GB775385A - Improvements relating to chromium-containing azo dyestuffs and their use - Google Patents
Improvements relating to chromium-containing azo dyestuffs and their useInfo
- Publication number
- GB775385A GB775385A GB34053/54A GB3405354A GB775385A GB 775385 A GB775385 A GB 775385A GB 34053/54 A GB34053/54 A GB 34053/54A GB 3405354 A GB3405354 A GB 3405354A GB 775385 A GB775385 A GB 775385A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aminophenol
- dyestuff
- chromium
- acid
- dyestuffs
- 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
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title abstract 10
- 229910052804 chromium Inorganic materials 0.000 title abstract 10
- 239000011651 chromium Substances 0.000 title abstract 7
- 239000000975 dye Substances 0.000 abstract 14
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 6
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 abstract 6
- 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 abstract 6
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- 125000001424 substituent group Chemical group 0.000 abstract 4
- SFLMBHYNCSYPOO-UHFFFAOYSA-N 2-amino-4-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC=C(O)C(N)=C1 SFLMBHYNCSYPOO-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229950011260 betanaphthol Drugs 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 3
- 229940124530 sulfonamide Drugs 0.000 abstract 3
- FHMMQQXRSYSWCM-UHFFFAOYSA-N 1-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=C(O)C=CC2=C1 FHMMQQXRSYSWCM-UHFFFAOYSA-N 0.000 abstract 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 2
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 abstract 2
- JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-UHFFFAOYSA-N 0.000 abstract 2
- -1 aldehyde compounds Chemical class 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 230000003381 solubilizing effect Effects 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 abstract 1
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 abstract 1
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 abstract 1
- TUADYTFWZPZZTP-UHFFFAOYSA-N 2-amino-4-methoxyphenol Chemical compound COC1=CC=C(O)C(N)=C1 TUADYTFWZPZZTP-UHFFFAOYSA-N 0.000 abstract 1
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001845 chromium compounds Chemical class 0.000 abstract 1
- 230000009918 complex formation Effects 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000001465 metallisation Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 1
- 229920001184 polypeptide Polymers 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 102000004196 processed proteins & peptides Human genes 0.000 abstract 1
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229960004889 salicylic acid Drugs 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises complex chromium compounds of formula:-(F1 - M1 - F2)M2 wherein M1 is a chromium atom bound in complex linkage, M2 is a monovalent cation, F1 is a metallizable monoazo dyestuff and F2 is a metallizable azo-methine dyestuff, which dyestuffs apart from any carboxyl groups taking part in the complex formation contain no further acid water-solubilizing groups. The above compounds are prepared by reacting simultaneously or in any order desired, a chroming agent, a metallizable monoazo dyestuff and a metallizable azomethine dyestuff, or the appropriate amino and aldehyde compounds which form the azomethine dyestuff, the dyestuffs containing no acid water solubilizing groups except complexforming carboxyl groups, under conditions such that a compound of the above formula is obtained. The monoazo and azomethine dyestuffs used in the process contain in the neighbouring positions to the azo or azomethine bridge a metallizable substituent or a group convertible thereto (e.g. on one side a hydroxyl or enolizable carbonyl group and on the other a hydroxyl or carboxy or alkoxy group). The monoazo dyestuffs are obtained from diazotized o - hydroxy - or - alkoxy - or -carboxy - amino aromatic compounds by coupling with azo components which couple ortho to a hydroxy or enolizable carbonyl group. The metallizable azomethine dyestuffs are obtained by reacting an aromatic o - hydroxy - or - carboxy - amino compound with an aromatic o - hydroxyaldehyde. The dyestuff components may contain further substituents such as halogen atoms and alkyl, alkoxy, nitro, acylamino, alkyl and aryl sulphonyl, sulphonic acid dialkylamide groups or sulphonic acid phenyl alkylamide groups. The preferred substituents for use in the dyestuffs used for textile dyeing are non-acid water solubilizing substituents such as sulphonamide, N-monosubstituted sulphonamide, sulphonic acid N - alkyl - N - alkanolamide, alkyl and alkenyl sulphonyl and acetylamino groups. The specified chroming agents are normal and complex salts of chromium including salts of chromosalicyclic acid. The metallization may be carried out in the warm in organic or inorganic diluents in a neutral to alkaline medium and using at least one atom of chromium to two dyestuff molecules. A preferred procedure is to convert one dyestuff component, preferably the monoazo component, into a chromium complex containing a chromium atom to one dyestuff molecule, in known manner, and then to react with the other dyestuff in aqueous or organic solution at a pH of 3-9. The 1 : 1 chromium : dyestuff complex used in above process may be an addition compound thereof with metallizable organic compounds which are not dyestuffs such as salicylic acid or sulphosalicyclic acid. The dyestuffs dye wool and synthetic polypeptides in orange, yellow, brown, green and blue shades. In examples: (1) 2 - hydroxybenzaldehyde or 3 : 5 - dichloro - 2 - hydroxybenzaldehyde is reacted with 2 - aminophenol or 4 - chloro - or - nitro - or - methylsulphonyl - 2 - aminophenol and the reaction mixture reacted further with the 1 : 1 chromium complex of 4 - methylsulphonyl - 2 - aminophenol --> 1 - (31 - chlorophenyl) - 3 - methyl - 5-pyrazolone; (2) the chromium complex consisting of one molecule of 4 - nitro - 2 - aminophenol --> 1 - phenyl - 3 -methyl-5 - pyrazolone, one chromium atom and one molecule of sulphosalicylic acid is reacted with a mixture of 2 - hydroxybenzaldehyde and 4 - methylsulphonyl - 2 - aminophenol; (3) 4-methylsulphonyl - 2 - aminophenol --> 2-naphthol, 2 - aminophenol and 2 - hydroxybenzaldehyde are reacted together with ammonium chromosalicylate. In a Table the following additional reaction components are specified (a) 1 : 1 complexes of the monoazo dyes: - 2 - aminobenzoic acid or 4 - chloro - 2 - aminobenzoic acid --> 1 - phenyl - 3 -methyl - 5 - pyrazolone, 5 - nitro - 2 - aminophenol --> 1 - phenyl-3 - methyl - 5 - pyrazolone, 4 - nitro - 2 - aminophenol --> p - cresol or 3 : 4 dimethylphenol, 2 - aminophenol - 4 - sulphonamide --> 1 - 31 - sulphonamido - phenyl) - 3 - methyl - 5 - pyrazolone, 4 - methoxy - 2 - aminophenol --> 1 - hydroxynaphthalene - 3 - sulphodimethylamide and 1 - amino - 2 - naphthol --> 2 - naphthol or 2 - hydroxynaphthalene - 6 - sulphomethyl - ethanolamide; (b) azomethine dyestuff components:- 2 - hydroxy - 1 - naphthaldehyde; 1 - amino - 2 - naphthol, 2 - aminobenzoic acid, 4 - chloro - 2 - amino - benzoic acid and 2 - aminophenol-4 - sulphonamide.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH775385X | 1953-11-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB775385A true GB775385A (en) | 1957-05-22 |
Family
ID=4535779
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB34053/54A Expired GB775385A (en) | 1953-11-26 | 1954-11-24 | Improvements relating to chromium-containing azo dyestuffs and their use |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB775385A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2985646A (en) * | 1957-03-14 | 1961-05-23 | Geigy Ag J R | Chromium-containing dyestuffs |
-
1954
- 1954-11-24 GB GB34053/54A patent/GB775385A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2985646A (en) * | 1957-03-14 | 1961-05-23 | Geigy Ag J R | Chromium-containing dyestuffs |
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