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Process for preparing a benzoxazinone

A technology of benzoxazine and alkylimidazole, which is applied in the field of preparation of benzoxazine, can solve the problems of increasing the complexity of the method, generating additional costs, loss of raw materials, etc.

Inactive Publication Date: 2009-03-25
TEMSA EURO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The recrystallization step adds to the complexity of the process
Recrystallization also causes loss of raw material, creates additional costs (extra solvents, equipment) and is undesirable from an environmental point of view (incineration)

Method used

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  • Process for preparing a benzoxazinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043]125gm Technical Grade* Itatoic Anhydride (ISA) was dissolved in 1475gm N-Methylimidazole (NMI), the mixture was heated to 60°C and 91.3gm Terephthaloyl Chloride (TPC) was added over 30 minutes with good stirring. The temperature was raised to 120 to 130°C and maintained at this temperature for a further 4 hours. The mixture was cooled to 30°C and the precipitate was filtered. The pellet was reslurried in 400 ml isopropanol (99%) (IPA) and washed 3 times with 150 ml IPA. The resulting precipitate was reslurried in 450 gm NMI heated to 95°C, kept under stirring for 30 minutes and filtered. The wet cake was washed with hot IPA and dried under vacuum (20mm) at 80°C.

[0044] The product 107 gm [2,2-p-phenylene-bis(3,1-benzoxazin-4-one)] was a white powder and was 98.5% pure by HPLC analysis. The product was extracted using dimethylformamide (DMF), and the extract was found to have a color value of <50 APHA.

[0045] * Technical grade itatoic anhydride (sold in Europe an...

Embodiment 2A

[0047] Dissolve 32.6 gm of isatoic anhydride (ISA) (0.2 mol) in a mixture of dimethylformamide (DMF) (150 mol) and 18.2 gm (0.22 mol) of N-methylimidazole (NMI) at 86 to 90°C middle. At this temperature, 21.7 gm (0.107 mol) of terephthaloyl chloride (TPC) were added to the mixture within 30 minutes with stirring. The temperature of the reaction mixture was raised to 110 to 120°C and stirred for 4 hours. The mixture was cooled to 20 to 25°C and stirred for a further 2 hours. Subsequently, the product was filtered and washed on the filter with 150 mL of methanol and dried at 60°C. The yield of 2,2-p-phenylene-bis[4H-3,1-benzoxazin-4-one] / (PBBOX) was 29.8 gm (81%).

Embodiment 2B

[0048] Embodiment 2B (reference example)

[0049] In the reaction of itatoic anhydride (0.2mol), DMF (150mL), pyridine (0.22mol) and TPC (0.107mol) under the above reaction conditions, the yield of PBBOX was only 45.9%.

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PUM

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Abstract

The invention relates to a method for preparing a benzoxazinone comprising reacting an isatoic anhydride with an acylating compound in the presence of an N-alkyl imidazole, to a method for preparing a photo-stabilised composition, comprising adding a benzoxazinone and to the use of a benzoxazinone as a light-absorber or as a stabiliser for a light-sensitive compound.

Description

technical field [0001] The present invention relates to a method for preparing benzoxazines and the use of the prepared benzoxazines. Background technique [0002] Benzoxazines can be used to stabilize polymers against photolysis as described in US 4,446,262 or US 3,989,698. The benzoxazines obtained by the described process for the preparation of benzoxazines have some notable undesirable properties, either imparting high chroma to clear plastics which limits certain applications thereof, or containing high concentrations of sodium ions . [0003] US patent application 2003 / 0096889 A1 describes a process for the preparation of benzoxazines. The method utilizes the reaction between itatoic anhydride (ISA) recrystallized in the presence of pyridine, preferably anhydrous pyridine, and an acylated compound. The method requires recrystallization of the ISA to remove colored contaminants from the ISA that would otherwise contaminate the final product. The recrystallization st...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/22
CPCC08K5/357C07D265/22
Inventor A·K·萨卡尔
Owner TEMSA EURO
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