Bisphenol, Diethylstilbestrol, Polycarbonate and the Thermomechanical Properties of Epoxy–Silica Nanostructured Composites
DOI:
https://doi.org/10.6000/1929-5995.2013.02.04.1Keywords:
Polycarbonate, polymer, nanocomposite, nanosphere, nanosilica, amine, nanostructure, nanomaterialAbstract
The report has a double character: it deals with the synthesis and preparation of a series of polymers based on bisphenol-A (BPA) monomer; a series of physical and thermomechanical properties are examined for one type (diglycidyl ether of BPA, DGEBA with nanosilica) of the prepared materials. The reactions involved in diepoxy curing with a diamine, functional group modelling for cross-linked polymers, formation of a polymer DGEBA, BPA polyaddition to DGEBA forming a polyether, DGEBA curing with Jeffamine and cross-linking to form a resin are analyzed. Nanocomposites of silica, coated with cross-linked epoxy–amine, are synthesized and examined by 29Si-magic-angle-spinning nuclear magnetic resonance and Fourier-transform infrared spectroscopies, thermogravimetric and dynamic mechanical analyses, differential scanning calorimetry and scanning electron microscopy. Epoxy matrix is filled with nanosilica to design materials with defined properties. A low weight percentage of filler results in matrix improvement.
References
Krishnan AV, Stathis P, Permuth SF, Tokes L, Feldman D. Bisphenol-A: An estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrinology 1993; 132: 2279-86. http://dx.doi.org/10.1210/en.132.6.2279 DOI: https://doi.org/10.1210/endo.132.6.8504731
Deligio T. The BPA debate from two perspectives. Mod Plast Worldwide 2010; 87(6): 12-8.
Stillman RJ. In utero exposure to diethylstilbestrol: Adverse effects on the reproductive tract and reproductive performance of male and female offspring. Am J Obstet Gynecol 1982; 142: 905-21. DOI: https://doi.org/10.1016/S0002-9378(16)32540-6
Schrager S, Potter BE. Diethylstilbestrol exposure. Am Fam Physician 2004; 69: 2395-400.
Olsen CM, Meussen-Elholm ETM, Samuelsen M, Holme JA, Hongslo JK. Effects of the environmental oestrogens bisphenol A, tetrachlorobisphenol A, tetrabromobisphenol A, 4 hydroxybiphenyl and 4,4’-dihydroxybiphenyl on oestrogen receptor binding, cell proliferation and regulation of oestrogen sensitive proteins in the human breast cancer cell line MCF-7. Pharmacol Toxicol 2003; 92: 180-8. http://dx.doi.org/10.1034/j.1600-0773.2003.920408.x DOI: https://doi.org/10.1034/j.1600-0773.2003.920408.x
Birnbaum LS, Staskal DF. Brominated flame retardants: Cause for concern? Environ Health Perspect 2004; 112: 9-17. http://dx.doi.org/10.1289/ehp.6559 DOI: https://doi.org/10.1289/ehp.6559
Song W, Li Z, Ding F. Determination of bisphenol A in effluent water of analogue MBR wastewater treatment system using high-performance liquid chromatography. Res J Chem Environ 2011; 15(2): 8-12.
Herrero-Hernández E, Carabias-Martínez R, Rodríguez-Gonzalo E. Behavior of phenols and phenoxyacids on a bisphenol-A imprinted polymer. Application for selective solid-phase extraction from water and urine samples. Int J Mol Sci 2011; 12: 3322-39. http://dx.doi.org/10.3390/ijms12053322 DOI: https://doi.org/10.3390/ijms12053322
Singh S, Li SSL. Epigenetic effects of environmental chemicals bisphenol A and phthalates. Int J Mol Sci 2012; 13: 10143-53. http://dx.doi.org/10.3390/ijms130810143 DOI: https://doi.org/10.3390/ijms130810143
Sourour S, Kamal MR. Differential scanning calorimetry of epoxy cure: Isothermal cure kinetics. Thermochim Acta 1976; 14: 41-59. http://dx.doi.org/10.1016/0040-6031(76)80056-1 DOI: https://doi.org/10.1016/0040-6031(76)80056-1
Núñez L, Fraga F, Fraga L, Castro A. Kinetic and thermodynamic studies of an epoxy system diglycidyl ether of bisphenol-A/1,2 diamine cyclohexane. J Appl Polym Sci 1997; 63: 635-41. http://dx.doi.org/10.1002/(SICI)1097-4628(19970131)63:5<635::AID-APP11>3.0.CO;2-T DOI: https://doi.org/10.1002/(SICI)1097-4628(19970131)63:5<635::AID-APP11>3.0.CO;2-T
