Copolymerization Phenylcyclopropylmetacrylates with Glycidyl Methacrylate and Their Properties

Kazim Gafar Guliyev; Aysel Elshad Rzayeva; Afet Mirza Aliyeva

doi:doi:10.11648/j.ajaic.20220601.12

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Copolymerization Phenylcyclopropylmetacrylates with Glycidyl Methacrylate and Their Properties

Kazim Gafar Guliyev, Aysel Elshad Rzayeva, Afet Mirza Aliyeva

Published in American Journal of Applied and Industrial Chemistry (Volume 6, Issue 1)

Received: 25 October 2021 Accepted: 12 November 2021 Published: 25 February 2022

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Abstract

New phenylcyclopropyl methacrylates (PhCMA) have been synthesized and studied in detail new monomers radical copolymerization with glycidyl methacrylate (GMA). As a result of laboratory experiments were obtained new cyclopropane and epoxy-containing photosensitive copolymers. PhCMA is a new reactive monomer, its synthesis and homopolymerization have been presented. The choice of this compound to copolymerize it with GMA has been stipulated by the presence of light absorbing carbonyl, cyclopropane and epoxide groups or double bond in the molecule. In the copolymerization of the studied GMAPhCMA system is an important task is choosing the conditions when the polymerization is proceeded only by participation of vinyl group and the reactive fragments would be remained in the side chain without changes. The relative activity of monomers and the parameters of Q and e have been determined by Alfrey-Price method. The copolymerization constants of the specified compound (PhCMA) (r₁) with glycidyl methacrylate (r₂), calculated by the Fineman-Ross method, are: r₁=0.57, r₂=0.65 (Cl); r₁=0.68, r₂=0.55 (NO₂), respectively; the values of the parameters Q and e: Q₁=1.19, e₁=-0.8 (Cl); Q₁=1.42, e₁=-0.9 (NO₂), respectively. The composition and structure of this copolymer have been established. Photochemical studies of the synthesized copolymer have been carried out. It was found that structuring proceeds due to the opening of the cyclopropane ring and epoxy groups, as well as the carbonyl group. The structure and composition monomers and polymers which were synthesized were studied by İR and NMR spectroscopy. An availability of the synthesized copolymer of the reactive groups of various chemical nature in links of macromolecule arouses interest for investigation of photochemical structuring of this copolymer, i.e. to crosslinking under action of UV-irradiation and such polymers showing as negative type photoresists. These polymers with properties of high light sensitivity, film-forming ability, good solubility before irradiation, resistance to solvents, plasma and etchants after cross-linking and good thermal stability, which are very important for photoresist. Due to availability of strongly absorbing light energy of groups (cyclopropane, glycidyl, >С=О etc.) the synthesized copolymers are photosensitive and under the influence of UV-irradiation are subjected to the photochemical conversions leading to formation of crosslinked structures.

Published in	American Journal of Applied and Industrial Chemistry (Volume 6, Issue 1)
DOI	10.11648/j.ajaic.20220601.12
Page(s)	7-12
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Microstructure, Monomers, Copolymerization, Phenylcyclopropyl Methacrylates, Photosensitivity

