REVIEW

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A Review on Lignin-Based Phenolic Resin Adhesive

Xiaoyu Gong, Yi Meng, Jie Lu, Yehan Tao, Yi Cheng,* and Haisong Wang*

genotoxicity by the World Health Organiza-

Replacing petroleum-based chemicals with biomass-based alternatives is tion’s International Agency.[4] Meanwhile,
becoming more and more important for the development of a low-carbon the growing concerns toward environmen-
economy around the world. The latest life cycle assessment displayed that tal friendliness, the increasing price of the
partially replacing phenol with biobased lignin in the process of synthesizing phenol and the desire to reduce the depen-
dence on crude oil give impetus to increase
phenolic resin adhesives used in wood panels industry can remarkably reduce
the use of the green and renewable alterna-
carbon emissions and negative environmental impact. The macromolecular tives in the production.[5]
structure of lignin is similar to that of phenolic resin and the basic structure As only nonpetroleum source of renew-
unit is similar to that of the phenol, thus endowing it with the potential to able aryl compounds in nature, lignin is
substitute phenol and reduce the release of formaldehyde in the preparation an appropriate alternative for phenol be-
cause it also contains phenylpropane units
process of phenolic resin. Importantly, the lignin-based adhesive exhibits
and its structure has similarity to that of
improved performance and reduced cost compared with the petroleum-based phenol.[6] However, the high steric hin-
adhesive due to the reduced adding amount of petroleum-based volatile drance, complex structure, small number of
components. However, the intrinsic large steric hindrance, structural active groups, and large resistance of aro-
heterogeneity, and low activity of the natural lignin limit its further application matic ring structure have restricted its wide
in the adhesive. Many researchers have developed the activation methods application in adhesive production.[7] In or-
der to increase the reactivity of lignin, acti-
such as physical modification, chemical modification, and biological
vation modification is often used to increase
modification to overcome these issues. The different modification of the lignin the content of existing active groups or in-
and their application in the adhesive area are mainly summarized here. troduce new active groups and the modi-
Besides, the modification methods and the curing mechanism are also fied lignin can be used to fabricate different
discussed. types of adhesives with high performances.
Based on the above facts, we will review
the recent status of the production of lignin-
based adhesives, the preparation methods
1. Introduction of the modified lignin-based adhesives, the curing and the ad-
hesive mechanism. In addition, the challenge and the future
As one of the largest economies in recent years, the wood com- prospect of the lignin-based adhesives are also discussed.
posite industries particularly the wood-based panel have brought
forward a new impetus.[1] Wood product industries widely use
the aldehydes adhesives (including phenol-formaldehyde (PF), 2. The Structure of Lignin
urea-formaldehyde (UF), and melamine formaldehyde adhe-
sives) in the manufacturing process. Among them, the pheno- As a by-product of traditional pulp and paper industry and emerg-
lic resin adhesive is most widely used due to the advantages of ing biomass refining industry, traditional lignin not only has
high adhesive strength, good water resistance, and good heat the advantages of large production, low cost, and renewable but
resistance.[2] However, the phenolic resin adhesive was synthe- also has the defects of complex structure, low reactivity, and
sized from the formaldehyde and phenol. As we all know, the phe- difficult degradation, so the industrial application of lignin is
nol and its vapors are also harmful to human eyes, skin, and the still very limited. Lignin is natural aromatic polymer with a
respiratory tract as well as the central nervous system and heart.[3] 3D network structure, including guaiacyl (G), syringyl propane
And the formaldehyde is also classified to be a carcinogen with (S), and p-hydroxyphenylpropane (H) (Figure 1a),[8] which are
highly crosslinked by C–O bonds and C–C bonds through the
dehydrogenation polymerization of phenylpropane structural
X. Gong, Y. Meng, J. Lu, Y. Tao, Y. Cheng, H. Wang units through monomers[9] Lignin contains phenolic hydroxyl,
Liaoning Key Laboratory of Lignocellulose Chemistry and BioMaterials aliphatic hydroxyl, aldehydes, and carboxyl groups that can react
Dalian Polytechnic University
Dalian, Liaoning 116034, China
with aldehydes or phenol, the process of which is similar to the re-
E-mail: chengyi18@dlpu.edu.cn; wanghs@dlpu.edu.cn action between phenol and formaldehyde to form phenolic resin
adhesives, thus implying the potential of lignin to partly substi-
The ORCID identification number(s) for the author(s) of this article tute phenol or formaldehyde when preparing wood adhesives.[10]
can be found under https://doi.org/10.1002/macp.202100434 Lignin not only can reduce the production cost of phenolic resin
DOI: 10.1002/macp.202100434 adhesives, but also decrease the content of free formaldehyde and

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Figure 1. a) Chemical structure of lignin (R: point of linkages with
other subunits of lignin) and b) active position on the phenolic lignin
structure.[8]
free phenol in phenolic resin that are harmful to the human’s
health and also the environment. In addition, it can decrease the
curing temperature of the resin, accelerate the curing speed, and
not easy to penetrate the glue.
However, lignin is an amorphous, highly branched, 3D struc-
ture polymer composed of three structural units with strong
steric hindrance. It should be noted that the active sites shown
in Figure 1b are the theoretical active sites, whereas in reality
most of them are hardly accessible. To enhance the reactivity of
lignin, its structure is modified to increase the content of methy-
lol, phenolic hydroxyl, or alcoholic hydroxyl, thereby enhancing
the polymerization degree of lignin based phenolic resin (lignin
phenol-formaldehyde, LPF) that can improve the resultant bond-
ing strength of LPF.[11] This review focuses on introducing differ-
ent kinds of modification methods of lignin and their reactivity
in the synthesis of LPF adhesives for the production of composite
wood panels.
3. Synthesis of LPF Adhesives and Their Curing
Mechanism
3.1. Synthesis of LPF Adhesives
Lignin has a natural advantage in the preparation of adhesives
because of its adhesiveness, which can be enhanced by vari-
ation of lignin itself.[9a] Most researches about LPF adhesives
focus on their applications, but few explore their copolymer-
ization mechanism. Mohamad Ibrahim[12] reported that the C5
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position of G-type lignin can undergo methylolation reaction
with formaldehyde to obtain methylolated lignin, which could
then undergo polycondensation reaction with phenol formalde-
hyde, whereas this theory has not been verified by experimental
data. Zhao et al.[13] used 13 C isotope-rich formaldehyde to react
with lignin to track the reaction sites of lignin. It was found that
the main site where the hydroxymethylation reaction occurs was
the C5 site of the lignin based on the analysis of the 13 C-NMR
spectrum.
In fact, it is difficult to clarify the copolymerization mecha-
nism of lignin, phenol, and formaldehyde directly because lignin
has a quite complex molecular structure with no exact molecu-
lar formula.[14] Some scholars[15] have expounded the possible
chemical reaction process of lignin, phenol, and formaldehyde by
studying the synthesis mechanism of lignin model compound-
phenol-formaldehyde copolymer resin, the process of which is
shown in Figure 2. The first hydroxymethyl reaction step happens
between phenol and formaldehyde as the hydroxymethyl rate of
lignin is slower than that of phenol. The mono-methylolation
product of phenol is mainly para-hydroxymethyl phenol and
the dimethylolation product is mainly ortho-para-hydroxymethyl
phenol, as shown in Figure 2. Next, the hydroxymethyl phenol
would preferably undergo condensation reaction with the unsub-
stituted active site on the benzene ring to form a dimer connected
by a methylene bond. With the progress of the polycondensation
reaction, in the later stage of the reaction, the polycondensation
reaction between the methylol groups of each type of prepoly-
mer begins to form a network crosslinked structure and a lignin
model compound-PF adhesive connected by methylene bond and
methylene ether bond is formed.[15c,16]
3.2. Curing Mechanism
The curing reaction of thermosetting PF resin is very complicated
and its specific curing reaction mechanism is still under study
and not yet fully understood.[16a,17] During this change, the main
curing reactions are
1) The hydroxymethyl group on the phenol nucleus undergoes
condensation reaction with the ortho- or para-position active hy-
drogen on other phenol nuclei, losing one molecule of water and
forming a methine bond.
2) The hydroxymethyl groups on the phenol nucleus under-
goes condensation reaction, losing one molecule of water and
forming two benzyl ether.
Under alkaline conditions, the curing reaction of phenolic
resin mainly generates methylene bonds. Under acidic condi-
tions, methylene bonds and ether bonds are formed simultane-
ously, but relatively stable methylene bonds are mainly formed
under strong acid conditions. At the same time, the size and
chemical properties of the substituents in the phenolic molecule
will affect the formation of ether bonds during the reaction.[18]
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Figure 2. Chemical synthesis of lignin model-phenolic resin. Reproduced with permission.[15c] Copyright 2015, Wiley Periodicals.

