CH199192A - Process for the preparation of a new, water-soluble dye of the anthraquinone series. - Google Patents
Process for the preparation of a new, water-soluble dye of the anthraquinone series.Info
- Publication number
- CH199192A CH199192A CH199192DA CH199192A CH 199192 A CH199192 A CH 199192A CH 199192D A CH199192D A CH 199192DA CH 199192 A CH199192 A CH 199192A
- Authority
- CH
- Switzerland
- Prior art keywords
- new
- water
- preparation
- dye
- soluble
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims description 3
- 150000004056 anthraquinones Chemical class 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 239000001000 anthraquinone dye Substances 0.000 claims 1
- -1 arylamino radical Chemical group 0.000 description 4
- 239000002253 acid Substances 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B3/02—Benzathrones
- C09B3/06—Preparation from starting materials already containing the benzanthrone nucleus
- C09B3/10—Amino derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines neuen, wasserlöslichen Farbstoffes der Anthraehinonreihe. Es wurde die überraschende Beobachtung gemacht, dass man neue Farbstoffe der An- thrachinonreihe erhält, wenn man Anthra- chinonderivate der allgemeinen Formel
EMI0001.0010
worin X = Wasserstoff oder einen Amino-, Alkylamino- oder Arylaminorest bedeutet und wobei sowohl der Arylamino-,
der An- thraehinon, wie auch der Benzanthronrest Substituenten, wie z. B. Halogen, Cyan, Oxy, Alkoxy, Phenoxy und Alkyl enthalten kön nen, mit sulfierenden Mitteln behandelt.
Die Sulfierung der oben genannten An- thrachinonderivate wird vorteilhafterweise mit Oleum geeigneter Konzentration bezw. mit Chlorsulfonsäure und bei zum Beispiel 20 bis<B>150'</B> C gegebenenfalls in Gegenwart von Borsäure bezw. von Metallsalzen durch geführt.
Enthalten. die Ausgangsprodukte gegen Sulfogruppen austauschfähige Atome oder Gruppen, so kann man die Sulfogruppe durch Erhitzen dieser Verbindungen mit Alkalisulfiten in Gegenwart von geeigneten Lösungsmitteln, wie z. B. Phenol, einführen.
Die nach dem vorliegenden Verfahren er hältlichen Farbstoffe färben tierische Fasern und besitzen ausgezeichnete Echtheitseigen schaften, insbesondere eine aussergewöhnliche Beständigkeit gegen die saure Walke.
Das vorliegende Verfahren betrifft die Darstellung eines neuen, wasserlöslichen An- thrachinonfarbstoffes und ist dadurch gekenm- zeiohnet, @dass@ man 1-Anilido-4-(Bz-l,:benz- anthronylamino)-ianth!racMno#n mit @Scahwie- feJsäure behandelt.
Der erhaltene Farbstoff stellt ein grau schwarzes Pulver dar, welches in Schwefel- säure mit blauer Farbe löslich ist und Wolle in schönen rötlichgrauen Tönen von grosser Echtheit anfärbt.
<I>Beispiel:</I> 5 Teile 1-Anilido-4-(Bz-l-benzantlii-onyl- amino)-antliraehinon (erhalten durch Kon densation von 1.4-Aminoanilidoanthraehinon mit Bz-l-halogenbenzanthron), 4 Teile Glau- bersalz entwässert, werden so lange mit 40 Teilen Oleum 10 bis 15 % bei Temperaturen von 40 bis 80 gerührt, bis eine Probe voll ständig wasserlöslich geworden ist. Der Farb stoff wird durch Eingiessen in Eis oder Was ser isoliert.
Der neue Farbstoff entspricht der Formel
EMI0002.0010
und färbt Wolle in schönen rötlichgrauen Tönen von grosser Echtheit an. Der Farbstoff stellt ein grauschwarzes Pulver dar, welches in SehNvefelsäure mit blauer Farbe löslich ist.
Process for the preparation of a new, water-soluble dye of the anthraehinone series. The surprising observation was made that new dyes of the anthrachinone series are obtained if anthrachinone derivatives of the general formula are obtained
EMI0001.0010
where X = hydrogen or an amino, alkylamino or arylamino radical and where both the arylamino,
the anthraehinone, as well as the benzanthrone radical substituents such. B. halogen, cyano, oxy, alkoxy, phenoxy and alkyl contain NEN treated with sulfonating agents.
The sulphonation of the abovementioned anthraquinone derivatives is advantageously BEZW with oleum of suitable concentration. with chlorosulfonic acid and at, for example, 20 to 150 ° C, optionally in the presence of boric acid or. of metal salts carried out.
Contain. the starting materials for atoms or groups which can be exchanged for sulfo groups, the sulfo group can be removed by heating these compounds with alkali metal sulfites in the presence of suitable solvents, such as. B. phenol, introduce.
The dyes obtainable by the present process dye animal fibers and have excellent fastness properties, especially exceptional resistance to acidic fulling.
The present method relates to the preparation of a new, water-soluble anthrachinone dye and is characterized by the fact that @ one 1-anilido-4- (Bz-1,: benz-anthronylamino) -ianth! RacMno # n with @ Scahwie- FeJ acid treated.
The dye obtained is a gray-black powder which is soluble in sulfuric acid with a blue color and dyes wool in beautiful reddish-gray shades of great fastness.
<I> Example: </I> 5 parts of 1-anilido-4- (Bz-l-benzantlii-onyl-amino) -antliraehinone (obtained by condensation of 1,4-aminoanilidoanthraehinone with Bz-l-halogenobenzanthrone), 4 parts of Glau - Dehydrated oversalt, are stirred with 40 parts of oleum 10 to 15% at temperatures of 40 to 80 until a sample has become completely water-soluble. The dye is isolated by pouring it into ice or water.
The new dye conforms to the formula
EMI0002.0010
and dyes wool in beautiful reddish-gray tones of great authenticity. The dye is a gray-black powder, which is soluble in septic acid with a blue color.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH199192T | 1937-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199192A true CH199192A (en) | 1938-08-15 |
Family
ID=4441698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199192D CH199192A (en) | 1937-07-13 | 1937-07-13 | Process for the preparation of a new, water-soluble dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199192A (en) |
-
1937
- 1937-07-13 CH CH199192D patent/CH199192A/en unknown
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