NO326677B1 - Azo-fargestoffer, deres fremstilling, deres anvendelse, og aminoforbindelser - Google Patents
Azo-fargestoffer, deres fremstilling, deres anvendelse, og aminoforbindelser Download PDFInfo
- Publication number
- NO326677B1 NO326677B1 NO20033513A NO20033513A NO326677B1 NO 326677 B1 NO326677 B1 NO 326677B1 NO 20033513 A NO20033513 A NO 20033513A NO 20033513 A NO20033513 A NO 20033513A NO 326677 B1 NO326677 B1 NO 326677B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- denotes
- formula
- independently
- unsubstituted
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000000987 azo dye Substances 0.000 title description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 60
- -1 cycloaliphatic Chemical group 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 238000007639 printing Methods 0.000 claims description 18
- 230000008878 coupling Effects 0.000 claims description 16
- 238000010168 coupling process Methods 0.000 claims description 16
- 238000005859 coupling reaction Methods 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 238000004043 dyeing Methods 0.000 claims description 11
- 150000001450 anions Chemical class 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 239000003086 colorant Substances 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 239000012954 diazonium Substances 0.000 claims description 5
- 239000002657 fibrous material Substances 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 150000001989 diazonium salts Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- PJOUURZOYJMYPA-UHFFFAOYSA-N OClC#N Chemical group OClC#N PJOUURZOYJMYPA-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 235000011054 acetic acid Nutrition 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
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- 238000006243 chemical reaction Methods 0.000 description 6
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- UXEAWNJALIUYRH-UHFFFAOYSA-N [8-[(4-aminophenyl)hydrazinylidene]-7-oxonaphthalen-2-yl]-trimethylazanium;chloride Chemical compound [Cl-].C12=CC([N+](C)(C)C)=CC=C2C=CC(=O)\C1=N/NC1=CC=C(N)C=C1 UXEAWNJALIUYRH-UHFFFAOYSA-N 0.000 description 5
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- 238000003786 synthesis reaction Methods 0.000 description 4
- MHOFGBJTSNWTDT-UHFFFAOYSA-M 2-[n-ethyl-4-[(6-methoxy-3-methyl-1,3-benzothiazol-3-ium-2-yl)diazenyl]anilino]ethanol;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC(N(CCO)CC)=CC=C1N=NC1=[N+](C)C2=CC=C(OC)C=C2S1 MHOFGBJTSNWTDT-UHFFFAOYSA-M 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 229940037003 alum Drugs 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
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- 230000015572 biosynthetic process Effects 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
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- 239000002250 absorbent Substances 0.000 description 2
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- 239000010893 paper waste Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LLWJPGAKXJBKKA-UHFFFAOYSA-N victoria blue B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=CC=C1 LLWJPGAKXJBKKA-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/50—Tetrazo dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/378—Trisazo dyes of the type
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Paper (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cosmetics (AREA)
- Steroid Compounds (AREA)
- Liquid Crystal Substances (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0103240.8A GB0103240D0 (en) | 2001-02-09 | 2001-02-09 | Organic compounds |
