DE264293C - - Google Patents
Info
- Publication number
- DE264293C DE264293C DENDAT264293D DE264293DA DE264293C DE 264293 C DE264293 C DE 264293C DE NDAT264293 D DENDAT264293 D DE NDAT264293D DE 264293D A DE264293D A DE 264293DA DE 264293 C DE264293 C DE 264293C
- Authority
- DE
- Germany
- Prior art keywords
- sulfur
- parts
- thiourea
- dyes
- sodium
- 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
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 239000000988 sulfur dye Substances 0.000 claims description 3
- AAQTWLBJPNLKHT-UHFFFAOYSA-N 1H-perimidine Chemical compound N1C=NC2=CC=CC3=CC=CC1=C32 AAQTWLBJPNLKHT-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- ZJHHPAUQMCHPRB-UHFFFAOYSA-N urea urea Chemical compound NC(N)=O.NC(N)=O ZJHHPAUQMCHPRB-UHFFFAOYSA-N 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 description 8
- -1 sulfur-sodium Chemical compound 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 229960000583 Acetic Acid Drugs 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N carbon bisulphide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 150000005052 perimidines Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 1
- 241000189705 Dunedin group Species 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N Sodium sulfide Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- IQZPDFORWZTSKT-UHFFFAOYSA-N nitrosulphonic acid Chemical class OS(=O)(=O)[N+]([O-])=O IQZPDFORWZTSKT-UHFFFAOYSA-N 0.000 description 1
- KHEZAZQZWQJLAE-UHFFFAOYSA-N nitrothiourea Chemical compound [O-][N+](=O)NC(S)=N KHEZAZQZWQJLAE-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 238000010792 warming Methods 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
- C09B49/00—Sulfur dyes
- C09B49/12—Sulfur dyes from other compounds, e.g. other heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 264293 KLASSE 22 d. GRUPPE- M 264293 CLASS 22 d. GROUP
Verfahren zur Darstellung von Schwefelfarbstoffen. Zusatz zum Patent 253934.*)Process for the preparation of sulfur dyes. Addition to patent 253934. *)
Patentiert im Deutschen Reiche vom 20. Oktober 1912 ab. Längste Dauer: 4, November 1926.Patented in the German Empire on October 20, 1912. Longest duration: November 4, 1926.
Durch das Hauptpatent und sein Zusatzpatent 264292 sind Verfahren geschützt zur Darstellung von braunen Schwefelfarbstoffen, welche darin bestehen, daß man Perimidin, seine Homologen und Derivate, wie insbesondere seine Nitro- bzw. Amidoverbindungen und Sulfosäuren, in Gegenwart oder Abwesenheit von Kupfer oder Kupferverbindungen mit Polysulfäden verschmilzt.The main patent and its additional patent 264292 protect processes for Representation of brown sulfur dyes, which consist in the fact that perimidine, its homologues and derivatives, such as in particular its nitro or amido compounds and Sulphonic acids, in the presence or absence of copper or copper compounds with Polysulfate fuses.
Es wurde nun gefunden, daß man zu ähnlichen Farbstoffen gelangt, wenn man an Stelle der oben genannten Perimidine und Perimidinderivate Perinaphtylenharnstoff bzw. -thioharnstoff und deren Substitutionsprodukte, wie insbesondere ihre Nitro- bzw. Amidoverbindungen, Sulfosäuren oder Nitrosulfosäuren, der Schwefelschmelze unterwirft. Die Farbstoffe färben Baumwolle in satten braunen bis schwarzbraunen Tönen von sehr guter Kochechtheit an.It has now been found that similar dyes are obtained by replacing them of the above-mentioned perimidines and perimidine derivatives perinaphthylene urea or thiourea and their substitution products, such as in particular their nitro or amido compounds, Sulphonic acids or nitrosulphonic acids, which subjects molten sulfur. The dyes dye cotton in rich brown to black-brown shades of very good cooking fastness at.
15 Teile Perinaphtylenthioharnstoff (Sachs, Annalen 365, 141), 135 Teile Schwefelnatrium, kristallisiert, 40 Teile Schwefel und 10 Teile Kupfer werden langsam eingedickt und etwa 10 Stunden bei 200 bis 250° gebacken. Die gepulverte Schmelze kann direkt zum Färben benutzt werden. Sie färbt Baumwolle im Schwefelnatriumbade in echten dunkelbraunen Tönen.15 parts perinaphthylene thiourea (Sachs, Annals 365, 141), 135 parts of sodium sulphide, crystallized, 40 parts of sulfur and 10 parts of copper are slowly thickened and about Baked for 10 hours at 200 to 250 °. The powdered melt can be used directly for coloring to be used. It dyes cotton in a sulfur-sodium bath in real dark brown Tones.
30 Teile Perinaphtylenthioharnstoff-3-6-disulfosäure werden mit 140 Teilen Schwefelnatrium, kristallisiert, 40 Teilen Schwefel und 10 Teilen Kupfer eingedickt und, wie in Beispiel ι angegeben, etwa 10 Stunden bei 200 bis 250° erhitzt. Der Farbstoff färbt Baumwolle im Schwefelnatriumbade in echten schwarzbraunen Tönen.30 parts of perinaphthylene thiourea-3-6-disulfonic acid are crystallized with 140 parts of sodium sulfur, 40 parts of sulfur and 10 parts of copper thickened and, as indicated in Example ι, about 10 hours at 200 heated to 250 °. The dye dyes cotton in a sulfur sodium bath in real ones black-brown tones.
Die Perinaphtylenthioharnstoff - 3 - 6 - disulfosäure kann durch Einwirkung von Schwefelkohlenstoff auf i-S-Naphtylendiamin-s-o-disulfosäure in wäßrig alkoholischer Lösung erhalten werden. Sie kristallisiert aus Wasser in gelblichweißen Blättchen — leicht löslich in heißem Wasser und Alkalien —, sehr schwer löslich oder unlöslich in den meisten organischen Lösungsmitteln, wie Alkohol, Eisessig, Benzol u. a.Perinaphtylenethiourea - 3 - 6 - disulfonic acid can be caused by the action of carbon disulfide on i-S-naphthylenediamine-s-o-disulfonic acid can be obtained in aqueous alcoholic solution. It crystallizes from water in yellowish white flakes - easily soluble in hot water and alkalis -, very sparingly soluble or insoluble in most organic Solvents such as alcohol, glacial acetic acid, benzene and others.
20 Teile Dinitroperinaphtylenthioharnstofi werden mit 75 Teilen Schwefelnatrium, kristallisiert, 20 Teilen Schwefel und 3 Teilen Kupfer eingedickt und etwa 10 Stunden auf 200 bis 250 ° erhitzt. Der Farbstoff färbt20 parts of Dinitroperinaphtylenenthiourstofi are crystallized with 75 parts of sodium sulfur, 20 parts of sulfur and 3 parts of copper and thickened for about 10 hours 200 to 250 ° heated. The dye stains
*) Früheres Zusatzpatent: 264292.*) Previous additional patent: 264292.
Baumwolle im Schwefelnatriumbade in echten schwarzbraunen Tönen.Cotton in a sulfur sodium bath in real black-brown tones.
Dinitroperinaphtylenthioharnstoff wird hergestellt durch gelindes Erwärmen (50°) einer Suspension des Naphtylenthioharnstoffes · in Eisessig mit 2 Mol. Salpetersäure. Gelbbraunes Pulver ist in Wasser spuren weise löslich, schwer löslich in Alkohol, Äther, Benzol, Eisessig, leichter in Äther, in konzentrierter Schwefelsäure mit bräunlicher Farbe, in verdünnter Natronlauge örangerot.Dinitroperinaphthylene thiourea is made by gently warming (50 °) a Suspension of naphthylene thiourea in glacial acetic acid with 2 mol. Nitric acid. Yellow-brown Powder is slightly soluble in water, hardly soluble in alcohol, ether, benzene, glacial acetic acid, lighter in ether, in concentrated sulfuric acid with a brownish color, in dilute Soda lye orange-red.
Mononitrothioharnstoff entsteht bei der Nitrierung mit der berechneten Menge Salpetersäure.
Er ist ein graubraunes Pulver, schwer löslich in Alkohol, Äther, Benzol, Eisessig,
leichter in Aceton, in konzentrierter Schwefelsäure mit bräunlicher Farbe, in verdünnter
Natronlauge mit orangeroter Farbe löslich.
Die Perinaphtylenthioharnstoff- 4 - sulfosäure kann durch Einwirkung von Schwefelkohlenstoff
auf i-8-Naphtylendiamin-4-sulfosäure hergestellt werden; sie verhält sich in ihren
physikalischen und chemischen Eigenschaften der 3-6-Disulfosäure ganz analog. Sie kristallisiert
aus Wasser in grauweißen Blättchen.Mononitrothiourea is formed during nitration with the calculated amount of nitric acid. It is a gray-brown powder, sparingly soluble in alcohol, ether, benzene, glacial acetic acid, more easily in acetone, in concentrated sulfuric acid with a brownish color, in dilute sodium hydroxide solution with an orange-red color.
Perinaphthylenethiourea-4-sulfonic acid can be prepared by the action of carbon disulfide on i-8-naphthylenediamine-4-sulfonic acid; In terms of its physical and chemical properties, it behaves quite analogously to the 3-6-disulfonic acid. It crystallizes from water in gray-white flakes.
Verwendet man an Stelle der oben genannten Thioharnstoffe den entsprechenden Perinaphtylenharnstoff und seine Derivate, so gelangt man zu ähnlichen Farbstoffen. Die Mengenverhältnisse von Schwefelnatrium und Schwefel sowie Temperatur und Verschmelzungsdauer können natürlich innerhalb weiter Grenzen abgeändert werden.If the corresponding perinaphthylene urea is used instead of the thioureas mentioned above and its derivatives, similar dyes are obtained. The proportions of sulfur sodium and sulfur as well as temperature and fusion time can of course be changed within wide limits.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE264293C true DE264293C (en) |
Family
ID=521619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT264293D Active DE264293C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE264293C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5299464A (en) * | 1991-11-22 | 1994-04-05 | Bennett James A | Hot stick transformer sampler |
-
0
- DE DENDAT264293D patent/DE264293C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5299464A (en) * | 1991-11-22 | 1994-04-05 | Bennett James A | Hot stick transformer sampler |
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