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  • 1.
    Hua, Geng
    et al.
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Franzén, Johan
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi.
    Odelius, Karin
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi, Polymerteknologi.
    Phosphazene-Catalyzed Regioselective Ring-Opening Polymerization of rac-1-Methyl Trimethylene Carbonate: Colder and Less is Better2019Inngår i: Macromolecules, ISSN 0024-9297, E-ISSN 1520-5835, Vol. 52, nr 7, s. 2681-2690Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The regioselective organocatalytic ring-opening polymerization (ROP) of a 6-membered cyclic carbonate, rac-1-methyl trimethylene carbonate, was studied using phosphazene base (t-BuP2) as the principle catalyst. The influence on the reaction kinetics caused by the reaction temperature (-74-60 degrees C), catalyst loading (0.5-2.5%), and reaction solvent (toluene and tetrahydrofuran) was systematically tuned and followed by H-1 NMR. All studied reactions reached close to or above 90% monomer conversion in 3 h, and all exhibited typical equilibrium polymerization behavior that is inherent to 6-membered cyclic carbonates. Good control over the molecular weight and distribution of the polycarbonate product was obtained in most studied conditions, with M-n ranging from similar to 4k to similar to 20k and D < 1.2. The regioregularity (X-reg) of the resulting polycarbonate was thoroughly studied using various NMR techniques, with the highest X-reg obtained being.0.90. The major influence from the reaction conditions on both the ROP kinetics and X-reg are as follows: higher reaction temperature resulted in a decrease of both; higher catalyst loading resulted in a faster ROP reaction but a slight decrease in X-reg; and toluene being a better solvent resulted in both faster reaction and higher X-reg. Throughout this study, we have demonstrated the possibility to synthesize regioregular aliphatic polycarbonate using an organic base as the ROP catalyst, contrary to the existing studies on similar systems where only metal-base catalysts were in focus and our systems showed similar high X-reg of the product.

  • 2.
    Hua, Geng
    et al.
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Polymerteknologi.
    Johan, Franzén
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Odelius, Karin
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Polymerteknologi.
    One-pot inimer promoted ROCP synthesis of branched copolyesters using α-hydroxy-γ-butyrolactone as the branching reagent2016Inngår i: Journal of Polymer Science Part A: Polymer Chemistry, ISSN 0887-624X, E-ISSN 1099-0518, Vol. 54, nr 13, s. 1908-1918Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    An array of branched poly(ɛ-caprolactone)s was successfully synthesized using an one-pot inimer promoted ring-opening multibranching copolymerization (ROCP) reaction. The biorenewable, commercially available yet unexploited comonomer and initiator 2-hydroxy-γ-butyrolactone was chosen as the inimer to extend the use of 5-membered lactones to branched structures and simultaneously avoiding the typical tedious work involved in the inimer preparation. Reactions were carried out both in bulk and in solution using stannous octoate (Sn(Oct)2) as the catalyst. Polymerizations with inimer equivalents varying from 0.01 to 0.2 were conducted which resulted in polymers with a degree of branching ranging from 0.049 to 0.124. Detailed ROCP kinetics of different inimer systems were compared to illustrate the branch formation mechanism. The resulting polymer structures were confirmed by 1H, 13C, and 1H-13C HSQC NMR and SEC (RI detector and triple detectors). The thermal properties of polymers with different degree of branching were investigated by DSC, confirming the branch formation. Through this work, we have extended the current use of the non-homopolymerizable γ-butyrolactone to the branched polymers and thoroughly examined its behaviors in ROCP.