| PCT/IB2002/000398 WO2002062902A1 (en) | 2001-02-09 | 2002-02-11 | Azo dyestuffs |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20033513D0 NO20033513D0 (no) | 2003-08-07 |
| NO20033513L NO20033513L (no) | 2003-10-09 |
| NO326677B1 true NO326677B1 (no) | 2009-01-26 |
Family
ID=9908431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20033513A NO326677B1 (no) | 2001-02-09 | 2003-08-07 | Azo-fargestoffer, deres fremstilling, deres anvendelse, og aminoforbindelser |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7371831B2 (xx) |
| EP (1) | EP1360242B1 (xx) |
| JP (1) | JP4354697B2 (xx) |
| KR (1) | KR100837047B1 (xx) |
| CN (1) | CN100526392C (xx) |
| AT (1) | ATE344828T1 (xx) |
| BR (1) | BRPI0206939B1 (xx) |
| DE (1) | DE60215918T2 (xx) |
| ES (1) | ES2274007T3 (xx) |
| GB (1) | GB0103240D0 (xx) |
| HK (1) | HK1077596A1 (xx) |
| NO (1) | NO326677B1 (xx) |
| TW (1) | TWI303262B (xx) |
| WO (1) | WO2002062902A1 (xx) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0215015A (pt) * | 2001-12-19 | 2004-11-09 | Clariant Finance Bvi Ltd | Corantes mono azo ácidos |
| EP1716211B1 (en) * | 2003-12-04 | 2018-02-28 | Archroma IP GmbH | Concentrated aqueous compositions of dyestuffs |
| US20070251030A1 (en) * | 2004-05-26 | 2007-11-01 | Martin Oberholzer | Concentrated Dye Solution |
| US7381253B2 (en) * | 2004-12-03 | 2008-06-03 | Xerox Corporation | Multi-chromophoric azo pyridone colorants |
| EP1863885B1 (en) * | 2005-02-18 | 2014-12-24 | Clariant Finance (BVI) Limited | Concentrated dye solution |
| TWI588214B (zh) * | 2008-07-02 | 2017-06-21 | 克瑞特財力（Ｂｖｉ）有限公司 | 酸性染料之用途 |
| JP2012041461A (ja) * | 2010-08-20 | 2012-03-01 | Sumitomo Chemical Co Ltd | 化合物 |
| CN102408743B (zh) * | 2011-08-10 | 2013-04-17 | 吴江梅堰三友染料化工有限公司 | 一种直接混纺藏青d-r染料的生产工艺 |
| EP2868705A1 (en) * | 2013-10-29 | 2015-05-06 | DyStar Colours Distribution GmbH | Metal free acid dyes, process for their production and their use |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3211717A (en) * | 1961-03-20 | 1965-10-12 | Gen Aniline & Film Corp | Azo dyes from pentaerythritol esters |
| CH531610A (de) | 1969-01-20 | 1972-08-31 | Sandoz Ag | Verfahren zur Herstellung von für die Textilbehandlung gebrauchsfertigen, konzentrierten Farbstofflösungen von Monoazofarbstoffen |
| NL157802B (nl) | 1969-01-23 | 1978-09-15 | Hoffmann La Roche | Werkwijze voor de bereiding van een therapeutisch preparaat voor de behandeling van gastrointestinale ziekten. |
| US3817940A (en) * | 1970-08-17 | 1974-06-18 | Bayer Ag | Aromatic diamines |
| US3971741A (en) | 1971-07-29 | 1976-07-27 | Bayer Aktiengesellschaft | Water-insoluble polyazo dyestuff comprising two or three identical azo dyestuffs joined to a central nucleus by carboxyl bridges |
| BE786837A (fr) | 1971-07-29 | 1973-01-29 | Bayer Ag | Colorants polyazoiques |
| US3975428A (en) * | 1971-12-07 | 1976-08-17 | Bayer Aktiengesellschaft | Aromatic amines formed by the reaction of isatoic acid anhydride with compounds containing at least one tertiary nitrogen atom and at least two hydroxyl groups |
| CH629520A5 (de) | 1977-08-12 | 1982-04-30 | Sandoz Ag | Verfahren zur herstellung von azofarbstoffen. |
| DE2915323A1 (de) | 1978-04-26 | 1979-11-08 | Sandoz Ag | Basische bzw. kationische, sulfonsaeuregruppenhaltige monoazo- oder disazoverbindungen |
| US4180644A (en) * | 1978-07-31 | 1979-12-25 | Texaco Development Corp. | Polyurethane chain-extenders |
| DE2841243C2 (de) | 1978-09-22 | 1983-11-24 | Basf Farben + Fasern Ag, 2000 Hamburg | Kupplungskomponente, Verfahren zu deren Herstellung und deren Verwendung |
