Melt grafting of maleimides having hindered phenol antioxidant onto low molecular weight polyethylene

Kim, Taek Hyeon; Oh, Dong Ryun

doi:10.1016/j.polymdegradstab.2004.01.008

Cited by 57 publications

(11 citation statements)

References 8 publications

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“…Only a few researchers propose the method of increasing the volume of hindered phenols to improve dispersion stability. For example, by constructing bulk-like structures, such as grafting hindered phenol to polymer chains [38,39] or to the surface of inorganic nanoparticles [40] and by synthesizing hyperbranched hindered phenol molecules [41], the intramolecular HBs are remarkably weakened. Thus, the self-aggregation and crystallization are successfully restricted.…”

Section: Introductionmentioning

confidence: 99%

Towards a Stable and High-Performance Hindered Phenol/Polymer-Based Damping Material Through Structure Optimization and Damping Mechanism Revelation

Wang

et al. 2019

Polymers

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Although hindered phenol/polymer-based hybrid damping materials, with excellent damping performance, attract more and more attention, the poor stability of hindered phenol limits the application of such promising materials. To solve this problem, a linear hindered phenol with amorphous state and low polarity was synthesized and related polyurethane-based hybrid materials were prepared in this study. The structure and state of the hindered phenol were confirmed by nuclear magnetic resonance spectrum, Fourier transform infrared spectroscopy (FT-IR) and X-ray diffraction (XRD). The existence of intermolecular hydrogen bonds (HBs) between hindered phenol and polyurethane was confirmed by FT-IR, and the amorphous state of the hybrids was confirmed by XRD. Moreover, by a combination of molecular dynamics simulation and dynamic mechanical analysis, the relationship between the structure optimization of the hindered phenol and the high damping performance of the hybrids was quantitatively revealed. By constructing the synthetic hindered phenol, the intramolecular HBs between hindered phenols were restricted, while the strength and concentration of the intermolecular HBs increased by increasing the amount of hindered phenol. Thus, intermolecular interactions were enhanced, which lead to the compact chain packing of polyurethane, extended chain packing of hindered phenol, and good dispersion of hindered phenol in polyurethane. Therefore, the stability of the hindered phenol and the damping properties of the hybrids were both improved. The experiment results are expected to provide some useful information for the design and fabrication of high-performance polymeric damping materials.

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Section: Introductionmentioning

confidence: 99%

Towards a Stable and High-Performance Hindered Phenol/Polymer-Based Damping Material Through Structure Optimization and Damping Mechanism Revelation

Wang

et al. 2019

Polymers

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“…Two general methods to synthesize these larger antioxidant polymers have been reported: chemical modification of pre-formed polymers, or polymerization of antioxidant monomers. The first approach involves the post-functionalization of reactive groups of natural (Arefjev et al, 1999 ; Sousa et al, 2009 ) or synthetic (Kim and Oh, 2004 ) polymer chains with sterically hindered phenol groups (SHP) with the aim to improve their antioxidant activity. This method is quite efficient and easily accessible, but may trigger undesirable side reactions, especially regarding the difficulty to obtain full distribution of stabilizers at the reactive sites of the matrix.…”

Section: Introductionmentioning

confidence: 99%

Biocatalytic Synthesis and Polymerization via ROMP of New Biobased Phenolic Monomers: A Greener Process toward Sustainable Antioxidant Polymers

et al. 2017

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Antioxidant norbornene-based monomers bearing biobased sterically hindered phenols (SHP)—NDF (norbornene dihydroferulate) and NDS (norbornene dihydrosinapate)—have been successfully prepared through biocatalysis from naturally occurring ferulic and sinapic acids, respectively, in presence of Candida antarctica Lipase B (Cal-B). The ring opening metathesis polymerization (ROMP) of these monomers was investigated according to ruthenium catalyst type (GI) vs. (HGII) and monomer to catalyst molar ratio ([M]/[C]). The co-polymerization of antioxidant functionalized monomer (NDF or NDS) and non-active norbornene (N) has also been performed in order to adjust the number of SHP groups present per weight unit and tune the antioxidant activity of the copolymers. The polydispersity of the resulting copolymers was readily improved by a simple acetone wash to provide antioxidant polymers with well-defined structures. After hydrogenation with p-toluenesulfonylhydrazine (p-TSH), the radical scavenging ability of the resulting saturated polymers was evaluated using α,α-diphenyl-β-picrylhydrazyl (DPPH) analysis. Results demonstrated that polymers bearing sinapic acid SHP exhibited higher antiradical activity than the polymer bearing ferulic acid SHP. In addition it was also shown that only a small SHP content was needed in the copolymers to exhibit a potent antioxidant activity.

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“…Another important method is grafting or binding antioxidants onto the polymer backbone to increase the molecular weight and the compatibility between antioxidant and polymer. The polymer backbone included polybutadiene, 23,24 polyolefin, 25,26 NR, 27,28 and others. 29 –34 For example, El-Wakil and Barakat studied the grafting of o-aminophenol 27 and 1, 2-phenylenediamine 28 onto NR.…”

Section: Introductionmentioning

confidence: 99%

Thermo-oxidative aging resistance and mechanism of a macromolecular hindered phenol antioxidant for natural rubber

Yang

et al. 2017

Journal of Elastomers & Plastics

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Macromolecular antioxidant due to its low physical loss, high thermal stability, and good compatibility has been considered to be a promising candidate to inhibit polymer aging. In this study, thermo-oxidative aging resistance and antioxidative mechanism of a macromolecular hindered phenol antioxidant, namely, polyhydroxylated polybutadiene containing thioether binding 2, 2 0-thiobis (4-methyl-6-tert-butylphenol) (PHPBT-b-TPH) for natural rubber (NR) vulcanizate was studied in detail by oxidation induction time and accelerated thermal aging tests. The results showed that the antioxidative efficiency of PHPBT-b-TPH was very high. When the amount of PHPBT-b-TPH was only 1 phr, the NR vulcanizate could exhibit excellent thermo-oxidative aging resistance, obviously higher than that of NR vulcanizate with low-molecular-weight antioxidant TPH. After aged at 100 C for 168 h, the retentions of tensile strength and elongation at break of NR vulcanizate with PHPBT-b-TPH were 43.6% and 58.6%, respectively. However, those of NR vulcanizate with TPH were 35.6% and 54.5%. In addition, it was found that both thioether and urethane groups in PHPBT-b-TPH had antioxidative ability and had synergistic effect with hindered phenol. Through our findings, new strategy to design and synthesize the macromolecular antioxidant with multi-antioxidative groups for rubber materials and other polymer materials could be developed.

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Melt grafting of maleimides having hindered phenol antioxidant onto low molecular weight polyethylene

Cited by 57 publications

References 8 publications

Towards a Stable and High-Performance Hindered Phenol/Polymer-Based Damping Material Through Structure Optimization and Damping Mechanism Revelation

Towards a Stable and High-Performance Hindered Phenol/Polymer-Based Damping Material Through Structure Optimization and Damping Mechanism Revelation

Biocatalytic Synthesis and Polymerization via ROMP of New Biobased Phenolic Monomers: A Greener Process toward Sustainable Antioxidant Polymers

Thermo-oxidative aging resistance and mechanism of a macromolecular hindered phenol antioxidant for natural rubber

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