CN102652155B - 分散偶氮染料、其制备方法及其用途 - Google Patents
分散偶氮染料、其制备方法及其用途 Download PDFInfo
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- CN102652155B CN102652155B CN201080057113.5A CN201080057113A CN102652155B CN 102652155 B CN102652155 B CN 102652155B CN 201080057113 A CN201080057113 A CN 201080057113A CN 102652155 B CN102652155 B CN 102652155B
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- ethyl
- dyestuff
- hydrogen
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- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title abstract description 14
- 230000008569 process Effects 0.000 title abstract description 5
- 239000000987 azo dye Substances 0.000 title 1
- 239000000975 dye Substances 0.000 claims abstract description 67
- 238000004043 dyeing Methods 0.000 claims abstract description 24
- 239000000463 material Substances 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 16
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 12
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 10
- 229910052736 halogen Chemical group 0.000 claims abstract description 10
- 150000002367 halogens Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 238000007639 printing Methods 0.000 claims abstract description 7
- 230000008878 coupling Effects 0.000 claims abstract description 6
- 238000010168 coupling process Methods 0.000 claims abstract description 6
- 238000005859 coupling reaction Methods 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 22
- -1 methoxyl group Chemical group 0.000 claims description 21
- 238000006193 diazotization reaction Methods 0.000 claims description 19
- 229910052794 bromium Chemical group 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 230000002194 synthesizing effect Effects 0.000 claims description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 abstract description 9
- 239000004753 textile Substances 0.000 abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000835 fiber Substances 0.000 abstract description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract description 4
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 abstract 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 32
