CA1048494A - Chromium complex dyes, their manufacture and use - Google Patents
Chromium complex dyes, their manufacture and useInfo
- Publication number
- CA1048494A CA1048494A CA75217543A CA217543A CA1048494A CA 1048494 A CA1048494 A CA 1048494A CA 75217543 A CA75217543 A CA 75217543A CA 217543 A CA217543 A CA 217543A CA 1048494 A CA1048494 A CA 1048494A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- chromium complex
- hydrogen
- formula
- chromium
- 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
- 239000000975 dye Substances 0.000 title claims abstract description 32
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 229910052804 chromium Inorganic materials 0.000 title claims abstract description 21
- 239000011651 chromium Substances 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 150000001768 cations Chemical class 0.000 claims abstract description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000001844 chromium Chemical class 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- -1 1-(2'-ethylphenyl)-3-methyl-5-pyrazolone-1-(4'-bromophenyl)-3-methyl-5-pyrazolone 1-(2'-chloro-6'-methylphenyl)-3-methyl-5-pyrazolone Chemical compound 0.000 description 5
- 239000004952 Polyamide Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 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 description 4
- 210000002268 wool Anatomy 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000006519 CCH3 Chemical group 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- FZCQMIRJCGWWCL-UHFFFAOYSA-N 2-amino-5-chlorophenol Chemical compound NC1=CC=C(Cl)C=C1O FZCQMIRJCGWWCL-UHFFFAOYSA-N 0.000 description 1
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 1
- BNILDNQGLCOHLV-UHFFFAOYSA-N 5-methyl-2-(3-nitrophenyl)-4h-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 BNILDNQGLCOHLV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GDBFSJLHQMUHPQ-UHFFFAOYSA-N COC1=CC=C(C=C1)N1N=C(CC1=O)C.ClC1=C(C(=CC(=C1)Cl)Cl)N1N=C(CC1=O)C.BrC1=C(C=C(C=C1)Br)N1N=C(CC1=O)C Chemical compound COC1=CC=C(C=C1)N1N=C(CC1=O)C.ClC1=C(C(=CC(=C1)Cl)Cl)N1N=C(CC1=O)C.BrC1=C(C=C(C=C1)Br)N1N=C(CC1=O)C GDBFSJLHQMUHPQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 125000004432 carbon atom Chemical group C* 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
- 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 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
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate 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
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH28774A CH589125A5 (en, 2012) | 1974-01-10 | 1974-01-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1048494A true CA1048494A (en) | 1979-02-13 |
Family
ID=4183544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA75217543A Expired CA1048494A (en) | 1974-01-10 | 1975-01-08 | Chromium complex dyes, their manufacture and use |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3970615A (en, 2012) |
| JP (1) | JPS5837340B2 (en, 2012) |
| AR (1) | AR207580A1 (en, 2012) |
| AU (1) | AU7681674A (en, 2012) |
| BR (1) | BR7500116A (en, 2012) |
| CA (1) | CA1048494A (en, 2012) |
| CH (1) | CH589125A5 (en, 2012) |
| DE (1) | DE2500550C2 (en, 2012) |
| ES (1) | ES433681A1 (en, 2012) |
| FR (1) | FR2257656B1 (en, 2012) |
| GB (1) | GB1489386A (en, 2012) |
| IT (1) | IT1026265B (en, 2012) |
| NL (1) | NL7417050A (en, 2012) |
| ZA (1) | ZA75159B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4159983A (en) * | 1975-07-25 | 1979-07-03 | Sandoz Ltd. | Pure and substantially pure asymmetric 1:2 cobalt complexes of monoazo compounds |
| CH616953A5 (en, 2012) * | 1975-08-27 | 1980-04-30 | Sandoz Ag | |
| EP0357554A3 (de) * | 1988-08-31 | 1990-09-12 | Ciba-Geigy Ag | Metallkomplexverbindungen |
| JPH09296591A (ja) * | 1996-05-02 | 1997-11-18 | Yoshiwara Naisou:Kk | 畳 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB765355A (en) * | 1953-06-08 | 1957-01-09 | Ciba Ltd | Mixed complexes of metalliferous mono-azo-dyestuffs and process for making them |
| DE1259482B (de) * | 1962-04-28 | 1968-01-25 | Basf Ag | Verfahren zur Herstellung von sulfonsaeuregruppenhaltigen Chromkomplexfarbstoffen |
-
1959
- 1959-02-18 DE DE2500550A patent/DE2500550C2/de not_active Expired
-
1974
- 1974-01-10 CH CH28774A patent/CH589125A5/xx not_active IP Right Cessation
- 1974-12-19 GB GB54980/74A patent/GB1489386A/en not_active Expired
- 1974-12-24 US US05/536,059 patent/US3970615A/en not_active Expired - Lifetime
- 1974-12-24 AU AU76816/74A patent/AU7681674A/en not_active Expired
- 1974-12-31 NL NL7417050A patent/NL7417050A/xx not_active Application Discontinuation
-
1975
- 1975-01-01 AR AR257221A patent/AR207580A1/es active
- 1975-01-06 FR FR7500206A patent/FR2257656B1/fr not_active Expired
- 1975-01-08 CA CA75217543A patent/CA1048494A/en not_active Expired
- 1975-01-08 IT IT47564/75A patent/IT1026265B/it active
- 1975-01-08 BR BR116/75A patent/BR7500116A/pt unknown
- 1975-01-09 ES ES433681A patent/ES433681A1/es not_active Expired
- 1975-01-09 ZA ZA00750159A patent/ZA75159B/xx unknown
- 1975-01-10 JP JP50005059A patent/JPS5837340B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2500550A1 (de) | 1975-07-17 |
| FR2257656B1 (en, 2012) | 1978-03-10 |
| CH589125A5 (en, 2012) | 1977-06-30 |
| NL7417050A (nl) | 1975-07-14 |
| AR207580A1 (es) | 1976-10-15 |
| GB1489386A (en) | 1977-10-19 |
| ZA75159B (en) | 1976-01-28 |
| AU7681674A (en) | 1976-06-24 |
| FR2257656A1 (en, 2012) | 1975-08-08 |
| DE2500550C2 (de) | 1983-11-03 |
| JPS50101423A (en, 2012) | 1975-08-12 |
| IT1026265B (it) | 1978-09-20 |
| ES433681A1 (es) | 1976-12-01 |
| BR7500116A (pt) | 1975-11-04 |
| JPS5837340B2 (ja) | 1983-08-16 |
| US3970615A (en) | 1976-07-20 |
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