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Synthesis and Application of New Lignin-Based Polymers and Composites
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Synthesis and Application of New Lignin-Based Polymers and Composites

A special issue of Materials (ISSN 1996-1944). This special issue belongs to the section "Advanced Composites".

Deadline for manuscript submissions: closed (21 February 2023) | Viewed by 26300

Special Issue Editor

Prof. Dr. Dmitry V. Evtuguin

E-Mail Website
Guest Editor
Department of Chemistry & CICECO, Universidade de Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal
Interests: chemistry and technology of lignocellulosics; lignin chemistry; lignin-based polymers and composites; hybrid materials; catalysis; paper materials; analytic tools for natural polymers

Special Issue Information

Dear Colleagues,

Lignin is an amorphous aromatic irregular biopolymer, second in natural occurrence only to cellulose. In addition to its important physiological functions in vascular plants (promoting tissue binding, rigidity, antiseptic, and hydrophobicity properties), lignin is a promising renewable organic resource, with an annual increase resulting from biosynthesis of more than 20 billion tons. In practice, lignin is available mainly as a byproduct of the wood processing industries, whose annual production exceeds 50 million tons. This issue is a major challenge for chemists in relation to the valorization of lignin.

Although most technical lignins are burned for energy, their great potential is recognized for producing chemicals and advanced polymeric materials. Currently, water-soluble lignins, especially lignosulfonates from sulfite pulping, are widely valued for different purposes. However, remarkable progress in the use of lignins from kraft pulping and chemical/biochemical deconstruction of wood instills confidence in its wide applicability in materials instead of burning. Lignin can be used in its polymeric form as (i) unmodified additive in polymeric formulations by blending, or as (ii) a macromonomer, with or without modification to bring new functionalities, in advanced polymers/copolymers or (iii) after depolymerization to produce chemicals suitable for organic synthesis or as a fuel.

In conventional applications, technical lignins are essentially limited to being used as unmodified additives to different polymer blends and composites, in construction materials (concrete, cement, breaks, asphalt, etc.), in the extractive (oil production and mining) and manufacturing (ceramic, leather-processing, paint and varnish, carbon black, etc.) industries, agriculture (fertilizers, auxiliary chemicals, remediation, etc.), and in medicine. The most recent trends point to high-performance advanced lignin-based materials obtained by targeted modification, controlled polymerization, and nanostructuring techniques.

This Special Issue encourages researchers to contribute with their recent works (original research articles and reviews) related to advances in lignin utilization in new polymeric formulations, composites, functional and nanostructured materials.

Prof. Dr. Dmitry V. Evtuguin
Guest Editor

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Keywords

  • lignin
  • chemical modification
  • controlled polymerization
  • nanostructuring
  • resins
  • adhesives
  • adsorbents
  • hybrid materials
  • hydrogels
  • sensors
  • composite materials
  • functional materials
  • conductive composites
  • delivery systems
  • bioremediation

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Published Papers (7 papers)

