CH199185A - Process for the preparation of a highly substantive 2,3-oxynaphthoic acid arylide. - Google Patents
Process for the preparation of a highly substantive 2,3-oxynaphthoic acid arylide.Info
- Publication number
- CH199185A CH199185A CH199185DA CH199185A CH 199185 A CH199185 A CH 199185A CH 199185D A CH199185D A CH 199185DA CH 199185 A CH199185 A CH 199185A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- oxynaphthoic acid
- acid
- highly substantive
- acid arylide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 title claims 3
- 238000002360 preparation method Methods 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- KYPCUWHXFBFCTI-UHFFFAOYSA-N 3-methoxydibenzofuran-2-amine Chemical compound O1C2=CC=CC=C2C2=C1C=C(OC)C(N)=C2 KYPCUWHXFBFCTI-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- -1 amino compound Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines hochsnbstantiven 2,3-Ogynaphthoesäurearylids. Es wurde gefunden, dass man durch Kon densation von 2,3rOgynaphthoesäure mit 2 - Amino - 3 - alkogydiphenylenogyden oder ihren Substitutiomprodukten zu 2,3-Ogy- naphthoesäurearyliden gelangt, die sich als Grundierungen in der Eisfärberei durch be merkenswerte Eigenschaften auszeichnen.
Sie zeigen in alkalischer Lösung gegenüber pflanzlichen Fasern eine sehr hohe Substan- tivi.tät, so dass die Grundierungsbäder prak tisch weitgehend erschöpft werden.
Derartige Kochsubstantive Grundierungen sind zwar bereits aus den deutschen Patentschriften Nr. 556477 und. 572473 bekannt geworden, doch zeichnen sich die nach dem vorliegen den Verfahren erhältlichen Arylide vor die sen bekannten Grundierungen überTa;schender- weise durch eine viel bessere Löslichkeit aus.
Sie neigen insbesondere nicht zur Hydrolyse, was bei .den bisher bekannten Kochsubstan tiven 2,3-Ogynaphthoesäurearyliden durch Verwendung von viel Natronlauge zum Lösen und langes Stehenlassen .der Lösung mit Formaldehyd einigermassen verhindert werden konnte. Infolge ihrer einfacheren Handhabung stellen die nach dem vor liegenden Verfahren erhältlichen Farbstoff- zwischenprodukte eine wesentliche Bereiche rung der Technik dar.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines hoch- substantiven 2,3 - Ogynaphthoesäurearylids, welches dadurch gekennzeichnet ist, .dass man 2,3-Ogynaphthoesäure mit 2-Amino-3-me- thogyydiphenylenogyd kondensiert. <I>Beispiel:
</I> 98 Gewichtsteile 2,3-Ogynaphthoesäure werden mit 108 Gewichtsteilen 2-Amino-3- methogydiphenylenogyd vom F.92-93' C, das zum Beispiel in der Weise erhältlich ist, dass man 3-Methogydiphenylenogyd nitriert und die erhaltene Nitroverhindung zu der entsprechenden Aminoverbindung reduziert, und<B>1000</B> Gewichtsteilen Chlorbenzol unter Rühren auf<B>80'</B> C erwärmt.
Man lässt bei dieser Temperatur langsam 30 Gewichtsteile Phosphortri.chlorid eintropfen und erhitzt dann mehrere Stunden zum Sieden. Man trennt heiss von der abgeschiedenen phos- phorigen Säure und lässt die Chlorbenzol- lösung erkalten, wobei das Kondensations produkt fast vollkommen auskristallisiert.
Das erhaltene 2-(2',3'-Oxyna.phthoylamino)- 3-methoxydiphenylenoxyd kann mit wesent lich weniger Natronlauge und Formaldehyd zur Herstellung einer stabilen Grundierungs- lösung verwendet werden als beispielsweise das 4-(2',3'-Oxyna.phthoylamino)-diphenyl. Die neue Verbindung kristallisiert aus Eisessig in feinen Nadeln vom F. 227 bie 229 C.
Process for the preparation of a highly stable 2,3-gynaphthoic acid arylide. It has been found that the condensation of 2,3-ogynaphthoic acid with 2-amino-3-alkogydiphenylenogyden or its substitute products leads to 2,3-ogynaphthoic acid arylides, which are notable for use as primers in ice dyeing.
In an alkaline solution they show a very high substantivity compared to vegetable fibers, so that the primer baths are practically largely exhausted.
Such cooking substance primers are already from German patents No. 556477 and. 572473 has become known, but the arylides obtainable by the present process are distinguished over these known primers by a much better solubility.
In particular, they do not tend to hydrolysis, which in the case of the previously known boiling substances 2,3-Ogynaphthoesäurearyliden by using a lot of sodium hydroxide to dissolve and long standing .der solution with formaldehyde could be prevented to some extent. Due to their simpler handling, the dye intermediates obtainable according to the present process represent an essential area of technology.
The subject of the present patent is a process for the production of a highly substantive 2,3-ogynaphthoic acid arylide, which is characterized in that 2,3-ogynaphthoic acid is condensed with 2-amino-3-methogyydiphenylenogyd. <I> example:
98 parts by weight of 2,3-ogynaphthoic acid are mixed with 108 parts by weight of 2-amino-3-methogydiphenylenogyd from F.92-93'C, which can be obtained, for example, by nitrating 3-methogydiphenylenogyd and the nitro compound obtained reduced to the corresponding amino compound, and <B> 1000 </B> parts by weight of chlorobenzene heated to <B> 80 ° C with stirring.
30 parts by weight of phosphorus trichloride are slowly added dropwise at this temperature and the mixture is then heated to the boil for several hours. The separated phosphoric acid is separated in a hot state and the chlorobenzene solution is allowed to cool, the condensation product crystallizing out almost completely.
The 2- (2 ', 3'-Oxyna.phthoylamino) -3-methoxydiphenylene oxide obtained can be used with considerably less sodium hydroxide solution and formaldehyde to produce a stable primer solution than, for example, 4- (2', 3'-Oxyna. phthoylamino) diphenyl. The new compound crystallizes from glacial acetic acid in fine needles from F. 227 to 229 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE205790X | 1936-02-19 | ||
| DE199185X | 1936-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199185A true CH199185A (en) | 1938-08-15 |
Family
ID=32963182
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199185D CH199185A (en) | 1936-02-19 | 1937-02-15 | Process for the preparation of a highly substantive 2,3-oxynaphthoic acid arylide. |
| CH205790D CH205790A (en) | 1936-02-19 | 1937-02-15 | Process for the preparation of a highly substantive 2,3-oxynaphthoic acid arylide. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH205790D CH205790A (en) | 1936-02-19 | 1937-02-15 | Process for the preparation of a highly substantive 2,3-oxynaphthoic acid arylide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH199185A (en) |
-
1937
- 1937-02-15 CH CH199185D patent/CH199185A/en unknown
- 1937-02-15 CH CH205790D patent/CH205790A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH205790A (en) | 1939-06-30 |
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