Hansen solubility parameters for octahedral oligomeric silsesquioxanes

Industrial and Engineering Chemistry Research

Volumn 51, Issue 38, 2012, Pages 12282-12293

  Guenthner, Andrew J ^a   Lamison, Kevin R ^a   Lubin, Lisa M ^a   Haddad, Timothy S ^a   Mabry, Joseph M ^a  

^a AIR FORCE RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GROUP CONTRIBUTIONS; HANSEN SOLUBILITY PARAMETERS; ISOBUTYL; ORGANIC-INORGANIC COMPOUND; POLYHEDRAL OLIGOMERIC SILSESQUIOXANES; POOR SOLVENTS; SILSESQUIOXANES; SOLUBILITY PARAMETERS;

HYDROGEN BONDS; INORGANIC COMPOUNDS; NAPHTHALENE; OLIGOMERS; ORGANIC COATINGS; UNCERTAINTY ANALYSIS;

SOLUBILITY;

EID: 84867546239     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie300767p     Document Type: Article

References (70)

1. Hansen, C. M. Hansen Solubility Parameters: A User's Handbook, 2nd ed.; CRC Press: Boca Raton, FL, 2007.
2. Vink, P.; Bots, T. L. Formulation parameters influencing selfstratification of coatings. Prog. Org. Coat. 1996, 28, 173-181.
3. Hansen, C. M. 50 Years with solubility parameters - past and future. Prog. Org. Coat. 2004, 51, 77-84.
4. Hansen, C. M. Cohesion parameters for surfaces, pigments, and fillers. JOCCA-Surf. Coat. Int. 1997, 80, 386-&.
5. Hansen, C. M. The three-dimensional solubility parameter - key to paint component affinities I. J. Paint Technol. 1967, 39, 104-117.
6. Dong, G. X.; Li, H. Y.; Chen, V. Factors affect defect-free Matrimid (R) hollow fiber gas separation performance in natural gas purification. J. Membr. Sci. 2010, 353, 17-27.
7. Hellsten, S.; Qu, H. Y.; Louhi-Kultanen, M. Screening of Binary Solvent Mixtures and Solvate Formation of Indomethacin. Chem. Eng. Technol. 2011, 34, 1667-1674.
8. Dwan'Isa, J. P. L.; Rouxhet, L.; Preat, V.; Brewster, M. E.; Arien, A. Prediction of drug solubility in amphiphilic di-block copolymer micelles: the role of polymer-drug compatibility. Pharmazie 2007, 62, 499-504.
9. Breitkreutz, J. Prediction of intestinal drug absorption properties by three-dimensional solubility parameters. Pharm. Res. 1998, 15, 1370-1375.
10. Ho, D. L.; Glinka, C. J. Effects of solvent solubility parameters on organoclay dispersions. Chem. Mater. 2003, 15, 1309-1312.
11. Li, F. H.; Bao, Y.; Chai, J.; Zhang, Q. X.; Han, D. X.; Niu, L. Synthesis and Application of Widely Soluble Graphene Sheets. Langmuir 2010, 26, 12314-12320.
12. Hansen, C. M.; Smith, A. L. Using Hansen solubility parameters to correlate solubility of C-60 fullerene in organic solvents and in polymers. Carbon 2004, 42, 1591-1597.
13. Rostami, M.; Mohseni, M.; Ranjbar, Z. Investigating the effect of pH on the surface chemistry of an amino silane treated nano silica. Pigm. Resin Technol. 2011, 40, 363-373.
14. Schreuder, M. A.; Gosnell, J. D.; Smith, N. J.; Warnement, M. R.; Weiss, S. M.; Rosenthal, S. J. Encapsulated white-light CdSe nanocrystals as nanophosphors for solid-state lighting. J. Mater. Chem. 2008, 18, 970-975.
15. Wieneke, J. U.; Kommoss, B.; Gaer, O.; Prykhodko, I.; Ulbricht, M. Systematic Investigation of Dispersions of Unmodified Inorganic Nanoparticles in Organic Solvents with Focus on the Hansen Solubility Parameters. Ind. Eng. Chem. Res. 2012, 51, 327-334.
16. Cordes, D. B.; Lickiss, P. D.; Rataboul, F. Recent Developments in the Chemistry of Cubic Polyhedral Oligosilsesquioxanes. Chem. Rev. 2010, 110, 2081-2173.
17. Ghanbari, H.; Cousins, B. G.; Seifalian, A. M. A Nanocage for Nanomedicine: Polyhedral Oligomeric Silsesquioxane (POSS). Macromol. Rapid Commun. 2011, 32, 1032-1046.
18. Phillips, S. H.; Haddad, T. S.; Tomczak, S. J. Developments in nanoscience: polyhedral silsesquioxane (POSS)-polymers oligomeric. Curr. Opin. Solid State Mater. Sci. 2004, 8, 21-29.
19. Hartmann-Thompson, C. Applications of Polyhedral Oligomeric Silsesquioxanes; Springer: New York, 2011.
20. Pakjamsai, C.; Kawakami, Y. Study on effective synthesis and properties of ortho-alkyl-substituted phenyl octasilsesquioxane. Des. Monomers Polym. 2005, 8, 423-435.
21. Moore, B. M.; Ramirez, S. M.; Yandek, G. R.; Haddad, T. S.; Mabry, J. M. Asymmetric aryl polyhedral oligomeric silsesquioxanes (ArPOSS) with enhanced solubility. J. Organomet. Chem. 2011, 696, 2676-2680.
22. Hao, N.; Boehning, M.; Schoenhals, A. Dielectric properties of nanocomposites based on polystyrene and polyhedral oligomeric phenethyl-silsesquioxanes. Macromolecules 2007, 40, 9672-9679.
23. Iwamura, T.; Adachi, K.; Sakaguchi, M.; Chujo, Y. Synthesis of organic-inorganic polymer hybrids from poly(vinyl chloride) and polyhedral oligomeric silsesquioxane via CH/pi interaction. Prog. Org. Coat. 2009, 64, 124-127.
24. Misra, R.; Fu, B. X.; Plagge, A.; Morgan, S. E. POSS-Nylon 6 Nanocomposites: Influence of POSS Structure on Surface and Bulk Properties. J. Polym. Sci., Part B: Polym. Phys. 2009, 47, 1088-1102.
25. Jones, P. J.; Cook, R. D.; McWright, C. N.; Nalty, R. J.; Choudhary, V.; Morgan, S. E. Polyhedral Oligomeric Silsesquioxane- Polyphenylsulfone Nanocomposites: Investigation of the Melt-Flow Enhancement, Thermal Behavior, and Mechanical Properties. J. Appl. Polym. Sci. 2011, 121, 2945-2956.
26. Cook, R. D.; Wei, Y. H.; Misra, R.; Morgan, S. E. Determination of polyhedral oligomeric silsesquioxane (POSS) and nylon solubility parameters for predicting dispersion in polymer composites. Abstr. Pap. Am. Chem. Soc. 2010, 240.
27. Lim, S. K.; Hong, E. P.; Song, Y. H.; Choi, H. J.; Chin, I. J. Thermodynamic interaction and mechanical characteristics of Nylon 6 and polyhedral oligomeric silsesquioxane nanohybrids. J. Mater. Sci. 2012, 47, 308-314.
28. Lim, S. K.; Hong, E. P.; Choi, H. J.; Chin, I. J. Polyhedral oligomeric silsesquioxane and polyethylene nanocomposites and their physical characteristics. J. Ind. Eng. Chem. 2010, 16, 189-192.
29. Dintcheva, N. T.; Morici, E.; Arrigo, R.; La Mantia, F. P.; Malatesta, V.; Schwab, J. J. Structure-properties relationships of polyhedral oligomeric silsesquioxane (POSS) filled PS nanocomposites. eXPRESS Polym. Lett. 2012, 6 (7), 561-571.
30. Milliman, H. W.; Boris, D.; Schiraldi, D. A. Experimental Determination of Hansen Solubility Parameters for Select POSS and Polymer Compounds as a Guide to POSS-Polymer Interaction Potentials. Macromolecules 2012, 45, 1931-1936.
31. Barra, J.; Pena, M. A.; Bustamante, P. Proposition of group molar constants for sodium to calculate the partial solubility parameters of sodium salts using the van Krevelen group contribution method. Eur. J. Pharm. Sci. 2000, 10, 153-161.
32. Bustamante, P.; Pena, M. A.; Barra, J. The modified extended Hansen method to determine partial solubility parameters of drugs containing a single hydrogen bonding group and their sodium derivatives: benzoic acid/Na and ibuprofen/Na. Int. J. Pharm. 2000, 194, 117-124.
33. Arita, T.; Moriya, K.; Yoshimura, T.; Minami, K.; Naka, T.; Adschiri, T. Dispersion of Phosphonic Acids Surface-Modified Titania Nanocrystals in Various Organic Solvents. Ind. Eng. Chem. Res. 2010, 49, 9815-9821.
