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 macromonomer and polymer and methods of making and using the same, can solve the problems of easy degradation of materials such as plastics, elastomers, fuels, oils, etc., and achieve the effect of increasing the density of antioxidants

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

AI Technical Summary

Benefits of technology

[0007] The present invention relates to methods of preparing an antioxidant polymer comprising polymerizing macromonomers that comprise an antioxidant. By having the antioxidant as part of the macromonomer, a polymer with a higher density of antioxidants is prepared more efficiently than coordinating antioxidants to an already formed polymer. The methods of polymerization of the present invention also encompass methods of copolymerization wherein different macromonomers comprising different antioxidants may be used. Alternatively, the other macromonomer,

Problems solved by technology

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

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

[0154] 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 subjec...

example 2

[0156] 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

[0157] 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

Methods of preparing an antioxidant polymer are described comprising polymerizing macromonomers that comprise an antioxidant. By having the antioxidant as part of the macromonomer, a polymer with a higher density of antioxidants is prepared more efficiently than coordinating antioxidants to an already formed polymer. The methods of polymerization also encompass copolymerization wherein different macromonomers comprising different antioxidants may be used. Alternatively, the other macromonomer, or monomer, may not include an antioxidant depending on the intended use of the copolymer and desired properties. The macromonomer comprising a antioxidant may comprise more than one antioxidant which may be the same or different. In one embodiment, the macromonomer is benzene or olefin based, wherein the benzene or olefin is substituted with an antioxidant.

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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IPC IPC(8): C08F4/00A23L35/00
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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