CN101778907A - 1,3-噻唑基偶氮染料、它们的制备及应用 - Google Patents
1,3-噻唑基偶氮染料、它们的制备及应用 Download PDFInfo
- Publication number
- CN101778907A CN101778907A CN200880102724A CN200880102724A CN101778907A CN 101778907 A CN101778907 A CN 101778907A CN 200880102724 A CN200880102724 A CN 200880102724A CN 200880102724 A CN200880102724 A CN 200880102724A CN 101778907 A CN101778907 A CN 101778907A
- Authority
- CN
- China
- Prior art keywords
- formula
- dye
- alkyl
- disperse dye
- dyes
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 239000000987 azo dye Substances 0.000 title description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title 1
- 239000000986 disperse dye Substances 0.000 claims description 25
- -1 n-octyl Chemical group 0.000 claims description 20
- 238000004043 dyeing Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000004753 textile Substances 0.000 claims description 7
- 230000002209 hydrophobic effect Effects 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 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 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
- 241000764238 Isis Species 0.000 claims 1
- 239000000975 dye Substances 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 239000004744 fabric Substances 0.000 description 15
- 239000002270 dispersing agent Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000976 ink Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 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 3
- 238000003756 stirring Methods 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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229920001410 Microfiber Polymers 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008055 alkyl aryl sulfonates 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
- 239000007853 buffer solution Substances 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000003658 microfiber Substances 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 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
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 239000000984 vat dye Substances 0.000 description 2
- 229940015975 1,2-hexanediol Drugs 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 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
- KJRBYUWRYRRPKN-UHFFFAOYSA-N 2-amino-4-chloro-1,3-thiazole-5-carbaldehyde Chemical compound NC1=NC(Cl)=C(C=O)S1 KJRBYUWRYRRPKN-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-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
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 1
- 240000008886 Ceratonia siliqua Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229920000926 Galactomannan Polymers 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 239000004952 Polyamide 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 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
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000002095 anti-migrative effect Effects 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000000872 buffer Substances 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
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 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
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- NLFIMXLLXGTDME-UHFFFAOYSA-N propyl 2-cyanoacetate Chemical compound CCCOC(=O)CC#N NLFIMXLLXGTDME-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 229940080263 sodium dichloroacetate Drugs 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
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 235000010294 sodium orthophenyl phenol Nutrition 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
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- 150000003672 ureas Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/30—Ink jet printing
-
- 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
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0085—Thiazoles or condensed thiazoles
-
- 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
-
- 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
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/26—Amino phenols
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
- D06P3/8228—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye
- D06P3/8233—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye using dispersed dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Abstract
本发明提供式I的分散染料、它们的制备方法以及它们的应用，其中R1～R4、A和B各自如权利要求1中所定义。
Description
本发明涉及包含1，3-噻唑基重氮成分的分散偶氮染料。
包含这种重氮成分的偶氮染料为已知的并描述于例如GB 2071684A、DE 3313797A1、EP 0352006A2、EP 0453020A1、DE 4121754A1和EP 0578870A1中。描述于GB 2071684A和EP 0352006A2中的染料具体地包含取代的噻唑基重氮成分并且在后者情况下还以高耐光性而引人注目。
EP 0313918A2公开了红色染色的分散偶氮染料，它们包含二烷氧羰基烷基氨基酚作为偶合成分。
出人意料，目前已经发现包含描述于GB 2071684A或EP 0352006A2中的1，3-噻唑基重氮成分和描述于EP 0313918A2中的偶合成分的染料表现出优异的耐湿性以及良好的耐光性。这使得有可能满足对于具有优异耐湿性和良好耐光性的蓝色染色的市场需求。
因此本发明提供式1的分散染料：
其中，
R1和R2各自为C1-C4烷基或OH或C1-C4烷氧基取代的C1-C4烷基；
R3和R4各自为氢或甲基；
A和B中的一个为氰基，另一个为-COOX；并且
X为C2-C12烷基，被O间断的C2-C12烷基，C3-C4烯基或苯基-C1-C4烷基。
C1-C4烷基可以为直链的或支链的，并且为例如甲基、乙基、正丙基、异丙基、正丁基、异丁基或叔丁基。类似的考虑适用于烷氧基，例如它们为甲氧基或乙氧基。
C2-C12烷基同样可以为直链的或支链的，并且不但可以为以上对C1-C4烷基所提到的含义，还可以为例如正戊基、正己基、正庚基、正辛基、正壬基、正癸基、正十一烷基或正十二烷基或相应的支链基团。
被O间断的C2-C12烷基符合下式H3C-(CH2)n-O-(CH2)m-，其中n为0～10，m为1～11并且m+n为1～11。优选地，n为0～2并且m为2。
C3-C4烯基具体有烯丙基，苯基-C1-C4烷基具体有苯甲基和苯乙基。
式(1)的分散染料具体包含式(Ia)的分散染料：
而且还包含式(Ib)的分散染料：
其中在每一情况中R1～R4以及X各自如以上所定义。
特别优选的式(I)的分散染料符合式(Ic)：
其中X如以上所定义并且具体为乙基，正丙基，正丁基，异丁基，叔丁基，正戊基，正己基，正辛基，甲氧乙基，乙氧乙基，异丙氧乙基，正丁氧乙基，烯丙基或苯甲基。
本发明的通式(I)的染料可以通过本领域技术人员熟知的方法获得。例如，可以将通式(II)的化合物与式(III)的氰基乙酸烷基酯缩合，以形成本发明的式(I)的分散染料。
其中R1～R4各自如以上所定义，
其中X如以上所定义。
该反应可以通过EP 0578870A1中所描述的步骤来进行。
