GB963426A - Improvements relating to metal-containing formazane reactive dyestuffs and their use - Google Patents

Improvements relating to metal-containing formazane reactive dyestuffs and their use

Info

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
Application number
GB152861A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
JR Geigy AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from CH43260A external-priority patent/CH441571A/en
Application filed by JR Geigy AG filed Critical JR Geigy AG
Publication of GB963426A publication Critical patent/GB963426A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/002Reactive 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
    • C09B62/018Formazane 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.
GB152861A 1960-01-15 1961-01-13 Improvements relating to metal-containing formazane reactive dyestuffs and their use Expired GB963426A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (2)

* Cited by examiner, † Cited by third party
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

Similar Documents

Publication Publication Date Title
GB1474343A (en) Process for dyeing polyurethane plastics
GB1101750A (en) New copper complexes of disazo dyestuffs containing a triazine nucleus
US2155755A (en) Mono-azo dyestuffs
GB963426A (en) Improvements relating to metal-containing formazane reactive dyestuffs and their use
GB1425029A (en) Azo dyes derived from thiophene diazo components
GB1004059A (en) Monoazo dyes free from sulfonic acid groups
GB1052002A (en)
DE2001821A1 (en) Water-insoluble monoazo dyes
US2832762A (en) Monoazo dyestuffs and complex metal compounds thereof
DE1904111C3 (en) Fiber-reactive formazan dyes containing heavy metals, processes for their production and their use for dyeing or printing textile materials
GB916532A (en) Water-soluble dyes of the phthalocyanine-azo series
US2602788A (en) Tetrakisazo dyestuffs
DE1186572B (en) Process for the preparation of metal complex dyes
DE2022453C3 (en) Azo dyes and their 1 to 1 metal complexes, their production and use
GB974403A (en) Mixed chromium complexes of monoazo dyes containing sulphonic acid groups
DE2540588C2 (en) New leather dyes, their production and use
GB1106048A (en) Disazo dyes containing a heterocyclic residue and free from sulphonic acid groups
ES262953A1 (en) Improvements relating to metal-containing reactive azo dyestuffs containing pyrimidylamino groups and their use
GB1033901A (en) Azo dyes containing n-alkoxy-sulphonamide groups and metal complexes thereof
GB816991A (en) Dyestuffs of the benzene-monoazo-naphthalene series and metal derivatives thereof
GB951452A (en) Water-insoluble metalliferous triazole azo-dyestuffs and process for their manufacture
GB1150010A (en) Copper Complexes of Azo Dyes containing Sulphonic Acid Groups and Their Production
DE2232080A1 (en) Basic azo dyes, free from sulphonic acid gas - as coupling components , for writing fluids and dyeing/printing cellulosics or polyamides
GB927771A (en) New metallised disazo-triazine dyestuffs
GB1079965A (en) Metallised mono-azo dyestuffs containing a sulphonamide-triazine residue