DE98321C - - Google Patents
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- Publication number
- DE98321C DE98321C DENDAT98321D DE98321DA DE98321C DE 98321 C DE98321 C DE 98321C DE NDAT98321 D DENDAT98321 D DE NDAT98321D DE 98321D A DE98321D A DE 98321DA DE 98321 C DE98321 C DE 98321C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- benzaldehyde
- dyes
- ethylbenzylaniline
- acids
- 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
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- 239000002253 acid Substances 0.000 claims description 15
- 239000000975 dye Substances 0.000 claims description 11
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 9
- HSZCJVZRHXPCIA-UHFFFAOYSA-N N-benzyl-N-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC=C1 HSZCJVZRHXPCIA-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 229940095076 benzaldehyde Drugs 0.000 claims description 4
- LXZGVFCKZRHKMU-UHFFFAOYSA-N N-benzyl-N-methylaniline Chemical compound C=1C=CC=CC=1N(C)CC1=CC=CC=C1 LXZGVFCKZRHKMU-UHFFFAOYSA-N 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N Diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 1
- QFRIIGBAHKSVIU-UHFFFAOYSA-N N-benzyl-2-methylaniline Chemical compound CC1=CC=CC=C1NCC1=CC=CC=C1 QFRIIGBAHKSVIU-UHFFFAOYSA-N 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- SLXZZXJPFRYIKN-UHFFFAOYSA-N benzyl-(2-ethylphenyl)sulfamic acid Chemical compound CCC1=CC=CC=C1N(S(O)(=O)=O)CC1=CC=CC=C1 SLXZZXJPFRYIKN-UHFFFAOYSA-N 0.000 claims 1
- JNACZTITPIYADC-UHFFFAOYSA-N benzyl-(2-methylphenyl)sulfamic acid Chemical compound CC1=CC=CC=C1N(S(O)(=O)=O)CC1=CC=CC=C1 JNACZTITPIYADC-UHFFFAOYSA-N 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- VFCNQNZNPKRXIT-UHFFFAOYSA-N malachite green cation Chemical class C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 VFCNQNZNPKRXIT-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- -1 monoethyl-otoluidine Chemical compound 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HXCKBNWJXWNEMZ-UHFFFAOYSA-N 1,4-dichlorocyclohexa-2,4-diene-1-carbaldehyde Chemical compound ClC1=CCC(Cl)(C=O)C=C1 HXCKBNWJXWNEMZ-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- GDQLHKHFHWLXES-UHFFFAOYSA-N ClC1=CC=CC(Cl)(C=O)C1 Chemical compound ClC1=CC=CC(Cl)(C=O)C1 GDQLHKHFHWLXES-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N amino(phenyl)azanium;chloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine 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
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 1
- 230000036545 exercise Effects 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 239000002966 varnish 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
- C09B11/14—Preparation from aromatic aldehydes, aromatic carboxylic acids or derivatives thereof and aromatic amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
Description
PATENTAMT.PATENT OFFICE.
■ A"■ A "
PATENTSCHRIFTPATENT LETTERING
KLASSE 22:^Farbstoffe, Firnisse, Lacke. '" iy CLASS 22: ^ dyes, varnishes, lacquers. '" iy
JOH. RUD. GEIGY & CO. in BASEL.JOH. RUD. GEIGY & CO. in Basel.
2>4-disulfosäure.2> 4-disulfonic acid.
Vierter Zusatz zum Patente Ju 89397 vom 25- FebruarFourth amendment to patent Ju 89397 of February 2-5
Patentirt im Deutschen Reiche vom 3. Januar 1897 ab. Längste Dauer: 24. Februar 1911.Patented in the German Empire on January 3, 1897. Longest duration: February 24, 1911.