34. Chen, H. J.; Wang, L.; Chiu, W. Y. Chelation and solvent effect on the preparation of titania colloids. Mater. Chem. Phys. 2007, 101, 12-19.
35. Lafaurie, A.; Azema, N.; Ferry, L.; Lopez-Cuesta, J. M. Stability parameters for mineral suspensions: Improving the dispersion of fillers in thermoplastics. Powder Technol. 2009, 192, 92-98.
36. Shibata, J.; Fujii, K.; Horai, K.; Yamamoto, H. Dispersion and flocculation behavior of metal oxide powders in organic solvent. Kag. Kog. Ronbunshu 2001, 27, 497-501.
37. Shibata, J.; Fujii, K.; Yamamoto, H. Dispersion and flocculation behavior of rare earth oxide powders in organic solvent. Kag. Kog. Ronbunshu 2002, 28, 641-646.
38. Klingenfus, J.; Palmas, P. Weak molecular associations investigated by (1)H-NMR spectroscopy on a neat organosiloxanesolvent mixture. Phys. Chem. Chem. Phys. 2011, 13, 10661-10669.
39. Schierholz, J. M. Physico-chemical properties of a rifampicinreleasing polydimethylsiloxane shunt. Biomaterials 1997, 18, 635-641.
40. Zhou, H. L.; Su, Y.; Chen, X. R.; Wan, Y. H. Separation of acetone, butanol and ethanol (ABE) from dilute aqueous solutions by silicalite-1/PDMS hybrid pervaporation membranes. Sep. Purif. Technol. 2011, 79, 375-384.
41. Orme, C. J.; Klaehn, J. R.; Harrup, M. K.; Lash, R. P.; Stewart, F. F. Characterization of 2-(2-methoxyethoxy)ethanol-substituted phosphazene polymers using pervaporation, solubility parameters, and sorption studies. J. Appl. Polym. Sci. 2005, 97, 939-945.
42. Cataldo, F. On the Solubility Parameter of C60 and Higher Fullerenes. Fullerenes, Nanotubes, Carbon Nanostruct. 2009, 17, 79-84.
43. Acevedo, S.; Castro, A.; Vasquez, E.; Marcano, F.; Ranaudo, M. A. Investigation of Physical Chemistry Properties of Asphaltenes Using Solubility Parameters of Asphaltenes and Their Fractions A1 and A2. Energy Fuels 2010, 24, 5921-5933.
44. Aray, Y.; Hernandez-Bravo, R.; Parra, J. G.; Rodriguez, J.; Coll, D. S. Exploring the Structure-Solubility Relationship of Asphaltene Models in Toluene, Heptane, and Amphiphiles Using a Molecular Dynamic Atomistic Methodology. J. Phys. Chem. A 2011, 115, 11495- 11507.
45. Mutelet, F.; Ekulu, G.; Solimando, R.; Rogalski, M. Solubility parameters of crude oils and asphaltenes. Energy Fuels 2004, 18, 667- 673.
46. Nikooyeh, K.; Shaw, J. M. On the Applicability of the Regular Solution Theory to Asphaltene plus Diluent Mixtures. Energy Fuels 2012, 26, 576-585.
47. Redelius, P. Bitumen solubility model using Hansen solubility parameter. Energy Fuels 2004, 18, 1087-1092.
48. Wang, T.; Zhang, Y. Z. Methods for Determining the Solubility Parameter of Bitumen. J. Test. Eval. 2010, 38, 383-389.
49. Hao, N.; Bohning, M.; Schonhals, A. CO(2) Gas Transport Properties of Nanocomposites Based on Polyhedral Oligomeric Phenethyl-Silsesquioxanes and Poly(bisphenol A carbonate). Macromolecules 2010, 43, 9417-9425.
50. Voronkov, M. G.; Kovrigin, V. M.; Lavrent'ev, V. I.; Moralev, V. M. Reaction of pervinyloctasilsesquioxane with benzene in the presence of aluminum trichloride. Perphenethyloctasilsesquioxane. Dokl. Akad. Nauk SSSR 1985, 281 (6).
51. Sanchez-Soto, M.; Schiraldi, D. A.; Illescas, S. Study of the morphology and properties of melt-mixed polycarbonate-POSS nanocomposites. Eur. Polym. J. 2009, 45, 341-352.
52. Hosaka, N.; Otsuka, H.; Hino, M.; Takahara, A. Control of dispersion state of silsesquioxane nanofillers for stabilization of polystyrene thin films. Langmuir 2008, 24, 5766-5772.
