WO2006060801A3 - Process for the synthesis of polyalkylphenol antioxidants - Google Patents

Process for the synthesis of polyalkylphenol antioxidants Download PDF

Info

Publication number
WO2006060801A3
WO2006060801A3 PCT/US2005/044021 US2005044021W WO2006060801A3 WO 2006060801 A3 WO2006060801 A3 WO 2006060801A3 US 2005044021 W US2005044021 W US 2005044021W WO 2006060801 A3 WO2006060801 A3 WO 2006060801A3
Authority
WO
WIPO (PCT)
Prior art keywords
synthesis
sterically hindered
antioxidants
hindered polymeric
disclosed
Prior art date
Application number
PCT/US2005/044021
Other languages
French (fr)
Other versions
WO2006060801A2 (en
Inventor
Suizhou Yang
Ashok L Cholli
Original Assignee
Polnox Corp
Suizhou Yang
Ashok L Cholli
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Polnox Corp, Suizhou Yang, Ashok L Cholli filed Critical Polnox Corp
Priority to CA002589855A priority Critical patent/CA2589855A1/en
Priority to EP05853056A priority patent/EP1817393A2/en
Publication of WO2006060801A2 publication Critical patent/WO2006060801A2/en
Publication of WO2006060801A3 publication Critical patent/WO2006060801A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/312—Non-condensed aromatic systems, e.g. benzene

Abstract

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 (I): 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.
PCT/US2005/044021 2004-12-03 2005-12-02 Process for the synthesis of polyalkylphenol antioxidants WO2006060801A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CA002589855A CA2589855A1 (en) 2004-12-03 2005-12-02 Process for the synthesis of polyalkylphenol antioxidants
EP05853056A EP1817393A2 (en) 2004-12-03 2005-12-02 Process for the synthesis of polyalkylphenol antioxidants

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US63289304P 2004-12-03 2004-12-03
US60/632,893 2004-12-03

Publications (2)

Publication Number Publication Date
WO2006060801A2 WO2006060801A2 (en) 2006-06-08
WO2006060801A3 true WO2006060801A3 (en) 2006-07-06

Family

ID=36263980

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/044021 WO2006060801A2 (en) 2004-12-03 2005-12-02 Process for the synthesis of polyalkylphenol antioxidants

Country Status (4)

Country Link
US (1) US7678877B2 (en)
EP (1) EP1817393A2 (en)
CA (1) CA2589855A1 (en)
WO (1) WO2006060801A2 (en)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7595074B2 (en) * 2002-04-05 2009-09-29 University Of Massachusetts Lowell Polymeric antioxidants
JP2005522564A (en) 2002-04-05 2005-07-28 ユニバーシティ オブ マサチューセッツ ロウエル Polymer antioxidant
EP1846460A2 (en) * 2004-01-21 2007-10-24 University Of Massachusetts Lowell Post-coupling synthetic approach for polymeric antioxidants
JP2008507276A (en) * 2004-07-23 2008-03-13 ポルノクス コーポレーション Antioxidant macromonomer and antioxidant polymer, and method for producing and using the same
WO2006060802A1 (en) * 2004-12-03 2006-06-08 Polnox Corporation Synthesis of sterically hindered phenol based macromolecular antioxidants
CA2589883A1 (en) 2004-12-03 2006-06-08 Polnox Corporation Synthesis of aniline and phenol-based antioxidant macromonomers and corresponding polymers
US20060128939A1 (en) * 2004-12-03 2006-06-15 Vijayendra Kumar One pot process for making polymeric antioxidants
WO2006060801A2 (en) 2004-12-03 2006-06-08 Polnox Corporation Process for the synthesis of polyalkylphenol antioxidants
CA2598703A1 (en) 2005-02-22 2006-08-31 Polnox Corporation Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis , performances and applications
US7705185B2 (en) 2005-03-25 2010-04-27 Polnox Corporation Alkylated and polymeric macromolecular antioxidants and methods of making and using the same
US20070106059A1 (en) * 2005-10-27 2007-05-10 Cholli Ashok L Macromolecular antioxidants and polymeric macromolecular antioxidants
EP1966293A1 (en) * 2005-10-27 2008-09-10 Polnox Corporation Stabilized polyolefin compositions
US7705176B2 (en) * 2005-10-27 2010-04-27 Polnox Corporation Macromolecular antioxidants based on sterically hindered phenols and phosphites
EP1963468A1 (en) * 2005-12-02 2008-09-03 Polnox Corporation Lubricant oil compositions
WO2008005358A2 (en) 2006-07-06 2008-01-10 Polnox Corporation Novel macromolecular antioxidants comprising differing antioxidant moieties: structures, methods of making and using the same
US7767853B2 (en) 2006-10-20 2010-08-03 Polnox Corporation Antioxidants and methods of making and using the same
US9808675B2 (en) 2012-09-13 2017-11-07 Acushnet Company Golf ball compositions
US10294423B2 (en) 2013-11-22 2019-05-21 Polnox Corporation Macromolecular antioxidants based on dual type moiety per molecule: structures, methods of making and using the same
US10035043B2 (en) 2016-12-15 2018-07-31 Acushnet Company Golf ball incorporating highly crosslinked thermoset fluorescent microspheres and methods of making same
US20180251695A1 (en) 2017-03-01 2018-09-06 Polnox Corporation Macromolecular Corrosion (McIn) Inhibitors: Structures, Methods Of Making And Using The Same
US10252112B2 (en) 2017-03-20 2019-04-09 Acushnet Company Golf ball composition
US11697048B2 (en) 2021-08-12 2023-07-11 Acushnet Company Colored golf ball and method of making same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4447657A (en) * 1982-11-10 1984-05-08 Uop Inc. Preparation of ortho-alkylated phenols
EP0688805A1 (en) * 1994-06-24 1995-12-27 Mitsui Toatsu Chemicals, Incorporated Phenol aralkyl resins, preparation process thereof and epoxy resin compositions
US20030191242A1 (en) * 2000-02-22 2003-10-09 Alessandro Zedda Romp with oligomeric uv-absorbers
WO2003087260A1 (en) * 2002-04-05 2003-10-23 University Of Massachusetts Lowell Polymeric antioxidants

