Synthesis and Functionalization of α-Olefines (6 and 10 Carbons)/Maleic Anhydride Comb-like Copolymers and Their Application in Silica Nanohybrid and Hydrogel

Document Type : Research Paper

Authors

Department of Polymerization Engineering, Faculty of Petrochemical, Iran Polymer and Petrochemical Institute, P.O. Box: 14975-112, Tehran, Iran

Abstract

Hypothesis: Poly(α-olefins) have non-polar structures and the development of polarity with different functionalities expands their application. The structure, number and size of the branches of the main chain affect the properties and design of new macromolecules. Active groups in α-olefin chains improve their interaction with silica nanoparticles. Furthermore, the amount of crosslinking changes the adsorption properties of hydrocarbon solvents.
Methods: The free radical copolymerization of 1-hexene and 1-decene with maleic anhydride was performed under different conditions. The structure and thermal properties of α-olefin (6 and 10 carbon) -maleic anhydride comb-like copolymers with different numbers and sizes of branches were investigated by Fourier-transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance (1H NMR), gel permeation chromatography (GPC) and thermogravimetric and differential thermal analysis (TGA/DTGA) methods. The effect of functionalized monomers of 2-ethylhexyl acrylate (2-EHA) and 3-chloro-2-methylpropene (3-C2MP) on the copolymerization reaction and their final structure was investigated. Polymerization reactions of styrene, maleic anhydride and 1-hexene were performed in the presence of silica nanoparticles. New hydrogels were synthesized with esterified poly1-hexene/ maleic anhydride with 2-decanol. The steps of nanohybrid and hydrogel synthesis and their thermal properties were characterized by FTIR and TGA/DTGA methods.
Findings: Various functionalized 1-hexane and 1-decen/ maleic anhydride comb-like copolymers with different molecular structures were synthesized and characterized. The results showed that by increasing the branch size of α-olefin from 4 to 8 carbons, the reaction conversion percent decreases and the branched of 2-EHA comonomer increases the reaction conversion. In the obtained nanocomposite, there is an interaction between maleic anhydride monomer and silica nanoparticles. Styrene/1-hexene/maleic anhydride nanocomposites containing 4 and 5.6% by weight of nanosilica were also synthesized. Structural design including functionalities and branch size, and also reaction conditions have a great influence on the properties of synthesized macromolecules and hydrogels.

