CN101778908A - 分散染料、它们的制备及应用 - Google Patents
分散染料、它们的制备及应用 Download PDFInfo
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- CN101778908A CN101778908A CN200880102708A CN200880102708A CN101778908A CN 101778908 A CN101778908 A CN 101778908A CN 200880102708 A CN200880102708 A CN 200880102708A CN 200880102708 A CN200880102708 A CN 200880102708A CN 101778908 A CN101778908 A CN 101778908A
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- China
- Prior art keywords
- group
- hydrogen
- alkyl
- perhaps
- dyestuff
- 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
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- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000000975 dye Substances 0.000 claims abstract description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 54
- 239000000460 chlorine Substances 0.000 claims description 35
- -1 3-C 4Thiazolinyl Chemical group 0.000 claims description 31
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 238000007639 printing Methods 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 238000004043 dyeing Methods 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 claims description 5
- 230000002209 hydrophobic effect Effects 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000004753 textile Substances 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 238000006193 diazotization reaction Methods 0.000 claims description 3
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 13
- 239000006185 dispersion Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 238000000859 sublimation Methods 0.000 description 6
- 230000008022 sublimation Effects 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- 239000012752 auxiliary agent Substances 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000080 wetting agent Substances 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
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 2
- 240000008886 Ceratonia siliqua Species 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000009980 pad dyeing Methods 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000000843 powder 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
- 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
