GB812151A - Improvements relating to metal-containing tricyclic chelating monoazo dyestuffs and their use - Google Patents
Improvements relating to metal-containing tricyclic chelating monoazo dyestuffs and their useInfo
- Publication number
- GB812151A GB812151A GB28467/55A GB2846755A GB812151A GB 812151 A GB812151 A GB 812151A GB 28467/55 A GB28467/55 A GB 28467/55A GB 2846755 A GB2846755 A GB 2846755A GB 812151 A GB812151 A GB 812151A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- complex
- nitro
- amino
- acid
- 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
- 229910052751 metal Inorganic materials 0.000 title abstract 2
- 239000002184 metal Substances 0.000 title abstract 2
- 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 title 1
- 239000000975 dye Substances 0.000 abstract 5
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 3
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 abstract 2
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 abstract 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 2
- 229910052804 chromium Inorganic materials 0.000 abstract 2
- 239000011651 chromium Substances 0.000 abstract 2
- 229910017052 cobalt Inorganic materials 0.000 abstract 2
- 239000010941 cobalt Substances 0.000 abstract 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 2
- 210000002268 wool Anatomy 0.000 abstract 2
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical class O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 abstract 1
- HYJQAGLKMHBVDU-UHFFFAOYSA-N 2-amino-5-nitrophenol 2-aminophenol Chemical compound NC1=C(C=CC=C1)O.[N+](=O)([O-])C=1C=CC(=C(C1)O)N HYJQAGLKMHBVDU-UHFFFAOYSA-N 0.000 abstract 1
- YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical class NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 abstract 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 abstract 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 abstract 1
- RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-UHFFFAOYSA-N 0.000 abstract 1
- UNFNRIIETORURP-UHFFFAOYSA-N 7-methoxynaphthalen-2-ol Chemical compound C1=CC(O)=CC2=CC(OC)=CC=C21 UNFNRIIETORURP-UHFFFAOYSA-N 0.000 abstract 1
- 150000004325 8-hydroxyquinolines Chemical class 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical class C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 abstract 1
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 abstract 1
- 229950011260 betanaphthol Drugs 0.000 abstract 1
- 150000003940 butylamines Chemical class 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000013522 chelant Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000009918 complex formation Effects 0.000 abstract 1
- 150000004696 coordination complex Chemical class 0.000 abstract 1
- 125000005028 dihydroxyaryl group Chemical group 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical class O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002736 metal compounds Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 1
- 150000004780 naphthols Chemical class 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229920001184 polypeptide Polymers 0.000 abstract 1
- 102000004196 processed proteins & peptides Human genes 0.000 abstract 1
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical group O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003870 salicylic acids Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000565 sulfonamide group Chemical group 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)
- Coloring (AREA)
Abstract
