Yellow-luminescence colorless organic luminophor and a method for preparation thereof

FIELD: organic synthesis.

SUBSTANCE: invention provides novel compound: 1-[2-(4,6-dichloro-[1,3,5]triazine-2-ylamino)phenyl]-benzo[d][1,3]oxazine-4-one, characterized by yellow luminescence. Preparation of this compound comprises preliminarily preparing 2-(2-aminophenyl)-benzo[d][1,3]oxazine-4-one by reaction of anthralic acid with thionyl chloride followed by reaction of thus prepared compound with cyanuric acid chloride. Compound is characterized by fluorescence maximum at 560 nm and spare solubility in most organic solvents. The latter enables use of the compound in polygraphic inks as fluorescent pigment.

EFFECT: enlarged assortment of luminophors.

2 cl, 1 dwg

 

The invention relates to organic phosphors with abnormally large Stokes shift, particularly to those which are colorless in daylight. Such phosphors are used in forensics and remedies of securities and documents from tampering. Widespread colorless in daylight blue phosphors glow (Bmikeandvicki, Bambooteen. Organic phosphors. - L.: Chemistry, 1976, S. 25, 34). Known colorless organic phosphors green fluorescence (UK patent No. 1070326, C 07 D 87/20, 1967)alaca of the present invention was to expand the color gamut of fluorescence. To solve a new phosphor - 2-[2-(4,6-dichloro-[1,3,5]triazine-2-ylamino)-phenyl]-benzo[d][1,3]oxazin-4-one with the maximum fluorescence powder 560 nm. This substance is very trudnorastvorim in most organic solvents and can therefore be used in printing inks as a fluorescent pigment.

The method of obtaining this compound consists of two stages and is to obtain 2-(2-AMINOPHENYL)-benzo[d][1,3]oxazin-4-she's from Anthranilic acid and chloride tiomila and subsequent interaction of the compounds with chloride cianuro.

Example. The flask 27,43 g (0.2 mole) of Anthranilic acid, 120 ml of methylene chloride and 25.3 g (0.25 mol) of triethylamine. If p is remesiana cool the mass to 10-15° C and at this temperature was added a solution of 28,56 g (0,24 mol) chloride tiomila in 50 ml of methylene chloride or chloroform.

Upon completion of addition, the reaction mass is stirred for another 1.5 h at 10-15°and then 1 h at 20-25°C. the resulting mass is cooled, the precipitate is filtered off and washed with water until neutral wash water. The pressed product is dried at 50-60°C. Obtain 12.4 g (52% of theory based on Anthranilic acid) 2-(2-AMINOPHENYL)-benzo[d][1,3]oxazin-4-she (compound 1). Yellow powder with TPL 162°C.

In the flask is charged with a solution of 30 g (0,126 mole) of compound 1 in 1000 ml of acetone, add 18 g of nonionic surfactants, for example, OP-10, and under vigorous stirring was added a solution of 25 g (0,136 mole) of cyanuric chloride in 170 ml of acetone, maintaining the temperature of the reaction mass to 25-30°C. Then the reaction mass is heated to boiling and at this temperature, stirred for 2-3 hours

The precipitated product is filtered, washed with water and dried at 110-130°C. Output 32,8, After crystallization from chloroform receive almost colourless powder with a yellow fluorescence (fluorescence maximum at 560 nm). TPL 235-236°C. Received:

WITH 52,93%; N 2,31%; N 18,31%. Calculated for C17H9Cl2N5About2: 52,87%; N - 2,35%; N - 18,13%. Molecular ion, determined by the method of mass spectrometry, has a weight of 385.

Technical usefulness of C which show the connection lies in the possibility of its use as a colorless organic phosphor yellow glow. In comparison with the known phosphor yellow glow - 2-(2-totalminutes)-4H-oil-[2,3-d]-1,3-oxazin-4-on - new phosphor get easier and cheaper raw materials. In addition, the maximum luminescence is 5 nm bathrope.

New phosphor can be used in fluorescent printing inks.

The drawing shows the fluorescence spectra and excitation of new powder phosphor at room temperature.

1. 2-[2-(4,6-dichloro-[1,3,5]triazine-2-ylamino)-phenyl]-benzo[d][1,3]-oxazin-4-one as a colorless organic phosphor yellow glow.

2. The method of obtaining 2-[2-(4,6-dichloro[1,3,5]triazine-2-ylamino)-phenyl]-benzo[d][1,3]-oxazin-4-she according to claim 1, which consists in the fact that Anthranilic acid is subjected to interaction with chloride tiomila environment methylene chloride or chloroform, followed by the interaction of the resulting 2-(2-AMINOPHENYL)-benzo[d][1,3]oxazin-4-one with cyanuric chloride in the medium of acetone at boiling.



 

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SUBSTANCE: invention provides novel compound: 1-[2-(4,6-dichloro-[1,3,5]triazine-2-ylamino)phenyl]-benzo[d][1,3]oxazine-4-one, characterized by yellow luminescence. Preparation of this compound comprises preliminarily preparing 2-(2-aminophenyl)-benzo[d][1,3]oxazine-4-one by reaction of anthralic acid with thionyl chloride followed by reaction of thus prepared compound with cyanuric acid chloride. Compound is characterized by fluorescence maximum at 560 nm and spare solubility in most organic solvents. The latter enables use of the compound in polygraphic inks as fluorescent pigment.

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29 cl, 36 dwg, 11 tbl, 6 ex

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12 cl, 6 ex, 4 dwg, 4 tbl

FIELD: organic synthesis.

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1 tbl

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