References

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[3]	Ohe, Y., Ito, H., Watanabe, N., Ichimura, K., A novel dry photopolymer for volume-phase holograms. Journal of Applied Polymer Science, 2000, Vol 77, №10, 2189-2200.
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[7]	A. Ya. Vayner, K. M. Dyumayev, I. A. Likhachev, A. D. Shalatonova, Yu. A. Yartsev, “Methacrylate Derivatives of Carboxyl-Containing Polyimides: Synthesis and Photochemical Transformations,” Doklady Physical Chemistry. vol. 396, May 2004, pp. 115-118. DOI: 10.1023/B:DOPC.0000029167.69210.4c].
[8]	Hou H., Jiang J., Ding M. Ester-type precursor of polyimide and photosensitivity// Eur. Polym. J. 1999. V. 35. N 11. P. 1993-2000. https://doi.org/10.1016/S0014-3057(98)00290-0.
[9]	K. G. Guliyev, G. Z. Ponomareva, A. M. Guliyev, “Photosensitivity of Polymers Based on Epoxy-Substituted Vinylphenylcyclopropanes,” Russian Journal of Appl. Chem. vol. 79, March 2006, pp. 488-491.
[10]	K. G. Guliyev, G. Z. Ponomareva, A. M. Guliyev, “Synthesis and properties of epoxy-containing poly(cyclopropylstyrenes),” Polymer Science. Vol. 49B, August 2007, pp. 196-199. DOI: 10.1134/S1560090407070068].
[11]	K. G. Guliyev, G. Z. Ponomareva, and A. M. Guliyev, “Influence of substituents on copolymerization of p(2-substituted) cyclopropyl styrenes with methylmethacrylate,” Processes of Petrochemistry and Oil-refining, pp. 40-43, January 2003.
[12]	K. Subramanian, A. V. Ramai Reddy, V. Krishnasamy, “Photopolymers: synthesis and characterization of poly(4-cinnamoylphenyl methacrylate),” Macromol. Chem. Rapid Commun. vol. 12, April 1991, pp. 211-214.
[13]	A. Rehab, N. Salahuddin, “Photocrosslinked polymers based on pendant extended chalcone as photoreactive moieties,” Polymer. vol. 40, April 1999, pp. 2197-2207.
[14]	K. G. Guliyev, A. E. Rzayeva, A. M. Guliyev. Synthesis of photosensitive cyclopropa¬ne-containing polymers. Russian Journal of Applied Chemistry, 2019; 92; 9; 1131-1140.
[15]	K. G. Guliyev, G. Z. Ponomareva, S. B. Mamedli, and A. M. Guliyev, “Ultraviolet absorption spectra of 2-substituted-1(n-vinylphenyl)cyclopropanes,” Journal of Structural Chemistry, vol. 50, pp. 693-695, August 2009.
[16]	K. G. Guliyev, А. А. Garayeva, G. Z. Ponomareva, A. M. Aliyeva, A. M. Guliyev, “Radical Copolymerization of p-(2,2-Dichlorocyclopropyl)styrene with Glycidyl Methacrylate and Properties of the Polymer Obtained,” Russian Journal of Appl. Chem. vol. 88, June 2015, pp. 1047-1051.
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APA Style

Kazim Gafar Guliyev, Aysel Elshad Rzayeva, Afet Mirza Aliyeva. (2022). Copolymerization Phenylcyclopropylmetacrylates with Glycidyl Methacrylate and Their Properties. American Journal of Applied and Industrial Chemistry, 6(1), 7-12. https://doi.org/10.11648/j.ajaic.20220601.12

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ACS Style

Kazim Gafar Guliyev; Aysel Elshad Rzayeva; Afet Mirza Aliyeva. Copolymerization Phenylcyclopropylmetacrylates with Glycidyl Methacrylate and Their Properties. Am. J. Appl. Ind. Chem. 2022, 6(1), 7-12. doi: 10.11648/j.ajaic.20220601.12

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AMA Style

Kazim Gafar Guliyev, Aysel Elshad Rzayeva, Afet Mirza Aliyeva. Copolymerization Phenylcyclopropylmetacrylates with Glycidyl Methacrylate and Their Properties. Am J Appl Ind Chem. 2022;6(1):7-12. doi: 10.11648/j.ajaic.20220601.12

