DE217556C - - Google Patents
Info
- Publication number
- DE217556C DE217556C DENDAT217556D DE217556DA DE217556C DE 217556 C DE217556 C DE 217556C DE NDAT217556 D DENDAT217556 D DE NDAT217556D DE 217556D A DE217556D A DE 217556DA DE 217556 C DE217556 C DE 217556C
- Authority
- DE
- Germany
- Prior art keywords
- oxy
- dioxindole
- leuco
- thionaphtenes
- carbonate
- 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
- SGZFJWQQBHYNNF-UHFFFAOYSA-N 3-hydroxyindolin-2-one Chemical compound C1=CC=C2C(O)C(=O)NC2=C1 SGZFJWQQBHYNNF-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- JXDYKVIHCLTXOP-UHFFFAOYSA-N Isatin Natural products C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- LTERBHLYBWXCPT-UHFFFAOYSA-N 4-methoxy-1H-indole-2,3-dione Chemical compound COC1=CC=CC2=C1C(=O)C(=O)N2 LTERBHLYBWXCPT-UHFFFAOYSA-N 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LILHXQCLSOZSRO-UHFFFAOYSA-J dizinc;oxozinc;dicarbonate;tetrahydrate Chemical compound O.O.O.O.[Zn+2].[Zn+2].[Zn]=O.[Zn]=O.[Zn]=O.[O-]C([O-])=O.[O-]C([O-])=O LILHXQCLSOZSRO-UHFFFAOYSA-J 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0077—Preparations with possibly reduced vat, sulfur or indigo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE \2p. GRUPPE %„.. CLASS \ 2p. GROUP % "..
Zusatz zum Patente 213714 vom 29. März 1908. Addendum to patent 213714 of March 29, 1908.
Patentiert im Deutschen Reiche vom 6. Juni 1908 ab. Längste Dauer: 28. März 1923.Patented in the German Empire on June 6, 1908. Longest duration: March 28, 1923.
In dem Hauptpatent 213714 wurde gezeigt, daß Dioxindol sich mit 3-Oxy-(i)-thionaphtenen bzw. deren 2-Carbonsäuren, zweckmäßig in Gegenwart von kohlensauren Alkalien, zu schwefelhaltigen Leukokörpern kondensieren läßt.In the main patent 213714 it was shown that dioxindole reacts with 3-oxy- (i) -thionaphtenes or their 2-carboxylic acids, expediently in The presence of carbonate alkalis condense to form sulphurous leuco bodies leaves.
Es wurde nun weiter gefunden, daß man zu den Leukoverbindungen von sehr wertvollen braunen bis gelben Farbstoffen gelangt, wenn man die alkoxylierten Dioxindole der allgemeinen Formel:It has now been found that the leuco compounds are very valuable brown to yellow dyes, if you use the alkoxylated dioxindoles of the general Formula:
(A-OJ-C6H/,(A-OJ-C 6 H /,
,CH(OHX, CH (OHX
NHNH
(worin -»A« gleich »Alkyl«, ζ. B. C H3 oder C2H5 bedeutet) mit 3-Oxy-(i)-thionaphtenen bzw. deren 2-Carbonsäuren kondensiert.(where - "A " equals "alkyl", ζ. B. CH 3 or C 2 H 5 ) condensed with 3-oxy- (i) -thionaphtenes or their 2-carboxylic acids.
Die alkoxylierten Dioxindole lassen sich in analoger Weise wie Dioxindol darstellen; es ist jedoch nicht erforderlich, diese sehr schwer rein zu erhaltenden Dioxindole zu isolieren, vielmehr genügt eine wäßrige Lösung dieser Körper, wie sie z. B. durch Reduktion der entsprechenden Isatine mit Zink und Salzsäure (vgl. Ber. 12 [1879], S. 1309) erhalten wird.The alkoxylated dioxindoles can be prepared in a manner analogous to dioxindole; it However, it is not necessary to isolate these dioxindoles, which are very difficult to obtain in pure form, rather, an aqueous solution of this body is sufficient, as it is, for. B. by reducing the corresponding isatins with zinc and hydrochloric acid (cf. Ber. 12 [1879], p. 1309) will.
Das beispielsweise durch Oxydation des Dimethoxyindigo (Ber. 22 [1889], S. 2351) erhältliche 4-MethoxyisatinThat obtainable, for example, by oxidation of dimethoxyindigo (Ber. 22 [1889], p. 2351) 4-methoxyisatin
3535
0CH% 0CH %
(blaurote, in Wasser und Alkohol schwer lösliehe, bei 240 bis 242 ° schmelzende Kristallnadeln) wird mit Zink und Salzsäure zu dem entsprechenden Dioxindol reduziert. ·(blue-red crystal needles that are poorly soluble in water and alcohol, melting at 240 to 242 °) is reduced to the corresponding dioxindole with zinc and hydrochloric acid. ·
Eine heiße Lösung von 18 Teilen 4-Methoxydioxindol in etwa 4000 Teilen Wasser wird mit 15 Teilen 3-Oxy-(i)-thionaphten versetzt, worauf man unter Umrühren Natriumcarbonat bis zur alkalischen Reaktion einträgt und zur Vollendung der Umsetzung noch einige Zeit auf dem Wasserbad unter Luftabschluß erwärmt. Nach dem Erkalten wird das Gemenge des Leukokörpers mit Zinkcarbonat abfiltriert und zur Entfernung des letzteren mit verdünnter Säure gewaschen. Die Leuko-A hot solution of 18 parts of 4-methoxydioxindole in about 4000 parts of water is made mixed with 15 parts of 3-oxy- (i) -thionaphthene, whereupon sodium carbonate is added with stirring until an alkaline reaction occurs and for Completion of the reaction heated for some time on the water bath with the exclusion of air. After cooling, the mixture of the leuco body with zinc carbonate is filtered off and the latter is removed washed with dilute acid. The leuco
Verbindung bleibt hierbei als ein schwach bräunlich gefärbtes, in den gebräuchlichen Lösungsmitteln schwer lösliches, nicht ohne Zersetzung schmelzendes Pulver zurück, löslich in Alkalilaugen zu einer gelblichen Küpe, welche an der Luft einen braunen Farbstoff ausscheidet und zur Erzeugung braunroter Färbungen auf der Faser dient.Compound remains here as a slightly brownish colored, in the usual Solvents poorly soluble powder that does not melt without decomposition, soluble in alkaline solutions to a yellowish vat, which in the air turns a brown dye separates and serves to produce brownish-red colorations on the fiber.
Ersetzt man in obigem Beispiel das 3-Oxy-(i)-thionaphten in sinngemäßer Weise durch 6 -Äthoxy-3-oxy-(i)-thionaphten - 2 - carbonsäure (vgl. französische Patentschrift 384418; amerikanische Patentschrift 867305), so erhält man die Leukoverbindung eines gelben Farbstoffs.If the 3-oxy- (i) -thionaphthene is replaced in the above example in a corresponding manner by 6-ethoxy-3-oxy- (i) -thionaphthene - 2 - carboxylic acid (see French patent specification 384418; American Patent specification 867305), the leuco compound of a yellow dye is obtained.
Diese ist schwer löslich in Wasser und Alkohol, leicht oxydabel und schmilzt nicht ohne Zersetzung. This is sparingly soluble in water and alcohol, easily oxidizable and does not melt without decomposition.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE217556C true DE217556C (en) |
Family
ID=478852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT217556D Active DE217556C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE217556C (en) |
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0
- DE DENDAT217556D patent/DE217556C/de active Active
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