CN1711319A - 邻苯二甲酰亚胺-偶氮染料,其制备方法和其应用 - Google Patents
邻苯二甲酰亚胺-偶氮染料,其制备方法和其应用 Download PDFInfo
- Publication number
- CN1711319A CN1711319A CNA2003801029505A CN200380102950A CN1711319A CN 1711319 A CN1711319 A CN 1711319A CN A2003801029505 A CNA2003801029505 A CN A2003801029505A CN 200380102950 A CN200380102950 A CN 200380102950A CN 1711319 A CN1711319 A CN 1711319A
- Authority
- CN
- China
- Prior art keywords
- dyestuff
- formula
- ethyl
- dyeing
- methyl
- 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
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 230000008569 process Effects 0.000 title abstract description 9
- 239000000987 azo dye Substances 0.000 title 1
- 239000000975 dye Substances 0.000 claims abstract description 70
- 238000004043 dyeing Methods 0.000 claims abstract description 25
- 239000000463 material Substances 0.000 claims abstract description 20
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 14
- -1 2-ethoxyethyl Chemical group 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
- 238000007639 printing Methods 0.000 claims abstract description 10
- 239000004753 textile Substances 0.000 claims abstract description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 8
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 24
- 239000002657 fibrous material Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 9
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 238000006193 diazotization reaction Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims 1
- 239000000835 fiber Substances 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 210000004243 sweat Anatomy 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920004935 Trevira® Polymers 0.000 description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 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
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
- ZMESHQOXZMOOQQ-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)naphthalene Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZMESHQOXZMOOQQ-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-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
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 1
- 240000008886 Ceratonia siliqua Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 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
- 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 1
- BDKZHNJTLHOSDW-UHFFFAOYSA-N [Na].CC(O)=O Chemical compound [Na].CC(O)=O BDKZHNJTLHOSDW-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 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
- 125000000217 alkyl group Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000305 astragalus gummifer gum Substances 0.000 description 1
- 244000309464 bull Species 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
- 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
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940095399 enema Drugs 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
