GB590426A - Manufacture of new stilbene dyestuffs - Google Patents
Manufacture of new stilbene dyestuffsInfo
- Publication number
- GB590426A GB590426A GB897645A GB897645A GB590426A GB 590426 A GB590426 A GB 590426A GB 897645 A GB897645 A GB 897645A GB 897645 A GB897645 A GB 897645A GB 590426 A GB590426 A GB 590426A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphonic acid
- aminophenol
- replaced
- mol
- aminoazo
- 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
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 title abstract 4
- 235000021286 stilbenes Nutrition 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 aminoazo compounds Chemical class 0.000 abstract 17
- KLSJWNVTNUYHDU-UHFFFAOYSA-N 4H-1,2,4-triazol-3-amine Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 abstract 7
- 239000000047 product Substances 0.000 abstract 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- NCBZRJODKRCREW-UHFFFAOYSA-N M-Anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 abstract 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N Sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 abstract 4
- 239000005708 Sodium hypochlorite Substances 0.000 abstract 4
- 230000001808 coupling Effects 0.000 abstract 4
- 238000010168 coupling process Methods 0.000 abstract 4
- 238000005859 coupling reaction Methods 0.000 abstract 4
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2H-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 abstract 3
- 229920000742 Cotton Polymers 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 3
- 159000000000 sodium salts Chemical class 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 239000003518 caustics Substances 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 239000007800 oxidant agent Substances 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-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
- XFXOLBNQYFRSLQ-UHFFFAOYSA-N 3-aminonaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(N)=CC2=C1 XFXOLBNQYFRSLQ-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
- ZDTXQHVBLWYPHS-UHFFFAOYSA-N 4-nitrotoluene-2-sulfonic acid Chemical compound CC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O ZDTXQHVBLWYPHS-UHFFFAOYSA-N 0.000 abstract 1
- RPJXLEZOFUNGNZ-UHFFFAOYSA-N 5-methoxy-2-methylaniline Chemical compound COC1=CC=C(C)C(N)=C1 RPJXLEZOFUNGNZ-UHFFFAOYSA-N 0.000 abstract 1
- OBWAZTVVUBYJFW-UHFFFAOYSA-M COC1=CC(=CC=C1)NCS(=O)(=O)[O-] Chemical compound COC1=CC(=CC=C1)NCS(=O)(=O)[O-] OBWAZTVVUBYJFW-UHFFFAOYSA-M 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
- 210000004940 Nucleus Anatomy 0.000 abstract 1
- 240000007817 Olea europaea Species 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000012084 conversion product Substances 0.000 abstract 1
- 150000001879 copper Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- SXBOEBVXYQFVJM-UHFFFAOYSA-L copper;2-azanidylpentanedioate Chemical compound [Cu+2].[O-]C(=O)C([NH-])CCC([O-])=O SXBOEBVXYQFVJM-UHFFFAOYSA-L 0.000 abstract 1
- 230000000875 corresponding Effects 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000005755 formation reaction Methods 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000002452 interceptive Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002790 naphthalenes Chemical class 0.000 abstract 1
- 150000005002 naphthylamines Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical class [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 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)
- Coloring (AREA)
Abstract
Stilbene dyestuffs are manufactured by condensing, in the presence of caustic alkalies, one molecular proportion of 4 : 41-dinitro-stilbene- or - dibenzyl-2 : 21-disulphonic acid or the conversion products obtained by the action of caustic alkalies (with or without the application of pressure) on 4-nitrotoluene-2-sulphonic acid, and 0.5-1.5 molecular proportions of one or more aminotriazoles (P) of the formula <FORM:0590426/IV/1> containing in the naphthalene nucleus at least one water-solubilizing group, e.g. a carboxylic or sulphonic acid radical, but no amino or substituted amino groups, together with one or more aminoazo compounds (Q) of the formula <FORM:0590426/IV/2> (wherein Y stands for a sulphonic acid or carboxyl group and wherein the amino group may carry substituents capable of being split off by alkalies and the benzene nuclei may contain further substituents not interfering with the formation of the aminoazo compound), or with the copper complex of such an aminoazo compound, the sum of the molecular proportions of P and Q not exceeding 2, and, in so far as metallizable groups are still present, treating the product with copper-yielding agents (e.g. water-soluble copper salts), and, if desired, treating the coppered dyestuff with a mild oxidizing agent. The condensation may be carried out at the boil under atmospheric or superatmospheric pressure. The aminotriazoles (P) are obtainable by diazotizing 4-nitro-41-aminostilbene-2 : 21-disulphonic acid, coupling with such naphthylamine derivatives as are capable of coupling in o-position to the amino group and contain at least one water-solubilizing group, treating the products with oxidizing agents, e.g. sodium hypochlorite, copper salts or chlorine, and reducing the nitro group. The aminoazo compounds (Q) are obtainable by coupling the appropriate o-substituted diazonium compounds with the appropriate m-substituted anilines, or with N-methane-o -sulphonates thereof, with or without subsequent hydrolysis. The products of the invention dye cellulosic materials, e.g. cotton, including the cotton in a wool-cotton mixture, in brown and olive shades. In examples: (1) 1 mol. of the disodium salt of 4 : 41-dinitrostilbene-2 : 21-disulphonic acid is refluxed in aqueous caustic soda solution with 1 mol. of the trisodium salt of the aminotriazole from 2-naphthylamine-6-sulphonic acid and 1 mol. of the sodium salt of the aminoazo compound 2-aminophenol-4-sulphonic acid --> m-anisidine, and the product is heated with ammoniacal copper sulphate solution; (2) the aminoazo compound in (1) is replaced by 2-aminophenol-4-sulphonic acid --> 2 : 5-dimethoxyaniline; (3) the aminotriazole in (2) is replaced by that from 1-naphthylamine-4-sulphonic acid; (4) the aminoazo compound in (1) is replaced by 4-chloro-2-aminophenol-6-sulphonic acid --> m-anisidine, and (5) by 6-chloro-2-aminophenol-4-sulphonic acid --> m-anisidine; (6) the aminotriazole in (4) or (5) is replaced by that from 2-naphthylamine-7-sulphonic acid; (7) the aminotriazole in (1) is replaced by that from 1-naphthylamine-4-sulphonic acid, and the product is heated with sodium hypochlorite solution; (8) 0.3 mol. of the aminoazo compound in (1) is replaced by 0.3 mol. of the sodium salt of 2-aminophenol-4-sulphonic acid --> 2 : 5-dimethoxyaniline; the product may be treated with sodium hypochlorite as in (7); (9) the aminoazo compound in (1) is replaced by its copper complex compound, and the coppering step is omitted; (10) the aminotriazole in (1) is replaced by that from 2-amino-3-naphthoic acid; (11) the amount of the aminotriazole in (1) is increased to 1.5 mols. and that of the aminoazo compound reduced to 0.5 mol.; the product may be treated with an aqueous solution of sodium hypochlorite and caustic soda; (12) the amount of the aminotriazole in (2) is reduced to 0.5 mol. and that of the aminoazo compound increased to 1.5 mol.; (13) the aminoazo compound in (1) is replaced by 0.5 mol. each of the sodium salts of 6-chloro-2-aminophenol-4-sulphonic acid --> m-anisidine and 2 : 5-dimethoxyaniline respectively, or the corresponding compounds from 4-chloro-2-aminophenol-6-sulphonic acid; (14) the aminoazo compound in (2) is replaced by 4-chloro-2-aminophenol-6-sulphonic acid --> 2 : 5-dimethoxyaniline. Other starting materials specified are: for the preparation of the aminotriazoles: 2-naphthylamine - 5 - monosulphonic and -3 : 6-, -5 : 7- and -6 : 8-disulphonic acids; for the preparation of the aminoazo compounds: diazo components: 2-aminophenol-4 : 6-disulphonic acid, 3 - amino - 2 - hydroxy - 5 - sulphobenzoic acid and 4-chloro-2-aminophenol-5-sulphonic acid; coupling components: m-anisidine-N-methanesulphonate, m-phenetidine and 1 - amino - 2 - methyl - 5 - methoxybenzene. Specifications 311,384, [Class 2 (iii)], 348,283 and 427,241 are referred to.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US659147A US2467262A (en) | 1945-04-11 | 1946-04-02 | Stilbene triazole azo dyes |
FR925498D FR925498A (en) | 1945-04-11 | 1946-04-11 | Stilbene dyes |
Publications (1)
Publication Number | Publication Date |
---|---|
GB590426A true GB590426A (en) | 1947-07-17 |
Family
ID=1629582
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB897645A Expired GB590426A (en) | 1945-04-11 | 1945-04-11 | Manufacture of new stilbene dyestuffs |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB590426A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2684966A (en) * | 1954-07-27 | Triazole dyestuffs |
-
1945
- 1945-04-11 GB GB897645A patent/GB590426A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2684966A (en) * | 1954-07-27 | Triazole dyestuffs |
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