- 238000003756 stirring Methods 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 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
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- TURPNXCLLLFJAP-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl hydrogen sulfate Chemical class OCCOCCOCCOS(O)(=O)=O TURPNXCLLLFJAP-UHFFFAOYSA-N 0.000 description 1
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 1
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 description 1
- LDTCWISGJYTXDC-UHFFFAOYSA-N 5-nitro-1,2-benzothiazol-3-amine Chemical compound C1=C([N+]([O-])=O)C=C2C(N)=NSC2=C1 LDTCWISGJYTXDC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- 241000233866 Fungi Species 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
- 239000004117 Lignosulphonate Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 239000002202 Polyethylene glycol 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000008431 aliphatic amides Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 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
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000002650 habitual effect Effects 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229940045641 monobasic sodium phosphate 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000011218 segmentation Effects 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
- 235000017281 sodium acetate Nutrition 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical group 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
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0815—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)-
- C09B29/0816—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR
- C09B29/0817—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR having N(-aliphatic residue-COOR)2 as substituents
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
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Abstract
本发明提供通式(I)的染料、它们的制备方法以及它们的应用，其中D、R1～R6、X、m和n各自如权利要求1中所定义。
Description
本发明涉及分散偶氮染料，其中苯乙酮酯被连接到生色团上。包含这种结构要素的染料为已知的并且例如在WO05/056690中进行了描述。
现已发现，其中苯乙酮酯被另一个苯基或者苯氧基取代的分散偶氮染料具有突出的特性，并且由它们制备的染色品以良好的耐洗性和突出的升华牢度而引人注目。更具体地，这种染色品满足了工业洗烫的特殊要求，其中织物在洗涤循环后暴露于高温。
出人意料，我们业已发现，尽管它们相对高的分子量，本发明的染料容易染在聚酯和聚酯混纺织物上。
本发明提供通式(I)的染料：
其中
D为重氮成分的残基；
R1为氢、C1-C6烷基、C1-C4烷氧基、羟基、卤素、-NHCHO、-NHCO-C1-C6烷基或者-NHSO2-C1-C6烷基；
R2为氢、C1-C6烷基、C1-C4烷氧基或者卤素；
R3为氢、C1-C6烷基、取代的C1-C6烷基、C3-C4烯基或者取代的C3-C4烯基；或者
R2和R3结合形成基团-C*H(CH3)CH2C(CH3)2-，其中标记*的碳原子连接至苯核上；
R4为氢或者C1-C6烷基；
R5为氢或者C1-C6烷基；
R6为氢或者C1-C6烷基；
X为苯基、苯硫基、苯磺酰基或者苯氧基；
n为0、1或者2；和
m为0或者1。
重氮成分的残基D具体为分散染料领域中惯用的残基并且对于本领域技术人员来说是已知的。
优选地，D
表示式(IIa)的基团
其中
T1和T2独立地为氢、卤素、C1-C4烷基、C1-C4烷氧基、氰基、-SO2-C1-C4烷基或者硝基；和
T4和T3独立地为氢、卤素、三氟甲基、氰基、-SO2CH3、-SCN或者硝基；
条件为T1、T2、T3和T4中的至少一个不为氢；
或者表示式(IIb)的基团
其中
T5和T5’独立地为氢或者卤素；和
T6为氢、-SO2CH3、-SCN、C1-C4烷氧基、卤素、氰基或者硝基；
条件为T5、T5’和T6中的至少一个不为氢；
或者表示式(IIc)的基团
其中
T12为氢或者卤素；
或者表示式(IId)的基团
其中
T7为硝基、-CHO、-COCH3、氰基或者下式的基团
其中T10为氢、卤素、硝基或者氰基；
T8为氢、(C1-C6)烷基或者卤素；和
T9为硝基、氰基、-COCH3或者-COOT11；其中T11为C1-C4烷基；
或者表示式(IIe)的基团
其中T7和T8各自如以上所定义；
或者表示式(IIf)的基团
其中T13为苯基或者C1-C4烷硫基；
或者表示式(IIg)的基团
其中T14为氰基或者-COCH3或者-COOT11，其中T11为C1-C4烷基；并且T15为苯基或者C1-C4烷基；
或者表示式(IIh)的基团
其中T14如以上所定义并且T16为C1-C4烷基；
或者表示式(IIi)的基团
其中T17为氰甲基、苯甲基或者烯丙基；
或者表示式(IIj)的基团
C1-C6烷基R1～R7可为直链的或支链的，并且例如为甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基或者正己基。
相似考虑适用于C1-C6烷氧基。
取代的C1-C6烷基R3具体被选自卤素、氰基、羟基、C1-C6烷氧基、-COO-C1-C6烷基、-OCOO-C1-C6烷基和-OCO-C1-C6烷基中的1至3个取代基所取代。
C3-C4烯基R3具体有烯丙基。
卤素优选为氯或者溴。
R1优选为氢、氯、甲基、乙基、羟基、甲氧基、乙氧基、乙酰氨基、丙酰氨基、甲磺酰氨基或者乙磺酰氨基。
R2优选为氢、氯、甲基、乙基、甲氧基或者乙氧基。
R3优选为氢、甲基、乙基、丙基、丁基、甲氧基乙基、氰乙基、C2H4OCOCH3、C2H4OCOC2H5、C2H4COOCH3、C2H4COOC2H5或者烯丙基。
R4、R5和R6各自优选为甲基或者氢，更优选为氢。
X优选为苯基或者苯氧基，并且更优选为苯基。
n优选为0或者1，更优选为0。
m优选为1。
m+n优选为1。
本发明优选的染料符合通式(Ia)
其中T1～T4、R1～R6、m和n各自如以上所定义。
本发明特别优选的该类型染料符合以下通式(Iaa)
其中
T1为硝基；
T3为氢、氰基、氯或者溴；
T4为氢、氰基、硝基、氯、溴或者三氟甲基；
R1为氢、羟基、甲基、乙酰氨基或者丙酰氨基；
R2为氢、氯、甲基或者甲氧基；
R3为氢、甲基、乙基、丁基或者烯丙基。
本发明进一步优选的染料符合通式(Ib)
其中T1～T4、R1～R6、m和n各自如以上所定义。
本发明特别优选的该类型染料符合通式(Iba)
其中
T1为硝基；
T3为氢、氰基、氯或者溴；
T4为氢、氰基、硝基、氯、溴或者三氟甲基；
R1为氢、羟基、甲基、乙酰氨基或者丙酰氨基；
R2为氢、氯、甲基或者甲氧基；
R3为氢、甲基、乙基、丁基或者烯丙基。
本发明通式(I)的染料可通过本领域技术人员已知的方法制备。
例如，将通式(III)的化合物重氮化并偶合在通式(IV)的化合物上，
D-NH2 (III)
其中D如以上所定义，
其中R1～R6、X、m和n各自如以上所定义。
通式(III)的化合物通常按照已知的方式被重氮化，例如在酸性水介质中，例如在用盐酸或者硫酸使之呈酸性的水性介质中用亚硝酸钠进行，或者在稀硫酸、磷酸或者乙酸与丙酸的混合物中用亚硝基硫酸进行。优选的温度范围为0～15℃。
这些重氮化的化合物通常以已知的方式同样偶合在通式(IV)的化合物上，例如在酸性、水性、水性-有机或有机介质中，在低于10℃的温度下特别有利。所使用的酸具体为硫酸、乙酸或丙酸。
这些通式(III)和(IV)的化合物为已知的并且可通过已知的方法制备。
本发明的这些通式(I)的染料突出地适用于疏水性材料的染色和印花，因为所得到的染色品和印花品因在均染色调(level shade)和高耐用性而引人注目。