Due to the similar molecular structures of phenol and lignin Table 1. Modification method and properties of LPF adhesives.
molecules, the curing mechanism of LPF adhesives, mainly the
condensation reaction between the hydroxyl group and the con- Lignin Bonding
densation reaction between the hydroxyl group and the hydrogen content strength
Raw material Modification methods [%] [MPa] Ref.
on the aromatic ring has been reported to be similar to that of PF.
Moreover, it has been reported that the addition of lignin can re- Corncob lignin Phenolic 50 1.00 [20]

duce the activation energy and increase the curing speed of LPF Alkali lignin Phenolic 50 1.3 [ 19a]

effectively.[18] Wheat straw lignin Steam explosion 70 0.72 [21]

Wheat straw lignin Steam explosion 40 1.11 [21]

Acetic acid lignin Methylolation 30 0.7 [22]

4. Modification of the Lignin for Preparing Wood Wheat straw lignin Demethylation 60 2.11 [23]

Adhesives Alkali lignin Demethylation 50 0.88 [24]

Alkali lignin Demethylation 50 1.07 [ 16b]

Although some research results have been achieved in LPF resin,
Bagasse lignin Microwave hydrothermal 20 1.017 [25]
whereas the large molecular weight, large steric hindrance, few
[26]
C5 active sites, and low reactivity of lignin hinder the high-value Soda bagasse lignin Ionic liquids 20 0.71
utilization of lignin as substitution of phenol or aldehydes.[19] Black liquor lignin Deep eutectic solvent 40 1.3 [27]

Therefore, the modification of lignin is highly desirable to en- Cornstalk lignin Enzymatic hydrolysis 20 1.8 [28]

hance the its reactivity and the bonding strength of the formed
resin as wood adhesives. The modification methods were clas-
sified to three different kinds, namely, chemical modification,
physical modification, and bioactivation modification. Table 1
summarizes part of the studies about the LPF-adhesives in which
the modified lignin content and bonding strength of the LPF-
adhesives were reported.
4.1. Chemical Modification of Lignin
4.1.1. Phenolic Modification
Phenolic modification of lignin is the most commonly used mod-
ification method of lignin, which refers to the chemical reac-
tion between lignin and phenol. The content of phenolic hy-
droxyl groups can be increased by introducing phenol groups
to increase the reactivity of lignin and the number of reactive
sites.[29] Both alkaline and acidic solvent have been used for this
process.[30] Under alkaline conditions, only phenolic lignin can
break the 𝛼-ether bond or double bond of the side chain to form
the methylene quinone structure through the electron-induced
effect of phenolic hydroxyl group, and then undergo nucleophilic
substitution reaction with the ortho or para-phenolic hydroxyl
group of phenol (Figure 3a).Under acidic conditions, the ether
bonds at the 𝛼-position of the lignin-phenylpropane structural
unit are prone to breaking via combining with hydrogen ions
to form oxonium, and the positively charged carbon atoms will
be generated, and then play a substitution role in the ortho-para
position of phenol (Figure 3b). After phenolic modification, the
molecular weight of lignin decreases and the polydispersity de-
creases. The method is simple and can be achieved under mild
reaction conditions.
Khan et al.[31] used bagasse lignin as raw material for alka-
line phenolic modification and used it to prepare LPF adhesive.
Through the optimization of lignin concentration, formaldehyde
to phenol molar ratio, catalyst concentration, reaction time, and
reaction temperature, it was found that when the phenol substi-
tution amount was 50%, the modified resin had a faster curing

