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Oxime ester compound and its production method

A compound and oxime ester technology, applied in the field of functional material research, can solve the problems of unfavorable commercialization, difficult synthesis, complex structure, etc., and achieve the effects of less three wastes, stable product quality, and high content

Active Publication Date: 2021-03-19
维思普新材料(苏州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although the above-mentioned compounds have good photoinitiation performance and stability, they are difficult to synthesize and expensive due to their complex structures, which are not conducive to commercialization.

Method used

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  • Oxime ester compound and its production method
  • Oxime ester compound and its production method
  • Oxime ester compound and its production method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0128] The present invention is further described in detail below by way of examples.

Synthetic example 1

[0130] Step 1: Synthesis of ethyl 2-cyano-3-(4-dimethylamino-phenyl)-N-hydroxyacrylimide (compound 1-1)

[0131]

[0132] In a 250mL three-neck flask with a thermometer and a stirrer, add 12.2g of 2-cyano-3-(4-dimethylamino-phenyl)-ethyl acrylate, 4.0g of hydroxylamine hydrochloride, and 5.33 g of anhydrous sodium acetate in sequence. g, 100mL of absolute ethanol, heated to reflux for 5h, cooled to room temperature, then poured into 300g of ice water, stirred, filtered, and dried to obtain 2-cyano-3(4-dimethylamino-phenyl)- N-hydroxyacrylimide ethyl ester (compound 1-1) 12.38g, yield: 95.5%. As determined by HPLC, content: 98.3%. MS(EI): 259.13; Calculated for elemental analysis C 14 h 17 N 3 o 2 (%): C 64.85, H 6.61; Found: C 64.63, H 6.72.

[0133] Step 2: Synthesis of ethyl 2-cyano-3-(4-dimethylamino-phenyl)-N-acetoxyacrylimide (compound 1)

[0134]

[0135] In a 250mL three-neck flask with a thermometer and a stirrer, add the 2-cyano-3-(4-dimethylamino-phenyl)...

Synthetic example 2

[0137] Step 1: Synthesis of ethyl 2-cyano-3-(4-dimethylamino-phenyl)-N-hydroxyacrylimide

[0138] Ethyl 2-cyano-3-(4-dimethylamino-phenyl)-N-hydroxyacrylimide (Compound 1-1) was prepared in the same manner as in Step 1 of Synthesis Example 1.

[0139] Step 2: Synthesis of ethyl 2-cyano-3-(4-dimethylamino-phenyl)-N-benzoyloxyacrylimide (compound 2)

[0140]

[0141] In a 250mL three-neck flask with a thermometer and a stirrer, add the ethyl 2-cyano-3-(4-dimethylamino-phenyl)-N-hydroxyacrylimide (compound 1-1) 9.73g, 5.68g of triethylamine, and 150mL of dichloromethane were completely dissolved and then cooled to 0°C. At 0-5°C, 7.91g of benzoyl chloride was added dropwise, and continued at this temperature after the dropwise addition was completed. Stir for 50min, then warm up to room temperature, continue to stir for 2h, then pour it into 200g of ice water, fully wash with water, separate layers, collect the organic layer, extract the aqueous layer twice with 20mL dichlorom...

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Abstract

The present invention relates to oxime ester compound and its preparation method. The oxime ester compound is represented by the following general formula (I), in the formula (I), X represents Y represents -CN or R 2 means R 1 ’ or ‑OR 1 ’; 1 and R 1 ' each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 12 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms , substituted or unsubstituted aryl group with 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl group with 3 to 20 carbon atoms, substituted or unsubstituted alkoxy group with 1 to 20 carbon atoms, substituted or An unsubstituted aroyl group with 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaroyl group with 3 to 20 carbon atoms; R 3 and R 4 Each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; n represents an integer of 1 to 8.

Description

technical field [0001] The present invention relates to an oxime ester compound and a manufacturing method thereof, in particular to a novel oxime ester compound useful as a photoinitiator used in a polymerizable composition and a manufacturing method thereof, and belongs to the field of functional material research. Background technique [0002] Color photoresist is an important material to form a color filter, mainly composed of three polymer materials of red, green and blue. In recent years, with the increase in demand for TVs and the continuous expansion of panel factories, the demand for color photoresists has continued to grow. The traditional methods of making color photoresist include dyeing method and electrodeposition method. These traditional methods all use metal Cr. However, metal Cr is highly toxic and pollutes seriously. Therefore, the relatively advanced pigment dispersion method is currently used, and its operation process is simple, and its color character...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C259/06C07D295/155C07D213/80C07D213/803C08F2/48
CPCC07C259/06C07D213/80C07D213/803C07D295/155C08F2/48
Inventor 袁晓冬刘海丰陈潇陈华
Owner 维思普新材料(苏州)有限公司