CA2476762C - Anthraquinone dyes - Google Patents
Anthraquinone dyes Download PDFInfo
- Publication number
- CA2476762C CA2476762C CA2476762A CA2476762A CA2476762C CA 2476762 C CA2476762 C CA 2476762C CA 2476762 A CA2476762 A CA 2476762A CA 2476762 A CA2476762 A CA 2476762A CA 2476762 C CA2476762 C CA 2476762C
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- compound
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- aryl
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- Prior art date
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- 239000001000 anthraquinone dye Substances 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 13
- 229920003023 plastic Polymers 0.000 claims abstract description 12
- 239000004033 plastic Substances 0.000 claims abstract description 12
- 239000002245 particle Substances 0.000 claims abstract description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 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 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 239000011368 organic material Substances 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 239000003086 colorant Substances 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 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
- 238000006068 polycondensation reaction Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 62
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 27
- -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
- 239000000975 dye Substances 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000004952 Polyamide Substances 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 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
- 238000004040 coloring Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002244 precipitate Substances 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 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
- 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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 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 2
- 150000004056 anthraquinones Chemical class 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
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 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
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000004973 liquid crystal related substance 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
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 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
- 239000000047 product Substances 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
- 239000000126 substance Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 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
- KNOYUKKOVLJJRM-UHFFFAOYSA-N 1,5-diamino-2,4,6,8-tetrabromoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C(Br)=CC(Br)=C2C(=O)C2=C1C(Br)=CC(Br)=C2N KNOYUKKOVLJJRM-UHFFFAOYSA-N 0.000 description 1
- VWBVCOPVKXNMMZ-UHFFFAOYSA-N 1,5-diaminoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC=C2C(=O)C2=C1C=CC=C2N VWBVCOPVKXNMMZ-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
- 241000052343 Dares Species 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
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 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
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 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
- 230000005540 biological transmission Effects 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
- 239000000919 ceramic Substances 0.000 description 1
- 239000000549 coloured material Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000003822 epoxy resin Substances 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
- 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
- 238000000227 grinding Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 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
- 150000002605 large molecules Chemical class 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
- 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
- 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
- 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
- 238000007493 shaping process Methods 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
- 238000003756 stirring Methods 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
- 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
- 229910052726 zirconium Inorganic materials 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Optical Filters (AREA)
- Coloring (AREA)
- Materials For Photolithography (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02405225.0 | 2002-03-22 | ||
| EP02405225 | 2002-03-22 | ||
| PCT/EP2003/002615 WO2003080735A1 (en) | 2002-03-22 | 2003-03-13 | Anthraquinone dyes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2476762A1 CA2476762A1 (en) | 2003-10-02 |
| CA2476762C true CA2476762C (en) | 2010-05-11 |
Family
ID=28051879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2476762A Expired - Fee Related CA2476762C (en) | 2002-03-22 | 2003-03-13 | Anthraquinone dyes |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7160335B2 (OSRAM) |
| EP (1) | EP1487921A1 (OSRAM) |
| JP (1) | JP4500053B2 (OSRAM) |
| KR (1) | KR20050006132A (OSRAM) |
| CN (1) | CN1643075A (OSRAM) |
| AU (1) | AU2003227058A1 (OSRAM) |
| BR (1) | BR0308599A (OSRAM) |
| CA (1) | CA2476762C (OSRAM) |
| MX (1) | MXPA04009117A (OSRAM) |
| RU (1) | RU2315791C2 (OSRAM) |
| TW (1) | TWI294901B (OSRAM) |
| WO (1) | WO2003080735A1 (OSRAM) |
Families Citing this family (4)
| 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 |
| CN118176265B (zh) * | 2021-11-04 | 2026-04-28 | 日本化药株式会社 | 蒽醌化合物、含该化合物的液晶组合物及调光元件 |
Family Cites Families (19)
| 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 |
| DE2259970A1 (de) * | 1972-12-07 | 1974-06-12 | Bayer Ag | Massefaerben von polyestern |
| DE2360875A1 (de) * | 1973-12-06 | 1975-06-12 | Bayer Ag | Massefaerben von polyestern |
| 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 |
| RU2004558C1 (ru) * | 1990-12-25 | 1993-12-15 | Институт химии нефти СО РАН | 1-Алкокси-4-(N-толиламино)антрахиноны в качестве красителей дл полиолефинов |
| 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 |
| 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 |
| EP1127922A1 (de) * | 1999-12-29 | 2001-08-29 | Ciba SC Holding AG | Pigmentfarbstoffe zum Färben von synthetischen Materialien in der Masse |
| KR20040010577A (ko) | 2000-12-22 | 2004-01-31 | 시바 스페셜티 케미칼스 홀딩 인크. | 착색 플라스틱 또는 중합체성 염료 입자의 제조방법 |
| CA2430606C (en) | 2000-12-22 | 2011-01-11 | Ciba Specialty Chemicals Holding Inc. | Dyeing or printing of manufactured natural polymer and synthetic hydrophobic fibre materials |
| WO2002051941A1 (en) | 2000-12-22 | 2002-07-04 | Ciba Specialty Chemicals Holding Inc. | Anthraquinone dyes, preparation thereof and use thereof |
-
2003
- 2003-03-13 JP JP2003578473A patent/JP4500053B2/ja not_active Expired - Fee Related
- 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 RU RU2004131533/04A patent/RU2315791C2/ru not_active IP Right Cessation
- 2003-03-13 CA CA2476762A patent/CA2476762C/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 EP EP03744798A patent/EP1487921A1/en not_active Withdrawn
- 2003-03-13 US US10/508,715 patent/US7160335B2/en not_active Expired - Fee Related
- 2003-03-13 MX MXPA04009117A patent/MXPA04009117A/es active IP Right Grant
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| CN1643075A (zh) | 2005-07-20 |
| US7160335B2 (en) | 2007-01-09 |
| RU2004131533A (ru) | 2005-06-27 |
| RU2315791C2 (ru) | 2008-01-27 |
| BR0308599A (pt) | 2005-02-09 |
| MXPA04009117A (es) | 2004-12-07 |
| TWI294901B (en) | 2008-03-21 |
| WO2003080735A1 (en) | 2003-10-02 |
| TW200307017A (en) | 2003-12-01 |
| US20050177958A1 (en) | 2005-08-18 |
| CA2476762A1 (en) | 2003-10-02 |
| AU2003227058A1 (en) | 2003-10-08 |
| JP2005520907A (ja) | 2005-07-14 |
| KR20050006132A (ko) | 2005-01-15 |
| EP1487921A1 (en) | 2004-12-22 |
| JP4500053B2 (ja) | 2010-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |