N-hydroxyphthalimide-initiated radical polymerization of vinyl monomers

Opeida, I. A.; Kompanets, M. O.; Kushch, О. V.; Matvienko, A. G.

doi:10.1134/s1070427207100230

Cited by 6 publications

(16 citation statements)

References 4 publications

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“…By taking the reported E p and E t values, E i was calculated ( E i = 2 E a + E t – 2 E p ) as 9.6 and 11.6 kcal mol −1 for the AIBN + NHPI and only NHPI‐initiated polymerizations, respectively. These values are in line with the reported 5.0 kcal mol −1 activation energy of initiation by NHPI (in the absence of oxygen) for the free radical polymerization of methyl methacrylate and acrylonitrile . The difference may arise from the occurrence of chain transfer reactions during the polymerization, which we did not consider during our calculations.…”

Section: Resultssupporting

confidence: 88%

N‐Hydroxyphthalimide‐Mediated Oxidation of Styrene by Molecular Oxygen

Khan

Pal

2013

Macro Chemistry & Physics

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In this work, the N‐hydroxyphthalimide (NHPI) is used for the oxidative polymerization of styrene at 25–100 psi oxygen pressure at 35–55 °C to obtain a faster rate of polymerization than in 2,2′‐azobisisobutyronitrile (AIBN)‐initiated polymerizations. The rates for oxidative polymerization are determined from the oxygen consumption (Δp) against time plots and NHPI shows a reaction rate increased several fold compared with AIBN. The kinetics of the oxidative polymerization reactions are studied at various concentrations of oxygen, NHPI, AIBN, and monomer. The polymerization rate of styrene is almost the same when the NHPI analogue, N‐hydroxysuccinimide (NHSI), is employed. A mechanism of oxidative polymerization in the presence of NHPI is suggested on the basis of the kinetic data and characterization results of poly(styrene peroxide) (PSP). The NHPI is efficient in initiation of the oxidative radical polymerization of styrene.

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Section: Resultssupporting

confidence: 88%

N‐Hydroxyphthalimide‐Mediated Oxidation of Styrene by Molecular Oxygen

Khan

Pal

2013

Macro Chemistry & Physics

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“…A solution containing 1.5·10 -4 mol/L of Pb(OAc) 4 and 1.5·10 -3 mol/L NHPI in acetic acid was stirred in a cuvette and purged with argon for 15 min, the purging was then ceased and the UV absorption spectrum of the solution was recorded. For several minutes, while the oxidation reaction was proceeding, some increase in the optical density of the solution was observed.…”

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confidence: 99%

“…The process of polymerization, initiated by NHPI, according to previously obtained experimental data [4], was described by the following scheme:…”

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confidence: 99%

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Kinetics and mechanism of the addition of the phthalimid-n-oxyl radical to the double bond of vinyl compounds

et al. 2010

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The kinetics of the decomposition of the phthalimid-N-oxyl radical (PINO) in acetic acid has been studied. The rate constants of the addition of the radical to p bonds of molecules of vinyl compounds -styrene, methyl methacrylate, acrylonitrile, and methyl acrylate -have been measured. It was shown that electron-donor substituents in the monomer molecule increase, while electron-acceptor substituents decrease the rate of addition. The reactivity of monomers in the elementary step of addition of the PINO radical decreases in the order CH

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“…In previous work [5], we showed that N-hydroxyphthalimide (NHPI) is an efficient initiator of the radical polymerization of vinyl monomers. The initiation step in the presence of NHPI proceeds through formation of a complex between NHPI and the vinyl compound due to hydrogen bonding.…”

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Action of N-hydroxyphthalimide on chain stereoregularity in the radical polymerization of methyl methacrylate

Opeida¹,

Kompanets²,

Kushch³

et al. 2011

Theor Exp Chem

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UDC 541.64+541.63+678.7 I. A. Opeida, M. A. Kompanets, O. V. Kushch, and E. S. Papayanina N-Hydroxyphthalimide (NHPI) has a dual function in the radical polymerization of methyl methacrylate (MMA): this compound acts as an initiator and also provides for stereochemical control of the polymer chain. Lowering the polymerization temperature leads to increased syndiotactic specificity in the polymethyl methacrylate molecule. The action of NHPI as an initiator and stereoregulator is attributed to the capacity of this compound to form a hydrogen bond with the monomer molecule and growing macroradical.

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N-hydroxyphthalimide-initiated radical polymerization of vinyl monomers

Cited by 6 publications

References 4 publications

N‐Hydroxyphthalimide‐Mediated Oxidation of Styrene by Molecular Oxygen

N‐Hydroxyphthalimide‐Mediated Oxidation of Styrene by Molecular Oxygen

Kinetics and mechanism of the addition of the phthalimid-n-oxyl radical to the double bond of vinyl compounds

Action of N-hydroxyphthalimide on chain stereoregularity in the radical polymerization of methyl methacrylate

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