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Effect of the Size of the Molecular Mass of Some Amine Groups Modified to Maleic anhydride-alt-1-Octadecene Copolymer on Thermal Stability

Year 2024, Volume: 45 Issue: 3, 530 - 536, 30.09.2024

Hacıbayram Zengin

https://doi.org/10.17776/csj.1485308

Abstract

In this study, 1-octadecene-alt-maleic anhydride (OC-MA) copolymer was synthesized by radical polymerization method. The synthesized copolymer was first time modified with ammonia, methylamine, aniline and hexamethylenediamine reagents in acetone environment. The modified amidic acid derivatives were divided into two parts as quantity. One of these amounts was dried as an amidic acid derivative, and the other was imidized in dimethylformamide environment with constant stirring at 150 °C for 5 hours. Structural characterizations of the obtained samples were determined from the FTIR spectra. Thermal stability was compared from Thermogravimetric Analysis (TGA) and Differential Scanning Calorimetry (DSC) curves. It was established that the modified copolymers were thermally more stable than that of the original OC-MA copolymer. However, it was observed that the size of the molar masses of the reagents participating in the modification reactions showed linear or parabolic increases according to thermal parameter temperature of the decomposition reaction obtained from the TGA and DSC curves.

Keywords

Copolymerization Radical polymerization Thermal analysis Modification

Ethical Statement

-

Supporting Institution

Cumhuriyet University in Sivas, Turkey.

Project Number

F-105

Thanks

The present paper has been funded by the Research Foundation of Cumhuriyet University in Sivas, Turkey.

