Porous Polymeric Monoliths by Less Common Pathways: Preparation and Characterization

(1)

(2)

(3)

iii

(4)

iv

(5)

v

.

I. Monolithic Space-filling Porous Materials from Engineering Plastics by Thermally Induced Phase Separation

II. Porous Space-filling Monolithic Polyvinylidene Difluoride (PVDF) Materials by Thermally Induced Phase Separation

III. Porous Melamine-Formaldehyde Monoliths by Step-Growth Polymerization Reactions via an Organic Sol-gel Process

IV. Porous Polyvinylidene Difluoride (PVDF) Monoliths via Thermally Induced Dissolution/Precipitation. Three Strategies to Pore-Tuning

Probing the possibilities of further controlling of the PVDF monolith pore formation process

.

(6)

vi

(7)

vii

(8)

viii

(9)

ix

Table of Contents

1 Introduction ... 1

2 Chromatography – An Overview ... 3

2.1 Fundamental Considerations in a Chromatographic Column ... 5

2.2 Types of HPLC Stationary Phases ... 6

2.2.1 Particulate Packing Materials ... 6

2.2.2 Porous Monolithic Support Materials ... 8

3 Synthesis of Porous Polymeric Monoliths ... 9

3.1 Overview and historical perspective... 9

3.2 Thermally Induced Dissolution/Precipitation ... 10

3.2.1 Thermally Induced Phase-Separation (TIPS) Process ... 10

3.2.2 Solubility of Polymers ... 11

3.3 Preparation of Porous Polymeric Monoliths via Dissolution/Precipitation Process ... 15

3.3.1 Commodity Polymers ... 16

3.3.2 Porogenic Solvents (Diluents) ... 17

3.3.3 Polymers as Co-porogens ... 20

3.3.4 Pore Formation Control in PVDF Monoliths ... 24

3.4 Synthesis of Porous Polymeric Monoliths via Step-Growth Polymerization Reaction ... 25

3.4.1 Highly Mesoporous Melamine-Formaldehyde Monoliths ... 26

4 Monolithic Materials Characterizations ...30

4.1 Morphology Characterization Techniques ... 31

4.1.1 Porous Properties and Surface Area ... 31

4.1.1.1 Nitrogen Adsorption Desorption Analysis – BET/BJH ...32

4.1.1.2 Mercury Intrusion Porosimetry – MIP ...37

4.1.2 Surface Imaging by Scanning Electron Microscopy – SEM ... 39

4.2 Chemical Composition Characterization Techniques ... 42

4.2.1 Elemental Composition and Functional Group Determination... 43

4.2.1.1 Attenuated Total Reflectance-Fourier Transform Infrared Spectroscopy – (ATR-FTIR) ...43

4.2.1.2 Energy-Dispersive X-ray Spectroscopy – EDS ...44

4.2.1.3 X-ray Photoelectron Spectroscopy – XPS ...44

4.2.2 Electrophoretic Light Scattering (ELS) – ζ-(zeta)-potential measurements ... 48

4.2.3 X-ray Diffraction – XRD ... 49

5 Porous Polymeric Monolith Applications ...51

6 Concluding Remarks and Future Aspects ...53

7 Acknowledgements ...55

8 References ...57

(10)

x

(11)

1

1 Introduction

(12)

2

(13)

3

2 Chromatography – An Overview

(14)

4

(15)

5

2.1 Fundamental Considerations in a Chromatographic Column

(16)

6

2.2 Types of HPLC Stationary Phases

2.2.1 Particulate Packing Materials

(17)

7 above

(18)

8

2.2.2 Porous Monolithic Support Materials

(19)

9

3 Synthesis of Porous Polymeric Monoliths 3.1 Overview and historical perspective

(20)

10

3.2 Thermally Induced Dissolution/Precipitation

3.2.1 Thermally Induced Phase-Separation (TIPS) Process

(21)

11 3.2.2 Solubility of Polymers

(22)

12

∆

δ δ

δ

δ (equation 2)

δ

vap m

H RT V

= -

 ^

2 2 2

D P H

= + +

   

(

, ,

) (

² , ,

)

²

(

, ,

)

²

4 _{D s} _{D p} _{P s} _{P p} _{H s} _{H s}

RED Ro

- + - + -

=      

(23)

13 δ

δ δ

δ

(24)

