Synthesis and Characterization of Polyurethanes with High Renewable Carbon Content and Tailored Properties

Calvo‐Correas, Tamara; Martín, María Dolores; Retegi, Aloña; Gabilondo, Nagore; Corcuera, María Ángeles; Eceiza, Arantxa

doi:10.1021/acssuschemeng.6b01578

Cited by 55 publications

(51 citation statements)

References 42 publications

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“…The final properties of the PUs are strongly dependent on the nature of the components and their equivalent weight ratio . For instance, when asymmetric or branched diisocyanate (or polyol) are used, PUs with lower glass transition temperatures ( T g ) and a lower ability to crystallize are obtained . Moreover, the reactivity of hydroxyl groups is other important factor .…”

Section: Introductionmentioning

confidence: 99%

“…15,16 For instance, when asymmetric or branched diisocyanate (or polyol) are used, PUs with lower glass transition temperatures (T g ) and a lower ability to crystallize are obtained. [17][18][19] Moreover, the reactivity of hydroxyl groups is other important factor. 20 Several studies have shown that secondary hydroxyl group exhibits significant lower reactivity than primary hydroxyl group [the reactivity of secondary hydroxyl group at the same temperature (range considered: 25-50 C) is between 3 and 200 times lower than that of the primary ones].…”

Section: Introductionmentioning

confidence: 99%

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Comparative effects of two different crosslinkers on the properties of vegetable oil‐based polyurethanes

Meiorin

Calvo‐Correas

Mosiewicki

et al. 2019

J of Applied Polymer Sci

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Thermoset polyurethanes (PUs) were prepared from a polyol derived from castor oil, 4,4′‐methylene diphenyl diisocyanate (MDI) and different trifunctional low‐molecular‐weight crosslinkers, biobased glycerol (Gly) and petroleum‐derived trimethylolpropane (TMP). The synthesis was carried out in bulk and without catalyst via one‐step polymerization varying the components equivalent weight ratio, Polyol:MDI:Gly and Polyol:MDI:TMP, respectively. The physicochemical, morphological, thermal, dynamic–mechanical, and mechanical properties of the PUs were determined. The success of the reaction between the polyol and MDI was confirmed by Fourier transform infrared spectroscopy. The dynamic–mechanical and the mechanical properties as well as hardness were determined and related to the concentration of the low‐molecular‐weight crosslinkers utilized (Gly or TMP). However, important differences were observed between the synthesized two series, due to phase separation produced during the curing reaction, which affected more the materials prepared from TMP. Scanning electron microscopy images and dynamic–mechanical results confirmed this difference, related to the reactivity of primary and secondary hydroxyls present in the crosslinkers. Thermogravimetric analysis also showed to be sensible to the different structure of the crosslinkers with TMP leading to more thermally stable samples. Finally, measurements of water contact angle indicated that the surfaces were mostly hydrophobic with minor differences between the samples. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2020, 137, 48741.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Comparative effects of two different crosslinkers on the properties of vegetable oil‐based polyurethanes

Meiorin

Calvo‐Correas

Mosiewicki

et al. 2019

J of Applied Polymer Sci

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“…Polyurethane films possessing water contact angles below 90 °C are considered to be hydrophilic with increased wettability . The surface wettability of polyurethane films was determined by water contact angle measurements and the data for parent polyurethanes and click‐functionalized polyurethanes are summarized in Table and Table .…”

Section: Resultsmentioning

confidence: 99%

Clickable polyurethanes based on s‐triazine ring containing aromatic diisocyanate bearing pendent alkyne group: Synthesis and postmodification

Garg

Chatterjee

Wadgaonkar

2017

J. Polym. Sci. Part A: Polym. Chem.

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A new s-triazine ring containing aromatic diisocyanate bearing a pendent alkyne group, namely, 2,4-bis(4-isocyanatophenoxy)26-(prop-2-yn-1-yloxy)21,3,5-triazine was synthesized and reacted with various diols viz., 1,10-decanediol, tetraethylene glycol and polyethylene glycols in the presence of dibutyltin dilaurate as the catalyst to obtain a series of linear polyurethanes. The selected polyurethanes possessing pendent alkyne groups were postmodified with chemically diverse azides viz., 1-(azidomethyl)benzene, 1-(azidomethyl)pyrene, and methoxy end-caped poly(ethylene glycol) azide via coppercatalysed azide-alkyne Huisgen 1,3-dipolar cycloaddition. FTIR and 1 H NMR spectra indicated quantitative click reaction. UVvis and fluorescence spectroscopic analysis confirmed complete incorporation of pyrenyl groups indicating the formation of fluorescence active polyurethane by postmodification with 1-(azidomethyl)pyrene. TG analysis of polyurethanes indicated two stage weight loss and their thermal stability, as judged by T 10 values, was governed by weight percent of urethane linkages. The water contact angle measurements revealed improved wettability with increased content of PEG either in the backbone of polyurethanes or as grafted chains. DLS and TEM studies confirmed that certain polyurethanes possessing PEG segments displayed self-assembly in aqueous solution, which was further supported by pyrene encapsulation studies using UV-vis spectroscopy.

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“…Castor oil in combination with diethyl phosphate has been used to form of PUs with fire resistant properties (Zhang et al, 2014). Biobased polyurethanes (Calvo-Correas et al, 2016) have also been synthesized from oils. Preparation of bio-based PUs using oils showed that mechanical and morphology of the products depended on the overall crystallinity which itself was dependent upon the molar ratio of the components.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Bio-based Polyurethane Polymers

Emrani¹,

Benrashid²,

Mohtarami³

et al. 2018

American Journal of Engineering and Applied Sciences

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This paper describes the development of new biobased Polyurethanes (PU) starting from swine manure bio-resin and diisocyanates. The bio-resin is produced from swine manure via a hydrothermal process. For sustainability, today, many PUs in new specialized applications, are biobased. In this study, different commercial diisocyanates including MDI, Desmodur W, Desmodur H and Demodur I and swine manure, which is an agricultural waste were used to make the biobased PUs. The reactions were performed at refluxing THF, or in neat form at temperatures that ranged from room temperature to 100°C. Dibutyltin dilaurate was used as catalyst for the polymerization. Composites were characterized by FTIR, GPC, ICP and Rheometry. GPC confirmed the increase in the size of the molecules consistent with the increase in the viscosity and complex modulus of the reaction mixtures as a function of reaction time. One composite reached to elastic modulus of 10 MP at the end of the reaction process, which was marked by depletion of isocyanates peak in the IR. Progress of the polymerization reaction was monitored by the disappearance of the isocyanate band in the IR at ~2274 cm −1. By monitoring the FTIR spectra of the reaction mixtures while increasing MDI dosage in a step-wise manner, the number of the molar equivalents of the functional groups active towards isocyanate (including OH, H 2 S, NH 2 and COOH) in the bioresin was also determined.

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Synthesis and Characterization of Polyurethanes with High Renewable Carbon Content and Tailored Properties

Cited by 55 publications

References 42 publications

Comparative effects of two different crosslinkers on the properties of vegetable oil‐based polyurethanes

Comparative effects of two different crosslinkers on the properties of vegetable oil‐based polyurethanes

Clickable polyurethanes based on s‐triazine ring containing aromatic diisocyanate bearing pendent alkyne group: Synthesis and postmodification

Synthesis and Characterization of Bio-based Polyurethane Polymers

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