Carbohydrate Polymers 136 (2016) 121127

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Carbohydrate Polymers
journal homepage: www.elsevier.com/locate/carbpol

Improve the ame retardancy of cellulose bers by grafting zinc ion

KeKe Zhang, Lu Zong, Yeqiang Tan, Quan Ji , Weicai Yun, Ran Shi, Yanzhi Xia
Collaborative Innovation Center for Marine Biomass Fibers, Materials and Textiles of Shandong Province, Key Laboratory for Advanced Fiber Materials and
Modern Textiles, College of Chemical Engineering, Qingdao University, Qingdao 266071, China

a r t i c l e i n f o a b s t r a c t

Article history: Zinc ion as the only ame retardant of cellulose bers was successfully grafted onto cellulose bers. Graft-
Received 21 July 2015 ing maleic anhydride onto cellulose bers via homogeneous acylation reaction between N,N-dimethyl
Received in revised form 7 September 2015 formamide (DMF) as the rst step. Then, graft zinc ion onto the formed cellulose bers was conducted
Accepted 10 September 2015
with zinc carbonate. The resulting copolymers were characterized by FTIR. Flame retardancy and ther-
Available online 11 September 2015
mal degradation of zinc-ion-modied cellulose bers (celluloseZn bers) was investigated by limiting
oxygen index (LOI), cone calorimeter (CONE), XRD, TG and SEM. Zinc ion could effectively improve ame
Keywords:
retardancy and thermal degradation when its content increases up to 4.96 wt%.
Maleic anhydride grafting
Cellulose bers 2015 Elsevier Ltd. All rights reserved.
CelluloseZn bers
Flame retardancy
Thermal degradation

1. Introduction pollution or secondary damage to human beings (Cheema, El-

Recently, cellulose bers are widely used, especially in tex-
tiles, due to their numerous advantages (Sonnier, Otazaghine,
Viretto, Apolinario, & Ienny, 2015; Yu & Qin, 2014; Zhuo & Sun,
2014): biodegradability, recyclability, hydrophilicity, non-toxicity,
low density, low cost, excellent air permeability. However, low
compatibility with hydrophobic polymer matrix, thermal sensitiv-
ity and the high ammability limit their utilization (Avila Ramirez,
Suriano, Cerrutti, & Foresti, 2014; Sonnier et al., 2015).
Cellulose bers are easily burnt and are difcult to extinguish.
Once ignited, cellulose bers are engulfed rapidly due to bers
density and structure (Jiang, Li, Hu, & Fan, 2010). Since numerous
injuries and fatalities are caused by re accidents, ame retardant
textile is in high demand for work clothing, reghter apparel,
institutional draperies, institutional upholstery, institutional and
commercial carpet, transportation, military garments and bedding
(Abou-Okeil, El-Sawy, & Abdel-Mohdy, 2013).
In the 19501980s, treatments, formulations and additives were
developed to improve the ame retardancy (Horrocks, Kandola,
Davies, Zhang, & Padbury, 2005). Flame retardants, containing halo-
gen, nitrogen, and phosphorus are widely used to impart ame
retardancy property (Gaan & Sun, 2007; Horrocks, 2011; Jiang, Jin,
& Park, 2015; La Guardia & Hale, 2015). However, it is well known
that those traditional ame retardants can cause environmental
Corresponding authors.
E-mail addresses: jiquan@188.com (Q. Ji), xiayz@qdu.edu.cn (Y. Xia).
Shafei, & Hauser, 2013; Liu, 2014).
In the present study, metal oxides can positively improve the
ame retardancy such as itanium dioxide (TiO2 ) and zinc oxide
(ZnO), which have been used separately to improve the ame
retardancy of cellulosic fabrics (Poon & Kan, 2015). In addition,
additional functional properties are obtained by adding the nano-
ZnO such as improved UV-absorption and strength.
Chemical modications could be a good solution to improve the
ame retardancy of cellulose bers. Grafting of an ideal functional
group is a good alternative to modify cellulose. Therefore, grafting
zinc ions onto cellulose bers appears as a good way to improve the
ame retardancy, which can minimize the side effects of the tradi-
tional ame retardant treatment such as emitting very low smoke
or toxic gases during combustion, reducing some harmful effects to
the marine environment, causing less environment problems and
eventually doing less secondary damage to human beings.
In this study, the effect of zinc ions as the only ame retardant of
cellulose bers was studied. We employed chemical modications
to graft zinc ion onto the cellulose bers and successfully prepared
celluloseZn bers with different zinc ions contents. First step,
maleic anhydride were grafted onto cellulose bers via homoge-
neous acylation reaction using N,N-dimethyl formamide (DMF) as
reaction medium. Then, grafting zinc ion onto the formed cellulose
bers was conducted with zinc carbonate. The ame retardancy
and thermal degradation of modied cellulose bers were investi-
gated. Moreover, grafting degree of maleic anhydride onto cellulose
bers and the zinc ion ame-retardant mechanism for the cellulose
bers were also discussed.

http://dx.doi.org/10.1016/j.carbpol.2015.09.026
0144-8617/ 2015 Elsevier Ltd. All rights reserved.
122 K. Zhang et al. / Carbohydrate Polymers 136 (2016) 121127

Scheme 1. Synthesis of maleic acid grafted cellulose bers and celluloseZn bers.

2. Experimental

2.1. Materials

Cellulose bers (viscose bers) was obtained from Hailong

Industrial Co., Ltd. (Shandong, China); N,N-dimethyl formamide
(DMF), maleican hydride, zinc carbonate (ZnCO3 ) and acetone were
purchased from China Pharmaceutical Group Chemical Reagent Co.,
Ltd. (Shanghai, China).

2.2. Methods

2.2.1. Preparation of maleic anhydride grafted cellulose bers

In a rst step cellulose bers (16.2 g, drying 2 h at 50 C) were
added to solutions of maleic anhydride and DMF. Then, the grafting
reaction was carried out in a 500 mL three-necked ask equipped
with a reux condenser, nitrogen line, and magnetic stirring bar
immersed in an oil bath. The solution was stirred at 100 C for 3 h
after nitrogen bubbling. The ratio of the cellulose bers to maleic
anhydride to DMF was changed by 1:3:6, 1:5:6, and 1:6:6 to prepare
different graft degree of maleic acid grafted cellulose bers. The
grafted cellulose bers were extensively washed with deionized
water and aceton to remove the unreacted maleic anhydride. Then,
they were subsequently dried in an oven at 50 C. Finally, pure
Fig. 1. FTIR spectra of cellulose bers, maleic acid grafted cellulose bers and
different graft degree of maleic acid grafted cellulose bers were celluloseZn bers.
obtained.

2.2.2. Preparation of celluloseZn bers 40 C for 1 h. CelluloseZn bers were washed with deionized water
In a rst step 1 g ZnCO3 was added into 0.5 L deionized water. and dried in an oven at 50 C. Finally, different zinc ion contents of
Then, different graft degrees of maleic acid grafted cellulose bers celluloseZn bers were successfully prepared. According to the
were added into the above solution and stirred magnetically at ratio of cellulose bers to maleic anhydride to zinc ion (g/g/g),
 K. Zhang et al. / Carbohydrate Polymers 136 (2016) 121127 123

Fig. 2. (a) Heat release rates (HRR), (b) total heat released (THR) and (c) total smoke release (TSR) for cellulose bers, 1#celluloseZn, 2#celluloseZn, (d) 3#celluloseZn.

the obtained samples were labeled as 1#celluloseZn (the ratio
is 1:3:5), 2#celluloseZn (the ratio is1:5:6), and 3#celluloseZn
(the ratio is 1:6:6) for later tests. The synthesis procedure of maleic
acid grafted cellulose bers and celluloseZn bers was shown in
Scheme 1.
2.3.2. Fourier transform infrared (FTIR) spectroscopy
FTIR spectroscopic study was performed with Nicolet 5700
Fourier-transform infrared spectrometer for the maleic acid grafted
cellulose bers, celluloseZn bers and cellulose bers to conrm
the formation of the grafted cellulose by using KBr pellets.

