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Materials · 2019 ·Vol. 12 ·期 9 ·1507 · IF 2.972

Synthesis, Properties of Biodegradable Poly(Butylene Succinate-co-Butylene 2-Methylsuccinate) and Application for Sustainable Release

Jiarui Han,Jiaxin Shi,Zhining Xie,Jun Xu,Baohua Guo

A novel biobased and biodegradable polyester, i.e., poly(butylene succinate-co-butylene 2-methylsuccinate) (P(BS-BMS)) was synthesized by succinic acid (SA), 2-methylsuccinic acid (MSA), and 1,4-butanediol (BDO) via a typically two-step esterification and polycondensation procedure. The chemical structure and macromolecular weight of obtained copolymers were characterized by1H NMR,13C NMR, and GPC. The melting temperature and degree of crystallinity were also studied by DSC, and it was found that the values were gradually decreased with increasing of MSA content, while the thermal stability remained almost unchanged which was tested by TGA. In addition, the biodegradation rate of the P(BS-BMS) copolymers could be controlled by adjusting the ratio of SA and MSA, and such biodegradability could make P(BS-BMS) copolymers avoid microplastic pollution which may be brought to the environment for applications in agricultural field. When we applied P(BS-BMS) copolymers as pesticide carriers which were prepared by premix membrane emulsification (PME) method for controlling Avermectin delivery, an improvement of dispersion and utilization of active ingredient was obviously witnessed. It showed a burst release process first followed by a sustained release of Avermectin for a long period, which had a great potential to be an effective and environmental friendly pesticide-release vehicle.Keywords:biodegradable copolyesters;crystallinity;degradation property;pesticide-loaded microparticles;pesticide release

CAS / MDL: 9002-89-5
研究领域: 材料科学 · 环境科学 · 农业科学
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POLYMER · 2025 · IF 4.5

Development of biocompatible azelaic acid-based copolyester plasticizers for PVC applications

Wanjing Zhang,Liyan Wang,Yunsheng Chong,Wei Liu,Xin Qian

In this study, the copolyester plasticizers PHNAZ, synthesized from azelaic acid and hexanediol and modified by neopentyl glycol (NPG), was prepared via direct esterification. A series of characterization tests revealed that the number-average molecular weight of the PHNAZ copolyester plasticizers was less than 2000 with a dispersion coefficient of less than 2, demonstrating excellent thermal stability below 250 °C. PVC samples plasticized with PHNAZ showed thermal degradation temperatures above 250 °C, reduced glass transition temperatures to −33 °C, and significantly improved hydrophilicity. Notably, the water contact angle of PHNAZ-50/PVC was smallest, averaging 53.956°. The highlight of the study is the cytotoxicity testing of the prepared PHNAZ copolyester plasticizer at concentrations of 1 μg/mL, 10 μg/mL, and 50 μg/mL, where the average cell survival rate exceeded 100 %, indicating excellent biocompatibility. Additionally, PHNAZ displayed outstanding plasticizing effects, particularly PHNAZ-20/PVC, which achieved an elongation at break of 913.6 % and a plasticizing efficiency of 260.0 %. These results suggest that PHNAZ not only excels in chemical and thermal properties but also exhibits good biocompatibility and high plasticizing capability, indicating broad application prospects.

CAS / MDL: 123-99-9
研究领域: 材料科学 · 生物学
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ACS Applied Polymer Materials · 2024 · IF 4.4

Naphthyl Copolyester with High Glass Transition Temperatures: Tunable Structure and Performance

Yang Hu,Hongdong Zhang,Xinming Pu,Liping Yang

A series of poly(ethylene bis[4-(2-hydroxyethoxy)phenyl]sulfone 1,4-cyclohexanedimethylene 2,6-naphthalate) (PESCNs) copolyesters from amorphous to crystalline were prepared by melt polymerization. The chemical structure and compositions were explored by hydrogen and carbon nuclear magnetic spectroscopy (1H NMR and 13C NMR). The glass transition temperature (Tg) of copolyesters (128.1–134.5 °C) was higher than that of PEN (about 120 °C) and showed tunable characteristics with the composition of polymerization. With the incorporation of CHDM, the thermal stability of the copolyesters decreased slightly while the fluidity improved, owing to the easier conformational transition ability of CHDM. An interesting transition from brittleness to toughness was also achieved via regulating CHDM content. In addition, all the prepared copolyesters exhibited good transmittance (∼85%) under both UV and C light sources. In view of these unusual performances, PESCNs exbibit potential for use in the fields of electronic devices, fibers, and cosmetic packaging.

