Synthesis of polymeric antioxidants based on ring-opening metathesis polymerization (ROMP) and their antioxidant ability for preventing polypropylene (PP) from thermal oxidation degradation

Xue, Boyong; Ogata, Kenichi; Toyota, Akinori

doi:10.1016/j.polymdegradstab.2007.12.001

Cited by 44 publications

(27 citation statements)

References 20 publications

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“…The potential antioxidant ability of bamboo could protect LDPE against thermal oxidation. Monitoring this behavior can be accomplished by OIT measurements, which have been previously performed 20 . In this case, the authors prepared polymeric antioxidants to protect polypropylene (PP) from degradation by thermal oxidation.…”

Section: Resultsmentioning

confidence: 99%

The potential of bamboo in the design of polymer composites

et al. 2012

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Bamboo is an alternative sustainable material for use in product design and has been incorporated into the concepts of eco-design. Here, we investigated the mechanical properties and morphologies of low density polyethylene (LDPE)/bamboo flour (BF) composites that were modified with polyethylene-graft-maleic anhydride (PE-g-MA) and glycerol. Scanning electron microscopy (SEM) and tensile tests of the composites demonstrated poor adhesion between the filler and matrix. Contact angle measurement showed that the surface of LDPE was modified by the presence of the load. The thermal stability of the composites was studied by measuring the oxidation induction time (OIT). Preliminary bacterial penetration tests were performed using culture inoculums of E. coli and S. aureus to investigate the natural antibacterial and bacteriostatic properties attributed to bamboo. Furthermore, bamboo may have interesting antioxidant activity with potential for use in food packaging applications.

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Section: Resultsmentioning

confidence: 99%

The potential of bamboo in the design of polymer composites

et al. 2012

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“…The organic layer was extracted by saturated naHCO 3 solution and dried over na 2 SO 4 followed by evaporation of extra solvent under reduced pressure. The chemical structures of synthesized antioxidants along with 13 C nMR spectra are shown in Figures 1 and 2 proved the potential antioxidant ability and revealed that polarity and hydrophobicity of stabilizers can be determining factors in efficiency of antioxidants. [18,19] Torres and coworkers [4,20] investigated the antioxidant ability of a new class of lipophilic phenolic-based stabilizers and their fatty acid esters.…”

Section: Synthesis Of Esters Of 35-di-tert-butyl-4-hydroxybenzoic Acmentioning

confidence: 87%

“…The structure of POE-g-gP and POE-g-gB were characterized with 13 C nMR in comparison to pure polymer, as shown in Figure 5. The peaks at 31.7 and 38.6 ppm were assigned to methine groups of POE according to literature.…”

Section: Radical Grafting Of Antioxidants Onto Polymermentioning

confidence: 99%

“…[1,2,9] There have been research efforts to develop supramolecular stabilizers with reduced mobility and volatility to improve the long-term stability of polymeric products, especially packaging films and pipes. [10][11][12] The reports generally categorized as two approaches: stabilizer immobilization and high molecular weight, olefin-based antioxidants [13] to provide homogeneous distribution in polymer. In 1991, Munteanu and Cunderlik reported the synthesis of three monomeric antioxidants bearing 3,5-di-tert-butyl-4-hydroxyphenyl as radical scavenging group and successful melt grafting onto polyethylene.…”

Section: Introductionmentioning

confidence: 99%

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Polyolefin elastomer grafted unsaturated hindered phenol esters: synthesis and antioxidant behavior

Manteghi

Ahmadi

Arabi

2016

Designed Monomers and Polymers

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Monomeric antioxidants are synthesized from esterification of 3,5-di-tert-butyl-4-hydroxybenzoic acid and 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with unsaturated fatty alcohols. The antioxidant activity is evaluated both in blending and radical grafting processes. The effect of chain length and phenolic group is investigated on efficiency of antioxidants. It is demonstrated that the esters of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid exhibit significantly longer induction time. The results of radical grafting reaction shows synthesized antioxidants can be successfully grafted onto polymer chains and the phenolic moiety is functional after extraction process, while pure and commercially stabilized samples are degraded instantaneously. Also, different initiator systems are utilized to enhance the extent of grafting. Among MEK, DCP, and DHBP peroxides, DHBP can be more effective in increasing the antioxidant grafted onto polymer. In addition, possibility of rising in graft content is investigated in presence of redox initiator. Using this approach, polymerbound antioxidant with prolonged thermal stability can be achieved.

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“…Among these, radical scavenging functional polymers have emerged as powerful tools that are suitable for polymeric stabilizers, self-stabilized materials, biomedical materials and packing materials [2][3][4][5][6]. Our interest in the development of radical scavenging polymer based on sterically hindered phenol (SHP) function-alized norbornene derivatives and ring-opening metathesis polymerization (ROMP) strategies had led us to recently communicate a series of polymers bearing SHP group in the side-chain and their performance in the scavenging of radicals.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Radical Scavenging Ability of 3,5-di-tert-Butyl-4-hydroxyphenoxy-Functionalized Polynorbornenes Synthesized Using Ring-Opening Metathesis Polymerization

Xue

Ogata

Toyota

2009

Designed Monomers and Polymers

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Novel norbornene derivatives bearing a 3,5-di-tert-butyl-4-hydroxyphenoxy (DBHO) group were synthesized and used as sterically hindered phenol functionalized norbornene monomers (1-4). The ring-opening metathesis polymerization (ROMP) of these functional monomers was carried out with a typical ruthenium catalyst (bis(tricyclohexylphosphine)benzylidene ruthenium (IV) dichloride, a Grubbs first-generation catalyst) to prepare sterically-hindered phenol-functionalized polymers possessing radical scavenging function. The resulting polymers bearing a DBHO side-chain were characterized by means of gel-permeation chromatography, 1 H-NMR and 13 C-NMR. The radical scavenging ability of polymers was determined using the α,α-diphenyl-β-picrylhydrazyl (DPPH·) free radical. Due to the electron-donating effect of the oxygen atom located in the para-position of phenol, the resulting polymers showed high efficiency to scavenge DPPH· free radical. The molecular weight of polymers was dependent on the molar ratio of monomer to catalyst ([M]/[C]), and the ROMP activity was dependent on the stereostructure of monomers themselves.

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Synthesis of polymeric antioxidants based on ring-opening metathesis polymerization (ROMP) and their antioxidant ability for preventing polypropylene (PP) from thermal oxidation degradation

Cited by 44 publications

References 20 publications

The potential of bamboo in the design of polymer composites

The potential of bamboo in the design of polymer composites

Polyolefin elastomer grafted unsaturated hindered phenol esters: synthesis and antioxidant behavior

Synthesis, Characterization and Radical Scavenging Ability of 3,5-di-tert-Butyl-4-hydroxyphenoxy-Functionalized Polynorbornenes Synthesized Using Ring-Opening Metathesis Polymerization

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