Hydrogen‐bonded supramolecular polymers as self‐healing hydrogels: Effect of a bulky adamantyl substituent in the ureido‐pyrimidinone monomer
Identifieur interne : 003D90 ( Main/Exploration ); précédent : 003D89; suivant : 003D91Hydrogen‐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 ] ; 2014-02-15.
Descripteurs français
- Pascal (Inist)
- Acrylamide dérivé copolymère, Acrylamide(N,N-diméthyl) copolymère, Adamantane dérivé, Assemblage supramoléculaire, Auto-cicatrisation, Biomatériau, Cicatrisation, Copolymérisation solution, Dérivé de la pyrimidine, Etude expérimentale, Extrusion, Gel physique, Hydrogel, Liaison hydrogène, Méthacrylate copolymère, Propriété rhéologique, Préparation, Relation structure propriété, Structure moléculaire, Structure supramoléculaire, Urées, Viscoélasticité.
- 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 N,N‐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. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 39932.
Url:
DOI: 10.1002/app.39932
Affiliations:
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Nicholson</name><affiliation wicri:level="1"><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemical Engineering, The University of Queensland, Queensland, 4072, St Lucia</wicri:regionArea><wicri:noRegion>St Lucia</wicri:noRegion></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Journal of Applied Polymer Science</title><title level="j" type="alt">JOURNAL OF APPLIED POLYMER SCIENCE</title><idno type="ISSN">0021-8995</idno><idno type="eISSN">1097-4628</idno><imprint><biblScope unit="vol">131</biblScope><biblScope unit="issue">4</biblScope><biblScope unit="page-count">13</biblScope><date type="published" when="2014-02-15">2014-02-15</date></imprint><idno type="ISSN">0021-8995</idno></series></biblStruct></sourceDesc><seriesStmt><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>Acrylamide dérivé copolymère</term><term>Acrylamide(N,N-diméthyl) copolymère</term><term>Adamantane dérivé</term><term>Assemblage supramoléculaire</term><term>Auto-cicatrisation</term><term>Biomatériau</term><term>Cicatrisation</term><term>Copolymérisation solution</term><term>Dérivé de la pyrimidine</term><term>Etude expérimentale</term><term>Extrusion</term><term>Gel physique</term><term>Hydrogel</term><term>Liaison hydrogène</term><term>Méthacrylate copolymère</term><term>Propriété rhéologique</term><term>Préparation</term><term>Relation structure propriété</term><term>Structure moléculaire</term><term>Structure supramoléculaire</term><term>Urées</term><term>Viscoélasticité</term></keywords><keywords scheme="Wicri" type="topic" xml:lang="fr"><term>Biomatériau</term></keywords></textClass></profileDesc></teiHeader><front><div type="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 N,N‐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. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 39932.</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></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. 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