2.3. Characterization 2.3.3. Limiting oxygen index (LOI)

The LOI method was used to assess the ignition and ease of
2.3.1. Graft degree extinction of a sample. LOI was performed according to an inter-
The maleic anhydride content of maleic acid grafted cellulose national standard ASTM D2863 by means of HC-2 type instrument.
bers (Wm ) was calculated according to Eq. (1). The sample of 100 mm 40 mm 2 mm was for the LOI test.

98 (V1 V2 ) c 2.3.4. Cone calorimetry (CONE)

Wm = (1)
2 m 1000 The cone calorimeter was used to evaluate the ammability
of a sample. This test was performed according to the ISO 5660
where V1 and V2 are the consumption volume of hydrochloric
standard. 10 g sample of 100 mm 100 mm 4 mm was for the test.
acid standard solution by cellulose bers before and after grafting
The heat release rate (HRR), total heat release (THR) and total smoke
maleic acid, c is the concentration of the hydrochloric acid standard
release (TSR) were recorded.
solution and m is the mass of determined maleic acid grafted cel-
lulose bers.
2.3.5. X-ray diffractions (XRD) measurements
162 Wm Samples burned in a tube furnace at 280 C and 400 C were
Graft degree = 100% (2)
98 (1 Wm ) recorded on XRD DX2700 at the accelerating voltage of 40 kV and
124 K. Zhang et al. / Carbohydrate Polymers 136 (2016) 121127
Fig. 3. X-ray diffraction patterns of (a) cellulose bers, (b) 3#celluloseZn, (c) 3#celluloseZn pyrolyzed at 280 C and (d) 3#celluloseZn pyrolyzed at 400 C.
a current of 30 mA under Cu-K radiation. X-ray diffractions (XRD)
were carried out in the 2 range from 5 to 80 .
2.3.6. Thermogravimetric analysis (TG)
Thermogravimetric analysis (TG) was performed with a NET-
ZSCH TG 209 F1 Libra from room temperature to 800 C at a
heating rate of 20 C/min under 40 mL/min ow rate of nitrogen.
2.3.7. Scanning electron microscopy (SEM)
Samples burned in a tube furnace at 400 C and sputtered with
gold were examined using a Hitachi TM-3000 (Japan) SEM at a beam
voltage of 3.0 kW.
3. Results and discussion
3.1. FTIR spectroscopic analysis
FTIR spectroscopic analysis was used to verify the formation of
the graft cellulose bers as shown in Fig. 1. The FTIR spectra of
all the samples exhibited a broad band from 3100 to 3500 cm1 ,
which is assigned to O H stretching vibrations. The band at
10101030 cm1 is assigned to C O C stretching vibrations in
the ether group from the pyran ring. The stretching vibrations of
C O C bonds in the glycosidic is located at 10601100 cm1 .
The bands at 2891 cm1 in the cellulose bers, 2920 cm1 in
the maleic acid grafted cellulose bers, and 2918 cm1 in the
celluloseZn bers are the C H stretching vibrations of the pyran
ring (de Melo, da Silva Filho, Santana, & Airoldi, 2009). The weak
band at 3057 cm1 in the maleic acid grafted cellulose bers is
attributed to an intramolecular hydrogen stretching bond from
the maleate conformations. The peaks at 1728 and 1165 cm1
in maleic acid grafted cellulose bers and 1733 and 1171 cm1
in celluloseZn bers are attributed to C O stretching vibra-
tions in the ester group from the carbonyl (Gurgel, Freitas, & Gil,
2008; Schwanninger, Rodrigues, Pereira, & Hinterstoisser, 2004).
The characteristic peaks at 1637 cm1 are attributed to C C
double bond stretching vibrations of the carboxyl group, which
demonstrate that the C6 primary hydroxyl group of cellulose
macromolecules formed an ester bond with maleic anhydride by
dehydrations. The bands at 2597 and 1214 cm1 are attributed to
O H (carboxylic) and CO OH stretching vibrations in the maleic
acid grafted cellulose bers, respectively. Also, worthy of note is
that the absence of any band at 25002800 cm1 conrms zinc
ions were completely grafted on the carboxyl of maleic acid. More-
over, a new band at 819 cm1 in the maleic acid grafted cellulose
bers related to the out-of-plane deformations for carboxyl groups
is shifted and weakened in celluloseZn bers (Wibowo, Desai,
Mohanty, Drzal, & Misra, 2006). This also supports the successful
grafting of zinc ion
3.2. Flame retardancy analysis
3.2.1. LOI analysis
LOI is the minimum concentration of oxygen in an oxy-
gen/nitrogen gas stream mixture to maintain combustion, which
is a simple method to measure ammability of materials (Tomak &
Cavdar, 2013). A higher LOI value of the material indicates that the
material is more difcult to combustion. The LOI value of a sample
is 21 or below ignites easily and burns rapidly in air. Fibers with
LOI values between 24 and 27 are difcult to combust and when
 K. Zhang et al. / Carbohydrate Polymers 136 (2016) 121127 125

