DE69916055T2 - Verwendung von lithiumsalzen anionischer farbstoffe zur verbesserung ihrer lichtechtheit - Google Patents
Verwendung von lithiumsalzen anionischer farbstoffe zur verbesserung ihrer lichtechtheit Download PDFInfo
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- DE69916055T2 DE69916055T2 DE69916055T DE69916055T DE69916055T2 DE 69916055 T2 DE69916055 T2 DE 69916055T2 DE 69916055 T DE69916055 T DE 69916055T DE 69916055 T DE69916055 T DE 69916055T DE 69916055 T2 DE69916055 T2 DE 69916055T2
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- dye
- lithium
- formula
- cations
- ink
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- 159000000002 lithium salts Chemical class 0.000 title claims description 53
- 229910003002 lithium salt Inorganic materials 0.000 title claims description 50
- 125000000129 anionic group Chemical group 0.000 claims description 40
- -1 lithium cations Chemical class 0.000 claims description 30
- 229910052744 lithium Inorganic materials 0.000 claims description 28
- 239000011734 sodium Substances 0.000 claims description 27
- 229910052708 sodium Inorganic materials 0.000 claims description 27
- 150000001768 cations Chemical class 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 24
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 19
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
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- 239000004753 textile Substances 0.000 claims description 6
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 5
- SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 claims description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- UZZFFIUHUDOYPS-UHFFFAOYSA-L disodium 4-amino-3,6-bis[[4-[(2,4-diaminophenyl)diazenyl]phenyl]diazenyl]-5-oxido-7-sulfonaphthalene-2-sulfonate Chemical compound [Na+].[Na+].Nc1ccc(N=Nc2ccc(cc2)N=Nc2c(N)c3c(O)c(N=Nc4ccc(cc4)N=Nc4ccc(N)cc4N)c(cc3cc2S([O-])(=O)=O)S([O-])(=O)=O)c(N)c1 UZZFFIUHUDOYPS-UHFFFAOYSA-L 0.000 claims description 2
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- VVNXEADCOVSAER-UHFFFAOYSA-N lithium sodium Chemical compound [Li].[Na] VVNXEADCOVSAER-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000001018 xanthene dye Substances 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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0072—Preparations with anionic dyes or reactive dyes
-
- 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
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
- C09B69/045—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds of anionic azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9812119.7A GB9812119D0 (en) | 1998-06-05 | 1998-06-05 | Composition |
| GB9812119 | 1998-06-05 | ||
| PCT/GB1999/001483 WO1999064526A1 (en) | 1998-06-05 | 1999-05-28 | Use of lithium salts of anionic dyes to enhance their light-fastness |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69916055D1 DE69916055D1 (de) | 2004-05-06 |
| DE69916055T2 true DE69916055T2 (de) | 2005-03-03 |
Family
ID=10833271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69916055T Expired - Fee Related DE69916055T2 (de) | 1998-06-05 | 1999-05-28 | Verwendung von lithiumsalzen anionischer farbstoffe zur verbesserung ihrer lichtechtheit |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6395885B1 (enExample) |
