GB775005A - Improvements relating to monoazo dyestuffs containing heavy metal and their use - Google Patents

Improvements relating to monoazo dyestuffs containing heavy metal and their use

Info

Publication number
GB775005A
GB775005A GB24426/53A GB2442653A GB775005A GB 775005 A GB775005 A GB 775005A GB 24426/53 A GB24426/53 A GB 24426/53A GB 2442653 A GB2442653 A GB 2442653A GB 775005 A GB775005 A GB 775005A
Authority
GB
United Kingdom
Prior art keywords
methyl
sulphonic acid
amino
acid
phenol
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
GB24426/53A
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
National Starch and Chemical Investment Holding Corp
Original Assignee
JR Geigy AG
National Starch and Chemical Investment Holding Corp
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
Application filed by JR Geigy AG, National Starch and Chemical Investment Holding Corp filed Critical JR Geigy AG
Publication of GB775005A publication Critical patent/GB775005A/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
    • C09B45/00Complex metal compounds of azo dyes
    • C09B45/02Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14Monoazo compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Coloring (AREA)

Abstract

The preparation, by conventional methods, of the following diazo and azo components 2-aminophenol-4-, 2-aminobenzoic acid-5-, 1-naphthol-3-and 2-naphthol-6-sulphonic acid-N-methylhydroxyethylamides and 2-aminophenol-4-sulphonic acid-N-ethylhydroxyethyl amide is described. Specification 709,495, [Group IV (c)], is referred to. Reference has been directed by the Comptroller to Specifications 637,404 and 745,641, [both in Group IV (c)].ALSO:The invention comprises dyestuffs of formula [D - M1 - D] M2 where M1 is Cr or Co, M2 is an alkali metal or ammonium cation and D is of formula <FORM:0775005/IV(b)/1> where A is a radicle of a diazo component of the benzene series, B is a radicle of an azo component coupled in the o - position to the hydroxyl group, X is an OH or COOH group in the o - position to the azo group or a substituent which under the conditions of the metallization can be converted into such a group, R and R1 are aliphatic hydrocarbon radicles neither containing more than 6 carbon atoms, which together have not more than 8 carbon atoms, and n is 1 or 2 the sulphonic acid amide groups being aromatically bound and A and B may contain non salt-forming substituents. They may be made by treating with chromium - or cobalt - yielding substances dyestuffs of the above formula in which X may also be a group convertible to OH or COOH during the metallization: substantially 1 atom of metal is present for two unmetallized dyestuff molecules, non salt-forming groupings mentioned are halogen, alkyl, alkoxy, aryloxy, nitroacylamino, alkylsulphonyl, arylsulphonyl, sulphonic acid dialkylamide, or sulphonic acid aryl ester and carboxylic acid ester and amide groups. Unmetallized dyestuffs may be made by alkaline coupling a diazotized o - hydroxy, o - carboxy - or o - alkoxy - amino compound of the benzene series with a component of the aliphatic, aliphatic-aromatic, aromatic-isocyclic or aromatic-heterocyclic series which couples in the o - position to a phenolic or enolic hydroxyl group, especially acylacetic acid arylamides, phenols, naphthols and 5 - pyrazolones. Preferably the sulphonamide group is derived from a methylamino or ethylamino alkanol where the alkanol contains 2-6C atoms and advantageously the hydroxyl and amino groups are adjacent to one another. Metallization is advantageously effected in aqueous solution or suspension in the warm with salts of cobalt or trivalent chromium. Preferably alkali metal salts of chromosalicylic acid are used. Dispersing agents or diluents may be present, turkey red oil, formamide, dimethyl formamide and a urea melt being specified. The metallised dyestuffs dye wool and synthetic polypeptide fibres in yellow, red and blue shades. In examples 2 - amino - 1 - hydroxybenzene - 4 - sulphonic acid - N - methyl - hydroxyethylamide is diazotised and coupled with (1) 1 - (31 - chloro -) - or (31, 41 - dichloro) - phenyl - 3 - methyl - 5 - pyrazolone and the products chromed, (2) 1 - (31 - chloro) - phenyl - 3 - methyl - 5 - pyrazolone and the product cobalted, (3) 1 - carbomethoxyamino - or - acetylamino - 7 - hydroxynaphthalene or 7 - hydroxy - naphthyl - (1) - carbamic acid methoxy ethyl ester and the products chromed, (4) b - naphthol and the product chromed, (5) b - naphthol and the product cobalted, (6) acetoacetic acid anilide or 21 - chloranilide and the product cobalted, (7) 1 - phenyl - 3 - methyl - 5 - pyrazolone - 31 - sulphonic acid - N - methyl - hydroxyethylamide and the product chromed, (8) 4 - methyl - 6 - nitro - 2 - amino - 1 - hydroxy - benzene is diazotized and coupled with 1 - phenyl - 3 - methyl - 5 - pyrazolone - 31 - sulphonic acid - N - methyl - hydroxyethylamide the product being chromed, (9) 2 - aminobenzoic acid - 5 - sulphonic acid - N - methyl - hydroxyethylamide is diazotized and coupled with 1 - (31 - chloro-) - phenyl - 3 - methyl - 5 - pyrazolone and the product chromed, (10) 2 - amino - 1 - hydroxybenzene - 4 - sulphonic acid - N - ethyl - hydroxyethyl - amide is diazotized and coupled with 1 - (31 - chloro) - phenyl - 5 - pyrazolone - 3 - carboxylic acid amide and the product chromed, (11) 4 - chloro - 2 - amino - 1 - phenol is diazotized and coupled with 1 - naphthol - 3 - sulphonic acid - N - methyl - hydroxyethylamide and the product chromed and (12) 4 - chloro - 2 - amino - 1 - phenol is diazotised and coupled with 2 - naphthol - 6 - sulphonic acid - N - hydroxyethylmethylamide and the product chromed. A table is provided of metallized dyestuffs the following diazo components additional to those already specified being given 5 - chloro - 2 - amino - 1 - phenol - 4 - sulphonic acid - N - methyl - hydroxyethylamide, 4 - methyl - 2 - amino - 1 phenol - 5 - sulphonic acid - N - methyl - hydroxyethylamide, 4 - chloro - 2 - amino - 1 - phenol - 6 - sulphonic acid - N - methyl - hydroxyethylamide, 4 - nitro - 2 - amino - 1 - phenol - 6 - sulphonic acid - N - ethyl - hydroxyethylamide, 4 -, 5 - and 6 - nitro - 2 amino - 1 - phenol, 4 - chloro - 5 - and - 6 - nitro - and 4, 6 - dinitro - 2 - amino - 1 - phenol, 2 - amino - 1 - phenol - 5 - sulphonic acid - N - methyl - hydroxyethylamide anthranilic acid and 2 - amino - 1 - phenol - 4 - sulphonic acid - N - dimethylamide together with the following additional coupling components 1 - phenyl - 3 - methyl - 5 - pyrazolone, 3, 4 - dimethyl-, 3 - methoxy - 4 - methyl - and 4 - amyl - 1 - phenol, 1 - hydroxy - naphthalene - 3 -, - 4 - and - 5 - sulphonic acid - N - methyl - hydroxyethylamides, 2 - hydroxynaphthalene - 4 - and 8 - sulphonic acid - N - methyl - hydroxyethylamides and 1 - (31 - sulphonic acid - N - methyl - hydroxyethylamidophenyl) - 3 - methyl - 5 - pyrazolone. Specification 709,495 is referred to. Reference has been directed by the Comptroller to Specifications 637,404 and 745,641.
GB24426/53A 1952-09-10 1953-09-03 Improvements relating to monoazo dyestuffs containing heavy metal and their use Expired GB775005A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH775005X 1952-09-10

