3-alkyl-4-nitrofurazans – plasticizers for polymers

Article abstract of DOI:10.1007/s10593-017-2120-y

Oxidation of 4-alkylfurazan-3-amines to the corresponding nitrofurazans was achieved using mixtures of hydrogen peroxide. The volatility of the products as a function of the size of substituent R, has been studied. The phase and relaxation transitions were characterized and the thermodynamic compatibility with polyester urethane was established. The melting points and melting enthalpies of alkylnitrofurazans were determined.

Full text of DOI:10.1007/s10593-017-2120-y

DOI 10.1007/s10593-017-2120-y
Chemistry of Heterocyclic Compounds 2017, 53(6/7), 740–745
3-Alkyl-4-nitrofurazans – plasticizers for polymers
1
1
1
Yury M. Lotmentsev *, Natalya N. Kondakova , Artem V. Bakeshko ,
2
2
Andrei M. Kozeev , Aleksei B. Sheremetev
1
D. I. Mendeleev University of Chemical Technology of Russia,
Miusskaya Sq., Moscow 125047, Russia; e-mail: yulotm@gmаil.com
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,
7 Leninsky Ave., Moscow 119991, Russia; e-mail: sab@ioc.ac.ru
9
2
4
Translated from Khimiya Geterotsiklicheskikh Soedinenii,
017, 53(6/7), 740–745
Submitted January 30, 2017
Accepted March 7, 2017
2
Oxidation of 4-alkylfurazan-3-amines to the corresponding nitrofurazans was achieved using mixtures of hydrogen peroxide. The
volatility of the products as a function of the size of substituent R, has been studied. The phase and relaxation transitions were
characterized and the thermodynamic compatibility with polyester urethane was established. The melting points and melting enthalpies
of alkylnitrofurazans were determined.
Keywords: nitrofurazans, compatibility with polymers, glass transition, melting, volatility.
Nitrofurazans attract significant interest as components
Scheme 1
1
of energetic materials. In particular, such compounds are
considered as potential energetic plasticizers for powders
2
and solid rocket propellants. The advantages of
nitrofurazans include high enthalpies of formation, high
density, chemical stability, and resistance to thermal
degradation. The most important physicochemical
properties that determine the possibility of using energetic
compounds as plasticizers for energetic materials are the
effectiveness of the plasticizing effect and the thermo-
dynamic compatibility with the polymer components, the
stability of the component and phase composition of the
amines in aqueous hydrogen peroxide solutions. Low
solubility interferes the oxidation process, leaving a lot of
the starting amine. We have shown that the addition of
acetic acid to the oxidizing mixtures allows to eliminate
these obstacles. All nitro derivatives 1a–f were obtained in
good yields and were characterized by spectral methods.
The NMR spectra of the obtained products were similar to
those previously described for other nitrofurazans.6
3
material in the required temperature range. Accordingly,
the goal of this study was to determine the volatility,
relaxation and phase transitions, as well as the
thermodynamic compatibility of 3-alkyl-4-nitrofurazans
with polymeric components of energetic materials.
The desired nitrofurazans 1a–f, differing in the size of
the alkyl substituent, were obtained by oxidizing 4-alkyl-
furazan-3-amines 2a–f with mixtures based on hydrogen
The properties of compounds are listed in Table 1.
Similarly to the previously studied methylfurazans,7
compounds 1a–f were stable at elevated temperatures and
could be distilled at atmospheric pressure without
decomposition (Table 1). Standard testing for the
4
peroxide (Scheme 1).
The ability of amino group to undergo oxidation to nitro
group is known to strongly depend on the properties of the
second substituent, which is present at the furazan ring.5
The presence of alkyl substituents that are longer than a
methyl group results in decreased solubility of the starting
8
sensitivity to impact and friction in accordance with
GOST 4545-80 on a K-44-II fall hammer apparatus
(apparatus No. 3, hammer mass 10 kg, drop height 50 mm)
produced frequency of explosions equal to 0% for all of the
0
009-3122/17/53(6/7)-0740©2017 Springer Science+Business Media New York
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Chemistry of Heterocyclic Compounds 2017, 53(6/7), 740–745
Table 1. Properties of nitrofurazans 1a–f
Enthalpy of formation,
Com-
pound
Bp, °С
Density,
o
R
Empirical formula
M, g/mol
ρ, g/cm3
f
ΔH ,
(atmospheric pressure)
kJ/mol
146.69
121.5*
96.4*
1
a
Me
Et
C
C
C
C
3
4
5
6
H
3
H
5
H
7
H
9
N
3
N
3
N
3
N
3
O
3
O
3
O
3
O
3
129.07
143.10
157.13
171.15
185.18
155.11
170
167
187
203
**
1.3816
1.2822
1.2123
1.16722
1.12423
1.31325
1
b
1
c
n-Pr
n-Bu
75.49
1
d
1
e
n-C
5
H
11
C
7
H
11
N
3
O
3
50.3*
1
f
Cyclopropyl
C
5
H
5
N
3
O
3
**
234.6*
*
*
Calculated by the method of additive schemes, based on group contributions.10
* Not determined at atmospheric pressure.
tested compounds. It should be noted that the traditional
energetic plasticizers – nitroglycerin (NG) and diethylene
glycol dinitrate (DEGDN) – produced explosions in 100%
of the tests under analogous conditions.
plasticizer as NG was performed by using the ratio (7):
0.5
P
G  M 
i
i
i
fr 

