TWI448515B - １，３－噻唑基偶氮染料、它們之製備及用途 - Google Patents
１，３－噻唑基偶氮染料、它們之製備及用途 Download PDFInfo
- Publication number
- TWI448515B TWI448515B TW097130068A TW97130068A TWI448515B TW I448515 B TWI448515 B TW I448515B TW 097130068 A TW097130068 A TW 097130068A TW 97130068 A TW97130068 A TW 97130068A TW I448515 B TWI448515 B TW I448515B
- Authority
- TW
- Taiwan
- Prior art keywords
- formula
- dye
- alkyl
- disperse dye
- patent application
- Prior art date
Links
- -1 1,3-thiazolyl Chemical group 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 239000000987 azo dye Substances 0.000 title description 4
- 239000000986 disperse dye Substances 0.000 claims abstract description 26
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 238000004043 dyeing Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000004744 fabric Substances 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 11
- 230000002209 hydrophobic effect Effects 0.000 claims description 6
- 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
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000002270 dispersing agent Substances 0.000 description 13
- 239000000976 ink Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 229920000728 polyester Polymers 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
- 239000000654 additive Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000012360 testing method 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
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical group 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
- 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
- 238000005406 washing 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
- 239000011149 active material Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 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
- 239000001045 blue dye Substances 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 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
- 239000012943 hotmelt 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
- 238000000926 separation method Methods 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
- 239000007921 spray Substances 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 239000000984 vat dye Substances 0.000 description 2
- OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical class O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 description 1
- 229940015975 1,2-hexanediol 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
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-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
