GB998522A - Metalliferous water-insoluble benzimidazole bis-azo dyestuffs and processes for their manufacture - Google Patents
Metalliferous water-insoluble benzimidazole bis-azo dyestuffs and processes for their manufactureInfo
- Publication number
- GB998522A GB998522A GB128462A GB128462A GB998522A GB 998522 A GB998522 A GB 998522A GB 128462 A GB128462 A GB 128462A GB 128462 A GB128462 A GB 128462A GB 998522 A GB998522 A GB 998522A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bath containing
- aromatic
- treated
- fibres
- carboxylic acid
- 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 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 239000000975 dye Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 239000002184 metal Substances 0.000 abstract 4
- 229910052751 metal Inorganic materials 0.000 abstract 4
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 238000004043 dyeing Methods 0.000 abstract 3
- -1 heterocyclic radical Chemical group 0.000 abstract 3
- 235000013311 vegetables Nutrition 0.000 abstract 3
- 229920003043 Cellulose fiber Polymers 0.000 abstract 2
- 229920000742 Cotton Polymers 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 239000000987 azo dye Substances 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 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
- 150000001989 diazonium salts Chemical class 0.000 abstract 2
- 239000000835 fiber Substances 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 238000005470 impregnation Methods 0.000 abstract 2
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 abstract 2
- 239000004627 regenerated cellulose Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 210000002268 wool Anatomy 0.000 abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 150000002736 metal compounds Chemical class 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- BNHPGZHAXVLMKZ-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)acetamide Chemical compound COC1=CC(OC)=C(NC(C)=O)C=C1Cl BNHPGZHAXVLMKZ-UHFFFAOYSA-N 0.000 abstract 1
- GXFGVXXEQKKDGE-UHFFFAOYSA-N n-(6-ethoxy-1,3-benzothiazol-2-yl)-3-oxobutanamide Chemical compound CCOC1=CC=C2N=C(NC(=O)CC(C)=O)SC2=C1 GXFGVXXEQKKDGE-UHFFFAOYSA-N 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/18—Trisazo or higher polyazo dyes
- C09B33/28—Tetrazo dyes of the type A->B->K<-C<-D
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo 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
- C09B45/00—Complex metal compounds of azo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
- D06P1/10—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes containing metal
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
- D06P1/12—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes prepared in situ
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises complex metal compounds of water-insoluble azo dyes of the general formula <FORM:0998522/C4-C5/1> in which A represents aromatic or heterocyclic radical, R1 represents a hydrogen atom or an alkyl group, R2 and R3 represent hydrogen atoms, alkyl or alkoxy groups, 2 represents the radical of an arylamide of an aromatic or heterocyclic ortho-hydroxy carboxylic acid or of an acylacetic acid, the acyl group being derived from a carboxylic acid and n stands for one of the integers 1 and 2 and a process for the preparation thereof wherein a diazonium compound of an amine of the formula <FORM:0998522/C4-C5/2> in which A, R1, R2 and R3 have the meanings given above is coupled with an appropriate arylamide and the dye obtained is treated with an agent yielding metal. The treatment with agents yielding metal may be carried out by known methods during or after the coupling in substance or on the fibre (see Division D1). In Example (3) 7-amino-5-methyl-4-(21-methoxyphenyl - 11 - azo) - benzimidazole is diazotized and coupled with 2,3-hydroxynaphthoyl-aminobenzene and an aqueous copper sulphate solution containing triethanolamine is added and the mixture heated to obtain a dye. Additional diazo components are specified and among the many coupling components specified are terephthaloyl - bis - (1 - acetylamino - 2,4 -dimethoxy-5-chlorobenzene); 1-(31-hydroxy-diphenylene oxide - 21 - carboylamino - 2 - ethoxybenzene) 2 - acetoacetylamino - 6 - ethoxy - benzthiazole and 2,3 - hydroxynaphthoyl aminobenzene. Metals specified include copper, cobalt, nickel, iron and zinc and these may be employed in the form of inorganic or organic salts or complexes, e.g. with hydroxy alkylamines. Many of the products are black dies and they are suitable for dyeing or printing vegetable fibres and regenerated cellulose fibres and for dyeing animal fibres such as wool or silk.ALSO:In a process for forming metalliferous water insoluble azo dyes on animal or vegetable fibres a diazonium compound of an amine of the general formula <FORM:0998522/D1-D2/1> in which A represents an aromatic or heterocyclic radical, R, represents a hydrogen atom or an alkyl group and R2 and R3 represent hydrogen atoms, alkyl or alkoxy groups is coupled on the fibre with an arylamide of an aromatic or heterocyclic ortho-hydroxy carboxylic acid or of an acylocetic acid, the acyl group being derived from a carboxylic acid, the components being selected so that they are free from groups imparting solubility in water and the dyestuff obtained is treated with an agent yielding metal. The dyes may be produced on vegetable fibres, regenerated cellulose fibres and wool and silk by the usual methods. In examples (1) cotton yarn is treated in an impregnation bath containing 1-(21, 31-hydroxynaphthoylamino)-2.4-dimethoxy-5-chlorobenzene and subsequently in a developing bath containing diazotised 7-amino-5-methyl-4-(31-methyl phenyl-11-azo)-benyimidazole and nickel sulphate to obtain a black dyeing; and (2) cotton yarn is treated in an impregnation bath containing 2-(21, 31-hydroxynaphthoylamino)-naphtholene, then in a developing bath containing diazotised 7-amino-5-methyl-4-(21-mechoxy-51-introphenyl-11 -azo)-benzimidazole and the dyed yarn is metallised in a bath containing nickel sulphate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1961F0032946 DE1210962C2 (en) | 1961-01-12 | 1961-01-12 | Process for the production of metal-containing, water-insoluble azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB998522A true GB998522A (en) | 1965-07-14 |
Family
ID=7094872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB128462A Expired GB998522A (en) | 1961-01-12 | 1962-01-12 | Metalliferous water-insoluble benzimidazole bis-azo dyestuffs and processes for their manufacture |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE612591A (en) |
| CH (1) | CH377464A (en) |
| DE (1) | DE1210962C2 (en) |
| GB (1) | GB998522A (en) |
| NL (1) | NL273283A (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR981432A (en) * | 1943-04-08 | 1951-05-25 | Francolor Sa | Process for the preparation of azo dyes and their metalliferous comoplexes, and new industrial products resulting therefrom |
-
0
- NL NL273283D patent/NL273283A/xx unknown
-
1961
- 1961-01-12 DE DE1961F0032946 patent/DE1210962C2/en not_active Expired
-
1962
- 1962-01-10 CH CH27162A patent/CH377464A/en unknown
- 1962-01-12 GB GB128462A patent/GB998522A/en not_active Expired
- 1962-01-12 BE BE612591A patent/BE612591A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1210962B (en) | 1966-02-17 |
| BE612591A (en) | 1962-07-12 |
| CH27162A4 (en) | 1963-11-30 |
| DE1210962C2 (en) | 1966-09-15 |
| CH377464A (en) | 1964-06-30 |
| NL273283A (en) |
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