CN101578338A - 分散性染料，彼之制造与应用 - Google Patents
分散性染料，彼之制造与应用 Download PDFInfo
- Publication number
- CN101578338A CN101578338A CNA2008800013697A CN200880001369A CN101578338A CN 101578338 A CN101578338 A CN 101578338A CN A2008800013697 A CNA2008800013697 A CN A2008800013697A CN 200880001369 A CN200880001369 A CN 200880001369A CN 101578338 A CN101578338 A CN 101578338A
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- CN
- China
- Prior art keywords
- group
- alkyl
- hydrogen
- base
- nitro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 239000006185 dispersion Substances 0.000 title description 15
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000000975 dye Substances 0.000 claims description 54
- -1 vinyloxy group Chemical group 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000004043 dyeing Methods 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 238000007639 printing Methods 0.000 claims description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000000976 ink Substances 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 230000002209 hydrophobic effect Effects 0.000 claims description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000004753 textile Substances 0.000 claims description 4
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 238000006193 diazotization reaction Methods 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 150000001721 carbon Chemical class 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 239000002585 base Substances 0.000 description 23
- 239000007788 liquid Substances 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 14
- 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
- 239000000203 mixture Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000052 vinegar Substances 0.000 description 9
- 235000021419 vinegar Nutrition 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- 239000004744 fabric Substances 0.000 description 5
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 230000000740 bleeding effect Effects 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 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
