CH186848A - Process for the preparation of a dioxazine dye sulfonic acid. - Google Patents
Process for the preparation of a dioxazine dye sulfonic acid.Info
- Publication number
- CH186848A CH186848A CH186848DA CH186848A CH 186848 A CH186848 A CH 186848A CH 186848D A CH186848D A CH 186848DA CH 186848 A CH186848 A CH 186848A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonic acid
- preparation
- dye
- acid
- benzoquinone
- Prior art date
Links
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000004744 fabric Substances 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 235000013311 vegetables Nutrition 0.000 claims description 3
- 229920000297 Rayon Polymers 0.000 claims description 2
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- -1 permanganate Chemical compound 0.000 description 4
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 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 2
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 2
- USAYMJGCALIGIG-UHFFFAOYSA-N 2,3-dichlorocyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=C(Cl)C(=O)C=CC1=O USAYMJGCALIGIG-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- NXLOLUFNDSBYTP-UHFFFAOYSA-N retene Chemical compound C1=CC=C2C3=CC=C(C(C)C)C=C3C=CC2=C1C NXLOLUFNDSBYTP-UHFFFAOYSA-N 0.000 description 2
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical compound C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- RZFVLEJOHSLEFR-UHFFFAOYSA-N phenanthridone Chemical compound C1=CC=C2C(O)=NC3=CC=CC=C3C2=C1 RZFVLEJOHSLEFR-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfabren zur Darstellung einer Diogazinfarbstoffsulfosäure. Es wurde gefunden, dass man wertvolle Farbstoffsulfosäure erhält, wenn man ;Sulfo- gruppen enthaltende 1.4-Benzochinonderi- vate der Formel:
EMI0001.0010
in der R und R' einen sulfierten, mehr als zwei Ringe enthaltenden einwertigen Rest bedeutet und X und X'=Wasserstoff, Alkyl, Aryl oder Halogen sein kann, mit sauren oder alkalischen Kondensationsmitteln, z. B.
Schwefelsäure, Chlorsulfonsäure, Oleum oder Ammoniak, Soda, Natronlauge und andere mehr, zweckmässig in Gegenwart von orga nischen oder anorganischen Oxydationsmit- teln, beispielsweise Chloranil, Benzochinon, Braunstein, Permanganat, Bleisuperoxyd, Wasserstoffsuperoxyd usw., behandelt.
Unter sulfierten, mehr als zwei Ringe enthaltenden einwertigen Resten sind zu ver stehen beispielsweise diejenigen des Carba- zols, Diphenylenoxyds, Diphenylendioxyds, Fluorens, Anthracens, Phenathrens, Phen- anthridons, Fluoranthrens, Chrysens, Benz- anthracens, Benzofluorens,
Benzodiphenylen- oxyds, Benzophenanthrens, Retens, Perylens und andere mehr.
Die als Ausgangsverbindungen dienenden 1. 4-Benzochinonderivate obiger Formel kön nen zum Beispiel dadurch erhalten werden, ,ass man Chloranil oder ein anderes 1.4- Benzochinon mit .den Aminosulfosäuren der obengenannten, mehr als zwei Ringe enthal tenden Verbindungen, in Reaktion bringt.
Die aus diesen 1. 4-Benzoehinonderivaten gemäss vorliegender Erfindung erhaltenen Kondensationsprodukte sind ihrer Zusam mensetzung nach Dioxazinsulfosäuren und färben .die tierische und pflanzliche Faser, sowie ,gemischte Gewebe in sehr echten Tönen an.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung einer Dioga- zinfarbstoffsulfosäure, welches dadurch ge kennzeichnet ist; dass man 2 . 5-D.i-(N-äthyl- carbazolyl-3'-amino- 6'-sulfosäure) -3 . 6-,di- chlor-l.4-benzochinon mit einem Konden sationsmittel behandelt.
<I>Beispiele:</I> 1. 100 Gewichtsteile 2 . 5 - Di - (N - äthyl - carbazolyl -3' - amino - 6' -sulf osäure) - 3 . 6 --di- chlor-1 .4-benzochinon, hergestellt zum Bei spiel aus Chloranil und 3-Amino-(N)-äthyl- carbazol-6-sulfos:
äure -durch Umsetzen in Alkohol oder wässrigem Alkohol in Gegen wart von säurebindenden Mitteln, werden bei etwa 60 bis<B>70'C</B> .in 2000 Gewichtsteilen konzentrierte Schwefelsäure eingetragen und mehrere Stunden, zum Beispiel etwa 2 bis 5 Stunden, auf etwa 90 bis l00 C erhitzt.
Nach dem Erkalten wird diese Lösung in Eiswasser gegeben und die abgeschiedene Farbstoffsulfonsäure abfiltriert, mit Koch salzlösung neutral gewaschen und getrocknet. Der erhaltene Farbstoff färbt die tierische, pflanzliche und. Viskosefaser, sowie ge- mischte Gewebe in echten klaren Blautönen.