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Figure 3. Phenolic reaction of lignin in different medium:[30] a) alkaline
and b) acidic.
speed, and its shear strength (32 kg cm−2 ) was better than the con-
trol sample of PF (15 kg cm−2 ). Yang et al.[32] performed alkaline
phenolic modification on four kinds of lignin (corn cob lignin
(L1), poplar wood lignin (L2 and L3), and wheat straw lignin (L4))
respectively, the activity of the lignin obtained after phenolic mod-
ification increased significantly, which is more conducive for the
substitution of phenol to prepare LPF resin and the L1 should
be the best feedstock among the four kinds of technical lignin
tested considering the reactivity of the lignin. Our group[33] pre-
pared a lignin-based wood adhesive using the phenol modified
lignin and polyvinylpyrrolidone. The shear strength of the pre-
pared adhesive reached up to 1.70 MPa and it was still as high as
1.02 MPa after soaked for 24 h in water, satisfying the National
Primary Standard of plywood.
At present, there have been corresponding research reports on
the influencing factors of phenolic modification of lignin, but
there is a lack of systematic elaboration on the optimization of
lignin on the phenolic modification process parameters and the
significance of the influencing factors.
4.1.2. Oxidative Modification
Lignin contains a large number of side-chain aliphatic hy-
droxyl groups, terminal phenolic hydroxyl groups and ac-
tive benzyl sites, the selective oxidation of these structural
units enable to yield highly functionalized, monomeric or
oligomeric products such as vanillin, syringaldehyde, and 4-
hydroxybenzaldehyde.[30,34] Thus, oxidative degradation of lignin
is a very promising method to reduce the bond energy of lignin
and increase its reactivity.[35] The reaction conditions are rela-
tively mild. One example of oxidative modification is shown in
Figure 4.
Azarpira et al.[35b] reported that low molecular weight aromatic
compounds were successfully generated by oxidizing lignin
model compounds and pine milled wood lignin with copper(II)
sulfate pentahydrate catalyst. It was found that oxidized units
appear to be derived from 𝛽-aryl ether, phenylcoumaran, and
biphenyl ether components. To date, this method breaks down
the lignin polymeric structure reasonably effectively, producing
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Figure 4. The oxidation mechanism of lignin.[35b]
low molecular mass products. Akhil et al.[8] used laccase to oxi-
dize bagasse lignin for the preparation of lignin-based formalde-
hyde resin without using phenol. It was found that the reactivity
of lignin was enhanced by the oxidation, leading to an improved
adhesion performance of the formed adhesive.
Although green and efficient oxidative degradation of lignin is
an effective way for enhance the reactivity of lignin, the selectivity
and yield of the oxidized lignin are low.
4.1.3. Hydroxymethylation Modification
Another typical kind of chemical modification method is hydrox-
ymethylation or methylolation.[36] The aromatic ring and aro-
matic ring side chain of lignin are hydroxymethylated, but this
method would not increase the number of active sites. However,
the introduced methylol groups can not only copolymerize with
phenol or C5 of lignin structure but also with methylol phenol
or methylolated lignin, so the reaction activity of lignin can be
significantly improved.[37] Under alkaline conditions, the ortho
position of the phenol hydroxyl group of lignin and C𝛼 and C𝛽
of aromatic ring side chain can undergo an addition reaction
with formaldehyde to form a methylol group, which can further
polymerize with the active groups of phenol or lignin to pro-
duce lignin-phenolic copolymer resin.[38] According to different
hydroxymethyl reaction sites, lignin and formaldehyde may un-
dergo three hydroxymethylation reactions shown in Figure 5.
Chakar et al.[39] reported that formation of methylene bridges
led by the condensation reaction accomplished the polymeriza-
tion and crosslinking reactions of hydroxymethylated (or glyox-
alated) of kraft lignin with formaldehyde in an alkaline medium.
Malutan et al.[38b] reported that three different kinds of lignin
(wheat straw, sarkanda grass, and protobind 1000) were methy-
lolated with formaldehyde at different reaction temperatures (50
and 90 °C) and pH (10.5 and 12). Under the optimum reaction
conditions, hydroxymethyl groups were significantly increased
in wheat straw and sarkanda grass, meanwhile, sarkanda grass
lignin exhibited the highest reactivity compared to wheat straw
and protobind 1000. Yang et al.[15c,20,40] modified lignin by biore-
fining technology, hydrothermal degradation, hydroxymethyla-
tion, and phenol reaction to endow lignin with higher activity
for preparing adhesive for plywood. The prepared lignin-based
adhesive was efficient for reducing the emission of formalde-
hyde (0.11–0.24 mg L−1 ), meanwhile not significantly decreased
the bonding strength of plywood (1.35 MPa). Some studies[7a] re-
ported that although the hydroxymethyl modification of lignin
cannot increase the active site of lignin, it can improve the wet
strength of plywood when it is used to prepare adhesives.
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Figure 5. Type of lignin hydroxymethylation reaction.[37b]
Figure 6. The demethylation reaction mechanism of lignin.[7a]
