GB810207A - Improvements in metalliferous complexes of mono-azo dyestuffs of the acylacetic amide series and in their preparation - Google Patents
Improvements in metalliferous complexes of mono-azo dyestuffs of the acylacetic amide series and in their preparationInfo
- Publication number
- GB810207A GB810207A GB21089/55A GB2108955A GB810207A GB 810207 A GB810207 A GB 810207A GB 21089/55 A GB21089/55 A GB 21089/55A GB 2108955 A GB2108955 A GB 2108955A GB 810207 A GB810207 A GB 810207A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methoxy
- acetoacetylamino
- dyestuffs
- chloro
- substituents
- 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
- 150000001408 amides Chemical class 0.000 title abstract 3
- 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
- -1 nitro, methoxy Chemical group 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052751 metal Inorganic materials 0.000 abstract 3
- 239000002184 metal Substances 0.000 abstract 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- 150000001805 chlorine compounds Chemical class 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
- 239000000975 dye Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 210000002268 wool Anatomy 0.000 abstract 2
- PDZPVKKEDKMGAW-UHFFFAOYSA-N 3-oxo-N-(2-phenyl-1,3-benzothiazol-6-yl)butanamide Chemical compound C1(=CC=CC=C1)C=1SC2=C(N1)C=CC(=C2)NC(CC(=O)C)=O PDZPVKKEDKMGAW-UHFFFAOYSA-N 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
- 229920003043 Cellulose fiber Polymers 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000684 Cobalt-chrome Inorganic materials 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 1
- HXOQBPHESQQXQH-UHFFFAOYSA-N N-(2-ethylsulfanyl-1,3-benzothiazol-6-yl)-3-oxobutanamide Chemical compound C(C)SC=1SC2=C(N1)C=CC(=C2)NC(CC(=O)C)=O HXOQBPHESQQXQH-UHFFFAOYSA-N 0.000 abstract 1
- TVWJQOJGSDYNOI-UHFFFAOYSA-N N-(2-methoxy-1,3-benzothiazol-6-yl)-3-oxobutanamide Chemical compound C(CC(=O)C)(=O)NC1=CC2=C(N=C(S2)OC)C=C1 TVWJQOJGSDYNOI-UHFFFAOYSA-N 0.000 abstract 1
- ZBTUXPQMMKQUNX-UHFFFAOYSA-N N-(5-methoxy-1,3-benzothiazol-6-yl)-3-oxobutanamide Chemical class COC=1C(=CC2=C(N=CS2)C=1)NC(CC(=O)C)=O ZBTUXPQMMKQUNX-UHFFFAOYSA-N 0.000 abstract 1
- CCQWEVZIUATCBD-UHFFFAOYSA-N N-(6-methyl-2-methylsulfanyl-1,3-benzothiazol-5-yl)-3-oxobutanamide Chemical class CC1=CC2=C(N=C(S2)SC)C=C1NC(CC(=O)C)=O CCQWEVZIUATCBD-UHFFFAOYSA-N 0.000 abstract 1
- ULABNNPITCNAEE-UHFFFAOYSA-N N-(9H-carbazol-3-yl)-3-oxobutanamide Chemical compound C(CC(=O)C)(=O)NC=1C=CC=2NC3=CC=CC=C3C2C1 ULABNNPITCNAEE-UHFFFAOYSA-N 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- 229920000297 Rayon Polymers 0.000 abstract 1
- 229910006074 SO2NH2 Inorganic materials 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001448 anilines Chemical class 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 150000001716 carbazoles Chemical group 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 229920003086 cellulose ether Polymers 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052804 chromium Inorganic materials 0.000 abstract 1
- 239000011651 chromium Substances 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 239000010952 cobalt-chrome Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 239000011572 manganese Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- KRVAVIMTIIEASB-UHFFFAOYSA-N n-(1,3-benzothiazol-2-yl)-3-oxobutanamide Chemical class C1=CC=C2SC(NC(=O)CC(=O)C)=NC2=C1 KRVAVIMTIIEASB-UHFFFAOYSA-N 0.000 abstract 1
- XLBAOZAFVOGBMQ-UHFFFAOYSA-N n-(2-methylsulfanyl-1,3-benzothiazol-6-yl)-3-oxobutanamide Chemical compound C1=C(NC(=O)CC(C)=O)C=C2SC(SC)=NC2=C1 XLBAOZAFVOGBMQ-UHFFFAOYSA-N 0.000 abstract 1
- GXFGVXXEQKKDGE-UHFFFAOYSA-N n-(6-ethoxy-1,3-benzothiazol-2-yl)-3-oxobutanamide Chemical class CCOC1=CC=C2N=C(NC(=O)CC(C)=O)SC2=C1 GXFGVXXEQKKDGE-UHFFFAOYSA-N 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N ortho-hydroxyaniline Natural products NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- 125000000565 sulfonamide group Chemical group 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- 150000003673 urethanes Chemical class 0.000 abstract 1
- 239000002966 varnish Substances 0.000 abstract 1
- 235000013311 vegetables Nutrition 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 complexes of dyestuffs of formula: <FORM:0810207/IV (c)/1> where X is OH or COOH, A may contain substituents other than SO3H or COOH groups and R is a benzthiazole or carbazole nucleus which may contain substituents which do not confer water-solubility. They may be made by diazotizing an appropriately substituted aniline, coupling with the desired amide and metallizing the product. Indicated as substituents for R are halogen, alkyl, aryl, alkoxy and alkylthio groups and as substituents for A are halogen, alkyl, nitro, methoxy, acyl- and aryl-amino, sulphonamido, alkyl- and aryl-sulphonylamino, ketoalkyl and sulphone groups. Complexes containing less than one atom of metal per mol. of dyestuff may be obtained by convention processes. Metallizing agents yielding cobalt chromium, copper, nickel, iron, manganese and aluminium are mentioned. The metal dyestuffs may be used to colour solvents, lacquers, varnishes and products based on cellulose ethers and esters. Some of the dyestuffs, especially those containing an SO2NH2, SO2NHCH3, SO2CH3 or SO2C2H2 group in A dye, from a neutral or acetic acid bath, wool, silk, leather, animalized cellulose fibres and fibres of superpoly-amides and urethanes whilst leaving vegetable and acetate rayon fibres uncoloured. In examples illustrative of the preparation of cobalt and chromium dyestuffs and their use in dyeing wool in yellow shades the diazo components used are 2-amino-4-sulphonamido-1-phenol, 4 - nitro - 2 - aminophenol and 4-chloro - 2 - amino - 5 - sulphonamidophenol the coupling components being 2-acetoacetylamino-and 2 - acetoacetylamino - 6 - ethoxy benzthiazoles, 5 - chloro - and methoxy - 6 - acetoacetylaminobenzthiazole, 2 - methoxy and methylthio - 5 - acetoacetylamino - 6 - methylbenzthiazoles, 2 - ethylthio - 6 - acetoacetylamino - benzthiazole and its 5 - methyl, methoxy and chloro derivatives, 2-methylthio-6 - acetoacetylaminobenzthiazole and its 5-methyl, methoxy and chloro - derivatives, 2-ethylthio - and methyl - 5 - acetoacetylamino-6 - methoxy -, 2 - ethoxy - 5 - acetoacetylamino or methoxy - 6 - methoxy or acetoacetylamino - benzthiazoles, 2 - methoxy - 5 - methoxy - 5 - acetoacetylamino and 5 - methoxy - 6-acetoacetylamino - benzthiazoles, 2 - phneyl - 5-acetoacetylamino - 6 - methoxybenthiazole, 2-phenyl - 6 - acetoacetylaminobenzthiazole and 3 - acetoacetylaminocarbazole. Specifications 516,851, 598,985 and 598,986, [all in Group IV], are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR810207X | 1954-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB810207A true GB810207A (en) | 1959-03-11 |
Family
ID=9254789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21089/55A Expired GB810207A (en) | 1954-07-26 | 1955-07-21 | Improvements in metalliferous complexes of mono-azo dyestuffs of the acylacetic amide series and in their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB810207A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2592054A1 (en) * | 1985-12-23 | 1987-06-26 | Ciba Geigy Ag | ASYMMETRIC CHROME COMPLEX DYES 1: 1, PROCESS FOR THEIR PREPARATION AND THEIR USE |
-
1955
- 1955-07-21 GB GB21089/55A patent/GB810207A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2592054A1 (en) * | 1985-12-23 | 1987-06-26 | Ciba Geigy Ag | ASYMMETRIC CHROME COMPLEX DYES 1: 1, PROCESS FOR THEIR PREPARATION AND THEIR USE |
| US4874849A (en) * | 1985-12-23 | 1989-10-17 | Ciba-Geigy Corporation | Asymmetric 1:2-chromium complex dyes containing two azo dyes, one containing an acetoacetanilide coupling component |
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