DE109063C - - Google Patents
Info
- Publication number
- DE109063C DE109063C DENDAT109063D DE109063DA DE109063C DE 109063 C DE109063 C DE 109063C DE NDAT109063 D DENDAT109063 D DE NDAT109063D DE 109063D A DE109063D A DE 109063DA DE 109063 C DE109063 C DE 109063C
- Authority
- DE
- Germany
- Prior art keywords
- black
- acid
- blue
- dyes
- precipitation
- 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.)
- Active
Links
- 239000000975 dye Substances 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 14
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 7
- -1 4 -sulfo- azo- benzene aniline Chemical compound 0.000 claims description 6
- 229920000742 Cotton Polymers 0.000 claims description 6
- 150000008049 diazo compounds Chemical class 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000001264 neutralization Effects 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims 6
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims 3
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-Chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims 2
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 claims 2
- 229910000906 Bronze Inorganic materials 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000010974 bronze Substances 0.000 claims 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 claims 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N P-Phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N Tolidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 claims 1
- YFGRSOGKVQIGKG-UHFFFAOYSA-N [Cl].NC1=CC=CC=C1 Chemical compound [Cl].NC1=CC=CC=C1 YFGRSOGKVQIGKG-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive Effects 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000003973 paint Substances 0.000 claims 1
- 150000004986 phenylenediamines Chemical class 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 238000010186 staining Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000005415 aminobenzoic acids Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 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 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229950000244 sulfanilic acid Drugs 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
- C09B35/38—Trisazo dyes ot the type
- C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
- C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Werden die aus der Amidonaphtoldisulfosä'ure K oder H mit Monodiazoverbindungen in saurer Lösung dargestellten Farbstoffe durch die Einwirkung gleicher Molecule einer Tetrazoverbindung in Zwischenproducte übergeführt und diese mit der m-Naphtylendiamin-ßg-sulfosäure des Patentes 89061 vereinigt, so erhält man sehr werthvolle Polyazofarbstoffe. Diese sind von allen anderen, . nach dem gleichen Verfahren unter Ersatz der Naphtylendiaminsulfosäure durch andere Componenten erhaltenen Farbstoffen in erster Reihe durch ihre erhöhte Farbstärke ausgezeichnet. Weder andere Amine noch Naphtole oder Amidonaphtole können in dieser Beziehung die Naphtylendiaminsulfosäure auch nur annähernd ersetzen. Nur mit dieser erhält man einen Farbstoff, der bereits mit wenigen Procenten ungeheizte Baumwolle schwarz färbt. Zudem sind diese Färbungen durch sehr gute Wasch-, Wasser- und Säure-Echtheit ausgezeichnet. Auch zum Färben von. Halbwolle sind die Producte geeignet. Die Componenten zur Darstellung der Monoazofarbstoffe sind durch die Natur der verwendeten Amidonaphtoldisulfosäure bestimmt. Bei der Η-Säure eignen sich in erster Linie nur die Nitrodiazokörper und sonst nur sehr vereinzelte ß-Naphtylaminsulfosäuren, bei ,der K-Säure hingegen hauptsächlich a-Naphtylamin, Anilin, Amidoazobenzol, Sulfanilsäure, Acetyl - ρ - Phenylendiamin , Nitrodiazokörper, sowie Amidosalicylsäure, Aminobenzoesäuren.Are the from the Amidonaphtoldisulfosä'ure K or H with monodiazo compounds Dyes represented in acidic solution by the action of identical molecules of a tetrazo compound converted into intermediate products and these with m-naphthylenediamine-βg-sulfonic acid of patent 89061 are combined, very valuable polyazo dyes are obtained. These are different from everyone else,. using the same procedure replacing the naphthylenediamine sulfonic acid dyes obtained by other components primarily through their increased Color strength excellent. Neither other amines nor naphthols or amidonaphthols can only approximately replace naphthylenediamine sulfonic acid in this respect. This is the only way to obtain a dye that is unheated with just a few percent Dyes cotton black. In addition, these colors are very easy to wash, water and and acid fastness excellent. Also for coloring. The products are suitable for semi-wool. The components for representing the monoazo dyes are due to the nature of the Amidonaphthol disulfonic acid used. With the Η-acid are primarily suitable Line only the nitrodiazo bodies and otherwise only very isolated ß-naphthylamine sulfonic acids , the K acid, on the other hand, is mainly a-naphthylamine, Aniline, amidoazobenzene, sulfanilic acid, acetyl - ρ - phenylenediamine, nitrodiazo bodies, and amidosalicylic acid, aminobenzoic acids.
