GB591354A - Process for the production of metallisable dyestuffs, the products and their use - Google Patents
Process for the production of metallisable dyestuffs, the products and their useInfo
- Publication number
- GB591354A GB591354A GB2139343A GB2139343A GB591354A GB 591354 A GB591354 A GB 591354A GB 2139343 A GB2139343 A GB 2139343A GB 2139343 A GB2139343 A GB 2139343A GB 591354 A GB591354 A GB 591354A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- nitro
- dyestuffs
- aminophenol
- replaced
- 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
- 239000002253 acid Substances 0.000 abstract 7
- 239000000975 dye Substances 0.000 abstract 7
- 239000005749 Copper compound Substances 0.000 abstract 4
- -1 aminoazo Chemical group 0.000 abstract 4
- 150000001880 copper compounds Chemical class 0.000 abstract 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- 230000008878 coupling Effects 0.000 abstract 3
- 238000010168 coupling process Methods 0.000 abstract 3
- 238000005859 coupling reaction Methods 0.000 abstract 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 2
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 abstract 2
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 abstract 2
- 229920003043 Cellulose fiber Polymers 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 229960004889 salicylic acid Drugs 0.000 abstract 2
- OIWJQYPZFXSJRU-UHFFFAOYSA-N 2-(3-aminophenoxy)acetic acid Chemical compound NC1=CC=CC(OCC(O)=O)=C1 OIWJQYPZFXSJRU-UHFFFAOYSA-N 0.000 abstract 1
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 abstract 1
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 abstract 1
- ZLTOYIGWKLTQBJ-UHFFFAOYSA-N 3-amino-2-hydroxy-5-sulfobenzoic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(C(O)=O)=C1O ZLTOYIGWKLTQBJ-UHFFFAOYSA-N 0.000 abstract 1
- NUNAWQZKZVVELQ-UHFFFAOYSA-N 3-amino-4-methylphenol Chemical compound CC1=CC=C(O)C=C1N NUNAWQZKZVVELQ-UHFFFAOYSA-N 0.000 abstract 1
- WEZAHYDFZNTGKE-UHFFFAOYSA-N 3-ethoxyaniline Chemical compound CCOC1=CC=CC(N)=C1 WEZAHYDFZNTGKE-UHFFFAOYSA-N 0.000 abstract 1
- NJESAXZANHETJV-UHFFFAOYSA-N 4-methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 abstract 1
- BWKDAAFSXYPQOS-UHFFFAOYSA-N Benzaldehyde glyceryl acetal Chemical compound O1CC(O)COC1C1=CC=CC=C1 BWKDAAFSXYPQOS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000906 Bronze Inorganic materials 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 240000007817 Olea europaea Species 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000010974 bronze Substances 0.000 abstract 1
- 239000003518 caustics Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001844 chromium Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Metallizable dyestuffs are manufactured by condensing, in the presence of caustic alkalies, aminoazo dyestuffs of the general formula <FORM:0591354/IV/1> (wherein X represents a hydroxy or carboxyl group, Y a hydroxy, O-alkylene-carboxyl or alkoxy group, and Z hydrogen or a sulphonic acid, sulphonamide or carboxyl group, and wherein the two benzene nuclei may further contain one or more indifferent substituents, and the amino group may be acylated) with azo dyestuffs from diazotized 4-nitro-41-aminostilbene- or -dibenzyl-2 : 21-disulphonic acid and monohydric phenolic coupling components of the benzene series, in which the hydroxyl group, if it is in p-position to the azo group and is not in o-position to a carboxyl group, must, after formation of the azo dyestuff, be etherified. The products may be after-treated with oxidizing agents, and may be treated with metal-yielding agents in substance or on the fibre, or the aminoazo dyestuffs of the above general formula may be replaced by their copper compounds. The metal-containing dyestuffs yield brown, olive, khaki or grey shades on cellulose fibres. In examples: (1) the dyestuffs 4-nitro-41-aminostilbene-2 : 21-disulphonic acid --> salicylic acid and 2-aminophenol-4-sulphonic acid --> 2 : 5-dimethoxyaniline are refluxed in dilute soda lye; the product may be converted into its copper compound, which dyes cellulose fibres in bronze shades which may be after-treated with copper or chromium salts; (2) the 2 : 5-dimethoxyaniline in (1) is replaced by m-anisidine; (3) the aminoazo dyestuff in (2) is replaced by its copper compound, yielding the copper compound of the final dyestuff directly; (4) the 2-aminophenol-4-sulphonic acid in (2) is replaced by its 6-chloro-derivative, and (5) by 4-chloro-2-aminophenol; (6) the first dyestuff in (1) is replaced by 4-nitro-41-aminodibenzyl-2 : 21-disulphonic acid --> o-cresotic acid; (7) the first dyestuff in (2) is replaced by the ethylated (or methylated, propylated or butylated) dyestuff 4-nitro-41-aminostilbene-2 : 21-disulphonic acid --> phenol; (8) the dyestuffs 4-nitro-41-amino-stilbene - (or -dibenzyl - ) 2 : 21 - disulphonic acid --> salicylic acid and 4-nitro-2-aminophenol --> 2 - amino - 4 - hydroxytoluene are condensed as in (1). Additional components specified are: for the production of the aminoazo dyestuffs: diazo components: 2-aminophenol - 4 - sulphamide, 4 - chloro - 2 - aminophenol-5- and 6-sulphonic acids, 2-aminobenzoic acid and its 5-nitro- and 4-chloroderivatives, 3-amino-4-hydroxybenzoic acid and 2 - hydroxy - 3 - amino - 5 - sulphobenzoic acid; coupling components: m-phenetidine, 1-amino2-methyl-5-methoxy- or -ethoxy-benzene, 2 : 5-diethoxy- or -dipropyloxy-aniline and 3-aminophenoxyacetic acid; for coupling with the diazotized 4-nitro-41-amino-stilbene- or -dibenzyl-2 : 21-disulphonic acid: m-cresotic acid. Specification 404,613 is referred to.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB591354A true GB591354A (en) | 1947-08-15 |
Family
ID=1736169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2139343A Expired GB591354A (en) | 1943-12-21 | Process for the production of metallisable dyestuffs, the products and their use |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB591354A (en) |
-
1943
- 1943-12-21 GB GB2139343A patent/GB591354A/en not_active Expired
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