- 235000013312 flour Nutrition 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
- 239000003292 glue Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011159 matrix material Substances 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
- 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
- 239000002245 particle Substances 0.000 description 1
- 230000000176 photostabilization Effects 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
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000004576 sand Substances 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
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 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
- 235000012976 tarts Nutrition 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0033—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with one nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—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
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
- C09B43/42—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms by substituting radicals containing hetero atoms for —CN radicals
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Abstract
Description
R1 | R2 | R3 |
-CH2CH2OCH3 | -CH2CH2OCH3 | -CH3 |
″ | -C2H5 | ″ |
″ | -CH2CH2CH3 | ″ |
″ | -CH2COOCH3 | ″ |
″ | -CH2COOC2H5 | ″ |
″ | -CH(CH3)-COOCH3 | ″ |
″ | -CH(CH3)-COOC2H5 | ″ |
″ | -CH2CH2COOCH3 | ″ |
″ | -CH2CH2COOC2H5 | ″ |
″ | -CH2CH2O-CO-CH3 | ″ |
″ | -CH2CH2O-CO-C2H5 | ″ |
″ | 苄基 | ″ |
″ | -C2H5 | -NH-CO-CH3 |
″ | -CH2CH2CH3 | ″ |
″ | -CH2COOCH3 | ″ |
″ | -CH2COOC2H5 | ″ |
″ | -CH(CH3)-COOCH3 | ″ |
″ | -CH(CH3)-COOC2H5 | ″ |
″ | -CH2CH2COOCH3 | ″ |
″ | -CH2CH2COOC2H5 | ″ |
″ | -CH2CH2O-CO-CH3 | ″ |
″ | -CH2CH2O-CO-C2H5 | ″ |
″ | 苄基 | ″ |
″ | -CH2CH2OCH3 | -NH-CO-C2H5 |
″ | -C2H5 | ″ |
″ | -CH2CH2CH3 | ″ |
R1 | R2 | R3 |
″ | -CH2COOCH3 | ″ |
″ | -CH2COOC2H5 | ″ |
″ | -CH(CH3)-COOCH3 | ″ |
″ | -CH(CH3)-COOC2H5 | ″ |
″ | -CH2CH2COOCH3 | ″ |
″ | -CH2CH2COOC2H5 | ″ |
″ | -CH2CH2O-CO-CH3 | ″ |
″ | -CH2CH2O-CO-C2H5 | ″ |
″ | 苄基 | ″ |
″ | -CH2CH2OCH3 | -NH-SO2-CH3 |
″ | -C2H5 | ″ |
″ | -CH2CH2CH3 | ″ |
″ | -CH2COOCH3 | ″ |
″ | -CH2COOC2H5 | ″ |
″ | -CH(CH3)-COOCH3 | ″ |
″ | -CH(CH3)-COOC2H5 | ″ |
″ | -CH2CH2COOCH3 | ″ |
″ | -CH2CH2COOC2H5 | ″ |
″ | -CH2CH2O-CO-CH3 | ″ |
″ | -CH2CH2O-CO-C2H5 | ″ |
″ | 苄基 | ″ |
″ | -CH2CH2OCH3 | -NH-SO2-CH3 |
″ | -C2H5 | ″ |
″ | -CH2CH2CH3 | ″ |
″ | -CH2COOCH3 | ″ |
″ | -CH2COOC2H5 | ″ |
″ | -CH(CH3)-COOCH3 | ″ |
″ | -CH(CH3)-COOC2H5 | ″ |
″ | -CH2CH2COOCH3 | ″ |
″ | -CH2CH2COOC2H5 | ″ |
R1 | R2 | R3 |
″ | -CH2CH2O-CO-CH3 | ″ |
″ | -CH2CH2O-CO-C2H5 | ″ |
″ | 苄基 | ″ |
″ | -CH2CH2OCH3 | -NH-CO-CH2OCH3 |
″ | -C2H5 | ″ |
″ | -CH2CH2CH3 | ″ |
″ | -CH2COOCH3 | ″ |
″ | -CH2COOC2H5 | ″ |
″ | -CH(CH3)-COOCH3 | ″ |
″ | -CH(CH3)-COOC2H5 | ″ |
″ | -CH2CH2COOCH3 | ″ |
″ | -CH2CH2COOC2H5 | ″ |
″ | -CH2CH2O-CO-CH3 | ″ |
″ | -CH2CH2O-CO-C2H5 | ″ |
″ | 苄基 | ″ |