The invention comprises metal compounds which contain one atom of chromium or cobalt in complex union with one molecule of a dyestuff of formula X1-A-N = N-B-X2 where A is a benzene residue with X1 oto the azo group, B is a naphthalene or pyrazolone residue with X2 in a neighbouring position to the azo group, one X is a metallizable group and the other is the residue -(SO2)n-NH-D where D is an organic residue containing a group taking part in the complex formation and n is 0 or 1 and with one molecule of a coordinative divalent complex former. The complexes are readily water-soluble and the dyestuffs occupy 4 co-ordination positions at the complex metal atom whilst forming three 5- or 6-membered chelate rings. The dyestuffs are made by treating a dyestuff of the above formula with an agent yielding chromium or cobalt in the presence of a co-ordinative divalent complex former, by reacting a 1,1-metal complex of a dyestuff of the above formula with the divalent complex former or by reacting the dyestuff with a metal complex of a divalent complex former. Specified values for one X are OH, COOH and alkoxy and the other X may be b -aminopropionic acid, o-carboxy and -hydroxy-phenyl-amino, quinolinyl-8-amino, sulphonic acid glycinide, sulphonic acid amide-b -propionic acid and sulphonic acid-o-carboxy-and -hydroxy phenylamide radicles. Indicated as diazo components are 2-aminobenzenesulphonic acid amides which contain a propionic, o-carboxy or -hydroxy-phenyl residue as substituents at the N atom of the amide group and 2-amino-phenols, -alkoxyphenols and -1-carboxylic acids. Coupling components mentioned are 5-pyrazolones, naphthols, 2-naphthyl - b - aminopropionic acid and 2-(o-carboxy- and -hydroxy - phenylamino) - naphthalenes. Divalent complex formers mentioned are a -hydroxy- and -amino-carboxylic acids, vicinol dihydroxyaryls, o - amino - hydroxyaryls, 8-hydroxy-quinolines or benzoquinolines, o-hydroxy-aldehydes and -ketones, o-hydroxy-azo and -benzene - azo - methenes, 1,2 - diaminoalkanes, pyridine, benzopyridine - 2 - carboxylic acids and o-nitrosonaphthols and they may contain halogen, sulphonic acid and sulphonamide substituents. The dyestuffs dye polypeptide fibres such as wool and superpolyamides and -urethanes. In examples and a table which illustrate the preparation of the dyestuffs and their use in dyeing wool in yellow or green shades, the diazo components are 2-aniline - 1 - sulphonic acid glycinide and 21-carboxyphenylamide, 5-nitro-2-aminophenol- and 2 - aminophenol - 4 - methyl and -ethylsulphones, 3 - amino - 4 - hydroxy - 31 - sulphonamido - diphenyl sulphone, 5 - nitro - 4 - chloro- and 5 - nitro - 2 - aminophenol, 5 - nitro - 2 - and 5 - nitro - 2 - aminophenols, 5 - nitro - 2 - aminobenzoic acid and 2-aminobenzoic acid, the coupling components being 1-(31-chlorophenyl)- and 1 - phenyl - 3 - methyl - 5 - pyrazolones, 2 - (21 - carboxyphenyl)-, -(51 - chloro - 21-carboxyphenyl)-and -b -carboxyethyl - naphthylamines, 2-naphthol and 7-methoxy-2-naphthol and the complex formers are 8-hydroxy- and 5 - chloro - 8 - hydroxy - quino - lines, picolinic, quinaldic and salicylic acids, salicylaldehyde, o - hydroxyacetophenone, the reaction products of salicylaldehyde with aniline and methyl and butylamines, 5-hydroxy-aza-(4)-phenanthrene and ammonium chromosalicylate. Specification 560,787, [Group IV], is referred to. Reference has been directed by the Comptroller to Specifications 778,262 and 790,904.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH812151X | 1954-10-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB812151A true GB812151A (en) | 1959-04-22 |
Family
ID=4538585
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB28467/55A Expired GB812151A (en) | 1954-10-08 | 1955-10-06 | Improvements relating to metal-containing tricyclic chelating monoazo dyestuffs and their use |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB812151A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4019857A (en) * | 1973-03-20 | 1977-04-26 | Produits Chimiques Ugine Kuhlmann | Process for the coloration of hydrophobic chemical fibers by metalliferous dyestuffs of cationic character |
US4617382A (en) * | 1974-07-05 | 1986-10-14 | Ciba-Geigy Corporation | 8-hydroxyquinoline sulfonic acid-azo chromium complexes |
-
1955
- 1955-10-06 GB GB28467/55A patent/GB812151A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4019857A (en) * | 1973-03-20 | 1977-04-26 | Produits Chimiques Ugine Kuhlmann | Process for the coloration of hydrophobic chemical fibers by metalliferous dyestuffs of cationic character |
US4617382A (en) * | 1974-07-05 | 1986-10-14 | Ciba-Geigy Corporation | 8-hydroxyquinoline sulfonic acid-azo chromium complexes |
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