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  • 1.
    Arseneault, Mathieu
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
    Granskog, Viktor
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
    Khosravi, Sara
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
    Heckler, Ilona
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
    Antunez, Pablo Mesa
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
    Hult, Daniel
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
    Zhang, Yuning
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
    Malkoch, Michael
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
    The Dawn of Thiol-Yne Triazine Triones Thermosets as a New Material Platform Suited for Hard Tissue Repair2018In: Advanced Materials, ISSN 0935-9648, E-ISSN 1521-4095, Vol. 30, no 52, article id 1804966Article in journal (Refereed)
    Abstract [en]

    The identification of a unique set of advanced materials that can bear extraordinary loads for use in bone and tooth repair will inevitably unlock unlimited opportunities for clinical use. Herein, the design of high-performance thermosets is reported based on triazine-trione (TATO) monomers using light-initiated thiol-yne coupling (TYC) chemistry as a polymerization strategy. In comparison to traditional thiol-ene coupling (TEC) systems, TYC chemistry has yielded highly dense networks with unprecedented mechanical properties. The most promising system notes 4.6 GPa in flexural modulus and 160 MPa in flexural strength, an increase of 84% in modulus and 191% in strength when compared to the corresponding TATO system based on TEC chemistry. Remarkably, the mechanical properties exceed those of polylactide (PLA) and challenge poly(ether ether ketone) PEEK and today's methacrylate-based dental resin composites. All the materials display excellent biocompatibility, in vitro, and are successfully: i) molded into medical devices for fracture repair, and ii) used as bone adhesive for fracture fixation and as tooth fillers with the outstanding bond strength that outperform methacrylate systems used today in dental restoration application. Collectively, a new era of advanced TYC materials is unfolded that can fulfill the preconditions as bone fixating implants and for tooth restorations.

  • 2.
    Arseneault, Mathieu
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Granskog, Viktor
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Khosravi, Sara
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Heckler, Ilona
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Mesa-Antunez, Pablo
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Hult, Daniel
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Zhang, Yuning
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Malkoch, Michael
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Highly crosslinked triazine-trione materials for fracture fixation based on TEC and TYC chemistryManuscript (preprint) (Other academic)
  • 3.
    Granskog, Viktor
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Thiol-Ene/Yne Adhesives for Tissue Fixation2018Doctoral 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.

  • 4.
    Granskog, Viktor
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Andren, Oliver C. J.
    Cai, Yanling
    Gonzalez-Granillo, Marcela
    Fellander-Tsai, Li
    von Holst, Hans
    KTH, School of Technology and Health (STH), Health Systems Engineering, Ergonomics.
    Haldosen, Lars-Arne
    Malkoch, Michael
    Linear Dendritic Block Copolymers as Promising Biomaterials for the Manufacturing of Soft Tissue Adhesive Patches Using Visible Light Initiated Thiol-Ene Coupling Chemistry2015In: Advanced Functional Materials, ISSN 1616-301X, E-ISSN 1616-3028, Vol. 25, no 42, p. 6596-6605Article in journal (Refereed)
    Abstract [en]

    A library of dendritic-linear-dendritic (DLD) materials comprising linear poly(ethylene glycol) and hyperbranched dendritic blocks based on 2,2-bis(hydroxymethyl) propionic acid is successfully synthesized and post-functionalized with peripheral allyl groups. Reactive DLDs with pseudo-generations of 3 to 6 (G3-G6) are isolated in large scale allowing their thorough evaluation as important components for the development of biomedical adhesives. Due to their branched nature and inherent degradable ester-bonds, promising biomaterial resins are accomplished with suitable viscosity, eliminating the excessive use of co-solvents. By utilizing benign high-energy visible light initiated thiol-ene coupling chemistry, DLDs together with tris[2-(3-mercaptopropionyloxy) ethyl] isocyanurate and surgical mesh enable the fabrication of soft tissue adhesive patches (STAPs) within a total irradiation time of 30 s. The STAPs display the ability to create good adhesion to wet soft tissue and encouraging results in cytotoxicity tests. All crosslinked materials are also found to degrade after being stored in human blood plasma and phosphate buffered saline. The proposed benign methodology coupled with the promising features of the crosslinked materials is herein envisioned as a soft tissue adhesive with properties that do not exist in currently available tissue adhesives.

  • 5.
    Granskog, Viktor
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Garcia-Gallego, Sandra
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Zhang, Yuning
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Malkoch, Michael
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Adhesion-enhancing primer for high-performance bone adhesive2017In: Abstracts of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 253Article in journal (Other academic)
  • 6.
    Granskog, Viktor
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    García-Gallego, Sandra
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    von Kieseritzky, Johanna
    Department of Clinical Science and Education and the Department of Hand Surgery, Karolinska Institutet.
    Rosendahl, Jennifer
    RISE Research Institutes of Sweden, Bioscience and Materials–Medical Device Technology.
    Stenlund, Patrik
    RISE Research Institutes of Sweden, Bioscience and Materials–Medical Device Technology.
    Zhang, Yuning
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Petronis, Sarunas
    RISE Research Institutes of Sweden, Bioscience and Materials–Medical Device Technology.
    Lyvén, Benny
    RISE Research Institutes of Sweden, Bioscience and Materials–Medical Device Technology.
    Arner, Marianne
    Department of Clinical Science and Education and the Department of Hand Surgery, Karolinska Institutet.
    Håkansson, Joakim
    RISE Research Institutes of Sweden, Bioscience and Materials–Medical Device Technology.
    Malkoch, Michael
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    High-Performance Thiol–Ene Composites Unveil a New Era of Adhesives Suited for Bone Repair2018In: Advanced Functional Materials, ISSN 1616-301X, E-ISSN 1616-3028, Vol. 28, no 26, article id 1800372Article in journal (Refereed)
    Abstract [en]

    The use of adhesives for fracture fixation can revolutionize the surgical procedures toward more personalized bone repairs. However, there are still no commercially available adhesive solutions mainly due to the lack of biocompatibility, poor adhesive strength, or inadequate fixation protocols. Here, a surgically realizable adhesive system capitalizing on visible light thiol–ene coupling chemistry is presented. The adhesives are carefully designed and formulated from a novel class of chemical constituents influenced by dental resin composites and self-etch primers. Validation of the adhesive strengthis conducted on wet bone substrates and accomplished via fiber-reinforced adhesive patch (FRAP) methodology. The results unravel, for the first time, on the promise of a thiol–ene adhesive with an unprecedented shear bondstrength of 9.0 MPa and that surpasses, by 55%, the commercially available acrylate dental adhesive system Clearfil SE Bond of 5.8 MPa. Preclinical validation of FRAPs on rat femur fracture models details good adhesion to the bone throughout the healing process, and are found biocompatible not giving rise to any inflammatory response. Remarkably, the FRAPs are found to withstand loads up to 70 N for 1000 cycles on porcine metacarpal fractures outperforming clinically used K-wires and match metal plates and screw implants.

1 - 6 of 6
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