CN101454402A - 分散染料、其制备和其应用 - Google Patents
分散染料、其制备和其应用 Download PDFInfo
- Publication number
- CN101454402A CN101454402A CNA2007800191079A CN200780019107A CN101454402A CN 101454402 A CN101454402 A CN 101454402A CN A2007800191079 A CNA2007800191079 A CN A2007800191079A CN 200780019107 A CN200780019107 A CN 200780019107A CN 101454402 A CN101454402 A CN 101454402A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- hydrogen
- ethyl
- compound
- butyl
- 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
- 239000000986 disperse dye Substances 0.000 title description 2
- 239000000975 dye Substances 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- -1 hydroxyl- Chemical group 0.000 claims description 20
- 238000007639 printing Methods 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 239000004753 textile Substances 0.000 claims description 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000006193 diazotization reaction Methods 0.000 claims description 5
- 230000002209 hydrophobic effect Effects 0.000 claims description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 description 26
- 239000000203 mixture Substances 0.000 description 20
- 239000006185 dispersion Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 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 4
- 230000009467 reduction Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000009980 pad dyeing Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-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
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 150000008431 aliphatic amides Chemical class 0.000 description 2
- 125000002877 alkyl aryl 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 239000000661 sodium alginate Substances 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
- 238000000967 suction filtration Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000012976 tarts Nutrition 0.000 description 2
- 239000004034 viscosity adjusting agent Substances 0.000 description 2
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-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
- ATACSYDDCNWCLV-UHFFFAOYSA-N 2-chloroacetic acid;sodium Chemical compound [Na].OC(=O)CCl ATACSYDDCNWCLV-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