- 239000000203 mixture Substances 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000005406 washing Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000012065 filter cake Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000002657 fibrous material Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- HZZFBUZSKAVIOV-UHFFFAOYSA-N 6-nitro-1,1-dioxo-1,2-benzothiazol-3-one Chemical compound [O-][N+](=O)C1=CC=C2C(=O)NS(=O)(=O)C2=C1 HZZFBUZSKAVIOV-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000001117 sulphuric acid Substances 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- CBGSTCTXIDWYMD-UHFFFAOYSA-N 2-ethyl-6-nitro-1,1-dioxo-1,2-benzothiazol-3-one Chemical compound C1=C([N+]([O-])=O)C=C2S(=O)(=O)N(CC)C(=O)C2=C1 CBGSTCTXIDWYMD-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- PLAWCFOMHQCJBK-UHFFFAOYSA-N 1-(2,2-dimethylpropylperoxy)pentane Chemical compound CCCCCOOCC(C)(C)C PLAWCFOMHQCJBK-UHFFFAOYSA-N 0.000 description 1
- DQIYDCGGBPKJJW-UHFFFAOYSA-N 2-nitro-1,1-dioxo-1,2-benzothiazol-3-one Chemical compound C1=CC=C2S(=O)(=O)N([N+](=O)[O-])C(=O)C2=C1 DQIYDCGGBPKJJW-UHFFFAOYSA-N 0.000 description 1
- KABUZPWVPGUDIR-UHFFFAOYSA-N 5-nitro-1,1-dioxo-1,2-benzothiazol-3-one Chemical compound [O-][N+](=O)C1=CC=C2S(=O)(=O)NC(=O)C2=C1 KABUZPWVPGUDIR-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 0 Cc(c([N+]([O-])=O)c1)c(*)c(SN2*)c1C2=O Chemical compound Cc(c([N+]([O-])=O)c1)c(*)c(SN2*)c1C2=O 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000000305 astragalus gummifer gum Substances 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010019 resist printing Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 239000002759 woven fabric 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
本发明涉及下式(I)的染料;其中A为-CO-,并且Q为-SO2-;或者A为-SO2-,并且Q为-CO-;R1表示C1-C6烷基、苄基、烯丙基、-CnH2n-COOR或-CnH2n-CN,其中n为1至3的数,R表示氢或C1-C6烷基;X为硝基、氰基或卤素;Y为氢、硝基、氰基或卤素;并且K为苯、萘、吡唑啉酮、6-羟基吡啶酮-(2)或N-芳基-乙酰乙酰胺系列的偶联组分的残基;本发明还涉及式(I)的染料的制备方法和用于染色或印刷半合成(尤其是合成)疏水性纤维材料(更尤其是纺织材料)的用途。
Description
本发明涉及基于作为重氮化组分的N-烷基-1,1,3-三氧代-2,3-二氢苯并异噻唑(N-烷基糖精)的胺的分散偶氮染料、这些染料的制备方法及其用于染色或印刷半合成(尤其是合成)疏水性纤维材料(更尤其是纺织材料)的用途。