14

(25)

15

3.3 Preparation of Porous Polymeric Monoliths via Dissolution/Precipitation Process

(26)

16 3.3.1 Commodity Polymers

(27)

17 3.3.2 Porogenic Solvents (Diluents)

(28)

18

(29)

19



(30)

20



3.3.3 Polymers as Co-porogens

(31)

21

<

< <

(32)

22

(33)

23

(34)

24

3.3.4 Pore Formation Control in PVDF Monoliths

(35)

25

3.4 Synthesis of Porous Polymeric Monoliths via Step- Growth Polymerization Reaction

(36)

26

3.4.1 Highly Mesoporous Melamine-Formaldehyde Monoliths

(37)

27

(38)

28

(39)

29

(40)

30

4 Monolithic Materials Characterizations

(41)

31

4.1 Morphology Characterization Techniques

4.1.1 Porous Properties and Surface Area

(42)

32

4.1.1.1 Nitrogen Adsorption Desorption Analysis – BET/BJH

^𝑃

𝑉_𝑎(𝑃₀−𝑃) = _𝑉¹

𝑚𝐶 +^𝐶−1_𝑉

𝑚𝐶[_𝑃^𝑃

0]

(43)

33



.

(44)

34 γ

ɛ

(45)

35

γ



(46)

36

(47)

37

4.1.1.2 Mercury Intrusion Porosimetry – MIP

𝐷 = 1

𝑃4𝛾 cos 𝜑

𝛾 𝜑

(48)

38

(49)

39

4.1.2 Surface Imaging by Scanning Electron Microscopy – SEM

(50)

40



(51)

41



(52)

42



4.2 Chemical Composition Characterization Techniques

(53)

43

4.2.1 Elemental Composition and Functional Group Determination

4.2.1.1 Attenuated Total Reflectance-Fourier Transform Infrared Spectroscopy – (ATR-FTIR)

α β γ

(54)

44

4.2.1.2 Energy-Dispersive X-ray Spectroscopy – EDS

4.2.1.3 X-ray Photoelectron Spectroscopy – XPS

(55)

45

Element Line Type Apparent Concentration

k Ratio Wt% Wt%

Sigma

Standard Label

Factory Standard

C K series 0.24 0.00242 70.97 1.91 C Vit Yes

F K series 0.43 0.00085 29.03 1.91 CaF2 Yes

Total: 100.00

(56)

46

Peak Bond

energy (eV)

Atomic concentration (%)

MF9 GCS MF16 WBS MF8 WIS

C 1s [C-(C,H)] 284.7 4.15 3.06 2.3

C 1s [C-(O,N)] 286.4 12.27 12.49 9.4

C 1s [N=C-N, C=O] 287.4 35.38 33.94 37.93

O 1s [C=O] 530.6 0.92 0.6 0.27

O 1s [(C-OH),(C-O-C)] 532.5 7.73 5.35 5.81

N 1s [C=N-C] 398.1 13.67 16.75 14.27

N 1s [N-(C,H)] 399.4 25.88 27.82 30.02

[C-(C,H)]:[C -

(O,N)]:[N=C-N, C=O] N/A 1:2.96:8.5 1:4.08:11.09 1:4.09:16.49

C:N N/A 1.31:1 1.11:1 1.12:1

[N-(C,H)]:[(C-OH),(C-O-

C)] N/A 3.35:1 5.2:1 5.1:1

(57)

47

(58)

48

4.2.2 Electrophoretic Light Scattering (ELS) – ζ-(zeta)-potential measurements

(59)

49 4.2.3 X-ray Diffraction – XRD

(60)

50

(61)

51

5 Porous Polymeric Monolith Applications

(62)

52

(63)

53

6 Concluding Remarks and Future Aspects

(64)

54

(65)

55

7 Acknowledgements



(66)

56



(67)

57

8 References

[1] Roddy, F. M., U.S. Patent 2,478,013 1949.

[2] Smith, W. F., Hashemi, J. (Eds.), Foundations of Materials Science and Engineering, 4th Ed., Mcgraw-Hill Publishing 2006.

[3] Merline, D. J., Vukusic, S., Abdala, A. A., Polymer journal 2013, 45, 413-419.

[4] Coullerez, G., Léonard, D., Lundmark, S., Mathieu, H. J., Surface and interface analysis 2000, 29, 431-443.