Im dritten Zasatz, Patent Nr. 91315 , zum Patent Nr. 89397 s^n^ a^s Beispiele der Darstellung von alkaliechten, blaugrünen Farbstoffen aus Benzaldehyddisulfosäuren einige von der Benzaldehyd-o, m-disulfosäure,In the third addition, Patent No. 91315, to Patent No. 89397 s ^ n ^ a ^ s Examples of the preparation of alkaline, blue-green dyes from benzaldehyde disulfonic acids, some of the benzaldehyde-o, m-disulfonic acid,
C^: S O3H: S O3H= 1 : 2 : 5,C ^: SO 3 H: SO 3 H = 1: 2: 5,
derivirende Farbstoffe beschrieben. Obgleich in letzteren, ganz wie bei den Farbstoffen des Haupt-Patentes, sowohl die blaue Nuance, wie ' die Alkaliechtheit einzig von der Orthosteilung der einen Sulfogruppe zum Methanrest abhängt, so übt die zweite Sulfogruppe insofern ebenfalls einen Einflufs aus, als bei Aenderung ihrer Stellung z. B. nach para hin die Nuance der Farbstoffe sich wieder dem Grün nähert. Die zu diesem Zwecke nöthige Benzaldehyd-o, p-disulfosäure,derivating dyes described. Although in the latter, just as with the dyes of the Main patent, both the blue shade, as well as the alkali fastness only from the ortho division which depends on one sulfo group to form the methane residue, the second sulfo group also exercises in this respect an influence from when changing their position z. B. after para out the nuance the dyes approach the green again. The benzaldehyde required for this purpose, p-disulfonic acid,
C^: S O3H: SO3H = 1:2:4, C ^: SO 3 H: SO 3 H = 1: 2: 4,
läfst sich analog der Benzaldehyd-o-sulfosäure (Patent Nr. 88952, Kl. 12) in der Weise gewinnen, dafs man o, p-Dichlorbenzaldehyd mit Natriumsulfit in einem geschlossenen Gefäfs auf höhere Temperatur erhitzt. Im Gegensatz zu dem o, m-Dichlorbenzaldehyd, in dem das metaständige Chlor intact bleibt (Patent Nr. 91818), tauscht der o, p-Dichlorbenzaldehyd beide Chloratome gegen Sulfogruppen aus. Mit salzsaurem Phenylhydrazin giebt die so gewonnene Lösung von Benzaldehyddisulfosä'ure keinen Niederschlag, selbst nicht auf Zusatz von Kochsalz, während die Benzaldehyd-o-sulfosäure noch in sehr verdünnter Lösung das Hydrazon in Kryställchen ausscheidet.can be carried out analogously to benzaldehyde-o-sulfonic acid (Patent No. 88952, class 12) win in such a way that one o, p-dichlorobenzaldehyde with Sodium sulfite heated to a higher temperature in a closed vessel. In contrast to the o, m-dichlorobenzaldehyde, in which the meta-permanent chlorine remains intact (patent No. 91818), the o, p-dichlorobenzaldehyde exchanges both chlorine atoms for sulfo groups. The solution of benzaldehyde disulphonic acid thus obtained gives with hydrochloric acid phenylhydrazine no precipitate, even on the addition of table salt, while the benzaldehyde-o-sulfonic acid even in very dilute solution the hydrazone precipitates in small crystals.
70 kg 40 proc. Natriumbisulfitlösung werden mit 100 kg Wasser verdünnt, mit Natronlauge genau neutralisirt und hierauf mit 100 kg ο,,ρ-Dichlorbenzaldehyd in einem Autoclaven 9 bis 10 Stunden auf 190, bis 200° C. erhitzt. Nach dem Oeffnen des Autoclaven wird die resultirende Lösung von Benzaldehyd-o, p-disulfosäure mit 10 kg Schwefelsäure versetzt und bis zur Entfernung der überschüssigen schwefligen Säure zum Kochen erhitzt, worauf sie direct zur Farbstoffdarstellung verwendet werden kann. Letztere schliefst sich vollständig den in der Patentschrift Nr. 89397 un(^ dem Zusätze Nr. 90486 gegebenen Beispielen an, nur mit dem Unterschied, dafs die in der70 kg 40 proc. Sodium bisulfite solutions are diluted with 100 kg of water, exactly neutralized with sodium hydroxide solution and then heated with 100 kg of ο ,, ρ-dichlorobenzaldehyde in an autoclave at 190 to 200 ° C. for 9 to 10 hours. After opening the autoclave, the resulting solution of benzaldehyde-o, p-disulphonic acid is mixed with 10 kg of sulfuric acid and heated to the boil until the excess sulphurous acid is removed, whereupon it can be used directly for the preparation of the dye. The latter fully follows the examples given in Patent Specification No. 89397 and Addendum No. 90486, only with the difference that those in
letztgenannten Patentschrift angeführten Combinationen mit Methyl- und Aethylbenzylanilin infolge genügender Löslichkeit ohne weitere Sulfurirung sich zu Farbstoffen oxydiren lassen.combinations mentioned in the latter patent with methyl- and ethylbenzylaniline, owing to sufficient solubility, can be oxidized to dyes without further sulfurization.
132 kg einer 10 proc. Lösung von Benzaldehyd - ο , ρ - disulfosäure werden mit 22 kg Aethylbenzylanilin und 1 1J2 kg Schwefelsäure während 15 Stunden unter Rückflufs und ständigem Rühren im Sieden erhalten. Das Reactionsproduct, eine grünliche, in der Kälte spröde Masse wird mit Soda in kochendem Wasser gelöst, die Lösung nach Erkalten von dem überschüssigen Aethylbenzylanilin getrennt, auf 2500 1 verdünnt und mit Essigsäure vorsichtig angesäuert. Unter gutem Rühren giebt man nun die berechnete Menge einer Bleisuperoxydpaste hinzu und läfst hierauf noch 30 kg 40 proc. Essigsäure zufliefsen. Nach 3 Stunden wird die Lösung mit Ammoniak übersättigt, aufgekocht, filtrirt, der Farbstoff ausgesalzen und getrocknet. Derselbe bildet ein kupferglänzendes Pulver, das sich in Wasser mit blaugrüner Farbe löst. Auf Zusatz von Säure scheidet seine Lösung die freie Farbstoffsäure ab, die beim Erwärmen sich aber wieder löst.132 kg of a 10 proc. Solution of benzaldehyde - ο, ρ - disulfonic acid are obtained with 22 kg of ethylbenzylaniline and 1 1 J 2 kg of sulfuric acid for 15 hours under reflux and constant stirring at the boil. The reaction product, a greenish mass brittle in the cold, is dissolved with soda in boiling water, the solution is separated from the excess ethylbenzylaniline after cooling, diluted to 2500 liters and carefully acidified with acetic acid. The calculated amount of lead peroxide paste is then added, with thorough stirring, and 30 kg 40 per cent. Acetic acid flow in. After 3 hours the solution is supersaturated with ammonia, boiled, filtered, the dye is salted out and dried. It forms a shiny copper powder that dissolves in water with a blue-green color. When acid is added, its solution separates the free dye acid, which, however, dissolves again when heated.
Claims (2)
Patentes Nr. 89397,: sowie demj^nigfcn desf dritten Zusatzes 'Nr. 9*131 5'';zur, DaFSt'elluna von blaugrünen, alkaliechten Farbstoffen der! Malachitgrünreihe, darin 'bestehendj 'Haß man an Stelle der dort genannten Benzaldehyd-o-sulfosäure und Benzaldehyd-o, mdisulfosäure die Benzaldehyd-o, p-disulfosäure, Innovation in the ' Vterfajhren .des * p
Patent No. 89397,: as well as the current version of the third addition No. 9 * 131 5 "; zur, DaFSt'elluna of blue-green, alkaline dyes of the! Malachite green series, in which 'consisting', instead of the benzaldehyde-o-sulfonic acid and benzaldehyde-o, mdisulfonic acid mentioned there, benzaldehyde-o, p-disulfonic acid is hated,
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE98321C true DE98321C (en) |
Family
ID=369296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| DENDAT98321D Active DE98321C (en) |
Country Status (1)
| Country | Link |
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| DE (1) | DE98321C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0175226A2 (en) * | 1984-09-17 | 1986-03-26 | Hoechst Aktiengesellschaft | Process for the preparation of salts of alkaline or earth-alkaline metals of benzaldehyde-2,4-disulfonic acid |
| US4715995A (en) * | 1984-09-17 | 1987-12-29 | Hoechst Aktiengesellschaft | Process for the preparation of alkali metal and alkaline earth salts of benzaldehyde-2,4-disulfonic acid |
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0
- DE DENDAT98321D patent/DE98321C/de active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0175226A2 (en) * | 1984-09-17 | 1986-03-26 | Hoechst Aktiengesellschaft | Process for the preparation of salts of alkaline or earth-alkaline metals of benzaldehyde-2,4-disulfonic acid |
| EP0175226A3 (en) * | 1984-09-17 | 1986-05-14 | Hoechst Aktiengesellschaft | Process for the preparation of salts of alkaline or earth-alkaline metals of benzaldehyde-2,4-disulfonic acid |
| US4710322A (en) * | 1984-09-17 | 1987-12-01 | Hoechst Aktiengesellschaft | Process for the preparation of alkali metal and alkaline earth salts of benzaldehyde-2,4-di-sulfonic acid |
| US4715995A (en) * | 1984-09-17 | 1987-12-29 | Hoechst Aktiengesellschaft | Process for the preparation of alkali metal and alkaline earth salts of benzaldehyde-2,4-disulfonic acid |
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