JOURNAL OF APPLIED POLYMER SCIENCE
·
2024
·
IF 2.7
Youwei Zhu,Jiaming Liu,Jingjing Qin,Dingsong Wang,Wanyan Li,Chang-An Xu,Liyan Liang
The poor dielectric properties of epoxy resins limit their application in microelectronics, and active ester curing agent is an effective means to enhance the dielectric properties of epoxy resins. However, the phenyl active ester curing resins nowadays have the problem of low mechanical properties. In this work, a novel naphthalene-based active ester-cured resveratrol epoxy resin system (REP/NDA) was prepared for the first time. Compared with the phenyl-active ester-cured epoxy resin (REP/PDA), the naphthyl-active ester prepared epoxy resin has obvious advantages in mechanical properties. The experimental results indicated a tensile strength measurement for REP/NDA at 91.9 MPa, the tensile strength of REP/PDA was 65.3 MPa, and the tensile strength of REP/NDA was 141% of that of REP/PDA. The prepared REP/NDA epoxy resin exhibits favorable dielectric properties, evidenced by a dielectric constant of 3.02 at 10 MHz and a dielectric loss of 0.0042, very good thermal stability ( T 5% of 379°C), excellent water absorption (only 0.49% for 7 days from 2 to 8°C) and good dimensional stability (coefficient of thermal expansion below T g of 77 ppm). The first synthesis of naphthalene-based active ester curing agent offers a reference for creating new low dielectric epoxy resin materials that work out exceptionally.
研究领域:
材料科学
·
高分子化学
·
微电子
✓ 已验证
DOI
高影响因子
ACS Sustainable Chemistry & Engineering
·
2024
·
IF 7.1
Chang-An Xu,Wenzi Liang,Shaoheng Yang,Yang Hu,Zhuohong Yang,Hao Pang
At present, the dielectric constant of anticorrosion coatings is relatively high, which limits its application in electronic devices, and the epoxy curing agent currently used is mostly from fossil resources, which is not conducive to sustainable development. Therefore, a vanillin-based active ester curing agent (VAEI) containing an imine bond was prepared by the esterification reaction and amine aldehyde condensation reaction. Subsequently, VAEI and amino curing agents cured the epoxy resin to prepare a coating with antibacterial properties, low dielectric, and corrosion resistance. The results showed that when the content of VAEI was 5 wt %, its anticorrosion properties were basically equivalent to that of the coating prepared by the pure amino curing agent. When the content of VAEI was 14 wt %, the impedance modulus of the coating was as high as 1.00 × 109 Ω cm2 after soaking in salt water for 150 days, which was 2 orders of magnitude higher than that of the control group. In addition, the dielectric constant of the coating at 10 MHz decreased from 4.16 to 3.64, and it also exhibited excellent antibacterial properties against Escherichia coli (7.0%) and Staphylococcus aureus (19.6%). This work expands the added value of vanillin and provides a reference for the preparation of various performance coatings.
研究领域:
材料科学
·
化学工程
·
生物学
✓ 已验证
产品关联
DOI
高影响因子
HIGH PERFORMANCE POLYMERS
·
2021
·
IF 2.161
Huifa Meng,Qian Zhang,Maoping Lu,Zhencai Qu,Bing Chen,Chang-an Xu,Mangeng Lu
Benzene-1,3,5-triyl tribenzoate (TBB), both 3,5-bis(benzoyloxy)benzoate-terminated poly (aryl ether ketone) oligomers (BPAPK and TMPK), containing active ester (Ph−O−(C=O)− structure), were prepared and served as curing agents for dicyclopentadiene novoalc epoxy (DCPD). The curing kinetics and properties of three epoxy thermosets were systematically investigated. The model reaction of TBB and glycidyl phenyl ether was designed to understand the curing mechanism of oxirane ring with active ester. TMPK/DCPD displays the lowest reaction activation energy, which is the result of the combined influence of free volume and diffusion. In addition, TMPK/DCPD has the highest Tg value (218°C), which enhances 34.6% and 42.5% compared with BPAPK/DCPD and TBB/DCPD, respectively. Meanwhile, TMPK/DCPD also shows superior dielectric and water resistance properties due to no secondary alcohol generated after curing and hydrophobic tetramethyl-substituted biphenyl structure. Herein, TMPK/DCPD as high-performance epoxy thermosets has potential applications in electronic packaging fields.
研究领域:
材料科学
·
化学工程
✓ 已验证
DOI
高影响因子
Polymer Chemistry
·
2023
·Vol. 14
·期 14
·1665-1679
·
IF 4.6
Jiaming Liu,Xiaohong Liu,Xiaohua Cui,Jingjing Qin,Mengqin Wu,Lifu Fu,Min Shi,Dingsong Wang,Liyan Liang
Using biomass resources to prepare thermosets seems to have become a trend in the future of a sustainable society, and an active ester may be an excellent epoxy hardener for the electronic packaging field. In this work, we synthesized a resveratrol-derived epoxy (REP) and two resveratrol-derived active ester hardeners (triacetyl resveratrol (TAR), tri(m-toluoyl) resveratrol (TTR)), and then two resveratrol-derived bio-based epoxy thermosets (REP/TAR, REP/TTR) were prepared by the curing reaction of the epoxy and the hardener. The properties and structures of the thermosets were characterized and investigated. Results showed that the properties of REP/TAR in all aspects were better than those of REP/TTR; to be specific, the REP/TAR exhibited a higher gel fraction and better solvent resistance, indicating its better cross-linked network; the glass transition temperature of REP/TAR was higher and reached 177 °C (DMA) and the thermal stability of TEP/TAR was also better and the char yield at 600 °C was 46.5%. The main reason could be that the steric hindrance of acetyl groups in REP/TAR was smaller than that of m-toluoyl groups in REP/TTR. What's more, a novel analytical method was proposed for use in thermogravimetric analysis (TGA) to analyze the degradation process of thermosets, revealing a degradation process that was unique to the active ester cured epoxy thermosets. In all, the resveratrol-derived biobased epoxy thermosets could be a promising candidate for replacing fossil-derived thermosets and have potential application in the electronic packaging field, and the study on active ester hardeners might inspire the design and synthesis of subsequent active ester hardeners.
研究领域:
材料科学
·
有机化学
·
可持续发展
✓ 已验证
产品关联
DOI
高影响因子
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
·
2024
·
IF 3.8
Jiaming Liu,Jingjing Qin,Xiaohua Cui,Min Shi,Dingsong Wang,Youwei Zhu,Wanyan Li,Liyan Liang,Chaolong Yang
Cycloaliphatic epoxy resins are known for their synthesis process that eliminates hydrolyzable chlorine, thus avoiding the hydrolysis of hydrolyzable chlorine to hydroxyl groups in conventional epoxies, which is very favorable for the preparation of low dielectric epoxy resins. The curing process using active ester generates no hydroxyl groups, also indicating a promising approach for producing low dielectric epoxy resins. However, the resistance of cycloaliphatic epoxy to nucleophilic reactions restricts it from reacting usually only with anhydrides. This study investigates the reactivity of the active ester with cycloaliphatic epoxy, demonstrating its capability to undergo complete curing reactions at temperatures near 150 °C. Factors influencing this process, including the volatilization of the catalyst DMAP and its reactivity, are examined. Two types of cycloaliphatic epoxies (3,4-epoxycyclohexylmethyl-3′,4’-epoxycyclohexane carboxylate (EEC) and bis (3,4-epoxycyclohexylmethyl) adipate (BEA)) are combined with an active ester hardener, triacetyl resveratrol (TAR), to prepare epoxy resins. The activation energies for the curing reactions are determined, and the optimal concentration of catalyst 4-dimethylaminopyridine (DMAP) is identified for each resin. The use of catalysts at specific concentrations results in resins with superior mechanical properties (91.7 and 71.4 MPa for EEC/TAR and BEA/TAR), excellent thermal stability (Td5% of 354 and 347 °C), and good dielectric properties (dielectric constant of 3.68 and 3.95 at 10 MHz), outperforming anhydride-cured cycloaliphatic epoxy resins. These findings expand the selection of hardeners for cycloaliphatic epoxy resins and highlight the potential of the prepared resins in electronic packaging materials, offering enhanced properties suitable for various applications.
研究领域:
材料科学
·
化学工程
✓ 已验证
产品关联
DOI
高影响因子
POLYMER
·
2025
·
IF 4.5
Yonghao Lv,Hongyan Li,Zhubao Shao,Zhiming Jiang
Cycloaliphatic epoxy resins exhibit excellent dielectric properties but are often harder to be flame retarded. To address this issue, a magnolol-derived active ester DDA was synthesized and employed to prepare flame-retardant cycloaliphatic epoxy resins through the intrinsic incorporation of a phosphaphenanthrene moiety (DOPO). Compared with anhydride MHHPA-cured resins, DDA demonstrated superior char-forming capability and enhanced the compactness of carbon residues. Under equivalent phosphorus loadings, the DDA-cured resin (CFDAP) exhibited a significantly higher limiting oxygen index (LOI) value of 30.2 %, notably surpassing the 26.7 % LOI of the MHHPA-cured counterpart. CFDAP effectively achieved reductions of 44 % in peak heat release rate and 50 % in total heat release during combustion. Importantly, ether bonds instead of ester bonds in the main chain of CFDAP enhanced the thermal stability and tensile strength relative to MHHPA-cured system. The chemical integration of DOPO moiety further improved the dielectric properties of epoxy resins at high frequencies by increasing free volume within the matrix. Collectively, the active ester curing agent DDA enables simultaneous enhancements in flame retardancy, thermal stability, mechanical properties, and dielectric performance of epoxy resins, presenting an efficient strategy for designing advanced electronic packaging materials suitable for high-frequency and high-speed electronic communication.
研究领域:
高分子科学
·
材料工程
·
阻燃材料
·
介电材料
·
电子封装材料
✓ 已验证
产品关联
DOI
高影响因子
POLYMER
·
2025
·
IF 4.5
Yunhong Liao,Xiang Wang,Huawei Zou,Pengbo Liu
C-Si bond was widely used to enhance the dielectric characteristics of polymers owing to its inherent low polarity. However, the potential of silicon-containing branched chains for modifying epoxy resins has been rarely explored. In this research, two active esters with silicon-containing branched chains of different chain lengths (DASIO, DASIOL), and another active ester with silicon-free branched chains (DAO) have been synthesized and utilized as curing agents of DCPD epoxy resins. After introducing silicon-containing branched chains, the loss factor (D f ) value of the cured epoxy system was significantly reduced. At 10 GHz, the D f values of DASIO/EP and DASIOL/EP systems were 6.47‰ and 6.82‰ respectively, reflecting decreases of 29.8% and 26% from the DAO/EP system value. With the extension of the chain length of silicon-containing branched chains, the cured epoxy system's dielectric constant (D k ) value exhibited a downward trend. When compared to the DASIO/EP system, the D k value of the DASIOL/EP system showed a reduction from 2.84 to 2.62. The silicon-containing branched chains could improve the flexibility of the cured epoxy system. The elongation at break of DASIOL/EP system was 4.2%, which have increased by 30%, in comparison to the DAO/EP system. In addition, through introduction of silicon-containing branched chains, the cured epoxy system also showed improved thermo-mechanical properties, hydrophobic properties and thermal stability. The research findings indicated that the silicon-containing branched chains were capable of enhancing the dielectric performances of the epoxy system. Additionally, by regulating the length of the silicon-containing branched chains, a balance of mechanical properties, thermal properties, etc. could be achieved. This provided a novel approach for developing low-D f epoxy materials in the electronics industry.
研究领域:
材料科学
·
高分子化学
·
电气工程
·
化学合成
✓ 已验证
产品关联
DOI
高影响因子
PROGRESS IN ORGANIC COATINGS
·
2023
·
IF 6.6
Zhixi Zhao,Xiang Wang,Jizhen Tian,Yunfei Gao,Fei Chen,Shuai Li,Huawei Zou,Pengbo Liu
The production of epoxy resins with low dissipation factor ( D f ) remains an alluring yet challenging task. In this work, we successfully synthesized a novel resveratrol based active ester (ResE) by a one-step method using the renewable resveratrol as raw material. The structure of ResE was characterized using FTIR and NMR techniques. The phenol biphenyl epoxy (SQXN-324) was cured with ResE, the SQXN/ResE system boasted a favorable dielectric constant ( D k ) of 2.78 and dissipation factor ( D f ) of 3.5 × 10 −3 at a high frequency of 10 GHz. Additionally, the SQXN/ResE system exhibited impressive thermal performances, with a 5 % weight loss temperature ( T 5% ) of 368 °C, a residual carbon of 34 wt% at 800 °C in N 2 atmosphere, a glass transition temperature ( T g ) of 154 °C, a coefficient of thermal expansion (CTE) of 61.9 ppm/°C from 25 °C to T g and the CTE of 130 ppm/°C from T g to 250 °C. These findings suggested that a biomass curing agent for epoxy with low D f and high thermal performances were successfully developed, it had potential applications in the high frequency communication field and microelectronics industry.