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@article{10.11648/j.ajaic.20220601.12,
  author = {Kazim Gafar Guliyev and Aysel Elshad Rzayeva and Afet Mirza Aliyeva},
  title = {Copolymerization Phenylcyclopropylmetacrylates with Glycidyl Methacrylate and Their Properties},
  journal = {American Journal of Applied and Industrial Chemistry},
  volume = {6},
  number = {1},
  pages = {7-12},
  doi = {10.11648/j.ajaic.20220601.12},
  url = {https://doi.org/10.11648/j.ajaic.20220601.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajaic.20220601.12},
  abstract = {New phenylcyclopropyl methacrylates (PhCMA) have been synthesized and studied in detail new monomers radical copolymerization with glycidyl methacrylate (GMA). As a result of laboratory experiments were obtained new cyclopropane and epoxy-containing photosensitive copolymers. PhCMA is a new reactive monomer, its synthesis and homopolymerization have been presented. The choice of this compound to copolymerize it with GMA has been stipulated by the presence of light absorbing carbonyl, cyclopropane and epoxide groups or double bond in the molecule. In the copolymerization of the studied GMAPhCMA system is an important task is choosing the conditions when the polymerization is proceeded only by participation of vinyl group and the reactive fragments would be remained in the side chain without changes. The relative activity of monomers and the parameters of Q and e have been determined by Alfrey-Price method. The copolymerization constants of the specified compound (PhCMA) (r1) with glycidyl methacrylate (r2), calculated by the Fineman-Ross method, are: r1=0.57, r2=0.65 (Cl); r1=0.68, r2=0.55 (NO2), respectively; the values of the parameters Q and e: Q1=1.19, e1=-0.8 (Cl); Q1=1.42, e1=-0.9 (NO2), respectively. The composition and structure of this copolymer have been established. Photochemical studies of the synthesized copolymer have been carried out. It was found that structuring proceeds due to the opening of the cyclopropane ring and epoxy groups, as well as the carbonyl group. The structure and composition monomers and polymers which were synthesized were studied by İR and NMR spectroscopy. An availability of the synthesized copolymer of the reactive groups of various chemical nature in links of macromolecule arouses interest for investigation of photochemical structuring of this copolymer, i.e. to crosslinking under action of UV-irradiation and such polymers showing as negative type photoresists. These polymers with properties of high light sensitivity, film-forming ability, good solubility before irradiation, resistance to solvents, plasma and etchants after cross-linking and good thermal stability, which are very important for photoresist. Due to availability of strongly absorbing light energy of groups (cyclopropane, glycidyl, >С=О etc.) the synthesized copolymers are photosensitive and under the influence of UV-irradiation are subjected to the photochemical conversions leading to formation of crosslinked structures.},
 year = {2022}
}

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TY  - JOUR
T1  - Copolymerization Phenylcyclopropylmetacrylates with Glycidyl Methacrylate and Their Properties
AU  - Kazim Gafar Guliyev
AU  - Aysel Elshad Rzayeva
AU  - Afet Mirza Aliyeva
Y1  - 2022/02/25
PY  - 2022
N1  - https://doi.org/10.11648/j.ajaic.20220601.12
DO  - 10.11648/j.ajaic.20220601.12
T2  - American Journal of Applied and Industrial Chemistry
JF  - American Journal of Applied and Industrial Chemistry
JO  - American Journal of Applied and Industrial Chemistry
SP  - 7
EP  - 12
PB  - Science Publishing Group
SN  - 2994-7294
UR  - https://doi.org/10.11648/j.ajaic.20220601.12
AB  - New phenylcyclopropyl methacrylates (PhCMA) have been synthesized and studied in detail new monomers radical copolymerization with glycidyl methacrylate (GMA). As a result of laboratory experiments were obtained new cyclopropane and epoxy-containing photosensitive copolymers. PhCMA is a new reactive monomer, its synthesis and homopolymerization have been presented. The choice of this compound to copolymerize it with GMA has been stipulated by the presence of light absorbing carbonyl, cyclopropane and epoxide groups or double bond in the molecule. In the copolymerization of the studied GMAPhCMA system is an important task is choosing the conditions when the polymerization is proceeded only by participation of vinyl group and the reactive fragments would be remained in the side chain without changes. The relative activity of monomers and the parameters of Q and e have been determined by Alfrey-Price method. The copolymerization constants of the specified compound (PhCMA) (r1) with glycidyl methacrylate (r2), calculated by the Fineman-Ross method, are: r1=0.57, r2=0.65 (Cl); r1=0.68, r2=0.55 (NO2), respectively; the values of the parameters Q and e: Q1=1.19, e1=-0.8 (Cl); Q1=1.42, e1=-0.9 (NO2), respectively. The composition and structure of this copolymer have been established. Photochemical studies of the synthesized copolymer have been carried out. It was found that structuring proceeds due to the opening of the cyclopropane ring and epoxy groups, as well as the carbonyl group. The structure and composition monomers and polymers which were synthesized were studied by İR and NMR spectroscopy. An availability of the synthesized copolymer of the reactive groups of various chemical nature in links of macromolecule arouses interest for investigation of photochemical structuring of this copolymer, i.e. to crosslinking under action of UV-irradiation and such polymers showing as negative type photoresists. These polymers with properties of high light sensitivity, film-forming ability, good solubility before irradiation, resistance to solvents, plasma and etchants after cross-linking and good thermal stability, which are very important for photoresist. Due to availability of strongly absorbing light energy of groups (cyclopropane, glycidyl, >С=О etc.) the synthesized copolymers are photosensitive and under the influence of UV-irradiation are subjected to the photochemical conversions leading to formation of crosslinked structures.
VL  - 6
IS  - 1
ER  -

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Author Information

Kazim Gafar Guliyev

Azerbaijan National Academy of Sciences, Institute of Polymer Materials, Sumgait City, Azerbaijan
Aysel Elshad Rzayeva

Azerbaijan National Academy of Sciences, Institute of Polymer Materials, Sumgait City, Azerbaijan
Afet Mirza Aliyeva

Azerbaijan National Academy of Sciences, Institute of Polymer Materials, Sumgait City, Azerbaijan

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APA Style

Kazim Gafar Guliyev, Aysel Elshad Rzayeva, Afet Mirza Aliyeva. (2022). Copolymerization Phenylcyclopropylmetacrylates with Glycidyl Methacrylate and Their Properties. American Journal of Applied and Industrial Chemistry, 6(1), 7-12. https://doi.org/10.11648/j.ajaic.20220601.12

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ACS Style

Kazim Gafar Guliyev; Aysel Elshad Rzayeva; Afet Mirza Aliyeva. Copolymerization Phenylcyclopropylmetacrylates with Glycidyl Methacrylate and Their Properties. Am. J. Appl. Ind. Chem. 2022, 6(1), 7-12. doi: 10.11648/j.ajaic.20220601.12

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AMA Style

Kazim Gafar Guliyev, Aysel Elshad Rzayeva, Afet Mirza Aliyeva. Copolymerization Phenylcyclopropylmetacrylates with Glycidyl Methacrylate and Their Properties. Am J Appl Ind Chem. 2022;6(1):7-12. doi: 10.11648/j.ajaic.20220601.12

Copy | Download

@article{10.11648/j.ajaic.20220601.12,
  author = {Kazim Gafar Guliyev and Aysel Elshad Rzayeva and Afet Mirza Aliyeva},
  title = {Copolymerization Phenylcyclopropylmetacrylates with Glycidyl Methacrylate and Their Properties},
  journal = {American Journal of Applied and Industrial Chemistry},
  volume = {6},
  number = {1},
  pages = {7-12},
  doi = {10.11648/j.ajaic.20220601.12},
  url = {https://doi.org/10.11648/j.ajaic.20220601.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajaic.20220601.12},
  abstract = {New phenylcyclopropyl methacrylates (PhCMA) have been synthesized and studied in detail new monomers radical copolymerization with glycidyl methacrylate (GMA). As a result of laboratory experiments were obtained new cyclopropane and epoxy-containing photosensitive copolymers. PhCMA is a new reactive monomer, its synthesis and homopolymerization have been presented. The choice of this compound to copolymerize it with GMA has been stipulated by the presence of light absorbing carbonyl, cyclopropane and epoxide groups or double bond in the molecule. In the copolymerization of the studied GMAPhCMA system is an important task is choosing the conditions when the polymerization is proceeded only by participation of vinyl group and the reactive fragments would be remained in the side chain without changes. The relative activity of monomers and the parameters of Q and e have been determined by Alfrey-Price method. The copolymerization constants of the specified compound (PhCMA) (r1) with glycidyl methacrylate (r2), calculated by the Fineman-Ross method, are: r1=0.57, r2=0.65 (Cl); r1=0.68, r2=0.55 (NO2), respectively; the values of the parameters Q and e: Q1=1.19, e1=-0.8 (Cl); Q1=1.42, e1=-0.9 (NO2), respectively. The composition and structure of this copolymer have been established. Photochemical studies of the synthesized copolymer have been carried out. It was found that structuring proceeds due to the opening of the cyclopropane ring and epoxy groups, as well as the carbonyl group. The structure and composition monomers and polymers which were synthesized were studied by İR and NMR spectroscopy. An availability of the synthesized copolymer of the reactive groups of various chemical nature in links of macromolecule arouses interest for investigation of photochemical structuring of this copolymer, i.e. to crosslinking under action of UV-irradiation and such polymers showing as negative type photoresists. These polymers with properties of high light sensitivity, film-forming ability, good solubility before irradiation, resistance to solvents, plasma and etchants after cross-linking and good thermal stability, which are very important for photoresist. Due to availability of strongly absorbing light energy of groups (cyclopropane, glycidyl, >С=О etc.) the synthesized copolymers are photosensitive and under the influence of UV-irradiation are subjected to the photochemical conversions leading to formation of crosslinked structures.},
 year = {2022}
}

