CA1088051A - Chromium complex dyes, process for their manufacture and use thereof - Google Patents
Chromium complex dyes, process for their manufacture and use thereofInfo
- Publication number
- CA1088051A CA1088051A CA270,887A CA270887A CA1088051A CA 1088051 A CA1088051 A CA 1088051A CA 270887 A CA270887 A CA 270887A CA 1088051 A CA1088051 A CA 1088051A
- Authority
- CA
- Canada
- Prior art keywords
- group
- dye
- 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 abstract description 26
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 229910052804 chromium Inorganic materials 0.000 title claims abstract description 24
- 239000000975 dye Substances 0.000 title claims description 85
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 19
- 229910006069 SO3H Inorganic materials 0.000 claims abstract description 15
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 15
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 150000001768 cations Chemical class 0.000 claims abstract description 4
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract 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 claims description 26
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 23
- 238000004043 dyeing Methods 0.000 claims description 9
- -1 sulpho groups Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000987 azo dye Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen 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
- 150000001844 chromium Chemical class 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000010985 leather Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 210000002268 wool Anatomy 0.000 description 7
- 229950011260 betanaphthol Drugs 0.000 description 6
- 239000004952 Polyamide Substances 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 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 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 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
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 241000896693 Disa Species 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- 239000003513 alkali Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 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
- 230000007935 neutral effect Effects 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
- AWMLROSUUNZXQP-UHFFFAOYSA-N 2-amino-4-phenyldiazenylphenol Chemical compound C1=C(O)C(N)=CC(N=NC=2C=CC=CC=2)=C1 AWMLROSUUNZXQP-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 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
- 125000000217 alkyl 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
- 125000003118 aryl group 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
- 239000003795 chemical substances by application 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
- 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
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000991 leather dye Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 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
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH135676A CH619977A5 (en, 2012) | 1976-02-04 | 1976-02-04 | |
| CH1356/76 | 1976-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1088051A true CA1088051A (en) | 1980-10-21 |
Family
ID=4208545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA270,887A Expired CA1088051A (en) | 1976-02-04 | 1977-02-02 | Chromium complex 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 |
|---|---|
| GB1566327A (en) | 1980-04-30 |
| 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 |
| 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 |
|---|---|---|
| CA1088051A (en) | Chromium complex dyes, process for their manufacture and use thereof | |
| CA1059997A (en) | Chromium complex dyes, their manufacture and use | |
| US2933488A (en) | Heavy metal-containing azo dyestuffs | |
| US3514439A (en) | 1:2 homogeneous cobalt complexes of phenyl-azo-phenol,phenyl-azo-naphthol or phenyl-azo pyrazolone dyes having bound to the phenyl nucleus an anilino or naphthylamino substitutent | |
| US2711404A (en) | Brown chrome containing dyestuffs | |
| US2776956A (en) | Soinhi | |
| HU182574B (en) | Process for producing 1:2 metal complexes of bis-diazo-compounds | |
| US3221003A (en) | Chrgmium cqmplex mixed azo dyestuffs | |
| US2708193A (en) | Water-soluble chromium-containing azo dyestuffs | |
| HU184830B (en) | Process for producing chromocomplexes of diazo-compounds | |
| US2839521A (en) | Azo dyestuffs containing heavy metal | |
| US3516979A (en) | Heterogenous 1:2 metal complexes of monoazo dyes | |
| CA1063599A (en) | Chromium complex dyes, their manufacture and their use | |
| US2856397A (en) | Production of metal-containing azo dyestuffs | |
| US3632568A (en) | Monazo dyes and their metal complexes | |
| US3213077A (en) | Metallized azo dyes | |
| US3943122A (en) | Polyazo compounds containing benzhydrol as a component | |
| CA1049001A (en) | Chromium complex dyes, their manufacture and use | |
| 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 | |
| CA1097620A (en) | Copper, cobalt or chromium complex monoazo compounds, processes for their manufacture, their use as dyestuffs and fiber materials dyed with these dyestuffs | |
| US2599147A (en) | Chromiferous monoazo-dyestuffs | |
| JPH06287460A (ja) | １：２クロム錯体染料 | |
| CA1049000A (en) | Chromium complex dyes, their manufacture and use | |
| US3169951A (en) | Chromhjm-containing azo dyestuffs | |
| US3040020A (en) | Metal complex of x-cyanonaphtkyl- |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |