SK283764B6 - Azopyrazolónové zlúčeniny, spôsob ich prípravy a ich použitie ako pigmenty - Google Patents
Azopyrazolónové zlúčeniny, spôsob ich prípravy a ich použitie ako pigmenty Download PDFInfo
- Publication number
- SK283764B6 SK283764B6 SK988-97A SK98897A SK283764B6 SK 283764 B6 SK283764 B6 SK 283764B6 SK 98897 A SK98897 A SK 98897A SK 283764 B6 SK283764 B6 SK 283764B6
- Authority
- SK
- Slovakia
- Prior art keywords
- compound
- formula
- salt
- azopyrazolone
- solution
- Prior art date
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 8
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 5
- -1 azo pyrazolone compound Chemical class 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 150000001448 anilines Chemical class 0.000 claims description 4
- 229910001385 heavy metal Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 230000000485 pigmenting effect Effects 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- DUOCAITVQWIVJB-UHFFFAOYSA-N 2-amino-4-benzamidobenzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC(NC(=O)C=2C=CC=CC=2)=C1 DUOCAITVQWIVJB-UHFFFAOYSA-N 0.000 claims description 2
- YMJXNYUOEJPKHH-UHFFFAOYSA-N 2-amino-4-nitrobenzenesulfonic acid Chemical compound NC1=CC([N+]([O-])=O)=CC=C1S(O)(=O)=O YMJXNYUOEJPKHH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 239000011248 coating agent Substances 0.000 claims 2
- 159000000007 calcium salts Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 239000000243 solution Substances 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 239000008367 deionised water Substances 0.000 description 20
- 229910021641 deionized water Inorganic materials 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 8
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- FHXUYFKYRBLZJU-UHFFFAOYSA-N 3-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical group N1C(C)=CC(=O)N1C1=CC=CC(S(O)(=O)=O)=C1 FHXUYFKYRBLZJU-UHFFFAOYSA-N 0.000 description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 5
- 239000001110 calcium chloride Substances 0.000 description 5
- 229910001628 calcium chloride Inorganic materials 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 4
- 239000012670 alkaline solution Substances 0.000 description 4
- 239000001052 yellow pigment Substances 0.000 description 3
- OMQCGHBXGJBBOL-UHFFFAOYSA-N 2-amino-4-chlorobenzenesulfonic acid Chemical compound NC1=CC(Cl)=CC=C1S(O)(=O)=O OMQCGHBXGJBBOL-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- VFMNIJOKAXPZLE-UHFFFAOYSA-N 4-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC=C(S(O)(=O)=O)C=C1 VFMNIJOKAXPZLE-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KZQYIMCESJLPQH-UHFFFAOYSA-N Demethylated antipyrine Chemical class N1C(C)=CC(=O)N1C1=CC=CC=C1 KZQYIMCESJLPQH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 208000032400 Retinal pigmentation Diseases 0.000 description 1
- 101150071661 SLC25A20 gene Proteins 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical class [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 101150102633 cact gene Proteins 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001031 chromium pigment Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical class [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 239000001043 yellow 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B63/00—Lakes
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
-
