Process for the synthesis of polyalkylphenol antioxidants
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C08G-065/38
C08G-065/40
C08G-061/00
C08G-061/02
출원번호
UP-0292813
(2005-12-02)
등록번호
US-7678877
(2010-04-21)
발명자
/ 주소
Yang, Suizhou
Cholli, Ashok L.
출원인 / 주소
Polnox Corporation
대리인 / 주소
Hamilton, Brook, Smith & Reynolds, P.C.
인용정보
피인용 횟수 :
7인용 특허 :
45
초록▼
Disclosed is a method for the synthesis of sterically hindered polymeric antioxidants based on phenol type antioxidant monomers. The method includes partially etherifying, polymerizing and thermally rearranging a phenol containing monomer represented by the following structural formula: to produ
Disclosed is a method for the synthesis of sterically hindered polymeric antioxidants based on phenol type antioxidant monomers. The method includes partially etherifying, polymerizing and thermally rearranging a phenol containing monomer represented by the following structural formula: to produce a sterically hindered polymeric macromolecular antioxidant. X, R10 and q are as defined herein. The disclosed method is a simple, direct and economical process for the synthesis of sterically hindered polymeric macromolecular antioxidants.
대표청구항▼
What is claimed is: 1. A method of synthesizing an antioxidant polymer, comprising the steps of a) partially etherifying a phenol derivative represented by the following structural formula: wherein: at least one ring carbon atom substituted with an —OH group is adjacent to one unsubstit
What is claimed is: 1. A method of synthesizing an antioxidant polymer, comprising the steps of a) partially etherifying a phenol derivative represented by the following structural formula: wherein: at least one ring carbon atom substituted with an —OH group is adjacent to one unsubstituted ring carbon atom; X is —O—, —NH— or —S—; each R10 is independently an optionally substituted C1-C10 alkyl group, an optionally substituted aryl group, and optionally substituted alkoxy group, an optionally substituted carbonyl group, an optionally substituted alkoxycarbonyl group, an optionally substituted aryloxycarbonyl group, —OH, —SH or —NH2; or two R10 groups on adjacent carbon atoms join together to form an optionally substituted aromatic ring or an optionally substituted carbocyclic or heterocyclic non-aromatic ring; and q is an integer from 0 to 2; by contacting the phenol derivative with an alkyl halide, alcohol or olefin to produce an alkoxy phenol derivative represented by the following structural formula: R is an optionally substituted C1-C10 alkyl group; b) polymerizing the alkoxy phenol derivative to produce an alkoxy phenol polymer comprising at least one repeat unit selected from: n is an integer greater than or equal to 2; and c) thermally rearranging the alkyl portion of the alkoxy group of the polymer repeat units to the adjacent ring carbon atom to give a polymeric alkyl phenol derivative antioxidant comprising at least one repeat unit selected from: 2. The method of claim 1, wherein the phenol derivative is represented by one of the following structural formulas: 3. The method of claim 2, wherein the phenol derivative is represented by one of the following structural formulas: 4. The method of claim 3, wherein the etherification in step a) is carried out in the presence of an alkyl halide and a catalyst selected from pyridine, triethyl amine, trimethyl amine, or diethyl amine. 5. The method of claim 3, wherein the etherification in step a) is carried out in the presence of an alcohol or an olefin and a catalyst selected from the group comprising an inorganic acid and a cationic exchange resin bearing sulfonic acid groups or metal halides. 6. The method of claim 3, wherein the polymerization in step b) is carried out in the presence of a biocatalyst or biomimetic catalyst. 7. The method of claim 6, wherein the biocatalyst or biomimetic catalyst is selected from Iron(II)-salen complexes, horseradish peroxidase, soybean peroxidase, hematin, laccase, tyroniase, or a tyroniase—model complex. 8. The method of claim 3, wherein the thermal rearrangement in step c) is carried out in the presence of catalyst selected from hydrofluoric acid, silica gel or zeolites. 9. The method of claim 3, wherein sterically hindered polymeric macromolecular antioxidant produced in step c) comprises at least one repeat unit selected from: 10. The method of claim 2, wherein the phenol derivative is represented by the following structural formula: wherein: q is 0 or 1. 11. The method of claim 10, wherein sterically hindered polymeric macromolecular antioxidant produced in step c) comprises at least one repeat unit selected from: 12. The method of claim 2, wherein sterically hindered polymeric macromolecular antioxidant produced in step c) comprises at least one repeat unit selected from: 13. The method of claim 1, wherein each R10 is independently c1-c10 alkyl, —OH, —SH or —NH2, or two R10 groups on adjacent carbon atoms join together to form an optionally substituted aromatic ring or an optionally substituted carbocyclic or heterocyclic non-aromatic ring. 14. The method of claim 13, wherein the phenol derivative is represented by the following structural formula: wherein: Ring C is a five or six membered aromatic or carbocyclic or heterocyclic non-aromatic ring; each R10 is independently C1-C10 alkyl group, —OH, —SH or —NH2; R11 is ═O, —OH, C1-C3 alkyl, optionally substituted aryl, —OC(O)(C1-C3 alkyl), —OC(O)(aryl), —OC(O)(substituted aryl), —OC(O)(aralkyl), or —OC(O)(substituted aralkyl); q is 0 or 1; and m is an integer from 0 to 3. 15. The method of claim 14, wherein Ring C is a non-aromatic heterocyclic ring. 16. The method of claim 15, wherein Ring C is tetrahydropyranyl or dihydropyranyl. 17. The method of claim 16, wherein the phenol derivative is represented by the following structural formula: 18. The method of claim 16, wherein the phenol derivative is represented by the following structural formula: 19. The method of claim 16, wherein the phenol derivative is represented by the following structural formula: 20. The method of claim 16, wherein the phenol derivative is represented by the following structural formula:
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Farng L. Oscar (Lawrenceville NJ) Horodysky Andrew G. (Cherry Hill NJ), Dihydrocarbyl substituted phenylenediamine-derived phenolic products as antioxidants.
Tse Mun-Fu (Seabrook TX) Dias Anthony J. (Houston TX) Meka Prasadarao (Seabrook TX) McElrath Kenneth O. (Waterloo BEX), Entanglement-inhibited macromolecules.
Joseph A. Akkara ; Madhu S. R. Ayyagari ; David L. Kaplan, Large-scale production of polyphenols or polyaromatic amines using enzyme-mediated reactions.
Nakauchi Jun (Tokyo JPX) Uematsu Mioko (Kawasaki JPX) Sakashita Keiichi (Akishima JPX) Kageyama Yoshitaka (Tokyo JPX) Hayashi Seiji (Kawasaki JPX) Mori Kenji (Tokyo JPX), Mesomorphic compound having b
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Tripathy Sukant ; Samuelson Lynne A. ; Alva K. Shridhara ; Kumar Jayant ; Marx Kenneth A., Method of forming water-soluble, electrically conductive and optically active polymers.
Cotter Robert J. (Bernardsville NJ) Rimsa Stephen B. (Lebanon NJ) Barclay ; Jr. Robert (Trenton NJ) Kwiatkowski George T. (Greenbrook NJ) Harris James E. (Piscataway NJ), Novel poly(aryl ethers).
Wang Patricia C. (Palo Alto CA) Dale James A. (Menlo Park CA), One step preparation of linear antioxidant phenolic polymers involving use of impure diolefin feedstock and aluminum cat.
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