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GB774150A - Improvements in or relating to metalliferous polyazo dyestuffs - Google Patents

Improvements in or relating to metalliferous polyazo dyestuffs

Info

Publication number
GB774150A
GB774150A GB1973/55A GB197355A GB774150A GB 774150 A GB774150 A GB 774150A GB 1973/55 A GB1973/55 A GB 1973/55A GB 197355 A GB197355 A GB 197355A GB 774150 A GB774150 A GB 774150A
Authority
GB
United Kingdom
Prior art keywords
amino
methoxy
acid
sulphonic acid
sulphonic
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
GB1973/55A
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.)
Sandoz AG
Original Assignee
Sandoz 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
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB774150A publication Critical patent/GB774150A/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
    • C09B45/22Monoazo compounds containing other metals
    • 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
    • C09B45/18Monoazo compounds containing copper
    • 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
    • C09B45/24Disazo or polyazo compounds
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/66Natural or regenerated cellulose using reactive dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises metalliferous polyazo dyestuffs having in the metal-free state the formula <FORM:0774150/IV(b)/1> where one R is the radicle of a diazo compound of an aminoazo dyestuff, obtained by coupling a diazo-mono- or -disazo compound containing a metallizable substituent o to the diazo group, in the 7-position of a 1-amino-8- naphthol-mono- or -disulphonic acid and the other R is the radicle of a diazo or diazomonoazo compound containing a metallizable substituent p to the diazo group the product containing from 2-5 sulphonic acid groups. The compounds are made by coupling diazo-compounds of appropriate amines RNH2 in any order with resorcinol and treating the products with metal yielding agents or by first coupling one of the diazo-compounds with resorcinol, metallizing, coupling with the other diazo-compound and finally metallizing. Specified diazo components corresponding to those containing the naphthoasulphonic acid are derived from the following amines: 3-methoxy-4-amino-6-methyl-41-hydroxy 1, 11-azobenzene-31-carboxylic acid, 3-methoxy-4-amino-6-methyl-31-carboxy-41-hydroxy-1, 11-azo-benzene-51-sulphonic acid, 1-amino-3-carboxy-4-phenol-5-sulphonic acid --> 3-methylaniline --> 1-amino-2-methoxy-5-methyl-benzene, 4-amino-1, 11- azobenzene-3-mono-and 3, 41-id-sulphonic acids --> 1-amino-2-methoxy-5-methylbenzene and 1-amino-2-methoxynaphthalene - 6 - sulphonic acid, 2-(41 - amino)-phenyl-6-methylbenzthiazole-monosulphonic acid --> 1-amino-2-methoxy-benzene and its 5-methyl- and acetylamino derivatives, 2-(41-amino)-phenyl-6-methyl-benzthiazolemono- and -di-sulphonic acids --> 3-methylaniline --> 1-amino-2-methoxynaphthalene-6-sulphonic acid, 2-1-amino -2- methoxy -5- methylbenzene, 2-naphthylamine - 4, 8 - and 6, 8 - disulphonic acids --> 3 - methylaniline --> 1 - amino - 2 - methoxy - 5 - methylbenzene, 4 - amino - 41 - nitro - 1, 11 - stilbene-2, 21 - disulphonic acid --> - amino - 2 - methoxy - 5 - methylbenzene and 1 - amino - 2 - methoxynaphthalene - 6 - sulphonic acid, 1 - carboxy - 2 - aniline - 5 - sulphonic acid --> 1 - (41 - amino) - phenyl - 3 - methyl - 5 - pyrazolone --> 1 - amino - 2 - methoxy - 5 - methylbenzene, salicylic acid \sM 4, 41 - diamino - 1, 11 - diphenyl --> 1 - amino-2 - methoxy - 5 - methyl - benzene and 1 - amino - 2 - methoxynaphthalene - 6 - sulphonic acid, salicylic acid \sM 3, 31 - dimethoxy - 4, 41 - diamino - 1, 11 - diphenyl --> 1 - amino - 2 - methoxy - 5 - methylbenzene and 1 - amino - 2 - methoxynaphthalene - 6 - sulphonic acid, 3, 31 - dimethoxy - 4, 41 - diamino - 1, 11 - diphenyl, 1 - amino - 4 - (41 - amino) - benzoylamino benzene - 2 - carboxylic acid and 1 - amino - 4 - (31 - methyl - 41 - amino) - benzoyl - aminobenzene - 2 - carboxylic acid --> salicylic acid, salicylic acid \sM 1 - amino - 4 - (41 - amino) - benzoylaminobenzene --> 1 - amino - 2 - methoxy - 5 - methylbenzene and 1 - amino - 2 - methoxy - naphthalene - 6 - sulphonic acid and 1 - amino - 2 - naphthol - 4 - sulphonic acid \sM 3 - aminophenol --> 1 - amino - 2 - methoxy - 5 - methylbenzene. The 4 - mono - and 3, 6 - or 4, 6 - disulphonic acids are preferred 1 - amino - 8 - naphthol - sulphonic acids. Coupling of the above diazo components with the naphthol sulphonic acids may be effected in weakly alkaline solution, advantageously when using a 1 - amino - 2 - alkoxynaphthalene - 6 - sulphonic acid with the addition of an agent such as pyridine, the diazotization of the intermediates generally being effected by the indirect method. Specified amines for the preparation of the diazo compounds corresponding to the second R are 1 - hydroxy - and - methoxy - 2 - aminobenzene - 4 - sulphonic acids and their amides, 2 - amino - 4 - nitrophenol and its 6 - nitro - and - sulpho - derivatives, anthranilic acid, 2 - amino - 6 - chlorophenol - 4 - sulphonic acid, 1 - methoxy - 2 - amino - 5 - nitrobenzene and its - 4 - sulphonic acid, 1 - amino - 2 - naphthol - 4 - sulphonic acid, 1 - amino-2 - methoxynaphthalene - 6 - sulphonic acid, 3 - methoxy - 4 - amino - 6 - methyl - 41 - hydroxy - 1, 11 - azobenzene - 31 - carboxylic acid, 3 - methoxy - 4 - amino - 6 - methyl - 31 - carboxy - 41 - hydroxy - 1, 11 - azobenzene - 51 - sulphonic acid, 3 - methoxy - 4 - amino - 6 - methyl - 1, 11 - azobenzene - 31 - and - 41 - sulphonic acid and 3 - amino - 4 - hydroxy - 1, 11 - azobenzene - 31 - sulphonic acid. The first coupling with resorcinol may take place in acetic acid, neutral or weakly alkaline solution the second coupling generally requiring in addition to an alkaline agent such as ammonia or sodium carbonate, a diazo stabilizer such as naphthalene - 2 - sulphonic acid and, in some cases, an agent such as pyridine. Metallization may be effected in known fashion most advantageously by heating the aqueous dyestuff paste with metal-yielding agents in the presence of alkali metal salts of lowmolecular aliphatic carboxylic acids. Specified metals are nickel and copper the latter being preferred. The dyestuffs may be after-coppered. Colour shades obtained vary between blue, olive, khaki, brown and grey. Examples are provided of the preparation of the dyestuffs and their use in dyeing cotton and regenerated cellulose additional specified components corresponding to the first diazo component being salicylic acid \sM 1, 4 - diaminobenzene --> 1 - amino - 2 - methoxynaphthalene - 6 - sulphonic acid, 2 - (41 - amino) - phenyl - 6 - methylbenzthiazole monosulphonic acid --> 1 - amino - 2 - hydroxy - 5 - methylbenzene, 2 - (41 - amino) - phenyl - 6 - methylbenzthiazole 1 31 - sulphonic acid --> 1 - methoxy - 2 - amino - 4 - methylbenzene, 1 - amino - 4 - phenol - 3 - carboxylic acid --> 1 - amino - 2 - methoxy - 5 - methylbenzene, 1 - amino - 3 - carboxy - 2 - phenol - 5 - sulphonic acid --> 1 - amino - 2 methoxy - 5 - methylbenzene, 1 - amino - 2 - phenol - 5 - sulphonic acid --> 1 - (41 - amino) - phenyl - 3 - methyl - 5 - pyrazolone --> 1 - amino - 2 - methoxy - 5 - methyl - benzene and 1 - naphthylamine - 4, 8 - disulphonic acid --> 3 - methylaniline --> 1 - amino - 2 - methoxy - 5 - methylbenzene and additional components corresponding to the second diazo component are derived from 1 - methoxy - 2 - amino - 6 - chlorobenzene - and 2 - amino - 6 - nitrophenol - 4 - sulphonic acids.
GB1973/55A 1954-01-22 1955-01-21 Improvements in or relating to metalliferous polyazo dyestuffs Expired GB774150A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH774150X 1954-01-22

Publications (1)

Publication Number Publication Date
GB774150A true GB774150A (en) 1957-05-08

Family

ID=4535674

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1973/55A Expired GB774150A (en) 1954-01-22 1955-01-21 Improvements in or relating to metalliferous polyazo dyestuffs

Country Status (1)

Country Link
GB (1) GB774150A (en)

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