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Research

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16 pages, 2417 KiB  
Article
Modification of Paper Surface by All-Lignin Coating Formulations
by Patricia I. F. Pinto, Sandra Magina, Sara Fateixa, Paula C. R. Pinto, Falk Liebner and Dmitry V. Evtuguin
Materials 2022, 15(22), 7869; https://doi.org/10.3390/ma15227869 - 8 Nov 2022
Cited by 6 | Viewed by 2841
Abstract
All-lignin coating formulations were prepared while combining water-soluble cationic kraft lignin (quaternized LignoBoost®, CL) and anionic lignosulphonate (LS). The electrostatic attraction between positively charged CL and negatively charged LS led to the formation of insoluble self-organized macromolecule aggregates that align [...] Read more.
All-lignin coating formulations were prepared while combining water-soluble cationic kraft lignin (quaternized LignoBoost®, CL) and anionic lignosulphonate (LS). The electrostatic attraction between positively charged CL and negatively charged LS led to the formation of insoluble self-organized macromolecule aggregates that align to films. The structures of the formed layers were evaluated by atomic force microscopy (AFM), firstly on glass lamina using dip-coating deposition and then on handsheets and industrial uncoated paper using roll-to-roll coating in a layer-by-layer mode. Coated samples were also characterized by optical microscopy, scanning electron microscopy (SEM) coupled with energy dispersive spectroscopy (SEM/EDS), and contact angle measurements. It was suggested that the structure of all-lignin aggregates is the result of the interaction of amphiphilic water-soluble lignin molecules leading to their specifically ordered mutual arrangement depending on the order and the mode of their application on the surface. The all-lignin coating of cellulosic fiber imparts lower air permeability and lower free surface energy to paper, mainly due to a decrease in surface polarity, thus promoting the paper’s hydrophobic properties. Moderate loading of lignin coating formulations (5–6 g m−2) did not affect the mechanical strength of the paper. Full article
(This article belongs to the Special Issue Synthesis and Application of New Lignin-Based Polymers and Composites)
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17 pages, 4609 KiB  
Article
Oxyalkylation of Lignoboost™ Kraft Lignin with Propylene Carbonate: Design of Experiments towards Synthesis Optimization
by Fernanda Rosa Vieira, Ana Barros-Timmons, Dmitry Victorovitch Evtuguin and Paula C. O. R. Pinto
Materials 2022, 15(5), 1925; https://doi.org/10.3390/ma15051925 - 4 Mar 2022
Cited by 12 | Viewed by 2558
Abstract
Oxyalkylation with propylene carbonate (PC) is a safe process to convert lignin into a reactive liquid polyol to be used in polyurethane formulations. In this study, the effect of operating conditions of oxyalkylation (temperature, time and quantify of PC) on the quality of [...] Read more.
Oxyalkylation with propylene carbonate (PC) is a safe process to convert lignin into a reactive liquid polyol to be used in polyurethane formulations. In this study, the effect of operating conditions of oxyalkylation (temperature, time and quantify of PC) on the quality of lignin-based polyol in terms hydroxyl number (IOH) and viscosity was studied. Full factorial modeling and response surface methodology (RSM) were applied to study the effect and interaction of process variables on the IOH and viscosity of lignin-based polyols. The results revealed that the IOH is highly affected by the reaction time, while the viscosity is affected by the amount of PC. Validation experiments confirmed the model is reliable. Furthermore, RSM optimization allowed to reduce the amount of PC by about 50% and to increase the lignin content in the polyol from 12.5% to 25% (w/w) depending on the temperature and time of the process and also on the purpose of the polyol produced (i.e., application in rigid foams or adhesives). Full article
(This article belongs to the Special Issue Synthesis and Application of New Lignin-Based Polymers and Composites)
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14 pages, 4439 KiB  
Article
Structural Analysis of Lignin-Based Furan Resin
by Xuhai Zhu, Bardo Bruijnaers, Tainise V. Lourençon and Mikhail Balakshin
Materials 2022, 15(1), 350; https://doi.org/10.3390/ma15010350 - 4 Jan 2022
Cited by 11 | Viewed by 3068
Abstract
The global “carbon emission peak” and “carbon neutrality” strategic goals promote us to replace current petroleum-based resin products with biomass-based resins. The use of technical lignins and hemicellulose-derived furfuryl alcohol in the production of biomass-based resins are among the most promising ways. Deep [...] Read more.
The global “carbon emission peak” and “carbon neutrality” strategic goals promote us to replace current petroleum-based resin products with biomass-based resins. The use of technical lignins and hemicellulose-derived furfuryl alcohol in the production of biomass-based resins are among the most promising ways. Deep understanding of the resulting resin structure is a prerequisite for the optimization of biomass-based resins. Herein, a semiquantitative 2D HSQC NMR technique supplemented by the quantitative 31P NMR and methoxyl group wet chemistry analysis were employed for the structural elucidation of softwood kraft lignin-based furfuryl alcohol resin (LFA). The LFA was fractionated into water-insoluble (LFA-I) and soluble (LFA-S) parts. The analysis of methoxyl groups showed that the amount of lignin was 85 wt% and 44 wt% in LFA-I and LFA-S fractions, respectively. The HSQC spectra revealed the high diversity of linkages formed between lignin and poly FA (pFA). The HSQC and 31P results indicated the formation of new condensed structures, particularly at the 5-position of the aromatic ring. Esterification reactions between carboxyl groups of lignin and hydroxyl groups of pFA could also occur. Furthermore, it was suggested that lignin phenolic hydroxyl oxygen could attack an opened furan ring to form several aryl ethers structures. Therefore, the LFA resin was produced through crosslinking between lignin fragments and pFA chains. Full article
(This article belongs to the Special Issue Synthesis and Application of New Lignin-Based Polymers and Composites)
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18 pages, 2054 KiB  
Article
Synthesis of Lignosulfonate-Based Dispersants for Application in Concrete Formulations
by Sandra Magina, Ana Barros-Timmons and Dmitry V. Evtuguin
Materials 2021, 14(23), 7388; https://doi.org/10.3390/ma14237388 - 2 Dec 2021
Cited by 11 | Viewed by 3287
Abstract
Lignosulfonates (LS) are products from the sulfite pulping process that could be applied as renewable environmentally-friendly polymeric surfactants. Being widely used as plasticizers and water-reducing admixtures in concrete formulations LS compete in the market with petroleum-based superplasticizers, such as naphthalene sulfonate formaldehyde polycondensate [...] Read more.
Lignosulfonates (LS) are products from the sulfite pulping process that could be applied as renewable environmentally-friendly polymeric surfactants. Being widely used as plasticizers and water-reducing admixtures in concrete formulations LS compete in the market with petroleum-based superplasticizers, such as naphthalene sulfonate formaldehyde polycondensate (NSF) and copolymer polycarboxylate ethers (PCE). In this work, different chemical modification strategies were used to improve LS performance as dispersants for concrete formulations. One strategy consisted in increasing the molecular weight of LS through different approaches, such as laccase and polyoxometalate-mediated polymerization, glyoxalation, and reversible addition-fragmentation chain transfer (RAFT) polymerization. The other strategy consisted of preparing LS-based non-ionic polymeric dispersants using two different epoxidized oligomer derivatives of poly(ethylene glycol) (PEG) and poly(propylene glycol) (PPG). Modified LS were used to prepare cement pastes, which were examined for their fluidity. Results revealed that the most promising products are PPG-modified LS due to the introduction of PPG chains by reaction with phenolic moieties in LS. The enhanced dispersant efficiency of the ensuing products is probably related not only to electrostatic repulsion caused by the sulfonic ionizable groups in LS but also to steric hindrance phenomena due to the grafted bulky PPG chains. Full article
(This article belongs to the Special Issue Synthesis and Application of New Lignin-Based Polymers and Composites)
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18 pages, 5628 KiB  
Article
Lignosulfonate-Based Polyurethane Adhesives
by Sandra Magina, Nuno Gama, Luísa Carvalho, Ana Barros-Timmons and Dmitry Victorovitch Evtuguin
Materials 2021, 14(22), 7072; https://doi.org/10.3390/ma14227072 - 21 Nov 2021
Cited by 13 | Viewed by 3299
Abstract
The feasibility of using lignosulfonate (LS) from acid sulphite pulping of eucalyptus wood as an unmodified polyol in the formulation of polyurethane (PU) adhesives was evaluated. Purified LS was dissolved in water to simulate its concentration in sulphite spent liquor and then reacted [...] Read more.
The feasibility of using lignosulfonate (LS) from acid sulphite pulping of eucalyptus wood as an unmodified polyol in the formulation of polyurethane (PU) adhesives was evaluated. Purified LS was dissolved in water to simulate its concentration in sulphite spent liquor and then reacted with 4,4′-diphenylmethane diisocyanate (pMDI) in the presence or absence of poly(ethylene glycol) with Mw 200 (PEG200) as soft crosslinking segment. The ensuing LS-based PU adhesives were characterized by infrared spectroscopy and thermal analysis techniques. The adhesion strength of new adhesives was assessed using Automated Bonding Evaluation System (ABES) employing wood strips as a testing material. The results showed that the addition of PEG200 contributed positively both to the homogenization of the reaction mixture and better crosslinking of the polymeric network, as well as to the interface interactions and adhesive strength. The latter was comparable to the adhesive strength recorded for a commercial white glue with shear stress values of almost 3 MPa. The optimized LS-based PU adhesive formulation was examined for the curing kinetics following the Kissinger and the Ozawa methods by non-isothermal differential scanning calorimetry, which revealed the curing activation energy of about 70 kJ·mol−1. Full article
(This article belongs to the Special Issue Synthesis and Application of New Lignin-Based Polymers and Composites)
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20 pages, 5747 KiB  
Article
Lignosulfonate-Based Conducting Flexible Polymeric Membranes for Liquid Sensing Applications
by Sandra Magina, Alisa Rudnitskaya, Sílvia Soreto, Luís Cadillon Costa, Ana Barros-Timmons and Dmitry V. Evtuguin
Materials 2021, 14(18), 5331; https://doi.org/10.3390/ma14185331 - 15 Sep 2021
Cited by 4 | Viewed by 2756
Abstract
In this study, lignosulfonate (LS) from the acid sulfite pulping of eucalypt wood was used to synthesize LS-based polyurethanes (PUs) doped with multiwalled carbon nanotubes (MWCNTs) within the range of 0.1–1.4% w/w, yielding a unique conducting copolymer composite, which was [...] Read more.
In this study, lignosulfonate (LS) from the acid sulfite pulping of eucalypt wood was used to synthesize LS-based polyurethanes (PUs) doped with multiwalled carbon nanotubes (MWCNTs) within the range of 0.1–1.4% w/w, yielding a unique conducting copolymer composite, which was employed as a sensitive material for all-solid-state potentiometric chemical sensors. LS-based PUs doped with 1.0% w/w MWCNTs exhibited relevant electrical conductivity suitable for sensor applications. The LS-based potentiometric sensor displayed a near-Nernstian or super-Nernstian response to a wide range of transition metals, including Cu(II), Zn(II), Cd(II), Cr(III), Cr(VI), Hg(II), and Ag(I) at pH 7 and Cr(VI) at pH 2. It also exhibited a redox response to the Fe(II)/(III) redox pair at pH 2. Unlike other lignin-based potentiometric sensors in similar composite materials, this LS-based flexible polymeric membrane did not show irreversible complexation with Hg(II). Only a weak response toward ionic liquids, [C2mim]Cl and ChCl, was registered. Unlike LS-based composites comprising MWCNTs, those doped with graphene oxide (GO), reduced GO (rGO), and graphite (Gr) did not reveal the same electrical conductivity, even with loads up to 10% (w/w), in the polymer composite. This fact is associated, at least partially, with the different filler dispersion abilities within the polymeric matrix. Full article
(This article belongs to the Special Issue Synthesis and Application of New Lignin-Based Polymers and Composites)
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Review

