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JOURNAL OF VINYL & ADDITIVE TECHNOLOGY · 2019 ·Vol. 26 ·期 2 ·180-186 · IF 1.292

Rosin-derived poly(vinyl chloride) plasticizer: Synthesis, structure, and properties

Fei Song,Puyou Jia,Haoyu Xia,Meng Zhang,Lihong Hu,Yonghong Zhou

In this work, rosin-based plasticizer was synthesized by Diels–Alder (DA) and esterification. First, the maleopimaric acid (RT) was obtained by DA between the double bond of rosin and maleic anhydride. Then, the carboxyl group and anhydride group of RT was esterified with tetrahydro geraniol to obtain the rosin-based polyacid esters (RTT) under the catalysis of p-toluene sulfonic acid. The structure of RT and RTT was detected by FTIR and 1 H-NMR. RTT was used as main plasticizer to obtain plasticized polyvinyl chloride (PVC) materials and compared with DOP. The results showed that RTT improved the thermal stability and reduced T g of PVC film. Plasticized PVC films had excellent mechanical properties with the elastic modulus of −4,793.67 MPa and tensile strength of −111.86 MPa, higher than that of pure PVC and DOP-6. RTT showed better volatility stability, migration, and solvent extraction in PVC compared to DOP. J. VINYL ADDIT. TECHNOL., 26:180–186, 2020. © 2019 Society of Plastics Engineers

研究领域: 材料科学 · 化学工程
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STARCH-STARKE · 2021 · IF 2.741

Response Surface Optimization of Lipase-Catalyzed Surface Esterification for Modification of Cassava Starch with Rosin Acid

Hui Yang,Rihui Lin,Yanye Fan,Sai Jiang,Yujiao Lin

The rosin acid starch (RAS) is prepared under the catalysis of lipase, by esterification on the starch particles' surface in a two-phase reaction system, using rosin acid and native cassava starch as starting materials. The effects of reaction time, solvent types, substrate ratio, reaction temperature, and lipase dosage on the degree of substitution (DS) of RAS are investigated. Based on the single factor experiments, the reaction conditions are optimized according to the principle of the combination Box-behnken centered design and response surface methodology analysis. The mathematical model of the influence of reaction temperature, material ratio, and enzyme addition amount on DS is established. The optimum synthesis conditions are determined as follows: solvent, trichloromethane; reaction time, 10 h; reaction temperature, 59 °C; substrate ratio (m Rosin acid :m starch) , 4.1; and lipase dosage, 264 µL. Under these conditions, it is found that the DS is 0.0608. The analysis of variance and verification experiments show that the mathematical model has good fit degree and high credibility. Compared with the native cassava starch, RAS has improved contact angle, emulsion capacity, and emulsion stability.

研究领域: 食品科学 · 生物化学
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NORDIC PULP & PAPER RESEARCH JOURNAL · 2021 ·Vol. 36 ·期 3 ·503-511 · IF 1.04

Preparation and characterization of tung oil-rosin-based polyester internal sizing agent

Yazhou Xu,Songlin Dai,Liangwu Bi,Yuxiang Chen

A series of tung oil-rosin-based polyester (TRP) used as internal sizing agents were prepared using rosin, tung oil, maleic anhydride, and glycerol. TRP structure and properties were examined using Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC) and gel permeation chromatography (GPC). The TRP latexes were subsequently used as internal sizing agents, and the sizing properties were evaluated using a scanning electron microscope (SEM), a video-based dynamic contact angle measuring device and a Cobb absorbency tester. The optimal conditions for preparing the TRP sizing agent were as follows: the hydroxy-carboxyl ratio of the material was 0.25; the maleic anhydride dosage was 20 % of rosin; and the tung oil dosage was 40 % of rosin. Under the best conditions, the sized paper Cobb-60 was 15.6  g / m 2 , the tensile index was 45.1 N·m/g, the burst index was 3.1 kPa· m 2 /g, and the tear index was 15.6 mN· m 2 /g.

研究领域: 材料科学 · 化学工程
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Biomass Conversion and Biorefinery · 2023 · IF 4

Synthesis, characterization, antifungal properties of quaternary ammonium salts derived from natural rosin

Xu Yanran,Niu Yanfei,Wu Chunhua,Yan Jia,Rao Xiaoping,Shi Zhengjun,Xu Kaimeng,Algadi Hassan,Guo Zhanhu

In the paper, five quaternary ammonium salts derived from rosin were synthesized, characterized and their antifungal activities against different molds were studied. Choline quaternary ammonium salt and tetramethylammonium hydroxide were synthesized from dehydroabietic acid and the rosin ethanolamine ester quaternary ammonium salts which are new compounds were synthesized from propylene pimaric acid. Their structures were confirmed by FTIR, 1 HNMR, 13 CNMR, and high resolution mass spectrometry. The antifungal activities of the synthesized quaternary ammonium salts from rosin acid were tested by Oxford cup method, and their minimum inhibitory concentration was determined. The results show that quaternary ammonium salts derived from rosin acid have inhibitory effects on bamboo slices to some extent. Among them, propylene pimaric acid ethanolamine ester quaternary ammonium salts (A 1 and A 2 ) showed obvious antifungal activity in the Oxford cup test. The Oxford cup activity test and anti-mildew effect of quaternary ammonium salts (B 1 and B 2 ) synthesized from rosin acid are significant, and there are almost no mould growth on bamboo slices. It can be inferred that A 1 , A 2 , B 1 and B 2 are expected to be used as bamboo mildew inhibitors. Graphical abstract Five quaternary ammonium salts derived from rosin were synthesized and characterized; and their antifungal activities against different molds were studied.

研究领域: 化学 · 生物学 · 材料科学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2024 · IF 7.7

Sustainable, temperature-tolerant, dual network conductive pressure sensitive adhesive from cellulose and rosin for wearable sensing

Tong Luo,Xiaoliang Guo,Yuling Qiu,Daihui Zhang,Chuanwei Lu,Chunpeng Wang,Jifu Wang,Tongqi Yuan,Fuxiang Chu

Conductive pressure sensitive adhesives (PSA) used for wearable and smart electronic sensors have attracted a significant amount of attention recently. However, achieving multifunctional conductive PSA with the feature of temperature tolerance and sustainability via a convenient and environment-friendly approach still remains challenge. Herein, a novel cellulose-rosin based poly(esterimide) (PEI) was first prepared by esterification and imidization. Then, the cellulose-rosin based PEI was integrated with polymerizable deep eutectic solvents (PDES, 2-hydroxyethyl acrylate and triethanolamine as hydrogen bond donor, choline chloride as hydrogen bond receptor) and performed UV-induced polymerization for formation of the conductive PSA with dual network (DN). The DN structure and the existence of extensive hydrogen bonds endowed these cellulose-rosin based conductive PSA with excellent adhesion property (shear resistance more than 70 h, tack of 14.6 N and 180° peel strength of 148.1 N/m, are higher than that of some typical commercial PSA), exceptional UV-blocking, solvent-resistance (usable in low polar solvent) and temperature tolerance (perform well between −25 °C to 140 °C). Furthermore, these conductive PSA could be used as wearable sensor to monitor subtle movements and achieve real-time monitoring of interface adhesion states even under extreme environmental conditions. This work provides a green strategy for the next-generation of multifunctional PSA.

研究领域: 材料科学 · 可持续发展 · 传感器技术
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Polymers · 2021 ·Vol. 13 ·期 19 ·3386 · IF 4.329

Rosin-Based Epoxy Vitrimers with Dynamic Boronic Ester Bonds

Yanning Zeng,Jiawei Li,Shuxin Liu,Bin Yang

Rosin is an abundantly available natural product. In this paper, for the first time, a rosin derivative is employed as the main monomer for preparation of epoxy vitrimers to improve the mechanical properties of vitrimers. Novel epoxy vitrimer networks with dynamic reversible covalent boronic ester bonds are constructed by a reaction between thiols in 2,2′–(1,4–phenylene)–bis (4–mercaptan–1,3,2–dioxaborolane) (BDB) as a curing agent and epoxy groups in the rosin derivative. The rosin-based epoxy vitrimer networks are fully characterized by Fourier transform infrared spectroscopy (FTIR), an equilibrium swelling experiment, and dynamic mechanical analysis (DMA). The obtained rosin-based epoxy vitrimers possess superior thermostability and good mechanical properties. Due to transesterification of boronic ester bonds, rosin epoxy vitrimer network topologies can be altered, giving welding, recycle, self-healing, and shape memory abilities to the fabricated polymer. Besides, the effects of treating time and temperature on welding capability is investigated, and it is found that the welding efficiency of the 20% C-FPAE sample is >93% after treatment for 12 h at 160 °C. Moreover, through a hot press, the pulverized samples of 20% C-FPAE can be reshaped several times and most mechanical properties are restored after reprocessing at 200 °C for 60 min. Finally, chemical degradation is researched for the rosin-based epoxy vitrimers.

研究领域: 材料科学 · 化学工程
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CARBOHYDRATE POLYMERS · 2018 · IF 5.158

Fabrication of UV-absorbent cellulose-rosin based thermoplastic elastomer via “graft from” ATRP

Chuanwei Lu,Juan Yu,Chunpeng Wang,Jifu Wang,Fuxiang Chu

Cellulose-rosin based thermoplastic elastomers with UV absorption properties were fabricated by a combination of rosin, poly(butyl acrylate) (PBA) and ethyl cellulose (EC) via “graft from” ATRP with the aid of EC-rosin macroinitiator (EC- g -(DA)-Br) prepared by a simple esterification reaction between EC, dehydroabietic acid (DA, one of rosin’s resin acids) and 2-bromoisobutylryl bromide. The introduction of rosin affords these elastomers with UV absorption property. And the glass transition temperature of these EC-rosin grafted copolymers could be tuned by changing the content of PBA. Moreover, the introduction of PBA to EC endowed EC- g -(DA)- g -PBA with a good film-forming property and excellent thermoplastic elastomer behavior. All of these EC-rosin grafted copolymers showed an excellent UV absorption performance, and maintained outstanding UV absorption capability after continuous UV-irradiation or being heated to 115 °C for 1 h. As a result, these EC-rosin grafted copolymers have a potential application in coating materials with UV absorption property.

研究领域: 材料科学 · 高分子化学
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MATERIALS & DESIGN · 2020 · IF 6.289

Surface modification of silicone elastomer with rosin acid-based quaternary ammonium salt for antimicrobial and biocompatible properties

Zhaoshuang Li,He Liu,Xu Xu,Lina Ma,Shibin Shang,Zhanqian Song

Despite advanced sterilized and aseptic techniques, biomaterial-associated infections are still posing a great threat to human life. Therefore, constructing antimicrobial coating that exerts potent antimicrobial activity combined with low cytotoxicity is of great significance. Herein, an antimicrobial coating on the surface of silicone elastomer (PDMS) has been successful constructed, which based on maleopimaric acid quaternary ammonium cation (MPA-N + ). The surface morphology and chemical composition of modified PDMS (PDMS- g -MPA-N + ) were confirmed by scanning electron microscopy (SEM), energy dispersive spectrometry (EDS), and X-ray photoelectron spectroscopy (XPS). The PDMS- g -MPA-N + possess excellent antimicrobial activity against both Gram-positive bacterial ( Staphylococcus aureus ) and Gram-negative bacterial ( Escherichia coli , Pseudomonas aeruginosa ) strains. In addition, confocal laser scanning microscopy imaging demonstrated that it also can effectively inhibit bacterial biofilm formation over 5 days. Most importantly, PDMS- g -MPA-N + exhibited excellent biocompatibility, which induced no significant hemolysis and cytotoxicity toward mammalian cells. The study demonstrated that the silicone elastomer surface grafted with MPA-N + enabled the incorporation of a renewable biomass to effectively combat bacteria and biofilm formation for biomedical applications.

CAS / MDL: 298-93-1
研究领域: 生物医学工程 · 材料科学 · 微生物学
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MATERIALS & DESIGN · 2022 · IF 9.417

Superhydrophobic coating constructed from rosin acid and TiO2 used as blood repellent dressing

Yingxuan Wang,Zhaoshuang Li,Jiping Wang,Jingran Wang,Xiangzhou Li,Chuntao Kuang

Blood repellent dressings plays an important role in trauma medicine. However, such dressings have poor hemostatic efficacy, and can cause infection, rendering them unsatisfactory for clinical application. We prepared a durable superhydrophobic coating for blood repellent dressing based on rosin acid and TiO 2 with a water contact angle of 155.7° and a sliding angle of 5°. The morphology and chemical composition of the coating were characterized by scanning electron microscopy-energy dispersive spectroscopy (SEM-EDS) and X-ray spectroscopy (XPS), respectively. The superhydrophobic coating can withstand at least thirty sandpaper abrasions and sixteen washing treatments without losing its superhydrophobic properties. Meanwhile, the superhydrophobic coating demonstrated excellent antimicrobial activities against Gram-positive Staphylococcus aureus ( S. aureus ) (with log reduction = 1.73) and Gram-negative Escherichia coli ( E. coli ) (with log reduction = 1.74) and effectively prevented biofilm formation. Besides, the excellent biocompatibility of the superhydrophobic coating was verified by hemocompatible and cytotoxic assays. Finally, it was confirmed that the superhydrophobic coating can reduce blood loss and allows for high air permeability in in vitro tests. The superhydrophobic coating based on rosin acid and TiO 2 provides a simple way for preparing novel blood repellent dressings, which may have promising applications in wound dressings.