Family Cites Families (104)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3294836A (en) 1962-09-17 1966-12-27 Geigy Chem Corp Stabilization of organic material with certain esters of substituted hydroquinones and organic acids
US3441545A (en) 1963-11-01 1969-04-29 Du Pont Modification of olefin-carboxylic acid halide copolymers
CA969192A (en) 1968-06-21 1975-06-10 Ciba-Geigy Corporation Polymeric antioxidants
US3516963A (en) 1968-07-22 1970-06-23 Weston Chemical Corp Phenolic phosphites used as stabilizers
US3632785A (en) 1969-02-19 1972-01-04 Georgia Pacific Corp Method of forming shell molds
US3907939A (en) 1969-06-16 1975-09-23 Ashland Oil Inc Phosphite esters of hindered phenols
US3645970A (en) 1969-10-01 1972-02-29 Ciba Geigy Corp Benzoate homopolymers hindered phenolic groups as stabilizers
CH547335A (en) 1970-10-13 1974-03-29 Sandoz Ag STABILIZED, NON-TEXTILE PLASTICS AND DOMESTIC WEBS.
GB1389442A (en) 1971-03-02 1975-04-03 Kodak Ltd P-phenylene-diamine derivatives and uses therefor
CH564047A5 (en) 1972-05-09 1975-07-15 Sandoz Ag
CA1053832A (en) 1973-11-08 1979-05-01 Polysar Limited Polymeric antioxidants
IT1033433B (en) 1974-03-06 1979-07-10 Scott G PROCESS FOR THE PREPARATION OF POLYMERS STABLE TO OXIDATION
GB1469245A (en) 1974-10-24 1977-04-06 Kodak Ltd Substituted p-phenylenediamines
US4054676A (en) 1974-12-04 1977-10-18 Dynapol Edible with polymeric hydroquinone antioxidant
US3996198A (en) 1975-02-24 1976-12-07 Dynapol One step preparation of linear antioxidant phenolic polymers involving use of impure diolefin feedstock and aluminum catalyst under ortho alkylation conditions
US3996160A (en) 1975-02-24 1976-12-07 Dynapol Corporation Hydroquinonoid ortho-alkylation polymers and the process of their production
US4205151A (en) 1975-04-04 1980-05-27 Dynapol Polymeric N-substituted maleimide antioxidants
US4202816A (en) 1975-06-19 1980-05-13 Ciba-Geigy Corporation Novel light stabilizers
US4094857A (en) 1977-09-01 1978-06-13 E. I. Du Pont De Nemours And Company Copolymerizable phenolic antioxidant
JPS5933138B2 (en) 1977-09-22 1984-08-14 旭化成株式会社 Film containing inorganic filler
NL7905000A (en) 1978-09-25 1980-03-27 Cincinnati Milacron Chem Hindered phenol cpds. useful as antioxidants - comprising 3,5-di:alkyl-4-hydroxyphenyl-alkyl ester or amide cpds.
FR2439769A1 (en) 1978-10-26 1980-05-23 Oreal N- (2,5-DIHYDROXY-TRIMETHYL-3,4,6) BENZYL ACRYLAMIDE AND METHACRYLAMIDE, THEIR PREPARATION METHOD AND THEIR USE FOR MAKING ANTIOXIDANT POLYMERS
US4283572A (en) 1979-12-27 1981-08-11 Borg-Warner Corporation Conversion of alkyl phenyl ether to alkylphenol
US4267358A (en) 1980-03-13 1981-05-12 Borg-Warner Corporation Phenolic ester inhibitor
US4341879A (en) 1980-03-17 1982-07-27 Mitsubishi Gas Chemical Company, Inc. Polyphenylene ether resin composition having improved heat stability and impact strength
US4355148A (en) 1980-09-18 1982-10-19 The B. F. Goodrich Company Norbornene polymers containing bound phenolic antioxidant
JPS5785366A (en) 1980-11-14 1982-05-28 Sankyo Co Ltd 2-mercaptoquinone derivative
US4377666A (en) 1981-08-17 1983-03-22 Phillips Petroleum Company Age-resistant polymers containing chemically bound antioxidant functional groups
US4511491A (en) 1982-07-26 1985-04-16 Sumitomo Chemical Co., Ltd. Stabilizers for synthetic resins