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000008431 aliphatic amides Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 230000003139 buffering effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical class OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004258 Ethoxyquin Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229920000926 Galactomannan Polymers 0.000 description 1
- 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 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002334 Spandex Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 244000042295 Vigna mungo Species 0.000 description 1
- 235000010716 Vigna mungo Nutrition 0.000 description 1
- 235000011453 Vigna umbellata Nutrition 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- VDEMCTLJTJCOEB-UHFFFAOYSA-N [Cl].C(C)(=O)N Chemical compound [Cl].C(C)(=O)N VDEMCTLJTJCOEB-UHFFFAOYSA-N 0.000 description 1
- NMSPEXDFLSMWMC-UHFFFAOYSA-N [O-2].[Na+].[Na+].ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl Chemical compound [O-2].[Na+].[Na+].ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl NMSPEXDFLSMWMC-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
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- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
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- 239000003139 biocide Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000009954 braiding Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
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- 150000002170 ethers Chemical class 0.000 description 1
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 1
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- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
- NFIYTPYOYDDLGO-UHFFFAOYSA-N phosphoric acid;sodium Chemical compound [Na].OP(O)(O)=O NFIYTPYOYDDLGO-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940080263 sodium dichloroacetate Drugs 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- LUPNKHXLFSSUGS-UHFFFAOYSA-M sodium;2,2-dichloroacetate Chemical compound [Na+].[O-]C(=O)C(Cl)Cl LUPNKHXLFSSUGS-UHFFFAOYSA-M 0.000 description 1
- LIOTZBNOJXQXIL-UHFFFAOYSA-M sodium;3-chloropropanoate Chemical compound [Na+].[O-]C(=O)CCCl LIOTZBNOJXQXIL-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明提供通式(I)染料其中D为重氮成分的残基；R1至R7及L各为申请专利范围第1项中所定义者；其制备方法及其用途。
Description
技术领域
本发明系关于分散性偶氮染料，其中包含某些酯基的取代基系通过联结质(linker)联结到发色团。
先前技术
具有此结构要素的染料系已知者且载于，例如，GB9 09843、WO95/20014和WO05/056690之中。类似地，其中此等酯基系通过对偶氮桥联呈邻位的醯胺基联结质联结到发色团之染料系已知者且载于JP58-002352中。
