Antioxidative activity of 3-aryl-benzofuran-2-one stabilizers (Irganox®HP-136) in polypropylene

Marin, Alexander; Greci, Lucedio; Dubs, Paul

doi:10.1016/s0141-3910(02)00053-8

Cited by 20 publications

(17 citation statements)

References 5 publications

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“…Its stabilization has taken a long time for solving by various kinds of antioxidants (stabilizers). [1][2][3][4][5][6][7] From the view point of the various principles of degradation processes antioxidants are divided into a few series such as scavengers of free radicals, hydroperoxide decompositors, metal deactivators, antiozonants, photoantioxidants, photostabilizers and heat stabilizers. 8,9 Generally, free radical character of degradation is considered for very frequent mode.…”

Section: Introductionmentioning

confidence: 99%

Radical scavenging capacity of lignin and its effect on processing stabilization of virgin and recycled polypropylene

Gregorová

Košíková

Staško

2007

J of Applied Polymer Sci

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ABSTRACT:The radical scavenging capacity of lignin was determined using spectrophotometric method by means of scavenging of the free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH ) and compared with that of synthetic antioxidant Irganox 1010. Lignin reacted progressively with the DPPH reaching a steady state in 6 h, showing high antiradical activity with a stochiometry of 5.5 reduced DPPH molecules. Irganox 1010 showed lower antiradical activity reaching a steady state with DPPH after 13 h. Moreover, stabilization efficiency of lignin has been investigated in virgin and recycled polypropylene. The stabilization effect of lignin was evaluated by melt volume rate (MVR). The efficiency of lignin as processing stabilizer in both series polypropylene samples was compared with that of synthetic antioxidant Irganox 1010. The presence and behavior of free radicals in the lignin/polypropylene composites formed during processing was determined by electron paramagnetic resonance (EPR). It was observed that used lignin sample could stabilise both virgin and recycled polypropylene.

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Section: Introductionmentioning

confidence: 99%

Radical scavenging capacity of lignin and its effect on processing stabilization of virgin and recycled polypropylene

Gregorová

Košíková

Staško

2007

J of Applied Polymer Sci

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“…In reality, in 3‐ary‐3H‐benzofuranone derivatives, the free electron of radical A formed because of the hydrogen donation of hydrogen in the three‐position can delocalize in two benzene rings (the process is shown in Scheme ), so the hydrogens in the three‐position are very reactive and can react with carbon‐centered radicals and oxygen‐centered radicals (including phenol radicals) easily . As a result, benzofuranone derivatives are used with conventional binary antioxidants together to increase the stability of PP in the repeated melt processing, especially at the higher temperature . Unfortunately, until now, 3‐aryl‐benzofuranone had not been widely commercially available as a stand‐alone product, and there was no report on the degradation and the changes of mechanical properties of PP stabilized with benzofuranone derivatives alone.…”

Section: Introductionmentioning

confidence: 99%

Effect of benzofuranone on degradation and mechanical properties of polypropylene in processing

Meng

Chen

Xin

et al. 2016

Vinyl Additive Technology

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Melt flow index, polydistribution index, Fourier‐transform infrared spectroscopy, and differential scanning calorimetry have been used for the assessment of the degradation of virgin polypropylene (PP) and PP stabilized with benzofuranone derivatives. When PP samples were subjected to five extrusion cycles, the melt flow index and polydistribution index values of virgin PP sharply increased with the number of extrusion cycles, but the corresponding changes of PP stabilized with benzofuranone derivatives were not as great as those of virgin PP. Furthermore, the results of Fourier‐transform infrared spectroscopy and differential scanning calorimetry showed that benzofuranone prevented the increasing of double bonds and the moving of crystal peak temperature to the higher temperature. All those changes indicate that the degradation of PP is inhibited efficiently by benzofuranone derivatives, and the stabilization with benzofuranone derivative in PP is beneficial to the maintenance of mechanical properties of PP. J. VINYL ADDIT. TECHNOL., 24:124–129, 2018. © 2016 Society of Plastics Engineers

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“…5,7‐Di‐ tert ‐butyl‐3‐(3′,4′‐dimethylphenyl)3 H ‐benzofuran‐2‐one (Irganox HP‐136), a representative of 3‐arylbenzofuranone analogs, has attracted the special attention of biochemists and industrial chemists because of its harmlessness to organic materials and its strong ability to scavenge oxygen and carbon‐centered radicals . Antioxidant systems which consist of phenol, phosphate, and HP‐136 have been used to increase the stability of hydrocarbon polymers in melt processing at high temperatures in recent years . Examination of the structure of HP‐136 reveals that the 3‐position is a good hydrogen donor site and that a substituent in the 2′‐position can prevent attack of the 3‐position reactive hydrogen by radicals, thus lowering the rate constant for the reaction of radicals with the benzofuranone .…”

Section: Introductionmentioning

confidence: 99%

Antioxidant mechanism of a 3-arylbenzofuranone containing a 2′-hydroxyl group

Meng

Qiu

Xin

2013

J Vinyl Addit Technol

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5‐Methyl‐7‐tert‐butyl‐3‐(2′hydroxyl‐5′‐methylphenyl)3H‐benzofuran‐2‐one (PCRBF2), is a better scavenger of 2,2‐diphenyl‐1‐picrylhydrazyl radicals than benzofuranone analogs without the 2′‐substituent, which indicates that PCRBF2 will cause good stabilization in polymers. To prove this further, antioxidation by PCRBF2 and other benzofuranone analogs, namely, 5‐methyl‐7‐tert‐butyl‐3‐(3′,4′‐dimethylphenyl)3H‐benzofuran‐2‐one (OXBF2) and 5‐methyl‐7‐tert‐butyl‐3‐(2′,5′‐dimethylphenyl)3H‐benzofuran‐2‐one (PXBF2), was comparatively studied in polypropylene. The resulting antioxidant activity order of these benzofuranones was PCRBF2 > OXBF2 > PXBF2, an observation showing that the hydroxyl group in the 2′‐position does not weaken the antioxidant activity of benzofuranone, but, on the contrary, increases it. Analyses by FTIR revealed intramolecular hydrogen bonding between the 3‐position hydrogen and the oxygen of the 2′‐hydroxyl group, which makes the 2′‐hydroxyl hydrogen of PCRBF2 more reactive than the 3‐position reactive hydrogen. Thus the hydroxyl group reacts with radicals first. J. VINYL ADDIT. TECHNOL., 19:198‐202, 2013. © 2013 Society of Plastics Engineers

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Antioxidative activity of 3-aryl-benzofuran-2-one stabilizers (Irganox®HP-136) in polypropylene

Cited by 20 publications

References 5 publications

Radical scavenging capacity of lignin and its effect on processing stabilization of virgin and recycled polypropylene

Radical scavenging capacity of lignin and its effect on processing stabilization of virgin and recycled polypropylene

Effect of benzofuranone on degradation and mechanical properties of polypropylene in processing

Antioxidant mechanism of a 3-arylbenzofuranone containing a 2′-hydroxyl group

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