GB601369A - Process for the production of metallizable azo dyestuffs and complex metal compounds thereof - Google Patents
Process for the production of metallizable azo dyestuffs and complex metal compounds thereofInfo
- Publication number
- GB601369A GB601369A GB192346A GB192346A GB601369A GB 601369 A GB601369 A GB 601369A GB 192346 A GB192346 A GB 192346A GB 192346 A GB192346 A GB 192346A GB 601369 A GB601369 A GB 601369A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carboxylic acid
- hydroxybenzene
- aminobenzoyl
- acid
- methyl
- 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 4
- 150000002736 metal compounds Chemical class 0.000 title abstract 2
- 239000000975 dye Substances 0.000 abstract 13
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 abstract 8
- 210000002268 wool Anatomy 0.000 abstract 8
- 239000002253 acid Substances 0.000 abstract 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 6
- 239000000047 product Substances 0.000 abstract 6
- 229920002678 cellulose Polymers 0.000 abstract 5
- 239000001913 cellulose Substances 0.000 abstract 5
- 230000008878 coupling Effects 0.000 abstract 5
- 238000010168 coupling process Methods 0.000 abstract 5
- 238000005859 coupling reaction Methods 0.000 abstract 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 4
- 238000004043 dyeing Methods 0.000 abstract 4
- 229960001047 methyl salicylate Drugs 0.000 abstract 4
- 238000007127 saponification reaction Methods 0.000 abstract 4
- NZDXSXLYLMHYJA-UHFFFAOYSA-M 4-[(1,3-dimethylimidazol-1-ium-2-yl)diazenyl]-n,n-dimethylaniline;chloride Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1N=NC1=[N+](C)C=CN1C NZDXSXLYLMHYJA-UHFFFAOYSA-M 0.000 abstract 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 3
- 239000005749 Copper compound Substances 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 3
- 229910052804 chromium Inorganic materials 0.000 abstract 3
- 239000011651 chromium Substances 0.000 abstract 3
- 150000001880 copper compounds Chemical class 0.000 abstract 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
- 229910052742 iron Inorganic materials 0.000 abstract 3
- IWLGXPWQZDOMSB-UHFFFAOYSA-N 4-chloro-3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC=C1Cl IWLGXPWQZDOMSB-UHFFFAOYSA-N 0.000 abstract 2
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 2
- 125000004442 acylamino group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- -1 aromatic carboxylic acid halide Chemical class 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 239000004202 carbamide Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 239000007859 condensation product Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000010446 mirabilite Substances 0.000 abstract 2
- IQZPDFORWZTSKT-UHFFFAOYSA-N nitrosulphonic acid Chemical compound OS(=O)(=O)[N+]([O-])=O IQZPDFORWZTSKT-UHFFFAOYSA-N 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 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 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 abstract 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 abstract 1
- LBBNSTRZKADJGJ-UHFFFAOYSA-N 3-amino-2-benzoyloxybenzoic acid Chemical class NC1=C(C(C(=O)O)=CC=C1)OC(C1=CC=CC=C1)=O LBBNSTRZKADJGJ-UHFFFAOYSA-N 0.000 abstract 1
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 abstract 1
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 abstract 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 abstract 1
- DXMHBBURYDVYAI-UHFFFAOYSA-N 4-methyl-3-nitrobenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1[N+]([O-])=O DXMHBBURYDVYAI-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
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 abstract 1
- IMZSHPUSPMOODC-UHFFFAOYSA-N 5-oxo-1-phenyl-4h-pyrazole-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)=NN1C1=CC=CC=C1 IMZSHPUSPMOODC-UHFFFAOYSA-N 0.000 abstract 1
- DLPPBXHQUPWGTJ-UHFFFAOYSA-N 8-hydroxynaphthalene-1,2-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(S(O)(=O)=O)=C2C(O)=CC=CC2=C1 DLPPBXHQUPWGTJ-UHFFFAOYSA-N 0.000 abstract 1
- 235000011468 Albizia julibrissin Nutrition 0.000 abstract 1
- 229920003043 Cellulose fiber Polymers 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 240000005852 Mimosa quadrivalvis Species 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 150000001845 chromium compounds Chemical class 0.000 abstract 1
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 abstract 1
- 150000001879 copper Chemical class 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
- DCCIFKZACWAKSD-UHFFFAOYSA-N ethyl 3-oxo-2-phenyl-1h-pyrazole-5-carboxylate Chemical compound N1C(C(=O)OCC)=CC(=O)N1C1=CC=CC=C1 DCCIFKZACWAKSD-UHFFFAOYSA-N 0.000 abstract 1
- 229910001385 heavy metal Inorganic materials 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- HMIBDRSTVGFJPB-UHFFFAOYSA-N methyl 1-hydroxynaphthalene-2-carboxylate Chemical compound C1=CC=CC2=C(O)C(C(=O)OC)=CC=C21 HMIBDRSTVGFJPB-UHFFFAOYSA-N 0.000 abstract 1
- JQYUQKRFSSSGJM-UHFFFAOYSA-N methyl 2-hydroxy-5-methylbenzoate Chemical class COC(=O)C1=CC(C)=CC=C1O JQYUQKRFSSSGJM-UHFFFAOYSA-N 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- ALNWQAFPXMGLTJ-UHFFFAOYSA-N n-(7-hydroxynaphthalen-1-yl)acetamide Chemical compound C1=C(O)C=C2C(NC(=O)C)=CC=CC2=C1 ALNWQAFPXMGLTJ-UHFFFAOYSA-N 0.000 abstract 1
- XHOWGWWNFSHBAM-UHFFFAOYSA-N n-(8-hydroxynaphthalen-1-yl)acetamide Chemical compound C1=CC(O)=C2C(NC(=O)C)=CC=CC2=C1 XHOWGWWNFSHBAM-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 1
- 229960003742 phenol Drugs 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000004627 regenerated cellulose Substances 0.000 abstract 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 1
- 235000010265 sodium sulphite Nutrition 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 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
- 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
- C09B45/14—Monoazo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Aminobenzoylsalicylic acids of the general formula A-CO-B-NH2 (wherein A represents an o-hydroxycarboxyarl residue and B an aryl residue and wherein A or B or both may be further substituted, e.g. by halogen or an alkyl, carboxyl, nitro, sulphonic acid, hydroxy, alkoxy or aryloxy group) are obtainable by condensing an aromatic carboxylic acid halide which contains a nitrogen-containing group other than but convertible to an amino group (e.g. an acylamino or nitro group), with a methyl ester of an aromatic o-hydroxycarboxylic acid in the presence of a Friedel-Crafts condensing agent, saponifying the ester, and previously, subsequently or (in the case of an acylamino group) simultaneously converting to an amino group the group so convertible, any desired substituents not present in the starting materials being introduced at an intermediate stage. Examples describe the preparation of: (1) 1-(31- or 41-aminobenzoyl)-4-hydroxybenzene-5-carboxylic acid by alkaline saponification and reduction from 1-(31-nitrobenzoyl) - 4 - hydroxybenzene - 5 - carboxylic acid methyl ester and from the condensation product of 4-nitrobenzoyl chloride with methyl salicylate; (2) 1 - (31 p - aminobenzoyl) - 3 or -2-methyl - 4 - hydroxylbenzene - 5 - carboxylic acid, 1 - (31 - aminobenzoyl) - 5 - methyl - 2 - hydroxybenzene - 3 - carboxylic acid and 1-(31-amino-41-methylbenzoyl) -4-hydroxy-benzene-5-carboxylic acid similarly from 3-nitrobenzoyl chloride and o-, m- and p-cresotinic acid methyl esters and from 3-nitro-4-methylbenzoyl chloride and methyl salicylate; (3) 1-(31-aminobenzoyl)-3-sulpho-4-hydroxybenzene - 5 - carboxylic acid by sulphonation of 1-(31-nitrobenzoyl) - 4 - hydroxybenzene - 5 - carboxylic acid with oleum, and reduction of the nitro group; (4) 1-(31-aminobenzoyl)-4-hydroxynaphthalene - 3 - carboxylic acid from 1-hydroxy-2-naphthoic acid methyl ester as in (2); (8) 1-(31-amino-41-sulphobenzoyl) -4-hydroxybenzene-5-carboxylic acid by condensation of 4-chloro-3-nitrobenzoyl chloride and methyl salicylate, followed by saponification in an alkaline soda medium, replacement of the chlorine atom by a sulphonic acid group by boiling with sodium sulphite solution and reduction of the nitro group with iron; (9) 1-(41-hydroxy - 31 - aminobenzoyl) - 4 - hydroxybenzene-5-carboxylic acid from the same condensation product by saponification, replacement of the chlorine atom by a hydroxy group by refluxing in a solution alkaline to mimosa indicator and reduction of the nitro group with sodium sulphide; (11)1-(41-methoxy-31-aminobenzoyl) - 4 - hydroxybenzene - 5 - carboxylic acid similarly, using methyl alcoholic potassium hydroxide to replace the chlorine atom by a methoxy group and iron for the reduction step; (13) 1-(41-chloro-31-aminobenzoyl) - 4 - hydroxybenzene - 5 - carboxylic acid by condensation of 4-chloro-3-nitrobenzoyl chloride with methyl salicylate, followed by saponification in an alkaline soda medium and reduction of the nitro group with iron and hydrochloric acid. Specification 519,454 is referred to.ALSO:Metallizable azo dyestuffs and complex metal compounds thereof are manufactured by diazotizing a compound of the general formula A-CO-B-NH2 (wherein A represents an o-hydroxycarboxyaryl residue and B an aryl residue and wherein A or B or both may be further substituted, e.g. by halogen or an alkyl, carboxyl, nitro, sulphonic acid, hydroxy, alkoxy or aryloxy group) and coupling with any coupling component, especially a 5-pyrazolone, and, if desired, treating the products with metallizing agents. The components may be so chosen that the products have sufficient solubility in water for the purpose desired, which may be dyeing by the single bath chroming process, dyeing wool by the after-chroming process, dyeing cellulose with after-treatment of the dyeings with copper salts, or chromium printing. If the diazo component contains a lake-forming group (e.g. a hydroxy, alkoxy or carboxyl group) in o-position to the amino group, there is preferably chosen a coupling component which also contains a lake-forming group in o-position to the coupling position, in which case the product may be treated in substance with a metallizing agent in an amount insufficient to combine with all the metallizable groups in the dyestuff. Examples describe the preparation of the following dyestuffs: (1) 1-(31- or 41-aminobenzoyl)-4-hydroxybenzene-5-carboxylic acid --> 1-(21-chloro-51-sulpho- or 21 : 51-dichloro-41-sulphophenyl) - 3 - methyl - 5 - pyrazolone, which dye wool from acid baths in greenish yellow shades which may be after-chromed; (2) 1-(31-aminobenzoyl)-3- or -2-methyl-4-hydroxybenzene-5-carboxylic acid, 1-(31-aminobenzoyl)-5-methyl-2-hydroxybenzene-3-carboxylic acid or 1-(31-amino-41-methylbenzoyl) -4-hydroxybenzene-5-carboxylic acid --> the coupling components of (1), which dye wool similarly in yellow shades; (3) 1-(31-aminobenzoyl)-3-sulpho-4-hydroxybenzene-5-carboxylic acid --> 1-(21-chlorophenyl) - 3 - methyl - 5 - pyrazolone, which has similar properties to the products of (1); (4) 1-(31-aminobenzoyl)-4-hydroxynaphthalene-3-carboxylic acid --> 1-(21-chloro-51-sulphophenyl) - 3 - methyl - 5 - pyrazolone, which has similar properties to the products of (2); (5) 1 - (31-aminobenzoyl) - 4 - hydroxybenzene - 5 - carboxylic acid --> 2-acetylamino-8-naphthol-6-sulphonic acid, which dyes wool from acid baths in yellowish-red shades which may be after-chromed; (6) 1-(31- or 41-aminobenzoyl)-4 - hydroxybenzene - 5 - carboxylic acid --> 2 : 3 : 6-, 1 : 3 : 6- or 2 : 6 : 8-hydroxynaphthalenedisulphonic acid, which yield orange shades by chromium printing on cotton; (7) the same diazo components --> 1-acetylamino-8 - naphthol - 3 : 6 - disulphonic acid, which similarly yield bluish-red prints; (8) 1-(31-amino-41-sulphobenzoyl) -4-hydroxybenzene-5-carboxylic acid --> (alkaline) 2 : 8 : 6-amino-naphtholsulphonic acid, which has similar properties to the product of (5); (9) 1-(41-hydroxy31-aminobenzoyl) -4-hydroxybenzene-5-carboxylic acid --> 1-acetylamino-7-hydroxynaphthalene, which is refluxed with a solution of chromsalicylate of ammonia to form its chromium compound, which dyes wool from acid baths in grey shades which may be further treated with compounds of hexavalent chromium; (10) the same diazo component (2 mols.) \sQ J-acid urea or 5 : 51-dihydroxy-2 : 21-dinaphthylamine-7 : 71-disulphonic acid, which dye cellulose from a bath containing Glauber's salt in reddish- and blueish-violet shades which become ruby red and violet respectively on after-treatment with cupric salts, and of which the copper compounds prepared in substance dye cellulose in ruby red and violet shades which may be further treated with salts of heavy metals, e.g. of tervalent chromium; (11) 1-(41-methoxy- or -hydroxy - 31 - aminobenzoyl) - 4 - hydroxybenzene-5-carboxylic acid --> J-acid urea -->- anthranilic acid, which similarly dye cellulose in yellowish-red shades becoming bluish-red on after-coppering, and which may be heated with copper sulphate solution to yield copper compounds which similarly dye cellulose in bluish-red shades; (12) 1-(41-hydroxyl-31-aminobenzoyl) -4-hydroxybenzene-5-carboxylic acid --> 2-benzoylamino-, 2-phenylamino- or 2 - (41 - hydroxy - 31 - carboxyphenylamino) - 5 - naphthol-7-sulphonic acid, the copper compounds of which dye regenerated cellulose fibres from a bath containing Glauber's salt in blueish-red, ruby red and reddish-violet shades; (13) 1-(31-aminobenzoyl)-4-hydroxybenzene-5-carboxylic acid or its 41-chloro-derivative --> 1 - (31 - sulphonamidophenyl) - 3 - methyl - 5 - pyrazolone, which dye wool by the single bath chroming process in greenish- and reddish-yellow shades; the diazo components in any of the foregoing examples may be replaced by 1-(21-amino-51-nitrobenzoyl)-, 1-(31-amino-61-acylamino-, -chloro-, -alkoxy-, -aryloxy- or -aralkyloxy - benzoyl)- or 1 - (31 - amino - 41 - aryloxy-, -aralkyloxy-, -carboxymethoxy- or -carboxy - benzoyl) - 4 - hydroxybenzene - 5 - carboxylic acid; (14) 1 - (31 - aminobenzoyl) - 3 - sulpho-4-hydroxybenzene-5-carboxylic acid or 1 - (31 - amino - 41 - sulphobenzoyl) - 4 - hydroxybenzene-5-carboxylic acid --> 3-methyl-5-pyrazolone, which dye wool from an acid bath in greenish-yellow shades which may be after-chromed; (15) 1-(31-aminobenzoyl)-3-sulpho-4-hydroxybenzene-5-carboxylic acid or 1-(31-amino-41-sulphobenzoyl) -4-hydroxybenzene-5-carboxylic acid --> 1-phenyl-3-carbethoxy-5-pyrazolone or 1-(31-chlorophenyl)-5-pyrazolone-3-carboxylic acid or its esters or amides, and 1 - (31 - amino - 41 - sulphobenzoyl) - 4 - hydroxybenzene-5-carboxylic acid --> 1-phenyl-5-pyrazolone-3-carboxylic acid or its amide, which dye wool similarly in yellow to greenish-yellow shades. Specification 591,454 is referred to.
Publications (1)
Publication Number | Publication Date |
---|---|
GB601369A true GB601369A (en) | 1948-05-04 |
Family
ID=1627054
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB192346A Expired GB601369A (en) | 1946-01-21 | Process for the production of metallizable azo dyestuffs and complex metal compounds thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB601369A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021010340A1 (en) * | 2019-07-12 | 2021-01-21 | 日本化薬株式会社 | Luminescent compound or salt thereof, and polarized light emitting element, polarized light emitting plate and display device each using same |
-
1946
- 1946-01-21 GB GB192346A patent/GB601369A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021010340A1 (en) * | 2019-07-12 | 2021-01-21 | 日本化薬株式会社 | Luminescent compound or salt thereof, and polarized light emitting element, polarized light emitting plate and display device each using same |
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