Polyglycidyl nitrate (PGN)-based energetic thermoplastic

polyurethane elastomers with bonding functions

Zaijuan Zhang,1 Nan Luo,2 Zhen Wang,1 Yunjun Luo1
1
School of Material Science and Engineering, Beijing Institute of Technology, Beijing 100081, Peoples Republic of China
2
Environmental Protection Research Institute of Light Industry, Beijing 100089, China
Correspondence to: Y. Luo (E - mail: [email protected])

ABSTRACT: PGN-based ETPUEs were synthesized using mixture of chain extenders including 1, 4-butanediol and Diethyl Bis(hydrox-
ymethyl)malonate (DBM). Through the special chain extenders DBM, the COOR was introduced into the energetic thermoplastic
polyurethane elastomers (ETPUEs) and further enhances the adhesion between ETPUE and nitramine solid ingredients in propellants.
From the analysis, with the percentage of DBM increasing, the work of adhesion (Wa) between nitramine solid ingredients and
ETPUEs increased and the maximum stress (rm) of ETPUEs decreased on the other hand. In order to test the bonding functions of
different ETPUEs, the RDX/ETPUE propellants were prepared and the stressstrain curves of all propellants were tested. The results
showed that the ETPUE-75 with 75% DBM can prevent the dewetting and improve the mechanical properties of propellants. The
ETPUE prepared with chain extender including 1, 4-butanediol and DBM were valuable for application in propellants. V C 2015 Wiley

Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 42026.

KEYWORDS: elastomers; polyurethanes; thermoplastics

Received 16 September 2014; accepted 22 January 2015

DOI: 10.1002/app.42026

INTRODUCTION phology of polyurethane makes it a good thermoplastic elasto-

mer and a good kind of binders.3 Energetic thermoplastic
Propellant is mainly composed of solid ingredients like oxidiz-
polyurethane elastomers (ETPUEs) have been widely studied
ers, metallic fuels, and other minor additives and polymer
because high energy and excellent properties.46
binder. The oxidizer in the propellants is to provide necessary
oxygen for complete combustion of the fuel. An important kind The poly (glycidyl nitrate) (PGN) with nitrato group is a good
of oxidizers is nitramine solid ingredients, such as hexogeon kind of macro glycol of ETPUE because of its high energy, high
(RDX), cyclotetramethy-lene tetranitramine (HMX) and hexani- density, and high oxygen content.7 In 1950, PGN was first syn-
trohexaazaisowurtzitane (CL-20).1 thesized.8 The development of PGN was delayed because of the
hazardous processes of monomer preparation, purification, and
The binders of solid propellants provide a matrix to bind the
polymerization. It took years to recover its synthetic investiga-
solid ingredients together. They give desired shape and struc-
tion. Until 1990s, commercial production of PGN was started
tural integrity to the propellants. Conventional binders which
and the researches of its application were begun.9 Until now,
used cross-linked elastomers are difficult to dispose and usually
there has been little research on the PGN-based ETPE. Emma-
cause environmental problems. There has been profound inter-
nuela Diaz et al. synthesized the PGN-based ETPUEs using
est to develop thermoplastic elastomers (TPEs) as suitable can-
PGN and 4, 4-methylene diphenyl isocyanate (MDI) and stud-
didate for binder applications. TPEs avoid a process that
ied the heats of combustion of them.10 Zaijuan Zhang et al.
involves curing reactions and hence has no pot life, and they
synthesized the PGN-based ETPUEs using PGN and hexamethy-
are recyclable. Of the several forms of TPEs, thermoplastic poly-
lene diisocyanate (HMDI) and studied the thermal decomposi-
urethane elastomers (TPUEs) have been extensively researched
tion behavior of PGN-based ETPUE.11 Further research on
as binders of solid propellants.2 TPUEs have unique morphol-
PGN-based ETPUEs in this area would be needed.
ogy and properties. They typically exhibit a two-phase morphol-
ogy because of the incompatibility of the soft and hard Because of the incorporation of the considerable amount of
segments. The mechanical strength of the TPUEs is determined solid energetic materials, dewetting behavior have become seri-
by the agglomeration of the hard segments, and the flexibility is ous problems in solid propellants. When the adhesion between
because of the soft segments. The unique phase separation mor- solid ingredients and ETPUE is not particularly strong, the

C 2015 Wiley Periodicals, Inc.

