WO2006014605A3 - Anti-oxidant macromonomers and polymers and methods of making and using the same - Google Patents

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

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Publication number
WO2006014605A3
WO2006014605A3 PCT/US2005/025513 US2005025513W WO2006014605A3 WO 2006014605 A3 WO2006014605 A3 WO 2006014605A3 US 2005025513 W US2005025513 W US 2005025513W WO 2006014605 A3 WO2006014605 A3 WO 2006014605A3
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WO
WIPO (PCT)
Prior art keywords
antioxidant
methods
macromonomer
same
macromonomers
Prior art date
Application number
PCT/US2005/025513
Other languages
French (fr)
Other versions
WO2006014605A2 (en
Inventor
Ashok L Cholli
Original Assignee
Polnox Corp
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, Ashok L Cholli filed Critical Polnox Corp
Priority to EP05772822A priority Critical patent/EP1771530B1/en
Priority to DE602005016559T priority patent/DE602005016559D1/en
Priority to JP2007522638A priority patent/JP2008507276A/en
Priority to AU2005269780A priority patent/AU2005269780A1/en
Priority to CA002574581A priority patent/CA2574581A1/en
Priority to AT05772822T priority patent/ATE442426T1/en
Publication of WO2006014605A2 publication Critical patent/WO2006014605A2/en
Publication of WO2006014605A3 publication Critical patent/WO2006014605A3/en

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    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
    • C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F112/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F112/02—Monomers containing only one unsaturated aliphatic radical
    • C08F112/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F112/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F112/22—Oxygen
    • C08F112/24—Phenols or alcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F12/22—Oxygen
    • C08F12/24—Phenols or alcohols
    • 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
    • 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
    • C08G61/025—Polyxylylenes
    • 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
    • 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
    • C09K15/12—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen
    • 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
    • C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
    • 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
    • C09K15/28—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen, oxygen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/22—Preparation of oxygen-containing organic compounds containing a hydroxy group aromatic
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
    • C12P7/26—Ketones
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/62—Carboxylic acid esters
    • 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
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/142—Side-chains containing oxygen
    • C08G2261/1422—Side-chains containing oxygen containing OH groups
    • 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
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/142—Side-chains containing oxygen
    • C08G2261/1424—Side-chains containing oxygen containing ether groups, including alkoxy
    • C—CHEMISTRY; METALLURGY
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/142—Side-chains containing oxygen
    • C08G2261/1426—Side-chains containing oxygen containing carboxy groups (COOH) and/or -C(=O)O-moieties
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/148—Side-chains having aromatic units
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    • 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
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    • C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
    • C08G2261/342—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3424—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms non-conjugated, e.g. paracyclophanes or xylenes
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    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
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  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
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  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Cosmetics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Wrappers (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)

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.
PCT/US2005/025513 2004-07-23 2005-07-19 Anti-oxidant macromonomers and polymers and methods of making and using the same WO2006014605A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP05772822A EP1771530B1 (en) 2004-07-23 2005-07-19 Anti-oxidant macromonomers and polymers and methods of making and using the same
DE602005016559T DE602005016559D1 (en) 2004-07-23 2005-07-19 ANTIOXIDATIVE MACROMONOMERS, THEIR PREPARATION AND USE
JP2007522638A JP2008507276A (en) 2004-07-23 2005-07-19 Antioxidant macromonomer and antioxidant polymer, and method for producing and using the same
AU2005269780A AU2005269780A1 (en) 2004-07-23 2005-07-19 Anti-oxidant macromonomers and polymers and methods of making and using the same
CA002574581A CA2574581A1 (en) 2004-07-23 2005-07-19 Anti-oxidant macromonomers and polymers and methods of making and using the same
AT05772822T ATE442426T1 (en) 2004-07-23 2005-07-19 ANTIOXIDANT MACROMONOMERS, THEIR PREPARATION AND USE

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US59057504P 2004-07-23 2004-07-23
US59064604P 2004-07-23 2004-07-23
US60/590,575 2004-07-23
US60/590,646 2004-07-23

Publications (2)

Publication Number Publication Date
WO2006014605A2 WO2006014605A2 (en) 2006-02-09
WO2006014605A3 true WO2006014605A3 (en) 2006-05-04

Family

ID=35457401

Family Applications (2)

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PCT/US2005/025513 WO2006014605A2 (en) 2004-07-23 2005-07-19 Anti-oxidant macromonomers and polymers and methods of making and using the same
PCT/US2005/025646 WO2006014674A2 (en) 2004-07-23 2005-07-19 Anti-oxidant macromonomers and polymers and methods of making and using the same

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PCT/US2005/025646 WO2006014674A2 (en) 2004-07-23 2005-07-19 Anti-oxidant macromonomers and polymers and methods of making and using the same

Country Status (8)

Country Link
US (3) US20060041087A1 (en)
EP (2) EP1771530B1 (en)
JP (2) JP2008507613A (en)
AT (1) ATE442426T1 (en)
AU (3) AU2005269754A1 (en)
CA (2) CA2574588A1 (en)
DE (1) DE602005016559D1 (en)
WO (2) WO2006014605A2 (en)

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US7323511B2 (en) * 2004-01-21 2008-01-29 University Of Massachusetts Lowell Post-coupling synthetic approach for polymeric antioxidants
US20060041087A1 (en) * 2004-07-23 2006-02-23 Cholli Ashok L Anti-oxidant macromonomers and polymers and methods of making and using the same
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CA2589883A1 (en) 2004-12-03 2006-06-08 Polnox Corporation Synthesis of aniline and phenol-based antioxidant macromonomers and corresponding polymers
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EP1861484A2 (en) 2005-02-22 2007-12-05 Polnox Corporation Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis , performances and applications
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US7767853B2 (en) 2006-10-20 2010-08-03 Polnox Corporation Antioxidants and methods of making and using the same
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US9808675B2 (en) 2012-09-13 2017-11-07 Acushnet Company Golf ball compositions
EP3071544B1 (en) 2013-11-22 2022-07-06 Polnox Corporation Macromolecular antioxidants based on dual type moiety per molecule: structures methods of making and using the same
KR101781509B1 (en) 2016-05-19 2017-09-26 한국화학연구원 Polyamide based polymer compositions comprising hyperbranched polymer having enhanced flowability and preparation method thereof
KR101815577B1 (en) 2016-11-18 2018-01-05 한국화학연구원 Polyamide based polymer compositions comprising hyperbranched polyamide having enhanced flowability and preparation method thereof
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
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CN109279800A (en) * 2018-11-19 2019-01-29 河海大学 A kind of reinforcing steel bar corrosion inhibitor and preparation method and application based on radish extracting solution
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EP1771530B1 (en) 2009-09-09
US7923587B2 (en) 2011-04-12
DE602005016559D1 (en) 2009-10-22
AU2005269780A1 (en) 2006-02-09
ATE442426T1 (en) 2009-09-15
WO2006014674A2 (en) 2006-02-09
JP2008507613A (en) 2008-03-13
CA2574588A1 (en) 2006-02-09
WO2006014674A3 (en) 2006-04-20
JP2008507276A (en) 2008-03-13

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