研究领域:
材料科学
·
化学工程
·
电气工程
✓ 已验证
产品关联
DOI
高影响因子
CHEMICAL ENGINEERING JOURNAL
·
2024
·
IF 13.3
Zhenye Fu,Zirui Ma,Jiuhong Liu,Chunhui Li,Chuanmei Liu,Qidong Wang,Liang Song,Qing Yu,Guiqing Cheng,Yuxi Han,Hailong Liu,Zhongwei Wang
In the pursuit of epoxy thermosets with low dielectric properties and excellent flame retardancy, the 2- (diphenylphosphino)-1,4-benzenediol active ester (DPO-HQ-AE). and 10-(2,5-dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide active ester (DOPO-HQ-AE) were synthesized as bifunctional phosphorus-containing active ester flame retardants. The molecular structures of DPO-HQ-AE and DOPO-HQ-AE were characterized by MS, 1 H NMR, 13 C NMR, 31 P NMR and FTIR. The flame retardancy, thermal stability, crosslink density, water absorption and dielectric properties of active ester cured dicyclopentadiene (DCPD) epoxy resins were investigated. DCPD/DPO-HQ-AE with a phosphorus content of 0.9 wt% passed the UL-94 V-0 test. Meanwhile, DCPD/DOPO-HQ-AE containing 1.2 wt% phosphorus achieved a V-0 rating. DPO-HQ-AE and DOPO-HQ-AE showed noticeable gas-phase flame-retardant mechanism with active phosphorus species in the gas phase of pyrolysis. At the frequency of 1 GHz, the dielectric constant and dielectric loss of DCPD/DPO-HQ-AE-0.9 were 2.67 and 0.0042, respectively. Compared with the unmodified epoxy resin , the dielectric loss was reduced by approximately 5.5 times. The as-prepared epoxy thermosets with high thermal stability, excellent flame retardancy, low dielectric properties and low water absorption satisfied the requirements of high-speed and high-frequency encapsulation materials.
研究领域:
材料科学
·
高分子化学
·
电气工程
✓ 已验证
产品关联
DOI
高影响因子
Journal of Materials Chemistry B
·
2022
·Vol. 10
·期 19
·3687-3695
·
IF 7.571
Zhuangzhang Ma,Jin Sun,Xiaohan Dong,Donglin Gan,Wan Peng,Youxin Li,Weijian Qian,Pingsheng Liu,Jian Shen
Bacterial-associated infection, blood coagulation, and tissue adhesion are severe issues associated with biomedical implants and devices in clinic applications. Here, we report a general strategy to simultaneously tackle these issues on polyurethane (PU)-based substrates. Taking advantage of reversible addition–fragmentation chain transfer (RAFT) polymerization, well-defined zwitterionic/active ester block polymers (pSBMA-b-pNHSMA) with an identical pNHSMA segment (polymerization degree of 15) but varied zwitterionic pSBMA segments (polymerization degrees of 40 and 100) were precisely prepared. The pSBMA-b-pNHSMA block polymers could be easily covalently constructed on PU substrates that were pretreated with a polydopamine coating based on highly efficient anime-active ester chemistry, as evidenced by the water contact angle and XPS tests. The relationship between the length of pSBMA segments in the coating and the antifouling ability of PU substrates was established. The results indicated that block polymers with a pSBMA segment of 40 repeat units could significantly prevent protein adsorption, bacterial/platelet adhesion, and cell attachment on PU substrates within 24 h, while a longer pSBMA segment (repeat units of 100) could endow long-term antibacterial (14 days without biofilm formation) and anti-cell attachment (5 days without cell attachment) properties to the PU substrates. Furthermore, the coating significantly improved the surface lubricating property of PU substrates without compromising on the mechanical property. This strategy may find many applications in PU-based implants and devices.
研究领域:
材料科学
·
生物医学工程
·
聚合物化学
·
表面科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）