CH246581A - Process for the preparation of a new anthraquinone dye. - Google Patents
Process for the preparation of a new anthraquinone dye.Info
- Publication number
- CH246581A CH246581A CH246581DA CH246581A CH 246581 A CH246581 A CH 246581A CH 246581D A CH246581D A CH 246581DA CH 246581 A CH246581 A CH 246581A
- Authority
- CH
- Switzerland
- Prior art keywords
- vat
- anthraquinone
- dye
- benzoylamino
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000001000 anthraquinone dye Substances 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 5
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 3
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 claims description 3
- 229960005369 scarlet red Drugs 0.000 claims description 3
- IPEIDGXNXFPGBG-UHFFFAOYSA-N 4-methylsulfonylbenzoyl chloride Chemical compound CS(=O)(=O)C1=CC=C(C(Cl)=O)C=C1 IPEIDGXNXFPGBG-UHFFFAOYSA-N 0.000 claims description 2
- IETILUZZBZOQPD-UHFFFAOYSA-N CS(C(C=C1)=CC=C1C(NC(C(C(C1=CC=CC=C11)=O)=C2C1=O)=CC=C2NC(C(C=C1)=CC=C1S(C)(=O)=O)=O)=O)(=O)=O Chemical compound CS(C(C=C1)=CC=C1C(NC(C(C(C1=CC=CC=C11)=O)=C2C1=O)=CC=C2NC(C(C=C1)=CC=C1S(C)(=O)=O)=O)=O)(=O)=O IETILUZZBZOQPD-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000984 vat dye Substances 0.000 claims description 2
- 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 claims 1
- 150000004056 anthraquinones Chemical class 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- QPKPDUOUPHQMDL-UHFFFAOYSA-N CCCCS(C(C=C1)=CC=C1C(NC(C(C(C1=CC=CC=C11)=O)=C2C1=O)=CC=C2NC(C(C=C1)=CC=C1S(CCCC)(=O)=O)=O)=O)(=O)=O Chemical compound CCCCS(C(C=C1)=CC=C1C(NC(C(C(C1=CC=CC=C11)=O)=C2C1=O)=CC=C2NC(C(C=C1)=CC=C1S(CCCC)(=O)=O)=O)=O)(=O)=O QPKPDUOUPHQMDL-UHFFFAOYSA-N 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- ZBKOZGCANJUKEY-UHFFFAOYSA-N 4-butylsulfonylbenzoic acid Chemical compound CCCCS(=O)(=O)C1=CC=C(C(O)=O)C=C1 ZBKOZGCANJUKEY-UHFFFAOYSA-N 0.000 description 1
- LFQVRSPZFDFCKY-UHFFFAOYSA-N 4-butylsulfonylbenzoyl chloride Chemical compound C(CCC)S(=O)(=O)C1=CC=C(C(=O)Cl)C=C1 LFQVRSPZFDFCKY-UHFFFAOYSA-N 0.000 description 1
- AJBWNNKDUMXZLM-UHFFFAOYSA-N 4-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=C(C(O)=O)C=C1 AJBWNNKDUMXZLM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- -1 p-methylsulfonyl-benzoylamino Chemical group 0.000 description 1
- 239000007787 solid Substances 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
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 241209. Verfahren zur Herstellung eines neuen Anthraebinon-Farbstoffes. Gegenstand vorliegender Erfindung ist ein Verfahren zur Herstellung eines neuen An- thraehinon-Küpenfarbstoffes durch Umset zen von 1,4-Diaminoanthrachinon mit einem Gemisch von p-Methylsulfonyl-benzoylchlo- rid und p-n-Butylsulfonyl-benzoylchlorid.
Der so erhaltene neue Farbstoff färbt Baumwolle aus einer bläulichgrauen, alka lischen Hydrosulfitküpe in hellen scharlach roten Farbtönen von sehr guten Echtheits eigenschaften, wobei die so erzielten Fär bungen insbesondere in bezug auf ihre Echt heit beim Kochen in der Küpe denjenigen Färbungen überlegen sind, welche bei Ver wendung von 1,4-Di-(p-methylsulfonyl-ben- zoylamino)-anthrachinon oder von 1,4-Di-(p- n-butylsulfonyl-benzoylamino) - anthrachinon erhalten werden.
Die Erfindung sei durch das nachste hende Beispiel erläutert. Die Teile bedeuten Gewichtsteile.
Beispiel: 9 Teile p-Methylsulfonyl-benzoesäure und 4,84 Teile p-Butylsulfonyl-benzoesäure wer den durch Behandeln mit überschüssigem Thionylchlorid in einer Nitrobenzollösung in ein Gemisch der entsprechenden Säure chloride übergeführt und dieses Gemisch wird hierauf während 2i/2 Stunden bei 120 C mit 4,76 Teilen 1,4-Diaminoanthra- chinon erhitzt.
