DE267418C - - Google Patents
Info
- Publication number
- DE267418C DE267418C DENDAT267418D DE267418DA DE267418C DE 267418 C DE267418 C DE 267418C DE NDAT267418 D DENDAT267418 D DE NDAT267418D DE 267418D A DE267418D A DE 267418DA DE 267418 C DE267418 C DE 267418C
- Authority
- DE
- Germany
- Prior art keywords
- violet
- blue
- aminoviolanthrene
- parts
- amino
- 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
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000000984 vat dye Substances 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- HUKPVYBUJRAUAG-UHFFFAOYSA-N Benzanthrone Chemical class C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 5
- YDQNUMLZOCJDKZ-UHFFFAOYSA-N violanthren-1-ylamine Chemical compound C1C(C2=C34)=CC=C3C(C3=C56)=CC=C5CC5=CC=CC=C5C6=CC=C3C4=CC=C2C2=C1C=CC=C2N YDQNUMLZOCJDKZ-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- GZUWHLLVZWEXDX-UHFFFAOYSA-N isoviolanthren-1-ylamine Chemical compound C1C(C2=C34)=CC=C3C(C3=C56)=CC=C5C5=CC=CC=C5CC6=CC=C3C4=CC=C2C2=C1C(N)=CC=C2 GZUWHLLVZWEXDX-UHFFFAOYSA-N 0.000 description 4
- 241000394591 Hybanthus Species 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- -1 iodoethyl Chemical group 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 240000000358 Viola adunca Species 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000131971 Bradyrhizobiaceae Species 0.000 description 1
- 230000036881 Clu Effects 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- HKSRHNHDUAHAAT-UHFFFAOYSA-N Isoviolanthrene Chemical compound C12=C3C4=CC=C2CC2=CC=CC=C2C1=CC=C3C1=CC=C2CC3=CC=CC=C3C3=CC=C4C1=C32 HKSRHNHDUAHAAT-UHFFFAOYSA-N 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
- JAIHDOVRCZNXDU-UHFFFAOYSA-N Violanthrene Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2CC1=CC=C3C1=CC=C2CC3=CC=CC=C3C3=CC=C4C1=C32 JAIHDOVRCZNXDU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- IVNZBWNBYXERPK-DZGBHZPSSA-K trisodium;(8Z)-7-oxo-8-[(4-sulfonatonaphthalen-1-yl)hydrazinylidene]naphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N\N=C3/C(=O)C=CC=4C=C(C=C(C=43)S([O-])(=O)=O)S(=O)(=O)[O-])=CC=C(S([O-])(=O)=O)C2=C1 IVNZBWNBYXERPK-DZGBHZPSSA-K 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/22—Dibenzanthrones; Isodibenzanthrones
- C09B3/30—Preparation from starting materials already containing the dibenzanthrone or isodibenzanthrone nucleus
- C09B3/38—Preparation from starting materials already containing the dibenzanthrone or isodibenzanthrone nucleus by introduction of hydrocarbon or acyl residues into amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 267418 — KLASSE 22 b. GRUPPE- M 267418 - CLASS 22 b. GROUP
<L<L
Patentiert im Deutschen Reiche vom 12. Oktober 1912 ab.Patented in the German Empire on October 12, 1912.
Es hat sich gezeigt, daß man neue wertvolle Küpenfarbstoffe erhält, wenn man in die Aminoderivate von Dibenzanthronen (welche früher unter den Bezeichnungen Cyananthren B, Violanthren B, Violanthren R extra im Handel waren und in den Patentschriften 177574, 194252 und 217570 kurzweg mit Cyananthren, Violanthren und Isoviolänthren bezeichnet wurden) Radikale, wie Alkyle, Aryle, Alkaryle, Aldehydreste, Säurereste u. dgl., einführt. Die erhaltenen Küpenfarbstoffe besitzen andere Nuancen als die verwendeten AminoderivateIt has been shown that you get new valuable vat dyes if you in the amino derivatives of dibenzanthrones (which used to be called cyananthrene B, Violanthren B, Violanthren R extra were in the trade and in the patent specifications 177574, 194252 and 217570 were briefly designated as cyananthrene, violanthrene and isoviolanthrene) Introduces radicals such as alkyls, aryls, alkaryls, aldehyde residues, acid residues and the like. the The vat dyes obtained have different shades than the amino derivatives used
und sind im allgemeinen diesen insbesondere gegenüber Oxydationsmitteln an Echtheit überlegen. and are generally superior to these in terms of fastness, in particular to oxidizing agents.
