GB907382A - Disazo and trisazo dyestuffs and nickel complexes thereof - Google Patents
Disazo and trisazo dyestuffs and nickel complexes thereofInfo
- Publication number
- GB907382A GB907382A GB3952558A GB3952558A GB907382A GB 907382 A GB907382 A GB 907382A GB 3952558 A GB3952558 A GB 3952558A GB 3952558 A GB3952558 A GB 3952558A GB 907382 A GB907382 A GB 907382A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitro
- acid
- azo
- group
- reacted
- 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
-
- 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
- C09B27/00—Preparations in which the azo group is formed in any way other than by diazotising and coupling, e.g. oxidation
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/08—Preparation of azo dyes from other azo compounds by reduction
- C09B43/10—Preparation of azo dyes from other azo compounds by reduction with formation of a new azo or an azoxy bridge
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
-
- 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
- C09B45/04—Azo compounds in general
-
- 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
- C09B45/24—Disazo or polyazo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
6 - Nitro - 1:2-naphthoquinone-4-mono- and 4:8-disulphonic acids are prepared by oxidising the diazo-oxide of 1-amino-2-hydroxy-6-nitro-naphthalene-4-mono- or 4:8-disulphonic acid with, for example, chlorine, bromine or sodium chlorate and hydrochloric acid. The disulphonic acid may also be prepared by treating 6 - nitro - 2-amino-naphthalene-4:8-disulphonic acid with chlorine in 3% aqueous hydrochloric acid. N : N - bis[1:2-di-oxo-4:8-disulphonaphthyl-(6)]-urea is prepared by reducing 6-nitro-1:2-naphthoquinone - 4:8 - disulphonic acid to 6-amino - 1:2 - dihydroxy-naphthalene-4:8-disulphonic acid reacting this with phosgene and treating the urea formed, in acid solution, with an excess of sodium nitrite. Specifications 660,447, 721,495, 790,386, 820,476, 837,996, 866,914, 907,383 and 907,384 are referred to.ALSO:The invention comprises dyes of formula: <FORM:0907382/IV (b)/1> wherein R is a monoazo dye radical, B is an azo, azoxy, urea, secondary or tertiary triazinylamino, terephthaloylamino or fumaroylamino bridge member, X1 is a hydrogen atom or a sulphonic acid group, R1 is an aromatic radical containing Y1 in o-position to the azo bridge and Y1 is a metal-complex forming a group other than hydroxyl or alkoxy and the nickel and copper complexes thereof. The invention also comprises a process for the preparation of azo dyes wherein an aromatic or heterocyclic hydrazine compound or the corresponding N-b -sulphonic acid having in o-position to the hydrazine group a substituent capable of forming a metal complex or a substituent or atom convertible thereto under metallising conditions is reacted with a 6-nitro-or-acylamino-1 : 2-naphthoquinone-4- or - 8-mono- or -4 : 8-disulphonic acid, the dye coppered or nickelled if desired, the 6-nitro-or-acylaminogroup converted into an azo, azoxy, urea, secondary or tertiary triazinylamino, terephthaloylamino or fumaroylamino bridge member by reductively linking the nitro group to form an azo or azoxy group, by reduction of the nitro group or saponification of the acylamino group to an amino group which is diazotized and coupled with an azo component or reacted with phosgene, a di- or tri-halotriazine, terephthaloyl or fumaroyl chloride or first with phenyl chloroformate to form the phenylurethane which is then reacted with a 1-hydroxy-2-azo-6-aminonaphthalene sulphonic acid to form the urea. In a modification of the process the quinone p reactant is replaced by the corresponding 1-oxime (or 1-nitroso-2-hydroxy compound). The 1-hydroxylamino-2-azo compound formed in the first stage is further reacted with sodium nitrite and hydrochloric acid to give a 1-hydroxy-2-azo-compound which is further reacted as above. The dyes give blue shades on cellulose fibres. In Examples: (1) 6-nitro-1 : 2-naphthoquinone-4-sulphonic acid is reacted with 2-hydrazinonaphthalene-3: 6-disulphonic and the monoazo dye is