Fraga F, Penas M, Castro C, Rodríguez-Núñez E, Martínez-Ageitos JM. Cure kinetics of a diglycidyl ether of bisphenol A epoxy network (n = 0) with isophorone diamine. J Appl Polym Sci 2007; 106: 4169-73. http://dx.doi.org/10.1002/app.26989 DOI: https://doi.org/10.1002/app.26989
Ghosh NN, Kiskan B, Yagci Y. Polybenzoxazines—New high performance thermosetting resins: Synthesis and properties. Prog Polym Sci 2007; 32: 1344-91. http://dx.doi.org/10.1016/j.progpolymsci.2007.07.002 DOI: https://doi.org/10.1016/j.progpolymsci.2007.07.002
Takeichi T, Saito Y, Agag T, Muto H, Kawauchi T. High-performance polymer alloys of polybenzoxazine and bismaleimide. Polymer 2008; 49: 1173-9. http://dx.doi.org/10.1016/j.polymer.2008.01.041 DOI: https://doi.org/10.1016/j.polymer.2008.01.041
Sharifi S. Dielectric spectroscopy of diglycidyl ether of bisphenol-A at glass transition temperature. Nat Sci 2012; 4: 136-41. DOI: https://doi.org/10.4236/ns.2012.42020
Wang Q, Chen G. Effect of nanofillers on the dielectric properties of epoxy nanocomposites. Adv Mater Res 2012; 1: 93-107. http://dx.doi.org/10.12989/amr.2012.1.1.093 DOI: https://doi.org/10.12989/amr.2012.1.1.093
Zhao C, Zhang G, Zhao L. Effect of curing agent and temperature on the rheological behavior of epoxy resin systems. Molecules 2012; 17: 8587-94. http://dx.doi.org/10.3390/molecules17078587 DOI: https://doi.org/10.3390/molecules17078587
Prolongo SG, Gude MR, Urena A. Adhesive strength and toughness improvement of epoxy resin modified with polystyrene-b-polybutadiene-b-poly (methyl methacrylate) block copolymer. J Mater Sci Eng 2012; 1: 109–1-5. DOI: https://doi.org/10.4172/2169-0022.1000109
Akande IS, Hassan O, Adeshakin A. Gas chromatography-mass spectrophotometry evaluation of the concentration of bisphenol-A (BPA) in five selected canned food products consumed in Lagos Area, Nigeria. Br J Appl Sci Technol 2014; 4: 187-97. DOI: https://doi.org/10.9734/BJAST/2014/5881
Tarko L, Putz MV, Ionascu C, Putz AM. QSTR studies regarding the ECOSAR toxicity of benzene-carboxylic acids’ esters to fathead minnow fish (Pimephales promelas). Curr Comput Aided Drug Des, submitted for publication.
Piscitelli F, Lavorgna M, Buonocore GG, Verdolotti L, Galy J, Mascia L. Plasticizing and reinforcing features of siloxane domains in amine-cured epoxy/silica hybrids. Macromol Mater Eng 2013; 298: 896-909. http://dx.doi.org/10.1002/mame.201200222 DOI: https://doi.org/10.1002/mame.201200222
Verdolotti L, Lavorgna M, Oliviero M, Sorrentino A, Iozzino V, Buonocore G, Iannace S. Functional zein–siloxane bio-hybrids. ACS Sust Chem Eng, in press.
Torrens F, Soria V, Monzó IS, Abad C, Campos A. Treatment of poly(styrene-co-methacrylic acid)/poly(4-vinylpyridine) blends in solution under liquid–liquid phase-separation conditions. A new method for phase-separation data attainment from viscosity measurements. J Appl Polym Sci 2006; 102: 5039-49. http://dx.doi.org/10.1002/app.25082 DOI: https://doi.org/10.1002/app.25082
Torrens F, Soria V, Codoñer A, Abad C, Campos A. Compatibility between polystyrene copolymers and polymers in solution via hydrogen bonding. Eur Polym J 2006; 42: 2807-23. http://dx.doi.org/10.1016/j.eurpolymj.2006.04.020 DOI: https://doi.org/10.1016/j.eurpolymj.2006.04.020
Torrens F, Monzó IS, Gómez-Clarí CM, Abad C, Campos A. Study and comparison of interaction parameters and phase behaviour of epoxy/polystyrene and epoxies copolymer polystyrene–b–poly(methyl methacrylate) blends. Polym Compos 2008; 29: 1337-45. http://dx.doi.org/10.1002/pc.20518
Torrens F, Castellano G. Determination of binodal curves in ternary polymer systems: Co /polymers compatibility. In: Kumar SA, Thiagarajan S, Wang SF, editors. New developments in polymer composites research. New York: Nova, in press.
Torrens F, Gómez CM, León LM, Abad C, Campos A. Modelling studies of the phase behaviour of monomer/polymer/disk composites. Macromol Theory Simul 2008; 17: 325-40. http://dx.doi.org/10.1002/mats.200800013 DOI: https://doi.org/10.1002/mats.200800013
Torrens F, Gómez CM, Monzó IS, Abad C, Campos A. Modelling Monomer/Disc Composites Phase Behaviour. Macromol Symp 2012; 311: 49-56. http://dx.doi.org/10.1002/masy.201000108 DOI: https://doi.org/10.1002/masy.201000108
Torrens F, Castellano G. Experimental studies for modelling the phase behaviour of monomer/polymer/disc composites. Macromol Symp 2010; 296: 557-65. http://dx.doi.org/10.1002/masy.201051073 DOI: https://doi.org/10.1002/masy.201051073
Torrens F, Monzó IS, Gómez-Clarí CM, Abad C, Campos A. Study and comparison of interaction parameters and phase behaviour of epoxy/polystyrene and epoxies copolymer polystyrene–b–poly(methyl methacrylate) blends. Polym Compos 2008; 29: 1337-45. http://dx.doi.org/10.1002/pc.20518 DOI: https://doi.org/10.1002/pc.20518
Torrens F, Solar L, Puchol V, Latorre J, Abad C, Campos A. Incorporation of silica nanospherical particles into epoxy-amine cross-linked materials. Polym Polym Compos 2008; 16: 139-52. DOI: https://doi.org/10.1177/096739110801600207
Torrens F, Castellano G. Incorporation of silica nanospheres into epoxy–amine materials: Polymer nanocomposites. In: Lechkov M, Prandzheva S, editors. Encyclopedia of polymer composites: Properties, performance and applications. Polymer Science and Technology No. 5. New York: Nova 2010; p. 823-44.
Torrens-Zaragozá F. Polymer bisphenol-A, the incorporation of silica nanospheres into epoxy–amine materials and polymer nanocomposites. Nereis 2011; (3): 17-23.
León LM, Laza M, Torrens F, Puchol V, Abad C, Campos A. Incorporation of silica nanospherical particles in epoxy–amine cross-linked materials II. Dynamic mechanical measurements of epoxy matrix-silica nanocomposites. Polym Polym Compos 2009; 17: 457-65. DOI: https://doi.org/10.1177/096739110901700707
León LM, Laza M, Puchol V, Torrens F, Abad C, Campos A. Dynamic mechanical measurements of epoxy matrix-silica nanocomposites II. Polym Polym Compos 2009; 17: 313-24. DOI: https://doi.org/10.1177/096739110901700505
Fiege H, Voges HW, Hamamoto T, Umemura S, Iwata T, Miki H, Fujita Y, Buysch HJ, Garbe D, Paulus W. Phenol derivatives. In: Ullmann’s encyclopedia of industrial chemistry. Weinheim (Ger.): Wiley-VCH 2002.
Bateman C. Get your coat. Hydrocarbon Eng 2012; 17(3): 74-80.
Kharasch MS, Kleiman M. Synthesis of polyenes. III. A new synthesis of diethylstilbestrol. J Am Chem Soc 1943; 65: 11-5. http://dx.doi.org/10.1021/ja01241a004 DOI: https://doi.org/10.1021/ja01241a004
Barton JM. The application of differential scanning calorimetry (DSC) to the study of epoxy resin curing reactions. Adv Polym Sci 1985; 72: 112-54. http://dx.doi.org/10.1007/3-540-15546-5_5 DOI: https://doi.org/10.1007/3-540-15546-5_5
Rozenberg BA. Kinetics, thermodynamics and mechanism of reactions of epoxy oligomers with amines. Adv Polym Sci 1986; 75: 113-65. http://dx.doi.org/10.1007/BFb0017916 DOI: https://doi.org/10.1007/BFb0017916
Riccardi CC, Adabbo HE, Williams RJJ. Curing reaction of epoxy resins with diamines. J Appl Polym Sci 1984; 29: 2481-92. http://dx.doi.org/10.1002/app.1984.070290805 DOI: https://doi.org/10.1002/app.1984.070290805
Kim DH, Kim SC. Vitrification effect on the curing reaction of epoxy resin. Polym Bull (Berlin) 1987; 18: 533-9. DOI: https://doi.org/10.1007/BF00255338
Laza JM, Julian CA, Larrauri E, Rodriguez M, Leon LM. Thermal scanning rheometer analysis of curing kinetic of an epoxy resin: 2. An amine as curing agent. Polymer 1998; 40: 35-45. http://dx.doi.org/10.1016/S0032-3861(98)00217-1 DOI: https://doi.org/10.1016/S0032-3861(98)00217-1
Carrozzino S, Levita G, Rolla P, Tombari E. Calorimetric and microwave dielectric monitoring of epoxy resin cure. Polym Eng Sci 1990; 30: 366-73. http://dx.doi.org/10.1002/pen.760300608 DOI: https://doi.org/10.1002/pen.760300608
Vyazorkin S, Shinazzuoli N. Mechanism and kinetics of epoxy–amine cure studied by differential scanning calorimetry. Macromolecules 1996; 29: 1867-73. http://dx.doi.org/10.1021/ma951162w DOI: https://doi.org/10.1021/ma951162w
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