 .
(7)


P
Gst
Mst
st

The volatility of compounds 1b–e was studied by using
the method of thermogravimetric analysis. The measure-
ments were performed by applying the dynamic method of
Price,11 according to which saturated vapor pressure is
described by the Langmuir equation (1):
where f
r
– coefficient of relative volatility, P
i
i
and Pst, G
i
and Gst, М
and Мst – pressure of saturated vapor, rate of
evaporation, and molecular mass of the studied compound
and reference compound, respectively.
The enthalpies of evaporation ΔHvap were calculated
according to the equation (8) on the basis of linear
approximation results for the dependence of saturated
vapor pressure on temperature:
0
.5

T


1
0.5



P  

2R

 G


  ,
M 
(1)



where α – evaporation coefficient, R – universal gas
constant, J/mol/K, T – temperature, M – molecular mass,
S – evaporation area, G – rate of evaporation (the mass lost
from a unit of area in a unit of time).
logP ABT , where В  
Hvap
, A  const .
1
(8)
R
The characteristics of phase and relaxation transitions
were measured on a Mettler Toledo DSC 822е differential
scanning calorimeter over the temperature range from –120
to 50°С at the heating rate of 10 deg/min and nitrogen flow
rate through the heating chamber set at 50 ml/min.
Accurately weighed samples (±0.01 mg) with masses
between 15 and 20 mg were placed on standard aluminum
pans with the volume of 40 µl. The calibration of
calorimeter was performed with reference samples of zinc
and indium. The melting point was determined from the
position of onset point.
For the purposes of equipment calibration, the equation
(1) was transformed into the equation (2):
0
.5



T
1 dm 

1
0.5



 

P  

2R


(2)
 



M   s dt 

or
P = kν,
(3)
(4)

1
0.5
where
k  

2R

,
0.5
0.5
1
dm  T 
 T 


 G



 .
(5)
s dt  M 
 M 
The thermodynamic compatibility of alkylnitrofurazans
with polyester urethane elastomer (PU) as one potential
component of energetic materials13 was studied by multi-
beam interference method on an ODA-2 laser diffusio-
meter.14 The method is based on the analysis of plasticizer
concentration profile in the mutual diffusion zone in
contact with the polymer. A commercial sample of PU
(polyester on the basis of propanediol, butanediol, adipic
acid, and tolylene-2,4-diisocyanate), produced by SUREL
Ltd., had the following characteristics: number-average
molecular mass 35000 g/mol, the content of urethane
groups 10 mass %, intrinsic viscosity of solution in ethyl
When measured at identical conditions, the calibration
coefficient k does not depend on the type of compound and
vapor pressure (the method for the determination of coef-
ficient k is described in the Supplementary information file).
The saturated vapor pressure of nitrofurazans was measured
with a Mettler-Toledo TGA/SDTA 851 thermogravimetric
analyzer over the temperature range from 25 to 90°С at the
heating rate of 1 deg/min. The studied sample with a mass
between 100 and 160 mg was placed into an open cylindri-
cal aluminum pan with 9.3 mm inner diameter and 2 mm
height. The heating chamber was flushed with nitrogen at
the flow rate of 50 ml/min. In contrast to the published
procedure,11 the value of calibration coefficient k was
determined by using diethylene glycol dinitrate as a reference
compound, the vapor pressure of which was previously
determined via the method of dynamic chromatography.12
Comparative assessment of the volatility of nitro-
furazans 1b–e relative to such well-known energetic
–2
3
acetate [η] 0.3·10 m /kg.
The volatility of nitrofurazans. The volatility of
compounds 1b–e, DEGDN, and NG is characterized in
Figures 1, 2, and in Table 2. The increasing length of alkyl
chain in compounds 1b–е led to decreased volatility. The
obtained data indicate that the saturated vapor pressure of
alkylnitrofurazans was higher by 1–2 orders of magnitude
7
41

