CH426832A - Process for the preparation of derivatives of pyromellitic acid - Google Patents
Process for the preparation of derivatives of pyromellitic acidInfo
- Publication number
- CH426832A CH426832A CH604862A CH604862A CH426832A CH 426832 A CH426832 A CH 426832A CH 604862 A CH604862 A CH 604862A CH 604862 A CH604862 A CH 604862A CH 426832 A CH426832 A CH 426832A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyromellitic acid
- derivatives
- dyeings
- good
- fastness
- Prior art date
Links
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical class OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000004043 dyeing Methods 0.000 claims description 12
- 229920000297 Rayon Polymers 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 6
- 239000004800 polyvinyl chloride Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 229920003002 synthetic resin Polymers 0.000 claims description 6
- 239000000057 synthetic resin Substances 0.000 claims description 6
- 239000004753 textile Substances 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000004922 lacquer Substances 0.000 claims description 4
- 239000004033 plastic Substances 0.000 claims description 4
- 229920003023 plastic Polymers 0.000 claims description 4
- 150000003142 primary aromatic amines Chemical class 0.000 claims description 4
- 229920002955 Art silk Polymers 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims description 2
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 claims description 2
- 229940081735 acetylcellulose Drugs 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000004061 bleaching Methods 0.000 claims description 2
- 229920002301 cellulose acetate Polymers 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 239000000986 disperse dye Substances 0.000 claims description 2
- 238000005108 dry cleaning Methods 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 230000002209 hydrophobic effect Effects 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000000976 ink Substances 0.000 claims description 2
- 230000005012 migration Effects 0.000 claims description 2
- 238000013508 migration Methods 0.000 claims description 2
- 238000010422 painting Methods 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- -1 polypropylene Polymers 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000009987 spinning Methods 0.000 claims description 2
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002966 varnish Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Verfahren zur Herstellung von Derivaten der Pyromellitsäure
Es wurde gefunden, dass man neue Derivate der Pyromellitsäure erhält, wenn man 1 Mol Pyromellitsäure oder eines ihrer Derivate mit 2-3 Mol eines von Ringsubstituenten freien, primären aromatischen Amins umsetzt.
Besonders geeignete Derivate der Pyromellitsäure sind Pyromellitsäuren, deren Anhydrid oder Ester, die in l-Stellung oder 1- und 4-Stellung einen Substituenten, z. B. ein Halogenatom, enthalten. Als Amine, die für die Umsetzung verwendet werden können, kommt besonders Anilin in Betracht.
Die Reaktion, die zu N-substituierten Pyromellitsäure-di-imiden führt, die in l-Stellung durch den Rest eines der verwendeten Amine substituiert sein können, kann unter den für Kondensationsreaktionen üblichen Bedingungen, also bei erhöhter Temperatur, z. B. zwischen etwa 60 und 2800 C, erfolgen. Die Kondensation kann mit oder ohne indifferentes Lösungs- bzw. Verdünnungsmittel durchgeführt werden. Gegebenenfalls kann das überschüssige Amin als Lösungsmittel verwendet werden.
Die erhaltenen Verbindungen sind als Farbstoffe geeignet. Sie können z. B. zum Färben von Kunststoffen, Harzen und Cellulosederivaten und deren Lösungen, von Kautschuk und Papier dienen, vorzugsweise von Polyvinylchlorid, wässrigen Kunstharzdispersionen zu Anstrichzwecken, Drucktinten, Lacken, Spinnmassen aus Cellulosexanthogenat (Viskosekunstseide) und Acetylcellulose (Zweieinhalbund Triacetatkunstseide) und für den Pigmentdruck auf Textilien. Sie eignen sich auch als Dispersionsfarbstoffe zum Färben von Polypropylen, synthetischen Polyamiden, linearen aromatischen Polyestern und anderen hydrophoben Kunststoffen.