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32 pages, 3128 KiB  
Review
Lignin as a Renewable Building Block for Sustainable Polyurethanes
by Fernanda Rosa Vieira, Sandra Magina, Dmitry V. Evtuguin and Ana Barros-Timmons
Materials 2022, 15(17), 6182; https://doi.org/10.3390/ma15176182 - 5 Sep 2022
Cited by 37 | Viewed by 6991
Abstract
Currently, the pulp and paper industry generates around 50–70 million tons of lignin annually, which is mainly burned for energy recovery. Lignin, being a natural aromatic polymer rich in functional hydroxyl groups, has been drawing the interest of academia and industry for its [...] Read more.
Currently, the pulp and paper industry generates around 50–70 million tons of lignin annually, which is mainly burned for energy recovery. Lignin, being a natural aromatic polymer rich in functional hydroxyl groups, has been drawing the interest of academia and industry for its valorization, especially for the development of polymeric materials. Among the different types of polymers that can be derived from lignin, polyurethanes (PUs) are amid the most important ones, especially due to their wide range of applications. This review encompasses available technologies to isolate lignin from pulping processes, the main approaches to convert solid lignin into a liquid polyol to produce bio-based polyurethanes, the challenges involving its characterization, and the current technology assessment. Despite the fact that PUs derived from bio-based polyols, such as lignin, are important in contributing to the circular economy, the use of isocyanate is a major environmental hot spot. Therefore, the main strategies that have been used to replace isocyanates to produce non-isocyanate polyurethanes (NIPUs) derived from lignin are also discussed. Full article
(This article belongs to the Special Issue Synthesis and Application of New Lignin-Based Polymers and Composites)
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