GB719363A - Manufacture of metalliferous azo-dyestuffs - Google Patents
Manufacture of metalliferous azo-dyestuffsInfo
- Publication number
- GB719363A GB719363A GB32481/52A GB3248152A GB719363A GB 719363 A GB719363 A GB 719363A GB 32481/52 A GB32481/52 A GB 32481/52A GB 3248152 A GB3248152 A GB 3248152A GB 719363 A GB719363 A GB 719363A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- azo
- group
- acid
- bound
- 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
- 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
- C09B45/22—Monoazo compounds containing other metals
-
- 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
- C09B45/18—Monoazo compounds containing copper
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/09—Colouring agents for toner particles
- G03G9/0906—Organic dyes
- G03G9/091—Azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Coloring (AREA)
Abstract
The invention comprises metalliferous azo dyestuffs of formula:- <FORM:0719363/IV(c)/1> where R1 is a heterocyclic residue having a five-membered hetero-ring containing two hetero-atoms of which at least one is a nitrogen atom bound exclusively in the ring, <FORM:0719363/IV(c)/2> is the residue of a middle component of the benzene or naphthalene series to which the azo linkages are bound in paraposition relatively to one another and the substituent U is bound in ortho-position relatively to the azo-linkage connecting R2 with R3, U is O or -COO of which the carbon atom is bound to R2, <FORM:0719363/IV(c)/3> is the residue of a 1-oxy-naphthalene-3-sulphonic acid bound in the 2-position to the azo linkage and contains in a b -position an amino group, and Me is Ni or Cu. They may be made by treating a dyestuff of formula <FORM:0719363/IV(c)/4> with an agent yielding nickel or copper under conditions such that an o, o1-dioxy-azo-or o-oxy-o1-carboxy-azo-metal complex is formed, when necessary, with the splitting off of the alkyl group from the group U. The metal free dyestuffs may be made by coupling, advantageously in a weakly acid to weakly alkaline medium, a diazo compound of R1NH2 with, <FORM:0719363/IV(c)/5> , diazotizing and coupling the diazo-azo-compound with H-R3 -OH in an alkaline medium optionally with the addition of agents such as pyridine or picoline. Specified initial components which advantageously contain a group imparting solubility e.g. a sulphonic acid group, are 5- or 6-amino-indazole, 6-amino-benzimidazole, 2-methyl-6-amino-benzimidazole, 2-methyl-5-amino-benzimidazole-7-sulphonic acid and 1,2-dimethyl-5-amino-benzimidazole-7-sulphonic acid. Advantageously the initial component contains the diazotizable amino group attached to an aryl nucleus which is bound to the hetero-ring by a simple bound as in 2-(41-aminophenyl)-benzimidazole and its 1-methyl derivative and 2-(41aminophenyl)-benzoxazole and their sulphonic acids. Other specified initial components are 2- and 6-amino-benzthiazole, 6-amino-2-methylbenzthiazole, 2-aminothiazole, 2-(41- and 31-aminophenyl)-benzthiazole, 2-(41-aminophenyl)-5- and 6-chloro-, 6-methoxy and -ethoxy-benzthiazole and their sulphonic acids preferred being 2-(41-aminophenyl)-6-methyl-benzthiazole and its mono- and di-sulphonic acids. The middle components are advantageously of the benzene series and contain a methoxy group specified being 2-amino-4-methyl-1-oxybenzene, 2-aminobenzene-1-carboxylic acid, 1-amino-2-methoxy-, 2, 5-dimethoxy- and 2, 5-diethoxy-benzene, 1-amino-2-methoxy - 5-methylbenzene, 1 - amino-2-methoxy and 2-ethoxy-naphthalene and their 6- or 7-sulphonic acids. Middle components of poor coupling power may be used as their o -methane sulphonic acids. Specified end components are 2-amino- 2-acetylamino-, 2-benzoylamino-, 2-phenylamino- and 2-(41-carboxymethoxyphenylamino)-5-oxynaphthalene - 7 - sulphonic acid, 2 - amino-, 2 acetylamino-, 2 - benzoylamino-, 2 - b - oxyethylamino-, 2 - methylamino-, 2 - phenylamino-, 2 - (41-carboxy - methoxyphenyl amino) - and 2 - (N - methyl - phenylamino - 8 - oxynaphthalene - 6 - sulphonic acid, 2-phenylamino-8-oxynaphthalene-6-sulphonic acid-31- or -41-carboxylic acid or 31-sulphonic acid amide, 2-phenylamino-8-oxynaphthalene-6, 