DE205216C - - Google Patents
Info
- Publication number
- DE205216C DE205216C DENDAT205216D DE205216DA DE205216C DE 205216 C DE205216 C DE 205216C DE NDAT205216 D DENDAT205216 D DE NDAT205216D DE 205216D A DE205216D A DE 205216DA DE 205216 C DE205216 C DE 205216C
- Authority
- DE
- Germany
- Prior art keywords
- sulfur
- dyes
- parts
- derivatives
- alkali metal
- 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.)
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- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 239000000988 sulfur dye Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-Methylenedianiline Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- 239000000975 dye Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VDOSWXIDETXFET-UHFFFAOYSA-N Afloqualone Chemical compound CC1=CC=CC=C1N1C(=O)C2=CC(N)=CC=C2N=C1CF VDOSWXIDETXFET-UHFFFAOYSA-N 0.000 description 1
- DRXXLSUQUQDFPQ-UHFFFAOYSA-N C(C)C=1C(=C(C(=C(C1)C(C1=CC=CC=C1)(N)N)CC1=CC=CC=C1)CC1=CC=CC=C1)CC Chemical compound C(C)C=1C(=C(C(=C(C1)C(C1=CC=CC=C1)(N)N)CC1=CC=CC=C1)CC1=CC=CC=C1)CC DRXXLSUQUQDFPQ-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- QYZIDAZFCCVJNS-UHFFFAOYSA-M [6-(dimethylamino)thioxanthen-3-ylidene]-dimethylazanium;chloride Chemical compound [Cl-].C1=CC(=[N+](C)C)C=C2SC3=CC(N(C)C)=CC=C3C=C21 QYZIDAZFCCVJNS-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- MRVNLKITQIBNKU-UKOJIYRKSA-L disodium;(4E)-4-(naphthalen-1-ylhydrazinylidene)-3-oxonaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(N\N=C3/C4=CC=C(C=C4C=C(C3=O)S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 MRVNLKITQIBNKU-UKOJIYRKSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 235000011121 sodium hydroxide 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
- C09B49/00—Sulfur dyes
- C09B49/04—Sulfur dyes from amino compounds of the benzene, naphthalene or anthracene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- Jig 205216 -KLASSE-22 Ä GRUPPE - Jig 205216 - CLASS 22 Ä GROUP
Dr. B. RASSOW in LEIPZIG. Verfahren zur Herstellung von Schwefelfarbstoffen. Patentiert im Deutschen Reiche vom 26. September 1907 ab. Dr. B. RASSOW in LEIPZIG. Process for the production of sulfur dyes. Patented in the German Empire on September 26, 1907.
Durch Einwirkung von Schwefelsesquioxyd auf Tetraalkyldiaminodiphenylmetrian erhält man nach der Patentschrift 65739 basische Farbstoffe, die nach den Angaben der Patentschrift und nach den Untersuchungen von Biehringer und Topaloff, Journ. f. prakt. Chem. (2) 65, 501 ff., als Thiopyronine zu betrachten sind und demgemäß die folgende Formel . ■ ·Obtained by the action of sulfur sesquioxide on tetraalkyldiaminodiphenylmetrian one after the patent specification 65739 basic dyes, which according to the information of the patent specification and according to the investigations of Biehringer and Topaloff, Journ. f. pract. Chem. (2) 65, 501 ff., Are to be considered as thiopyronines and accordingly the following Formula. ■ ·
(AIk)2 N — C6 H3 (AIk) 2 N - C 6 H 3
C9H9=N (AIk)2 Cl C 9 H 9 = N (AIk) 2 Cl
haben. Verwendet man für die gleiche Κει 5 aktion die Disulfosäure des Diäthyldibenzyldiaminodiphenylmethans, also ebenfalls ein Tetraalkyldiaminoderivat, so entsteht die Disulfosäure eines Thiopyronins, welche einen saueren Wollfarbstoff darstellt.to have. If you use the disulfonic acid of diethyldibenzyldiaminodiphenylmethane for the same Κει 5 action, thus also a tetraalkyl diamino derivative, this is how the disulfonic acid is formed a thiopyronine, which is an acidic wool dye.
Es hat sich nun gezeigt, daß man gänzlich andere Produkte erhält, wenn man Schwefelsesquioxyd in schwefelsaurer Lösung einwirken läßt auf das Diaminodiphenylmethan selber, seine Homologen oder Derivate sowie auf die am Stickstoff alkylierten symmetrischen Disubstitutionsprodukte der genannten Körper, überhaupt auf solche Verbindungen, in denen mindestens zwei Aminwasserstoffatome des Diaminbdiphenylmethans bzw. seiner Derivate nicht substituiert sind.It has now been shown that completely different products are obtained if sulfur sesquioxide is used in sulfuric acid solution can act on the diaminodiphenylmethane itself, its homologues or derivatives and on the symmetrical disubstitution products of these bodies alkylated on nitrogen, in general to those compounds in which at least two amine hydrogen atoms of the diaminobdiphenylmethane or its derivatives are not substituted.
Die auf diese Weise entstehenden FarbstoffeThe dyes produced in this way
stellen hochmolekulare, schwefelreiche, amorphe Produkte dar, die in allen neutralen Mitteln gänzlich unlöslich sind, sich aber in konzentrierter Schwefelsäure mit tiefroter Farbe lösen; starke Natronlauge nimmt sie unter teilweiser Zersetzung auf. Von Schwefelalkalilösung werden sie leicht mit schmutzig grünblauer Farbe gelöst; aus diesen Lösungen ziehen die neuen Farbstoffe mit dunkelgrüner. Farbe auf ungeheizte Baumwolle auf; die Färbung' schlägt bei. der Behandlung mit oxydierenden Mitteln, wie z. B. Wasserdampf und Luft oder Bichromat und Essigsäure, in Bordeauxrot bis Ziegelrot um.represent high-molecular, sulfur-rich, amorphous products that are used in all neutral agents Completely insoluble, but in concentrated sulfuric acid with a deep red color to solve; strong caustic soda absorbs it with partial decomposition. From alkaline sulfur solution they are easily solved with dirty green-blue paint; from these solutions draw the new dyes with dark green. Paint on unheated cotton; the coloring 'contributes. treatment with oxidizing agents Means such as B. water vapor and air or bichromate and acetic acid, in Bordeaux red until brick red around.
Es entstehen demnach nach dem neuen Verfahren typische Schwefelfarbstoffe, die sich durch ihre Nuance und die Reinheit der Färbung von allen bisher bekannten roten Schwefelfarbstoffen auszeichnen.According to the new process, typical sulfur dyes are created which due to their nuance and the purity of the coloring from all previously known red sulfur dyes distinguish.
Die Farbstoffe lassen sich noch nachträglich mit Schwefelalkali oder Alkalipolysulfid behandeln, wobei eine Erhöhung der Echtheitseigenschaften eintreten kann.The dyes can be treated with alkali sulfur or alkali polysulphide afterwards, with an increase in the fastness properties can occur.
Unter andauerndem Rühren trägt man in 15 Teile rauchende Schwefelsäure von 25 Prozent Anhydridgehalt 0,4 Teile Schwefelblumen ein und rührt, bis die Flüssigkeit vollkommen homogen geworden ist. Dann fügt man 1,5 Teile trockenes ^-^-Diaminodiphenylmethan in kleinen Portionen hinzu und sorgt dafür, daß die Mischung nicht über 400 warm wird. Sodann rührt man noch 4 bis 5 Stunden bei gewöhnlicher Temperatur und gießt darauf das Reaktionsgemisch in 80 Teile kaltes Wasser. Der Farbstoff scheidet sich zum Teil sofort aus; man kocht bis zum Verschwinden des Schwefeldioxydgeruchs, saugt den Farbstoff ab undWith constant stirring, add 0.4 parts of sulfur flowers to 15 parts of fuming sulfuric acid with an anhydride content of 25 percent and stir until the liquid has become completely homogeneous. Then add 1.5 parts of dry ^ - ^ - diaminodiphenylmethane in small portions and make sure that the mixture does not get over 40 0 warm. The mixture is then stirred for a further 4 to 5 hours at ordinary temperature and the reaction mixture is then poured into 80 parts of cold water. Some of the dye separates out immediately; one boils until the smell of sulfur dioxide disappears, sucks off the dye and
7070
bringt ihn, ohne ihn zu trocknen, in die Form einer Paste von beliebiger Konzentration.without drying it, puts it in the form of a paste of any concentration.
... Man löst 1 Teil Schwefel in 20 Teilen rauchender Schwefelsäure von 33 Prozent Anhydridgehalt auf und trägt dann eine Lösung von 2 Teilen 3-31-Dichlor-4-41-diaminodiphe-, nylmethan in 10 Teilen Schwefelsäuremonohydrat unter Vermeidung einer Temperatursteigerung über 400 ein; weiterhin kann man wie im Beispiel 1 verfahren.... Dissolve 1 part of sulfur in 20 parts of fuming sulfuric acid with 33 percent anhydride content and then apply a solution of 2 parts of 3-3 1 -dichloro-4-4 1 -diaminodiphe-, nylmethane in 10 parts of sulfuric acid monohydrate, avoiding an increase in temperature over 40 0 a; you can continue to proceed as in example 1.
Claims (1)
Verfahren zur Herstellung von Schwefelfarbstoffen, darin bestehend, daß man Diaminodiphenylmethan, seine Homologen oder Derivate sowie diejenigen am Stickstoff substituierten Abkömmlinge dieser Verbindungen, in welchen noch mindestens zwei Wasserstoffatome der Aminogruppen unbesetzt sind, mit Schwefelsesquioxyd behandelt und eventuell auf die so erhaltenen Produkte Schwefelalkali oder Alkalipolysulfid einwirken läßt.Patent claim: ■
Process for the preparation of sulfur dyes, consisting in treating diaminodiphenylmethane, its homologues or derivatives and those nitrogen-substituted derivatives of these compounds in which at least two hydrogen atoms of the amino groups are still unoccupied with sulfur sesquioxide and possibly on the products thus obtained alkali metal or alkali metal polysulphide can act.
Publications (1)
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DE205216C true DE205216C (en) |
Family
ID=467480
Family Applications (1)
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Country Status (1)
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DE (1) | DE205216C (en) |
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