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-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
- 241000894006 Bacteria Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 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
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003139 biocide Substances 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
- 239000004202 carbamide Substances 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
- 239000003638 chemical reducing 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
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 238000007796 conventional method 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
- 238000006193 diazotization reaction Methods 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
- RZENBPJFABIAGL-UHFFFAOYSA-N dinitro sulfate Chemical compound [O-][N+](=O)OS(=O)(=O)O[N+]([O-])=O RZENBPJFABIAGL-UHFFFAOYSA-N 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
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000000227 grinding Methods 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
- 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
- 238000013508 migration 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000573 polyethylene 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
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000010008 shearing Methods 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
- 229920005552 sodium lignosulfonate Polymers 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
- 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
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-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
- 150000003459 sulfonic acid esters 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
- 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
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002759 woven fabric Substances 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)
- Dispersion Chemistry (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Description
本發明涉及包含1,3－噻唑基重氮組分之分散偶氮染料。
包含這種重氮組分之偶氮染料係已知並描述於例如GB 2 071 684 A、DE 33 13 797 A1、EP 0 352 006 A2、EP 0 453 020 A1、DE 41 21 754 A1和EP 0 578 870 A1中。描述於GB 2 071 684 A和EP 0 352 006 A2中之染料確切的說包含取代之噻唑基重氮組分並且在後者情況下還以高耐光性而引人注目。
EP 0 313 918 A2公開了紅色染色之分散偶氮染料，它們包含二烷氧羰基烷基氨基酚作為偶合組分。
出人意料，目前已經發現包含描述於GB 2 071 684 A或EP 0 352 006 A2中的1,3－噻唑基重氮組分和描述於EP 0 313 918 A2中的偶合組分的染料表現出優異的耐濕牢度以及良好的耐光性。這使之有可能滿足對於具有優異耐濕牢度和良好耐光性的藍色染色的市場需求。
因此本發明提供了具有式1之分散染料
其中，R1
和R2
各自係(C1
-C4
)-烷基或氫或(C1
-C4
)-烷氧基取代的(C1
