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Publications (10 of 11) Show all publications
Andrén, O. C. J., Ingverud, T., Hult, D., Håkansson, J., Bogestål, Y., Caous, J. S., . . . Malkoch, M. (2019). Antibiotic-Free Cationic Dendritic Hydrogels as Surgical-Site-Infection-Inhibiting Coatings. Advanced Healthcare Materials, 8(5)
Open this publication in new window or tab >>Antibiotic-Free Cationic Dendritic Hydrogels as Surgical-Site-Infection-Inhibiting Coatings
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2019 (English)In: Advanced Healthcare Materials, ISSN 2192-2640, E-ISSN 2192-2659, Vol. 8, no 5Article in journal (Refereed) Published
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.

Place, publisher, year, edition, pages
John Wiley & Sons, Ltd, 2019
Keywords
antibacterial, dendrimer, hydrogels, surgical-site infection
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-249169 (URN)10.1002/adhm.201801619 (DOI)000461575200014 ()2-s2.0-85061270456 (Scopus ID)
Note

QC 20190412

Available from: 2019-04-11 Created: 2019-04-11 Last updated: 2019-04-12Bibliographically approved
Arseneault, M., Granskog, V., Khosravi, S., Heckler, I., Antunez, P. M., Hult, D., . . . Malkoch, M. (2018). The Dawn of Thiol-Yne Triazine Triones Thermosets as a New Material Platform Suited for Hard Tissue Repair. Advanced Materials, 30(52), Article ID 1804966.
Open this publication in new window or tab >>The Dawn of Thiol-Yne Triazine Triones Thermosets as a New Material Platform Suited for Hard Tissue Repair
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2018 (English)In: Advanced Materials, ISSN 0935-9648, E-ISSN 1521-4095, Vol. 30, no 52, article id 1804966Article in journal (Refereed) Published
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.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2018
Keywords
biomedical applications, dental fillers, implants, polymeric materials, thiol-yne photochemistry
National Category
Other Engineering and Technologies
Identifiers
urn:nbn:se:kth:diva-240993 (URN)10.1002/adma.201804966 (DOI)000454124800004 ()30387212 (PubMedID)2-s2.0-85055928738 (Scopus ID)
Note

QC 20190110

Available from: 2019-01-10 Created: 2019-01-10 Last updated: 2019-04-09Bibliographically approved
Hult, D. (2018). Versatile Synthetic Strategies to Highly Functional Polyesters and Polycarbonates. (Doctoral dissertation). KTH Royal Institute of Technology
Open this publication in new window or tab >>Versatile Synthetic Strategies to Highly Functional Polyesters and Polycarbonates
2018 (English)Doctoral thesis, comprehensive summary (Other academic)
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.

Place, publisher, year, edition, pages
KTH Royal Institute of Technology, 2018. p. 60
Series
TRITA-CBH-FOU ; 2018:6
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-224754 (URN)978-91-7729-711-6 (ISBN)
Public defence
2018-04-13, Kollegiesalen, Brinellvägen 8, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

QC 20180322

Available from: 2018-03-22 Created: 2018-03-22 Last updated: 2018-03-22Bibliographically approved
Olsson, J. V., Hult, D., Garcia-Gallego, S. & Malkoch, M. (2017). Fluoride-promoted carbonylation polymerization: A facile step-growth technique to polycarbonates. Chemical Science, 8(7), 4853-4857
Open this publication in new window or tab >>Fluoride-promoted carbonylation polymerization: A facile step-growth technique to polycarbonates
2017 (English)In: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 8, no 7, p. 4853-4857Article in journal (Refereed) Published
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.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2017
Keywords
Carbonylation, Fluorine compounds, Glass transition, Monomers, Polycarbonates, Activating reagents, Building blockes, Carbonyldiimidazole, Catalytic polymerization, Efficient catalysts, Growth techniques, Proof of concept, Step-growth polymerizations, Polymerization
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-216581 (URN)10.1039/c6sc05582f (DOI)000404617300018 ()2-s2.0-85021739063 (Scopus ID)
Note

QC 20171101

Available from: 2017-11-01 Created: 2017-11-01 Last updated: 2018-03-22Bibliographically approved
Torron, S., Hult, D., Pettersson, T. & Johansson, M. (2017). Tailoring Soft Polymer Networks Based on Sugars and Fatty Acids toward Pressure Sensitive Adhesive Applications. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 5(3), 2632-2638
Open this publication in new window or tab >>Tailoring Soft Polymer Networks Based on Sugars and Fatty Acids toward Pressure Sensitive Adhesive Applications
2017 (English)In: ACS SUSTAINABLE CHEMISTRY & ENGINEERING, ISSN 2168-0485, Vol. 5, no 3, p. 2632-2638Article in journal (Refereed) Published
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.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2017
Keywords
Pressure sensitive adhesives, Soft polymer networks, Lipase catalysis, Fatty acids, Biobased, Vegetable oils, Sorbitol
National Category
Polymer Chemistry Polymer Technologies
Identifiers
urn:nbn:se:kth:diva-205478 (URN)10.1021/acssuschemeng.6b02978 (DOI)000395846900067 ()2-s2.0-85014509029 (Scopus ID)
Note

QC 20170510

Available from: 2017-05-10 Created: 2017-05-10 Last updated: 2017-11-10Bibliographically approved
Garcia Gallego, S., Hult, D., Olsson, J. V. & Malkoch, M. (2015). Fluoride-Promoted Esterification with Imidazolide-Activated Compounds: A Modular and Sustainable Approach to Dendrimers. Angewandte Chemie International Edition, 54(8), 2416-2419
Open this publication in new window or tab >>Fluoride-Promoted Esterification with Imidazolide-Activated Compounds: A Modular and Sustainable Approach to Dendrimers
2015 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 54, no 8, p. 2416-2419Article in journal (Refereed) Published
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.

Keywords
Accelerated synthesis, Esterification, Fluoride; Imidazole, Polyester dendrimers
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-161958 (URN)10.1002/anie.201411370 (DOI)000350100000019 ()25605503 (PubMedID)2-s2.0-84922800982 (Scopus ID)
Funder
Knut and Alice Wallenberg FoundationMarcus and Amalia Wallenberg FoundationSwedish Research Council, 2011-5358, 2010-435
Note

QC 20150408

Available from: 2015-04-08 Created: 2015-03-20 Last updated: 2018-03-22Bibliographically approved
Olsson, J. V., Hult, D., Cai, Y., Garcia-Gallego, S. & Malkoch, M. (2014). Reactive imidazole intermediates: simplified synthetic approach to functional aliphatic cyclic carbonates. Polymer Chemistry, 5(23), 6651-6655
Open this publication in new window or tab >>Reactive imidazole intermediates: simplified synthetic approach to functional aliphatic cyclic carbonates
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2014 (English)In: Polymer Chemistry, ISSN 1759-9954, E-ISSN 1759-9962, Vol. 5, no 23, p. 6651-6655Article in journal (Refereed) Published
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).

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2014
Keywords
Cyclic carbonates, Synthetic approach
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-157251 (URN)10.1039/c4py00911h (DOI)000344374500003 ()2-s2.0-84908471876 (Scopus ID)
Funder
Knut and Alice Wallenberg Foundation, 2012-0196Swedish Research Council, 2010-453
Note

QC 20141208

Available from: 2014-12-08 Created: 2014-12-08 Last updated: 2018-03-22Bibliographically approved
Olsson, J. V., Hult, D. & Malkoch, M. (2014). Simplified and scalable synthetic methodology towards functional cyclic carbonate monomers and polymers. Paper presented at 248th National Meeting of the American-Chemical-Society (ACS), AUG 10-14, 2014, San Francisco, CA. Abstract of Papers of the American Chemical Society, 248
Open this publication in new window or tab >>Simplified and scalable synthetic methodology towards functional cyclic carbonate monomers and polymers
2014 (English)In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 248Article in journal, Meeting abstract (Other academic) Published
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-162001 (URN)000349167404500 ()
Conference
248th National Meeting of the American-Chemical-Society (ACS), AUG 10-14, 2014, San Francisco, CA
Note

QC 20150327

Available from: 2015-03-27 Created: 2015-03-20 Last updated: 2017-12-04Bibliographically approved
Walter, M. V., Lundberg, P., Hult, D., Hult, A. & Malkoch, M. (2013). A one component methodology for the fabrication of honeycomb films from biocompatible amphiphilic block copolymer hybrids: a linear-dendritic-linear twist. Polymer Chemistry, 4(9), 2680-2690
Open this publication in new window or tab >>A one component methodology for the fabrication of honeycomb films from biocompatible amphiphilic block copolymer hybrids: a linear-dendritic-linear twist
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2013 (English)In: Polymer Chemistry, ISSN 1759-9954, Vol. 4, no 9, p. 2680-2690Article in journal (Refereed) Published
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.

Keywords
Porous Polymer-Films, Water-Assisted Formation, Breath Figures, Morphology Control, Microporous Films, Membranes, Patterns, Adhesion, Growth, Cells
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-119933 (URN)10.1039/C3PY00053B (DOI)000316965200007 ()2-s2.0-84875818911 (Scopus ID)
Funder
Swedish Research Council, 2011-4477 2010-453
Note

QC 20130514

Available from: 2013-03-26 Created: 2013-03-26 Last updated: 2013-05-14Bibliographically approved
Lundberg, P., Walter, V. M., Montañez, M. I., Hult, D., Hult, A. & Malkoch, M. (2011). Linear dendritic polymeric amphiphiles with intrinsic biocompatibility: synthesis and characterization to fabrication of micelles and honeycomb membranes. Polymer Chemistry, 2, 394-402
Open this publication in new window or tab >>Linear dendritic polymeric amphiphiles with intrinsic biocompatibility: synthesis and characterization to fabrication of micelles and honeycomb membranes
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2011 (English)In: Polymer Chemistry, ISSN 1759-9954, Vol. 2, p. 394-402Article in journal (Refereed) Published
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.

National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-26392 (URN)10.1039/C0PY00258E (DOI)000286327400019 ()2-s2.0-78751533187 (Scopus ID)
Funder
Swedish Research Council, 2009-3259Swedish Research Council, 2006-3617Knut and Alice Wallenberg Foundation
Note
QC 20101125Available from: 2010-11-25 Created: 2010-11-25 Last updated: 2013-03-27Bibliographically approved
Organisations
Identifiers
ORCID iD: ORCID iD iconorcid.org/0000-0001-7543-5322

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