Alsdann wird das Gemisch gekühlt und der Festkörper, der sich hierbei ausscheidet, abfiltriert und so lange durch Einleiten eines Wasserdampfstromes erhitzt, bis alles Nitrobenzol entwichen ist. Der so erhaltene Farbstoff färbt Baum wolle aus einer bläulichgrauen, alkalischen Hydrosulfitküpe in hellen scharlachroten Farbtönen von sehr guten Echtheitseigen schaften, wobei die so erzielten Farbtöne insbesondere in bezug auf ihre Echtheit beim Kochen in der Küpe denjenigen Färbungen überlegen sind, welche bei der Verwendung von 1,4-Di-(p-methylsulfonyl-benzoylamino)
- anthraehinon oder von 1,4-Di-(p-n-butylsul- fonyl-benzoylamino) -anthrachinon erhalten werden.
Additional patent to main patent No. 241209. Process for the production of a new anthraebinone dye. The present invention relates to a process for the preparation of a new anthraehinone vat dye by reacting 1,4-diaminoanthraquinone with a mixture of p-methylsulfonyl-benzoyl chloride and p-n-butylsulfonyl-benzoyl chloride.
The new dye obtained in this way dyes cotton from a bluish-gray, alkaline hydrosulfite vat in light scarlet red shades of very good fastness properties, the dyeings thus obtained, especially with regard to their authenticity when boiled in the vat, are superior to those dyeings that are used in Use of 1,4-di- (p-methylsulfonyl-benzoylamino) -anthraquinone or of 1,4-di- (p-n-butylsulfonyl-benzoylamino) - anthraquinone can be obtained.
The invention is illustrated by the following example. The parts mean parts by weight.
Example: 9 parts of p-methylsulfonyl-benzoic acid and 4.84 parts of p-butylsulfonyl-benzoic acid are converted into a mixture of the corresponding acid chlorides by treatment with excess thionyl chloride in a nitrobenzene solution and this mixture is then converted at 120 ° C. for 2½ hours heated with 4.76 parts of 1,4-diaminoanthraquinone.
The mixture is then cooled and the solid that separates out is filtered off and heated by passing in a stream of steam until all of the nitrobenzene has escaped. The dye obtained in this way dyes cotton from a bluish-gray, alkaline hydrosulfite vat in light, scarlet-red shades with very good fastness properties, the shades obtained in this way, in particular with regard to their fastness when boiled in the vat, are superior to those dyes which are obtained when using 1 , 4-di (p-methylsulfonyl-benzoylamino)
- Anthraehinone or 1,4-di- (p-n-butylsulfonyl-benzoylamino) -anthraquinone are obtained.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB246581X | 1943-08-03 | ||
| CH241209T | 1944-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH246581A true CH246581A (en) | 1947-01-15 |
Family
ID=25728583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH246581D CH246581A (en) | 1943-08-03 | 1944-10-31 | Process for the preparation of a new anthraquinone dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH246581A (en) |
-
1944
- 1944-10-31 CH CH246581D patent/CH246581A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH246581A (en) | Process for the preparation of a new anthraquinone dye. | |
| DE565426C (en) | Process for the production of Kuepen dyes | |
| CH246580A (en) | Process for the preparation of a new anthraquinone dye. | |
| DE581793C (en) | Process for the preparation of anthraquinone naphthacridone derivatives | |
| DE605937C (en) | Process for the production of Kuepen dyes | |
| DE651249C (en) | Process for the production of Kuepen dyes | |
| DE568035C (en) | Process for the preparation of a gray Kuepen dye of the thionaphthenindolindigo series | |
| DE639731C (en) | Process for the preparation of a real Kuepen dye | |
| DE575326C (en) | Process for the production of Kuepen dyes of the dibenzanthrone series | |
| CH122761A (en) | Process for the preparation of a violet vat dye of the 2-thionaphthene-2-indolindigo series. | |
| AT214029B (en) | Process for the preparation of new monoazo dyes | |
| CH217245A (en) | Process for the production of a vat dye. | |
| CH122762A (en) | Process for the preparation of a violet vat dye of the 2-thionaphthene-2-indolindigo series. | |
| CH156023A (en) | Process for the production of a new vat dye. | |
| CH145873A (en) | Process for the production of a new dye. | |
| CH202860A (en) | Process for the preparation of a dye of the 2-naphthalene-2'-indolindigo series. | |
| CH157526A (en) | Process for the production of a new azo dye. | |
| CH157560A (en) | Process for the preparation of a vat dye of the anthraquinone series. | |
| CH181721A (en) | Process for the production of a new dye of the anthraquinone series. | |
| CH122282A (en) | Process for the preparation of a violet vat dye of the 2-thionaphthene-2-indolindigo series. | |
| CH259731A (en) | Process for the production of a lively acidic milled dye of the anthraquinone series. | |
| CH239007A (en) | Process for the production of a new anthraquinone dye. | |
| CH122275A (en) | Process for the preparation of a violet vat dye of the 2-thionaphthene-2-indolindigo series. | |
| CH122281A (en) | Process for the preparation of a violet vat dye of the 2 - thionaphtene - 2 - indolindigo series. | |
| CH122276A (en) | Process for the preparation of a violet vat dye of the 2-thionaphthene-2-indolindigo series. |