V

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soft segment is polyglycidyl nitrate (PGN). The dosage of raw

materials can be decided in the three following formulas:
7:6234  mHMDI
R5
0:454  mPGN 122:22  mBDO 19:09  mDBM
mHMDI 1mBDO 1mDBM
wt %B5 mi ; mass:
mHMDI 1mBDO 1mDBM 1mPGN
mDBM
x%DBM5
mBDO 1mDBM
The R was mole ratio of NCO and OH and in this article
the R 5 1. The wt % B was hard segment content by weight
and in this article the wt % B 5 30%. The x% DBM was the
mass fraction of DBM in the mixture of chain extenders. The
sample with x% DBM was named as ETPUE-x. In this article
the mass fraction of DBM was 0%, 25%, 50%, 75%, and 100%
in the mixture, respectively.
In this article, the synthesis process of PGN-based ETPUEs is
Figure 1. Chemical structure of (a) PGN, (b) HMDI, (c) BDO, and (d) divided into three primary processes: (1) a certain amount of
DBM. PGN, HMDI, and catalyst (the mass fraction to total materials
was 1%) was added into reactor. The mixture was stirred and
dewetting occurs rather suddenly.12 The ETPUE with bonding kept for 2 h at 90 C in the nitrogen atmosphere. (2) The differ-
functions itself is hoping to be produced to enhance the interac- ent proportional chain extender (BDO and DBM) was added to
tions of binder and solid ingredients. And they can decrease the mixture at 60 C, and reacted for 35 min. (3) The product was
dewetting and improve the mechanical property of propellants. poured in a mold to cure at 100 C for around 10 h. Finally the
PGN-based ETPUEs with different proportional chain extender
Many studies on structureproperty relationships of polyur-
were obtained.
ethanes were focused on chain extenders.13 They give the special
physical properties to polyurethane through the special chain Synthesis of RDX/ETPUE Propellants. The RDX/ETPUE pro-
extenders.14,15 Based on the above ideas, in this article, a chain pellants were prepared with the following steps: The ETPUE
extender diethyl bis(hydroxymethyl)malonate (DBM) with ester was dissolved in tetrahydrofuran, and the RDX was introduced
group (-COOR) was introduced into the PGN-based ETPUEs.16 in the ETPUE solution at 80% weight percentages. Then the tet-
The induced effect of -COOR and NO2 gives ETPUEs bonding rahydrofuran was evaporated. Finally the mixture of ETPUE
functions and further enhances the adhesion between ETPUE and RDX was mixed on open mill and tableted by flat-panel
and nitramine solid ingredients. curing. The propellant of ETPUE-x was named as RDX/
ETPUE-x.
EXPERIMENTAL
Materials Measurements
Polyglycidyl nitrate (PGN; Mn: 4770 g/mol; OH equivalent: Fourier transform infrared spectra were recorded on FTIR
0.454 mmol/g; Liming Research Institute of Chemical Industry, (Nicolet FTIR- 8700, Thermo) with a wavenumber resolution of
Henan China) was used after vacuum drying for 2 h at 90 C. 4 cm21 and a single average of 32 scans at room temperature.
Hexamethylene diisocyanate (HMDI; Bayer (Germany); NCO Each sample for infrared analysis was obtained with Attenuated
equivalent: 7.6234 mmol/g) was used as received. Catalyst was Total Reflection (ATR).
prepared by dissolving Dibutyltin Dilaurate (DBTDL; Beijing The molecular weights (Mw and Mn) and the polydispersity
Chemical Plant) into dibutyl phthalate. 1, 4-butanediol (BDO; index (PDI5Mw /Mn) were obtained using GPC (LC-20A, Shi-
Beijing Chemical Plant; OH equivalent: 22.22 mmol/g) was madzu). The operating temperature was 40 C, the mobile phase
used after vacuum drying for 4 h at 85 C. Diethyl Bis(hydroxy- was THF, the flow rate was 1.0 mL/min and the raw data were
methyl)malonate (DBM) was made in our laboratory and calibrated using a universal calibration with polystyrene
obtained with a purity of 97.6% using isopropyl ether recrystal- standards.
lization. The OH equivalent of DBM is 9.09 mmol/g.17 RDX
Thermo gravimetric analysis was carried out in TGA analyzer
was provided by Baiyin Yinguang Chemical Material Factory.
(TGA/DSC1SF/ 417-2, Mettler Toledo) at heating rates of 10 C/
Synthesis min from room temperature to 600 C in a nitrogen atmosphere
Synthesis of PGN-Based ETPUEs. The PGN-based ETPUEs (40 mL/min).
were synthesized using mixture of chain extenders including
Differential scanning calorimetric analysis (DSC) was made over
BDO and DBM (Figure 1). The synthesis process was illustrated
the temperature range from 2100 C to 150 C on Mettler DSC1
in Figure 2.
with a 10 K/min heating rate in a nitrogen atmosphere (40 mL/
As Figure 2 shows, the hard segments consist of hexamethylene min). 25 mg of each sample was placed in a small confined
diisocyanate (HMDI) chain extended with BDO and DBM. The aluminum cell.

