CS207599B2 - Method of making the inner complex salts of the azo-dyes with cobalt or chrome of the type 1:2 - Google Patents
Method of making the inner complex salts of the azo-dyes with cobalt or chrome of the type 1:2 Download PDFInfo
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- CS207599B2 CS207599B2 CS254978A CS254978A CS207599B2 CS 207599 B2 CS207599 B2 CS 207599B2 CS 254978 A CS254978 A CS 254978A CS 254978 A CS254978 A CS 254978A CS 207599 B2 CS207599 B2 CS 207599B2
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- parts
- dyes
- chromium
- cobalt
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- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000000987 azo dye Substances 0.000 title claims abstract description 9
- 229910017052 cobalt Inorganic materials 0.000 title claims abstract description 7
- 239000010941 cobalt Substances 0.000 title claims abstract description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 150000003839 salts Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims abstract description 23
- 239000000725 suspension Substances 0.000 claims abstract description 13
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 9
- 239000011651 chromium Substances 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 239000004952 Polyamide Substances 0.000 claims abstract description 6
- 229920002647 polyamide Polymers 0.000 claims abstract description 6
- 210000002268 wool Anatomy 0.000 claims abstract description 5
- 238000001465 metallisation Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 5
- 239000007921 spray Substances 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- MQJUTXAYGNUBKO-UHFFFAOYSA-M sodium;3,7-ditert-butylnaphthalene-2-sulfonate Chemical compound [Na+].C1=C(C(C)(C)C)C(S([O-])(=O)=O)=CC2=CC(C(C)(C)C)=CC=C21 MQJUTXAYGNUBKO-UHFFFAOYSA-M 0.000 claims description 3
- 239000000080 wetting agent Substances 0.000 claims description 2
- -1 O-hydroxy-O-carboxyazo Chemical group 0.000 claims 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- BMRVLXHIZWDOOK-UHFFFAOYSA-N 2-butylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCC)=CC=C21 BMRVLXHIZWDOOK-UHFFFAOYSA-N 0.000 claims 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 claims 1
- RHZUVFJBSILHOK-UHFFFAOYSA-N anthracen-1-ylmethanolate Chemical group C1=CC=C2C=C3C(C[O-])=CC=CC3=CC2=C1 RHZUVFJBSILHOK-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 claims 1
- 239000000796 flavoring agent Substances 0.000 claims 1
- 235000019634 flavors Nutrition 0.000 claims 1
- 229910021432 inorganic complex Inorganic materials 0.000 claims 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 239000010985 leather Substances 0.000 abstract description 2
- 239000004677 Nylon Substances 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 229920001778 nylon Polymers 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- AVQFHKYAVVQYQO-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonamide Chemical compound NC1=CC(S(N)(=O)=O)=CC=C1O AVQFHKYAVVQYQO-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- FLJPGEWQYJVDPF-UHFFFAOYSA-L caesium sulfate Chemical compound [Cs+].[Cs+].[O-]S([O-])(=O)=O FLJPGEWQYJVDPF-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- AFTOVGIFYVNBID-UHFFFAOYSA-M sodium;2-butylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(CCCC)=CC=C21 AFTOVGIFYVNBID-UHFFFAOYSA-M 0.000 description 2
- CJLSDBRIXZFCKV-UHFFFAOYSA-N 4-chloro-3-oxo-n-phenylbutanamide Chemical compound ClCC(=O)CC(=O)NC1=CC=CC=C1 CJLSDBRIXZFCKV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004532 chromating Methods 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- NFMHSPWHNQRFNR-UHFFFAOYSA-N hyponitrous acid Chemical group ON=NO NFMHSPWHNQRFNR-UHFFFAOYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 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
- C09B45/01—Complex metal compounds of azo dyes characterised by the method of metallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Description
Předmětem vynálezu je způsob výroby vnitřně komplexních solí azobarviv s kobaltem nebo cihromem, typu 1:2, určených pro barvení bílkovinných vláken, polyamidových vláken a kůže z neutrálních nebo slabě kyselých lázní.SUMMARY OF THE INVENTION The present invention relates to a process for the production of 1: 2 cobalt or broth azo dyes with a colorant content for coloring protein fibers, polyamide fibers and leather from neutral or weakly acid baths.
Jsou již známy způsoby výroby vnitřně komplexních solí azobarviv s kovy typu 1; 2, majících složení vhodné pro léčiva; těmito azobalrvivy jsou o,o‘-dihydroxyaizo, o-hydroxy-o‘-ikarboxyiazo nebo o-hydroxy-o‘-aminoazo.Methods for producing intrinsically complex azo dyes with type 1 metals are already known; 2 having compositions suitable for pharmaceuticals; these azo-coatings are o, o-dihydroxyaizo, o-hydroxy-o-ocarboxyiazo or o-hydroxy-o-aminoazo.
