Polyurethane films formation from microcrystalline cellulose as a polyol and cellulose nanocrystals as additive: Reactions favored by the low viscosity of the source of isocyanate groups used

Porto, Deyvid S.; Faria, Clara Maria Gonçalves de; Inada, Natália Mayumi; Frollini, Elisabete

doi:10.1016/j.ijbiomac.2023.124035

Cited by 10 publications

(6 citation statements)

References 49 publications

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“…(a) Stress–strain curves of VBD-TMP x and (b) mechanical performance of VBD-TMP 60 in this work compared with some biorenewable crosslinked polyurethanes in other research studies and commercial nonrenewable crosslinked polyurethanes. ,,,,,− …”

Section: Resultsmentioning

confidence: 95%

“…Therefore, bio-based thermosetting polyurethanes with different mechanical properties can be facilely prepared by tuning the content of crosslinker TMP. Within the context of biorenewable crosslinked polyurethanes, these VBD-TMP x lie at the high end of mechanical performances (Figure b). ,,,,,− They offer comparable tensile strengths and elongation at break values, but stand out in terms of their high bio-contents and degradability. It is also noteworthy that the stress–strain profiles for VBD-TMP 60 are comparable to or better than some of the commercial nonrenewable crosslinked polyurethanes, such as the Durethane R series and Desmodur MP-101 (Figure b).…”

Section: Resultsmentioning

confidence: 99%

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Vanillin-Based Degradable Polyurethane Thermosets Demonstrating High Bio-Content and Mechanical Properties

Zhao

Liu

Wang

et al. 2023

ACS Appl. Polym. Mater.

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Polyurethanes are widely used polymeric materials, but they are rarely biorenewable and degradable. Although some previously reported bio-based polyurethanes exhibit good thermal and mechanical properties, their bio-content is usually low, resulting from the only replacement of the diol monomer instead of the whole diol/diisocyanate pairs. In addition, traditional polyurethanes are often difficult to degrade, leading to environmental issues. To address these issues, we propose a solution by sourcing both the diols and isocyanates from biorenewable resources and introducing degradability into diols via the Tishchenko reaction, which is the disproportionation of two aldehydes to afford an ester bond with an atom economy of 100%. Commercially available bio-based vanillin was selected as the precursor for a vanillin-based diol (VBD) containing ester bonds. By reacting VBD with L-lysine diisocyanate (LDI) and trimethylolpropane (TMP) as a crosslinker, a series of bio-based thermosetting polyurethanes, VBD-TMP x , with high bio-based carbon content (>70.0%) were synthesized. The chemical structures and properties of monomers as well as polymers were characterized using nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) spectroscopy, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), dynamic mechanical analysis (DMA), and tensile tests. The obtained VBD-TMP x polyurethanes exhibit comparable mechanical properties (σ = 32.0 MPa; E′ = 2.7 GPa) to commercial thermosetting polyurethanes and demonstrate higher toughness (34 MJ/m 3 ) than previously reported bio-based analogues. Additionally, the inherent ester bond in the VBD monomer enables the complete degradation of VBD-TMP x in a 0.1 M NaOH solution (THF/H 2 O = 1:1, v/v) within 3.5 h. This greatly broadens the available end-of-life choices, including the recovery of the monomers. This study presents a facile approach for creating degradable polyurethane materials with high bio-content and mechanical properties.

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Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

Vanillin-Based Degradable Polyurethane Thermosets Demonstrating High Bio-Content and Mechanical Properties

Zhao

Liu

Wang

et al. 2023

ACS Appl. Polym. Mater.

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“…According to ISO 10993-5, PUs are nontoxic to the L929 and HDFa cells, as the reduction in viability is less than 30%. A sign of cytotoxicity of biomaterials is a reduction in viability of 70% [ 28 ].…”

Section: Discussionmentioning

confidence: 99%

Incorporation of Chitosan in Polyurethanes Based on Modified Castor Oil for Cardiovascular Applications

Morales-González,

Navas-Gómez,

Diaz

et al. 2023

Polymers

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The increased demand for vascular grafts for the treatment of cardiovascular diseases has led to the search for novel biomaterials that can achieve the properties of the tissue. According to this, the investigation of polyurethanes has been a promising approach to overcome the present limitations. However, some biological properties remain to be overcome, such as thrombogenicity and hemocompatibility, among others. This paper aims to synthesize polyurethanes based on castor oil and castor oil transesterified with triethanolamine (TEA) and pentaerythritol (PE) and with the incorporation of 1% chitosan. Analysis of the wettability, enzymatic degradation, mechanical properties (tensile strength and elongation at break), and thermal stability was performed. Along with the evaluation of the cytotoxicity against mouse fibroblast (L929) and human dermal fibroblast (HDFa) cells, the hemolysis rate and platelet adhesion were determined. The castor-oil-based polyurethanes with and without 1% chitosan posed hydrophobic surfaces and water absorptions of less than 2% and enzymatic degradation below 0.5%. Also, they were thermally stable until 300 °C, with tensile strength like cardiovascular tissues. The synthesized castor oil/chitosan polyurethanes are non-cytotoxic (cell viabilities above 80%) to L929 and HDFa cells and non-thrombogenic and non-hemolytic (less than 2%); therefore, they are suitable for cardiovascular applications.

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“…11, the PU networks produced in this work exhibited comparable or higher tensile strength and elongation at break than most biobased PU thermosets reported in the literature or non-renewable commercially available crosslinked polyurethanes. 3,6,[48][49][50][51][52][53][54][55][56][57][58][59] The attractive features of the developed PU thermosets such as good and easily tunable mechanical performance, including a very broad range of elongation at break (15-188%), Young's moduli (6.1-648.8 MPa) and tensile strength (3.3-31.1 MPa), together with their high heat resistance and good optical transparency could cement these PUs as a promising class of high-performance amorphous polyurethane materials.…”

Section: Mechanical Properties Of the Polyurethane Thermosetsmentioning

confidence: 99%

“…11 Comparison of the mechanical performance of synthesized PU networks in this work with other biobased crosslinked polyurethanes in the literature and commercial non-renewable crosslinked polyurethanes. 3,6,[48][49][50][51][52][53][54][55][56][57][58][59] Fig. 12 Mass loss of the films against time of the enzymatic hydrolysis of (A) partially crosslinked and (B) fully crosslinked polyurethane networks.…”

Section: Enzymatic Degradation Of Pu Thermosetsmentioning

confidence: 99%

Highly transparent polyurethane thermosets with tunable properties and enzymatic degradability derived from polyols originating from hemicellulosic sugars

Kasmi,

Chebbi,

Lorenzetti

et al. 2023

Green Chem.

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Polyurethane films formation from microcrystalline cellulose as a polyol and cellulose nanocrystals as additive: Reactions favored by the low viscosity of the source of isocyanate groups used

Cited by 10 publications

References 49 publications

Vanillin-Based Degradable Polyurethane Thermosets Demonstrating High Bio-Content and Mechanical Properties

Vanillin-Based Degradable Polyurethane Thermosets Demonstrating High Bio-Content and Mechanical Properties

Incorporation of Chitosan in Polyurethanes Based on Modified Castor Oil for Cardiovascular Applications

Highly transparent polyurethane thermosets with tunable properties and enzymatic degradability derived from polyols originating from hemicellulosic sugars

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