然而，对于缩合来说，将会发现在乙酸钠的存在下，在醇中进行，在关于产物的纯度和易于分离方面是特别有利的，所述醇可以含有水。优选的醇为甲醇和乙醇。水含量可以为0～40％，优选0～10％。该反应理想地在室温下进行。
所示的过程导致优先形成式(Ia)的分散染料，即在烯烃双键处具有E构型的化合物。这可以通过NMR-J-HMBC实验确认，在该实验中发现烯属的质子与羰基碳的偶合常数为6～7Hz，与腈碳的偶合常数为13～14Hz。
分离式(Ia)和(Ib)的分散染料对于它们以下描述的用作染料的用途不是必需的，但是如果需要当然可以采用常规的方法进行。
式(II)的化合物可以通过式(IV)的胺的重氮化并偶合到式(V)的化合物上而获得，
其中R1～R4各自如以上所定义。
式(IV)的化合物一般根据已知的方式重氮化，例如使用在稀硫酸、磷酸或者乙酸和丙酸的混合物中的亚硝基硫酸来进行。优选的温度范围为-10～10℃。
重氮化合物一般同样地以已知的方式偶合在式(V)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。
式(IV)的胺为已知的并且例如可如GB 2071684A中所述而获得。
式(V)的化合物同样为已知的并且例如可根据M.Lipp等人，Chem.Ber.1958，91，2239ff而获得。在乙酸中获得的反应混合物可直接使用。
本发明的通式(I)的分散染料突出地适用于疏水性材料的染色和印花，从而给出具有突出的耐洗性和耐汗性的紫色至蓝色染色和印花。这也特别适用于聚酯微纤维和含聚酯的混纺织物，例如与棉和弹性织物的混纺织物。
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为。特别地根据“Hoechst结合试验”所达到的耐湿性是突出的。在Hoechst结合试验中，将染色的织物暴露于160～190℃的接触热达5～10分钟，随后经受ISO 105C05或ISO 105-C06E2耐洗性试验。这模拟了工业洗烫条件，其中洗净的织物材料在干蒸汽装置中在非常高的温度下进行干燥。在该操作中，染料会迁移到表面并在随后的洗涤中造成临近织物着色或污染。此处本发明的染料由于极低的着色或污染而引人注目。
因此本发明还提供通式I的分散染料在疏水性材料的染色和印花中的应用，以及以常规步骤染色和印花此类材料的方法，这些方法使用根据本发明的一种或多种通式(I)的分散染料作为着色剂。
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地为基于聚对苯二甲酸乙二醇酯类的材料。
该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，适当时在载体的存在下，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)法进行，在该方法中用染色液对织物进行轧染，随后在约180～230℃下固色/定色。
所提及的材料的印花可以以本身已知的方式进行，通过将本发明的通式(I)的分散染料结合在印花浆中，并在180～230℃的温度下用HT蒸汽、高压蒸汽或干热，适当时在载体的存在下，处理以此印花的织物，从而使染料固色。
当本发明的通式(I)的分散染料被用在染色液、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的含量为有限的。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)的分散染料。
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)的分散染料，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各成分来制备。
以下的实施例对本发明进行了阐述。份数为按重量计。
实施例1
a)向808份乙酸和199份丙酸的混合物中加入100份2-氨基-4-氯-5-甲酰-1，3-噻唑(式(IV)的化合物)。随后搅拌30分钟后将温度降到0℃。然后，经过2小时向黄色的悬浮液中逐滴加入205份40％的亚硝基硫酸，同时温度保持在0～2℃。在该温度下继续搅拌3小时。
在1503份甲醇中存在335.3份用乙酸使之呈酸性并含有按重量计为51.6％的甲基3-[(3-羟基苯基)-(2-甲氧羰基乙基)氨基]丙酸酯的溶液，作为首次加料。加入400份按重量计为18％的氨基磺酸水溶液和1250份冰。在起始温度为-12℃下，于30分钟内将重氮化混合物逐滴加入到该偶合溶液中，在此过程中温度升到-1℃。随后将该混合物搅拌15分钟，然后用约930份按重量计为30％的氢氧化钠水溶液调节至pH 4.2。通过加入约1240份冰，将温度保持在低于10℃。搅拌过夜后，吸滤沉淀物。将强含盐的吸滤饼再次悬浮于1500份水中并搅拌2小时。吸滤后，获得228.5份式(IIa)的化合物，用水洗涤并干燥。这对应于理论产量的81.7％的收率。
b)将25份化合物(IIa)悬浮在314份乙醇中并搅拌30分钟。加入5.5份无水乙酸钠和21.85份氰基乙酸丙酯。随后将该混合物搅拌过夜。通过薄层色谱法测定反应的完全性。反应完全后，吸滤固体并用乙醇和水洗涤，干燥后得到18.55份下式的染料，对应于理论产量的60％：
λmax＝604nm(DMF)
与实施例1中所描述的步骤相似也可以获得以下的实施例2～16的分散染料。
| 实施例 | X | R1＝R2 | R3＝R4 | λmax(DMF)[nm] |
| 2 | 乙基 | Me | H | 604 |
| 3 | 乙基 | Et | H | 603 |
| 4 | 乙基 | Me | Me | 606 |
| 5 | 烯丙基 | Me | H | 600 |
| 6 | 正丁基 | Me | H | 600 |
| 7 | 异丁基 | Me | H | 606 |
| 8 | 叔丁基 | Me | H | 602 |
| 9 | 正戊基 | Me | H | 604 |
| 10 | 正己基 | Me | H | 604 |
| 11 | 正辛基 | Me | H | 604 |
| 12 | 苯甲基 | Me | H | 604 |
| 13 | CH2CH2OMe | Me | H | 604 |
| 14 | CH2CH2OEt | Me | H | 606 |
| 15 | CH2CH2O-i-Pr | Me | H | 606 |
| 16 | CH2CH2O-n-Bu | Me | H | 604 |
实施例17