顷发现于其中此等或类似的结构要素系以某种方式联结之分散性偶氮染料具有优良的性质且提供具有优良耐洗性及非常好的耐升华性之染色件。
发明内容
本发明提供通式(I)染料
其中
D为重氮成分的残基；
R1为氢、(C1-C6)-烷基、(C1-C4)-烷氧基或卤素，或与R2合并形成-*CH(CH3)CH2C(CH3)2-，此处以*标志的碳原子系接着到苯基核；
R2和R3各独立地为氢、(C1-C6)-烷基、经取代(C1-C6)-烷基、(C3-C4)-烯基或经取代(C3-C4)-烯基；
R4为-CHR5CN、-CHR6COR7或-CH＝CH2；
R5为氢、(C1-C6)-烷基或经取代(C1-C6)-烷基；
R6为氢、(C1-C6)-烷基或经取代(C1-C6)-烷基；
R7为(C1-C6)-烷基、经取代(C1-C6)-烷基、乙烯氧基、(C1-C6)-烷氧基、经取代(C1-C6)-烷氧基、苯氧基、经取代苯氧基、苯基或经取代苯基；且
L为(C2-C6)-伸烷基、氧插接(C2-C6)-伸烷基、(C2-C6)-伸烯基、伸芳基或经取代伸芳基；
但其限制条件为当R5为氢时，L不为C2-伸烷基。
重氮成分的D残基特别为分散性染料领域中习用且为谙于此技者所知者。较佳地，D表式(IIa)之基
其中
T1和T2各独立地为氢、(C1-C6)-烷基、(C1-C4)-烷氧基、-SO2-(C1-C6)-烷基、-SO2-芳基、氰基、卤素或硝基；且
T3和T4各独立地为氢、卤素、氰基、三氟甲基、-SCN、-SO2-CH3或硝基；
但其限制条件为T1、T2、T3和T4中至少有一者不为氢；
或表式(IIb)之基
其中
T5和T5’各独立地为氢、硝基或卤素；且
T6为氢、-SO2-CH3、-SCN、(C1-C4)-烷氧基、卤素或硝基；
但其限制条件为T5、T5’和T6中至少有一者不为氢；
或表式(IIc)之基
其中T12为氢或卤素；
或表式(IId)之基
其中
T7为硝基、-CHO、氰基、-COCH3或下式之基；
其中T10为氢、卤素、硝基或氰基；
T8为氢、(C1-C4)-烷基或卤素；且
T9为硝基、氰基、-COCH3或-COOT11，其中T11为(C1-C4)-烷基；
或表式(IIe)之基
其中T7和T8皆为上面所定义者；
或表式(IIf)之基
其中T13为苯基或S-(C1-C4)-烷基；
或表式(IIg)之基
其中T14为氰基、-COCH3或-COOT11，其中T11为(C1-C4)-烷基且T15为苯基或(C1-C4)-烷基；
或表式(IIh)之基
其中T14为上面定义者且T16为(C1-C4)-烷基；
或表式(IIi)之基
其中T17为氰基甲基、苯甲基或烯丙基；
或表式(IIj)之基
上面和下面的定义中所提及的烷基可为直链或支链者且为，例如，甲基、乙基、正丙基、异丙基、正丁基、异丁基、第三丁基、正戊基或正己基。类似的逻辑应用于烷氧基和(C2-C6)-伸烷基。氧插接(C2-C6)-伸烷基特别符合式-(CH2)n-O-(CH2)m-，其中n和m各为从1至5的数且彼等的总和为从2至6的数。
经取代烷基特别者为经1至3个选自下列的群组中之取代基所取代者：卤素、氰基、羟基、(C1-C6)-烷氧基、-COO(C1-C6)-烷基、-COO芳基、-OCOO(C1-C6)-烷基、-OCOO芳基、-OCO(C1-C6)-烷基、苯基、-OCO苯基和苯氧基。
烯基特别者为烯丙基。经取代烯基特别者为载有选自甲基、乙基和苯基所组成的群组中之取代基。
芳基特别者为苯基和萘基。伸芳基特别者为伸苯基和伸萘基。当此等或苯氧基经取代时，彼等可载一或更多，特别者1、2或3个选自下列所组成的群组中之取代基：卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、苯基、硝基、氰基、三氟甲基和-SO2-CH3。
卤素较佳者表氯或溴。
R1较佳者为氢、氯、甲基、乙基、甲氧基或乙氧基；
R2和R3较佳者各独立地为氢、甲基、乙基、正丙基、正丁基、氰基乙基、-C2H4OCOCH3、-C2H4OCOC2H4、-C2H4COOCH3、-C2H4COOC2H5、甲氧基乙基、乙氧基乙基、苯氧基乙基、苯乙基、苯甲基或烯丙基；
R5和R6较佳地各为氢；
R7较佳地为甲基、乙基、苯基、甲氧基、乙氧基、丙氧基、乙烯氧基、苯甲氧基或苯氧基；且
L较佳地为伸乙基、伸丙基、伸丁基、伸乙烯基、伸丁烯基、1，3-伸苯基、1，4-伸苯基或-CH2OCH2-。
较佳的本发明染料系符合通式(Ia)
其中T1至T4、R1至R4和L各上面所定义者。
特佳的本发明染料系符合通式(Iaa)
其中
T3’为氢、氰基、氯或溴；
T4’为氢、氰基、硝基、氯或溴；
R1’为氢或甲氧基；
R2’为氢、乙基、烯丙基或甲氧基乙基；
R3’为乙基、烯丙基、甲氧基乙基或氰基乙基；
R4’为氰基甲基、-CH2COR7’或-CH＝CH2；
R7’为甲基、乙基、苯基、甲氧基、乙氧基或乙烯氧基；且
L’为伸乙基、伸丙基、伸丁基、1，3-伸苯基、1，4-伸苯基或-C2OCH2-；
但其限制条件为当R4’为氰基甲基时，L’不为伸乙基。
其他较佳的本发明染料系符合通式(Ib)
其中R1至R4和L各为上面所定义者且D’表3，5-二氰基-4-氯-2-噻吩基、3，5-二氰基-2-噻吩基、3，5-二氰基-4-甲基-2-噻吩基、3-氰基-5-硝基-2-噻吩基、3-氰基-4-氯-5-甲醯基-2-噻吩基、3，5-二硝基-2-噻吩基、3-乙醯基-5-硝基-2-噻吩基、5-乙醯基-3-硝基-2-噻吩基、3-((C1-C4)-烷氧基羰基)-5-硝基-2-噻吩基、5-苯基偶氮基-3-氰基-2-噻吩基、5-(4-硝基苯基偶氮基)-3-氰基-2-噻吩基、5-硝基-2-噻唑基、4-氯-5-甲醯基-2-噻唑基、5-硝基-3-苯并异噻唑基、7-溴-5-硝基-3-苯并异噻唑基、7-氯-5-硝基-3-苯并异噻唑基、3-甲基-4-氰基-5-异噻唑基、3-苯基-1，2，4-噻二唑-2-基、5-((C1-C2)-烷基氢硫基)-1，3，4-噻二唑-2-基、1-氰基甲基-4，5-二氰基-2-咪唑基、6-硝基苯并噻唑-2-基、5-硝基苯并噻唑-2-基、6-硫氰酸基-2-苯并噻唑基、6-氯-2-苯并噻唑基或(5)，6，(7)-二氯-2-苯并噻唑基。
本发明通式(I)染料可以使用谙于此技者所知方法得到。例如，将通式(III)化合物
D-NH2 (III)
其中D为上面所定义者，予以重氮化且偶合到通式(IV)化合物上
其中R1至R4和L各为上面所定义者。
通式(III)化合物的重氮化通常是以已知方式完成，例如使用亚硝酸钠在呈酸性，例如用盐酸-或硫酸的水性介质中，或使用亚硝基硫酸在浓硫酸、磷酸或在醋酸与丙酸的混合物中。较佳的温度范围为0℃与15℃之间。
经重氮化的化合物在通式(IV)化合物上的偶合通常系同样地以已知方式完成，例如在酸性、水性、水-有机性或有机性介质中，特别有利者系在低于10℃的温度下。所用的酸特别者系硫酸、醋酸或丙酸。
通式(III)和(IV)化合物皆为已知者且可用已知方法制备。
本发明通式(I)染料非常可用于染色和印刷疏水性材料，所得染色件和印刷件具有显著的均匀色彩及高使用坚牢性(fastness)。值得特别提及者为优良的耐洗性及非常好的耐升华性。
本发明因而也提供通式I染枓于染色和印刷疏水性材料上之用途，即，以习用方式染色或印刷此等材料之方法，其中使用一或多种本发明通式(I)染料。
所提及的疏水性材料可为合成来源或半合成来源。可用的疏水性材料包括例如二次纤维素醋酸酯、纤维素三醋酸酯、聚醯胺、聚乳交酯及，特别者，高分子量聚酯。高分子量聚酯材料特别者为以聚对苯二甲酸乙二酯和聚对苯二甲酸丁二酯为基者。此外也包括由聚酯-棉或聚酯-elastane所组成的混纺织物和混纺纤维。
该等疏水性合成材料可呈膜或片或线状构造之形式且可经加工成为，例如，纱、或编织或针织物材料。较佳者为纤维状纺织材料，其也可呈例如微纤维之形式。
根据本发明所提供的用途之染色可用习用方式进行，较佳者用水分散液，恰当时在载剂(carrier)存在中，于80至约110℃的温度，以耗尽法(exhaust process)或在110℃至140℃的染色压热器内以HT法进行，且也可用所谓的热固定法(thermofix process)进行，其中将织物用染色液压染且随后在约180至230℃下固定/变定。
上述材料的印刷可用已知方式经由将本发明通式(I)染料掺加到印刷糊中且用来在180至230℃之间的温度下，使用HT蒸汽，高压蒸汽或干热处理要印刷的织物，恰当时在载剂存在中进行以固定该染料。
本发明通式(I)染料在用于染液、压染液或印刷糊中时，应呈非常细分之状态。
该染料系以习用方式经由将刚制成的染料与分散剂一起在液体介质，较佳者水中搅和，且对该混合物施以剪力作用以将原染料粒子机械地细研到达到最优比表面积且染料沉着为之减到最低之程度而转变成细分状态。此系在适当的磨机，诸如球磨机或砂磨机中完成。染料的粒度通常是在0.5与5微米之间且较佳者等于约1微米。
研磨操作中所用的分散剂可为非离子性或阴离子性者。非离子性分散剂包括例如环氧烷类，例如环氧乙烷或环氧丙烷，与可烷基化的化合物，例如脂肪醇、脂肪胺、脂肪酸、酚、烷基的和羧醯胺之反应产物。阴离子分散剂为例如木质素磺酸盐、烷基-或烷基芳基磺酸盐或烷基芳基聚二醇醚硫酸盐。
经如此得到的染料制备物对于大部份应用为可倾注者。据此，染料和分散剂的含量在此等情况中受到限制。通常，该分散液系经调整到高达50重量％的染料含量及高达约25重量％的分散剂含量。为了经济理由，于大部份情况中，都不让染料含量低于15重量％。该分散液也可含其它辅助剂，例如作为氧化剂者，例如间-硝基苯磺酸钠；或作为杀真菌剂者，例如邻-苯基苯氧化钠及五氯苯氧化钠；及特别是所谓的“酸予体”，例如丁内酯、一氯乙醯胺、氯醋酸钠、二氯醋酸钠、3-氯丙酸钠盐、一硫酸酯类诸如月桂基硫酸酯、以及乙氧化和丙氧化醇的硫酸酯，例如丁基二醇硫酸酯。
如此所得染料分散液非常有利于制作染液及印刷糊。
有某些使用领域系以粉末调合物为较佳者。此等粉末包含染料、分散剂和其它助剂，例如温润剂、氧化剂、防腐剂和防尘剂及上述“酸予体”。
制造粉化染料制备物的较佳方法包括将上述液体染料分散液的液体去除，例如以真空干燥、冷冻干燥，经由在桶式干燥机上干燥，但较佳者为经由喷雾干燥。
染液系经由用染色介质，较佳者水，将所需量的上述染料调合物稀释以得到用于染色的5∶1至50∶1之液体比(liquor ratio)而制成。此外，染液习惯上常包括其它染色助剂，诸如分散剂、湿润剂和固定剂。其中包括有机酸和无机酸诸如醋酸、丁二酸、硼酸或磷酸以调定pH在从4至5的范围内，较佳者4.5。有利地为缓冲pH调定及加入定量的缓冲系统。醋酸/醋酸钠系统为一有利缓冲系统之例子。
要使用该染料或染料混合物于纺织品印刷中之时，系将需要量的上述染料调合物与增稠剂，例如碱金属海藻酸盐或类似者，及于恰当处的其它添加剂，例如固定加速剂、湿润剂及氧化剂，以习用方式一起捏合而给出印刷糊。
本发明也提供以喷墨法进行数字纺织物印刷所用的墨液，其中包含本发明通式(I)染料。
本发明墨液较佳者为水性者且包含一或多种本发明的通式(I)染料，例如其量为以墨液总重量为基准之0.1至50重量％，较佳者其量为1至30重量％且更佳者其量为1至15重量％。彼等进一步包含特别者从0.1至20重量％的分散剂。适当的分散剂系谙于此技者所知者，可自商业上取得且包括例如磺酸化或磺酸基甲基化之木质素、芳族磺酸和甲醛的缩合产物，经取代或未经取代的酚与甲醛之缩合产物，聚丙烯酸酯和相应的共聚物，改质聚胺基甲酸酯及环氧烷类与可烷基化的化合物，诸如脂肪醇、脂肪胺、脂肪酸、羧醯胺类与经取代或未经取代的酚类之反应产物。
本发明墨液可进一步包含习用的添加剂，例如，黏度缓和剂以将黏度调定在于20至50℃温度范围中的从1.5至40.0mPas范围内。较佳的墨液具有在从1.5至20mPas范围内的黏度且特佳的墨液具有在从1.5至15mPas范围内的黏度。
可用的黏度缓和剂包括流变学添加剂，例如聚乙烯基己内醯胺、聚乙烯基吡咯烷酮和彼等的共聚物、聚醚多元醇、缔合性增稠剂、聚脲、海藻酸钠、改质聚半乳甘露糖、聚醚脲、聚胺基甲酸酯和非离子纤维素醚类。作为其它添加剂者，本发明墨液可包括表面活性物质以将表面张力调定在从20至65mv/m的范围内，此于恰当处系依所用目的而调整(热或压电技术)。可用的表面活性物质包括例如任何类别的界面活性剂，较佳者非离子界面活性剂、丁基二甘醇及1，2-己二醇。该墨液可进一步包括习用添加剂，例如抑制真菌和细菌生长用的化学物种，其量为以墨液总重量为基准约0.01至1重量％。
本发明的墨液可用习用方式经由将诸成分在水中混合而制备成。
具体实施方式
实施例1
将5.2克6-溴-2，4-二硝基苯胺在30至35℃下导到含9.8毫升硫酸(96％)，0.5毫升水和3.5毫升亚硝基硫酸(40％)的混合物中。于30-35℃下搅拌3小时之后，用醯胺基磺酸破坏掉过多的亚硝酸盐。将经如此所得重氮翁盐敏捷地滴加到含6.4克N-(3-二乙胺基苯基)丁醯胺酸2-酮基丙酯、50毫升甲醇和200克冰的混合物中。于搅拌1小时后，抽气过滤出固体，用水洗且干燥而得10.7克式(Iab)的N-[2-(2-溴-4，6-二硝基苯基偶氮基)-5-二乙胺基苯基]丁醯胺酸2-酮基丙酯。
(λmax[DMF]＝556奈米)，其可将聚酯染成紫色调且具有优良的洗涤和升华坚牢性。
实施例2
将5.9克的N-[2-(2-溴-4，6-二硝基苯基偶氮基)-5-二乙胺基苯基]-丁醯胺酸2-酮基丙酯和0.9克的氰化铜(I)在30毫升N-甲基吡咯烷酮中于80℃下搅拌4小时。于冷却后，于该批料中滴加200毫升甲醇和50毫升水。抽气滤出沉淀物，用5％盐酸和水洗，且在减压下干燥而留下4.8克的式(Iac)染料
(λmax[DMF]＝588奈米)，其可将聚酯染成亮蓝色调且具有优良的洗涤和升华坚牢性。
实施例3至98
可用上面的方法得到之其它本发明染料为表1中所示出者。
实施例99
将4.7克的2-胺基-3，5-二硝基噻吩在15℃下导到含8.0毫升硫酸(96％)，0.5毫升水和9.4克亚硝基硫酸(40％)的混合物中。在-5℃下搅拌1小时之后，用醯胺基磺酸破坏过剩的亚硝酸盐。将如此所得重氮翁盐溶液迅速地滴加到含7.9克4-(3-二乙胺基苯基胺基甲醯基)丁酸氰基甲酯、40毫升甲醇和200克冰之混合物中。于搅拌1小时后，抽气滤出固体，用水洗且干燥而留下7.0克式(Iba)4-[5-二乙胺基-2-(3，5-二硝基噻吩-2-基偶氮基)丁酸氰基甲酯
(λmax[丙酮]＝635奈米)，其可将聚酯染成绿蓝色调且具有优良的洗涤和升华坚牢性。
实施例100至104
可用上述方法得到的其它本发明染料为表2所示者。
表2
实施例105
使用由50克/升8％海藻酸钠溶液，100克/升8-12％稻子豆粉醚溶液和5克/升磷酸-钠在水中所组成的染液予以压染后，予以干燥。湿摄取率(wet pickup)为70％。然后将经如此预处理过的纺织物用根据上述程序制备且包含
3.5％实施例1染料，
2.5％Disperbyk 190分散剂，
30％1，5-戊二醇，
5％二乙二醇一甲醚，
0.01％Mergal K9N杀生物剂，
58.99％水
的水性墨，使用drop-on-demand(压电型)喷墨印刷头予以印刷。将印刷体完全干燥。利用超热蒸汽在175℃进行固定化7分钟。随后对印刷件施以碱性还原清除，用温水冲洗及随后干燥。
Claims (9)
1.一种通式(I)染料，
其中
D为重氮成分的残基；
R1为氢、(C1-C6)-烷基、(C1-C4)-烷氧基或卤素，或与R2合并形成-*CH(CH3)CH2C(CH3)2-，此处以*标志的碳原子系接着到苯基核；
R2和R3各独立地为氢、(C1-C6)-烷基、经取代(C1-C6)-烷基、(C3-C4)-烯基或经取代(C3-C4)-烯基；
R4为-CHR5CN、-CHR6COR7或-CH＝CH2；
R5为氢、(C1-C6)-烷基或经取代(C1-C6)-烷基；
R6为氢、(C1-C6)-烷基或经取代(C1-C6)-烷基；
R7为(C1-C6)-烷基、经取代(C1-C6)-烷基、乙烯氧基、(C1-C6)-烷氧基、经取代(C1-C6)-烷氧基、苯氧基、经取代苯氧基、苯基或经取代苯基；且
L为(C2-C6)-伸烷基、氧插接(C2-C6)-伸烷基、(C2-C6)-伸烯基、伸芳基或经取代伸芳基；
但其限制条件为当R5为氢时，L不为C2-伸烷基。
2.如权利要求1所述的染料，其中D表式(IIa)之基
其中
