DE239916C - - Google Patents
Info
- Publication number
- DE239916C DE239916C DENDAT239916D DE239916DA DE239916C DE 239916 C DE239916 C DE 239916C DE NDAT239916 D DENDAT239916 D DE NDAT239916D DE 239916D A DE239916D A DE 239916DA DE 239916 C DE239916 C DE 239916C
- Authority
- DE
- Germany
- Prior art keywords
- mol
- oxythionaphthene
- indoxyl
- diketones
- dialdehyde
- 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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- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- YEQRASMGLPZYDE-UHFFFAOYSA-N Indoxyl Chemical group C1=CC=C[C]2C(O)=CN=C21 YEQRASMGLPZYDE-UHFFFAOYSA-N 0.000 description 6
- 125000005594 diketone group Chemical group 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- -1 hydrocarbon radical Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- 241000854350 Enicospilus group Species 0.000 description 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N Glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- 229940015043 Glyoxal Drugs 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
- 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
- 210000002268 Wool Anatomy 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 239000001043 yellow dye 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
- C09B7/00—Indigoid dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 239916 KLASSE 22 e. GRUPPE- M 239916 CLASS 22 e. GROUP
KALLE & CO. AKT.-GES. in BIEBRICH a. Rh. Verfahren zur Darstellung indigoider Farbstoffe. Patentiert im Deutschen Reiche vom 15. Mai 1910 ab.KALLE & CO. ACT.-TOTAL in BIEBRICH a. Rh. Process for the preparation of indigoid dyes. Patented in the German Empire on May 15, 1910.
Es ist die überraschende Beobachtung gemacht worden, daß sich Dialdehyde" sowie nicht zyklische Diketone mit 2 Mol. von Körpern der Konstitution des Indoxyls oder Oxythionaphtens kondensieren lassen, und daß dabei beständige Küpenfarbstoffe entstehen, die in üblicher Weise durch Überführung in ihre Leuko verbindungen zum Färben der thierischen und pflanzlichen Faser geeignet sind.The surprising observation has been made that dialdehydes "as well non-cyclic diketones with 2 moles of bodies of the constitution of indoxyl or oxythionaphthene let condense, and that stable vat dyes are formed in the usual way by conversion into Their leuco compounds are suitable for dyeing animal and vegetable fibers are.
Die hiernach entstehenden Produkte besitzen folgende allgemeine Zusammensetzung:The resulting products have the following general composition:
C — R — CC - R - C
wobei R eliminiert sein kann oder einen die beiden Kohlenstoff atome verbindenden Kohlenwasserstoffrest darstellt. R1 und R2 können Wasserstoffatome oder Kohlenwasserstoffreste, X und Y gleiche oder verschiedene Atome oder Radikale, wie S, ·—NH, O sein.where R can be eliminated or represents a hydrocarbon radical connecting the two carbon atoms. R 1 and R 2 can be hydrogen atoms or hydrocarbon radicals, X and Y identical or different atoms or radicals, such as S, · - NH, O be.
Überraschenderweise haben die so erhaltenen Körper die Eigenschaft, die Faser je nach der Art des angewendeten Dialdehyds, Indoxyls oder Oxythionaphtens usw. in Farbtönen, die die. ganze Skala durchlaufen, anzufärben. So entsteht z. B. beim Zusammenbringen von 2 Mol. Oxythionaphten mit 1 Mol. Terephtalaldehyd ein kristallinisches gelbes Kondensationsprodukt folgender Konstitution:Surprisingly, the bodies obtained in this way have the property that the fiber ever according to the type of dialdehyde, indoxyl or oxythionaphthene used, etc. in color shades, the the. run through the whole range to color. So z. B. when bringing them together of 2 mol. Oxythionaphten with 1 mol. Terephthalaldehyde a crystalline yellow Condensation product of the following constitution:
-CO-CO
C=C-C = C-
HH >-C = i> -C = i
C OC O
Der Körper läßt sich mit Alkali und Hydrosulfit leicht in eine schwach gelb gefärbte Küpe überführen, aus der die Leukoverbindung sowohl auf Baumwolle als auch auf Wolle, je nach dem Grade der Alkalinität der Küpe, farblos bis bläulich aufzieht. Bei der Oxydation, z. B. beim Verhängen an der Luft, bildet sich auf der Faser der ursprüngliche gelbe Farbstoff zurück.The body can easily be turned into a pale yellow color with alkali and hydrosulfite Transfer vat from which the leuco compound on both cotton and wool, colorless to bluish, depending on the degree of alkalinity of the vat. In the case of oxidation, z. B. when hanging in the air, the original forms on the fiber yellow dye back.
Behandelt man 1 Mol. Glyoxal, ζ. B. inTreating 1 mole of glyoxal, ζ. Am
Form der Bisulfitverbindung, mit 2 Mol. Oxythionaphten in wässeriger oder alkoholischer Lösung, so entsteht beim Erwärmen ein in bräunlichroten Nadeln kristallisierender Körper, der bei der Verküpung eine dunkelgelbe Leukolösung liefert, die die tierische und pflanzliche Faser gelb anfärbt; beim Verhängen an der Luft erhält man tiefe bordeauxrote Töne, die beim Waschen einenForm of the bisulfite compound, with 2 mol. Oxythionaphten in aqueous or alcoholic Solution, when heated, a body emerges that crystallizes in brownish-red needles, which delivers a dark yellow leuco solution when vatting, which the animal and vegetable fiber stains yellow; when hanging in the air you get deep burgundy red Sounds that make you wash
ίο gelblicheren Stich annehmen.ίο take on a more yellowish tinge.
In gleicher Weise erhält man unter Anwendung von Indoxyl an Stelle von Oxythionaphten einen blauvioletten Farbstoff. An Stelle von 2 Mol. Indoxyl oder Oxythionaphten kann man den Dialdehyd oder das Diketon mit 1 Mol. Indoxyl und 1 Mol. Oxythionaphten kondensieren. Ebenso können an Stelle der Körper von der Zusammensetzung des Oxythionaphtens oder Indoxyls deren Substitutionsprodukte oder analog zusammengesetzte Körper und an Stelle der Dialdehyde oder Diketone deren Substitutionsprodukte angewendet werden, ebenso Substanzen, welche bei den vorhandenen Reäktionsbedingungen in Dialdehyde oder Diketone in Indoxyl, Oxythionaphten u. dgl. übergehen. In the same way, using indoxyl in place of oxythionaphthene is obtained a blue-violet dye. Instead of 2 mol. Indoxyl or Oxythionaphten one can use the dialdehyde or the Diketone with 1 mole of indoxyl and 1 mole of oxythionaphthene condense. Likewise, in place of the body can depend on the composition of oxythionaphthene or indoxyls their substitution products or similarly composed bodies and in place of the Dialdehydes or diketones their substitution products can be used, as well as substances which under the existing reaction conditions in dialdehydes or diketones in indoxyl, oxythionaphthene and the like.
Die Reaktion kann durch Erhitzen der Reagentien für sich oder in Gegenwart von Lösungs- oder Verdünnungsmitteln, gegebenenfalls unter Zusatz von Kondensationsmitteln vorgenommen werden.The reaction can be carried out by heating the reagents alone or in the presence of Solvents or diluents, optionally with the addition of condensing agents be made.
Von den Diketonen eignen sich zu dieser Kondensation sowohl aliphatische als auch aromatische Diketone, wie z. B. Diacetyl oder Benzyl.Of the diketones, both aliphatic and aliphatic ones are suitable for this condensation aromatic diketones, e.g. B. diacetyl or benzyl.
Claims (1)
Publications (1)
Publication Number | Publication Date |
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DE239916C true DE239916C (en) |
Family
ID=499317
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT239916D Active DE239916C (en) |
Country Status (1)
Country | Link |
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DE (1) | DE239916C (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5005283A (en) * | 1990-09-19 | 1991-04-09 | Rockwell International Corporation | Method of manufacturing an E/M shielded RF circuit board |
US5297007A (en) * | 1990-09-19 | 1994-03-22 | Rockwell International Corporation | E/M shielded RF circuit board |
DE10039748C1 (en) * | 2000-08-16 | 2002-06-13 | Agfa Gevaert Ag | Production of benzothiophenone methine dyes, comprises cyclizing a 2-carboxyphenylthioacetic acid with acetic anhydride and reacting the resulting 3-acetoxybenzothiophene with a carbonyl compound |
-
0
- DE DENDAT239916D patent/DE239916C/de active Active
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5005283A (en) * | 1990-09-19 | 1991-04-09 | Rockwell International Corporation | Method of manufacturing an E/M shielded RF circuit board |
US5297007A (en) * | 1990-09-19 | 1994-03-22 | Rockwell International Corporation | E/M shielded RF circuit board |
DE10039748C1 (en) * | 2000-08-16 | 2002-06-13 | Agfa Gevaert Ag | Production of benzothiophenone methine dyes, comprises cyclizing a 2-carboxyphenylthioacetic acid with acetic anhydride and reacting the resulting 3-acetoxybenzothiophene with a carbonyl compound |
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