Die Färbungen von Lacken, Kunstharzdispersionen, Polyvinylchlorid, die Spinnfärbungen von Viscose, Acetatkunstseide und die Drucke auf Textilien haben gute Allgemeinechtheiten, reine Nuancen und eine sehr gute bis hervorragende Lichtechtheit. Besonders hervorzuheben sind noch die gute Überlackierbarkeit der Kunstharzdispersions- und der Lackfärbungen, die Migrationsechtheit der Polyvinylchloridfärbungen sowie die gute bis sehr gute Wasser-, Wasch-, Schweiss-, Überfärbe-, Alkali-, Säure-, Peroxyd bleich- und Trockenreinigungsechtheit der Viscoseund Acetatkunstseidefärbungen und der Drucke auf Textilien.
PATENTANSPRUCH
Verfahren zur Herstellung von Derivaten der Pyromellitsäure, dadurch gekennzeichnet, dass man 1 Mol Pyromellitsäure oder eines ihrer Derivate mit 2 bis 3 Mol eines von Ringsubstituenten freien, primären aromatischen Amins umsetzt.
UNTERANSPRUCH
Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass Pyromellitsäure, deren Anhydrid oder Ester, die in l-Stellung oder 1- und 4-Stellung ein Halogenatom enthalten, umgesetzt werden.
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the preparation of derivatives of pyromellitic acid
It has been found that new derivatives of pyromellitic acid are obtained if 1 mol of pyromellitic acid or one of its derivatives is reacted with 2-3 mol of a primary aromatic amine free of ring substituents.
Particularly suitable derivatives of pyromellitic acid are pyromellitic acids, their anhydride or esters which have a substituent in the l-position or the 1- and 4-positions, e.g. B. a halogen atom. Particularly suitable amines which can be used for the reaction are aniline.
The reaction which leads to N-substituted pyromellitic acid di-imides, which may be substituted in the l-position by the remainder of one of the amines used, can take place under the conditions customary for condensation reactions, that is to say at elevated temperature, e.g. B. between about 60 and 2800 ° C. The condensation can be carried out with or without an inert solvent or diluent. Optionally, the excess amine can be used as a solvent.
The compounds obtained are suitable as dyes. You can e.g. B. for coloring plastics, resins and cellulose derivatives and their solutions, rubber and paper, preferably polyvinyl chloride, aqueous synthetic resin dispersions for painting purposes, printing inks, varnishes, spinning masses made of cellulose xanthogenate (viscose rayon) and acetylcellulose (two and a half and triacetate printing on) and for the pigment Textiles. They are also suitable as disperse dyes for dyeing polypropylene, synthetic polyamides, linear aromatic polyesters and other hydrophobic plastics.
The dyeings of lacquers, synthetic resin dispersions, polyvinyl chloride, the spin dyeings of viscose, acetate artificial silk and the prints on textiles have good all-round fastness properties, pure nuances and very good to excellent lightfastness. Particularly noteworthy are the good recoatability of the synthetic resin emulsion and the lacquer dyeings, the migration fastness of the polyvinyl chloride dyeings and the good to very good fastness to water, washing, perspiration, overdyeing, alkali, acid, peroxide bleaching and dry cleaning fastness of the viscose and acetate synthetic silk dyeings and prints on textiles.
PATENT CLAIM
Process for the preparation of derivatives of pyromellitic acid, characterized in that 1 mole of pyromellitic acid or one of its derivatives is reacted with 2 to 3 moles of a primary aromatic amine free of ring substituents.
SUBClaim
Process according to patent claim, characterized in that pyromellitic acid, its anhydride or esters which contain a halogen atom in the l-position or the 1- and 4-positions are reacted.
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH604862A CH426832A (en) | 1962-05-18 | 1962-05-18 | Process for the preparation of derivatives of pyromellitic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH604862A CH426832A (en) | 1962-05-18 | 1962-05-18 | Process for the preparation of derivatives of pyromellitic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH426832A true CH426832A (en) | 1966-12-31 |
Family
ID=4303381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH604862A CH426832A (en) | 1962-05-18 | 1962-05-18 | Process for the preparation of derivatives of pyromellitic acid |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH426832A (en) |
-
1962
- 1962-05-18 CH CH604862A patent/CH426832A/en unknown
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