DE156828C - - Google Patents
Info
- Publication number
- DE156828C DE156828C DENDAT156828D DE156828DA DE156828C DE 156828 C DE156828 C DE 156828C DE NDAT156828 D DENDAT156828 D DE NDAT156828D DE 156828D A DE156828D A DE 156828DA DE 156828 C DE156828 C DE 156828C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- blue
- brown
- purple
- red
- 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.)
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- 239000002253 acid Substances 0.000 claims description 13
- 239000000975 dye Substances 0.000 claims description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 5
- 238000004040 coloring Methods 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 210000002268 Wool Anatomy 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MNURPFVONZPVLA-UHFFFAOYSA-N 2-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1Cl MNURPFVONZPVLA-UHFFFAOYSA-N 0.000 description 1
- SGBQUMZTGSQNAO-UHFFFAOYSA-N 2-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(O)=CC=C21 SGBQUMZTGSQNAO-UHFFFAOYSA-N 0.000 description 1
- IQOJIHIRSVQTJJ-UHFFFAOYSA-N 3-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(Cl)=C1 IQOJIHIRSVQTJJ-UHFFFAOYSA-N 0.000 description 1
- 229940018564 M-PHENYLENEDIAMINE Drugs 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N Naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- 240000000358 Viola adunca Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- CVNRIKWXNAAZKB-UHFFFAOYSA-M [N+](=O)([O-])C1=C(C(=C(C=C1)S(=O)(=O)[O-])Cl)[N+](=O)[O-] Chemical compound [N+](=O)([O-])C1=C(C(=C(C=C1)S(=O)(=O)[O-])Cl)[N+](=O)[O-] CVNRIKWXNAAZKB-UHFFFAOYSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000001816 cooling 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
- 238000007747 plating Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/44—Preparation of azo dyes from other azo compounds by substituting amine groups for hydroxyl groups or hydroxyl groups for amine groups; Desacylation of amino-acyl groups; Deaminating
-
- 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
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In der Patentschrift 150373 ist gezeigt worden, daß man aus der Diamidochlorbenzolsulfosäure (N: N: Cl: S = 1:3:2:5) durch Tetrazotieren und Kombinieren der Tetrazoverbindung in Gegenwart von Alkalien bezw. salzsäurebindenden Mitteln mit 2 Molekülen ein und desselben oder zweier verschiedener Chromogene nachchromierbare Disazofarbstoffe erhält, welche identisch sind mit denjenigen, die aus der Tetrazoverbindung der o-o-Diamidophenolsulfosäure erhalten werden.In patent specification 150373 it has been shown that from the diamidochlorobenzenesulfonic acid (N: N: Cl : S = 1: 3: 2: 5) by tetrazotizing and combining the tetrazo compound in the presence of alkalis or. Hydrochloric acid binding agents with 2 molecules of the same or two different chromogens are obtained after-chromable disazo dyes which are identical to those obtained from the tetrazo compound of oo-diamidophenolsulfonic acid.
Es hat sich nun gezeigt, daß die Diamidochlorbenzolsulfosäure von der FormelIt has now been shown that the diamidochlorobenzenesulfonic acid of the formula
ClCl
NH1,NH 1 ,
NH-,NH-,
welche durch Reduktion der im Patent 116339 beschriebenen 1 · 3 - Dinitro - 4 · 5 - chlorbenzolsulf osäure erhalten werden kann, ein ganz ähnliches Verhalten zeigt, indem die Tetrazoverbindung dieser Diamidosäure mit Chromogenen bei Gegenwart von Alkalien oder salzsäurebindenden Mitteln kombiniert nicht die entsprechenden chlorhaltigen Disazofarbstoffe liefert, sondern Kombinationen, welche identisch sind mit denjenigen, die aus der Tetrazoverbindung der entsprechenden Diamidophenolsulfosäure entstehen.which by reducing the 1 · 3 - dinitro - 4 · 5 - chlorobenzenesulf described in patent 116339 Acid can be obtained showing a very similar behavior by the tetrazo compound this diamido acid with chromogens in the presence of alkalis or hydrochloric acid binding agents Agents combined do not provide the corresponding chlorine-containing disazo dyes, but combinations which are identical are with those derived from the tetrazo compound of the corresponding diamidophenolsulfonic acid develop.