4.1.4. Demethylation Modification
In some types of lignin fiber raw materials, the active C3 /C5 po-
sitions on the aromatic ring are occupied by methoxy groups,
which limit the reactivity of lignin. Therefore, partial or complete
conversion of methoxy groups into phenolic hydroxyl groups
through demethylation reaction can significantly improve the re-
activity of lignin.[16b,25] And at present, sulfur demethylation is
the most commonly used modification method for the demethy-
lation modification of lignin. When lignin is attacked by nucle-
ophiles such as SO3 2– , CH3 S– , and HS– , a demethylation reaction
would occur (Figure 6) and dimethyl sulfide is produced. Most
of these demethylation reactions require high temperature and
high-pressure conditions.[7b]
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Softwood kraft lignin was demethylated by biophysical meth-
ods to improve its reactivity.[41] In this study, softwood kraft lignin
was demethylated utilizing a mixture of iodocyclohexane and
dimethyl formamide under reflux for 3 h during 145 °C, bring-
ing a resulting yield of 87%. Song et al.[23] used an in situ gen-
erated Lewis’s acid to demethylate wheat straw alkali lignin. The
results showed that the relative content of the phenolic hydroxyl
group increased from 5.2% to 16.0%, while the relative value of
methoxy group decreased significantly from 0.82% to 0.17% af-
ter the demethylation process. Demethylation by Enzymes (O-
demethylases) also showed potential for their application in re-
moving the methoxyl groups of lignin, and producing a demethy-
lated kraft lignin enriched in vicinal-hydroxyl groups (see Figure
7).[42] It was found that carbohydrate substrates played a key role
in this modification process. However, the demethoxy process
generally requires complex processes such as high temperature
and high pressure with a high cost.[24]
4.2. Physical Modification of Lignin
4.2.1. Ionic Liquids Modification
Ionic liquids (ILs) are completely composed of anions and cations
and usually liquid or salts with low melting points at room tem-
perature, which have the advantages of good thermal stability and
strong solubility to a variety of biobased chemicals.[43] As a new
type of green solvent, ILs have shown good performance and ap-
plication potential in the dissolution and modification of ligno-
cellulosic raw materials.[6] It is found that during the dissolu-
tion of ionic liquids, lignin with high phenolic hydroxyl content,
small molecular weight, and high activity is obtained due to the
cleavage of aryl ether bonds.[43a,44] Among numerous ILs, 1-ethyl-
3-methylimidazolium acetate, (Emim)(OAc), was reported to ef-
fectively extract lignin from wood,[45] the proposed (Emim)(OAc)
pretreatment mechanism of lignin is shown in Figure 8.[46]
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Figure 7. Various types of O-demethylases and their enzymatic
demethylation reactions on lignin model compounds. Reproduced with
permission.[42] Copyright 2019, Elsevier.
Younesi-Kordkheili et al.[47] modified soda bagasse lignin by
(Emim)(OAc) ionic liquid and then the various content of un-
modified and modified lignins (10%, 15%, and 20%) were used
separately to replace urea in neutral UF resin. It was found
that the UF resin containing lignin modified by ILs had lower
formaldehyde emission and water absorption content than those
made from unmodified lignin, indicating that lignin modified by
ILs was better than unmodified lignin as an improving additive
in UF resin synthesis. In addition, the authors also reported the
effects of applying lignin modified by ionic liquids (Emim)(OAc)
or glyoxalated lignin on the synthesis of UF resins which were
further used for the preparation of wood-based panels. It was
found that the panels prepared with an ionic liquid modified UF
had higher mechanical strength than those made from UF resins
containing glyoxalated lignin. In order to investigate the physical
and mechanical properties of plywood panels bonded with ILs-
modified lignin-PF resin, Younesi-Kordkheili et al.[26] modified
soda bagasse lignin by (Emim)(OAc) ionic liquid, and then the
modified lignins were added as a substitute of phenol in PF resin
synthesis. It was found that the mechanical properties of the pan-
els could be significantly enhanced with increased percentage of
treated lignin content from 0 to 20 wt% and the new synthesized
resin can also help to reduce resin costs.
Imidazole-based ILs are most commonly used in biomass pre-
treatment and have achieved high success. However, the above-
mentioned ILs are derived from fossil resources, have certain tox-
icity, and are not biodegradable. Ionic liquid modified lignin used
to prepare PF adhesive has a low substitution rate for phenol,
which certainly is an obstacle for its industrial application.
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4.2.2. Deep Eutectic Solvent (DES) Modification
The DES refer to a two-component or three-component eutec-
tic mixture composed of a hydrogen bond acceptor and a hydro-
gen bond donor in a certain stoichiometric ratio, and its freezing
point is significantly lower than the melting point of the pure sub-
stance of each component. The modification of lignin by DES is
a new method that has emerged in recent years. Figure 9 shows
the structure of some halide salts (most commonly used hydro-
