GB1566327A - Chromium complex azo dyes process for their manufacture and use thereof - Google Patents
Chromium complex azo dyes process for their manufacture and use thereof Download PDFInfo
- Publication number
- GB1566327A GB1566327A GB4268/77A GB426877A GB1566327A GB 1566327 A GB1566327 A GB 1566327A GB 4268/77 A GB4268/77 A GB 4268/77A GB 426877 A GB426877 A GB 426877A GB 1566327 A GB1566327 A GB 1566327A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dye
- group
- formula
- nitro
- chromium complex
- 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
Links
- 239000011651 chromium Substances 0.000 title claims description 27
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 26
- 229910052804 chromium Inorganic materials 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 20
- 239000000987 azo dye Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 91
- 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 claims description 30
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- -1 sulpho groups Chemical group 0.000 claims description 11
- 238000004043 dyeing Methods 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001844 chromium Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000010985 leather Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 210000002268 wool Anatomy 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229950011260 betanaphthol Drugs 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- LJAOOBNHPFKCDR-UHFFFAOYSA-K chromium(3+) trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Cr+3] LJAOOBNHPFKCDR-UHFFFAOYSA-K 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical compound OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 101000831256 Oryza sativa subsp. japonica Cysteine proteinase inhibitor 1 Proteins 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 229910021563 chromium fluoride Inorganic materials 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 0.000 description 1
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical class [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000991 leather dye Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
-
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/26—Disazo or polyazo compounds containing chromium
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
- D06P1/10—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes containing metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH135676A CH619977A5 (en, 2012) | 1976-02-04 | 1976-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1566327A true GB1566327A (en) | 1980-04-30 |
Family
ID=4208545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4268/77A Expired GB1566327A (en) | 1976-02-04 | 1977-02-02 | Chromium complex azo dyes process for their manufacture and use thereof |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4314937A (en, 2012) |
| JP (1) | JPS5295742A (en, 2012) |
| AR (1) | AR226022A1 (en, 2012) |
| AU (1) | AU511366B2 (en, 2012) |
| BR (1) | BR7700662A (en, 2012) |
| CA (1) | CA1088051A (en, 2012) |
| CH (1) | CH619977A5 (en, 2012) |
| DE (1) | DE2704364A1 (en, 2012) |
| ES (1) | ES455626A1 (en, 2012) |
| FR (1) | FR2340354A1 (en, 2012) |
| GB (1) | GB1566327A (en, 2012) |
| PT (1) | PT66143B (en, 2012) |
| ZA (1) | ZA77607B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3263035D1 (en) * | 1981-12-15 | 1985-05-15 | Ciba Geigy Ag | Chromium complexes of polyazo dyestuffs |
| US4502860A (en) * | 1982-07-02 | 1985-03-05 | Ciba-Geigy Corporation | Bis-1:2-chromium complexes of disazo dyes, and their preparation and use |
| US4623606A (en) * | 1986-01-24 | 1986-11-18 | Xerox Corporation | Toner compositions with negative charge enhancing additives |
| DE59510091D1 (de) * | 1994-12-21 | 2002-04-11 | Ciba Sc Holding Ag | 1:2-Chromkomplexfarbstoffe enthaltende Farbstoffmischungen und 1:2 Chromkomplexfarbstoffe |
| US5916722A (en) * | 1998-02-05 | 1999-06-29 | Xerox Corporation | Toner compositions |
| US5948583A (en) * | 1998-04-13 | 1999-09-07 | Xerox Corp | Toner composition and processes thereof |
| US6420078B1 (en) | 2000-12-28 | 2002-07-16 | Xerox Corporation | Toner compositions with surface additives |