| CH668977A5 (de) | 1985-08-19 | 1989-02-15 | Sandoz Ag | Basische, sulfonsaeuregruppenhaltige monoazo- oder disazoverbindungen. |
| DE3625576A1 (de) | 1985-08-19 | 1987-02-19 | Sandoz Ag | Basische, sulfonsaeuregruppenhaltige monoazo- oder disazoverbindungen |
| CH672496A5 (xx) * | 1986-05-14 | 1989-11-30 | Sandoz Ag | |
| DE4007535A1 (de) | 1990-03-09 | 1991-09-12 | Hoechst Ag | Wasserunloesliche azofarbmittel, ihre herstellung und verwendung |
| CH690650A5 (de) | 1995-07-21 | 2000-11-30 | Clariant Finance Bvi Ltd | Basische Azoverbindungen mit zwei Pyridonringen, deren Herstellung und Verwendung. |
| EP0855387A4 (en) * | 1995-09-07 | 1999-09-15 | Kissei Pharmaceutical | 2-ACYLAMINOBENZAMIDE DERIVATIVES, PREVENTIVE AND REMEDY AGAINST DISEASES CAUSED BY OVERMULTIPLICATION OF INTIMA VASCULAR CELLS |
| DE19548785A1 (de) | 1995-12-27 | 1997-07-03 | Basf Ag | Saure Polyazofarbstoffe |
| US5929215A (en) | 1996-03-27 | 1999-07-27 | Clariant Finance (Bvi) Limited | Basic monoazo compounds |
| US6015885A (en) | 1996-07-11 | 2000-01-18 | Sumitomo Chemical Company, Limited | Polyazo compound and method for dyeing or textileprinting fiber material using the same |
| DE19820400A1 (de) * | 1998-05-07 | 1999-11-11 | Basf Ag | Kationische Azofarbstoffe auf der Bais von Aminobenzoesäure |
| DE19845640A1 (de) | 1998-10-05 | 2000-04-06 | Bayer Ag | Azofarbstoffe |
| DE19851026A1 (de) * | 1998-11-05 | 2000-05-11 | Basf Ag | Kationische Azofarbstoffe |
| US7381253B2 (en) * | 2004-12-03 | 2008-06-03 | Xerox Corporation | Multi-chromophoric azo pyridone colorants |
-
2001
- 2001-02-09 GB GBGB0103240.8A patent/GB0103240D0/en not_active Ceased
-
2002
- 2002-02-07 TW TW091102181A patent/TWI303262B/zh not_active IP Right Cessation
- 2002-02-11 ES ES02711136T patent/ES2274007T3/es not_active Expired - Lifetime
- 2002-02-11 WO PCT/IB2002/000398 patent/WO2002062902A1/en active IP Right Grant
- 2002-02-11 CN CNB028047621A patent/CN100526392C/zh not_active Expired - Lifetime
- 2002-02-11 US US10/467,136 patent/US7371831B2/en not_active Expired - Lifetime
- 2002-02-11 KR KR1020037010509A patent/KR100837047B1/ko active IP Right Grant
- 2002-02-11 BR BRPI0206939A patent/BRPI0206939B1/pt active IP Right Grant
- 2002-02-11 DE DE60215918T patent/DE60215918T2/de not_active Expired - Lifetime
- 2002-02-11 EP EP02711136A patent/EP1360242B1/en not_active Expired - Lifetime
- 2002-02-11 JP JP2002563246A patent/JP4354697B2/ja not_active Expired - Lifetime
- 2002-02-11 AT AT02711136T patent/ATE344828T1/de not_active IP Right Cessation
-
2003
- 2003-08-07 NO NO20033513A patent/NO326677B1/no not_active IP Right Cessation
-
2005
- 2005-10-21 HK HK05109413.5A patent/HK1077596A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP4354697B2 (ja) | 2009-10-28 |
| HK1077596A1 (en) | 2006-02-17 |
| EP1360242A1 (en) | 2003-11-12 |
| GB0103240D0 (en) | 2001-03-28 |
| ES2274007T3 (es) | 2007-05-16 |
| NO20033513D0 (no) | 2003-08-07 |
| KR100837047B1 (ko) | 2008-06-11 |
| KR20030072406A (ko) | 2003-09-13 |
| NO20033513L (no) | 2003-10-09 |
| US7371831B2 (en) | 2008-05-13 |
| CN100526392C (zh) | 2009-08-12 |
| EP1360242B1 (en) | 2006-11-08 |
| US20040083924A1 (en) | 2004-05-06 |
| DE60215918D1 (de) | 2006-12-21 |
| BRPI0206939B1 (pt) | 2016-02-10 |
| BR0206939A (pt) | 2004-02-03 |
| DE60215918T2 (de) | 2007-03-01 |
| CN1633473A (zh) | 2005-06-29 |
| WO2002062902A1 (en) | 2002-08-15 |
| TWI303262B (en) | 2008-11-21 |
| JP2004518794A (ja) | 2004-06-24 |
| ATE344828T1 (de) | 2006-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC2A | Withdrawal, rejection or dismissal of laid open patent application | ||
| MM1K | Lapsed by not paying the annual fees |