53. Hao, N.; Bohning, M.; Goering, H.; Schonhals, A. Nanocomposites of polyhedral oligomeric phenethylsilsesquioxanes and poly(bisphenol A carbonate) as investigated by dielectric spectroscopy. Macromolecules 2007, 40, 2955-2964.
54. Blanski, R. L.; Phillips, S. H.; Chaffee, K.; Lichtenhan, J.; Lee, A.; Geng, H. P. Preparation and properties of organic-inorganic hybrid materials by blending polyhedral oligosilsesquioxanes into organic polymers. Polym. Prepr. 2000, 41, 585-586.
55. Blanski, R. L.; Phillips, S. H.; Chaffee, K.; Lichtenhan, J.; Lee, A.; Geng, H. P. The Synthesis of Hybrid Materials by the Blending of Polyhedral Oligosilsesquioxanes into Organic Polymers. Mater. Res. Soc. Symp. Proc. 2000, 628, CC6.27.1-CC6.27.6.
56. Feher, F. J.; Soulivong, D.; Eklund, A. G.; Wyndham, K. D. Cross-metathesis of alkenes with vinyl-substituted silsesquioxanes and spherosilicates: A new method for synthesizing highly-functionalized Si/O frameworks. Chem. Commun. 1997, 1185-1186.
57. Chhatre, S. S.; Guardado, J. O.; Moore, B. M.; Haddad, T. S.; Mabry, J. M.; McKinley, G. H.; Cohen, R. E. Fluoroalkylated Silicon- Containing Surfaces-Estimation of Solid-Surface Energy. ACS Appl. Mater. Interfaces 2010, 2, 3544-3554.
58. Mabry, J. M.; Vij, A.; Iacono, S. T.; Viers, B. D. Fluorinated polyhedral oligomeric silsesquioxanes (F-POSS). Angew. Chem., Int. Ed. 2008, 47, 4137-4140.
59. Tuteja, A.; Choi, W.; Ma, M. L.; Mabry, J. M.; Mazzella, S. A.; Rutledge, G. C.; McKinley, G. H.; Cohen, R. E. Designing superoleophobic surfaces. Science 2007, 318, 1618-1622.
60. Belmares, M.; Blanco, M.; Goddard, W. A.; Ross, R. B.; Caldwell, G.; Chou, S. H.; Pham, J.; Olofson, P. M.; Thomas, C. Hildebrand and Hansen solubility parameters from molecular dynamics with applications to electronic nose polymer sensors. J. Comput. Chem. 2004, 25, 1814-1826.
61. Choi, P.; Kavassalis, T. A.; Rudin, A. Estimation of Hansen Solubility Parameters for (Hydroxyethyl)-Cellulose and (Hydroxypropyl)Cellulose through Molecular Simulation. Ind. Eng. Chem. Res. 1994, 33, 3154-3159.
62. Jarvas, G.; Quellet, C.; Dallos, A. Estimation of Hansen solubility parameters using multivariate nonlinear QSPR modeling with COSMO screening charge density moments. Fluid Phase Equilib. 2011, 309, 8-14.
63. Tantishaiyakul, V.; Worakul, N.; Wongpoowarak, W. Prediction of solubility parameters using partial least square regression. Int. J. Pharm. 2006, 325, 8-14.
64. Zeng, F. L.; Sun, Y.; Zhou, Y.; Li, Q. K. Molecular simulations of the miscibility in binary mixtures of PVDF and POSS compounds. Modell. Simul. Mater. Sci. Eng. 2009, 17 (7).
65. Zeng, Z. Y.; Xu, Y. Y.; Li, Y. W. Calculation of Solubility Parameter Using Perturbed-Chain SAFT and Cubic-Plus-Association Equations of State. Ind. Eng. Chem. Res. 2008, 47, 9663-9669.
66. Stefanis, E.; Tsivintzelis, I.; Panayiotou, C. The partial solubility parameters: An equation-of-state approach. Fluid Phase Equilib. 2006, 240, 144-154.
67. Constantinou, L.; Gani, R.; Oconnell, J. P. Estimation of the acentric factor and the liquid molar volume at 298-K using a new group-contribution method. Fluid Phase Equilib. 1995, 103, 11-22.
68. Stefanis, E.; Panayiotou, C. Prediction of Hansen solubility parameters with a new group-contribution method. Int. J. Thermophys. 2008, 29, 568-585.
69. Lavrent'ev, V. I. Per(gamma-trifluoropropyl)octasilsesquioxane. Russ. J. Gen. Chem. 2004, 74, 1188-1193.
70. Iacono, S. T.; Vij, A.; Grabow, W.; Smith, D. W.; Mabry, J. M. Facile synthesis of hydrophobic fluoroalkyl functionalized silsesquioxane nanostructures. Chem. Commun. 2007, 4992-4994.