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Enzyme-catalyzed synthesis of 4-methylcatechol oligomer and preliminary evaluations as stabilizing agent in polypropylene

  • Yanpeng Wang , Fan Jiang and Lei Zhang EMAIL logo
Published/Copyright: February 15, 2023
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e-Polymers
From the journal e-Polymers Volume 23 Issue 1

Abstract

In the present work, 4-methylcatechol oligomer has been prepared by using enzyme-catalyzed polymerization in water and preliminary evaluations as stabilizing agent in polypropylene (PP) was performed. In comparison with intrinsic PP, the oxidation onset temperature of the 4-methylcatechol oligomer/PP composite increased by 66°C, and the oxidation induction time increased by 40 min. In addition, the mixing of a 4-methylcatechol oligomer with PP (i.e., in the formation of a 4-methylcatechol oligomer/PP composite) did significantly enhance the long-term stability of PP in a thermal oxidative environment. Moreover, the tensile strength of this composite did not significantly decrease after aging for 800 h in an air atmosphere at 120°C. These results show that the addition of a 4-methylcatechol oligomer will markedly delay the aging and degradation of PP materials, even under extreme conditions. Thus, an enzyme-catalyzed polymerization of phenol compounds may provide a new avenue toward the preparation of novel antioxidants.

Keywords: enzymatic polymerization; green synthesis; antioxidant; thermal oxidative stability; polypropylene

1 Introduction

Despite the increasing attention on biodegradable polymers, polyolefins are still the most commonly used polymer in the industry (1). Among these polyolefins, polypropylene (PP) shows excellent mechanical and processing properties and is widely used for pipes, packaging, home appliances, automobiles, etc. (2,3,4). However, PP materials are susceptible to undergo oxidization and degradation in thermal oxidative environments, which will result in a significant deterioration of their properties (5,6,7). The addition of antioxidants is an effective way to prevent the thermal oxidative degradation of PPs. Phenol compounds, especially hindered ones, are widely used as antioxidants in PP materials (8,9). Unfortunately, the phenol antioxidants with low molecular weight do easily migrate in the polymer and can even desorb from its surface, which not only affects the antioxidant effect but also pollutes the environment (10,11). Many methods have been used in the strive to develop both efficient and stable phenolic antioxidants, e.g., the grafting of small-molecule hindered phenolic antioxidants onto polymers (12,13,14) or functionalized materials (such as silicone materials (15,16,17), carbon nanotubes (18,19), graphene (20,21,22), and TiO2 nanorods (23)). However, the preparation of these antioxidants usually requires complicated steps, or harsh reaction conditions, which causes great obstacles for their practical applications.

In recent years, enzyme-catalyzed polymerization has become a research hotspot in the field of polymer synthesis. Compared with traditional polymerization methods, enzyme-catalyzed polymerization has the advantage of simple operation steps, high efficiency, mild reaction conditions, etc. (24,25,26). Also, the enzyme-catalyzed polymerization of phenolic compounds is a new facile method for the synthesis of phenol polymers (27,28). We have earlier found that the enzyme-catalyzed polymerization method usually produces phenol oligomer with improved thermal and antioxidant properties. The free radicals 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) can, thereby, be effectively removed (29,30). In addition, it has been found that 4-methoxyphenol oligomer will efficiently prevent the thermal oxidative degradation of PP (31). Thus, the enzymatic polymerization of small-molecule phenol compounds can be an efficient method for the synthesis of novel antioxidants with excellent performances.

Based on the above analysis, we have used in the present study 4-methylcatechol (a polyphenolic compound that is produced during the metabolism of quercetin) as a substrate for the preparation of a new phenolic oligomer by using enzyme-catalyzed polymerization. The efficiency of 4-methylcatechol oligomer in the stabilization of PP materials was then systemically investigated by analyzing the oxidation induction time (OIT) and oxidation onset temperature (OOT), and by performing accelerated aging tests. In addition, the antioxidant properties of the 4-methylcatechol oligomer were compared with the corresponding properties of 4-methylcatechol monomer, and of the commercially available butylated hydroxytoluene and n-octadecyl-β-(4-hydroxy-3,5-di-tert-butyl-phenyl)-propionate (1076) antioxidants.

2 Experiments

2.1 Materials and instruments

Horseradish peroxidase (HRP, activity = 200 IU‧mg−1) was purchased from Shanghai Guoyuan Biotechnology Co., Ltd. 4-Methylcatechol (99%) was purchased from Alfa Aesar. Irganox 1076 and butylated hydroxytoluene (BHT) were purchased from J&K Scientific Ltd. Virgin PP powder was kindly donated by PetroChina Dushanzi Petrochemical Company. All other reagents were of analytic grade and used as received without further purification.

Fluorescence spectrophotometer (F-7000, Hitachi, Japan), FTIR spectrometer (VERTEX 70, Bruker, Germany), electrospray ion trap mass spectrometry (AmaZon SL, Bruker, Germany), thermal gravimetric analyzer (TGA/SDTA851e, Mettler-Toledo Company, Switzerland), differential scanning calorimeter (DSC822e, Mettler-Toledo Company, Switzerland), and universal testing machine (WDW-20E, Jinan Heng shi sheng da Co., Ltd, China) were used.

