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Çeşitli Uzunluklardaki PEG’ler Vasıtasıyla PVC’nin “Klik” Kimyası ile Çapraz Bağlanması

Yıl 2022, Cilt: 12 Sayı: 1, 59 - 66, 01.06.2022

Nilgün Asan , Temel Öztürk , Hasibe Kudu , Ergül Meyvacı , Efkan Çatıker

Öz

Çapraz bağlı poli(vinil klorür) (c-PVC), azit grup ekli poli(vinil klorür) (PVC-N3) ile dipropargillenmiş polietilen glikolün (dp-PEG)
“klik” kimyası reaksiyonuyla sentezlendi. Bu amaç için, dp-PEG’ler, farklı molekül ağırlıklarına sahip polietilen glikollerin (400 Da,
600 Da, 1000 Da, 1500 Da, 2000 Da, 3000 Da, and 10000 Da) propargil klorür ile muamelesinden elde edildiler. PVC-N3, PVC
zincirleri üzerindeki asılı klorürlerle azid iyonu arasındaki yer değiştirme reaksiyonuyla sentezlendi. PVC-N3 ve çeşitli uzunluklardaki
dp-PEG’ler kullanılarak farklı derecelerde çapraz bağlamaya sahip c-PVC’ler elde edildi. PVC-N3, dp-PEG ve c-PVC’nin
karakterizasyonları, Fourier dönüşümlü kızılötesi spektroskopisi, nükleer manyetik rezonans spektroskopisi, termogravimetrik analiz,
taramalı elektron mikroskobu ve elementel analiz teknikleri kullanılarak gerçekleştirildi. N,N-dimetilformamid içinde farklı çapraz
bağlanma yoğunluklarına sahip c-PVC’lerin şişme dereceleri nicel ölçümlerle belirlendi.

Anahtar Kelimeler

"Klik" kimyası çapraz bağlanma poli(vinil klorür) polietilen glikol şişme derecesi