Chemistry of Heterocyclic Compounds 2017, 53(6/7), 740–745
Table 2. The volatility parameters for alkylnitrofurazans 1b–e and nitroesters DEGDN and NG
Coefficients for the equation
Com-
pound
Vapor pressure*
Rate of evaporation*,
Coefficient of relative volatility*,
–1
Enthalpy of evaporation
log P = A – BT
–6
–1
–2
Р, Pa
G·10 , kg·s ·m
f
rel, NG
ΔHvap, kJ/mol
А
В
1
b
897
437
328
149
9.09
4.5
231.0
118.0
92.3
43.6
2.2
211
103
77
10.2
10.8
11.4
10.9
10.95
13.6
2438
2727
2963
2912
3329.7
4340
46.7
52.2
56.7
55.7
63.7
83.0
1
c
1
d
1
e
35
DEGDN
NG
1.6
1
1.4
*
Measured at 60°С.
Figure 1. Thermogravimetry data for compounds 1b–e and NG:
− NG; 2 – 1e, 3 – 1d, 4 – 1c, 5 – 1b.
1
Figure 2. Dependence of vapor pressure on temperature for
compounds 1b–e and NG: 1 – 1b; 2 – 1c; 3 – 1d; 4 – 1e; 5 – NG.
than the vapor pressure of nitroester plasticizers DEGDN
and NG.
Phase and relaxation transitions in nitrofurazans 1a–f.
The results accumulated from phase and relaxation
transition studies for compounds 1a–f are presented in
Figures 3–5 and in Table 4. All compounds with the
exception of compound 1c crystallized at temperatures
below 0°C. The thermograms obtained for compound 1e
upon cooling and subsequent heating are presented in
Figure 3 (the thermograms obtained for other compounds
are available in the Supplementary information file).
Crystallization of compound 1e occurred over a narrow
temperature interval, with the peak of crystallization
observed at Tpeak –59°C. No glass transition effects were
observed in the thermograms of compounds that
crystallized (Fig. 4), due to the complete crystallization of
the compounds. Cyclopropyl derivative 1f had the highest
melting point. Increasing the alkyl chain length resulted in
lower melting points.
Figure 3. The thermograms for compound 1e: 1 – cooling, 2 –
heating.
A characteristic property of compound 1c, which had an
n-propyl substituent, was its ability to form supercooled
liquid phase, as it did not crystallize at low temperatures,
but rather was transformed into a glassy state. The thermo-
gram of compound 1c (Fig. 5) showed only a relaxation
transition, associated with glass transition (T ) at –107°С.
g
No crystallization of this compound was observed even
after its prolonged cooling at –50°С for 60 days.
Compound 1c had a low glass transition temperature,
which was lower by approximately 35°С compared to the
Figure 4. The thermograms obtained by heating of compounds
1a–f: 1 – 1f; 2 – 1a; 3 – 1b; 4 – 1d; 5 – 1e.
T of NG (Table 4). It should be noted that the glass
g
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42

Chemistry of Heterocyclic Compounds 2017, 53(6/7), 740–745
Table 4. The characteristics of crystallization and glass transition for compounds 1a–f, NG, and DEGDN
Com-
pound
Melting
Crystallization, Tpeak,°С
g
Glass transition, Т ,°С
T
onset,°С
ΔНfus, J/g
126.5
1
a
–2.4
–20
Does not occur
Does not occur
–107
1
b
–5.6
118.4
Not measured
1
c
No crystallization
104.7
1
d
–16.2
–21.5
–48
–59
Does not occur
Does not occur
Does not occur
–72*
1
e
128.4
1
f
29.1
153.7
–3.3
–27*
NG
12.3* stable form
99.3*
1
5a
15b
1
3.2 ; 10.9
DEGDN
3.0* stable form
116.7* stable form
–49* stable form
–7.6* unstable form
–83*
1
5a
2
.0
–
11.5* unstable form
1
5a
–
10.9
*
Data obtained by the authors (DSC method).
Figure 5. Differential scanning calorimetry data for compound 1c.
transition temperature of plasticizer is an important
characteristic that affects the effectiveness of plasticizer,
including the technological properties of polymer material
at processing temperatures and its mechanical properties at
the temperatures encountered during use.
Figure 6. Interferogram and concentration profile in the mutual
diffusion zone between compound 1c and PU. Temperature 60°С,
duration of diffusion 1 h.
Thermodynamic compatibility of alkylnitrofurazans
with PU. The interferogram with the respective concentra-
tion profile of nitrofurazan 1c through the zone of mutual
diffusion with PU is shown in Figure 6. The concentration
profile in the diffusion zone has a continuous nature, with
the concentration of diffusing compounds gradually
changing from 0 to 1. This observation provides evidence
for unlimited mutual solubility of components. Analogous
distribution at the temperature range from 20 to 60°С was
also observed for the rest of the alkylnitrofurazans. Thus,
compounds 1a–f had unlimited compatibility with
polyester urethane elastomers in this range of positive
temperatures. It should be noted that the thermodynamic
stability of binders prepared on the basis of PU and
alkylnitrofurazans that crystallize at temperatures below
their melting points may be considerably lower.
of evaporation and melting for a series of 3-alkyl-4-nitro-
furazans. These compounds, in contrast to such nitroester
plasticizers as nitroglycerin and diethylene glycol dinitrate,
are not sensitive to impact and friction, but have relatively
higher volatility. 3-Alkyl-4-nitrofurazans have unlimited
compatibility with polyester urethane elastomer. Compared
to other energetic plasticizers, 4-nitro-3-propylfurazan is a
compound that does not crystallize and has a considerably
lower glass transition temperature, which can provide for
its high plasticizing ability.
Experimental
IR spectra were recorded on a Bruker ALPHA
1
13
15
14
spectrometer in KBr pellets. Н, С, N, and N NMR
spectra were acquired on a Bruker AМ-300 instrument
Thus, as a result of the performed studies, we have
determined the saturated vapor pressure, melting points,
and glass transition temperatures, as well as the enthalpies
(300, 75, 50, and 22 MHz, respectively) in CDCl
3
, internal
(for
1
13
standards – TMS (for Н and С nuclei) and MeNO
2
7
43