值得强调的是良好的耐洗性，特别是与非常良好的升华牢度组合的耐洗性。
已经进一步确定本发明的分散染料突出地适用于例如用于工作装的聚酯-棉混纺品的连续染色。特别是根据“Hoechst结合试验”所达到的耐湿性突出，“Hoechst结合试验”对于这种应用特别相关并且其中经染色的材料在ISO 105-C05试验之前暴露于190℃的温度达5分钟。
本发明因此还提供通式I的染料在疏水性材料的染色和印花中的应用，以及在常规步骤中对这类材料进行染色和印花的方法，这些方法使用本发明的一种或多种通式(I)的染料作为着色剂。
所提及的疏水性材料可以具有合成起源或纤维素起源。所考虑的疏水性材料包括例如二乙酸酯纤维素、三乙酸酯纤维素、聚酰胺以及特别是大分子聚酯。由大分子聚酯组成的材料具体为基于聚对苯二甲酸乙二醇酯类的材料。
这些疏水性合成材料可以为片形结构或线形结构，并可以被加工成例如纱或者纺织或针织的织物。优选纤维性纺织材料，它们还能够以例如微纤维的形式存在。
与根据本发明的用途一致的染色可以按常规方式进行，优选在水性分散体中，如果合适的话在载体的存在下，在80～约110℃下通过浸染法或在110～140℃下于染色高压釜中通过HT法进行，并且还可以通过所谓的热固法(thermofix method)进行，其中用染色液对织物进行轧染，随后在约180～230℃固色/定色。
所提及的材料的印花能够以本身已知的方式进行，通过在印花浆中结合本发明的通式(I)的染料，并对以此印花的织物在180～230℃的温度下用HT蒸汽、高压蒸汽或干热，如果适合的话在载体的存在下，进行处理，从而使该染料固色。
当本发明的通式(I)的染料被用在染色液、轧染液或印花浆中时，它们应该处于非常精细的细分状态。
该染料以常规方式转化成细分的精细状态，通过在液态介质中、优选在水中将已制成的染料与分散剂一起调成浆状，并使该混合物经受剪切力作用以机械地粉碎原始的染料颗粒至达到最佳的比表面积并使染料的沉淀最小化的程度。这在适当的研磨机如球磨机或砂磨机中完成。染料的颗粒大小通常为0.5～5μm并优选等于约1μm。
在研磨操作中所使用的分散剂可以为非离子型或阴离子型。非离子型分散剂包括，例如，环氧烷烃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、酚类、烷基酚类和羧酰胺类的反应产物。阴离子型分散剂为，例如，木素磺酸盐类、烷基或烷芳基磺酸酯类或烷芳基聚乙二醇醚硫酸酯类。
由此获得的染料制品对于多数应用应当可倾倒。因此，在这些情况下该染料和分散剂含量是有限的。总体来说，这些分散体被调节到染料含量按重量计高达50％以及分散剂含量按重量计高达约25％。出于节约的原因，在大多数情况下染料含量按重量计不低于15％。
该分散体还可以包含其它助剂，例如充当氧化剂的助剂如间-硝基苯磺酸钠，或杀真菌试剂如邻-苯基苯酚钠和五氯苯酚钠，以及特别是所谓的“酸供体”，例子为丁内酯、一氯乙酰胺、氯乙酸钠、二氯乙酸钠、3-氯丙酸的钠盐、单硫酸酯如硫酸月桂酯，以及还有乙氧基化和丙氧基化醇类的硫酸酯如丁基乙二醇硫酸酯(butylglycol sulfate)。
由此获得的染料分散体对于构成染色液和印花浆非常有利。
存在其中优选粉末配制品的某些应用领域。这些粉末包含所述的染料、分散剂和其它助剂，例如润湿剂、氧化剂、防腐剂和防尘剂以及以上提及的“酸供体”。
制备染料的粉状制剂的优选的方法在于对上述液体染料分散体去掉它们的液体，例如通过真空干燥、冷冻干燥、在转鼓式干燥器上进行干燥，但是优选通过喷雾干燥。
这些染色液为通过对必需量的上述染料配制品用染料介质，优选水，进行稀释而制得，这样就获得了用于染色的1∶5～1∶50浴比。此外，总体来说常规的是在这些液体中包括另外的染色助剂，如分散剂、润湿剂和固色助剂。有机酸和无机酸类如乙酸、琥珀酸、硼酸或磷酸包括在内以设定4～5的范围内、优选4.5的pH值。有利的是对pH设定进行缓冲并加入足够量的缓冲体系。乙酸/乙酸钠体系为有利的缓冲体系的实例。
为了在织物印花中使用染料或染料混合物，必需量的以上提及的染料配制品与增稠剂例如碱金属藻酸盐类等以及适当时另外的添加剂如固色促进剂、润湿剂和氧化剂，以常规方式混炼在一起以产生印花浆。
本发明还提供通过喷墨法进行数字织物印花用的油墨，其包含本发明的通式(I)的染料。
本发明的油墨优选为水性的并包含一种或多种本发明的通式(I)的染料，例如以基于该油墨的总重量按重量计为0.1％～50％的量，优选以按重量计为1％～30％的量以及更优选以按重量计为1％～15％的量。它们进一步包含特别是按重量计0.1％～20％的分散剂。适合的分散剂对于本领域技术人员是已知的，为市售的并包括例如磺化的或磺甲基化的木素、芳磺酸与甲醛的缩合产物、取代的或未取代的苯酚与甲醛的缩合产物、聚丙烯酸酯和相应的共聚物、改性的聚氨酯以及环氧烷烃与可烷基化的化合物例如脂肪醇类、脂肪胺类、脂肪酸类、羧酰胺类以及取代或未取代的酚类的反应产物。
本发明的油墨可以进一步包含常规的添加剂，例如粘度缓和剂以便将粘度设定为在20～50℃的温度范围内1.5～40.0mPas的范围。优选的油墨具有在1.5～20mPas范围内的粘度并且特别优选的油墨具有在1.5～15mPas范围内的粘度。
