。
或者当a为1时,与偶联组分B-NH2偶联,由此偶联产物进一步重氮化并偶联至式(II)所示化合物。
式(II)所示化合物的制备包括式C-NH2所示化合物的重氮化,其中C与上述所定义的相同,并且当b为0时,将重氮化产物与2,4-二氨基苯磺酸偶联,或者当a为1时,与偶联组分D-NH2偶联,由此偶联产物进一步重氮化并偶联至2,4-二氨基苯磺酸。
重氮化反应,通常,可通过本领域技术人员已知的重氮化方法进行,优选在酸性介质中使用亚硝酸钠或亚硝基硫酸,所述酸性介质采用无机酸比如盐酸,硫酸或磷酸或它们的混合物,或者有机酸比如乙酸或丙酸或它们的混合物。无机酸和有机酸的混合物也可以有利地使用。因此,所得的重氮盐含有相反阴离子,作为用于重氮化反应酸的相应共轭碱,或其混合物,当使用了两种或多种酸的混合物时。
偶联反应通常可通过已知方法进行。
式A-NH2,B-NH2,C-NH2和D-NH2所示的化合物是已知的并且可商购获得,或者通过本领域技术人员已知的常用化学反应方法来合成。
最终产物也可以选择性地进行乙烯化反应。举例来说,将乙烯化反应基团如β-硫酸根合乙基磺酰基转化成其乙烯基的形式。这样的反应是本领域技术人员已知的。此类反应通常在中性至碱性介质中,于温度例如20~80℃,pH为例如7~14的条件下进行。
式(I)所示的染料是纤维活性的,包含纤维活性官能团。纤维活性官能团指的是能够与纤维素材料的羟基,羊毛和丝绸中的氨基,羧基,羟基和硫醇基团反应的基团,或者能够与合成聚酰胺的氨基及其可能含有的羧基反应以形成共价化学键的基团。
本发明的染料通过使用在活性染料领域中所描述的大量方法,适用于天然的,人造的,再生的,物理或化学改性的,回收的或合成的包含羟基,羟基,和/或甲酰氨基的纤维材料及其混纺物的染色和印花。因此,本发明还提供了一种用于上述纤维材料及其混纺物的染色和印花的方法,其中用到了根据本发明的染料或染料混合物。
如上所述的天然纤维材料的实例是植物纤维,比如种子纤维,即棉,有机棉,木棉,椰壳纤维;韧皮纤维,即亚麻,大麻,黄麻,红麻,苎麻,藤;叶纤维,即剑麻,赫纳昆纤维,香蕉纤维;秸秆纤维,即竹纤维;来自动物的纤维,如羊毛,有机羊毛,蚕丝,山羊绒羊毛,羊驼毛纤维,马海毛,安哥拉毛纤维以及毛皮和皮革材料。
人造的和再生的纤维实例是纤维素纤维,如纸纤维和纤维素再生纤维如粘胶人造丝纤维,醋酸酯和三醋酸酯纤维和莱赛尔纤维。
如上所述的合成纤维材料的实例是尼龙材料,像尼龙-6,尼龙-6.6和芳纶纤维。
上述进行染色的基材可以是各种形式的,比如但不限于纱,机织织物,成圈型编织织物或地毯。
本发明染料及其盐或混合物可作为单一的染料产品在染色或印花工艺中使用,或者在染色或印花组合物中,它可以是二/三或多组分混合产品的一部分。
本发明染料及其盐或混合物与其他已知的和/或可商购的染料高度相容,并且它们可与此类染料一起使用以获得技术性能同样良好的特定色调。技术性能包括提升力,固色性能和均染性。
由于根据本发明的染料的水溶性非常好,它们还可以有利地在常规的连续染色工艺中使用。
本发明的染料还可以用于数字印花工艺,特别是数字织物印花。用于数字印花的包含本发明染料的水性油墨同样构成本发明主题的一部分。
基于油墨的总重量,本发明油墨中本发明染料的含量优选0.1wt%~50wt%,更加优选1wt%~30wt%,最优选1wt%~15wt%。
所述油墨,以及本发明染料可能,如果需要,包含进一步的染料用于数字印花。