References

  • [1] Dongdan C., Jianfeng S., Mei H., Yanhua L., Jianjun W., Lixing D., Synthesis, characterization and hydrolytic stability of poly (amic acid) ammonium salt, Polymer Degradation and Stability, 96 (2011) 2174-2180.
  • [2] Nafeesa M., Qiaodi W., Guofei C., Beenish B., Haoji L., Yuanming Z., Lala R. S., Xingzhong F., Synthesis of polyamide-imides with different monomer sequence and effect on transparency and thermal properties, Polymer, 190 (2020) 122218.
  • [3] Liaw D. J., Liaw B.Y., Synthesis and characterization of new polyamide-imides containing pendent adamantyl groups, Polymer, 42 (2001) 839–845.
  • [4] Rathanawan M., Wittaya L., Anuvat S.,. Schwank J. W., Preparation, structure, properties and thermal behavior of rigid-rod polyimide/montmorillonite nanocomposites, Composites Science and Technology, 61 (2001) 1253–1264.
  • [5] Liu. Y. L., Chen Y. W., Thermally Reversible Cross-Linked Polyamides with High Toughness and Self-Repairing Ability from Maleimide and Furan-Functionalized Aromatic Polyamides, Macromol. Chem. Phys, 208, (2007) 224–232.
  • [6] Zengin H. B.,. Boztuğ A., Basan S.¸ Synthesis and Comparative Study of Thermal Stabilities of the Imidization of Some Maleic Anhydride Copolymers, Journal of Applied Polymer Science, 101 ( 2006) 2250–2254.
  • [7] Jana R.N., Mukunda P. G., Nando G. B., Polym. Degrad. Stabil. “Thermogravimetric analysis of compatibilized blends of low density polyethylene and poly(dimethyl siloxane), Rubber, 80 (2003) 75–82.
  • [8] Yen H. Y., Lee F. S., and Yang M. H., Polym. Test, Thermal degradation of polysulfones. VI: evaluation of thermal pyrolysis of acrylonitrile-butadiene-styrene terpolymer 22, (2003) 31–36.
  • [9] Su W. Y., Wang Y., Min K., Quirk R. P., In situ copolymerization and compatibilization of polyester and polystyrene blends. I. Synthesis of functionalized polystyrenes and the reactions with polyester, Polymer, 42 (2001) 5107–5119.
  • [10] Zulfiqar S., Masud K., Stabil, Thermal degradation of blends of allyl methacrylate–methyl methacrylate copolymers with aluminum isopropoxide, Polym. Degrad, 78 (2002) 305–313.
  • [11] Yang M. H., The thermal degradation of acrylonitrile-butadiene-styrene terpolymer under various gas conditions, Polym. Test, 19 (2000) 105–110.
  • [12] Gabriele B.,. Veltri L., Salerno G., Costa M., Chiusoli G. P., Synthesis of Maleic Anhydrides and Maleic Acids by Pd-Catalyzed Oxidative Dicarbonylation of Alk-1-ynes, Eur. J. Org. Chem., 9 (2003) 1722–1728.
  • [13] Qian L., Shurong W., Yun Z., Zhongyang L., Cen K., Mechanism study of wood lignin pyrolysis by using TG–FTIR analysis, J. Anal. Appl. Pyrolysis, 82 ( 2008) 170–177.
  • [14] You Y. Z., Hong C. Y., Pan C. Y., Controlled alternating copolymerization of St with MAh in the presence of DBTTC, Eur. Polym. J., 38 ( 2002) 1289–1295.
  • [15] Li H. M., Chen H. B., Shen Z. G., Lin S., Preparation and characterization of maleic anhydride-functionalized syndiotactic polystyrene, Polymer, 43 ( 2002) 5455–5461.
  • [16] Zhaohui L., Zhang X., Tasaka S., Inagaki N., The interfacial tension and morphology of reactive polymer blends, Mater. Lett. , 48 ( 2001) 81–88.
  • [17] Jeong J. H., Byoun Y. S., Lee Y. S., Poly(styrene-alt-maleic anhydride)-4-aminophenol conjugate: synthesis and antibacterial activity, React. Funct. Polym., 50 (2002) 257–263.
  • [18] Zengin H. B., Boztuğ A., Yılmaz E., Chemical modification and thermal characterisation of poly(allylpropionate-altmaleic anhydride) copolymer modified by hexamethylenediamine, Materials Research Innovations,12(2) (2008),90-93.
  • [19] Patel H., Raval D. A., Madamwar D., Patel S. R., Polymeric prodrug: Synthesis, release study and antimicrobial property of poly(styrene-co-maleic anhydride)-bound acriflavine, Angew. Makromol. Chem., , 263 ( 1998) 25–30.
  • [20] Roux M. V, Jimenez P., Angeles M., Luengo M., Davalos J. Z., Sun Z., Hosmane R. S., Liebman J. F., The Elusive Antiaromaticity of Maleimides and Maleic Anhydride:  Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide, J. Org. Chem., 62 ( 1997) 2732–2737.
  • [21] Molaeia H., Zaaerib F., h Sharific S., Ramazania A., Safaeid S., Abdolmohammadie J., Khoobif M., Polyethylenimine-graft-poly (maleic anhydride-alt-1-octadecene) coated Fe3O4 magnetic nanoparticles: promising targeted pH-sensitive system for curcumin delivery and MR imaging, International Journal Of Polymeric Materials And Polymeric Biomaterials, 70(18) (2021) 1344–1353.
  • [22] Ute Schmidt, Stefan Zschoche, Carsten Werner, Modification of Poly(octadecene-alt-maleic anhydride) Films by Reaction with Functional Amines, Journal of Applied Polymer Science, 87 (2003) 1255–1266.
  • [23] Ayman M., Atta S., El-Hamouly H., AlSabagh M. A., Moataz M. G., Crosslinked Poly(octadecene-alt-maleic anhydride) Copolymers as Crude Oil Sorbers, Journal of Applied Polymer Science, 105 (2007) 2113–2120.
  • [24] Karakus G., Zengin H. B., Akin Polat Z., Yenidunya A F., Aydin Semiha., Cytotoxicity of three maleic anhydride copolymers and common solvents used for polymer solvation, Polym. Bull, 70 (2013) 1591–1612.
  • [25] Zengin H.B., Gürkan R., Novel amide- and imide-co-polymers modified with sulfathiazole as efficient chelator for selective extraction, pre-concentration and determination of trace inorganic antimony (as Sb(III)) from edible vegetable oils by ultrasound assisted-cloud point extraction coupled to micro-volume UV-spectrophotometry, Journal of Food Composition and Analysis, 115 (2023) 104931.
  • [26] Ahokas M., Wilén Carl-Eric, Synthesis of poly (styrene-co-maleimide) and poly(octadecene-co-maleimide) nanoparticles and their utilization in paper coating, Progress in Organic Coatings, 66 (2009) 377–381.

