GB825431A - Improvements relating to copper containing disazo dyestuffs of the stilbene series - Google Patents
Improvements relating to copper containing disazo dyestuffs of the stilbene seriesInfo
- Publication number
- GB825431A GB825431A GB38194/56A GB3819456A GB825431A GB 825431 A GB825431 A GB 825431A GB 38194/56 A GB38194/56 A GB 38194/56A GB 3819456 A GB3819456 A GB 3819456A GB 825431 A GB825431 A GB 825431A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphonic
- acids
- naphthylamine
- coupling
- naphthol
- 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title 1
- 229910052802 copper Inorganic materials 0.000 title 1
- 239000010949 copper Substances 0.000 title 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 7
- 150000007513 acids Chemical class 0.000 abstract 7
- 230000008878 coupling Effects 0.000 abstract 4
- 238000010168 coupling process Methods 0.000 abstract 4
- 238000005859 coupling reaction Methods 0.000 abstract 4
- -1 aminoazo stilbenes Chemical class 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 150000001879 copper Chemical class 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 235000021286 stilbenes Nutrition 0.000 abstract 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 abstract 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 abstract 1
- KPJCYEKVSQUUIL-UHFFFAOYSA-N 3-(2-phenylethenyl)-2-[[2-(2-phenylethenyl)phenyl]diazenyl]aniline Chemical compound NC=1C(=C(C=CC=1)C=CC1=CC=CC=C1)N=NC1=C(C=CC=C1)C=CC1=CC=CC=C1 KPJCYEKVSQUUIL-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000010446 mirabilite Substances 0.000 abstract 1
- GVUHTLABICJQTO-UHFFFAOYSA-N n-(1-hydroxynaphthalen-2-yl)acetamide Chemical class C1=CC=CC2=C(O)C(NC(=O)C)=CC=C21 GVUHTLABICJQTO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004957 naphthylene group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000004627 regenerated cellulose Substances 0.000 abstract 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 150000003852 triazoles Chemical class 0.000 abstract 1
- 125000001425 triazolyl group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B56/00—Azo dyes containing other chromophoric systems
- C09B56/04—Stilbene-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
- 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
- C09B45/28—Disazo or polyazo compounds containing copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises copper complexes of dyestuffs of formul <FORM:0825431/IV(c)/1> where Ar is a naphthylene residue, which may be substituted by sulphonic acid groups, bound to the N atoms by adjacent carbon atoms, B is an acyl residue and R is CH3, C2H5 or CH2COOH. They are made by coupling an appropriate diazotized aminoazo stilbene with a 2-acylamino-6-naphthol-8-sulphonic acid and coppering the product or by coupling a diazo compound of an amine of formula <FORM:0825431/IV(c)/2> with a 2-acylamino-6-naphthol-8-sulphonic acid, reducing the NO2 group to NH2 and, after diazotizing, coupling the disazo dyestuff with a naphthalenic end component which couples o to the NH2 group, oxidizing the product, and either simultaneously or subsequently coppering the triazole thus produced. The acyl residue may be derived from a sulphonic or preferably a carboxylic or carbonic acid. The aminoazo stilbenes used in the first method are made by coupling diazotized 41-amino-4-[4,5-naphtho-1,2,3 - triazolyl - (2)] - stilbene - 2,21 - disulphonic acids with appropriate 2-alkoxynaphthylamine sulphonic acids. Specified naphthylamine end components from which the triazole ring may be derived are 2-naphthylamine and its -1-, -5-, -6-, -7- and -8-mono- and -3,6-, -5,7- and -6,8-disulphonic acids and 1-naphthylamine-3- and -4-sulphonic acids. Specified acetylaminonaphthols are 2-acetyl-, -carbomethoxy-, -sulphoacetyl-, -benzyl- and -m- and -p-aminobenzoyl-6-naphthol-8-sulphonic acids. The alkali metal salts of the copper complexes are soluble in water and dye cellulosic material from a bath containing Glauber's salt in green shades. Examples are provided illustrating the preparation of the dyestuffs and their use in dyeing cotton and regenerated cellulose, the components used being chosen from those listed above with the addition of methyl- and chloromethyl-sulphonyl-, propionyl- and carboethoxy-amino as 2-acetylamino groups and the 2-alkoxynaphthylamine sulphonic acids used are 2-methoxy and methoxycarboxy-1-naphthylamine-6-sulphonic acids. Specification 503,576, [Group IV], is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH825431X | 1955-12-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB825431A true GB825431A (en) | 1959-12-16 |
Family
ID=4539885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB38194/56A Expired GB825431A (en) | 1955-12-16 | 1956-12-14 | Improvements relating to copper containing disazo dyestuffs of the stilbene series |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB825431A (en) |
-
1956
- 1956-12-14 GB GB38194/56A patent/GB825431A/en not_active Expired
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