-C4
)-烷基；R3
和R4
各自係氫或甲基；A和B一係氰基而另一係-COOX；並且X係(C2
-C12
)-烷基，O-中斷的(C2
-C12
)-烷基，(C3
-C4
)-鏈烯基或苯基-(C1
-C4
)-烷基。
(C1
-C4
)-烷基基團可以係直鏈或支鏈並且係例如甲基、乙基、正丙基、異丙基、正丁基、異丁基或叔丁基。類似的考慮適用於烷氧基基團，例如它們係甲氧基或乙氧基。
(C2
-C12
)-烷基基團同樣可以係直鏈的或支鏈的，並且同樣以上對(C1
-C4
)-烷基所提到的含義還可以係，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應的支鏈基團。
O-間斷的(C2
-C12
)-烷基基團符合下式H3
C-(CH2
)n
-O-(CH2
)m
-，其中n係從0到10，m係從1到11並且m+n係從1到11。優選地，n係0到2而m係2。
(C3
-C4
)-鏈烯基基團具體係烯丙基，而苯基-(C1
-C4
)-烷基基團具體係苯甲基和苯乙基。
式(1)之分散染料具體係包含具有式(Ia)之分散染料
而且還包含具有式(Ib)之分散染料
其中在每一情況中R1到R4以及X各自如以上所定義。
特別優選的具有式(I)之分散染料符合式(Ic)
其中X如以上所定義並且具體係乙基，正丙基，正丁基，異丁基，叔丁基，正戊基，正己基，正辛基，甲氧乙基
，乙氧乙基，異丙氧乙基，正丁氧乙基，烯丙基或苯甲基。
本發明之具有通式(I)的染料可以籍由熟習該項技術者熟知的方法獲得。例如，一具有通式(II)之化合物
其中R1
到R4
各自如以上所定義，可以與式(III)的一種氰基乙酸烷基酯縮合
其中X如以上所定義，以形成根據本發明之式(I)的一分散染料。
該反應可以籍由例如EP 0 578 870 A1中所描述之程序來進行。
然而，在醋酸鈉的存在下使縮合在一醇(它可以含有水)中進行，在關於產品的純度和易於分離方面它將會發現係特別有利的。優選的醇係甲醇和乙醇。水含量可以係0－40%，優選0－10%。該反應理想地係在室溫下進行。
所指示的過程導致優先形成具有式(Ia)之分散染料
，即在烯烴雙鍵處具有一種E構型之化合物。這可以籍由NMR－J－HMBC實驗確認，在該實驗中發現烯屬的質子與羰基碳的偶合常數在6 Hz和7 Hz之間，與腈碳的偶合常數在13 Hz和14 Hz之間。
分離具有式(Ia)和(Ib)之分散染料的對於以下描述的用作染料的用途不係必需的，但是如果希望當然可以採用常規之方法進行。
具有式(II)之化合物係可以籍由具有式(IV)的胺的重氮化作用並偶合到具有式(V)之化合物上而獲得
其中R1
到R4
各自如以上所定義。
具有式(IV)之化合物一般係根據已知的方式重氮化，例如使用在稀硫酸、磷酸或者乙酸和丙酸的一混合物中的亞硝基硫酸來進行。優選的溫度範圍在－10℃和10℃之間。
重氮化合物一般係同樣地以已知方式(例如在酸性、水性、水性－有機的或有機介質中)，特別有利的係在低
於10℃的溫度下偶合至具有式(V)之化合物上。所使用的酸具體係硫酸、乙酸或丙酸。
式(IV)的胺係已知的並且例如可按GB 2 071 684 A中的說明而獲得。
具有式(V)之化合物同樣係已知的並且例如可根據M.Lipp等人,Chem.Ber.1958,91,2239 ff而獲得。在乙酸中獲得的反應混合物可直接使用。
本發明之具有通式(I)之分散染料在疏水性材料的染色和印染方面具有突出的作用，給出具有出色的耐洗滌性和耐汗性的紫色到藍色的印染色澤。這特別對於聚酯微纖維和含聚酯的混紡織物(例如與棉和彈性紗)也係成立的。
已經進一步確定本發明之分散染料對例如被用作工作裝的聚酯－棉混紡品的連續染色係出色地有效。所達到的耐濕性特別係根據“Hoechst結合測試”係出色的。在Hoechst結合測試中，將染色的紡織品暴露於160－190℃的接觸熱中達5－10分鐘並隨後經受ISO 105 C05或ISO 105－C06 E2耐洗滌性試驗。這模擬了工業洗燙條件，其中洗淨的紡織品材料在一干蒸汽裝置中在非常高的溫度下進行乾燥。在該操作中，染料會遷移到表面並在隨後的洗滌中造成臨近織物著色或污染。此處本發明之染料由於有極低的著色或污染而引人注目。
因此本發明還提供了具有通式I之分散染料用於疏水性材料的染色和印染的用途，以及在常規程式中染色和印
染此類材料的方法，這些方法使用了根據本發明之具有通式(I)的一或多種分散染料作為著色劑。
所提及的疏水性材料可以係合成的或纖維素源的。所考慮的疏水性材料包括例如二乙酸酯纖維素、三乙酸酯纖維素、聚醯胺以及，特別係大分子聚酯。大分子聚酯組成的材料具體的係基於聚對苯二甲酸乙二醇酯類的那些。
該疏水性合成材料可以係片狀或線形結構並可以被加工成例如紗或紡織或針織的紡織品。優選纖維性紡織材料，它們還能以例如微纖維的形式存在。
與根據本發明之用途一致的染色可以按常規方式進行，優選從水性分散液，適當時在載體的存在下，在80℃到約110℃之間籍由耗盡法或在110℃到140℃於染色高壓釜中籍由HT法進行，並且還可以籍由所謂的熱固法(thermofix)法，在該方法中用染色液對織物進行軋染並隨後在約180℃到230℃下固定/定色。
所提及的材料的印染可以籍由將本發明之具有通式(I)之分散染料結合在一印花糊漿中以本身已知的一方式來進行，並在180℃到230℃之間溫度下用HT蒸汽、高壓蒸汽或幹熱(適當時在載體的存在下)處理以此印製的織物來使染料固定。
當本發明之具有通式(I)之分散染料被用在染色液、軋染液或印染糊漿中時它們應該係處於非常精細的細分狀態。
該染料係以常規方式籍由在一液態介質中(優選在水
中)將已製成的染料與分散劑一起調成漿狀來轉化成細分的精細狀態，並使該混合物經受剪力以機械地粉碎原始的染料顆粒以達到最佳的比表面積並使染料的沉澱最小化的程度。這係在適當的研磨機中完成的，如球磨機或砂磨機。染料的顆粒大小通常在0.5μm和5μm之間並優選等於約1μm。
