Synthesis and oxidative stability of phenolic antioxidants immobilized by cellulose nanocrystals

Weigl, Sabrina; Bretterbauer, Klaus; Schöfberger, Wolfgang; Paulik, Christian

doi:10.1016/j.polymdegradstab.2016.03.022

Cited by 7 publications

(3 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The here-attained OIT values point out that these natural phenolic compounds are very promising additives to improve the oxidative thermal degradation of bio-HDPE. Similar results have been reported for α-tocopherol, which was also compared in terms of thermal protection with synthetic antioxidants such as butylated hydroxytoluene (BHT) [ 77 ]. Similarly, the work of Li et al [ 78 ] showed that the incorporation of 0.1 wt% of dendritic antioxidant delayed the OIT of PP and LDPE at 200 °C by approximately 40 and 50 min, respectively.…”

Section: Resultssupporting

confidence: 65%

On the Use of Phenolic Compounds Present in Citrus Fruits and Grapes as Natural Antioxidants for Thermo-Compressed Bio-Based High-Density Polyethylene Films

et al. 2020

View full text Add to dashboard Cite

This study originally explores the use of naringin (NAR), gallic acid (GA), caffeic acid (CA), and quercetin (QUER) as natural antioxidants for bio-based high-density polyethylene (bio-HDPE). These phenolic compounds are present in various citrus fruits and grapes and can remain in their leaves, peels, pulp, and seeds as by-products or wastes after juice processing. Each natural additive was first melt-mixed at 0.8 parts per hundred resin (phr) of bio-HDPE by extrusion and the resultant pellets were shaped into films by thermo-compression. Although all the phenolic compounds colored the bio-HDPE films, their contact transparency was still preserved. The chemical analyses confirmed the successful inclusion of the phenolic compounds in bio-HDPE, though their interaction with the green polyolefin matrix was low. The mechanical performance of the bio-HDPE films was nearly unaffected by the natural compounds, presenting in all cases a ductile behavior. Interestingly, the phenolic compounds successfully increased the thermo-oxidative stability of bio-HDPE, yielding GA and QUER the highest performance. In particular, using these phenolic compounds, the onset oxidation temperature (OOT) value was improved by 43 and 41.5 °C, respectively. Similarly, the oxidation induction time (OIT) value, determined in isothermal conditions at 210 °C, increased from 4.5 min to approximately 109 and 138 min. Furthermore, the onset degradation temperature in air of bio-HDPE, measured for the 5% of mass loss (T5%), was improved by up to 21 °C after the addition of NAR. Moreover, the GA- and CA-containing bio-HDPE films showed a high antioxidant activity in alcoholic solution due to their favored release capacity, which opens up novel opportunities in active food packaging. The improved antioxidant performance of these phenolic compounds was ascribed to the multiple presence of hydroxyl groups and aromatic heterocyclic rings that provide these molecules with the features to permit the delocalization and the scavenging of free radicals. Therefore, the here-tested phenolic compounds, in particular QUER, can represent a sustainable and cost-effective alternative of synthetic antioxidants in polymer and biopolymer formulations, for which safety and environmental issues have been raised over time.

show abstract

Section: Resultssupporting

confidence: 65%

On the Use of Phenolic Compounds Present in Citrus Fruits and Grapes as Natural Antioxidants for Thermo-Compressed Bio-Based High-Density Polyethylene Films

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Xie et al 22 prepared a macromolecular antioxidant (β‐CD‐DBHMP) by the reaction of phenolic antioxidant and β‐cyclodextrin and found that β‐CD‐DBHMP possessed superior extraction resistance and could markedly improve the thermo‐oxidative resistance of rubber. Weigl et al 23 prepared a novel macromolecular antioxidant (CNC‐AO + C18) by grafting phenolic antioxidants onto cellulose nanocrystals and then reacting with octadecylamine. Compared with the commercially available antioxidants 264, antioxidant CNC‐AO + C18 exhibited better anti‐aging effects.…”

Section: Introductionmentioning

confidence: 99%

Fabrication of a novel chitosan‐based macromolecular antioxidant and its effects on the anti‐aging properties of styrene‐butadiene rubber/silica composites

Pan

Xie

et al. 2023

Vinyl Additive Technology

View full text Add to dashboard Cite

In this work, a novel chitosan‐based macromolecular rubber antioxidant (denoted as COS‐AO) was successfully synthesized by using chitosan (COS) and 3‐(3,5‐di‐tert‐butyl4‐hydroxyphenyl) propionic acid (antioxidant, AO) via esterification reaction. The FTIR, 1H NMR, 13C NMR, and elemental analysis measurements were used to confirm the structure of COS‐AO. The performance of COS‐AO as a macromolecular antioxidant for styrene‐butadiene rubber (SBR)/silica composites were examined by oxidation induction time (OIT) test, methanol extraction experiments, accelerated thermo‐oxidative aging tests as well as thermogravimetric (TG) test. The results indicated that the macromolecular antioxidant COS‐AO presented better extraction resistance and migration resistance in SBR/silica composites compared to the small molecular antioxidant AO. Moreover, COS‐AO significantly improved the thermal stability as well as the value of the oxidation induction time of SBR/silica composites, exhibiting superior thermo‐oxidative aging resistance. In addition, the potential antioxidative mechanism of COS‐AO in SBR/silica composites was also discussed.

show abstract

“…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. The results confirmed that the thermal aging resistance of the NR-graft-antioxidant in rubber was better than that of the commercial antioxidant with low molecular weight.…”

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

View full text Add to dashboard Cite

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.

show abstract

Synthesis and oxidative stability of phenolic antioxidants immobilized by cellulose nanocrystals

Cited by 7 publications

References 25 publications

On the Use of Phenolic Compounds Present in Citrus Fruits and Grapes as Natural Antioxidants for Thermo-Compressed Bio-Based High-Density Polyethylene Films

On the Use of Phenolic Compounds Present in Citrus Fruits and Grapes as Natural Antioxidants for Thermo-Compressed Bio-Based High-Density Polyethylene Films

Fabrication of a novel chitosan‐based macromolecular antioxidant and its effects on the anti‐aging properties of styrene‐butadiene rubber/silica composites

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

Contact Info

Product

Resources

About