  • 3.
    Hua, Geng
    et al.
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Polymerteknologi.
    Odelius, Karin
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Polymerteknologi.
    Exploiting Ring-Opening Aminolysis–Condensation as a Polymerization Pathway to Structurally Diverse Biobased Polyamides2018Inngår i: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A pathway to biobased polyamides (PAs) via ring-opening aminolysis–condensation (ROAC) under benign conditions with diverse structure was designed. Ethylene brassylate (EB), a plant oil-derived cyclic dilactone, was used in combination with an array of diamines of diverse chemical structure, and ring-opening of the cyclic dilactone EB was revealed as a driving force for the reaction. The ROAC reactions were adjusted, and reaction conditions of 100 °C under atmospheric pressure using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as a catalyst for 24 h were optimal. The structures of the polyamides were confirmed by mass spectroscopy, FTIR, and NMR, and the PAs had viscosity average molecular weights (Mη) of ∼5–8 kDa. Glassy or semicrystalline PAs with glass transition temperatures between 48 and 55 °C, melting temperatures of 120–200 °C for the semicrystalline PAs, and thermal stabilities above 400 °C were obtained and were comparable to the existing PAs with similar structures. As a proof-of-concept of their usage, one of the PAs was shown to form fibers by electrospinning and films by melt pressing. Compared to conventional methods for PA synthesis, the ROAC route portrayed a reaction temperature at least 60–80 °C lower, could be readily carried out without a low-pressure environment, and eliminated the use of solvents and toxic chemicals. Together with the plant oil-derived monomer (EB), the ROAC route provided a sustainable alternative to design biobased PAs.

  • 4.
    Hua, Geng
    et al.
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Polymerteknologi.
    Odelius, Karin
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Polymerteknologi.
    From Food Additive to High-Performance Heavy Metal Adsorbent: A Versatile and Well-Tuned Design2016Inngår i: ACS Sustainable Chemistry & Engineering, ISSN 2168-0485Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A biosourced, cross-linked hydrogel-type heavy metal adsorbent is presented. Various factors such as the highly efficient chemical interactions, the various network structures, the decreased energy consumption during cross-linking, and the negligible amount of generated waste are considered when designing the adsorbent. The widely applied, naturally occurring food additive δ-gluconolactone is studied as a building block for the adsorbent. Aminolysis reactions were applied to form linear dimer precursors between diamines and δ-gluconolactones. The abundant hydroxyl groups on the dimers from δ-gluconolactone were fully exploited by using them as the cross-linking sites for reactions with ethylenediaminetetraacetic dianhydride, a well-known metal-chelating moiety. The versatility of the adsorbent and its metal-ion binding capacity is well tuned using dimers with different structures and by controlling the feed ratios of the precursors. Buffers with different pH values were used as the conditioning media to examine the swelling properties and the mechanical properties of the hydrogels, revealing that both properties can be controlled. High heavy metal chelating performance of the adsorbent was determined by isothermal adsorption kinetics, titration, and thermal gravimetric analysis. The adsorbent exhibits an outstanding chelating ability toward the three tested heavy metals (Cu(II), Co(II), Ni(II)), and the maximum adsorption capacity (qm ∼ 121 mg·g–1) is higher than that of the majority of the reported biosourced adsorbents.

  • 5.
    Hua, Geng
    et al.
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Polymerteknologi.
    Odelius, Karin
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Polymerteknologi.
    Isocyanate-Free, UV-Crosslinked Poly(Hydroxyurethane) Networks: A Sustainable Approach toward Highly Functional Antibacterial Gels2017Inngår i: Macromolecular Bioscience, ISSN 1616-5187, E-ISSN 1616-5195Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    An increased sustainabile awarness has inspired the development of new polymeric networks in a remarkable way and this strive should be combined with environmentally concerned end-uses. Therefore, a UV-crosslinked polyhydroxyurethane film with antibacterial properties is developed. First, a hydroxyurethane precursor is synthesized using aminolysis condensation, circumventing the use of isocyanates. The films are subsequently crosslinked under solvent-free conditions through a UV-triggered thiol-ene mechanism. The reactions are monitored by 1H nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and Raman spectroscopy, and the networks have gel contents above 90%, and are transparent, hydrophilic, and highly flexible. Antibacterial properties are achieved by a controlled quaternization of the network's tertiary-amine and methylation of thiol-ether functionality, resulting in quaternary ammonium compounds (QACs) and sulfonium compounds. The antibacterial properties are evaluated against both Escherichia coli and Staphylococcus aureus using the agar plate diffusion and tube shaking methods. The QAC-loaded films exhibit outstanding bactericide properties (>99.9%) and the antibacterial mechanism is demonstrated to be a dual killing mechanism, i.e., diffusion killing and contact active killing.

