Abstract
Maleic anhydride was modified with 1-decanol at two different ratios to obtain derivatives named MD-75 (75% modified) and MD-100 (100% modified). By using these derivatives and acrylamide (AAm), many hydrogels with different AAm/MD ratios were synthesized. Ammonium persulphate (APS), N,N,N′,N′-tetramethyl ethylenediamine (TMEDA) and N,N′-methylene bisacrylamide (MBAAm) were used as initiator, catalyts and crosslinker agent respectively in the synthesis reaction. The modification reactions were clarified by FTIR and 1H-NMR methods. Swelling behaviours, swelling capacities and effect of temperature, pH of the swelling medium and hydrogel composition on these parameters were studied. The swelling capacity of the hydrogels increased up to 82700% with decreasing the AAm/MD ratio. Temperature and pH of the swelling medium and the composition of the hydrogels were found to have a strong effect on the swelling behaviour and the swelling capacity of the hydrogels. The gels showed low swelling capacity with single-step swelling behaviour at low temperatures (T≤50 °C) and high swelling capacity with two-step swelling behaviour at higher temperatures. The swelling and diffusion kinetics of the hydrogels were also determined. All of the synthesized hydrogels showed uniform diffusion type at low temperatures while two types of diffusion observed at high temperatures.
Graphic abstract
Hydrogels of modified maleic anhydride were prepared by chemical cross-linking. Hydrogels showed excellent swelling capacity up to 82,700%. Temperature and pH have a strong effect on the swelling capacity of the hydrogels. Hydrogels showed two-step swelling behaviour.
Similar content being viewed by others
References
Peppas N A and Khare A R 1993 Preparation, structure and diffusional behavior of hydrogels in controlled release Adv. Drug Deliv. Rev. 11 1
Zohuriaan-Mehr M J and Kabiri K 2008 Superabsorbent Polymer Materials: A Review Iran. Polym. J. 17 451
Sharma K, Kaith B S, Kumar V, Kalia S and Swart H C 2014 Synthesis and biodegradation studies of gamma irradiated electrically conductive hydrogels Polym. Degrad. Stabil. 107 166
Yang B, Lu Y, Ren T and Luo G 2013 One-step synthesis of pH-sensitive poly(Acrylamide-co-Sodium Acrylate) beads with core–shell structure React. Funct. Polym. 73 122
Ali A E-H, Shawky H A, Rehim H A A E and Hegazy E A 2003 Synthesis and characterization of PVP/AAc copolymer hydrogel and its applications in the removal of heavy metals from aqueous solution Eur. Polym. J. 39 2337
Atta A M, Ismail H S, Mohamed H M and Mohamed Z M 2011 Acrylonitrile/Acrylamidoxime/2-Acrylamido-2-Methylpropane Sulfonic Acid-Based Hydrogels: Synthesis, Characterization and Their Application in the Removal of Heavy Metals J. Appl. Polym. Sci. 122 999
Kosemund K, Schlatter H, Ochsenhirt J L, Krause E L, Marsman D S and Erasala G N 2009 Safety Evaluation of Superabsorbent Baby Diapers Regulat. Toxicol. Pharmacol. 53 81
Ozdemir Y and Mazi H pH and Thermo Sensitive Superabsorbent Poly(N-Hydroxymethylacrylamide-co-Itaconic Acid) Hydrogels: Synthesis, Characterization and Kinetic Studies J. Macromol. Sci. Part A 51 983
Wang L, Zhang J P and Wang A Q 2008 Removal of methylene blue from aqueous solution using chitosan-g-poly(acrylic acid)/montmorillonite superadsorbent nanocomposite Colloid Surf. A 322 47
Paulino A T, Guilherme M R, Reis A V, Campase G M, Muniz E C and Nozaki J 2006 Removal of methylene blue dye from an aqueous media using superabsorbent hydrogel supported on modified polysaccharide J. Colloid Interf. Sci. 301 55
Li S, Zhang H, Feng J, Xu R and Liu X 2011 Facile preparation of poly(acrylic acid–acrylamide) hydrogels by frontal polymerization and their use in removal of cationic dyes from aqueous solution Desalination 280 95
Dey A, Bera R and Chakrabarty D 2017 Synthesis of poly(ethylene glycol) di-itaconate and investigation of its influence on acrylamide based hydrogels meant for water treatment Polymer 116 178
Sadeghi M and Hosseinzadeh H J 2008 Synthesis of Starch—Poly(Sodium Acrylate-co-Acrylamide) Superabsorbent Hydrogel with Salt and pH-Responsiveness Properties as a Drug Delivery System J. Bioact. Compat. Polym. 23 381
Jeong H J, Nam S J, Song J Y and Park S N 2019 Synthesis and physicochemical properties of pH-sensitive hydrogel based on carboxymethyl chitosan/2-hydroxyethyl acrylate for transdermal delivery of nobiletin J. Drug Deliv. Sci. Technol. 51 194
Feng Q, Li F, Yan Q, Zhu Y and Ge C 2010 Frontal polymerization synthesis and drug delivery behavior of thermo-responsive poly(N-isopropylacrylamide) hydrogel Colloid Polym. Sci. 288 915
Ghandehari H, Kopeckova P and Kopecek J 1997 In vitro degradation of pH-sensitive hydrogels containing aromatic azo bonds Biomaterials 18 861
Chen J, Blevins W E, Park H and Park K 2000 Gastric retention properties of superporous hydrogel composites J. Control. Rel. 64 39
Nguyen K T and West J L 2002 Photopolymerizable hydrogels for tissue engineering applications Biomaterials 23 4307
Fekete T, Borsa J, Takacs E and Wojnarovits L 2017 Synthesis and characterization of superabsorbent hydrogels based on hydroxyethylcellulose and acrylic acid Carbohyd. Polym. 166 300
Calo E and Khutoryanskiy V V 2015 Biomedical applications of hydrogels: A review of patents and commercial products Eur. Polym. J. 65 252
Nita L E, Chiriac A P, Rusu A G, Bercea M, Ghilan A, Dumitriu R P and Mititelu-Tartau L 2019 New self-healing hydrogels based on reversible physical interactions and their potential applications Eur. Polym. J. 118 176
Chauhan G S, Chauhan S, Chauhan K and Sen U 2006 Synthesis and characterization of acrylamide and 2-hydroxylpropyl methacrylate hydrogels for specialty applications J. Appl. Polym. Sci. 99 3040
Chauhan G S and Chauhan S 2008 Use of novel hydrogels based on modified cellulosics and methacrylamide for separation of metal ions from water systems J. Appl. Polym. Sci. 109 47
Tanaka T 1987 Encyclopedia of Polymer Science and Engineering Vol. 7. (New York: Wiley)
Chauhan G S, Lal H and Mahajan S 2004 Synthesis, characterization, and swelling responses of poly(N -isopropylacrylamide)- and hydroxypropyl cellulose-based environmentally sensitive biphasic hydrogels J. Appl. Polym. Sci. 91 479
Mazi H, Kibarer G, Emregul E and Rzaev Z M O 2006 Bioengineering Functional Copolymers. IX. Poly[(maleic anhydride-co-hexene-1)-g-poly(ethylene oxide)] Macromol. Biosci. 6 311
Davies M C, Dawkins J V, Hurston D J and Meehan E 2002 Molar mass determination of poly(octadecene-alt-maleic anhydride) copolymers by size exclusion chromatography and dilute solution viscometry Polymer 43 4311
Mazi H, Emregül E, Rzaev Z M O and Kibarer G 2006 Preparation and properties of invertase immobilized on a poly(maleic anhydride-hexen-1) membrane J. Biomater. Sci. Polym. Edit. 17 821
Wang Y, Chen D, Wang C, Zhao C, Ma Y and Yang W 2018 Immobilization of cellulase on styrene/maleic anhydride copolymer nanoparticles with improved stability against pH changes Chem. Eng. J. 336 152
Lee S J, Tatavarty R and Gu M B 2012 Electrospun polystyrene–poly(styrene-co-maleic anhydride) nanofiber as a new aptasensor platform Biosens. Bioelectron. 38 302
Derkus B, Emregul K C, Mazi H, Emregul E, Yumak T and Sinag A 2014 Protein A immunosensor for the detection of immunoglobulin G by impedance spectroscopy Bioproc. Biosys. Eng. 37 965
Shafaghi S, Moghadam P N, Fareghi A R and Baradarani M M 2014 Synthesis and Characterization of a Drug-Delivery System Based on Melamine-Modified Poly(vinyl acetate-co-maleic anhydride) Hydrogel J. Appl. Polym. Sci. 131 40389
Shohraty F, Moghadam P N, Fareghi A R, Movagharnezhad N and Khalafy J 2018 Synthesis and Characterization of New pH-Sensitive Hydrogels Based on Poly(glycidyl methacrylate- co -maleic anhydride) Adv. Polym. Technol. 37 120
Chitanu G C, Zaharia L I and Carpov A 1997 International, Review: Analysis and Characterization of Maleic Copolymers J. Polym. Anal. Character. 4 1