- SLBQXWXKPNIVSQ-UHFFFAOYSA-N 4-nitrophthalic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1C(O)=O SLBQXWXKPNIVSQ-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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
- 229920001747 Cellulose diacetate Polymers 0.000 description 1
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 1
- 240000008886 Ceratonia siliqua Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 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
- KSQXVLVXUFHGJQ-UHFFFAOYSA-M Sodium ortho-phenylphenate Chemical compound [Na+].[O-]C1=CC=CC=C1C1=CC=CC=C1 KSQXVLVXUFHGJQ-UHFFFAOYSA-M 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
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 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
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 244000309464 bull Species 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
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 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
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000009940 knitting Methods 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
- 235000010755 mineral Nutrition 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- HSPSCWZIJWKZKD-UHFFFAOYSA-N n-chloroacetamide Chemical compound CC(=O)NCl HSPSCWZIJWKZKD-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- PPSSQRUPSRPZON-UHFFFAOYSA-N nitrobenzene;sodium Chemical compound [Na].[O-][N+](=O)C1=CC=CC=C1 PPSSQRUPSRPZON-UHFFFAOYSA-N 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 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
- 235000007715 potassium iodide Nutrition 0.000 description 1
- 229960004839 potassium iodide Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material 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
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical class [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 229920002994 synthetic fiber Polymers 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
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 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
- 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
-
- 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
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
