Synthesis and Characterization of Isobutylene-Based Ammonium and Phosphonium Bromide Ionomers

Parent, J. Scott; Penciu, Anca; Guillen-Castellanos, Sergio A.; Liskova, and Andrea; Whitney, Ralph A.

doi:10.1021/ma049158k

Cited by 53 publications

(64 citation statements)

References 33 publications

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“…Because of the presence of the active allylic bromide functionality, the bromobutyl rubbers significantly improved the rate of sulfur vulcanization and enhanced the curing compatibility with unsaturated elastomers. [13][14][15][16][17] Recently, Amit et al 18 developed a selfhealing elastomeric material based on BIIR through the chemical modification of BIIR with butyl imidazolium into an imidazolium-modified BIIR. 9 When BIIR was reacted with ZnO at high temperatures, the exomethylene isomer of the bromobutyl rubber produced the conjugated diene butyl via the dehydrobromination reaction.…”

Section: Introductionmentioning

confidence: 99%

Thermally stable bromobutyl rubber with a high crosslinking density based on a 4,4′‐bismaleimidodiphenylmethane curing agent

Sathi

Jang

Jeong

et al. 2016

J of Applied Polymer Sci

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The development of thermally stable bromobutyl rubbers has been a challenge in rubber chemistry and engineering. In this circumstance, 4,4 0 -bismaleimidodiphenylmethane (BMI) was newly applied as a novel crosslinking agent for thermally stable brominated isobutylene-isoprene rubber (BIIR) with a high crosslinking density. With oscillating disk rheometry and differential scanning calorimetry, the curing characteristics of BIIR were systematically investigated with respect to the content of BMI. We found that BMI alone could crosslink BIIR at higher temperature, and a corresponding possible chemical reaction mechanism was proposed. With the introduction of zinc oxide, the curing reaction of BIIR with BMI was significantly accelerated, and the resulting vulcanizate provided a higher state of curing with excellent overcure reversion stability even at a temperature of 190 8C for 2 h. The content of the dicumyl peroxide (DCP) reaction accelerator was also optimized to be BMI/DCP 5 1:0.05 on the basis of considerations of the curing rate, scorch safety, maximum rheometric torque, and reversion resistance at 160 8C. Compared with the conventional sulfurcured BIIR, the BMI-cured BIIR exhibited a higher crosslinking density with a superior low compression set property at elevated temperatures and an excellent thermal stability.

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Section: Introductionmentioning

confidence: 99%

Thermally stable bromobutyl rubber with a high crosslinking density based on a 4,4′‐bismaleimidodiphenylmethane curing agent

Sathi

Jang

Jeong

et al. 2016

J of Applied Polymer Sci

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“…Note that the addition of 5 wt % deuterated methanol to the ionomer solution affected the chemical shift and resolution of allylic resonances. This is typical of ionomer derivatives of BIIR, in which ion‐pair aggregation affects local chain segment mobility to the extent that 1 H NMR spin‐spin relaxation times are significantly reduced …”

Section: Resultsmentioning

confidence: 94%

Hybrid ionic/covalent polymer networks derived from functional imidazolium ionomers

Ozvald

Parent

Whitney

2013

J. Polym. Sci. Part A: Polym. Chem.

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A new class of ionomers is described wherein ionpairs bear reactive functionality, thereby facilitating further chemical modification. Halide displacement from brominated poly(isobutylene-co-isoprene) by 1-vinylimidazole is used to prepare ionomer derivatives that can be crosslinked by radical oligiomerization of pendant vinyl groups. The resulting thermosets contain a labile network of imidazolium bromide ion-pair aggregates as well as a stable covalent network. As a result of their hybrid ionic/covalent composition, these thermoset elastomers provide a unique combination of rheological, tensile and stress relaxation properties that cannot be achieved from conventional covalent or ionic networks.

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“…To our knowledge, the chemical modification of butyl rubber is carried out by the chemical modification of a halobutyl rubber such as bromobutyl rubber rather than the butyl rubber itself. Amine,5 ester,6 ether,7 ammonium, and phosphonium salt8 functionalities have been reported to be introduced to butyl rubber by reactions with halobutyl rubbers. Polyethers such as polyethylene glycol can be grafted onto butyl rubber9, 10 by a bimolecular nucleophilic substitution (S N 2) reaction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of peroxide‐curable butyl rubber via suzuki–miyaura coupling of halogenated butyl rubber with 4‐vinylphenylboronic acid

Takenaka

Suzuki

Takeshita

et al. 2011

J. Polym. Sci. A Polym. Chem.

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The Suzuki–Miyaura coupling reaction of brominated butyl rubber (BIIR) and/or chlorinated butyl rubber with a mixture of 4‐vinylphenylboronic acid and phenylboronic acid was carried out in THF under various conditions using a di‐μ‐chlorobis [5‐hydroxy‐2‐[1‐(hydroxyimino‐κN)ethyl]phenylκC] palladium(II) dimer, which is a type of cyclopalladated complex, as a catalyst. When BIIR and a small amount (Pd/Br ≈ 1/1000) of complex were used as the substrate and catalyst, respectively, a 4‐vinylphenyl and phenyl group could be introduced to butyl rubber in a high yield. Isomerization of the exo carbon–carbon double bond in BIIR was observed during the coupling reaction to give a cis and trans endo structure. The peroxide curing behavior of the resulting polymer at 170 °C indicated that the polymer could be cured by dicumyl peroxide, and the maximum torque of the resulting material, which reflects the crosslink density, was controllable by the composition of the boronic acids used. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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Synthesis and Characterization of Isobutylene-Based Ammonium and Phosphonium Bromide Ionomers

Cited by 53 publications

References 33 publications

Thermally stable bromobutyl rubber with a high crosslinking density based on a 4,4′‐bismaleimidodiphenylmethane curing agent

Thermally stable bromobutyl rubber with a high crosslinking density based on a 4,4′‐bismaleimidodiphenylmethane curing agent

Hybrid ionic/covalent polymer networks derived from functional imidazolium ionomers

Synthesis of peroxide‐curable butyl rubber via suzuki–miyaura coupling of halogenated butyl rubber with 4‐vinylphenylboronic acid

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