2‐Mercapto thioxanthone as a chain transfer agent in free‐radical polymerization: A versatile route to incorporate thioxanthone moieties into polymer chain‐ends

Karasu, Feyza; Arsu, Nergis; Yaǧcı, Yusuf

doi:10.1002/app.25467

Cited by 33 publications

(29 citation statements)

References 22 publications

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“…This compound is thermally stable and does not initiate itself in the absence of AIBN. The addition of a millimolar concentration of this compound to the polymerization of both styrene and MMA decreased the molecular weight of the polymer formed [8].…”

Section: Thiolmentioning

confidence: 97%

“…ME (structure: HS-CH 2 CH 2 OH) at the indicated concentrations acted as an inhibitor due to H abstraction from the -SH group in the ME molecule by free radicals (Figure 2). The weakness of the S-H bond and the high reactivity of the thiyl radical (RS*) are the two crucial parameters for a chain transfer agent [7,8]. Nucleophilic thiyl radicals are expected to be more reactive toward the α,β-unsaturated carbonyl group in the MMA molecule because of their higher electrophilicity.…”

Section: Thiolmentioning

confidence: 99%

“…Quantitative inhibition of auto-oxidation by various synthetic and natural phenols and organic sulfur compounds has been investigated by many researchers [1][2][3][4][5][6][7][8][9]. Burton and Ingold studied the radical-scavenging activity of various phenolic compounds using the induction period method in a chlorobenzene-styrene system initiated by AIBN, and found that phenolic compounds act as potent chain-breaking antioxidants [1].…”

Section: Introductionmentioning

confidence: 99%

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Radical-Scavenging Activity of Thiols, Thiobarbituric Acid Derivatives and Phenolic Antioxidants Determined Using the Induction Period Method for Radical Polymerization of Methyl Methacrylate

Kadoma

Fujisawa

2012

Polymers

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Abstract:The radical-scavenging activities of two thiols, eight (thio)barbituric acid derivatives and six chain-breaking phenolic antioxidants were investigated using the induction period method for polymerization of methyl methacrylate (MMA) initiated by thermal decomposition of 2,2'-azobisisobutyronitrile (AIBN) and monitored by differential scanning calorimetry (DSC). The induction period (IP) for the thiols 2-mercaptoethanol (ME) and 2-mercapto-1-methylimidazole (MMI) was about half that for phenolic antioxidants. Except for the potent inhibitor 5,5-dimethyl-2-thiobarbituric acid (3), the IP for thiobarbituric acid derivatives was about one tenth of that for phenolic antioxidants. The IP for 1,3,5-trimethyl-2-thiobarbituric acid (1) and 5-allyl-1, 3-dimethyl-2-thiobarbituric acid (7) was less than that of the control, possibly due to inhibition by a small amount of atmospheric oxygen in the DSC container. The ratio of the chain inhibition to that of chain propagation (CI/CP) for the thiols and thiobarbituric acid compounds except for 1, 3 and 7 was about 10 times greater or greater than that for phenolic compounds. A kinetic chain length (KCL) about 10% greater than that of the control was observed for 1, suggesting that 1 had chain transfer reactivity in the polymerization of MMA. The average molecular weight of polymers formed from thiobarbituric acid derivatives is discussed. OPEN ACCESSPolymers 2012, 4 1026

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Section: Thiolmentioning

confidence: 97%

Section: Thiolmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Radical-Scavenging Activity of Thiols, Thiobarbituric Acid Derivatives and Phenolic Antioxidants Determined Using the Induction Period Method for Radical Polymerization of Methyl Methacrylate

Kadoma

Fujisawa

2012

Polymers

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“…Thiols and sulphides perform important biological functions, especially in life processes. There are also known other applications of thiols, e.g., as chain transfer agents in the synthesis of polymers used for optical devices [1][2][3][4].…”

Section: Introductionmentioning

confidence: 99%

“…The chemical structure of PSM was confirmed by the ATR-FTIR, GC-MS, 1 H and 13 C NMR spectroscopy. Next bulk copolymerization of PSM with styrene (St) and methyl methacrylate (MMA) was performed.…”

Section: Introductionmentioning

confidence: 99%

Thermal and spectral analysis of copolymers with sulphur groups

Fila

Grochowicz

Podkościelna

2017

J Therm Anal Calorim

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The paper presents the synthesis, structure and polymerization of S-phenyl 2-methylprop-2-enethioate (PSM). This compound was prepared in the reaction of thiophenol with methacryloyl chloride. The obtained PSM was purified on the chromatographic column. Chemical structure of the monomer was confirmed by spectroscopic methods (ATR-FTIR, GC-MS, 1 H and 13 C NMR). Next bulk polymerization of PSM with styrene (St) or methyl methacrylate (MMA) was performed. In this way, linear copolymers were obtained. The number and mass average molar mass of the obtained copolymers were determined by gel permeation chromatography (GPC). Additionally, crosslinked copolymers of the commercial monomer S,S 0 -thiodi-4,1-phenylene bis(thiomethacrylate) (DMSPS) under the same conditions were synthesized. The influence of thiol monomers on the physico-chemical properties of the obtained copolymers was determined. Thermal properties of the synthesized materials were investigated by means of DSC and TG/DTG.

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Synthesis and characterization of polyacrylate composite with thiol‐modified nanosilica as chain transfer agent

Wu¹,

Li²,

Ma³

et al. 2015

J of Applied Polymer Sci

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Polyacrylate composites with thiol-modified nanosilica as chain transfer agent were prepared. The FTIR results indicated that the chemical bond has formed between polyacrylate and modified nanosilica. The change of molecular weight distribution proved that the thiol group on the nanosilica surface played the chain transfer agent role just as common thiol. A possible mechanism of modified nanosilica in the polymerization was proposed and the core-shell may be formed finally. In addition, the dispersion of nanosilica in the polyacrylate also improved as a result of the organic bridge structure between the nanosilica and polyacrylate. The thermal decomposition temperature increased as much as 108C for polyacrylate with 10 wt % modified nanosilica composites compared to polyacrylate. The coatings hardness increased from 2 to 6 H and the abrasion resistance improved from 28 to 10 mg under the same conditions. Especially, the gloss change of coatings with different content of modified nanosilica indicated that the polyacrylate composites have obviously better aging resistance performance compared to polyacrylate. It may be ascribed to the property that nanosilica can absorb large UV light.

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2‐Mercapto thioxanthone as a chain transfer agent in free‐radical polymerization: A versatile route to incorporate thioxanthone moieties into polymer chain‐ends

Cited by 33 publications

References 22 publications

Radical-Scavenging Activity of Thiols, Thiobarbituric Acid Derivatives and Phenolic Antioxidants Determined Using the Induction Period Method for Radical Polymerization of Methyl Methacrylate

Radical-Scavenging Activity of Thiols, Thiobarbituric Acid Derivatives and Phenolic Antioxidants Determined Using the Induction Period Method for Radical Polymerization of Methyl Methacrylate

Thermal and spectral analysis of copolymers with sulphur groups

Synthesis and characterization of polyacrylate composite with thiol‐modified nanosilica as chain transfer agent

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