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Polymerisation Via Macrozwitterions, 3. Ethyl And Butyl Cyanoacrylates Polymerised By Benzyldimethyl, Triethyl And Tribenzylamines

D. S. Johnston, D. C. Pepper
Published 1981 · Chemistry

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Anionic polymerisations of ethyl and butyl cyanoacrylates (ECA and BCA) in THF, initiated by benzyldimethylamine (BDMA), triethylamine (TEA) and tribenzylamine (TBA) were studied between 50 and −78°C. Initiator utilisation was very low, and polymer molecular weights correspondingly high, though believed to be depressed by acid impurities in the monomer samples. Conversion curves reached internal 1st order kinetics, almost instantaneously when the initiator was BDMA, more slowly with TEA, and only after a long acceleration period with TBA, which gave overall rates some two orders of magnitude lower than those induced by the other amines. With BCA initiated by BDMA or TEA, the rate constants increased as reaction temperature was lowered. A general kinetic scheme is suggested, postulating no intrinsic termination reactions, and complex initiation processes, which according to the nature of amine and monomer may involve either one or two pre-initiation equilibria.



This paper is referenced by
In vitro characterization of cyanoacrylate embolic glues used for vascular embolization
Y. Li (2017)
10.1002/PEN.760330302
Dielectric monitoring of the curing process in cyanoacrylate resin
S. Radhakrishnan (1993)
10.1002/9781119006671.CH3
Controlled Photopolymerization and Novel Architectures
S. Doran (2015)
10.1080/1061186X.2019.1579822
From poly(alkyl cyanoacrylate) to squalene as core material for the design of nanomedicines
S. Mura (2019)
10.1016/J.POLYMDEGRADSTAB.2008.04.012
Synthesis and degradation behavior of poly(ethyl cyanoacrylate)
M. G. Han (2008)
10.1007/978-94-007-1248-5_9
Poly(Alkyl Cyanoacrylate) Nanosystems
J. Nicolas (2011)
10.1002/9781119526445.CH10
Cyanoacrylates: Towards High Temperature Resistant Instant Adhesives. A Critical Review
Barry N. Burns (2017)
10.1002/wnan.15
Synthesis of poly(alkyl cyanoacrylate)-based colloidal nanomedicines.
J. Nicolas (2009)
10.1007/S00289-010-0416-5
Anionic polymerization of N-substituted maleimide with achiral and chiral amines as an initiator
Motohisa Azechi (2011)
10.1016/0141-3910(86)90029-7
The thermal degradation of polymers of n-butylcyanoacrylate prepared using tertiary phosphine and amine initiators
C. Birkinshaw (1986)
10.1016/S0032-3861(00)00618-2
The isolation of a zwitterionic initiating species for ethyl cyanoacrylate (ECA) polymerization and the identification of the reaction products between 1°, 2°, and 3° amines with ECA
P. Klemarczyk (2001)
10.1002/POLA.27606
Rubbery wound closure adhesives. I. design, synthesis, characterization, and testing of polyisobutylene-based cyanoacrylate homo- and co-networks
István Szanka (2015)
10.1002/(SICI)1099-0518(19991215)37:24<4570::AID-POLA14>3.0.CO;2-#
Degradation and stabilization of polycyanoacrylates
Douglas R. Robello (1999)
10.1002/POLA.27605
Rubbery Wound Closure Adhesives. II. Initiators for and Initiation of 2-Octyl Cyanoacrylate Polymerization
Istvan Szanka (2015)
10.1039/c8sc04729d
Controlled living anionic polymerization of cyanoacrylates by frustrated Lewis pair based initiators† †Electronic supplementary information (ESI) available: Devices, methods and procedures, analytical supporting material: NMR spectra, GPC traces and MALDI-TOF chromatograms. See DOI: 10.1039/c8sc0472
Rubén Sáez (2019)
10.1016/J.CEJ.2019.122400
Controllable polymerization of n-butyl cyanoacrylate using a high-gravity rotating packed bed
Xingzheng Liu (2020)
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