GB819314A - Improvements relating to metallisable monoazo dyestuffs of the benzene-azo-pyrazolone series, complex metal compounds thereof, and their use - Google Patents
Improvements relating to metallisable monoazo dyestuffs of the benzene-azo-pyrazolone series, complex metal compounds thereof, and their useInfo
- Publication number
- GB819314A GB819314A GB16709/56A GB1670956A GB819314A GB 819314 A GB819314 A GB 819314A GB 16709/56 A GB16709/56 A GB 16709/56A GB 1670956 A GB1670956 A GB 1670956A GB 819314 A GB819314 A GB 819314A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aminophenol
- nitro
- acid
- methyl
- group
- 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
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title abstract 4
- 150000002736 metal compounds Chemical class 0.000 title 1
- 239000000975 dye Substances 0.000 abstract 8
- 229910052751 metal Chemical class 0.000 abstract 4
- 239000002184 metal Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 229910052804 chromium Inorganic materials 0.000 abstract 2
- 239000011651 chromium Substances 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 239000000835 fiber Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 abstract 1
- ZARYBZGMUVAJMK-UHFFFAOYSA-N 2-amino-4-chloro-5-nitrophenol Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1O ZARYBZGMUVAJMK-UHFFFAOYSA-N 0.000 abstract 1
- AJWIWEGQLDDWQC-UHFFFAOYSA-N 2-amino-4-methyl-6-nitrophenol Chemical compound CC1=CC(N)=C(O)C([N+]([O-])=O)=C1 AJWIWEGQLDDWQC-UHFFFAOYSA-N 0.000 abstract 1
- ZDMBLPBTZZZSIW-UHFFFAOYSA-N 2-amino-6-methyl-4-nitrophenol Chemical compound CC1=CC([N+]([O-])=O)=CC(N)=C1O ZDMBLPBTZZZSIW-UHFFFAOYSA-N 0.000 abstract 1
- AACMNEWXGKOJJK-UHFFFAOYSA-N 2-amino-6-nitrophenol Chemical compound NC1=CC=CC([N+]([O-])=O)=C1O AACMNEWXGKOJJK-UHFFFAOYSA-N 0.000 abstract 1
- FQHYQCXMFZHLAE-UHFFFAOYSA-N 25405-85-0 Chemical compound CC1(C)C2(OC(=O)C=3C=CC=CC=3)C1C1C=C(CO)CC(C(C(C)=C3)=O)(O)C3C1(O)C(C)C2OC(=O)C1=CC=CC=C1 FQHYQCXMFZHLAE-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- -1 alkali metal chromates Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 abstract 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000000751 azo group Chemical class [*]N=N[*] 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001868 cobalt Chemical class 0.000 abstract 1
- 229940011182 cobalt acetate Drugs 0.000 abstract 1
- 150000004700 cobalt complex Chemical class 0.000 abstract 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 abstract 1
- 230000009918 complex formation Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 abstract 1
- 239000004312 hexamethylene tetramine Substances 0.000 abstract 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 abstract 1
- 150000007857 hydrazones Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
1-benzyl- or (a - or b -phenylethyl)-3-methyl-5-pyrazolones are prepared by condensing a suitable aldehyde or ketone, e.g. benzaldehyde with a hydrazinoformic acid alkyl ester, hydrogenating the hydrazone so obtained to yield the corresponding hydrazine, saponifying the ester group and reacting the compounds so obtained with ethyl acetoacetate or acetoacetic acid amide. Reference has been directed by the Comptroller to Specifications 637,404, [Group IV (c)], 667,168, 736,034, [Group IV (c)], and 743,583.ALSO:The invention comprises monoazo dyes of formula <FORM:0819314/IV (c)/1> wherein A and B are phenyl radicals, R is a methylene or ethylene group and X is a hydroxyl or carboxyl group in o-position to the azo group and metal complexes thereof. The dyes are prepared by diazotizing a 2-amino-1-hydroxy- or -carboxy-benzene which may be substituted by halogen atoms or alkyl, alkoxy, nitro, acylamino, alkyl or arylsulphonyl, acyl, sulphonic acid, or sulphonic acid-N-alkyl, -hydroxyalkyl, -dialkyl, -aryl or -aralkyl amide groups and coupling with a 1-phenylmethyl- or -phenylethyl-3-methyl-5-pyrazolone. The metal complexes are produced in known manner in substance or on the fibre. Specified metallizing agents are alkali metal chromates, chromic and cobalt acetate or sulphate, hexamine cobaltitrichloride and alkali metal or ammonium salts of chromosalicylic acid. The preferred metal complexes are the chromium or cobalt complexes, containing one atom of metal to two molecules of dyestuffs which contain no water-solubilizing groups dissociating acid in neutral water other than carboxyl groups taking part in the complex formation. The dyes may be used to prepare mixed complexes with other metallizable monoazo dyes. The metallized dyes dye wool in light yellow, brown to red shades and may also be used to dye leather or synthetic polyamide fibres or to colour lacquers. In examples monoazo dyes of the above formula are prepared from the following components and converted into the chromium or cobalt complex in substance or on the fibre: diazo components-2-aminobenzene-1-carboxylic acid, 4-chloro- or -nitro-or -tert. amyl-2-aminophenol-6-sulphonic acid, 6 - nitro - 2 - aminophenol - 4 - sulphonic acid, 4 - nitro - 6 - methyl - 2 - aminophenol, 4-nitro - 2 - aminophenol, 2 - amino - 1 - carboxybenzene - 4 - sulphomethylamide, 6 - nitro - 4-methyl - 2 - aminophenol, 5 - nitro - 4 - chloro-2 - aminophenol, 2 - aminophenol - 4 - ethylsulphone or -sulphomethylamide and 6-nitro-2-aminophenol-4- or -5-methylsulphone; coupling components-1 - benzyl - or - (a - or b - phenylethyl)-3-methyl-5-pyrazolone. Reference has been directed by the Comptroller to Specifications 637,404, 667,168, 736,034 and 743,583.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH819314X | 1955-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB819314A true GB819314A (en) | 1959-09-02 |
Family
ID=4539257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16709/56A Expired GB819314A (en) | 1955-06-01 | 1956-05-30 | Improvements relating to metallisable monoazo dyestuffs of the benzene-azo-pyrazolone series, complex metal compounds thereof, and their use |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB819314A (en) |
-
1956
- 1956-05-30 GB GB16709/56A patent/GB819314A/en not_active Expired
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