Facile route to multigram synthesis of environmentally friendly non-isocyanate polyurethanes

Tryznowski, Mariusz; Świderska, Aleksandra; Żołek‐Tryznowska, Zuzanna; Gołofit, Tomasz; Parzuchowski, Paweł G.

doi:10.1016/j.polymer.2015.10.055

Cited by 56 publications

(94 citation statements)

References 38 publications

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“…In recent years, numerous studies have investigated PHU synthesis with strong emphasis on the production of single-phase PHUs, crosslinked PHU networks, reaction catalysis and the synthesis of carbonate monomers . For example, Endo and coworkers [14][15][16][17][18][19][20][21][22][23], as well as others [24][25][26][27][28][29], synthesized PHUs from carbonated epoxy resins (such as Bisphenol A diglycidyl ether, hydroquinone diglycidyl ether, and butanediol diglycidyl ether) and small-molecule diamines (such as hexamethylene diamine) resulting in single-phase PHUs [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29]. The reaction kinetics of five-, six- [17][18][19]51], seven- [20] and eight-membered ring carbonates [12], the influence of substituent on reactivity [21,52], and the effects of catalysts [22,[30][31][32] were also characterized.…”

Section: Introductionmentioning

confidence: 99%

Novel thermoplastic polyhydroxyurethane elastomers as effective damping materials over broad temperature ranges

Beniah

Liu

Heath

et al. 2016

European Polymer Journal

101

111

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a b s t r a c tNon-isocyanate thermoplastic polyhydroxyurethane (PHU) elastomers were synthesized from cyclic carbonate aminolysis using polytetramethylene oxide (PTMO) as soft segment and divinylbenzene dicyclocarbonate and three diamine chain extenders as hard segment with a range of hard-segment content. Characterization was done via Fourier transform infrared spectroscopy, small-angle X-ray scattering (SAXS), uniaxial tensile testing, and dynamic mechanical analysis (DMA). SAXS reveals that these PHUs possess nanophaseseparated morphology with 10-20 nm interdomain spacings. These PHUs display elastomeric response and tunable tensile properties with Young's modulus ranging from 27 to 200 MPa, tensile strength from 0.3 to 9.7 MPa and elongation at break ranging up to greater than 2000%. DMA reveals that nanophase separation in these PHUs is accompanied by broad interphases having a wide range of local composition; this nanophase separation differs significantly from that manifested by thermoplastic polyurethane elastomer (TPU) due to hydrogen bonding of hydroxyl groups in the hard segments to the PTMO soft segment. These PHUs show very good damping performance with tan d P 0.30 over broad temperature ranges (P60°C), which are tunable through simple variation of hardsegment content and chain extender structures.

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Section: Introductionmentioning

confidence: 99%

Novel thermoplastic polyhydroxyurethane elastomers as effective damping materials over broad temperature ranges

Beniah

Liu

Heath

et al. 2016

European Polymer Journal

101

111

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“…[130] A shorter chain analogue of 4f (4f')w as used for the synthesis of nanocapsules for drug delivery. [140] In this case, the authors were able to separate pure 4l from other carbonated diglycerol regioisomers. [131] 4g was preparedb yP lasseraud and co-workerss tarting from undecylenic acid (UA), at erminally unsaturated fatty acid that can be obtained from the pyrolysis of the ricinoleic acid chains of castor oil (Scheme 12, route a).…”

Section: Terminal Biscarbonatesmentioning

confidence: 99%

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization

et al. 2019

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Given the large amount of anthropogenic CO2 emissions, it is advantageous to use CO2 as feedstock for the fabrication of everyday products, such as fuels and materials. An attractive way to use CO2 in the synthesis of polymers is by the formation of five‐membered cyclic organic carbonate monomers (5CCs). The sustainability of this synthetic approach is increased by using scaffolds prepared from renewable resources. Indeed, recent years have seen the rise of various types of carbonate syntheses and applications. 5CC monomers are often polymerized with diamines to yield polyhydroxyurethanes (PHU). Foams are developed from this type of polymers; moreover, the additional hydroxyl groups in PHU, absent in classical polyurethanes, lead to coatings with excellent adhesive properties. Furthermore, carbonate groups in polymers offer the possibility of post‐functionalization, such as curing reactions under mild conditions. Finally, the polarity of carbonate groups is remarkably high, so polymers with carbonates side‐chains can be used as polymer electrolytes in batteries or as conductive membranes. The target of this Review is to highlight the multiple opportunities offered by polymers prepared from and/or containing 5CCs. Firstly, the preparation of several classes of 5CCs is discussed with special focus on the sustainability of the synthetic routes. Thereafter, specific classes of polymers are discussed for which the use and/or presence of carbonate moieties is crucial to impart the targeted properties (foams, adhesives, polymers for energy applications, and other functional materials).

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“…Our initial efforts focused on using diglycerol, which is a promising biorenewable tetraol monomer derived from glycerol . Glycerol, a coproduct of biodiesel production, is a relatively low cost commodity chemical formed in large excess when compared to its current demand . Previous efforts to employ diglycerol for polymer synthesis include copolymerization with an anhydride, converting to the dicarbonate, or diketal prior to copolymerization, or use as a tetraol initiator .…”

Section: Introductionmentioning

confidence: 99%

“…Glycerol, a coproduct of biodiesel production, is a relatively low cost commodity chemical formed in large excess when compared to its current demand . Previous efforts to employ diglycerol for polymer synthesis include copolymerization with an anhydride, converting to the dicarbonate, or diketal prior to copolymerization, or use as a tetraol initiator . The commercially available form of diglycerol contains three structural isomers (α,α‐, α,β‐, and β,β‐), with the α,α‐form predominating [Figure (a)] .…”

Section: Introductionmentioning

confidence: 99%

“…Previous efforts to employ diglycerol for polymer synthesis include copolymerization with an anhydride, converting to the dicarbonate, or diketal prior to copolymerization, or use as a tetraol initiator . The commercially available form of diglycerol contains three structural isomers (α,α‐, α,β‐, and β,β‐), with the α,α‐form predominating [Figure (a)] . Work from other research groups focused on derivatizing diglycerol prior to polymerization.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and material properties of elastomeric high molecular weight polycycloacetals derived from diglycerol and meso‐erythritol

Law

Stankowski

Bomann

et al. 2019

J of Applied Polymer Sci

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Copolymerizing glutaraldehyde with tetraols such as diglycerol, meso‐erythritol, and pentaerythritol is particularly effective for forming very high molecular weight polycycloacetals (Mn up to 65,000 g/mol) with elastomeric properties and up to 70% biorenewable content by weight. Altering the tetraol monomer feed ratio provides control over the polycycloacetal's tensile properties. The polymerizations are high‐yielding, readily scalable, and employ commercially available starting materials that are used without further purification. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2020, 137, 48780.

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Facile route to multigram synthesis of environmentally friendly non-isocyanate polyurethanes

Cited by 56 publications

References 38 publications

Novel thermoplastic polyhydroxyurethane elastomers as effective damping materials over broad temperature ranges

Novel thermoplastic polyhydroxyurethane elastomers as effective damping materials over broad temperature ranges

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization

Synthesis and material properties of elastomeric high molecular weight polycycloacetals derived from diglycerol and meso‐erythritol

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Facile route to multigram synthesis of environmentally friendly non-isocyanate polyurethanes

Cited by 56 publications

References 38 publications

Novel thermoplastic polyhydroxyurethane elastomers as effective damping materials over broad temperature ranges

Novel thermoplastic polyhydroxyurethane elastomers as effective damping materials over broad temperature ranges

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO2 Utilization

Synthesis and material properties of elastomeric high molecular weight polycycloacetals derived from diglycerol and meso‐erythritol

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Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization