Preparation and characterization of lignin demethylated at atmospheric pressure and its application in fast curing biobased phenolic resins

Li, Jiongjiong; Wang, Wen; Zhang, Shifeng; Gao, Qiang; Zhang, Wei

doi:10.1039/c6ra11966b

Cited by 95 publications

(70 citation statements)

References 48 publications

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“…For the demethylation, a procedure reported by Li et al was used and slightly modified [33]. The sample (1 g), 0.1 g of Na 2 SO 3 as the demethylating reagent and 6 g of 2.5 mol NaOH solution were introduced into a 15 mL rolled rim glass on an analytical balance and homogenized.…”

Section: Synthesis Of Demethylated Kraft Ligninmentioning

confidence: 99%

“…So far, various procedures have been explored to incorporate more OH groups into the lignin structure including hydroxymethylation, phenolation, demethylation, oxidation and reduction [31]. These modifications have been studied primarily in conjunction with phenol-formaldehyde (PF) resins or PU research using lignin as a replacement for fossil-based phenols and polyols [32].In 2016, Li et al reported using demethylation to enhance the chemical reactivity at atmospheric pressure to produce fast curing phenolic resins [33]. Another possibility for lignin demethylation is an enzymatically catalyzed reaction using fungi (i.e., white and brown rot fungi) or bacteria (i.e., Pseudomonas, Sphingomonas).…”

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confidence: 99%

“…In 2016, Li et al reported using demethylation to enhance the chemical reactivity at atmospheric pressure to produce fast curing phenolic resins [33]. Another possibility for lignin demethylation is an enzymatically catalyzed reaction using fungi (i.e., white and brown rot fungi) or bacteria (i.e., Pseudomonas, Sphingomonas).…”

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Antimicrobial Activity of Lignin-Derived Polyurethane Coatings Prepared from Unmodified and Demethylated Lignins

et al. 2019

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Due to global ecological and economic challenges that have been correlated to the transition from fossil-based to renewable resources, fundamental studies are being performed worldwide to replace fossil fuel raw materials in plastic production. One aspect of current research is the development of lignin-derived polyols to substitute expensive fossil-based polyol components for polyurethane and polyester production. This article describes the synthesis of bioactive lignin-based polyurethane coatings using unmodified and demethylated Kraft lignins. Demethylation was performed to enhance the reaction selectivity toward polyurethane formation. The antimicrobial activity was tested according to a slightly modified standard test (JIS Z 2801(JIS Z :2010. Besides effects caused by the lignins themselves, triphenylmethane derivatives (brilliant green and crystal violet) were used as additional antimicrobial substances. Results showed increased antimicrobial capacity against Staphylococcus aureus. Furthermore, the coating color could be varied from dark brown to green and blue, respectively.Coatings 2019, 9, 494 2 of 16 and DNA in cells of mice against oxidation damage [19] have been tested. Gao [20] and Bshena [21] studied the antimicrobial activity of various textiles, using lignin incorporated into polyethylene films and applied in the finishing processes. For textiles, there are special requirements such as non-toxicity to the consumer, namely cytotoxicity, allergy or irritation and sensitization. In other recent studies, lignosulfonic acid is reported to exhibit broad-spectrum anti-HIV (human immunodeficiency virus) and anti-HSV (herpes simplex virus) properties [22,23]. Thus, Qiu investigated the anti-HIV-1 activity-potential of lignosulfonates as a microbicide to prevent HIV-1 sexual transmission [23]. Another recently reported study revealed that the antimicrobial capacity of lignin correlates with the phenolic components, specifically the side chain structure and the nature of further functional groups [24]. Typically, the presence of a double bond in α, β positions of the side chain and a methyl group in the γ position grants the phenolic fragments with the most potency against microorganisms. However, none of the hitherto published studies included the investigation of the antibacterial activity of lignin when included in polymeric matrices.Unmodified lignin is widely studied as a component for polymer production with a focus on phenol-formaldehyde resins and polyurethanes (PUs) [25], where lignin is used as polyol substitute due to the high amount of hydroxyl groups resulting in high crosslinking densities and variable mechanical properties [26][27][28]. In previous studies, lignin-derived polyurethane coatings have been prepared using Kraft lignin isolated at room temperature from aqueous media (black liquor) at different pH values [29]. In addition, their antioxidative activity has been investigated using the Folin-Ciocalteu (FC) assay [30]. Although lignin contains many functionalities, they are often diff...

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Section: Synthesis Of Demethylated Kraft Ligninmentioning

confidence: 99%

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confidence: 99%

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Antimicrobial Activity of Lignin-Derived Polyurethane Coatings Prepared from Unmodified and Demethylated Lignins

et al. 2019

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“…The 4,000–400 cm −1 infrared spectral region of BPF and PF resins before and after aging were shown in Fig. , and the structural changes during aging was ascertained by a semiquantitative analysis method . The peak at 1,600 cm −1 was assigned to the aromatic skeletal vibration, which was almost unchanged in each reaction during aging.…”

Section: Resultsmentioning

confidence: 99%

“…The rising price of petroleum together with the scarcity of fossil feedstock and promoting environment‐friendly products have encouraged renewable resources . Hence, considerable efforts have been made to replace phenol partially with cheaper materials or renewable resources, such as urea , lignin , and plant oil .…”

Section: Introductionmentioning

confidence: 99%

Investigation of aging performance of bio‐oil phenol‐formaldehyde resin with the treatment of artificial accelerated aging method

Xing

et al. 2017

Polymer Engineering & Sci

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The aging performance of bio‐oil phenol‐formaldehyde (BPF) resin was investigated using artificial accelerated aging method. After the treatment, the variations on the mass and bonding strength of plywood with BPF resin were determined. The changes in the microstructure, functional groups, and chemical bonds of adhesive films with BPF resin were also analyzed by scanning electron microscope, Fourier transform infrared spectroscopy, and X‐ray photoelectron spectroscopy analysis. The decrease of mass loss and bonding strength of BPF resin were smaller, the surface of BPF resin was smoother, and the amounts of CH2 groups and COC groups of BPF resin were larger than that of phenol‐formaldehyde (PF) resin at the same aged period. These results indicated that the bio‐oil could be used to improve the aging performance of PF resin. POLYM. ENG. SCI., 58:1810–1816, 2018. © 2017 Society of Plastics Engineers

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Advances in Bio‐based Thermosetting Polymers

Rouméas

Billerach

Aouf

et al. 2019

Recent Advances in Polyphenol Research

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Preparation and characterization of lignin demethylated at atmospheric pressure and its application in fast curing biobased phenolic resins

Abstract: Agricultural crop-based lignin was utilized to modify phenol-formaldehyde (PF) resin to prepare fast curing biobased phenolic resins by copolymerization.

Cited by 95 publications

References 48 publications

Antimicrobial Activity of Lignin-Derived Polyurethane Coatings Prepared from Unmodified and Demethylated Lignins

Antimicrobial Activity of Lignin-Derived Polyurethane Coatings Prepared from Unmodified and Demethylated Lignins

Investigation of aging performance of bio‐oil phenol‐formaldehyde resin with the treatment of artificial accelerated aging method

Advances in Bio‐based Thermosetting Polymers

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