DE229029C - - Google Patents
Info
- Publication number
- DE229029C DE229029C DENDAT229029D DE229029DA DE229029C DE 229029 C DE229029 C DE 229029C DE NDAT229029 D DENDAT229029 D DE NDAT229029D DE 229029D A DE229029D A DE 229029DA DE 229029 C DE229029 C DE 229029C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- water
- molecules
- oil
- dye
- 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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- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- -1 diacetyl compound Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 description 1
- 241000947840 Alteromonadales Species 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant 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
- 230000000694 effects Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000155 melt Substances 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
- 230000000802 nitrating Effects 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium 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
- 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
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
- C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
- C09B35/14—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from hydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Paints Or Removers (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
e 229029 KLASSE 22 a. GRUPPE e 229029 CLASS 22 a. GROUP
CHEMISCHE FABRIK GRIESHEIM-ELEKTRON in FRANKFURT a. M.CHEMICAL FACTORY GRIESHEIM-ELEKTRON in FRANKFURT a. M.
Läßt man auf die Diacetylverbindung des m-m'-Dichlorbenzidins (N H2: Cl = ι : 3) die zwei Molekülen entsprechende Menge Salpetersäure einwirken, so erhält man nach der Verseifung des Reaktionsproduktes ein Dichlordinitrobenzidin, dem wahrscheinlich die Konstitution :If the diacetyl compound of m-m'-dichlorobenzidine (NH 2 : Cl = ι: 3) is allowed to act in the amount of nitric acid corresponding to two molecules, a dichlorodonitrobenzidine is obtained after the saponification of the reaction product, which probably has the constitution:
NO0 NO 0
NH,NH,
zukommt.comes to.
Es wurde nun gefunden, daß die Tetrazoverbindung dieses Dichlordinitrobenzidins bei der Kombination mit 2 Molekülen ß-Naphtol einen roten Disazofarbstoff liefert, der wegen seiner Wasserunlöslichkeit und hervorragenden ölechtheit zur Darstellung von Pigmentfarben sehr geeignet ist.It has now been found that the tetrazo compound of this dichloro nitrobenzidine the combination with 2 molecules of ß-naphtol produces a red disazo dye, which because of its insolubility in water and excellent oiliness for the representation of pigment colors is very suitable.
Der Monoazofarbstoff der Patentschrift 202908 aus 5-Chlor-2-nitroanilin, der ähnliche Konstitution besitzt, ist bekanntlich nicht vollständig ölunlöslich. Es konnte deshalb nicht vorausgesehen werden, daß das vorliegende Benzidinderivat einen so hervorragend ölechten Disazofarbstoff liefern würde.The monoazo dye of patent 202908 from 5-chloro-2-nitroaniline, the similar one Has constitution, is known to be not completely oil-insoluble. It could therefore the present benzidine derivative cannot be foreseen to make one so excellent would provide oleic disazo dye.
3535
Darstellung des Dichlordinitrobenzidins. Representation of the dichloroditrobenzidine.
m - m' - Dichlorbenzidin wird in üblicher Weise in die Diacetylverbindung übergeführt. 16,8 Teile des erhaltenen m-m'-Dichlordiacetylbenzidins werden unter guter Kühlung in 100 Teilen Schwefelsäure von 66° Be. gelöst, worauf zu der Lösung bei 0 bis 50 die zwei Molekülen entsprechende Menge Nitriersäure allmählich zufließen gelassen wird. Hierauf steigert man die Temperatur langsam auf 200 und gießt dann das Reaktionsgemisch in Eiswasser. Dabei scheidet sich das Dichlordinitrodiacetylbenzidin aus; es wird abfiltriert und durch Erwärmen mit 25 prozentiger Schwefelsäure verseift. Das Dichlordinitrobenzidin bildet ein gelbes Pulver und schmilzt bei ungefähr 255 ° C.m - m '- dichlorobenzidine is converted into the diacetyl compound in the usual way. 16.8 parts of the m-m'-dichlorodiacetylbenzidine obtained are in 100 parts of sulfuric acid at 66 ° Be with good cooling. dissolved, whereupon the amount of nitrating acid corresponding to two molecules is gradually allowed to flow into the solution at 0 to 5 0. The temperature is then slowly increased to 20 0 and the reaction mixture is then poured into ice water. The dichloronitrodiacetylbenzidine separates out; it is filtered off and saponified by heating with 25 percent sulfuric acid. The dichloroditrobenzidine forms a yellow powder and melts at about 255 ° C.
5555
Darstellung des Farbstoffs.Representation of the dye.
34,3 Teile Dichlordinitrobenzidin werden mit 200 Teilen Wasser und 80 Teilen Salzsäure von 20° Be. fein angeschlämmt und mit einer Lösung von 14 Teilen Natriumnitrit versetzt. Die, wenn nötig, nitrierte Diazolösung läßt man zu einer Suspension von 29 Teilen ß-Naphtol, die durch Fällen einer Lösung der ent-34.3 parts of dichlorodonitrobenzidine are mixed with 200 parts of water and 80 parts of hydrochloric acid from 20 ° Be. finely slurried and mixed with a solution of 14 parts of sodium nitrite. The, if necessary, nitrated diazo solution is added to a suspension of 29 parts of ß-naphtol, by finding a solution to the
sprechenden Menge ß-Naphtolnatrium in 500 Teilen Wasser bei Gegenwart von Türkischrotöl erhalten wurde, und der noch 140 Teile Natriumacetat zugefügt waren, fließen. Der Farbstoff bildet sich rasch und scheidet sich in roten Flocken aus. Er wird abfiltriert, mit Wasser gewaschen und vorteihaft in Pastenform verwendet.speaking amount of ß-naphtol sodium in 500 Parts of water was obtained in the presence of Turkish red oil, and that still 140 parts Sodium acetate were added, flow. The dye forms and separates quickly in red flakes. It is filtered off, washed with water and advantageously in Paste form used.
Statt des Türkischrotöls können auch andere ähnlich wirkende Stoffe, z. B. Seife oder Harzleim, zugesetzt werden, oder es kann die Kombination bei Abwesenheit eines dieser Stoffe ausgeführt werden. Selbstverständlich kann man die Kupplung der Tetrazoverbindung mit ß-Naphtol auch bei Gegenwart eines Substrats vornehmen.Instead of Turkish red oil, other substances with a similar effect, e.g. B. Soap or resin glue, can be added, or the combination can be carried out in the absence of one of these substances. Of course you can the coupling of the tetrazo compound with ß-naphtol in the presence of a Make the substrate.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE229029C true DE229029C (en) |
Family
ID=489375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT229029D Active DE229029C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE229029C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3218311A (en) * | 1961-12-21 | 1965-11-16 | Sandoz Ltd | Water-insoluble disazo dyes |
-
0
- DE DENDAT229029D patent/DE229029C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3218311A (en) * | 1961-12-21 | 1965-11-16 | Sandoz Ltd | Water-insoluble disazo dyes |
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