Reactions of dimethyl sulfide with oxidized polypropylene

Falicki, S.; Carlsson, D. J.; Gosciniak, D. J.; Cooke, J. M.

doi:10.1016/0141-3910(93)90045-k

Cited by 17 publications

(3 citation statements)

References 12 publications

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“…Hydroperoxide accumulation plays a key role in the oxidation process and estimating its concentration in oxidized polymeric materials has become an extensively studied topic . Particularly interesting has been the study of polypropylene peroxides using dimethyl sulfide (DMS); previous reports demonstrate DMS reacts quickly with polymer peroxides to form dimethyl sulfoxide . This reaction has significant implications in CWA decontamination particularly as bis(2‐chloroethyl) sulfide, also known as sulfur mustard (HD) gas, may be oxidized via its sulfide moiety into a less toxic, sulfoxide byproduct .…”

Section: Resultsmentioning

confidence: 99%

Air Activated Self‐Decontaminating Polydicyclopentadiene PolyHIPE Foams for Rapid Decontamination of Chemical Warfare Agents

McGann

Daniels

Giles

et al. 2018

Macromol. Rapid Commun.

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The threat of chemical warfare agents (CWA) compels research into novel self-decontaminating materials (SDM) for the continued safety of first-responders, civilians, and active service personnel. The capacity to actively detoxify, as opposed to merely sequester, offending agents under typical environmental conditions defines the added value of SDMs in comparison to traditional adsorptive materials. Porous polymers, synthesized via the high internal phase emulsion (HIPE) templating, provide a facile fabrication method for materials with permeable open cellular structures that may serve in air filtration applications. PolyHIPEs comprising polydicyclopentadiene (polyDCPD) networks form stable hydroperoxide species following activation in air under ambient conditions. The hydroperoxide-containing polyDCPD materials react quickly with CWA simulants, Demeton-S and 2-chloroethyl ethyl sulfide, forming oxidation products as confirmed via gas chromatography mass spectrometry. The simplicity of the detoxification chemistry paired with the porous foam form factor presents an exciting opportunity for the development of self-decontaminating filter media.

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Section: Resultsmentioning

confidence: 99%

Air Activated Self‐Decontaminating Polydicyclopentadiene PolyHIPE Foams for Rapid Decontamination of Chemical Warfare Agents

McGann

Daniels

Giles

et al. 2018

Macromol. Rapid Commun.

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“…The carbonyl carbon of a peracid would also resonate from 170 to 175 ppm. The detection of peracids has been reported with the infrared spectroscopic analysis of oxidatively aged polypropylenes treated with dimethyl sulfide, − although these findings have been disputed …”

Section: Resultsmentioning

confidence: 99%

“…The detection of peracids has been reported with the infrared spectroscopic analysis of oxidatively aged polypropylenes treated with dimethyl sulfide, [37][38][39] although these findings have been disputed. 40 Two small, reasonably narrow resonances were observed at 105.7 and 114.1 ppm in the C(2) labeled sample spectra (peaks labeled "g" in the C(2) spectrum of Figure 1). The peak at 114.1 ppm was not detected in the sample γ-irradiated at 24 °C.…”

Section: C(2) Sample Resonancesmentioning

confidence: 96%

Solid-State ¹³C NMR Investigation of the Oxidative Degradation of Selectively Labeled Polypropylene by Thermal Aging and γ-Irradiation

et al. 2005

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Unstabilized polypropylene (PP) films having selective 13 C isotopic labeling were subjected to thermal aging at 50, 80, and 109°C and to γ-irradiation at 24 and 80°C. The oxidized films were examined using solid-state 13 C nuclear magnetic resonance (NMR) spectroscopy. Dramatic differences were found in the type and distribution of oxidation products originating from the three carbon atom sites within the PP macromolecule (tertiary carbon, secondary carbon, and methyl side group). Most of the oxidation products that formed on the polymer chain originated through chemical reactions at the PP tertiary carbons. Under all of the aging conditions examined, tertiary peroxides (from the PP tertiary site) were the most abundant functional group produced. Also originating from the PP tertiary carbon were significant amounts of tertiary alcohols, together with several more minor products that included "chain-end" methyl ketones. No significant amount of peroxides or alcohols associated with the PP secondary carbon sites was detected. A substantial yield of carboxylate groups was identified (acids, esters, etc.). The majority of these originated from the PP secondary carbon site, from which other minor products also formed, including in-chain ketones. We found no measurable yield of oxidation products originating from reaction at the PP methyl group. Remarkably similar distributions of the major oxidation products were obtained for thermal aging at different temperatures, whereas the product distributions obtained for irradiation at the different temperatures exhibited significant differences. Time-dependent concentration plots have been obtained, which show the amounts of the various oxidation products originating at the different PP sites, as a function of the extent of material oxidation.

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Photogenerated hydroperoxides of EPDM rubbers and their characterization

Chmela

Lacoste

1995

J. Polym. Sci. A Polym. Chem.

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Three different ethylene/propylene/diene (EPDM) rubbers were allowed to react with singlet oxygen. This reaction leads to the production of polymeric pendant hydroperoxides only in one case. Terpolymer ethylene/propylene/5‐ethylidene‐2‐norbornene reacts with singlet oxygen and isolated and associated secondary hydroperoxides are formed. Anthracene was used as a sensitizer for production of singlet oxygen under 365‐nm irradiation. The course of hydroperoxide formation was similar in the solid state as well as in the toluene solution. Reactivity of hydroperoxides prepared was tested in their reaction with gaseous dimethyl sulfide (DMS). Both the isolated and associated hydroperoxides react with DMS by dual fast and slow process. Fast process is more significant in the case of the isolated hydroperoxides. © 1995 John Wiley & Sons, Inc.

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Reactions of dimethyl sulfide with oxidized polypropylene

Cited by 17 publications

References 12 publications

Air Activated Self‐Decontaminating Polydicyclopentadiene PolyHIPE Foams for Rapid Decontamination of Chemical Warfare Agents

Air Activated Self‐Decontaminating Polydicyclopentadiene PolyHIPE Foams for Rapid Decontamination of Chemical Warfare Agents

Solid-State ¹³C NMR Investigation of the Oxidative Degradation of Selectively Labeled Polypropylene by Thermal Aging and γ-Irradiation

Photogenerated hydroperoxides of EPDM rubbers and their characterization

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Reactions of dimethyl sulfide with oxidized polypropylene

Cited by 17 publications

References 12 publications

Air Activated Self‐Decontaminating Polydicyclopentadiene PolyHIPE Foams for Rapid Decontamination of Chemical Warfare Agents

Air Activated Self‐Decontaminating Polydicyclopentadiene PolyHIPE Foams for Rapid Decontamination of Chemical Warfare Agents

Solid-State 13C NMR Investigation of the Oxidative Degradation of Selectively Labeled Polypropylene by Thermal Aging and γ-Irradiation

Photogenerated hydroperoxides of EPDM rubbers and their characterization

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Solid-State ¹³C NMR Investigation of the Oxidative Degradation of Selectively Labeled Polypropylene by Thermal Aging and γ-Irradiation