基于作为重氮化组分的N-烷基-1,1,3-三氧代-2,3-二氢苯并异噻唑的胺的偶氮染料为已知,例如参见美国专利3,878,189。然而,已发现用目前已知的染料得到的染色或印刷并不能满足今天的所有需要,尤其在耐光牢度和耐洗牢度方面更是如此。因此,特别需要具有良好的耐洗牢度性质的新染料。
我们意外地发现,基于作为重氮化组分的N-烷基糖精的偶氮染料显示非常好的耐光牢度和极佳的耐洗牢度结果。
本发明涉及下式的染料
其中
A为-CO-,并且Q为-SO2-;或者A为-SO2-,并且Q为-CO-;
R1表示C1-C6烷基、苄基、烯丙基、-CnH2n-COOR或-CnH2n-CN,其中n为1至3的数,R表示氢或C1-C6烷基;
X为硝基、氰基或卤素;
Y为氢、硝基、氰基或卤素;并且
K为苯、萘、吡唑啉酮、6-羟基吡啶酮-(2)或N-芳基-乙酰乙酰胺系列的偶联组分的残基。
根据取代基在重氮化组分的苯基部分的位置,本发明的染料相应具有式(1a)或(1b)的结构:
其中R1、X、Y和K如上所定义。
优选式(1)的染料,其中K表示式(2a) - (2d)的基团
其中Z1为氢、卤素、C1-C6烷基、未取代或用一个或多个C1-C3烷基羰基氧基取代的C1-C6烷氧基、苄基、-NH-SO2-R10或-NH-CO-R11,并且R10和R11为甲基或乙基;
Z2为氢、卤素或未取代或用一个或多个C1-C3烷基羰基氧基取代的C1-C6烷氧基;
R2和R3各自独立为氢、乙烯基、烯丙基或未取代或由羟基、氰基、C1-C6烷基羰基氧基、C1-C6烷基氧基羰基、C1-C6烷氧基或C6-C24芳基取代的C1-C6烷基;
R4为氢、乙烯基、烯丙基或未取代或由氰基、羧基、羟基、C1-C6烷氧基、C2-C8烷氧基烷氧基或C6-C24芳基取代的C1-C6烷基;
R5和R6各自独立为氢、乙烯基、烯丙基或未取代或由氰基、羧基、羟基、C1-C6烷氧基、C2-C8烷氧基烷氧基或C6-C24芳基取代的C1-C6烷基;
R7为C1-C6烷基、C6-C24芳基或苄基;并且
R8和R9各自独立为氢、乙烯基、烯丙基或未取代或由氰基、羧基、羟基、C1-C6烷氧基或C6-C24芳基取代的C1-C6烷基。
表示烷基的任何基团可以为直链或支链烷基。
烷基的实例包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基和正己基。
C1-C6烷氧基可以为例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、新戊氧基或正己氧基。
表示卤素的任何基团可以为氟、氯或溴。
C6-C24芳基为例如苯基、甲苯基、2,4,6-三甲基苯基、2,4,6-三异丙基苯基(isityl)、萘基和蒽基。
Y优选为氢或溴。
R1优选为乙基。
优选式(1)的偶氮染料,其中K表示式(2a)的基团,其中Z1为甲基或乙酰氨基,Z2表示氢或甲氧基,R2和R3各自独立为乙基、正丙基、烯丙基、2-甲氧基乙基、2-氰基乙基、苄基或甲氧基羰基甲基。
更优选式(1)的偶氮染料,其中K表示式(2b)的基团,其中R4为乙基或3-甲氧基丙基。
另一个优选的实施方案为式(1)的偶氮染料,其中K表示式(2c)的基团,其中R5和R6各自独立为氢、2-甲氧基乙基、3-甲氧基丙基、3-(2-甲氧基乙氧基)丙基、苯基或苄基。
还优选式(1)的偶氮染料,其中K表示式(2d)的基团,其中R7为苯基,R8和R9表示乙基。
特别优选下式的染料
(100),
。
本发明还涉及制备权利要求1的式(1)的偶氮染料的方法,所述方法包括根据常规方法使(3)式的化合物重氮化
其中R1和A、Q、X和Y如上限定;
然后使经重氮化化合物与式K-H的偶联组分偶联,其中K如权利要求1中限定。
可以下列方式制备重氮化组分(3):
适合的起始化合物为5-硝基糖精(5-硝基-1,1-二氧代-1,2-苯并噻唑-3-酮)或6-硝基糖精(6-硝基-1,1-二氧代-1,2-苯并噻唑-3-酮),这些化合物可如J. Macromol. Sci.,A3(5),pp.941 -958(1969)中所述制备。
根据Eur. J. Org. Chem. 2006,4483-4489使硝基糖精烷基化。
烷基化可通过在100℃下,使用包含碳酸钠的二甲基甲酰胺中的烷基卤化物或烷基硫酸盐来进行。
以下还原反应可例如在盐酸中,用锡或铁进行,从而得到式(4a)或(4b)的化合物:
氨基糖精可被单或二卤化。卤化可例如通过在90至100℃下,使式(4a)或(4b)的化合物与乙酸钠和卤素在乙酸中反应来进行。这产生重氮化化合物(5a)和(5b):
其中Hal=Cl,Br。
化合物(4a)和(4b)也可被硝基取代。在硝化反应前,氨基化合物可通过与乙酸酐或氯甲酸烷酯反应进行保护。硝化在60至90℃下,在硫酸中用浓硝酸和浓硫酸的混合酸来进行。在酸性或微碱性介质中去保护产生重氮化化合物(6a)和(6b)
。
可进一步卤化化合物(6a)和(6b),得到重氮化化合物(7a)和(7b)
。