gen bond accepter) and hydrogen bond donors that used to pre-
pare DES.[48] The synergistic effect of the hydrogen bond donor
and acceptor in the DES would affect the structure and relative
molecular weight of lignin, so that the lignin is degraded into the
target product and its activity is improved.[48,49] DES synthesized
by choline chloride and a variety of hydrogen bond donors has
been studied for the dissolution of lignin.[50] It has been shown
that the regenerated lignin after DES pretreatment has good an-
tioxidant activity.[51]
Hong et al.[27] used Choline chloride-ZnCl2 DES, mole ratio
1:2, to improve the chemical reactivity of wheat straw alkali lignin
under different temperatures and time of pretreatment. Then the
modified lignin was used to synthesize PF adhesives as a phe-
nol replacement. Remarkably, the strength of the modified resin
(1.3 MPa) compared with PF resin was practically the same when
40 wt% of the phenol was replaced by the modified lignin. This
work shows that lignin can be readily modified in DES to im-
prove its reactivity and to advance its prospective further use in
the wood industry.
The simple, rapid, and low-cost synthesis process, the mild
treatment conditions, and the environmental friendliness have
attracted more and more research attention for DES. Currently,
the main research focus is the separation and modification pro-
cess of lignin in DES, whereas the modification mechanism of
lignin in DES and the better synthesis process of PF resin still
need further research.
4.2.3. Microwave Hydrothermal Method
Microwave is electromagnetic wave with short wavelength (1 m–
1 mm), high frequency (300 MHz–300 GHz), and fast radiation.
Under the irradiation of microwave, certain chemical bonds in
the compound can be made to vibrate or rotate due to the quan-
tum effects, leading to the weakening of these chemical bonds,
thereby reducing the activation energy of the reaction.[10b,52]
Microwave-assisted extraction has been reported to effectively in-
crease the lignin yield in biomass extraction and reduce the reac-
tion time, thus making the microwave hydrothermal technique
an efficient alternative to conventional isolation techniques in
lignin extraction process.[53] The 𝛽-O-4 ether bond structure in
the molecular structure of lignin is weakened in chemical bond
after microwave treatment, and being prone to fracture to gener-
ate more hydroxyl structures, as shown in Figure 10.[54]
With the aim of applying liquefaction product of bagasse lignin
(LPBL) as a partial substitute for petroleum-based phenol in the
preparation of PF adhesives, Li et al.[55] degraded bagasse lignin
in hot-compressed water by microwave heating using oxalic acid
as catalyst. They found that the molecular weight, viscosity, and
adhesive strength of LPBL-PF adhesives were found to be lower
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Figure 8. The proposed (Emim)(OAc) pretreatment mechanism of lignin. Reproduced with permission.[46] Copyright 2014, the Royal Society of Chem-
istry.
than those of pure PF adhesives. With the phenol replaced by
LPBL up to 20%, the viscosity and adhesive strength of the resin
were 4.046 Pa s and 1.017 MPa, respectively. In addition, com-
mercial Kraft lignin was successfully valorized into recyclable and
flexible polyester thermosets by microwave hydrolysis,[56] and it
was found that microwave processing compared to liquid-solid
extraction paved the way for higher yields of narrow dispersity
lignin fractions and matching final properties, providing an at-
tractive approach to LPF resins.
4.3. Bioactivation Modification of Lignin
Bioactivation modification refers to pretreatment techniques that
degrade lignocellulose through the action of microorganisms or
enzymes produced by microorganisms.[57] Biological pretreat-
ment is different from physical and chemical modification meth-
ods and the whole pretreatment process does not produce by-
products that are not conducive to the reaction, which is low-cost,
pollution-free and meets the requirements of green chemistry.[30]
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However, the instability and heat sensitivity of the enzyme limit
its large-scale application in industry.
Using biological methods to modify lignin mainly uses the
specific degradation reaction of fungi on specific functional
groups of lignin, such as removing some methoxy groups as
shown in Figure 11.[58] Fungi are most commonly used in bi-
ological pretreatment of biomass.[59] The most abundant fungi
that can degrade lignin in nature are white rot fungi[30,60] and
brown rot fungi.[61] For example, the cells of white rot fungi can
secrete a large number of polyphenol oxidase enzymes using oxy-
gen, mainly laccase, which has obvious demethoxy effects un-
der aerobic conditions.[30,60] Laccase modified Kraft lignin was
used to prepare PF adhesives,[62] which showed a reasonable
degree of water resistance property. Using 13 C-labeled tetram-
ethylammonium hydroxide thermochemolysis (13 C-TMAH) and
solid state 13 C NMR, Filley et al.[61] investigated the relation-
ship between lignin oxidation/demethylation and polysaccharide
metabolism study of spruce sapwood inoculated with one of two
brown-rot fungi (Postia placenta and Gloeophyllum trabeum). It
was found that a close relationship between lignin demethyla-
tion and polysaccharide loss and suggest demethylation may play
© 2022 Wiley-VCH GmbH

