DE236983C - - Google Patents
Info
- Publication number
- DE236983C DE236983C DENDAT236983D DE236983DA DE236983C DE 236983 C DE236983 C DE 236983C DE NDAT236983 D DENDAT236983 D DE NDAT236983D DE 236983D A DE236983D A DE 236983DA DE 236983 C DE236983 C DE 236983C
- Authority
- DE
- Germany
- Prior art keywords
- yellow
- chloride
- well
- anthraquinonylurea
- flakes
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000975 dye Substances 0.000 claims description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- QONRLFCAYFCGBW-UHFFFAOYSA-M [Cl-].C1(=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O)NC(=O)N Chemical compound [Cl-].C1(=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O)NC(=O)N QONRLFCAYFCGBW-UHFFFAOYSA-M 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 3
- 239000000984 vat dye Substances 0.000 claims description 3
- -1 Anthraquinonyl Chemical group 0.000 claims description 2
- 229940018564 M-PHENYLENEDIAMINE Drugs 0.000 claims description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- GNCOVOVCHIHPHP-UHFFFAOYSA-N 2-[[4-[4-[(1-anilino-1,3-dioxobutan-2-yl)diazenyl]-3-chlorophenyl]-2-chlorophenyl]diazenyl]-3-oxo-N-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(C)=O)C(=O)NC1=CC=CC=C1 GNCOVOVCHIHPHP-UHFFFAOYSA-N 0.000 claims 1
- 210000002700 Urine Anatomy 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 210000002268 Wool Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002035 prolonged Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-Methylenedianiline Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 241000131971 Bradyrhizobiaceae Species 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N Martius yellow Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/38—Urea and thiourea derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
Vr 236983 KLASSE 22 b. GRUPPEVr 236983 CLASS 22 b. GROUP
Zusatz zum Patente 236375 vom 2. Februar 1909.Addendum to patent 236375 of February 2, 1909.
Patentiert Im Deutschen Reiche vom 11. April 1909 ab. Längste Dauer: 1. Februar 1924.Patented in the German Empire on April 11, 1909. Longest duration: February 1, 1924.
In der Patentschrift 236375 wurde beschrieben, daß die Harnstoffe, die man durch Umsetzung von Anthrachinonylharnstoffchloriden mit Aminen herstellen kann, Küpenfarbstoffe sind; nunmehr wurde gefunden, daß in gleicher Weise aus Anthrachinonylbarnstoffchloriden mit aromatischen Diaminen gelbe Küpenfarbstoffe entstehen, die sich durch Waschechtheit und Chlorechtheit auszeichnen.In the patent specification 236375 it was described that the ureas obtained by reaction of anthraquinonylurea chlorides with amines can produce vat dyes are; it has now been found that anthraquinonyl barnstoffchloriden in the same way With aromatic diamines, yellow vat dyes are created, which are distinguished by their fastness to washing and chlorine fastness.
100 Teile ß-Anthrachinonylharnstoffchlorid werden fein gemahlen, in 1500 Teilen Benzol suspendiert und sodann eine Lösung von 18 Teilen ρ - Phenylendiamin in 1800 Teilen Benzol unter Rühren zugegeben. Die Farbstoffbildung wird durch längeres Erhitzen im Wasserbade vollendet. Der Farbstoff bildet ein bräunlichgelbes Pulver, das in Wasser, Äther, Benzol sowie den meisten anderen organischen Lösungsmitteln so gut wie unlöslich, in heißem Nitrobenzol etwas mit gelber Farbe löslich ist. Die Lösung in konzentrierter Schwefelsäure ist bräunlichrot, Wasser fällt daraus den Farbstoff in Form gelber Flocken aus. Er schmilzt über 300 ° unter Schwarzfärbung und Zersetzung und färbt Wolle und Baumwolle aus alkalischer Hydrosulfitküpe in rötlichgelben Tönen von hervorragender Wasch- und Chlorechtheit.100 parts of ß-anthraquinonylurea chloride are finely ground, suspended in 1500 parts of benzene and then a solution of 18 parts of ρ-phenylenediamine in 1,800 parts of benzene were added with stirring. The dye formation is completed by prolonged heating in a water bath. The dye forms a brownish-yellow powder, which in water, Ether, benzene and most other organic solvents as good as insoluble, is somewhat soluble in hot nitrobenzene with a yellow color. The solution in concentrated Sulfuric acid is brownish red, water precipitates the dye from it in the form of yellow Flakes off. It melts over 300 ° with blackening and decomposition and stains Wool and cotton from alkaline hydrosulphite vat in reddish yellow tones of excellent Fastness to washing and chlorine.