| EP (1) | EP1084201B1 (enExample) |
| JP (1) | JP2002517592A (enExample) |
| AU (1) | AU4050099A (enExample) |
| DE (1) | DE69916055T2 (enExample) |
| GB (1) | GB9812119D0 (enExample) |
| WO (1) | WO1999064526A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6746526B1 (en) * | 1999-10-29 | 2004-06-08 | Avecia Limited | Disazodyestuffs for ink jet printing |
| DE50001223D1 (de) * | 2000-12-21 | 2003-03-13 | Ilford Imaging Ch Gmbh | Monoazofarbstoffe, deren Herstellung und Verwendung |
| JP2004067925A (ja) * | 2002-08-08 | 2004-03-04 | Konica Minolta Holdings Inc | インクジェットインク、インクジェットインクセット及びインクジェット記録方法 |
| JP2004075767A (ja) * | 2002-08-13 | 2004-03-11 | Konica Minolta Holdings Inc | インクジェットインク、インクジェットインクセット及びインクジェット記録方法 |
| JP2004075768A (ja) * | 2002-08-13 | 2004-03-11 | Konica Minolta Holdings Inc | インクジェットインク、インクジェットインクセット及びインクジェット記録方法 |
| US20040068102A1 (en) * | 2002-10-07 | 2004-04-08 | Holloway Ann P. | Yellow dyes and ink compositions |
| DE10325808A1 (de) * | 2003-06-06 | 2004-12-23 | Basf Ag | Anionische Azofarbstoffe und ihre Metallkomplexe für die Lederfärbung |
| EP1753824B1 (en) * | 2004-05-19 | 2010-09-29 | Clariant Finance (BVI) Limited | Stable liquid formulations of anionic dyes |
| TW200722487A (en) * | 2005-12-15 | 2007-06-16 | Benq Corp | Yellow dyes and ink compositions comprising the same |
| KR100823285B1 (ko) | 2006-10-20 | 2008-04-17 | 삼성전자주식회사 | 아조계 착색제를 포함하는 잉크 조성물 및 이를 포함하는잉크 세트 |
| CN102675915B (zh) * | 2012-04-05 | 2014-03-26 | 上海贝通化工科技有限公司 | 一种含苯甲酰基h酸的水溶性染料组合物及其制备方法 |
| FR2990852A1 (fr) * | 2012-05-24 | 2013-11-29 | Oreal | Colorant ou azurant anionique a contre ion ammonium ou phosphonium, composition de teinture les comprenant et procede de coloration des fibres keratiniques a partir de ces colorants |
| JP6262142B2 (ja) * | 2012-10-26 | 2018-01-17 | 日本化薬株式会社 | インクジェット捺染用インクセット及びそれを用いた繊維の捺染方法 |
| WO2014065335A1 (ja) * | 2012-10-26 | 2014-05-01 | 日本化薬株式会社 | インクジェット捺染用インク及びそれを用いた繊維の捺染方法 |
| JP2014189663A (ja) * | 2013-03-27 | 2014-10-06 | Mitsubishi Chemicals Corp | 着色樹脂組成物、カラーフィルタ、液晶表示装置及び有機ｅｌ表示装置 |
| JP6801305B2 (ja) * | 2016-03-24 | 2020-12-16 | セイコーエプソン株式会社 | インクジェット捺染用インク組成物、インクセット及び記録方法 |
| CN115449233A (zh) * | 2022-10-12 | 2022-12-09 | 浙江亿得新材料股份有限公司 | 一种用于喷墨打印的红色染料及其组合物和制备方法 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3600376A (en) | 1968-10-03 | 1971-08-17 | Du Pont | Method of preparing j-acid urea disazo dyestuffs |
| US3635944A (en) | 1969-05-12 | 1972-01-18 | Allied Chem | Highly water soluble disazo dyestuffs |
| GB1318111A (en) | 1970-01-09 | 1973-05-23 | Ici Ltd | Reactive dyestuff compositions |
| US4260391A (en) * | 1979-01-18 | 1981-04-07 | Ciba-Geigy Corporation | Stable concentrated solution of a dye of the disazo class |
| EP0014180B1 (de) | 1979-01-18 | 1983-07-27 | Ciba-Geigy Ag | Stabile konzentrierte Lösung eines Farbstoffes der Disazoreihe, Verfahren zu deren Herstellung und Verwendung dieser Lösung |
| DE3109351A1 (de) | 1981-03-12 | 1982-09-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur spinnfaerbung von linearen synthetischen polyamiden, sowie verfahren zur herstellung von lithiumsalzen von metallkomplexfarbstoffen |
