GB744406A - Manufacture of azo-dyestuffs - Google Patents
Manufacture of azo-dyestuffsInfo
- Publication number
- GB744406A GB744406A GB27772/52A GB2777252A GB744406A GB 744406 A GB744406 A GB 744406A GB 27772/52 A GB27772/52 A GB 27772/52A GB 2777252 A GB2777252 A GB 2777252A GB 744406 A GB744406 A GB 744406A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- acid
- dyestuffs
- naphthol
- sulphonic 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 8
- 230000008878 coupling Effects 0.000 abstract 4
- 238000010168 coupling process Methods 0.000 abstract 4
- 238000005859 coupling reaction Methods 0.000 abstract 4
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 abstract 2
- 229920003043 Cellulose fiber Polymers 0.000 abstract 2
- 229920000742 Cotton Polymers 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- -1 amino-azo Chemical group 0.000 abstract 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 238000001465 metallisation Methods 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- VIFBEEYZXDDZCT-UHFFFAOYSA-N 2-(2-phenylethenyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=CC1=CC=CC=C1 VIFBEEYZXDDZCT-UHFFFAOYSA-N 0.000 abstract 1
- FAOJNWOJCPKVTM-UHFFFAOYSA-N 2-methoxynaphthalen-1-amine Chemical compound C1=CC=CC2=C(N)C(OC)=CC=C21 FAOJNWOJCPKVTM-UHFFFAOYSA-N 0.000 abstract 1
- ZYSOYLBBCYWEMB-UHFFFAOYSA-N 7-aminonaphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(N)=CC=C21 ZYSOYLBBCYWEMB-UHFFFAOYSA-N 0.000 abstract 1
- 229920002955 Art silk Polymers 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract 1
- 241000031711 Cytophagaceae Species 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
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract 1
- 229940045803 cuprous chloride Drugs 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 150000002736 metal compounds Chemical class 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 abstract 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 abstract 1
- 239000004627 regenerated cellulose Substances 0.000 abstract 1
- 235000021286 stilbenes Nutrition 0.000 abstract 1
- 239000000126 substance Substances 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
- 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
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
4 - Nitro - 41 - aminostilbene - 2,21 - disulphonic acid is diazotized and treated with cuprous chloride and hydrochloric acid to yield the corresponding 41-chloro-compound which is then reduced by the Bechamp method to 4 - amino - 41 - chlorostilbene - 2,21 - disulphonic acid. The product is used in the preparation of stilbene azo dyestuffs (c.f. Group IV (c)).ALSO:The invention comprises dyestuffs of formula <FORM:0744406/IV(c)/1> where R1 is the residue of a middle component and R2 is the residue of an aminonaphthol sulphonic acid bound to the azo group in ortho position to the oxy group and complex metal compounds of such dyestuffs as contain in R1 in a position vicinal to the azo linkage between R1 and R2 a group capable of metallization. The dyestuffs are made by coupling in an alkaline medium an aminonaphthol sulphonic acid with a diazo compound obtained by coupling diazotized 4-amino-41-chlorostilbene-2, 21-disulphonic acid with a middle component advantageously in an acid to neutral medium. Especially valuable dyestuffs may be made by diazotizing the stilbene sulphonic acid, coupling with a 1 - amino - 2 - alkoxynaphthol - sulphonic acid, diazotizing the amino-azo dyestuff thus obtained and coupling with a 1-acylamino-8-naphthol-3, 6-disulphonic acid. Specified middle components are 1-amino-2-methoxy-naphthalene and -benzene, 1-amino-2-methoxy-5-methyl- and -2, 5-dimethoxy-benzene and 1-amino-2-methoxy- and -ethoxy-naphthalene-6- and -7-sulphonic acid. End components indicated are 2-acyl- or -aryl-amino-5-naphthol-7-sulphonic acids, 2-amino-8-naphthol 6-sulphonic acid, 1-amino-8-naphthol-3, 6-disulphonic acid, 2-phenyl-, -(41-carboxymethoxy-phenyl)-, -benzyl- and -(41-chlorobenzyl)-amino -5- naphthol -7- sulphonic acid. Nickel and especially copper are specified metals metallization being effected in known fashion, in substance or on the fibre. The metallized and unmetallized dyestuffs dye and print wool, silk, leather and particularly cellulose fibres such as cotton, linen, artificial silk and regenerated cellulose fibres, the coppered dyestuffs yielding green and blue tints on cotton. Examples illustrate the use of certain of the above specified components in the preparation of the dyestuffs additional end components used being 2-acetylamino-5-naphthol-7-sulphonic acid, 1-benzoylamino-8-naphthol-3, 6-disulphonic acid and 2-phenylamino-8-naphthol-6-sulphuric acid-31-carboxylic acid. Specification 644,883 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH744406X | 1951-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB744406A true GB744406A (en) | 1956-02-08 |
Family
ID=4533377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27772/52A Expired GB744406A (en) | 1951-11-12 | 1952-11-04 | Manufacture of azo-dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB744406A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5548073A (en) * | 1992-08-26 | 1996-08-20 | Mitsui Toatsu Chemicals, Inc. | Water-soluble azo compounds |
-
1952
- 1952-11-04 GB GB27772/52A patent/GB744406A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5548073A (en) * | 1992-08-26 | 1996-08-20 | Mitsui Toatsu Chemicals, Inc. | Water-soluble azo compounds |
| US5739298A (en) * | 1992-08-26 | 1998-04-14 | Mitsui Toatsu Chemicals, Inc. | Water-soluble azo compounds |
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