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cardanol
JOURNAL OF APPLIED POLYMER SCIENCE · 2017 ·Vol. 134 ·期 23 · IF 1.86

Preparation of cardanol based epoxy plasticizer by click chemistry and its action on poly(vinyl chloride)

Leilei Yao,Qinhui Chen,Wenqin Xu,Zhibin Ye,Zhaodi Shen,Meijin Chen

In recent years, the using of reproducible resource and economical and efficient synthesis method has got wide concern. Herein, an environmental-friendly plasticizer originated from cardanol was synthesized by click chemistry. First, the cardanol sulfide (CS) was obtained by click chemistry reaction between the double bond of the side chain of cardanol and mercaptoethanol. The degree of the click reaction was estimated to reach 84.7% by testing the content of sulfur. Then, the epoxidation of the hydroxyl was performed to get cardanol based epoxy plasticizer (CEP) in the presence of epichlorohydrin. The epoxy value was 0.32. The structure of CS and CEP was confirmed by FT-IR and NMR techniques. A Haake torque rheometer was used to research the action of CEP on polyvinyl chloride (PVC). Results showed that it possessed favorable plasticization effect and stabilization effect on PVC. CEP had good heat stabilization in PVC, and could decrease the T g of PVC significantly. Moreover, CEP could increase the tensile strength of PVC when in a small amount, and could increase the plasticity of PVC when in a larger quantity significantly. The characteristics of volatile, migration and solvent extraction of PVC plasticized by CEP is similar to by dioctyl phthalate (DOP). © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017 , 134 , 44890.

CAS / MDL: 1112-67-0
研究领域: 材料科学 · 高分子化学 · 环境化学
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CHEMICAL ENGINEERING JOURNAL · 2022 · IF 16.744

Cardanol-derived anhydride cross-linked epoxy thermosets with intrinsic anti-flammability, toughness and shape memory effect

Jia-Li Huang,Hong-Liang Ding,Xin Wang,Lei Song,Yuan Hu

With the increasing awareness of environmental protection, the development of high-performance bio-based epoxy resins has attracted more and more attention to reduce the dependence on the petroleum-based 4,4′-diaminodiphenylmethane (DDM). In this work, we synthesized two kinds of cardanol-based curing agents (Car-DCP-MAH and Car-DPC-MAH) as alternatives for petroleum-based DDM. The chemical structures of Car-DCP-MAH and Car-DPC-MAH were confirmed by 1 H and 31 P NMR. Compared with the traditional DGEBA/DDM thermoset, the cured DGEBA/Car-DCP-MAH and DGEBA/Car-DPC-MAH thermosets both displayed good intrinsic fire resistance in terms of higher LOI values (29% and 28%, respectively, versus 24.5%) and V-0 rating in the UL-94 test. Furthermore, the results of the cone calorimeter test showed a significant reduction in the peak heat release rate (PHRR) values of the cured DGEBA/Car-DCP-MAH and DGEBA/Car-DPC-MAH which were 42.3% and 47.7%. The flame retardancy of these two systems was mainly due to the great carbonization ability and the formation of the intact and compact char layer. Owning to the flexible long alkyl chain in the crosslinking network, the toughness of the cured DGEBA/Car-DCP-MAH and DGEBA/Car-DPC-MAH products was greatly improved with the higher elongation at break and impact strength. Additionally, the cured DGEBA/Car-DCP-MAH and DGEBA/Car-DPC-MAH thermosets both showed preferable shape memory properties with a high shape recovery efficiency of 98.6% and 96.3%. This study provides a novel strategy to achieve bio-based epoxy thermosets with intrinsic anti-flammability, toughness and shape memory effect.

研究领域: 材料科学 · 化学工程
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RSC Advances · 2022 ·Vol. 12 ·期 17 ·10766-10777 · IF 4.036

Two-dimensional lamellar polyimide/cardanol-based benzoxazine copper polymer composite coatings with excellent anti-corrosion performance

Xiangyang Chen,Xinmei Zhang,Jipeng Chen,Weibin Bai,Xiaoxiao Zheng,Qi Lin,Fengcai Lin,Yanlian Xu