| JPS6033145B2 (ja) | 1982-10-27 | 1985-08-01 | 三菱化学株式会社 | 記録液 |
| DE3322502A1 (de) | 1983-06-23 | 1985-01-10 | Basf Ag, 6700 Ludwigshafen | Fluessige farbstoffzubereitungen |
| US4626284A (en) | 1983-10-08 | 1986-12-02 | Mitsubishi Chemical Industries Ltd. | Recording liquid |
| GB8421551D0 (en) | 1984-08-24 | 1984-09-26 | Ici Plc | Water-soluble dye |
| DE3443305A1 (de) * | 1984-11-28 | 1986-05-28 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von lithiumsalzen von anionischen farbstoffen mit vorzugsweise faserreaktiven gruppen |
| JPH0686576B2 (ja) * | 1986-04-18 | 1994-11-02 | 住友化学工業株式会社 | 反応染料液状組成物 |
| DE3775464D1 (de) | 1986-05-13 | 1992-02-06 | Ici Plc | Wasserloeslicher farbstoff. |
| JPS63241071A (ja) * | 1987-03-27 | 1988-10-06 | Mitsubishi Kasei Corp | スルホン酸リチウム基を有する水溶性染料の製造方法 |
| DE3710176A1 (de) | 1987-03-27 | 1988-10-13 | Hoechst Ag | Verfahren zur herstellung des lithiumsalzes eines faserreaktiven azofarbstoffes |
| DE3735078A1 (de) * | 1987-10-16 | 1989-04-27 | Cassella Ag | Wasserloesliche gelbe monoazofarbstoffe |
| JP2502637B2 (ja) * | 1987-11-30 | 1996-05-29 | 株式会社リコー | 水性インク組成物 |
| US5075428A (en) | 1988-07-30 | 1991-12-24 | Bayer Aktiengesellschaft | 2,4-diamino-6-fluorotriazine disazo reactive dyestuffs |
| GB8917764D0 (en) * | 1988-08-24 | 1989-09-20 | Ici Plc | Anionic dye |
| US4963189A (en) | 1989-08-24 | 1990-10-16 | Hewlett-Packard Company | Waterfast ink formulations with a novel series of anionic dyes containing two or more carboxyl groups |
| US5062892A (en) * | 1989-10-27 | 1991-11-05 | Hewlett-Packard Company | Ink additives for improved ink-jet performance |
| GB9016448D0 (en) * | 1990-07-26 | 1990-09-12 | Ici Plc | Anionic compounds |
| GB9325454D0 (en) * | 1993-01-12 | 1994-02-16 | Zeneca Ltd | Azo compound |
| GB9502341D0 (en) * | 1995-02-07 | 1995-03-29 | Ilford Ag | Magenta dyes |
| US5948154A (en) * | 1995-11-02 | 1999-09-07 | Seiko Epson Corporation | Color ink set for ink-jet recording |
| JP4367867B2 (ja) * | 1995-11-02 | 2009-11-18 | セイコーエプソン株式会社 | 黒色再現性に優れたインク組成物およびそれを用いたインクジェット記録方法 |
-
1998
- 1998-06-05 GB GBGB9812119.7A patent/GB9812119D0/en not_active Ceased
-
1999
- 1999-05-28 DE DE69916055T patent/DE69916055T2/de not_active Expired - Fee Related
- 1999-05-28 AU AU40500/99A patent/AU4050099A/en not_active Abandoned
- 1999-05-28 WO PCT/GB1999/001483 patent/WO1999064526A1/en not_active Ceased
- 1999-05-28 JP JP2000553520A patent/JP2002517592A/ja active Pending
- 1999-05-28 US US09/701,901 patent/US6395885B1/en not_active Expired - Fee Related
- 1999-05-28 EP EP99923735A patent/EP1084201B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999064526A1 (en) | 1999-12-16 |
| US6395885B1 (en) | 2002-05-28 |
| EP1084201A1 (en) | 2001-03-21 |
| DE69916055D1 (de) | 2004-05-06 |
| AU4050099A (en) | 1999-12-30 |
| EP1084201B1 (en) | 2004-03-31 |
| GB9812119D0 (en) | 1998-08-05 |
| JP2002517592A (ja) | 2002-06-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: AVECIA INKJET LTD., BLACKLEY, MANCHESTER, GB |
|
| 8328 | Change in the person/name/address of the agent |
Representative=s name: VOSSIUS & PARTNER, 81675 MUENCHEN |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: FUJIFILM IMAGING COLORANTS LTD., BLACKLEY, MANCHES |
|
| 8339 | Ceased/non-payment of the annual fee |