T1和T2各独立地为氢、(C1-C6)-烷基、(C1-C4)-烷氧基、-SO2-(C1-C6)-烷基、-SO2-芳基、氰基、卤素或硝基；且
T3和T4各独立地为氢、卤素、氰基、三氟甲基、-SCN、-SO2CH3或硝基；
但其限制条件为T1、T2、T3和T4中至少有一者不为氢；
或表式(IIb)之基
其中
T5和T5’各独立地为氢、硝基或卤素；且
T6为氢、-SO2CH3、-SCN、(C1-C4)-烷氧基、卤素或硝基；
但其限制条件为T5、T5’和T6中至少有一者不为氢；
或表式(IIc)之基
其中T12为氢或卤素；
或表式(IId)之基
其中
T7为硝基、-CHO、氰基、-COCH3或下式之基；
其中T10为氢、卤素、硝基或氰基；
T8为氢、(C1-C4)-烷基或卤素；且
T9为硝基、氰基、-COCH3或-COOT11，其中T11为(C1-C4)-烷基；
或表式(IIe)之基
其中T7和T8皆为上面所定义者；
或表式(IIf)之基
其中T13为苯基或S-(C1-C4)-烷基；
或表式(IIg)之基
其中T14为氰基、-COCH3或-COOT11，其中T11为(C1-C4)-烷基且T15为苯基或(C1-C4)-烷基；
或表式(IIh)之基
其中T14为上面定义者且T16为(C1-C4)-烷基；
或表式(IIi)之基
其中T17为氰基甲基、苯甲基或烯丙基；
或表式(IIj)之基
3.如权利要求1或2所述的染料，其中
R1为氢、氯、甲基、乙基、甲氧基或乙氧基；
R2和R3各独立地为氢、甲基、乙基、正丙基、正丁基、氰基乙基、-C2H4OCOCH3、-C2H4OCOC2H4、-C2H4COOCH3、-C2H4COOC2H5、甲氧基乙基、乙氧基乙基、苯氧基乙基、苯乙基、苯甲基或烯丙基；
R5和R6各为氢；
R7为甲基、乙基、苯基、甲氧基、乙氧基、丙氧基、乙烯氧基、苯甲氧基或苯氧基；且
L为伸乙基、伸丙基、伸丁基、伸乙烯基、伸丁烯基、1，3-伸苯基、1，4-伸苯基或-CH2OCH2-。
4.如权利要求1或2所述的染料，其符合通式(Ia)
其中T1至T4、R1至R4和L各为权利要求1中所定义者。
5.如权利要求取所述的染料，其符合通式(Iaa)
其中
T3’为氢、氰基、氯或溴；
T4’为氢、氰基、硝基、氯或溴；
R1’为氢或甲氧基；
R2’为氢、乙基、烯丙基或甲氧基乙基；
R3’为乙基、烯丙基、甲氧基乙基或氰基乙基；
R4’为氰基甲基、-CH2COR7’或-CH＝CH2；
R7’为甲基、乙基、苯基、甲氧基、乙氧基或乙烯氧基；且
L’为伸乙基、伸丙基、伸丁基、1，3-伸苯基、1，4-伸苯基或-CH2-O-CH2-；
但其限制条件为当R4’为氰基甲基时，L’不为伸乙基。
6.如权利要求1或2所述的染料，其符合通式(Ib)
其中R1至R4和L各为权利要求1中所定义者且D’表
3，5-二氰基-4-氯-2-噻吩基、3，5-二氰基-2-噻吩基、3，5-二氰基-4-甲基-2-噻吩基、3-氰基-5-硝基-2-噻吩基、3-氰基-4-氯-5-甲醯基-2-噻吩基、3，5-二硝基-2-噻吩基、3-乙醯基-5-硝基-2-噻吩基、5-乙醯基-3-硝基-2-噻吩基、3-((C1-C4)-烷氧基羰基)-5-硝基-2-噻吩基、5-苯基偶氮基-3-氰基-2-噻吩基、5-(4-硝基苯基偶氮基)-3-氰基-2-噻吩基、5-硝基-2-噻唑基、4-氯-5-甲醯基-2-噻唑基、5-硝基-3-苯并异噻唑基、7-溴-5-硝基-3-苯并异噻唑基、7-氯-5-硝基-3-苯并异噻唑基、3-甲基-4-氰基-5-异噻唑基、3-苯基-1，2，4-噻二唑-2-基、5-((C1-C2)-烷基氢硫基)-1，3，4-噻二唑-2-基、1-氰基甲基-4，5-二氰基-2-咪唑基、6-硝基苯并噻唑-2-基、5-硝基苯并噻唑-2-基、6-硫氰酸基-2-苯并噻唑基、6-氯-2-苯并噻唑基或(5)，6，(7)-二氯-2-苯并噻唑基。
7.一种制备如权利要求1所述的通式(I)染料的方法，其包括将通式(III)化合物
D-NH2 (III)
其中D为在权利要求1中所定义者，予以重氮化且偶合到通式(IV)化合物上
其中R1至R4和L各为权利要求1中所定义者。
8.一种如权利要求1所述通式(I)染料于染色和印刷疏水性材料的用途。
9.一种以喷墨法进行数位纺织品印刷所用的墨，其包含如权利要求1所述的通式(I)染料。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007003372A DE102007003372A1 (de) | 2007-01-23 | 2007-01-23 | Dispersionsfarbstoffe, ihre Herstellung und ihre Verwendung |
| DE102007003372.0 | 2007-01-23 |
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| Publication Number | Publication Date |
|---|---|
| CN101578338A true CN101578338A (zh) | 2009-11-11 |
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ID=39323660
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| Application Number | Title | Priority Date | Filing Date |