有用的粘度缓和剂包括流变性能添加剂，例如聚乙烯基己内酰胺、聚乙烯基吡咯烷酮以及还有它们的共聚物、聚醚多元醇、缔合性增稠剂、聚脲、海藻酸钠、改性半乳甘露聚糖、聚醚脲、聚氨酯和非离子型纤维素醚类。
通过另外的添加剂，本发明的油墨可以包括表面活性物质以将表面张力设定在20～65mN/m的范围内，适当时根据所使用的方法(热或压电技术)对其进行调整。有用的表面活性物质包括例如任何类型的表面活性剂，优选非离子型表面活性剂、丁基二甘醇和1，2-己二醇。
这些油墨可以进一步包含常规添加剂，例如抑制真菌和细菌生长的材料，其量为基于该油墨总重量按重量计0.01％～1％。
本发明的油墨可以按照常规的方式通过在水中混合这些成分来制备。
实施例1
在室温下，将66.2g的6-溴-2，4-二硝基苯胺悬浮在185ml乙酸中。在轻度冷却下加入7.5ml硫酸(96％)。在15～20℃下逐滴加入45ml亚硝基硫酸(40％)。随后将该混合物在15～20℃下搅拌一小时。由此获得的重氮盐溶液在5～10℃下于一小时内逐滴加入到111.6g的2-联苯-4-基-2-氧代乙基3-(5-乙酰氨基-2-甲氧基苯氨基)丙酸酯、11的丙酮和10g尿素的混合物中。随后搅拌1小时，用500ml水稀释，吸滤，用水洗涤并进行干燥，从而得到86g式(Iab)的染料
(λmax[DMF]＝594nm)该染料在聚酯上产生具有良好的耐洗性和升华牢度的蓝色调。
实施例2
在室温下，将51.6g的2-氯-4-硝基苯胺与100ml水以及85ml盐酸(30％)搅拌18小时。加入160g冰后，在1～2分钟内加入40ml亚硝酸溶液(53g/l)。随后该混合物在不高于5℃下搅拌2小时并且过剩的亚硝酸盐随后被氨基磺酸破坏。由此得到的重氮盐溶液在0～5℃下于1小时内逐滴加入116.3g的2-联苯-4-基-2-氧代乙基3-(乙基苯氨基)丙酸酯在1.41丙酮的溶液中。该混合物随后于5～10℃下搅拌18小时并倒在6.51水上。吸滤沉淀物，用水洗涤并干燥，从而得到167g式(Iac)的染料
(λmax[DMF]＝514nm)该染料在聚酯上产生具有良好耐洗性和优异的升华牢度的红色调。
实施例3
在100℃下，将14.3g的2-联苯-4-基-2-氧代乙基3-{[3-乙酰氨基-4-(2-溴-4，6-二硝基苯基偶氮)苯基]乙氨基}丙酸酯以及1.9g的氰化铜(I)在80ml的N-甲基吡咯烷酮中搅拌2小时。冷却后，将250ml甲醇逐滴加入到该批料中。吸滤沉淀物，用少量甲醇和水洗涤。水湿固体在150ml盐酸(10％)中搅拌一小时，吸滤并用水洗涤。在减压下干燥得到8.8g式(Iad)的染料
(λmax[DMF]＝602nm)该染料将聚酯染成亮丽的蓝色调并且具有良好的耐洗性和优异的升华牢度。
类似于实施例1～3中描述的方法，制备表1中实施例4～45的化合物。
表1
| 实施例 | T1 | T2 | T3 | T4 | R1 | R2 | R3 | R4 | R5 | n | m | X | λmax(nm)DMF |
| 4 | NO2 | H | Br | NO2 | NHCOCH3 | OCH3 | CH2CH3 | H | H | 0 | 1 | C6H5 | 604 |
| 5 | NO2 | H | Cl | NO2 | NHCOCH3 | OCH3 | CH2CH3 | H | H | 0 | 1 | C6H5 | 604 |
| 6 | NO2 | H | H | NO2 | NHCOCH3 | OCH3 | CH2CH3 | H | H | 0 | 1 | C6H5 | 582 |
| 7 | NO2 | H | Br | NO2 | NHCOCH3 | OCH3 | CH2CH3 | H | H | 0 | 0 | C6H5 | 590 |
| 实施例 | T1 | T2 | T3 | T4 | R1 | R2 | R3 | R4 | R5 | n | m | X | λmax(nm)DMF |
| 8 | NO2 | H | Cl | NO2 | NHCOCH3 | OCH3 | H | H | H | 2 | 0 | C6H5 | 600 |
| 9 | NO2 | H | Cl | NO2 | NHCOCH3 | OCH3 | CH2CH＝CH2 | H | H | 0 | 1 | C6H5 | 598 |
| 10 | NO2 | H | Cl | NO2 | NHCOCH3 | OCH3 | CH3 | H | H | 0 | 1 | C6H5 | 600 |
| 11 | NO2 | H | Cl | NO2 | NHCOCH3 | OCH3 | H | H | H | 0 | 1 | C6H5 | 594 |
| 12 | NO2 | H | Br | NO2 | NHCOCH3 | OCH3 | H | H | H | 0 | 1 | OC6H5 | 594 |
| 13 | NO2 | H | Cl | NO2 | NHCOC2H5 | OCH3 | H | H | H | 0 | 1 | C6H5 | 594 |
| 14 | NO2 | H | Br | CN | NHCOCH3 | OCH3 | H | H | H | 0 | 1 | C6H5 | 624 |