  • 6.
    Hua, Geng
    et al.
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Olsen, Peter
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Franzen, Johan
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi.
    Odelius, Karin
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Anionic polycondensation and equilibrium driven monomer formation of cyclic aliphatic carbonates2018Inngår i: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 8, nr 68, s. 39022-39028Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The current work explores the sodium hydride mediated polycondensation of aliphatic diols with diethyl carbonate to produce both aliphatic polycarbonates and cyclic carbonate monomers. The lengths of the diol dictate the outcome of the reaction; for ethylene glycol and seven other 1,3-diols with a wide array of substitution patterns, the corresponding 5-membered and 6-membered cyclic carbonates were synthesized in excellent yield (70-90%) on a 100 gram scale. Diols with longer alkyl chains, under the same conditions, yielded polycarbonates with an M-w ranging from 5000 to 16000. In all cases, the macromolecular architecture revealed that the formed polymer consisted purely of carbonate linkages, without decarboxylation as a side reaction. The synthetic design is completely solvent-free without any additional post purification steps and without the necessity of reactive ring-closing reagents. The results presented within provide a green and scalable approach to synthesize both cyclic carbonate monomers and polycarbonates with possible applications within the entire field of polymer technology.

  • 7.
    Hua, Geng
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi, Polymerteknologi.
    Ring-opening Approaches to Functional Renewable Polymers2018Doktoravhandling, med artikler (Annet vitenskapelig)
  • 8.
    Pronoitis, Charalampos
    et al.
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Hua, Geng
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Hakkarainen, Minna
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Odelius, Karin
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Biobased Polyamide Thermosets: From a Facile One-Step Synthesis to Strong and Flexible Materials2019Inngår i: Macromolecules, ISSN 0024-9297, E-ISSN 1520-5835, Vol. 52, nr 16, s. 6181-6191Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Biobased polyamide (PA) thermosets composed of renewable ethylene brassylate were synthesized through a one-step reaction under solvent-free conditions, at 100 degrees C in the presence of an organocatalyst. Under these conditions, thermoset formation times as low as 10 min were achieved. The thermosets were easily prepared as thin, transparent films with high strength, flexibility, and high thermal stability. The ester-to-amine content and formation of ethylene glycol in situ as a byproduct of the reaction were studied and correlated with the final properties of the materials. Crystalline oligoester segments were identified as a result of ring-opening polymerization and were shown to have a beneficial effect on the mechanical properties of the thermosets and endowed shape-memory behavior. In contrast to other routes, employing multistep monomer preparation, harsh conditions, and chlorinated reagents, this procedure contributed to the development of sustainable, functional PA thermosets.

  • 9. Tang, Wen
    et al.
    Policastro, Gina M.
    Hua, Geng
    University of Akron, United States .
    Guo, Kai
    Zhou, Jinjun
    Wesdemiotis, Chrys
    Doll, Gary L.
    Becker, Matthew L.
    Bioactive Surface Modification of Metal Oxides via Catechol-Bearing Modular Peptides: Multivalent-Binding, Surface Retention, and Peptide Bioactivity2014Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 136, nr 46, s. 16357-16367Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A series of multivalent dendrons containing a bioactive osteogenic growth peptide (OGP) domain and surface-binding catechol domains were obtained through solid phase synthesis, and their binding affinity to hydroxyapatite, TiO2, ZrO2, CeO2, Fe3O4 and gold was characterized using a quartz crystal microbalance with dissipation (QCM-d). Using the distinct difference in binding affinity of the bioconjugate to the metal oxides, TiO2-coated glass slides were selectively patterned with bioactive peptides. Cell culture studies demonstrated the bioavailability of the OGP and that OGP remained on the surface for at least 2 weeks under in vitro cell culture conditions. Bone sialoprotein (BSP) and osteocalcein (OCN) markers were upregulated 3-fold and 60-fold, respectively, relative to controls at 21 days. Similarly, 3-fold more calcium was deposited using the OGP tethered dendron compared to TiO2. These catechol-bearing dendrons provide a fast and efficient method to functionalize a wide range of inorganic materials with bioactive peptides and have the potential to be used in coating orthopaedic implants and fixation devices.

