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N-苯基马来酰亚胺
JOURNAL OF APPLIED POLYMER SCIENCE · 2025 · IF 2.8

Synthesis and Characterization of EPBT Low Temperature Cured Cationic Photosensitive Resin

Ruobing Xu,Qingming Xu,Wenfei Li,Yuming Liu,Yunhui Li,Jianwei Zhu,Jianhua Tang

This paper addresses the issue of high post-baking temperature (230°C) in the photolithography process of liquid crystal displays under ultraviolet irradiation by designing and preparing a low-temperature curing cationic photosensitive resin. First, a monomer containing carbon – carbon double bonds and bis-epoxy groups, (Z)-1,4-bis(oxiran - 2-ylmethoxy)but-2-ene (EPBT), was synthesized via the Williamson ether synthesis method. Subsequently, poly(methacrylic acid/methylmethacrylate/ N- phenylmaleimide/(Z)-1,4-bis(oxiran - 2-ylmethoxy)but-2-ene/oxetane methacrylate) photosensitive resin (PMMENL) was prepared by radical polymerization of various monomers. The structure of the EPBT monomer and the polymer was characterized, along with their properties. Finally, the prepared resin was uniformly mixed with photoinitiators, solvents, and other components, and micro-patterns on the mask were obtained through the photolithography process. The resolution and morphology of the patterns were examined. The results indicate that the thermal stability of the resin improved after the incorporation of N- phenylmaleimide, with a thermal decomposition temperature of approximately 225°C when the weight loss reached about 10%. Compared to the conventional post-baking temperature of 230°C required for LCD photoresists, the post-baking temperature of PMMENL resin with EPBT monomer was significantly reduced to 150°C, while maintaining an adhesion strength of 8 MPa, equivalent to that of commercially available polyacrylic photosensitive resins baked at 230°C.

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JOURNAL OF THERMOPLASTIC COMPOSITE MATERIALS · 2021 · IF 3.33

Structure and properties of heat-resistant ABS resins innovated via MSAMI random copolymer

BY Hou,L Ren,YN Sun,MY Zhang,HX Zhang

This work proposed an efficient method to synthesize acrylonitrile-butadiene-styrene (ABS) copolymer and α-Methylstyrene (α-MSt)/N-phenylmaleimide (NPMI)/Acrylonitrile (AN) (MSAMI) random copolymer via emulsion polymerization, aiming to combine the excellent heat resistance of MSAMI and numerous advantages of ABS resin including mechanical properties, processing and recyclability. The effects of the MSAMI content and α-MSt/AN ratio on the thermal performance, mechanical properties and the morphology of heat-resistant ABS were investigated by FITR, dynamic mechanical analyses (DMA), Vicat Softening Temperature (VST), Thermogravimetric Analysis (TGA) and Scanning Electron Microscope (SEM). As a result, the heat-resistant of ABS resin was obviously enhanced by MSAMI, and its glass transition temperature (Tg) could be extended with the increase of NPMI content. The Tg could reach 173°C when NPMI content was 20% at the same trend as the VST. Synthetically, the contradiction between the heat resistance and mechanical properties of ABS resin reached a good balance when the NPMI content was 15% and α-MSt/AN ratio was 69/31. In SEM, the fracture morphology of the heat-resistant ABS resin was gradually tended to be smooth with the increase of the NPMI content. Therefore, the MSAMI random copolymer was successful prepared, which provided insight for the synthesis of heat-resistant modifiers and promoted the potential application of heat-resistant modifiers in automobiles and aircraft.

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Science China-Chemistry · 2023 · IF 9.6

Design and synthesis of thiol-terminated imidothioether oligomer as thermally latent hardener and modifier for high-performance epoxy/thiol thermosets

