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Progress in Natural Science-Materials International · 2020 · IF 4

Acyl-chloride functionalized graphene oxide chemically grafted with hindered phenol and its application in anti-degradation of polypropylene

Jialu Yao,Shixiang Liu,Yajiang Huang,Shijie Ren,Yadong Lv,Miqiu Kong,Guangxian Li

In this study, graphene oxide (GO) nanosheets were first functionalized by the acyl-chloride reaction and then reacted with hindered phenol (HP) to obtain HP grafted GO (GO-g-HP). The GO-g-HP prepared under the optimized condition exhibited a high efficiency against both thermal and photo oxidation of isotactic polypropylene (iPP). GO-g-HP exhibited a much better anti-aging efficiency than that of HP and GO used individually or that of their physical mixture. The outstanding anti-aging effect of GO-g-HP was attributed to the excellent synergistic effect produced between the chemically bonded GO and HP, which resulted in an improved oxygen barrier property of GO and excellent utilization of the free radical scavenging capability of GO and HP. Also, thanks to the grafting of HP on GO, the physical loss of HP, which was one of the main shortcomings for traditional small molecular antioxidants , was largely suppressed. It is expected that the GO-g-HP prepared can well meet the requirement of long-term applications of polymers in some harsh service conditions.

研究领域: 材料科学 · 高分子化学
✓ 已验证 DOI 高影响因子
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POLYMER ENGINEERING AND SCIENCE · 2019 ·Vol. 60 ·期 3 ·446-454 · IF 1.92

Molecular Insights Into Chain Length Effects of Hindered Phenol on the Molecular Interactions and Damping Properties of Polymer-Based Hybrid Materials

Kangming Xu,Hongdi Zhou,Qiaoman Hu,Junhui Wang,Yue Huang,Jinlei Chen

For hindered phenol (HP)/polymer-based hybrid damping materials, the unclear relationship between the structure of HP and the damping properties limits the application of such promising materials. Herein, three kinds of HPs with different chain lengths were synthesized to explore the mechanism. The structures of the HPs were confirmed by nuclear magnetic resonance spectrum, the Fourier Transform Infrared Spectroscopy (FT-IR), and X-ray Diffraction (XRD). For further prepared HP/polyurethane hybrids, FT-IR and XRD were adopted to confirm the hydrogen bonding interactions and micromorphologies. Moreover, molecular dynamics simulation was used to characterize the effects of chain length variation on the inter- and intramolecular hydrogen bonds (HBs) and the chain packing of the hybrids in a quantitative manner. Subsequently, combined with the dynamic mechanical analysis, the relationship between the chain length variation and the damping properties was established. The results showed that with the increasing of chain length, the intramolecular HBs between HPs can be prevented, and the loose HP chain within tight polymer matrix can be achieved, which results in a maximum increase of loss factor. While the homogeneity of the chain packing increases with the chain length increasing, which results in a decrease of the temperature range of loss factor ≥ 0.3. POLYM. ENG. SCI., 60:446–454, 2020. © 2019 Society of Plastics Engineers

研究领域: 材料科学 · 高分子化学
✓ 已验证 DOI 高影响因子
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JOURNAL OF POLYMER ENGINEERING · 2020 ·Vol. 40 ·期 5 ·394-402 · IF 1.126

Effects of chain polarity of hindered phenol on the damping properties of polymer-based hybrid materials: insights into the molecular mechanism

Qiaoman Hu,Junhui Wang,Kangming Xu,Hongdi Zhou,Yue Huang,Jinlei Chen

For hindered phenol (HP)/polymer-based hybrid damping materials, the damping properties are greatly affected by the structure variation of HPs. However, the unclear relationship between them limits the exploitation of such promising materials. Therefore, three HPs with different chain polarity were synthesized to explore the relationship in this paper. The structures of the HPs were firstly confirmed by Nuclear Magnetic Resonance Spectrum, Fourier Transform Infrared Spectroscopy (FT-IR) and X-ray Diffraction (XRD). For further prepared HP/polyurethane hybrids, FT-IR and XRD were also adopted to confirm the hydrogen bonding interactions and micromorphologies. And, Molecular dynamics simulation was further used to characterize the effects of polarity variation on the hydrogen bonding interactions and chain packing of the hybrids in a quantitative manner. Then, combined with dynamic mechanical analysis, the relationship between the chain polarity variation of the hindered phenols and the damping properties was established.