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Figure 2. The synthesis process of PGN-based ETPUEs with different proportional chain extender.

The contact angle was measured using OCA contact angle ana-
lyzer (Datephysics). The drop volume was 2 lL and the drop
flow was medium speed. The surface free energy was calculated
using the contact angle measurement software SCA20.
The stressstrain test of dumb-bell specimens was measured by
using a tensile testing machine (Instron-6022, Shimadzu) at a
constant strain rate of 100 mm/min and at room temperature.
The dimensions of the samples were 20 mm (neck area length)
x 4 mm (width) x 2 mm (thickness).

RESULTS AND DISCUSSION

Molecular Weight Analysis
The number-average molecular weight (Mn) and polydispersity
index (PDI; Mw /Mn) of synthesized PGN-based ETPUEs were
tested by GPC. The Mn of prepared ETPUEs were between
20,000 and 32,000 g mol21 and the PDI were between 1.83 and
2.13.
FTIR Analysis
Figure 3 showed the infrared spectra of synthesized PGN-based
ETPUEs with different proportional chain extender. According
to the references, the polyurethane syntheses were successful in
making no residual -OH and -NCO groups and appearance of Figure 3. FTIR spectra of ETPUEs.

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fitting the carbonyl stretching region of ETPUEs were shown in

Figure 4 and Table I. As shown in Table I, the hydrogen bond-
ing carbonyl decreases as the amount of DBM in chain extender
increased. The steric hindrance of the bulk ester side chain leads
to the difficulty of hydrogen bonding. After adding DBM, the
distance between the hydrogen bonding sites along the chains
increased which lead to the decreased hydrogen bonding and
aggregation ability of hard segments.
DSC Analysis
The glass transition temperature of ETPUEs is correlated with
the lowest application temperature. So it is important to study
the glass transition temperature of ETPUEs. Figure 5 and Table
II show the DSC results of PGN-based ETPUEs with different
proportional chain extender. Two glass transition temperatures
were found for ETPUEs. The first is the glass transition temper-
ature of soft segment (Tgs) and the second one is the glass tran-
sition temperature of hard segment (Tgh). The Tgs of all
ETPUEs are lower than 230.0 C and indicate that the PGN-
based ETPUEs have good low temperature properties. Upon
further analysis, we may find that the Tgs shifted to higher tem-
perature and the Tgh shifted to lower temperature with the per-
centage of DBM increasing. The two glass transition
temperatures were closer to the middle, which indicated that
Figure 4. Curve fitting for carbonyl region of ETPUEs. the compatibility of soft and hard segment was increased. This
was because of the reduced hydrogen bond between hard seg-
ments which was proved by FTIR.
urethane. In Figure 3, the infrared spectra of ETPUEs did not
show the -OH absorption band of PGN and -NCO absorption TGA/DTG Analysis
band of HMDI at 3450 and 2265 cm21.18,19 The absorption Thermal decomposition could be correlated with the processing
bands at 3340 cm21 were assigned to -NH stretching of ure- temperature of ETPUEs.5,24 So it is necessary to understand the
thane. Also the characteristic peaks of -ONO2 group from PGN thermal decomposition process of PGN-based ETPUEs.
at 1634 and 1279 cm21 were shown.20,21 Those results proved Figure 6 shows the thermal curves of ETPUEs with different
the structure of the ETPUE. proportional chain extender recorded at a heating rate of 10 K/
Hydrogen bonding in ETPUEs, which reflect the microphase min. The initial 5% weight loss for total ETPUEs occurs around
separation, has an important effect on the properties of the elas- 190 C which showed that the PGN-based ETPUEs have good
tomer.22 One of the most useful methods of studying the hydro- thermal stability. The DTG curves of ETPUEs showed that as
gen bonding was FTIR. In these ETPUEs, the carbonyl the percentage of DBM is increased, the thermal transition
absorption included the absorption of amide and DBM, and around 270 C became apparent and the stage around 327 C
they all belong to the hard segment. Traditionally, the hydrogen became weak. This indicates that with the percentage of DBM
bond between NH and carbonyl of hard segment can reflect increasing, the decomposition of hard segment moved to lower
the aggregation ability of hard segments. So we studied the temperature. This is also because the accumulation between
infrared spectra of the carbonyl of hard segment. hard segments was weaker.
In Figure 4 the infrared spectra of the carbonyl stretching region Interfacial Characteristics
are shown for various proportional chain extenders. The spectra The adhesion between nitramine solid ingredients and ETPUEs
could be fitted with two Gauss lines.23 The results of curve- has important effects on the mechanical properties of propellants.