研究领域: 材料科学 · 高分子化学
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Journal of Materials Chemistry C · 2017 ·Vol. 5 ·期 37 ·9702-9711 · IF 5.256

Novel liquid crystalline copolyester containing amphi-mesogenic units toward multiple stimuli-response behaviors

Hai-Yi Zhong,Li Chen,Xiao-Feng Liu,Rong Yang,Yu-Zhong Wang

Novel liquid crystalline copolyesters named as P(BH-co-BPn)PS, with azobenzene and biphenyl group mesogenic units, were designed and synthesized conveniently by one pot melt polycondensation. All P(BH-co-BPn)PS copolyesters showed good thermal stability, smectic liquid crystalline behavior with π–π interactions in the polymer chains. As the three different functional building blocks (azobenzene and biphenyl chromophores, liquid crystals, π–π interactions) work together, P(BH-co-BPn)PS were responsive to external stimuli at the molecular level, exhibiting thermal shape memory, photo-induced bending and self-healing behaviors at the macroscopic level. It was noteworthy that the different responsive properties of the photo-active azobenzene and photo-inert biphenyl mesogenic units made a great contribution in the photo responsive behavior of these copolyesters, resulting in reversible bending and unbending behaviors for P(BH-co-BP30)PS. In addition, without the chemical crosslink, these copolyesters could be reshaped and reprocessed. Taking advantage of the features, these copolyesters containing amphi-mesogenic units can help to facilitate numerous applications like soft actuators and smart materials.

CAS / MDL: 2009-83-8 635-51-8
研究领域: 材料科学 · 高分子化学
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E-POLYMERS · 2020 ·Vol. 20 ·期 1 ·214-225 · IF 1.675

Lipase-catalyzed synthesis and post-polymerization modification of new fully bio-based poly(hexamethylene γ-ketopimelate) and poly(hexamethylene γ-ketopimelate-co-hexamethylene adipate) copolyesters

Wan-Xia Wu

A novel full bio-based ketone-containing aliphatic polyester was prepared by enzyme-catalyzed polycondensation of diethyl γ-ketopimelate (DEK) with 1,6-hexanediol (HDO) using immobilized lipase B from Candida antarctica (CALB). The influences of polymerization conditions such as temperature, time, enzyme amount, and solvent amount on the molecular weight of poly(hexamethylene γ-ketopimelate) (PHK) were investigated. New fully bio-based poly(hexamethylene γ-ketopimelate- co -hexamethylene adipate) (poly(HK- co -HA)) copolymers with narrow polydispersity and well-defined composition were synthesized by copolymerization of DEK, HDO, and diethyl adipate. The structures of PHK and poly(HK- co -HA) copolymers were characterized by nuclear magnetic resonance, and their thermal characterization was examined by thermogravimetric analysis and differential scanning calorimetry. The degradation of PHK and poly(HK- co -HA) copolymers was studied. The post-polymerization modification of these polyketoesters via oxime click chemistry was further demonstrated. Graphical

研究领域: 材料科学 · 生物化学
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CHEMOSPHERE · 2019 · IF 5.108

Synthesis, characterization of phosphorus-containing copolyester and its application as flame retardants for poly(butylene succinate) (PBS)

Xiaoming Zhou,Tonghao Wu

Two novel phosphorus-containing copolyesters were synthesized by direct polycondensation reaction of phenyl dichlorophosphate, 1,4-succinic acid and 1,4-butanediol using stannous chloride (SnCl 2 ) and 4-Methylbenzenesulfonic acid as catalyst, and its chemical structures were identified by 1 H and 31 P nuclear magnetic resonances ( 1 H and 31 P NMR). The resulting phosphorus-containing poly(butylene succinate) (PPBS) was characterized by X-ray diffraction (XRD), polarized optical microscope (POM), thermogravimetry analysis (TGA) and differential scanning calorimetry (DSC). PPBS can be as a flame retardant for commercial poly(butylene succinate) (PBS). A series of flame retardant composite materials were produced by melt-blending of PBS and PPBS. The comprehensive flame retardant property of composite materials was evaluated by limited oxygen index (LOI). While 20 wt % of PPBS was added into PBS resin, good flame retardant properties could be obtained. Composite materials can have much better flame retardancy (LOI = 30) than neat PBS resin. Thermogravimetric analysis (TGA) showed that the weight loss of PBS was decreased by the introduction of PPBS. In addition, possible flame retardancy mechanism of PPBS in composite materials was analyzed by SEM photos of char residue.