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Abstract
本发明涉及通式(I)的染料，其中X和R1至R5各自如权利要求1所定义，其制备方法以及其用途。
Description
技术领域
本发明涉及包含N-取代的邻苯二甲酰亚胺重氮成分以及苯胺系列偶联成分的分散染料，涉及其制备以及涉及其用于对纺织材料染色的用途。
背景技术
这类分散染料是已知的且描述于例如FR 1,358,145，US 3,980,634，US 4,039,522，EP 0 051 563 A1，EP 0 443 984 A1，EP 0 667 376 A1，WO 00/40656，WO 02/68539，WO 02/74864和WO 04/44058中。然而，它们具有某些缺点，例如它们不符合现今关于某些耐洗牢度的要求。现已令人惊讶地发现，下文所限定的染料符合规定的要求并还具有出色的提升力(buildup)、出色的染色温度依赖性以及更高的pH稳定性。
发明内容
相应地，本发明提供通式(I)的染料
其中
X1和X2都是氢或都是氰基；
R1是乙基、直链或支链的(C3-C10)-烷基或-(CH2)nCOOR6；
R2是氢、甲基、氰甲基、卤代甲基、乙基、氰乙基、卤代乙基、卤素、-NH-CO-R7或-NH-SO2-R7；
R3是(C1-C8)-烷基，或者被羟基-、(C1-C4)-烷氧基、氰基、卤素、R7OCO-、R7OOC-、乙烯基或苯基取代的(C1-C8)-烷基；
R4是氢，(C1-C8)-烷基，或者被羟基-、(C1-C4)-烷氧基、氰基、卤素、R7OCO-、R7OOC-、乙烯基或苯基取代的(C1-C8)-烷基；
R5是氢，卤素，(C1-C4)-烷基，(C1-C8)-烷氧基，或者被卤素、氰基或苯基取代的(C1-C8)-烷氧基；
R6是(C1-C4)-烷基；
R7是(C1-C8)-烷基，或者被卤素或氰基取代的(C1-C8)-烷基；且
n是1、2、3、4或5，
但是应排除
R1是乙基或正丁基，X1和X2都是氰基且R2是-NH-CO-R7，其中R7是C1-烷基的化合物；
R1是乙基或正丁基，X1和X2都是氢且R2是-NH-CO-R7或NH-SO2-R7的化合物；
R1是-(CH2)nCOOR6(其中n＝2且R6是C1-烷基)，X1和X2都是氢，R2是-NH-CO-R7(其中R7是C2-烷基)，R3和R4之一是C2-烷基且另一个是被R7OCO取代的C2-烷基(其中R7是C1-烷基)并且R5是氢的化合物；
R1是支链的C3-烷基，X1和X2都是氢，R2是-NH-CO-R7(其中R7是C3-烷基)，R3和R4都是C2-烷基且R5是氢的化合物；
R1是异丁基，X1和X2都是氢，R2是-NH-CO-R7(其中R7是C6-烷基)或是-NH-SO2-R7(其中R7是C1-烷基)，R3和R4都是C2-烷基且R5是氢的化合物。
直链的(C3-C10)-烷基R1可以是正丙基、正丁基、正戊基、正己基、正庚基、正辛基、正壬基或正癸基。支链的(C3-C10)-烷基R1可以是例如异丙基、异丁基、仲丁基或叔丁基。直链的(C3-C10)-烷基是优选的。
当R1是乙基或正丁基时，R2优选是氰甲基、卤代甲基、乙基、氰乙基、卤代乙基、卤素、-NH-CO-R7或-NH-SO2-R7。-NH-CO-R7(R2)特别是乙酰氨基和丙酰氨基；而-NH-SO2-R7(R2)特别是甲基磺氨基及乙基磺氨基。
R3或R7即被取代或未被取代的(C1-C8)-烷基，可以是直链或支链的，并且是例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、或叔丁基或者直链或支链的戊基、己基、庚基或辛基。(C1-C4)-烷基是优选的并且甲基和乙基是特别优选的。相同的逻辑适用于R6即(C1-C4)-烷基，其相应地优选是甲基或乙基，且亦适用于R5中的(C1-C8)-烷氧基，其相应地优选是(C1-C4)-烷氧基且更优选是甲氧基或乙氧基。作为在R3或R4中(C1-C8)-烷基上的取代基，(C1-C4)-烷氧基同样优选是甲氧基或乙氧基。卤素优选是氟、氯或溴且更优选是氯或溴。
R5优选是氢。
根据本发明优选的染料符合通式(Ia)
其中
R1是正戊基或-(CH2)nCOOR6；
R2是甲基、-NH-CO-甲基或-NH-SO2-甲基；
R3和R4独立地是乙基、-(CH2)2CN、-(CH2)2OMe、-(CH2)2OAc或正丁基；
R6是甲基、乙基或丁基；以及
n是1、2或3。
根据本发明优选的染料也符合通式(Ib)
其中
R1是乙基或-(CH2)nCOOR6；
R3和R4独立地是乙基、-(CH2)2CN、-(CH2)2OMe、-(CH2)2OAc或正丁基；
R6是甲基、乙基或丁基；以及
n是1、2、3或5。
依本发明优选的染料也符合通式(Ic)
R1是异丙基、异丁基、仲丁基或叔丁基；且
R3和R4独立地是乙基、-(CH2)2CN、-(CH2)2OMe、-(CH2)2OAc或正丁基。
本发明的通式(I)的染料可使用本领域技术人员已知的方法来获得。例如，通过氰化通式(II)化合物
其中R1至R5各自如以上所定义，获得X1和X2都是氰基的本发明的化合物。氰化优选用已知的方式实现，比如说使用氰化铜(I)和氰化锌(II)的混合物在碘化钾与咪唑的存在下于热的NMP中进行。