Popescu I, Suflet D M, Pelin I M and Chitanu G C 2011 Biomedical Applications Of Maleic Anhydride Copolymers Revue Roumaine de Chimie 56 173
Zhu L P, Yi Z, Liu F, Wei X Z, Zhu B K and Xu Y Y 2008 Amphiphilic graft copolymers based on ultrahigh molecular weight poly(styrene-alt-maleic anhydride) with poly(ethylene glycol) side chains for surface modification of polyethersulfone membranes Eur. Polym. J. 44 1907
Mazi H and Gulpinar A 2014 Cu(II), Zn(II) and Mn(II) complexes of poly(methyl vinyl ether-alt-maleic anhydride). Synthesis, characterization and thermodynamic parameters J. Chem. Sci. 126 239
Potorac S, Popa M, Maier V, Lisa G and Verestiuc L 2012 New hydrogels based on maleilated collagen with potential applications in tissue engineering Mater. Sci. Eng. C 32 236
Ilgin P, Ozay H and Ozay O 2019 A new dual stimuli responsive hydrogel: Modeling approaches for the prediction of drug loading and release profile Eur. Polym. J. 113 244
Jafari A, Hassanajili S, Azarpira N, Karimi M B and Geramizadeh B 2019 Development of thermal-crosslinkable chitosan/maleic terminated polyethylene glycol hydrogels for full thickness wound healing: In vitro and in vivo evaluation Eur. Polym. J. 118 113
Wang Y, Yang N, Wang D, He Y, Chen L and Zhao Y 2018 Poly (MAH-β-cyclodextrin-co-NIPAAm) hydrogels with drug hosting and thermo/pH-sensitive for controlled drug release Polym. Degrad. Stabil. 147 123
Bajpai S K 2001 Swelling–deswelling behavior of poly(acrylamide-co-maleic acid) hydrogels J. Appl. Polym. Sci. 80 2782
Kasgoz H, Aydin I and Kasgoz A 2005 The effect of PEG(400)DA crosslinking agent on swelling behaviour of acrylamide-maleic acid hydrogels Polym. Bull. 54 387
Tiwari A 2014 Advanced Healthcare Materials (Location: John Wiley and Sons)
Li Z and Guan J 2011 Thermosensitive Hydrogels for Drug Delivery Expert Opin. Drug Deliv. 8 991
Koetting M C, Peters J T, Steichen S D and Peppas N A 2015 Stimulus-responsive hydrogels: Theory, modern advances, and applications Mater. Sci. Eng.: R: Rep. 93 1
Andrei M, Turturica G, Stanescu P O and Teodorescu M 2016 Thermosensitive injectable hydrogels from poly(N-isopropylacrylamide)–dextran aqueous solutions: Thermogelation and drug release properties Soft Mater. 14 162
Li R, Li Y, Wu Y, Zhao Y, Chen H, Yuan Y, Xu K, Zhang H, Lu Y, Wang J, Li X, Jia X and Xiao J 2018 Heparin-Poloxamer Thermosensitive Hydrogel Loaded with bFGF and NGF Enhances Peripheral Nerve Regeneration in Diabetic Rats Biomaterials 168 24
Ghizal R, Fatima G R and Srivastava S 2014 Smart Polymers and Their Applications, International Journal of Latest Technology in Engineering Manag. Appl. Sci. 2 104
Qureshi D, Nayak S K, Maji S, Anis A, Kim D and Pal K 2019 Environment sensitive hydrogels for drug delivery applications Eur. Polym. J. 120 1
Lim H L, Hwang Y, Kar M and Varghese S 2014 Smart hydrogels as functional biomimetic systems Biomater. Sci. 2 603
Wu S, Li H and Chen P 2004 Modeling Investigation of Volume Variation Kinetics of Fast Response Hydrogels J. Macromol. Sci. Part C 44 113
Peppas N A and Franson N M 1983 The swelling interface number as a criterion for prediction of diffusional solute release mechanisms in swellable polymers J. Polym. Sci. Polym. Phys. Edit. 21 983
Ende M T and Peppas N A 1997 Transport of ionizable drugs and proteins in crosslinked poly(acrylic acid) and poly(acrylic acid-co-2-hydroxyethyl methacrylate) hydrogels II. Diffusion and release studies J. Control. Rel. 48 47
Escobar J L, Garcia D M, Valerino A, Zaldivar D, Hernaez E and Katime I 2004 Cephazoline sodium release from poly(N-isopropyl acrylamide-co-N,N-dimethylacrylamide) hydrogels J. Appl. Polym. Sci. 91 3433
Acknowledgement
This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
MAZİ, H., SURMELİHİNDİ, B. Temperature and Ph-sensıtıve Super absorbent Polymers based on Modıfıed Maleıc Anhydrıde. J Chem Sci 133, 10 (2021). https://doi.org/10.1007/s12039-020-01873-3
Received:
Revised:
Accepted:
Published:
DOI: https://doi.org/10.1007/s12039-020-01873-3