Free‐radical homopolymerization and copolymerization of ethyl α‐hydroxymethylacrylate in tetrahydrofuran

Fernández‐Monreal, M. C.; Cuervo, R.; Madruga, Enrique López

doi:10.1002/pola.1992.080301104

Cited by 18 publications

(18 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Furthermore, acrylates, having capto‐substituents, produce more stable propagating radicals as compared with allyl radicals and therefore, the propagation reaction is more exothermic in the case of acrylates 7, 23. Insertion of a heteroatom on the methylene group has a positive effect on the polymerizability of the monomer 13–17. Wong and Radom 8 have reported that large substituents would not affect the maximum overlap between the unpaired electron of the propagating radical and the unoccupied π orbitals of the double bond.…”

Section: Mechanistic Overview Of Free Radical Polymerization Of Acrylmentioning

confidence: 99%

“…Thus, the k p / k

_{1/2}^{ct}

ratio has been considered as a descriptor for the polymerizability behavior of the monomers in every group. Values of k p / k

_{1/2}^{ct}

for the same reaction conditions have been used to analyze the kinetic behavior of acrylic monomers 13, 25.…”

Section: Rate Of Polymerizationmentioning

confidence: 99%

“…Polymerization of acrylates is one of the most efficient processes for the rapid production of polymeric materials in high performance inks, coatings, stereo‐lithography, dental restorative fillers and the preparation of contact lenses 7. Because of the wide variety of their industrial usage, acrylate derivatives have been synthesized and studied extensively 5–19.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Modeling the free radical polymerization of acrylates

Günaydın

Salman

Tüzün

et al. 2005

Int J of Quantum Chemistry

View full text Add to dashboard Cite

ABSTRACT:Acrylates have gained importance because of their ease of conversion to high-molecular-weight polymers and their broad industrial use. Methyl methacrylate (MMA) is a well-known monomer for free radical polymerization, but its ␣-methyl substituent restricts the chemical modification of the monomer and therefore the properties of the resulting polymer. The presence of a heteroatom in the methyl group is known to increase the polymerizability of MMA. Methyl ␣-hydroxymethylacrylate (MHMA), methyl ␣-methoxymethylacrylate (MC 1 MA), methyl ␣-acetoxymethylacrylate (MAcMA) show even better conversions to high-molecular-weight polymers than MMA. In contrast, the polymerization rate is known to decrease as the methyl group is replaced by ethyl in ethyl ␣-hydroxymethylacrylate (EHMA) and t-butyl in t-butyl ␣-hydroxymethylacrylate (TBHMA). In this study, quantum mechanical tools (B3LYP/6-31G*) have been used in order to understand the mechanistic behavior of the free radical polymerization reactions of acrylates. The polymerization rates of MMA, MHMA, MC 1 MA, MAcMA, EHMA, TBHMA, MC 1 AN (␣-methoxymethyl acrylonitrile), and MC 1 AA (␣-methoxymethyl acrylic acid) have been evaluated and rationalized. Simple monomers such as allyl alcohol (AA) and allyl chloride (AC) have also been modeled for comparative purposes.

show abstract

Section: Mechanistic Overview Of Free Radical Polymerization Of Acrylmentioning

confidence: 99%

“…Thus, the k p / k

_{1/2}^{ct}

ratio has been considered as a descriptor for the polymerizability behavior of the monomers in every group. Values of k p / k

_{1/2}^{ct}

for the same reaction conditions have been used to analyze the kinetic behavior of acrylic monomers 13, 25.…”

Section: Rate Of Polymerizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Modeling the free radical polymerization of acrylates

Günaydın

Salman

Tüzün

et al. 2005

Int J of Quantum Chemistry

View full text Add to dashboard Cite

show abstract

“…A search of literature reveals that N-VP has been copolymerized with cyclohexyl acrylate using BPO [2] as initiator, maleic anhydride and maleimide initiated by laser rays [3] , monoalkyl Itaconate initiated by AIBN [4] . MMA have been copolymerized with different monomers [5,6] , initiated by conventional initiators as well as ylides [7] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Methylmethacrylate-alt-N-vinyl-2-pyrrolidone Initiated by Phosphorus Containing 1,2 Dipolar Compound

Prajapati

Varshney

2007

Polymer-Plastics Technology and Engineering

View full text Add to dashboard Cite

Copolymerization of methylmethacrylate (MMA) with 1-vinyl-2-pyrrolidone (N-VP), initiated by p-nitrobenzyl triphenyl phosphonium ylide in dioxane at 60 C for 60 min under inert atmosphere of nitrogen yields alternating copolymer as evidenced by the values of r 1 ¼ 0.01 and r 2 ¼ 0.02. The kinetic expression was R p / [I] 0.75 [MMA] 1.2 [VP] 1.2 . The overall activation energy is 45.4 kJ/mol. The FTIR bands of OCH 3 of MMA at 1725 cm À1 and ÀC=O of N-VP at 1679 cm À1 , confirms the incorporation of both the monomers in the copolymer. The glass transition temperature of the copolymer is 133 C. The GPC data shows the polydispersity index at about 1.5. The ESR spectroscopy confirm phenyl radical responsible for initiation.

show abstract

“…Recently, there have been wide exploraethylenes such as methyl methacrylate, vinylitions about its synthesis, polymerization, and dene vinyl acetate, and styrene, [2][3][4][5][6][7][8][9] and in all cases copolymerization with styrene, methyl methacry-MI and its comonomers readily underwent therlate, and 2-vinyl-4,4-dimethylazlactone. [17][18][19][20][21][22][23][24] Because of the presence of the hydroxyl group, EHMA has been widely used as a new crosslink-example, EHMA has been utilized to improve the mechanical properties of wood 24 ; the thermal properties of 2-vinyl-4,4 -dimethylazlactone-EHMA copolymers have been studied to evaluate the stability and crosslinking activity of various functional groups in polymers.…”

Section: Introductionmentioning

confidence: 99%