US4465871A (en) 1982-11-10 1984-08-14 Uop Inc. Preparation of 2-t-butyl-4-alkoxy- and 4-hydroxyphenols
IT1177022B (en) 1984-10-24 1987-08-26 Anic Spa STABILIZING COMPOSITION FOR ORGANIC POLYMERS AND STABILIZED POLYMER COMPOSITIONS CONTAINING THEM
JPS6245546A (en) 1985-08-22 1987-02-27 Hitachi Chem Co Ltd Production of phenolic polymer
US4647952A (en) 1985-11-13 1987-03-03 The Mead Corporation Phenolic developer resins
US4855345A (en) 1986-06-19 1989-08-08 Ciba-Geigy Corporation Stabilizers for organic polymers
GB8710171D0 (en) 1987-04-29 1987-06-03 Shell Int Research Copolymer composition
US4857596A (en) 1987-08-12 1989-08-15 Pennwalt Corporation Polymer bound antioxidant stabilizers
US4977004A (en) 1987-09-28 1990-12-11 Tropicana Products, Inc. Barrier structure for food packages
US4849503A (en) 1987-12-21 1989-07-18 Amoco Corporation Novel poly(aryl ethers)
US4925591A (en) 1987-12-22 1990-05-15 Mitsubishi Rayon Co., Ltd. Mesomorphic compound having β-hydroxycarboxyl group as chiral source and liquid crystal composition
EP0358157B1 (en) 1988-09-07 1993-12-15 Yoshitomi Pharmaceutical Industries, Ltd. Individual alpha-form particle crystals of tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyl-oxymethyl]methane and process for its production
US5320889A (en) 1989-01-17 1994-06-14 Tropicana Products, Inc. Plastic bottle for food
DE3920616A1 (en) 1989-06-23 1991-01-03 Boehringer Mannheim Gmbh MEDICINAL PRODUCTS CONTAINING DI-TERT.-BUTYLHYDROXYPHENYL DERIVATIVES AND NEW DERIVATIVES
US5013470A (en) 1989-10-10 1991-05-07 Texaco Inc. Antioxidant VII lubricant additive
US4994498A (en) * 1990-03-02 1991-02-19 Union Carbide Chemicals And Plastics Company Inc. Tantalum-containing catalyst useful for producing alcohols from synthesis gas
US5017727A (en) 1990-07-10 1991-05-21 Copolymer Rubber & Chemical Corporation Polymerizable antioxidant composition
US5207939A (en) 1990-08-23 1993-05-04 Mobil Oil Corporation Dihydrocarbyl substituted phenylenediamine-derived phenolic products as antioxidants
US5574118A (en) 1990-11-02 1996-11-12 Dsm Copolymer, Inc. Olefin polymers containing bound antioxidant
US5206303A (en) 1990-12-27 1993-04-27 Exxon Chemical Patents Inc. Entanglement-inhibited macromolecules
US5652201A (en) 1991-05-29 1997-07-29 Ethyl Petroleum Additives Inc. Lubricating oil compositions and concentrates and the use thereof
US5117063A (en) 1991-06-21 1992-05-26 Monsanto Company Method of preparing 4-aminodiphenylamine
US5449715A (en) 1991-09-17 1995-09-12 Isp Investments Inc. Colorless, non-toxic, stabilized aqueous solution of a C1-C5 alkyl vinyl ether and maleic acid copolymers
US5143828A (en) 1991-12-31 1992-09-01 The United States Of America As Represented By The Secretary Of The Army Method for synthesizing an enzyme-catalyzed polymerized monolayer
IL107927A0 (en) 1992-12-17 1994-04-12 Exxon Chemical Patents Inc Oil soluble ethylene/1-butene copolymers and lubricating oils containing the same
JP3165279B2 (en) 1993-03-29 2001-05-14 三井農林株式会社 Oil-soluble antioxidant containing 3-acylated catechin
JP3377833B2 (en) 1993-08-06 2003-02-17 三井化学株式会社 Molded article made of cyclic olefin resin and method for producing the same
US5911937A (en) 1995-04-19 1999-06-15 Capitol Specialty Plastics, Inc. Desiccant entrained polymer
JP3320307B2 (en) 1996-06-06 2002-09-03 株式会社エス・ディー・エス バイオテック Method for polymerizing phenolic compounds and its use