通式(II)的化合物可通过重氮化通式(III)的化合物
且偶联至通式(IV)的化合物而获得
其中R2至R5各自如以上所定义。
通式(III)的化合物的重氮化通常用已知方式实现，例如将亚硝酸钠用于例如用盐酸或硫酸产生酸性的水性介质中，或将亚硝酰基硫酸用于稀硫酸、磷酸或者用于乙酸与丙酸的混合物中。优选的温度范围介于0℃与15℃之间。
重氮化的化合物偶联至通式(IV)的化合物通常同样用已知的方式实现，例如在酸性的、水性、水性-有机或有机介质中，特别有利地在低于10℃的温度下进行。所用的酸特别是硫酸、乙酸或丙酸。
通式(IV)的化合物是已知的且能通过已知的方法来制备。
通式(III)的化合物例如可以如下程序从邻苯二甲酰亚胺制备。
例如Organic Synthesis(有机合成)，CV 2，第459页(第5版)中所描述的那样，将邻苯二甲酰亚胺硝化，将得到的4-硝基邻苯二甲酰亚胺用氢氧化钠水溶液处理以将之转化为4-硝基邻苯二甲酸。与乙酸酐一同加热除去一分子水以获得相应的酸酐。它与通式(V)的胺反应
R1-NH2(V)
其中R1如上所定义，以形成通式(VI)的化合物
其中R1如上所定义。
邻苯二甲酸酐与通式(VI)的胺的反应优选通过将邻苯二甲酸酐引入胺中并且使反应在升高的温度下进行数小时而完成。
将通式(VI)的化合物还原，从而得到通式(VII)的化合物
其中R1如上所定义。该反应有利地通过Chem.Pharm.Bull.42(9)，1994，1817页中所描述的方法进行。通式(VII)的化合物最后在冰醋酸中溴化以获得式(III)的化合物。
以通式(VII)的化合物(代替通式(III)的化合物)进行上述重氮化和偶联反应，得到通式(I)的本发明染料，其中X1和X2都是氢。根据本发明的这些最终的染料因此可通过将通式(VII)化合物
其中R1如以上所定义，进行重氮化且偶联至通式(IV)的化合物而获得
其中R2至R5各自如上所定义。
本发明通式(I)的染料对于疏水性材料的染色及印染极其有用，所得染色物和印染物在匀色调和高实用牢度方面均很显著。值得特别提及的是良好的耐光、耐干热定型和褶皱、耐水和汗的牢度，特别是非常好的耐洗牢度，以及高的还原稳定性。所提及的疏水性材料可以是合成或半合成的原料。
本发明因此也提供通式I的染料用于疏水性材料染色和印染的用途，即以常规方式将这种材料染色和印染的方法，其中使用一种或多种根据本发明通式(I)的染料作为着色剂。
有用的疏水性材料包括例如纤维素二乙酸酯、纤维素三乙酸酯、聚酰胺以及特别是高分子量聚酯。高分子量聚酯材料特别是基于聚对苯二甲酸乙二醇酯的那些。疏水性合成材料可以片或丝状的形式存在，并可被加工成例如纱线或机织或针织的纺织材料。优选的是纤维纺织材料，其也可以例如微纤维状的形式存在。
根据本发明所提供的用途的染色可以以常规方式完成，优选是在110至140℃下的染色压热器中由80至约110℃温度的水性分散体(如果合适的话在载体的存在下)、通过竭染法或通过HT方法进行，以及还通过所谓的热固色方法进行，其中织物用染色液轧染(padded)并随后在约180至230℃下固色/定型。
所提及材料的印染可以以本身已知的方式完成，通过将本发明式(I)的染料或染料混合物引入到印染糊料中，并对以该印染糊料印染后的织物在180至230℃的温度下用HT蒸气、高压蒸气或干热(如果合适的话在载体存在下)进行处理从而将染料固色。
本发明式(I)的染料或染料混合物当用于染色液、轧染液或印染糊料时呈细分散的状态。染料以常规方式通过以下步骤转化成细分的细分散状态：将所制造的染料连同分散剂在液体介质(优选是水)中成浆状，且使混合物受到剪切力的作用以机械粉碎初始的染料粒子至达到获得最佳比表面积且染料沉淀被最小化的程度。这是在合适的磨机中完成的，例如球磨机或砂磨机。染料粒度通常介于0.5至5微米间，且优选等于约1微米。在研磨操作中所用的分散剂可以是非离子或阴离子的。非离子分散剂包括例如氧化烯(例如氧化乙烯或氧化丙烯)与可烷基化的化合物(例如脂肪醇、脂肪胺、脂肪酸、酚、烷基酚及甲酰胺)的反应产物。阴离子分散剂是例如木质磺酸盐、烷基-或烷基芳基磺酸盐或烷基芳基聚二醇醚硫酸盐。
由此所得的染料制剂对大部分应用而言是可倾倒的。因此，染料和分散剂含量在这些情况中是受限制的。通常，分散体被调节成最多50重量％的染料含量和最多约25重量％的分散剂含量。因为经济上的理由，染料含量在大部分之情况中不能低于15重量％。分散体也可含有另外的助剂，例如作为氧化剂的那些，例如间硝基苯磺酸钠，或作为杀真菌剂的那些，例如邻苯基苯酚钠及五氯苯酚钠，以及特别是所谓的“酸供体”，例如丁内酯、单氯乙酰胺、氯代乙酸钠、二氯乙酸钠、3-氯丙酸的钠盐、诸如硫酸月桂酯的单硫酸酯、以及诸如丁二醇硫酸酯的乙氧基化及丙氧基化醇的硫酸酯。
由此所得的染料分散体对于制造染色液及印染糊料是极有利的。
有某些优选使用粉末配方的领域。这些粉末包含染料或染料混合物、分散剂及其它助剂，例如润湿剂、氧化剂、防腐剂和防尘剂以及上述的“酸供体”。制造粉末状的染料制剂优选的方法在于例如通过真空干燥、冷冻干燥、通过在鼓式干燥器上干燥，但优选通过喷雾干燥，对上述液态染料分散体的液体进行汽提。
染色液通过用染色介质(优选是水)稀释必要量的上述染料配方，以获得用于染色的5:1至50:1的液体比例。此外，通常惯例上在液体中包含另外的染色助剂，例如分散剂、润湿剂及固色助剂。加入有机酸及无机酸，例如乙酸、丁二酸、硼酸或磷酸以将pH设定在4至5的范围内，优选4.5。对pH设定进行缓冲且添加足量缓冲体系是有利的。乙酸/乙酸钠体系是有利的缓冲体系的实例。
