CA2476886C - Anthraquinone dyes - Google Patents
Anthraquinone dyes Download PDFInfo
- Publication number
- CA2476886C CA2476886C CA2476886A CA2476886A CA2476886C CA 2476886 C CA2476886 C CA 2476886C CA 2476886 A CA2476886 A CA 2476886A CA 2476886 A CA2476886 A CA 2476886A CA 2476886 C CA2476886 C CA 2476886C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- radical
- hydrogen
- radicals
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000001000 anthraquinone dye Substances 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229920003023 plastic Polymers 0.000 claims abstract description 11
- 239000004033 plastic Substances 0.000 claims abstract description 11
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 10
- 239000002245 particle Substances 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000000460 chlorine Chemical group 0.000 claims description 6
- 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
- 239000003086 colorant Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000006068 polycondensation reaction Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910004727 OSO3H Inorganic materials 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical group 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 19
- 150000003254 radicals Chemical class 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- -1 1,4,5,8-tetrasubstituted anthraquinones Chemical class 0.000 description 6
- 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
- 239000000758 substrate Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- DMPCQDXYSIJPPL-UHFFFAOYSA-N 1-amino-2-chloro-4-[4-(2-hydroxyethyl)anilino]anthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(Cl)C=C1NC1=CC=C(CCO)C=C1 DMPCQDXYSIJPPL-UHFFFAOYSA-N 0.000 description 2
- QXHDYMUPPXAMPQ-UHFFFAOYSA-N 2-(4-aminophenyl)ethanol Chemical compound NC1=CC=C(CCO)C=C1 QXHDYMUPPXAMPQ-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-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
- 238000001816 cooling Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010348 incorporation Methods 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
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 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
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- PLUFITIFLBGFPN-UHFFFAOYSA-N 1,2-dichloroanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3C(=O)C2=C1 PLUFITIFLBGFPN-UHFFFAOYSA-N 0.000 description 1
- MEHLXACDLXEVBE-UHFFFAOYSA-N 1,4-dichloro-5,8-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C(O)=CC=C2O MEHLXACDLXEVBE-UHFFFAOYSA-N 0.000 description 1
- QGEVKHANUWPORJ-UHFFFAOYSA-N 1,4-dihydroxy-5,8-bis[4-(2-hydroxyethyl)anilino]anthracene-9,10-dione Chemical compound C1=CC(CCO)=CC=C1NC(C=1C(=O)C2=C(O)C=CC(O)=C2C(=O)C=11)=CC=C1NC1=CC=C(CCO)C=C1 QGEVKHANUWPORJ-UHFFFAOYSA-N 0.000 description 1
- HVNFHSIIPHSECS-UHFFFAOYSA-N 1-amino-2,4-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC(Cl)=C2N HVNFHSIIPHSECS-UHFFFAOYSA-N 0.000 description 1
- UZQBNNOMGOHXFL-UHFFFAOYSA-N 1-amino-4-[4-(2-hydroxyethyl)anilino]-2-(2-hydroxyethylsulfanyl)anthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(SCCO)C=C1NC1=CC=C(CCO)C=C1 UZQBNNOMGOHXFL-UHFFFAOYSA-N 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 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
- 239000002253 acid 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
- BKNBVEKCHVXGPH-UHFFFAOYSA-N anthracene-1,4,9,10-tetrol Chemical compound C1=CC=C2C(O)=C3C(O)=CC=C(O)C3=C(O)C2=C1 BKNBVEKCHVXGPH-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 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
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 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
- IPHJYJHJDIGARM-UHFFFAOYSA-M copper phthalocyaninesulfonic acid, dioctadecyldimethylammonium salt Chemical compound [Cu+2].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC.C=1C(S(=O)(=O)[O-])=CC=C(C(=NC2=NC(C3=CC=CC=C32)=N2)[N-]3)C=1C3=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 IPHJYJHJDIGARM-UHFFFAOYSA-M 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
