DE97210C - - Google Patents
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- Publication number
- DE97210C DE97210C DENDAT97210D DE97210DA DE97210C DE 97210 C DE97210 C DE 97210C DE NDAT97210 D DENDAT97210 D DE NDAT97210D DE 97210D A DE97210D A DE 97210DA DE 97210 C DE97210 C DE 97210C
- Authority
- DE
- Germany
- Prior art keywords
- toluidine
- nitroaniline
- blue
- dyes
- nitro
- 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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- 239000000975 dye Substances 0.000 claims description 25
- 150000008049 diazo compounds Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 5
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 claims description 4
- GDIIPKWHAQGCJF-UHFFFAOYSA-N 4-Amino-2-nitrotoluene Chemical compound CC1=CC=C(N)C=C1[N+]([O-])=O GDIIPKWHAQGCJF-UHFFFAOYSA-N 0.000 claims description 3
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 claims description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 claims description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 2
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-Nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 claims 2
- VBEGHXKAFSLLGE-UHFFFAOYSA-N N-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 claims 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims 2
- GEMYPJWUMFLPSQ-UHFFFAOYSA-N (2-methylphenyl)sulfamic acid Chemical compound CC1=CC=CC=C1NS(O)(=O)=O GEMYPJWUMFLPSQ-UHFFFAOYSA-N 0.000 claims 1
- QFCSRGLEMDRBMN-UHFFFAOYSA-N N-(2-methylphenyl)nitramide Chemical compound CC1=CC=CC=C1N[N+]([O-])=O QFCSRGLEMDRBMN-UHFFFAOYSA-N 0.000 claims 1
- AGKHYRYULQFGQA-UHFFFAOYSA-N N-(4-methylphenyl)nitramide Chemical compound CC1=CC=C(N[N+]([O-])=O)C=C1 AGKHYRYULQFGQA-UHFFFAOYSA-N 0.000 claims 1
- 239000000982 direct dye Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003929 acidic solution Substances 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- POCJOGNVFHPZNS-ZJUUUORDSA-N (6S,7R)-2-azaspiro[5.5]undecan-7-ol Chemical compound O[C@@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-ZJUUUORDSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- POCJOGNVFHPZNS-UWVGGRQHSA-N Nitramine Natural products O[C@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-UWVGGRQHSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N β-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- PGLRGMMNMUPZTG-UHFFFAOYSA-N (4-methylphenyl)sulfamic acid Chemical compound CC1=CC=C(NS(O)(=O)=O)C=C1 PGLRGMMNMUPZTG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N Tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- VOTFXKJPNQELOG-UHFFFAOYSA-N arsenic acid Chemical compound O[As](=O)=O VOTFXKJPNQELOG-UHFFFAOYSA-N 0.000 description 1
- 229940000488 arsenic acid Drugs 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 235000013311 vegetables 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/08—Preparation of azo dyes from other azo compounds by reduction
- C09B43/10—Preparation of azo dyes from other azo compounds by reduction with formation of a new azo or an azoxy bridge
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paper (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Durch das Verfahren wird die Darstellung von Azofarbstoffen erzielt, welche die vegetabilische Faser, ohne vorhergehendes Beizen, in dunklen satten Farben anfärben, die gegen Säuren und Alkalien beständig sind. Dieses Verfahren ist eine Erweiterung des durch das Patent Nr. 56456 geschützten.Through the process the representation of azo dyes is achieved, which the vegetable Dye fibers, without prior pickling, in dark, rich colors that are resistant to acids and Resistant to alkalis. This method is an extension of that described in Patent No. 56456 protected.
Die nach dem vorliegenden Verfahren erhaltenen Farbstoffe zeichnen sich vor denjenigen des Patentes Nr. 56456 durch folgende Eigenschaften aus:The dyes obtained by the present process stand out above those of patent no. 56456 by the following properties:
i. Durch leichtere Anwendbarkeit. Dienach dem Patent Nr. 56456 erhaltenen Farbstoffe erfordern nämlich die Gegenwart von Aetznatron und von bedeutenden Mengen Kochsalz, ohne dafs jedoch das Farbbad ausgezogen würde. Die nach dem vorliegenden Verfahren erhaltenen Farbstoffe färben dagegen in wässeriger Lösung, der geringe Mengen der üblichen Salzlösungen, wie Kochsalz oder kohlensaures Natron, zugesetzt sein können. Dabei wird mit ι oder 3 pCt. das Farbbad vollständig ausgenutzt.i. By making it easier to use. The after Namely, the dyes obtained in Patent No. 56456 require the presence of caustic soda and of considerable quantities of table salt, without, however, having drawn out the dye bath would. The dyes obtained by the present process, on the other hand, dye in aqueous media Solution containing small amounts of common salt solutions, such as table salt or carbonate Baking soda, can be added. With ι or 3 pCt. the dye bath completely exploited.
' 2. Durch die grofse Verschiedenheit der Nuancen. Nach dem Patent Nr. 56456 werden rothe bis blaurothe Farbstoffe erhalten, während das vorliegende Verfahren dunkel blaugrüne Töne giebt.2. By the great diversity of the Nuances. According to Patent No. 56456, red to bluish-red dyes are obtained, while the present process gives dark blue-green tones.
Als Ausgangsmaterial dienen diejenigen Wolle färbenden Farbstoffe, welche nach den Patenten Nr. 65651 und 75015 entstehen, wenn p- und m-Nitranilih mit Amidonaphtoldisulfosäure H in saurer Lösung gepaart und dann weiter alkalisch combinirt werden mit den im Ansprach angegebenen Diazoverbindungen.The starting material used are those dyes that dye wool, which according to the Patents No. 65651 and 75015 arise when p- and m-Nitranilih with amidonaphtholdisulfonic acid H can be paired in acidic solution and then combined further in an alkaline way with the im Addressed diazo compounds.
Zu diesen Farbstoffen kommen noch diejenigen , welche man aus p-Nitro-o-toluidin und m-Nitro-p-toluidin erhält, und die in den oben genannten Patentschriften nicht beschrieben sind. In addition to these dyes, there are those which are obtained from p-nitro-o-toluidine and m-nitro-p-toluidine, and which are not described in the above-mentioned patents.
Diese Farbstoffe werden leicht und quantitativ in Azoxyaminfarbstoffe übergeführt durch Reduction in alkalischer Lösung mittelst Traubenzucker, Zinnoxydul oder arseniger Säure, d. h. durch Reductionsmittel, die auch in dem Verfahren des Patentes Nr. 56456 Anwendung gefunden haben.These dyes are easily and quantitatively converted into azoxyamine dyes Reduction in an alkaline solution by means of glucose, tin oxide or arsenic Acid, d. H. by reducing agents, which are also used in the process of patent no. 56456 have found.
Die Darstellung kann auf zweierlei Art erfolgen :The presentation can be done in two ways:
I. Die Diazoverbindung des Nitramins wird zuerst nach den Verfahren der Patente Nr. 65651 und 75015 in saurer Lösung mit Amidonaphtoldisulfosäure H gepaart, dann weiter mit einer anderen Diazoverbindung in alkalischer Lösung verbunden und endlich in Azoxyaminverbindung übergeführt, oderI. The diazo compound of nitramine is first prepared by the procedures of Patent Nos. 65651 and 75015 in acidic solution with amidonaphthol disulfonic acid H paired, then further connected with another diazo compound in alkaline solution and finally in azoxyamine compound convicted, or
II. die Diazoverbindung des Nitramins wird mit Amidonaphtoldisulfosäure H gepaart, der Farbstoff in Azoxyaminfarbstoff übergeführt und dieser weiter mit einer Diazoverbindung gekuppelt. Die auf beiden Wegen erhaltenen Farbstoffe sind identisch.II. The diazo compound of nitramine is paired with amidonaphthol disulfonic acid H, the Dye converted into azoxyamine dye and this further with a diazo compound coupled. The dyes obtained by both routes are identical.
Man löst den nach den Verfahren der Patente Nr. 75015 bezw. 65651 aus 13,8 kg p-NitranilinOne solves the BEZW after the method of the patents No. 75015. 65651 from 13.8 kg p-nitroaniline
und Diazobenzol erhaltenen Farbstoff in 1500I Wasser, giebt der Lösung 150 1 Natronlauge von 40° B. und 11 kg Traubenzucker hinzu und erwärmt 4 bis 5 Stunden auf 40 bis 500 C. Der gebildete Farbstoff wird ausgesalzen, gepreist und getrocknet; er stellt ein schwarzes, bronzeglänzendes Pulver dar, dessen wässerige Lösung ungebeizte Baumwolle dunkelgrün ausfärbt.and diazobenzene dye obtained in 1500I water, the solution gives 150 1 sodium hydroxide solution of 40 ° for example, and 11 kg of dextrose are added and heated for 4 to 5 hours at 40 to 50 0 C. The dye formed is salted out, priced and dried; it is a black, bronze-shining powder, the aqueous solution of which turns unstained cotton a dark green color.
14,2 kg p-Nitro-o-toluidin (Schmp. 1270) werden mit Amidonaphtoldisulfosäure H in saurer Lösung gepaart und, wie in der Patentschrift Nr. 91507 angegeben, mit Traubenzucker in Azoxyaminfarbstoff übergeführt.14.2 kg of p-nitro-o-toluidine (melting point 127 0 ) are paired with amidonaphthol disulfonic acid H in acidic solution and, as indicated in patent specification No. 91507, converted into azoxyamine dye with grape sugar.
Dieser Farbstoff ist gegen Säure sehr empfindlich und ohne technischen Werth. Dieser Uebelstand verschwindet aber durch darauf folgende Paarung mit einem zweiten Diazokörper. Zu dem Zwecke löst man die aus oben angegebenen Gewichtsmengen erhaltene Paste in 1500 1 Wasser und läfst in die alkalisch gehaltene Lösung die Diazoverbindung von 9,3 kg Anilin oder 10,7 kg p-Toluidin einfliefsen.This dye is very sensitive to acids and has no technical merit. This The disadvantage disappears, however, by the subsequent pairing with a second diazo body. For this purpose, the paste obtained from the amounts by weight given above is dissolved in 1,500 liters of water and made alkaline held solution the diazo compound of 9.3 kg of aniline or 10.7 kg of p-toluidine flow in.
Der erhaltene Farbstoff, der durch Aussalzen, Pressen und Trocknen gewonnen wird, stellt ein dunkles, bronzeglänzendes Pulver dar, das sich leicht in Wasser löst und ungebeizte Baumwolle mit dunkelblaugrüner Farbe ausfärbt.The dye obtained, which is obtained by salting out, pressing and drying, is a dark, shiny bronze powder that dissolves easily in water and is unpickled Dyes cotton with a dark blue-green color.
In nachstehender Tabelle sind die wichtigsten der auf obige Weise erhaltbaren Farbstoffe angegeben. The table below shows the most important of the dyes obtainable in the above manner.
Amidonaphtoldisulfosäure H in saurer Lösung combinirtAmidonaphthol disulfonic acid H combined in acidic solution
mit den Diazoverbindungen vonwith the diazo compounds of
p- m-p- m-
t^1 t ^ 1
NN
in alkalischer Lösung weiter
combinirt mitin an alkaline solution
combined with
, Anilin , Aniline
ρ -Toluidin ρ-toluidine
ο -Toluidin ο -Toluidine
a-Naphtylamin α-naphthylamine
m-Sulfanilsäure ; m-sulfanilic acid;
p-Sulfanilsäure '. p-sulfanilic acid '.
p-Toluidinsulfosäure (1, 2,4) p-toluidine sulfonic acid (1, 2,4)
ο-Toluidinsulfosäure (1, 2, 5) ο-toluidine sulfonic acid (1, 2, 5)
Claims (1)
Schmp. 147c a) ', either converted into azoxyamine dyes and from these further according to the patents No. 65651 and 75015 in alkaline solution nitroaniline
M.p. 147 c
Schmp. no0 Nitroaniline
M.p. no 0
Publications (1)
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DE97210C true DE97210C (en) |
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ID=368276
Family Applications (1)
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Country Status (1)
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