DE500625C - Process for the preparation of wool dyes of the antraquinone series - Google Patents
Process for the preparation of wool dyes of the antraquinone seriesInfo
- Publication number
- DE500625C DE500625C DEF56973D DEF0056973D DE500625C DE 500625 C DE500625 C DE 500625C DE F56973 D DEF56973 D DE F56973D DE F0056973 D DEF0056973 D DE F0056973D DE 500625 C DE500625 C DE 500625C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- dyes
- antraquinone
- series
- wool dyes
- 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.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 6
- 210000002268 wool Anatomy 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 238000006277 sulfonation reaction Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 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
- C09B1/48—Anthrimides
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung von Wollfarbstoffen der Antrachinonreihe 'Zusatz zum Patent 414865 Durch das Hauptpatent 414 ä 65 ist ein Verfahren zur Darstellung von sauren Wollfarbstoffen geschützt. Es besteht darin, daß man Amino- bzw. Alkylaminodianthrachinonylamine mit sulfierenden Mitteln behandelt. Man erhält so Farbstoffe von dunkelblauen bis grünlichgrauen Tönen, welche hervorragende Echtheitseigenschaften besitzen.Process for the preparation of wool dyes of the antraquinone series 'Addition to patent 414865 by the main patent 414 ä 65 is a method of representation protected from acidic wool dyes. It consists in having amino or alkylaminodianthraquinonylamines treated with sulphurizing agents. This gives dyes from dark blue to greenish-gray tones, which have excellent fastness properties.
Es wurde nun gefunden, :daß man zu Farbstoffen gelangen kann, welche die gleichen wertvollen Färbeeigenschaften wie die Produkte des Hauptpatents, insbesondere auch ihre Lichtechtheit besitzen, wenn man a-a,'-Dianthrachinonylamin selbst mit sulfierenden Mitteln unter solchen Bedingungen behandelt; daß wohl Sulfierung, jedoch keine Oxydation eintritt.It has now been found: that you can get to dyes, which the same valuable coloring properties as the products of the main patent, in particular also have their lightfastness if one uses a-a, '- dianthraquinonylamine itself sulfating agents treated under such conditions; that probably sulfation, however no oxidation occurs.
Dieses Resultat war nicht vorauszusehen. Die Farbstoffe des Hauptpatents, enthalten auxochrome Gruppen, welche für Charakter und Eigenschaften der Farbstoffe wesentlich sind. Im vorliegenden Falle sind solche Gruppen nicht vorhanden. Trotzdem erhält man kräftige Farbstoffe von gleichen vorzüglichen Echtheitseigenschaften, deren Nuancen aber nach dem Verfahren des Hauptpatents nicht erhältlich sind. Auch aus der deutschen Pa-Lentschrift i7¢ 699 war nicht zu entnehmen, daß es möglich sein würde, a-a'-Dianthrachinonylamin nach dem vorliegenden Verfahren in reine Sulfosäuren überzuführen, da das nach obiger Patentschrift durch Sulfierung des a . (3'-Dianthrachinonylamins erhaltbare Produkt ein Gemisch von wahrscheinlich Sulfos,äuren derselben und Oxydationsprodukten der letzteren darstellt.This result could not be foreseen. The dyes of the main patent contain auxochromic groups, which are essential for the character and properties of the dyes. In the present case, there are no such groups. In spite of this, strong dyes with the same excellent fastness properties are obtained, the nuances of which, however, cannot be obtained by the process of the main patent. Also from the German Pa-Lentschrift 17 [ 699 ] it was not to be inferred that it would be possible to convert a-a'-dianthraquinonylamine into pure sulfonic acids by the present process, since according to the above patent by sulfonation of the a. (3'-Dianthraquinonylamine is a mixture of probably sulfonic acids, and oxidation products of the latter.
