Polymerization of allylamines in the presence of protonic acids

Masterova, M.N.; Andreyeva, L.I.; Zubov, V.P.; Polak, L.S.; Kabanov, V.A.

doi:10.1016/0032-3950(76)90096-4

Cited by 12 publications

(19 citation statements)

References 4 publications

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“…This reaction occurs with the abstraction of the α‐hydrogen atom of the allyl group by the radicals so that a stable low‐reactive allyl ≪transfer≫ radical is formed. This results in the kinetic chain termination and formation of only low‐molecular‐weight oligomeric products 1–7. It was established that the polymerization rates of allyl and diallyl monomers substantially increase in complex‐forming and acidic media, viz., they grow as the acid (solvent) proton–donor (or complex‐forming) properties become more pronounced or the basicity of the said monomers increases 2–6.…”

Section: Introductionmentioning

confidence: 99%

Impact of various intravascular ultrasound criteria for stent optimization on the six‐month angiographic restenosis

Hong

Lee

Kim

et al. 2002

Cathet Cardio Intervent

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We evaluated the impact of different intravascular ultrasound (IVUS) criteria on 6-month angiographic restenosis in 511 patients with 560 lesions. Seven IVUS criteria were evaluated in this study; stent area at lesion segment 1) > or = 100% of distal reference lumen area, 2) > or = 90% of distal reference lumen area, 3) > or = 80% of average reference lumen area, 4) > or = 90% of average reference lumen area, 5) > or = 55% of average reference vessel area, 6) >/= 7 mm(2), and 7) > or = 2). Using the relative measurement (criteria 1-5), the angiographic restenosis rate was not statistically different. However, absolute measurement of stent area > or = 9 mm(2) (criteria 6 and 7) were associated with significantly lower restenosis rate (14.8% vs. 30.9%, P = 0.001, and 13.5% vs. 24.6%, P = 0.006, respectively). In conclusions, using the relative measurement of IVUS criteria, the occurrence of angiographic restenosis might not be predicted. The absolute measurement of IVUS stent area was the predictor of angiographic restenosis.

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Section: Introductionmentioning

confidence: 99%

Impact of various intravascular ultrasound criteria for stent optimization on the six‐month angiographic restenosis

Hong

Lee

Kim

et al. 2002

Cathet Cardio Intervent

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“…Obviously, it is difficult to reach an equilibrium at which the base could exist only in its protonated form in the acid-base system and it seems likely this was the case in the polymerization systems studied previously [3][4][5][6]8]. Thus, the key point for solving the discussed problem is to create the stable protonated forms of monomers 2 (i.e., attain the state when nonprotonated forms are virtually absent in polymerizing media).…”

Section: Table III __________________________________________________mentioning

confidence: 94%

“…ered previously [3][4][5][6]8] was the acid-base equilibrium achieved so that the monomer would be mainly in the protonated form.…”

Section: Structurementioning

confidence: 99%

“…The first is the strength of the ␣-COH bonds of allyl groups, which increases upon protonation or quaternization of the amines (see Table I). Selected energy and structural characteristics of monomers 1, 5, 6, and 2 calculated by the AM1 method 4 are listed in Table III. It can be seen that protonation or quaternization causes jumpwise changes in the characteristics of the systems as compared to the nonionized amines 1 and 2.…”

Section: Hmw Polymers From Monomers Of the Daa Seriesmentioning

confidence: 99%

“…b No polymer was isolated [3][4][5][6]. c Polymer salts synthesized on the base of 1 ⅐ HCl at 30 and 65°C [8].…”

Section: Reactions Comparedmentioning

confidence: 99%

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Radical polymerization of diallylamine compounds: From quantum chemical modeling to controllable synthesis of high‐molecular‐weight polymers

Timofeeva

Vasilieva

Kleshcheva

et al. 2002

Int J of Quantum Chemistry

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ABSTRACT:We investigated the possibility to obtain high-molecular-weight (HMW) polymers from the monomers of the diallylamine (DAA) series using quantum chemical and experimental methods. Such monomers are known to polymerize into oligomeric products due to the reaction of the degradative chain transfer to the monomer. We studied potential energy profiles of the chain propagation and competing chain transfer reactions, viz., the free radical double bond addition and ␣-hydrogen radical abstraction, respectively, for a number of polymerization processes. Calculations were carried in the framework of the polarized continuum solvent model utilizing the procedure based on the semiempirical MNDO-PM3 background. It was found that the necessary condition for decreasing competitiveness of the chain transfer to the monomer is the availability of monomer molecules in only protonated form in the polymerizing system. Using these results, we developed the strategy for obtaining HMW polymers based on said monomers. We synthesized a monomer system (the equimolar salt of N,N-diallyl-N-methylamine and trifluoroacetic acid) that fully corresponds to such requirements. Novel HMW polymers were then synthesized by radical polymerization of this salt at soft conditions. We established that chain termination is controlled by the bimolecular mechanism. We showed that the degradative chain transfer transforms into the effective chain transfer. The mechanisms of the observed phenomena are discussed.

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Synthesis of High‐Molecular Weight Polymers Based on N,N‐Diallyl‐N‐Methylamine

Timofeeva

Vasilieva

Klescheva

et al. 2002

Macro Chemistry & Physics

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High‐molecular weight polymers, namely poly(N,N‐diallyl‐N‐methylammonium trifluoroacetate) and poly(N,N‐diallyl‐N‐methylamine), were prepared by radical polymerization of N,N‐diallyl‐N‐methylamine in aqueous solution in the presence of an equimolar amount of trifluoroacetic acid and by polymerization of the newly synthesized equimolecular salt N,N‐diallyl‐N‐methylammonium trifluoroacetate in gentle conditions. We have established that chain termination is controlled by the bimolecular mechanism and that degradative chain transfer to monomer transforms into effective chain transfer (see Scheme). The possibility of controlling the polymerization rate and molecular weight of polymers is demonstrated. The mechanisms of the observed phenomena are discussed.

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Polymerization of allylamines in the presence of protonic acids

Cited by 12 publications

References 4 publications

Impact of various intravascular ultrasound criteria for stent optimization on the six‐month angiographic restenosis

Impact of various intravascular ultrasound criteria for stent optimization on the six‐month angiographic restenosis

Radical polymerization of diallylamine compounds: From quantum chemical modeling to controllable synthesis of high‐molecular‐weight polymers

Synthesis of High‐Molecular Weight Polymers Based on N,N‐Diallyl‐N‐Methylamine

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