Thermal stability and degradation mechanisms of poly(acrylic acid) and its salts: Part 1—Poly(acrylic acid)

McNeill, I.C.; Sadeghi, S.M.T.

doi:10.1016/0141-3910(90)90034-5

Cited by 173 publications

(81 citation statements)

References 15 publications

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“…The most intense peak, observed at m/z 241.1, indicates the elimination of a water molecule from the precursor ion. Water was shown to be one major product in thermal degradation study of PAA [33,34,[43][44][45] or PMAA [43]. This dehydration process would occur with the formation of a six-membered ring anhydride from two pendant acid groups (Scheme 1), as previously demonstrated studying thermally degraded PAA and PMAA resins by nuclear magnetic resonance (NMR) [43] or mass spectrometry [33].…”

Section: Tandem Mass Spectrometry Of Singly Charged Oligomersmentioning

confidence: 61%

“…This reaction could proceed in a charge-induced mechanism, as described in Scheme 1. Elimination of a carbon dioxide molecule was systematically found to be a major thermal degradation route for PAA [33,34,[43][44][45] and PMAA [43]. All thermal degradation studies also indicate that decarboxylation was slower than dehydration and required higher temperatures to proceed.…”

Section: Tandem Mass Spectrometry Of Singly Charged Oligomersmentioning

confidence: 96%

“…The fragment ion detected at m/z 215 (C 11 H 19 O 4 Ϫ ; DBE: 2.5; error: ϩ8.9 ppm) would indicate the loss of a carbon dioxide molecule from the precursor ion m/z 259, as described in Scheme 2. This direct decarboxylation, poorly detected at a 20 eV collision energy, does not appear to proceed at a high rate and would not compete efficiently with the dehydration process, as concluded from thermal degradation studies of neutral PAA and PMAA [33,34,[43][44][45] ; DBE 3.5; error: ϩ16.2 ppm) was to consider a different structure for m/z 197, as depicted in Scheme 4. This structure implies deprotonation has occurred on the MAA monomer linked to the initiating group; then, after a first dehydration step has occurred, a decarboxylation reaction would have proceeded in a direct mechanism.…”

Section: Tandem Mass Spectrometry Of Singly Charged Oligomersmentioning

confidence: 99%

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Tandem mass spectrometry of poly(methacrylic acid) oligomers produced by negative mode electrospray ionization

Giordanengo

Viel

Allard-Breton

et al. 2009

J. Am. Soc. Mass Spectrom.

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Dissociation of small poly(methyl acrylic acid) (PMAA) anions produced by electrospray was characterized by tandem mass spectrometry. Upon collisional activation, singly, and doubly deprotonated PMAA oligomers were shown to fragment via two major reactions, dehydration and decarboxylation. The elimination of a water molecule would occur between two consecutive acid groups in a charged-remote mechanism, giving rise to cyclic anhydrides, and was shown to proceed as many times as pairs of neutral pendant groups were available. As a result, the number of dehydration steps, together with the abundance of the fragment ions produced after the release of all water molecules, revealed the polymerization degree of the molecule in the particular case of doubly charged oligomers. For singly deprotonated molecules, the exact number of MAA units could be reached from the number of carbon dioxide molecules successively eliminated from the fully dehydrated precursor ions. In contrast to dehydration, decarboxylation reactions would proceed via a charge-induced mechanism. The proposed dissociation mechanisms are consistent with results commonly reported in thermal degradation studies of poly(acrylic acid) resins and were supported by accurate mass measurements. These fragmentation rules were successfully applied to characterize a polymeric impurity detected in the tested PMAA sample. (J Am Soc Mass

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Section: Tandem Mass Spectrometry Of Singly Charged Oligomersmentioning

confidence: 61%

Section: Tandem Mass Spectrometry Of Singly Charged Oligomersmentioning

confidence: 96%

Section: Tandem Mass Spectrometry Of Singly Charged Oligomersmentioning

confidence: 99%

See 1 more Smart Citation

Tandem mass spectrometry of poly(methacrylic acid) oligomers produced by negative mode electrospray ionization

Giordanengo

Viel

Allard-Breton

et al. 2009

J. Am. Soc. Mass Spectrom.

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“…The last stage during the pyrolysis of PAA/D probably was associated with the release of acrylic acid (depolymerisation), decomposition of polymer chains (poly(acrylic acid), dextrin), or oxidation process of the partially decomposed matter in a wide temperature range, from 400 to 600°C. Above 400°C in nitrogen atmosphere, a carbonaceous residue was generated (a residual mass of 35.3%) [13,21,22].…”

Section: Resultsmentioning

confidence: 99%

“…The gasses which are adsorbed by the activated carbon of the measuring and control layers, after any carbon disulphide (CS 2 ) has been extracted, are subjected to analysis by gas chromatography (GC) using a flame ionisation detector (FID). In this study, an analysis of the thermal degradation process of polymer binders in the form of a composition of PAA/D was conducted, based on the literature regarding the degradation of polyacrylic acid polymers and polysaccharides, as well as on the results of the authors' own research (TG-DSC, TG-MS, TG-IR) [3,[17][18][19][20][21]. To determine the values of degradation temperatures and the thermal effects which took place during heating of composition samples, TG and DSC thermal analysis (TA) methods were used.…”

Section: Introductionmentioning

confidence: 99%

Thermal analysis in foundry technology

Grabowska

Hodor²,

Kaczmarska

et al. 2017

J Therm Anal Calorim

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In this study, a polymer composition of poly (acrylic acid) and dextrin (PAA/D) cross-linked with microwave radiation, belonging to the new BioCo group of environmentally friendly foundry binders, was subjected to thermal analysis (TG-DTG-DSC, TG-MS, TG-IR) in a temperature range of 20-600°C. A thermal analysis of PAA/D compositions enables the determination of a temperature range at which the composition is not susceptible to thermal degradation and thus does not lose its binding properties. The study showed that the process of thermal degradation of PAA/D is complex and multi-stage (TG-DTG-DSC). Within a temperature range of 20-250°C, physical and chemical changes take place associated with the evaporation of the water fraction of the solvent (20-100°C), next with the evaporation of the water hydration and finally with intermolecular dehydration reactions (100-250°C). Above a temperature of 300°C, the decomposition of the polymer chains takes places, and thereafter, the intensive degradation of PAA/D occurs together the creation of gaseous substances, primarily low molecular weight inorganic (CO 2 , H 2 O, CO) and organic compounds, including methane (TG-IR, TG-MS).

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Synthesis, characterization and thermal degradation of poly[2-(3-p-bromophenyl-3-methylcyclobutyl)-2-hydroxyethylmethacrylate]

Demirelli

Çoşkun

1999

Polym. Int.

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In this work, 2‐(3‐p‐bromophenyl‐3‐methylcyclobutyl)‐2‐hydroxyethylmethacrylate (BPHEMA) [monomer] was synthesized by the addition of methacrylic acid to 1‐epoxyethyl‐3‐bromophenyl‐3‐methyl cyclobutane. The monomer and poly(BPHEMA) were characterized by FT‐IR and [1H] and [13C]NMR. Average molecular weight, glass transition temperature, solubility parameter, and density of the polymer were also determined. Thermal degradation of poly[BPHEMA] was studied by thermogravimetry (TG), FT‐IR. Programmed heating was carried out at 10 °C min−1 from room temperature to 500 °C. The partially degraded polymer was examined by FT‐IR spectroscopy. The degradation products were identified by using FT‐IR, [1H] and [13C]NMR and GC‐MS techniques. Depolymerization is the main reaction in thermal degradation of the polymer up to about 300 °C. Percentage of the monomer in CRF (Cold Ring Fraction) was estimated at 33% in the peak area of the GC curve. Intramolecular cyclization and cyclic anhydride type structures were observed at temperatures above 300 °C. The liquid products of the degradation, formation of anhydride ring structures and mechanism of degradation are discussed. © 1999 Society of Chemical Industry

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Thermal stability and degradation mechanisms of poly(acrylic acid) and its salts: Part 1—Poly(acrylic acid)

Cited by 173 publications

References 15 publications

Tandem mass spectrometry of poly(methacrylic acid) oligomers produced by negative mode electrospray ionization

Tandem mass spectrometry of poly(methacrylic acid) oligomers produced by negative mode electrospray ionization

Thermal analysis in foundry technology

Synthesis, characterization and thermal degradation of poly[2-(3-p-bromophenyl-3-methylcyclobutyl)-2-hydroxyethylmethacrylate]

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