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  • 1.
    Andrén, Oliver C. J.
    et al.
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Ingverud, Tobias
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Hult, Daniel
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Håkansson, Joakim
    Bogestål, Yalda
    Caous, Josefin S.
    Blom, Kristina
    Zhang, Yuning
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Andersson, Therese
    Pedersen, Emma
    Björn, Camilla
    Löwenhielm, Peter
    Malkoch, Michael
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Antibiotic-Free Cationic Dendritic Hydrogels as Surgical-Site-Infection-Inhibiting Coatings2019Inngår i: Advanced Healthcare Materials, ISSN 2192-2640, E-ISSN 2192-2659, Vol. 8, nr 5Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Abstract A non-toxic hydrolytically fast-degradable antibacterial hydrogel is herein presented to preemptively treat surgical site infections during the first crucial 24 h period without relying on conventional antibiotics. The approach capitalizes on a two-component system that form antibacterial hydrogels within 1 min and consist of i) an amine functional linear-dendritic hybrid based on linear poly(ethylene glycol) and dendritic 2,2-bis(hydroxymethyl)propionic acid, and ii) a di-N-hydroxysuccinimide functional poly(ethylene glycol) cross-linker. Broad spectrum antibacterial effect is achieved by multivalent representation of catatonically charged ?-alanine on the dendritic periphery of the linear dendritic component. The hydrogels can be applied readily in an in vivo setting using a two-component syringe delivery system and the mechanical properties can accurately be tuned in the range equivalent to fat tissue and cartilage (G? = 0.5?8 kPa). The antibacterial effect is demonstrated both in vitro toward a range of relevant bacterial strains and in an in vivo mouse model of surgical site infection.

  • 2.
    Arseneault, Mathieu
    et al.
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Granskog, Viktor
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Khosravi, Sara
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Heckler, Ilona
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Antunez, Pablo Mesa
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Hult, Daniel
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Zhang, Yuning
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Malkoch, Michael
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    The Dawn of Thiol-Yne Triazine Triones Thermosets as a New Material Platform Suited for Hard Tissue Repair2018Inngår i: Advanced Materials, ISSN 0935-9648, E-ISSN 1521-4095, Vol. 30, nr 52, artikkel-id 1804966Artikkel i tidsskrift (Fagfellevurdert)
    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.

  • 3. Garcia Gallego, Sandra
    et al.
    Hult, Daniel
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Olsson, Johan V.
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Malkoch, Michael
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Fluoride-Promoted Esterification with Imidazolide-Activated Compounds: A Modular and Sustainable Approach to Dendrimers2015Inngår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 54, nr 8, s. 2416-2419Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Based on the growing demand for facile and sustainable synthetic methods to structurally perfect polymers, we herein describe a significant improvement of esterification reactions capitalizing on 1,1-carbonyldiimidazole (CDI). Cesium fluoride was shown to be an essential catalyst for these reactions to reach completion. This approach was successfully applied to the synthesis of structurally flawless and highly functional polyester dendrimers employing traditional and accelerated growth strategies. A sixth generation bis-MPA dendrimer with a molecular weight of 22.080Da and 192 peripheral hydroxy groups was isolated in less than one day of total reaction time. Large quantities of dendrimerswere obtained in high yields (>90%) using simple purification steps under sustainable conditions. The fluoride-promoted esterification (FPE) via imidazolide-activated compounds is wide in scope and constitutes a potentially new approach toward functional polymers and other materials.

  • 4.
    Hult, Daniel
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Versatile Synthetic Strategies to Highly Functional Polyesters and Polycarbonates2018Doktoravhandling, med artikler (Annet vitenskapelig)
    Abstract [en]

    Polymers have become ubiquitous in today’s society and are found in everything from household items to airplanes and automobiles. Synthetic polymeric materials are as diverse as their applications and their final properties are highly reliant on the building blocks and methods used to assemble them. In the field of biomedical materials, polyesters and polycarbonates have been hailed as excellent materials in large part due to their inherent hydrolytic degradability. With this in mind, careful choice of monomers can ensure that materials not only conform to the desired physical properties, but also elicit a favorable biological response. The utilization of post-polymerization modification of these promising materials has the capability of opening up further avenues to target even more advanced applications. Unfortunately, rigorous and difficult reaction conditions, including multi-step synthesis have to a certain extent held back the adoption of these complex functional materials in applied research. In a pragmatic approach, a sustainable framework was developed in this thesis to seek out more practical methods, limiting the amount of reaction steps and overtly hazardous chemicals.

    In a first study, we set out to simplify and scale-up the synthesis of cyclic carbonates with pendant functional groups, capable of undergoing controlled ring-opening polymerization. By avoiding the use of protective-group chemistry we were able two devise a two-step method to create a library of functional monomers. Results in this study show that reactive intermediates could be isolated on 100 g scales, which in a second step was functionalized with a desired alcohol.