www.advancedsciencenews.com
Figure 9. Structures of some halide salts and hydrogen bond donors used in the formation of DES. Reproduced with permission.[48] Copyright 2014,
American Chemical Society.
Figure 10. Lignin degradation process by microwave.
Figure 11. Lignin biological modification by fungi.[30]
a mechanistic role in polysaccharide loss. Jin et al.[59] demon-
strated that the brown-rotted lignin (BRL) had a somewhat higher
formaldehyde reactivity than a purified kraft lignin. The high
formaldehyde reactivity of BRL might be useful as a partial re-
placement for phenol in PF adhesives. This contention was ver-
ified in this study when satisfactory flakeboards were produced
with a PF resin that had a 35% phenol substitution with BRL.
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4.4. Life Cycle Assessment (LCA)
LCA is a technique and method used to assess the environmen-
tal impact of a product throughout its life cycle, from the acqui-
sition of raw materials, production of the product to the disposal
of the product after use.[63] Pang et al.[64] separated the prod-
ucts after xylose residue alkali treatment for solid-liquid separa-
tion and the lignin-rich liquid obtained was directly concentrated
to prepare adhesives with excellent bonding strength(0.87 MPa)
and ultralow formaldehyde emission(0.07 mg L−1 ), without addi-
tional separation links, which reduced the chemical consump-
tion caused by lignin separation and reduced the difficulty of
wastewater treatment. Finally, the whole LCA evaluation of the
new and old processes was carried out (Figure 12). After each
step was evaluated, the results showed that the new strategy had
a lower carbon footprint. Steam has the greatest impact, followed
by electricity consumption in dilute alkali treatment, ethanol pro-
duction, and chemicals used in the production of adhesives and
xylose. In short, the new process is more efficient in terms of en-
vironmental benefits.
5. Future Prospects
As a by-product of the traditional pulp and paper industry
and meanwhile as an important composition of the emerg-
ing biomass refining industry, lignin has great potential and
economic benefits in the production of phenolic resin instead
of petrochemical raw materials considering its advantages like
abundance, low cost, and renewability. However, lignin has com-
plex structure and low reactivity, leading to some disadvantages
of the lignin-based adhesives such as high viscosity, difficult
sizing operation, and not easy to place for a long time, low
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Figure 12. “Cradle-to-gate” LCA system boundary for the current and proposed corncob biorefinery designs.