| 15 | NO2 | H | Cl | NO2 | NHCOCH3 | OCH3 | H | CH3 | H | 0 | 1 | C6H5 | 596 |
| 16 | NO2 | H | Cl | NO2 | NHCOCH3 | OCH3 | H | H | CH3 | 0 | 1 | C6H5 | 592 |
| 17 | NO2 | H | H | NO2 | NHCOCH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 548 |
| 18 | NO2 | H | Cl | NO2 | NHCOCH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 560 |
| 19 | NO2 | H | CN | NO2 | NHCOCH3 | H | CH2CH3 | H | H | 0 | 0 | C6H5 | 584 |
| 20 | NO2 | H | Br | NO2 | NHCOCH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 558 |
| 21 | NO2 | H | H | CN | NHCOCH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 552 |
| 22 | NO2 | H | Br | CN | NHCOCH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 584 |
| 23 | NO2 | H | H | Cl | NHCOCH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 534 |
| 24 | NO2 | H | H | Cl | NHCOCH3 | H | 正丁基 | H | H | 0 | 1 | C6H5 | 534 |
| 25 | NO2 | H | H | H | NHCOCH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 514 |
| 26 | NO2 | H | H | H | NHCOCH3 | Cl | H | H | H | 0 | 1 | C6H5 | 450 |
| 27 | NO2 | H | H | CN | CH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 548 |
| 28 | NO2 | H | H | Cl | CH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 524 |
| 实施例 | T1 | T2 | T3 | T4 | R1 | R2 | R3 | R4 | R5 | n | m | X | λmax(nm)DMF |
| 29 | NO2 | H | Cl | Cl | CH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 462 |
| 30 | NO2 | H | Br | Cl | CH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 460 |
| 31 | NO2 | H | CN | CN | CH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 598 |
| 32 | NO2 | H | CN | CN | CH3 | H | 正丁基 | H | H | 0 | 1 | C6H5 | 600 |
| 33 | NO2 | H | Br | CN | CH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 560 |
| 34 | NO2 | H | H | CN | H | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 536 |
| 35 | NO2 | H | H | CN | H | H | 正丙基 | H | H | 0 | 1 | C6H5 | 538 |
| 36 | NO2 | H | Cl | Cl | H | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 442 |
| 37 | NO2 | H | Br | Cl | H | Hl | CH2CH3 | H | H | 0 | 1 | C6H5 | 440 |
| 38 | NO2 | H | H | H | H | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 488 |
| 39 | NO2 | H | H | H | H | H | CH2CH3 | H | H | 0 | 0 | C6H5 | 476 |
| 40 | NO2 | H | H | CN | H | H | CH2CH3 | H | H | 0 | 0 | C6H5 | 522 |
| 41 | NO2 | H | H | Cl | H | H | CH2CH3 | H | H | 0 | 1 | OC6H5 | 514 |
| 42 | NO2 | H | H | H | H | Cl | H | H | H | 0 | 1 | C6H5 | 452 |
| 43 | NO2 | Cl | H | Cl | H | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 510 |
| 44 | H | NO2 | H | H | CH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 452 |
| 45 | CH3 | H | CN | CN | NHCOCH3 | H | CH2CH3 | H | H | 0 | 1 | C6H5 | 532 |
实施例46
将6.5g的3-氨基-5-硝基苯并异噻唑引入到16.6ml硫酸(96％)和6ml磷酸(85％)的混合物中。然后，在10～15℃下逐滴加入6.9ml亚硝基硫酸(40％)。随后，在10～15℃下将该混合物搅拌4小时。在0～5℃下，将由此得到的重氮盐溶液迅速滴加到12.9g的2-联苯-4-基-2氧代乙基3-(乙基苯氨基)丙酸酯、250ml丙酮、1.7g尿素的混合物中。此后在室温下搅拌过夜，吸滤并用甲醇洗涤，然后用水洗涤并干燥，从而得到13.7g式(Ibb)的染料
(λmax[DMF]＝604nm)该染料将聚酯染成蓝色调并且具有非常好的耐洗性和升华牢度。
类似于实施例46中描述的方法，制备表2中实施例47～55的化合物。
表2
实施例56
由聚酯组成的织物用由50g/l的8％藻酸钠溶液、100g/l的8～12％角豆粉醚(carob flour ether)溶液和5g/l磷酸二氢钠在水中组成的液体进行轧染，然后干燥。吸湿量为70％。
由此预处理的织物随后用根据以上描述的方法制备并含有下列成分的水性油墨，采用按需喷墨(drop-on-demand)(压电)喷墨印刷头进行印花：
3.5％的实施例1的染料，
2.5％的Disperbyk 190分散剂，
30％的1，5-戊二醇，
5％的二乙二醇单甲醚，
0.01％的Mergal K9N杀菌剂，以及
58.99％的水。
该印花品充分干燥。在175℃下，借助过热蒸汽实现固色7分钟。该印花品随后经受碱性还原清洗，温水漂洗，随后干燥。
Claims (8)
1.通式(I)的染料：
其中
D为重氮成分的残基；
R1为氢、C1-C6烷基、C1-C4烷氧基、羟基、卤素、-NHCHO、-NHCO-C1-C6烷基或者-NHSO2-C1-C6烷基；
R2为氢、C1-C6烷基、C1-C4烷氧基或者卤素；
R3为氢、C1-C6烷基、取代的C1-C6烷基、C3-C4烯基或者取代的C3-C4烯基；
或者R2和R3结合形成基团-C*H(CH3)CH2C(CH3)2-，其中标记*的碳原子连接至苯核上；
R4为氢或者C1-C6烷基；
R5为氢或者C1-C6烷基；
R6为氢或者C1-C6烷基；
X为苯基、苯硫基、苯磺酰基或者苯氧基；
n为0、1或者2；和
m为0或者1。
2.如权利要求1所述的染料，其中D表示
式(IIa)的基团
其中
T1和T2独立地为氢、卤素、C1-C4烷基、C1-C4烷氧基、氰基、-SO2-C1-C4烷基或者硝基；和
T4和T3独立地为氢、卤素、三氟甲基、氰基、-SO2CH3、-SCN或者硝基；
条件为T1、T2、T3和T4中的至少一个不为氢；
或者表示式(IIb)的基团
其中
T5和T5’独立地为氢或者卤素；和
T6为氢、-SO2CH3、-SCN、C1-C4烷氧基、卤素、氰基或者硝基；
条件为T5、T5’和T6中的至少一个不为氢；
或者表示式(IIc)的基团
其中
T12为氢或者卤素；
或者表示式(IId)的基团
其中
T7为硝基、-CHO、-COCH3、氰基或者下式的基团
其中T10为氢、卤素、硝基或者氰基；
T8为氢、C1-C6烷基、苯基或者卤素；
T9为硝基、氰基、-COCH3或者-COOT11；其中T11为C1-C4烷基；
或者表示式(IIe)的基团
其中T7和T8各自如以上所定义；
或者表示式(IIf)的基团
其中T13为苯基或者C1-C4烷硫基；
或者表示式(IIg)的基团
其中T14为氰基或者-COCH3或者-COOT11，其中T11为C1-C4烷基；并且T15为苯基或者C1-C4烷基；
或者表示式(IIh)的基团
其中T14如以上所定义并且T16为C1-C4烷基；
或者表示式(IIi)的基团
其中T17为氰甲基、苯甲基或者烯丙基；
或者表示式(IIj)的基团
3.如权利要求1和/或2所述的染料，其中
R1为氢、氯、甲基、乙基、羟基、甲氧基、乙氧基、乙酰氨基、丙酰氨基、甲磺酰氨基或者乙磺酰氨基；
R2为氢、氯、甲基、乙基、甲氧基或者乙氧基；
R3为氢、甲基、乙基、丙基、丁基、甲氧基乙基、氰乙基、C2H4OCOCH3、C2H4OCOC2H5、C2H4COOCH3、C2H4COOC2H5或者烯丙基；
R4、R5和R6各自为甲基或者氢；
X为苯基或者苯氧基；并且
m和n各自为0或者1。