  • 10.
    Xu, Huan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Polymerteknologi.
    Hua, Geng
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Polymerteknologi.
    Odelius, Karin
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Polymerteknologi.
    Hakkarainen, Minna
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Polymerteknologi.
    Stereocontrolled Entanglement-Directed Self-Alignment of Poly(lactic acid) Cylindrites2016Inngår i: Macromolecular Chemistry and Physics, ISSN 1022-1352, E-ISSN 1521-3935Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The concept of stereocontrolled entanglements, in which the tunable H-bonded chiral pairs serve as crosslinks to create topological constraints on the local chain dynamics, is introduced to tailor the crystalline morphology of stereocomplex poly(lactic acid). For the entanglements to be interconnected and activated, poly(d-lactic acid) with statistical branched architecture is incorporated, enabling the construction of 3D association with linear poly(l-lactic acid) chains. With thermodynamically graded disentanglement relaxation for the blends, the profound influence of entanglements on the crystalline morphology is revealed during isothermal crystallization. Orderly aligned cylindrites some with an exceptional length of over 500 μm, resembling the structural features of the classical shish-kebab superstructure, are observed in the blends penetrated with dense entanglement constraints. By contrast, only dendritic spherulites are formed in the highly disentangled blends. The selectively suppressed homo-crystallization by the entanglements offers insights into the contribution of constraints. This bottom-up strategy opens up pathways to engender oriented crystals of long-range order under quiescent conditions, which has potential implications for other chiral polymers.

  • 11.
    Xu, Yunsheng
    et al.
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Hua, Geng
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Hakkarainen, Minna
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi, Polymerteknologi.
    Odelius, Karin
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi.
    Isosorbide as Core Component for Tailoring Biobased Unsaturated Polyester Thermosets for a Wide Structure- Property Window2018Inngår i: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 19, nr 7, s. 3077-3085Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Biobased unsaturated polyester thermosets as potential replacements for petroleum-based thermosets were designed. The target of incorporating rigid units, to yield thermosets with high thermal and mechanical performance, both in the biobased unsaturated polyester (UP) and reactive diluent (RD) while retaining miscibility was successfully achieved. The biobased unsaturated polyester thermosets were prepared by varying the content of isosorbide, 1,4-butanediol, maleic anhydride, and succinic anhydride in combination with the reactive diluent isosorbide-methacrylate (IM). Isosorbide was chosen as the main component in both the UP and the RD to enhance the rigidity of the formed thermosets, to overcome solubility issues commonly associated with biobased UPs and RDs and volatility and toxicity associated with styrene as RD. All UPs had good solubility in the RD and the viscosity of the mixtures was primarily tuned by the feed ratio of isosorbide but also by the amount of maleic anhydride. The flexural modulus and storage modulus were tailorable by altering the monomer composition The fabricated thermosets had superior thermal and mechanical properties compared to most biobased UP thermosets with thermal stability up to about 250 degrees C and a storage modulus at 25 degrees C varying between 0.5 and 3.0 GPa. These values are close to commercial petroleum-based UP thermosets. The designed tailorable biobased thermosets are, thus, promising candidates to replace their petroleum analogs.

  • 12.
    Zander, Zachary K.
    et al.
    University of Akron, United States.
    Hua, Geng
    University of Akron, United States.
    Wiener, Clinton G.
    University of Akron, United States.
    Vogt, Bryan D.
    University of Akron, United States.
    Becker, Matthew L.
    University of Akron, United States.
    Control of Mesh Size and Modulus by Kinetically Dependent Cross-Linking in Hydrogels2015Inngår i: Advanced Materials, ISSN 0935-9648, E-ISSN 1521-4095, s. n/a-n/aArtikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Kinetically controlled cross-linking processes produce mechanically distinguishable hydrogels using identical precursor chemistry. The oxime ligation demonstrates tunable reaction kinetics with pH and buffer strength, which induce changes in the structural features of hydrogels and determine their mechanical properties. Small-angle neutron scattering and swelling studies provide an insight into how structural properties correlate with mechanical properties for this hydrogel system.