在研磨操作中所使用的分散劑可以係非離子型或陰離子型的。非離子型分散劑包括，例如，環氧烷烴例如環氧乙烷或環氧丙烷，與可烷基化之化合物例如脂肪醇、脂肪胺、脂肪酸、酚類、烷基酚類和羧醯胺類的反應產物。陰離子型分散劑係，例如，木素磺酸酯類、烷基或烷芳基磺酸酯類或烷芳基聚乙二醇醚硫酸酯類。
如此獲得的染料製品對於多數應用應當係可傾流。因此，在這些情況下該染料和分散劑的含量係有限的。總體來說，這些分散液被調節到染料含量按重量計高達50%以及分散劑的含量按重量計高達約25%。出於節約的原因，在大多數情況下染料含量按重量計不低於15%。
該分散液還可以包含其他助劑，例如那些作為氧化劑的乙二醇如間－硝基苯磺酸鈉，或殺真菌試劑如鄰－苯基苯酚鈉和五氯苯酚鈉，以及特別係所謂的“酸供體”，例子係丁內酯、一氯乙醯胺、氯乙酸鈉、二氯乙酸鈉、3－氯丙酸的鈉鹽、單硫酸酯例如像月桂基硫酸酯，以及還有乙氧基化和丙氧基化醇類的磺酸酯，如乙二醇硫酸丁酯(butylglycol sulfate)。
如此獲得的染料分散體對於製備染液和印染糊漿係非常有利。
存在某些應用領域其中優選的係使用粉末配製品。這些粉末包含所述的染料、分散劑和其他助劑，例如潤濕劑、氧化劑、防腐劑和防塵劑以及以上提及之“酸供體”。
製備染料的粉末製劑的優選的方法包括對上述液體染料分散液去掉它們的液體，例如籍由真空乾燥、冷凍乾燥、在轉鼓式乾燥器上進行乾燥，但係優選籍由噴霧乾燥。
這些染料液體係籍由對必需量的上述染料配製品用染料介質，優選水，進行稀釋而制得，這樣就獲得了用於染色的1：5到1：50的一液體比。此外，總體來說常規的係在這些液體中包括另外的染色助劑，如分散劑、潤濕劑和固定助劑。有機酸和無機酸類如乙酸、琥珀酸、硼酸或磷酸包括在內以設定從4到5的範圍內的pH值，優選4.5。有利的係對pH的設定進行緩衝並加入足夠量的緩衝體系。乙酸/乙酸鈉體系係一有利的緩衝體系的實例。
為了在織物印染中使用染料或染料混合物，以上提及的染料配製品的必需量與增稠劑(例如鹼金屬藻酸鹽類及類似物)以及適當時另外的添加劑(如定色促進劑、潤濕劑和氧化劑)以常規方式揉合在一起以產生印染糊漿。
本發明還提供了籍由墨噴射法進行數位化織物印染用的墨，包含本發明之具有通式(I)的一分散染料。
本發明之墨優選係水性的並包含一或多種本發明之具有通式(I)之分散染料，例如以基於該墨的總重按重量
計0.1%到50%的量，優選以按重量計為1%到30%的量以及更優選以按重量計為1%到15%的量。
它們進一步包含特別係按重量計從0.1%到20%的一分散劑。適合的分散劑對於熟習該項技術者係已知的，係市售的並包括例如磺化的或磺甲基化的木素、芳磺酸與甲醛的縮合產物、取代的或未取代的苯酚與甲醛的縮合產物、聚丙烯酸酯和相應的共聚物、改性的聚氨酯以及環氧烷烴與可烷基化之化合物的反應產物，例如脂肪醇類、脂肪胺類、脂肪酸類、羧醯胺類以及取代或未取代的酚類。
本發明之墨可以進一步包含常規的添加劑，例如黏度緩和劑以便將黏度設定為在溫度從20℃到50℃的範圍內從1.5到40.0 mPas的範圍。優選的墨具有範圍在從1.5到20 mPas的黏度並且特別優選的墨具有範圍在從1.5到15 mPas的黏度。
有用的黏度緩和劑包括流變性能添加劑，例如聚乙烯己內醯胺、聚乙烯基吡咯烷酮以及還有它們的共聚物、聚醚多元醇、締合性增稠劑、聚脲、海藻酸鈉、改性半乳糖甘露聚糖、聚醚脲、聚氨酯和非離子型纖維素醚類。
籍由另外的添加劑，本發明之墨可以包括表面活性物質以將表面張力設定在20到65 mN/m的範圍內，適當時根據所使用的方法(熱或壓電技術)對其進行調整。有用的表面活性物質包括例如任何類型的表面活性劑，優選非離子型表面活性劑、丁基二甘醇和1,2－己二醇。
這些墨可以進一步包括常規添加劑，例如抑制真菌和
細菌生長的材料，其量值係基於該墨總重量按重量計從0.01%到1%。
本發明之墨可以按照常規的方式籍由在水中混合各成分來製備。
以下的實例對本發明進行了闡述。份數係按重量計。
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－甲醯－1,3－噻唑(式(IV)之化合物)。隨後攪拌30 min後將溫度降到0℃。然後，經過2小時向黃色的懸浮液中逐滴加入205份40%的亞硝基硫酸同時溫度保持在0－2℃。在該溫度下繼續攪拌3小時。在1503份甲醇中加入335.3份用乙酸使之呈酸性並含有按重量計為51.6%的甲基3－[(3－羥基苯基)－(2－甲氧羰基乙基)氨基]丙酸酯的溶液作為首次加料。加入400份按重量計為18%的氨基磺酸水溶液和1250份冰。在起始溫度為－12℃下，於30分鐘的過程中將重氮化混合物逐滴加入到該偶合溶液中，在此過程中溫度升到－1℃。隨後將該混合物攪拌15分鐘然後用約930份按重量計為30%的氫氧化鈉水溶液調節至pH4.2。加入約1240份冰將溫度保持在10℃以下。攪拌一夜後將沉澱抽吸濾除。將強含鹽的吸濾餅再次懸浮於1500份水中並攪拌2小時。吸濾後獲得228.5
份具有式(IIa)之化合物，用水洗滌並乾燥。這對應於理論產量的81.7%。
b)將25份化合物(IIa)懸浮在314份乙醇中並攪拌30分鐘。加入5.5份無水乙酸鈉和21.85份氰乙酸丙酯。隨後將該混合物攪拌一夜。籍由薄層色譜法測定反應的完全度。反應完全後，用抽濾法濾除固體並用乙醇和水洗滌，乾燥後得到18.55份具有下式的染料，對應於60%的理論值：
λmax
＝604 nm(DMF)
與實例1中所描述的程式相似也可以獲得以下的實例2－16之分散染料。
根據實例1獲得的30g染料(處於水濕壓餅的形式)與63g木質素磺酸鈉和3g非離子型分散劑(松香酸和50摩爾當量的環氧乙烷的加成產物)在200ml水中混合並用25%的硫酸調節至pH7。隨後在室溫下用球磨法研磨1小時(90%<1μm)，篩選並在噴霧乾燥器中乾燥。
將由此獲得的2g粉末分散在1000g水中。將該分散液與基於萘磺酸鈉鹽和甲醛的縮合產物的0.5到2g/l的市售分散劑的液體，0.5到2g/l磷酸二氫鈉的液體和2g/l市售的均染助劑液體進行混合並用乙酸將調節到pH4.5至5.5。將由此獲得的染料液引入100g基於聚對苯二甲酸乙二醇酯的變形的(textured)聚酯織物並在130℃進行60分鐘的染色。還原清洗留下具有優異洗滌性和耐汗牢度以及非常好的耐昇華牢度的紅藍色的染色。
