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cardanol
ACS Sustainable Chemistry & Engineering · 2017 · IF 5.951

Renewable Cardanol-Based Phosphate as a Flame Retardant Toughening Agent for Epoxy Resins

Xin Wang,Shun Zhou,Wen-Wen Guo,Pei-Long Wang,Weiyi Xing,Lei Song,Yuan Hu

A biobased flame retardant toughening agent, phosphaphenanthrene groups-containing triscardanyl phosphate (PTCP), was successfully synthesized via debydrochlorination, epoxidation and ring opening reaction from renewable resource cardanol. The chemical structure of PTCP was confirmed by the proton and phosphorus nuclear magnetic resonance. Epoxy resins (EPs) with different contents of PTCP were prepared through a simple mixing method. Thermogravimetric analysis results indicated that the earlier degradation of PTCP catalyzed the char formation of epoxy resins that was beneficial to protecting underlying polymers from further decomposition. The flame retardant properties were enhanced with the increase of the PTCP content. The EP composite containing 30 wt % PTCP showed a limiting oxygen index of 30.5%. Meanwhile, its peak heat release rate, total heat release and average effective heat of combustion values were decreased by 50%, 27% and 32%, respectively, in comparison to those of neat EP. The enhanced flame retardant behavior was attributed to the improved quality of char residue, which effectively inhibited the flammable volatiles, oxygen and heat transfer between degradation zone and flame zone. The impact strength was increased to 19.14 kJ/m2 for EP/PTCP-30% composite from 14.85 kJ/m2 for neat EP, indicating the toughening effect of PTCP on EP. The findings in this study demonstrated that PTCP could be used as a promising flame retardant toughening agent for epoxy resins to overcome their drawbacks of intrinsic brittle and high flammability.

CAS / MDL: 35948-25-5
研究领域: 材料科学 · 化学工程
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ACS Sustainable Chemistry & Engineering · 2021 · IF 8.198

Synthesis and Characterization of Cardanol-Based Methacrylate Oligomers for Three-Dimensional Printing Resins

Shaoyun Chen,Yongqiang Luo,Yihao Xu,Yanyu Zheng,Xiaoying Liu,Rui Wang,Bo Qu,Dongxian Zhuo

A novel bio-based prepolymer methacrylate cardan phenolic polycondensate (MCPP) was successfully synthesized via prepolymerization and methacrylation of cardanol. Its chemical structure was determined by Fourier transform infrared spectroscopy and proton nuclear magnetic resonance spectroscopy. MCPP-based three-dimensional (3D) printing resins with excellent coating properties were prepared. The MCPP-based 3D printing resins were cured using digital light processing, while some samples also underwent ultraviolet (UV) postprocessing. MCPP-based 3D-printed products exhibit excellent thermal and mechanical properties, including a glass-transition temperature and thermal stability temperature of 80.2 and 313.0 °C, respectively, along with tensile strength, storage modulus, and hardness values of 38.5 MPa, 5371.8 MPa, and 80.3 HD, respectively. The good performance of the MCPP-based 3D printing resins was attributed to the rigidity of their compact cross-linked structures. This study pioneers a method for the production of photoactive acrylates like cardanol-based methacrylate oligomer resins from renewable, low-cost, aromatic biomass for use in photocurable 3D printing.

研究领域: 材料科学 · 化学工程 · 3D打印
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JOURNAL OF APPLIED POLYMER SCIENCE · 2022 ·Vol. 139 ·期 40 ·e52956 · IF 3.057

Synthesis and property study of novel maleimide-cardanol based modifiers for epoxy resins

Mengyu Chen,Licheng Liu,Gang Wang,Zhuoyu Liu,Yingfeng Yu

The biomass-based chemicals from renewable resources are countermeasures to ease the problem of fossil fuel shortage. This work is to develop a biobased functional reactive modifier for thermosetting epoxy resins appropriate for excellent overall performance. The novel maleimide-cardanol modifiers (CA-HPM) is synthesized from natural extract cardanol (CA) and N -(4-hydroxyphenyl) maleimide (HPM), which is then mixed with phenolic epoxy resin and linear phenolic novolac resin systems. CA-HPM plays a versatile role in tuning the comprehensive properties of epoxy such as thermal property, adhesive property, and thermo-mechanical property. Systems with CA-HPM show slightly lower curing activity and distinct decreased single glass transition temperature ( T g ). Besides, the crosslinking density of the cured resin increases, meanwhile the thermal stability keeps at high level, which is due to the rigid five-membered ring structure of maleimide. Metal lap shear test results manifest that the adhesion between epoxy resin and metal interface augments. With 10% CA-1HPM, the cured resin exhibits lower equilibrium water sorption (1.88%) and diffusion coefficient (2.94 × 10 −8 s −1 cm 2 ). This biobased functional reactive modifier has provided balanced overall performance and would pave the way to a wide range of possible “eco-friendly” applications.

CAS / MDL: 123-30-8 108-31-6
研究领域: 材料科学 · 化学工程 · 可持续发展
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COMPOSITES SCIENCE AND TECHNOLOGY · 2021 · IF 8.528

Solvent-free synthesis, plasticization and compatibilization of cardanol grafted onto liquid isoprene rubber

Peng Wang,Jinling Liu,Chongyi Chi,Yuxia Zhang,Denglong Chen,Qinhui Chen

Liquid isoprene rubber (LIR) is commonly used as plasticizer in rubber processing industry. It shows poor compatibility with inorganic fillers . Herein, cardanol grafted onto LIR (CA- g -LIR) was synthesized by solvent-free method and used as the dispersed matrix of silica particles. Results show that the optimum reactive condition is that 7 phr of cardanol monomer and 0.2 wt % of 2, 2-Azobisisobutyronitrile (AIBN) initiator per 100 g LIR react for 12 h at 70 °C. At these conditions, grafting ratio is 6.01%. CA- g -LIR shows obvious plasticizing effect, as is certified by its far high elongation at break (increase of 800%), decreased viscosity (reduction of 62%) and glass transition temperature (T g , decline of 5.0 °C) compared with LIR. Moreover, CA- g -LIR shows good interfacial performance. The dispersion of silica particles in CA- g -LIR is better than that in LIR. CA- g -LIR is obtained by a simple and green way, low-cost, easy for industrial production. It is expected to be acted as plasticizer and compatibilizer at the same time in rubber industry.

研究领域: 材料科学 · 化学工程
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JOURNAL OF POLYMERS AND THE ENVIRONMENT · 2023 · IF 5.3

Synergistic Effect of Thermal Stabilization and Plasticization of Epoxidized Cardanol Esters on PVC

Luo Wei,Yang Yang,Han Yu,Weng Yunxuan,Zhang Caili

The development of a heat stabilizer with good thermal stability, plasticizing performance, and migration resistance for polyvinyl chloride (PVC) is still a notable challenge. In this work, two bio-based heat stabilizers, epoxidized cardanol oleate (ECD-OA) and epoxidized cardanol myristate (ECD-MA), were designed and synthesized with different lengths of their alkyl chains and different epoxy contents to provide outstanding compatibility with PVC. After confirming the chemical structures of ECD-OA and ECD-MA by proton nuclear magnetic resonance and Fourier-transform infrared spectroscopy, the thermal stabilizing effects of both epoxidized cardanol esters were compared with those of the traditional CaSt 2 /ZnSt 2 stabilizer and bio-based epoxidized soybean oil. Then, the effects of four different heat stabilizers on the mechanical, thermal, rheological, and optical properties of PVC films were fully studied. The results suggested that the ECD-MA showed the best thermal stability, and the PVC/30DOP/5ECD-MA film did not turn black after 2 h of thermal aging at 200 °C. In addition, the ECD-MA had good compatibility with PVC, and it had a synergistic plasticizing effect, which caused the film to have a high ductility and tensile strength (320.1% and 19.8 MPa, respectively).