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| CNA2008800013697A Pending CN101578338A (zh) | 2007-01-23 | 2008-01-14 | 分散性染料，彼之制造与应用 |
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| Country | Link |
|---|---|
| US (1) | US7833291B2 (zh) |
| EP (1) | EP2125962B1 (zh) |
| JP (1) | JP2010516826A (zh) |
| KR (1) | KR101600092B1 (zh) |
| CN (1) | CN101578338A (zh) |
| BR (1) | BRPI0806817B1 (zh) |
| CA (1) | CA2676212C (zh) |
| DE (1) | DE102007003372A1 (zh) |
| ES (1) | ES2424157T3 (zh) |
| MX (1) | MX2009007823A (zh) |
| TW (1) | TWI427123B (zh) |
| WO (1) | WO2008090042A1 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104220535A (zh) * | 2012-03-19 | 2014-12-17 | 美利肯公司 | 羧酸盐染料 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0625624D0 (en) * | 2006-12-21 | 2007-01-31 | Dystar Textilfarben Gmbh & Co | Disperse dye mixtures |
| US8715368B2 (en) | 2010-11-12 | 2014-05-06 | The Procter & Gamble Company | Thiophene azo dyes and laundry care compositions containing the same |
| DE102011008683A1 (de) | 2011-01-15 | 2012-07-19 | Dystar Colours Distribution Gmbh | Dispersionsfarbstoffmischungen, ihre Herstellung und Verwendung |
| PT2943537T (pt) | 2013-01-14 | 2019-02-15 | Dystar Colours Distrib Gmbh | Misturas de corantes com humidade elevada e dispersão rápida |
| EP2754697A1 (en) | 2013-01-14 | 2014-07-16 | DyStar Colours Distribution GmbH | High wet-fast disperse dye mixtures |
| EP2754698A1 (en) | 2013-01-14 | 2014-07-16 | DyStar Colours Distribution GmbH | High wet-fast disperse dye mixtures |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB909843A (en) | 1959-02-10 | 1962-11-07 | Ici Ltd | New monoazo dyestuffs containing ester groups |
| JPS4896621A (zh) * | 1972-03-16 | 1973-12-10 | ||
| JPS4936725A (zh) * | 1972-08-11 | 1974-04-05 | ||
| JPS5429331A (en) * | 1977-08-08 | 1979-03-05 | Mitsui Toatsu Chem Inc | Water-insoluble azo dye, its preparation, and dyeing of synthetic fiber using the same |
| JPS582352A (ja) | 1981-06-30 | 1983-01-07 | Nippon Kayaku Co Ltd | 水不溶性モノアゾ化合物及びそれを用いる合成繊維の染色法 |
| GB9126351D0 (en) | 1990-12-21 | 1992-02-12 | Ici Plc | Mixed crystal dyes |
| GB9400972D0 (en) | 1994-01-19 | 1994-03-16 | Zeneca Ltd | Process |
| JP3632994B2 (ja) * | 1994-02-04 | 2005-03-30 | 日本化薬株式会社 | 染料組成物及びそれを用いる疎水性繊維の染色方法 |
