DE229708C - - Google Patents
Info
- Publication number
- DE229708C DE229708C DENDAT229708D DE229708DA DE229708C DE 229708 C DE229708 C DE 229708C DE NDAT229708 D DENDAT229708 D DE NDAT229708D DE 229708D A DE229708D A DE 229708DA DE 229708 C DE229708 C DE 229708C
- Authority
- DE
- Germany
- Prior art keywords
- gallocyanin
- dyes
- product
- condensation products
- aromatic amines
- 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 7
- LNTHITQWFMADLM-UHFFFAOYSA-N Gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 6
- 239000007859 condensation product Substances 0.000 claims description 5
- YBGOLOJQJWLUQP-UHFFFAOYSA-N Gallocyanin Chemical class OC(=O)C1=CC(=O)C(O)=C2OC3=CC(N(C)C)=CC=C3N=C21 YBGOLOJQJWLUQP-UHFFFAOYSA-N 0.000 claims description 4
- 229940074391 Gallic acid Drugs 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 235000004515 gallic acid Nutrition 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- UCMYJOPIPDLTRT-UHFFFAOYSA-N N,N-diethyl-2-nitrosoaniline Chemical compound CCN(CC)C1=CC=CC=C1N=O UCMYJOPIPDLTRT-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 241000182341 Cubitermes group Species 0.000 description 1
- LGDPTPLJZGPOJL-UHFFFAOYSA-N N,N-dimethyl-2-nitrosoaniline Chemical compound CN(C)C1=CC=CC=C1N=O LGDPTPLJZGPOJL-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
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- XOSXWYQMOYSSKB-UHFFFAOYSA-L water blue Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=C(N)C(C)=CC(C(=C2C=CC(C=C2)=NC=2C=CC(=CC=2)S([O-])(=O)=O)C=2C=CC(NC=3C=CC(=CC=3)S(O)(=O)=O)=CC=2)=C1 XOSXWYQMOYSSKB-UHFFFAOYSA-L 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
- C09B19/00—Oxazine dyes
- C09B19/005—Gallocyanine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 229708 KLASSE 22 c. GRUPPE- M 229708 CLASS 22 c. GROUP
Sulfosäuren von Farbstoffen der Gallocyaninreihe, die sich durch ihre außergewöhnliche
Klarheit auszeichnen, werden erhalten, wenn man die nach dem Beispiel des Patentes 206465
durch Kondensation von Gallocyanin mit organischen Aminen in der Kälte bei Gegenwart
von Sauerstoff und nachträgliches Erwärmen erhältlichen Kondensationsprodukte sulfiert.
Es wurde nun gefunden, daß man Farbstoffe, die bei derselben Klarheit erheblich grünere
Nuancen liefern, erhalten kann, wenn man an Stelle der bisher zur Sulfierung verwendeten
Kondensationsprodukte von Gallocyanin (Farbstoff aus Nitrosodimethylanilin und Gallussäure)
mit aromatischen Aminen die unter Beobachtung der im Patent 206465 angegebenen Arbeitsweise erhältlichen analogen Kondensationsprodukte
aus Diäthylgallocyanin (Farb-■ stoff aus Nitrosodiäthylanilin und Gallussäure)
und aromatischen Aminen der Sulfierung unterwirft. Sulphonic acids of dyes of the gallocyanin series, which are distinguished by their extraordinary clarity, are obtained if the condensation products obtainable according to the example of patent 206465 by condensation of gallocyanin with organic amines in the cold in the presence of oxygen and subsequent heating are sulphated.
It has now been found that dyes which give considerably greener nuances with the same clarity can be obtained if, instead of the condensation products of gallocyanine (dye made from nitrosodimethylaniline and gallic acid) with aromatic amines, which have been previously used for sulfonation, the products described in patent 206465 are used The analogous condensation products obtained from diethylgallocyanine (dye made from nitrosodiethylaniline and gallic acid) and aromatic amines are subjected to sulfonation.
50 Teile des unter Beobachtung der im Patent 206465 angegebenen Arbeitsweise erhältlichen entkarboxylierten Kondensationsproduktes aus Diäthylgallocyanin, und Anilin werden in 200 Teile rauchender Schwefelsäure von 25 Prozent Anhydridgehalt bei einer Temperatur von 10 bis 15 ° eingetragen. Man erhitzt allmählich unter Rühren auf 30 bis 40 °, bis eine Probe in Soda löslich ist. Die Reaktionsmasse wird darauf in Wasser gegossen, ausgesalzen und in das Ammoniumsalz übergeführt. Letzteres löst sich leicht in Wasser mit blauer Färbe, die auf Zusatz von Soda nach blauviolett umschlägt und auf Zugabe von wenig Essigsäure grünblau, von mehr Essigsäure grün wird, ohne daß eine Abscheidung eintritt, wie dies bei Zugabe von Mineralsäuren der Fall ist. In konzentrierter Schwefelsäure löst sich der Farbstoff weinrot.50 parts of that obtainable by observing the procedure given in patent 206465 decarboxylated condensation product from diethylgallocyanine, and aniline in 200 parts of fuming sulfuric acid of 25 percent anhydride content at one temperature entered from 10 to 15 °. One heats up gradually with stirring to 30 to 40 ° until a sample is soluble in soda. The reaction mass is then poured into water and salted out and converted into the ammonium salt. The latter dissolves easily in water blue color, which changes to blue-violet on the addition of soda and on the addition of a little acetic acid turns green-blue, with more acetic acid it turns green without any separation occurs, as is the case with the addition of mineral acids. In concentrated sulfuric acid the dye dissolves wine-red.
Er gibt im Druck sehr klare grünstichig blaue Töne, die bedeutend grüner sind als diejenigen des entsprechenden Produktes aus Dimethylgallocyanin.In the print it gives very clear greenish blue tones that are significantly greener than those of the corresponding product from dimethylgallocyanin.
Selbstverständlich können auch andere SuI-fierungsmittel zur Anwendung gelangen, wie auch an Stelle des im obigen Beispiel erwähnten Anilidoproduktes die Analogen und Homologen, wie z. B. das Toluido-, das Chloranilidoprodukt verwendet werden können. Die hieraus entstehenden Farbstoffe verhalten sich ähnlich wie das im Beispiel beschriebene Produkt.Of course, other suI-fierungsmittel can also be used come to use, as well as in place of the anilido product mentioned in the above example, the analogs and homologues, such as B. the toluido, the chloranilido product can be used. The one from here The resulting dyes behave similarly to the product described in the example.
Claims (1)
Publications (1)
Publication Number | Publication Date |
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DE229708C true DE229708C (en) |
Family
ID=489988
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT229708D Active DE229708C (en) |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE229708C (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2545874A1 (en) * | 1975-10-14 | 1977-05-05 | Plate Bonn Gmbh | HOT SEAL MELT ADHESIVE |
US5409532A (en) * | 1992-01-23 | 1995-04-25 | Lenzing Aktiengesellschaft | Amine-oxides |
US5618483A (en) * | 1994-06-10 | 1997-04-08 | Fraunhofer Gesellschaft Petentabteilung | Process of making flexible cellulose fibers |
US5679146A (en) * | 1993-09-14 | 1997-10-21 | Lenzing Aktiengesellschaft | Moulding materials and spinning materials containing cellulose |
US6676739B2 (en) | 2000-02-28 | 2004-01-13 | Thuringishces Institut Fur Textil Und Kunststoff-Forschung E.V. | Method for producing a cellulose solution in an aqueous amine oxide, said solution having an increased thermal stability |
-
0
- DE DENDAT229708D patent/DE229708C/de active Active
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2545874A1 (en) * | 1975-10-14 | 1977-05-05 | Plate Bonn Gmbh | HOT SEAL MELT ADHESIVE |
US5409532A (en) * | 1992-01-23 | 1995-04-25 | Lenzing Aktiengesellschaft | Amine-oxides |
US5679146A (en) * | 1993-09-14 | 1997-10-21 | Lenzing Aktiengesellschaft | Moulding materials and spinning materials containing cellulose |
US5618483A (en) * | 1994-06-10 | 1997-04-08 | Fraunhofer Gesellschaft Petentabteilung | Process of making flexible cellulose fibers |
US6676739B2 (en) | 2000-02-28 | 2004-01-13 | Thuringishces Institut Fur Textil Und Kunststoff-Forschung E.V. | Method for producing a cellulose solution in an aqueous amine oxide, said solution having an increased thermal stability |
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