CH228844A - Process for the preparation of a tetrakisazo dye. - Google Patents
Process for the preparation of a tetrakisazo dye.Info
- Publication number
- CH228844A CH228844A CH228844DA CH228844A CH 228844 A CH228844 A CH 228844A CH 228844D A CH228844D A CH 228844DA CH 228844 A CH228844 A CH 228844A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- amino
- parts
- obtainable
- alkaline
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 15
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 claims description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- SSQQBRZUIXIPIP-UHFFFAOYSA-N 5-diazo-2-nitrocyclohexa-1,3-diene Chemical compound [O-][N+](=O)C1=CCC(=[N+]=[N-])C=C1 SSQQBRZUIXIPIP-UHFFFAOYSA-N 0.000 claims description 3
- 238000006193 diazotization reaction Methods 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 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 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- WDFSYFIRFAWWGG-UHFFFAOYSA-N N-(4-diazocyclohexa-1,5-dien-1-yl)acetamide Chemical compound C(C)(=O)NC1=CCC(C=C1)=[N+]=[N-] WDFSYFIRFAWWGG-UHFFFAOYSA-N 0.000 claims 1
- 238000005530 etching Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000000203 mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000188250 Idas Species 0.000 description 1
- 101150057104 MCIDAS gene Proteins 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000725 suspension 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/50—Tetrazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Tetrakisazofarbstoffes. Es wurde gefunden, dass man einen neuen Tetrakis#azofa#rbs:toff erhält, wenn man die Diaminoverbindung, die erhältlich ist durch Verseifen des Disazofarbstoffes"de-r .selbst er hältlich ist durch Vereinigen von 1-Diazo-4- acetylaminobenzal mit 1-Amino-3-methylben- zol,
WeiterdiazotieTen des so erhaltenen Mo- noazofarbstoffes und Vereinigen in akaIi- schem Medium milder 2-Amino-8-oxynaph- thalin-6-sulfonsäure, tetrazotiert und mit 2 Mol 1-Amino-3,oxybenzol vereinigt.
Der neue Farbstoff bildet ein dunkles, bronzierendes Pulver, Idas sich in Wasser mit violetter, in konzentriertem Schwefelsäure mit blauem Farbe löst. Der Farbstoff färbt Baum- wolle in violettschwarzen Tönen, die durch Behandeln mit Formaldehyd oder mit 4-Ni- tro,diazo#benzol nachentwickelt werden können.
Die mit 4-Nitrodiazobenzol erhaltenen, braun schwarzen Töne sind .gut waschecht und, iso- woh.l neutral als auch alkalisch, ausgezeichnet ätzbar. <I>Beispiel:</I> 15,0 Teile 1-Aminoi-4-acetylaminobenzo#l werden in. bekannter Weise :diazotiert;
die Diazolösung wird durch Zusatz von 20 % iger Natriumacetatlössung kongoneutral gestellt;
dann wird eine Lösung von 10,7 Teilen 1- Amino-3-methylbenzol, gelöst in 50 Teilen Wasser mit Hilfe von 13 Teilen 30 %iger Salzsäure, zugegeben. Nach 24 Stunden wird .der unlösliche 31#onoazofarbs@toff abfiltriert,
dann mit 100 Teilen Wasser gut veTpastet, mit weiteren 500 Teilen Wasser verdünnt. Dann werden,eine Lösung von 6,9 Teilen Na triumnitrit und 28 Teile Salzsäure von 30 zugegeben.
Das Diazotierungsgemisch wird bei 15 bis 20 während 2 biss 21/2 Stunden gut gerührt und dann zu einer Lösung gegeben, die durch Lösen von 23,9 Teilen 2-Amino-8- oxynaphthalin,-6-.sulfonisiäure unter Zusatz von 30 Teilen Natriumcarbonat bereitet wunde.