根据实施例1获得的30g染料(处于水湿压饼的形式)与63g木质素磺酸钠和3g非离子型分散剂(松香酸和50摩尔当量的环氧乙烷的加成产物)在200ml水中混合并用25％的硫酸调节至pH 7。随后在室温下进行球磨1小时(90％＜1μm)，筛选并在喷雾干燥器中干燥。
将由此获得的2g粉末分散在1000g水中。将该分散体与基于萘磺酸钠盐和甲醛的缩合产物的0.5～2g/l的市售分散剂的液体，0.5～2g/l磷酸二氢钠的液体和2g/l市售的均染助剂的液体进行混合，并用乙酸将调节到pH 4.5～5.5。将由此获得的染色液引入100g基于聚对苯二甲酸乙二醇酯的织构的(textured)聚酯织物并在130℃下进行染色60分钟。还原清洗留下具有优异耐洗性和耐汗性以及非常好的升华牢度的红蓝色的染色。
用实施例2～16的染料重复实施例17同样给出具有优异的耐湿性的紫色至蓝色的染色。
实施例18
将实施例16的染料研磨并如实施例17的第一部分所描述的那样进行喷雾干燥。由此获得的染料通过热溶胶法施用于聚酯-棉混纺织物。为此目的，构成了含有30g/l上述分散染料、30g/l蓝色还原染料、2g/l
Wet C-AS润湿剂、10g/l
Gal M-IP抗迁移剂以及0.5ml/l60％乙酸的染料轧染剂。设定吸湿量为60～80％。在该织物通过轧染机后，它在120℃下干燥1～3分钟。随后在210～225℃下进行热溶胶60秒。此后，该织物通过含有60～120ml的38°Bé的烧碱和35～70g/l的次硫酸纳(这些量取决于还原染料的用量)的化学轧染剂。吸湿量应该为70～100％。随后在102℃下蒸发1分钟。随后该织物的最后定型为通过漂洗周期、用50％的过氧化氢氧化、用1g/l
Sperse C-SN螯合剂在98℃下皂洗并酸化至pH 5～6。再经过2次水漂洗浴后，将该织物进行干燥。
由此获得的红蓝色染色具有优异的耐洗性，特别是符合“Hoechst结合试验”的要求。用实施例1～15的染料获得了类似的结果。
实施例19
由聚酯组成的纺织织物用由50g/l 8％藻酸钠溶液、100g/l 8～12％角豆粉醚溶液和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％。
将由此预处理的织物随后用根据以上描述的步骤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)的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％的二乙二醇一甲醚，
0.01％的Mergal K9N杀菌剂，以及
58.99％的水。
将该印花品充分干燥。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 (7)
1.式I的分散染料：
其中
R1和R2各自为C1-C4烷基或OH或C1-C4烷氧基取代的C1-C4烷基；
R3和R4各自为氢或者甲基；
A和B中的一个为氰基，另一个为-COOX；并且
X为C2-C12烷基、被O间断的C2-C12烷基、C3-C4烯基或苯基-C1-C4烷基。
2.如权利要求1所述的分散染料，其符合式(Ia)：
3.如权利要求1和/或2所述的分散染料，其符合式(Ic)：
4.如权利要求1至3中一项或多项所述的分散染料，其中X为乙基、正丙基、正丁基、异丁基、叔丁基、正戊基、正己基、正辛基、甲氧乙基、乙氧乙基、异丙氧乙基、正丁氧乙基、烯丙基或苯甲基。
5.权利要求1所述的通式(I)的分散染料的制备方法，该方法包括将通式(II)的化合物与式(III)的氰基乙酸烷基酯进行缩合，
其中R1～R4各自如权利要求1中所定义，
其中X如权利要求1中所定义。
6.权利要求1中所述的通式I的分散染料在疏水性材料的染色和印花中的应用。
7.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)的分散染料。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007037524.9 | 2007-08-09 | ||
| DE102007037524A DE102007037524A1 (de) | 2007-08-09 | 2007-08-09 | 1, 3-Thiazolyl-Azofarbstoffe, deren Herstellung und Verwendung |
| PCT/EP2008/060113 WO2009019206A2 (en) | 2007-08-09 | 2008-08-01 | 1,3-thiazolyl azo dyes, their preparation and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101778907A true CN101778907A (zh) | 2010-07-14 |
| CN101778907B CN101778907B (zh) | 2013-06-12 |
Family
ID=40226963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200880102724XA Expired - Fee Related CN101778907B (zh) | 2007-08-09 | 2008-08-01 | 1,3-噻唑基偶氮染料、它们的制备及应用 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7892295B2 (zh) |
| EP (1) | EP2254950B1 (zh) |
| JP (1) | JP5485887B2 (zh) |
| KR (1) | KR101377330B1 (zh) |
| CN (1) | CN101778907B (zh) |
| AT (1) | ATE527317T1 (zh) |
| BR (1) | BRPI0815000B1 (zh) |
| CA (1) | CA2695949C (zh) |
| DE (1) | DE102007037524A1 (zh) |
| DK (1) | DK2254950T3 (zh) |
| MX (1) | MX2010001497A (zh) |
| PT (1) | PT2254950E (zh) |
| TW (1) | TWI448515B (zh) |
