Journal of Molecular Structure: THEOCHEM 716 (2005) 193 198
www.elsevier.com/locate/theochem
Prediction of high weight polymers glass transition
temperature using RBF neural networks
Antreas Afantitis, Georgia Melagraki, Kalliopi Makridima, Alex Alexandridis,
Haralambos Sarimveis*, Olga Iglessi-Markopoulou
School of Chemical Engineering, National Technical University of Athens, 9, Heroon Polytechniou Str., Zografou Campus, Athens 15780, Greece
Received 9 September 2004; accepted 4 November 2004
Available online 5 January 2005
Abstract
A novel approach to the prediction of the glass transition temperature (Tg) for high molecular polymers is presented. A new quantitative
structure property relationship (QSPR) model obtained using Radial Basis Function (RBF) neural networks and a set of four-parameter
P Pis
descriptors, MVðterÞðRterÞ, LF, DXSB and PEI. The produced QSPR model (R2Z0.9269) proved to be considerably more accurate
compared to a multiple linear regression model (R2Z0.8227).
q 2004 Elsevier B.V. All rights reserved.
Keywords: RBF neural network; QSPR; Glass transition temperature
1. Introduction Katrinzky et al. [7] there are two kinds of approaches,
the empirical and the theoretical. Empirical methods
Determination of the physical properties of organic correlate the target property with other physical or chemical
compounds based on their structure is a major research properties of the polymers, for example, group additive
subject in computational chemistry. Quantitative struc- properties (GAP) [8]. The most widely referenced model of
ture property relationship (QSPR) correlations have been the theoretical estimations produced by Bicerano [6]
widely applied for the prediction of such properties over combines a weighted sum of structural parameters along
the last decades [1 3]. A breakthrough has occurred in with the solubility parameter of each polymer. In his work, a
this field with the appearance of artificial neural networks regression model was produced for 320 polymers but no
(ANNs). external data set compounds were used to validate this
The glass transition is the most important transition and model.
relaxation that occurs in amorphous polymers. It has a
Cameilio et al. [9] calculated the parameters of 50
significant effect on the properties and processing charac- acrylates and methylacrylates with molecular mechanics
teristics of this type of polymers [4]. The glass transition
and correlated them with Tg. Katrizky et al. [10] introduced
(Tg) is difficult to be determined because the transition
a model for 22 medium molecular weight polymers using
happens over a comparatively wide temperature range and
four parameters. Following this work, Katrinzky et al. [7]
depends on the method, the duration and the pressure of the
and Cao and Lin [11] obtained two separate models for 88
measuring device [5,6]. Besides these difficulties, the
un-cross-linked homopolymers including polyethylenes,
experiments are costly and time consuming.
polyacrylates, polymethylacrylates, polystyrenes, poly-
In the past, numerous attempts have been made to predict
ethers, and polyoxides. The models were used as predictors
Tg for polymers by different approaches. According to
of the molar glass transition temperatures [7] (Tg/M) and
glass transition temperatures [11]. Joyce et al. [12] used
neural networks for the prediction of Tg based on monomer
* Corresponding author. Tel.: C30 210 772 3237; fax: C30 210 772
structure of polymers. Another approach with neural
3138.
E-mail address: hsarimv@central.ntua.gr (H. Sarimveis). network was proposed by Sumpter and Noid [13] using
0166-1280/$ - see front matter q 2004 Elsevier B.V. All rights reserved.
doi:10.1016/j.theochem.2004.11.021
194 A. Afantitis et al. / Journal of Molecular Structure: THEOCHEM 716 (2005) 193 198
the repeating unit structure as representative of the polymer. 2.2. RBF network training methodology
Finally Jurs and Mattioni [14] obtained a QSPR model
which predicts Tg values for a diverse set of polymers. Training methodologies for the RBF network architec-
An ANN-based modeling method could produce a more ture are based on a set of input output training pairs (x(k);
accurate QSPR model compared to linear methods, since it y(k)) (kZ1,2,.,K). The training procedure used in this
has the ability to approximate the possible non-linear work consists of three distinct phases:
relationships between structural information and properties
(i) Selection of the network structure and calculation of
of compounds during the training process. The resulting
the hidden node centers using the fuzzy means
model can generalize the knowledge among homologous
clustering algorithm [15]. The algorithm is based on
series without need for theoretical formulas [6]. In this work
a fuzzy partition of the input space, which is produced
we explore these neural network capabilities, by introducing
by defining a number of triangular fuzzy sets on the
a new QSPR model for the prediction of Tg values that is
domain of each input variable. The centers of these
based on the RBF architecture. The database consists of
fuzzy sets produce a multidimensional grid on the input
88 un-cross-linked homopolymers and contains the exper-
space. A rigorous selection algorithm chooses the most
imental values of Tg and the values of following
P Pthe
appropriate knots of the grid, which are used as hidden
descriptors MVðterÞðRterÞ, LF, DXSB and PEI. All the
node centers in the produced RBF network model. The
data are taken from Cao and Lin [11].
