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  • Open Access

    ARTICLE

    Enhanced Water Resistance Performance of Castor Oil—Based Waterborne Polyurethane Modified by Methoxysilane Coupling Agents via Thiol-Ene Photo Click Reaction

    Zhipeng He1,2, Junqi Xue1,2, Yanzi Ke1,2, Ying Luo1,2,*, Qiming Lu1,2, Yuehua Xu1,2, Chaoqun Zhang1,2,*

    Journal of Renewable Materials, Vol.10, No.3, pp. 591-604, 2022, DOI:10.32604/jrm.2022.017790 - 28 September 2021

    Abstract Nowadays, waterborne polyurethanes (WPUs) prepared from renewable resources has attracted more and more attention. However, due to its structure, the prepared films easily swells in water and greatly affects the application range of WPUs. Therefore, solving the problem of water resistance is a way to improve the application range of WPUs. In this study, a series of WPU dispersions were prepared using castor oil as the bio-based polyol. Besides, the thiol-ene photo click reaction was carried out on the WPU films for silane modification. The effect of the silane modification on the chemical structures of… More > Graphic Abstract

    Enhanced Water Resistance Performance of Castor Oil—Based Waterborne Polyurethane Modified by Methoxysilane Coupling Agents via Thiol-Ene Photo Click Reaction

  • Open Access

    ARTICLE

    New Biobased Polyurethane Materials from Modified Vegetable Oil

    Chakib Mokhtari1, Fouad Malek1, Sami Halila2, Mohamed Naceur Belgacem3,*, Ramzi Khiari3,4,5,*

    Journal of Renewable Materials, Vol.9, No.7, pp. 1213-1223, 2021, DOI:10.32604/jrm.2021.015475 - 18 March 2021

    Abstract Bio-based polyurethanes (PUs) have been occurred a large attention nowadays. It was found to be an alternative to the petrochemical based materials to the fact of their weak environmental influence, availability, good price and biodegradability. In addition, the nature shows several bio-derived compounds as raw materials for the synthesis of polyols, including the vegetable oils, polyphenol, terpene, and other bio-renewable sources. With the aim to develop a new family of biobased polyurethanes (PUs) via vegetable oils, the elaboration of new Jojoba-based PUs was performed by catalyst-free polycondensation reaction of a synthesized Jojoba diol with various More > Graphic Abstract

    New Biobased Polyurethane Materials from Modified Vegetable Oil

  • Open Access

    ARTICLE

    Synthesis of a Fully Biobased Polyfunctional Vinyl Oligomer and Their UV Cured Films Prepared via Thiol-ene Coupling

    Changqing Fu1,2, Jiahui Wang1,2, Lie Chen1,2, Liang Shen1,2,*

    Journal of Renewable Materials, Vol.7, No.8, pp. 795-805, 2019, DOI:10.32604/jrm.2019.07503

    Abstract In this paper, a fully bio-based vinyl oligomer with high functionalities was successfully prepared from rapeseed oil by three modification steps: epoxidation of rapeseed oil, solvent-free and catalyst-free ring opening by 10-undecylenic acid followed by esterification with 10-undecenoyl chloride. Then, the renewable polymers were prepared by photo-polymerization of these modified vegetable oils with typical thiol monomers: pentaerythritol tetrakis (3-mercaptopropionate), pentaerythritol tris (3-mercaptopropionate) and 1,2-ethanedithiol. The synthesis of the vinyl oligomer was monitored by nuclear magnetic resonance and Fourier-transform infrared spectroscopy. The average number of the carbon-carbon double bonds of the resulting vinyl oligomer is high… More >

  • Open Access

    ARTICLE

    Biobased Aromatic-Aliphatic Polyols by Thiol-Ene Reactions of Propoxylated Mercaptanized Cardanol

    Maha L. Shrestha1,2,*, Mihail Ionescu1, Xianmei Wan1, Thomas Upshaw3

    Journal of Renewable Materials, Vol.6, No.6, pp. 630-641, 2018, DOI:10.7569/JRM.2018.634106

    Abstract Aromatic-aliphatic polyols were obtained previously from the thiol-ene reactions of propoxylated cardanol with hydroxyalkyl mercaptans; these aromatic-aliphatic polyols were then utilized in the preparation of rigid polyurethane foams with excellent properties. The current work describes a variant of cardanol polyol synthesis by thiol-ene reactions in three steps. The first step is propoxylation of cardanol by reacting cardanol with propylene oxide; the second step is mercaptanization of propoxylated cardanol by reacting double bonds with hydrogen sulfide; and the third step involves the addition of the thiol groups of mercaptanized propoxylated cardanol to the double bonds of More >

  • Open Access

    ARTICLE

    Cardanol-Based Polyurethane Coatings via Click Chemistry: An Eco-friendly Approach

    Kunal Wazarkar, Anagha Sabnis*

    Journal of Renewable Materials, Vol.6, No.5, pp. 517-528, 2018, DOI:10.7569/JRM.2017.634181

    Abstract This research work discloses the preparation of polyurethane coatings from cardanol modified using thiolene chemistry, wherein unsaturated long alkyl chain of cardanol was successfully utilized via thiol-ene click reaction to synthesize polyol. For this purpose, cardanol and thioglycerol was reacted in the presence of Irgacure 184 (photoinitiator) and 1,8-Diazabicyclo[5.4.0]undec-7-ene (catalyst) and exposed to UV light for 12 h at 80 °C. One mole of thioglycerol was successfully added across the double bond of fatty chain of cardanol and confirmed by chemical and spectroscopic analysis. Further, the polyol thus prepared was cured with various polyisocyanates, viz., More >

