Preparation of lignin/glycerol-based bis(cyclic carbonate) for the synthesis of polyurethanes

Chen, Qin; Gao, Keke; Peng, Chang; Xie, Haibo; Zhao, Zongbao K.; Bao, Ming

doi:10.1039/c5gc01340b

Cited by 89 publications

(73 citation statements)

References 50 publications

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“…Aminolysis products were obtained in 95% apparent yield. About 100 mg of the crude were acetylated to improve the solubility in DMSO-d 6 and analyzed by 13 C NMR.…”

Section: Lignin Cyclocarbonationmentioning

confidence: 99%

“…The 13 C NMR spectrum of the aminolysis derivative is also characterized by two, partially overlapped signals placed at 155.7 and 156.0 ppm (Fig. 2, below, centre), accounting for carbamate carbonyls provided by b-hydroxycarbamate derivatives bearing either primary or secondary hydroxyl groups, respectively.…”

Section: Aminolysis Reaction Of Cyclocarbonate Groups On Ligninmentioning

confidence: 99%

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Utilization of cyclocarbonated lignin as a bio-based cross-linker for the preparation of poly(hydroxy urethane)s

et al. 2017

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In this work, cyclocarbonated modified lignin, the most abundant reservoir of aromatic moieties in nature, was used as a green bio-based cross-linker on polyhydroxy urethane formulations. As a preliminary study, a complete 13 C NMR characterization of the aminolysis products of cyclocarbonated lignin with 1,12diaminododecane was provided. The best reaction conditions found for the aminolysis reaction were applied for the preparation of thermoset resins. Cyclocarbonated lignin was then reacted with 1,12diaminododecane, acting as a chain extender, in the presence of poly(ethylene glycol) bis cyclic carbonate, a soft segment used to tune the resin properties. Different (total cyclocarbonates)/(total amines) equivalent ratios and diverse poly(ethylene glycol)/lignin stoichiometry were tested. The evolution in time of the molecular weight distribution of a selected composition was followed by gel permeation chromatography until the solubility in THF was appreciable. Moreover, some significant resin samples were subjected to DSC analysis to evaluate favourable changes in the glass transition temperature and compared to blank experiments that did not include lignin in the composition.

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“…Aminolysis products were obtained in 95% apparent yield. About 100 mg of the crude were acetylated to improve the solubility in DMSO-d 6 and analyzed by 13 C NMR.…”

Section: Lignin Cyclocarbonationmentioning

confidence: 99%

Section: Aminolysis Reaction Of Cyclocarbonate Groups On Ligninmentioning

confidence: 99%

Utilization of cyclocarbonated lignin as a bio-based cross-linker for the preparation of poly(hydroxy urethane)s

et al. 2017

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“…[20] Hernandez et al described fully biobased bisphenols obtained from guaiacaol and vanillyl alcohol and their application towards epoxy resins. [21] Recently,b iscreosol [22] was transformed into biscyclocarbonate for the synthesis of polyhydroxyurethanes, [23] or into biscyanate for cyanate-ester resin. [24] Vanillinbased bisphenols obtained through achemoenzymatic process have been described as ap latform of high interest for the design of new rigid biobased polymers.…”

Section: Introductionmentioning

confidence: 99%

Syringaresinol: A Renewable and Safer Alternative to Bisphenol A for Epoxy‐Amine Resins

et al. 2017

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A renewable bisepoxide, SYR-EPO, was prepared from syringaresinol, a naturally occurring bisphenol deriving from sinapic acid, by using a chemo-enzymatic synthetic pathway. Estrogenic activity tests revealed no endocrine disruption for syringaresinol. Its glycidylation afforded SYR-EPO with excellent yield and purity. This biobased, safe epoxy precursor was then cured with conventional and renewable diamines for the preparation of epoxy-amine resins. The resulting thermosets were thermally and mechanically characterized. Thermal analyses of these new resins showed excellent thermal stabilities (T =279-309 °C) and T ranging from 73 to 126 °C, almost reaching the properties of those obtained with the diglycidylether of bisphenol A (DGEBA), extensively used in the polymer industry (T =319 °C and T =150 °C for DGEBA/isophorone diamine resins). Degradation studies in NaOH and HCl aqueous solutions also highlighted the robustness of the syringaresinol-based resins, similar to bisphenol A (BPA). All these results undoubtedly confirmed the potential of syringaresinol as a greener and safer substitute for BPA.

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“…In addition, PHUs synthesized in the presence of TBD at room temperature showed higher molar mass than the corresponding polymers produced in the absence of catalyst. 26 However, with or without catalyst, the soproduced PHUs exhibited low molar masses which probably arose from side reactions as recently proposed by Caillol et al…”

Section: 2022-25mentioning

confidence: 74%

DFT investigation of the reaction mechanism for the guanidine catalysed ring-opening of cyclic carbonates by aromatic and alkyl-amines

et al. 2017

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The guanidine catalysed aminolysis of propylene carbonate has been investigated using density functional theory (DFT) and highlights that different reaction pathways are involved, depending on the aromatic or aliphatic nature of the amine. The structural ability of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) to simultaneously give and receive protons was demonstrated by a detailed mechanistic investigation. The bifunctional activity (base/H-bond donor) of TBD significantly reduces the Gibbs energy of the reaction and allows understanding of its higher efficiency compared to its methyl counterpart (MTBD).

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Preparation of lignin/glycerol-based bis(cyclic carbonate) for the synthesis of polyurethanes

Cited by 89 publications

References 50 publications

Utilization of cyclocarbonated lignin as a bio-based cross-linker for the preparation of poly(hydroxy urethane)s

Utilization of cyclocarbonated lignin as a bio-based cross-linker for the preparation of poly(hydroxy urethane)s

Syringaresinol: A Renewable and Safer Alternative to Bisphenol A for Epoxy‐Amine Resins

DFT investigation of the reaction mechanism for the guanidine catalysed ring-opening of cyclic carbonates by aromatic and alkyl-amines

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