Die wenigen bereits bekannten Fälle, in denen durch Einführung von Radikalen in die Aminogruppe Farbstoffe von anderen Nuancen entstanden, konnten keine Anhaltspunkte dafür bieten, daß bei den hier benutzten Aminoderivaten eine außerordentlich weitgehende Verschiebung der Nuance, nämlich z. B. von Grün zu sehr wertvollem Bordeaux, stattfinden werde. Abgesehen von derThe few already known cases in which the introduction of radicals into the amino group dyes originated from other shades, could not give any clues offer that with the amino derivatives used here an extraordinary extensive shift in the nuance, namely z. B. from green to very valuable Bordeaux, will take place. Apart from the
4040
4545
des trockenen
FarbstoffsAppearance
of the dry
Dye
der Lösung
in
konz. Schwefel
säurecolour
the solution
in
conc. sulfur
acid
auf Baumwolle
aus der
alkalischen
Hydrosulfitküpecoloring
on cotton
from the
alkaline
Hydrosulfite vat
Aminoviolanthren + Jodäthyl 20 f
Aminoviolanthrene + iodoethyl
Pulverdark brown
powder
Pulverdark brown
powder
Pulverpurple black
powder
30 Aminoisoviolanthrene + iodoethyl
30th
bronzeglänzendes
Pulverdark
shiny bronze
powder
bronzeglänzendes
Pulverdark
shiny bronze
powder
Aminoisoviolanthren + Formaldehyd35
Aminoisoviolanthrene + formaldehyde
bronzeglänzendes
Pulverdark
shiny bronze
powder
5050
5555
6060
7070
wertvollen Nuance besitzen die erhaltenen Produkte eine bedeutend höhere Echtheit als die Ausgangsprodukte, insbesondere eine vorzügliche Chlorechtheit.valuable nuance, the products obtained have a significantly higher authenticity than the starting products, especially excellent chlorine fastness.
ι Teil Aminoviolanthren (vgl. Patentschrift 185222) wird mit 5 Teilen Jo'däthyl im Autoklaven während etwa 6 Stunden auf 150 ° erhitzt; danach wird das überschüssige Jodäthyl abdestilliert, der Rückstand in konzentrierter Schwefelsäure gelöst, durch Eingießen in Wasser ausgefällt, abfiltriert und in Teigform gebracht.ι part of aminoviolanthrene (see. Patent 185222) is with 5 parts of Jo'däthyl in the autoclave heated to 150 ° for about 6 hours; then the excess iodoethyl distilled off, the residue dissolved in concentrated sulfuric acid by pouring into Water precipitated, filtered off and made into dough form.
ι Teil Aminoviolanthren wird mit 10 Teilen Benzoylchlorid so lange zum Kochen erhitzt, bis die Entwicklung von Salzsäure aufgehört hat; nach dem Erkalten wird das abgeschiedene Reaktionsprodukt abfütriert, mit Alkohol gewaschen und getrocknet.ι part aminoviolanthrene is 10 parts Benzoyl chloride heated to a boil until the development of hydrochloric acid ceased Has; after cooling, the separated reaction product is filtered off with alcohol washed and dried.
3 Teile Aminoisoviolanthren (vgl. Patentschrift 234749) werden in 100 Teilen Schwefelsäure 66° Be. gelöst und bei etwa 30 ° mit 20 Teilen 40 prozentiger Formaldehydlösung langsam unter Schütteln versetzt. Die Temperatur steigt dabei auf etwa 100 bis iio°, und die anfangs grüne Farbe der Lösung geht in Blau über. Zur Beendigung der Reaktion erwärmt man noch etwa eine Stunde lang auf 90 bis ioo°. Die Schmelze wird in Wasser gegossen, der ausgeschiedene Farbstoff abfiltriert, gewaschen und in Teigform gebracht.3 parts of aminoisoviolanthrene (cf. patent specification 234749) are used in 100 parts of sulfuric acid 66 ° Be. dissolved and slowly added at about 30 ° with 20 parts of 40 percent formaldehyde solution with shaking. The temperature increases to about 100 to 10 °, and the initially green color of the solution changes to blue. To stop the reaction it is heated to 90 to 100 ° for about an hour. The melt is in water poured, the precipitated dye filtered off, washed and made into dough shape.
Die Eigenschaften der nach vorstehenden Beispielen erhaltenen sowie einiger weiterer, auf analoge Weise dargestellter Farbstoffe ergeben sich aus vorstehender Tabelle.The properties of those obtained according to the preceding examples as well as some other, Dyes presented in an analogous manner are shown in the table above.
Statt der genannten kann man auch andere Radikale in die erwähnten Aminoverbindungen einführen.Instead of those mentioned, other radicals can also be converted into the amino compounds mentioned introduce.
Claims (1)
Publications (1)
Publication Number | Publication Date |
---|---|
DE267418C true DE267418C (en) |
Family
ID=524481
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT267418D Active DE267418C (en) |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE267418C (en) |
-
0
- DE DENDAT267418D patent/DE267418C/de active Active
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE267418C (en) | ||
DE517442C (en) | Process for the preparation of Kuepen dyes | |
DE177574C (en) | ||
DE240276C (en) | ||
DE235364C (en) | ||
DE253714C (en) | ||
DE583936C (en) | Process for the preparation of 1íñ4-diamino-2-aryloxyanthraquinone-3-sulfonic acids | |
DE555937C (en) | Process for the preparation of high molecular weight condensation products of the anthraquinone series | |
DE225319C (en) | ||
DE108546C (en) | ||
DE186597C (en) | ||
DE767692C (en) | Process for the production of azo dyes | |
DE632447C (en) | Process for the preparation of Kuepen dyes | |
DE241343C (en) | ||
DE280649C (en) | ||
DE246581C (en) | ||
DE69933C (en) | Process for the preparation of dyes from the class of the alizarin cyanines. (9 | |
DE252287C (en) | ||
DE172609C (en) | ||
DE1120043B (en) | Process for converting a cobalt phthalocyanine into a Kuepen dye with improved solubility in the Kuepe | |
AT148470B (en) | Process for the production of etchable, green-blue dyeings and prints on cellulose esters and ethers. | |
DE227105C (en) | ||
DE101372C (en) | ||
DE563061C (en) | Process for the production of insoluble azo dyes on the fiber | |
DE203436C (en) |