为了在织物印染中使用染料或染料混合物，以常规方式将必要量的上述染料配方连同增稠剂(例如海藻酸碱金属盐)、以及如果恰当的话另外的添加剂(例如固色促进剂、润湿剂和氧化剂)进行捏合，以得到印染糊料。
本发明也提供用于通过喷墨方法进行纺织品数字印染的油墨，其包含通式(I)的本发明的染料。
本发明的油墨优选是水性的且包含一种或多种通式(I)的本发明的染料，例如基于油墨的总重量，染料的量是0.1重量％至50重量％，优选1重量％至30重量％，更优选1重量％至15重量％。它们还包含特别是0.1重量％至20重量％的分散剂。适合的分散剂对本领域技术人员是已知的，是可商业获得的并且包括例如磺酸化或磺甲基化的木质素、芳香磺酸与甲醛的缩合产物、被取代或未被取代的酚与甲醛的缩合产物、聚丙烯酸酯和相应的共聚物、改性的聚氨酯以及氧化烯与可烷基化的化合物(例如脂肪醇、脂肪胺、脂肪酸、甲酰胺和被取代或未被取代的酚)的反应产物。
本发明的油墨还可以包含惯常的添加剂，例如粘度调节剂以将粘度在20至50℃温度下设定为1.5至40.0mPas的范围内。优选的油墨具有在1.5至20mPas范围内的粘度且特别优选的油墨具有在1.5至15mPas范围内的粘度。
有用的粘度调节剂包括流变添加剂，例如聚乙烯基己内酰胺、聚乙烯基吡咯烷酮及它们的共聚物、聚醚多元醇、缔合型增稠剂、聚脲、海藻酸钠、改性的半乳甘露聚糖、聚醚脲、聚氨酯和非离子型纤维素醚。通过由另外的添加剂，本发明的油墨可以包含表面活性物质以将表面张力设定于20至65mN/m范围内，取决于所用的方法(热或压电技术)如合适的话可进行变更。有用的表面活性物质包括例如任何种类的表面活性剂，优选是非离子型表面活性剂、丁基二甘醇以及1，2-己二醇。油墨还可以包括惯常的添加剂，例如抑制真菌或细菌生长的化学物质，基于油墨的总重量其量是0.01重量％至1重量％。
本发明的油墨可以以常规方式通过将各成分在水中混合而制备。
【实施方式】
实例1
a)将8.0克的式(IIIa)化合物
在室温下引入84毫升乙酸和28毫升丙酸的混合物中。在0至5℃下搅拌5分钟后，逐滴添加5毫升的40％亚硝基硫酸并且混合物随后在该温度下搅拌2小时。在搅拌2小时之前，反应的混合物在0至5℃下逐渐添加至4.5克N，N-二乙基-间甲苯胺在39毫升乙酸和13毫升丙酸中的溶液中。在pH用乙酸钠调升至4.0之后，添加314毫升的水并随后将混合物搅拌5小时。将所得的悬浮液抽滤，用水洗涤并干燥以留下10.9克的式(IIa)化合物
b)将7.0克的式(IIa)化合物悬浮在圆底烧瓶的70毫升NMP中。添加0.5克咪唑、0.7克氰化铜(I)、1.1克氰化锌和1.3克碘化钠，接着在70℃搅拌下1.5小时。冷却后，逐滴添加2.9克氯化铁(III)在150毫升水中的溶液，再搅拌5小时。将悬浮液抽滤，用稀盐酸和水洗涤并干燥以留下6.2克的本发明式(Ic)染料。
其将聚酯染成稍带红的蓝色。
通过以上方法可获得的本发明另外的染料列于表1中。
表1
实施例30
1重量份的式(Ic)染料与17份的水和2份的可商业获得的分散剂在珠磨后转变成3％的分散体。
通过在130℃的高温竭染法，使用该分散体在聚酯纺织品上产生出1％的染色品，且该染色品用连二亚硫酸钠还原清洁。由此所得的染色品具有极高的耐洗牢度。
实施例31
由聚酯组成的纺织品用由50克/升8％的海藻酸钠溶液、100克/升8至12％的角豆粉醚溶液和5克/升的磷酸单钠在水中组成的液体进行轧染且干燥。湿轧染率是70％。
使用按需喷墨(压电)的喷墨印染头，以依照上述程序制备且含以下成分的水性油墨对经上述预处理的纺织品进行印染
3.5％的式(Ia)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生物杀灭剂，和
58.99％的水。
印染物被完全干燥。利用过热蒸气在175℃进行固色7分钟。该印染物随后经历碱还原清洁，温热漂洗且干燥。
Claims (9)
1.一种通式(I)的染料
其中
X1和X2都是氢或都是氰基；
R1是乙基，直链或支链的(C3-C10)-烷基，或者-(CH2)nCOOR6；
R2是氢，甲基，氰甲基，卤代甲基，乙基，氰乙基，卤代乙基，卤素，-NH-CO-R7，或-NH-SO2-R7；
R3是(C1-C8)-烷基，或者被羟基-、(C1-C4)-烷氧基、氰基、卤素、R7OCO-、R7OOC-、乙烯基或苯基取代的(C1-C8)-烷基；
R4是氢，(C1-C8)-烷基，或者被羟基-、(C1-C4)-烷氧基、氰基、卤素、R7OCO-、R7OOC-、乙烯基或苯基取代的(C1-C8)-烷基；
R5是氢，卤素，(C1-C4)-烷基，(C1-C8)-烷氧基，或者被卤素、氰基或苯基取代的(C1-C8)-烷氧基；
R6是(C1-C4)-烷基；
R7是(C1-C8)-烷基，或者被卤素或氰基取代的(C1-C8)-烷基；且
n是1、2、3、4或5，
但是应排除
R1是乙基或正丁基，X1和X2都是氰基且R2是-NH-CO-R7，其中R7是C1-烷基的化合物；
R1是乙基或正丁基，X1和X2都是氢且R2是-NH-CO-R7或-NH-SO2-R7的化合物；
R1是-(CH2)nCOOR6其中n＝2且R6是C1-烷基，X1和X2都是氢，R2是-NH-CO-R7其中R7是C2-烷基，R3和R4中之一是C2-烷基而另一个是R7OCO取代的C2-烷基其中R7是C1-烷基，并且R5是氢的化合物；