- 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
- C09B63/00—Lakes
- C09B63/005—Metal lakes of 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)
- Plural Heterocyclic Compounds (AREA)
- Coloring (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Developing Agents For Electrophotography (AREA)
- Holo Graphy (AREA)
- Photoreceptors In Electrophotography (AREA)
- Paper (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9501088.0A GB9501088D0 (en) | 1995-01-20 | 1995-01-20 | Monoazo pigments |
| PCT/GB1995/002832 WO1996022333A1 (en) | 1995-01-20 | 1995-12-05 | Monoazo pigments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK98897A3 SK98897A3 (en) | 1997-11-05 |
| SK283764B6 true SK283764B6 (sk) | 2004-01-08 |
Family
ID=10768288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK988-97A SK283764B6 (sk) | 1995-01-20 | 1995-12-05 | Azopyrazolónové zlúčeniny, spôsob ich prípravy a ich použitie ako pigmenty |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5919915A (cs) |
| EP (1) | EP0804509B1 (cs) |
| JP (1) | JP3963397B2 (cs) |
| KR (1) | KR100406648B1 (cs) |
| CN (1) | CN1090656C (cs) |
| AT (1) | ATE221101T1 (cs) |
| AU (1) | AU694285B2 (cs) |
| BR (1) | BR9510230A (cs) |
| CA (1) | CA2208742C (cs) |
| CZ (1) | CZ289924B6 (cs) |
| DE (1) | DE69527545T2 (cs) |
| DK (1) | DK0804509T3 (cs) |
| ES (1) | ES2180661T3 (cs) |
| GB (2) | GB9501088D0 (cs) |
| MY (1) | MY113896A (cs) |
| SK (1) | SK283764B6 (cs) |
| TW (1) | TW343221B (cs) |
| WO (1) | WO1996022333A1 (cs) |
| ZA (1) | ZA9510619B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9623231D0 (en) | 1996-11-07 | 1997-01-08 | Clariant Int Ltd | Improvements in or relating to organic compounds |
| US6235100B1 (en) * | 1999-06-24 | 2001-05-22 | Engelhard Corporation | Metallized azo yellow pigments |
| DE10062130A1 (de) | 2000-12-13 | 2002-06-27 | Basf Ag | Transparente grünstichige gelbe Pyraziolonazopigmente |
| DE102011112853A1 (de) | 2011-09-12 | 2013-03-14 | GM Global Technology Operations LLC (n. d. Gesetzen des Staates Delaware) | Hybridsensor |
| KR101881300B1 (ko) * | 2016-06-30 | 2018-07-25 | 영남대학교 산학협력단 | 아조피라졸 화합물 및 은 촉매 반응을 이용한 이의 신규한 합성방법 |
| CN107353669B (zh) * | 2017-06-30 | 2018-11-06 | 深圳市国华光电科技有限公司 | 一种黄色染料、油墨和电润湿显示器 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1731150A (en) * | 1926-12-04 | 1929-10-08 | Chem Ind Basel | Monoazo dyestuffs |
| CH128906A (de) * | 1926-12-04 | 1928-11-16 | Chem Ind Basel | Verfahren zur Herstellung eines neuen Farbstoffes. |
| CH128907A (de) * | 1926-12-04 | 1928-11-16 | Chem Ind Basel | Verfahren zur Herstellung eines neuen Farbstoffes. |
| CH128909A (de) * | 1926-12-04 | 1928-11-16 | Chem Ind Basel | Verfahren zur Herstellung eines neuen Farbstoffes. |
| US3388651A (en) | 1966-01-28 | 1968-06-18 | Top Flite Models Inc | Covering for airplanes and method for applying same |
| DE3133404A1 (de) * | 1981-08-24 | 1983-03-10 | Basf Ag, 6700 Ludwigshafen | Sulfonsaeuregruppenhaltige verlackte azofarbstoffe |
| DE3135763A1 (de) * | 1981-09-09 | 1983-03-17 | Fa. Aug. Winkhaus, 4404 Telgte | Treibstangengetriebe |
| DE3543512A1 (de) * | 1985-12-10 | 1987-06-11 | Bayer Ag | Azofarblacke |
| EP0241413B1 (de) * | 1986-03-10 | 1993-03-03 | Ciba-Geigy Ag | Neue Aminsalze von Azoverbindungen |
| DE3833226A1 (de) * | 1988-09-30 | 1990-04-05 | Hoechst Ag | Monoazopigment, verfahren zu seiner herstellung und seine verwendung |