| US6566025B1 (en) | 2002-01-16 | 2003-05-20 | Xerox Corporation | Polymeric particles as external toner additives |
| US7229735B2 (en) * | 2004-07-26 | 2007-06-12 | Xerox Corporation | Toner compositions |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2933489A (en) * | 1960-04-19 | Heavy metal-containing dyestuffs | ||
| AT198397B (de) * | 1956-01-26 | 1958-06-25 | Geigy Ag J R | Verfahren zur Herstellung von neuen, schwermetallhaltigen Azofarbstoffen |
| NL130114C (en, 2012) * | 1964-10-29 | |||
| US3576771A (en) * | 1968-05-14 | 1971-04-27 | Koppers Co Inc | Self-extinguishing polymer compositions containing brominated arylidene ketones |
-
1976
- 1976-02-04 CH CH135676A patent/CH619977A5/de not_active IP Right Cessation
-
1977
- 1977-02-02 DE DE19772704364 patent/DE2704364A1/de active Granted
- 1977-02-02 AR AR266408A patent/AR226022A1/es active
- 1977-02-02 PT PT66143A patent/PT66143B/pt unknown
- 1977-02-02 GB GB4268/77A patent/GB1566327A/en not_active Expired
- 1977-02-02 CA CA270,887A patent/CA1088051A/en not_active Expired
- 1977-02-02 JP JP981877A patent/JPS5295742A/ja active Granted
- 1977-02-03 ES ES455626A patent/ES455626A1/es not_active Expired
- 1977-02-03 BR BR7700662A patent/BR7700662A/pt unknown
- 1977-02-03 ZA ZA770607A patent/ZA77607B/xx unknown
- 1977-02-03 FR FR7703072A patent/FR2340354A1/fr active Granted
- 1977-02-04 AU AU21955/77A patent/AU511366B2/en not_active Expired
-
1980
- 1980-03-07 US US06/128,228 patent/US4314937A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ZA77607B (en) | 1977-12-28 |
| PT66143A (en) | 1977-03-01 |
| JPS6112950B2 (en, 2012) | 1986-04-10 |
| DE2704364C2 (en, 2012) | 1988-04-14 |
| JPS5295742A (en) | 1977-08-11 |
| CH619977A5 (en, 2012) | 1980-10-31 |
| FR2340354B1 (en, 2012) | 1981-01-09 |
| DE2704364A1 (de) | 1977-08-18 |
| FR2340354A1 (fr) | 1977-09-02 |
| US4314937A (en) | 1982-02-09 |
| CA1088051A (en) | 1980-10-21 |
| AU2195577A (en) | 1978-08-10 |
| PT66143B (en) | 1978-07-06 |
| ES455626A1 (es) | 1978-01-01 |
| AR226022A1 (es) | 1982-05-31 |
| AU511366B2 (en) | 1980-08-14 |
| BR7700662A (pt) | 1977-10-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1566327A (en) | Chromium complex azo dyes process for their manufacture and use thereof | |
| CA1059997A (en) | Chromium complex dyes, their manufacture and use | |
| US3915952A (en) | Polyazo compounds containing 2,4,2{40 ,4{40 -tetrahydroxy-dibenzylamine as coupling component | |
| US3041327A (en) | Chj sojh | |
| US3975369A (en) | 2:1 Metal complexes of 2,2',4'-trihydroxy-3,5-dinitroazobenzene bound to a diphenylamine through an azo bridge | |
| US3516979A (en) | Heterogenous 1:2 metal complexes of monoazo dyes | |
| CA1063599A (en) | Chromium complex dyes, their manufacture and their use | |
| US3943122A (en) | Polyazo compounds containing benzhydrol as a component | |
| DE1644164A1 (de) | Verfahren zur Herstellung von 2:1-Chromkomplexmonoazofarbstoffen | |
| US3925346A (en) | Mixed chromium-containing azo dyestuffs containing, per atom of chromium, one molecule of an o,o'-dihydroxy-sulphophenylene-azo-naphthalene and one molecule of an -o-hydroxyphenylene-azo-acetoacetamide | |
| JPH06287460A (ja) | １：２クロム錯体染料 | |
| US3189593A (en) | Polyazo dyes | |
| US2741655A (en) | Cupriferous azo-dyestuffs | |
| US3169951A (en) | Chromhjm-containing azo dyestuffs | |
| US3213077A (en) | Metallized azo dyes | |
| US3970615A (en) | Unsymmetrical mono-sulfo containing chromium complexes of azo dyes | |
| CA1148538A (en) | Metal complex compounds, processes for their manufacture and their use | |
| US2472965A (en) | Metallized tetrakisazo dyes | |
| GB2048295A (en) | Diazo compounds and their metal complexes | |
| US3891617A (en) | Metallized and non-metallized diphenol methane containing azo dyestuffs | |
| EP0148121A2 (de) | Unsymmetrische 1:2-Chromkomplexfarbstoffe | |
| US2749333A (en) | Metal-containing polyazo dyestuffs | |
| NZ272701A (en) | Bis(azaheterocyclylaryl)disulphanilamide derivatives; azo dyes and use in dyeing leather | |
| US3189595A (en) | Metal comples dies containing 2-dibenzofuranol | |
| US1786272A (en) | Azo dyestuffs containing metals and process of making same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940202 |