An Stelle von konzentrierter Schwefelsäure kann man zur Bildung des Farbstoffes auch Chlorsulfonsäure verwenden.
2. 58 Gewichtsteile 2.5-Di-(N-äthyl- carbazolyl-3'-amino-6'-sulfosäure-3 . 6,d.ichlor- 1 . 4-benzochinon, hergestellt zum Beispiel aus Chloranil und 3-Amino-(N)-äthylcarbazol-6- sulfosäure durch Umsetzen in Alkohol oder wässrigem Alkohol in Gegenwart von säure bindenden Mitteln, werden bei gewöhnlicher Temperatur in 1000 Gewichtsteilen konzen trierte Schwefelsäure gelöst,
dazu 40 Ge- wichtsteile Braunstein gegeben und damit verrührt. Nach beendeter Reaktion wird ,das Gemisch in Eiswasser gegeben, die abgeschie dene Farbstoffsulfosäure abfiltriert, neutral gewaschen und getrocknet. Sie färbt wie der nach Beispiel 1 dargestellte Farbstoff.
Procedure for the preparation of a diogazine dye sulfonic acid. It has been found that valuable dye sulfonic acid is obtained if 1,4-benzoquinone derivatives containing sulfo groups of the formula:
EMI0001.0010
in which R and R 'denote a sulfated monovalent radical containing more than two rings and X and X' can be hydrogen, alkyl, aryl or halogen, with acidic or alkaline condensation agents, e.g. B.
Sulfuric acid, chlorosulfonic acid, oleum or ammonia, soda, caustic soda and others, conveniently in the presence of organic or inorganic oxidizing agents, such as chloranil, benzoquinone, manganese dioxide, permanganate, lead peroxide, hydrogen peroxide, etc., treated.
Sulfated monovalent radicals containing more than two rings are to be understood as meaning, for example, those of carbazole, diphenylene oxide, diphenylene dioxide, fluorene, anthracene, phenathrene, phenanthridone, fluoranthrene, chrysene, benzanthracene, benzofluorene,
Benzodiphenylene oxide, benzophenanthrene, retene, perylene and others.
The 1,4-benzoquinone derivatives of the above formula used as starting compounds can be obtained, for example, by reacting chloranil or another 1,4-benzoquinone with the aminosulfonic acids of the above-mentioned compounds containing more than two rings.
The condensation products obtained from these 1,4-benzoehinone derivatives according to the present invention are composed of dioxazine sulfonic acids and dye the animal and vegetable fibers and mixed fabrics in very real shades.
The subject matter of the present patent is a process for the preparation of a diogaine dye sulfonic acid, which is characterized; that one 2. 5-D.i- (N-ethyl-carbazolyl-3'-amino-6'-sulfonic acid) -3. 6-, dichloro-1.4-benzoquinone treated with a condensation agent.
<I> Examples: </I> 1. 100 parts by weight 2. 5 - Di - (N - ethyl - carbazolyl -3 '- amino - 6' - sulfonic acid) - 3. 6 - dichloro-1 .4-benzoquinone, produced for example from chloranil and 3-amino- (N) -ethyl-carbazole-6-sulfos:
acid - by reaction in alcohol or aqueous alcohol in the presence of acid-binding agents, concentrated sulfuric acid is introduced in 2000 parts by weight at about 60 to 70 ° C and for several hours, for example about 2 to 5 hours, heated to about 90 to 100 ° C.
After cooling, this solution is poured into ice water and the deposited dyestuff sulfonic acid is filtered off, washed neutral with sodium chloride solution and dried. The dye obtained stains the animal, vegetable and. Viscose fiber and mixed fabrics in real clear shades of blue.
Instead of concentrated sulfuric acid, chlorosulfonic acid can also be used to form the dye.
2. 58 parts by weight of 2,5-di- (N-ethyl-carbazolyl-3'-amino-6'-sulfonic acid-3,6, i.e. dichloro-1,4-benzoquinone, prepared for example from chloranil and 3-amino ( N) -äthylcarbazol-6- sulfonic acid by reacting in alcohol or aqueous alcohol in the presence of acid-binding agents, are dissolved in 1000 parts by weight of concentrated sulfuric acid at normal temperature,
add 40 parts by weight of brownstone and stir it. When the reaction has ended, the mixture is poured into ice water, the dyestuff sulfonic acid deposited is filtered off, washed neutral and dried. It colors like the dye shown in Example 1.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE186848X | 1934-07-27 | ||
| CH186848T | 1935-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH186848A true CH186848A (en) | 1936-10-15 |
Family
ID=25721425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH186848D CH186848A (en) | 1934-07-27 | 1935-07-26 | Process for the preparation of a dioxazine dye sulfonic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH186848A (en) |
-
1935
- 1935-07-26 CH CH186848D patent/CH186848A/en unknown
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