Table I. Results of Curve Fitting for Carbonyl Region of FTIR Spectra for ETPUEs

Bonded carbonyl Free carbonyl

Samples Wavenumber (cm21) Peak area Wavenumber (cm21) Peak area Ratio of hydrogen bonding (%)
ETPUE-0 1689.1 0.97 1713.4 0.68 58.8
ETPUE-25 1698.7 0.67 1722.1 0.72 48.2
ETPUE-50 1695.4 0.46 1720.4 0.76 37.7
ETPUE-75 1701.2 0.36 1727.4 0.82 30.5
ETPUE-100 1732.8

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Figure 5. The DSC thermograms of ETPUEs.

Figure 6. (a) TGA and (b) DTG curves of PGN-ETPUEs.
In this article, the work of adhesion between nitramine solid qq qq
ingredients and ETPUEs was tested by measurement of contact cS1S2 5cS1 1cS2 22 cdS1 cdS2 22 cS1 cS2
p p
(1)
angle. Through the contact angle analysis, the surface free qq qq
energy of ETPUEs was calculated. W a 52 cdS1 cdS2 12 cs1 cS2
p p
(2)
The fundamental equation which relates the interfacial tension
where cs1s2 is the interfacial tension between s1 and s2; cs1 and
between solid and liquid (cSL) to solid surface tension (cS), liq-
cs2 are the surface tensions of s1 and s2 separately; cdS1 and cdS2
uid surface tension (cL), and the contact angle (h) between a p
are the dispersion surface tensions of s1 and s2 separately; cS1
drop of liquid and the solid surface is given by the well-known p
and cS2 are the dipolar surface tensions of s1 and s2 separately.
Young s equation: cSL 5cS -cL coshh>0. The polar molecule
would have two terms making up its surface tension, dispersion As shown in Table IV, with the increasing of percentage of
p
force (d) and dipolar interaction (p), so that cs 5cds 1cs where DBM of the ETPUEs the cs1s2 between three solid ingredients
p
cds and cs are the dispersion and dipolar contributions to the and ETPUEs decreased and the Wa improved generally. The Wa
total surface tension. The contact angle and the calculated sur- value between three solid ingredients and ETPUEs containing -
face free energy using SCA20 were listed in Table III. COOR (ETPUE-25, ETPUE-50, ETPUE-75, and ETPUE-100)
are greatly improved compared with ETPUE-0. This showed
The surface free energy of RDX, HMX, and CL-20 was theoreti-
that PGN-ETPUEs synthesized with mixture extender including
cal values.26 The cs of them is 41.81, 49.76, and 42.65 mJ m22
DBM have bonding functions themselves.
separately. The cds of them is 24.17, 45.63, and 40.61 mJ m22
separately.
Mechanical Properties of ETPUEs
The interfacial tension (cs1s2) and work of adhesion (Wa) The mechanical properties of binders affect the mechanical
between three different nitramine solid ingredients and ETPUEs properties of the final propellants. Thus it is necessary to study
were calculated by the following equations, separately. The cs1s2 the mechanical properties (tensile strength and elongation at
and Wa results of theoretic calculation were listed in Table IV:
Table III. The Contact Angle and Surface Free Energy of ETPUEs
Table II. The Glass Transition Temperature of ETPUEs
Water Formamide
Samples Tgs ( C) Tgh ( C) Samples (deg) (deg) cs(mJ m22) cds (mJ m22)
ETPUE-0 236.4 114.8 ETPUE-0 104.9 95.8 11.76 8.01
ETPUE-25 235.6 105.7 ETPUE-25 100.5 91.0 14.05 9.34
ETPUE-50 234.7 105.5 ETPUE-50 98.8 89.2 14.96 9.81
ETPUE-75 233.4 102.8 ETPUE-75 97.3 87.3 15.95 10.54
ETPUE-100 230.2 100.7 ETPUE-100 94.7 85.0 17.23 10.85