Kaynakça

  • Asan, N., Öztürk, T. 2017. Synthesis and Characterization of Poly(Vinyl Chloride-graft-Ethylene Glycol) Graft Copolymers by "Click" Chemistry. Hacettepe J. Biol. Chem., 45:35–42. doi:10.15671/HJBC.2017.139
  • Grishin, D. F. 2015. Synthesis of Vinyl Chloride Homo- and Copolymers under the Conditions of Controlled Radical Polymerization. Russ. J. Appl. Chem., 88:361–376. doi:10.1134/S1070427215030015
  • Savaş, B., Öztürk, T. 2020. Synthesis and Characterization of Poly(vinyl chloride-g-methyl methacrylate) Graft Copolymer by Redox Polymerization and Cu Catalyzed Azide-alkyne Cycloaddition Reaction. J. Macromol. Sci. Part A., 57:819–825. doi:10.1080/10601325.2020.1788393
  • Wang, H., Dong, J. H., Qiu, A. Y., Gu, Z. W. 1998. Studies on Properties and Drug Delivery Systems of PTMC-b-PEG-b-PTMC Block Copolymers. J. Macromol. Sci. Part A, 35:811–820. doi:10.1080/10601329808002013
  • Aydinli, M., Tutas, M., Bozdemir, O. A. 2004. Mechanical and light transmittance properties of locust bean gum based edible films. Turk. J. Chem., 28:163–171.
  • Riess, G. 2003. Micellization of Block Copolymers. Prog. Polym. Sci., 28:1107–1170. doi:10.1016/S0079-6700(03)00015-7
  • Gacal, B., Durmaz, H., Tasdelen, M. A., Hizal, G., Tunca, U., Yagci, Y., Demirel, A. L. 2006. Anthracene-Maleimide-Based Diels-Alder "Click Chemistry" as a Novel Route to Graft Copolymers. Macromolecules, 39:5330–5336. doi:10.1021/ma060690c
  • Pispas, S., Hadjichristidis, N. 2003. Aggregation Behavior of Poly(Butadiene-b-Ethylene Oxide) Block Copolymers in Dilute Aqueous Solutions: Effect of Concentration, Temperature, Ionic Strength, and Type of Surfactant. Langmuir, 19:48–54. doi:10.1021/la020561z
  • Göktaş, M., Öztürk, T., Atalar, M. N., Tekeş, A. T., Hazer, B. 2014. One-Step Synthesis of Triblock Copolymers via Simultaneous Reversible-Addition Fragmentation Chain Transfer (RAFT) and Ring-Opening Polymerization using a Novel Difunctional Macro-RAFT Agent Based on Polyethylene Glycol. J. Macromol. Sci. Part A, 51:854–863. doi:10.1080/10601325.2014.953366
  • Kolb, H.C., Finn, M.G., Sharpless, K.B. 2001. Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew. Chem. Int. Edit., 40:2004–2021. doi:10.1002/1521-3773(20010601)40:11%3c2004:AIDANIE2004%3e3.0.CO,2-5
  • Hein, C.D., Liu, X.M., Wang, D. 2008. Click Chemistry: A Powerful Tool for Pharmaceutical Sciences. Pharm. Res., 25:2216–2230. doi:10.1007/s11095-008-9616-1
  • Moses, J. E., Moorhouse, A. D. 2007. The Growing Applications of Click Chemistry. Chem. Soc. Rev., 36:1249–1262. doi:10.1039/B613014N
  • Savaş, B., Çatıker, E., Öztürk, T. 2020. Synthesis and Characterization of Poly(α-methyl β-alanine)-poly(ε-caprolactone) Tri Arm Star Polymer by Hydrogen Transfer Polymerization, Ring-Opening Polymerization and "Click" Chemistry. J. Polym. Res., 28:30. doi:10.1007/s10965-020-02367-z
  • Xu, J., Ye, J., Liu, S. Y. 2007. Synthesis of Well-Defined Cyclic Poly(N-Isopropylacrylamide) via Click Chemistry and Its Unique Thermal Phase Transition Behavior. Macromolecules, 40:9103–9110. doi:10.1021/ma0717183
  • Tunca, U. 2013. Triple Click Reaction Strategy for Macromolecular Diversity. Macromol. Rapid. Commun., 34:38–46. doi:10.1002/marc.201200656
  • Altıntas, O., Tunca, U. 2011. Synthesis of Terpolymers by Click Reactions. Chem. Asian J., 6:2584-2591. doi:10.1002/asia.201100138
  • Xi, W., Scott, T. F., Kloxin, C. J., Bowman, C. N. 2014. Click Chemistry in Materials Science. Adv. Funct. Mater., 24:2572–2590. doi:10.1002/adfm.201302847
  • Çatıker, E., Meyvacı, E., Atakay, M., Salih, B., Öztürk, T. 2019. Synthesis and Characterization of Amphiphilic Triblock Copolymers Including β-alanine/α-methyl-β-alanine and Ethylene Glycol by "Click" Chemistry. Polym. Bull., 76:2113–2128. doi:10.1007/s00289-018-2561-1
  • Binder, W. H., Sachsenhofer, R. 2007. ‘Click’ Chemistry in Polymer and Materials Science. Macromol. Rapid Commun., 28:15–54. doi:10.1002/marc.200600625
  • Moshaverinia, A., Thirumamagal, B. T. S., Schricker, S. R. 2012. Click Chemistry: A Potential Platform for Development of Novel Dental Restorative Materials. J. Macromol. Sci. Part A, 49:288–292. doi:10.1080/10601325.2012.662027
  • Öztürk, T., Yörümez, C. 2020. Synthesis of Block Copolymer Including Polyepichlorohydrin and Polyethylene Glycol by "Click" Chemistry: Evaluation of Primary Parameters of Copolymerization. Polym. Bull., 77:4773–4788. doi:10.1007/s00289-019-02989-4
  • Öztürk, T., Kılıçlıoğlu, A., Savaş, B., Hazer, B. 2018. Synthesis and Characterization of Poly(ɛ-caprolactone-co-ethylene glycol) Star-Type Amphiphilic Copolymers by "Click" Chemistry and Ring-Opening Polymerization. J. Macromol. Sci. Part A, 55:588–594. doi:10.1080/10601 325. 2018.1481344
  • Barner-Kowollik, C., Du Prez, F. E., Espeel, P., Hawker, C. J., Junkers, T., Schlaad, H., Camp, W. V. 2011. “Clicking” Polymers or Just Efficient Linking: What Is the Difference? Angew. Chem. Int. Ed., 50:60-62. doi:10.1002/anie.201003707
  • Tunca, U. 2018. Click and Multicomponent Reactions Work Together for Polymer Chemistry. Macromol. Chem. Phys., 219:1800163. doi:10.1002/macp.201800163
  • Öztürk, T., Cavicchi, C. A. 2018. Synthesis and Characterization of Poly(epichlorohydrin-g-ε-caprolactone) Graft Copolymers by Click Chemistry. J. Polym. Mater., 35:209–220. doi:10.32381/JPM.2018.35.02.6
  • Kiskan, B., Demiray, G., Yagci, Y. 2008. Thermally Curable Polyvinylchloride via Click Chemistry. J. Polym. Sci. Part A, 46:3512–3518. doi:10.1002/pola.22685
  • Pawlak, M., Grygolowicz-Pawlak, E., Crespo, G.A., Mistlberger, G., Bakker, E. 2013. PVC-Based Ion-Selective Electrodes with Enhanced Biocompatibility by Surface Modification with "Click" Chemistry. Electroanalysis, 25:1840–1846. doi:10.1002/elan.201300212
  • Zhang, Z., Xiong, J., He, G., Dang, D., Xie, Y., Wang, Q. 2020. Fluorous Effect-Induced Emission Of Azido Substituted Poly(Vinylidene Fluoride) with High Photostability and Film Formation. Polym. Chem., 11:1307–1313. doi:10.1039/C9PY01622H
  • Öztürk, T., Meyvacı, E., Bektaş, H., Menteşe, E. 2019. Synthesis and Characterization of Ring-Type and Branched Polymers Including Polyethylene Glycols by "Click" Chemistry. SN Appl. Sci., 1:343. doi:10.1007/s42452-019-0360-4
  • Öztürk, T., Meyvacı, E. 2017. Synthesis and Characterization Poly(ɛ-Caprolactone-b-Ethylene Glycol-b-ɛ-Caprolactone) ABA Type Block Copolymers via "Click" Chemistry and Ring-Opening Polymerization. J. Macromol. Sci. Part A, 54:575–581. doi:10.1080/10601325.2017.1309251
  • Öztürk, T., Göktaş, M., Savaş, B., Işıklar, M., Atalar M.N., Hazer, B. 2014. Synthesis and Characterization of Poly(vinyl chloride-graft-2-vinylpyridine) Graft Copolymers using a Novel Macroinitiator by Reversible Addition-Fragmentation Chain Transfer Polymerization. e-Polymers, 14:27–34. doi:10.1515/epoly-2013-0011
  • Öztürk, T., Meyvacı, E., Arslan, T. 2020. Synthesis and Characterization of Poly(Vinyl Chloride-g-ε-Caprolactone) Brush Type Graft Copolymers by Ring-Opening Polymerization and "Click" Chemistry. J. Macromol. Sci. Part A, 57:171–180. doi:10.1080/10601325.2019.1680253
  • Collins, E. A., Bares, J., Billmeyer, F. W. Jr. 1973. Experiments in Polymer Science; John Wiley and Sons: New York
  • Hamurcu, E., Baysal, B. M. 1993. Interpenetrating Polymer Networks of Poly(dimethylsiloxane): 1. Preparation and Characterization. Polymer, 34:5163-5167. doi:10.1016/0032-3861(93)90264-B
  • Hazer, B., Baysal, B. M. 1986. Preparation of Block Copolymers Using a New Polymeric Peroxycarbamate. Polymer, 27:961–968. doi:10.1016/0032-3861(86)90312-5

Cross-linking of PVC by Various Lengths of PEG via “Click” Chemistry

Yıl 2022, Cilt: 12 Sayı: 1, 59 - 66, 01.06.2022

Nilgün Asan , Temel Öztürk , Hasibe Kudu , Ergül Meyvacı , Efkan Çatıker

Öz

Cross-linked poly(polyvinyl chloride) (c-PVC) was synthesized by “click” reaction of polyvinyl chloride with azido pendant group
(PVC-N3) and dipropargyllated polyethylene glycol (dp-PEG). For this purpose, dp-PEGs were obtained from polyethylene glycols
with different molecular weights (400 Da, 600 Da, 1000 Da, 1500 Da, 2000 Da, 3000 Da, and 10000 Da) via treatment with
propargyl chloride. PVC-N3 was synthesized through the substitution reaction between the pendant chloride on the PVC chains
and azide ion. By using PVC-N3 and dp-PEGs with various lengths, c-PVCs with various degrees of cross-linking was obtained.
The characterization of the PVC-N3, dp-PEG and c-PVC were performed using Fourier transform infrared spectroscopy, nuclear
magnetic resonance spectroscopy, thermogravimetric analysis, scanning electron microscopy and elemental analysis. Degrees of
swelling of c-PVCs with different cross-linking densities in N,N-dimethylformamide were determined by quantitative measurements

Anahtar Kelimeler

"Click" chemistry cross-linking poly(vinyl chloride) polyethylene glycol degree of swelling