R1是支链的C3-烷基，X1和X2都是氢，R2是-NH-CO-R7其中R7是C3-烷基，R3和R4都是C2-烷基并且R5是氢的化合物；以及
R1是异丁基，X1和X2都是氢，R2是-NH-CO-R7其中R7是C6-烷基，或R2是-NH-SO2-R7其中R7是C1-烷基，R3和R4都是C2-烷基并且R5是氢的化合物。
2.如权利要求1所述的染料，其中R5是氢。
3.如权利要求1和/或2所述的染料，其符合通式(Ia)
其中
R1是正戊基或-(CH2)nCOOR6；
R2是甲基、-NH-CO-甲基或-NH-SO2-甲基；
R3和R4独立地是乙基、-(CH2)2CN、-(CH2)2OMe、-(CH2)2OAc或正丁基；
R6是甲基、乙基或丁基；且
n是1、2或3。
4.如权利要求1和/或2所述的染料，其符合通式(Ib)
其中
R1是乙基或-(CH2)nCOOR6；
R3和R4独立地是乙基、-(CH2)2CN、-(CH2)2OMe、-(CH2)2OAc或正丁基；
R6是甲基、乙基或丁基；且
n是1、2、3或5。
5.如权利要求1和/或2所述的染料，其符合通式(Ic)
其中R1是异丙基、异丁基、仲丁基或叔丁基；且
R3和R4独立地是乙基、-(CH2)2CN、-(CH2)2OMe、-(CH2)2OAc或正丁基。
6.一种制备如权利要求1到3或5的一项或多项中所述的其中X1和X2都是氰基的通式(I)染料的方法，所述方法包含将通式(II)的化合物氰化
其中R1至R5各自如权利要求1所定义。
7.一种制备如权利要求1、2和4的一项或多项中所述的其中X1和X2都是氢的通式(I)染料的方法，所述方法包含将通式(VII)的化合物重氮化
其中R1如权利要求1所定义，并偶联至通式(IV)的化合物
其中R2至R5各自如权利要求1所定义。
8.权利要求1所述的通式I染料在对疏水性材料进行染色和印染中的用途。
9.一种用于通过喷墨方法进行纺织品数字印染的油墨，其包含如权利要求1所述的通式(I)染料。
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| DE102006027535A DE102006027535A1 (de) | 2006-06-14 | 2006-06-14 | Dispersionsfarbstoffe, ihre Herstellung und ihre Verwendung |
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| EP (1) | EP2032659A2 (zh) |
| JP (1) | JP2009540077A (zh) |
| KR (1) | KR20090016558A (zh) |
| CN (1) | CN101454402A (zh) |
| BR (1) | BRPI0712753A2 (zh) |
| CA (1) | CA2655255A1 (zh) |
| DE (1) | DE102006027535A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105647224A (zh) * | 2016-01-28 | 2016-06-08 | 俞杏英 | 一种邻苯二甲酰亚胺-偶氮分散染料单体化合物及其制备方法和应用 |
| CN107722663A (zh) * | 2017-10-10 | 2018-02-23 | 浙江万丰化工有限公司 | 一种偶氮染料化合物及其制备方法和应用 |
| CN108864732A (zh) * | 2018-07-06 | 2018-11-23 | 浙江万丰化工有限公司 | 一种含甲磺酰胺基团的偶氮染料化合物及其制备方法和应用 |
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| US3980634A (en) * | 1973-07-02 | 1976-09-14 | Eastman Kodak Company | Phthalimidyl-azo aniline type compounds and polyester fibers dyed therewith |
| CA1041998A (en) * | 1973-07-02 | 1978-11-07 | Max A. Weaver | Phthalimidyl-azo-m-acylamidoaniline compounds and polyester fibers dyed therewith |
| US4039522A (en) * | 1974-02-01 | 1977-08-02 | Eastman Kodak Company | Phthalimidyl-azo-m-acylamido-n-substituted aniline compounds and polyester fibers dyed therewith |
| DE3170172D1 (en) * | 1980-10-30 | 1985-05-30 | Ciba Geigy Ag | Mono-azo compounds |