Beispiel 1. 36,2 kg des neutralen Natriumsalzes der Amidonaphtoldisulfosäure K werden in 1000 1 Wasser gelöst, mit 14 kg tone. Salzsäure angesäuert und mit der aus 9,3 kg Anilin, 30 kg cone. Salzsäure und 6,9 kg Nitrit in der üblichen Weise erhaltenen Diazoverbindung combinirt. Nach etwa 10 Stunden macht man durch Zusatz von Soda alkalisch und versetzt mit der aus 18,4 kg Benzidin in der üblichen Weise dargestellten Tetrazoverbindung. Der Zwischenkörper bildet sich sofort und scheidet sich als grünschwarzer Niederschlag ab. Man läfst nun unter Rühren zur Reactionsmasse die Lösung von 23,3 kg m-Naphtylendiamin - ß3-sulfosäure in 500 1 Wasser und 1 5 kg Soda zulaufen. Der Niederschlag geht allmälig wieder in Lösung, man wärmt alsdann nach 3 Stunden an und salzt den Farbstoff aus. Er färbt ungebeizte Baumwolle tief blauschwarz.Example 1. 36.2 kg of the neutral sodium salt of amidonaphthol disulfonic acid K are dissolved in 1000 l of water, with 14 kg of clay. Hydrochloric acid and acidified with the from 9.3 kg of aniline, 30 kg of cone. Hydrochloric acid and 6.9 kg of nitrite combined in the usual way obtained diazo compound. After about 10 hours it is made alkaline by adding soda and mixed with the tetrazo compound prepared in the usual way from 18.4 kg of benzidine. The intermediate body forms immediately and separates out as a greenish-black precipitate. The solution of 23.3 kg of m-naphthylenediamine-ß 3 -sulfonic acid in 500 l of water and 15 kg of soda is now run in to the reaction mass while stirring. The precipitate gradually goes into solution again, then after 3 hours the mixture is warmed up and the dye is salted out. It dyes unstained cotton a deep blue-black.
Beispiel 2. 23,4kg salzsaures Amidoazobenzol werden mit 15 kg Salzsäure und 6,9 kg Nitrit in 1000 1 Wasser diazotirt. Die erhaltene Diazoverbindung wird zu einer Lösung von 34,1 kg des sauren Natronsalzes der K-Säure laufen gelassen. Die Kuppelung ist nach etwa 12 Stunden beendigt. Macht man nun alkalisch und verfährt im Uebrigen wie bei Beispiel i, so erhält man schliefslich einen Farbstoff, der Baumwolle tiefschwarz färbt.Example 2. 23.4 kg of hydrochloric acid amidoazobenzene are diazotized with 15 kg of hydrochloric acid and 6.9 kg of nitrite in 1000 liters of water. The received Diazo compound becomes a solution of 34.1 kg of the acidic sodium salt of K-acid run. The coupling is completed after about 12 hours. You now make alkaline and if the rest of the procedure is the same as in example i, a dye is finally obtained, which dyes cotton deep black.
Beispiel 3. 14,3 kg a-Naphtylamin werden in der üblichen Weise diazotirt. Die Diazoverbindung combinirt man mit 34,5 kg sauremExample 3. 14.3 kg of a-naphthylamine become diazotized in the usual way. The diazo compound is combined with 34.5 kg of acid
Claims (1)
diaminphenylene
diamine
ß4-sulfo-tylamine
ß 4 -sulfo-
benzolazo-
benzene
K-Säureacid +
K acid
wässerigen Lösung:Color of
aqueous solution:
in Schwefelsäure:Color of the solution
in sulfuric acid:
mit Wasser:When diluting
with water:
Niederschlag purple
Precipitation
schwarz
blau
schwarz
violett
schwarz
roth
violetter
Nieder
schlagGray
black
blue
black
violet
black
red
purple
Low
blow
schwarz
violett
schwarz
blau
roth
violetter
Nieder
schlagGray
black
violet
black
blue
red
purple
Low
blow
schwarz
tiefblau
blau
violette
FällungGray
black
deep blue
blue
purple
precipitation
schwarz
blau
schwarz
blau
blaue
FällungGray
black
blue
black
blue
blueness
precipitation
schwarz
blau
schwarz
blau
violette
FällungGray
black
blue
black
blue
purple
precipitation
grün
schwarz
grün
blau
blaue
Fällungblack
green
black
green
blue
blueness
precipitation
schwarz
violett
schwarz
roth-
stichiges
blau
roth
violette
Fällungbronze
black
violet
black
red
prickly
blue
red
purple
precipitation
Publications (1)
Publication Number | Publication Date |
---|---|
DE109063C true DE109063C (en) |
Family
ID=378992
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT109063D Active DE109063C (en) |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE109063C (en) |
-
0
- DE DENDAT109063D patent/DE109063C/de active Active
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