The economic loss and environmental damage caused by metal corrosion is irreversible. Thus, effective methods, such as coating technologies are used to protect metal surfaces from corrosion. In this work, cardanol-based benzoxazine (CB) was synthesized by a solvent-free method using cardanol, paraformaldehyde and n-octylamine. A cardanol-based benzoxazine copper polymer (CBCP) with good mechanical properties was then prepared by CuCl2 catalysis and can be cured at room temperature. Subsequently, polyimide corrosion inhibitors with a two-dimensional sheet structure (pyromellitic dianhydride polyimide (PDPI) and 1,4,5,8-naphthalene tetracarboxylic dianhydride polyimide (NDPI)) were designed and prepared. Lastly, PDPI or NDPI was mixed with CBCP to obtain two-dimensional lamellar polyimide/cardanol-based benzoxazine copper polymer composite coatings. The Tafel curves and electrochemical impedance spectroscopy (EIS) measurements showed composite coatings with good corrosion resistance in different corrosive media. Compared to CBCP coating, the anticorrosion performance of the composite coatings improved obviously, especially the coating obtained with 0.5 wt% PDPI. It exhibits a high polarization resistance (3.874 × 109 Ω), a high protection efficiency (99.99% and 97.98%) and low corrosion rate (3.376 × 10−6 mm year−1). This work suggested a facile and eco-friendly strategy for preparing bio-based anticorrosive composite coatings from low cost and abundant cardanol and polyimide corrosion inhibitors, which will significantly promote their application in metal anticorrosion.

CAS / MDL: 30525-89-4 89-32-7
研究领域: 材料科学 · 腐蚀与防护 · 绿色化学
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IRANIAN POLYMER JOURNAL · 2022 ·Vol. 31 ·期 9 ·1107-1115 · IF 2.485

Mechanical and thermal properties of elastic epoxy thermoset cured by cardanol-based diglycidyl epoxy modified polyetheramine

Jia Lingxiao,Chen Bin,Zhao Haichao,Lan Xijian

The highly cross-linked epoxy cured network suffers from the brittle nature and poor elongation, which hinders many potential applications. In this study, a biology-based cardanol NC-514S-modified polyether amine D230 was synthesized and used as an epoxy hardener (NC-D230). The effects of NC-514S content on the mechanical and thermal properties of the prepared samples were investigated. At the same time, we used cyclic stretching to further characterize its mechanical strength, and characterized the curing agent before and after modification through SEM and FTIR. Mechanical tests on the samples showed that the increase of NC-514S content results in lower tensile strength and Young’s modulus but an increase in elongation-at-breaks. DSC and TGA analyses showed a decreasing trend of glass transition temperature with the addition of NC-514S. Typically, the epoxy thermoset without/with 75% (by wt) NC-514S-modified D230 decreased tensile strength from 61.7 to 17.74 MPa, and Young’s modulus from 496 to 11.56 MPa. It increased elongation from 13.43% to 97.97%, and decreased glass temperature from 87.5 to 51.9 °C by DSC and 87.8 to 54.7 °C by DMA, respectively. This novel bio-based renewable cashew phenol-modified polyetheramine may provide an ideal candidate for toughening an epoxy-based thermosetting materials. At the same time, it also provides a new way for the toughening of epoxy resin. Graphical abstract

CAS / MDL: 9046-10-0
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/triazine-based polyol and DOPO derivative for thermally insulating and flame retardancy rigid polyurethane foam composites

Kumar Selvaraj,Hongfei He,Marisa E. Spontón,Na Sun,Hongliang Ding,Yao Yuan,Chuanshen Wang,Lu Liu,Yuxiang Yi,Bin Yu

Researchers are increasingly focusing on the development of biobased polyol derived rigid polyurethane foams (RPUFs) as sustainable alternatives to traditional polyether polyol based RPUFs targeting improvements in flame resistance, mechanical strength and thermal insulation. In this context novel biobased cardanol/triazine based polyol was synthesized through co-condensation of cardanol, melamine and paraformaldehyde and its chemical structure and functional groups was confirmed by FT-IR and ¹H NMR analyses. Using this polyol cardanol/triazine based rigid polyurethane foam (C/N-RPUF) was fabricated via a one-pot reaction under –NCO/–OH ratio of 1.1. To enhance fire safety C/N-RPUF composites were produced by incorporating 1, 3 and 5 wt% of a reactive DOPO derived polyol (DOPOP). Structural characterizations of composites were performed using FTIR and SEM-EDS techniques. Remarkably C/N-RPUF with 5 wt% DOPOP demonstrated superior flame retardancy achieving a UL-94 V-0 classification, limiting oxygen index (LOI) of 26.5%. Compressive strength values of neat C/N-RPUF and C/N-RPUF/5wt% DOPOP were 0.081 and 0.127 MPa respectively with the improvement attributed to additional cross-linking interactions within the foam structure. Additionally, the 5 wt% DOPOP composites showed a thermal conductivity of 0.051 W/(m·K), which is lower than that of conventional RPUFs, suggested its superior thermal insulation performance. In terms of fire performance composite showed significant reductions compared to pristine C/N-RPUF with 39.6% decrease in peak heat release rate (PHRR) and a 64.2 % reduction in CO emission. Overall, this work introduces an eco-friendly and efficient strategy for producing high-performance biobased rigid polyurethane foams combining flame resistance, compressive strength and superior insulation properties.