针对在连续流动工艺中使用的本发明所述油墨,可通过加入电解质设置电导率为0.5~25mS/m。适用的电解质包括例如硝酸锂和硝酸钾。本发明油墨可包含基于总量1wt%~50wt%的有机溶剂,优选5wt%~30wt%。适合的有机溶剂例如醇类,如甲醇,乙醇,1-丙醇,异丙醇,1-丁醇,叔丁醇,戊醇,多元醇例如:1,2-乙二醇,1,2,3-丙三醇,丁二醇,1,3-丁二醇,1,4-丁二醇,1,2-丙二醇,2,3-丙二醇,戊二醇,1,4-戊二醇,1,5-戊二醇,己二醇,D,L-1,2-己二醇,1,6-己二醇,1,2,6-己三醇,1,2-辛二醇,聚亚烷基二醇类,例如:聚乙二醇,聚丙二醇,具有1~8亚烷基的亚烷基二醇,例如:单乙二醇,二甘醇,三甘醇,四甘醇,硫甘醇,硫二甘醇,丁基三甘醇,己二醇,丙二醇,二丙二醇,三丙二醇,多元醇的低烷基醚,例如:乙二醇单甲醚,乙二醇单乙醚,乙二醇单丁醚,二甘醇单甲醚,二甘醇单乙醚,二甘醇单丁醚,二甘醇单己醚,三甘醇单甲醚,三甘醇单丁醚,三丙二醇单甲醚,四甘醇单丁醚,四甘醇二甲醚,丙二醇单甲醚,丙二醇单乙醚,丙二醇单丁醚,三丙二醇异丙醚,聚亚烷基二醇醚类,例如:聚乙二醇单甲醚,聚丙二醇甘油醚,聚乙二醇十三烷基醚,聚乙二醇壬基苯基醚,胺类,例如:甲胺,乙胺,三乙胺,二乙胺,二甲胺,三甲胺,二丁胺,二乙醇胺,三乙醇胺,N-乙酰乙醇胺,N-甲酰乙醇胺,乙二胺,脲衍生物,例如:脲,硫脲,N-甲基脲,N,N’-ε二甲基脲,亚乙基脲,1,1,3,3-四甲基脲,酰胺类,例如:二甲基甲酰胺,二甲基乙酰胺,乙酰胺,酮类或酮醇类,例如:丙酮,二丙酮醇,环醚类,例如:四氢呋喃,三羟甲基乙烷,三羟甲基丙烷,2-丁氧基乙醇,苯甲醇,2-丁氧基乙醇,γ-丁内酯,ε-己内酰胺,进一步为环丁砜,二甲基环丁砜,甲基环丁砜,2,4-二甲基环丁砜,二甲基砜,丁二烯砜,二甲亚砜,二丁基亚砜,N-环己基吡咯烷酮,N-甲基-2-吡咯烷酮,N-乙基吡咯烷酮,2-吡咯烷酮,1-(2-羟乙基)-2-吡咯烷酮,1-(3-羟丙基)-2-吡咯烷酮,1,3-二甲基-2-咪唑烷酮,1,3-二甲基-2-咪唑啉酮,1,3-二甲氧基甲基咪唑烷,2-(2-甲氧基乙氧基)乙醇,2-(2-乙氧基乙氧基)乙醇,2-(2-丁氧基乙氧基)乙醇,2-(2-丙氧基乙氧基)乙醇,吡啶,哌啶,1,3-二甲基-2-咪唑烷酮,丁内酯,三甲基丙烷,1,2-二甲氧基丙烷,二恶烷乙酸乙酯,乙二胺四乙酸乙基戊基醚,1,2-二甲氧基丙烷和三甲基丙烷。
本发明油墨可进一步包括常用的添加剂,例如粘度调节剂以调节粘度于20~50℃下在1.5~40.0mPas的范围内。优选油墨具有1.5~20mPas的粘度,特别优选油墨具有1.5~15mPas的粘度。
适用的粘度调节剂包括流变添加剂,例如:聚乙烯己内酰胺,聚乙烯吡咯烷酮以及它们的共聚物聚醚多元醇,缔合增稠剂,聚脲,聚氨酯,海藻酸钠,改性半乳甘露聚糖,聚醚脲,聚氨酯,非离子纤维素醚。
作为进一步的添加剂,本发明油墨可包括表面活性物质以调节表面张力为20~65mN/m,如果需要的话作为所用工艺(热或压电技术)的一种功能使用。适用的表面活性物质包括例如所有的表面活性剂,优选非离子表面活性剂,丁基二甘醇和1,2-己二醇。
本发明油墨可进一步包括常用的添加剂,例如抑制真菌和细菌生长的物质,其含量基于油墨的总重量为0.01wt%~1wt%。
所述油墨可通过将各组分在水中混合的常规方式来制备。
本发明油墨特别适用于喷墨印花工艺,用于印花多种类型的材料,特别是羊毛和聚酰胺纤维的材料。
下面的实施例用于说明本发明。除非另有说明,份数和百分比都是按重量计。重量份数和体积份数之间的关系是千克和升的关系。
实施例1:
ⅰ)将7.6份2-[(3-磺基-4-氨基苯基)磺酰基]乙氧基}磺酸悬浮在70份水中。用冰将反应容器冷却至0~5℃。将5.2份37%盐酸加到反应混合物中。搅拌30分钟后,加入4.3毫升5M硝酸钠溶液。反应在0~5℃下搅拌1小时,然后加入0.2份氨基磺酸。
将4.5份5-氨基-2-萘磺酸加到重氮盐中。用15%苏打溶液调节pH至1~1.5。反应搅拌1小时,未经分离得到中间体(b)。
ⅱ)上述合成的(b)的溶液用15%苏打溶液调节pH至5~6,并用冰冷却至0~5℃。加入4.8毫升5M亚硝酸钠溶液。将该反应混合物加到19.7份37%盐酸和30份冰的混合物中。反应在0~5℃下搅拌直至完成,然后加入0.2份氨基磺酸。
将3.6份2,4-二氨基-苯磺酸溶于40份水中,用15%苏打溶液调节pH至6~6.5。用冰将该溶液冷却至10~15℃。向此溶液中滴加重氮盐。pH降至2.5~3,之后用15%苏打溶液维持pH值在这个范围。反应搅拌直到完成,未经分离得到中间体(c)。
ⅲ)将5.6份2-(对氨基苯基磺酰基)乙基硫酸氢盐悬浮在70份水中。用冰将反应容器冷却至0~5℃。将5.9份37%盐酸加到反应混合物中。搅拌10分钟后,加入4.3毫升5M硝酸钠溶液。反应在0~5℃下搅拌1小时,然后加入0.2份氨基磺酸。
将重氮盐缓慢加到上述合成的(c)的溶液中,同时保持pH为5~5.5。反应搅拌直到完成。产物析出,通过过滤收集并干燥,得到16.5份染料I2,为棕色固体。
通过类比,所有式(I1-I336)所示的染料可根据上述实施例1中所述的方法合成。
染色实施例1
将3份本发明染料I6溶于2000份水中,并加入1份流平剂(基于高级脂族胺和环氧乙烷的缩合产物)。然后用乙酸(60%)调节pH至3.8~4.2。染浴中放入100份羊毛织物。温度在30分钟内升至40℃,在此温度下保持15分钟,然后在58分钟内升温至98℃,在该温度下进行染色90分钟。之后冷却到90℃,并移出染色材料。将羊毛织物用热水和冷水洗,碱处理,然后离心并干燥。所染的深黑色在纤维中显示出良好的匀染性,以及优异的耐光性,在氙LFISO 195 B02试验中,即使在织物重量中浓度较低,耐光性依然超过基于活性黑5的市售品。此外,该染色显示出非常好的湿牢度性能,在洗涤牢度60℃ISO 105 C03测试,以及碱性汗液ISO 105 E04测试中,颜色深度是基于活性黑5的商业产品的两倍。
染色实施例2
将2份本发明染料I6和60份氯化钠溶于1000份水中,加入12份碳酸钠和0.5份润湿剂。在此染浴中放入100份漂白的棉针织物。染浴温度以0.5℃/分钟的梯度升至30℃,并在该温度下保持30分钟,然后在30分钟内升温至60℃,在此温度下进一步维持60分钟。之后,染色物首先用自来水漂洗5分钟。染色物用60%浓度的乙酸在50℃下中和30~40分钟。染色物用沸腾的自来水漂洗30~40分钟,接着在40~50℃下最后冲洗20分钟并干燥。漂洗用自来水。所染的深棕色具有良好的整体固色性能。
染色实施例3
将1份本发明染料I6溶于2000份水中,再加入1份流平剂(基于高级脂族胺和环氧乙烷的缩合产物)和6份乙酸钠。然后用乙酸(80%)调节pH至4.5。染浴加热到50℃持续10分钟,然后放入100份编织聚酰胺织物。在50分钟内将温度升至110℃,然后在该温度下进行染色60分钟。之后冷却至60℃并移出染色材料。聚酰胺织物用热水和冷水洗,皂洗,然后离心并干燥。所得染色具有良好的整体固色性能,以及在纤维中良好的匀染性。
染色实施例4
由丝光棉构成的纺织织物用含有35g/L碳酸钙钠,100g/L脲和150g/L低粘度海藻酸钠溶液(6%)的液剂浸轧,然后干燥。液剂利用率为70%。经此预处理的纺织品通过按需点滴(气泡喷墨)的喷墨打印头用水性油墨印花,所述水性油墨包含2%本发明染料I6,20%环丁砜,0.01%Mergal K9N和77.99%的水。将印花产品充分干燥。在102℃下用饱和水蒸气方式固色8分钟。然后将印花产品进行热冲洗,在95℃下用热水进行色牢度洗涤,温水冲洗,然后干燥。所得印花具有非常好的整体固色性能。
Claims (10)
