Polymerization of Acrylamide N-methylene Lactic and Glycolic Acid
Main Article Content
Abstract
In this research work, the novel polymer base on acrylamide N-methylene lactic and glycolic acid was synthesized and its structural performances were identified by the IR, 1H NMR and 13C NMR spectroscopic investigations. The influencing factors and kinetics of polymerization, viscosity performance were studied and quantum chemical calculations were used to identify the correlation between the structure and properties. It was determined that the polymerization rate of the examined monomers in an aqueous solution, in the presence of DAA, adheres to the standard rules for radical polymerization of acrylamide monomers in solution. An investigation into the pH solution's impact on the kinetics of radical polymerization of acrylamido-N-methylene glycolic and acrylamido-N-methylene lactic acids revealed an extreme dependence with a minimum in a neutral medium. It was found the linear correlation between pH and viscosity. The physical and chemical performance of this polymer depends on the structural parameters related the results of quantum chemical calculation. Biological tests conducted on polyacrylamido-N-methylene lactic acid indicated its potential as a plant growth stimulator. The polymeric form of lactic acid was found to enhance the growth of Dustlik variety wheat seedlings by 40% more efficiently than lactic acid alone.
Received 16/05/2023
Revised 10/07/2023
Accepted 12/07/2023
Article Details
This work is licensed under a Creative Commons Attribution 4.0 International License.
How to Cite
References
1.Biswas A, Shukla A, Maiti P. Biomaterials for interfacing cell imaging and drug delivery: An overview. Langmuir. 2019; 35 (38):12285-12305.https://doi.org/10.1021/acs.langmuir.9b00419
Retnaningtyas Y, Supriyanto G, Irawan R, Siswodihardjo S. Noncovalently D-arabinitol Molecularly Imprinted Polymers (MIPs) to Identify Different Sugar Alcohols. Baghdad Sci J. 2021; 30 (18): 1536. https://doi.org/10.21123/bsj.2021.18.4(Suppl.).1536
Zhang A, Jung K, Li A, Liu J, Boyer C. Recent advances in stimuli-responsive polymer systems for remotely controlled drug release. Prog Polym Sci. 2019; 99: 101164. https://doi.org/10.1016/j.progpolymsci.2019.101164
Al-Issa MA, Mohammed AH. Copolymerization of Acrylamide with Acrylic acid. Baghdad Sci J. 2012; 9(2): 285-8. https://doi.org/10.21123/bsj.2012.9.2.285-288
.Rizwan M, Gilani SR, Durani AI, Naseem S. Materials diversity of hydrogel: Synthesis, polymerization process and soil conditioning properties in agricultural field. J Adv Res. 2021; 33: 15-40.https://doi.org/10.1016/j.jare.2021.03.007
Andrade F, Roca-Melendres MM, Durán-Lara EF, Rafael D, Schwartz Jr S. Stimuli-responsive hydrogels for cancer treatment: The role of pH, light, ionic strength and magnetic field. Cancers. 2021; 13(5): 1164.https://doi.org/10.3390/cancers13051164
Babaluei M, Mottaghitalab F, Seifalian A, Farokhi M. Injectable multifunctional hydrogel based on carboxymethylcellulose/polyacrylamide/polydopamine containing vitamin C and curcumin promoted full-thickness burn regeneration. Int J Biol Macromol. 2023; 236: 124005. https://doi.org/10.1016/j.ijbiomac.2023.124005
Daliri K, Pfannkuche K, Garipcan B. Effects of physicochemical properties of polyacrylamide (PAA) and (polydimethylsiloxane) PDMS on cardiac cell behavior. Soft Matter. 2021; 17(5): 1156-1172.https://doi.org/10.1039/D0SM01986K
Sung YK, Kim SW. Recent advances in polymeric drug delivery systems. Biomater Res. 2020 Dec; 24(1): 1-2.https://doi.org/10.1186/s40824-020-00190-7
Arican F, Uzuner-Demir A, Sancakli A, Ismar E. Synthesis and characterization of superabsorbent hydrogels from waste bovine hair via keratin hydrolysate graft with acrylic acid (AA) and acrylamide (AAm). Chem Pap. 2021; 75: 6601-6610. https://doi.org/10.1007/s11696-021-01828-z
Mi HY, Jiang Y, Jing X, Enriquez E, Li H, Li Q, Turng LS. Fabrication of triple-layered vascular grafts composed of silk fibers, polyacrylamide hydrogel, and polyurethane nanofibers with biomimetic mechanical properties. Mater Sci Eng C. 2019; 98: 241-9.https://doi.org/10.1016/j.msec.2018.12.126
Yang J. PLGA microsphere/P (NIPAAm-co-AAm) hydrogel combination systems for drug delivery. IOP Conf Ser.: Mater Sci Eng. 2019; 504(1): 012013. https://doi.org/10.1088/1757-899X/504/1/012013
Gorantla S, Waghule T, Rapalli VK, Singh PP, Dubey SK, Saha RN, Singhvi G. Advanced hydrogels based drug delivery systems for ophthalmic delivery. Recent Pat Drug Deliv Formul. 2019; 13(4): 291-300.https://doi.org/10.2174/1872211314666200108094851
Zou F, Xu J, Yuan L, Zhang Q, Jiang L. Recent progress on smart hydrogels for biomedicine and bioelectronics. Biosurface Biotribol. 2022; 8(3): 212-24.https://doi.org/10.1049/bsb2.12046
Aktas N, Alpaslan D, Dudu TE. Polymeric organo-hydrogels: novel biomaterials for medical, pharmaceutical, and drug delivery platforms. Front Mater. 2022; 9: 845700.https://doi.org/10.3389/fmats.2022.845700
Xiao Y, Wang ZY, Luo SH, Lin JY, Cao XY, Fang YG. One-pot preparation of thermosensitive polylactic acid materials by modifying with N-Isopropyl acrylamide. Polymer. 2021; 231: 124126.https://doi.org/10.1016/j.polymer.2021.124126
Amiryaghoubi N, Fathi M, Pesyan NN, Samiei M, Barar J, Omidi Y. Bioactive polymeric scaffolds for osteogenic repair and bone regenerative medicine. Med Res Rev. 2020; 40(5): 1833-1870.https://doi.org/10.1002/med.21672
Bashir MH, Korany NS, Farag DB, Abbass MM, Ezzat BA, Hegazy RH, Dörfer CE, Fawzy El-Sayed KM. Polymeric nanocomposite hydrogel scaffolds in craniofacial bone regeneration: A comprehensive review. Biomolecules. 2023; 13(2) :205.https://doi.org/10.3390/biom13020205
Hu Y, Shin Y, Park S, Jeong JP, Kim Y, Jung S. Multifunctional Oxidized Succinoglycan/Poly (N-isopropylacrylamide-co-acrylamide) Hydrogels for Drug Delivery. Polymers. 2022; 15(1): 122.https://doi.org/10.3390/polym15010122
Arican F, Uzuner-Demir A, Sancakli A, Ismar E. Synthesis and characterization of superabsorbent hydrogels from waste bovine hair via keratin hydrolysate graft with acrylic acid (AA) and acrylamide (AAm). Chem Pap. 2021; 75: 6601-10.https://doi.org/10.1007/s11696-021-01828-z
Lysáková K, Hlinakova K, Kutalkova K, Chaloupková R, Zidek J. Novel approach in control release monitoring of protein-based bioactive substances from injectable PLGA-PEG-PLGA hydrogel. Express Polym Lett. 2022; 16(8): 798-811.https://doi.org/10.3144/expresspolymlett.2022.59
de Brito AE, Pessoa Jr A, Converti A, de Oliveira Rangel-Yagui C, da Silva JA, Apolinário AC. Poly (lactic-co-glycolic acid) nanospheres allow for high l-asparaginase encapsulation yield and activity. Mater Sci Eng C. 2019; 98: 524-34.https://doi.org/10.1016/j.msec.2019.01.003
Kongprayoon A, Ross G, Limpeanchob N, Mahasaranon S, Punyodom W, Topham PD, Ross S. Bio-derived and biocompatible poly (lactic acid)/silk sericin nanogels and their incorporation within poly (lactide-co-glycolide) electrospun nanofibers. Polym Chem. 2022; 13(22): 3343-3357.https://doi.org/10.1039/D2PY00330A