用實例2到16的染料重複實例17同樣給出具有優異的耐濕牢度的紫色到藍色的染色。
將實例16的染料研磨並如實例17的第一部分所描述的那樣進行噴霧乾燥。這樣獲得的染料籍由熱溶膠法施用於聚酯棉混紡織物。為此目的，製備了含有30g/l上述分散染料、30g/l的藍色還原染料、2g/l SERAWet C－AS潤濕劑、10g/l的SERAGal M－IP抗遷移劑以及0.5ml/l的60%乙酸的染料軋染劑。設定吸濕量為60－80%。在該織物籍由軋車後，它在120℃下乾燥1－3分鐘。隨後係在210℃－225℃下的熱熔膠化60秒。此後，該織物籍由含有60－120ml的38° B的燒鹼和35－70g/l的亞硫酸氫鹽(這些量取決於還原染料的用量)的化學軋染。吸濕量應該係70－100%。隨後在102℃下汽蒸1分鐘。隨後該織物的最後定型係籍由漂洗週期、用50%的過氧化氫氧化、用1g/l
的SERASperse C－SN螯合劑在98℃皂洗並酸化至pH5－6。再經過2次水漂洗浴後將該織物進行乾燥。
如此獲得的紅藍色染色具有優異的耐洗牢度，符合特別係“Hoechst組合測試”的要求。用實例1－15的染料獲得了類似的結果。
一由聚酯組成的織物用由50g/l的8%藻酸鈉溶液、100g/l的8－12%角豆粉醚溶液和5g/l磷酸二氫鈉在水中組成的液體進行軋染然後乾燥。吸濕量係70%。
將這樣預處理的織物隨後用根據以上描述的程式製備的水性墨採用按需噴墨(drop－on－demand)(壓電)的墨噴射印染頭進行印染，該墨含有3.5%的實例1的染料，2.5%的Disperbyk 190分散劑，30%的1,5－戊二醇，5%的二乙二醇一甲醚，0.01%的Mergal K9N生物殺蟲劑，以及58.99%的水。
將該印染充分乾燥。在175℃下借助過熱蒸汽的方式固色7分鐘。該印染品隨後經受鹼性還原清洗，溫水漂洗並隨後乾燥。
Claims (7)
- 一種具有式I之分散性染料
- 如申請專利範圍第1項之分散性染料，其係符合式(Ia)
- 如申請專利範圍第1或2項之分散性染料，其係符合式(Ic)
- 如申請專利範圍第1或2項之分散性染料，其中X係乙基、正丙基、正丁基、異丁基、叔丁基、正戊基、正己基、正辛基、甲氧乙基、乙氧乙基、異丙氧乙基、正丁氧乙基、烯丙基或苯甲基。
- 一製備如申請專利範圍第1項之通式(I)之分散性染料之方法，該方法包括使通式(II)之化合物
- 如申請專利範圍第1項之通式I之分散性染料之用途，其用於使疏水性材料染色和印染。
- 一種用於藉由噴墨法之數位式織物印染之墨汁，包含如申請專利範圍第1項之通式(I)之分散性染料。
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007037524A DE102007037524A1 (de) | 2007-08-09 | 2007-08-09 | 1, 3-Thiazolyl-Azofarbstoffe, deren Herstellung und Verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200916532A TW200916532A (en) | 2009-04-16 |
| TWI448515B true TWI448515B (zh) | 2014-08-11 |
Family
ID=40226963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097130068A TWI448515B (zh) | 2007-08-09 | 2008-08-07 | １，３－噻唑基偶氮染料、它們之製備及用途 |
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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3380990A (en) * | 1965-05-24 | 1968-04-30 | Eastman Kodak Co | Thiazolyl azo dyestuffs |
| US4542207A (en) * | 1982-04-15 | 1985-09-17 | Research Association Of Synthetic Dyestuffs | Heterocyclic monoazo dyes for polyester fibers |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH647253A5 (de) | 1980-03-13 | 1985-01-15 | Sandoz Ag | Azoverbindungen mit einer diazokomponente der thiazolreihe. |
| 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 |
| EP0453020B1 (en) | 1990-04-20 | 1995-01-18 | Agfa-Gevaert N.V. | Black colored thermal dye sublimation transfer donor element |
| 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 BR BRPI0815000-1A patent/BRPI0815000B1/pt not_active IP Right Cessation
- 2008-08-01 KR KR1020107005140A patent/KR101377330B1/ko not_active Expired - Fee Related
- 2008-08-01 JP JP2010519439A patent/JP5485887B2/ja not_active Expired - Fee Related