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JOURNAL OF VINYL & ADDITIVE TECHNOLOGY · 2024 · IF 3.8

Bio-based and effective: Cardanol-piperidine derivatives for enhanced polypropylene resistance against thermo- and photo-oxidative aging

Xuemei Zeng,Jianxiang Feng,Yulin He,Siyu Cao,Cheng Zhou,Kangqi Li,Jinjing Tan,Shuyi Chen,Yong Xia,Yuejun Liu,Pu Shi,Jin Zhu

Bio-based antioxidants have garnered attention for their sustainability and environmental benefits. In this study, we designed and synthesized three cardanol-piperidine derivatives (HSs) by utilizing hydrogenated cardanol (HC) and piperidine derivatives to improve the aging inhibition of polypropylene (PP). These bio-based antioxidants were intended as eco-friendly alternatives to conventional synthetic antioxidants. The impact of these HSs on the thermal stability, thermo-oxidative stability, and light stability of PP was thoroughly evaluated. The results unveiled that after 5 h of interaction with 2,2-diphenyl-1-picrylhydrazyl free radical, HSs exhibited a remarkable over 5-fold increase in free radical scavenging efficiency as compared to HC. Moreover, the addition of HSs significantly increased the oxidation induction time and the initial oxidation temperature compared to pristine PP. After photo-oxidative aging and thermo-oxidative aging, the HS-dosed PP demonstrated remarkable retention of elongation at break, reaching more than 72% and 69%. From the comparison with physical mixtures and the density functional theory calculations, an intramolecular synergism mechanism is proposed. The intramolecular synergism between hydrogenated cardanol and piperidine derivatives may be the main reason for the inhibition of PP aging. Highlights A method for constructing simultaneous efficient light, thermal, and oxygen stable polypropylene. The mechanism for achieving simultaneous stabilization of light, heat, and oxygen is the intramolecular synergy of phenol piperidine. The essence of intramolecular synergy of cardanol and piperidine derivatives is its' reduced hydrogen bond dissociation energy and energy gap.

CAS / MDL: 7144-05-0 36768-62-4
研究领域: 材料科学 · 化学工程 · 高分子科学 · 可持续化学
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JOURNAL OF APPLIED POLYMER SCIENCE · 2014 ·Vol. 131 ·期 11 · IF 1.64

Preparation of a liquid benzoxazine based on cardanol and the thermal stability of its graphene oxide composites

Guo-mei Xu,Tiejun Shi,Jianhua Liu,Qidong Wang

A novel liquid benzoxazine was synthesized by Mannich reaction of cardanol, paraformaldehyde, and allylamine. The benzoxazine structure was characterized by 1 H-NMR and FTIR. The liquid benzoxazine could dissolve easily in many solvents. The curing behavior of the benzoxazine was characterized by differential scanning calorimetry (DSC) and its curing temperature was about 233°C. A benzoxazine-functional silane coupling agent (BFSca) was synthesized with paraformaldehyde, phenolphthalein, and aminopropyltriethoxysilane. Graphene oxide (GO) was also made via improved Hummer's method. Then benzoxazine/GO composites were prepared using BFSca by solution blending and the curing behaviors of the composites were also characterized by IR, DSC, and thermogravimetric analysis. The minimum curing temperature and the highest 5% weight loss temperature for the composites was, respectively, 185 and 399.8°C. The SEM images of benzoxazine/GO composites demonstrated that BFSca had improved the dispersion of GO in the benzoxazine and also enhanced the thermal decomposition temperature of the composites. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014 , 131 , 40353.

研究领域: 高分子化学 · 材料科学
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Applied Materials Today · 2026 · IF 7

Cardanol-based fluorescent polyurethane with multi-stimulus-responsive shape memory behavior for ion recognition and information encryption

Yiran Fu,Caiying Bo,Miao Li,Hongfu Zhu,Yufeng Ma,Yonghong Zhou,Yuntong Li,Yanbo Ji

A cardanol PU with fluorescence/shape memory was built via B←N coordination boron ester. • Cardanol-derived B←N units enable ion-recognition functionality. • Optical, ion-recognition and shape-memory integration enables 2D/3D encryption. In this study, biomass-derived cardanol was employed as a sustainable material to construct multifunctional polyurethanes by introducing reversible B←N coordination boron ester bonds as alternatives to conventional organic dyes. Cardanol-based B←N coordination boron esters (C-BNEs) were first synthesized and exhibited intrinsic fluorescence and selective ion-recognition capability, with a fluorescence quenching efficiency toward Fe³ ⁺ as high as 98%. Based on these C-BNEs, a series of C-BNE-based polyurethanes (C-BNE-PUs) were subsequently fabricated. The resulting polyurethanes showed excellent mechanical performance, with a maximum tensile strength of 18.15 MPa and an elongation at break of up to ∼900%, together with good environmental stability after immersion in H₂O, HCl, and NaOH solutions for one week. Owing to the dynamic B←N coordination boron ester, the C-BNE-PUs also exhibited versatile multi-stimulus-responsive shape-memory behavior, achieving rapid shape recovery within 15 s at 37 °C under thermal stimulation and within approximately 60 s under infrared (IR) and ultraviolet (UV) irradiation. By integrating fluorescence, ion-recognition, and shape memory performance, 2D/3D information anti-counterfeiting platforms were successfully constructed, enabling multi-level encryption and controlled information decoding. This work demonstrates a sustainable strategy for transforming biomass-derived cardanol into multifunctional smart materials and highlights the potential of C-BNE-PUs for advanced applications in information storage and anti-counterfeiting technologies. Download: Download high-res image (152KB) Download: Download full-size image

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FIBERS AND POLYMERS · 2020 ·Vol. 21 ·期 8 ·1649-1656 · IF 1.797

Cardanol with a Covalently Attached Organophosphate Moiety as a Halogen-Free, Intrinsically Flame-Retardant PVC Bio-Plasticizer

Hou Delong,Wang Songhang,Chang Jinming,Xu Zhou,Zeng Qi,Wang Zhonghui,Yang Yongcheng,Yan Jun,Chen Yi

Plasticizers that enable flexible polyvinyl chloride (PVC) are usually combustible, restricting the application of PVC in fire-prone scenarios. In this context, intrinsically flame-retardant plasticizers displaying dual function continue to be the focus of intensive research. Despite their efficiency, the majority of these dual-functional plasticizers previously reported contain halogen elements, which, once ignited, emanate toxic and potentially carcinogenic substances, along with toxic gases and smoke, polluting the environment, damaging the biota, and threatening human health. Here, we report a strategy to obtain a halogen-free, intrinsically flame-retardant PVC bio-plasticizer that harnesses the phenolic hydroxyl of naturally occurring cardanol and covalent attachment of an organophosphate moiety. When combined with di-(2-ethylhexyl) phthalate (DOP), the organophosphate-containing cardanol is qualified as a co-plasticizer, while endowing the PVC materials with flame retardancy. Unlike inorganic flame-retardants, the engineered cardanol is compatible with PVC such that the mechanical properties of the PVC materials are not compromised. The rationale underlying the present effort may provide guidance for developing sustainable alternatives to halogen-containing plasticizers to address the sustainability challenge now confronting PVC industry.

CAS / MDL: 75-05-8 67-66-3
研究领域: 材料科学 · 化学工程 · 可持续发展
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CHEMICAL ENGINEERING JOURNAL · 2021 · IF 13.273

Cardanol as a versatile platform for fabrication of bio-based flame-retardant epoxy thermosets as DGEBA substitutes

Xin Wang,Haoxin Niu,Wenwen Guo,Lei Song,Yuan Hu

The development of high-performance thermosetting polymers has spawn extensive research interest over the past decade because of increasing awareness of environmental protection and sustainable policy. In this work, three cardanol-derived epoxy monomers named after CFGE, ECF, and ECFGE were synthesized, and ECFGE was selected to be further treated by flame-retardant owing to its superior thermal stability and mechanical strength. ECFGE was subsequently combined with cardanol-derived phosphate (DPP-CFR) to obtain flame-retardant bio-based epoxy materials as diglycidyl ether bisphenol A (DGEBA)-type epoxy substitutes. The chemical structure of CFGE, ECF, ECFGE, and DPP-CFR was well characterized by nuclear magnetic resonance and elemental analysis. The influence of DPP-CFR on the curing kinetics of the ECFGE/DDM system was investigated by the non-isothermal DSC . The addition of DPP-CFR imparted excellent flame-retardancy to the cured ECFGE/DDM system. Specifically, the cured ECFGE/DDM system with 15 wt% of DPP-CFR exhibited UL-94V-0 classification and LOI value of 31.0%, and its peak heat release rate was declined by 48% and 72%, respectively, compared to the cured ECFGE/DDM and DGEBA/DDM. Additionally, the cured ECFGE/DDM system with 15 wt% of DPP-CFR also showed better tensile strength and toughness than the cured DGEBA/DDM counterpart. This study demonstrates that cardanol can be utilized as a versatile platform for the fabrication of high-performance bio-based thermosetting polymers with excellent comprehensive properties.

研究领域: 材料科学 · 聚合物化学 · 可持续化学
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POLYMER DEGRADATION AND STABILITY · 2014 · IF 2.633

Synthesis and fire properties of rigid polyurethane foams made from a polyol derived from melamine and cardanol

Meng Zhang,Jinwen Zhang,Shuigen Chen,Yonghong Zhou

In this work, a melamine and cardanol-derived Mannich base polyol (MCMP) was synthesized via a two-step process. First, cardanol was allowed to react with paraformaldehyde melamine and diethanolamine to yield mixed Mannich bases which were subsequently propoxylated to give the MCMP. Rigid polyurethane foams (RPUFs) were prepared using MCMP and a polyisocyanate. Effects of expandable graphite (EG), ammonium polyphosphate (APP) and diethyl ethylphosphate (DEEP) on the flame retardancy, mechanical properties , thermal stability and morphology of the resultant RPUFs were studied. It was demonstrated that the melamine incorporated into the MCMP molecular structure increased the thermal stability and the flame retardancy of the RPUF. The fire resistance of the foam could be further enhanced by the addition of flame retardants . EG is more effective than APP and DEEP in enhancing the limiting oxygen index of MCMP-based RPUFs. The flame-retardant-filled RPUFs display a better compressive strength , thermal stability, char residue, heat release and smoke emission than does the non-filled foams.

研究领域: 材料科学 · 化学工程
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Journal of Materials Chemistry B · 2022 ·Vol. 10 ·期 45 ·9413-9423 · IF 7.571

Sheet-like Janus hemostatic dressings with synergistic effects of cardanol hemostasis and quaternary ammonium salt antibacterial action

Yuxia Zhang,Xiaoyu Lu,Chongyi Chi,Yanyan Zheng,Qinhui Chen

It is of utmost importance that bleeding should be stopped and infection be prevented in people with trauma. In this study, an anisotropic Janus mesoporous silica nanosheet (MSNS) with different functional groups was designed and prepared. In order to endow both sides of the MSNS with independent fast hemostasis and effective antibacterial action, the MSNS was modified with cardanol (CA) and 2,3-epoxypropyltrimethylammonium (GTA). The addition of CA significantly improved the hemostatic property of the MSNS. In a SD rat femoral artery injury model, the hemostatic time of CA-MSNS-GTA was 47% shorter than that of the MSNS, attributed to the sealing of the hydrophobic alkyl side chain and the adhesion of phenolic hydroxyl groups in CA. CA-MSNS-GTA could form a three-dimensional network with fibrin to further accelerate the coagulation process. This Janus material exhibited excellent antibacterial effects (∼90%) against Gram-positive bacteria (S. pneumoniae) and Gram-negative bacteria (E. coli) due to the presence of GTA. The cytotoxicity test showed that CA-MSNS-GTA exhibited biosafety, which provided safety guarantee for clinical applications in the future. This Janus dressing with different functions on two opposite sides provides synergetic multifunctional effects during wound healing.

CAS / MDL: 919-30-2 2530-85-0
研究领域: 材料科学 · 生物医学工程 · 创伤护理
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