US5994498A (en) 1997-08-21 1999-11-30 Massachusetts Lowell, University Of Lowell Method of forming water-soluble, electrically conductive and optically active polymers
US6018018A (en) 1997-08-21 2000-01-25 University Of Massachusetts Lowell Enzymatic template polymerization
US6207842B1 (en) 1997-10-09 2001-03-27 Mars Incorporated Process for preparing procyanidin(4-6 or 4-8) oligomers and their derivatives
US5834544A (en) 1997-10-20 1998-11-10 Uniroyal Chemical Company, Inc. Organic materials stabilized by compounds containing both amine and hindered phenol functional functionalities
DE19747644C2 (en) 1997-10-29 2001-02-22 Inst Polymerforschung Dresden Sterically hindered phenols and processes for their preparation
US6444450B2 (en) 1998-01-28 2002-09-03 The United States Of America As Represented By The Secretary Of The Army Large-scale production of polyphenols or polyaromatic amines using enzyme-mediated reactions
DE19843875A1 (en) 1998-09-25 2000-03-30 Basf Ag Metal salen preparation in high yield for use as oxidation catalyst especially for enantiomeric oxidations, using metal oxide as inexpensive metal source
US6150491A (en) 1998-11-06 2000-11-21 The United States Of America As Represented By The Secretary Of The Army Polyaromatic compounds and method for their production
KR20010099984A (en) 1998-12-29 2001-11-09 에프. 아. 프라저, 에른스트 알테르 (에. 알테르), 한스 페터 비틀린 (하. 페. 비틀린), 피. 랍 보프, 브이. 스펜글러, 페. 아에글러 New hydroquinone derivatives as scavengers for oxidised developer
JP3816697B2 (en) 1999-07-07 2006-08-30 大日精化工業株式会社 Functional agent bound with polymer, method for producing the same, method for using them, and article using the same
US7176252B2 (en) 1999-07-29 2007-02-13 Dover Chemical Corporation Solid melt blended phosphite composites
ITMI991896A1 (en) 1999-09-09 2001-03-09 Carlo Ghisalberti MELANINES AND VEGETABLE PIGMENTS
NL1013942C2 (en) 1999-12-23 2001-06-26 Dsm Nv Multifunctional thermal-oxidative stabilizer.
CA2394823A1 (en) 1999-12-30 2001-07-12 Uniroyal Chemical Company, Inc. Antioxidant amines based on n-(4-anilinophenyl)amides
EP1142491A3 (en) 2000-04-06 2002-04-03 Kyowa Hakko Kogyo Co., Ltd. Method of removing off-flavor from foods and deodorizer
US6828364B2 (en) 2000-07-14 2004-12-07 Ciba Specialty Chemicals Corporation Stabilizer mixtures
US20020183470A1 (en) 2000-11-27 2002-12-05 Sukant Tripathy Polymerization of aromatic monomers using derivatives of hematin
WO2002079130A1 (en) 2001-03-30 2002-10-10 Council Of Scientific And Industrial Research A process for preparing alkylated dihydroxybenzene
ATE432313T1 (en) 2001-08-15 2009-06-15 Ciba Holding Inc FLAME-RESISTANT COMPOSITIONS
JP2003138258A (en) 2001-11-07 2003-05-14 Univ Kyoto Antioxidant
US7595074B2 (en) 2002-04-05 2009-09-29 University Of Massachusetts Lowell Polymeric antioxidants
ATE330963T1 (en) 2002-05-30 2006-07-15 Ciba Sc Holding Ag AMORPHOUS SOLID MODIFICATION OF BIS(2,4-DICUMYLPHENYL) PENTAERYTHRITOL DIPHOSPHITE
US7271209B2 (en) 2002-08-12 2007-09-18 Exxonmobil Chemical Patents Inc. Fibers and nonwovens from plasticized polyolefin compositions
WO2004024070A2 (en) 2002-09-10 2004-03-25 The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Factors that bind intestinal toxins
WO2004050795A2 (en) 2002-11-27 2004-06-17 Tufts University Antioxidant-functionalized polymers