    With this framework in mind, key practical decisions were made to drastically re-think the work up procedures for greater scalability of bis-MPA dendrimers. In this work, a more efficient, scalable and sustainable approach was devised. Elimination of traditional arduous purification steps led to the synthesis of monodisperse dendrimers up to the sixth generation, with 192 functional groups on 50 g scales. Further work included the omission of protective group-chemistry, using orthogonal functional groups to cut the number of synthetic steps by half.

    The know-how developed in the first two projects led us to pursue greater scalability of functional polycarbonates through a simpler polymerization technique. The method allowed the step-growth polymerization of functional materials from more easily accessible monomers isolated on 100 g scales. Subsequent polymerization afforded materials with glass transition temperatures in the range of -45 °C to 169 °C. The method served as a complement to cyclic carbonates, offering a wider range of functional monomers. Furthermore, by careful choice of assembly method, both alternating and scrambled compositions could be achieved.

    In a final study, we set out to take advantage of the scrambling mechanism. Control of the final composition of highly rigid degradable polycarbonates was pursued, using renewable building-blocks derived from sugar. In a proof of concept study, thermal and hydrolytic stability of these materials is shown to be dependent on both amount and configuration of each monomer in the final material.

  • 5.
    Hult, Daniel
    et al.
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Garcia-Gallego, Sandra
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Ingverud, Tobias
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Andrén, Oliver
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Malkoch, Michael
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Degradable High Tg Sugar Derived Polycarbonates from Isosorbide and Dihydroxyacetone2018Inngår i: Polymer Chemistry, ISSN 1759-9954, E-ISSN 1759-9962, Vol. 9, nr 17, s. 2238-2246Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Polycarbonates from isosorbide and dihydroxyacetone (DHA) have been synthesised using organocatalytic step-growth polymerization of their corresponding diols and bis-carbonylimidazolides monomers. By choice of feed ratio and monomer activation, either isosorbide or ketal protected DHA, random and alternating poly(Iso-co-DHA) carbonates have been formed. Thermal properties by DSC and TGA were herein strongly correlated to monomer composition. Dilution studies using 1H-NMR of a model compound DHA-diethyl carbonate in acetonitrile and deuterated water highlighted the influence of α-substituents on the keto/hydrate equilibrium of DHA. Further kinetics studies of in the pH* range of 4.7 to 9.6 serve to show the hydrolytic pH-profile of DHA-carbonates. The Hydrolytic degradation of deprotected polymer pellets show an increased degradation with increasing DHA content. Pellets with a random or alternating configuration show different characteristics in terms of mass loss and molecular weight loss profile over time.

  • 6.
    Lundberg, Pontus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknik, Ytbehandlingsteknik.
    Walter, Valérie Marie
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknik, Ytbehandlingsteknik.
    Montañez, Maria I.
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknik, Ytbehandlingsteknik.
    Hult, Daniel
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknik, Ytbehandlingsteknik.
    Hult, Anders
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknik, Ytbehandlingsteknik.
    Malkoch, Michael
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknik, Ytbehandlingsteknik.
    Linear dendritic polymeric amphiphiles with intrinsic biocompatibility: synthesis and characterization to fabrication of micelles and honeycomb membranes2011Inngår i: Polymer Chemistry, ISSN 1759-9954, Vol. 2, s. 394-402Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Linear dendritic hybrid materials enable a range of architectural variations which offers novel possibilities in the tailoring of polymeric materials. In this study dendrons based on the 2,2-bis(methylol)propionic acid (bis-MPA) building block, bearing click chemistry moieties in the core and peripheral hydroxyl functionalities, have been used as macroinitiators for ring opening polymerization of ε-caprolactone. A library of star branched polymers with poly(ε-caprolactone) chains was initially constructed using dendrons up to 4th generation. In a second step, the popular CuAAC or thiol–ene click reaction was efficiently used to attach poly(ethylene glycol) chains of different lengths to the core. Potential applications of the resulted amphiphilic linear dendritic hybrids were investigated. Both self-assembled micelles loaded with doxorubicin anticancer drug and ordered honeycomb membranes with enhanced surface area were successfully fabricated and characterized.

  • 7.
    Olsson, J. V.
    et al.
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Hult, Daniel
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Garcia-Gallego, Sandra
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Malkoch, Michael
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Fluoride-promoted carbonylation polymerization: A facile step-growth technique to polycarbonates2017Inngår i: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 8, nr 7, s. 4853-4857Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Fluoride-Promoted Carbonylation (FPC) polymerization is herein presented as a novel catalytic polymerization methodology that complements ROP and unlocks a greater synthetic window to advanced polycarbonates. The overall two-step strategy is facile, robust and capitalizes on the synthesis and step-growth polymerization of bis-carbonylimidazolide and diol monomers of 1,3- or higher configurations. Cesium fluoride (CsF) is identified as an efficient catalyst and the bis-carbonylimidazolide monomers are synthesized as bench-stable white solids, easily obtained on 50-100 g scales from their parent diols using cheap commercial 1,1′-carbonyldiimidazole (CDI) as activating reagent. The FPC polymerization works well in both solution and bulk, does not require any stoichiometric additives or complex settings and produces only imidazole as a relatively low-toxicity by-product. As a proof-of-concept using only four diol building-blocks, FPC methodology enabled the synthesis of a unique library of polycarbonates covering (i) rigid, flexible and reactive PC backbones, (ii) molecular weights 5-20 kg mol-1, (iii) dispersities of 1.3-2.9 and (iv) a wide span of glass transition temperatures, from -45 up to 169 °C.

  • 8.
    Olsson, Johan V.
    et al.
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Hult, Daniel
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi.
    Cai, Yanling
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi.
    Garcia-Gallego, Sandra
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi.
    Malkoch, Michael
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Reactive imidazole intermediates: simplified synthetic approach to functional aliphatic cyclic carbonates2014Inngår i: Polymer Chemistry, ISSN 1759-9954, E-ISSN 1759-9962, Vol. 5, nr 23, s. 6651-6655Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Reactive imidazole intermediates based on AB(2) and A(3) monomers, i.e. bis(methylol) propionic acid (bis-MPA) and trimethylolpropane (TMP) have successfully been synthesized and isolated on a 100 gram scale via a facile synthetic protocol using 1,1' -carbonyldiimidazole (CDI) as a key reagent. The robustness of the imidazole intermediates as bench stable precursors enabled the synthesis of a library of functional cyclic carbonates bearing relevant functionalities including hydrophilic PEGs, bioactive cholesterol and clickable groups. A number of functional polycarbonates were obtained by ring-opening polymerization, and their relevance in biomedical applications was highlighted by their low cytotoxicity on human dermal fibroblasts (hDF).

  • 9. Olsson, John V.
    et al.
    Hult, Daniel
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Malkoch, Michael
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Simplified and scalable synthetic methodology towards functional cyclic carbonate monomers and polymers2014Inngår i: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 248Artikkel i tidsskrift (Annet vitenskapelig)
  • 10.
    Torron, Susana
    et al.
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi.
    Hult, Daniel
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi.
    Pettersson, Torbjörn
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi.
    Johansson, Mats
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi.
    Tailoring Soft Polymer Networks Based on Sugars and Fatty Acids toward Pressure Sensitive Adhesive Applications2017Inngår i: ACS SUSTAINABLE CHEMISTRY & ENGINEERING, ISSN 2168-0485, Vol. 5, nr 3, s. 2632-2638Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The present work describes the synthesis and characterization of fully biobased soft polymer networks for pressure sensitive adhesives applications. The incorporation of different sugars into fatty-acid-based monomers, made it possible to tailor the viscoelastic properties of the materials. Lipase catalysis allowed to afford monomers with varying hydroxyl content and epoxy-functionalities. Step-growth polymerization catalyzed by DBU resulted in soft-polyester networks through combination of the monomers with a biobased diacid. Rheological and adhesion studies were performed to elucidate the different viscoelastic and adhesive properties of the materials as a function of their composition.

  • 11.
    Walter, Marie V.
    et al.
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknik, Ytbehandlingsteknik.
    Lundberg, Pontus
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknik.
    Hult, Daniel
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknik, Ytbehandlingsteknik.
    Hult, Anders
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknik, Ytbehandlingsteknik.
    Malkoch, Michael
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknik, Ytbehandlingsteknik.
    A one component methodology for the fabrication of honeycomb films from biocompatible amphiphilic block copolymer hybrids: a linear-dendritic-linear twist2013Inngår i: Polymer Chemistry, ISSN 1759-9954, Vol. 4, nr 9, s. 2680-2690Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The development of a facile method for the fabrication of breath figure (BF) films from hydrophobic polymers is gaining significant importance for their accessibility as templates in fields ranging from electronics and cell culturing to sensing and catalysis. By introducing polyester-based dendritic linkers, a library of micrometre sized honeycomb structures was successfully fabricated from amphiphilic linear-dendritic-linear hybrids comprising hydrophobic PCL or PLA and hydrophilic PEG blocks. From the array of produced films, the incorporation of a third generation dendritic linker was found to generate well-ordered honeycomb films in the several hundreds of micrometre range. This one component approach minimizes the number of unknown parameters and represents a fully reliable methodology for the fabrication of functional BFs from challenging and biocompatible polymers.

  • 12.
    Walter, Marie Valérie
    et al.
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Pontus, Lundberg
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Hult, Daniel
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Hult, Anders
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Malkoch, Michael
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
    Honeycomb films from amphiphilic linear-dendritic-linear hybrids: effect of branching and of the block lengthManuskript (preprint) (Annet vitenskapelig)
1 - 12 of 12
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