RU2315791C2 - Антрахиноновые красители - Google Patents
Антрахиноновые красители Download PDFInfo
- Publication number
- RU2315791C2 RU2315791C2 RU2004131533/04A RU2004131533A RU2315791C2 RU 2315791 C2 RU2315791 C2 RU 2315791C2 RU 2004131533/04 A RU2004131533/04 A RU 2004131533/04A RU 2004131533 A RU2004131533 A RU 2004131533A RU 2315791 C2 RU2315791 C2 RU 2315791C2
- Authority
- RU
- Russia
- Prior art keywords
- formula
- aryl
- dyes
- mixture
- compounds
- Prior art date
Links
- 239000001000 anthraquinone dye Substances 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 claims description 3
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 20
- 238000004043 dyeing Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- 239000002861 polymer material Substances 0.000 abstract 2
- -1 1,4,5,8-tetrasubstituted anthraquinones Chemical class 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000004040 coloring Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000004952 Polyamide Substances 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
- 125000005843 halogen group Chemical group 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- BBANGWRUXDHLCL-UHFFFAOYSA-N 1,3,5,7-tetrabromoanthracene-9,10-dione Chemical compound BrC1=CC(Br)=C2C(=O)C3=CC(Br)=CC(Br)=C3C(=O)C2=C1 BBANGWRUXDHLCL-UHFFFAOYSA-N 0.000 description 2
- BGLDZSXVOYZKHW-UHFFFAOYSA-N 1,5-dianilino-3,7-dibromoanthracene-9,10-dione Chemical compound C=12C(=O)C3=CC(Br)=CC(NC=4C=CC=CC=4)=C3C(=O)C2=CC(Br)=CC=1NC1=CC=CC=C1 BGLDZSXVOYZKHW-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- OZWNTJNFQILZTQ-UHFFFAOYSA-N 3,7-dibromo-1,5-bis(2,4,6-trimethylanilino)anthracene-9,10-dione Chemical compound CC1=CC(C)=CC(C)=C1NC1=CC(Br)=CC2=C1C(=O)C1=CC(Br)=CC(NC=3C(=CC(C)=CC=3C)C)=C1C2=O OZWNTJNFQILZTQ-UHFFFAOYSA-N 0.000 description 2
- ULJPDXIDBQRDCG-UHFFFAOYSA-N 3,7-dibromo-1,5-bis(2-hydroxyethylamino)anthracene-9,10-dione Chemical compound O=C1C2=C(NCCO)C=C(Br)C=C2C(=O)C2=C1C=C(Br)C=C2NCCO ULJPDXIDBQRDCG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000976 ink Substances 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
- 239000000049 pigment Substances 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
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- HEEAHTSGNNYQEW-UHFFFAOYSA-N 1,3,5,7-tetrakis(phenylsulfanyl)anthracene-9,10-dione Chemical compound C=1C(SC=2C=CC=CC=2)=C2C(=O)C3=CC(SC=4C=CC=CC=4)=CC(SC=4C=CC=CC=4)=C3C(=O)C2=CC=1SC1=CC=CC=C1 HEEAHTSGNNYQEW-UHFFFAOYSA-N 0.000 description 1
- ZAKMBYDHPRZEHW-UHFFFAOYSA-N 1,5-bis(2-hydroxyethylamino)-3,7-bis(phenylsulfanyl)anthracene-9,10-dione Chemical compound C=1C=2C(=O)C3=C(NCCO)C=C(SC=4C=CC=CC=4)C=C3C(=O)C=2C(NCCO)=CC=1SC1=CC=CC=C1 ZAKMBYDHPRZEHW-UHFFFAOYSA-N 0.000 description 1
- LXOOQPXNJPRKAI-UHFFFAOYSA-N 1,5-dianilino-3,7-bis(2-hydroxyethylsulfanyl)anthracene-9,10-dione Chemical compound C=12C(=O)C3=CC(SCCO)=CC(NC=4C=CC=CC=4)=C3C(=O)C2=CC(SCCO)=CC=1NC1=CC=CC=C1 LXOOQPXNJPRKAI-UHFFFAOYSA-N 0.000 description 1
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-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
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- PDOQHLICOZEXKW-UHFFFAOYSA-N 3,7-bis(phenylsulfanyl)-1,5-bis(2,4,6-trimethylanilino)anthracene-9,10-dione Chemical compound CC1=CC(C)=CC(C)=C1NC1=CC(SC=2C=CC=CC=2)=CC2=C1C(=O)C1=CC(SC=3C=CC=CC=3)=CC(NC=3C(=CC(C)=CC=3C)C)=C1C2=O PDOQHLICOZEXKW-UHFFFAOYSA-N 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
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 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
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 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