idea behind the selection algorithm is to place the
centers in the multidimensional input space, so that
there is a minimum distance between the center
2. Modeling methodology locations. At the same time the algorithm assures that
for any input example in the training set, there is at
In this section we present the basic characteristics of the least one selected hidden node that is close enough
RBF neural network architecture and the training method according to a distance criterion. It must be empha-
that was used to develop the QSAR neural network models. sized that opposed to both the k-means [16] and the
c-means clustering [17] algorithms, the fuzzy means
technique does not need the number of clusters to be
2.1. RBF network topology and node characteristics
fixed before the execution of the method. Moreover,
due to the fact that it is a one-pass algorithm, it is
RBF networks consist of three layers: the input layer, the
extremely fast even if a large database of input output
hidden layer and the output layer. The input layer collects
examples is available.
the input information and formulates the input vector x. The
(ii) Following the determination of the hidden node
hidden layer consists of L hidden nodes, which apply non-
centers, the widths of the Gaussian activation
linear transformations to the input vector. The output layer
function are calculated using the p-nearest neighbour
delivers the neural network responses to the environment. A
heuristic [18]
typical hidden node l in an RBF network is described by a
!1=2
^
vector xl, equal in dimension to the input vector and a scalar
p
1X
width sl. The activity nl(x) of the node is calculated as the
^ ^
sl Z kxl Kxik2 (4)
p
Euclidean norm of the difference between the input vector iZ1
and the node center and is given by:
^ ^ ^
where x1, x2,.,xp are the p nearest node centers to
the hidden node l. The parameter p is selected, so
^
vlðxÞ Z kx Kxlk (1)
that many nodes are activated when an input vector
The response of the hidden node is determined by
is presented to the neural network model.
passing the activity through the radially symmetric
(iii) The connection weights are determined using linear
Gaussian function:
regression between the hidden layer responses and the
corresponding output training set.
vlðxÞ2
flðxÞ Åºexp K (2)
sl2
Finally, the output values of the network are computed as
3. Results and discussion
linear combinations of the hidden layer responses:
L
X
The data set of 88 polymers was divided into a training
^
ym Z gmðxÞ Z flðxÞwl;m; m Z 1; .; M (3)
set of 44 polymers, and a validation set of 40 polymers,
lZ1
while 4 polymers were rejected as outliers. The selection of
where ½w1;m; w2;m; .; wL;mŠ is the vector of weights, which the compounds in the training set was made according to the
multiply the hidden node responses in order to calculate the structure of the polymers, so that representatives of a wide
mth output of the network. range of structures (in terms of the different branching
A. Afantitis et al. / Journal of Molecular Structure: THEOCHEM 716 (2005) 193 198 195
and length of the carbon chain) were included. The parameters express the intermolecular forces of the poly-
P
polymers in the training set and validation sets along with mers. MVðterÞðRterÞ expresses the no free rotation part of
the collected from the literature [11] experimental glass the side chain and LF (free length) expresses the bond count
transition temperatures are presented in Tables 1 and 2, of the free rotation part of side chain [11]. The four
respectively. descriptors are very attractive because they can be
Structural parameters for the 84 polymers were calcu- calculated easily, rapidly and they have clear physical
lated by the equations provided in the literature [11]. Two meanings.
sets of descriptors were formulated. The first one (set 1) The RBF training method described in Section 2 was
P
includes four parameters MVðterÞðRterÞ, LF, DXSB and implemented using the Matlab computing language in order
P
PEI, while second one (set 2) incorporates only three to produce the ANN models. It should be emphasized that
Pthe P
parameters MVðterÞðRterÞ, PEI and DXSB. DXSB is the method has been developed in-house, so no commercial
related to the polarity of the repeating unit, while dipole packages were utilized to build the neural network models.
P
of the side group depends on PEI [11]. These two For comparison purposes, a standard multivariate regression
Table 1
Training set
A/A Name Tg(K),exp Tg(K),train (set 1 ANN), Tg(K),train (set 2 ANN), Tg(K),train (set 1 linear), Tg(K),train (set 2 linear),
[7] R2Z0.9968 R2Z0.9699 R2Z0.9305 R2Z0.7978
1 Poly(ethylene) 195 198.5551 198.5575 206.2141 180.7988
2 Poly(butylethylene) 220 218.7587 221.2788 235.0911 232.7334
3 Poly(cyclohexylethylene) 363 366.3575 358.4639 344.6778 325.4238
4 Poly(methyl acrylate) 281 281.7356 283.8484 275.8405 266.8474
5 Poly(sec-butyl acrylate) 253 253.3203 230.8956 253.2285 253.0170
6 Poly(vinyl chloride) 348 347.5609 350.5647 342.3186 313.8412
7 Poly(vinyl acetate) 301 300.9527 302.0354 301.0322 292.5775
8 Poly(2-chrolostyrene) 392 387.1948 389.7748 365.8097 348.3518
9 Poly(4-chrolostyrene) 389 384.5742 386.5308 365.7563 348.7295
10 Poly(3-methylstyrene) 374 373.9529 374.5706 364.4905 348.2874
11 Poly(4-fluorostyrene) 379 388.5550 385.5003 362.0613 343.8790
12 Poly(1-pentene) 220 221.4911 215.7971 244.9158 232.5792
13 Poly(tert-butyl acrylate) 315 313.5255 315.9148 320.2125 321.7363
14 Poly(vinyl hexyl ether) 209 204.7662 205.8718 207.1528 243.3611
15 Poly(1,1-dichloroethylene) 256 256.2872 256.2894 247.1680 193.4119
16 Poly(a-methylstyrene) 409 408.4218 391.5212 401.2537 376.0410
17 Poly(ethyl methylacrylate) 324 325.1226 333.8064 316.7212 312.6020
18 Poly(ethyl chloroacrylate) 366 365.1200 348.3090 369.4096 365.8042
19 Poly(tert-butyl methylacrylate) 380 380.6744 355.6613 392.4762 392.3873
20 Poly(chlorotrifluoroethylene) 373 372.8955 369.6086 370.0549 335.4887
21 Poly(oxyethylene) 206 198.5551 198.5575 206.2141 180.7988
22 Poly(oxytetramethylene) 190 198.5551 198.5575 206.2141 180.7988
23 Poly(vinyl-n-octyl ether) 194 195.1257 202.8784 185.9801 242.6692
24 Poly(oxyoctamethylene) 203 198.5551 198.5575 206.2141 180.7988
25 Poly(vinyl-n-pentyl ether) 207 213.3238 208.3135 217.8674 243.8824
26 Poly(n-octyl acrylate) 208 208.4627 220.8631 187.1082 248.5577
27 Poly(n-heptyl acrylate) 213 210.4768 221.5301 198.0531 249.2561
28 Poly(n-hexyl acrylate) 216 218.3827 222.6153 209.1625 250.1351
29 Poly(vinyl-n-butyl ether) 221 216.9422 211.9548 228.7795 244.6534
30 Poly(vinylisobutyl ether) 251 252.1121 251.0763 289.1591 292.7876
31 Poly(pentafluoroethyl ethylene) 314 314.6488 321.3212 333.3871 324.1696
32 Poly(3,3-dimethylbutyl 318 317.5529 359.6010 365.0133 385.2956
methacrylate)
33 Poly(vinyl trifluoroacetate) 319 319.0651 318.1759 304.0800 311.4646
34 Poly(n-butyl a-chloroacrylate) 330 329.7446 348.2495 350.1299 366.8521
35 Poly(heptafluoropropyl ethylene) 331 330.5015 322.4316 322.2799 322.6774
36 Poly(5-methyl-1-hexene) 259 267.9876 281.9314 285.4562 280.9634
37 Poly(n-hexyl methacrylate) 268 268.3445 263.7424 266.4187 302.5932
38 Poly[p-(n-butyl)styrene] 279 278.0939 273.3399 250.3024 247.1930
39 Poly(2-methoxyethyl methacrylate) 293 292.1270 289.0940 278.0316 307.6720
40 Poly(4-methyl-1-pentene) 302 291.4458 281.6227 295.7158 280.9432
41 Poly(n-propyl methacrylate) 306 304.5211 304.7446 302.5679 308.3655
42 Poly(3-phenyl-1-propene) 333 333.0387 333.3597 319.1753 309.1556
43 Poly(sec-butyl a-chloroacrylate) 347 348.2163 348.9745 360.7427 366.9406
44 Poly(vinyl acetal) 355 354.5809 354.8202 356.0620 353.4776
196 A. Afantitis et al. / Journal of Molecular Structure: THEOCHEM 716 (2005) 193 198
Table 2
Validation set
A/A Name Tg(K),exp [7] Tg(K),pred (set 1 ANN), Tg(K),pred (set 2 ANN), Tg(K),pred (set 1 linear), Tg(K),pred (set 2 linear),
R2Z0.9269 R2Z0.9252 R2Z0.8227 R2Z0.7097