合成重氮化化合物的另一条路线从6-溴糖精(6-溴-1,1-二氧代-1,2-苯并噻唑-3-酮(8))开始,这种化合物可根据Bioorg. Med. Chem. 13,949-961(2005)制备
。
(8)的烷基化可在100℃下,在二甲基甲酰胺中,利用烷基卤化物或烷基硫酸盐和碱金属碳酸盐来进行,随后在硫酸中用浓硝酸和浓硫酸的混合酸硝化。此后,例如在盐酸中用锡或铁还原溴/硝基化合物,生成重氮化化合物(9),其中R1如上所述
。
重氮化式(3a)和(3b)的化合物可以本领域已知的方式进行,
其中R1、X和Y如上定义,
例如,在含水酸性介质,例如含水氢氯酸介质或含水硫酸介质中,用亚硝酸钠来进行。然而,也可用其它重氮化剂(例如亚硝基硫酸)进行重氮化。在重氮化过程中,反应介质中可存在另外的酸,例如磷酸、硫酸、乙酸、丙酸、盐酸或这些酸的混合物,例如丙酸和乙酸的混合物。重氮化有利地在-10至+30℃温度 (例如0℃至室温)下进行。
单或二氰基偶氮化合物可根据WO2004044058所描述的方法制备,所述方法通过在二甲亚砜中,使单或二溴偶氮化合物((1a)或(1b),其中X=Br; Y=H, Br)与氰化钠或铜反应进行溴/氰交换。
本发明的染料可用于染色或印刷半合成(尤其是合成)疏水性纤维材料,更尤其是纺织材料。包含这些半合成或合成疏水性纤维材料的混合织物组成的纺织材料也可用本发明的染料染色或印刷。
特别考虑的半合成纤维材料为21/2-乙酸纤维素和三乙酸纤维素。
合成的疏水性纤维材料尤其由直链、芳族聚酯组成,例如对苯二甲酸和二醇(尤其是乙二醇)的酯;或对苯二甲酸和1,4-双(羟甲基)环己烷的缩合产物;聚碳酸酯,例如,α,α-二甲基-4,4-二羟基-二苯基甲烷和光气的聚碳酸酯;和基于聚氯乙烯或基于聚酰胺的纤维。
根据已知染色方法将本发明的染料施用于纤维材料。例如,在尽染法中,在常用阴离子或非离子分散剂和任选的常用溶胀剂(载体)存在下,在80至140℃温度下,以含水分散体的形式将聚酯纤维材料染色。21/2-乙酸纤维素优选在65至85℃下染色,三乙酸纤维素在65至115℃下染色。
本发明的染料不使同时存在于染浴的羊毛和棉着色,或者只使这些材料轻微着色(很好地防染),因此,它们也可令人满意地用于聚酯/羊毛和聚酯/纤维素性纤维混合织物的染色。
本发明的染料适用于根据热溶胶法进行的染色、可用于尽染法染色,以及用于印刷方法。
在这些方法中,所述纤维材料可为多种加工形式,例如纤维、纱或非织造、针织织物或机织织物的形式。
在使用前,可有利地使本发明的染料转化成染料制剂。为此,将染料研磨,以使其粒径为平均0.1至10微米。可在分散剂存在下进行研磨。例如,将经干燥的染料与分散剂一起研磨,或者与分散剂一起捏和成糊,然后在真空中干燥,或者雾化。加水后,可用所得制剂制备印刷糊和染浴。
为了印刷,使用常用增稠剂,例如改性或未改性天然产物,例如藻酸盐、印染胶、阿拉伯胶、结晶胶、刺槐豆胶粉、黄蓍胶、羧甲基纤维素、羟乙基纤维素;淀粉或合成产物,例如聚丙烯酰胺、聚丙烯酸或其共聚物;或聚乙烯醇。
本发明的染料赋予所述材料(尤其是聚酯材料)很好的使用牢度性质的均色调,例如,尤其是具有良好的耐光牢度、耐热定形牢度、耐褶裥牢度、耐氯牢度和耐湿牢度(例如耐水牢度、耐汗渍牢度和耐洗牢度);最终的染色件(finished dyeings)的另一个特征是很好的耐摩擦牢度。尤其应强调的是所得的染色件(dyeings)具有与排汗和尤其是洗涤相关的良好牢度性质。
本发明的染料也可令人满意地与其它染料一起产生混合色调。
另外,本发明的染料和染料混合物也很好地适用于以超临界CO2为介质使疏水性纤维材料染色的应用。
本发明涉及本发明的染料的上述用途,还涉及染色或印刷半合成或合成疏水性纤维材料(尤其是纺织材料)的方法,在所述方法中,将本发明的染料施加给所述材料或加入到所述材料中。所述疏水性纤维材料优选为聚酯纺织材料。可根据本发明的方法和优选的加工条件处理的其它基材可参见以上关于本发明的染料的使用的更详细说明。
本发明还涉及由所述方法染色或印刷的疏水性纤维材料,优选聚酯纺织材料。
另外,本发明的染料还适用于现代再生产方法,例如热转印。
以下实施例用于举例说明本发明。除非另外指明,否则本发明申请文件中所用的份数为重量份,百分数为重量百分数。温度以摄氏度给出。重量份和体积份之间的关系与克和立方厘米之间的关系相同。
I.制备实施例
I.1前体的合成:
I.1.1重氮化组分(10)的合成:
(10)
合成(10)的第一步骤,6-硝基糖精(6-硝基-1,1-二氧代-1,2-苯并噻唑-3-酮)的制备根据J. Macromol. Sci., A3(5), pp.941 - 958 (1969)进行。
在第二步骤,根据以下方法使6-硝基糖精烷基化:
将180g 6-硝基糖精放入500ml二甲基甲酰胺中。然后加入40g碳酸钠和120g乙基溴。在80℃加热所得溶液两天。冷却后,将混合物倒入3l水中,并再搅拌30分钟。滤出反应混合物,滤饼在真空中干燥。
产量:100g N-乙基-6-硝基-1,1-二氧代-1,2-苯并噻唑-3-酮(11)
