GB924452A - Metalliferous azo-dyestuffs and process for their manufacture - Google Patents
Metalliferous azo-dyestuffs and process for their manufactureInfo
- Publication number
- GB924452A GB924452A GB28254/60A GB2825460A GB924452A GB 924452 A GB924452 A GB 924452A GB 28254/60 A GB28254/60 A GB 28254/60A GB 2825460 A GB2825460 A GB 2825460A GB 924452 A GB924452 A GB 924452A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dyestuff
- free
- dyestuffs
- chromium
- azo
- 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
- 238000000034 method Methods 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000000975 dye Substances 0.000 abstract 10
- 229910052804 chromium Inorganic materials 0.000 abstract 5
- 239000011651 chromium Substances 0.000 abstract 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 4
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 abstract 4
- 125000004429 atom Chemical group 0.000 abstract 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 1
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical class C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000003172 aldehyde group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 abstract 1
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000001845 chromium compounds Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 229910001385 heavy metal Inorganic materials 0.000 abstract 1
- 150000005204 hydroxybenzenes Chemical class 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- -1 sulphonamido Chemical group 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
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
- C09B45/24—Disazo or polyazo compounds
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises metalliferous azodyestuffs which contain one atom of chromium bound in complex union to two molecules of two dyestuffs, one of which is an ortho-hydroxy-ortho1-amino-monoazo-dyestuff containing a primary amino group in the ortho1-position and the other is an azomethine or monoazo dyestuff free from secondary amino groups and both of which dyestuffs are free from carboxylic groups not present in ortho-position to the azo linkage and from sulphonic groups, and a process for the manufacture of metalliferous azo-dyestuffs which contain one atom of chromium bound in complex union to two molecules of monoazo dyestuffs or to one molecule of a monoazo dyestuff and one molecule of an azomethine dyestuff wherein a metal-free metallizable mono-azo dyestuff or azomethine dyestuff and a complex chromium compound of an ortho-hydroxy-ortho1-amino-monoazo dyestuff which contains one atom of chromium bound in complex union to one molecule of dyestuff are reacted together in a molecular ratio of about 1:1 and the starting materials are free from carboxylic acid groups not in ortho position to the azo linkage and from sulphonic acid groups. The 1:1-chromium complex compounds may contain non-ionic substituents such as chlorine atoms, nitro, alkyl, alkoxy, alkylsulphonide, alkyl sulphone, cyclic alkanesulphonyl, sulphonamido and acylamino groups. Azo dyes free from heavy metal for use in the process may be prepared by coupling o-hydroxyamines or o-carboxyamines of the naphthalene or benzene series with hydroxybenzenes, hydroxynaphthalenes, 2, 4-dihydroxyquinolines, pyrazolones and acetoacetylaminobenzenes capable of coupling in a position vicinal to a hydroxyl group or an enolisable keto group. Metal-free azomethine dyes for use in the process are prepared by reacting aromatic aldehydes which contain a hydroxyl group in a position vicinal to the aldehyde group and amines which contain in a position vicinal to the amino group a complex forming group. The chromium containing starting materials may be prepared by chroming the appropriate metal free dyes by conventional methods. The complexes are suitable for dyeing and printing silk, leather, wool and polyamide and polyurethane fibres. Examples are furnished.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7691659A CH373841A (en) | 1959-08-13 | 1959-08-13 | Process for the production of metal-containing azo dyes |
| CH7769159 | 1959-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB924452A true GB924452A (en) | 1963-04-24 |
Family
ID=25738319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28254/60A Expired GB924452A (en) | 1959-08-13 | 1960-08-15 | Metalliferous azo-dyestuffs and process for their manufacture |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB924452A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3978037A (en) * | 1973-12-07 | 1976-08-31 | Ciba-Geigy Corporation | Azo, azo methine 1:2 chromium complex dyes |
-
1960
- 1960-08-15 GB GB28254/60A patent/GB924452A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3978037A (en) * | 1973-12-07 | 1976-08-31 | Ciba-Geigy Corporation | Azo, azo methine 1:2 chromium complex dyes |
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