Munim SA, Raza ZA. Poly (lactic acid) based hydrogels: Formation, characteristics and biomedical applications. J Porous Mater. 2019; 26(3): 881-901. https://doi.org/10.1007/s10934-018-0687-z
Qamruzzaman M, Ahmed F, Mondal MIH. An overview on starch-based sustainable hydrogels: Potential applications and aspects. J Polym Environ. 2022; 30(1): 19-50.https://doi.org/10.1007/s10924-021-02180-9
Seow WY, Kandasamy K, Purnamawati K, Sun W, Hauser CA. Thin peptide hydrogel membranes suitable as scaffolds for engineering layered biostructures. Acta Biomater. 2019; 88: 293-300.https://doi.org/10.1016/j.actbio.2019.02.001
Allen R, Ivtchenko E, Thuamsang B, Sangsuwan R, Lewis JS. Polymer-loaded hydrogels serve as depots for lactate and mimic “cold” tumor microenvironments. Biomater Sci. 2020; 8(21): 6056-68.https://doi.org/10.1039/D0BM01196G
Ghorbanizamani F, Moulahoum H, Celik EG, Timur S. Ionic liquids enhancement of hydrogels and impact on biosensing applications. J Mol Liq. 2022; 357: 119075.https://doi.org/10.1016/j.molliq.2022.119075
Kesharwani P, Bisht A, Alexander A, Dave V, Sharma S. Biomedical applications of hydrogels in drug delivery system: An update. J Drug Deliv Sci Technol. 2021; 66: 102914.https://doi.org/10.1016/j.jddst.2021.102914
Cao X, Liu H, Yang X, Tian J, Luo B, Liu M. Halloysite nanotubes@ polydopamine reinforced polyacrylamide-gelatin hydrogels with NIR light triggered shape memory and self-healing capability. Compos Sci Technol. 2020; 191: 108071.https://doi.org/10.1016/j.compscitech.2020.108071
Attia MF, Montaser AS, Arifuzzaman M, Pitz M, Jlassi K, Alexander-Bryant A, Kelly SS, Alexis F, Whitehead DC. In Situ Photopolymerization of Acrylamide Hydrogel to Coat Cellulose Acetate Nanofibers for Drug Delivery System. Polymers. 2021; 13(11): 1863.https://doi.org/10.3390/polym13111863
Chafran L, Carfagno A, Altalhi A, Bishop B. Green Hydrogel Synthesis: Emphasis on Proteomics and Polymer Particle-Protein Interaction. Polymers. 2022; 14(21): 4755.https://doi.org/10.3390/polym14214755
Dewangan Y, Verma DK, Berdimurodov E, Haldhar R, Dagdag O, Tripathi M, Mishra VK, Kumar PA. N-hydroxypyrazine-2-carboxamide as a new and green corrosion inhibitor for mild steel in acidic medium: experimental, surface morphological and theoretical approach. J Adhes Sci Technol. 2022: 1-21.https://doi.org/10.1080/01694243.2022.2068884
Berdimurodov E, Kholikov A, Akbarov K, Guo L, Kaya S, Kumar Verma D, Rbaa M, Dagdag O. Novel glycoluril pharmaceutically active compound as a green corrosion inhibitor for the oil and gas industry. J Electroanal Chem. 2022; 907: 116055.https://doi.org/10.1016/J.JELECHEM.2022.116055
Dagdag O, Haldhar R, Kim SC, Guo L, El Gouri M, Berdimurodov E, Hamed O, Jodeh S, Akpan ED, Ebenso EE. Recent progress in epoxy resins as corrosion inhibitors: design and performance. J Adhes Sci Technol. 2022: 1-22.https://doi.org/10.1080/01694243.2022.2055347
Berdimurodov E, Kholikov A, Akbarov K, Guo L, Kaya S, Katin KP, Verma DK, Rbaa M, Dagdag O, Haldhar R. Novel gossypol–indole modification as a green corrosion inhibitor for low–carbon steel in aggressive alkaline–saline solution. Colloids Surf A Physicochem Eng Asp. 2022; 637: 128207.https://doi.org/10.1016/J.COLSURFA.2021.128207
Berdimurodov E, Kholikov A, Akbarov K, Guo L. Inhibition properties of 4,5-dihydroxy-4,5-di-p-tolylimidazolidine-2-thione for use on carbon steel in an aggressive alkaline medium with chloride ions: Thermodynamic, electrochemical, surface and theoretical analyses. J Mol Liq. 2021; 327: 114813.https://doi.org/https://doi.org/10.1016/j.molliq.2020.114813