[5] Petrović, M., Hernando, M. D., Díaz-Cruz, M. S., Barceló, D., Journal of Chromatography A 2005, 1067, 1-14.

[6] Marquet, P., Lachatre, G., Journal of Chromatography B: Biomedical Sciences and Applications 1999, 733, 93-118.

[7] Vollmer, M., Hörth, P., Nägele, E., Analytical chemistry 2004, 76, 5180-5185.

[8] Yu, C., Davey, M. H., Svec, F., Fréchet, J. M., Analytical Chemistry 2001, 73, 5088- 5096.

[9] Tswett, M. S., Berichte der Deutschen Botanischen Gesellschaft 1906, 24, 316- 323.

[10] Engelhardt, H., Journal of Chromatography B 2004, 800, 3-6.

[11] Willstätter, R., Stoll, A., Untersuchungen über Chlorophyll, Springer-Verlag, Berlin 1913.

[12] Kuhn, R., Lederer, E., Ber 1931, 64, 1349.

[13] Martin, A., Synge, R. M., Biochemical Journal 1941, 35, 1358.

[14] Snyder, L. R., Kirkland, J. J., Dolan, J. W. (Eds.), Introduction to Modern Liquid Chromatography, 3rd Ed., John Wiley & Sons, Hoboken 2011.

[15] McNaught, A. D., Wilkinson, A. (Eds.), IUPAC Compendium of Chemical Terminology, Blackwell Scientific Publications, Oxford 1997.

[16] Van Deemter, J. J., Zuiderweg, F. J., Klinkenberg, A. V., Chemical Engineering Science 1956, 5, 271-289.

[17] Svec, F., Journal of separation science 2004, 27, 1419-1430.

[18] Unger, K. K., Skudas, R., Schulte, M. M., Journal of Chromatography A 2008, 1184, 393-415.

[19] MacNair, J. E., Lewis, K. C., Jorgenson, J. W., Analytical chemistry 1997, 69, 983- 989.

[20] Ohmacht, R., Boros, B., Kiss, I., Jelinek, L., Chromatographia 1999, 50, 75-81.

[21] Chen, H., Horváth, C., Journal of Chromatography A 1995, 705, 3-20.

[22] Gustavsson, P.-E., Larsson, P.-O., Journal of Chromatography A 1996, 734, 231- 240.

[23] Xie, S., Allington, R. W., Fréchet, J. M. J., Svec, F., Modern Advances in Chromatography, Springer-Verlag Berlin Heidelberg 2002, pp. 87-125.

[24] Kłodzińska, E., Moravcova, D., Jandera, P., Buszewski, B., Journal of Chromatography A 2006, 1109, 51-59.

(68)

58

[25] Guiochon, G., Journal of Chromatography A 2007, 1168, 101-168.

[26] Hjerten, S., Liao, J.-L., Zhang, R., Journal of Chromatography A 1989, 473, 273- 275.

[27] Svec, F., Fréchet, J. M., Analytical Chemistry 1992, 64, 820-822.

[28] Mould, D., Synge, R., Analyst 1952, 77, 964-969.

[29] Svec, F., Journal of chromatography A 2010, 1217, 902-924.

[30] Peters, E. C., Svec, F., Fréchet, J., Advanced Materials 1999, 11, 1169-1181.

[31] Svec, F., Tennikova, T. B., Deyl, Z. (Eds.), Monolithic Materials: Preparation, Properties and Applications, Elsevier, Amsterdam 2003.

[32] Mai, N. A., Duc, N. T., Irgum, K., Chemistry of Materials 2008, 20, 6244-6247.

[33] Nguyen, A. M., Nordborg, A., Shchukarev, A., Irgum, K., Journal of separation science 2009, 32, 2619-2628.

[34] Work, W., Horie, K., Hess, M., Stepto, R., Pure and applied chemistry 2004, 76, 1985-2007.

[35] Barker, J., Fock, W., Discussions of the Faraday Society 1953, 15, 188-195.

[36] Matsuyama, H., Okafuji, H., Maki, T., Teramoto, M., Kubota, N., Journal of membrane science 2003, 223, 119-126.

[37] Lin, Y., Chen, G., Yang, J., Wang, X., Desalination 2009, 236, 8-15.