  • Open Access

    ARTICLE

    Biobased Aromatic-Aliphatic Polyols from Cardanol by Photochemical Thiol-ene Reaction

    Maha L. Shrestha1, 2,*, Mihail Ionescu1, Xianmei Wan1, Zoran S. Petrović1

    Journal of Renewable Materials, Vol.6, No.5, pp. 504-516, 2018, DOI:10.7569/JRM.2017.634187

    Abstract Biobased aromatic-aliphatic polyols were previously synthesized from a thermal thiol-ene reaction of propoxylated cardanol with 2-mercaptoethanol (ME) in the presence of azobisisobutyronitrile (AIBN) as a radical initiator. Cardanol used for this purpose was obtained as a dark-brown liquid (Gardner Color Reference ∼18). The photochemical thiol-ene reaction can also be used to prepare aromatic-aliphatic polyols by employing cardanol. Via the photochemical thiol-ene reaction, 2-mercaptoethanol was added successfully to C=C double bond of cardanol, suggesting that phenolic group may not play an inhibitory role in the radical thiol-ene reaction. However, we preferred to alkoxylate the phenolic hydroxyl More >

  • Open Access

    ARTICLE

    Biobased Aromatic-Aliphatic Polyols from Cardanol by Thermal Thiol-Ene Reaction

    Maha L. Shrestha1, Mihail Ionescu1*, Xianmei Wan1, Nikola Bilić1, Zoran S. Petrović1, Tom Upshaw2

    Journal of Renewable Materials, Vol.6, No.1, pp. 87-101, 2018, DOI:10.7569/JRM.2017.634153

    Abstract Cardanol is a natural phenol which is obtained from high vacuum distillation of cashew nut shell liquid. It contains a hydrocarbon chain of 15 carbon atoms in the meta position, either with one, two or three non-conjugated double bonds. This article describes thermal thiol-ene reaction to synthesize new cardanol-based polyols for polyurethanes with aromatic-aliphatic structure. Phenolic hydroxyl group was blocked by alkoxylation and 2-mercaptoethanol was added to the double bonds of propoxylated cardanol. The resultant product is a mixture of polyols that may contain one, two, three or four hydroxyl groups, as a function of the More >

  • Open Access

    Synthesis of Novel Biobased Polyol via Thiol-Ene Chemistry for Rigid Polyurethane Foams

    N. Elbers1, C. K. Ranaweera1, M. Ionescu2, X. Wan2, P. K. Kahol3, Ram K. Gupta1,2*

    Journal of Renewable Materials, Vol.5, Suppl.1, pp. 74-83, 2017, DOI:10.7569/JRM.2017.634137

    Abstract The objective of this research is to prepare rigid polyurethane (PU) foams from α-phellandrene, a biobased compound. Two types of polyols were synthesized by reacting α-phellandrene with 2-mercaptoethanol and α-thioglycerol via thiol-ene chemistry route. The completion of the reaction was identified by using FTIR. PU foams from α-phellandrene polyols and commercial polyol were compared with regard to foam characteristics and properties. All the PU foams showed apparent density of 28–39 kg/m3 with closed-cell content above 90%. The highest glass transition temperature of 229 °C and compressive strength of 220 kPa were observed for the polyol synthesized More >

  • Open Access

    Biobased Polyols Using Thiol-Ene Chemistry for Rigid Polyurethane Foams with Enhanced Flame-Retardant Properties

    C. K. Ranaweera1, M. Ionescu2, N. Bilic2, X. Wan2, P. K. Kahol3, Ram K. Gupta1,2*

    Journal of Renewable Materials, Vol.5, Suppl.1, pp. 1-12, 2017, DOI:10.7569/JRM.2017.634105

    Abstract Biobased polyol was synthesized using 1-thioglycerol and limonene, an extract of orange peel, via thiol-ene chemistry as an alternative to petrochemical-based polyol for preparation of rigid polyurethane foams (RPFs). Fire-retardant polyurethane foams were prepared by addition of different amounts of dimethyl methyl phosphonate (DMMP) in the polyol. The effect of DMMP on the properties of RPFs was studied. All the biobased RPFs maintained a regular cell structure with uniform cell distribution and over 90% of closed cell. The RPFs showed excellent compressive strength of ~230 kPa without addition of DMMP. These RPFs almost retained their… More >

  • Open Access

    REVIEW

    Marriage of Furans and Vegetable Oils through Click Chemistry for the Preparation of Macromolecular Materials: A Succinct Review

    Talita M. Lacerda1,2,*, Alessandro Gandini1,2

    Journal of Renewable Materials, Vol.2, No.1, pp. 2-12, 2014, DOI:10.7569/JRM.2013.634127

    Abstract The inevitable future scarcity of fossil resources, coupled with sustainability considerations, have stimulated the use of renewable resources for material synthesis, and highly effi cient polymerization methods that meet the requirements of green chemistry have drawn attention to fatty acid-based polymers. Additionally, the polymerization of furan monomers and the exploitation of some of the chemical peculiarities of the furan heterocycle have generated a wide diversity of macromolecular materials. A novel approach is reviewed here, calling upon the combined use of both vegetable oils and their derivatives together with furans, as a promising technique to obtain More >

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