  • 13.
    Zheng, Jukuan
    et al.
    University of Akron, United States .
    Hua, Geng
    University of Akron, United States .
    Yu, Jiayi
    University of Akron, United States .
    Lin, Fei
    University of Akron, United States .
    Wade, Mary Beth
    University of Akron, United States .
    Reneker, Darrell H.
    University of Akron, United States .
    Becker, Matthew L.
    University of Akron, United States .
    Post-Electrospinning “Triclick” Functionalization of Degradable Polymer Nanofibers2015Inngår i: ACS Macro Letters, E-ISSN 2161-1653, Vol. 4, nr 2, s. 207-213Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    4-Dibenzocyclooctynol (DIBO) was used as an initiator for the ring-opening copolymerization of ε-caprolactone and 1,4,8-trioxaspiro[4.6]-9-undecanone (TOSUO) resulting in a series of DIBO end-functionalized copolymers. Following deprotection of the ketone group, the polymers were derivatized with aminooxyl-containing compounds by oxime ligation. Mixtures of keto- and alkyne-derivatized polymers were co-electrospun into well-defined nanofibers containing three separate chemical handles. Strain-promoted azide alkyne cycloaddition (SPAAC), oxime ligation, and copper-catalyzed azide alkyne cycloaddition (CuAAC) were used to sequentially functionalize the nanofibers first with fluorescent reporters and then separately with bioactive Gly-Arg-Gly-Asp-Ser (GRGDS), BMP-2 peptide, and dopamine. This translationally relevant approach facilitates the straightforward derivatization of diverse bioactive molecules that can be controllably tethered to the surface of nanofibers.

  • 14.
    Zheng, Jukuan
    et al.
    University of Akron, United States .
    Kontoveros, Dimitria
    University of Akron, United States .
    Lin, Fei
    University of Akron, United States .
    Hua, Geng
    University of Akron, United States .
    Reneker, Darrell H.
    University of Akron, United States .
    Becker, Matthew L.
    University of Akron, United States .
    Willits, Rebecca K.
    University of Akron, United States .
    Enhanced Schwann Cell Attachment and Alignment Using One-Pot “Dual Click” GRGDS and YIGSR Derivatized Nanofibers2015Inngår i: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 16, nr 1, s. 357-363Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Using metal-free click chemistry and oxime condensation methodologies, GRGDS and YIGSR peptides were coupled to random and aligned degradable nanofiber networks postelectrospinning in a one-pot reaction. The bound peptides are bioactive, as demonstrated by Schwann cell attachment and proliferation, and the inclusion of YIGSR with GRGDS alters the expression of the receptor for YIGSR. Additionally, aligned nanofibers act as a potential guidance cue by increasing the aspect ratio and aligning the actin filaments, which suggest that peptide-functionalized scaffolds would be useful to direct SCs for peripheral nerve regeneration.

  • 15.
    Zheng, Jukuan
    et al.
    University of Akron, United States .
    Xie, Sibai
    University of Akron, United States .
    Lin, Fei
    University of Akron, United States .
    Hua, Geng
    University of Akron, United States .
    Yu, Tianyi
    University of Akron, United States .
    Reneker, Darrell H.
    University of Akron, United States .
    Becker, Matthew L.
    University of Akron, United States .
    4-Dibenzocyclooctynol (DIBO) as an initiator for poly([varepsilon]-caprolactone): copper-free clickable polymer and nanofiber-based scaffolds2013Inngår i: Polymer Chemistry, ISSN 1759-9954, E-ISSN 1759-9962, Vol. 4, nr 7, s. 2215-2218Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Utilization of 4-dibenzocyclooctynol (DIBO) as an initiator for the ring-opening polymerization of [varepsilon]-caprolactone yields well-defined, high molecular weight poly([varepsilon]-caprolactone) end functionalized with DIBO (DIBO-PCL). Nanofibers bearing reactive DIBO groups were generated via electrospinning and functionalized post-fabrication with azide-tethered molecules.

1 - 15 of 15
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