Error message

  • Deprecated function: Unparenthesized `a ? b : c ? d : e` is deprecated. Use either `(a ? b : c) ? d : e` or `a ? b : (c ? d : e)` in include_once() (line 1439 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Array and string offset access syntax with curly braces is deprecated in include_once() (line 3557 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Unparenthesized `a ? b : c ? d : e` is deprecated. Use either `(a ? b : c) ? d : e` or `a ? b : (c ? d : e)` in include_once() (line 1439 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Array and string offset access syntax with curly braces is deprecated in include_once() (line 3557 of /home/science2016/public_html/includes/bootstrap.inc).

An Oligomer with Terminal Unsaturated Double Bonds Based on Epidian 5 and Ethylacrylic Acid

Olena Astakhova1, Mykhailo Bratychak Jr2, Ananiy Kohut3, Taras Chervinskyy1
Affiliation: 
1 Department of Chemical Technology of Oil and Gas Processing, Lviv Polytechnic National University 12, S. Bandery St., 79013 Lviv, Ukraine. olena.brat@gmail.com 2 Department of Chemical Technology of Plastics Processing, Lviv Polytechnic National University. 3 Department of Organic Chemistry, Lviv Polytechnic National University.
DOI: 
https://doi.org/10.23939/chcht17.01.070
AttachmentSize
PDF icon full_text.pdf652.16 KB

Keywords:

Abstract: 
An oligomer with terminal unsaturated double bonds (unsaturated oligomer, UO) has been synthesized from epoxy resin Epidian 5 and ethylacrylic acid. The impact of the catalyst nature, temperature, and reaction duration on the progress of the reaction between the resin and the acid has been studied. A synthetic technique is proposed for producing the UO. The UO has been characterized by chemical and FTIR-spectroscopic analyses. The UO has been examined in the cross-linking processes with oligoesteracrylates TGM 3 and MGP 9 as well as unsaturated polyester PE 246. In order to prepare structurally colored films, unsaturated azo dyes have been additionally used. A mixture of cumene hy-droperoxide and cobalt naphthenate dissolved in styrene has been utilized as an initiating system for the cross-linking of the formulations. By using FTIR-spectroscopy, the chemistry of the development of the cross-linked structures of the oligoester mixtures in the presence of the UO has been revealed.
References: 

[1] Chudzik, J.; Bieliński, D.M.; Demchuk, Y.; Bratychak, M.; Astakhova, O. Influence of Modified Epoxy Dian Resin on

Properties of Nitrile-Butadiene Rubber (NBR). Materials 2022, 15, 2766. https://doi.org/10.3390/ma15082766
https://doi.org/10.3390/ma15082766

[2] Chudzik, J.; Bieliński, D.M.; Bratychak, M.; Demchuk, Y.; Astakhova, O.; Jędrzejczyk, M.; Celichowski, G. Influence of

Modified Epoxy Resins on Peroxide Curing, Mechanical Properties and Adhesion of SBR, NBR and XNBR to Silver Wires-Part II: Application of Carboxy-Containing Peroxy Oligomer (CPO).

Materials 2021, 14, 1285. https://doi.org/10.3390/ma14051285
https://doi.org/10.3390/ma14051285

[3] Chudzik, J.; Bieliński, D. M.; Bratychak, M.; Demchuk, Y.; Astakhova, O.; Jędrzejczyk, M.; Celichowski, G. Influence

of Modified Epoxy Resins on Peroxide Curing, Mechanical Proper-ties and Adhesion of SBR, NBR and XNBR to Silver Wires. Part I: Application of Monoperoxy Derivative of Epoxy Resin (PO).

Materials 2021, 14, 1320. https://doi.org/10.3390/ma14051320
https://doi.org/10.3390/ma14051320

[4] Piesowicz, E.; Irska, I.; Bryll, K.; Gawdzinska, K.; Bratychak, M. Poly(butyleneterephthalate) Carbon Nanotubes Nanocomposites. Part II. Structure and Properties. Polimery 2016, 61, 24-30. https://doi.org/10.14314/polimery.2016.024
https://doi.org/10.14314/polimery.2016.024

[5] Papathanassiou, A.; Sulikowski, B.; Bratychak, M.; Zubyk, H.; Mykhailiv, O.; Zambrzycka-Szelewa, E.; Plonska-Brzezinska, M. A Phenol-Formaldehyde Polymeric Network to Generate Organic Aerogels: Synthesis, Physicochemical Characteristics and Potential Applications. J. Mater. Chem. A 2018, 6, 845-852. https://doi.org/10.1039/C7TA08814K
https://doi.org/10.1039/C7TA08814K

[6] Voronov, S.; Kohut, A.; Tarnavchyk, I.; Voronov, A. Advances in Reactive Polymeric Surfactants for Interface Modification. Curr. Opin. Colloid Interface Sci. 2014, 19, 95-121. https://doi.org/10.1016/j.cocis.2014.03.010
https://doi.org/10.1016/j.cocis.2014.03.010

[7] Varvarenko, S.;Voronov, A.; Samaryk, V.; Tarnavchyk, I.; Nosova, N.; Kohut, A.; Voronov, S. Covalent Grafting of

Polyacrylamide-Based Hydrogels to a Polypropylene Surface Acti-vated with Functional Polyperoxide. React. Funct. Polym. 2010, 70, 647-655. https://doi.org/10.1016/j.reactfunctpolym.2010.05.014
https://doi.org/10.1016/j.reactfunctpolym.2010.05.014

[8] Brozowski, Z.K.; Szymanska, E.; Bratychak, M.M. New Epoxy-Unsaturated Polyester Resin Copolymers. React. Funct. Polym. 1997, 33, 217-224. https://doi.org/10.1016/S1381-5148(97)00045-X
https://doi.org/10.1016/S1381-5148(97)00045-X

[9] Bratychak, M.; Astakhova, O.; Shyshchak, O. Epoxy Compo-sites Filled with Natural Calcium Carbonate. 3. Epoxy Composites Obtained in the Presence of Monocarboxylic Derivative of

Epidian-6 Epoxy Resin. Chem. Chem. Technol. 2020, 14, 504-513. https://doi.org/10.23939/chcht14.04.504
https://doi.org/10.23939/chcht14.04.504

[10] Bratychak, M.M.; Bratychak, Mykh.Mykh. Peroksydni pokhidni epoksydnykh smol; Publishing House of Lviv Polytechnic National University: Lviv, 2003.

[11] Bratychak, M.; Brostow, W.; Castano, V.M.; Donchak, V.; Gargai, H. Crosslinking Agents of Unsaturated Polymers: Evalua-tion of the Agent Efficiency. Mater. Res. Innov. 2002, 6, 153-159. https://doi.org/10.1080/14328917.2002.11784726
https://doi.org/10.1080/14328917.2002.11784726

[12] Bashta, B.; Astakhova, O.; Shyshchak, O.; Bratychak, M. Epoxy Resins Chemical Modification by Dibasic Acids. Chem. Chem. Technol. 2014, 8, 309 - 316]. https://doi.org/10.23939/chcht08.03.309
https://doi.org/10.23939/chcht08.03.309

[13] Bratychak, M.; Bashta, B.; Bruzdziak, P.; Astakhova, O.; Shyshchak, O. Cross-linking of Epoxy-Oligoesteric Mixtures in the Presence of Carboxy-Containing Derivative of ED-24 Epoxy Resin. Chem. Chem. Technol. 2013, 7, 41-46. https://doi.org/10.23939/chcht07.01.041
https://doi.org/10.23939/chcht07.01.041

[14] Bratychak, M.M.; Ivashkiv, O.P.; Astakhova, O.T. Khimichna modyfikacia epoksydnoho olihomeru ED-20 1,4-butandiolom. Dopovidi NAN Ukrainy 2014, 8, 97-102. http://dspace.nbuv.gov.ua/handle/123456789/88149
https://doi.org/10.15407/dopovidi2014.08.097

[15] Dukh, O.І.; Bratychak, M.M. Olihoefirni kompozytsii na osnovi dianovoi epoksydnoi smoly, modyfikovanoi nenasychenymy kyslotamy. Ukrainski khimichnyi zhurnal 1997, 63, 51-55.

[16] Boutevin, B.; Pietrasanta, Y.; Parisi, J.P. Synthèse de

composéas photoréticulables, 8. Réaction des téalomères du méthac-rylate d'époxy-2,3 propyle avec l'acide acrylique et

cinnamique. Macromol. Chem. Phys. 1987, 188, 1621-1629. https://doi.org/10.1002/macp.1987.021880708
https://doi.org/10.1002/macp.1987.021880708

[17] Iatsyshyn, O.; Astakhova, O.; Shyshchak, O.; Lazorko, O.; Bratychak, M. Monomethacrylate Derivative of ED-24 Epoxy Resin and its Application. Chem. Chem. Technol. 2013, 7, 73-77. https://doi.org/10.23939/chcht07.01.073
https://doi.org/10.23939/chcht07.01.073

[18] Bratychak, M.M.; Iatsyshyn, O.I.; Mitina, N.Ye.; Zaichenko, O.S. Kopolimeryzatsia monometakrylatnoi pokhidnoi dyhlitsydy-lovoho eteru dioksydiphenilpropanu iz styrolom. Ukrainski

khimichnyi zhurnal 2015, 81, 122-128.
https://doi.org/10.5406/jamerfolk.128.507.0122

[19] Bratychak, M.M.; Dukh, O.I.; Brzozowski, Z.K. Synthesis of Oligomers with Unsaturated End-Groups Based on Dianic Epoxy Resin and Crotonic Acid. J. Macromol. Sci. - Pure Appl. 1997, 34, 389-396. https://doi.org/10.1080/10601329708014965
https://doi.org/10.1080/10601329708014965

[20] Chikanishi, K.; Isuruta, T. Reactivity of α-Alkylacrylic Esters. I. Homopolymerization Behaviours of Methyl α-Alkylacrylates. Macromol. Chem. Phys. 1965, 81, 198-210. https://doi.org/10.1002/macp.1965.020810122
https://doi.org/10.1002/macp.1965.020810122

[21] Pikh, Z. Selektyvne okyslennia nenasychenukh spoluk zv'iazannym kysnem. D.Sc. Thesis, Lviv Polytechnic National University, Lviv, 1994.

[22] Nomenclature of Organic Chemistry : IUPAC

Recommendations and Preferred Names 2013; Royal Society of Chemistry: Cambridge, England, 2014.

[23] Lipatov, Yu.; Nesterov, T. Spravochnik po Khimii Polimerov; Naukova dumka: Kiev, 1971.

[24] Lange's Handbook of Chemistry; Dean, J.A., Ed.;

McGraw-Hill: New York, 1999.

[25] Metody vyznachennia iodnoho chysla. http://online.budstandart.com/ua/catalog/doc-page?id_doc=92574

[26] Bratychak, M.; Shyshchak, O.; Astakhova, O.; Ivashkiv, O. Oligomers with Functional Groups Based on Epoxy Resins.

Synthesis, Properties and Application; Publishing House of Lviv Polytechnic National University: Lviv, 2019.