CA1049000A - Chromium complex dyes, their manufacture and use - Google Patents
Chromium complex dyes, their manufacture and useInfo
- Publication number
- CA1049000A CA1049000A CA75217832A CA217832A CA1049000A CA 1049000 A CA1049000 A CA 1049000A CA 75217832 A CA75217832 A CA 75217832A CA 217832 A CA217832 A CA 217832A CA 1049000 A CA1049000 A CA 1049000A
- Authority
- CA
- Canada
- Prior art keywords
- nitro
- methyl
- chromium
- dye
- 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
- 239000000975 dye Substances 0.000 title claims abstract description 57
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 229910052804 chromium Inorganic materials 0.000 title claims abstract description 38
- 239000011651 chromium Substances 0.000 title claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- -1 nitro, methyl Chemical group 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 150000001768 cations Chemical class 0.000 claims abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 2
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
- 239000000243 solution Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 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 12
- 239000011780 sodium chloride Substances 0.000 description 12
- 238000007792 addition Methods 0.000 description 11
- 239000004952 Polyamide Substances 0.000 description 9
- 239000000987 azo dye Substances 0.000 description 9
- 229920002647 polyamide Polymers 0.000 description 9
- 210000002268 wool Anatomy 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 6
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 6
- 239000001166 ammonium sulphate Substances 0.000 description 6
- 235000011130 ammonium sulphate Nutrition 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000004552 water soluble powder Substances 0.000 description 6
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 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
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 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
- PEHCLPGYMNFIOV-UHFFFAOYSA-N 2-(2-chloro-6-methylphenyl)-5-methyl-4h-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=C(C)C=CC=C1Cl PEHCLPGYMNFIOV-UHFFFAOYSA-N 0.000 description 1
- HRBCDVLFVGOSIC-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-methyl-1h-pyrazol-3-one Chemical compound N1C(C)=CC(=O)N1C1=CC=CC(Cl)=C1 HRBCDVLFVGOSIC-UHFFFAOYSA-N 0.000 description 1
- FBFCBNWVKOBJLV-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-methyl-4h-pyrazol-3-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)CC(C)=N1 FBFCBNWVKOBJLV-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
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 1
- FEDLEBCVFZMHBP-UHFFFAOYSA-N 2-amino-3-methylphenol Chemical compound CC1=CC=CC(O)=C1N FEDLEBCVFZMHBP-UHFFFAOYSA-N 0.000 description 1
- AJWIWEGQLDDWQC-UHFFFAOYSA-N 2-amino-4-methyl-6-nitrophenol Chemical compound CC1=CC(N)=C(O)C([N+]([O-])=O)=C1 AJWIWEGQLDDWQC-UHFFFAOYSA-N 0.000 description 1
- FZCQMIRJCGWWCL-UHFFFAOYSA-N 2-amino-5-chlorophenol Chemical compound NC1=CC=C(Cl)C=C1O FZCQMIRJCGWWCL-UHFFFAOYSA-N 0.000 description 1
- RHPXYZMDLOJTFF-UHFFFAOYSA-N 3-amino-4-hydroxy-5-nitrobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC([N+]([O-])=O)=C1O RHPXYZMDLOJTFF-UHFFFAOYSA-N 0.000 description 1
- QGTXBWMKRGHPDD-UHFFFAOYSA-N 3-amino-5-chloro-4-hydroxybenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(Cl)=C1O QGTXBWMKRGHPDD-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- 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