2.2 Enzyme-catalyzed polymerization of 4-methylcatechol

At first, 0.62 g of 4-methylcatechol was dissolved in 50 mL of distilled water in a 100 mL round-bottomed flask. The mixture was electromagnetically stirred and kept at a constant temperature of 25°C. About 0.5 mg of HRP was, thereafter, added to the solution, followed by dropwise addition of 0.25 mL of a 5% H2O2 aqueous solution. This peroxide solution was added in total 14 times, with a time interval of 5 min. The resulting precipitate was, thereafter, collected by filtration and washed with water. It was dried in a vacuum oven at 60°C for 24 h, and the 4-methylcatechol polymerization product was finally obtained. The reaction scheme is shown in Figure 1.

Figure 1 Synthetic route of 4-methylcatechol oligomer.
Figure 1

Synthetic route of 4-methylcatechol oligomer.

2.3 TGA of 4-methylcatechol and 4-methylcatechol oligomer

Thermogravimetric analyses of 4-methylcatechol and 4-methylcatechol oligomer were performed on a TGA/SDTA851e in air atmosphere.

2.4 Preparation of PP and PP composites

An appropriate amount of PP powder was weighed and dried in an oven at 80°C for 10 h in the preparation of the 4-methylcatechol oligomer/PP composite. Then, 4-methylcatechol oligomer and PP powder were blended uniformly at a mass ratio of 1:200, followed by extrusion and pelletizing by using a twin screw extruder. The temperature gradient of the heating part of the extruder was set to 165–180°C, with the lowest temperature at the hopper end and the highest at the die end. The resulting granules were finally dried in an oven at 80°C for later use.

Furthermore, dumbbell-shaped specimens (width: 10.00 mm, gage length: 50 mm, and thickness: 4.00 mm) for tensile tests were prepared by injection, using a horizontal injection molding machine at 175°C.

2.5 Determination of OOT and OIT

The OOT is the temperature at which the DSC curve of the PP composite begins to turn sharply in the exothermic direction (after the occurrence of the melting peak) (32). This test was performed by using the DSC instrument at a heating rate of 10°C‧min−1 and with a flow rate of 50 cm3‧min−1 (in air).

Furthermore, the detection of OIT was carried out in accordance with international standards (ISO 11357-6:2008). At first, the PP composite was kept at 25°C for 5 min in a nitrogen flow of 50 cm3‧min−1. Second, the PP composite was heated to 190°C at a rate of 20°C‧min−1 and hold for 5 min in an unchanged nitrogen flow. Finally, the nitrogen flow was switched to a 50 mL‧min−1 oxygen flow. OIT is the time interval between the initiation of oxygen flow and the onset of the oxidative reaction (33).

2.6 Accelerated aging experiments of PP and PP composite materials

The PP sheets and the dumbbell-shaped PP sample strips were placed in an aging test box (at 120°C) for a specific time, and the infrared spectra of these samples were detected in an attenuated total reflection mode. In addition, a WDW-20E universal testing machine was used to test the tensile strength of the dumbbell-shaped PP sample strips (with a tensile rate of 50 mm‧min−1). The temperature was set to 21–25°C, and the relative humidity to 40–50%, in these tests. Five samples were tested for each group of samples, and the results were averaged in each group.

3 Results and discussion

3.1 Water-phase synthesis and structural analysis of 4-methylcatechol

The enzyme-catalyzed polymerization of phenolic compounds is usually carried out in a mixed medium of organic solvent and buffer (34,35). However, the addition of an organic solvent usually inhibits the catalytic activity of enzyme and causes problems such as a large amount of enzyme, long reaction times, and high costs. Moreover, the extensive use of an organic solvent does not meet the requirements of green chemistry. The enzyme-catalyzed polymerization of phenolic compound reaction can also be carried out smoothly by adding to surfactant (36) or another water-soluble organic compound (37). However, the additives made it difficult to purify the target product. Interestingly, we have recently found that 4-methoxyphenol can successfully undergo an enzyme-catalyzed polymerization reaction in water. It was also found that 4-methoxyphenol can easily form aggregates in an aqueous solution. In fact, the existence of aggregates in the water phase was found to be a crucial factor for the occurrence of a smooth enzyme-catalyzed polymerization (31).

It is gratifying that the enzyme-catalyzed polymerization of 4-methylcatechol can also be carried out in a water medium and that the reaction yield can reach as high as 82.8%. This is a result that may be caused by the formation of phenolic molecule aggregates in the water. To confirm this assumption, we have analyzed the fluorescence spectra of the 4-methylcatechol solutions at different concentrations. As can be seen in Figure 2, for a 4-methylcatechol concentration less than 0.4 mmol‧L−1, the fluorescence emission intensity will increase with the 4-methylcatechol concentration. However, for a concentration more than 0.6 mmol‧L−1, the fluorescence emission intensity becomes gradually weakened and basically disappears at a concentration of 8.0 mmol‧L−1. This is a typical aggregation-caused quenching phenomenon, which indicates that an aggregation of 4-methylcatechol has been formed in the water. It is, thus, the existence of 4-methylcatechol aggregates that induces a successful enzyme-catalyzed polymerization of 4-methylcatechol in the water medium.

Figure 2 Fluorescence emission spectra of 4-methylcatechol aqueous solutions of different concentrations.
Figure 2

Fluorescence emission spectra of 4-methylcatechol aqueous solutions of different concentrations.

Figure 3 shows the FTIR spectrum of a 4-methylcatechol oligomer, where the broad peak at 3,424 cm−1 is ascribed to the O–H stretching vibration. Furthermore, the peaks at 2,933 and 2,866 cm−1 belong to the stretching vibrations of the methyl group, and the ones at 1,615, 1,502, 872, and 805 cm−1 are the vibration absorption peaks for the C–H and C–C bonds in the benzene ring. Also, the peak at 1,204 cm−1 belongs to the C–O stretching vibration, and the peak at 1,100 cm−1 is ascribed to the asymmetric stretching vibration of the ether bond. Therefore, the FTIR analysis indicates that the 4-methoxyphenol oligomer contains two different chain structures of the Ph–O and Ph–Ph linkages.

Figure 3 Infrared spectrum of a 4-methylcatechol oligomer.
Figure 3

Infrared spectrum of a 4-methylcatechol oligomer.

High-resolution mass spectrometry was used to measure the polymerization degree of the 4-methylcatechol oligomer. As can be seen in Figure 4, the spectrum of the 4-methylcatechol oligomer indicates that the molecular weight distribution is in the range of 200–900 g‧mol−1. Moreover, the m/z value (i.e., the mass divided by charge value) of every two adjacent peaks is 122, which is exactly the molar mass of each repetitive unit in the 4-methylcatechol oligomer. In addition, it is clear that the 4-methylcatechol oligomer is mainly composed of trimers, tetramers, and pentamers.

Figure 4 Mass spectrum of the 4-methylcatechol oligomer.
Figure 4

Mass spectrum of the 4-methylcatechol oligomer.

3.2 Thermal properties of 4-methylcatechol oligomer

The low thermal stability is a major cause of the mediocre performance of small-molecule antioxidants at elevated temperatures. Figure 5 shows the thermal weight-loss curve of 4-methylcatechol and 4-methylcatechol oligomer in air atmosphere. It can be seen that the weight loss of 4-methylcatechol reaches 5% at 122°C, and it completely decomposes at 182°C. Moreover, a 5% weight loss of 4-methylcatechol oligomer occurs at 212°C, followed by a gradual carbonization above 400°C. Although the degree of 4-methylcatechol oligomer is not high, the thermal stability is greatly improved in comparison with 4-methylcatechol. The results also indicate that the 4-methylcatechol oligomer shows good antioxidant properties at elevated temperatures.

Figure 5 Thermal weight-loss curves of 4-methylcatechol (a) and 4-methylcatechol oligomer (b).
Figure 5

Thermal weight-loss curves of 4-methylcatechol (a) and 4-methylcatechol oligomer (b).

3.3 Analyses of OOT and OIT

The thermal oxidation of PP is an exothermic reaction and can, therefore, simply be detected by using a DSC. This is a well-known method by which it is possible to quickly evaluate the stability of the polymer samples against thermo-oxidative degradation in the melt state (in particular for polyolefins) (5,38). Figure 6 shows the DSC curves for intrinsic PP, BHT/PP, 1076/PP, 4-methylcatechol/PP, and 4-methylcatechol oligomer/PP in air atmosphere. The OOTs of the five PP samples could be obtained by analyzing the DSC curves. As can be seen in Table 1, the intrinsic PP shows the lowest OOT value. By adding 4-methylcatechol monomer, commercial BHT, or 1076 to the intrinsic PP sample, the OOT could be increased to various extents. Furthermore, the OOT increased considerably (by about 66°C) when adding the same amount of 4-methylcatechol oligomer. This temperature is much higher than those of 4-methylcatechol/PP, BHT/PP, 1076/PP, and the one previously reported for oligo(4-methoxyphenol)/PP (31). These results clearly show that although 4-methylcatechol has a certain antioxidation effect on the PP, the 4-methylcatechol oligomer shows more excellent antioxidation performances.

Figure 6 OOT curves of PP (a), BHT/PP (b), 1076/PP (c), 4-methylcatechol/PP (d), and 4-methylcatechol oligomers/PP (e).
Figure 6

OOT curves of PP (a), BHT/PP (b), 1076/PP (c), 4-methylcatechol/PP (d), and 4-methylcatechol oligomers/PP (e).

Table 1

OOT and OIT values of PP, BHT/PP, 1076/PP, 4-methylcatechol/PP, and 4-methylcatechol oligomer/PP

Sample OOT (°C) OIT (min)
PP 196 0.5
BHT/PP 218 4.5
1076/PP 231 20.5
4-Methylcatechol/PP 241 19.5
4-Methylcatechol oligomer/PP 262 40.5

The OIT curves of intrinsic PP, BHT/PP, 1076/PP, 4-methylcatechol/PP, and 4-methylcatechol oligomer/PP are shown in Figure 7, and the obtained OIT values are listed in Table 1. As can be seen in Figure 7, the intrinsic PP quickly oxidizes and decomposes when the gas flow in the environment is switched from nitrogen to oxygen (and thereby releases heat). The OIT value was found to increase to 19.5 min when adding 4-methylcatechol to the intrinsic PP. This is a value that is longer than the corresponding one for BHT/PP (4.5 min), but it is similar to the one for 1076/PP (20.5 min). Interestingly, the OIT became much longer when adding the 4-methylcatechol oligomer to the intrinsic PP sample (40.5 min), which is 21 min longer than that of 4-methylcatechol/PP. This result is consistent with the result from the OOT analysis. It proves that the 4-methylcatechol oligomer can prevent the thermal oxidative degradation of PP and thereby considerably improve the application performances of the PP material. Excellent antioxidative properties of the 4-methylphenol oligomer are probably related to the hindered phenol structure in its molecular chain. The hydrogen atoms provided by the phenolic hydroxyl group can easily react with the active radicals to form stable free radicals and, thereby, preventing the PP molecular chain from further oxidative dissociation. In addition, the relatively high molecular weight and good thermal stability of the 4-methylphenol oligomer are also important reasons for its excellent oxidation resistance.

Figure 7 OIT curves of PP (a), BHT/PP (b), 4-methylcatechol/PP (c), 1076/PP (d), and 4-methylcatechol oligomer/PP (e).
Figure 7

OIT curves of PP (a), BHT/PP (b), 4-methylcatechol/PP (c), 1076/PP (d), and 4-methylcatechol oligomer/PP (e).

3.4 Analysis of thermal aging performance

The accelerated aging experiment is a laboratory analysis method that simulates and strengthens the natural environment’s destructive effect on the polymer materials. As compared with the methods that quickly determine the antioxidant performances (such as OOT and OIT), the results of the accelerated aging experiments are closer to actual application conditions (8,38). We have, therefore, evaluated the long-term stability of the 4-methylphenol oligomer/PP composite in an air atmosphere at 120°C by using an accelerated thermal aging test and compared it with the corresponding results for intrinsic PP and 4-methylcatechol/PP. The infrared spectrum of intrinsic PP, 4-methylcatechol/PP, and 4-methylcatechol oligomer/PP for various aging times is shown in Figure 8. For intrinsic PP, a carbonyl stretching vibration peak appeared at 1,714 cm−1 after 72 h of aging, which indicates that the intrinsic PP had undergone oxidative degradation (8,38). In addition, it can be observed that new absorption peaks appear in the range of 3,560–3,760 cm−1, which is ascribed to the generation of hydroperoxide or other oxidized species containing hydroxyl group in aging process. A carbonyl stretching vibration peak did also appear for 4-methylcatechol/PP after 156 h of aging. This prolongation of aging time indicates that the 4-methylcatechol had a certain antioxidative effect on PP. On the contrary, no obvious new peaks could be observed for the 4-methylcatechol oligomer/PP, not even after 230 h of aging. This result shows that the 4-methylcatechol oligomer has an even better antioxidative effect on PP.

Figure 8 Changes of infrared spectra of PP (a), 4-methylcatechol/PP (b), and 4-methylcatechol oligomer/PP (c) with aging time.
Figure 8

Changes of infrared spectra of PP (a), 4-methylcatechol/PP (b), and 4-methylcatechol oligomer/PP (c) with aging time.

The aging of the PP material will cause changes in the structural configuration and, thereby, lead to deterioration of the mechanical properties (8). The variation in tensile strength for the intrinsic PP, 4-methylcatechol/PP, and 4-methylcatechol oligomer/PP, with aging time, can be seen in Figure 9. The tensile strength of intrinsic PP was found to significantly decrease (from 33.6 to 9.6 MPa) after 72 h of aging in an air atmosphere at 120°C. The addition of 4-methylcatechol improved the thermal oxidative degradation properties of PP to a certain extent. The tensile strength did not significantly decrease after aging for 72 h, while it decreased sharply when exceeding 200 h. However, the addition of 4-methylcatechol oligomer did not cause any apparent change after aging for 800 h. These results are in good agreement with the results of the infrared (IR) analyses. Thus, it can be concluded that the 4-methylcatechol oligomer exhibits an excellent antioxidant reactivity toward the PP material.

Figure 9 Variations of tensile strength of PP, 4-methylcatechol/PP, and 4-methylcatechol oligomer/PP with aging time.
Figure 9

Variations of tensile strength of PP, 4-methylcatechol/PP, and 4-methylcatechol oligomer/PP with aging time.

4 Conclusion

In the present study, 4-methylcatechol oligomer has been prepared by using enzyme-catalyzed polymerization in water. The 4-methylcatechol oligomer was, further on, investigated as a plausible antioxidant for PP material protection from thermal oxidative degradation. Thermogravimetric analyses showed that the 4-methylcatechol oligomer has a good thermal stability, which ensures structural integrity in a thermal oxidative environment. By adding the oligomer to PP, the OOT value was found to increase by 62°C, and OIT to increase by 40 min, as compared with the corresponding values for intrinsic PP. Furthermore, in comparison with the commercial antioxidants BHT and 1076, the 4-methylcatechol oligomer was found to exhibit much better antioxidant reactivity toward PP. In addition, the tensile strength of 4-methylcatechol oligomer/PP did not apparently decrease after aging for 800 h in an air environment. These results show that the long-term stability of PP in harsh environments is significantly enhanced. The high antioxidant efficiency of the 4-methylcatechol oligomer can be ascribed to the relatively high molecular weight and good thermal stability of the oligomer. Therefore, enzyme-catalyzed polymerizations of small-molecule phenol compounds may provide a new avenue for the preparation of new antioxidants with high performances.

Acknowledgements

The authors sincerely acknowledge Prof. Wenshan Zhao (Henan University) for the instrument testing service.

  1. Funding information: The authors are grateful to the financial support from the discipline construction funds of Henan University (No. 152300410059).

  2. Author contributions: Yanpeng Wang: writing – original draft, methodology, formal analysis; Fan Jiang: formal analysis, methodology, visualization; Lei Zhang: writing – review and editing, project administration, resources.

  3. Conflict of interest: The authors state no conflict of interest.

  4. Data availability statement: All data generated or analyzed during this study are included in this published article.

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Received: 2022-08-06
Revised: 2022-11-26
Accepted: 2022-12-12
Published Online: 2023-02-15

© 2023 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  2. Chitosan nanocomposite film incorporating Nigella sativa oil, Azadirachta indica leaves’ extract, and silver nanoparticles
  3. Effect of Zr-doped CaCu3Ti3.95Zr0.05O12 ceramic on the microstructure, dielectric properties, and electric field distribution of the LDPE composites
  4. Effects of dry heating, acetylation, and acid pre-treatments on modification of potato starch with octenyl succinic anhydride (OSA)
  5. Loading conditions impact on the compression fatigue behavior of filled styrene butadiene rubber
  6. Characterization and compatibility of bio-based PA56/PET
  7. Study on the aging of three typical rubber materials under high- and low-temperature cyclic environment
  8. Numerical simulation and experimental research of electrospun polyacrylonitrile Taylor cone based on multiphysics coupling
  9. Experimental investigation of properties and aging behavior of pineapple and sisal leaf hybrid fiber-reinforced polymer composites
  10. Influence of temperature distribution on the foaming quality of foamed polypropylene composites
  11. Enzyme-catalyzed synthesis of 4-methylcatechol oligomer and preliminary evaluations as stabilizing agent in polypropylene
  12. Molecular dynamics simulation of the effect of the thermal and mechanical properties of addition liquid silicone rubber modified by carbon nanotubes with different radii
  13. Incorporation of poly(3-acrylamidopropyl trimethylammonium chloride-co-acrylic acid) branches for good sizing properties and easy desizing from sized cotton warps
  14. Effect of matrix composition on properties of polyamide 66/polyamide 6I-6T composites with high content of continuous glass fiber for optimizing surface performance
  15. Preparation and properties of epoxy-modified thermosetting phenolic fiber
  16. Thermal decomposition reaction kinetics and storage life prediction of polyacrylate pressure-sensitive adhesive
  17. Effect of different proportions of CNTs/Fe3O4 hybrid filler on the morphological, electrical and electromagnetic interference shielding properties of poly(lactic acid) nanocomposites
  18. Doping silver nanoparticles into reverse osmosis membranes for antibacterial properties
  19. Melt-blended PLA/curcumin-cross-linked polyurethane film for enhanced UV-shielding ability
  20. The affinity of bentonite and WO3 nanoparticles toward epoxy resin polymer for radiation shielding
  21. Prolonged action fertilizer encapsulated by CMC/humic acid
  22. Preparation and experimental estimation of radiation shielding properties of novel epoxy reinforced with Sb2O3 and PbO
  23. Fabrication of polylactic acid nanofibrous yarns for piezoelectric fabrics
  24. Copper phenyl phosphonate for epoxy resin and cyanate ester copolymer with improved flame retardancy and thermal properties
  25. Synergistic effect of thermal oxygen and UV aging on natural rubber
  26. Effect of zinc oxide suspension on the overall filler content of the PLA/ZnO composites and cPLA/ZnO composites
  27. The role of natural hybrid nanobentonite/nanocellulose in enhancing the water resistance properties of the biodegradable thermoplastic starch
  28. Performance optimization of geopolymer mortar blending in nano-SiO2 and PVA fiber based on set pair analysis
  29. Preparation of (La + Nb)-co-doped TiO2 and its polyvinylidene difluoride composites with high dielectric constants
  30. Effect of matrix composition on the performance of calcium carbonate filled poly(lactic acid)/poly(butylene adipate-co-terephthalate) composites
  31. Low-temperature self-healing polyurethane adhesives via dual synergetic crosslinking strategy
  32. Leucaena leucocephala oil-based poly malate-amide nanocomposite coating material for anticorrosive applications
  33. Preparation and properties of modified ammonium polyphosphate synergistic with tris(2-hydroxyethyl) isocynurate for flame-retardant LDPE
  34. Thermal response of double network hydrogels with varied composition
  35. The effect of coated calcium carbonate using stearic acid on the recovered carbon black masterbatch in low-density polyethylene composites
  36. Investigation of MXene-modified agar/polyurethane hydrogel elastomeric repair materials with tunable water absorption
  37. Damping performance analysis of carbon black/lead magnesium niobite/epoxy resin composites
  38. Molecular dynamics simulations of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate (TKX-50) and TKX-50-based PBXs with four energetic binders
  39. Preparation and characterization of sisal fibre reinforced sodium alginate gum composites for non-structural engineering applications
  40. Study on by-products synthesis of powder coating polyester resin catalyzed by organotin
  41. Ab initio molecular dynamics of insulating paper: Mechanism of insulating paper cellobiose cracking at transient high temperature
  42. Effect of different tin neodecanoate and calcium–zinc heat stabilizers on the thermal stability of PVC