Year 2024, Volume: 45 Issue: 3, 530 - 536, 30.09.2024

Hacıbayram Zengin

https://doi.org/10.17776/csj.1485308

Abstract

Project Number

F-105

References

  • [1] Dongdan C., Jianfeng S., Mei H., Yanhua L., Jianjun W., Lixing D., Synthesis, characterization and hydrolytic stability of poly (amic acid) ammonium salt, Polymer Degradation and Stability, 96 (2011) 2174-2180.
  • [2] Nafeesa M., Qiaodi W., Guofei C., Beenish B., Haoji L., Yuanming Z., Lala R. S., Xingzhong F., Synthesis of polyamide-imides with different monomer sequence and effect on transparency and thermal properties, Polymer, 190 (2020) 122218.
  • [3] Liaw D. J., Liaw B.Y., Synthesis and characterization of new polyamide-imides containing pendent adamantyl groups, Polymer, 42 (2001) 839–845.
  • [4] Rathanawan M., Wittaya L., Anuvat S.,. Schwank J. W., Preparation, structure, properties and thermal behavior of rigid-rod polyimide/montmorillonite nanocomposites, Composites Science and Technology, 61 (2001) 1253–1264.
  • [5] Liu. Y. L., Chen Y. W., Thermally Reversible Cross-Linked Polyamides with High Toughness and Self-Repairing Ability from Maleimide and Furan-Functionalized Aromatic Polyamides, Macromol. Chem. Phys, 208, (2007) 224–232.
  • [6] Zengin H. B.,. Boztuğ A., Basan S.¸ Synthesis and Comparative Study of Thermal Stabilities of the Imidization of Some Maleic Anhydride Copolymers, Journal of Applied Polymer Science, 101 ( 2006) 2250–2254.
  • [7] Jana R.N., Mukunda P. G., Nando G. B., Polym. Degrad. Stabil. “Thermogravimetric analysis of compatibilized blends of low density polyethylene and poly(dimethyl siloxane), Rubber, 80 (2003) 75–82.
  • [8] Yen H. Y., Lee F. S., and Yang M. H., Polym. Test, Thermal degradation of polysulfones. VI: evaluation of thermal pyrolysis of acrylonitrile-butadiene-styrene terpolymer 22, (2003) 31–36.
  • [9] Su W. Y., Wang Y., Min K., Quirk R. P., In situ copolymerization and compatibilization of polyester and polystyrene blends. I. Synthesis of functionalized polystyrenes and the reactions with polyester, Polymer, 42 (2001) 5107–5119.
  • [10] Zulfiqar S., Masud K., Stabil, Thermal degradation of blends of allyl methacrylate–methyl methacrylate copolymers with aluminum isopropoxide, Polym. Degrad, 78 (2002) 305–313.
  • [11] Yang M. H., The thermal degradation of acrylonitrile-butadiene-styrene terpolymer under various gas conditions, Polym. Test, 19 (2000) 105–110.
  • [12] Gabriele B.,. Veltri L., Salerno G., Costa M., Chiusoli G. P., Synthesis of Maleic Anhydrides and Maleic Acids by Pd-Catalyzed Oxidative Dicarbonylation of Alk-1-ynes, Eur. J. Org. Chem., 9 (2003) 1722–1728.
  • [13] Qian L., Shurong W., Yun Z., Zhongyang L., Cen K., Mechanism study of wood lignin pyrolysis by using TG–FTIR analysis, J. Anal. Appl. Pyrolysis, 82 ( 2008) 170–177.
  • [14] You Y. Z., Hong C. Y., Pan C. Y., Controlled alternating copolymerization of St with MAh in the presence of DBTTC, Eur. Polym. J., 38 ( 2002) 1289–1295.
  • [15] Li H. M., Chen H. B., Shen Z. G., Lin S., Preparation and characterization of maleic anhydride-functionalized syndiotactic polystyrene, Polymer, 43 ( 2002) 5455–5461.
  • [16] Zhaohui L., Zhang X., Tasaka S., Inagaki N., The interfacial tension and morphology of reactive polymer blends, Mater. Lett. , 48 ( 2001) 81–88.
  • [17] Jeong J. H., Byoun Y. S., Lee Y. S., Poly(styrene-alt-maleic anhydride)-4-aminophenol conjugate: synthesis and antibacterial activity, React. Funct. Polym., 50 (2002) 257–263.
  • [18] Zengin H. B., Boztuğ A., Yılmaz E., Chemical modification and thermal characterisation of poly(allylpropionate-altmaleic anhydride) copolymer modified by hexamethylenediamine, Materials Research Innovations,12(2) (2008),90-93.
  • [19] Patel H., Raval D. A., Madamwar D., Patel S. R., Polymeric prodrug: Synthesis, release study and antimicrobial property of poly(styrene-co-maleic anhydride)-bound acriflavine, Angew. Makromol. Chem., , 263 ( 1998) 25–30.
  • [20] Roux M. V, Jimenez P., Angeles M., Luengo M., Davalos J. Z., Sun Z., Hosmane R. S., Liebman J. F., The Elusive Antiaromaticity of Maleimides and Maleic Anhydride:  Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide, J. Org. Chem., 62 ( 1997) 2732–2737.
  • [21] Molaeia H., Zaaerib F., h Sharific S., Ramazania A., Safaeid S., Abdolmohammadie J., Khoobif M., Polyethylenimine-graft-poly (maleic anhydride-alt-1-octadecene) coated Fe3O4 magnetic nanoparticles: promising targeted pH-sensitive system for curcumin delivery and MR imaging, International Journal Of Polymeric Materials And Polymeric Biomaterials, 70(18) (2021) 1344–1353.
  • [22] Ute Schmidt, Stefan Zschoche, Carsten Werner, Modification of Poly(octadecene-alt-maleic anhydride) Films by Reaction with Functional Amines, Journal of Applied Polymer Science, 87 (2003) 1255–1266.
  • [23] Ayman M., Atta S., El-Hamouly H., AlSabagh M. A., Moataz M. G., Crosslinked Poly(octadecene-alt-maleic anhydride) Copolymers as Crude Oil Sorbers, Journal of Applied Polymer Science, 105 (2007) 2113–2120.
  • [24] Karakus G., Zengin H. B., Akin Polat Z., Yenidunya A F., Aydin Semiha., Cytotoxicity of three maleic anhydride copolymers and common solvents used for polymer solvation, Polym. Bull, 70 (2013) 1591–1612.
  • [25] Zengin H.B., Gürkan R., Novel amide- and imide-co-polymers modified with sulfathiazole as efficient chelator for selective extraction, pre-concentration and determination of trace inorganic antimony (as Sb(III)) from edible vegetable oils by ultrasound assisted-cloud point extraction coupled to micro-volume UV-spectrophotometry, Journal of Food Composition and Analysis, 115 (2023) 104931.
  • [26] Ahokas M., Wilén Carl-Eric, Synthesis of poly (styrene-co-maleimide) and poly(octadecene-co-maleimide) nanoparticles and their utilization in paper coating, Progress in Organic Coatings, 66 (2009) 377–381.
There are 26 citations in total.

Details

Primary Language English
Subjects Macromolecular and Materials Chemistry (Other)
Journal Section Natural Sciences
Authors

Hacıbayram Zengin 0000-0003-3861-6671

Project Number F-105
Publication Date September 30, 2024
Submission Date May 16, 2024
Acceptance Date September 23, 2024
Published in Issue Year 2024Volume: 45 Issue: 3

Cite

APA Zengin, H. (2024). Effect of the Size of the Molecular Mass of Some Amine Groups Modified to Maleic anhydride-alt-1-Octadecene Copolymer on Thermal Stability. Cumhuriyet Science Journal, 45(3), 530-536. https://doi.org/10.17776/csj.1485308
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