(11)
将20g N-乙基-6-硝基糖精(11)置于90ml盐酸(32%)和60ml丙酮中。加入23g锡粒,将如此得到的悬浮体在60至70℃下加热2.5小时。冷却到2℃后,加入碳酸钠,直到产物完全沉淀。滤出反应混合物,滤饼用水和用碳酸氢钠溶液洗涤两次,然后在真空中干燥。
产量:18g N-乙基-6-氨基-1,1-二氧代-1,2-苯并噻唑-3-酮(12)
(12)
在对N-乙基-6-氨基糖精(12)的5-位进行硝化需要保护氨基:
向120ml二甲基甲酰胺(DMF)加入45.6g N-乙基-6-氨基糖精(12)和18.5g吡啶。将反应混合物冷却到-12℃。然后滴加氯甲酸乙酯。搅拌2.5h后,将反应混合物倒在500g冰和水上。加水到1500ml总体积。在60℃搅拌所得反应混合物,冷却并滤出。滤饼用1l水洗涤,并在真空中干燥。
产量:52.8g N-乙基-(6-甲氧基羰基氨基)糖精(13)
(13)
化合物(13)的硝化:
将52.8g经保护胺(13)引入250g硫酸中。在冷却到1℃后,滴加30g浓硝酸和浓硫酸的混合酸(47% HNO3)。将混合物在0至5℃下搅拌15分钟。温热至室温后,将混合物在此温度下再搅拌2小时,然后倒入1500ml冰和水上。用水将过滤得到的黄色结晶洗至中性,并在真空中干燥。
产量:55.6g N-乙基-5-硝基-(6-甲氧基羰基氨基)糖精(14)
(14)
将10g经保护氨基-硝基化合物(14)引入30ml硫酸(97%)中。在100℃加热混合物2.25h,冷却,倒在300ml水上,并滤出。滤饼洗涤至中性,并在真空中干燥。
产量:6.2g N-乙基-5-硝基-6-氨基糖精(10)
(10)
将18g N-乙基-5-硝基-6-氨基糖精(10)和8.2g乙酸钠引入200g乙酸中。在室温下滴加16.1g溴在100g乙酸中的溶液。再搅拌30min,加入300g水和100g冰。滤出固体,用300g水洗涤,并在真空中干燥。
产量:24g N-乙基-5-硝基-6-氨基-7-溴糖精(15)
(15)
I.1.2重氮化组分(16)的合成:
(16)
合成(16)的第一步骤,6-溴糖精(6-溴-1,1-二氧代-1,2-苯并噻唑-3-酮)(17)的制备根据Bioorg. Med. Chem. 13 (2005), 949-961进行
(17)。
在第二步骤,根据以下方法使6-溴糖精烷基化:
将60.5g 6-溴糖精(17)引入260ml二甲基甲酰胺。加入74.8g溴乙烷、32.0g碳酸钾和2.6g碘化钠后,将混合物在100℃下加热1小时。冷却至室温后,将混合物引入2.5l水中。随后,用100ml水洗涤反应烧瓶两次。滤出合并的含水混合物,将经过滤的固体引入730ml水中。在搅拌半小时后,再次过滤。将化合物在真空中干燥。
产量:54g N-乙基-6-溴糖精(18)
(18)
N-乙基-6-溴糖精的硝化:
将30.4g N-乙基-6-溴糖精(18)引入120g发烟硫酸(20%)。滴加40g浓硝酸和浓硫酸的混合酸,使得混合物的温度不超过55℃。然后,将反应混合物在70℃下搅拌4.5小时。在加入7.2g浓硝酸和浓硫酸的混合酸后,将混合物在80℃下搅拌24小时。在冷却到室温后,将反应混合物滴加到300g冰、300g水和32g氨基磺酸中。利用冰浴,并另外加入300g冰将温度保持在0至10℃之间。过滤后,将产物洗涤至中性,并在真空中干燥。
产量:28.3g N-乙基-6-溴-5-硝基糖精(19)
(19)
将20g N-乙基-6-溴-5-硝基糖精(19)引入72g盐酸中。随后加入40ml甲醇和13g锡粒。在两小时内使温度升至75℃,在此温度下将混合物搅拌8h,冷却至室温,并滤出。将过滤残余物溶于200ml二甲基甲酰胺,并用200ml水沉淀。将产物再次滤出,并在真空中干燥。
产量:10g N-乙基-6-溴-5-氨基糖精(16)
(16)
I.2合成染料
I.2.1式(100)的染料
(100)
将5.8g N-乙基-5-硝基-6-氨基-7-溴糖精(15)引入5g冰和25g硫酸(97%)的混合物中。滴加5.1g亚硝基硫酸(40%,硫酸溶液),使得温度不超过4℃。将混合物在4-10℃下搅拌6h,随后加入15g硫酸(100%),以使重氮盐完全溶解。然后,将重氮盐的溶液滴加到10℃的31g水、2.8g硫酸(97%)、9.5g乙酸和4.1g 3-[二-(2-甲氧基乙基)氨基]-N-乙酰苯胺的混合物。在室温搅拌过夜后,加入150g水。过滤混合物,将滤饼洗涤至中性,并在真空中干燥。
产量:6g
1H-NMR (DMSO-d6, 250 MHz):δ = 8.55 (s, 1H, 芳H), 7.98 (s, 1H, 芳H), 7.63, 6.86 (AB, 2H, 芳H), 3.82 (m, 2H, NCH2), 3.76 (m, 2H, CH2), 3.60 (m, 2H, CH2), 3.29 (s, 3H, OCH3), 2.21 (s, 3H, CH3), 1.35 (t, 3H, CH3).