Beispiel -Eine Auflösung von io Gewichtsteilen i # i'-Dianthrachinonylamn in ioo Gewichtsteilen Oleum von etwa 15 % S03-Gehalt wird kurze Zeit auf 95 bis ioo° erhitzt, bis eine Probe sich in heißem Wasser vollständig mit gelbbrauner Farbe löst. Nach dem Erkalten wird die Schmelze ohne K'ü'hlung in 6oo Gewichtsteile Wasser eingerührt und bei Siedetemperatur allmählich noch so viel gesättigte Kochsalzlösung zugegeben, bis der Farbstoff in einer Probe beim Abkühlen vollständig ausfällt. Nach dem Erkalten wirb das kristallinisch abgeschiedene Produkt auf :ein Filter gebracht und mit verdünnter Salz- Lösung bis zur neutralen Reaktion des Filtrats ausgewaschen.EXAMPLE A dissolution of 10 parts by weight of i # i'-dianthraquinonylamine in 100 parts by weight of oleum with about 15 % SO3 content is briefly heated to 95 to 100 ° until a sample dissolves completely in hot water with a yellow-brown color. After cooling, the melt is stirred into 600 parts by weight of water without cooling and enough saturated sodium chloride solution is gradually added at the boiling point until the dye completely precipitates in a sample on cooling. After cooling, the crystalline precipitated product is swirled up: put on a filter and washed out with dilute salt solution until the filtrate reacts neutral.
Auf Wolle zieht der neue Farbstoff aus saurem Bade in kräftigen, gelblichbraunen Tönen, die auf Chrombeizen sowie durch Nachchromieren nicht verändert werden und sehr gut licht-, walk- und karbonisierecht sind.On wool, the new dye from an acid bath takes on a strong, yellowish-brown color Tones that are not changed on chrome stains or by re-chrome plating and are very light, milled and carbonised.
Der Farbstoff enthält zwei Sulfogruppen in 4 # 4'- Stellung. Diese lassen sich in wwäBriger Lösung durch Brom ersetzen, wodurch das bekannte q. # 4'-Dibrom- i # i'-dianthrachinonylamin (Monatshefte f. Chemie Bd.35, Seite 113 5) entsteht.The dye contains two sulfo groups in the 4 # 4 'position. These can be replaced by bromine in aqueous solution, whereby the well-known q. # 4'-dibromo i # i'-dianthraquinonylamine (monthly journals for chemistry, vol. 35, page 113 5) arises.
Durch vorsichtiges Sulfieren, z. B. mittels Oleum von 25 % S03-Gehalt bei -etwa 3o°, läßt sich auch eine Monosulfosäure des i # i'-Dianthrachinonylamins erhalten, welche Wolle kräftig braunrot färbt.By careful sulfonation, e.g. B. by means of oleum with 25 % SO3 content at -about 30 °, a monosulfonic acid of i # i'-dianthraquinonylamine can also be obtained, which dyes wool a strong brown-red.
Claims (1)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF56973D DE500625C (en) | 1922-07-29 | 1924-09-27 | Process for the preparation of wool dyes of the antraquinone series |
| US50868A US1735123A (en) | 1924-09-27 | 1925-08-17 | Dianthraquinonylamine sulphonic acid dyestuff |
| AT103711D AT103711B (en) | 1922-07-29 | 1925-09-14 | Process for the preparation of acidic wool dyes of the anthraquinone series. |
| FR30955D FR30955E (en) | 1922-07-29 | 1925-09-22 | Production of new anthraquinone series dyes and resulting products |
| GB24165/25A GB240492A (en) | 1924-09-27 | 1925-09-28 | Process for the manufacture of wool dyestuffs of the anthraquinone series |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF52298D DE414865C (en) | 1922-07-29 | 1922-07-29 | Process for the preparation of acidic wool dyes of the anthraquinone series |
| DEF56973D DE500625C (en) | 1922-07-29 | 1924-09-27 | Process for the preparation of wool dyes of the antraquinone series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE500625C true DE500625C (en) | 1930-06-23 |
Family
ID=27789659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF56973D Expired DE500625C (en) | 1922-07-29 | 1924-09-27 | Process for the preparation of wool dyes of the antraquinone series |
Country Status (3)
| Country | Link |
|---|---|
| AT (1) | AT103711B (en) |
| DE (1) | DE500625C (en) |
| FR (1) | FR30955E (en) |
-
1924
- 1924-09-27 DE DEF56973D patent/DE500625C/en not_active Expired
-
1925
- 1925-09-14 AT AT103711D patent/AT103711B/en active
- 1925-09-22 FR FR30955D patent/FR30955E/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR30955E (en) | 1926-10-06 |
| AT103711B (en) | 1926-07-10 |
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