″ | -CH2CH2OCH3 | -OH |
″ | -C2H5 | ″ |
″ | -CH2CH2CH3 | ″ |
″ | -CH2COOCH3 | ″ |
″ | -CH2COOC2H5 | ″ |
″ | -CH(CH3)-COOCH3 | ″ |
″ | -CH(CH3)-COOC2H5 | ″ |
″ | -CH2CH2COOCH3 | ″ |
″ | -CH2CH2COOC2H5 | ″ |
″ | -CH2CH2O-CO-CH3 | ″ |
″ | -CH2CH2O-CO-C2H5 | ″ |
″ | 苄基 | ″ |
Claims (12)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02405967.7 | 2002-11-11 | ||
EP02405967 | 2002-11-11 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1711319A true CN1711319A (zh) | 2005-12-21 |
CN100379825C CN100379825C (zh) | 2008-04-09 |
Family
ID=32309516
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2003801029505A Expired - Lifetime CN100379825C (zh) | 2002-11-11 | 2003-11-04 | 邻苯二甲酰亚胺-偶氮染料,其制备方法和其应用 |
Country Status (8)
Country | Link |
---|---|
US (4) | US20060101594A1 (zh) |
EP (1) | EP1560883B1 (zh) |
JP (1) | JP4589726B2 (zh) |
KR (1) | KR101035841B1 (zh) |
CN (1) | CN100379825C (zh) |
AU (1) | AU2003276247A1 (zh) |
TW (1) | TWI338021B (zh) |
WO (1) | WO2004044058A1 (zh) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104403348A (zh) * | 2014-11-18 | 2015-03-11 | 李百春 | 一种高水洗牢度和升华牢度的紫色分散染料及其制备方法 |
CN104448893A (zh) * | 2014-11-18 | 2015-03-25 | 杭州福莱蒽特精细化工有限公司 | 一种高水洗牢度和升华牢度的红色分散染料及其制备方法 |
CN104448894A (zh) * | 2014-11-18 | 2015-03-25 | 昌邑福莱蒽特精细化工有限公司 | 高水洗牢度和升华牢度的分散绿光蓝染料及其制备方法 |
CN105602278A (zh) * | 2016-01-28 | 2016-05-25 | 俞杏英 | 一种蓝色分散染料单体化合物及其制备方法和应用 |
CN105647224A (zh) * | 2016-01-28 | 2016-06-08 | 俞杏英 | 一种邻苯二甲酰亚胺-偶氮分散染料单体化合物及其制备方法和应用 |
CN107722663A (zh) * | 2017-10-10 | 2018-02-23 | 浙江万丰化工有限公司 | 一种偶氮染料化合物及其制备方法和应用 |
CN108864732A (zh) * | 2018-07-06 | 2018-11-23 | 浙江万丰化工有限公司 | 一种含甲磺酰胺基团的偶氮染料化合物及其制备方法和应用 |
CN109054429A (zh) * | 2018-07-06 | 2018-12-21 | 浙江万丰化工有限公司 | 一种含乙酰胺基团的偶氮染料化合物及其制备方法和应用 |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002019260A (ja) | 2000-07-04 | 2002-01-23 | Seiko Epson Corp | 記録方法 |
CN1317337C (zh) * | 2004-12-28 | 2007-05-23 | 浙江龙盛集团股份有限公司 | 一种红色单偶氮染料组合物 |
US8088182B2 (en) * | 2008-10-21 | 2012-01-03 | Huntsman International Llc | Azo dyes, a process for the preparation thereof and the use thereof |
PT2513229E (pt) | 2009-12-16 | 2014-07-14 | Huntsman Adv Mat Switzerland | Corantes azo dispersos, um processo para o seu fabrico e o seu uso |
EP2754696A1 (en) | 2013-01-15 | 2014-07-16 | DyStar Colours Distribution GmbH | AOX-free navy and black disperse dye mixtures |
KR102287706B1 (ko) | 2013-01-14 | 2021-08-06 | 다이스타 컬러스 디스트리뷰션 게엠베하 | 고습윤 신속 분산 염료 혼합물 |
CN103965094B (zh) * | 2013-01-31 | 2016-07-06 | 江苏道博化工有限公司 | N-甲基-4-氨基-5-溴-邻苯二甲酰亚胺的合成方法 |
CN104448892B (zh) * | 2014-11-18 | 2017-04-05 | 李百春 | 一种高水洗牢度和升华牢度的宝蓝分散染料及其制备方法 |
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 |
EP3461861B1 (en) | 2017-10-02 | 2020-07-15 | DyStar Colours Distribution GmbH | High wet fast disperse dye mixtures |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3980634A (en) | 1973-07-02 | 1976-09-14 | Eastman Kodak Company | Phthalimidyl-azo aniline type compounds and polyester fibers dyed therewith |