1 Poly(ethylethylene) 228 225.7773 206.1942 254.3056 232.2911
2 Poly(cyclopentylethylene) 348 358.7344 343.5276 333.7406 312.7605
3 Poly(acrylic acid) 379 370.7699 383.7025 329.0515 303.8972
4 Poly(ethyl acrylate) 251 260.9209 246.7095 258.6331 259.2738
5 Poly(acrylonitrile) 378 345.0173 371.8758 313.8227 286.6382
6 Poly(styrene) 373 371.7688 347.9344 346.6853 326.8437
7 Poly(3-chrolostyrene) 363 384.5075 389.0822 368.3181 351.7191
8 Poly(4-methylstyrene) 374 374.1514 372.7100 361.5876 344.9300
9 Poly(propylene) 233 226.4469 187.9298 262.2846 231.5684
10 Poly(ethoxyethylene) 254 225.3849 228.6502 252.0064 247.9495
11 Poly(n-butyl acrylate) 219 245.6944 227.1540 232.2903 252.9285
12 Poly(1,1-difluoroethylene) 233 195.4623 198.3722 216.6780 184.0215
13 Poly(methyl methylacrylate) 378 353.2666 381.0222 334.3601 320.6272
14 Poly(isopropyl methylacrylate) 327 346.2991 335.9038 340.3382 329.0090
15 Poly(2-chloroethyl methyl 365 320.4176 374.1077 308.9656 314.1617
acrylate)
16 Poly(phenyl methylacrylate) 393 384.4661 383.4895 389.6478 387.7161
17 Poly(oxymethylene) 218 198.5551 198.5575 206.2141 180.7988
18 Poly(oxytrimethylene) 195 198.5551 198.5575 206.2141 180.7988
19 Poly(vinyl-n-decyl ether) 197 193.8290 194.0785 154.2539 230.9803
20 Poly(oxyhexamethylene) 204 198.5551 198.5575 206.2141 180.7988
21 Poly(vinyl-2-ethylhexyl ether) 207 203.3388 200.5523 207.2539 243.0972
22 Poly(n-octyl methylacrylate) 253 231.6752 251.2710 244.1416 300.7819
23 Poly(n-nonyl acrylate) 216 205.7941 220.5435 176.3024 248.0084
24 Poly(1-heptene) 220 215.2582 224.7551 225.0757 232.8289
25 Poly(n-propyl acrylate) 229 254.0266 233.0850 244.7675 255.3384
26 Poly(vinyl-sec-butyl ether) 253 212.4641 205.6889 239.7295 244.8458
27 Poly(2,3,3,3-tetrafluoropropylene) 315 302.9461 313.9999 376.8912 360.9749
28 Poly(N-butyl acrylamide) 319 287.7707 290.2156 292.0473 307.4908
29 Poly(3-methyl-1-butene) 323 315.5115 283.7897 306.5165 281.0895
30 Poly(sec-butyl methacrylate) 330 299.0857 283.5890 300.4798 305.8099
31 Poly(3-pentyl acrylate) 257 251.1566 230.2371 241.6161 251.4401
32 Poly(oxy-2,2-dichloromethyl 265 262.6800 250.3470 239.6464 195.2553
trimethylene)
33 Poly(vinyl isopropyl ether) 270 270.4936 252.7574 300.6332 294.0386
34 Poly(n-butyl methacrylate) 293 290.0164 285.9807 289.8661 305.7211
35 Poly(3,3,3-trifluoropropylene) 300 271.9207 316.5163 345.6684 327.9476
36 Poly(vinyl chloroacetate) 304 298.8250 345.7275 265.9810 272.7775
37 Poly(3-cyclopentyl-1-propene) 333 337.5040 338.5281 321.8972 312.2930
38 Poly(n-propyl a-chloroacrylate) 344 351.9808 348.1715 359.9544 366.4854
39 Poly(3-cyclohexyl-1-propene) 348 348.9284 351.6250 332.4757 324.8458
40 Poly(vinyl formal) 378 372.8332 369.3446 377.9002 366.2196
Table 3
Summary of the results produced by the different methods
Parameters Method Training set Validation Figure Equation
R2 R2
train pred
set
1 Set 1 Neural network 44 40 0.9968 0.9269 1
2 Set 2 Neural network 44 40 0.9699 0.9252 2
3 Set 1 Linear 44 40 0.9305 0.8227 3 5
4 Set 2 Linear 44 40 0.7978 0.7097 4 6
5 Set 1 Cross-validation, neural 84-i i 0.9269 5
network
6 Set 2 Cross-validation, neural 84-i i 0.8501
network
7 Set 1 Cross-validation, linear 84-i i 0.8719 6
8 Set 2 Cross-validation, linear 84-i i 0.7253
A. Afantitis et al. / Journal of Molecular Structure: THEOCHEM 716 (2005) 193 198 197
method for producing linear models was also utilized. Both
neural networks and linear models were trained using the 44
individuals in the training set and were tested on the
independent validation set consisting of 40 examples. The
models produced by multiple linear regression on the two
sets of descriptors are shown next:
X
Tg ðKÞ Z 0:3617 MVterðRterÞ K10:3254LF
C159:7984DXSB C9:3931SPEI C206:2141
(5)
X
Tg ðKÞ Z 0:4394 MVterðRterÞ C167:2681DXSB
C2:8929SPEI C180:7988 (6)
Fig. 2. Experimental vs predicted Tg for 40 polymers (set 2 ANN).
The RBF models generated using the two sets of
Figs. 5 and 6, where again the superiority of the neural
descriptors consisted of 34 and 25 hidden nodes, respecti-
network methodology over the multiple linear regression
vely. RBF models are more complex compared to the linear
method is clear. It should be mentioned, that contrary to the
models and are not shown in the paper for brevity, but can
aforementioned results, there is a decrease in the R2 statistic
be available to the interested reader. The produced ANN
in both modeling methodologies when the three-descriptor
QSPR models for the prediction of glass transition
set is utilized. However, the R2 statistic for the neural
temperature, proved to be more accurate compared to
network methodology using the second set of descriptors is
multiple linear regression models using both sets of
still high, meaning that the respective neural network model
descriptors as shown in Table 3, where the results are
is reliable.
summarized. More detailed results can be found in Tables 1
Summarizing the results presented in this work we can
and 2 where the estimations of the two modeling techniques
make the following observations:
for the training examples and the predictions for the
validation examples are depicted in an example-to-example
(i) The modeling procedures utilized in this work (separa-
basis. There are four columns of results in the two tables
tion of the data into two independent sets and leave-
corresponding to the two modeling methodologies and the
one-out cross-validation) illustrated the accuracy of the
two sets of descriptors. Figs. 1 4 show the experimental
produced models not only by calculating their fitness on
glass transition temperatures vs. the predictions produced by
sets of training data, but also by testing the predicting
the neural network and the multiple regression techniques in
abilities of the models.
a graphical representation format.
(ii) We showed that using the neural network methodology we
To further explore the reliability of the proposed method
can still have a reliable prediction, when the descriptor LF is
we also used the leave-one-out cross-validation method on
dropped. Therefore, a three-descriptor ANN model can be
the full set of the available data (excluding the outliers).
used for the prediction of the glass transition temperature at
The results are summarized in Table 3 and are shown in
Fig. 1. Experimental vs predicted Tg for 40 polymers (set 1 ANN). Fig. 3. Experimental vs predicted Tg for 40 polymers (set 1 linear).
198 A. Afantitis et al. / Journal of Molecular Structure: THEOCHEM 716 (2005) 193 198
Fig. 4. Experimental vs predicted Tg for 40 polymers (set 2 linear). Fig. 6. Experimental vs predicted Tg with cross-validation (set 1 linear).
transition temperatures or to the approximate empirical
the expense of the increased complexity of the model
equations with limited reliability.
compared to the simple structure of a linear model.
Acknowledgments
4. Conclusions
A. Af. wishes to thank the A.G. Leventis Foundation for
its financial support.
The results of this study show that a practical model can be
constructed based on the RBF neural network architecture for
References
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