[38] Guillen, G. R., Pan, Y., Li, M., Hoek, E. M., Industrial & Engineering Chemistry Research 2011, 50, 3798-3817.

[39] Matsuyama, H., Kim, M.-m., Lloyd, D. R., Journal of Membrane Science 2002, 204, 413-419.

[40] Gu, M., Zhang, J., Xia, Y., Wang, X., Journal of Macromolecular Science, Part B 2007, 47, 180-191.

[41] Cui, Z.-Y., Xu, Y.-Y., Zhu, L.-P., Deng, H.-Y., et al., Journal of Macromolecular Science® 2009, 48, 41-54.

[42] Lloyd, D. R., Kinzer, K. E., Tseng, H., Journal of Membrane Science 1990, 52, 239-261.

[43] Lloyd, D. R., Kim, S. S., Kinzer, K. E., Journal of Membrane Science 1991, 64, 1- 11.

[44] Kim, S. S., Lloyd, D. R., Journal of membrane science 1991, 64, 13-29.

[45] Chan, P. K., Modelling and Simulation in Materials Science and Engineering 2006, 14, 41-51.

[46] Matsuyama, H., Kudari, S., Kiyofuji, H., Kitamura, Y., Journal of applied polymer science 2000, 76, 1028-1036.

[47] Gu, M., Zhang, J., Wang, X., Tao, H., Ge, L., Desalination 2006, 192, 160-167.

[48] Soroko, I., Lopes, M. P., Livingston, A., Journal of Membrane Science 2011, 381, 152-162.

[49] Yave, W., Quijada, R., Serafini, D., Lloyd, D. R., Journal of Membrane Science 2005, 263, 146-153.

(69)

59

[50] Yave, W., Quijada, R., Ulbricht, M., Benavente, R., Polymer 2005, 46, 11582- 11590.

[51] Vanegas, M. E., Quijada, R., Serafini, D., Polymer 2009, 50, 2081-2086.

[52] Atkinson, P. M., Lloyd, D. R., Journal of Membrane Science 2000, 175, 225-238.

[53] Matsuyama, H., Maki, T., Teramoto, M., Asano, K., Journal of membrane science 2002, 204, 323-328.

[54] GUO, B., FAN, J., LIU, J., XU, J., Wang, X., Acta Polymerica Sinica 2009, 1, 008.

[55] Tao, Y., Yu, G., Wang, X., Wang, Z., International Journal of Polymeric Materials 2011, 60, 706-719.

[56] Svec, F., Journal of separation science 2004, 27, 747-766.

[57] Ghasem, N., Al-Marzouqi, M., Duidar, A., Separation and Purification Technology 2012, 98, 174-185.

[58] Yang, M.-C., Perng, J.-S., Journal of Polymer Research 1998, 5, 213-219.

[59] Matsuyama, H., Teramoto, M., Kudari, S., Kitamura, Y., Journal of applied polymer science 2001, 82, 169-177.

[60] Yeow, M., Liu, Y., Li, K., Journal of Applied Polymer Science 2004, 92, 1782- 1789.

[61] Cao, Y., Croll, T. I., O'Connor, A. J., Stevens, G. W., Cooper-White, J. J., Journal of Biomaterials Science, Polymer Edition 2006, 17, 369-402.

[62] Yang, J., Wang, X. L., Tian, Y., Lin, Y., Tian, F., Journal of Polymer Science Part B:

Polymer Physics 2010, 48, 2468-2475.

[63] Lin, D.-J., Beltsios, K., Young, T.-H., Jeng, Y.-S., Cheng, L.-P., Journal of membrane science 2006, 274, 64-72.

[64] Wang, X., Wang, X., Zhang, L., An, Q., Chen, H., Journal of Macromolecular Science, Part B 2009, 48, 696-709.

[65] Li, C.-L., Wang, D.-M., Deratani, A., Quémener, D., et al., Journal of Membrane Science 2010, 361, 154-166.

[66] Ahmad, A., Ideris, N., Ooi, B., Low, S., Ismail, A., Desalination 2011, 278, 318- 324.

[67] Ghasem, N., Al-Marzouqi, M., Abdul Rahim, N., Separation and Purification Technology 2012, 99, 91-103.

[68] Wang, X., Yue, X., Wang, X., Guo, Q., Journal of Macromolecular Science, Part B 2011, 50, 880-889.

[69] Lin, Y., Tang, Y., Ma, H., Yang, J., et al., Journal of applied polymer science 2009, 114, 1523-1528.

[70] Nakatsuka, K., Ohmukai, Y., Maruyama, T., Matsuyama, H., Desalination and Water Treatment 2010, 17, 275-280.

[71] Ghasem, N., Al-Marzouqi, M., Duaidar, A., International Journal of Greenhouse Gas Control 2011, 5, 1550-1558.

[72] Matsuyama, H., Berghmans, S., Batarseh, M. T., Lloyd, D. R., Journal of membrane science 1998, 142, 27-42.

(70)

60

[73] Yoo, S., Kim, C., Journal of applied polymer science 2008, 108, 3154-3162.

[74] Ma, W., Chen, S., Zhang, J., Wang, X., Journal of Macromolecular Science®, Part B: Physics 2010, 50, 1-15.

[75] Van de Witte, P., Dijkstra, P. J., Van den Berg, J. W. A., Feijen, J., Journal of Membrane Science 1996, 117, 1-31.

[76] Ulbricht, M., Polymer 2006, 47, 2217-2262.

[77] Castro, A. J., Oak, P., U.S. Patents 4,247,498 1981.

[78] Barton, A. F. M., Handbook of Solubility Parameters and Other Cohesion Parameters, CRC Press, Boca Raton, FL, USA 1983.

[79] Hildebrand, J., Scott, R., Annual Review of Physical Chemistry 1950, 1, 75-92.

[80] Huggins, M. L., The Journal of Physical Chemistry 1942, 46, 151-158.

[81] Flory, P. J., The Journal of chemical physics 2004, 10, 51-61.

[82] Hansen, C. M., The Three Dimensional Solubility Parameter and Solvent Diffusion Coefficient - Their Importance in Surface Coating Formulation, Danish Technical Press, Copenhagen 1967.

[83] Hansen, C. M., Journal of Paint Technology 1967, 39, 505-510.

[84] Hansen, C. M. (Ed.), Hansen Solubility Parameters: A User's Handbook, 2nd Ed., CRC Press, Boca Raton 2007.

[85] Barton, A., Pure and Applied Chemistry 1985, 57, 905-912.

[86] Luna-Bárcenas, G., Meredith, J. C., Sanchez, I. C., Johnston, K. P., et al., The Journal of chemical physics 1997, 107, 10782-10792.

[87] Ten Brinke, G., Karasz, F. E., Macromolecules 1984, 17, 815-820.

[88] Kanamori, K., Nakanishi, K., Hanada, T., Soft Matter 2009, 5, 3106-3113.

[89] Barrett, E. P., Joyner, L. G., Halenda, P. P., Journal of the American Chemical society 1951, 73, 373-380.

[90] Yan, H., Row, K. H., International journal of molecular sciences 2006, 7, 155- 178.

[91] Wu, D., Xu, F., Sun, B., Fu, R., et al., Chemical reviews 2012, 112, 3959-4015.

[92] Zalipsky, S., Harris, J. M., Poly (ethylene glycol) 1997, 680, 1-13.

[93] Saeki, S., Kuwahara, N., Nakata, M., Kaneko, M., Polymer 1977, 18, 1027-1031.

[94] Josic, D., Buchacher, A., Jungbauer, A., Journal of Chromatography B:

Biomedical Sciences and Applications 2001, 752, 191-205.

[95] Liu, F., Hashim, N. A., Liu, Y., Abed, M., Li, K., Journal of Membrane Science 2011, 375, 1-27.

[96] Ahmad, A., Idens, N., Ooi, B., Low, S., Ismail, A., Journal of Applied Sciences 2014, 14, 1299-1303.

[97] Zhang, Y., Ding, H., Wei, S., Liu, S., et al., Journal of Porous Materials 2010, 17, 693-698.

[98] Kanamori, K., Nakanishi, K., Hanada, T., Advanced Materials 2006, 18, 2407- 2411.

(71)

61

[99] Seo, M., Hillmyer, M. A., Science 2012, 336, 1422-1425.

[100] Kailasam, K., Jun, Y.-S., Katekomol, P., Epping, J. D., et al., Chemistry of Materials 2009, 22, 428-434.

[101] Baraka, A., Hall, P., Heslop, M., Reactive and Functional Polymers 2007, 67, 585-600.

[102] Mequanint, K., Sanderson, R., Polymer 2003, 44, 2631-2639.

[103] Du Fresne von Hohenesche, C., Schmidt, D., Schadler, V., Chemistry of Materials 2008, 20, 6124-6129.

[104] Rogers, M. E., Long, T. E. (Eds.), Synthetic methods in step-growth polymers, John Wiley & Sons, Hoboken 2003.

[105] Ruben, G. C., Pekala, R. W., Journal of non-crystalline solids 1995, 186, 219- 231.

[106] Kreibiehl, G., Mahnke, H., Weber, H., Woerner, F. P., U. S. Patent 4,540,717 1985.

[107] Bretterbauer, K., Schwarzinger, C., Current Organic Synthesis 2012, 9, 342- 356.

[108] Cheong, I. W., Shin, J. S., Kim, J. H., Lee, S. J., Macromolecular Research 2004, 12, 225-232.

[109] Bhattacharya, A., Rawlins, J. W., Ray, P. (Eds.), Polymer grafting and crosslinking, John Wiley & Sons, Hoboken 2009.

[110] Nicolau, V., Martinelli, M., Strumia, M., Estenoz, D., Meira, G., Journal of applied polymer science 2009, 113, 1030-1041.

[111] Rogers, M. E., Long, T. E. (Eds.), Synthetic methods in step-growth polymers, John Wiley & Sons, Hoboken 2003.

[112] Wu, Y., Li, Y., Qin, L., Yang, F., Wu, D., Journal of Materials Chemistry B 2013, 1, 204-212.

[113] Hench, L. L., West, J. K., Chemical Reviews 1990, 90, 33-72.

[114] Rouquerol, J., Rouquerol, F., Sing, K. S. W., Adsorption by Powders and Porous Solids: Principles, Methodology and Applications, Academic press Inc., Cornwall 1999.

[115] Altman, E. I. (Ed.), Numerical Data and Functional Relationships in Science and Technology: Group 3:@ Crystal and Solid State Physics. Vol. 42, Physics of Covered Solid Surfaces. Subvol. A: Adsorbed Layers on Surfaces. Part 1: Adsorption on Surfaces and Surface Diffusion of Adsorbates, Springer 2001.

[116] Brunauer, S., Emmett, P. H., Teller, E., Journal of the American Chemical Society 1938, 60, 309-319.

[117] Langmuir, I., Journal of the American Chemical Society 1916, 38, 2221-2295.

[118] Sing, K. S. W., Everett, D. H., Haul, R. A. W., Moscou, L., et al., Pure Appl Chem 1985, 57, 603-619.

[119] Sing, K., Colloids and Surfaces A: Physicochemical and Engineering Aspects 2001, 187, 3-9.

(72)

62

[120] Webb, P. A., Orr, C., Analytical methods in fine particle technology, Micromeritics Instrument Corp 1997.

[121] Buchmeiser, M. R. (Ed.), Polymeric materials in organic synthesis and catalysis, Wiley-VCH, Weinheim, Germany 2003.

[122] Rolando, M., Roque-Malherbe, R., CRC Press Taylor and Francis Group, NW Suite 2007.

[123] Ritter, H., Drake, L., Industrial & Engineering Chemistry Analytical Edition 1945, 17, 782-786.

[124] Webb, P. A., Micromeritics Instrument Corp, Norcross, Georgia 2001.

[125] Egger, C., Du Fresne, C., Raman, V., Schädler, V., et al., Langmuir 2008, 24, 5877-5887.

[126] Scherer, G. W., Smith, D. M., Stein, D., Journal of non-crystalline solids 1995, 186, 309-315.

[127] Scherer, G. W., Smith, D. M., Qiu, X., Anderson, J. M., Journal of non- crystalline solids 1995, 186, 316-320.

[128] McMullan, D., Scanning 1995, 17, 175-185.

[129] Goldstein, J. I., Newbury, D. E., Joy, D. C., Fiori, C., et al., Scanning electron microscopy and X-ray microanalysis, Plenum Press, New York 1981.

[130] Vernon-Parry, K. D., III-Vs Review 2000, 13, 40-44.

[131] Stuart, B., Infrared Spectroscopy: Fundamentals and Applications, John Wiley

& Sons, Chichester, England 2004.

[132] Gregorio, R., Journal of Applied Polymer Science 2006, 100, 3272-3279.

[133] Zhang, M., Zhang, A.-Q., Zhu, B.-K., Du, C.-H., Xu, Y.-Y., Journal of Membrane Science 2008, 319, 169-175.

[134] Shindo, D., Oikawa, T., Analytical Electron Microscopy for Materials Science, Springer, Tokyo 2002, pp. 81-102.

[135] Vickerman, J. C., Gilmore, I. S. (Eds.), Surface analysis: the principal techniques, 2nd Ed., John Wiley & Sons, Chichester, UK 2009.

[136] Van der Heide, P., X-ray photoelectron spectroscopy: an introduction to principles and practices, John Wiley & Sons, Hoboken, New Jersey 2011.

[137] Watts, J. F., Wolstenholme, J., An introduction to surface analysis by XPS and AES, Wiley, Chichester, England 2003.

[138] Ratner, B. D., Castner, D. G., Electron spectroscopy for chemical analysis, Nova Science Publisher, Inc., New York 2009.

[139] Briggs, D., Surface analysis of polymers by XPS and static SIMS Cambridge University Press, Cambridge, UK 1998, pp. 47-87.

[140] Derylo-Marczewska, A., Goworek, J., Pikus, S., Kobylas, E., Zgrajka, W., Langmuir 2002, 18, 7538-7543.

[141] Jiang, J., Oberdörster, G., Biswas, P., Journal of Nanoparticle Research 2009, 11, 77-89.

(73)

63

[142] Hunter, R. J., in: Hunter, R. J. (Ed.), Zeta Potential in Colloid Science, Academic Press, London 1981, pp. 11-58.

[143] Hunter, R. J., in: Hunter, R. J. (Ed.), Zeta Potential in Colloid Science, Academic Press, London 1981, pp. 59-124.

[144] Buszewski, B., Bocian, S., Dziubakiewicz, E., Journal of separation science 2010, 33, 1529-1537.

[145] Taylor, J. D., Terray, A., Hart, S. J., Analytica chimica acta 2010, 670, 78-83.

[146] Hammond, C., Hammond, C. (Eds.), Basics of crystallography and diffraction, 3rd Ed., Oxford 2001.

[147] Nischang, I., Teasdale, I., Brüggemann, O., Analytical and bioanalytical chemistry 2011, 400, 2289-2304.

[148] Urban, J., Svec, F., Fréchet, J. M., Analytical chemistry 2010, 82, 1621-1623.

[149] Liu, H., Bai, X., Wei, D., Yang, G., Journal of Chromatography A 2014, 1324, 128-134.

[150] Svec, F., Journal of Chromatography A 2012, 1228, 250-262.

[151] Saito, Y., Jinno, K., Greibrokk, T., Journal of separation science 2004, 27, 1379- 1390.

[152] Wu, R. a., Hu, L., Wang, F., Ye, M., Zou, H., Journal of Chromatography A 2008, 1184, 369-392.

[153] Courtois, J., Byström, E., Irgum, K., Polymer 2006, 47, 2603-2611.

[154] Hemström, P., Nordborg, A., Irgum, K., Svec, F., Fréchet, J. M., Journal of separation science 2006, 29, 25-32.

[155] Regnier, F. E., Journal of High Resolution Chromatography 2000, 23, 19-26.

[156] Svec, F., Peters, E. C., Sýkora, D., Yu, C., Frechet, J. M., Journal of High Resolution Chromatography 2000, 23, 3-18.

[157] Hilder, E. F., Svec, F., Frechet, J. M., Electrophoresis 2002, 23, 3934-3953.

[158] Štulík, K., Pacáková, V., Suchánková, J., Coufal, P., Journal of Chromatography B 2006, 841, 79-87.

[159] Hilder, E. F., Svec, F., Fréchet, J. M., Journal of Chromatography A 2004, 1044, 3-22.

[160] Sýkora, D., Peters, E. C., Svec, F., Fréchet, J. M., Macromolecular Materials and Engineering 2000, 275, 42-47.

[161] Vázquez, M., Paull, B., Analytica chimica acta 2010, 668, 100-113.

[162] Svec, F., Journal of Chromatography B 2006, 841, 52-64.