| WO (1) | WO2009019206A2 (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0625624D0 (en) * | 2006-12-21 | 2007-01-31 | Dystar Textilfarben Gmbh & Co | Disperse dye mixtures |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3380990A (en) * | 1965-05-24 | 1968-04-30 | Eastman Kodak Co | Thiazolyl azo dyestuffs |
| CH647253A5 (de) | 1980-03-13 | 1985-01-15 | Sandoz Ag | Azoverbindungen mit einer diazokomponente der thiazolreihe. |
| JPS58179268A (ja) * | 1982-04-15 | 1983-10-20 | Gosei Senriyou Gijutsu Kenkyu Kumiai | ポリエステル繊維用モノアゾ染料 |
| JPS59213765A (ja) * | 1983-05-18 | 1984-12-03 | Gosei Senriyou Gijutsu Kenkyu Kumiai | ポリエステル繊維用モノアゾ染料 |
| JPS59215355A (ja) * | 1983-05-24 | 1984-12-05 | Gosei Senriyou Gijutsu Kenkyu Kumiai | ポリエステル繊維用モノアゾ染料 |
| US5194598A (en) | 1987-10-24 | 1993-03-16 | Bayer Aktiengesellschaft | Azo dyestuffs in which the coupling component contains an N,N-bis(alkoxy carbonylalkyl) substituent |
| DE3736088A1 (de) | 1987-10-24 | 1989-05-03 | Bayer Ag | Azofarbstoffe |
| DE3804814A1 (de) * | 1987-11-17 | 1989-05-24 | Bayer Ag | Azofarbstoffe auf der basis von 2-hydrazinothiazolen, deren verwendung zum faerben und bedrucken von fasermaterialien sowie fuer den sublimationstransferdruck |
| GB8817220D0 (en) | 1988-07-20 | 1988-08-24 | Ici Plc | Thermal transfer printing |
| JPH03256793A (ja) * | 1990-03-07 | 1991-11-15 | Mitsubishi Kasei Corp | 感熱転写シート及び感熱転写シート用インキ組成物 |
| DE69106759T2 (de) | 1990-04-20 | 1995-07-06 | Agfa Gevaert Nv | Schwarzes Donorelement für thermische Farbstoffsublimationsübertragung. |
| US5550218A (en) | 1990-07-11 | 1996-08-27 | Sandoz Ltd. | Azo compounds having unsubstituted or substituted 2-phenoxycarbonylethyl groups |
| DE4121754B4 (de) | 1990-07-11 | 2005-11-03 | Clariant Finance (Bvi) Ltd. | Azo-Dispersionsfarbstoffe |
| ATE146135T1 (de) | 1992-07-14 | 1996-12-15 | Agfa Gevaert Nv | Thiazolylazoanilinfarbstoffe zur anwendung in der thermischen farbstoffsublimationsübertragung |
-
2007
- 2007-08-09 DE DE102007037524A patent/DE102007037524A1/de not_active Withdrawn
-
2008
- 2008-08-01 PT PT08802951T patent/PT2254950E/pt unknown
- 2008-08-01 DK DK08802951.7T patent/DK2254950T3/da active
- 2008-08-01 WO PCT/EP2008/060113 patent/WO2009019206A2/en active Application Filing
- 2008-08-01 EP EP08802951A patent/EP2254950B1/en active Active
- 2008-08-01 CN CN200880102724XA patent/CN101778907B/zh not_active Expired - Fee Related
- 2008-08-01 AT AT08802951T patent/ATE527317T1/de active
- 2008-08-01 US US12/672,602 patent/US7892295B2/en not_active Expired - Fee Related
- 2008-08-01 BR BRPI0815000-1A patent/BRPI0815000B1/pt not_active IP Right Cessation
- 2008-08-01 JP JP2010519439A patent/JP5485887B2/ja not_active Expired - Fee Related
- 2008-08-01 CA CA2695949A patent/CA2695949C/en not_active Expired - Fee Related
- 2008-08-01 MX MX2010001497A patent/MX2010001497A/es active IP Right Grant