Chemistry of Heterocyclic Compounds 2017, 53(6/7), 740–745
14N and 15
N nuclei). Mass spectrum of compound 1d was
(15), 83 [M+H–Pr–NO
]+ (10), 43 (100). Found, %:
2
recorded on a Varian MAT-311A spectrometer, using EI
ionization (70 eV). Elemental analysis was performed on a
PerkinElmer 2400 Series II instrument. Melting points
were determined on a Boetius hot stage and were not
corrected. The reaction progress and purity of the obtained
compounds were controlled by TLC method on Merck
C 42.05; H 5.33; N 24.48. С
6
H
9
N
3
O . Calculated, %:
3
C 42.11; H 5.30; N 24.55.
4-Nitro-3-pentylfurazan (1e). Yield 73%, light-yellow
–1
oil. Bp 92°С (7 mmHg). IR spectrum, ν, cm : 2960, 2935,
2873, 1582, 1543, 1455, 1356, 1168, 1157, 1034, 911, 830.
1
H NMR spectrum, δ, ppm (J, Hz): 0.87–0.91 (3H, m,
silica gel 60 F254 plates, using 5:1 CH
eluent.
Cl
2 2
–pentane as
(CH
2
)
4
CH
3
); 1.33–1.42 (4H, m, (CH
2
)
2
CH
2
CH
2
Me); 1.74–
Bu).
); 22.1
CH Pr);
1.83 (2H, m, CH
2
CH
C NMR spectrum, δ, ppm (J, Hz): 13.7 ((CH
((CH CH Me); 23.5 ((CH CH Et); 26.5 (CH
31.1 (CH Bu); 151.0 (C–C
2
Pr); 3.03 (2H, t, J = 7.6, CH
2
13
The starting 4-alkylfurazan-3-amines 2a–f were
2
)
4
CH
2
3
4
obtained according to a published procedure.
2
)
3
2
2
H
)
2
2
2
1
Preparation of 3-alkyl-4-nitrofurazans 1a–f (General
method). A solution of amine 2a–f (70.84 mmol) in AcOH
2
5
11); 159.7 (d, J13C,14N = 17.3,
1
4
C–NO
2
). N NMR spectrum, δ, ppm: –34.3 (NO
2
).
).
15
(70 ml) was added dropwise to a solution of Na
(23.37 g, 70.84 mmol) in 37% H
2
WO
4
·2H
2
O
N NMR spectrum, δ, ppm: 49.7; 40.7; –31.1 (NO
2
O
2 2
(250 ml) heated to 40°С.
Found, %: C 45.36; H 5.92; N 22.61. С
7
H
11
N
3
O
3
.
The reaction mixture was then heated to 70°С and stirred at
this temperature for 1.5 h, cooled to 50°С, and poured into
a mixture of ice (100 g) and water (100 ml). The obtained
Calculated, %: C 45.40; H 5.99; N 22.69.
3-Cyclopropyl-4-nitrofurazan (1f). Yield 82%, light-
yellow oil. Bp 72–73°С (7 mmHg), compound gradually
–1
solution was extracted with CH
combined extracts were washed with water (2×100 ml) and
dried over anhydrous MgSO . The solvent was removed by
evaporation and the residue was purified by distillation.
2
Cl
2
(3×100 ml). The
solidified, mp 25–26°С. IR spectrum, ν, cm : 3021, 1582,
1543, 1467, 1455, 1371, 1307, 1199, 1157, 1082, 1025, 884,
1
4
829. H NMR spectrum, δ, ppm: 1.10–1.14 (2H, m) and 1.25–
1
3
1.31 (2H, m, СH
2
CH ); 2.32–2.37 (1H, m, CH). C NMR
2
3
-Methyl-4-nitrofurazan (1a). Yield 83%, light-yellow
spectrum, δ, ppm (J, Hz): 3.7 (CH
2
CH
2
); 9.6 (CH); 153.0
1
14
oil, bp 65°С (16 mmHg). NMR spectral data were
(C–cyclo-Pr); 159.4 (t, J13C,14N = 17.4, C–NO
2
). N NMR
). N NMR spectrum, δ, ppm:
). Found, %: C 38.77; H 3.28;
. Calculated, %: C 38.72; H 3.25;
6
15
analogous to those previously reported in the literature.
spectrum, δ, ppm: –33.3 (NO
2
3
-Ethyl-4-nitrofurazan (1b). Yield 46%, colorless oil,
43.7; 40.2; –31.0 (NO
2
–
1
Bp 56°С (7 mmHg). IR spectrum, ν, cm : 2965, 2938,
874, 1582, 1543, 1455, 1355, 1168, 1157, 1030, 910, 831.
N 27.00. С
H
5 5
N
3
O
3
2
N 27.09.
1
H NMR spectrum, δ, ppm (J, Hz): 1.44 (3H, t, J = 7.5,
CH ); 2.86 (2H, dd, J = 7.5, J = 7.4, CH CH ).
C NMR spectrum, δ, ppm (J, Hz): 11.1 (CH CH ); 17.7