CAS / MDL: 110-15-6
研究领域: 材料科学 · 高分子化学
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EUROPEAN POLYMER JOURNAL · 2024 · IF 5.8

Biobased high barrier copolyesters derived from furandicarboxylic acid and citric acid

Xiaoqin Zhang,Manyuan Yin,Jinggang Wang,Chengcai Pang,Xiaoqing Liu,Jin Zhu

Biobased feedstocks developed from renewable resources play a crucial role in polymers. Dimethyl octahydro-2,5-pentalenediol (MeOPD) with excellent thermal stability and rigidity is a biobased bicyclic diol derived from citric acid . In this work, MeOPD was first reacted with dimethyl carbonate (DMC) to form oligo (dimethyl octahydro-2,5-pentalenediol carbonate) (OMC). Subsequently, a series of poly(butylene-co-dimethyl octahydro-2,5-pentalenediol furanoate-co-carbonate) (PBMFC) polyesters with MeOPD units ranging from 5 to 31 mol% were synthesized via melt polycondensation from OMC, dimethyl furan-2,5-dicarboxylate (DMFD) and 1,4-butanediol (BDO). Due to the low reactivity of MeOPD, its actual content in copolymer is much lower than that in the feed, and as the MeOPD content rises, the number-average molecular weight of PBMFCs drops from 25,200 g/mol of PBMFC5 to 12,800 g/mol of PBMFC31. Despite the presence of MC units weakens thermal stability, PBMFCs still maintain good thermal stability, evidenced by T d,5% ranging from 294-325 °C in N 2 and from 295-339 °C in air. The mechanical properties are also satisfactory, exhibiting tensile modulus ≥ 500 MPa, tensile strength ≥ 23 MPa, and elongation at break ≥ 150 %. Compared to PET, PBMFCs demonstrate commendable gas barrier properties, with CO 2 and O 2 barrier capability being 4.7–11.0 times and 2.0–3.6 times that of PET, respectively. All results indicate that PBMFCs can serve as a renewable potential material for packaging application.

研究领域: 材料科学 · 化学工程
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RSC Advances · 2024 ·Vol. 14 ·期 33 ·23662-23671 · IF 3.9

Synthesis of azelaic acid copolyester plasticizers and their application in PVC

Wanjing Zhang,Liyan Wang,Hong Chen,Liying Guo,Yaoyao Bai,Xin Qian

A series of 2-methyl-1,3-propanediol (MPO) modified azelaic acid and hexylene glycol copolyester (PHMAZ) plasticizers with varying contents were synthesized using a direct esterification melt polycondensation method, and their structures were characterized systematically. Analysis using infrared spectroscopy and nuclear magnetic resonance spectroscopy confirmed the synthesis of the designed copolyester structure. Gel permeation chromatography (GPC) tests indicated that the number average molecular weight of each copolyester sample ranged between 2000 and 3000. These copolyesters were used to plasticize polyvinyl chloride (PVC) resin, and the glass transition temperature of the plasticized PVC samples was tested using a differential scanning calorimeter (DSC). Further characterization of the plasticizing effects was conducted using an electronic universal testing machine. The research results showed that as the content of MPO increased, the plasticizing effect of the copolyester initially increased and then decreased. Specifically, the copolyester containing 45% MPO, PHMAZ-45, demonstrated the best plasticizing effect on PVC, with the glass transition temperature of the plasticized PVC system around −35 °C, elongation at break at 908.4%, and a plasticizing efficiency of 254.5%. Additionally, this new type of copolyester plasticizer uses bio-based raw materials, exhibits excellent plasticizing effects, and the preparation process is stable and controllable. It holds promising potential to replace traditional volatile and toxic phthalate esters, presenting significant industrial application value.

CAS / MDL: 123-99-9
研究领域: 材料科学 · 高分子化学
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JOURNAL OF APPLIED POLYMER SCIENCE · 2025 · IF 2.8

Synthesis of 2-Methyl-1,3-Propanediol Modified Azelaic Acid-Octanediol Copolyester Plasticizers and Their Plasticizing Effect on Polyvinyl Chloride

Wanjing Zhang,Yuqi Shan,Liyan Wang,Yanming Chen,Liying Guo,Yunsheng Chong,Xin Qian

Currently, mainstream phthalate plasticizers pose serious threats to the environment and human health. As an eco-friendly and harmless alternative, polyester plasticizers have garnered widespread attention. However, their complex preparation process and low plasticizing efficiency have limited their practical application. In this study, a series of copolyester plasticizers (POMAZ), synthesized from azelaic acid, octanediol, and various contents of 2-methyl-1,3-propanediol (MPO), were prepared via direct esterification. The preparation process is controllable, and the number-average molecular weight of POMAZ ranges from 1000 to 4000, with a thermal degradation temperature above 270°C, demonstrating excellent thermal stability. PVC samples plasticized with POMAZ showed a decrease in glass transition temperature to −30°C and increased hydrophilicity with higher MPO content. Measurements of the tensile elongation at break of plasticized PVC verified the outstanding plasticizing performance of the POMAZ series. Specifically, POMAZ-45/PVC exhibited an elongation at break of up to 975.3%, with a plasticizing efficiency reaching 273.2%.