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 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
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 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
- 235000011056 potassium acetate Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 239000001062 red colorant Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate 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
- 238000003756 stirring Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
- C09B1/5145—N-aryl derivatives only amino and hydroxy groups
-
- 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
-
- 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
- C09B1/60—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals substituted by aliphatic, cycloaliphatic or araliphatic 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)
- Processes Of Treating Macromolecular Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrane Compounds (AREA)
- Optical Filters (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02405226 | 2002-03-22 | ||
| EP02405226.8 | 2002-03-22 | ||
| PCT/EP2003/002616 WO2003080734A1 (en) | 2002-03-22 | 2003-03-13 | Anthraquinone dyes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2476886A1 CA2476886A1 (en) | 2003-10-02 |
| CA2476886C true CA2476886C (en) | 2011-02-15 |
Family
ID=28051880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2476886A Expired - Fee Related CA2476886C (en) | 2002-03-22 | 2003-03-13 | Anthraquinone dyes |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7456316B2 (OSRAM) |
| EP (1) | EP1487920B1 (OSRAM) |
| JP (1) | JP4503296B2 (OSRAM) |
| KR (1) | KR20050006133A (OSRAM) |
| CN (1) | CN100408640C (OSRAM) |
| AT (1) | ATE545681T1 (OSRAM) |
| AU (1) | AU2003227059A1 (OSRAM) |
| BR (1) | BR0308618B1 (OSRAM) |
| CA (1) | CA2476886C (OSRAM) |
| MX (1) | MXPA04009115A (OSRAM) |
| RU (1) | RU2340642C2 (OSRAM) |
| TW (1) | TWI293322B (OSRAM) |
| WO (1) | WO2003080734A1 (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007093536A2 (en) * | 2006-02-17 | 2007-08-23 | Ciba Holding Inc. | Blue colour filters with enhanced contrast |
| JP6054239B2 (ja) * | 2013-05-07 | 2016-12-27 | 山本化成株式会社 | イソインドリン系化合物およびその製造方法。 |
| US20170038686A1 (en) * | 2014-04-18 | 2017-02-09 | Rohm And Haas Electronic Materials Llc | Anthraquinone compound used for color filter of lcd |
| JP2017522407A (ja) * | 2014-06-17 | 2017-08-10 | ダウ グローバル テクノロジーズ エルエルシー | Ｌｃｄのカラーフィルタに使用されるアントラキノン化合物 |
| EP3489217A1 (de) * | 2017-11-24 | 2019-05-29 | LANXESS Deutschland GmbH | Verfahren zur herstellung von phenylaminohydroxyanthrachinonen |
| CN111087831A (zh) * | 2019-12-20 | 2020-05-01 | 南京金浩医药科技有限公司 | 一种新型蒽醌类溶剂蓝染料的制备方法 |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE705034C (de) | 1938-07-31 | 1941-04-13 | Messerschmitt Boelkow Blohm | Rueckstossantrieb mittels der Abgase einer Brennkraftmaschine |
| GB560817A (en) * | 1942-07-15 | 1944-04-21 | Du Pont | Anthraquinone dyestuffs |
| US2434765A (en) * | 1944-01-13 | 1948-01-20 | Chem Ind Basel | 1-amino-2-hydroxyalkylthio-4-arylamino-anthraquinones |
| US2487045A (en) | 1947-02-27 | 1949-11-08 | Eastman Kodak Co | 1,4-diamino-2-halogenoanthraquinone compounds |
| CH325464A (de) | 1953-12-04 | 1957-11-15 | Ciba Geigy | Verfahren zur Herstellung neuer Dioxy-di-(arylamino)-anthrachinone |
| FR1450641A (fr) * | 1964-07-04 | 1966-06-24 | Bayer Ag | Colorants de la série de l'anthraquinone et de la phtalocyanine, et leurs procédés de fabrication |
| CH472464A (de) * | 1964-08-08 | 1969-05-15 | Bayer Ag | Verfahren zur Herstellung von Verbindungen der Anthrachinonreihe |
| US3434792A (en) * | 1965-05-04 | 1969-03-25 | American Cyanamid Co | 1-amino- (and methylamino) 2-bromo-4-(p-(beta - hydroxyethyl) - anilino) - anthraquinone disperse dyes for nylon and polypropylene |
| GB1114936A (en) * | 1965-07-19 | 1968-05-22 | Ici Ltd | Process for mass coloring polyesters |