Keywords


  1. Matyjaszewski K., Macromnaolecular Engineering: From Rational Design through Precise Macromolecular Synthesis and Processing to Targeted Macroscopic Material Properties, Prog. Polym. Sci., 30, 858-875, 2005.
  2. Braunecker W.A. and Matyjaszewski K., Controlled/Living Radical Polymerization: Features, Developments, and Perspectives, Prog. Polym. Sci., 32, 93-146, 2007.
  3. Lynda N.A., Meulerb A.J., and Hillmyer M.A., Polydispersity and Block Copolymer Self-Assembly, Prog. Polym. Sci., 33, 875-893, 2008.
  4. Hadjichristidis N., Iatrou H., Pitsikalis M., Pispas S., and Avgeropoulos A., Linear and Non-Linear Triblock Terpolymers. Synthesis, Self-Assembly in Selective Solvents and in Bulk, Prog. Polym. Sci., 33, 725–782, 2005.
  5. Padwa A.R., Functionally Substituted Poly(α-olefins), Prog. Polym. Sci., 14, 811-833, 1989.
  6. Imanishi Y. and Naga N., Recent Developments in Olefin Polymerizations with Transition Metal Catalysts, Prog. Polym. Sci., 26, 1147-1198, 2001.
  7. Chum P.S. and Swogger K.W., Olefin Polymer Technologies-History and Recent Progress at the Dow Chemical Company, Prog. Polym. Sci., 33, 797-819, 2008.
  8. Zambelli A. and Ammendola P., Stereospecific Polymerization of α-Olefins: End Groups, Polymer Structure and Reaction Mechanism, Prog. Polym. Sci., 16, 203-218, 1991.
  9. Campos J.M., Lourenço J.P., Cramail H., and Ribeiro M.R., Nanostructured Silica Materials in Olefin Polymerisation: From Catalytic Behaviour to Polymer Characteristics, Prog. Polym. Sci., 37, 1764-1804, 2012.
  10. Bahri-Laleh N., Hanifpour A., Mirmohammadi S.A., Poater A., Nekoomanesh-Haghighi M., Talarico G., and Cavallo L., Computational Modeling of Heterogeneous Ziegler-Natta Catalysts for Olefins Polymerization, Prog. Polym. Sci., 84, 89-114, 2018.
  11. Chevron Phlips Chemical Company, http://www.cpchem.com/polymers/homopolymers and copolymers other than polyethylene, Available in 20 November 2020.
  12. Davies M.C., Dawkins J.V., Hourston D.J., and Meehan E., Molar Mass Determination of Poly(octadecene-alt-maleic anhydride) Copolymers by Size Exclusion Chromatography and Dilute Solution Viscometry, Polymer, 43, 4311-4314, 2002.
  13. Tóth B., Varga C., and Bartha L., OlefinMaleic-Anhydride Copolymer Based Additives: A Novel Approach for Compatibilizing Blends of Waste Polyethylene and Crumb Rubber, Was. Manag., 38, 65-71, 2015.
  14. Billman F.L., Shih L.B., and Verbrugge C.J., 1-Alkene/Excess Maleic Anhydride Polymers, EU Pat. 0306992A2, 1987.
  15. Blecke R. and Hill R., Process for Copolymerization of Maleic Anhydride with 1-Olefins, US Pat. 3729451A, 1972.
  16. Al-Sabagh A.M., Sabaa M.W.,  Saad G.R., Khidr T.T., and Khalil T.M., Synthesis of Polymeric Additives Based on Itaconic Acid and Their Evaluation as Pour Point Depressants for Lube Oil in Relation to Rheological Flow Properties, Egyp. J. Petrol., 21, 19-30, 2012.
  17. Moriceau G., Tanaka J., Lester D., Pappas G.S., Cook A.B., O’Hora P., Winn J., Smith T., and Perrier S., Influence of Grafting Density and Distribution on Material Properties Using Well-Defined Alkyl Functional Poly(styrene-co-maleicanhydride) Architectures Synthesized by RAFT, Macromolecules, 52, 1469-1478, 2019.
  18. Atta A.M. and Arndt K.F., Swelling and Network Parameters of High Oil-Absorptive Network Based on 1-Octene and Isodecyl Acrylate Copolymers, J. Appl. Polym. Sci., 97, 80-91, 2005.
  19. Xu J., Zhang X., Sun J., Li L., and Guo X., How Comb-Type Poly(maleic acid alkylamide-co-α-olefin) Assemble in Waxy Oils and Improve Flowing Ability, Asia-Pac. J. Chem. Eng., 4, 551-556, 2009.
  20. Abdel-Azim A., Nasser A.M., Ahmed N.S., and Kamal R.S., Multifunctional Lube Oil Additives Based on Octadecene-Maleic Anhydride Copolymer, Petrol. Sci. Tech., 29, 97-107, 2011.
  21. Szkudlarek M., Heine E., Keul H., Beginn U., and Möller M., Synthesis, Characterization, and Antimicrobial, Properties of Peptides Mimicking Copolymers of Maleic Anhydride and 4-Methyl-1-Pentene, In. J. Molec. Sci., 19, 2617-2639, 2018.
  22. Atta A.M.,  El-Hamouly S.H.,  Al-Sabagh A.M., and Gabr M.M., Crosslinking of Reactive α-Olefins and Maleic Anhydride Copolymers as Oil Sorbers, J. Appl. Polym. Sci., 104, 871-881, 2007.
  23. Schmidt U., Zschoche S., and Werner C., Modification of Poly(octadecene-alt-maleic anhydride) Films by Reaction with Functional Amines, J. Appl. Polym. Sci., 87, 1255-1266, 2003.
  24. Salimi K., Rzayev Z. M.O., and Pişkin E., Functional Organo-Mt/Copolymer Nanoarchitectures. XXII. Interlamellar Graft Copolymerisation of L-Lactic Acid onto Poly(maleic anhydride-alt-1-octadecene) in the Presence of Different Clays as Catalyst-Nanofillers, Appl. Clay Sci., 101, 106-118, 2004. 
  25. Wang X., Xin H., Zhu Y., Chen W., Tang E., Zhang J., and Tan Y., Synthesis and Characterization of Modified Xanthan Gum Using Poly(maleic anhydride/1-octadecene), Coll. Polym. Sci., 294, 1333-1341, 2016.
  26. Monir T.S.B., Afroz S., Khan R.A., Miah M.Y., Takafuji M., and Alam M.A., pH-Sensitive Hydrogel from Polyethylene Oxide and Acrylic acid by Gamma Radiation, J. Compos. Sci., 3, 58-69, 2019.
  27. Bozdoğan D.D., Kibarer G., and Rzayev Z.M.O., Functional Copolymer/Organo-MMT Nanoarchitectures. XV. Interlamellar Complex-Radical Alternating Copolymerization of α-Olefins (C6-12) with Maleic Anhydride in the Presence of Reactive and Non-Reactive Organoclays, Int. Rev. Chem. Eng., 4, 232-243, 2012.
  28. Rzayev Z.M.O., Salimi K., EğriÖ., and Pişkin E., Functional Copolymer/Organo-MMT Nanoarchitectures. XIX. Nanofabrication and Characterization of Poly(MA-alt-1-octadecene)-g-PLA Layered Silicate Nanocomposites with Nanoporous Core–Shell Morphology, Polym. Adv. Technol., 25, 294-306, 2014.
  29. Demircan D., Kibarer G., and Morzayev Z., Preparation of Poly(MA-alt-olefin-C6,8,12,18)/Silica Nanohybrids via In Situ Generated Nanofillers for Use as a Dual Function Organonanofiller, J. Chem. Sci.,127, 1993-2003, 2015.
  30. El-Ghazawy R.A. and Farag R.K., Synthesis and Characterization of Novel Pour Point Depressants Based on Maleic Anhydride-Alkyl Acrylates Terpolymers, J. App. Polym. Sci., 115, 72–78, 2010.
  31. Rostami Darounkola M.R., Bahri-Laleh N., Nekoomanesh-Haghighi M., and Rahmatiyan S., Effect of Catalyst Type on the Copolymerization of Styrene/1-Hexene and Exploring of Their Structural and Thermal Properties, Polym. Sci. Ser. B., 61, 762-770, 2019.
  32. Rostami Darounkola M.R., Novel Branched Polymers and Their Structural Effects on Intercalation into Na-MMT and Silica Fume Suspensions, Polym. Bull., 75, 4055–4072, 2018.
  33. Park E.J., Park B.Ch., Kim Y.J., Canlier A., and Hwang T.S., Elimination and Substitution Compete During Amination of Poly(vinyl chloride) with Ehtylenediamine: XPS Analysis and Approach of Active Site Index, Macromol. Res., 26, 913-923, 2018.
  34. Rostami M.R., Abbassi-Sourki F., and Bouhendi H., Synergistic Effect of Branched Polymer/Nanosilica on the Microstructures of Cement Paste and Their Rheological Behaviors, Constr. Build. Mater., 201, 159-170, 2019.
  35. Rostami Darounkola M.R. and Fallah M., Synthesis of Branched Polymers and Dispersion of Nanosilica and the Effect of Their Interaction on Hydrated Cement Morphology,Iran. J. Polym. Sci. Technol.  (Persian), 31,239-250, 2018.
  36. Ren Y.M., Wu Z.Ch., Yang R.Ch., Tao T.X., Shao J.J., Gao Y.G., Zhang Sh., and Li L., A Simple Procedure for the Esterification and Transesterification Using p-Toluene Sulfonic Acid as Catalyst, Advan. Mater. Res., 781-784, 259-262, 2013.
  37. Rostami Daronkola M.R., Synthesis and Characterization of Quaternary Polymers as Superplasticizer and Assessing Their Effectiveness on Micronized Cement Particles, Iran. J. Polym. Sci. Technol. (Persian), 30, 221-233, 2017.
  38. Lin Y., Genzer J., Li W., Qiao R., Dickey M.D., and Tang S.Y., Sonication-Enabled Rapid Production of Stable Liquid Metal Nanoparticles Grafted with Poly(1-octadecene-alt-maleic anhydride) in Aqueous Solutions, Nanoscale, 10, 19871, 2018.
  39. Wang A., Qiao M., Xu J., Pan Y., Ran Q., Wu Sh., and Chen Q., POEGMA-b-PAA Comb-like Polymer Dispersant for Al2O3 Suspensions, J. Appl. Polym. Sci., 133, 43352-43357, 2016.
  40. Miladinovic Z.R., Micic M., and Suljovrujic E., Temperature/pH Dual Responsive OPGMA Based Copolymeric Hydrogels Prepared by Gamma Radiation: An Optimisation Study, J. Polym. Res., 23, 77-88, 2016.