Table 1
Limiting oxygen index and cone calorimeter data.

Parameters and samples Cellulose ber 1#CelluloseZn 2#CelluloseZn 3#CelluloseZn

Zinc content (wt%) 0 1.52 3.51 4.96

LOI 19 24 27 30
Time to ignitions (s) 6 10 32 59
Peak HRR (kW/m2 ) 88.13 56.88 39.50 29.43
Total heat release (MJ/m2 ) 18.89 4.63 3.35 1.89
Mean HRR (kW/m2 ) 61.80 20.03 19.13 13.40
Total smoke release (m2 /m2 ) 4.97 9.19 2.92 1.28

values of LOI above 27, the bers are considered to be ame retar-
dant (Tomak & Cavdar, 2013; Xie, Gao, & Zhang, 2013). After zinc
ion grafted onto cellulose bers, the LOI value of the cellulose bers
increased from 19 to 30 depending on zinc ion contents as shown
in Table 1. Therefore, celluloseZn bers tend to be ame retardant
when zinc ion content increases up to 4.96 wt%.
3.2.2. CONE Analysis
Cone calorimeter (CONE) is another method used to measure
the ammability of materials (Spontn, Ronda, Gali, & Cdiz,
2009). Fig. 1 shows (a) heat release rates (HRR), (b) total heat
released (THR) and (c) total smoke release (TSR) for cellulose bers,
1#celluloseZn, 2#celluloseZn, 3#celluloseZn and Table 1 sum-
marizes the main data recorded.
According to Table 1, the TTI of cellulose bers is 6 s, and that of
the celluloseZn bers is 10 s, 32 s, and 59 s. The ignition time (TTI)
is described as the time needed to achieve sustained aming com-
bustion at a particular irradiance and represents the time people
have to escape from a re. Thus, celluloseZn bers take longer to
burn, and are more difcult to combust.
From Fig. 2(a), the HRR trend curve of cellulose bers is higher
than those of celluloseZn bers. The time to reach the peak of
HRR in all the ber samples increases, and the value of the peak
HRR gradually reduces due to the difference in zinc ion content. In
particular, the value of the peak HRR and the mean HRR decrease
from 88.13 kW/m2 (cellulose bers) to 29.43 kW/m2 (celluloseZn)
and 61.80 kW/m2 (cellulose bers) to 13.40 kW/m2 (celluloseZn),
respectively (Table 1). The higher the value of HRR, the more
combustion heat is transferred to the material surface, which can
accelerate burning and pyrolysis. These results show that grating
zinc ion onto cellulose bers can modify the ame retardancy.
Fig. 2(b) clearly shows that the THR curve of the cellulose bers
gradually decreases with increasing the zinc content in the bers.
As shown in Table 1, the value of THR decreases from 18.89 MJ/m2
for the cellulose bers to 1.89 MJ/m2 for the bers with the highest
zinc content. A lower value of THR during the combustion indicates
a better ame retardant property of the material. This nding sug-
gests that zinc ion can improve the ame-retardant properties of
cellulose bers.
For ame-retardant material, the total smoke release (TSR) in
the combustion process is essential information and determines
the degree of atmosphere toxicity in a re scene. A greater TSR
value indicates a higher combustion toxicity. The data in Table 1
show that the TSR value uctuates with increasing zinc ion content
in the ber samples. The TSR value of the 3#celluloseZn bers
is 1.28 m2 /m2 , which represents a signicant reduction compared
with that of the cellulose bers (4.97 m2 /m2 ).
Fig. 2(c) shows the TSR curve trend in detail. The TSR value of
1#celluloseZn is higher than that of the cellulose bers. How-
ever, the smoke release rapidly decreases with increasing zinc ion
content in the bers samples. Because a small amount of zinc
ion in the cellulose bers may promote incomplete combustion
in the inner bers, resulting in the production of a large amount
of carbon monoxide, carbon dioxide and other products of incom-
plete combustion. Therefore, we believe that the cellulose bers
containing moderate zinc ion content can not only improve the
ame-retardant properties of cellulose bers, but also have a good
effect to inhibit smoke release during their combustion.