I.2.2式(151)的染料
将5.0g N-乙基-5-硝基-6-氨基糖精(10)引入6g冰和26g硫酸(97%)的混合物中。随后,在-1℃滴加5.4g亚硝基硫酸(40%,硫酸溶液),并在0至5℃搅拌混合物40min。
然后,在3h内将溶液滴加到在-3至3℃的35g水、3.1g硫酸(96%)和3.5g 1-(3-甲氧基丙基)-6-羟基-4-甲基-2-氧代-1,2-二氢-吡啶-3-甲腈的混合物中。加入完成后,过滤混合物,将滤饼洗涤至中性。将化合物在真空中干燥。
产量:5g
1H-NMR (CDCl6, 250 MHz):δ = 8.95 (s, 1H, 芳H), 8.55 (s, 1H, 芳H), 4.15 (m, 2H, NCH2), 3.91 (m, 2H, NCH2), 3.48 (m, 2H, CH2), 3.28 (s, 3H, OCH3), 2.78 (s, 3H, CH3), 1.93 (m, 2H, CH2), 1.48 (t, 3H, CH3).
I.2.3式(163)的染料
(163)
将4.0g N-乙基-5-硝基-6-氨基糖精(10)引入5g冰和25g硫酸(97%)的混合物中。在0℃滴加5.4g亚硝基硫酸(40%,硫酸溶液),并在0℃下搅拌混合物20min。
然后,在3h内,将所得重氮盐溶液滴加到在-2至0℃的28g水、2.5g硫酸(96%)和3.6g 2,6-双-(2-甲氧基乙基氨基)-4-甲基烟腈的混合物中。加入完成后,在3.5h内使混合物温热至室温。随后过滤,将滤饼洗涤至中性,并在真空中干燥。
产量:3g
1H-NMR (CDCl6, 250 MHz):δ = 8.44 (s, 1H, 芳H), 8.35 (s, 1H, 芳H), 6.27 (t, 1H, NH), 3.87 (m, 4H, NCH2), 3.77 (m, 2H, CH2), 3.68 (m, 2H, CH2), 3.60 (m, 2H, CH2), 3.41 (s, 6H, OCH3), 2.75 (s, 3H, CH3), 1.47 (t, 3H, CH3).
I.2.4式(184)的染料
(184)
将3.5g N-乙基-6-溴-5-氨基糖精(16)引入15.9g硫酸(96%)和0.66g乙酸的混合物中。在15分钟内,在2℃下滴加4.0g亚硝基硫酸(40%,硫酸溶液),并在2℃下搅拌混合物3小时。随后,将重氮盐的溶液滴加到在3至6℃(加冰)且pH值为1.45至1.6(加入30%的氢氧化钠溶液)的25g水、28.9g乙酸、1.6g氨基磺酸和4.1g 3-(N-苄基-N-丙基氨基)-4-甲氧基-N-乙酰苯胺的混合物。在pH=2搅拌1小时后,过滤混合物,将滤饼洗涤至中性。产物在真空中干燥,并用于合成化合物193,不用进一步纯化。
产量:5g
I.2.5式(203)的染料
(203)
将3.6g化合物(184)加到31ml吡啶和1.5g乙酸酐的混合物中。加入0.55g氰化铜(I),并将混合物在70℃下加热4.5小时。冷却到4℃后,加入50g水。将混合物过滤,并用25ml水和25ml甲醇洗涤。将产物在真空中干燥。
产量:2.7g
1H-NMR (CDCl3, 250 MHz):δ = 8.42 (s, 1H, 芳H), 8.37 (s, 1H, 芳H), 8.17 (s, 1H, 芳H), 7.35 - 7.28 (m, 6H, 芳H), 2.21 (s, 2H, CH2), 3.86 (m, 2H, NCH2), 3.82 (s, 3H, OCH3), 3.48 (t, 2H, CH2), 2.33 (s, 3H, CH3), 1.80 (m, 2H, CH2), 1.47 (t, 3H, CH3), 0.96 (t, 3H, CH3).
