GB823945A - Improvements relating to metallisable monoazo dyestuffs, of the benzene-azo naphthalene series, complex heavy metal compounds thereof, and their use - Google Patents
Improvements relating to metallisable monoazo dyestuffs, of the benzene-azo naphthalene series, complex heavy metal compounds thereof, and their useInfo
- Publication number
- GB823945A GB823945A GB4219/56A GB421956A GB823945A GB 823945 A GB823945 A GB 823945A GB 4219/56 A GB4219/56 A GB 4219/56A GB 421956 A GB421956 A GB 421956A GB 823945 A GB823945 A GB 823945A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aminophenol
- naphthol
- sulphonic acid
- nitro
- 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
- 229910001385 heavy metal Inorganic materials 0.000 title abstract 3
- 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 2
- SOYBJIUDKRLQTA-UHFFFAOYSA-N benzene;dinaphthalen-1-yldiazene Chemical class C1=CC=CC=C1.C1=CC=C2C(N=NC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 SOYBJIUDKRLQTA-UHFFFAOYSA-N 0.000 title 1
- 150000002736 metal compounds Chemical class 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 6
- 239000000975 dye Substances 0.000 abstract 6
- 229940124530 sulfonamide Drugs 0.000 abstract 5
- 230000008878 coupling Effects 0.000 abstract 4
- 238000010168 coupling process Methods 0.000 abstract 4
- 238000005859 coupling reaction Methods 0.000 abstract 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 abstract 3
- 125000003277 amino group Chemical class 0.000 abstract 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 3
- 230000007935 neutral effect Effects 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- QSEKXHCIPQVPAF-UHFFFAOYSA-N (8-hydroxynaphthalen-1-yl)urea Chemical compound N(C(=O)N)C1=CC=CC2=CC=CC(=C12)O QSEKXHCIPQVPAF-UHFFFAOYSA-N 0.000 abstract 2
- -1 1 - ethylsulphonylamino Chemical group 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- IHGUECDAIUQEDD-UHFFFAOYSA-N N-(8-hydroxynaphthalen-1-yl)benzenesulfonamide Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC1=CC=CC2=CC=CC(=C12)O IHGUECDAIUQEDD-UHFFFAOYSA-N 0.000 abstract 2
- FGAPCPPHIBPFEI-UHFFFAOYSA-N N-(8-hydroxynaphthalen-1-yl)propanamide Chemical compound C(CC)(=O)NC1=CC=CC2=CC=CC(=C12)O FGAPCPPHIBPFEI-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 2
- 229910052804 chromium Inorganic materials 0.000 abstract 2
- 239000011651 chromium Substances 0.000 abstract 2
- 150000001869 cobalt compounds Chemical class 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 238000001465 metallisation Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- WQCDFBOFNQVREB-UHFFFAOYSA-N n-(8-hydroxynaphthalen-1-yl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=CC2=CC=CC(O)=C12 WQCDFBOFNQVREB-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- GDWLOSYUBLWPBT-UHFFFAOYSA-N 2-amino-3-ethylsulfonylphenol Chemical compound CCS(=O)(=O)C1=CC=CC(O)=C1N GDWLOSYUBLWPBT-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
- JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-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
- VGNIIYAZVPQCRI-UHFFFAOYSA-N 2-amino-4-ethylsulfonyl-5-nitrophenol Chemical compound CCS(=O)(=O)C1=CC(N)=C(O)C=C1[N+]([O-])=O VGNIIYAZVPQCRI-UHFFFAOYSA-N 0.000 abstract 1
- WZSBYBXNPKFJTA-UHFFFAOYSA-N 2-amino-4-methyl-5-nitrophenol Chemical compound CC1=CC(N)=C(O)C=C1[N+]([O-])=O WZSBYBXNPKFJTA-UHFFFAOYSA-N 0.000 abstract 1
- IFXKXCLVKQVVDI-UHFFFAOYSA-N 2-amino-5-chlorobenzoic acid Chemical compound NC1=CC=C(Cl)C=C1C(O)=O IFXKXCLVKQVVDI-UHFFFAOYSA-N 0.000 abstract 1
- TYFGMFQLFGWYBY-UHFFFAOYSA-N 2-amino-5-ethylsulfonylphenol Chemical compound CCS(=O)(=O)C1=CC=C(N)C(O)=C1 TYFGMFQLFGWYBY-UHFFFAOYSA-N 0.000 abstract 1
- QUIIUKFPLUUSGQ-UHFFFAOYSA-N 2-amino-6-chlorophenol Chemical compound NC1=CC=CC(Cl)=C1O QUIIUKFPLUUSGQ-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
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 abstract 1
- GDAIYFAMMVNXNI-UHFFFAOYSA-N 5-ethoxy-2-methoxyaniline Chemical compound CCOC1=CC=C(OC)C(N)=C1 GDAIYFAMMVNXNI-UHFFFAOYSA-N 0.000 abstract 1
- RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-UHFFFAOYSA-N 0.000 abstract 1
- TWLMSPNQBKSXOP-UHFFFAOYSA-N 6358-09-4 Chemical compound NC1=CC([N+]([O-])=O)=CC(Cl)=C1O TWLMSPNQBKSXOP-UHFFFAOYSA-N 0.000 abstract 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- MTZUMZXKBLJVFG-UHFFFAOYSA-N N-(5-acetyl-3-amino-2-hydroxyphenyl)acetamide Chemical compound C(C)(=O)C1=CC(=C(C(=C1)NC(C)=O)O)N MTZUMZXKBLJVFG-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001868 cobalt Chemical class 0.000 abstract 1
- 230000009918 complex formation Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 abstract 1
- AXZMVCWSNAGENE-UHFFFAOYSA-N n-(3-amino-2-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1O AXZMVCWSNAGENE-UHFFFAOYSA-N 0.000 abstract 1
- NYFNQFSVMWNXLT-UHFFFAOYSA-N n-(8-hydroxynaphthalen-1-yl)benzamide Chemical compound C=12C(O)=CC=CC2=CC=CC=1NC(=O)C1=CC=CC=C1 NYFNQFSVMWNXLT-UHFFFAOYSA-N 0.000 abstract 1
- SDCMRZGUPSGEFP-UHFFFAOYSA-N n-(8-hydroxynaphthalen-1-yl)methanesulfonamide Chemical compound C1=CC(O)=C2C(NS(=O)(=O)C)=CC=CC2=C1 SDCMRZGUPSGEFP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N ortho-hydroxyaniline Natural products NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 1
- 229920001184 polypeptide Polymers 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 102000004196 processed proteins & peptides Human genes 0.000 abstract 1
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000009987 spinning Methods 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
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052720 vanadium Inorganic materials 0.000 abstract 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1 - Acylamino - 8 - naphthols having in the 6-position a group R-SO2- wherein R is a possibly substituted hydrocarbon radical or an amino group which may be substituted on the nitrogen atom are used as coupling components in the preparation of azo dyestuffs (see Group IV (a)). They are obtained from 1-amino-8-naphthol-6-sulphonic acid by protecting the amino and hydroxy groups, for example by phosgenation to form the corresponding perinaphthoxazinone, the sulphonic acid group is converted in known manner to the sulphonic acid halide group, which is then reacted with ammonia or an amine, or reduced to the sulphinic acid and alkylated, or condensed 'with aromatic hydrocarbons by the Friedel Crafts reaction. The sulphone or sulphonamide thus obtained is saponified with alkali and the amino group is acylated. Specified compounds are 1-acetylamino-8-naphthol-6-sulphonamide or - sulphomethylamide or - sulphodimethylamide or -sulphonic acid anilide or -sulphonic acid - N - ethyl anilide or - methylsulphone, 1-propionylamino - 8 - naphthol - 6 - sulphopropylamide or - sulphonic acid anilide, 1 - ethoxyacetylamino - 8 - naphthol - 6 - sulphonamide, 1 - carbomethoxyamino - or - carboethoxyamino - 8 - naphthol - 6 - sulphamide, 1-methanesulphonylamino - 8 - naphthol - 6 - sulphonic acid morpholide, 1 - p - toluenesulphonylamino - 8 - naphthol - 6 - sulphonic acid piperidide, 1 - benzoylamino - 8 - naphthol - 6-sulphonic acid ethanolamide or - phenylsulphone, 1 - ureido - 8 - naphthol - 6 - sulphamide, 1 - benzenesulphonylamino - 8 - naphthol - 6 - phenylsulphone, 1 - b - chloropropionylamino - 8 - naphthol - 6 - sulphonic acid ethanolamide and 1 - ethylsulphonylamino - 8 - naphthol-6-sulphamide. Reference has been directed by the Comptroller to Specifications 637,404, [Group IV(c)], 667,168, 712,037, 736,034, [Group IV (c)], 737,619, 743,583 and 774,884.ALSO:The invention comprises the metallizable monoazo dyes of formula <FORM:0823945/IV(c)/1> wherein A is a phenyl radical, X is a metallizable group or a substituent convertible thereto during metallization ortho to -N=N-, Y is an acyl group, R is a possibly substituted hydrocarbon radical or an amino group which may be substituted at the nitrogen atom and wherein the naphthalene coupling component is free from water-solubilizing groups which dissociate acid in neutral water, and heavy metal complexes thereof containing 1 atom of heavy metal linked to two molecules of dyestuff. The dyes are prepared by coupling a suitably substituted benzene diazonium compound with a 1-acylamino - 8 - hydroxynaphthalene - 6 - sulphone or -sulphonamide (see Group IV (b)). The preferred dyestuffs are those wherein the diazo component contains, with the exception of any carboxyl group taking part in the complex formation, no water-solubilizing groups which dissociate acid in neutral water. Specified diazo components, other than those in examples are 2-aminophenol-4-sulphonic acid, 6-chloro-2-aminophenol - 4 - sulphonic acid, 4 - acetyl - or ethylsulphonyl - 2 - aminophenol - 6 - sulphonic acid, 4- or 6-acetylamino-2-aminophenol-6- or -4-sulphonic acid, 4-nitro-2-aminophenol-6-sulphonic acid, 3 : 4 : 6-trichloro-2-aminophenol, 5-nitro - 4 - methyl - 2 - aminophenol, 4 - nitro - 6 - chloro - 2 - aminophenol, 5 - ethylsulphonyl - 2 - aminophenol, 5 - nitro - 4 - ethylsulphonyl - 2 - aminophenol, 6-nitro-4-tert.-amyl-2-aminophenol, 4-acetyl-6-acetylamino-2-aminophenol, 2-methoxy-5-ethoxy-aniline, 2-aminobenzoic acid, 4- or 5-chloro-2-aminobenzoic acid and 5-nitro-2-aminobenzoic acid. The metallization is preferably carried out using chromic or cobalt compounds in aqueous solution or suspension, possibly with the addition of solvents such as ethylene glycol or dioxan. Alkali metal chromosalicylates are the preferred chroming agents. Dyestuffs containing an o-alkoxy group are preferably metallized in formamide or ethylene glycol with chromic salts at temperatures of over 100 DEG C. Mixtures of dyestuffs of the above formula and mixtures of dyestuffs of the above formula with similar metallizable dyestuffs may also be metallized. Metal complexes of the above formula which contain no groups dissociating acid in neutral water may be converted into the copper, vanadium, manganese, chromium, nickel, iron or cobalt compounds which may be used to dye cellulose lacquers or spinning solutions. The metal complexes dye natural and synthetic polypeptide fibres in blue shades. In examples, dyes are prepared from the following components and the chromium and cobalt complexes thereof are formed: diazo components:-4-chloro- or -nitro- or -methoxy-2-aminophenol, 4 - chloro - 2 - aminophenol - 6 - sulphonic acid, 4 : 6-dichloro-2-aminophenol, 6-nitro - 4 - chloro- or -methyl - 2 - aminophenol, 5-chloro- or -nitro-2-aminophenol, 5-nitro-4-chloro-2-aminophenol, 2 : 5-dimethoxy-aniline, 6 - nitro - 2 - aminophenol - 4 - sulphonic acid, 2-aminophenol-5-sulphonamide or -methylsulphone, 2-aminophenol-4-ethylsulphone, 4-nitro-or -chloro-6-acetylamino-2-aminophenol and 6 - acetylamino - 2 - aminophenol - 4 - methylsulphone; coupling components:-1 - acetylamino - 8 - naphthol - 6 - sulphamide or -sulphodimethylamide or -sulphonic acid phenylamide or -sulphomethylamide or -sulphonic acid-N-ethyl-anilide or -methylsulphone, 1-propionylamino - 8 - naphthol - 6 - sulphonic acid anilide or -sulphopropylamide, 1-ethoxyacetylamino-8-naphthol - 6 - sulphamide, 1 - carbomethoxyamino- or -carboethoxyamino-8-naphthol-6-sulphamide, 1 - methanesulphonylamino - 8 - naphthol-6-sulphonic acid morpholide, 1-p-toluenesulphonylamino - 8 - naphthol - 6 - sulphonic acid piperidide, 1-benzoylamino-8-naphthol-6-sulphonic acid ethanolamide or -phenylsulphone, 1 - ureido - 8 - naphthol - 6 - sulphamide, 1 - benzenesulphonylamino - 8 - naphthol - 6 - phenylsulphone, 1 - b - chloropropionylamino - 8 - naphthol - 6 - sulphonic acid ethanolamide and 1 - ethylsulphonylamino - 8 - naphthol-6-sulphamide. Reference has been directed by the Comptroller to Specifications 637,404, 667,168, 712,037, 736,034, 737,619, 743,583 and 774,884.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH823945X | 1955-02-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB823945A true GB823945A (en) | 1959-11-18 |
Family
ID=4539725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4219/56A Expired GB823945A (en) | 1955-02-11 | 1956-02-10 | Improvements relating to metallisable monoazo dyestuffs, of the benzene-azo naphthalene series, complex heavy metal compounds thereof, and their use |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB823945A (en) |
-
1956
- 1956-02-10 GB GB4219/56A patent/GB823945A/en not_active Expired
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