CN1659238A - 蒽醌-偶氮染料 - Google Patents
蒽醌-偶氮染料 Download PDFInfo
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- CN1659238A CN1659238A CN038127288A CN03812728A CN1659238A CN 1659238 A CN1659238 A CN 1659238A CN 038127288 A CN038127288 A CN 038127288A CN 03812728 A CN03812728 A CN 03812728A CN 1659238 A CN1659238 A CN 1659238A
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- azoic dyestuff
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- 239000000987 azo dye Substances 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 19
- 239000004033 plastic Substances 0.000 claims abstract description 12
- 229920003023 plastic Polymers 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 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 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 2
- 239000000975 dye Substances 0.000 claims description 41
- -1 anthraquinone compounds Chemical class 0.000 claims description 26
- 239000000463 material Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000004040 coloring Methods 0.000 claims description 9
- 239000008187 granular material Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000011368 organic material Substances 0.000 claims description 8
- 238000006193 diazotization reaction Methods 0.000 claims description 7
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000006068 polycondensation reaction Methods 0.000 claims description 3
- 238000012644 addition polymerization Methods 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000000176 photostabilization Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 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
- 229920000728 polyester Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-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
- 150000001408 amides Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004902 Softening Agent Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 150000004646 arylidenes Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- QXHDYMUPPXAMPQ-UHFFFAOYSA-N 2-(4-aminophenyl)ethanol Chemical compound NC1=CC=C(CCO)C=C1 QXHDYMUPPXAMPQ-UHFFFAOYSA-N 0.000 description 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229920006222 acrylic ester polymer Polymers 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229920001400 block copolymer Polymers 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
- 238000003490 calendering Methods 0.000 description 1
- 238000001444 catalytic combustion detection Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 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