可根据上述方法制备以下表1-6中所列式(100)-(216)的染料。
表1:式(1aa)的染料
表2:式(1ab)的染料
表3:式(1ac)的染料
表4:式(1ad)的染料
表5:式(1ba)的染料
表6:式(1bc)的染料
II.应用实施例
II.1:聚酯的染色
将实施例I.1中制备的1重量份式(100)的染料与4份市售分散剂和15份水一起研磨。使用所得制剂,在130℃下,通过高温尽染方法在织造聚酯上产生1%染色(基于染料和基材)。
试验结果:染色件的耐光牢度极佳,AATCC 61和ISO 105试验中的结果也是如此。染料的提升染深性质很好。
II.2:聚酯的染色
用式(101)-(216)的染料代替式(101)的染料重复实施例II.1。染料的提升染深性质很好,染色件显示很好的耐光牢度,并且在AATCC 61和ISO 105试验中显示很好的结果。
Claims (10)
1.一种下式的偶氮染料
其中A为-CO-,并且Q为-SO2-;或者A为-SO2-,并且Q为-CO-;
R1表示C1-C6烷基、苄基、烯丙基、-CnH2n-COOR或-CnH2n-CN,其中n为1至3的数,R表示氢或C1-C6烷基;
X为硝基、氰基或卤素;
Y为氢、硝基、氰基或卤素;并且
K表示式(2a) - (2d)中的一个基团:
其中Z1为甲基或乙酰氨基;
Z2表示氢或甲氧基;
R2和R3各自独立为乙基、正丙基、烯丙基、2-甲氧基乙基、2-氰基乙基、苄基、甲氧基羰基甲基或甲氧基羰基乙基;
R4为氢、乙烯基、烯丙基或未取代或由氰基、羧基、羟基、C1-C6烷氧基、C2-C8烷氧基烷氧基或C6-C24芳基取代的C1-C6烷基;
R5和R6各自独立为氢、乙烯基、烯丙基或未取代或由氰基、羧基、羟基、C1-C6烷氧基、C2-C8烷氧基烷氧基或C6-C24芳基取代的C1-C6烷基;
R7为C1-C6烷基、C6-C24芳基或苄基;并且
R8和R9各自独立为氢、乙烯基、烯丙基或未取代或由氰基、羧基、羟基、C1-C6烷氧基或C6-C24芳基取代的C1-C6烷基。
2.权利要求1的式(1)的偶氮染料,其中Y为氢或溴。
3.权利要求1或2的式(1)的偶氮染料,其中R1为乙基。
4.权利要求1的式(1)的偶氮染料,其中K表示式(2b)的基团,其中R4为乙基或3-甲氧基丙基。
5.权利要求1的式(1)的偶氮染料,其中K表示式(2c)的基团,其中R5和R6各自独立为氢、2-甲氧基乙基、3-甲氧基丙基、3-(2-甲氧基乙氧基)丙基、苯基或苄基。
6.权利要求1的式(1)的偶氮染料,其中K表示式(2d)的基团,其中R7为苯基,R8和R9表示乙基。
7.权利要求1的式(1)的偶氮染料,所述偶氮染料具有下式的结构:
(206)。
8.一种制备权利要求1的式(1)的偶氮染料的方法,所述方法包括根据常规方法使(3)式的化合物重氮化:
其中R1和A、Q、X和Y如权利要求1中限定,然后使经重氮化的化合物与式K-H的偶联组分偶联,其中K如权利要求1中限定。
9.一种染色或印刷半合成或合成疏水性纤维材料的方法,其中将权利要求1的式(1)的染料施加给所述材料或加入到所述材料中。
10.权利要求1的式(1)的染料用于染色或印刷半合成或合成疏水性纤维材料的用途。
11. 一种通过权利要求9的方法染色或印刷的半合成或合成疏水性纤维材料。
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EP09179457.8 | 2009-12-16 | ||
EP09179457 | 2009-12-16 | ||
PCT/EP2010/067436 WO2011072966A1 (en) | 2009-12-16 | 2010-11-15 | Disperse azo dyes, a process for the preparation thereof and the use thereof |
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CN102652155A CN102652155A (zh) | 2012-08-29 |
CN102652155B true CN102652155B (zh) | 2014-11-05 |
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EP (1) | EP2513229B1 (zh) |
KR (1) | KR20120104356A (zh) |
CN (1) | CN102652155B (zh) |
ES (1) | ES2467926T3 (zh) |
PT (1) | PT2513229E (zh) |
TW (1) | TWI526500B (zh) |
WO (1) | WO2011072966A1 (zh) |
Families Citing this family (7)
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JP6333811B2 (ja) * | 2012-06-06 | 2018-05-30 | ハンツマン アドバンスト マテリアルズ (スイッツァランド) ゲーエムベーハーHuntsman Advanced Materials (Switzerland) Gmbh | アントラキノンアゾ染料 |
CN103059603B (zh) * | 2013-01-10 | 2015-03-11 | 浙江山峪染料化工有限公司 | 分散黄染料组合物 |
CN103059602A (zh) * | 2013-01-10 | 2013-04-24 | 浙江山峪染料化工有限公司 | 多组份拼混型分散黄染料 |
CN103059604A (zh) * | 2013-01-10 | 2013-04-24 | 浙江山峪染料化工有限公司 | 分散黄染料 |
TWI707002B (zh) * | 2016-05-25 | 2020-10-11 | 瑞士商杭斯曼高級材料公司 | 分散偶氮染料、其製備方法及其用途 |
CN106243046B (zh) * | 2016-08-02 | 2019-07-05 | 南京工业大学 | 一种甲基二磺隆的制备方法 |
PL3772529T3 (pl) * | 2019-08-05 | 2023-08-07 | Sanko Tekstil Isletmeleri San. Ve Tic. A.S. | Wrażliwe na ph barwniki do materiałów włókienniczych, sposób ich wytwarzania oraz ich zastosowanie |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3878189A (en) * | 1973-07-02 | 1975-04-15 | Eastman Kodak Co | Azo dye compounds from amino-1,2-benzisothiazolon-1,1-dioxides |