); 152.1 (C–Et); 159.5 (t, J13C,14N = 18.7, C–NO ).
). Found, %:
. Calculated, %:
CH
2
3
2
3
Supplementary information file containing thermograms
of compounds 1а–f is available from the journal website at
http://link.springer.com/journal/10593.
1
3
2
3
1
(
CH
2
CH
3
2
1
4
N NMR spectrum, δ, ppm: –34.3 (NO
2
C 33.61; H 3.55; N 29.31. С
4
H
5
N
3
O
3
Specific parts of this work were performed with
financial support from OKhNM-04 programs of the
Russian Academy of Sciences.
The authors would like to express their gratitude to
Dr. M. I. Struchkova (Institute of Organic Chemistry, Russian
Academy of Sciences) for acquisition of NMR spectra and
to the leading engineer N. N. Il'icheva (D. I. Mendeleev
Russian Chemical Technology University) for her
assistance with performing calorimetric measurements.
C 33.57; H 3.52; N 29.36.
4
-Nitro-3-propylfurazan (1c). Yield 86%, colorless oil.
–1
Bp 72.5°С (9 mmHg). IR spectrum, ν, cm : 2972, 2940,
880, 1582, 1543, 1453, 1360, 1170, 1157, 1029, 913, 832.
2
1
H NMR spectrum, δ, ppm (J, Hz): 1.01–1.05 (3H, m,
CH CH CH ); 1.78–1.85 (2H, m, CH CH Me); 3.02 (2H, t,
Et). 13C NMR spectrum, δ, ppm (J, Hz): 13.3
); 20.3 (CH CH Me); 25.4 (CH Et); 150.8
2
2
3
2
2
J = 6.6, CH
2
(
(
CH
2
CH
2
CH
3
2
2
2
1
14
C–Pr); 159.6 (t,
J
13C,14N = 17.3, C–NO
2
). N NMR
). N NMR spectrum, δ, ppm:
). Found, %: C 38.37; H 4.45;
. Calculated, %: C 38.22; H 4.49;
1
5
spectrum, δ, ppm: –34.3 (NO
2
References
4
9.6; 40.4; –31.1 (NO
2
1
. (a) Pivina, T. S.; Sukhachev, D. V.; Evtushenko, A. V.;
N 26.69. С
5
H
7
N
3
O
3
Khmelnitskii, L. I. Propellants, Explos., Pyrotech. 1995, 20,
N 26.74.
5
. (b) Sheremetev, A. B.; Pivina, T. S. In Energetic Materials.
3
-Butyl-4-nitrofurazan (1d). Yield 58%, light-yellow
Technology, Manufacturing and Processing. 27th International
Annual Conference of ICT, June 25 – June 28, 1996,
Karlsruhe, Federal Republic of Germany; Karlsruhe, 1996,
pp. 30-1. (c) Sheremetev, A. B. Mendeleev Chem. J. 1997, 41(2),
62. [Ros. Khim. Zh. 1997, 41(2), 43.] (d) Sheremetev, A. B.;
Kulagina, V. O.; Aleksandrova, N. S.; Dmitriev, D. E.;
Strelenko, Yu. A.; Lebedev, V. P.; Matyushin, Yu. N.
Propellants, Explos., Pyrotech. 1998, 23, 142. (e) Stepanov, A. I.;
Dashko, D. V.; Astrat'ev, A. A. Cent. Eur. J. Energ. Mater.
–1
oil. Bp 80°С (8 mmHg). IR spectrum, ν, cm : 2964, 2937,
876, 1582, 1543, 1455, 1355, 1169, 1157, 1033, 910, 831.
2
1
H NMR spectrum, δ, ppm (J, Hz): 0.95–0.99 (3H, m,
CH CH ); 1.43–1.47 (2H, m, (CH CH Me); 1.76–1.78
2H, m, CH CH Et); 3.04 (2H, t, J = 7.5, CH
(
(
2 3
)
3
2
)
2
2
1
3
2
2
2
)
Pr). C NMR
CH ); 22.1
Et); 28.9 (CH Pr); 150.9
spectrum, δ, ppm (J, Hz): 13.4 ((CH
2
3
3
(
(
(CH
C–Bu); 159.6 (t,
spectrum, δ, ppm: –34.2 (NO
9.5; 40.4; –31.1 (NO
2
)
2
CH
2
Me); 23.3 (CH
2
CH
2
2
1
14
J
13C,14N = 17.1, C–NO
2
). N NMR
2
012, 9, 329. (f) Sheremetev, A. B.; Aleksandrova, N. S.;
15
2
). N NMR spectrum, δ, ppm:
Palysaeva, N. V.; Struchkova, M. I.; Tartakovsky, V. A.;
4
[
2
). Mass spectrum, m/z (Irel, %): 129
Suponitsky, K. Yu. Chem.–Eur. J. 2013, 19, 12446.
+
+
+
M+H–Pr] (30), 125 [M–NO
2
] (11), 95 [M–NO
2
–NO]
(g) Ilyushin, M. A.; Shugaley, I. V.; Tselinskii, I. V.;
7
44

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