研究领域: 材料科学 · 聚合物化学 · 可持续材料
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POLYMERS FOR ADVANCED TECHNOLOGIES · 2022 ·Vol. 34 ·期 1 ·181-194 · IF 3.348

Plasticizing and thermal stabilizing effect of bio-based epoxidized cardanol esters on PVC

Yang Yang,Caili Zhang,Yu Han,Yunxuan Weng

Poly(vinyl chloride) (PVC) is a widely used plastics in different industries. It is an intrinsically hard and brittle polymer and requires the use of plasticizers to improve the processability. Commonly used phthalate-based plasticizers have serious toxicity issues and we present alternatives based on epoxidized soybean oil (ESO) and epoxidized cardanol esters (ECEs). ECEs are synthesized from cardanol and three fatty acids (oleic, ricinoleic, and myristic) using 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) as a coupling agent. Their structure and purity are confirmed by Fourier transform infrared spectroscopy (FTIR) and Nuclear magnetic resonance. Moreover, plasticized PVC films are prepared using a solvent-free method. The replacement of 10 phr of ESO with 5 phr of ECE improves the plasticizing power due to the co-solvency effect. Mechanical properties and thermal stability of plasticized PVC films are correlated with the chain length and the number of epoxy groups in ECE. The best plasticizing effect is observed for epoxidized cardanol-myristate (ECD-MA). ECD-MA as a shorter-chain secondary plasticizer is more compatible with ESO and allows higher conformational mobility of PVC chains. PVC/30ESO/5ECD-MA polymer exhibits an exceptionally high initial thermal decomposition temperature (314.4°C) while preserving moderate ductility and tensile strength (263.4% and 23.3 MPa). Overall, this study highlights the potential applicability of ECD-MA in combination with ESO as a sustainable, bio-based plasticizer and heat stabilizer for flexible PVC products.

研究领域: 材料科学 · 高分子化学 · 环境科学
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ChemistrySelect · 2025 ·Vol. 10 ·期 47 ·e04397 · IF 2

Highly Selective Synthesis and Superior Antioxidant Performance of Cardanol-Derived Unsymmetrical Hindered-Phenol Additives

Xin Ji,Zuoxin Huang,Hanyuan Cao,Xiaowei Chen,Meiyi Tang

Using bio-based cardanol as raw material, the influence of alkylating agents and catalysts on the Friedel–Crafts alkylation was investigated. Screening of alkylating agents and catalysts enabled the efficient synthesis of the unsymmetrical-hindered phenol antioxidant 2-tert-butyl-5-pentadecylphenol (SAC, i.e., Saturated Alkylated Cardanol), which was evaluated as a novel lubricant antioxidant. The structure of SAC was characterized by mass spectrometry, infra-red spectroscopy, and nuclear magnetic resonance, and its thermal stability and antioxidant performance were studied in depth. The results show that SAC has superior antioxidant performance compared to market-available 2,6-di-tert-butylphenol and 3,5-di-tert-butyl-4-hydroxyphenylpropenoic acid octyl ester hindered phenol antioxidants. Through molecular simulation technology, the intrinsic reasons for SAC's superior antioxidant performance were further explained. The study indicates that the green SAC antioxidant has great potential to replace traditional mineral-based additives, providing a new choice and practice for efficient and environmentally friendly lubricating oil additives. Graphical Screening alkylating agents and catalysts for Friedel-Crafts alkylation enables highly selective synthesis of unsymmetrical hindered phenol SAC from bio-based cardanol. SAC outperforms commercial hindered phenol antioxidants (26P, T501, T512) in antioxidation and thermal stability, with its mechanism clarified by molecular simulation, offering a green lubricant additive.

CAS / MDL: 125643-61-0
研究领域: 绿色化学 · 材料科学 · 润滑技术 · 高分子添加剂 · 可持续材料
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JOURNAL OF APPLIED POLYMER SCIENCE · 2015 ·Vol. 132 ·期 35 · IF 1.768

Synthesis and application of a natural plasticizer based on cardanol for poly(vinyl chloride)