| CS274857B2 (en) * | 1989-05-11 | 1991-11-12 | Vychodoceske Chemicke Z S | Varnished azopigment |
-
1995
- 1995-01-20 GB GBGB9501088.0A patent/GB9501088D0/en active Pending
- 1995-12-04 GB GBGB9524737.5A patent/GB9524737D0/en active Pending
- 1995-12-05 DK DK95938543T patent/DK0804509T3/da active
- 1995-12-05 CN CN95197385A patent/CN1090656C/zh not_active Expired - Fee Related
- 1995-12-05 AU AU39902/95A patent/AU694285B2/en not_active Ceased
- 1995-12-05 WO PCT/GB1995/002832 patent/WO1996022333A1/en active IP Right Grant
- 1995-12-05 KR KR1019970704900A patent/KR100406648B1/ko not_active Expired - Fee Related
- 1995-12-05 CZ CZ19972283A patent/CZ289924B6/cs not_active IP Right Cessation
- 1995-12-05 AT AT95938543T patent/ATE221101T1/de not_active IP Right Cessation
- 1995-12-05 BR BR9510230A patent/BR9510230A/pt not_active IP Right Cessation
- 1995-12-05 CA CA002208742A patent/CA2208742C/en not_active Expired - Fee Related
- 1995-12-05 EP EP95938543A patent/EP0804509B1/en not_active Expired - Lifetime
- 1995-12-05 ES ES95938543T patent/ES2180661T3/es not_active Expired - Lifetime
- 1995-12-05 SK SK988-97A patent/SK283764B6/sk unknown
- 1995-12-05 US US08/875,073 patent/US5919915A/en not_active Expired - Fee Related
- 1995-12-05 DE DE69527545T patent/DE69527545T2/de not_active Expired - Fee Related
- 1995-12-05 JP JP52209496A patent/JP3963397B2/ja not_active Expired - Fee Related
- 1995-12-06 TW TW084113005A patent/TW343221B/zh active
- 1995-12-13 ZA ZA9510619A patent/ZA9510619B/xx unknown
-
1996
- 1996-01-18 MY MYPI96000207A patent/MY113896A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5919915A (en) | 1999-07-06 |
| CZ228397A3 (en) | 1997-10-15 |
| HK1003386A1 (en) | 1998-10-30 |
| BR9510230A (pt) | 1997-11-04 |
| MY113896A (en) | 2002-06-29 |
| DE69527545D1 (de) | 2002-08-29 |
| DE69527545T2 (de) | 2003-03-20 |
| EP0804509B1 (en) | 2002-07-24 |
| KR19980701509A (ko) | 1998-05-15 |
| ATE221101T1 (de) | 2002-08-15 |
| CN1090656C (zh) | 2002-09-11 |
| WO1996022333A1 (en) | 1996-07-25 |
| ZA9510619B (en) | 1996-07-22 |
| CA2208742C (en) | 2005-07-05 |
| CN1173193A (zh) | 1998-02-11 |
| DK0804509T3 (da) | 2002-10-21 |
| ES2180661T3 (es) | 2003-02-16 |
| AU694285B2 (en) | 1998-07-16 |
| MX9705128A (es) | 1997-10-31 |
| JP3963397B2 (ja) | 2007-08-22 |
| GB9524737D0 (en) | 1996-02-07 |
| CZ289924B6 (cs) | 2002-04-17 |
| AU3990295A (en) | 1996-08-07 |
| TW343221B (en) | 1998-10-21 |
| CA2208742A1 (en) | 1996-07-25 |
| JPH10512606A (ja) | 1998-12-02 |
| KR100406648B1 (ko) | 2004-03-31 |
| EP0804509A1 (en) | 1997-11-05 |
| GB9501088D0 (en) | 1995-03-08 |
| SK98897A3 (en) | 1997-11-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4628082A (en) | Derivatives of azobarbituric acid or salts or complexes thereof | |
| US5746821A (en) | Pigment compositions | |
| JPS6342672B2 (cs) | ||
| SK283764B6 (sk) | Azopyrazolónové zlúčeniny, spôsob ich prípravy a ich použitie ako pigmenty | |
| KR100406649B1 (ko) | 모노아조안료 | |
| JPH09217017A (ja) | ジスアゾレーキ顔料 | |
| EP0923622B1 (en) | 1:2 iron azo-dyestuff complexes | |
| JP3292749B2 (ja) | ２：１ アルミニウム錯体 | |
| CZ290587B6 (cs) | Ve vodě nerozpustná azobarviva na bázi aminochinazolindionů a způsob jejich výroby | |
| HK1003386B (en) | Monoazo pigments | |
| MXPA97005128A (en) | Mono pigments | |
| CA2208740C (en) | Monoazo pigments | |
| HK1003269B (en) | Monoazo pigments | |
| MXPA96003282A (en) | Aminekinazoline-diones-based water-insoluble azo dyes |