Kaynakça

  • Asan, N., Öztürk, T. 2017. Synthesis and Characterization of Poly(Vinyl Chloride-graft-Ethylene Glycol) Graft Copolymers by "Click" Chemistry. Hacettepe J. Biol. Chem., 45:35–42. doi:10.15671/HJBC.2017.139
  • Grishin, D. F. 2015. Synthesis of Vinyl Chloride Homo- and Copolymers under the Conditions of Controlled Radical Polymerization. Russ. J. Appl. Chem., 88:361–376. doi:10.1134/S1070427215030015
  • Savaş, B., Öztürk, T. 2020. Synthesis and Characterization of Poly(vinyl chloride-g-methyl methacrylate) Graft Copolymer by Redox Polymerization and Cu Catalyzed Azide-alkyne Cycloaddition Reaction. J. Macromol. Sci. Part A., 57:819–825. doi:10.1080/10601325.2020.1788393
  • Wang, H., Dong, J. H., Qiu, A. Y., Gu, Z. W. 1998. Studies on Properties and Drug Delivery Systems of PTMC-b-PEG-b-PTMC Block Copolymers. J. Macromol. Sci. Part A, 35:811–820. doi:10.1080/10601329808002013
  • Aydinli, M., Tutas, M., Bozdemir, O. A. 2004. Mechanical and light transmittance properties of locust bean gum based edible films. Turk. J. Chem., 28:163–171.
  • Riess, G. 2003. Micellization of Block Copolymers. Prog. Polym. Sci., 28:1107–1170. doi:10.1016/S0079-6700(03)00015-7
  • Gacal, B., Durmaz, H., Tasdelen, M. A., Hizal, G., Tunca, U., Yagci, Y., Demirel, A. L. 2006. Anthracene-Maleimide-Based Diels-Alder "Click Chemistry" as a Novel Route to Graft Copolymers. Macromolecules, 39:5330–5336. doi:10.1021/ma060690c
  • Pispas, S., Hadjichristidis, N. 2003. Aggregation Behavior of Poly(Butadiene-b-Ethylene Oxide) Block Copolymers in Dilute Aqueous Solutions: Effect of Concentration, Temperature, Ionic Strength, and Type of Surfactant. Langmuir, 19:48–54. doi:10.1021/la020561z
  • Göktaş, M., Öztürk, T., Atalar, M. N., Tekeş, A. T., Hazer, B. 2014. One-Step Synthesis of Triblock Copolymers via Simultaneous Reversible-Addition Fragmentation Chain Transfer (RAFT) and Ring-Opening Polymerization using a Novel Difunctional Macro-RAFT Agent Based on Polyethylene Glycol. J. Macromol. Sci. Part A, 51:854–863. doi:10.1080/10601325.2014.953366
  • Kolb, H.C., Finn, M.G., Sharpless, K.B. 2001. Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew. Chem. Int. Edit., 40:2004–2021. doi:10.1002/1521-3773(20010601)40:11%3c2004:AIDANIE2004%3e3.0.CO,2-5
  • Hein, C.D., Liu, X.M., Wang, D. 2008. Click Chemistry: A Powerful Tool for Pharmaceutical Sciences. Pharm. Res., 25:2216–2230. doi:10.1007/s11095-008-9616-1
  • Moses, J. E., Moorhouse, A. D. 2007. The Growing Applications of Click Chemistry. Chem. Soc. Rev., 36:1249–1262. doi:10.1039/B613014N
  • Savaş, B., Çatıker, E., Öztürk, T. 2020. Synthesis and Characterization of Poly(α-methyl β-alanine)-poly(ε-caprolactone) Tri Arm Star Polymer by Hydrogen Transfer Polymerization, Ring-Opening Polymerization and "Click" Chemistry. J. Polym. Res., 28:30. doi:10.1007/s10965-020-02367-z
  • Xu, J., Ye, J., Liu, S. Y. 2007. Synthesis of Well-Defined Cyclic Poly(N-Isopropylacrylamide) via Click Chemistry and Its Unique Thermal Phase Transition Behavior. Macromolecules, 40:9103–9110. doi:10.1021/ma0717183
  • Tunca, U. 2013. Triple Click Reaction Strategy for Macromolecular Diversity. Macromol. Rapid. Commun., 34:38–46. doi:10.1002/marc.201200656
  • Altıntas, O., Tunca, U. 2011. Synthesis of Terpolymers by Click Reactions. Chem. Asian J., 6:2584-2591. doi:10.1002/asia.201100138
  • Xi, W., Scott, T. F., Kloxin, C. J., Bowman, C. N. 2014. Click Chemistry in Materials Science. Adv. Funct. Mater., 24:2572–2590. doi:10.1002/adfm.201302847
  • Çatıker, E., Meyvacı, E., Atakay, M., Salih, B., Öztürk, T. 2019. Synthesis and Characterization of Amphiphilic Triblock Copolymers Including β-alanine/α-methyl-β-alanine and Ethylene Glycol by "Click" Chemistry. Polym. Bull., 76:2113–2128. doi:10.1007/s00289-018-2561-1
