Sulfur Compounds as Antioxidants

Thompson, Robert B.; Chenicek, J. A.; Symon, Ted

doi:10.1021/ie50511a048

Cited by 14 publications

(9 citation statements)

References 3 publications

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“…It was hypothesized that the thiocarbonyl functionality in RAFT agent hinders the autoxidative curing reactions. While several studies have focused on antioxidant activity of sulfur compounds, a comprehensive mechanistic study has not been reported thus far …”

Section: Discussionmentioning

confidence: 99%

“…While several studies have focused on antioxidant activity of sulfur compounds, a comprehensive mechanistic study has not been reported thus far. [32][33][34][35][36][37] Generally, antioxidant activity of sulfur-based compounds is explained by the oxidation of sulfur to give a sulfoxide in the initial reaction steps. [38] Sulfoxides are considered to be the most effective antioxidants due to the formation of active radical scavenger sulfenic acid.…”

Section: Discussionmentioning

confidence: 99%

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Acrylated Alkyds Synthesized via Quasi‐Living Radical Polymerization: ATRP and RAFT

Nalawade

Soucek

2017

Macro Chemistry & Physics

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A new method for the synthesis of autoxidatively curable acrylated alkyds is demonstrated. Acrylic block is grafted onto the backbone of the alkyd chain via atom transfer radical polymerization (ATRP) polymerization. The acrylated ATRP copolymers are compared to RAFT copolymer and both are characterized using quantitative 1H NMR, 13C NMR, and 2D‐NMR spectroscopy. In particular, the autoxidative curing of ATRP polymerized acrylated alkyd is compared to the RAFT polymerized acrylated alkyds using Fourier transform infrared spectroscopy (FTIR) spectroscopy. The analysis finds that the autoxidation of the RAFT acrylated alkyds is inhibited. It is postulated that the thiocarbonyl functionality hinders the autoxidative reactions. The performance of autoxidatively cured ATRP polymerized acrylated alkyd coatings is evaluated using tensile, viscoelastic, and general coating properties. Alkyd‐acrylic copolymer coatings show improved hardness, glass transition temperature, and drying time. General coating properties such as cross‐hatch adhesion, methyl ethyl ketone (MEK) resistance, and impact resistance are maintained except at higher acrylic concentrations.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Acrylated Alkyds Synthesized via Quasi‐Living Radical Polymerization: ATRP and RAFT

Nalawade

Soucek

2017

Macro Chemistry & Physics

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“…Among the substituted quinonic compounds, we synthesized compounds 9 [ 6 [ 10 [ 13 [ 12, especially the S,Ssubstituted naphthoquinones exhibited the highest antioxidant activity through the polymethylene side chains possibly contributing to enol formation. Besides, cyclic Ar-S-CH 2 -R compounds may also exhibit antioxidant activity, though to a significantly less extent than Ar-SH and R-SH thiols [26].…”

Section: Antioxidant Capacity Of Synthesized Compoundsmentioning

confidence: 99%

One-pot synthesis, characterization, and antioxidant capacity of sulfur- and oxygen-substituted 1,4-naphthoquinones and a structural study

et al. 2015

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In the present study, we reported the onepot synthesis of S,S-and S,O-substituted 1,4-naphthoquinones, their structural studies, and investigation of their antioxidant activity. The multicomponent reactions of 2,3-dichloro-1,4-naphthoquinone with sulfur-and oxygencontaining nucleophiles were investigated to obtain highly functionalized S,S-and S,O-substituted 1,4-naphthoquinone derivatives. All new compounds were characterized on the basis of 1 H, 19 F, and 13 C nuclear magnetic resonance spectroscopy, mass spectrometry, and Fourier transform infrared spectroscopy. Crystal structure of 2,3-dihydro-2-(hydroxymethyl)naphtho[2,3-b]-1,4-oxathiin-5,10-dione was determined by X-ray diffraction method. The synthesized compounds were screened for their antioxidant capacity and free radical scavenging activity using the cupric reducing antioxidant capacity method and DPPH method, respectively. 3-Chloro-2-[3-(3-chloro-1,4-dihydro-1,4-dioxonaphthalen-2-yloxy)propylsulfanyl]-1,4-naphthoquinone shows the highest antioxidant capacity with 0.63 cupric reducing antioxidant capacity-trolox equivalent antioxidant capacity coefficient. Graphical abstract

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“…To account for certain anomalous results in the experimental phenomena observed in hydrocarbon flames, it has been postulated that formation of highly unsaturated chain polymers occurs and is followed by subsequent rapid breakdown to active fragments and the oxidation of these fragments (176). Among the anomalies explained are the data on carbon formation, the differences between premixed and diffusion flames, and the abnormal spectroscopic temperatures in the reaction zone of certain free radicals.…”

Section: Flame Velocitiesmentioning

confidence: 99%