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SUXCALIDMIIJCK-UHFFFAOYSA-L disodium;4-amino-3-[[4-[4-[(1-amino-4-sulfonatonaphthalen-2-yl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(N=NC3=CC=C(C=C3C)C=3C=C(C(=CC=3)N=NC=3C(=C4C=CC=CC4=C(C=3)S([O-])(=O)=O)N)C)=CC(S([O-])(=O)=O)=C21 SUXCALIDMIIJCK-UHFFFAOYSA-L 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 239000008103 glucose Substances 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
- 229960003742 phenol Drugs 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH50674A CH583285A5 (is") | 1974-01-15 | 1974-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1049000A true CA1049000A (en) | 1979-02-20 |
Family
ID=4188557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA75217832A Expired CA1049000A (en) | 1974-01-15 | 1975-01-13 | Chromium complex dyes, their manufacture and use |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5839183B2 (is") |
| AR (1) | AR218427A1 (is") |
| AU (1) | AU7681774A (is") |
| BR (1) | BR7500117A (is") |
| CA (1) | CA1049000A (is") |
| CH (1) | CH583285A5 (is") |
| DE (1) | DE2501039C2 (is") |
| ES (1) | ES433766A1 (is") |
| FR (1) | FR2257657B1 (is") |
| GB (1) | GB1492683A (is") |
| IT (1) | IT1026317B (is") |
| NL (1) | NL7417051A (is") |
| ZA (1) | ZA75245B (is") |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH616953A5 (is") * | 1975-08-27 | 1980-04-30 | Sandoz Ag | |
| DE2835493C2 (de) * | 1978-08-12 | 1983-05-19 | Bayer Ag, 5090 Leverkusen | Chromkomplexfarbstoffe |
| DE4130806A1 (de) * | 1991-09-17 | 1993-03-18 | Bayer Ag | Unsymmetrische 1:2-chromkomplexfarbstoffe |
Family Cites Families (4)
| 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 |
| DE1133846B (de) * | 1958-04-30 | 1962-07-26 | Ciba Geigy | Verfahren zur Herstellung chromhaltiger Azofarbstoffe |
| FR1297014A (fr) * | 1960-08-09 | 1962-06-22 | Basf Ag | Sels d'ammonium de colorants à complexes métalliques |
| DE1271857B (de) * | 1962-10-17 | 1968-07-04 | Ciba Geigy | Verfahren zur Herstellung chromhaltiger Azofarbstoffe |
-
1974
- 1974-01-15 CH CH50674A patent/CH583285A5/xx not_active IP Right Cessation
- 1974-12-24 AU AU76817/74A patent/AU7681774A/en not_active Expired
- 1974-12-31 NL NL7417051A patent/NL7417051A/xx not_active Application Discontinuation
-
1975
- 1975-01-08 BR BR117/75D patent/BR7500117A/pt unknown
- 1975-01-13 CA CA75217832A patent/CA1049000A/en not_active Expired
- 1975-01-13 IT IT47644/75A patent/IT1026317B/it active
- 1975-01-13 GB GB1376/75A patent/GB1492683A/en not_active Expired
- 1975-01-13 FR FR7500877A patent/FR2257657B1/fr not_active Expired
- 1975-01-13 DE DE2501039A patent/DE2501039C2/de not_active Expired
- 1975-01-14 AR AR257283A patent/AR218427A1/es active
- 1975-01-14 ZA ZA00750245A patent/ZA75245B/xx unknown
- 1975-01-14 ES ES433766A patent/ES433766A1/es not_active Expired
- 1975-01-14 JP JP50005995A patent/JPS5839183B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES433766A1 (es) | 1976-12-16 |
| GB1492683A (en) | 1977-11-23 |
| JPS50102622A (is") | 1975-08-14 |
| NL7417051A (nl) | 1975-07-17 |
| DE2501039A1 (de) | 1975-07-17 |
| FR2257657B1 (is") | 1977-07-01 |
| DE2501039C2 (de) | 1983-10-27 |
| CH583285A5 (is") | 1976-12-31 |
| AR218427A1 (es) | 1980-06-13 |
| BR7500117A (pt) | 1975-11-04 |
| FR2257657A1 (is") | 1975-08-08 |
| IT1026317B (it) | 1978-09-20 |
| ZA75245B (en) | 1976-01-28 |
| AU7681774A (en) | 1976-06-24 |
| JPS5839183B2 (ja) | 1983-08-27 |
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