Liu Xing,Zhou Jianjun,Liu Shumei,Zhao Jianqing

Conventional base-catalyzed epoxy/aliphatic thiol systems have a poor storage stability, and are impossible to be one-pot systems. A widely accepted solution is to use the latent catalysts, which are usually insoluble anionic initiators sensitive to impurities and moisture, and have many limitations in practical use. In this work, a soluble thiol-terminated imidothioether oligomer (TPI) was synthesized and used as a latent hardener and modifier to prepare one-pot epoxy/thiol systems without the latent catalysts. The latent behavior and curing mechanism of epoxy systems (EP/TPI series), consisted of bisphenol A diglycidyl ether (DGEBA), pentaerythritol tetrakis(mercaptoacetate) (PETMP) and TPI, were proposed. The thiol exchange reaction between TPI and PETMP preceded the curing reaction of DGEBA, and produced aromatic thiols, which were unreactive at ambient conditions and reacted with DGEBA to form the thermosets at temperatures above 130 °C. At the loading of 24.4 wt% TPI, the epoxy system (EP/TPI-3)had a shelf life of 13 days and was completely cured within 20 min at 180 °C. Meanwhile, the catalyst-free curing process of EP/TPI-3 system was insensitive to impurities and moisture. Furthermore, the thermal and mechanical properties of EP/TPI-3 thermoset were simultaneously improved, thereinto, the glass transition temperature, Young’s modulus and ultimate tensile strength were increased by 16.7 °C, 12.9%, and 13.6%, respectively, compared with those of the commercial DGEBA/PETMP thermoset. This work shows that TPI has the potential to be a powerful alternative to commercial latent catalysts, and EP/TPI thermosets with high performance have broad application prospects.

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POLYMER · 2019 · IF 3.771

Synthesis of poly(2-dimethylaminoethyl methacrylate)-block- poly(styrene-alt-N-phenylmaleimide) and its thermo-tolerant nanoporous films prepared by selective swelling

Jiemei Zhou,Chenxu Zhang,Cailong Shen,Yong Wang

Block copolymers (BCPs) are interesting precursors to nanoporous films with well-defined and tunable porosities. So far, BCPs with polystyrene (PS) as the majority block are predominantly used, hindering the using of produced nanoporous films at elevated temperatures. Herein, we propose to use BCPs with poly (styrene- alt - N -phenylmaleimide) (P( S - alt -NMI)) as the majority block to develop thermally stable nanoporous films considering that this alternative copolymer has a much higher glass transition temperature than PS. We synthesized BCPs of poly (2-dimethylaminoethyl methacrylate) (PDMAEMA) and P( S - alt -NMI) (PDMAEMA- b -P( S - alt -NMI)) with four different block ratios by reversible addition-fragmentation chain transfer (RAFT) polymerization. The swelling behaviors of these BCPs in various solvents were investigated, and we found that nanoporosities will be generated in the BCP films following the mechanism of selective swelling induced pore generation when single solvents or solvent pairs having strong affinity to PDMAEMA and moderate affinity to P( S - alt -NMI) were used as the swelling agents. The pore sizes and porosities of thus-produced nanoporous films can be flexibly tuned by changing the compositions of the BCPs and the swelling conditions. Because of the excellent thermal stability of P( S - alt -NMI) blocks the nanoporous BCP films exhibited excellent thermal tolerance and they maintained intact at a temperature as high as 158 °C while the PS-based BCPs started to deform at the temperature of 75 °C. This thermal tolerance is very much desired in many applications, for example, high-temperature disinfection for medical purposes.

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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2018 · IF 3.141

Novel Synthesis of Down-/Up-Conversion Fluorescent Oligo(2-pyrazoline)s

Yan Li,Tao Li,Long-Qiang Xiao,Yue-Fei Zhang

The polycondensation of 2-pyrazolines is presented. The products are oligomers with the five-membered rings of the 2-pyrazoline as the backbone and the reaction is a polycondensation reaction by decomposition of ROH from the hydrogen atom in the −NH– group and the −OR in the ester group. Metal catalysts, reaction periods, and the addition amounts of the catalyst are investigated to optimize the reaction conditions. The products are down-/up-conversion fluorescence molecules that can significantly enhance cell imaging through the synchronized excitation of visible and near-infrared light and may be widely used in other optical fields.

CAS / MDL: 34946-82-2 941-69-5
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POLYMER · 2024 · IF 4.1

Highly enhanced toughness and thermal oxygen aging resistance of PA 6 via novel designed macromolecular antioxidants

Lulu He,Jinfen Lou,Xiang Nie,Min He,Qiao Fan,Jifei Yang,Yufei Liu,Shuhao Qin,Jie Yu

Polyamide 6 (PA6) is widely utilized, yet it confronts challenges such as susceptibility to thermal oxidative aging and high sensitivity to notch impact during usage. In addressing these issues, two novel toughening macromolecular antioxidants, 3-(3,5-di- tert -butyl-4-hydroxyphenyl) propionic acid 2-acrylamidoethyl ester styrene copolymer (PAS) and 3-(3,5-di- tert -butyl-4-hydroxyphenyl) propionic acid 2-acrylamidoethyl- N -phenylmaleimide copolymer (PAN), were synthesized via free radical copolymerization. Upon incorporation into PA6, their effects on PA6 performance were investigated. Relative to pure PA6, PA6/PAN and PA6/PAS exhibited significant improvements in fracture elongation, with increases of 136.91 % and 313.83 % respectively, along with notch impact strength enhancements of 18.55 % and 24.89 % respectively. This enhancement can be attributed to PAN and PAS reducing the hydrogen bond density between PA6 molecular chains. Subsequent long-term accelerated thermal aging tests conducted at 150 °C, as well as performance testing of samples before and after aging, revealed that the aging of PA6/PAN and PA6/PAS could be delayed by 4–12 days. The exceptional anti-thermal oxidative aging ability and toughening effect of these two macromolecular antioxidants in PA6 showcase promising prospects for its expanded applications.

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Materials Today Chemistry · 2024 · IF 6.7

Photo-thermal double-crosslinked second-order nonlinear optical materials with high orientation stability

Xingyue You,Peng Wang,Yongke Tan,Yujing Li,Jieqiong Wang,Zixuan Li,Yuhui Ao,Ming Li

Second-order nonlinear optical (NLO) materials have become the core of photonic devices. The stability of chromophore arrangement is a key factor limiting the service life of materials. In this study, we employed a novel photo-thermal double-crosslinking networks to enhance the orientation stability of chromophore for the first time by integrating photo and thermal crosslinking techniques. Benzocyclobutene (BCB) and double bonds were introduced as crosslinked units on the polymer and chromophore, respectively. Thermal crosslinking is achieved through the Diels-Alder (D-A) reaction between BCB, while photo crosslinking is accomplished via a thiol-ene click reaction. The UV–vis spectra results demonstrate that photo-thermal double-crosslinking can provide a certain level of protection to the chromophore against decomposition at elevated temperature. Maximum electro-optic coefficient ( r 33 ) of BCB-based double-crosslinking networks is 23.3 p.m. V −1 (at 1.3 μm, 25 wt%). Little difference is observed between the results of photo-thermal double-crosslinking polymer ( r 33 = 5.8 pm V −1 , 10 wt%) and host-guest polymer ( r 33 = 6.7 pm V −1 , 10 wt% ), illustrating that the double-crosslinking reaction does not impair r 33 . The analysis of the thermal simulated depolarization (TSD) curve indicates that the orientation stability of the double-crosslinked network structure (T peak  = 162 °C) is significantly enhanced compared to single thermal crosslinking (T peak  = 158 °C) or single photo crosslinking (T peak  = 144 °C), owing to the dual fixation of the chromophore through both photo and thermal crosslinking processes. It could be concluded that the enhancement of orientation stability does not come at the cost of the electro-optic coefficient. In a word, photo-thermal double-crosslinked second-order nonlinear materials are expected to be a promising option to research NLO optical applications.

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ACS Applied Polymer Materials · 2025 · IF 4.7

Phosphorus-Containing Polyimidothioether as a Latent Curing Agent and Flame Retardant for One-Component Epoxy Resins

Xing Liu,Zhenzhi Liu,Houqun Xiao,Lijing Han,Jianqing Zhao

The development of epoxy/thiol resins with long shelf life, satisfactory flame retardancy, good heat resistance, and high mechanical strength is challenging but essential for advanced applications. In this study, a phosphorus-containing polyimidothioether (DTPI) with good solubility was efficiently synthesized and employed as both a thermolatent curing agent and a flame retardant for the mixture of pentaerythritol tetra(3-mercaptopropionate) (PETMP) and diglycidyl ether of bisphenol A (DGEBA). The thiol exchange reaction between DTPI and PETMP occurred spontaneously prior to the ring-opening reaction of DGEBA, and the resulting aromatic thiols were dormant at 30 °C but reacted with DGEBA at temperatures above 130 °C, leading to good thermal latency of EP/DTPI systems. With a DTPI loading of 24.2 wt %, the EP/DTPI-3 system showed a shelf life of 20 days. Furthermore, the cured EP/DTPI exhibited simultaneously improved flame retardancy as well as enhanced thermal and mechanical properties. For example, the EP/DTPI-3 thermoset attained the UL-94 V0 rating and exhibited a 19.5 °C, 48.6%, and 32.1% increase in the glass transition temperature, ultimate tensile strength, and Young’s modulus, respectively, compared with the traditional DGEBA/PETMP thermoset. This work presents a simple and effective strategy for preparing flame-retardant and high-performance one-component epoxy resins with good thermal latency by bespoke multifunctional polyimidothioethers.

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