V závislostí na struktuře molekuly barvivá a metalizačního činidla se metalizační reakce provádí ve vodném prostředí nebo v organických rozpouštědlech za zvýšené teploty a normálního nebo zvýšeného tlaku.Depending on the structure of the dye molecule and the metallizing agent, the metallization reaction is carried out in an aqueous medium or in organic solvents at elevated temperature and normal or elevated pressure.
К nejdůležitějším způsobům výroby těchto sloučenin patří chromování o,o‘-dihydroxýazobarviv pomocí chiromsalicylolvých komplexních sloučenin ve vodném· prostředí podle německého patentu 741 46.2, chromování pomocí chrqmitých solí ve fcrmamidu podle německého patentu 715 082, koballtování o,o‘-dihydroxyazobarviv ve vodném roztoku v zásaditém prostředí za použití síranu nebo chloridu kobaltnatého podle francouzského· patentu 1 071 168 a německého patentu 934 905. Pro tvorbu vnitrně komplexních solí s kovy se azobarviva předem odfiltrují a pak znovu rozpulstí ve vodě nebo v organickém rozpouštědle nebo· se používá roztoků nelbo suspenzí barviiv v reaikční směsi získané po kopulaci.The most important processes for the preparation of these compounds include chromating o, o'-dihydroxyazo dyes with chiromsalicyl complex compounds in an aqueous medium according to German patent 741 46.2, chromium plating with chromium salts according to German patent 715 082, coballizing o, o'-dihydroxyazo dye in water in alkaline conditions using cobalt sulphate or chloride according to French patent 1,071,168 and German patent 934,905. For the formation of intrinsically complex metal salts, the azo dyes are first filtered off and then redissolved in water or an organic solvent, or solutions or suspensions are used dyes in the reaction mixture obtained after coupling.
Očelém vynálezu je metalizační projces podstatně urychlit a zjednodušit technologii získávání vnitřně komplexních solí azobariviv s kovy.It is an object of the invention to provide a metallization process to substantially speed up and simplify the technology for obtaining intrinsically complex azo dyes with metals.
Podle vynálezu se metalizace provádí současně se sušením pastovitého bar.viva ve fluidiizační rozprašovací sušárně nebo v sušárně jiného typu při vysdké teplotě, s výhodou až do 23Ó °C.According to the invention, the metallization is carried out simultaneously with the drying of the pasty dye in a fluidized-bed spray dryer or another type of dryer at a high temperature, preferably up to 23 ° C.
Je tedy předmětem vynálezu způlsoib výroby vnitřně komplexních solí azobarviv s kobaltem· nebo chromém, typu 1: 2, vyznačující se tím·, že se o,o‘-dihydroxyazobarviva, o-hydroxy-o^karbpxyazobariviva, o-hydroxy-o‘-aminoazobar.viya v podobě past, suspenzí nebo roztoků smísí se sloučeninami uvolňujícími chrom- a kobalt a suší se za teploty v rozmezí 160 až 230 °C.Accordingly, it is an object of the present invention to provide an internally complex salt of azo dye with cobalt or chromium, type 1: 2, characterized in that o, o'-dihydroxyazo dyes, o-hydroxy-o-carboxyxy dyes, o-hydroxy-o'- Aminoazobaric acid in the form of pastes, suspensions or solutions are mixed with chromium- and cobalt-releasing compounds and dried at a temperature in the range of 160-230 ° C.
Způsob podle vynálezů se účelně provádí tak, že se pasty o.o^dihydroxyazobarviiva, o-hydroxy-o‘-karboxyiazobarviva, o-hyd.roxy-o‘-ammoaizobairviva nebo jejich vodné Suspenze před sušením· mísí v mísící is vhodným množstvím metalizačního činidla, načež se odvádějí pro sušení nejvýhodněji při teplotách až 230 ÓC. Metalizace probíhá sou207599 časně se sušením· barviva. Pro usnadnění metálizačního · procesu je možno· k pastám, suspenzím nebo· roztokům určeným pro · sušení · přidávat smáčecí činidla, jako je například sodná sůl kyseliny butylnaftalensulfonové (Nekalin S) nebo Polikol · 42.The process according to the invention is expediently carried out by mixing the pastes of the dihydroxyazo dyes, the o-hydroxy-o'-carboxy-dyes, the o-hydroxy-o'-ammoisobarivatives or their aqueous suspensions before mixing with a suitable amount of metallizing agent. then are removed to drying preferably at temperatures up to 230 o C. the metallization extends sou207599 early drying · dyes. Wetting agents such as butylnaphthalenesulfonic acid sodium salt (Nekalin S) or Polikol 42 may be added to the pastes, suspensions or solutions to be dried to facilitate the metalization process.
Dále uvedené příklady způsob podle vynálezu blíže · objasňují.The following examples illustrate the process according to the invention.
Příklad 1 hmotnostních dílů momoazosloučeníny, připravené kopulací diazotovaného 2-aminofenol-4-sulfonamidu s 2-chlor-acetylacetanilidelm. v podobě · pasty, se· vnese do 300 objemových dílů vody a vzniklá směs se míchá až do rozplavení pasty, načež · se přidá 46 objemových dílů 13,5 % vodného roztoku chloridu · kobaltnaitého a 3,9 objemového dílu 45n/n roztoku hydroxidu sodného. Suspenze se míchá 15 minut, načež se· vede na talíř rozprašovací ' sušárny. Teplota přiváděného vzduchu je v rozmezí· 180 až 190° Celsia. Po skončení sušení a metaiizace se získá žlutohnědý · prášek, který z neutrální 'nebo slabě kyselé lázně uděluje vlně, polyamidovým vláknům a kůži žluté zbarvení.Example 1 parts by weight of a momoazo compound prepared by coupling a diazotized 2-aminophenol-4-sulfonamide with 2-chloroacetylacetanilide. in the form of a paste, is added to 300 parts by volume of water and the mixture is stirred until the paste is melted, then 46 parts by volume of a 13.5% cobalt (II) chloride aqueous solution and 3.9 parts by volume of a 45n / n hydroxide solution are added. sodium. The suspension is stirred for 15 minutes and then passed onto a spray drier plate. The supply air temperature is between 180 ° C and 190 ° C. Upon completion of drying and metallization, a tan powder is obtained which gives the wool, the polyamide fibers and the skin a yellow color from the neutral or slightly acidic bath.
Suspenzi barvMa je. nutno přivádět tak rychle, aby barvivo nelmOhlo ulpívat na stěnách sušárny.The color suspension is. the dye must not be allowed to adhere to the walls of the oven.
Příklad 2Example 2
37,3 hmotnostního dílu monnazosloučeniny, získané kopulací diazotovaného 2-aminofenol-4-sulfonamidu s l-feny--3-methyl-5pyrazolonem v podobě pasty, se vnese do 300 objemových dílů vody a 2 objemových dílů sodné soli kyseliny butylnaftalθnsulfnnůivé (Nekalin S), Siměs se míchá až do rozplavení pasty. Pak se přidá 45 objemových dílů 15,5% vodného roztoku · síranu · kohaltnatého a 3,9 objemového dílu 45·% -roztoku hydroxidu sodného.37.3 pbw of the mono compound obtained by coupling the diazotized 2-aminophenol-4-sulfonamide with 1-phenyl-3-methyl-5-pyrazolone as a paste is added to 300 pbw of water and 2 pbw of butylnaphthalenesulfonic acid sodium salt (Nekalin S). ) Simes mix until the paste is washed. Then 45 parts by volume of a 15.5% aqueous solution of cesium sulfate and 3.9 parts by volume of a 45% solution of sodium hydroxide are added.
Vzniklá sulSpenze se míchá 15 minut, načež se vede na talíř rozprašovací · sušárny. Teplota přiváděného vzduchu je v rozmezí 180 až 190 °C. Suspenzi barviva je putno přivádět tak rychle, aby barvivo nemohlo ulpívat na stěnách sušárny.The resulting suspension was stirred for 15 minutes and then passed onto a spray drier plate. The supply air temperature is between 180 ° C and 190 ° C. The dye suspension should be introduced so quickly that the dye cannot adhere to the walls of the dryer.
iPo· · skončení sušení a metaiizace· se získá žlutohnědý prášek, který z neutrální neboiPo · · end of drying and metallization · yellowish-brown powder is obtained which is neutral or
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL19751577A PL107997B1 (en) | 1977-04-20 | 1977-04-20 | METHOD OF MANUFACTURE OF AZO DYES OF METALOKOMPLEKMETHOD OF PRODUCING AZO METALLIZED DYES OF TYPE 1: TYPES 1: 2 CONTAINING KOBALT OR CHROME 2, CONTAINING COBALT OR CHROMIUM |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS207599B2 true CS207599B2 (en) | 1981-08-31 |
Family
ID=19982049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS254978A CS207599B2 (en) | 1977-04-20 | 1978-04-20 | Method of making the inner complex salts of the azo-dyes with cobalt or chrome of the type 1:2 |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH635362A5 (en) |
| CS (1) | CS207599B2 (en) |
| DE (1) | DE2817361A1 (en) |
| PL (1) | PL107997B1 (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE931793C (en) * | 1953-01-24 | 1955-08-18 | Bayer Ag | Process for the preparation of chromium compounds of metal complex-forming azo dyes |
-
1977
- 1977-04-20 PL PL19751577A patent/PL107997B1/en unknown
-
1978
- 1978-04-20 CH CH425578A patent/CH635362A5/en not_active IP Right Cessation
- 1978-04-20 CS CS254978A patent/CS207599B2/en unknown
- 1978-04-20 DE DE19782817361 patent/DE2817361A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE2817361A1 (en) | 1978-11-02 |
| CH635362A5 (en) | 1983-03-31 |
| PL197515A1 (en) | 1978-11-06 |
| PL107997B1 (en) | 1980-03-31 |
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