Comparative analysis of different lignins as phenol replacement in phenolic adhesive formulations

Kalami, Somayyeh; Chen, Nusheng; Borazjani, Hamid; Nejad, Mojgan

doi:10.1016/j.indcrop.2018.09.037

Cited by 74 publications

(80 citation statements)

References 31 publications

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“…Lignin valorization is critical for economic viability of biorefining processes, and is favored by a low degree of condensation, chemically labile groups for functionalization, and high purity 1 . Lignins with high molecular weight are suitable as fillers in composite materials 2 , while production of lignin-based adhesives replacing phenol requires low molecular mass and narrow weight distribution 3 . However, lignin is highly heterogeneous, with variations in its molecular weight, chemical composition, degree of cross-linking and functional groups, which makes its utilization challenging.…”

Section: Introductionmentioning

confidence: 99%

Fractionation by Sequential Antisolvent Precipitation of Grass, Softwood, and Hardwood Lignins Isolated Using Low-Cost Ionic Liquids and Water

Chambon

Fitriyanti

Verdía

et al. 2020

ACS Sustainable Chem. Eng.

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In this study, fractionation by sequential anti-solvent precipitation was applied to ionoSolv lignins for the first time. Pretreatment with the aqueous low-cost protic ionic liquid N,Ndimethylbutylammonium hydrogen sulfate ([DMBA][HSO 4 ], 80 wt% in water) was applied to Miscanthus (herbaceous), willow (hardwood) and pine (softwood) to extract lignin.Then, lignin was sequentially precipitated by addition of water as anti-solvent.Fractionation appeared to be controlled by molecular weight of lignin polymers. Fractions isolated with minimal water volumes were shown to have high molecular weight, polydispersity, thermal stability and T g (178 °C). Later precipitates were more monodisperse, had high phenolic and total hydroxyl content, lower thermal stability and T g (136 °C). Addition of 1 g of water per g of dry IL was able to precipitate up to 90 wt% Page 2 of 52 ACS Paragon Plus Environment ACS Sustainable Chemistry & Engineering 3 of lignin. Fractional precipitation represents a novel lignin isolation technique that can be performed as part of the lignin recovery procedure enabling a high degree of control of lignin properties. The effect of the fractionation on lignin structural, chemical and thermal properties was thoroughly examined by 2D HSQC NMR, GPC, TGA and DSC and compared to the unfractionated lignin precipitate obtained by addition of an excess of water.

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Section: Introductionmentioning

confidence: 99%

Fractionation by Sequential Antisolvent Precipitation of Grass, Softwood, and Hardwood Lignins Isolated Using Low-Cost Ionic Liquids and Water

Chambon

Fitriyanti

Verdía

et al. 2020

ACS Sustainable Chem. Eng.

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“…25 As a type of complex polyphenolic macromolecule, lignin source, molecular weight, purity, and structure have considerable effects on the characteristics of the lignin-containing PF resins. [26][27][28] Generally, the mechanical properties (bonding strength) of lignin-containing PF decrease with the increase in substitution of phenol by lignin, 29 although full substitution of phenol by lignin can produce adhesives having similar wet and dry shear strength to commercial phenol resorcinol formaldehyde ones. 30 Pizzi et al, demonstrated that under weakly acidic conditions, the divalent metal ions (e.g., manganese, zinc, magnesium oxides, or hydroxides) promote the production of ortho-phenolformaldehyde resin and accelerate the curing process.…”

Section: Introductionmentioning

confidence: 99%

“…Examples of chemical modifications of lignin include methylolation, demethylation, and introduction of phenolate . As a type of complex polyphenolic macromolecule, lignin source, molecular weight, purity, and structure have considerable effects on the characteristics of the lignin‐containing PF resins . Generally, the mechanical properties (bonding strength) of lignin‐containing PF decrease with the increase in substitution of phenol by lignin, although full substitution of phenol by lignin can produce adhesives having similar wet and dry shear strength to commercial phenol resorcinol formaldehyde ones …”