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 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 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000000038 blue colorant Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000000040 green colorant Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000001062 red colorant 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
- 239000007787 solid Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000011145 styrene acrylonitrile resin Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 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
- 238000001429 visible spectrum Methods 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/542—Anthraquinones with aliphatic, cycloaliphatic, araliphatic or aromatic ether groups
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Materials For Photolithography (AREA)
- Coloring (AREA)
- Optical Filters (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02405225 | 2002-03-22 | ||
| EP02405225.0 | 2002-03-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2004131533A RU2004131533A (ru) | 2005-06-27 |
| RU2315791C2 true RU2315791C2 (ru) | 2008-01-27 |
Family
ID=28051879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004131533/04A RU2315791C2 (ru) | 2002-03-22 | 2003-03-13 | Антрахиноновые красители |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7160335B2 (enExample) |
| EP (1) | EP1487921A1 (enExample) |
| JP (1) | JP4500053B2 (enExample) |
| KR (1) | KR20050006132A (enExample) |
| CN (1) | CN1643075A (enExample) |
| AU (1) | AU2003227058A1 (enExample) |
| BR (1) | BR0308599A (enExample) |
| CA (1) | CA2476762C (enExample) |
| MX (1) | MXPA04009117A (enExample) |
| RU (1) | RU2315791C2 (enExample) |
| TW (1) | TWI294901B (enExample) |
| WO (1) | WO2003080735A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5842446B2 (ja) * | 2010-08-06 | 2016-01-13 | 三菱化学株式会社 | アントラキノン系色素を含むインク及び該インクに用いられる色素 |
| BR112017005753B1 (pt) * | 2014-09-30 | 2022-01-25 | Compagnie Generale Des Etablissements Michelin | Composto poliol aromático sulfurado |
| TWI709617B (zh) * | 2019-08-06 | 2020-11-11 | 崑山科技大學 | 蒽醌類塗料、包含其之加工織物及其製備方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1402704A (en) * | 1972-12-07 | 1975-08-13 | Bayer Ag | Mass dyeing of polyesters |
| GB1445949A (en) * | 1973-12-06 | 1976-08-11 | Bayer Ag | Bulk dyeing of polyesters |
| RU2004558C1 (ru) * | 1990-12-25 | 1993-12-15 | Институт химии нефти СО РАН | 1-Алкокси-4-(N-толиламино)антрахиноны в качестве красителей дл полиолефинов |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2359373A (en) * | 1942-02-21 | 1944-10-03 | Du Pont | Anthraquinone compounds |
| CH432692A (de) * | 1964-01-20 | 1967-03-31 | Sandoz Ag | Verfahren zur Herstellung von Farbstoffen der Anthrachinonreihe |
| DE3007198A1 (de) * | 1980-02-26 | 1981-09-03 | Siemens AG, 1000 Berlin und 8000 München | Pleochroitischer anthrachinon-farbstoff, verfahren zu seiner herstellung und verwendung des farbstoffs |
| JPS573851A (en) * | 1980-05-08 | 1982-01-09 | Eastman Kodak Co | Copolymerizable dye as coloring agent for polyester polymer |
| DE3046904A1 (de) | 1980-12-12 | 1982-07-15 | Bayer Ag, 5090 Leverkusen | Anthrachinonfarbstoffe, verfahren zu ihrer herstellung ihre verwendung sowie fluessigkristalline materialien enthaltend anthrachinonfarbstoffe |
| JPH07100792B2 (ja) * | 1986-05-13 | 1995-11-01 | 三菱化学株式会社 | 液晶組成物 |
| JPH0657798B2 (ja) * | 1986-12-03 | 1994-08-03 | 三井東圧化学株式会社 | フイルタ−用青色色素 |
| JPS63268768A (ja) * | 1987-04-27 | 1988-11-07 | Mitsui Toatsu Chem Inc | フイルタ−用緑色色素 |
| US4846846A (en) * | 1988-06-20 | 1989-07-11 | Milliken Research Corporation | Process for preparing polyurethane resins colored with anthraquinone colorants and products produced thereby |
| JP3934729B2 (ja) * | 1996-03-29 | 2007-06-20 | 株式会社東芝 | 液晶表示素子 |
| JP2000129150A (ja) * | 1998-10-22 | 2000-05-09 | Asahi Denka Kogyo Kk | 重合可能な色素単量体および該単量体から得られる重合体 |
| EP1127922A1 (de) | 1999-12-29 | 2001-08-29 | Ciba SC Holding AG | Pigmentfarbstoffe zum Färben von synthetischen Materialien in der Masse |
| JP2001187844A (ja) * | 1999-12-29 | 2001-07-10 | Ciba Specialty Chem Holding Inc | 合成材料の練り込み着色のための新規顔料着色剤 |
| KR20030064845A (ko) | 2000-12-22 | 2003-08-02 | 시바 스페셜티 케미칼스 홀딩 인크. | 안트라퀴논 염료, 이의 제조방법 및 이의 용도 |
| CA2430604A1 (en) | 2000-12-22 | 2002-07-04 | Rainer Hildebrand | Preparation of dyed plastics or polymeric dye particles |
| KR100800984B1 (ko) | 2000-12-22 | 2008-02-05 | 시바 스페셜티 케미칼스 홀딩 인크. | 제조된 천연 중합체와 소수성 합성 섬유재료의 염색 또는 날염 방법 |
-
2003
- 2003-03-13 EP EP03744798A patent/EP1487921A1/en not_active Withdrawn
- 2003-03-13 BR BR0308599-6A patent/BR0308599A/pt not_active IP Right Cessation
- 2003-03-13 KR KR10-2004-7014873A patent/KR20050006132A/ko not_active Abandoned
- 2003-03-13 MX MXPA04009117A patent/MXPA04009117A/es active IP Right Grant
- 2003-03-13 JP JP2003578473A patent/JP4500053B2/ja not_active Expired - Fee Related
- 2003-03-13 US US10/508,715 patent/US7160335B2/en not_active Expired - Fee Related
- 2003-03-13 AU AU2003227058A patent/AU2003227058A1/en not_active Abandoned
- 2003-03-13 CN CNA038066262A patent/CN1643075A/zh active Pending
- 2003-03-13 CA CA2476762A patent/CA2476762C/en not_active Expired - Fee Related
- 2003-03-13 RU RU2004131533/04A patent/RU2315791C2/ru not_active IP Right Cessation
- 2003-03-13 WO PCT/EP2003/002615 patent/WO2003080735A1/en not_active Ceased
- 2003-03-20 TW TW092106153A patent/TWI294901B/zh not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1402704A (en) * | 1972-12-07 | 1975-08-13 | Bayer Ag | Mass dyeing of polyesters |
| GB1445949A (en) * | 1973-12-06 | 1976-08-11 | Bayer Ag | Bulk dyeing of polyesters |
| RU2004558C1 (ru) * | 1990-12-25 | 1993-12-15 | Институт химии нефти СО РАН | 1-Алкокси-4-(N-толиламино)антрахиноны в качестве красителей дл полиолефинов |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200307017A (en) | 2003-12-01 |
| MXPA04009117A (es) | 2004-12-07 |
| BR0308599A (pt) | 2005-02-09 |
| US7160335B2 (en) | 2007-01-09 |
| CA2476762A1 (en) | 2003-10-02 |
| TWI294901B (en) | 2008-03-21 |
| WO2003080735A1 (en) | 2003-10-02 |
| EP1487921A1 (en) | 2004-12-22 |
| CN1643075A (zh) | 2005-07-20 |
| KR20050006132A (ko) | 2005-01-15 |
| JP2005520907A (ja) | 2005-07-14 |
| JP4500053B2 (ja) | 2010-07-14 |
| AU2003227058A1 (en) | 2003-10-08 |
| US20050177958A1 (en) | 2005-08-18 |
| RU2004131533A (ru) | 2005-06-27 |
| CA2476762C (en) | 2010-05-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2315791C2 (ru) | Антрахиноновые красители | |
| RU2340642C2 (ru) | Антрахиноновые красители | |
| CN112771125B (zh) | 化合物、着色组合物、油墨、调色剂、着色树脂组合物及纤维染色用组合物 | |
| EP1509573B1 (en) | Anthraquinone-azo dyes | |
| KR101017849B1 (ko) | 아조 염료 | |
| CA2518707A1 (en) | Compounds, a process for their preparation and their use as dyes and pigments | |
| TW575639B (en) | Preparation of styryl dyes | |
| US20060124014A1 (en) | New heterocyclic compounds, a process for their preparation and their use as dyes and pigments | |
| CA2519157A1 (en) | New heterocyclic compounds, a process for their preparation and their use as dyes and pigments | |
| KR20050119126A (ko) | 신규한 화합물, 이의 제조방법, 및 염료 및 안료로서의이의 용도 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20110314 |