| DE59104277D1 (de) * | 1990-02-19 | 1995-03-02 | Ciba Geigy Ag | Phthalimidyl-Azofarbstoffe. |
| US5199956A (en) * | 1990-09-03 | 1993-04-06 | Ciba-Geigy Corporation | Process for dyeing hydrophobic textile material with disperse dyes from super-critical carbon dioxide |
| JPH06329930A (ja) * | 1993-05-06 | 1994-11-29 | Ciba Geigy Ag | アゾ染料 |
| US6008332A (en) * | 1994-02-11 | 1999-12-28 | Ciba Specialty Chemicals Corporation | Phthalimidylazo dyes, process for their preparation and the use thereof |
| TWI243192B (en) * | 1998-12-31 | 2005-11-11 | Ciba Sc Holding Ag | Phthalimidyl azo pigments, method for producing same and utilization thereof |
| CN1289607C (zh) * | 2001-02-07 | 2006-12-13 | 西巴特殊化学品控股有限公司 | 苯邻二甲酰亚胺基偶氮染料、其制备方法及其用途 |
| CZ20032383A3 (cs) * | 2001-02-07 | 2003-11-12 | Ciba Specialty Chemicals Holding Inc. | Ftalimidylová azobarviva, způsob jejich přípravy a jejich použití |
| KR100572257B1 (ko) * | 2002-06-20 | 2006-04-25 | 재단법인서울대학교산학협력재단 | 프탈이미드 구조를 가지는 아조계 알칼리 세정성 분산염료를 이용한 폴리에스테르 섬유재료의 염색 방법 |
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2007
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- 2007-06-06 KR KR1020087028587A patent/KR20090016558A/ko not_active Application Discontinuation
- 2007-06-06 EP EP07729953A patent/EP2032659A2/de not_active Withdrawn
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105647224A (zh) * | 2016-01-28 | 2016-06-08 | 俞杏英 | 一种邻苯二甲酰亚胺-偶氮分散染料单体化合物及其制备方法和应用 |
| CN107722663A (zh) * | 2017-10-10 | 2018-02-23 | 浙江万丰化工有限公司 | 一种偶氮染料化合物及其制备方法和应用 |
| CN108864732A (zh) * | 2018-07-06 | 2018-11-23 | 浙江万丰化工有限公司 | 一种含甲磺酰胺基团的偶氮染料化合物及其制备方法和应用 |
| CN108864732B (zh) * | 2018-07-06 | 2020-05-05 | 浙江万丰化工股份有限公司 | 一种含甲磺酰胺基团的偶氮染料化合物及其制备方法和应用 |
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| Publication number | Publication date |
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| DE102006027535A1 (de) | 2007-12-20 |
| MX2008015961A (es) | 2009-01-09 |
| CA2655255A1 (en) | 2007-12-21 |
| US20090209742A1 (en) | 2009-08-20 |
| WO2007144298A3 (de) | 2008-02-21 |
| KR20090016558A (ko) | 2009-02-16 |
| WO2007144298A2 (de) | 2007-12-21 |
| TW200808910A (en) | 2008-02-16 |
| BRPI0712753A2 (pt) | 2012-10-02 |
| JP2009540077A (ja) | 2009-11-19 |
| EP2032659A2 (de) | 2009-03-11 |
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