  43. High-strength polyvinyl alcohol-based hydrogel by vermiculite and lignocellulosic nanofibrils for electronic sensing
  44. Impacts of micro-size PbO on the gamma-ray shielding performance of polyepoxide resin
  45. Influence of the molecular structure of phenylamine antioxidants on anti-migration and anti-aging behavior of high-performance nitrile rubber composites
  46. Fiber-reinforced polyvinyl alcohol hydrogel via in situ fiber formation
  47. Preparation and performance of homogenous braids-reinforced poly (p-phenylene terephthamide) hollow fiber membranes
  48. Synthesis of cadmium(ii) ion-imprinted composite membrane with a pyridine functional monomer and characterization of its adsorption performance
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  50. Comprehensive study of the radiation shielding feature of polyester polymers impregnated with iron filings
  51. Preparation and characterization of polymeric cross-linked hydrogel patch for topical delivery of gentamicin
  52. Mechanical properties of rCB-pigment masterbatch in rLDPE: The effect of processing aids and water absorption test
  53. Pineapple fruit residue-based nanofibre composites: Preparation and characterizations
  54. Effect of natural Indocalamus leaf addition on the mechanical properties of epoxy and epoxy-carbon fiber composites
  55. Utilization of biosilica for energy-saving tire compounds: Enhancing performance and efficiency
  56. Effect of capillary arrays on the profile of multi-layer micro-capillary films
  57. A numerical study on thermal bonding with preheating technique for polypropylene microfluidic device
  58. Development of modified h-BN/UPE resin for insulation varnish applications
  59. High strength, anti-static, thermal conductive glass fiber/epoxy composites for medical devices: A strategy of modifying fibers with functionalized carbon nanotubes
  60. Effects of mechanical recycling on the properties of glass fiber–reinforced polyamide 66 composites in automotive components
  61. Bentonite/hydroxyethylcellulose as eco-dielectrics with potential utilization in energy storage
  62. Study on wall-slipping mechanism of nano-injection polymer under the constant temperature fields
  63. Synthesis of low-VOC unsaturated polyester coatings for electrical insulation
  64. Enhanced apoptotic activity of Pluronic F127 polymer-encapsulated chlorogenic acid nanoparticles through the PI3K/Akt/mTOR signaling pathway in liver cancer cells and in vivo toxicity studies in zebrafish
  65. Preparation and performance of silicone-modified 3D printing photosensitive materials
  66. A novel fabrication method of slippery lubricant-infused porous surface by thiol-ene click chemistry reaction for anti-fouling and anti-corrosion applications
  67. Development of polymeric IPN hydrogels by free radical polymerization technique for extended release of letrozole: Characterization and toxicity evaluation
  68. Tribological characterization of sponge gourd outer skin fiber-reinforced epoxy composite with Tamarindus indica seed filler addition using the Box–Behnken method
  69. Stereocomplex PLLA–PBAT copolymer and its composites with multi-walled carbon nanotubes for electrostatic dissipative application
  70. Enhancing the therapeutic efficacy of Krestin–chitosan nanocomplex for cancer medication via activation of the mitochondrial intrinsic pathway
  71. Variation in tungsten(vi) oxide particle size for enhancing the radiation shielding ability of silicone rubber composites
  72. Damage accumulation and failure mechanism of glass/epoxy composite laminates subjected to repeated low velocity impacts
  73. Gamma-ray shielding analysis using the experimental measurements for copper(ii) sulfate-doped polyepoxide resins
  74. Numerical simulation into influence of airflow channel quantities on melt-blowing airflow field in processing of polymer fiber
  75. Cellulose acetate oleate-reinforced poly(butylene adipate-co-terephthalate) composite materials
  76. Radiation shielding capability and exposure buildup factor of cerium(iv) oxide-reinforced polyester resins
  77. Recyclable polytriazole resins with high performance based on Diels-Alder dynamic covalent crosslinking
  78. Adsorption and recovery of Cr(vi) from wastewater by Chitosan–Urushiol composite nanofiber membrane
  79. Comprehensive performance evaluation based on electromagnetic shielding properties of the weft-knitted fabrics made by stainless steel/cotton blended yarn
  80. Review Articles
  81. Preparation and application of natural protein polymer-based Pickering emulsions
  82. Wood-derived high-performance cellulose structural materials
  83. Flammability properties of polymers and polymer composites combined with ionic liquids
  84. Polymer-based nanocarriers for biomedical and environmental applications
  85. A review on semi-crystalline polymer bead foams from stirring autoclave: Processing and properties
  86. Rapid Communication
  87. Preparation and characterization of magnetic microgels with linear thermosensitivity over a wide temperature range
  88. Special Issue: Biodegradable and bio-based polymers: Green approaches (Guest Editors: Kumaran Subramanian, A. Wilson Santhosh Kumar, and Venkatajothi Ramarao)
  89. Synthesis and characterization of proton-conducting membranes based on bacterial cellulose and human nail keratin
  90. Fatigue behaviour of Kevlar/carbon/basalt fibre-reinforced SiC nanofiller particulate hybrid epoxy composite
  91. Effect of citric acid on thermal, phase morphological, and mechanical properties of poly(l-lactide)-b-poly(ethylene glycol)-b-poly(l-lactide)/thermoplastic starch blends
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https://doi.org/10.1515/epoly-2023-0008
Keywords for this article
enzymatic polymerization; green synthesis; antioxidant; thermal oxidative stability; polypropylene
Creative Commons
BY 4.0

Articles in the same Issue

  1. Research Articles
  2. Chitosan nanocomposite film incorporating Nigella sativa oil, Azadirachta indica leaves’ extract, and silver nanoparticles
  3. Effect of Zr-doped CaCu3Ti3.95Zr0.05O12 ceramic on the microstructure, dielectric properties, and electric field distribution of the LDPE composites
  4. Effects of dry heating, acetylation, and acid pre-treatments on modification of potato starch with octenyl succinic anhydride (OSA)
  5. Loading conditions impact on the compression fatigue behavior of filled styrene butadiene rubber
  6. Characterization and compatibility of bio-based PA56/PET
  7. Study on the aging of three typical rubber materials under high- and low-temperature cyclic environment
  8. Numerical simulation and experimental research of electrospun polyacrylonitrile Taylor cone based on multiphysics coupling
  9. Experimental investigation of properties and aging behavior of pineapple and sisal leaf hybrid fiber-reinforced polymer composites
  10. Influence of temperature distribution on the foaming quality of foamed polypropylene composites
  11. Enzyme-catalyzed synthesis of 4-methylcatechol oligomer and preliminary evaluations as stabilizing agent in polypropylene
  12. Molecular dynamics simulation of the effect of the thermal and mechanical properties of addition liquid silicone rubber modified by carbon nanotubes with different radii
  13. Incorporation of poly(3-acrylamidopropyl trimethylammonium chloride-co-acrylic acid) branches for good sizing properties and easy desizing from sized cotton warps
  14. Effect of matrix composition on properties of polyamide 66/polyamide 6I-6T composites with high content of continuous glass fiber for optimizing surface performance
  15. Preparation and properties of epoxy-modified thermosetting phenolic fiber
  16. Thermal decomposition reaction kinetics and storage life prediction of polyacrylate pressure-sensitive adhesive
  17. Effect of different proportions of CNTs/Fe3O4 hybrid filler on the morphological, electrical and electromagnetic interference shielding properties of poly(lactic acid) nanocomposites
  18. Doping silver nanoparticles into reverse osmosis membranes for antibacterial properties
  19. Melt-blended PLA/curcumin-cross-linked polyurethane film for enhanced UV-shielding ability
  20. The affinity of bentonite and WO3 nanoparticles toward epoxy resin polymer for radiation shielding
  21. Prolonged action fertilizer encapsulated by CMC/humic acid
  22. Preparation and experimental estimation of radiation shielding properties of novel epoxy reinforced with Sb2O3 and PbO
  23. Fabrication of polylactic acid nanofibrous yarns for piezoelectric fabrics
  24. Copper phenyl phosphonate for epoxy resin and cyanate ester copolymer with improved flame retardancy and thermal properties
  25. Synergistic effect of thermal oxygen and UV aging on natural rubber
  26. Effect of zinc oxide suspension on the overall filler content of the PLA/ZnO composites and cPLA/ZnO composites
  27. The role of natural hybrid nanobentonite/nanocellulose in enhancing the water resistance properties of the biodegradable thermoplastic starch
  28. Performance optimization of geopolymer mortar blending in nano-SiO2 and PVA fiber based on set pair analysis
  29. Preparation of (La + Nb)-co-doped TiO2 and its polyvinylidene difluoride composites with high dielectric constants
  30. Effect of matrix composition on the performance of calcium carbonate filled poly(lactic acid)/poly(butylene adipate-co-terephthalate) composites
  31. Low-temperature self-healing polyurethane adhesives via dual synergetic crosslinking strategy
  32. Leucaena leucocephala oil-based poly malate-amide nanocomposite coating material for anticorrosive applications
  33. Preparation and properties of modified ammonium polyphosphate synergistic with tris(2-hydroxyethyl) isocynurate for flame-retardant LDPE
  34. Thermal response of double network hydrogels with varied composition
  35. The effect of coated calcium carbonate using stearic acid on the recovered carbon black masterbatch in low-density polyethylene composites
  36. Investigation of MXene-modified agar/polyurethane hydrogel elastomeric repair materials with tunable water absorption
  37. Damping performance analysis of carbon black/lead magnesium niobite/epoxy resin composites
  38. Molecular dynamics simulations of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate (TKX-50) and TKX-50-based PBXs with four energetic binders
  39. Preparation and characterization of sisal fibre reinforced sodium alginate gum composites for non-structural engineering applications
  40. Study on by-products synthesis of powder coating polyester resin catalyzed by organotin
  41. Ab initio molecular dynamics of insulating paper: Mechanism of insulating paper cellobiose cracking at transient high temperature
  42. Effect of different tin neodecanoate and calcium–zinc heat stabilizers on the thermal stability of PVC
  43. High-strength polyvinyl alcohol-based hydrogel by vermiculite and lignocellulosic nanofibrils for electronic sensing
  44. Impacts of micro-size PbO on the gamma-ray shielding performance of polyepoxide resin
  45. Influence of the molecular structure of phenylamine antioxidants on anti-migration and anti-aging behavior of high-performance nitrile rubber composites
  46. Fiber-reinforced polyvinyl alcohol hydrogel via in situ fiber formation
  47. Preparation and performance of homogenous braids-reinforced poly (p-phenylene terephthamide) hollow fiber membranes
  48. Synthesis of cadmium(ii) ion-imprinted composite membrane with a pyridine functional monomer and characterization of its adsorption performance
  49. Impact of WO3 and BaO nanoparticles on the radiation shielding characteristics of polydimethylsiloxane composites
  50. Comprehensive study of the radiation shielding feature of polyester polymers impregnated with iron filings
  51. Preparation and characterization of polymeric cross-linked hydrogel patch for topical delivery of gentamicin
  52. Mechanical properties of rCB-pigment masterbatch in rLDPE: The effect of processing aids and water absorption test
  53. Pineapple fruit residue-based nanofibre composites: Preparation and characterizations
  54. Effect of natural Indocalamus leaf addition on the mechanical properties of epoxy and epoxy-carbon fiber composites
  55. Utilization of biosilica for energy-saving tire compounds: Enhancing performance and efficiency
  56. Effect of capillary arrays on the profile of multi-layer micro-capillary films
  57. A numerical study on thermal bonding with preheating technique for polypropylene microfluidic device
  58. Development of modified h-BN/UPE resin for insulation varnish applications
  59. High strength, anti-static, thermal conductive glass fiber/epoxy composites for medical devices: A strategy of modifying fibers with functionalized carbon nanotubes
  60. Effects of mechanical recycling on the properties of glass fiber–reinforced polyamide 66 composites in automotive components
  61. Bentonite/hydroxyethylcellulose as eco-dielectrics with potential utilization in energy storage
  62. Study on wall-slipping mechanism of nano-injection polymer under the constant temperature fields
  63. Synthesis of low-VOC unsaturated polyester coatings for electrical insulation
  64. Enhanced apoptotic activity of Pluronic F127 polymer-encapsulated chlorogenic acid nanoparticles through the PI3K/Akt/mTOR signaling pathway in liver cancer cells and in vivo toxicity studies in zebrafish
  65. Preparation and performance of silicone-modified 3D printing photosensitive materials
  66. A novel fabrication method of slippery lubricant-infused porous surface by thiol-ene click chemistry reaction for anti-fouling and anti-corrosion applications
  67. Development of polymeric IPN hydrogels by free radical polymerization technique for extended release of letrozole: Characterization and toxicity evaluation
  68. Tribological characterization of sponge gourd outer skin fiber-reinforced epoxy composite with Tamarindus indica seed filler addition using the Box–Behnken method
  69. Stereocomplex PLLA–PBAT copolymer and its composites with multi-walled carbon nanotubes for electrostatic dissipative application
  70. Enhancing the therapeutic efficacy of Krestin–chitosan nanocomplex for cancer medication via activation of the mitochondrial intrinsic pathway
  71. Variation in tungsten(vi) oxide particle size for enhancing the radiation shielding ability of silicone rubber composites
  72. Damage accumulation and failure mechanism of glass/epoxy composite laminates subjected to repeated low velocity impacts
  73. Gamma-ray shielding analysis using the experimental measurements for copper(ii) sulfate-doped polyepoxide resins
  74. Numerical simulation into influence of airflow channel quantities on melt-blowing airflow field in processing of polymer fiber
  75. Cellulose acetate oleate-reinforced poly(butylene adipate-co-terephthalate) composite materials
  76. Radiation shielding capability and exposure buildup factor of cerium(iv) oxide-reinforced polyester resins
  77. Recyclable polytriazole resins with high performance based on Diels-Alder dynamic covalent crosslinking
  78. Adsorption and recovery of Cr(vi) from wastewater by Chitosan–Urushiol composite nanofiber membrane
  79. Comprehensive performance evaluation based on electromagnetic shielding properties of the weft-knitted fabrics made by stainless steel/cotton blended yarn
  80. Review Articles
  81. Preparation and application of natural protein polymer-based Pickering emulsions
  82. Wood-derived high-performance cellulose structural materials
  83. Flammability properties of polymers and polymer composites combined with ionic liquids
  84. Polymer-based nanocarriers for biomedical and environmental applications
  85. A review on semi-crystalline polymer bead foams from stirring autoclave: Processing and properties
  86. Rapid Communication
  87. Preparation and characterization of magnetic microgels with linear thermosensitivity over a wide temperature range
  88. Special Issue: Biodegradable and bio-based polymers: Green approaches (Guest Editors: Kumaran Subramanian, A. Wilson Santhosh Kumar, and Venkatajothi Ramarao)
  89. Synthesis and characterization of proton-conducting membranes based on bacterial cellulose and human nail keratin
  90. Fatigue behaviour of Kevlar/carbon/basalt fibre-reinforced SiC nanofiller particulate hybrid epoxy composite
  91. Effect of citric acid on thermal, phase morphological, and mechanical properties of poly(l-lactide)-b-poly(ethylene glycol)-b-poly(l-lactide)/thermoplastic starch blends
  92. Dose-dependent cytotoxicity against lung cancer cells via green synthesized ZnFe2O4/cellulose nanocomposites
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