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Halogen-Free Epoxy with Enhanced Corrosion Resistance for Microelectronics Packaging via γ SN2 Nucleophilic Substitution

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Chemistry of Materials 2025年第9期37卷 3311-3318页

作者： Qian, Zizhao Zhu, Xiao-Feng Chen, Zhiyu Li, Bo Yang, Guan-Wen Wu, Guang-Peng MOE Key Laboratory of Macromolecular Synthesis and Functionalization Key Laboratory of Adsorption and Separation Materials & Technologies of Zhejiang Province Department of Polymer Science and Engineering Zhejiang University Hangzhou310058 China College of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Hangzhou Normal University Zhejiang Hangzhou311121 China

Bisphenol A diglycidyl ether (DGEBA) is an essential epoxy resin in the microelectronics industry. However, circuit corrosion caused by hydrolyzable chlorine─a persistent issue associated with DGEBA─poses significant challenges in this field. In this study, we present a novel strategy for producing halogen-free DGEBA with high purity (up to 99%) and isolated yield (up to 94%) by utilizing glycidyl sulfonates as the starting material. A distinctive γ SN2 nucleophilic substitution pathway between glycidyl sulfonates and phenolic compounds effectively suppresses the formation of ring-opening byproducts and oligomers, as demonstrated through model reactions and kinetic studies. The scalability and versatility of our method are validated by its straightforward synthesis process and expanded substrate scope. Finally, the halogen-free DGEBA exhibits noncorrosive properties when employed as a matrix resin for prepreg and underfill applications. Our research underscores the potential of glycidyl sulfonate as a viable alternative to epichlorohydrin in large-scale epoxy production for electronics. © 2025 American Chemical Society.

关键词： Corrosion resistance

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Light-driven Self-sustained Rolling of Cylinder Hydrogels with Fast and Anisotropic Responses

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Chinese Journal of Polymer Science 2025年第4期43卷 548-555页

作者： Qing-Li Zhu Han-Lei Cheng Wei-Xuan Liu Yin-Bin Xiao Xin-Lei Wu Josef Breu Wei Hong Zhi-Jian Wang Qiang Zheng Zi-Liang Wu Ministry of Education Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and EngineeringZhejiang UniversityHangzhou310058China Department of Mechanics and Aerospace Engineering Southern University of Science and TechnologyShenzhen518055China Bavarian Polymer Institute and Department of Chemistry University of BayreuthUniversitätsstrasse 3095440BayreuthGermany Institute for Chemical Reaction Design and Discovery Hokkaido UniversitySapporo001-0021Japan

Achieving continuous motions typically requires dynamic external stimuli for cyclic deformation,or crafted geometries with intricate modules to form a self-regulated feedback loop upon static *** is still a grand challenge to realize self-sustained motion in soft robots subject to unchanging environment,without complex geometry or a control *** this work,we report soft robots based on an anisotropic cylindrical hydrogel showing self-regulated,continuous rolling motions under constant light *** robots are animated by mirror-symmetry-breaking induced by photothermal strain *** self-sustained motion is attributed to the fast and reversible deformation of the gel and the autonomous refresh of the irradiated region during the rolling *** hydrogel robots can reach a rolling speed of 1.27 mm·s^(-1)on a horizonal surface and even climb a ramp of 18°at a speed of 0.57 mm·s^(-1)in an aqueous ***,the hydrogel robots can overcome an obstacle,with rolling direction controllable through irradiation angle of the light and local irradiation on selective *** work suggests a facile strategy to develop hydrogel robots and may provide unforeseen inspirations for the design of self-regulated soft robots by using other intelligent materials.

关键词： Self-sustained motions Light-driven Rolling Anisotropic hydrogels Soft robots

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FERROFERRIC OXIDE/CHITOSAN SCAFFOLDS WITH THREE-DIMENSIONAL ORIENTED STRUCTURE

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Chinese Journal of Polymer Science 2012年第3期30卷 436-442页

作者：胡巧玲 Key Laboratory of Macromolecular Synthesis and Functionalization Ministry of EducationZhejiang University