- 2008-08-01 EP EP08802951A patent/EP2254950B1/en active Active
- 2008-08-01 DK DK08802951.7T patent/DK2254950T3/da active
- 2008-08-01 US US12/672,602 patent/US7892295B2/en not_active Expired - Fee Related
- 2008-08-01 CA CA2695949A patent/CA2695949C/en not_active Expired - Fee Related
- 2008-08-01 AT AT08802951T patent/ATE527317T1/de active
- 2008-08-01 WO PCT/EP2008/060113 patent/WO2009019206A2/en not_active Ceased
- 2008-08-01 CN CN200880102724XA patent/CN101778907B/zh not_active Expired - Fee Related
- 2008-08-01 PT PT08802951T patent/PT2254950E/pt unknown
- 2008-08-01 MX MX2010001497A patent/MX2010001497A/es active IP Right Grant
- 2008-08-07 TW TW097130068A patent/TWI448515B/zh not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3380990A (en) * | 1965-05-24 | 1968-04-30 | Eastman Kodak Co | Thiazolyl azo dyestuffs |
| US4542207A (en) * | 1982-04-15 | 1985-09-17 | Research Association Of Synthetic Dyestuffs | Heterocyclic monoazo dyes for polyester fibers |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2695949A1 (en) | 2009-02-12 |
| PT2254950E (pt) | 2012-01-09 |
| ATE527317T1 (de) | 2011-10-15 |
| KR20100055455A (ko) | 2010-05-26 |
| JP2010535877A (ja) | 2010-11-25 |
| TW200916532A (en) | 2009-04-16 |
| CN101778907B (zh) | 2013-06-12 |
| KR101377330B1 (ko) | 2014-03-27 |
| EP2254950B1 (en) | 2011-10-05 |
| JP5485887B2 (ja) | 2014-05-07 |
| EP2254950A2 (en) | 2010-12-01 |
| BRPI0815000B1 (pt) | 2018-03-06 |
| US20100205755A1 (en) | 2010-08-19 |
| DE102007037524A1 (de) | 2009-02-12 |
| WO2009019206A3 (en) | 2009-06-04 |
| DK2254950T3 (da) | 2012-01-23 |
| CN101778907A (zh) | 2010-07-14 |
| WO2009019206A2 (en) | 2009-02-12 |
| BRPI0815000A2 (pt) | 2015-10-27 |
| CA2695949C (en) | 2014-02-18 |
| MX2010001497A (es) | 2011-03-03 |
| US7892295B2 (en) | 2011-02-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI510558B (zh) | 分散性染料，其製備及其用途 | |
| TWI409301B (zh) | 分散性偶氮染料 | |
| 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 | |
| JP2013502474A (ja) | 分散染料混合物、それらの調製物及び使用 | |
| TWI427123B (zh) | 分散性染料，彼之製造與應用 | |
| CN109401359B (zh) | 一种蓝至黑色分散染料组合物和染料制品 | |
| TWI448515B (zh) | １，３－噻唑基偶氮染料、它們之製備及用途 | |
| JP2010535878A (ja) | 分散染料、それらの調製法、及び使用 | |
| CN105623298B (zh) | 一种橙色分散染料化合物及其应用 | |
| KR20090016558A (ko) | 분산 염료, 제조 및 용도 | |
| CN105111104B (zh) | 一种分散染料单体化合物、分散染料制剂及其应用 | |
| HK1142353A (zh) | 1，3-噻唑基偶氮染料、它们的制备及应用 | |
| HK1129232A (zh) | 分散染料、其制备和其应用 | |
| HK1142620A (zh) | 分散染料、它们的制备及应用 | |
| HK1133027A (zh) | 分散染料、它们的制备和用途 | |
| HK1158243B (zh) | 分散染料混合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |