Inhibition of the Oxidation and Polymerization of Methyl Methacrylate. II. Effect of Aromatic Amines<sup>1</sup>

Yates, W. Ross; Ihrig, Judson L.

doi:10.1021/ja01082a005

Cited by 15 publications

(5 citation statements)

References 3 publications

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“…This may result from the reaction of the isobutyronitrile radicals or the polymer chain radicals with the DDM amino groups forming less reactive amine radicals. This explanation is consistent with similar observations that the polymerization of methyl methacrylate can be inhibited by aromatic primary amines . This is also supported by Imoto's study of AIBN-initiated methyl methacrylate in the presence of dimethylaniline where it was found that the formation of less reactive amine radicals reduced the rate of polymerization of the methacrylate.…”

Section: Resultssupporting

confidence: 90%

“…This explanation is consistent with similar observations that the polymerization of methyl methacrylate can be inhibited by aromatic primary amines. 29 This is also supported by Imoto's 30 study of AIBN-initiated methyl methacrylate in the presence of dimethylaniline where it was found that the formation of less reactive amine radicals reduced the rate of polymerization of the methacrylate. In the VER/AIBN: DGEBA/DDM system, the DDM concentration is much higher than the 1-MeI concentration in the VER/AIBN: DGEBA/1-MeI system, and so the DDM radical reaction would be more likely and may explain its slower cure.…”

Section: Resultsmentioning

confidence: 69%

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Near-Infrared and Rheological Investigations of Epoxy−Vinyl Ester Interpenetrating Polymer Networks

et al. 2001

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Rheological and near-infrared (NIR) spectroscopic investigations have been undertaken for two different interpenetrating polymer networks (IPNs) based on a model vinyl ester (VER, composed of bisphenol A diglycidyl ether dimethacrylate, bisGMA, in 30 wt % styrene) cured with azobis(isobutyronitrile) (AIBN) and an epoxy monomer (diglycidyl ether of bisphenol A, DGEBA) cured either with 1-methylimidazole (1-MeI) or with a stoichiometric quantity of 4,4′-diaminodiphenylmethane (DDM). NIR studies showed that the vinyl ester resin component cured more quickly than the epoxy component. The rate of vinyl conversion within the 50:50 wt % VER/AIBN:DGEBA/DDM IPN system was slower than in the 50:50 wt % VER/AIBN:DGEBA/1-MeI IPN and was much slower than in the neat VER/AIBN system due to the dilution of the VER components by the epoxy system and retardation of the radical polymerization by the amines, as previously observed in DSC and mid-FTIR studies of similar systems. The rate of epoxy conversion in the 50:50 wt % VER/AIBN:DGEBA/1-MeI IPN was slower than in the neat 1-MeI cured epoxy, indicating that the presence of the vinyl ester component also had a dilutional effect within the IPN reducing the concentration of epoxy and imidazole species and hence slowing the reaction. In contrast, the rate of epoxy conversion in the 50:50 IPN of VER/AIBN:DGEBA/DDM was faster than in the neat DDM-cured epoxy, possibly due to the catalysis of the epoxy-amine reaction by the hydroxy groups in the bisGMA. The similarity between the rheology and gel times for the VER/AIBN system and the IPNs indicated that the gelation of the VER component determined the overall gel behavior of the IPN. The gel times correlated well with the vinyl NIR conversion data in that the gelation occurred first for the neat VER/AIBN resin and last for the VER/AIBN:DGEBA/DDM IPN. These observations are also consistent with the effects of dilution of the VER reactants by the epoxy component in the IPN and were confirmed by studies of VER/AIBN diluted with xylene. All systems appeared to vitrify after a period of time as the cure temperature was well below the maximally attainable glass transition temperature of all resins systems. The vinyl group conversion at the vitrification point was marginally higher in the IPNs than in the neat resin systems, but the epoxy conversions in the IPNs were significantly lower at vitrification. The neat resins approached vitrification faster than the IPNs which showed a much slower rise in modulus to the glassy plateau.

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Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 69%

Near-Infrared and Rheological Investigations of Epoxy−Vinyl Ester Interpenetrating Polymer Networks

et al. 2001

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“…I n general many aromatic amines are relatively strong inhibitors while the aliphatic analogs are weak.s. 7 The difference between the strongest phenylamines and the strongest naphthylamines is not great. The cyclic amine, phenothiazine, is much weaker than the strongest aromatic amines.…”

Section: Resultsmentioning

confidence: 99%

Relative inhibitory effect of various compounds on the rate of polymerization of vinyl acetate. III. Effect of compounds of various classes

Georgieff¹

1970

J of Applied Polymer Sci

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“…Also there is evidence that some tertiary aromatic amine accelerators themselves can have an inhibiting effect on the polymerization (24)(25)(26).…”

Section: Bmentioning

confidence: 99%

Properties and interactions of oral structures and restorative materials

Cassel¹

1978

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Inhibition of the Oxidation and Polymerization of Methyl Methacrylate. II. Effect of Aromatic Amines¹

Cited by 15 publications

References 3 publications

Near-Infrared and Rheological Investigations of Epoxy−Vinyl Ester Interpenetrating Polymer Networks

Near-Infrared and Rheological Investigations of Epoxy−Vinyl Ester Interpenetrating Polymer Networks

Relative inhibitory effect of various compounds on the rate of polymerization of vinyl acetate. III. Effect of compounds of various classes

Properties and interactions of oral structures and restorative materials

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Inhibition of the Oxidation and Polymerization of Methyl Methacrylate. II. Effect of Aromatic Amines1

Cited by 15 publications

References 3 publications

Near-Infrared and Rheological Investigations of Epoxy−Vinyl Ester Interpenetrating Polymer Networks

Near-Infrared and Rheological Investigations of Epoxy−Vinyl Ester Interpenetrating Polymer Networks

Relative inhibitory effect of various compounds on the rate of polymerization of vinyl acetate. III. Effect of compounds of various classes

Properties and interactions of oral structures and restorative materials

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Product

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Inhibition of the Oxidation and Polymerization of Methyl Methacrylate. II. Effect of Aromatic Amines¹