Identification of degradation products of antioxidants in polyolefins by liquid chromatography combined with atmospheric pressure photoionisation mass spectrometry

Reingruber, Eva; Himmelsbach, Markus; Sauer, Christian; Buchberger, Wolfgang

doi:10.1016/j.polymdegradstab.2010.02.015

Cited by 41 publications

(22 citation statements)

References 9 publications

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“…Other interesting APPI applications that were difficult to classify to the groups presented above, and which therefore are not included in Tables 2-6, include analysis of explosives and samples from polymer industry, the analysis of indigo-type compounds in natural dyes for studies of historical objects, and characterization of the organic residue in meteorite extracts (Duderstadt & Fischer, 2008;Papanastasiou et al, 2008Papanastasiou et al, , 2012Himmelsbach, Buchberger, & Reingruber, 2009;Song & Bartmess, 2009;Reingruber et al, 2010;Callahan et al, 2013;Reisinger, Beissmann, & Buchberger, 2013).…”

Section: F Other Applicationsmentioning

confidence: 99%

Recent developments in atmospheric pressure photoionization‐mass spectrometry

Kauppila

Syage

Benter

2015

Mass Spectrometry Reviews

110

108

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Recent developments in atmospheric pressure photoionization (APPI), which is one of the three most important ionization techniques in liquid chromatography-mass spectrometry, are reviewed. The emphasis is on the practical aspects of APPI analysis, its combination with different separation techniques, novel instrumental developments - especially in gas chromatography and ambient mass spectrometry - and the applications that have appeared in 2009-2014. © 2015 Wiley Periodicals, Inc. Mass Spec Rev 36:423-449, 2017.

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Section: F Other Applicationsmentioning

confidence: 99%

Recent developments in atmospheric pressure photoionization‐mass spectrometry

Kauppila

Syage

Benter

2015

Mass Spectrometry Reviews

110

108

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“…The decrease in stabilizing efficiency in the presence of certain fillers had already been recognized earlier [77,78], but was assigned to adsorption of stabilizer molecules on the surface of the filler only. Finally, it could be revealed that talcum was moreover degrading stabilizers leading to volatile products (namely 2-methylpropylene) [79] as well as to nonvolatile degradation products [80].…”

Section: Degradation Products Of Stabilizers Caused By Interaction Wimentioning

confidence: 99%

Analysis of polyolefin stabilizers and their degradation products

Reingruber

Buchberger

2010

J of Separation Science

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Polymeric materials are complex samples, as they contain various groups of additives, compounding ingredients, and fillers. An important group of additives are stabilizers. Efficient stabilization is essential especially for polypropylene, as it is sensitive to oxidation and radical attack due to the numerous tertiary carbon atoms in its structure. How long a polymer will be sufficiently stabilized can be deduced from the contained amount of intact stabilizer. Different approaches for the analysis of stabilizers in polyolefins are available, which include sample preparation with subsequent chromatographic separation as well as direct analysis techniques. In round-robin tests, stabilizer concentrations obtained varied strongly. This shows the demand for reliable and robust methods. Stabilizers get consumed while protecting the polymer and are then present as degradation products. They were observed while quantifying intact stabilizers, in migration studies, and - if volatile - in emission studies of polymers. Furthermore, e.g. interactions with other polymer ingredients or irradiation degraded stabilizers. The identification of degradation products provides a better insight into the reactions associated with stabilization. Their quantitation makes it possible to deduce the original level of stabilization. Furthermore, polymer ingredients degrading stabilizers can be identified. Knowledge on these interactions contributes significantly to improved polymer stabilization.

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“…Owing to its high sensitivity and specificity, and ability to characterize and quantify wide classes of molecules, mass spectrometry (MS) plays a very important role in characterizing plastic contaminants. Owing to their different chemical structures, different ionization techniques, 2 such as electron ionization, 3,4 laser desorption, 5 secondary‐ion MS, 6 desorption chemical ionization, 7,8 matrix‐assisted laser desorption ionization, 9 atmospheric solid analysis probe, 10 atmospheric pressure photoionization, 11,12 atmospheric pressure chemical ionization, 4,11,13,14 electrospray, 11,14–17 and ambient ionization MS, 18 have been used.…”

Section: Introductionmentioning

confidence: 99%

Characterization of additives in plastics: From MS to MS¹⁰ multistep mass analysis and theoretical calculations of tris(2,4‐di‐tert‐butylphenyl)phosphate

2020

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In the analysis by electrospray (+) of an extract of hemp sprouts put in a polypropylene vial, we found a large contamination of a plastic additive. It was characterized by multiple‐stage MSn experiments (MS ÷ MS10) and identified as tris(2,4‐di‐tert‐butylphenyl)phosphate, also known with the synonyms F32IRS6B46, oxidized Naugard 524, and others. The MS2 ÷ MS7 spectra are characterized by consecutive eliminations of six isobutene molecules from the tert‐butyl moieties, some of them also occurring in the ion source. The first three are calculated to occur preferentially from the ortho positions, whereas eliminations from the para positions are estimated to be less favored at about 5–6 kcal/mol in each step. Once the first three isobutene molecules are eliminated, the remaining three are lost from the tert‐butyl moieties in para positions (MS5 ÷ MS7), yielding protonated triphenylphosphate, whose structure has been confirmed by the MS2 spectrum of triphenylphosphate standard: the latter spectrum is almost superimposable with the MS8 spectrum of the analyte under investigation. MS8 and MS9 spectra show main losses of water and C6H4 molecules. The MS10 spectrum of precursor ions at m/z 215 shows the gas‐phase addition of water and methanol and ions at m/z 168, attributable to the loss of a phosphorus oxide radical. Density functional theory (DFT) calculations (Becke 3LYP [B3LYP] 6‐311+G(2d,2p)) have been used to evaluate structure and stability of different ionic and neutral species involved in the decomposition pathways and to calculate thermochemical data of the decomposition reactions. This multistep mass analysis combined with theoretical calculations resulted to be particularly useful and effective, yielding chemical, thermochemical, and mechanistic data of significant utility in the structural characterization and identification of the unknown analyte as well as to define its gas‐phase reactivity under a multistep low‐energy collision‐induced dissociation regime.

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Identification of degradation products of antioxidants in polyolefins by liquid chromatography combined with atmospheric pressure photoionisation mass spectrometry

Cited by 41 publications

References 9 publications

Recent developments in atmospheric pressure photoionization‐mass spectrometry

Recent developments in atmospheric pressure photoionization‐mass spectrometry

Analysis of polyolefin stabilizers and their degradation products

Characterization of additives in plastics: From MS to MS¹⁰ multistep mass analysis and theoretical calculations of tris(2,4‐di‐tert‐butylphenyl)phosphate

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Identification of degradation products of antioxidants in polyolefins by liquid chromatography combined with atmospheric pressure photoionisation mass spectrometry

Cited by 41 publications

References 9 publications

Recent developments in atmospheric pressure photoionization‐mass spectrometry

Recent developments in atmospheric pressure photoionization‐mass spectrometry

Analysis of polyolefin stabilizers and their degradation products

Characterization of additives in plastics: From MS to MS10 multistep mass analysis and theoretical calculations of tris(2,4‐di‐tert‐butylphenyl)phosphate

Contact Info

Product

Resources

About

Characterization of additives in plastics: From MS to MS¹⁰ multistep mass analysis and theoretical calculations of tris(2,4‐di‐tert‐butylphenyl)phosphate