Jie Chen,Zengshe Liu,Ke Li,Jinrui Huang,Xiaoan Nie,Yonghong Zhou

A natural plasticizer with multifunctional groups, similar in structure to phthalates, cardanol derivatives glycidyl ether (CGE) was synthesized from cardanol by a two-step modification process and characterized by FT-IR, 1 HNMR, and 13 CNMR. The resulting product was incorporated to PVC (CGE/PVC), and plasticizing effect was compared with PVC incorporated with two kinds of commercial phthalate ester plasticizers bis (2-ethylhexyl) benzene-1,4-dicarboxylate (DOTP) and diisononyl phthalate (DINP). Dynamic mechanical analysis and mechanical properties testing of the plasticized PVC samples were performed in order to evaluate their flexibility, compatibility, and plasticizing efficiency. SEM was employed to produce fractured surface morphology. Thermogravimetric analysis and discoloration tests were used to characterize the thermal stabilities. Dynamic stability analysis was used to test the processability of formulations. Compared with DOTP and DINP plasticized samples, CGE/PVC has a maximum decrease of 9.27% in glass transition temperature ( T g ), a maximum increase of 17.6% in the elongation at break, and a maximum increase of 31.59°C and 25.31 min in 50% weight loss (T50) and dynamic stability time, respectively. The obtained CGE also has slightly lower volatility resistance and higher exudation resistance than that of DOTP and DINP. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015 , 132 , 42465.

研究领域: 材料科学 · 化学工程
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CHEMICAL ENGINEERING JOURNAL · 2024 · IF 13.3

Production, thermal recycling, and application of cardanol-based polyurethane foam with phenol-carbamate bonds

Baozheng Zhao,Fei Song,Li Tan,Rui Yang,Zheng Pan,Meng Zhang,Yonghong Zhou

The economic processing, sustainable recycling, and environmentally friendly application of polyurethane (PU) foams are important issues that need to be addressed urgently. In this study, we propose a strategy for the comprehensive utilization of cardanol and cashew shells to design cardanol-based PU (CPU) foams and wood-plastic films that can be recycled and reused. Firstly, cardanol-based polyphenols (CBPs) with a phenolic hydroxyl content of 3.29 mmol/g were prepared by Friedel-Crafts alkylation reaction using cardanol and guaiacol as raw materials. Subsequently, CPU foams were prepared by reacting CBPs with isocyanate, and the vertical and parallel compressive strengths could reach up to 0.27 MPa and 0.32 MPa, respectively, when the addition of CBPs was 80 %. These CPU foams, containing dynamic phenol-carbamate bonds, could be hot-pressed into transparent and smooth CPU films with tensile strengths of up to 30.5 MPa and could be re-formed at least three times. Finally, CPU foam and cashew shell waste were mixed and hot-pressed to produce a green wood-plastic composite with a tensile strength of up to 38.8 MPa. The resulting CPU-Wood films could be repaired or reshaped at least five times (38.0 MPa and 38.1 MPa) and could be formed into various shapes. This research paves the way for large-scale industrial production of recyclable and regenerative bio-based foams, making effective use of waste materials to achieve environmentally friendly production processes.

研究领域: 材料科学 · 环境科学 · 化学工程
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Scientific Reports · 2020 ·Vol. 10 ·期 1 ·1-12 · IF 3.998

Cardanol derived P, Si and N based precursors to develop flame retardant phenolic foam

Bo Caiying,Shi Zhongyu,Hu Lihong,Pan Zheng,Hu Yun,Yang Xiaohui,Jia Puyou,Ren Xiaoli,Zhang Meng,Zhou Yonghong

A novel eco-friendly halogen-free cardanol-based flame retardant with P, Si, and N on the chain backbone (PSNCFR) was synthesized and incorporated into phenolic foams (PFs). PSNCFR was comprehensively investigated via Fourier transform infrared spectroscopy and nuclear magnetic resonance. PSNCFR endowed PFs with flame retardancy, contributed to generating a composite char defense against flames, and efficiently prevented smoking from PFs. PSNCFR introduction improved the flexural strength of the PFs to approximately 155% of that of pristine PF. PSNCFR-modified PFs displayed a high limiting oxygen index value of 41.9%. The results of cone calorimeter show that the mean heat release rate, mean effective heat of combustion, and total heat release of the PSNCFR-modified PFs reduced by 26.92%, 35.71%, and 31.25%, respectively. In particular, the total smoke production of the PSNCFR-modified PFs decreased by 64.55%, indicating excellent smoke inhibition. As for the mechanism, the condensation and gas phases during pyrolysis were responsible for the synergistic flame retardancy in the modified PFs. The findings demonstrate that PSNCFR can be used in PF preparation to overcome their drawbacks of internal brittleness and flammability.

