18 Random and block architectures of N-arylitaconimide monomers with methyl methacrylate
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Chetana Deoghare
Abstract
“Itaconimide” is the members of imide (-CO-NH-CO-) family with reactive exocyclic double bond and it is easily obtained from the renewable resource i.e. D-glucose. The polymerization of various N-arylitaconimide (NAI) monomers with methyl methacrylate (MMA) have been reported to improve the glass transition temperature (Tg) and thermal stability of poly(methyl methacrylate) (PMMA). In literature, these studies have been done mostly using conventional free radical polymerizationmethods, which restricts the architecture of copolymers to “random” only. The block copolymers of NAI and MMA are an important due to the combination of glassy PMMA and thermally stable poly(NAI), which offers its applications for higher temperature service. The architectural control of polymers in provisions of its topology, composition, and various functionalities is possibly obtained using reversible-deactivation radical polymerizations (RDRPs). In RDRPs, the concentration of free radical is controlled in such a way that the termination reactions are minimized (normally in range of 1-10 mol%), and not allowed to obstruct with the desired architecture. However, this is possible by achieving (or by establishing) a rapid dynamic equilibriumbetween propagating radical and dormant species (i.e. R-X).Among all RDRPs, the atom transfer radical polymerization (ATRP) is very popular and adaptable method for the synthesis of polymers with specifically controlled architecture. Two different architectures of NAI and MMA copolymers are reported using ATRP process. The effect of various pedant groups on the rate constants of propagation (kp) and thermal propertiesNAI and MMA copolymers is studied. The poly(NAI-ran-MMA)-b-poly(MMA) are stable up to 200 °C and degraded in three steps. Whereas, the poly(NAI-ran-MMA)-b-poly(NAI) are stable up to 330 °C and degraded in two steps. The density functional theory methods are used for calculation of equilibrium constants (KATRP) for the ATRP process for the series of laboratory synthesized alkyl halides. A good agreement was observed between the experimentally determined and theoretically calculated KATRP values. The mechanistic studies are carried for poly(NAI-ran-MMA) copolymer system using statistical model discrimination method along with 1H decoupled 13C NMR spectroscopy. For studying the mechanism of copolymerization of NAI and MMA via ATRP methods, “trimer model or penultimate model” will be more accurate than “dimer model or terminal model”.
Abstract
“Itaconimide” is the members of imide (-CO-NH-CO-) family with reactive exocyclic double bond and it is easily obtained from the renewable resource i.e. D-glucose. The polymerization of various N-arylitaconimide (NAI) monomers with methyl methacrylate (MMA) have been reported to improve the glass transition temperature (Tg) and thermal stability of poly(methyl methacrylate) (PMMA). In literature, these studies have been done mostly using conventional free radical polymerizationmethods, which restricts the architecture of copolymers to “random” only. The block copolymers of NAI and MMA are an important due to the combination of glassy PMMA and thermally stable poly(NAI), which offers its applications for higher temperature service. The architectural control of polymers in provisions of its topology, composition, and various functionalities is possibly obtained using reversible-deactivation radical polymerizations (RDRPs). In RDRPs, the concentration of free radical is controlled in such a way that the termination reactions are minimized (normally in range of 1-10 mol%), and not allowed to obstruct with the desired architecture. However, this is possible by achieving (or by establishing) a rapid dynamic equilibriumbetween propagating radical and dormant species (i.e. R-X).Among all RDRPs, the atom transfer radical polymerization (ATRP) is very popular and adaptable method for the synthesis of polymers with specifically controlled architecture. Two different architectures of NAI and MMA copolymers are reported using ATRP process. The effect of various pedant groups on the rate constants of propagation (kp) and thermal propertiesNAI and MMA copolymers is studied. The poly(NAI-ran-MMA)-b-poly(MMA) are stable up to 200 °C and degraded in three steps. Whereas, the poly(NAI-ran-MMA)-b-poly(NAI) are stable up to 330 °C and degraded in two steps. The density functional theory methods are used for calculation of equilibrium constants (KATRP) for the ATRP process for the series of laboratory synthesized alkyl halides. A good agreement was observed between the experimentally determined and theoretically calculated KATRP values. The mechanistic studies are carried for poly(NAI-ran-MMA) copolymer system using statistical model discrimination method along with 1H decoupled 13C NMR spectroscopy. For studying the mechanism of copolymerization of NAI and MMA via ATRP methods, “trimer model or penultimate model” will be more accurate than “dimer model or terminal model”.
Chapters in this book
- Frontmatter I
- Preface of the Book of Proceedings of the Virtual Conference on Chemistry and its Applications (VCCA-2022). V
- Contents VII
- List of contributing authors XIX
- 1 Dipeptidyl peptidase IV: a multifunctional enzyme with implications in several pathologies including cancer 1
- 2 A mini review on the prospects of Fagara zanthoxyloides extract based composites: a remedy for COVID-19 and associated replica? 57
- 3 Triterpenoids of antibacterial extracts from the leaves of Bersama abyssinica Fresen (Francoaceae) 75
- 4 Physicochemical assessment and insilico studies on the interaction of 5-HT2c receptor with herbal medication bioactive compounds used in the treatment of premature ejaculation 87
- 5 Xanthoangelol, geranilated chalcone compound, isolation from pudau leaves (Artocarpus kemando Miq.) as antibacterial and anticancer 121
- 6 Exploration of bioactive compounds from Mangifera indica (Mango) as probable inhibitors of thymidylate synthase and nuclear factor kappa-B (NF-Κb) in colorectal cancer management 137
- 7 Identification of potential inhibitors of thymidylate synthase (TS) (PDB ID: 6QXH) and nuclear factor kappa-B (NF–κB) (PDB ID: 1A3Q) from Capsicum annuum (bell pepper) towards the development of new therapeutic drugs against colorectal cancer (CRC) 165
- 8 Synthesis, characterization and in vitro activity study of some organotin(IV) carboxylates against leukemia cancer cell, L-1210 199
- 9 Phytochemicals from Annona muricata (Sour Sop) as potential inhibitors of SARS-CoV-2 main protease (Mpro) and spike receptor protein: a structure-based drug design studies and chemoinformatics analyses 207
- 10 Identification of novel inhibitors of P13K/AKT pathways: an integrated in-silico study towards the development of a new therapeutic agent against ovarian cancer 231
- 11 Immobilization of α-amylase from Aspergillus fumigatus using adsorption method onto zeolite 261
- 12 Phytochemical components and GC–MS analysis of Petiveria alliaceae L. fractions and volatile oils 273
- 13 Characterization of crude saponins from stem bark extract of Parinari curatellifolia and evaluation of its antioxidant and antibacterial activities 287
- 14 Physicochemical and free radical scavenging activity of Adansonia digitata seed oil 307
- 15 Photoprotection strategies with antioxidant extracts: a new vision 321
- 16 A systematic DFT study of arsenic doped iron cluster AsFen (n = 1–4) 335
- 17 Effect of case-based learning, team-based learning and regular teaching methods on secondary school students’ self-concept in chemistry in Maara sub-county, Tharaka Nithi county, Kenya 345
- 18 Random and block architectures of N-arylitaconimide monomers with methyl methacrylate 359
- 19 Evaluation of phytochemicals and amino acid profiles of four vegetables grown on a glyphosate contaminated soil in Southwestern Nigeria 399
- Index 411
Chapters in this book
- Frontmatter I
- Preface of the Book of Proceedings of the Virtual Conference on Chemistry and its Applications (VCCA-2022). V
- Contents VII
- List of contributing authors XIX
- 1 Dipeptidyl peptidase IV: a multifunctional enzyme with implications in several pathologies including cancer 1
- 2 A mini review on the prospects of Fagara zanthoxyloides extract based composites: a remedy for COVID-19 and associated replica? 57
- 3 Triterpenoids of antibacterial extracts from the leaves of Bersama abyssinica Fresen (Francoaceae) 75
- 4 Physicochemical assessment and insilico studies on the interaction of 5-HT2c receptor with herbal medication bioactive compounds used in the treatment of premature ejaculation 87
- 5 Xanthoangelol, geranilated chalcone compound, isolation from pudau leaves (Artocarpus kemando Miq.) as antibacterial and anticancer 121
- 6 Exploration of bioactive compounds from Mangifera indica (Mango) as probable inhibitors of thymidylate synthase and nuclear factor kappa-B (NF-Κb) in colorectal cancer management 137
- 7 Identification of potential inhibitors of thymidylate synthase (TS) (PDB ID: 6QXH) and nuclear factor kappa-B (NF–κB) (PDB ID: 1A3Q) from Capsicum annuum (bell pepper) towards the development of new therapeutic drugs against colorectal cancer (CRC) 165
- 8 Synthesis, characterization and in vitro activity study of some organotin(IV) carboxylates against leukemia cancer cell, L-1210 199
- 9 Phytochemicals from Annona muricata (Sour Sop) as potential inhibitors of SARS-CoV-2 main protease (Mpro) and spike receptor protein: a structure-based drug design studies and chemoinformatics analyses 207
- 10 Identification of novel inhibitors of P13K/AKT pathways: an integrated in-silico study towards the development of a new therapeutic agent against ovarian cancer 231
- 11 Immobilization of α-amylase from Aspergillus fumigatus using adsorption method onto zeolite 261
- 12 Phytochemical components and GC–MS analysis of Petiveria alliaceae L. fractions and volatile oils 273
- 13 Characterization of crude saponins from stem bark extract of Parinari curatellifolia and evaluation of its antioxidant and antibacterial activities 287
- 14 Physicochemical and free radical scavenging activity of Adansonia digitata seed oil 307
- 15 Photoprotection strategies with antioxidant extracts: a new vision 321
- 16 A systematic DFT study of arsenic doped iron cluster AsFen (n = 1–4) 335
- 17 Effect of case-based learning, team-based learning and regular teaching methods on secondary school students’ self-concept in chemistry in Maara sub-county, Tharaka Nithi county, Kenya 345
- 18 Random and block architectures of N-arylitaconimide monomers with methyl methacrylate 359
- 19 Evaluation of phytochemicals and amino acid profiles of four vegetables grown on a glyphosate contaminated soil in Southwestern Nigeria 399
- Index 411