A facile approach to construct ferroferric oxide/chitosan composite scaffolds with three-dimensional oriented structure has been explored in this research. Chitosan and ferroferric oxide are co-precipitated by using an in situ precipitation method, and then lyophilized to get the composite scaffolds. XRD indicated that Fe304 was generated during the gel formation process, and increasing the content of magnetic particles could destruct the crystal structure of chitosan. When the content of magnetic particles is lower than 10%, the layer-by-layer structure and wheel spoke structure are coexisting in the scaffolds. Increasing the content of magnetic particles, just layer-by-layer structure could be observed in the scaffolds. Ferroferric oxide particles were uniformly distributed in the matrix, the size of which was about 0.48 gm in diameter, 2 gm in length. Porosity of magnetic chitosan composite scaffolds is about 90%. When the ratio of ferroferric oxide to chitosan is 5/100, the compressive strength of the material is 0.4367 MPa, which is much higher than that of pure chitosan scaffolds, indicating that the layer-by-layer and wheel spokes complex structure is beneficial for the improvement of the mechanical properties of chitosan scaffolds. However, increasing the content of ferroferric oxide, the compressive strength of scaffolds decreased, because of the decreasing of chitosan crystallization and aggregation of magnetic particles as stress centralized body. Another reason is that the layer-by-layer and wheel spokes complex structure makes bigger contributions for the compressive strength than the layer-by-layer structure does. Three-dimensional ferroferric oxide/chitosan scaffolds could be used as hyperthermia generator system, improving the local circulation of blood, promoting the aggradation of calcium salt and stimulating bone tissue regeneration.

关键词： Chitosan Ferroferric oxide Scaffold Three-dimensional oriented structure.

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MECHANICAL AND THERMAL PROPERTIES OF NANOSIZED TITANIUM DIOXIDE FILLED RIGID POLY(VINYL CHLORIDE)

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Chinese Journal of Polymer Science 2013年第2期31卷 325-332页

作者： Yun-xiang Zhang 宋义虎 Qiang Zheng Key Laboratory of Macromolecular Synthesis and Functionalization of Ministry of Education Department of PolymerScience and Engineering Zhejiang University

Nano-sized rod-like titanium dioxide （TiO2） filled rigid poly（vinyl chloride）（PVC） nanocomposites were prepared by using injection-molding method. Vicat, Charpy impact and tensile tests as well as thermogravimetric and dynamic mechanical analyses were used to characterize the structure and properties of the nanocomposites. The results showed that nano-TiO2 could improve Vicat softening temperature and also improve thermal stability of PVC during the stages of dehydrochlorination and formation of carbonaceous conjugated polyene sequences, which can be ascribed to restriction of the nanoparticles on the segmental relaxation as being evidenced by raises in glass transition and β-relaxation temperatures of PVC upon filling TiO2. Addition of TiO2 nanoparticles less than 40 phr （parts per hundreds of resin） could significantly improve impact strength of the composites while the TiO2 agglomeration at high contents leads to a reduction in impact toughness.

关键词： Poly(vinyl chloride) (PVC) Titanium dioxide (TiO2) Thermal property Mechanical property Impact strength.

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PERVAPORATION FOR SEPARATING BENZENE/CYCLOHEXANE MIXTURE BY P(AA-MA) COPOLYMER MEMBRANES

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Chinese Journal of Polymer Science 2011年第3期29卷 288-295页

作者：朱蔚璞 Department of Polymer Science and Engineering Key Laboratory of Macromolecular Synthesis and Functionalization (Ministry of Education)Zhejiang University

P（AA-MA） copolymers composed of acrylic acid and methyl acrylate with different molecular weights and sequence structures were synthesized by combination of ATRP and selective hydrolysis. These copolymers were used as membrane materials to separate benzene/cyclohexane mixture by pervaporation. The effects of molecular weight and sequence structure of the copolymers on the pervaporation performance were investigated in detail. For the random copolymers, the permeate flux decreased rapidly with the increasing of molecular weight. The separation factor was also influenced by the molecular weight, which was changed from no selectivity to cyclohexane selectivity with increasing the molecular weight. Contrarily, the block copolymer membrane showed good benzene selectivity with separation factor of 4.3 and permeate flux of 157 g/（m2h） to 50 wt% benzene/cyclohexane mixture.

关键词： Pervaporation ATRP Copolymer Molecular weight Sequence structure Benzene/cyclohexane mixture.

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Mediating the Migration of Mesenchymal Stem Cells by Dynamically Changing the Density of Cell-selective Peptides Immobilized on β-Cyclodextrin-modified Cell-resisting Polymer Brushes

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Chinese Journal of Polymer Science 2020年第2期38卷 126-136,I0005页

作者： Wang Du De-Teng Zhang Xue-Mei Wang Tan-Chen Ren Chang-You Gao Ministry of Education Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and Engineering Zhejiang University

Dynamic control of mesenchymal stem cell(MSC)behaviors on biomaterial surface is critically involved in regulating the cell fate and tissue ***,a stimuli-responsive surface based on host-guest interaction with cell selectivity was developed to regulate migration of MSCs in situ by dynamic display of cell-specific ***-grafted MSC-affinitive peptides(EPLQLKM,Azo-E7)were grafted toβ-cyclodextran(β-CD)-modified poly(2-hydroxyethyl methacrylate)-b-poly(2-hydroxyethyl methacrylate-co-glycidyl methacrylate)(PHG)brushes,which were prepared by using surface-initiated atom transfer radical polymerization(SI-ATRP).X-ray photoelectron spectroscopy(XPS),quartz crystal microbalance(QCM),and water contact angle were used to characterize their structure and *** adhesion assay showed that the combination effect of resisting property of PHG and MSC-affinity of E7 could promote the selective adhesion of MSCs over other types of cells such as RAW264.7 macrophages and NIH3 T3 fibroblasts to some ***-Vis spectroscopy proved that the competing guest molecules,amantadine hydrochloride(Ama),could release Azo-E7 peptides from the CD surface to different extents,and the effect was enhanced when UV irradiation was employed *** a result,the decrease of cell adhesion density and migration rate could be achieved in *** cell density and migration rate could be reduced by over 40%by adding 20μmol/L Ama,suggesting that this type of surface is a new platform for dynamic regulation of stem cell behaviors in situ.

关键词： Host-guest interaction MSC-affinitive peptide Dynamic surface Cell adhesion Cell migration

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Mechanism of Janus Polymerization: A DFT StudyFig. S3 Energy profiles of anionic polymerization in Stage I under B3LYP/6-31G(d,p)(blue) and B3LYP/aug-cc-p VTZ//B3LYP/6-31G(d,p)(red). Scheme S1. Propagation process of CL/THF on cationic side in Stage I of J

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Chinese Journal of Polymer Science 2019年第10期37卷 990-994,I0004页

作者： Tian-Wen Bai Xu-Feng Ni Jun Ling Zhi-Quan Shen Ministry of Education Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and Engineering Zhejiang University

Janus polymerization is featured as a combination of cationic and anionic growing ends in one living polymer chain. In the copolymerization of THF and CL catalyzed by lutetium triflates and initiated by propylene oxide, three stages are identified by kinetic study including(1) fast cationic polymerization with slow anionic one,(2) fast anionic polymerization with dormant cationic one, and(3)reactivation of cationic polymerization with coupling of anionic and cationic chain ends. In this work, density functional theory(DFT)calculation is employed to investigate the reaction details of ionic polymerization and dormancy. A “tripedal crow” configuration is proposed to illustrate the unique high-coordinated ligand exchange configuration in anionic polymerization in different stages. The trigger of dormancy is determined as chain structures rather than concentration of triflate anion according to both calculation and experimental results.

关键词： Rare earth metal catalysts Ring-opening polymerization Ionic polymerization Reaction mechanism Quantum chemicalcomputation

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Facile synthesis of Functional Poly (ε-caprolactone) via Janus Polymerization

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Chinese Journal of Polymer Science 2019年第9期37卷 858-865页

作者： Huan Qiu Zhe-Ning Yang Jun Ling Ministry of Education Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and Engineering Zhejiang University

Functionalized aliphatic polyesters attract increasing attentions as biocompatible and biodegradable polymers with broad applications in biological science. In this contribution, we propose a facile and controllable synthetic technique for functional poly(ε-caprolactone)(PCL) via Janus polymerization, which comprises cationic ring-opening copolymerization (ROP) of ε-caprolactone (CL) with 3,3-bis(chloromethyl)oxacyclobutane (CO) and (coordinated) anionic ROP of CL at a single propagating chain by rare earth metal triflates (RE(OTf)3)and propylene oxide, thus generating block copolymers in one step. The compositions of the copolymers of poly(CLb-(CL-r-CO)) can be modulated by various RE(OTf)3. Scandium triflate catalyzes Janus polymerization to yield the copolymers containing the highest CO contents among all the RE(OTf)3 catalysts used with complete conversion of CL. The chlorine in CO repeating units is ready to be transferred into azide group which affords the modification sites to react with 9-ethynyl-9-fluorenol and mPEG-alkyne, respectively, via copper(I)-catalyzed azide-alkyne cycloaddition reaction with quantitative conversions of azides, as confirmed by FTIR analyses. According to NMR and SEC analyses, copolymers (PCC-g-PEG) bearing a homo-PCL block and a PEG-grafted block of poly(CO-co-CL) demonstrate well-defined chemical structures. The investigations on thermal properties reveal the strong phase separation between PCL and PEG blocks. The amphiphilic PCC-g-PEG is able to sei住assemble into micelles in aqueous solution while cylindrical and lamellar morphologies are observed in bulk. We provide an efficient protocol to synthesize functional PCL combining onestep Janus polymerization and precise post-polymerization click reaction.