- 239000007788 liquid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 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
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012429 reaction media 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/021—Disazo dyes characterised by two coupling components of the same type
- C09B35/03—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a heterocyclic compound
- C09B35/031—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a heterocyclic compound containing a six membered ring with one nitrogen atom as the only ring hetero 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
- C09B29/0018—Monoazo dyes prepared by diazotising and coupling from diazotized aminopolycyclic rings
- C09B29/0022—Monoazo dyes prepared by diazotising and coupling from diazotized aminopolycyclic rings from diazotized aminoanthracene
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
-
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerization Catalysts (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Coloring (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及式I、II或III的偶氮染料,其中R1和R2彼此独立地表示一种或多种选自以下的二价基团:亚烷基、亚芳基、亚芳烷基和亚环烷基,其可以被-O-、-S-、-NH-、-NR8-、-COO-、-CONH-或-CONR9-间隔,其中R8和R9是烷基或芳基,X是-O-或-NH-,R3是-CN或-CONH2,R4是甲基或三氟甲基,和R5、R6、R7和R8彼此独立地表示H、卤素或-CN,还涉及其制备方法及其在生产纺前着色塑料或聚合物着色粒料的方法中的用途。
Description
本发明涉及新的偶氮染料、其制备方法及其在生产纺前染色塑料或聚合物色料颗粒的方法中的用途和在生产滤色片中作为着色剂的用途。
用于纺前染色塑料的染料是公知的。例如在美国专利5 367 039中描述了具有(甲基)丙烯酰基的1,4,5,8-四取代蒽醌,它们可以与乙烯基单体共聚,从而适用于生产着色的乙烯基聚合物。
但是,目前使用的染料不能满足在耐光性方面的高要求,特别是在热稳定性方面。
因此需要一种新的热稳定性染料,其能实现具有高着色力和显示耐光性、特别是高温耐光性并且具有良好全面牢固性能的着色。
美国专利3 998 802描述了基于2,6-二氨基吡啶的偶氮染料,其适合于按照消耗法(exhaust process)着色合成聚酰胺和聚酯,其特征在于具有良好的耐热固化性和耐光性。
现在惊奇地发现,特定的基于2,6-二氨基吡啶的偶氮染料适合于纺前合成聚合物,实现具有高着色力和显示耐光性、特别是高温耐光性并且具有良好全面牢固性能的着色。
本发明涉及式I、II或III的偶氮染料:
其中
R1和R2彼此独立地表示一种或多种选自以下的二价基团:亚烷基、亚芳基、亚芳烷基和亚环烷基,其可以被-O-、-S-、-NH-、-NR8-、-COO-、-CONH-或-CONR9-间隔,其中R8和R9是烷基或芳基,
X是-O-或-NH-,
R3是-CN或-CONH2,
R4是甲基或三氟甲基,和
R5、R6、R7和R8彼此独立地表示氢、卤素或-CN。
取代基R1和R2可以是相同或不同的,优选R1和R2是相同的。
任何表示烷基的基团可以是直链或支链烷基,优选具有1-12个碳原子,可以被一个或多个羟基、氨基或卤素原子取代。
烷基的例子包括甲基、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、正己基、正庚基、正辛基、异辛基、正癸基和正十二烷基。
取代的烷基包括例如2-羟基乙基、2-羟基丙基、4-羟基丁基、2-氨基乙基、2-氨基丙基、4-氨基丁基、2-氯乙基、2-溴乙基和4-氯丁基。
作为R8或R9的芳基优选具有5-24个碳原子,特别是6-14个碳原子,和可以例如被C1-C4烷基、C1-C4烷氧基、卤素取代或被基团-NH-CO-R取代,其中R是氨基、C1-C4烷基、未取代的苯基,或被C1-C4烷基、C1-C4烷氧基或卤素取代的苯基。
合适的芳基的例子包括苯基、甲苯基、基、isityl、2-羟基苯基、4-羟基苯基、2-氯苯基、4-氯苯基、2-氨基苯基、3-氨基苯基、4-氨基苯基、4-甲氧基苯基、4-乙氧基苯基、4-乙酰氨基苯基、萘基和菲基。
当二价基团R1或R2之一是亚烷基时,优选是C1-C6亚烷基,例如亚乙基、亚丙基、三亚甲基、四亚甲基或六亚甲基。