31- or -6, 41-disulphonic acid advantageously 2-phenylamino-8-oxynaphthalene-6-sulphonic acids are used in which the phenyl group contains groups such as the sulphonic acid or carboxylic group which impart solubility. Desirably the disazo-dyestuff contains at least two groups imparting solubility. Metallization is effected in known manner e.g. with salts of divalent nickel or copper in a weakly acid medium or with a nickel or copper tetrammine in the presence or absence of an excess of amine or ammonium or as in Specification 644,883 in the presence of an oxyalkylamine or a copper complex derived therefrom. The metal dyestuffs may be used for dyeing wool, silk, leather, cotton, linen, artificial silk and regenerated cellulose in grey, blue, green or brown tints. Examples and a table describe the use of certain of the reagents specified above.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH719363X | 1951-12-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB719363A true GB719363A (en) | 1954-12-01 |
Family
ID=4531417
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB32481/52A Expired GB719363A (en) | 1951-12-21 | 1952-12-22 | Manufacture of metalliferous azo-dyestuffs |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB719363A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2835661A (en) * | 1956-04-19 | 1958-05-20 | Eastman Kodak Co | Metallized thiazoleazohydroxyamine compounds |
US2837507A (en) * | 1954-03-16 | 1958-06-03 | Ciba Ltd | Cupriferous azo-dyestuffs |
US5639809A (en) * | 1994-06-22 | 1997-06-17 | Mitsui Toatsu Chemicals, Inc. | Azo compounds and polarizing films using the compounds |
-
1952
- 1952-12-22 GB GB32481/52A patent/GB719363A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2837507A (en) * | 1954-03-16 | 1958-06-03 | Ciba Ltd | Cupriferous azo-dyestuffs |
US2835661A (en) * | 1956-04-19 | 1958-05-20 | Eastman Kodak Co | Metallized thiazoleazohydroxyamine compounds |
US5639809A (en) * | 1994-06-22 | 1997-06-17 | Mitsui Toatsu Chemicals, Inc. | Azo compounds and polarizing films using the compounds |
US5698682A (en) * | 1994-06-22 | 1997-12-16 | Mitsui Toatsu Chemicals, Inc. | Azo compounds and polarizing films using the compounds |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB719363A (en) | Manufacture of metalliferous azo-dyestuffs | |
GB978721A (en) | Improvements in or relating to reactive azo dyestuffs | |
ES416529A1 (en) | Azo dyes derived from thiophene diazo components | |
GB790904A (en) | Improvements relating to metallisable monoazo dyestuffs, complex heavy metal compounds thereof, and their use | |
GB756599A (en) | Manufacture of cupriferous disazo-dyestuffs | |
GB760347A (en) | Azo-dyestuffs, metalliferous azo-dyestuffs and process for making them | |
GB755113A (en) | New cobaltiferous azo-dyestuffs and process for making them | |
GB654744A (en) | Manufacture of new trisazo-dyestuffs | |
GB1056524A (en) | New reactive disazo dyestuffs and metal complexes thereof and processes for their manufacture and use | |
GB586840A (en) | Manufacture of disazo-dyestuffs | |
SE128026C1 (en) | ||
GB679604A (en) | Manufacture of new azo-dyestuffs | |
GB757047A (en) | New metalliferous trisazo-dyestuffs and process for making them | |
GB1111544A (en) | Azo dyestuffs containing metal and a reactive sulphonamide residue and processes for their manufacture | |
GB777050A (en) | Metalliferous monoazo-dyestuffs and processes for their manufacture and use | |
GB874355A (en) | New azo dyestuffs of the phthalocyanine series | |
GB772593A (en) | Process for producing azo-dyestuffs insoluble in water on mixtures of polyamide fibres with animal or vegetable fibres | |
GB821331A (en) | New disazo-dyestuffs and process for their manufacture | |
GB756190A (en) | New metalliferous azo-dyestuffs and process for making them | |
GB695330A (en) | Manufacture of trisazo-dyestuffs | |
GB744406A (en) | Manufacture of azo-dyestuffs | |
GB755853A (en) | Monoazo dyestuffs | |
GB784879A (en) | New polyazo-dyestuffs and process for making them | |
GB697136A (en) | Manufacture of disazo- and polyazo-dyestuffs | |
GB806050A (en) | Cupriferous dis-azo-dyestuffs of the benzthiazole series |