关键词： Janus polymerization Functional poly(ε-caprolactone) Poly(3,3-bis(chloromethyl)oxacyclobutane) Ring-opening polymerization Rare earth metal catalysts

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Tough Poly(L-DOPA)-containing Double Network Hydrogel Beads with High Capacity of Dye Adsorption

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Chinese Journal of Polymer Science 2018年第11期36卷 1251-1261页

作者： Pei-Bin Zhang An-Qi Tang Zhang-Hui Wang Jing-Yu Lu Bao-Ku Zhu Li-Ping Zhu Ministry of Education Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and Engineering Zhejiang University

Developing a low-cost and well-recyclable adsorbent with high adsorption capacity is greatly desirable in dye wastewater treatment. Here, we demonstrate a kind of novel tough and reusable hydrogel beads with quite high capacity of dye adsorption via incorporating mussel-bioinspired poly（L-DOPA）（PDOPA） into alginate/poly（acrylamide） double network （DN） hydrogels. The synthesized PDOPA nanoaggregates were introduced into the DN hydrogels by simple one-pot mixing with the monomers prior to polymerization. The fabricated hydrogel beads exhibited high mechanical strength and good elastic recovery due to the interpenetrating Ca2＋-alginate and poly（acrylamide） networks. It was shown that the beads exhibited relatively high dye adsorption capacity compared to other adsorbents reported in literature, and the introduction of PDOPA with an appropriate amount raised the adsorption capacity. It is believed that the addition of PDOPA and the matrix of double network architecture contributed synergistically to the high adsorption capacity of hydrogel beads. Moreover, the desorption of dyes could be easily realized via rinsing in acidic water and ethanol solution. The hydrogel beads remained the high adsorption capacity even after 5 times of adsorption and desorption cycles. This tough and stable hydrogel with high adsorption capacity may have potential in treatment of dye wastewater released by textile dyeing industry.

关键词： Dye adsorption Hydrogel beads Poly(L-DOPA) Double network High strength

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Comparative Studies on Properties of Polymers with Bulky Side Groups Synthesized by Cyclopolymerization of α,ω-Dienes and α,ω-Diynes

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Chinese Journal of Polymer Science 2019年第2期37卷 149-156页

作者： Shao-Fei Song Xiao-Yu Liu Hao Zhang Zhi-Sheng Fu Jun-Ting Xu Zhi-Qiang Fan Ministry of Education Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and Engineering Zhejiang University

Four polymers containing five-membered rings in the main chain, with or without conjugation structure along the backbone and with or without conjugated pendent groups, were designed and synthesized by metathesis cyclopolymerization of functionalized α,ω-diynes, and cyclopolymerization of functionalized α,ω-dienes catalyzed by the α-diimine palladium-based catalyst, respectively. High to moderate monomer conversions were achieved. Chain structure, molecular weight, and molecular weight distribution(MWD) of the cyclopolymerization products were characterized by ~1 H-, ^(13) C-NMR, FTIR, and GPC. The polymers showed regular main chain structures,moderately high molecular weight, and narrow MWD. Thermal properties and chain stacking behaviors of the polymers were investigated by differential scanning calorimetry(DSC) and X-ray diffraction(XRD) as well as atomic force microscopy(AFM). The polymer with conjugation system in both the backbone and the pendent groups exhibited UV-Vis absorption at a much longer wavelength than those with the conjugation only in the backbone or only in the side groups. The polymers with conjugated backbone need more space for chain stacking, and the conjugated backbone causes enhanced size of polymer particles assembled from solution. The results showed that primary microstructures of the polymer exerted significant influences on the physical properties.

关键词： Cyclopolymerization α,ω-Diene α,ω-Diyne Conjugation system Properties

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