bonding strength when lignin substitution rate is high, and
inconsistent performance of different batches of products, so
lignin-based adhesives cannot replace traditional phenolic resin
adhesives in large quantities at present.
The main factor limiting the wide application of lignin-based
adhesive in composite wood industry is its complex structure and
economic feasibility. As one of the rapidly developed biomass
adhesives in recent years, if the water resistance and bonding
strength of lignin can be further improved, lignin-based adhe-
sive will certainly have a broad application prospect. With the ef-
forts of many researchers, the reactivity of lignin has been mod-
ified and improved, and it is reported that some lignin-based
copolymer adhesives have meet the requirements of some rel-
evant standards. However, further research is needed to investi-
gate the mechanism of the adhesives synthesis and modification
process.
6. Conclusions
The different modification of the lignin and their application in
the adhesive area were mainly summarized in this review. Lignin-
based adhesives cannot replace traditional phenolic resin adhe-
sives in large quantities, but the cost of lignin-based phenolic ad-
hesives can be decreased by optimizing the reaction conditions

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Yi Cheng received her Ph.D. degree from the Dalian Institute of Chemical Physics in 2018. Her re-
search interest was biobased fiber materials and chemicals and functional material for Li-ion batteries.
She has published over 20 papers in leading peer-reviewed journals, including ACS Applied Materials
and Interfaces, Journal of Power Sources, Carbohydrate Polymers etc.

Haisong Wang received his M.Sc. degree from the China National Pulp and Paper Research Institute
in 2004 and got his Ph.D. degree from the Tianjin University of Science and Technology, in 2008. He
joined the Qingdao Institute of Bioenergy and Bioprocess Technology, CAS, in 2008, and conducted
his visiting scholarship at the University of Wisconsin-Madison from 2010 to 2011. He has been work-
ing in Dalian Polytechnic University from 2016. His research interests are pretreatment, fractiona-
tion and effective conversion of lignocelluloses. He has published over 100 papers in leading peer-
reviewed journals, including ACS Nano, Bioresource Technology, etc., and holds 12 patents.

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