Copy | Download

TY  - JOUR
T1  - Copolymerization Phenylcyclopropylmetacrylates with Glycidyl Methacrylate and Their Properties
AU  - Kazim Gafar Guliyev
AU  - Aysel Elshad Rzayeva
AU  - Afet Mirza Aliyeva
Y1  - 2022/02/25
PY  - 2022
N1  - https://doi.org/10.11648/j.ajaic.20220601.12
DO  - 10.11648/j.ajaic.20220601.12
T2  - American Journal of Applied and Industrial Chemistry
JF  - American Journal of Applied and Industrial Chemistry
JO  - American Journal of Applied and Industrial Chemistry
SP  - 7
EP  - 12
PB  - Science Publishing Group
SN  - 2994-7294
UR  - https://doi.org/10.11648/j.ajaic.20220601.12
AB  - New phenylcyclopropyl methacrylates (PhCMA) have been synthesized and studied in detail new monomers radical copolymerization with glycidyl methacrylate (GMA). As a result of laboratory experiments were obtained new cyclopropane and epoxy-containing photosensitive copolymers. PhCMA is a new reactive monomer, its synthesis and homopolymerization have been presented. The choice of this compound to copolymerize it with GMA has been stipulated by the presence of light absorbing carbonyl, cyclopropane and epoxide groups or double bond in the molecule. In the copolymerization of the studied GMAPhCMA system is an important task is choosing the conditions when the polymerization is proceeded only by participation of vinyl group and the reactive fragments would be remained in the side chain without changes. The relative activity of monomers and the parameters of Q and e have been determined by Alfrey-Price method. The copolymerization constants of the specified compound (PhCMA) (r1) with glycidyl methacrylate (r2), calculated by the Fineman-Ross method, are: r1=0.57, r2=0.65 (Cl); r1=0.68, r2=0.55 (NO2), respectively; the values of the parameters Q and e: Q1=1.19, e1=-0.8 (Cl); Q1=1.42, e1=-0.9 (NO2), respectively. The composition and structure of this copolymer have been established. Photochemical studies of the synthesized copolymer have been carried out. It was found that structuring proceeds due to the opening of the cyclopropane ring and epoxy groups, as well as the carbonyl group. The structure and composition monomers and polymers which were synthesized were studied by İR and NMR spectroscopy. An availability of the synthesized copolymer of the reactive groups of various chemical nature in links of macromolecule arouses interest for investigation of photochemical structuring of this copolymer, i.e. to crosslinking under action of UV-irradiation and such polymers showing as negative type photoresists. These polymers with properties of high light sensitivity, film-forming ability, good solubility before irradiation, resistance to solvents, plasma and etchants after cross-linking and good thermal stability, which are very important for photoresist. Due to availability of strongly absorbing light energy of groups (cyclopropane, glycidyl, >С=О etc.) the synthesized copolymers are photosensitive and under the influence of UV-irradiation are subjected to the photochemical conversions leading to formation of crosslinked structures.
VL  - 6
IS  - 1
ER  -

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