3.3. XRD measurement

During the LOI and CONE tests we noticed that 3#celluloseZn

compared to other samples exhibits the best ame retardancy
Fig. 4. (a) TG and (b) DTG thermograms of cellulose bers, 1#celluloseZn, of cellulose bers. The X-ray diffraction patterns of cellulose
2#celluloseZn, 3#celluloseZn. bers, 3#celluloseZn bers, 3#celluloseZn bers pyrolyzed at
126 K. Zhang et al. / Carbohydrate Polymers 136 (2016) 121127
Fig. 5. SEM of combustion residues of cellulose bers, 1#celluloseZn, 2#celluloseZn, 3#celluloseZn.
280 C and 3#celluloseZn bers pyrolyzed at 400 C are presented
in Fig. 3. The cellulose bers with a cellulose crystal structure
have peaks at 2 = 12.2 and 21.0 assigned to (1 0 1) and (0 0 2)
reections, respectively (de Melo et al., 2009; Enomoto-Rogers,
Kamitakahara, Yoshinaga, & Takano, 2011; Malucelli et al., 2014).
The cellulose bers and 3#celluloseZn are observed to have a
cellulose crystal structure. Fig. 3a and b shows that the intensity
of the peak at 2 = 21.0 is much higher than that of 2 = 12.2 ,
and the intensities of the two peaks are slightly higher in the
cellulose bers than in the 3#celluloseZn, which indicates that
the high-orientation structure of cellulose macromolecular chains
in celluloseZn bers have not been destroyed. Moreover, peaks
at 2 = 12.9 , 21 , and 59.5 in Fig. 3c are assigned to an unsta-
ble crystal compound alkaline zinc carbonate (Zn5 (OH)6 CO3 ) as
zinc ion could catalyze the pyrolytic process of the bers to form
more carbon dioxide and water; peaks at 2 = 31.7 , 34.4 , 36.2 ,
47.5 , 56.5 , 62.8 , and 67.8 in Fig. 3d are assigned to zinc oxide
(ZnO) as Zn5 (OH)6 CO3 would gradually convert into ZnO upon
increasing the pyrolytic temperature, which can explains why the
celluloseZn bers have a very small amount of smoke in the incipi-
ent stage of ber combustion. Those patterns support that different
chemical forms of zinc ions catalyze the pyrolytic process of the
cellulose bers to improve the ame retardancy.
3.4. Thermogravimetric analysis
The thermal degradation of cellulose bers, 1#celluloseZn,
2#celluloseZn and 3#celluloseZn were studied using thermo-
gravimetric analysis, which are plotted in Fig. 4a and b. All the
samples exhibited an initial weight loss in the temperature range of
30240 C, which can be attributed to dehydration in the bers that
was induced by the reduced graft degree and destroyed glycosidic
bonds. The next step, occurring at 240450 C, all the ber samples
underwent a rapid weight loss, yielding small molecule gaseous
products, including H2 , CO2 , CO, CH4 , C2 H6 , C2 H4 , water vapor and
gaseous organics. Above 300 C, celluloseZn have a lower initial
temperature for rapid weight loss when the amount of zinc ions
added was increased. As the temperature continues to increase
from 450 C to 800 C, a signicantly larger amount of solid residues
was produced from celluloseZn bers. In particular, the remained
residues for cellulose bers, 1#celluloseZn, 2#celluloseZn and
3#celluloseZn were 4.1%, 12.1%, 18.6%, and 33.6%, respectively.
 K. Zhang et al. / Carbohydrate Polymers 136 (2016) 121127
This indicates that more charred products were formed after zinc