  • Binder, W. H., Sachsenhofer, R. 2007. ‘Click’ Chemistry in Polymer and Materials Science. Macromol. Rapid Commun., 28:15–54. doi:10.1002/marc.200600625
  • Moshaverinia, A., Thirumamagal, B. T. S., Schricker, S. R. 2012. Click Chemistry: A Potential Platform for Development of Novel Dental Restorative Materials. J. Macromol. Sci. Part A, 49:288–292. doi:10.1080/10601325.2012.662027
  • Öztürk, T., Yörümez, C. 2020. Synthesis of Block Copolymer Including Polyepichlorohydrin and Polyethylene Glycol by "Click" Chemistry: Evaluation of Primary Parameters of Copolymerization. Polym. Bull., 77:4773–4788. doi:10.1007/s00289-019-02989-4
  • Öztürk, T., Kılıçlıoğlu, A., Savaş, B., Hazer, B. 2018. Synthesis and Characterization of Poly(ɛ-caprolactone-co-ethylene glycol) Star-Type Amphiphilic Copolymers by "Click" Chemistry and Ring-Opening Polymerization. J. Macromol. Sci. Part A, 55:588–594. doi:10.1080/10601 325. 2018.1481344
  • Barner-Kowollik, C., Du Prez, F. E., Espeel, P., Hawker, C. J., Junkers, T., Schlaad, H., Camp, W. V. 2011. “Clicking” Polymers or Just Efficient Linking: What Is the Difference? Angew. Chem. Int. Ed., 50:60-62. doi:10.1002/anie.201003707
  • Tunca, U. 2018. Click and Multicomponent Reactions Work Together for Polymer Chemistry. Macromol. Chem. Phys., 219:1800163. doi:10.1002/macp.201800163
  • Öztürk, T., Cavicchi, C. A. 2018. Synthesis and Characterization of Poly(epichlorohydrin-g-ε-caprolactone) Graft Copolymers by Click Chemistry. J. Polym. Mater., 35:209–220. doi:10.32381/JPM.2018.35.02.6
  • Kiskan, B., Demiray, G., Yagci, Y. 2008. Thermally Curable Polyvinylchloride via Click Chemistry. J. Polym. Sci. Part A, 46:3512–3518. doi:10.1002/pola.22685
  • Pawlak, M., Grygolowicz-Pawlak, E., Crespo, G.A., Mistlberger, G., Bakker, E. 2013. PVC-Based Ion-Selective Electrodes with Enhanced Biocompatibility by Surface Modification with "Click" Chemistry. Electroanalysis, 25:1840–1846. doi:10.1002/elan.201300212
  • Zhang, Z., Xiong, J., He, G., Dang, D., Xie, Y., Wang, Q. 2020. Fluorous Effect-Induced Emission Of Azido Substituted Poly(Vinylidene Fluoride) with High Photostability and Film Formation. Polym. Chem., 11:1307–1313. doi:10.1039/C9PY01622H
  • Öztürk, T., Meyvacı, E., Bektaş, H., Menteşe, E. 2019. Synthesis and Characterization of Ring-Type and Branched Polymers Including Polyethylene Glycols by "Click" Chemistry. SN Appl. Sci., 1:343. doi:10.1007/s42452-019-0360-4
  • Öztürk, T., Meyvacı, E. 2017. Synthesis and Characterization Poly(ɛ-Caprolactone-b-Ethylene Glycol-b-ɛ-Caprolactone) ABA Type Block Copolymers via "Click" Chemistry and Ring-Opening Polymerization. J. Macromol. Sci. Part A, 54:575–581. doi:10.1080/10601325.2017.1309251
  • Öztürk, T., Göktaş, M., Savaş, B., Işıklar, M., Atalar M.N., Hazer, B. 2014. Synthesis and Characterization of Poly(vinyl chloride-graft-2-vinylpyridine) Graft Copolymers using a Novel Macroinitiator by Reversible Addition-Fragmentation Chain Transfer Polymerization. e-Polymers, 14:27–34. doi:10.1515/epoly-2013-0011
  • Öztürk, T., Meyvacı, E., Arslan, T. 2020. Synthesis and Characterization of Poly(Vinyl Chloride-g-ε-Caprolactone) Brush Type Graft Copolymers by Ring-Opening Polymerization and "Click" Chemistry. J. Macromol. Sci. Part A, 57:171–180. doi:10.1080/10601325.2019.1680253
  • Collins, E. A., Bares, J., Billmeyer, F. W. Jr. 1973. Experiments in Polymer Science; John Wiley and Sons: New York
  • Hamurcu, E., Baysal, B. M. 1993. Interpenetrating Polymer Networks of Poly(dimethylsiloxane): 1. Preparation and Characterization. Polymer, 34:5163-5167. doi:10.1016/0032-3861(93)90264-B
  • Hazer, B., Baysal, B. M. 1986. Preparation of Block Copolymers Using a New Polymeric Peroxycarbamate. Polymer, 27:961–968. doi:10.1016/0032-3861(86)90312-5
Toplam 35 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Araştırma Makaleleri
Yazarlar