1.如式(I)所示的化合物,具有式(Ia)所示的结构:
其中,g为整数1,h为整数0;
选自
R34~R35,R42~R43,各自独立为,氢,卤素,烷基,N-酰氨基,烷氧基,硫代烷氧基,羟基,氰基,硝基,烷氧基羰基,烷氧基硫代羰基,酰基,硫代酰基,芳酰基,三氟甲基,酰氧基,芳酰氧基,环烷基,芳基,杂芳基,杂环烷基,N-肉桂酰氨基,SO3M或COOM;
或为被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
或为被一个或多个杂原子中断且被一个或多个取代基取代的烷基,所述取代基选自由下列基团组成的群组:羟基,芳基,环烷基,烷氧基,硫代烷氧基,N,N,N-三烷基铵,N,N,N-三芳基铵,N,N-二烷基-N-单芳基铵,N,N-二芳基-N-单烷基铵,N-酰氨基,N-肉桂酰氨基,N-烷基磺酰基-氨基,卤素,氰基,SO3M,COOM,硝基,酰基,硫代酰基,烷基磺酰基,芳酰基,三氟甲基,杂芳基,杂环烷基,烷氧基羰基,烷氧基硫代羰基,酰氧基,芳酰氧基;
X是乙烯基或基团–CH2CH2-Y,并且Y是在碱性条件下可离去的基团;M是氢,锂,钠,钾,铵或单,二,三或四-(C1-C4)-烷基铵,一个当量的碱土金属,或者一价有机阳离子。
2.根据权利要求1所述的化合物,其特征在于:所述的杂原子为氧或硫。
3.根据权利要求1所述的化合物,其特征在于:所述的在碱性条件下可离去的基团为OSO3M,SSO3M,OCOCH3,OPO3M或卤素。
4.根据权利要求2所述的化合物,其特征在于:所述的在碱性条件下可离去的基团为OSO3M,SSO3M,OCOCH3,OPO3M或卤素。
5.化学组合物,由两种或多种根据权利要求1所述的化合物组成。
6.化学组合物,包含一种或多种根据权利要求1所述的化合物。
7.用于染色的水溶液,包含一种或多种根据权利要求1所述的化合物。
8.一种如权利要求1所述的式(I)所示的化合物的制备方法,式(I)所示的化合物具有式(Ia)所示的结构,包括步骤:
a1)将A-NH2重氮化,得到重氮盐A-N≡N+相反阴离子-,
a2)将步骤a1所得重氮盐选择性地与B-NH2偶联,并将所得化合物重氮化,得到重氮盐A-N=N-B-N≡N+相反阴离子-,
b1)将C-NH2重氮化,得到重氮盐C-N≡N+相反阴离子-,
b2)将步骤b1所得C-双偶氮-化合物选择性地与D-NH2偶联,并将所得化合物重氮化,得到重氮盐C-N=N-D-N≡N+相反阴离子-,
c1)2,4-二氨基-苯磺酸与步骤a1或a2的产物偶联
c2)在步骤c1中的反应是与步骤a1的产物进行的情况下,将步骤c1的产物与b2的产物偶联,或者
在步骤c1中的反应是与步骤a2的产物进行的情况下,将步骤c1的产物与b1的产物偶联,
或者
d1)2,4-二氨基-苯磺酸与步骤b1或b2的产物偶联
d2)在步骤d1中的反应是与步骤b1的产物进行的情况下,将步骤d1的产物与a2的产物偶联,或者
在步骤c1中的反应是与步骤b2的产物进行的情况下,将步骤d1的产物与a1或a2偶联;
其中A,B,C,D的定义同权利要求1。
9.根据权利要求1所述的化合物,根据权利要求5或6所述的化学组合物或者根据权利要求7所述的水溶液在纤维以及纤维混纺物染色中的应用,所述纤维选自由如下纤维组成的群组:植物纤维;来自动物的纤维;人造的,再生的和回收的纤维;以及合成纤维材料。
10.含有一种或多种以化学和/或物理的形式结合的根据权利要求1所述的化合物的纤维和含有所述纤维的混纺物,所述纤维选自由如下纤维组成的群组:植物纤维;来自动物的纤维;人造的,再生的和回收的纤维;以及合成纤维材料。
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