被-O-或-NH-间隔的亚烷基可以是聚氧亚乙基、聚氧亚丙基、聚氨基亚乙基和聚氧亚丙基,例如-(OCH2CH2)n-、-(0CHCH3CH2)n-、-(NHCH2CH2)n-、-(NHCHCH3CH2)n-,其中n是1-10的数。
亚芳基的例子包括1,2-、1,3-和1,4-亚苯基,甲苯-2,4-二基,甲苯-2,5-二基,甲苯-2,6-二基,萘-1,4-二基,萘-1,5-二基和萘-1,8-二基。
亚芳烷基例如是下式的基团:
亚环烷基的例子有1,2-亚环戊基、1,3-亚环戊基、1,2-亚环己基、1,3-亚环己基和1,4-亚环己基。
卤素是氟、氯、溴或碘。
优选其中R3是-CN和R4是甲基的式I、II或III的偶氮染料。
还优选其中R1和R2是C2-C8亚烷基、C6-C14亚芳基或C8-C22亚芳烷基的式I、II或III的偶氮染料。
特别优选其中R1和R2各自是式IV基团的式I、II或III的偶氮染料:
XH与亚烷基键合,且X是-O-。
R5、R6、R7和R8优选是氢、氯或溴,特别是氢。
特别优选的式I偶氮染料是式Ia的化合物:
式I、II或III的化合物可以按照公知的方法制备,例如通过将二氨基蒽醌或氨基蒽醌进行重氮化,然后进行偶联反应。
本发明还涉及一种制备式I、II或III的偶氮染料的方法,包括将式V、VI或VII的蒽醌化合物按照常规方法进行重氮化,
其中R5、R6、R7和R8如上定义,
然后偶联式VIII的偶联组分,
其中R1、R2、R3、R4和X如上定义。
二氨基蒽醌化合物或氨基蒽醌化合物的重氮化按照本身已知的方法进行,例如使用亚硝酰基硫酸在酸性水溶液介质,例如盐酸水溶液介质或硫酸水溶液介质中进行。但是,重氮化也可以使用其他重氮化试剂进行,例如亚硝酸钠。在重氮化过程中,在反应介质中可以存在其它酸,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℃的温度下,例如在0℃至室温下进行。
将经过重氮化的蒽醌衍生物偶联到式VIII偶联组分上的反应按照公知方式类似地进行,例如在酸性、含水或含水有机的介质中进行,有利地在-10℃至30℃的温度下,特别是低于10℃下进行。所用的酸可以例如是盐酸、乙酸、丙酸、硫酸或磷酸。
式VIII的偶联组分是公知的,或可以按照本身已知的方式制备,例如通过使式IX的2,6-二氯吡啶衍生物
其中R3和R4如上定义,
同时或连续地与式X的胺和式XI的胺反应,
HX-R1-NH2 (X),
HX-R2-NH2 (XI),
其中R1和R2如上定义。
式IX的化合物以及式X和式XI的胺是公知的,和可以通过本身已知的方式制备。
本发明还涉及一种生产着色塑料或聚合物着色粒料的方法,包括将高分子量有机材料与着色有效量的至少一种式I、II或III的偶氮染料混合。
使用式I、II或III的偶氮染料染色高分子量有机物质的操作可以例如使用辊磨、混合装置或研磨装置进行,使得这种染料与这些物质混合,该染料溶解或细分散在高分子量材料中。混有染料的高分子量有机物质然后按照本身已知的方式加工,例如压延、压塑、挤出、涂覆、旋转、倾倒或注塑,使得着色物质形成最终形状。染料的混合也可以刚好在实际加工步骤之前进行,例如通过同时连续加料,将固体例如粉状染料和粒状或粉状高分子量有机物质和在合适时的其它成分例如添加剂直接加入挤出机的进料区,这些组分刚好在加工之前混合。但是,通常优选将染料预先混合加入高分子量有机物质中,因为这样能获得更均匀着色的基质。
为了生产非硬质的成型品或降低其脆性,通常希望在成型之前将所谓的增塑剂加入高分子量有机化合物中。可以使用的增塑剂例如是磷酸、邻苯二甲酸或癸二酸的酯。在本发明的方法中,增塑剂可以在加入着色剂之前或之后加入聚合物中。为了获得不同的色调,还可以向高分子量有机物质中加入除了式I、II或III偶氮染料之外的所需量的其它颜料或其它着色剂,任选与其它添加剂例如填料或催干剂一起加入。
优选特别是纤维形式的热塑性塑料进行着色。优选的能根据本发明着色的高分子量有机物质是介电常数≥2.5的普通聚合物,特别是聚酯、聚碳酸酯(PC)、聚苯乙烯(PS)、聚甲基丙烯酸甲酯(PMMA)、聚酰胺、聚乙烯、聚丙烯、苯乙烯/丙烯腈(SAN)或丙烯腈/丁二烯/苯乙烯(ABS)共聚物。聚酯和聚酰胺是特别优选的。更特别优选的是线型芳族聚酯,其可以通过对苯二甲酸与二元醇、特别是乙二醇的缩聚反应获得,或是对苯二甲酸与1,4-二(羟基甲基)环己烷的缩聚物,例如聚对苯二甲酸乙二酯(PET)或聚对苯二甲酸丁二酯(PBT);以及聚碳酸酯,例如从α,α-二甲基-4,4-二羟基-二苯基甲烷和光气获得的那些,或者基于聚氯乙烯和聚酰胺的聚合物,例如聚酰胺6或聚酰胺6.6。
因为本发明的式I、II和III化合物含有至少4个活泼氢原子(两个NH和两个XH基团),所以将染料与单体混合并将其以共聚单体形式直接引入聚合物主链是可能的,前提是这些单体含有能与NH或OH基团的活泼氢原子反应的活性基团。这种单体的例子包括环氧化物(环氧树脂)、异氰酸酯(聚氨酯)和羧酰氯(聚酰胺、聚酯)。
本发明因此涉及一种生产着色塑料或聚合物着色粒料的方法,包括将含有至少一种具有至少一个NH-或OH-活性基团且能进行聚合、加聚或缩聚反应的单体混合物与至少一种式I、II或III的化合物反应。
本发明还涉及式I、II或III的化合物在生产纺前染色塑料或聚合物着色粒料中的用途,和涉及使用式I、II或III化合物着色的塑料或聚合物着色粒料。
根据本发明的染料赋予上述材料、特别是聚酯材料以高着色力的色调水平,并且具有良好的使用牢固性,特别是优异的高温耐光性。
根据本发明的染料也可以与其它染料一起使用以产生混合色调。
此外,本发明的式I、II和III的偶氮染料适合作为在生产滤色片中的着色剂,特别是在400-700nm的可见光范围内,用于液晶显示器(LCDs)或电荷组合装置(CCDs)。