CAS / MDL: 123-99-9 629-41-4
研究领域: 材料科学 · 环境科学 · 高分子化学
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JOURNAL OF APPLIED POLYMER SCIENCE · 2025 · IF 2.8

A Novel Bio-Based Copolyester Elastomer—Itaconic Acid Modifying Poly(Butylene 2,5-Furandicarboxylate)

Zixuan Wang,Wenhao Gao,Zhengchun Cai,Haian Xia

Poly(ethylene 2,5-furandicarboxylate) (PEF) and poly(butylene 2,5-furandicarboxylate) (PBF) are regarded as two of the most promising materials derived from furandicarboxylic acid. The modification of these two polyesters has become one of the hot research topics. It was reported that their mechanical properties had significant shortcomings, particularly for low molecular weight PBF, whose brittleness limited its use. In this work, a novel monomer, itaconic acid, was introduced to modify PBF, and a new furan-based polyester-poly(1,4-butylene furanoate-co-itaconate) (PBFIs) was synthesized. For the first time, itaconic acid up to 47% was incorporated to synthesize the polyester materials. The structural and thermomechanical properties of these polyesters were investigated using Gel Permeation Chromatography (GPC), Proton Nuclear Magnetic Resonance ( 1 H NMR), Differential Scanning Calorimetry (DSC), Thermogravimetric Analysis (TGA), X-ray Diffraction (XRD), and tensile testing. Compared to PBF, the PBFIs exhibited reduced crystallization ability attributed to the formation of crosslinked networks; notably, their glass transition temperature decreased significantly to as low as 7°C, while thermal stability improved. Tensile tests further demonstrated that their elongation at break increased dramatically by up to 675%. In summary, the results suggest that PBFIs possess significant potential in the realm of thermoset elastomers, thereby expanding the application scope of furan-based polyesters.

研究领域: 材料科学 · 聚合物化学
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ACS Sustainable Chemistry & Engineering · 2025 · IF 7.3

Fully Biobased Copolyesters with High Gas Barrier and Enhanced Mechanical Properties Derived from 2,5-Thiophenedicarboxylic Acid and Long-Chain Dicarboxylic Acid

Jiyang Zuo,Tao Yang,Chen Lin,Hongxia Deng,Shanshan Gu,Fei Liu,Zhisen Shen,Jin Zhu,Jinggang Wang

This work provides an in-depth molecular structure design strategy for developing high-barrier polymer packaging films. A series of high-performance PPDThF copolyesters were prepared by utilizing the unique crystallization ability of poly(propylene 2,5-thiophenedicarboxylate) (PPThF), as well as a long-chain dicarboxylic acid, namely dodecanedioic acid (DA). The incorporation of a polyethylene-like polyester structure from DA into the main chain of polymers has been found to be random copolymerization, leading to limited crystallizable sequence lengths. The effects of the long-chain dicarboxylic acids on the thermal transition, aggregation structure, gas barrier properties, and optical properties of the copolyester PPDThF copolyesters were investigated. The results demonstrate that PPDThF-10 combines the benefits of conventional thermoplastics, like high strength (>30 MPa) and high modulus (>0.6 GPa), with the mechanical and physical characteristics of chemically cross-linked rubber, including high extensibility (ε = 730%) and toughness (134 MJ/m–3). The results obtained so far demonstrate that thiophene-based copolyesters can be used in food packaging applications.

研究领域: 材料科学 · 高分子化学
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JOURNAL OF MATERIALS CHEMISTRY · 2012 ·Vol. 22 ·期 8 ·3457-3461 · IF 5.968

The copolymerization reactivity of diols with 2,5-furandicarboxylic acid for furan-based copolyester materials

Jiping Ma,Yi Pang,Min Wang,Jie Xu,Hong Ma,Xin Nie

Furan-based copolyesters were synthesized via polytransesterification of 2,5-furandicarboxylic acid (FDCA) with ethylene glycol (EG) and 1,4-butylene glycol (BG). The composition and thermal properties of the obtained copolyesters were characterized in detail by 1H NMR and elemental analysis, differential scanning calorimeters (DSC) and thermogravimetric analysis (TGA). The 1H NMR results showed that the ethylene segment content was consistently lower than that of butylene in the obtained copolyesters in comparison with the comonomer feeds. The reactivities of EG and BG with FDCA were intensively investigated. On the basis of kinetic studies, EG was found to be less reactive than BG. The thermal properties of the obtained copolyesters could be adjusted by variation of the EG/BG molar ratios in the copolyesters.

CAS / MDL: 111-29-5 504-63-2
研究领域: 材料科学 · 化学工程
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