- 2008-08-01 KR KR1020107005140A patent/KR101377330B1/ko active IP Right Grant
- 2008-08-07 TW TW097130068A patent/TWI448515B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP2254950A2 (en) | 2010-12-01 |
| PT2254950E (pt) | 2012-01-09 |
| US7892295B2 (en) | 2011-02-22 |
| ATE527317T1 (de) | 2011-10-15 |
| JP5485887B2 (ja) | 2014-05-07 |
| CN101778907B (zh) | 2013-06-12 |
| DK2254950T3 (da) | 2012-01-23 |
| EP2254950B1 (en) | 2011-10-05 |
| MX2010001497A (es) | 2011-03-03 |
| JP2010535877A (ja) | 2010-11-25 |
| US20100205755A1 (en) | 2010-08-19 |
| BRPI0815000A2 (pt) | 2015-10-27 |
| DE102007037524A1 (de) | 2009-02-12 |
| KR101377330B1 (ko) | 2014-03-27 |
| CA2695949A1 (en) | 2009-02-12 |
| WO2009019206A2 (en) | 2009-02-12 |
| TW200916532A (en) | 2009-04-16 |
| TWI448515B (zh) | 2014-08-11 |
| WO2009019206A3 (en) | 2009-06-04 |
| CA2695949C (en) | 2014-02-18 |
| BRPI0815000B1 (pt) | 2018-03-06 |
| KR20100055455A (ko) | 2010-05-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101782194B1 (ko) | 분산 염료 혼합물, 그의 제조 및 용도 | |
| TWI444436B (zh) | 用於對疏水性材料染色和印製的偶氮染料 | |
| JP5613170B2 (ja) | 分散染料の混合物 | |
| TWI465522B (zh) | 偶氮吡啶酮分散染料，它們之製備及用途 | |
| EP2467531A1 (en) | Disperse dye mixtures, their preparation and use | |
| US7833291B2 (en) | Dispersion dye, the production and use thereof | |
| US8070832B2 (en) | Disperse dyes, their preparation and use | |
| EP2254950B1 (en) | 1,3-thiazolyl azo dyes, their preparation and use | |
| US20090209742A1 (en) | Disperse dyes, production and use | |
| US8906116B2 (en) | Mixtures of disperse dyes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| ASS | Succession or assignment of patent right |
Owner name: DYSTAR COLOURS GERMANY GMBH Free format text: FORMER OWNER: DYSTAR TEXTILFARBEN GMBH + CO. DEUTXCHLAND KG Effective date: 20100916 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20100916 Address after: Frankfurt, Germany Applicant after: DYSTAR TEXTILFARBEN GMBH & CO DEUTSCHLAND KG Address before: Frankfurt, Germany Applicant before: DYSTAR TEXTILFARBEN GMBH & CO. DEUTSCHLAND KG |
|
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 1142353 Country of ref document: HK |
|
| ASS | Succession or assignment of patent right |
Owner name: DYSTAR COLOURS DISTRIBUTION GMBH Free format text: FORMER OWNER: DYSTAR DYES GERMANY CO., LTD. Effective date: 20120919 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20120919 Address after: Frankfurt, Germany Applicant after: DYSTAR COLOURS DISTRIBUTION GmbH Address before: Frankfurt, Germany Applicant before: DYSTAR TEXTILFARBEN GMBH & CO DEUTSCHLAND KG |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: WD Ref document number: 1142353 Country of ref document: HK |
|
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20130612 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |