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Highly crosslinked triazine-trione materials for fracture fixation based on TEC and TYC chemistry
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.ORCID iD: 0000-0001-8595-0037
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
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(English)Manuscript (preprint) (Other academic)
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-227152OAI: oai:DiVA.org:kth-227152DiVA, id: diva2:1203211
Funder
Knut and Alice Wallenberg Foundation, 2012-0196
Note

QC 20180517

Available from: 2018-05-02 Created: 2018-05-02 Last updated: 2018-05-17Bibliographically approved
In thesis
1. Thiol-Ene/Yne Adhesives for Tissue Fixation
Open this publication in new window or tab >>Thiol-Ene/Yne Adhesives for Tissue Fixation
2018 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The utilization of adhesives in surgery has not reached its full potential and research in the field is encouraged by the surgeons’ desire for improved alternatives to today’s tissue fixation strategies. Here, adhesive resins based on thiol-ene coupling (TEC) chemistry or thiol-yne coupling (TYC) chemistry are exploited to develop tissue adhesives that cure fast and on-demand via photoinitiation. In order to make safer adhesives, macromolecular components and systems with high conversion of functional groups were developed to minimize leakage of unreacted monomers.To develop macromolecular resin components, allyl-functional dendritic-linear-dendritic (DLD) co-polymers were synthesized with a poly(ethylene glycol) (PEG) core chain and hyperbranched structures of 2,2-bis(hydroxymethyl) propionic acid (bis-MPA) to capitalize on the rheological properties of dendritic structures. The dendritic structures interfered with the crystallization of the PEG segment and the DLD’s liquid appearance enabled their use as macromolecular components without solvent. The DLDs were cured with a thiol crosslinker and the strategy disclosed degradable soft tissue adhesives with good adhesion to wet porcine skin.Mussel inspired dopamine derivatives was evaluated as adhesion-enhancing primers for bone adhesives. The addition of NaOH to the primer solutions increased the shear bond strengths of the adhesive to bone. The highest bond strengths with the tested dopamine derivatives were obtained when a combination of thiol and ene-functional derivatives were used.With inspiration from dental resin adhesives, a fully TEC based adhesive system was developed with excellent shear bond strength to wet bone substrates. The adhesive system enabled superior fixation of phalangeal fracture models compared to the daily used Kirschner wires and could even compete with a screw fixated metal plate. The adhesive materials proved biocompatible in initial in vitro and in vivo studies.Strong and rigid materials for fracture fixation were developed via a strategy of using highly crosslinked triazine-trione monomers and TEC or TYC chemistry. The development resulted in TYC resin based materials with mechanical properties that very well can compete with poly(ether ether ketone) (PEEK) that is used in biomedical load bearing applications due to its high strength, toughness and inertness.

Abstract [sv]

Användningen av lim inom kirurgin har ännu inte nått sin fulla potential och kirurgernas önskan om förbättrade alternativ till dagens metoder för vävnadsfixering uppmuntrar till forskning inom området. I det här arbetet har reaktioner mellan tiolgrupper och kol-kol dubbel- (TEC) eller trippelbindningar (TYC) använts för att utveckla vävnadslim som härdar snabbt via fotoinitiering. För att göra säkra lim har makromolekylära limkomponenter och system med hög omsättning av funktionella grupper utvecklats för att minimera läckage av oreagerade monomerer.För att utveckla makromolekylära limkomponenter som utnyttjar de reologiska egenskaperna från dendritiska strukturer, syntetiserades allylfunktionella dendritisk-linjär-dendritiska (DLD) sampolymerer med ett mittsegment av poly (etylenglykol) (PEG) och hyperförgrenade strukturer av 2,2-bis (hydroximetyl) propionsyra syra (bis-MPA). De dendritiska strukturerna hindrade kristallisationen av PEG-segmentet och flytande polymerer erhölls som kunde användas som limkomponenter utan lösningsmedel. DLD komponenterna härdade snabbt med hjälp av en tioltvärbindare, vilket resulterade i nedbrytbara lim för mjuk vävnad med god vidhäftning mot fuktig grishud.Musselinspirerade dopaminderivat utvärderades som adhesionsförhöjande primers för benlim. Genom att tillsätta NaOH i pirmerlösningarna ökade bindningsstyrkan för benlimmet. De högsta bindningsstyrkorna med hjälp av dopaminederivaten erhölls när tiolderivat och derivat med dubbelbindningar användes tillsammans.Med inspiration från dentallim utvecklades ett helt TEC baserat limsystem med utmärkt adhesion till våta bensubstrat. Limsystemet möjliggjorde fixering av falangfraktursmodeller som presterade bättre än fixeringar med Kirschnerstift som används dagligen för frakturfixering. Dessutom kunde limmet även konkurrera med en skruvfixerad metallplatta. Limmaterialet visade sig vara biokompatibelt vid initiala in vitro och in vivo studier.För att göra starka och styva material för frakturfixeringar utvecklades tätt tvärbundna material baserade på triazin-trion (TATO) monomerer via TEC eller TYC-kemi. Utvecklingen resulterade i material med mekaniska egenskaper som mycket väl kan konkurrera med poly(etereterketon) (PEEK) som används i lastbärande biomedicinska applikationer på grund av sin goda hållfasthet och stabilitet i fysiologisk miljö.

Place, publisher, year, edition, pages
KTH Royal Institute of Technology, 2018. p. 64
Series
TRITA-CBH-FOU ; 2018:17
National Category
Polymer Chemistry
Research subject
Fibre and Polymer Science
Identifiers
urn:nbn:se:kth:diva-227154 (URN)978-91-7729-784-0 (ISBN)
Public defence
2018-06-08, K1, Teknikringen 46, Stockholm, 10:00 (English)
Opponent
Supervisors
Funder
Knut and Alice Wallenberg Foundation, 2012-0196VINNOVA, 2014-03777
Note

QC 20180517

Available from: 2018-05-17 Created: 2018-05-16 Last updated: 2018-05-17Bibliographically approved

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