4.如权利要求1和/或2所述的染料，其符合通式(Ia)：
其中T1～T4、R1～R6、m和n各自如权利要求1中所定义。
5.如权利要求4所述的染料，其符合通式(Iaa)：
其中
T1为硝基；
T3为氢、氰基、氯或者溴；
T4为氢、氰基、硝基、氯、溴或者三氟甲基；
R1为氢、氯、羟基、甲基、乙酰氨基或者丙酰氨基；
R2为氢、氯、甲基或者甲氧基；
R3为氢、甲基、乙基、丁基或者烯丙基；并且
X为苯基或者苯氧基。
6.通式(I)的染料的制备方法，其包括将通式(III)的化合物重氮化并偶合在通式(IV)的化合物上，
D-NH2 (III)
其中D如权利要求1中所定义，
其中R1～R6、X、m和n各自如权利要求1中所定义。
7.权利要求1中所述的通式I的染料在疏水性材料的染色和印花中的应用。
8.用于通过喷墨法进行数字织物印花的油墨，其包含权利要求1中所述的通式(I)的染料。
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| DE102007037522.2 | 2007-08-09 | ||
| DE102007037522A DE102007037522A1 (de) | 2007-08-09 | 2007-08-09 | Dispersionsfarbstoffe, ihre Herstellung und Verwendung |
| PCT/EP2008/060114 WO2009019207A1 (en) | 2007-08-09 | 2008-08-01 | Disperse dyes, their preparation and use |
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| CN (1) | CN101778908A (zh) |
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| DE102011008683A1 (de) * | 2011-01-15 | 2012-07-19 | Dystar Colours Distribution Gmbh | Dispersionsfarbstoffmischungen, ihre Herstellung und Verwendung |
| CN102757660B (zh) * | 2012-07-10 | 2013-12-11 | 浙江龙盛集团股份有限公司 | 一种苯并异噻唑染料单体化合物及分散染料 |
| CN113801494A (zh) * | 2021-10-09 | 2021-12-17 | 菲诺染料化工(无锡)有限公司 | 一种高牢度黑色分散染料组合物 |
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| GB1541010A (en) * | 1976-02-11 | 1979-02-21 | Ici Ltd | Disperse monoazo dyestuffs |
| CH660746A5 (de) * | 1983-11-04 | 1987-06-15 | Sandoz Ag | Monoazo-dispersionsfarbstoffe. |
| JP2785365B2 (ja) * | 1988-10-11 | 1998-08-13 | 住友化学工業株式会社 | モノアゾ化合物およびそれを用いて疎水性繊維材料を染色または捺染する方法 |
| EP1411089A1 (en) * | 2002-10-18 | 2004-04-21 | Clariant International Ltd. | Azo compounds |
| TWI352103B (en) * | 2003-12-10 | 2011-11-11 | Clariant Finance Bvi Ltd | Disperse dyes |
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- 2008-08-01 CA CA2695810A patent/CA2695810A1/en not_active Abandoned
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| ATE529483T1 (de) | 2011-11-15 |
| EP2254951B1 (en) | 2011-10-19 |
| MX2010001496A (es) | 2011-03-03 |
| CA2695810A1 (en) | 2009-02-12 |
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| US20110247150A1 (en) | 2011-10-13 |
| KR20100037170A (ko) | 2010-04-08 |
| EP2254951A1 (en) | 2010-12-01 |
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