GB-A 2 182 165中描述了生产滤色片的方法,其中将红色、蓝色和绿色着色剂顺序涂到合适的基材例如无定形硅上。滤色片可以例如使用油墨、特别是印刷油墨涂覆,该油墨包含根据本发明的偶氮染料,或者可以例如通过将根据本发明的偶氮染料与能以化学、热或光解方式结构化的高分子量物质共混。其它的生产可以例如相似地按照EP-A654 711进行,其中涂覆在基材例如LCD上,然后进行光结构化和显影。其它描述生产滤色片的文献包括US-A 5 624 467,Displaysl4/2,115(1993)和WO 98/45756。
用于液晶显示器(LCD)的使用本发明偶氮染料的滤色片具有突出的色点高度传输性能。
本发明还涉及本发明偶氮染料在生产滤色片中作为着色剂的用途。
以下实施例用于说明本发明。
I.制备实施例
I.1式Ia化合物
A.2,6-二[4-(2-羟基乙基)苯基氨基]-3-氰基-4-甲基吡啶的合成
将495.0g的2-(4-氨基苯基)乙醇加入平底烧瓶中,并加热到140℃。在120-140℃,先向该熔体中加入255.8g的碳酸钠,然后加入190.8g的2,6-二氯-3-氰基-4-甲基吡啶。反应混合物于190-195℃搅拌18小时,然后分份加入1L的2N盐酸中,静置过夜。沉淀物进行过滤、洗涤和在真空干燥箱中干燥。
收率:380.8g(98%)。
B.用2,6-二氨基蒽醌进行重氮化
在10分钟内将14.4g的2,6-二氨基蒽醌加入75ml的浓硫酸中,使得该混合物的温度不超过40℃。在室温搅拌30分钟后,缓慢滴加入21.6ml的40%亚硝酰基硫酸,使得温度是22-25℃(约20分钟)。该混合物然后于室温搅拌4小时,得到重氮翁盐的棕色溶液。
将作为初始进料的1.5L冰醋酸加入配备有pH测量仪的6L玻璃烧瓶中;在搅拌下加入48g的2,6-二[4-(2-羟基乙基)苯基氨基]-3-氰基-4-甲基吡啶。在加入750ml的冰水后,在约10分钟内滴加入重氮翁盐溶液。通过加入240ml的30%氢氧化钠溶液将pH调节到0.25;在添加过程中,反应混合物的温度不超过35℃。该溶液然后于45-50℃搅拌4小时,并于室温静置过夜。沉淀物进行过滤,用80%乙酸、水、二甲基甲酰胺(DMF)洗涤和再次用水洗涤,并在真空干燥箱中于60-70℃干燥。
收率:57.2g(92%)。
II.应用实施例
II.1生产用于液晶显示器(LCD)的滤色片
在装有83.3g锆陶瓷珠的100ml玻璃容器中,使用Dispermat将实施例I.1的2.8g偶氮染料、0.28g的Solsperse 5000、4.10g的Disperbyk 161(分散剂,高分子量嵌段共聚物在乙酸正丁酯/乙酸1-甲氧基-2-丙基酯(1∶6)中的30%溶液,含有具有颜料亲合性的基团,BYK Chemie)和14.62g的乙酸1-甲氧基-2-丙基酯(MPA)于23℃在1000转/分钟下搅拌10分钟,和在3000转/分钟下搅拌180分钟。在添加4.01g的丙烯酸酯聚合物粘合剂(35%MPA溶液)之后,在室温下在3000转/分钟下搅拌30分钟。取出珠粒之后,用相等重量的MPA稀释该分散体。
使用旋涂装置,用所得的分散液涂覆玻璃基材(Corning1737-F型),并在1000转/分钟下离心30秒。涂层在热板上于100℃干燥2分钟,并于200℃干燥5分钟。所得的层厚度是0.4微米。
以下偶氮染料(表1-15)同样适用于纺前着色塑料,可以与实施例I.1类似地制备。
表1:
R′2=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
表2:
R′1=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
表3:
R1′=R2′=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
表4:
R′2=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
表5:
R′1=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
表6:
R′1=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
表7:
R′2=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
表8:
R′1=R′2=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
表9:
R′2=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
表10:
R′1=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
表11:
R′2=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
表12:
R′1=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
表13:
R1′=R2′=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
表14:
R′2=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
表15:
R′1=-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-O-(CH2CH2)-OH,
-NH-CH2-CHOH-CH2-OH,
-NH-(CH2CH2)-S-(CH2CH2)-OH,
-NH-(CH2CH2)-NH-(CH2CH2)-OH,
-NH-(CH2CH2)-NH2,
-NH-CH2-CHOH-CH2-NH2,
-NH-CH2-CON(CH2CH2OH)2,
-NH-CH2CH2-CON(CH2CH2OH)2,
Claims (11)
1.式I、II或III的偶氮染料:
其中
R1和R2彼此独立地表示一种或多种选自以下的二价基团:亚烷基、亚芳基、亚芳烷基和亚环烷基,其可以被-O-、-S-、-NH-、-NR8-、-COO-、-CONH-或-CONR9-间隔,其中R8和R9是烷基或芳基,
X是-O-或-NH-,
R3是-CN或-CONH2,
R4是甲基或三氟甲基,和
R5、R6、R7和R8彼此独立地表示氢、卤素或-CN。
2.根据权利要求1的式I、II或III偶氮染料,其中R3是-CN和R4是甲基。
3.根据权利要求1或2的式I、II或III偶氮染料,其中R1和R2是C2-C8亚烷基、C6-C14亚芳基或C8-C22亚芳烷基。
5.根据权利要求1的式Ia偶氮染料:
7.一种生产着色塑料或聚合物着色粒料的方法,包括将高分子量有机材料与着色有效量的至少一种权利要求1的式I、II或III偶氮染料混合。
8.一种生产着色塑料或聚合物着色粒料的方法,包括将含有至少一种具有至少一个NH-或OH-活性基团且能进行聚合、加聚或缩聚反应的单体的混合物与至少一种权利要求1的式I、II或III化合物反应。
9.权利要求1-5任一项的偶氮染料在生产纺前着色塑料或聚合物着色粒料中的用途,
10.根据权利要求7或8的方法着色的塑料或聚合物着色粒料。
11.权利要求1的式I、II或III偶氮染料在生产滤色片中作为着色剂的用途。
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EP02405444 | 2002-06-03 | ||
EP02405444.7 | 2002-06-03 |
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CN1659238A true CN1659238A (zh) | 2005-08-24 |
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US (1) | US7030229B2 (zh) |
EP (1) | EP1509573B1 (zh) |
JP (1) | JP2005528502A (zh) |
KR (1) | KR20050012772A (zh) |
CN (1) | CN1659238A (zh) |
AT (1) | ATE315614T1 (zh) |
AU (1) | AU2003238410A1 (zh) |
BR (1) | BR0311533A (zh) |
CA (1) | CA2483471A1 (zh) |
DE (1) | DE60303206T2 (zh) |
ES (1) | ES2256749T3 (zh) |
MX (1) | MXPA04012033A (zh) |
RU (1) | RU2004139052A (zh) |
TW (1) | TW200400231A (zh) |
WO (1) | WO2003102083A1 (zh) |
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EP1797146A1 (en) * | 2004-09-03 | 2007-06-20 | Huntsman Advanced Materials (Switzerland) GmbH | Cyanopyridine-based azo dyes |
EP2008995B1 (en) | 2007-06-29 | 2013-09-11 | Ricoh Company, Ltd. | Azo compound and method of preparing the azo compound |
ES2403068T3 (es) * | 2010-07-29 | 2013-05-13 | Clariant Finance (Bvi) Limited | Tintes ácidos |
EP3527628A1 (en) * | 2012-06-06 | 2019-08-21 | Huntsman Advanced Materials (Switzerland) GmbH | Anthraquinone azo dyes |
CN112679979B (zh) * | 2020-12-29 | 2023-09-01 | 浙江永合新材料科技有限公司 | 一种苯并三唑类紫外线吸收剂中间体偶氮染料的制备方法 |
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US3998802A (en) * | 1970-12-19 | 1976-12-21 | Basf Aktiengesellschaft | Azo dye with a 3-cyano- or 3-carbamoyl-4-methyl-2,6-diamino-pyridine coupling component |
CH592152A5 (zh) * | 1974-07-23 | 1977-10-14 | Ciba Geigy Ag | |
US4150943A (en) * | 1975-10-29 | 1979-04-24 | Basf Aktiengesellschaft | Uniformly dyed water-swellable cellulosic fibers |
AT373930B (de) * | 1975-10-29 | 1984-03-12 | Basf Ag | Farbstoffzubereitungen fuer das faerben und bedrucken von cellulose und cellulosehaltigem textilmaterial |
US4515716A (en) * | 1981-09-16 | 1985-05-07 | Mitsubishi Chemical Industries Limited | 2,6-Diaminopyridine-based azo dyes for cellulose-containing fibers |
GB8526155D0 (en) | 1985-10-23 | 1985-11-27 | Ici Plc | Colour filter |
US5367039A (en) * | 1988-07-06 | 1994-11-22 | Nippon Paint Company, Ltd. | Production of colored vinyl polymer particles by polymerizing a vinyl polymerizable monomer with a polymerizable dye |
US5624467A (en) * | 1991-12-20 | 1997-04-29 | Eastman Kodak Company | Microprecipitation process for dispersing photographic filter dyes |
DE69418826T2 (de) * | 1993-11-22 | 1999-10-21 | Ciba Specialty Chemicals Holding Inc., Basel | Zusammensetzungen zur Herstellung strukturierter Farbbilder und deren Anwendung |
AU7042198A (en) | 1997-04-09 | 1998-10-30 | Ciba Specialty Chemicals Holding Inc. | Highly transparent, colour-pigmented high molecular weight material |
EP1343845A1 (en) * | 2000-12-22 | 2003-09-17 | Ciba SC Holding AG | Anthraquinone dyes, preparation thereof and use thereof |
-
2003
- 2003-05-27 CA CA002483471A patent/CA2483471A1/en not_active Abandoned
- 2003-05-27 AU AU2003238410A patent/AU2003238410A1/en not_active Abandoned
- 2003-05-27 MX MXPA04012033A patent/MXPA04012033A/es unknown
- 2003-05-27 US US10/516,440 patent/US7030229B2/en not_active Expired - Fee Related
- 2003-05-27 RU RU2004139052/04A patent/RU2004139052A/ru not_active Application Discontinuation
- 2003-05-27 JP JP2004510329A patent/JP2005528502A/ja active Pending
- 2003-05-27 ES ES03732478T patent/ES2256749T3/es not_active Expired - Lifetime
- 2003-05-27 EP EP03732478A patent/EP1509573B1/en not_active Expired - Lifetime
- 2003-05-27 KR KR10-2004-7019617A patent/KR20050012772A/ko not_active Application Discontinuation
- 2003-05-27 WO PCT/EP2003/005562 patent/WO2003102083A1/en active IP Right Grant
- 2003-05-27 BR BR0311533-0A patent/BR0311533A/pt not_active Application Discontinuation
- 2003-05-27 DE DE60303206T patent/DE60303206T2/de not_active Expired - Lifetime
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EP1509573B1 (en) | 2006-01-11 |
RU2004139052A (ru) | 2005-10-10 |
TW200400231A (en) | 2004-01-01 |
MXPA04012033A (es) | 2005-03-07 |
CA2483471A1 (en) | 2003-12-11 |
EP1509573A1 (en) | 2005-03-02 |
DE60303206T2 (de) | 2006-07-20 |
DE60303206D1 (de) | 2006-04-06 |
WO2003102083A1 (en) | 2003-12-11 |
US7030229B2 (en) | 2006-04-18 |
JP2005528502A (ja) | 2005-09-22 |
US20050182247A1 (en) | 2005-08-18 |
KR20050012772A (ko) | 2005-02-02 |
BR0311533A (pt) | 2005-02-22 |
AU2003238410A1 (en) | 2003-12-19 |
ES2256749T3 (es) | 2006-07-16 |
ATE315614T1 (de) | 2006-02-15 |
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