研究领域: 创伤医学 · 材料科学 · 生物医学工程
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Desalination and Water Treatment · 2024 · IF 1

Effective and selective removal of cationic dye from aqueous solution using rosin derivative modified wheat straw

Lei Hu,Limin Zang,Qifan Liu,Jianhui Qiu,Chao Yang,Xu Xu,Jun Yang,Xuan Qiao

ABSTRACT This study developed an effective, low-cost and renewable bioadsorbent to remove dyes from wastewater. Wheat straw, an agricultural by-product with abundant resource, was modified with rosin derivative (maleated rosin) and applied as a biosorbent to improve adsorption capacity and selectivity for cationic dyes [(e.g., methylene blue (MB)]. The effects of pH, contact time, temperature and regeneration on adsorption were investigated and discussed. The MB adsorption capacity of the rosin derivative modified wheat straw was 113.34 mg/g, and low temperature and alkaline environment was in favor of the MB adsorption onto the bioadsorbent. The kinetic data was fitted well by pseudo-second-order kinetic model, and equilibrium adsorption isotherm data was fitted well by Freundlich and Temkin isotherm models. In addition, the bioadsorbent could be regenerated in acid condition and reused for several cycles. All the results indicate that the rosin derivative modified wheat straw is a promising bioadsorbent for wastewater treatment.

研究领域: 环境科学 · 材料科学
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Journal of Renewable Materials · 2020 ·Vol. 8 ·期 3 ·289-300 · IF 1.341

Synthesis and Kinetics of Hydrogenated Rosin Dodecyl Ester as an Environmentally Friendly Plasticizer

Li Qiaoguang,Gong Sheng,Yan Jie,Hu Hongchao,Shu Xugang,Tong Hanqing,Cai Zhiye

The plasticizer is an important polymer material additive. Non-toxic and environmentally friendly plasticizers are developed recently in order to decrease fossil fuel reserves, serious environmental pollution and the toxicity of phthalate esters. In this study, a new, efficient and environmentally friendly plasticizer of hydrogenated rosin dodecyl ester was prepared by an esterification reaction of hydrogenated rosin and dodecanol. The influences of different reaction conditions (including different catalysts, the catalyst concentration, the ratio of the reactants, reaction temperature, and reaction time) on the esterification yield are examined and discussed. Hydrogenated rosin dodecyl ester with 71.8% yield was synthesized under the optimized reaction conditions (1:0.8 molar ratio of rosin to dodecanol, 1 mol% tetrabutyl titanate concentration, and 210°C for 6 h). The esterification reaction is a second-order reaction, and kinetic calculations showed that the activation energy is 39.77 KJ·mol–1. The structure of the hydrogenated rosin dodecyl ester was confirmed by FT-IR spectroscopy and 13C NMR spectrum. Besides, the thermal stability of target product (hydrogenated rosin dodecyl ester) was also tested by thermal gravimetric analysis (TGA), which showed a good thermal stability.

研究领域: 材料科学 · 环境科学 · 化学工程
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ACS Applied Polymer Materials · 2024 · IF 4.4

Rosin-Modified Polyurethane Elastomers with Room-Temperature Self-Healing Ability, High Strength, and Recyclability Based on Oxime Dynamic Bonds

Shanling Lu,Yuehan Qian,Yuemin Zhou,He Liu,Xu Xu,Fuhao Dong

Rosin, with a rigid hydrogenated phenanthrene ring, is a widely available biomass, but its high-value utilization needs to be enhanced. Inspired by sustainable development strategies, the design of polymer elastomers with a room-temperature self-healing capability has been a hot focus topic. However, designing elastomers that combine the conflicting properties of high mechanical performance and room-temperature self-healing is a significant challenge. The hydrogenated phenanthrene ring of rosin provides a superior solution to this problem. In this work, the polyurethane elastomer (BPU-X% AP) based on rosin-hydrogenated phenanthrene ring structure, dynamic oxime, and hydrogen bonding was reported. The BPU-X% AP exhibits high tensile strength (37.8 MPa), and good toughness (126.9 MJ m–3). Due to the rosin structure that promotes the movement of the elastomer chain segments, the elastomers have fast room-temperature self-healing and recyclability. Benefiting from their excellent mechanical strength and self-healing properties, BPU-X% AP as adhesives exhibits a strong lap shear strength of 5.5 MPa, and they can be used as hot melt binders. Corresponding to the cycling of the elastomer, the adhesive strength of BPU-10% AP remains almost the same after three cycles of adhesion to the iron and aluminum plates. This work provides a viable approach for the preparation of high-performance biomodified polyurethanes.

研究领域: 材料科学 · 可持续发展 · 生物质利用
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