GB963426A - Improvements relating to metal-containing formazane reactive dyestuffs and their use - Google Patents
Improvements relating to metal-containing formazane reactive dyestuffs and their useInfo
- Publication number
- GB963426A GB963426A GB152861A GB152861A GB963426A GB 963426 A GB963426 A GB 963426A GB 152861 A GB152861 A GB 152861A GB 152861 A GB152861 A GB 152861A GB 963426 A GB963426 A GB 963426A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- group
- dyes
- diazo
- aryl
- 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
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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/018—Formazane dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises dyes of formula <FORM:0963426/C4-C5/1> where R1 is a monovalent radicle, A and B are diazo component residues, X is a metal complexing group o to the azo link, Y is an acid dissociating, salt forming, water solubilizing group, W is a m- or p-benzoyleneamido group, R2 is H or an alkyl group of 1 to 4 C atoms, Z is an acyl radicle which has at least one mobile halogen atom, of atomic number 17 to 35, which reacts with alkali whilst splitting off as an anion, or is a substituent containing such an amido group, Me is a metal of atomic number 24 to 29, n is 1 to 5 and q and m are 1 or 2. The dyes are made in conventional fashion by acylating dyes of the above formula in which Z is H, by metallizing appropriate metal-free dyes or by metallizing a compound of formula <FORM:0963426/C4-C5/2> and coupling the product with an appropriate diazo component. Nickel, cobalt, chromium and copper are specified metals the last named being preferred. Preferably, A and B are diazo components of the benzene or naphthalene series and R1 is also of these series. Cyclic carbimide halides, e.g. 2,4,6 - trichloro - 1,3,5 - triazine, 2-alkoxy, -alkyl, -phenyl, -amino, -alkylamino, -phenylamino, -sulphophenylamino, ureido or quanidino - 4,6 - dichloro - 1,3,5 - triazines, 4,6-dibromo-pyrimidines which contain halogen atoms or negative groups, e.g. nitro, acyl and cyano groups in the remaining positions, tetrameric cyanogen chloride,b -halogen alkanoyl and alkenoyl halides, e.g. b -chlorocrotonic bromide, and m - (b - bromoethylsulphamyl) - benzoyl chloride are indicated as compounds from which Z is derived. The formazone starting materials are obtained by conventional methods, e.g. by coupling 2 mols. of aryl diazonium compound with 1 mol. of a compound which may be coupled twice at a methylene or methine group, possibly whilst splitting off substituents, or via the hydrazones described in the parent Specification. Diazo components indicated are o-hydroxy- and -carboxy-aminobenzenes and -naphthyl-amines. They may be substituted by halogen, cyano, nitro, alkyl, amethyl, cycloalkyl, aryl, alkoxy, aryloxy, sulphonic acid, carboxylic acid, carboxylic acid ester, sulphonic acid ester, sulphonic acid alkylsulphonic acid aralkyl- or sulphonic acid aryl-amide, alkyl-carbonyl, aryl carbonyl, alkylsulphonyl, aryl-sulphonyl, alkylamino, aralkylamino, cycloalkylamino, arylamino, stilbylazo, arylazo, acylamino groups or a group of formula <FORM:0963426/C4-C5/3> Ether, acyloxy or desulphonylamide groups may be present in the diazo components in place of the o-hydroxy or o-carboxy groups. Illustrative of indicated non-metallizable diazo components are aminobenzenes, naphthylamines and aminoazoles, e.g. 2-aminothiazoles and -triazoles, 4-aminopyrazoles, 3-amino-indazoles, 4-aminopyridines and 3-aminoquinolines. If the group <FORM:0963426/C4-C5/4> is in a non-metallizable diazo component it is advantageously a m- or p-monoacylamino-benzene diazonium compound and especially a m- or p-monoacyl or monoazinyl-amino-diazo-benzene-o-sulphonic acid. As in the parent Specification a -carbonylalkanes, a -acyl- and -cyano-acetic acid esters and a -acylacetic acid arylamides are used as coupling components which couple twice at a methylene or methine carbon atom. Generally, aromatic-isocyclic aldehydes are used for hydrazone formation, e.g. benzaldehyde, tolualdehydes, 3-nitrobenzaldehyde, anisaldehyde, vanillin, 4-diethyl-aminobenzaldehyde, 4 - dihydroxy - ethyl-aminobenzaldehyde and furfurol, peperorial, pyridine and benzimidazole aldehydes and aliphatic or araliphatic aldehydes, e.g. acetaldehyde, crotonaldehyde and cinnamaldehyde. The intermediates of formula <FORM:0963426/C4-C5/5> aryldiazonium compound with an appropriate methylene or methine compound containing the COOH group, or a group convertible thereto, e.g. a cyanic or carboxylic ester group. The dyes colour natural and regenerated cellulose fibres in red-brown, violet, blue, green and grey shades. The dyeings are fixed with acid-binding agents. Natural and synthetic polyamides may be dyed in an acid bath, or printed with neutral to weakly acid inks, and subsequently treated with acid binding agents. The acid binding agents may be in the impregnating liquors or printing pastes. Numerous examples are given of the preparation of the dyes and their use in colouring cotton and wool.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH43260A CH441571A (en) | 1959-11-13 | 1960-01-15 | Process for the preparation of metal-containing reactive formazan dyes |
Publications (1)
Publication Number | Publication Date |
---|---|
GB963426A true GB963426A (en) | 1964-07-08 |
Family
ID=4186882
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB152861A Expired GB963426A (en) | 1960-01-15 | 1961-01-13 | Improvements relating to metal-containing formazane reactive dyestuffs and their use |
Country Status (2)
Country | Link |
---|---|
DK (1) | DK102873C (en) |
GB (1) | GB963426A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4556706A (en) * | 1974-12-20 | 1985-12-03 | Ciba Geigy Corporation | Heavy metal-containing formazane dyes containing a fiber-reactive fluorotriazine group |
US4757135A (en) * | 1984-11-03 | 1988-07-12 | Hoechst Aktiengesellschaft | Bicyclic formazan compounds containing a beta-sulfatoethyl-sulfonyl or vinyl sulfonyl group, suitable as fiber reactive dyestuffs |
-
1961
- 1961-01-13 GB GB152861A patent/GB963426A/en not_active Expired
- 1961-01-14 DK DK17161A patent/DK102873C/en active
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4556706A (en) * | 1974-12-20 | 1985-12-03 | Ciba Geigy Corporation | Heavy metal-containing formazane dyes containing a fiber-reactive fluorotriazine group |
US4757135A (en) * | 1984-11-03 | 1988-07-12 | Hoechst Aktiengesellschaft | Bicyclic formazan compounds containing a beta-sulfatoethyl-sulfonyl or vinyl sulfonyl group, suitable as fiber reactive dyestuffs |
Also Published As
Publication number | Publication date |
---|---|
DK102873C (en) | 1965-10-18 |
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