Publications (1)

Publication Number Publication Date
GB775005A true GB775005A (en) 1957-05-15

Family

ID=4535743

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24426/53A Expired GB775005A (en) 1952-09-10 1953-09-03 Improvements relating to monoazo dyestuffs containing heavy metal and their use

Country Status (1)

Country Link
GB (1) GB775005A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998037057A1 (en) * 1997-02-19 1998-08-27 Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts Preparation of acid amides and metallisation of compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998037057A1 (en) * 1997-02-19 1998-08-27 Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts Preparation of acid amides and metallisation of compounds

Similar Documents

Publication Publication Date Title
US2673199A (en) Metalliferous azo dyestuffs
US2194927A (en) Azo compound
GB851861A (en) Improvements relating to heavy metal-containing azo dyestuffs and their use
US2317387A (en) Dispersible disazo dye
GB775005A (en) Improvements relating to monoazo dyestuffs containing heavy metal and their use
US2370500A (en) Direct blue azo dyes
US2446662A (en) Chromium complexes of pyrazolone azo dyes
US2817655A (en) Azo dyestuffs containing heavy metal
CA1070296A (en) Chromium complexes, their manufacture and use
US2676957A (en) Deaminated trisazo dye
GB778262A (en) Improvements relating to monoazo dyestuffs containing heavy metal and their use
GB988972A (en) Monoazo dyestuffs, their metal complex compounds, and a process for their production
US2289210A (en) Soluble azo dye
US3933785A (en) Azo compounds
US2302530A (en) Azo dye
US2447867A (en) Azo dyestuffs of the pyrazolone series
US4625017A (en) Metal complexes of azo dyes containing a 2-(P-N-aceloacetylaminophenyl) benzothiozole moiety
US3078267A (en) Metallized azo dyes containing a 2-aminophenoldisulfonamide diazo component
US2160448A (en) Metal azo dyestuffs and a process for their manufacture
USRE22046E (en) Azo dyesttjffs containing a heavy
US1913384A (en) Trisazo dyestuff and process of preparing the same
US2780618A (en) Disazo dyestuffs and complex heavy metal compounds thereof
USRE22287E (en) Water-soluble azo dyes from
GB883131A (en) Metallisable azo dyestuffs containing sulphonimide groups and metal complex compounds thereof
US2024368A (en) Monoazo dyes and their production