100 Teile β - Anthrachinonylharnstoffchlorid werden in 1500 Teilen Benzol suspendiert und mit einer Lösung von 18 Teilen m- Phenylendiamin in Benzol unter Rühren versetzt. Man führt die eintretende Umsetzung nach Zusatz von 20 Teilen calcinierter Soda durch längeres Erwärmen auf dem Wasserbade zu Ende. Der Farbstoff bildet ein gelbes Pulver, das in Wasser, Äther, Benzol und den meisten anderen organischen Lösungsmitteln so gut wie unlöslich, in heißem Nitrobenzol etwas mit gelber Farbe löslich ist. Die Lösung in konzentrierter Schwefelsäure ist bräunlichrot, Wasser fällt das Produkt in Form gelber Flocken. Der Farbstoff schmilzt über 280 ° unter Schwarzfärbung und Zersetzung. Er färbt Wolle und Baumwolle aus alkalischer Hydrosulfitküpe in goldgelben, wasch- und chlorechten Tönen an.100 parts of β- anthraquinonylurea chloride are suspended in 1500 parts of benzene, and a solution of 18 parts of m-phenylenediamine in benzene is added while stirring. After the addition of 20 parts of calcined soda, the resulting reaction is brought to an end by prolonged heating on the water bath. The dye forms a yellow powder that is practically insoluble in water, ether, benzene and most other organic solvents, and somewhat soluble in hot nitrobenzene with a yellow color. The solution in concentrated sulfuric acid is brownish red, water falls the product in the form of yellow flakes. The dye melts over 280 ° with blackening and decomposition. He dyes wool and cotton from an alkaline hydrosulphite vat in golden yellow, washable and chlorine-proof tones.
Verwendet man andere Diamine, wie z. B. solche vom Typus des Benzidins, 1 · 5 - Naphtylendiamin, Diaminodiphenylmethan usw., so erhält man Farbstoffe von ähnlichen wertvollen Eigenschaften, von denen einige in folgender Tabelle zusammengestellt sind:If you use other diamines, such as. B. those of the benzidine type, 1 · 5 - naphthylenediamine, Diaminodiphenylmethane, etc., dyes of similar valuable properties are obtained, some of which are in are compiled in the following table:
Claims (1)
SchwefelsäureSolution in conc.
sulfuric acid
alkalischer Hydro
sulfitküpeColored from red
alkaline hydro
sulfite vat
chlorid -f- ρ - Phenylen-
diaminAnthraquinonylurea
chloride -f- ρ - phenylene-
diamine
meisten organi
schen Lösungs
mitteln so gut wie
unlöslich, in heißem
Nitrobenzol etwas
mit gelber Farbe
löslichIn water and the
most organi
different solutions
mean as good as
insoluble in hot
Nitrobenzene something
with yellow color
soluble
Wasser fällt .
gelbe Flockenbrownish red;
Water falls.
yellow flakes
chlorid + m-Phenylen-
diaminAnthraquinonylurea
chloride + m-phenylene-
diamine
chlorid + BenzidinAnthraquinonylurea
chloride + benzidine
chlorid + ι ■ 5-Naphty-
lendiaminAnthraquinonyl urine sioiV-
chloride + ι ■ 5-naphty-
lenediamine
Wasser fällt grün
gelbe Flocken .brownish red;
Water falls green
yellow flakes.
chlorid + Diaminodi-
phenylniethanAnthraquinonylurea
chloride + diaminodi-
phenylniethan
Wasser fällt gelbe
Flockenbrownish red;
Water falls yellow
Flakes
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE236983C true DE236983C (en) |
Family
ID=496629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT236983D Active DE236983C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE236983C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6802364B1 (en) * | 1999-02-19 | 2004-10-12 | Iowa State University Research Foundation, Inc. | Method and means for miniaturization of binary-fluid heat and mass exchangers |
| US7066241B2 (en) | 1999-02-19 | 2006-06-27 | Iowa State Research Foundation | Method and means for miniaturization of binary-fluid heat and mass exchangers |
-
0
- DE DENDAT236983D patent/DE236983C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6802364B1 (en) * | 1999-02-19 | 2004-10-12 | Iowa State University Research Foundation, Inc. | Method and means for miniaturization of binary-fluid heat and mass exchangers |
| US7066241B2 (en) | 1999-02-19 | 2006-06-27 | Iowa State Research Foundation | Method and means for miniaturization of binary-fluid heat and mass exchangers |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE236983C (en) | ||
| DE91150C (en) | METHOD OF INTRODUCING AMINE RESIDUES INTO OXYANTHRACHINONE | |
| DE386054C (en) | Process for the preparation of water-insoluble azo dyes | |
| DE127814C (en) | ||
| DE37021C (en) | Process for the preparation of yellow basic azo dyes from diazotized metanitraniline etc. and metaphenylenediamine | |
| DE256515C (en) | ||
| DE120266C (en) | ||
| DE447015C (en) | Process for the representation of dyes | |
| DE525110C (en) | Process for the preparation of Kuepen dyes of the N-dihydro-1íñ2íñ2'íñ1'-anthraquinonazine series | |
| DE254743C (en) | ||
| DE245232C (en) | ||
| DE659095C (en) | Process for the preparation of Kuepen dyes | |
| DE118078C (en) | ||
| DE502570C (en) | Process for the preparation of acidic wool dyes | |
| DE518335C (en) | Process for the preparation of clusters of the benzanthrone pyrazole anthrone series | |
| DE128845C (en) | ||
| DE665431C (en) | Process for the preparation of basic dyes of the triphenylmethane series | |
| DE236375C (en) | ||
| DE436828C (en) | Process for the production of green dyes of the benzanthrone series | |
| DE168115C (en) | ||
| DE37661C (en) | Process for the production of more or less blue or brown true black dyes directly on the fiber by simultaneous oxidation of aromatic monamine and diamine bases | |
| DE88954C (en) | ||
| DE499968C (en) | Process for the preparation of acidic wool dyes | |
| DE119958C (en) | ||
| DE491426C (en) | Process for the preparation of Kuepen dyes of the anthanthrone series |