Nilgün Asan 0000-0001-6388-3507

Temel Öztürk 0000-0002-7856-9809

Hasibe Kudu

Ergül Meyvacı 0000-0003-3530-1316

Efkan Çatıker 0000-0003-2493-7570

Yayımlanma Tarihi 1 Haziran 2022
Yayımlandığı Sayı Yıl 2022 Cilt: 12 Sayı: 1

Kaynak Göster

APA Asan, N., Öztürk, T., Kudu, H., Meyvacı, E., vd. (2022). Cross-linking of PVC by Various Lengths of PEG via “Click” Chemistry. Karaelmas Fen Ve Mühendislik Dergisi, 12(1), 59-66. https://doi.org/10.7212/karaelmasfen.992843
AMA Asan N, Öztürk T, Kudu H, Meyvacı E, Çatıker E. Cross-linking of PVC by Various Lengths of PEG via “Click” Chemistry. Karaelmas Fen ve Mühendislik Dergisi. Haziran 2022;12(1):59-66. doi:10.7212/karaelmasfen.992843
Chicago Asan, Nilgün, Temel Öztürk, Hasibe Kudu, Ergül Meyvacı, ve Efkan Çatıker. “Cross-Linking of PVC by Various Lengths of PEG via ‘Click’ Chemistry”. Karaelmas Fen Ve Mühendislik Dergisi 12, sy. 1 (Haziran 2022): 59-66. https://doi.org/10.7212/karaelmasfen.992843.
EndNote Asan N, Öztürk T, Kudu H, Meyvacı E, Çatıker E (01 Haziran 2022) Cross-linking of PVC by Various Lengths of PEG via “Click” Chemistry. Karaelmas Fen ve Mühendislik Dergisi 12 1 59–66.
IEEE N. Asan, T. Öztürk, H. Kudu, E. Meyvacı, ve E. Çatıker, “Cross-linking of PVC by Various Lengths of PEG via ‘Click’ Chemistry”, Karaelmas Fen ve Mühendislik Dergisi, c. 12, sy. 1, ss. 59–66, 2022, doi: 10.7212/karaelmasfen.992843.
ISNAD Asan, Nilgün vd. “Cross-Linking of PVC by Various Lengths of PEG via ‘Click’ Chemistry”. Karaelmas Fen ve Mühendislik Dergisi 12/1 (Haziran 2022), 59-66. https://doi.org/10.7212/karaelmasfen.992843.
JAMA Asan N, Öztürk T, Kudu H, Meyvacı E, Çatıker E. Cross-linking of PVC by Various Lengths of PEG via “Click” Chemistry. Karaelmas Fen ve Mühendislik Dergisi. 2022;12:59–66.
MLA Asan, Nilgün vd. “Cross-Linking of PVC by Various Lengths of PEG via ‘Click’ Chemistry”. Karaelmas Fen Ve Mühendislik Dergisi, c. 12, sy. 1, 2022, ss. 59-66, doi:10.7212/karaelmasfen.992843.
Vancouver Asan N, Öztürk T, Kudu H, Meyvacı E, Çatıker E. Cross-linking of PVC by Various Lengths of PEG via “Click” Chemistry. Karaelmas Fen ve Mühendislik Dergisi. 2022;12(1):59-66.
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