3535
Das Verfahren wird durch folgende Beispiele erläutert:The procedure is illustrated by the following examples:
Darstellung der 1 · 3-Diamido-4 · 5-Representation of the 1 · 3-Diamido-4 · 5-
chlorbenzolsulfosäure.
15 Teile dinitrochlorbenzolsulfosaures Natron werden allmählich in 100 Teile heißes
Wasser, zu dem vorher 30 Teile Eisen und I Teil Essigsäure gegeben wurde, eingetragen.
Nach erfolgter Reduktion wird mit 1,3 Teilen Soda alkalisch gemacht und aus
der vom Eisenschlamm abfiltrierten Lauge nach vorhergehendem Einengen die Diamidochlorbenzolsulfosäure
mittels Salzsäure gefällt. Dieselbe ist in kaltem Wasser schwer, leichter in heißem Wasser löslich, aus welchem
sie beim Erkalten in farblosen Nadeln kristallisiert. Sie ist leicht löslich in verdünnten
Alkalien sowie in Natriumacetat und wird durch Zusatz von Mineralsäuren wieder daraus abgeschieden. Sie liefert eine gelbe
Tetrazoverbindung.chlorobenzenesulfonic acid.
15 parts of dinitrochlorobenzenesulfonate are gradually introduced into 100 parts of hot water to which 30 parts of iron and 1 part of acetic acid have previously been added. After the reduction has taken place, 1.3 parts of soda are made alkaline and the diamidochlorobenzenesulfonic acid is precipitated from the liquor filtered off from the iron sludge after prior concentration. It is difficult to dissolve in cold water, and more easily soluble in hot water, from which it crystallizes in colorless needles on cooling. It is easily soluble in dilute alkalis and in sodium acetate and is separated out again by adding mineral acids. It gives a yellow tetrazo compound.
Tetrazotierung der I · 3'-Diamido-4 · 5-chlorbenzolsulfosäure und Kuppelung mit 2 Molekülen β-Naphtol bei Gegen-Tetrazotization of I · 3'-Diamido-4 · 5-chlorobenzenesulfonic acid and coupling with 2 molecules of β-naphtol with counter-
wart von Alkali.waiting for alkali.
Zu einer Suspension von 11,1 Teilen Diamidochlorbenzolsulf osäure in 120 Teilen Salzsäure von 210 B. und 20 Teilen WasserTo a suspension of 11.1 parts of hydrochloric acid Diamidochlorbenzolsulf 21 0 B. osäure and 20 parts in 120 parts of water
wird unter Rühren langsam eine konzentrierte wäßrige Lösung von 7 Teilen Natriumnitrit allmählich zugegeben. Die so erhaltene Tetrazolösung wird auf Eis gegossen, bei o° mit Soda deutlich alkalisch gemacht und dann sogleich zu einer Lösung von 14,5 Teilen ß-Naphtol in 13 Teilen Natronlauge von 400 B. und 125 Teilen Wasser gegeben. Nach 10 bis I2stündigem Rühren bei gewöhnlicher Temperatur wird aufgekocht, der als schwarzes Pulver vollständig abgeschiedenea concentrated aqueous solution of 7 parts of sodium nitrite is slowly added gradually with stirring. The tetrazo solution obtained in this way is poured onto ice, made clearly alkaline at 0 ° with soda and then immediately added to a solution of 14.5 parts of β-naphthol in 13 parts of 40% sodium hydroxide solution and 125 parts of water. After stirring for 10 to 12 hours at normal temperature, the mixture is boiled and the black powder has completely separated out
Farbstoff filtriert, gewaschen, gepreßt und 50 getrocknet.Filtered dye, washed, pressed and dried.
Er löst sich in Wasser mit violettschwarzer Farbe, welche auf Zusatz von Mineralsäuren nach dunkelrot, durch Zugabe von wenig Soda nach blau umschlägt. Die Nuance der direkten Färbung ist rotbraun und geht beim Nachchromieren in schwarz über.It dissolves in water with a purple-black color, which is due to the addition of mineral acids turns dark red, turns blue when a little soda is added. The nuance of the direct coloring is red-brown and goes with Chromium plating in black over.