研究领域: 材料科学 · 高分子化学
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Antioxidants · 2024 ·Vol. 13 ·期 8 ·894 · IF 6

Synthesis, Characterization, and Evaluation of a Hindered Phenol-Linked Benzophenone Hybrid Compound as a Potential Polymer Anti-Aging Agent

Shenshuai Wang,Yingjie Huang,Weiye Sun,Xufeng Lin

Hindered phenol antioxidants and benzophenone UV absorbers are common polymer additives and often used in combination applications to enhance the anti-aging performance of polymer materials. This study primarily aims to incorporate hindered phenol and benzophenone structures into a single molecule to develop a multifunctional polymer additive with good anti-aging performance. Thus, a novel potential polymer anti-aging agent, namely 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid 3-(4-benzoyl-3-hydroxyphenoxy)propyl ester (3C), was synthesized using 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, 3-bromo-1-propanol, and 2,4-dihydroxybenzophenone as raw materials by two-step procedure. The structure of compound3Cwas characterized by nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), Fourier-transform infrared (FT-IR) spectroscopy, and X-ray single crystal diffraction. Its thermal stability and UV resistance were assessed using thermogravimetric analysis (TGA) and UV absorption spectroscopy (UV). The compound3Cas an additive was incorporated into the preparation of polyolefin elastomer (POE) films. The anti-aging performance of POE films was evaluated by measuring parameters such as oxidation induction time, melt flow index, transmittance, and infrared spectra of the artificially aged POE films. The results indicate that the compound3Cexhibits a promising anti-aging performance in both thermo-oxidative aging and ultraviolet aging tests of POE films and is a potential polymer anti-aging agent.

CAS / MDL: 7757-93-9
研究领域: 材料科学 · 高分子化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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POLYMER BULLETIN · 2023 · IF 3.2

Structure and properties of damping chlorinated butyl rubber composites with hyperbranched polyester grafted hindered phenol

Gong Ting,Liu Jiancheng,Wang Jincheng,Tang Keya,Lu Wentong,Wang Liming

The damping performance of chlorinated butyl rubber (CIIR) cannot satisfy the rigorous requirements of damping and vibration reduction. Hindered phenol can endow rubber composites with good damping performance, but these small molecules may migrate from rubber matrices. Here, a novel type of damping agent based on the hyperbranched polyester grafted hindered phenol (AG-HP102) was prepared by grafting hindered phenol (AG) with hydroxyl terminated hyperbranched polyester (HP102). It was then incorporated into chlorinated butyl rubber (CIIR) to prepare damping rubber composites. The test results showed that tan δ max of CIIR/AG-HP102 (7 phr) was 1.40, which was 32.1% higher than that of pure CIIR, 1.05. In addition, the glass transition temperature ( T g ) was increased from − 26.0 to − 16 ℃. The mechanical property tests showed that the tensile strength and elongation at break of the CIIR/AG-HP102 (7 phr) composite reached 8.21 MPa and 1192%, respectively, which was 290.9% and 39.5% higher than those of pure CIIR, 2.11 MPa and 858%. These experiment results can offer some useful information for the design and fabrication of high-performance polymeric damping materials.

研究领域: 材料科学 · 高分子化学 · 机械工程
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JOURNAL OF APPLIED POLYMER SCIENCE · 2023 ·Vol. 140 ·期 30 ·e54085 · IF 3

Synthesis of the reactive hindered phenol antioxidant 3,5-di-tert-butyl-4-hydroxyphenyl methyl isobutylene ester and its application in ABS resin

Xiao-Peng Wang,Feng-Hang Yao,Jie Chen

In this study, a reactive hindered phenol antioxidant, 3,5-di- tert -butyl-4-hydroxyphenyl methyl isobutylene ester (DBHMIE), was synthesized and used to improve the antioxidant performance of ABS (acrylonitrile-butadiene-styrene terpolymer) resin. The chemical structure of DBHMIE was determined with Fourier transform infrared spectroscopy, 1 H nuclear magnetic resonance (NMR), and 13 C NMR spectroscopy. Moreover, the effects of the DBHMIE content on the antioxidant capabilities, thermal stabilities, tensile strengths, impact strengths, and morphologies of the ABS/antioxidant systems were investigated. The results indicated that the oxidation induction temperatures of the systems increased from 229.7 to 245.4°C as the DBHMIE content was increased from 0 to 0.5 wt%. The 5% mass loss temperature of the system was increased from 338.4 to 347.8°C by the addition of 0.3 wt% DBHMIE. The impact strengths of the systems increased with increasing DBHMIE content up to 0.1 wt% and then decreased. The addition of DBHMIE did not significantly affect the tensile strength of the ABS resin. SEM images showed that the DBHMIE was uniformly distributed in the ABS resin at low DBHMIE contents and agglomerated at high DBHMIE contents.

研究领域: 材料科学 · 高分子化学
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RSC Advances · 2025 ·Vol. 15 ·期 19 ·14594-14603 · IF 4.6

Electron structure variations in hindered phenolic antioxidant induced enhancement of thermo-oxidative aging performance in polyamide 6

Bingxue Guo,Jinfen Lou,Tingting Kuang,Yanping Wang,Kai Zhang,Jun Qin,Min He,Yufei Liu,Yong-Ji Gong

PA6 is widely used but vulnerable to thermo-oxidative aging, impacting its durability. Hindered phenols are key antioxidants that extend the service life of PA6 by slowing this aging process. However, the effect of molecular structural differences on their antioxidant activity is still elusive, impeding their development and application. Here, two antioxidants, 2-((3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl)oxy)ethyl acrylate (PEA) and 2-((3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl)oxy)propyl acrylate (PPA), were utilized to enhance the thermo-oxidative aging resistance of PA6. Their primary difference is that PPA possesses an electron-donating group in its molecular structure. The methyl functional group in the PPA molecule can increase the electron cloud density around the benzene ring, resulting in PPA having a higher free radical scavenging rate compared to PEA. In addition, in contrast to PEA, the low volatility and mobility of PPA ensure that its antioxidant activity can be fully utilized during aging. These factors collectively support the excellent antioxidant activity of PPA (PPA > PEA). As a result, the PA6/PPA composite maintains 88% of its original tensile strength after 12 days of continuous aging, whereas PA6/PEA and PA6/1010 (commercial antioxidant) composites retained 70% and methyl 30%, respectively. These encouraging findings provide a theoretical basis for the synthesis of antioxidants.

研究领域: 材料科学 · 化学工程
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF COLLOID AND INTERFACE SCIENCE · 2021 · IF 8.128

Hindered phenolic antioxidant passivation of black phosphorus affords air stability and free radical quenching

Shuilai Qiu,Jing Liang,Yanbei Hou,Xia Zhou,Yifan Zhou,Jingwen Wang,Bin Zou,Weiyi Xing,Yuan Hu

As an antioxidant , hindered phenol scavenges free radicals . Due to the oxidative degradation of black phosphorus (BP) in the presence of water and oxygen, free radical quenching of hindered phenol antioxidants can solve this issue and improve the environmental stability and flame retardant efficiency of BP. Herein, hydroxyl-modified BP (BP-OH) with active groups on the surface was obtained by hydroxylation , and then the hindered phenol antioxidant was grafted onto the surface of BP-OH through an isophorone diisocyanate bridging covalent reaction to obtain hindered phenol-modified BP (BP-HPL). The fire hazard of thermoplastic polyurethane (TPU) can be significantly reduced by introducing BP-HPL into TPU. Adding 2 wt% BP-HPL can reduce the heat release rate and total heat release values of TPU by 49.9% and 49.0%, respectively. In addition, the reductions in smoke volume and carbon monoxide production were also significant. Compared with BP-OH, the environmental stability of BP-HPL is significantly improved. This work provides a reference for the application of BP in the field of fire safety and simultaneously achieves the improvement of the environmental stability and flame retardant performance of BP.

研究领域: 材料科学 · 化学工程
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Energy Reports · 2023 · IF 5.2

Effect of hindered phenolic antioxidants on crosslinking characteristics of low-density polyethylene initiated by peroxide

Jiacai Li,Zhicheng Si,Shihang Wang,Shengtao Li,Hong Zhou,Jiajun Liu

Hindered phenolic antioxidants are the most prevalent antioxidants used in crosslinked polyethylene (XLPE) insulating materials of high-voltage (HV) cables. Doping antioxidants is conducive to delaying the low-temperature pre-crosslinking, but decreases final crosslinking degree. In order to comprehensively reveal the effect of hindered phenolic antioxidants on the crosslinking characteristics of XLPE insulating materials, four kinds of insulating materials doped with different hindered phenolic antioxidants are studied by experiment and simulation methods. The results demonstrate that antioxidant 300 is better for delaying low-temperature pre-crosslinking of insulating materials, but negative for maintaining high crosslinking efficiency and degree. Although insulating materials with antioxidant 1010 have higher crosslinking degree, it is poor to delay the low-temperature pre-crosslinking. Notably, antioxidant 245 with phenolic hydroxyl of lower bond dissociation energies can delay the low-temperature pre-crosslinking to some extent, meanwhile, crosslinking efficiency and degree of XLPE are still higher. Notably, the crosslinking characteristics of XLPE insulating materials are closely related to molecular structure of antioxidants, including functional group and ortho-substituents. Comprehensively considering the demands of delaying low-temperature pre-crosslinking and maintaining high crosslinking degree of insulating materials, antioxidant 245 is the better choice. This study provides a theoretical guidance for the choice of hindered phenolic antioxidants used for HV cable insulating materials.

