RAFT (Co)polymerization of 1,1,1,3,3,3-Hexafluoroisopropyl Acrylate as the Synthesis Technique of Amphiphilic Copolymers

Alexandra Grigoreva; Kseniia Tarankova; Sergey Zaitsev

Macromolecular Research, Vol.29, No.8, 524-533, August, 2021

DOI10.1007/s13233-021-9066-8 Export Citation

RAFT (Co)polymerization of 1,1,1,3,3,3-Hexafluoroisopropyl Acrylate as the Synthesis Technique of Amphiphilic Copolymers

Alexandra Grigoreva^†, Kseniia Tarankova, and Sergey Zaitsev

Lobachevsky State University of Nizhni Novgorod, Nizhni Novgorod, Russia, Russian Federation

E-mail:

The reversible addition-fragmentation chain transfer (RAFT) polymerization of 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) in the presence of dibenzyl carbonotrithioate (BTC) was studied. The effect of solvent used in polymerization process on kinetic features and molecular-weight characteristics was shown. It turns out that polymerization of HFIPA proceeds in a control mode at any conditions investigated that is confirmed by linear increase of M n with the rise of conversion and low values of dispersity (D= 1.09-1.3). The location of trithiocarbonate group was estimated both quantum-chemical calculation and experimental methods. Copolymerization monomer pairs of HFIPA-acrylic acid and HFIPA-tert-butyl acrylate in the presence of low molecular (BTC) and polymeric chain transfer agent were investigated. Reactivity ratios of monomers was determined by Fineman- Ross and Kelen-Tudos models. The use of polymeric RAFT agent leads to instance of preferential solvation effect and formation of copolymer with gradient microstructure at final conversion.

Keywords:RAFT polymerization;fluorinated polymers;poly(meth)acrylates;amphiphilic copolymers

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[2] Barner-Kowollik C, Handbook of RAFT Polymerization, Wiley, Weinheim, 2008.

[3] Matyjaszewski K, Xia JH, Chem. Rev., 101(9), 2921 (2001)

[4] Sciannamea V, Jerome R, Detrembleur C, Chem. Rev., 108(3), 1104 (2008)

[5] Moad G, Rizzardo E, Thang SH, Accounts Chem. Res., 41, 1133 (2008)

[6] Chu DSH, Schellinger JG, Shi J, Convertine AJ, Stayton PS, Pun SH, Accounts Chem. Res., 45, 1089 (2012)

[7] Moad G, Rizzardo E, Thang SH, Aust. J. Chem, 59, 669 (2006)

[8] Chong BYK, Le TPT, Moad G, Rizzardo E, Thang SH, Macromolecules, 32(6), 2071 (1999)

[9] Chong YK, Moad G, Rizzardo E, Thang SH, Macromolecules, 40(13), 4446 (2007)

[10] Bruno A, Macromolecules, 43(24), 10163 (2010)

[11] Gladysz JA, Curran DP, Horvath IT, Handbook of Fluorous Chemistry, Wiley-VCH, New York, 2004.

[12] Falireas PG, Ladmiral V, Ameduri B, Polym. Chem., 12, 277 (2021)

[13] Amado E, Kressler J, Soft Matter, 7, 7144 (2011)

[14] Zaitsev SD, Semchikov YD, Vasil’eva DV, Kurushina LV, J. Polym. Sci. B: Polym. Phys., 54, 205 (2012)

[15] Koiry BP, Moukwa M, Singha NK, J. Fluorine Chem., 153, 137 (2013)

[16] Grigoreva A, Polozov E, Zaitsev S, J. Fluorine Chem., 232, 109484 (2020)

[17] Koiry BP, Klok H, Singha NK, J. Fluorine Chem., 165, 109 (2014)

[18] Guo TY, Tang D, Song M, Zhang B, J. Polym. Sci. A: Polym. Chem., 45(22), 5067 (2007)

[19] Xu S, Liu W, J. Fluorine Chem., 129, 125 (2008)

[20] Jiang Y, Li L, Liu J, Wang R, Wang H, Tian Q, Li X, J. Fluorine Chem., 183, 82 (2016)

[21] Serkhacheva NS, Smirnov OI, Tolkachev AV, Prokopov NI, Plutalova AV, Chernikova EV, Khokhlov AR, RSC Adv., 7, 24522 (2017)

[22] Samanta SR, Cai R, Percec V, Polym. Chem., 6, 3259 (2015)

[23] David G, Boyer C, Tonnar J, Ameduri B, Lacroix-Desmazes P, Boutevin B, Chem. Rev., 106(9), 3936 (2006)

[24] Clerc S, Tonnar J, Lacroix-Desmazes P, Eur. Polym. J., 49, 682 (2013)

[25] Guerre M, Schmidt J, Talmon Y, Ameduri B, Ladmiral V, Polym. Chem., 8, 1125 (2017)

[26] Guerre M, Semsarilar M, Godiard F, Ameduri B, Ladmiral V, Polym. Chem., 8, 1477 (2017)

[27] Yang Q, Guerre M, Ladmiral V, Ameduri B, Polym. Chem., 9, 3388 (2018)

[28] Grigoreva A, Polozov E, Zaitsev S, Colloid Polym. Sci., 297, 1423 (2009)

[29] Vishnevetskii DV, Chernikova EV, Garina ES, Sivtsov EV, J. Polym. Sci. B: Polym. Phys., 55, 1221 (2013)

[30] Armarego WLF, Chai C, Purification of Laboratory Chemicals, 7th ed., Butterworth-Heinemann, Oxford, 2012.

[31] Chernikova EV, Terpugova PS, Garina ES, Golubev VB, Polym. Sci. Ser. A, 49, 108 (2007)

[32] Wood MR, Duncalf DJ, Findlay P, Rannard SP, Perrier S, Aust. J. Chem., 60, 772 (2007)

[33] Sato T, Masaki K, Kondo K, Seno M, Tanaka H, Polym. Bull., 35(3), 345 (1995)

[34] Chernikova EV, Sivtsov EV, J. Polym. Sci. B: Polym. Phys., 59, 117 (2017)

[35] Canniccioni B, Monge S, David G, Robin JJ, Polym. Chem.., 4, 3676 (2013)

[36] Benaglia M, Rizzardo E, Alberti A, Guerra M, Macromolecules, 38(8), 3129 (2005)