Chromogenic 4,4-diaryl-2-oxobenzo-3,1-oxazines
AssigneeBayer Aktiengesellschaft
InventorsKarlheinrich Meisel, Horst Berneth
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AssigneeBayer Aktiengesellschaft
InventorsKarlheinrich Meisel, Horst Berneth
Estimating the term…
4,4-Diaryl-2-oxobenzo-3,1-oxazines of the general formula ##STR1## wherein X.sup.1, X.sup.2 and X.sup.3, independently of one another, denote hydrogen, halogen, alkyl, aryl, alkanoylamino, aroylamino, heteryl, NY.sup.1 Y.sup.2, OY.sup.3 or SY.sup.3, at least one of the radicals X.sup.1, X.sup.2 or X.sup.3 standing for NY.sup.1 Y.sup.2, OY.sup.3 or SY.sup.3, R.sup.1 denotes hydrogen, alkyl, cycloalkyl, aralkyl, aryl or the members of a bridge to the o-carbon of ring B, Y.sup.1, Y.sup.2 and Y.sup.3, independently of one another, denote hydrogen, alkyl, cycloalkyl, aralkyl or aryl or the remaining members of a 5- or 6-membered ring which reaches to one of the o-position benzene C atoms and may contain further heteroatoms or Y.sup.1 +Y.sup.2 denote the remaining members of a 5- or 6-membered ring which may contain further heteroatoms and the rings A, B and C and the radicals mentioned can in turn carry nonionic substituents customary in dyestuff chemistry, find utility in pressure-copyable and thermoreactive recording materials.
A chromogenic 4,4-diaryl-2-oxobenzo-3,1-oxazine of the formula ##STR41## wherein X.sup.1, X.sup.2 and X.sup.3, independently of one another, denote hydrogen, halogen, alkyl, aryl, alkanoylamino, aroylamino, heteryl, NY.sup.1 Y.sup.2, OY.sup.3 or SY.sup.3, wherein at least one of the radicals X.sup.1, X.sup.2, and X.sup.3 denotes NY.sup.1 Y.sup.2
Dependencies are inferred from the claim text.
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Condensed with one six-membered ring: with hetero atoms directly attached in position 2
Chemical colour-forming components; Additives or binders therefor: organic colour formers, e.g. leuco dyes
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
Diaryl- or thriarylmethane dyes: derived from triarylmethanes , i.e. central C-atom is substituted by amino, cyano, alkyl
Term ended 21 Oct 2005 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
The invention relates to chromogenic 4,4-diaryl-2-oxobenzo-3,1-oxazines of the general formula ##STR2## wherein X.sup.1, X.sup.2 and X.sup.3, independently of one another, denote hydrogen, halogen, alkyl, aryl, alkanoylamino, aroylamino, heteryl, NY.sup.1 Y.sup.2, OY.sup.3 or SY.sup.3,
at least one of the radicals X.sup.1, X.sup.2 or X.sup.3 standing for NY.sup.1 Y.sup.2, OY.sup.3 or SY.sup.3,
R.sup.1 denotes hydrogen, alkyl, cycloalkyl, aralkyl, aryl or the members of a bridge to the o-carbon of ring B,
26.8 g of Michler's ketone, 10.8 g of ethyl 3-dimethylaminophenylcarbamate, 76.5 g of phosphorus oxychloride and 28.2 g of diphosphorus pentoxide are stirred at room temperature for 48 h. The mixture is subsequently discharged onto 500 g of ice-water, the aqueous solution is decanted from the precipitated oil, the oil is dissolved in 100 ml of glacial acetic acid, the solution is diluted with 500 ml of water and NaOH is added with cooling to precipitate the carbinol base. This carbinol base is dissolved in 750 ml of dimethoxyethane, 15 ml of concentrated NaOH are added, and the mixture is stirred at room temperature for 5 h. The organic phase is separated off and evaporated to dryness in vacuo, and the residue is stirred with methanol until crystallisation occurs. The result obtained is 35 g of product of the formula ##STR14## In glacial acetic acid this product forms a dyestuff having an intensity peak at .lambda..sub.max =596 nm.
An analogous procedure was used to prepare the following examples:
______________________________________ ##STR15## Example R.sup.1 R.sup.2 R.sup.3 .lambda..sub.max ______________________________________ 2 N(C.sub.2 H.sub.5).sub.2 N(CH.sub.3).sub.2 N(C.sub.2 H.sub.5).sub.2 594 nm 3 N(C.sub.4 H.sub.9).sub.2 N(CH.sub.3).sub.2 N(C.sub.2 H.sub.9).sub.2 597 nm 4 N(C.sub.12 H.sub.25).sub.2 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 595 nm ______________________________________