Novel thermal radical initiators based on a triazene moiety for radical polymerization

Seokwoo Kang; Taemin Kim; Beomjin Kim; Yeonkyu Jeong; Young Il Park; Seung Man Noh; Jongwook Park

Journal of Industrial and Engineering Chemistry, Vol.68, 1-5, December, 2018

DOI10.1016/j.jiec.2018.08.008 Export Citation

Novel thermal radical initiators based on a triazene moiety for radical polymerization

Seokwoo Kang, Taemin Kim, Beomjin Kim, Yeonkyu Jeong, Young Il Park¹, Seung Man Noh¹, and Jongwook Park^†

Department of Chemical Engineering, Kyung Hee University, Gyeonggi, 17104, Republic of Korea
¹Research Center for Green Fine Chemicals, Korea Research Institute of Chemical Technology, Ulsan 44412, Republic of Korea

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In this study, we designed and synthesized novel thermal radical initiators of BTAP (1-phenyl-3,3-dipropyltriazene), BTACP (1-(phenyldiazenyl)pyrrolidine), BTACH (1-(phenyldiazenyl)piperidine), and BTACH7 (1-(phenyldiazenyl)azepane) based on a triazene moiety to provide a thermal initiator for radical polymerization. The synthetic method is valuable due to the simplicity. In addition, the synthesized thermal initiator did not affect the color of the polymer. Among the four initiators, the polymerization time for the BTACH of the 6-membered ring decreased by 67%, as opposed to the polymerization time without initiator. Conversion after polymerization was over 92%. DSC experiments also showed that the initiator with hexagonal rings had the lowest peak polymerization temperature of 160 °C. Our study suggests a promising new initiator system that is effective for radical polymerization.

Keywords:Thermal radical initiator;Triazene;Radical polymerization

[References]

Endo T, Sanda F, Macromol. Symp., 107, 237 (1996)
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Kamigaito M, Ando T, Sawamoto M, Chem. Rev., 101(12), 3689 (2001)
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[Referenced By]

[1] Endo T, Sanda F, Macromol. Symp., 107, 237 (1996)

[2] Ghassemieh E, Marcello C, Materials in Automotive Application, State of the Art and Prospects. 20, 365 (2011).

[3] Kamigaito M, Ando T, Sawamoto M, Chem. Rev., 101(12), 3689 (2001)

[4] Cantor B, Grant P, Johnston C, Authomotive Enginnering: Lightweight, pp.1 (2008).

[5] Kardar P, Ebrahimi M, Bastani S, Prog. Org. Coat., 62, 321 (2008)

[6] Roche S, Pavan S, Loubet JL, Barbeau P, Magny B, Prog. Org. Coat., 47, 37 (2003)

[7] Valet A, Prog. Org. Coat., 35, 223 (1999)

[8] Seubert CM, Nichols ME, Prog. Org. Coat., 49, 218 (2004)

[9] Maag K, Lenhard W, Loffels H, Prog. Org. Coat., 40, 93 (2000)

[10] Odian G, Principles of Polymerization, fourth ed., Staten Island, New York, 2004.