JPS5818470B2 (ja) * | 1974-09-06 | 1983-04-13 | 三菱化学株式会社 | ゴウセイセンイルイ ノ センシヨクホウホウ |
EP0051563B1 (de) * | 1980-10-30 | 1985-04-24 | Ciba-Geigy Ag | Monoazoverbindungen |
EP0443984B1 (de) * | 1990-02-19 | 1995-01-18 | Ciba-Geigy Ag | Phthalimidyl-Azofarbstoffe |
JPH06329930A (ja) * | 1993-05-06 | 1994-11-29 | Ciba Geigy Ag | アゾ染料 |
US6008332A (en) * | 1994-02-11 | 1999-12-28 | Ciba Specialty Chemicals Corporation | Phthalimidylazo dyes, process for their preparation and the use thereof |
TW328094B (en) * | 1994-02-11 | 1998-03-11 | Ciba Sc Holding Ag | Phthalimidylazo dyes, process for their preparation and the use thereof |
TWI243192B (en) * | 1998-12-31 | 2005-11-11 | Ciba Sc Holding Ag | Phthalimidyl azo pigments, method for producing same and utilization thereof |
JP4260483B2 (ja) * | 2001-02-07 | 2009-04-30 | チバ ホールディング インコーポレーテッド | フタルイミドイルアゾ染料、それらの製造方法およびそれらの使用 |
RU2288242C2 (ru) * | 2001-02-07 | 2006-11-27 | Циба Спешиалти Кемикэлз Холдинг Инк. | Фталимидилазокрасители, способ их получения и их применение |
-
2003
- 2003-11-04 EP EP03810962.5A patent/EP1560883B1/en not_active Expired - Lifetime
- 2003-11-04 AU AU2003276247A patent/AU2003276247A1/en not_active Abandoned
- 2003-11-04 JP JP2004550922A patent/JP4589726B2/ja not_active Expired - Lifetime
- 2003-11-04 CN CNB2003801029505A patent/CN100379825C/zh not_active Expired - Lifetime
- 2003-11-04 US US10/533,010 patent/US20060101594A1/en not_active Abandoned
- 2003-11-04 WO PCT/EP2003/012282 patent/WO2004044058A1/en active Application Filing
- 2003-11-04 KR KR1020057008394A patent/KR101035841B1/ko not_active IP Right Cessation
- 2003-11-10 TW TW092131377A patent/TWI338021B/zh not_active IP Right Cessation
-
2008
- 2008-03-31 US US12/059,344 patent/US20080184499A1/en not_active Abandoned
-
2010
- 2010-12-09 US US12/964,053 patent/US20110078863A1/en not_active Abandoned
-
2014
- 2014-03-18 US US14/217,903 patent/US20140196224A1/en not_active Abandoned
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104403348A (zh) * | 2014-11-18 | 2015-03-11 | 李百春 | 一种高水洗牢度和升华牢度的紫色分散染料及其制备方法 |
CN104448893A (zh) * | 2014-11-18 | 2015-03-25 | 杭州福莱蒽特精细化工有限公司 | 一种高水洗牢度和升华牢度的红色分散染料及其制备方法 |
CN104448894A (zh) * | 2014-11-18 | 2015-03-25 | 昌邑福莱蒽特精细化工有限公司 | 高水洗牢度和升华牢度的分散绿光蓝染料及其制备方法 |
CN104448894B (zh) * | 2014-11-18 | 2016-08-24 | 昌邑福莱蒽特精细化工有限公司 | 高水洗牢度和升华牢度的分散绿光蓝染料及其制备方法 |
CN104448893B (zh) * | 2014-11-18 | 2017-04-05 | 杭州福莱蒽特精细化工有限公司 | 一种高水洗牢度和升华牢度的红色分散染料及其制备方法 |
CN105602278A (zh) * | 2016-01-28 | 2016-05-25 | 俞杏英 | 一种蓝色分散染料单体化合物及其制备方法和应用 |
CN105647224A (zh) * | 2016-01-28 | 2016-06-08 | 俞杏英 | 一种邻苯二甲酰亚胺-偶氮分散染料单体化合物及其制备方法和应用 |
CN107722663A (zh) * | 2017-10-10 | 2018-02-23 | 浙江万丰化工有限公司 | 一种偶氮染料化合物及其制备方法和应用 |
CN108864732A (zh) * | 2018-07-06 | 2018-11-23 | 浙江万丰化工有限公司 | 一种含甲磺酰胺基团的偶氮染料化合物及其制备方法和应用 |
CN109054429A (zh) * | 2018-07-06 | 2018-12-21 | 浙江万丰化工有限公司 | 一种含乙酰胺基团的偶氮染料化合物及其制备方法和应用 |
CN108864732B (zh) * | 2018-07-06 | 2020-05-05 | 浙江万丰化工股份有限公司 | 一种含甲磺酰胺基团的偶氮染料化合物及其制备方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
