Hydrogen-Bonded Supramolecular Polymers as Self-Healing Hydrogels: Effect of a Bulky Adamantyl Substituent in the Ureido-Pyrimidinone Monomer
Identifieur interne : 004185 ( Main/Merge ); précédent : 004184; suivant : 004186Hydrogen-Bonded Supramolecular Polymers as Self-Healing Hydrogels: Effect of a Bulky Adamantyl Substituent in the Ureido-Pyrimidinone Monomer
Auteurs : Traian V. Chirila [Australie] ; HUI HUI LEE [Australie] ; Mathieu Oddon [Australie, France] ; Marko M. L. Nieuwenhuizen [Pays-Bas] ; Idriss Blakey [Australie] ; Timothy M. Nicholson [Australie]Source :
- Journal of applied polymer science [ 0021-8995 ] ; 2014.
Descripteurs français
- Pascal (Inist)
- Liaison hydrogène, Gel physique, Cicatrisation, Hydrogel, Méthacrylate copolymère, Dérivé de la pyrimidine, Urées, Copolymérisation solution, Extrusion, Biomatériau, Structure supramoléculaire, Préparation, Structure moléculaire, Viscoélasticité, Relation structure propriété, Etude expérimentale, Acrylamide dérivé copolymère, Propriété rhéologique, Assemblage supramoléculaire, Acrylamide(N,N-diméthyl) copolymère, Adamantane dérivé, Auto-cicatrisation.
- Wicri :
- topic : Biomatériau.
English descriptors
- KwdEn :
- Acrylamide derivative copolymer, Biomaterial, Cicatrization, Experimental study, Extrusion, Hydrogel, Hydrogen bond, Methacrylate copolymer, Molecular structure, Physical gel, Preparation, Property structure relationship, Pyrimidine derivatives, Rheological properties, Solution copolymerization, Supramolecular structure, Ureas, Viscoelasticity.
Abstract
In an attempt to generate supramolecular assemblies able to function as self-healing hydrogels, a novel ureido-pyrimidinone (UPy) monomer, 2-(N'-methacryloyloxyethylureido)-6-(1-adamantyl)-4[1H]-pyrimidinone, was synthesized and then copolymerized with NN-dimethylacrylamide at four different feed compositions, using a solution of lithium chloride in N,N-dimethylacetamide as the polymerization medium. The assembling process in the resulting copolymers is based on crosslinking through the reversible quadruple hydrogen bonding between side-chain UPy modules. The adamantyl substituent was introduced in order to create a "hydrophobic pocket" that may protect the hydrogen bonds against the disruptive effect of water molecules. Upon hydration to equilibrium, all copolymers generated typical hydrogels when their concentration in the hydrated system was at least 15%. The small-deformation rheometry showed that all hydrated copolymers were hydrogels that maintained a solid-like behavior, and that their extrusion through a syringe needle did not affect significantly this behavior, suggesting a self-healing capacity in these materials. An application as injectable substitutes for the eye's vitreous humor was proposed.
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Nicholson</name><affiliation wicri:level="1"><inist:fA14 i1="08"><s1>School of Chemical Engineering, The University of Queensland</s1><s2>St Lucia, Queensland 4072</s2><s3>AUS</s3><sZ>6 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>St Lucia, Queensland 4072</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">INIST</idno><idno type="inist">14-0149801</idno><date when="2014">2014</date><idno type="stanalyst">PASCAL 14-0149801 INIST</idno><idno type="RBID">Pascal:14-0149801</idno><idno type="wicri:Area/PascalFrancis/Corpus">000402</idno><idno type="wicri:Area/PascalFrancis/Curation">005A60</idno><idno type="wicri:Area/PascalFrancis/Checkpoint">000261</idno><idno type="wicri:explorRef" wicri:stream="PascalFrancis" wicri:step="Checkpoint">000261</idno><idno type="wicri:doubleKey">0021-8995:2014:Chirila T:hydrogen:bonded:supramolecular</idno><idno type="wicri:Area/Main/Merge">004185</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a">Hydrogen-Bonded Supramolecular Polymers as Self-Healing Hydrogels: Effect of a Bulky Adamantyl Substituent in the Ureido-Pyrimidinone Monomer</title><author><name sortKey="Chirila, Traian V" sort="Chirila, Traian V" uniqKey="Chirila T" first="Traian V." last="Chirila">Traian V. Chirila</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Queensland Eye Institute</s1><s2>South Brisbane, Queensland 4101</s2><s3>AUS</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>Queensland Eye Institute</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Queensland University of Technology, Faculty of Science and Engineering</s1><s2>Brisbane, Queensland 4001</s2><s3>AUS</s3><sZ>1 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>Brisbane, Queensland 4001</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="03"><s1>The University of Queensland, Australian Institute for Bioengineering and Nanotechnology (AIBN)</s1><s2>St Lucia, Queensland 4072</s2><s3>AUS</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>St Lucia, Queensland 4072</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="04"><s1>The University of Queensland, Faculty of Health Sciences</s1><s2>Herston, Queensland 4006</s2><s3>AUS</s3><sZ>1 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>Herston, Queensland 4006</wicri:noRegion></affiliation></author><author><name sortKey="Hui Hui Lee" sort="Hui Hui Lee" uniqKey="Hui Hui Lee" last="Hui Hui Lee">HUI HUI LEE</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Queensland Eye Institute</s1><s2>South Brisbane, Queensland 4101</s2><s3>AUS</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>Queensland Eye Institute</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="03"><s1>The University of Queensland, Australian Institute for Bioengineering and Nanotechnology (AIBN)</s1><s2>St Lucia, Queensland 4072</s2><s3>AUS</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>St Lucia, Queensland 4072</wicri:noRegion></affiliation></author><author><name sortKey="Oddon, Mathieu" sort="Oddon, Mathieu" uniqKey="Oddon M" first="Mathieu" last="Oddon">Mathieu Oddon</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Queensland Eye Institute</s1><s2>South Brisbane, Queensland 4101</s2><s3>AUS</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>Queensland Eye Institute</wicri:noRegion></affiliation><affiliation wicri:level="4"><inist:fA14 i1="05"><s1>Ecole Supérieure d'Ingénieurs de Luminy (ESIL), Polytech Marseille, Aix-Marseille Université</s1><s2>13288 Marseille</s2><s3>FRA</s3><sZ>3 aut.</sZ></inist:fA14><country>France</country><wicri:noRegion>13288 Marseille</wicri:noRegion><placeName><settlement type="city">Marseille</settlement><region type="région" nuts="2">Provence-Alpes-Côte d'Azur</region><settlement type="city">Marseille</settlement></placeName><orgName type="university">Université d'Aix-Marseille</orgName></affiliation></author><author><name sortKey="Nieuwenhuizen, Marko M L" sort="Nieuwenhuizen, Marko M L" uniqKey="Nieuwenhuizen M" first="Marko M. L." last="Nieuwenhuizen">Marko M. L. Nieuwenhuizen</name><affiliation wicri:level="1"><inist:fA14 i1="06"><s1>Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology</s1><s2>5600 M B Eindhoven</s2><s3>NLD</s3><sZ>4 aut.</sZ></inist:fA14><country>Pays-Bas</country><wicri:noRegion>5600 M B Eindhoven</wicri:noRegion></affiliation></author><author><name sortKey="Blakey, Idriss" sort="Blakey, Idriss" uniqKey="Blakey I" first="Idriss" last="Blakey">Idriss Blakey</name><affiliation wicri:level="1"><inist:fA14 i1="03"><s1>The University of Queensland, Australian Institute for Bioengineering and Nanotechnology (AIBN)</s1><s2>St Lucia, Queensland 4072</s2><s3>AUS</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>St Lucia, Queensland 4072</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="07"><s1>Centre for Advanced Imaging (CAI), The University of Queensland</s1><s2>St Lucia, Queensland 4072</s2><s3>AUS</s3><sZ>5 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>St Lucia, Queensland 4072</wicri:noRegion></affiliation></author><author><name sortKey="Nicholson, Timothy M" sort="Nicholson, Timothy M" uniqKey="Nicholson T" first="Timothy M." last="Nicholson">Timothy M. Nicholson</name><affiliation wicri:level="1"><inist:fA14 i1="08"><s1>School of Chemical Engineering, The University of Queensland</s1><s2>St Lucia, Queensland 4072</s2><s3>AUS</s3><sZ>6 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>St Lucia, Queensland 4072</wicri:noRegion></affiliation></author></analytic><series><title level="j" type="main">Journal of applied polymer science</title><title level="j" type="abbreviated">J. appl. polym. sci.</title><idno type="ISSN">0021-8995</idno><imprint><date when="2014">2014</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">Journal of applied polymer science</title><title level="j" type="abbreviated">J. appl. polym. sci.</title><idno type="ISSN">0021-8995</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Acrylamide derivative copolymer</term><term>Biomaterial</term><term>Cicatrization</term><term>Experimental study</term><term>Extrusion</term><term>Hydrogel</term><term>Hydrogen bond</term><term>Methacrylate copolymer</term><term>Molecular structure</term><term>Physical gel</term><term>Preparation</term><term>Property structure relationship</term><term>Pyrimidine derivatives</term><term>Rheological properties</term><term>Solution copolymerization</term><term>Supramolecular structure</term><term>Ureas</term><term>Viscoelasticity</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Liaison hydrogène</term><term>Gel physique</term><term>Cicatrisation</term><term>Hydrogel</term><term>Méthacrylate copolymère</term><term>Dérivé de la pyrimidine</term><term>Urées</term><term>Copolymérisation solution</term><term>Extrusion</term><term>Biomatériau</term><term>Structure supramoléculaire</term><term>Préparation</term><term>Structure moléculaire</term><term>Viscoélasticité</term><term>Relation structure propriété</term><term>Etude expérimentale</term><term>Acrylamide dérivé copolymère</term><term>Propriété rhéologique</term><term>Assemblage supramoléculaire</term><term>Acrylamide(N,N-diméthyl) copolymère</term><term>Adamantane dérivé</term><term>Auto-cicatrisation</term></keywords><keywords scheme="Wicri" type="topic" xml:lang="fr"><term>Biomatériau</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">In an attempt to generate supramolecular assemblies able to function as self-healing hydrogels, a novel ureido-pyrimidinone (UPy) monomer, 2-(N'-methacryloyloxyethylureido)-6-(1-adamantyl)-4[1H]-pyrimidinone, was synthesized and then copolymerized with NN-dimethylacrylamide at four different feed compositions, using a solution of lithium chloride in N,N-dimethylacetamide as the polymerization medium. The assembling process in the resulting copolymers is based on crosslinking through the reversible quadruple hydrogen bonding between side-chain UPy modules. The adamantyl substituent was introduced in order to create a "hydrophobic pocket" that may protect the hydrogen bonds against the disruptive effect of water molecules. Upon hydration to equilibrium, all copolymers generated typical hydrogels when their concentration in the hydrated system was at least 15%. The small-deformation rheometry showed that all hydrated copolymers were hydrogels that maintained a solid-like behavior, and that their extrusion through a syringe needle did not affect significantly this behavior, suggesting a self-healing capacity in these materials. An application as injectable substitutes for the eye's vitreous humor was proposed.</div></front></TEI><affiliations><list><country><li>Australie</li><li>France</li><li>Pays-Bas</li></country><region><li>Provence-Alpes-Côte d'Azur</li></region><settlement><li>Marseille</li></settlement><orgName><li>Université d'Aix-Marseille</li></orgName></list><tree><country name="Australie"><noRegion><name sortKey="Chirila, Traian V" sort="Chirila, Traian V" uniqKey="Chirila T" first="Traian V." last="Chirila">Traian V. Chirila</name></noRegion><name sortKey="Blakey, Idriss" sort="Blakey, Idriss" uniqKey="Blakey I" first="Idriss" last="Blakey">Idriss Blakey</name><name sortKey="Blakey, Idriss" sort="Blakey, Idriss" uniqKey="Blakey I" first="Idriss" last="Blakey">Idriss Blakey</name><name sortKey="Chirila, Traian V" sort="Chirila, Traian V" uniqKey="Chirila T" first="Traian V." last="Chirila">Traian V. Chirila</name><name sortKey="Chirila, Traian V" sort="Chirila, Traian V" uniqKey="Chirila T" first="Traian V." last="Chirila">Traian V. Chirila</name><name sortKey="Chirila, Traian V" sort="Chirila, Traian V" uniqKey="Chirila T" first="Traian V." last="Chirila">Traian V. Chirila</name><name sortKey="Hui Hui Lee" sort="Hui Hui Lee" uniqKey="Hui Hui Lee" last="Hui Hui Lee">HUI HUI LEE</name><name sortKey="Hui Hui Lee" sort="Hui Hui Lee" uniqKey="Hui Hui Lee" last="Hui Hui Lee">HUI HUI LEE</name><name sortKey="Nicholson, Timothy M" sort="Nicholson, Timothy M" uniqKey="Nicholson T" first="Timothy M." last="Nicholson">Timothy M. Nicholson</name><name sortKey="Oddon, Mathieu" sort="Oddon, Mathieu" uniqKey="Oddon M" first="Mathieu" last="Oddon">Mathieu Oddon</name></country><country name="France"><region name="Provence-Alpes-Côte d'Azur"><name sortKey="Oddon, Mathieu" sort="Oddon, Mathieu" uniqKey="Oddon M" first="Mathieu" last="Oddon">Mathieu Oddon</name></region></country><country name="Pays-Bas"><noRegion><name sortKey="Nieuwenhuizen, Marko M L" sort="Nieuwenhuizen, Marko M L" uniqKey="Nieuwenhuizen M" first="Marko M. L." last="Nieuwenhuizen">Marko M. L. Nieuwenhuizen</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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