US7358383B2 (en) 2003-01-24 2008-04-15 University Of South Florida Polyphenol proteasome inhibitors, synthesis, and methods of use
US20040180994A1 (en) 2003-03-05 2004-09-16 Pearson Jason Clay Polyolefin compositions
US6770785B1 (en) 2003-03-25 2004-08-03 Council Of Scientific And Industrial Research Antiozonant cum antioxidant, process for preparation
EP1468968A1 (en) 2003-04-18 2004-10-20 Technische Universitat, Institut fur Mikrobiologie und Abfalltechnologie Biocatalyst containing a laccase
WO2005025646A2 (en) 2003-09-08 2005-03-24 U.S. Government As Represented By The Secretary Of The Army System and method for providing servo-controlled resuscitation
WO2005025513A2 (en) 2003-09-12 2005-03-24 The Regents Of The Univeristy Of California Guanidinium derivatives for improved cellular transport
US7342060B2 (en) 2003-12-11 2008-03-11 Dover Chemical Corporation Process for manufacture of pentaerythritol diphosphites
EP1846460A2 (en) 2004-01-21 2007-10-24 University Of Massachusetts Lowell Post-coupling synthetic approach for polymeric antioxidants
US7291669B2 (en) 2004-03-16 2007-11-06 Ciba Specialty Chemicals Corporation Stabilized polyolefin compositions
JP2008507276A (en) 2004-07-23 2008-03-13 ポルノクス コーポレーション Antioxidant macromonomer and antioxidant polymer, and method for producing and using the same
EP1776441A1 (en) 2004-08-18 2007-04-25 Ciba Specialty Chemicals Holding Inc. Lubricating oil compositions with improved performance
WO2006060801A2 (en) 2004-12-03 2006-06-08 Polnox Corporation Process for the synthesis of polyalkylphenol antioxidants
WO2006060802A1 (en) 2004-12-03 2006-06-08 Polnox Corporation Synthesis of sterically hindered phenol based macromolecular antioxidants
CA2589883A1 (en) 2004-12-03 2006-06-08 Polnox Corporation Synthesis of aniline and phenol-based antioxidant macromonomers and corresponding polymers
US20060128939A1 (en) 2004-12-03 2006-06-15 Vijayendra Kumar One pot process for making polymeric antioxidants
CA2598703A1 (en) 2005-02-22 2006-08-31 Polnox Corporation Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis , performances and applications
US7705185B2 (en) 2005-03-25 2010-04-27 Polnox Corporation Alkylated and polymeric macromolecular antioxidants and methods of making and using the same
US20070106059A1 (en) 2005-10-27 2007-05-10 Cholli Ashok L Macromolecular antioxidants and polymeric macromolecular antioxidants
EP1966293A1 (en) 2005-10-27 2008-09-10 Polnox Corporation Stabilized polyolefin compositions
US7705176B2 (en) 2005-10-27 2010-04-27 Polnox Corporation Macromolecular antioxidants based on sterically hindered phenols and phosphites
EP1963468A1 (en) 2005-12-02 2008-09-03 Polnox Corporation Lubricant oil compositions
US7767853B2 (en) 2006-10-20 2010-08-03 Polnox Corporation Antioxidants and methods of making and using the same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4447657A (en) * 1982-11-10 1984-05-08 Uop Inc. Preparation of ortho-alkylated phenols
EP0688805A1 (en) * 1994-06-24 1995-12-27 Mitsui Toatsu Chemicals, Incorporated Phenol aralkyl resins, preparation process thereof and epoxy resin compositions
US20030191242A1 (en) * 2000-02-22 2003-10-09 Alessandro Zedda Romp with oligomeric uv-absorbers
WO2003087260A1 (en) * 2002-04-05 2003-10-23 University Of Massachusetts Lowell Polymeric antioxidants