Section: Introductionmentioning

confidence: 99%

Zinc chloride/acetamide deep eutectic solvent‐mediated fractionation of lignin produces high‐ and low‐molecular‐weight fillers for phenol‐formaldehyde resins

Hong

Sun

Lian

et al. 2019

J of Applied Polymer Sci

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Lignin readily dissolves in a deep eutectic solvent (DES) composed of ZnCl 2 /acetamide 1:3 M ratio in concentrations up to 16.7 wt %, and upon addition of water, two fractions were obtained; one composed of lignin with low-molecular weight that remained dissolved in the DES/water mixture, whereas the other fraction of lignin with higher molecular weight (regenerated lignin, RL) was regenerated by precipitation. Both the RL fraction and the whole solution of lignin in DES were used to replace part of phenol (20 wt %) in the condensation of phenol and formaldehyde to introduce biomass in the resulting resins. The lignin treatment that produced the higher yield of RL consisted of lignin/DES ratio of 1:10 (w/w) stirred for 4 h at 100 C. By using 13 C NMR spectroscopy, a preferential cleavage of the S unit of lignin during DES treatment was identified. The modified phenol-formaldehyde resin (RLPF) containing the RL exhibited higher bonding strength (1.28 AE 0.16 MPa) and shorter Sunshine gel time (557 s) than PF (587 s), showing that the RL helps to improve the polycondensation process. The resin modified with the whole solution of lignin in DES exhibited the shortest Sunshine gel time due to the effect of zinc(II) accelerating the curing process.

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“…Lignin is a naturally occurring polymer which can be found in plants [ 1 ]. It has a heterogeneous amphiphilic structure containing benzene rings as well as reactive aliphatic and phenolic hydroxyl and phenolic functional groups, and is characterized as a biocompatible, biodegradable, and renewable material [ 1 , 2 , 3 , 4 ]. To date, this biopolymer has been widely used as a heating source to obtain energy, mostly for cellulose and hemicellulose-based industries, in which it is a waste product [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

Lignin-Based Spherical Structures and Their Use for Improvement of Cilazapril Stability in Solid State

et al. 2020

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Biopolymer-based spherical particles exhibit unique properties including narrow sizes and many functional groups on their surfaces. Therefore, they show great potential for application in many scientific and industrial processes. The main aim of this study was to prepare lignin-based spherical particles with the use of a cationic surfactant, hexadecyl(trimethyl)ammonium bromide (CTAB). In the first step, different preparation procedures were tested with varying parameters, including biopolymer and surfactant ratios, lignin filtration, and experimental time. The morphological and dispersion characteristics of the materials were determined to select the best samples with the most promising properties, which could then be tested for their acute toxicity. It was observed that almost all materials were characterized by spherical shapes in micro- and nanosizes. The sample with the best physicochemical properties was used for further analysis and then tested for medical applications: the improvement of the stability of a drug molecule, cilazapril (CIL). The formulated material (CIL@LC-2a 1:1 wt./wt.) exhibited outstanding properties and significantly improved the stability of cilazapril as tested in conditions of increased temperature and humidity. Lignin spherical particles may be employed as a promising material for shielding other active compounds from decomposition.

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Comparative analysis of different lignins as phenol replacement in phenolic adhesive formulations

Cited by 74 publications

References 31 publications

Fractionation by Sequential Antisolvent Precipitation of Grass, Softwood, and Hardwood Lignins Isolated Using Low-Cost Ionic Liquids and Water

Fractionation by Sequential Antisolvent Precipitation of Grass, Softwood, and Hardwood Lignins Isolated Using Low-Cost Ionic Liquids and Water

Zinc chloride/acetamide deep eutectic solvent‐mediated fractionation of lignin produces high‐ and low‐molecular‐weight fillers for phenol‐formaldehyde resins

Lignin-Based Spherical Structures and Their Use for Improvement of Cilazapril Stability in Solid State

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