| DE4419622A1 (de) | 1994-06-03 | 1995-12-07 | Cassella Ag | Monoazofarbstoffe, ihre Herstellung und Verwendung |
| JP3136300B2 (ja) * | 1994-09-28 | 2001-02-19 | 工業技術院長 | 導電性セラミックス、導電性セラミックス膜の製造方法、導電性セラミックス成形物の製造方法、導電性セラミックス成形用組成物及び電気発熱体 |
| GB9514524D0 (en) | 1995-07-15 | 1995-09-13 | Zeneca Ltd | Dye mixtures |
| JPH0936725A (ja) * | 1995-07-18 | 1997-02-07 | Omron Corp | 光電センサ |
| GB0324584D0 (en) | 2003-10-21 | 2003-11-26 | Dystar Textilfarben Gmbh & Co | Disperse azo dyestuffs |
| TWI352103B (en) * | 2003-12-10 | 2011-11-11 | Clariant Finance Bvi Ltd | Disperse dyes |
| GB0422403D0 (en) | 2004-10-08 | 2004-11-10 | Dystar Textilfarben Gmbh & Co | Disperse dye mixtures |
-
2007
- 2007-01-23 DE DE102007003372A patent/DE102007003372A1/de not_active Withdrawn
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2008
- 2008-01-14 ES ES08701452T patent/ES2424157T3/es active Active
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- 2008-01-14 CN CNA2008800013697A patent/CN101578338A/zh active Pending
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- 2008-01-14 BR BRPI0806817-8A patent/BRPI0806817B1/pt not_active IP Right Cessation
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- 2008-01-14 WO PCT/EP2008/050318 patent/WO2008090042A1/de active Application Filing
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- 2008-01-14 EP EP08701452.8A patent/EP2125962B1/de active Active
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104220535A (zh) * | 2012-03-19 | 2014-12-17 | 美利肯公司 | 羧酸盐染料 |
| CN104220535B (zh) * | 2012-03-19 | 2017-03-22 | 美利肯公司 | 羧酸盐染料 |
Also Published As
| Publication number | Publication date |
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| EP2125962B1 (de) | 2013-05-22 |
| EP2125962A1 (de) | 2009-12-02 |
| US20100076182A1 (en) | 2010-03-25 |
| TWI427123B (zh) | 2014-02-21 |
| BRPI0806817A2 (pt) | 2011-09-13 |
| MX2009007823A (es) | 2009-07-30 |
| WO2008090042A1 (de) | 2008-07-31 |
| BRPI0806817B1 (pt) | 2019-09-17 |
| US7833291B2 (en) | 2010-11-16 |
| KR20090122186A (ko) | 2009-11-26 |
| ES2424157T3 (es) | 2013-09-27 |
| CA2676212A1 (en) | 2008-07-31 |
| JP2010516826A (ja) | 2010-05-20 |
| TW200846418A (en) | 2008-12-01 |
| KR101600092B1 (ko) | 2016-03-04 |
| DE102007003372A1 (de) | 2008-07-24 |
| CA2676212C (en) | 2014-05-13 |
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