CH287099A - Process for the preparation of a chromium-containing azo dye. - Google Patents
Process for the preparation of a chromium-containing azo dye.Info
- Publication number
- CH287099A CH287099A CH287099DA CH287099A CH 287099 A CH287099 A CH 287099A CH 287099D A CH287099D A CH 287099DA CH 287099 A CH287099 A CH 287099A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- chromium
- process according
- complex
- azo dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 6
- 239000000987 azo dye Substances 0.000 title claims description 6
- 229910052804 chromium Inorganic materials 0.000 title claims description 6
- 239000011651 chromium Substances 0.000 title claims description 5
- 239000000975 dye Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 150000001845 chromium compounds Chemical class 0.000 claims description 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 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-N sodium;2-hydroxybenzoic acid Chemical compound [Na+].OC(=O)C1=CC=CC=C1O ABBQHOQBGMUPJH-UHFFFAOYSA-N 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
- C09B45/02—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
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Optical Filters (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Ilauptpatent Nr. <B>284075.</B> Verfahren zur Herstellung eines ehromhaltigen Azofarbstoffes. Es wurde gefunden, dass man -zu einem wertvollen, neuen ehromhaltigen Azofarbstoff gelangt, -,venn man auf den Monoazofarbstoff n der Formel
EMI0001.0013
ehromabgebende Mittel derart einwirken lässt,
dass ein ehroinhaltiger Azofarbstoff entsteht, der zwei 31oiloa7ofarbstoffmoleküle an ein Chromatom komple-# gebunden enthält.
Der neue ehromhaltige Farbstoff bildet ein bronzierendes schwarzes Pulver, das sieh in Wasser mit graublauer, in konzentrierter Schwefelsäure mit roter Farbe löst und Wolle aus neutralem oder essigsaurein Bade in grauen Tönen färbt.
über die verwendeten ehromabgebenden Mittel sowie über die Reaktionsbedingungen gibt das Hauptpatent Auskunft.
<I>Beispiel:</I> <B>23,3</B> Teile 6-NTitro-2-aniino-l-oxvbenzol-4- sulfonsliire,imid werden in 200 Teilen Wasser und<B>15</B> Volumteilen 10-n-Silzsiure aufge schlämmt und bei<B>5</B> bis<B>100</B> mit<B>25</B> Volumtei- len 4-n-Natriumnitritlösung diazotiert. Die durch Zugabe von Natriumearbonat neutrali sierte Diazoverbindung lässt man einlaufen in eine mit Eis auf<B>00</B> abgekühlte Lösung von <B>22,
9</B> Teilen 1-n-Butyrylaiuino-7-oxynaphthaliii in<B>52</B> Volumteilen 2-n-NLatriumhydro2z#vdlösu-ng und<B>50</B> Volumteilen 2-u-Natri-Liniearbonat- lösung. Nach beendeter Kupplung wird der abgeschiedene Farbstoff filtriert und mit ver dünnter Natriumehloridlösung gewasehen. Ge trocknet stellt er ein violettes Pulver dar, das sieh in heissem Wasser mit violetter und in konzentrierter Schwefelsäure mit reiner roter Farbe löst.
Der nach obigen Angaben erhaltene Filter kuchen des Farbstoffes wird in<B>1500</B> Teilen Wasser aufgeschlämmt und mit 200 Teilen einer Lösung von ehromsalicylsaurem Kalhim- Natrium mit einem Chromgehalt von 1,8511/a versetzt.
Die Lösung von ehronisalieylsaurein Kalium-Natrium erhält man zum Beispiel durch Aufkochen von<B>100</B> Teilen einer Chrom- sulfatlösung (Cr-SO,1011) mit einem Chrorn- gehalt von 3,71/o mit<B>19,6</B> Teilen Salieylsäure,
ljösen des entstandenen Niedersehlages durch Zugabe von<B>15</B> Voluniteilen 10-n-Natrium- hydroxydlösung und<B>15</B> Vol.umteilen 10-n-Ka- liumhydroxydlösung und Einstellen mit Was ser auf 200 Teile. Das Chron-iiergemiseh wird während etwa<B>5</B> Stunden bei Siedetemperatur halten und die so erhaltene Chromverbin dung des Parbstoffes durch Natriumehlorid- zu,gabe abgeschieden und abfiltriert.
Additional patent to main patent no. <B> 284075. </B> Process for the production of an azo dye containing Ehrom. It has been found that -a valuable, new Ehrom-containing azo dye is obtained - if one uses the monoazo dye n of the formula
EMI0001.0013
allows honorary funds to have an effect
that an azo-dye containing earring is formed which contains two 31oiloa7o-dye molecules completely bound to a chromium atom.
The new Ehrom-containing dye forms a bronzing black powder, which dissolves in water with a gray-blue color, in concentrated sulfuric acid with a red color, and dyes wool from a neutral or acetic acid bath in gray tones.
The main patent provides information about the used Ehrom-donating agents and about the reaction conditions.
<I> Example: </I> <B> 23.3 </B> parts of 6-Nitro-2-aniino-1-oxvbenzene-4-sulfonsliire, imide in 200 parts of water and <B> 15 </ B > Parts by volume 10-n-silicic acid slurried and diazotized at <B> 5 </B> to <B> 100 </B> with <B> 25 </B> parts by volume 4-N sodium nitrite solution. The diazo compound, neutralized by adding sodium carbonate, is allowed to run into a solution of <B> 22 which has been cooled with ice to <B> 00 </B>,
9 parts 1-n-Butyrylaiuino-7-oxynaphthaliii in <B> 52 </B> parts by volume 2-n-Natriumhydro2z # vdlösu-ng and <B> 50 </B> parts by volume 2-u-sodium Line carbonate solution. After the coupling has ended, the deposited dye is filtered and washed with dilute sodium chloride solution. When dried it is a violet powder that dissolves in hot water with violet color and in concentrated sulfuric acid with pure red color.
The filter cake of the dye obtained according to the above information is slurried in 1500 parts of water and mixed with 200 parts of a solution of sodium salicylic acid Kalhim with a chromium content of 1.8511 / a.
The solution of Ehronisalieylsaurein potassium-sodium is obtained, for example, by boiling <B> 100 </B> parts of a chromium sulfate solution (Cr-SO, 1011) with a chromium content of 3.71 / o with <B> 19 , 6 </B> parts of salicic acid,
Dissolve the resulting sediment by adding <B> 15 </B> parts by volume of 10 N sodium hydroxide solution and <B> 15 </B> by dividing the volume of 10 N potassium hydroxide solution and adjusting with water to 200 parts . The chronization mixture is kept at the boiling temperature for about 5 hours and the chromium compound of the paraffin thus obtained is separated off by adding sodium chloride and is filtered off.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH284075T | 1949-11-18 | ||
| CH287099T | 1949-11-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH287099A true CH287099A (en) | 1952-11-15 |
Family
ID=25732348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH287099D CH287099A (en) | 1949-11-18 | 1949-11-18 | Process for the preparation of a chromium-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH287099A (en) |
-
1949
- 1949-11-18 CH CH287099D patent/CH287099A/en unknown
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