研究领域: 材料科学 · 化学工程
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Polymers · 2024 ·Vol. 16 ·期 11 ·1528 · IF 4.7

Enhanced Thermal and Mechanical Properties of Cardanol Epoxy/Clay-Based Nanocomposite through Girard’s Reagent

Ji Xu,Lingxiao Jia,Qixin Lan,Daheng Wu

The green and environmentally friendly cardanol epoxy resin has a bright application prospect, but its insufficient thermal/mechanical properties seriously hinder its application. Adding nanoclay to polymer matrix is an effective method to enhance the thermal/mechanical properties of material, but the dispersion and compatibility of nanoclay in epoxy resin remain to be solved. In this work, active Girard’s reagent clay (PG-clay) and non-active Girard’s reagent clay (NG-clay) were prepared by using acethydrazide trimethylammonium chloride (Girard’s reagent) as the modifier, and cardanol epoxy resin/G-clay nanocomposites were synthesized by the “clay slurry composite method”. The results showed that both PG-clay and NG-clay were dispersed in the epoxy matrix in the form of random exfoliation/intercalation, which effectively improved the thermal/mechanical properties of the composites. Tg of the cardanol epoxy resin has raised from 19.8 °C to 38.1 °C (4 wt.% PG-clay). When the mass fraction of clay is 4%, the tensile strength of the non-reactive NG-clay increases by 128%, and the elongation at break also increases by 101%. Simultaneously, the active PG-clay can participate in the curing reaction of epoxy resin due to the amino group, forming a chemical bond between the clay layer and the resin matrix and establishing a strong interfacial force. The tensile strength of the composite is increased by 970%, and the elongation at break is also increased by 428%. This research demonstrates that the cardanol epoxy resin/G-clay nanocomposite stands as a highly promising candidate for bio-based epoxy resin materials.

CAS / MDL: 1126-58-5 123-46-6
研究领域: 材料科学 · 化学工程
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POLYMER DEGRADATION AND STABILITY · 2025 · IF 7.4

Cardanol-derived polybenzoxazine networks integrated with high glass transition temperatures, flame retardancy and toughness

Zhong-Qiong Qin,Ze-Tao Xiao,Xi-Yang Lan,Xin Wang,Yuan Hu,Lei Song

In this work, diphenolic acid- and furfuryl-based benzoxazine (MDP-FuBz) was synthesized from methyl diphenolic acid (DPA) via the Mannich reaction. The curing temperature of MDP-FuBz was studied via differential scanning calorimetry (DSC). Since the flame retardant effect of MDP-FuBz was not satisfactory after curing, two kinds of phosphorus-containing cardanol-derived benzoxazine monomers (C-BA-DOPOBz and C-BA-diDOPOBz) were synthesized and characterized via Fourier transform infrared (FTIR) spectroscopy and nuclear magnetic resonance (NMR) spectroscopy. C-BA-DOPOBz and C-BA-diDOPOBz were used to endow MDP-FuBz with anti-flammability and toughness. As expected, the addition of 10 wt. % C-BA-DOPOBz or C-BA-diDOPOBz to MDP-FuBz improved the flame retardancy and glass transition temperature of the resulting interpenetrating polybenzoxazine networks. Although C-BA-diDOPOBz showed higher flame retardancy than C-BA-DOPOBz, both MDP-FuBz/10%C-BA-DOPOBz and MDP-FuBz/10%C-BA-diDOPOBz could not reach the UL-94 V-0 rating. C-BA-diDOPOBz was selected to further increase the content to modify MDP-FuBz. With the addition of 30 wt. % C-BA-diDOPOBz, the resulting interpenetrating polybenzoxazine networks reached the UL-94 V-0 rating, and the impact strength of MDP-FuBz/C-BA-diDOPOBz was 43 % higher than that of MDP-FuBz polybenzoxazine. This work presents interpenetrating polybenzoxazine networks consisting of diphenolic acid-based benzoxazine (rigid segment) and cardanol-based benzoxazine (flexible segment), which are integrated with high glass transition temperatures, flame retardancy and toughness.

研究领域: 材料科学 · 化学工程
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