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Anti-oxidant macromonomers and polymers and methods of making and using the same

a macromonomer and polymer technology, applied in the field of anti-oxidant macromonomers and polymers and methods of making and using the same, can solve problems such as inefficiency of methods, and achieve the effects of less prone to oxidation, and short-term and long-term stability towards oxidation

Inactive Publication Date: 2006-02-23
POLNOX CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"The present invention relates to antioxidant polymers that can inhibit oxidation in a substance. These polymers have recurring units that contain antioxidant moieties, which makes them more effective than antioxidant monomers. The antioxidant polymers can be used to create compositions that are less prone to oxidation. The invention provides a way to achieve both short-term and longer-term stability towards oxidation by using both large and small molecules with different diffusion rates."

Problems solved by technology

The latter method is inefficient because not all active functional groups are accessible for reaction within the interior mass of the polymeric chains.

Method used

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  • Anti-oxidant macromonomers and polymers and methods of making and using the same
  • Anti-oxidant macromonomers and polymers and methods of making and using the same
  • Anti-oxidant macromonomers and polymers and methods of making and using the same

Examples

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example 1

[0194] Chemical coupling of acid chloride and antioxidant-alcohol. Thionyl chloride was added drop wise to the suspension of 4-acetoxy benzoic acid in chloroform and the reaction mixture was refluxed. After refluxing the reaction mixture for 4 hours; chloroform and excess thionyl chloride were distilled out under vacuum. The white colored acid chloride product was dried under vacuum for 2 hours and then dissolved in dry dichloromethane. The solution of triethylamine and 3, 5 di-tert-butyl-4-hydroxy-benzyl alcohol in dry dichloromethane was added drop wise to it to obtain a yellow colored clear solution and the reaction mixture was stirred for additional 5 hours at room temperature in nitrogen atmosphere. The saturated aqueous sodium bicarbonate solution was then added and the reaction mixture was stirred for additional 30 minutes. The organic layer was separated and triethylamine-hydrochloride was washed off with water, and the product was dried and evaporated under vacuum and subje...

example 2

[0196] Enzymatic synthesis of antioxidant macromonomer, 4-hydroxy phenyl acetic acid-3,5-di-tert butyl 4-hydroxybenzyl alcohol ester. To the suspension of 3, 5 di-tert-butyl-4-hydroxy-benzyl alcohol and 4-hydroxy-phenyl-acetic acid in toluene in the presence of molecular sieves was added Candida Antarctica LipaseB (novozyme 435). The reaction mixture was stirred at 60° C. for 20 hours. After the completion of reaction; macromonomer (Compound 5) was purified using column chromatography (ethyl acetate petroleum ether). The molecular structure of this compound was confirmed to Structure VII by high resolution proton NMR.

example 3

[0197] Enzymatic synthesis of antioxidant macromonomer, 4-hydroxy phenyl acetic acid-3,5-di-tert butyl 4-hydroxybenzyl alcohol ester involving transesterification. To the suspension of 3, 5 di-tert-butyl-4-hydroxy-benzyl alcohol and 4-hyroxy-phenyl-acetic acid methyl ester in toluene was added Candida Antarctica Lipase B(novozyme 435). The molecular sieves were added to trap methanol that was produced as a result of transesterification. The reaction mixture was stirred at 60° C. for 20 hours. Macromonomer compound (Compound 5) was separated using column chromatography. The formation of the compound was confirmed by high resolution proton NMR.

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Abstract

The present invention relates to macromonomer compounds possessing antioxidant properties, antioxidant polymers comprising the antioxidant macromonomers as a recurring unit, and methods of inhibiting oxidation in a substance comprising contacting the substance with the antioxidant polymers. In one embodiment, substantially all of the recurring macromonomeric units of the antioxidant polymers comprise an antioxidant moiety. In another embodiment, all of the recurring macromonomer units of the antioxidant polymers comprise an antioxidant moiety. The method of the present invention, yields antioxidant polymers with substantially all of the recurring units comprising an antioxidant moiety. These antioxidant polymers have greater bulk antioxidative properties than previously known.

Description

RELATED APPLICATIONS [0001] This application claims the benefit of U.S. Application No. 60 / 590,575, filed on Jul. 23, 2004 and U.S. Application No. 60 / 590,646, filed on Jul. 23, 2004. The entire teachings of the above applications are incorporated herein by reference.BACKGROUND OF THE INVENTION [0002] Most organic materials such as plastics, foods, elastomers, fuels, oils, gasoline and lubricants, fibers are susceptible to degradation due to thermal oxidative processes. Harmful, reactive and unstable free radicals are formed during the oxidation process and attack the nearby stable molecules (polymer chains or small molecules) of the materials, “stealing” their electron. The ‘attacked’ molecule loses its electron, resulting itself a free reactive radical to initiate a cascade of chain reactions. Deterioration of their molecular structures as a result of oxidation processes would affect their shelf life, physical and chemical properties. These oxidative reactions are further enhanced...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08F12/24A23L35/00
CPCC07C45/46Y02E60/324C08F12/24C08F112/14C08G61/02C08G61/025C08G61/10C08G2261/1422C08G2261/1424C08G2261/1426C08G2261/148C08G2261/312C08G2261/3424C09K15/08C09K15/12C09K15/20C09K15/28C12P7/22C12P7/26C12P7/62C12P13/02C07C49/83C07C37/002C07C39/16C08F112/24Y02E60/32
Inventor CHOLLI, ASHOK L.
Owner POLNOX CORP
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