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
OVERGAAG M ET AL: "Rearrangement of alkyl phenyl ethers over dealuminated HY zeolites under liquid-phase conditions", APPLIED CATALYSIS A: GENERAL, ELSEVIER SCIENCE, AMSTERDAM, NL, vol. 175, no. 1-2, 14 December 1998 (1998-12-14), pages 139 - 146, XP004271571, ISSN: 0926-860X *

Also Published As

Publication number Publication date
CA2589855A1 (en) 2006-06-08
US7678877B2 (en) 2010-03-16
US20060128929A1 (en) 2006-06-15
WO2006060801A2 (en) 2006-06-08
EP1817393A2 (en) 2007-08-15

Similar Documents

Publication Publication Date Title
WO2006060801A3 (en) Process for the synthesis of polyalkylphenol antioxidants
WO2006060803A3 (en) One pot process for making polymeric antioxidants
EP1826221A4 (en) Method for producing norbornene based addition (co)polymer
EP1911770A4 (en) Method for producing polymer composition and polymer composition
TW200621646A (en) Bimetallic zinc complex and process of producing polycarbonate using the same as polymerization catalyst
WO2003033454A1 (en) Norbornene derivative and norbornene polymer obtained therefrom through ring-opening polymerization
AU2685401A (en) Synthesis method for polymers by controlled radical polymerisation with xanthates
WO2009005003A1 (en) Transition metal complex compound, olefin polymerization catalyst containing the compound, and method for producing olefin polymer performed in the presence of the catalyst
WO2006130675A3 (en) Compositions having hase rheology modifiers
TW200502265A (en) Method to produce UV-curable solventless acrylate-contact-adhesives
WO2006091705A3 (en) Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis , performances and applications
WO2010127319A3 (en) Organisms for the production of 1,3-butanediol
EP1739070A4 (en) Magnesium compound, catalyst for olefin polymerization and method for producing olefin polymer
TW200613427A (en) Block copolymer composition for asphalt modification, process for producing the same, and asphalt composition
WO2002057201A3 (en) Polymerizable higher diamondoid derivatives
WO2006004653A3 (en) Synthesis of nanofibers of polyaniline and substituted derivatives
TW200708530A (en) Polymer, film-forming composition comprising the polymer, insulating film formed by using the composition and electronic device
TW200516094A (en) Pi-Conjugated copolymer, production method thereof, and capacitor using the copolymer
AU2555200A (en) Alkoxyamines issues de nitroxides ss-phosphores
Yoshida Nitroxide-mediated photo-living radical polymerization of methyl methacrylate in solution
Yoshida Photo-living radical polymerization of methyl methacrylate by 2, 2, 6, 6-tetramethylpiperidine-1-oxyl in the presence of a photo-acid generator
CA2402890A1 (en) Method for producing polymers
EP1721912A4 (en) Process for producing polymer with functional end
TW200602806A (en) Radiation-sensitive resin composition, interlayer insulation film, microlens and process for producing them
WO2007070342A3 (en) Regioregular polymerization of alpha-olefins to produce polyethylene with a predominance of methyl substituents

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KM KN KP KR KZ LC LK LR LS LT LU LV LY MA MD MG MK MN MW MX MZ NA NG NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SM SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU LV MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2589855

Country of ref document: CA

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2005853056

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 2005853056

Country of ref document: EP