CAS / MDL: 6683-19-8
研究领域: 材料科学 · 高分子化学
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Polymers · 2019 ·Vol. 11 ·期 5 ·884 · IF 3.164

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

Kangming Xu,Qiaoman Hu,Junhui Wang,Hongdi Zhou,Jinlei Chen

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.Keywords:hindered phenol/polymer-based hybrid damping materials;stability;high damping performance;structure optimization;damping mechanism

CAS / MDL: 141-78-6 5675-51-4
研究领域: 材料科学 · 化学工程
✓ 已验证 产品关联 DOI PubMed 高影响因子
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TRIBOLOGY INTERNATIONAL · 2025 · IF 6.9

A novel hindered phenol based multi-functional lubricant additive with enhanced antioxidant and tribological performance

Yuexia Huang,Qiang Chen,Jing Yang,Pingxia Guo,Xiao Liu,Kai Feng,Meirong Cai,Feng Zhou

A novel oil-miscible hindered phenol based multifunctional lubricant additive (BHT)-NP was synthesized and its antioxidant, tribological properties were thoroughly characterized. Compared with the commercially available hindered phenolic antioxidants (ST-135), the (BHT)-NP exhibited enhanced antioxidant and wear reduction properties at room temperature or 100 ℃. Specifically, adding 4 wt% (BHT)-NP to PAO10 could prolong its oxidation induction time from 4 to 70 min, which is 2.2 times that of ST-135. Additionally, this lubricant system could also decrease the wear volume of PAO10 + 4 wt% ST-135 by 88.67 % (rt), 88.42 % (100 ℃), respectively. Subsequently, lubrication mechanism analysis results suggested that an effective protection film was fabricated on the sliding steel surface, which significantly prevented the direct contact between the sliding pairs.

CAS / MDL: 64-19-7
研究领域: 材料科学 · 机械工程 · 化学工程 · 摩擦学
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CHEMICAL ENGINEERING JOURNAL · 2024 · IF 13.3

Double-hindered phenolic SiO2 composites with excellent oxidation resistance and thermal stability for enhanced thermal oxidation stability of PPS

Weilong Cai,Jian You,Wei Wang,Huaiyin Chen,Longmin Liu,Yuhan Ma,Jianying Huang,Yuying Zheng,Yuekun Lai

In recent years, loading antioxidants onto inorganic nanoparticles has attracted increasing interest. However, the existing studies not only have low antioxidant loading efficiency, but also ignore the relationship between structural changes and antioxidant properties before and after antioxidant modification, greatly limiting the improvement of the antioxidant properties of composites and their application scope. In this work, we successfully prepared bis-hindered phenolic antioxidants containing silica hydroxyl groups (Bis-mAO) and loaded them onto silicon dioxide (SiO 2 ) to get the nanocomposites (Bis-mAO-SiO 2 ). The melt blending method further prepared the corresponding polyphenylene sulfide (PPS)/Bis-mAO-SiO 2 composites. The results showed that the higher antioxidant loading and more suitable antioxidant structure made Bis-mAO-SiO 2 possess excellent antioxidant properties. The prepared PPS/Bis-mAO-SiO 2 composites remained stable under high temperatures and oxygen environments. Impressively, the maximum weight loss rate temperature of PPS/Bis-mAO-SiO 2 was increased by 11.60 °C compared to that of PPS, and after accelerated thermal oxidation at 220 °C for 24 h, the relative intensity ratio between O and C of PPS/Bis-mAO-SiO 2 only increased to 0.086, much lower than 0.132 for PPS. Moreover, the viscosity of PPS/Bis-mAO-SiO 2 only increased by 29.05 % and 88.75 % after accelerated thermal oxidation at 220 °C for 12, 24 h. Compared, PPS's viscosity increased substantially by 79.22 % and 250.3 %, respectively. This meant that the Bis-mAO-SiO 2 successfully achieved a synergistic integration of high antioxidant properties and thermal stability, implying that the work offered a strategy for fabricating high-temperature resistant antioxidant composites.

CAS / MDL: 20170-32-5 1760-24-3
研究领域: 材料科学 · 化学工程
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