Co-reporter:Dariusz Bogdal, Jaroslaw Gorczyk, and Beata Kwasek
ACS Sustainable Chemistry & Engineering 2016 Volume 4(Issue 6) pp:3024
Publication Date(Web):April 15, 2016
DOI:10.1021/acssuschemeng.5b01786
A new method of preparation of solid epoxy resins (SER) with desired epoxy-group content via an advanced process under microwave irradiation is presented together with the results of molecular weight measurements for narrow oligomeric fractions obtained from chromatographic separation of SER. All the measurements were performed using gel permeation chromatography (GPC) and matrix-assisted laser desorption ionization spectrometry–time of flight mass spectrometry (MALDI-TOF/MS). In the GPC analysis, two types of calibration were used: the first was a standard calibration based on polystyrene standards, while the second was done on the basis of a chromatograms of epoxy resins synthesized from bisphenol A (BPA) and diglycidyl ether of bisphenol A (EDBPA). On the basis of the MALDI-TOF analysis, it was assumed that the purity of starting materials, i.e., low molecular weight epoxy resin, clearly determined the structure of the SER. In order to obtain an SER with linear chain structures and an even number of polymerization degrees, the low molecular weight epoxy needs to be characterized by a high content of diglycidyl ether of bisphenol A (EDBPA) as it was observed for Rutapox 0162. In the case of low molecular weight epoxy resins that contained a higher oligomeric fraction of diglycidyl ether of bisphenol A (EDBPA) like Epikote 828, one can observe an even and odd polymerization degree which resulted in the branching of chain structures. Eventually, the procedure of chromatographic separation of SER allowed a better correlation of results from MALDI-TOF/MS and the GPC.Keywords: GPC; MALDI-TOF/MS; Microwave irradiation; Polyaddition; Solid epoxy resin
Co-reporter:Dariusz Bogdal, Mateusz Galica, Grzegorz Bartus, Jacek Wolinski and Stanislaw Wronski
Organic Process Research & Development 2010 Volume 14(Issue 3) pp:669-683
Publication Date(Web):May 21, 2010
DOI:10.1021/op100040x
The application of phase-transfer catalytic (PTC) conditions leading to substantial improvements in numerous polymerization reactions is described. Generally, better yields as well as faster and cleaner reactions are achieved compared to reactions under conventional conditions. Owing to their ionic mechanisms, polycondensation reactions are the most often applied among polymerization methods under PTC conditions; thus, a number of examples on gram scale are presented in this review.
Co-reporter:Dariusz Bogdal;Katarzyna Matras;Jerzy Sanetra;Monika Pokladko
Macromolecular Symposia 2008 Volume 268( Issue 1) pp:48-52
Publication Date(Web):
DOI:10.1002/masy.200850810
Abstract
Summary: The article focuses on the photovoltaic devices made from copolymers of 2-(carbazol-9-yl)ethyl methacrylate (CEM) with benzofuran-2-carboxylic acid 2-(methacryloyloxy)ethyl 6-(diethylamino)benzo[b]furan-2-carboxylate (MB) and poly(3-decylthiophene) (PDT) or poly(3-octylthiophene) (P3OT). Photovoltaic cell structure consisted of ITO/active materials/Al. The photophysics of such photoactive devices is based on the photo-induced charge transfer from donor-type semiconducting conjugated polymers to the acceptor-type polymers. The monomer synthesis and polymerization as well as the device fabrication are presented. The copolymers can be spin-coated from a solution at room temperature without subsequent processing and heat treatment. The photovoltaic properties of the devices are shown.