KR20050075390A (ko) | 2005-07-20 |
JP2006505662A (ja) | 2006-02-16 |
TW200420672A (en) | 2004-10-16 |
US20080184499A1 (en) | 2008-08-07 |
US20110078863A1 (en) | 2011-04-07 |
KR101035841B1 (ko) | 2011-05-20 |
AU2003276247A1 (en) | 2004-06-03 |
EP1560883A1 (en) | 2005-08-10 |
WO2004044058A1 (en) | 2004-05-27 |
JP4589726B2 (ja) | 2010-12-01 |
US20140196224A1 (en) | 2014-07-17 |
EP1560883B1 (en) | 2013-07-10 |
US20060101594A1 (en) | 2006-05-18 |
CN100379825C (zh) | 2008-04-09 |
TWI338021B (en) | 2011-03-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1711319A (zh) | 邻苯二甲酰亚胺-偶氮染料,其制备方法和其应用 | |
CN1099776A (zh) | 偶氮染料 | |
CN1249171C (zh) | 邻苯二甲酰亚胺基偶氮染料、其制备方法及其应用 | |
JP5031945B2 (ja) | フタルイミジルアゾ染料、それの製造方法およびその使用 | |
JP4205949B2 (ja) | アゾ染料、それらの製造方法および疎水性繊維材料の浸染または捺染におけるそれらの使用 | |
CN1069670C (zh) | 苯邻二甲酰亚胺基偶氮染料,它们的制备方法及其应用 | |
CN1289607C (zh) | 苯邻二甲酰亚胺基偶氮染料、其制备方法及其用途 | |
CN1103798C (zh) | 分散染料 | |
CN1729253A (zh) | 邻苯二甲酰亚胺偶氮染料、制备它们的方法和它们的用途 | |
CN101067047A (zh) | 一种分散红染料及其制备方法 | |
CN1176977A (zh) | 分散染料 | |
CN101067048A (zh) | 一种分散紫红染料及其制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: BASF SPECIALTY CHEMICALS HOLDING GMBH Free format text: FORMER OWNER: CIBA SC HOLDING AG Effective date: 20131018 Owner name: HUNTSMAN ADVANCED MATERIALS SW Free format text: FORMER OWNER: BASF SWITZERLAND CO., LTD. Effective date: 20131018 |
|
C41 | Transfer of patent application or patent right or utility model | ||
C56 | Change in the name or address of the patentee |
Owner name: CIBA SC HOLDING AG Free format text: FORMER NAME: CIBA SPECIALTY CHEMICALS HOLDING INC. Owner name: BASF SWITZERLAND CO., LTD. Free format text: FORMER NAME: BASF SPECIALTY CHEMICALS HOLDING GMBH |
|
CP01 | Change in the name or title of a patent holder |
Address after: Basel, Switzerland Patentee after: CIBA HOLDING Inc. Address before: Basel, Switzerland Patentee before: Ciba Specialty Chemicals Holding Inc. Address after: Basel, Switzerland Patentee after: BASF Ag AG Address before: Basel, Switzerland Patentee before: BASF Characteristic Chemicals Holding Co.,Ltd. |
|
TR01 | Transfer of patent right |
Effective date of registration: 20131018 Address after: Basel, Switzerland Patentee after: HUNTSMAN ADVANCED MATERIALS (SWITZERLAND) GmbH Address before: Basel, Switzerland Patentee before: BASF Ag AG Effective date of registration: 20131018 Address after: Basel, Switzerland Patentee after: BASF Characteristic Chemicals Holding Co.,Ltd. Address before: Basel, Switzerland Patentee before: CIBA HOLDING Inc. |
|
TR01 | Transfer of patent right |
Effective date of registration: 20230407 Address after: Basel, SUI Patentee after: Huntsman Textile Dyeing (Switzerland) Co.,Ltd. Address before: Basel, SUI Patentee before: HUNTSMAN ADVANCED MATERIALS (SWITZERLAND) GmbH |
|
TR01 | Transfer of patent right | ||
CX01 | Expiry of patent term |
Granted publication date: 20080409 |
|
CX01 | Expiry of patent term |