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3-arylbenzofuranone compound and composition formed thereby

A compound, furanone technology, applied in chemical materials and its application fields, can solve unsatisfactory problems and achieve good convenience, high molecular weight, and good application compatibility

Active Publication Date: 2015-03-25
EUTEC NEW MATERIALS TECH (SUZHOU) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above-mentioned technology provides many 3-arylbenzofuranone stabilizers, but these stabilizers still cannot meet the requirements of high-performance applications in various aspects, such as shelf life, moisture absorption, hydrolysis sensitivity, process stability, Color properties, volatility, mobility, compatibility, and improved heat and / or light-induced yellowing and degradation

Method used

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  • 3-arylbenzofuranone compound and composition formed thereby
  • 3-arylbenzofuranone compound and composition formed thereby
  • 3-arylbenzofuranone compound and composition formed thereby

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of 3-(7-tert-butyl-3-(2,3-dimethylphenyl)-2-oxo-2,3-dihydrobenzofuran-5-yl)-propionic acid methyl ester and 3 - Mixtures of methyl (7-tert-butyl-3-(3,4-dimethylphenyl)-2-oxo-2,3-dihydrobenzofuran-5-yl)propanoate.

[0030] In a four-neck round bottom 1000mL flask equipped with a mechanical stirrer, thermal controller and a reflux condenser, add 300g of 1,2-dichloroethane and 118g of methyl 3-(3-tert-butyl-4- Hydroxyphenyl) propionate, stir well to dissolve methyl 3-(3-tert-butyl-4-hydroxyphenyl)propionate in 1,2-dichloroethane. Then 89 g of glyoxylic acid (50% glyoxylic acid in water) and 0.9 g of p-toluenesulfonic acid monohydrate were added. At 85°C, the mixture was heated and refluxed for 6 hours. 1,2-Dichloroethane was then distilled off under reduced pressure. Then 300 mL of methyl tert-butyl ether was added to dissolve the crude product and washed with water. The organic phase was separated off and the methyl tert-butyl ether was then removed under ...

Embodiment 2

[0034] Preparation of 3-(7-tert-butyl)-3-(2,3-dimethylphenyl)-2-oxo-2,3-dihydrobenzofuran-5-yl)propanoic acid-6-methyl Heptyl ester and 3-(7-(tert-butyl)-3-(3,4-dimethylphenyl)-2-oxo-2,3-dihydrobenzofuran-5-yl)propane A mixture of isooctyl esters.

[0035] In a four-neck round bottom 500mL flask equipped with a mechanical stirrer, a thermal controller and a reflux condenser, 140g (0.4 moles) of the product of formula (II-1) prepared in Example 1, and 104 grams of isooctyl alcohol (EXXAL8 isooctyl alcohol 0.8 mole from ExxonMobil Chemical), 40 grams of toluene and 2 grams of aluminum triisopropoxide were mixed. The reaction mixture was stirred and heated to 85°C for 5 hours under nitrogen atmosphere, when the reaction was complete, 8.8 grams of aqueous citric acid solution (50%) was added, stirring was continued for 20 minutes, then 180 g of water was added and stirred for 20 minutes at 75°C minute. The organic phase was separated, washed twice with brine, and dried over sod...

Embodiment 3

[0038] Preparation of octyl 3-(7-(tert-butyl)-3-(2,3-dimethylphenyl)-2-oxo-2,3-dihydrobenzofuran-5-yl)propanoate and 3 - Mixtures of octyl (7-(tert-butyl)-3-(3,4-dimethylphenyl)-2-oxo-2,3-dihydrobenzofuran-5-yl)propanoate.

[0039] The preparation method is basically the same as in Example 2, except that n-octanol is used to replace the isooctyl alcohol in Example 2. 180 g of Compound (I-2) was isolated as a pale yellow viscous liquid. Analytical data of the compound of formula (I-2): MS (m / z: 478.31), 1H NMR (chemical shift of methine is 4.8),

[0040]

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Abstract

The invention discloses a 3-arylbenzofuranone compound. The 3-arylbenzofuranone compound is characterized in that R1-R6 in a structural formula of 3-arylbenzofuranone compound are H or C1-C20 alkyl independently; R7 is C7-C20 alkyl or C7-C20 mixed alkyl. Meanwhile, the invention also discloses a composition formed by 3-arylbenzofuranone compound as well as an application and a preparation method of the 3-arylbenzofuranone compound. The 3-arylbenzofuranone compound and the composition formed by the 3-arylbenzofuranone compound have the application superiority of difficulty in volatilization, difficulty in being extracted, migration resistance, and difficulty in frosting to be separated out on the surface of an organic material, and are wide in application range and have a good application effect.

Description

technical field [0001] The invention relates to a 3-arylbenzofuranone compound and its composition, application and preparation method, and belongs to the technical field of chemical materials and its application. Background technique [0002] Various compositions are known for stabilizing organic polymers against oxidative, thermal and / or light-induced degradation. Such compositions have potential applications in thermoplastics such as polyolefins, thermosetting resins such as polyurethanes, and coating formulations. For example, one of the problems with current polyurethane foams is that such foams tend to yellow over time. Yellowing of polyurethane foam products is undesirable in applications and is mainly caused by thermal and / or light-induced oxidation and fumigation caused by nitrogen oxides (Nox). [0003] The use of 3-arylbenzofuranone compounds as stabilizers for organic polymers is known, for example, in US Pat. It is used as a stabilizer in various organic poly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/83C08K5/1535
CPCC07D307/83C08G18/48C08G18/7621C08K5/1345C08K5/1535C08K5/18C08K5/521C08L25/08C08L2201/08C08G2110/0008C08L71/00C08L55/02C08K5/526C08G2110/0083C08G18/0838C08G18/14C08G18/165C08G18/1808C08G18/244C08J9/0023C08J9/0028C08J2205/06C08J2375/08C08L53/00
Inventor 胡汉民曾裕峰姜方园魏海涛
Owner EUTEC NEW MATERIALS TECH (SUZHOU) CO LTD
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