Co-reporter:Dariusz Bogdal;Michal Pajda;Jerzy Sanetra;Monika Pokladko;Katarzyna Matras;Andre-Jean Attias;Jean-Luis Fave
Macromolecular Symposia 2008 Volume 268( Issue 1) pp:110-114
Publication Date(Web):
DOI:10.1002/masy.200850823
Abstract
Summary: A novel acrylate polymer with a carbazole pendant group and bipyridine derivatives as side chains was synthesized, in which derivatives of bipyridine as electro-optic chromophores and carbazole as photoconductive moiety were covalently linked to the acrylate backbone. 2–(Carbazol-9-yl)ethyl methacrylate (CEM) and methacrylic 2-[5-(2-{5,5′-dimethyl-6′-[2-(5-pentylthiophen-2-yl)vinyl]-3,3′-bipyridin-6-yl}vinyl)thiophen-2-yl]ethyl methacrylate (BiPy) were synthesized and then copolymerized to give 99:1, 98:2, 92:8 (mol/mol) CEM/BiPy copolymers. Films of the copolymers blended with poly(3-octylthiophene) (P3OT) or poly(3-decylthiophene) (PDT) and sandwiched between the transparent ITO and Al electrode were examined for photovoltaic properties.
Co-reporter:D. Bogdal, M. Lukasiewicz and J. Pielichowski
Green Chemistry 2004 vol. 6(Issue 2) pp:110-113
Publication Date(Web):13 Jan 2004
DOI:10.1039/B312706K
Novel effective application of microwave irradiation to the chlorination, bromination, and iodination of carbazole and other aromatic compounds in the presence of a hydrogen peroxide–hydrohalic acids system is described as a new environmentally benign method for the synthesis of halogenoarenes.
Co-reporter:Dariusz Bogdal;Jaroslaw Gorczyk
Journal of Applied Polymer Science 2004 Volume 94(Issue 5) pp:1969-1975
Publication Date(Web):30 SEP 2004
DOI:10.1002/app.21018
A new microwave-assisted method of synthesis of solid epoxy resins (SER) with desired epoxy-groups content is described. The method is based on the polyaddition of 4,4′-isopropylidenediphenol (BPA) to a lower-molecular-weight epoxy resin [Rütapox 0162, epoxy value (EV) = 0.57 mol/100 g] in the presence of 2-methylimidazole (2-MI), as a catalyst. Analogical syntheses were performed using conventional heating (i.e., electric heating mantle) for the comparison of properties of SER under both conditions. All the microwave reactions were carried out in the multimode microwave reactor Plazmatronika (Poland) with microwave frequency of 2.45 GHz and maximum microwave power of 600 W. The main advantage of the microwave process is twofold reduction of reaction time in comparison to the conventional heating. Values of EV, Mn, Mw, Mw/Mn, and degree of branching of the products obtained were determined. It was found that the molecular weight distribution and degree of branching in resins synthesized under microwave irradiation was comparable with those obtained under conventional heating and was not influenced by the reduction in reaction time. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 94: 1969–1975, 2004
Co-reporter:Marcin Lukasiewicz;Jan Pielichowski
Advanced Synthesis & Catalysis 2003 Volume 345(Issue 12) pp:
Publication Date(Web):23 DEC 2003
DOI:10.1002/adsc.200303131
A commercial tetravalent chromium dioxide (MagtrieveTM) as a magnetically retrievable oxidant is shown to be a very useful compound for microwave-assisted and conventional transformation of aromatic and alkyl aromatic molecules into the corresponding aryl ketones, quinones or lactones.
Co-reporter:D. Bogdal;V. Yashchuk;V. Kudrya;J. Pielichowski;M. Warzala;T. Ogul'Chansky
Journal of Applied Polymer Science 2002 Volume 84(Issue 9) pp:1650-1656
Publication Date(Web):6 MAR 2002
DOI:10.1002/app.10469
The alkyl methacrylates with halogenated carbazolyl pendant groups were prepared, and the analysis of their absorption and emission spectra showed that the polymers containing monohalogenatged carbazole rings were capable of exhibiting a high singlet-triplet (S-T) conversion. The reasons that mainly triplet excitons could be observed in such polymers and additional bands appearance in the spectra of the polymers with dihalogenated carbazole rings are discussed. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 84: 1650–1656, 2002; DOI 10.1002/app.10469
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