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Table IV. The cs1s2 and Wa of ETPUEs and Nitramine Solid Ingredients (RDX, HMX, and CL-20)

RDX HMX CL-20

Samples cs1s2 (mJ m22) Wa (mJ m22) cs1s2 (mJ m22) Wa (mJ m22) cs1s2 (mJ m22) Wa (mJ m22)
ETPUE-0 9.48 44.09 15.42 46.10 12.80 41.61
ETPUE-25 7.58 48.28 13.71 50.10 11.55 45.15
ETPUE-50 6.91 49.86 13.19 51.53 11.21 46.40
ETPUE-75 6.30 51.46 12.40 53.31 10.57 48.03
ETPUE-100 5.43 53.61 12.23 54.76 10.68 49.20

break) of ETPUEs. The mechanical properties of ETPUEs were

shown in Figure 7. With the increasing of DBM, the elongation
at break (eb) increased and the maximum stress (rm) decreased.
Combining the FTIR analysis results, the reason was weakened
hydrogen bonding between hard segments.
Mechanical Properties of RDX/ETPUE
The mechanical properties of propellants are the combining
results of mechanical properties of ETPUEs and the work of
adhesion between solid ingredients and ETPUEs.
The stressstrain curves of all five propellants were shown in
Figure 8. Yield occurred in stressstrain curves of RDX/ETPUE-
0 propellants, which was considered as one of the indicators of
dewetting. The curves of RDX/ETPUE-75 propellants presented
no yield and its mechanical properties were higher than those
of RDX/ETPUE-0. When the mass fraction of DBM in the mix-
ture of chain extenders was 75%, the two kinds of factors
worked together best. The above results showed that the
ETPUE-75 can prevent the dewetting and improve the mechani-
Figure 7. The mechanical properties of ETPUEs (the ETPE-100 was too cal properties of propellants.
soft to test the mechanical properties).
CONCLUSIONS

The adhesion between solid ingredients and binders and the

properties of binders themselves jointly affect the mechanical
properties of the final propellants. The Polyglycidyl nitrate
(PGN)-based ETPUEs with functional COOR groups were syn-
thesized as binders to enhance the interactions of binders and
solid ingredients. The ETPUEs were given -COOR using differ-
ent proportional mixture of chain extenders including BDO and
DBM which has -COOR. The analysis showed that the ability of
ETPUEs to form hydrogen bond weakened with the percentage
of DBM increasing and further caused the maximum stress
(rm) of ETPUEs to decrease. On the contrary, the interfacial
tension and the work of adhesion between nitramine solid
ingredients and ETPUEs increased. In order to test the combin-
ing results of two factors, the RDX/ETPUE propellants with dif-
ferent ETPUEs were prepared. The tensile tests of propellants
showed that the RDX/ETPUE-75 propellants presented no dew-
etting and good mechanical properties. In conclusion, the
ETPUEs prepared with functional COOR groups have bonding
function and the potential applied value in propellants.

ACKNOWLEDGMENTS

The project was supported by the State Key Laboratory of Explo-

Figure 8. The stressstrain curves of RDX/ETPUE. sion Science and Technology (No.YBKT15-02).

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