| FR1516828A (fr) | 1965-11-29 | 1968-02-05 | Ici Ltd | Nouveaux colorants de la série de l'anthraquinone et leur procédé de fabrication |
| GB1166998A (en) | 1965-11-29 | 1969-10-15 | Ici Ltd | Anthraquinone Dyestuffs |
| GB1078092A (en) | 1966-03-08 | 1967-08-02 | Ici Ltd | Anthraquinone dyestuffs |
| BR6787718D0 (pt) | 1966-06-29 | 1973-06-07 | Eastman Kodak Co | Elemento fotografico sensivel a luz |
| GB1152244A (en) * | 1966-07-11 | 1969-05-14 | Ici Ltd | Anthraquinone Dyestuffs |
| FR1530985A (fr) | 1966-07-11 | 1968-06-28 | Ici Ltd | Procédé de fabrication de composés anthraquinoniques |
| US3734934A (en) * | 1970-04-01 | 1973-05-22 | Ciba Geigy Ag | Dispersible {60 -{11 and {62 -substituted anthraquinone dyestuffs containing an -alkyleneocoor group |
| GB1367933A (en) * | 1971-05-10 | 1974-09-25 | Ici Ltd | Mass colouration of polyesters |
| DE2123454A1 (en) | 1971-05-12 | 1972-11-23 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Dyeing of synthetic fibres - using 1,4-bis-(hydroxyanilino) anthraquinones as dispersions in org solvents |
| GB1592966A (en) | 1977-04-25 | 1981-07-15 | Ici Ltd | Colouration process |
| DE2843474A1 (de) | 1978-10-05 | 1980-04-17 | Bayer Ag | Verfahren zum faerben und bedrucken von cellulosefasern |
| JPS5790081A (en) * | 1980-11-27 | 1982-06-04 | Canon Inc | Liquid crystal display device |
| GB2101624B (en) | 1981-05-20 | 1984-09-19 | Mitsubishi Chem Ind | Anthraquinone dyes for cellulose-containing fibers and their synthesis |
| JPS5819363A (ja) * | 1981-07-27 | 1983-02-04 | Mitsubishi Chem Ind Ltd | アントラキノン化合物、その製造法及びセルロース含有繊維類用アントラキノン染料 |
| JPS62903A (ja) * | 1985-06-05 | 1987-01-06 | Sumitomo Chem Co Ltd | 近赤外線吸収フイルタ− |
| 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 |
| JPS63249693A (ja) | 1987-04-06 | 1988-10-17 | Sumitomo Chem Co Ltd | 昇華転写型感熱記録用シアン色素 |
| JPS63268768A (ja) * | 1987-04-27 | 1988-11-07 | Mitsui Toatsu Chem Inc | フイルタ−用緑色色素 |
| JPH0813930B2 (ja) | 1987-12-28 | 1996-02-14 | 三井東圧化学株式会社 | 近赤外線吸収フィルター用高純度アントラキノン系色素 |
| US4846846A (en) * | 1988-06-20 | 1989-07-11 | Milliken Research Corporation | Process for preparing polyurethane resins colored with anthraquinone colorants and products produced thereby |
| 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 RU RU2004131534/04A patent/RU2340642C2/ru not_active IP Right Cessation
- 2003-03-13 EP EP03744799A patent/EP1487920B1/en not_active Expired - Lifetime
- 2003-03-13 CN CNB038066092A patent/CN100408640C/zh not_active Expired - Fee Related
- 2003-03-13 BR BRPI0308618-6B1A patent/BR0308618B1/pt not_active IP Right Cessation
- 2003-03-13 AU AU2003227059A patent/AU2003227059A1/en not_active Abandoned
- 2003-03-13 KR KR10-2004-7014932A patent/KR20050006133A/ko not_active Abandoned
- 2003-03-13 JP JP2003578472A patent/JP4503296B2/ja not_active Expired - Fee Related
- 2003-03-13 AT AT03744799T patent/ATE545681T1/de active
- 2003-03-13 MX MXPA04009115A patent/MXPA04009115A/es active IP Right Grant
- 2003-03-13 WO PCT/EP2003/002616 patent/WO2003080734A1/en not_active Ceased
- 2003-03-13 CA CA2476886A patent/CA2476886C/en not_active Expired - Fee Related
- 2003-03-13 US US10/508,714 patent/US7456316B2/en not_active Expired - Fee Related
- 2003-04-03 TW TW092107595A patent/TWI293322B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE545681T1 (de) | 2012-03-15 |
| TWI293322B (en) | 2008-02-11 |
| BR0308618B1 (pt) | 2013-12-03 |
| CN1643074A (zh) | 2005-07-20 |
| TW200420673A (en) | 2004-10-16 |
| US7456316B2 (en) | 2008-11-25 |
| CN100408640C (zh) | 2008-08-06 |
| JP4503296B2 (ja) | 2010-07-14 |
| RU2340642C2 (ru) | 2008-12-10 |
| US20050150061A1 (en) | 2005-07-14 |
| BR0308618A (pt) | 2005-02-15 |
| WO2003080734A1 (en) | 2003-10-02 |
| KR20050006133A (ko) | 2005-01-15 |
| MXPA04009115A (es) | 2004-12-07 |
| AU2003227059A1 (en) | 2003-10-08 |
| JP2005520906A (ja) | 2005-07-14 |
| EP1487920A1 (en) | 2004-12-22 |
| RU2004131534A (ru) | 2005-07-10 |
| CA2476886A1 (en) | 2003-10-02 |
| EP1487920B1 (en) | 2012-02-15 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20170313 |