GB751974A - Improvements relating to metallisable monoazo dyestuffs and dyeings made therewith - Google Patents
Improvements relating to metallisable monoazo dyestuffs and dyeings made therewithInfo
- Publication number
- GB751974A GB751974A GB3057/54A GB305754A GB751974A GB 751974 A GB751974 A GB 751974A GB 3057/54 A GB3057/54 A GB 3057/54A GB 305754 A GB305754 A GB 305754A GB 751974 A GB751974 A GB 751974A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- hydroxy
- sulphonic acid
- acid
- carbomethoxy
- 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
- 238000004043 dyeing Methods 0.000 title 1
- 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 alkali metal salts Chemical class 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- 150000007513 acids Chemical class 0.000 abstract 3
- 230000008878 coupling Effects 0.000 abstract 3
- 238000010168 coupling process Methods 0.000 abstract 3
- 238000005859 coupling reaction Methods 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 abstract 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical class OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 abstract 1
- CUQJYQHDIVIFIF-UHFFFAOYSA-N 3-amino-5-benzamido-4-hydroxybenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(NC(=O)C=2C=CC=CC=2)=C1O CUQJYQHDIVIFIF-UHFFFAOYSA-N 0.000 abstract 1
- NWYPJANFHLUNFH-UHFFFAOYSA-N 7-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=C(O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 NWYPJANFHLUNFH-UHFFFAOYSA-N 0.000 abstract 1
- FFWLNOFHJLXQLC-UHFFFAOYSA-N 8-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=C2C(N)=CC=CC2=C1 FFWLNOFHJLXQLC-UHFFFAOYSA-N 0.000 abstract 1
- 229930194542 Keto Natural products 0.000 abstract 1
- 240000007817 Olea europaea Species 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamic acid group Chemical group C(N)(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001664 diethylamino group Chemical class [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 150000002148 esters Chemical group 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 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
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 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)
- Coloring (AREA)
Abstract
The invention comprises dyestuffs of formula:-<FORM:0751974/IV(c)/1> where R1 and R2 are carboxyl radicles and X any substituent and the alkali metal salts thereof. The are made by coupling in an alkaline solution, optionally in the presence of a tertiary nitrogen base, a diazotised 4-substituted - 6 - acylamino - 2 - amino - 1 - hydroxybenzene with a 2 - hydroxy - acylaminonaphthalene monosulphonic and X is preferably a group which has an attracting influence on the pair of electrons linking it to the residue of the component, such groups specified being nitro, cyano, keto, sulphonyl, sulphonic acid, sulphonic acid ester, sulphonamide, carboxyl, and carboxylic acid ester and amide; other groups specified for X being halogen, alkyl and alkoxy. Preferably X is a non-salt forming group. Specified acids which give rise to R1 and R2 are acetic, propionic, butyric, chloracetic, methoxyacetic, b - bromopropionic, dimethylacrylic, cyclohexane carboxylic, phenyl acetic, phenoxyacetic, benzoic, chlorobenzoic and furane - 2 - carboxylic acids. R1 and R2 may also represent carbonic acid half ester residues derived from methyl, ethyl, propyl, butyl and methoxy or ethoxy ethyl alcohols and carbamic acid residues derived from dimethyl- or diethyl-amines. Preferred diazo components are 6-acetylamino-4-nitro-, acetyl-, alkylsulphonyl- and -sulphonodialkylamido - 2 - amino-1-hydroxy-benzenes. Specified coupling components are acyl derivatives of 1-amino-7-hydroxy-naphthalene - 3 -, - 4 - or - 5 - sulphonic acids, 1 - amino - 6 - hydroxy - naphthalene - 8 - sulphonic acid and preferably 2 - amino - 6 - hydroxynaphthalene - 8 - sulphonic acid. The dyestuffs dye wool from acid baths in red to red-violet shades which become grey to olive green on after chroming. Examples are provided illustrating the preparation of the dyestuffs the diazo components used being 6-acetylamino-4-chloro-, -acetyl-, -nitro-, -carboxy-, sulpho-, -methylsulphonyl -, - ethylsulphonyl -, phenylsulphonyl-, -31-sulphophenylsulphonyl-, -31-sulphamidophenylsulphonyl-, -sulphonamido-, -sulphondimethylamido-, -sulphondiethylamido-, -sulphonmorpholido-, -sulphonethylphenylamido-, -sulphon - 21 - carboxyphenylamido-, methyl-, methoxy- and -benzoyl - 2 - amino - 1 - hydroxybenzene, 6-carbomethoxy-, -butyryl-, -21furoyl-, -dimethyl-, acrylyl- and b -bromo-propionyl-4-nitro - 2 amino - 1 - hydroxy-benzene and 6 - benzoylamino - 4 - sulpho-2-amino-1-hydroxybenzene and the coupling components are 2-carbomethoxy-, -carboethoxy-, carbutyroxy-, -acetyl-, -cyclohexoyl-, -chloroacetyl-, - b - bromopropionyl-, -41-chlorobenzoyl-, -phenylacetyl-, -benzoyl-, -phenoxyacetyl-, -21-furoyl- and -dimethyl - carbamyl - amino- 6 - hydroxy-naphthalene-8-sulphonic acid, 1-carbomethoxy-, -carboethoxy- and -acetyl-amino-7-hydroxy - 3 - sulphonic acid and 1-carbomethoxy- and -carboethoxy-7-hydroxy-4 and -5-sulphonic acids and 61-hydroxy-naphthyl-(21)-methoxy- and -ethoxy-ethyl-urethane-81-sulphonic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH751974X | 1953-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB751974A true GB751974A (en) | 1956-07-04 |
Family
ID=4533973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3057/54A Expired GB751974A (en) | 1953-02-04 | 1954-02-02 | Improvements relating to metallisable monoazo dyestuffs and dyeings made therewith |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB751974A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2202232A (en) * | 1987-03-19 | 1988-09-21 | Ciba Geigy Ag | Process for preparing metallizable monoazo dyes |
-
1954
- 1954-02-02 GB GB3057/54A patent/GB751974A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2202232A (en) * | 1987-03-19 | 1988-09-21 | Ciba Geigy Ag | Process for preparing metallizable monoazo dyes |
| GB2202232B (en) * | 1987-03-19 | 1991-03-06 | Ciba Geigy Ag | Process for preparing metallizable monoazo dyes |
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