ion grafted onto cellulose bers, which was corresponding to the
XRD analysis that (Zn5 (OH)6 CO3 ) and ZnO were formed through a
chain reaction with a gaseous product of water, carbon dioxide, and
carbonic oxide during the pyrolysis. The residues can insulate the
surface acting as barrier to heat and gases to prevent further decom-
position. This can also explain why cellulose bers containing zinc
ions generated small amounts of smoke.
3.5. Morphological analysis
The residues of the cellulose bers and celluloseZn bers after
CONE tests were studied by SEM, which are shown in Fig. 5. The
shape of cellulose bers had been destroyed after combustion,
and the residue had a aky morphology. However, celluloseZn
bers maintained the conventional structure morphology of cellu-
lose bers and the residue-briform structure was better retained
when the amount of zinc ions added was increased. In addition, the
residue surface layers of 2#celluloseZn bers and 3#celluloseZn
bers were dense and tight, which can act as a barrier to heat
and gasses and reduce the formation of volatile gases such as
carbon monoxide and carbon dioxide. This can explain why the
celluloseZn bers have a very low HRR, THR, and TSR.
According to the above results, we can explicitly speculate the
ame-retardant mechanism of zinc ions for cellulose bers. First,
the zinc ions in cellulose bers catalyzed dehydration and decar-
boxylation reactions, which promoted the formation of char and
inhibited the depolymerization of cellulose, and generated more
products of small molecules. In addition, the zinc ions in cellu-
lose bers generated metal intermediate compounds, which could
cover the ber surfaces as barrier to stop oxygen penetration and
prevent the spread of ammable gases.
4. Conclusion
The maleic anhydride was successfully grafted onto cellulose
bers using N,N-dimethyl formamide (DMF) as reaction medium.
Then, celluloseZn bers with different zinc ion contents were
obtained. The successful surface graft polymerizations of maleic
anhydride with three different contents were conrmed by FTIR.
Flame retardancy and thermal degradation of zinc-ion-modied
cellulose bers was investigated and conrmed by limiting oxygen
index (LOI), cone calorimeter (CONE) and X-ray diffraction, thermal
gravimetric analysis (TG), SEM, respectively.
CelluloseZn bers tend to be ame retardant when zinc ion
content increases up to 4.96 wt% as known from the LOI and
CONE data. The XRD analysis of cellulose bers, celluloseZn bers,
pyrolyzed celluloseZn bers, the TG results of all samples and the
SEM of combustion residues of cellulose bers and celluloseZn
bers suggested that the existence of zinc ions increased char for-
mation and modied the thermal degradation behavior of cellulose
bers, thereby improving the ame retardancy. And so, we pro-
posed a zinc ion ame retardancy mechanism for the cellulose
bers.
Acknowledgements
This work was nancially supported by the National Nat-
ural Science Foundation of China (50673046), the National
High Technology Research and Development Program of China
127
(2010AA093701), and the Program for Changjiang Scholars and
Innovative Research Team in University (IRT0970).
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