WO2007001407A3 - Light activated shape memory co-polymers - Google Patents

Light activated shape memory co-polymers Download PDF

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Publication number
WO2007001407A3
WO2007001407A3 PCT/US2005/035956 US2005035956W WO2007001407A3 WO 2007001407 A3 WO2007001407 A3 WO 2007001407A3 US 2005035956 W US2005035956 W US 2005035956W WO 2007001407 A3 WO2007001407 A3 WO 2007001407A3
Authority
WO
WIPO (PCT)
Prior art keywords
photo
monomer
shape memory
reactive monomer
group
Prior art date
Application number
PCT/US2005/035956
Other languages
French (fr)
Other versions
WO2007001407A2 (en
Inventor
Tat Hung Tong
Emily Snyder
Original Assignee
Cornerstone Res Group Inc
Tat Hung Tong
Emily Snyder
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 Cornerstone Res Group Inc, Tat Hung Tong, Emily Snyder filed Critical Cornerstone Res Group Inc
Priority to EP05858220A priority Critical patent/EP1799771A2/en
Priority to JP2007535804A priority patent/JP2008516051A/en
Priority to US11/576,749 priority patent/US8754179B2/en
Publication of WO2007001407A2 publication Critical patent/WO2007001407A2/en
Publication of WO2007001407A3 publication Critical patent/WO2007001407A3/en

Links

Classifications

    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/303—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one or more carboxylic moieties in the chain
    • 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
    • C08G2280/00—Compositions for creating shape memory

Abstract

The present discovery uses monomers which contain reversible photo­crosslinkable groups in addition to primary polymerizable groups. The mechanical properties of these materials and the reversibility of the photo-activated shape memory effect demonstrate the effectiveness of using photo-irradiation to effect change in modulus and shape memory effect. In the preferred embodiment the reaction mixture includes a photo-reactive monomer comprising a photo reactive group and a polymerizable group; a second monomer, which is more preferably a mixture of monomers, which are acrylate based; a multi-functional crosslinking agent, preferably 1,6 hexanediol diacrylate (HDODA); an initiator, preferably a free radical initiator; and a fifth, optional, component which is a modifying polymer. The mixture of the second monomer, crosslinking agent, and initiator comprise the base polymer matrix into which the photo-reactive monomer is incorporated. The polymeriziable group of the photo reactive monomer allows the photo reactive monomer to polymerize with the base polymer matrix.
PCT/US2005/035956 2004-10-06 2005-10-06 Light activated shape memory co-polymers WO2007001407A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP05858220A EP1799771A2 (en) 2004-10-06 2005-10-06 Light activated shape memory co-polymers
JP2007535804A JP2008516051A (en) 2004-10-06 2005-10-06 Photoactivated shape memory copolymer
US11/576,749 US8754179B2 (en) 2004-10-06 2005-10-06 Light activated shape memory co-polymers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US61644704P 2004-10-06 2004-10-06
US60/616,447 2004-10-06

Publications (2)

Publication Number Publication Date
WO2007001407A2 WO2007001407A2 (en) 2007-01-04
WO2007001407A3 true WO2007001407A3 (en) 2007-04-19

Family

ID=37395864

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/035956 WO2007001407A2 (en) 2004-10-06 2005-10-06 Light activated shape memory co-polymers

Country Status (4)

Country Link
US (1) US8754179B2 (en)
EP (1) EP1799771A2 (en)
JP (1) JP2008516051A (en)
WO (1) WO2007001407A2 (en)

Cited By (2)

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US8877114B2 (en) 2010-11-11 2014-11-04 Spirit Aerosystems, Inc. Method for removing a SMP apparatus from a cured composite part
US8945455B2 (en) 2010-11-11 2015-02-03 Spirit Aerosystems, Inc. Reconfigurable shape memory polymer support tooling

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US20060194896A1 (en) * 2004-05-26 2006-08-31 Sun Benjamin J Low shrinkage dental material and method
WO2007070877A2 (en) * 2005-12-15 2007-06-21 Cornerstone Research Group, Inc. Shape memory epoxy copolymers
EP1871306A4 (en) 2005-04-01 2012-03-21 Univ Colorado A graft fixation device and method
US8597630B2 (en) * 2007-04-19 2013-12-03 University Of Massachusetts Thermal-responsive polymer networks, compositions, and methods and applications related thereto
US8710166B2 (en) * 2008-05-30 2014-04-29 Cornerstone Research Group, Inc. Shape memory polymers formed by self-crosslinking of copolymers
US8937301B2 (en) * 2008-11-24 2015-01-20 Basf Se Photocurable polymeric dielectrics containing 6-substituted coumarin moieties and methods of preparation and use thereof
CN101747486B (en) * 2009-12-24 2011-09-28 浙江大学 Light-induced shape-memory polymer and preparation method thereof
FR2958778B1 (en) * 2010-04-07 2012-05-11 Centre Nat Rech Scient RECOVERY MEDIUM REVERSIBLE BY OPTICAL INFORMATION STORAGE, REVERSIBLE RECORDING METHOD ON SUCH A MEDIUM.
GB201015566D0 (en) * 2010-09-17 2010-10-27 Rolls Royce Plc A flexible tool
WO2012061702A1 (en) * 2010-11-04 2012-05-10 The Regents Of The University Of Colorado, A Body Corporate Dual-cure polymer systems
US8734703B2 (en) 2010-11-11 2014-05-27 Spirit Aerosystems, Inc. Methods and systems for fabricating composite parts using a SMP apparatus as a rigid lay-up tool and bladder
US8815145B2 (en) 2010-11-11 2014-08-26 Spirit Aerosystems, Inc. Methods and systems for fabricating composite stiffeners with a rigid/malleable SMP apparatus
US8668981B2 (en) * 2010-11-11 2014-03-11 Spirit Aerosystems, Inc. High temperature shape memory polymer via reactive extrusion
CN102153856B (en) * 2011-02-24 2014-02-12 中山大学 Photo-induced reversible self-repair polyurethane film and repair method
JP5961192B2 (en) * 2011-03-07 2016-08-02 ザ・リージェンツ・オブ・ザ・ユニバーシティ・オブ・コロラド・ア・ボディ・コーポレイトＴｈｅ Ｒｅｇｅｎｔｓ Ｏｆ Ｔｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｃｏｌｏｒａｄｏ Ａ Ｂｏｄｙ Ｃｏｒｐｏｒａｔｅ Shape memory polymer intraocular lens
US9427493B2 (en) 2011-03-07 2016-08-30 The Regents Of The University Of Colorado Shape memory polymer intraocular lenses
CN102787447B (en) * 2011-05-20 2014-12-10 中国科学院化学研究所 Shape memory material with fiber structure and preparation method of shape memory material
CN102276954B (en) * 2011-05-28 2012-12-19 河南工业大学 Shape memory polymer based on N-vinyl caprolactam and citric acid and preparation method thereof
US9665339B2 (en) * 2011-12-28 2017-05-30 Sonos, Inc. Methods and systems to select an audio track
US9527947B2 (en) 2012-10-11 2016-12-27 The Hong Kong Polytechnic University Semi-crystalline shape memory polymer and production method thereof
US10532125B1 (en) 2013-06-27 2020-01-14 Vanderbilt University Shape memory polymers and methods of use
ES2527229B1 (en) * 2013-07-19 2015-11-06 Universitat Politècnica De Catalunya METHOD FOR THE PREPARATION OF A POLYMER WITH FORM MEMORY FOR APPLICATION IN DENTAL ORTHODONTIC AND POLYMER ARCHES FOR DENTAL ORTHODONTIC ARCHES
US9340636B2 (en) 2013-07-26 2016-05-17 The Regents Of The University Of Colorado, A Body Corporate Thiol-containing dual cure polymers and methods using same
US9700492B2 (en) 2014-03-07 2017-07-11 The Regents Of The University Of Colorado, A Body Corporate Dental composites systems and methods of making the same and using same
JP2017526907A (en) 2014-07-10 2017-09-14 スミス アンド ネフュー ピーエルシーＳｍｉｔｈ ＆ Ｎｅｐｈｅｗ Ｐｕｂｌｉｃ Ｌｉｍｉｔｅｄ Ｃｏｍｐａｎｙ Improvements in and related to devices
JP6474814B2 (en) * 2014-08-08 2019-02-27 株式会社ダイセル Epoxy resin molding having a special shape and optical device including the same
CN104772761A (en) * 2015-03-27 2015-07-15 浙江大学 Manipulator device driven on basis of photo-induced shape memory polymers and method thereof
KR101676564B1 (en) 2015-04-24 2016-11-17 서울대학교산학협력단 Sequential joint behavior sheet using photo-deformation and folding and unfolding control method the same
GB201600746D0 (en) 2016-01-14 2016-03-02 Smith & Nephew Improvements in and relating to polymer materials
GB201600747D0 (en) 2016-01-14 2016-03-02 Smith & Nephew Improvements in and relating to devices
US10451195B2 (en) 2016-10-25 2019-10-22 International Business Machines Corporation Hose with tunable flexibility using cyclizable, photochromic molecules
EP3363793A1 (en) 2017-02-15 2018-08-22 Merck Patent GmbH Hydrophobic compounds for optically active devices
EP3492457A1 (en) * 2017-12-01 2019-06-05 Fundacion Gaiker Coumarin derivatives, and polyols and polyurethanes containing them
CN110003395A (en) * 2019-04-23 2019-07-12 深圳大学 Shape-memory material and its preparation method and application
CN110669188B (en) * 2019-10-21 2020-10-13 南京林业大学 Waterborne polyurethane coating capable of self-repairing through ultraviolet light and preparation method thereof
US20230273455A1 (en) 2020-07-15 2023-08-31 Johnson & Johnson Surgical Vision, Inc. Optically active devices
CN113181437B (en) * 2021-03-16 2022-09-23 浙江大学 Customizable polymer intravascular stent and preparation method thereof

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8877114B2 (en) 2010-11-11 2014-11-04 Spirit Aerosystems, Inc. Method for removing a SMP apparatus from a cured composite part
US8945325B2 (en) 2010-11-11 2015-02-03 Spirit AreoSystems, Inc. Methods and systems for forming integral composite parts with a SMP apparatus
US8945455B2 (en) 2010-11-11 2015-02-03 Spirit Aerosystems, Inc. Reconfigurable shape memory polymer support tooling
US8951375B2 (en) 2010-11-11 2015-02-10 Spirit Aerosystems, Inc. Methods and systems for co-bonding or co-curing composite parts using a rigid/malleable SMP apparatus
US8974217B2 (en) 2010-11-11 2015-03-10 Spirit Aerosystems, Inc. Reconfigurable shape memory polymer tooling supports

Also Published As

Publication number Publication date
JP2008516051A (en) 2008-05-15
EP1799771A2 (en) 2007-06-27
WO2007001407A2 (en) 2007-01-04
US20080021166A1 (en) 2008-01-24
US8754179B2 (en) 2014-06-17

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