DE2739769A1 (de) * | 1976-09-08 | 1978-03-16 | Acna | Verfahren zum faerben von polyamidfasern |
GB1540060A (en) * | 1975-01-23 | 1979-02-07 | Kodak Ltd | Disperse monoazo dyestuffs derived from trifluoromethyl-substituted 2-amino benzothiazoles |
US5539088A (en) * | 1994-02-04 | 1996-07-23 | Hoechst Aktiengesellschaft | Water-soluble azo compounds, containing a diazo component with a heterocyclic moiety, and a coupling component with a fibre-reactive group, suitable as dyestuffs |
CN1179446A (zh) * | 1997-11-06 | 1998-04-22 | 大连理工大学化工学院 | 染合纤用单偶氮红色复合染料 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5853667B2 (ja) * | 1976-01-01 | 1983-11-30 | サンド アクチエンゲゼルシヤフト | モノアゾ染料及びその製法 |
AU2003276247A1 (en) | 2002-11-11 | 2004-06-03 | Ciba Specialty Chemicals Holding Inc. | Phthalimidyl-azo dyes, process for their preparation and their use |
-
2010
- 2010-11-15 PT PT107850133T patent/PT2513229E/pt unknown
- 2010-11-15 CN CN201080057113.5A patent/CN102652155B/zh active Active
- 2010-11-15 ES ES10785013.3T patent/ES2467926T3/es active Active
- 2010-11-15 KR KR1020127018372A patent/KR20120104356A/ko not_active Application Discontinuation
- 2010-11-15 WO PCT/EP2010/067436 patent/WO2011072966A1/en active Application Filing
- 2010-11-15 EP EP10785013.3A patent/EP2513229B1/en active Active
- 2010-12-14 TW TW099143692A patent/TWI526500B/zh active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3878189A (en) * | 1973-07-02 | 1975-04-15 | Eastman Kodak Co | Azo dye compounds from amino-1,2-benzisothiazolon-1,1-dioxides |
GB1540060A (en) * | 1975-01-23 | 1979-02-07 | Kodak Ltd | Disperse monoazo dyestuffs derived from trifluoromethyl-substituted 2-amino benzothiazoles |
DE2739769A1 (de) * | 1976-09-08 | 1978-03-16 | Acna | Verfahren zum faerben von polyamidfasern |
US5539088A (en) * | 1994-02-04 | 1996-07-23 | Hoechst Aktiengesellschaft | Water-soluble azo compounds, containing a diazo component with a heterocyclic moiety, and a coupling component with a fibre-reactive group, suitable as dyestuffs |
CN1179446A (zh) * | 1997-11-06 | 1998-04-22 | 大连理工大学化工学院 | 染合纤用单偶氮红色复合染料 |
Also Published As
Publication number | Publication date |
---|---|
ES2467926T3 (es) | 2014-06-13 |
PT2513229E (pt) | 2014-07-14 |
TWI526500B (zh) | 2016-03-21 |
EP2513229A1 (en) | 2012-10-24 |
EP2513229B1 (en) | 2014-04-23 |
CN102652155A (zh) | 2012-08-29 |
WO2011072966A1 (en) | 2011-06-23 |
TW201137046A (en) | 2011-11-01 |
KR20120104356A (ko) | 2012-09-20 |
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Effective date of registration: 20230410 Address after: Basel, SUI Patentee after: Huntsman Textile Dyeing (Switzerland) Co.,Ltd. Address before: Basel, SUI Patentee before: HUNTSMAN ADVANCED MATERIALS (SWITZERLAND) GmbH |
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