Nach mehrstündigemRühren wird' der schwer lösliche Disazofarbstoff abfiltriert. Der ab- filtrierte Farbstoff wird:
mit 1000 Teilen Wasser wieder angerührt, zum Sieden er hitzt und dann, mit 140 Teilen 30%iger Na- triumhydroxydlösung versetzt und während 1 bis l1/2 Stunden unter Rühren im Sieden ier- halten. Hierauf wird mit Salzsäure neutraIi- siert, auf 15 abgekühlt,
die Diaminodisiazo- farbstofflüsung mit einer Lösung von 13,8 Teilen Natriumnitrit und 55 Teilen Salzsäure von<B>30%</B> versetzt und bei. 15 während 11/;
bis 2 Stunden gerührt. Die so erhaltene Sus- pen@sion wird in. eine Lösung eingerührt, die in 300 Teilen Wasser 21,8 Teile 1-Amino-3- oxybenzol und 60 Teile Natriumoarbonat ent hält.
Man rührt einige Stunden bei Raumtem- peratur, neutralisiert sorgfältig den grössten Teildes Alkaliearbona;tes mit Salzsäure und filtriert.
Process for the preparation of a tetrakisazo dye. It has been found that a new Tetrakis # azofa # rbs: toff is obtained when the diamino compound, which is obtainable by saponifying the disazo dye itself, is obtainable by combining 1-diazo-4-acetylaminobenzal with 1 -Amino-3-methylbenzene,
Further diazotization of the monoazo dye thus obtained and combining in an alkaline medium of mild 2-amino-8-oxynaphthalene-6-sulfonic acid, tetrazotized and combined with 2 moles of 1-amino-3-oxybenzene.
The new dye forms a dark, bronzing powder, Idas dissolves in water with a violet color, in concentrated sulfuric acid with a blue color. The dye dyes cotton in violet-black tones, which can be developed after treatment with formaldehyde or with 4-nitro, diazo-benzene.
The brown-black shades obtained with 4-nitrodiazobenzene are washable and, iso-neutral as well as alkaline, extremely etchable. <I> Example: </I> 15.0 parts of 1-aminoi-4-acetylaminobenzo # l are: diazotized in a known manner;
the diazo solution is made congoneutral by adding 20% sodium acetate solution;
then a solution of 10.7 parts of 1-amino-3-methylbenzene, dissolved in 50 parts of water with the aid of 13 parts of 30% strength hydrochloric acid, is added. After 24 hours, the insoluble 31 # onoazofarbs @ toff is filtered off,
then make a good paste with 100 parts of water, dilute with another 500 parts of water. Then, a solution of 6.9 parts of sodium nitrite and 28 parts of 30 hydrochloric acid are added.
The diazotization mixture is stirred well at 15 to 20 for 2 to 21/2 hours and then added to a solution which is obtained by dissolving 23.9 parts of 2-amino-8-oxynaphthalene, -6-sulfonic acid with the addition of 30 parts of sodium carbonate causes wound.
After several hours of stirring, the sparingly soluble disazo dye is filtered off. The filtered dye will:
stirred again with 1000 parts of water, heated to the boil and then mixed with 140 parts of 30% sodium hydroxide solution and kept at the boil for 1 to 11/2 hours with stirring. It is then neutralized with hydrochloric acid, cooled to 15,
a solution of 13.8 parts of sodium nitrite and 55 parts of hydrochloric acid of <B> 30% </B> is added to the diaminodisiazo dye solution and at. 15 during 11 /;
stirred for up to 2 hours. The suspension obtained in this way is stirred into a solution which contains 21.8 parts of 1-amino-3-oxybenzene and 60 parts of sodium carbonate in 300 parts of water.
The mixture is stirred for a few hours at room temperature, carefully neutralized most of the alkali carbonate with hydrochloric acid and filtered.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH228844T | 1941-09-02 | ||
CH226016T | 1942-07-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH228844A true CH228844A (en) | 1943-09-15 |
Family
ID=25726953
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH228844D CH228844A (en) | 1941-09-02 | 1941-09-02 | Process for the preparation of a tetrakisazo dye. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH228844A (en) |
-
1941
- 1941-09-02 CH CH228844D patent/CH228844A/en unknown
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