Für die Darstellung der übrigen Kombinationen sind die Angaben des Haupt-Patents, maßgebend. -For the representation of the other combinations, the information in the main patent, authoritative. -
Kombination der mit Soda
behandelten Tetrazo verbindung aus o-p-Diamidochlorbcnzolsulfosäure mitCombination of with soda
treated tetrazo compound of op-diamidochlorobenzene sulfonic acid with
Löslichkeit in Wassersolubility in water
Aufon
Zusatzadditive
von Soda Auf Zusatz von verdünnter Mineralsäure of soda on the addition of dilute mineral acid
Farbe der Lösung in konzentrierter Schwefel-Color of the solution in concentrated sulfur
Nuancenuance
derthe
direktendirect
Färbungcoloring
auf Wolleon wool
Nuancenuance
der, chro-the, chro-
miertenmated
Färbungcoloring
auf Wolleon wool
Nuancenuance
der ge-the
kupfertencoppered
Färbungcoloring
auf Wolleon wool
2 Moleküle ß-Naphtolsulfosäure Schäffer2 molecules of ß-naphthol sulfonic acid Schäffer
violettblau violet blue
violettblau rote Lösungpurple-blue red solution
rotviolettred-violet
rotbraunred-brown
violettschwarz purple black
schwärzlichviolett blackish purple
2 Moleküle m - Phenylendiamin 2 molecules of m - phenylenediamine
gelbbraunyellow-brown
rotbraunred-brown
ι Molekül ß-Naphtoldisulfosäure R und 1 Molekül ß-Naphtolι Molecule ß-Naphtholdisulfonic acid R and 1 molecule ß-naphtol
blaublue
violett braune Fällungviolet brown precipitate
schmutzigrote Lösungdirty red solution
i rotbrauni red-brown
gelbbraunyellow-brown
braunBrown
ι Molekül a-Naphtolsulfosäure ι ·\ und 1 MoIekül ß-Naphtolι Molecule of a-naphthol sulfonic acid ι · \ and 1 Molecule of ß-naphtol
violettblau violet blue
violett violettblaue Fällungviolet violet-blue precipitate
1 Molekül ci-Naphtolsulfosäure 1 -4 und 1 Molekül ι · 8 · 4-Amidonaphtolsulfosäure 1 molecule of ci-naphthol sulfonic acid 1 -4 and 1 molecule ι · 8 · 4-amidonaphthol sulfonic acid
dunkelblau dark blue
ι Molekül ß-Naphtol-ι molecule ß-naphthol-
sulfosäure Schäffer undsulfonic acid Schäffer and
ι Molekül ß-Naphtolι Molecule ß-naphtol
violettviolet
1 Molekül Naphthionsäure und 1 Molekül
β - Naphtol1 molecule of naphthionic acid and 1 molecule
β - naphtol
weinrotwine red
violettblau teilweise violettblaue Fällungviolet-blue partly violet-blue precipitation
violett weinrote Lösungpurple claret solution
weinrot wemrote Fällungclaret red precipitation
rötlichbraun reddish brown
tiefdeep
violettblau violet blue
violettbraun purple brown
violettschwarz purple black
violettschwarz purple black
tief blauviolettdeep blue-violet
rötlichviolett reddish purple
violettschwarz purple black
trübviolettcloudy purple
tiefblaudeep blue
bläulichviolett bluish purple
schwärzlichgrün blackish green
schwärzlichblau blackish blue
violettblauviolet blue
rotbraunred-brown
violettschwarz purple black
schwarzlichviolett blackish purple
violettblauviolet blue
braunrotbrownish red
gelbbraunyellow-brown
rotbraun.red-brown.
Claims (1)
Publications (1)
Publication Number | Publication Date |
---|---|
DE156828C true DE156828C (en) |
Family
ID=423163
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT156828D Active DE156828C (en) |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE156828C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2178065A1 (en) * | 1972-03-29 | 1973-11-09 | Basf Ag |
-
0
- DE DENDAT156828D patent/DE156828C/de active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2178065A1 (en) * | 1972-03-29 | 1973-11-09 | Basf Ag |
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