oxidatively coppered and reduced using glucose in alkaline medium; (2) 6-nitro-1-nitroso-2-naphthol-4-sulphonic acid is reacted with phenylhydrazine-2: 5-disulphonic acid, the monoazo dye formed is treated with sodium nitrate and hydrochloric acid, oxidatively coppered and linked by reduction; (3) 6-nitro-or-acetylamino- 1 : 2-naphthoquinone-4-sulphonic acid is reacted with 2-hydrazinonaphthalene-3:6:8-trisulphonic acid, the nitro group reduced with sodium sulphide or the acetylamino group hydrolysed, the aminoazo dye reacted with phosgene to form the disazo dye which is oxidatively coppered. Further examples are specified. Specifications 660,447, 721,495, 790,386, 820,472, 837,996, 866,914, 907,383 and 907,384 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF24681A DE1098644B (en) | 1957-12-23 | 1957-12-23 | Process for the production of azo dyes and their metal complex compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB907382A true GB907382A (en) | 1962-10-03 |
Family
ID=7091324
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3952558A Expired GB907382A (en) | 1957-12-23 | 1958-12-08 | Disazo and trisazo dyestuffs and nickel complexes thereof |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE574173A (en) |
CH (3) | CH461679A (en) |
DE (1) | DE1098644B (en) |
GB (1) | GB907382A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2033989C2 (en) * | 1969-07-18 | 1985-05-09 | Ciba-Geigy Ag, Basel | Storage-stable concentrated solutions of metal complexes of azo or azo-azomethine dyes and their uses |
DE4015591A1 (en) * | 1990-05-15 | 1991-11-21 | Boehringer Mannheim Gmbh | NAPHTHOL DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE528166C (en) * | 1927-10-08 | 1931-06-26 | Chemische Ind Ges | Process for the production of metal-containing azo dyes |
DE904228C (en) * | 1950-05-26 | 1954-02-15 | Sandoz Ag | Process for the preparation of copper-containing disazo dyes |
-
1957
- 1957-12-23 DE DEF24681A patent/DE1098644B/en active Pending
-
1958
- 1958-11-23 CH CH572764A patent/CH461679A/en unknown
- 1958-11-24 CH CH1540565A patent/CH460992A/en unknown
- 1958-12-08 GB GB3952558A patent/GB907382A/en not_active Expired
- 1958-12-23 BE BE574173A patent/BE574173A/en unknown
-
1959
- 1959-03-25 CH CH340967A patent/CH443524A/en unknown
Also Published As
Publication number | Publication date |
---|---|
DE1098644B (en) | 1961-02-02 |
BE574173A (en) | 1959-06-23 |
CH460992A (en) | 1968-08-15 |
CH461679A (en) | 1968-08-31 |
CH443524A (en) | 1967-09-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3226176A (en) | Cellulose, wool, silk and leather fibers fast-dyed with chlorotriazine containing reactive dyestuffs | |
GB907382A (en) | Disazo and trisazo dyestuffs and nickel complexes thereof | |
US3157630A (en) | Copper-containing monoazo dyestuffs having a cyanuric halide radical | |
US3342798A (en) | Pyrimidyl azo dyestuffs | |
GB907383A (en) | Disazo and trisazo dyestuffs and copper complexes thereof | |
US2987513A (en) | Azo dyestuffs and process for their manufacture | |
US2741655A (en) | Cupriferous azo-dyestuffs | |
US2476261A (en) | Process for the manufacture of asymmetrical polyazo-dyestuffs | |
US2251813A (en) | Azo dye | |
US2696486A (en) | Disazo-dyestuffs | |
US3660393A (en) | Anthraquinonyl-triazines | |
CA1049507A (en) | Polyazo dyestuffs, their production and their use | |
US1819080A (en) | Production of trisazo dyes | |
US1849573A (en) | Disazo-dyestuffs and process of making same | |
US2228416A (en) | Azo dyes | |
DE1544425A1 (en) | Process for the preparation of direct disazo dyes | |
US2155685A (en) | Azo dyes | |
US3202651A (en) | Process for the production of omicron-hydroxy azo compounds | |
US2055741A (en) | Azodyestuffs | |
US2858302A (en) | Polyazo dyestuffs and the metal complex compounds | |
US2199576A (en) | Process for the selective reduction of azo compounds | |
US2297801A (en) | Azo dyes | |
GB907384A (en) | Process for the preparation of disazo and trisazo dyestuffs and copper complexes thereof | |
US1904822A (en) | Azo dyestuffs and method of preparing same | |
US2164524A (en) | Azo dye |