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Plasticizers Derived from Biomass Resources: a Short Review

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Plasticizers Derived from Biomass Resources: a Short Review polymers Review Plasticizers Derived from Biomass Resources: A Short Review Puyou Jia 1,*, Haoyu Xia 2, Kehan Tang 2 and Yonghong Zhou 1,* 1 Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry (CAF); Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University; Key Lab of Biomass Energy and Materials, 16 Suojin North Road, Nanjing 210042, China 2 College of Chemical Engineering, Nanjing Tech University, 30 Pu Zhu Road, Nanjing 211800, China; [email protected] (H.X.); [email protected] (K.T.) * Correspondence: [email protected] (P.J.); [email protected] (Y.Z.); Tel.: +86-025-85482520 (P.J.); +86-025-85482777 (Y.Z.) Received: 1 November 2018; Accepted: 22 November 2018; Published: 24 November 2018 Abstract: With rising environmental concerns and depletion of petrochemical resources, biomass-based chemicals have been paid more attention. Polyvinyl chloride (PVC) plasticizers derived from biomass resources (vegetable oil, cardanol, vegetable fatty acid, glycerol and citric acid) have been widely studied to replace petroleum-based o-phthalate plasticizers. These bio-based plasticizers mainly include epoxidized plasticizer, polyester plasticizer, macromolecular plasticizer, flame retardant plasticizer, citric acid ester plasticizer, glyceryl ester plasticizer and internal plasticizer. Bio-based plasticizers with the advantages of renewability, degradability, hypotoxicity, excellent solvent resistant extraction and plasticizing performances make them potential to replace o-phthalate plasticizers partially or totally. In this review, we classify different types of bio-based plasticizers according to their chemical structure and function, and highlight recent advances in multifunctional applications of bio-based plasticizers in PVC products. This study will increase the interest of researchers in bio-based plasticizers and the development of new ideas in this field. Keywords: plasticizer; polyvinyl chloride; biomass resources; review 1. Introduction Plasticizers are among the most important additives required for the processing of polymer materials, especially polyvinyl chloride (PVC) plastics, which accounts for more than 60% of the total yield of plastic auxiliaries [1,2]. Traditional petroleum-based phthalate plasticizers are the most widely used globally. The yield and consumption of traditional phthalate plasticizers account for a large proportion of the total plasticizer production and sales, but they are gradually limited due to potential threats to human health and environment. Strict regulations on environmental protection and safety have been formulated and carried out. The development of environmentally-friendly non-toxic plasticizers and biodegradable bio-based plasticizers to replace phthalates has been a research hot spot. Non-toxic green plasticizers with high performance, oil resistance, extraction and migration resistance used in electrical insulation, food packaging, and medical and health products are constantly being developed, produced and applied. Plasticizers are functional additives, which are used to improve flexibility, plasticity, processability, and elongation of polymers, especially in PVC products [3]. When a plasticizer is added to a polymer, the intermolecular subvalent bond force is weakened, the crystallinity is lowered, the relative movement between the molecular segments is increased and the plasticity of the material is improved. Therefore, plasticizers are mainly used to decrease hardness, softening temperature, elastic modulus, and embrittlement temperature of Polymers 2018, 10, 1303; doi:10.3390/polym10121303 www.mdpi.com/journal/polymers Polymers 2018, 10, 1303 2 of 27 Polymers 2018, 10, x FOR PEER REVIEW 2 of 28 polymers,include citric while acid improving ester, phosphates, their flexibility polyesters, and halogenated elongation. Non-phthalatealkanes, and epoxy plasticizer compounds alternatives [4–7]. includeWith the citric increase acid ester,in people’s phosphates, awareness polyesters, of environmental halogenated protection, alkanes, and especially epoxy compoundsthe discovery [4– 7of]. Withpotential the increasethreats to in human people’s health awareness by phthalate of environmental plasticizers and protection, environmental especially pollution the discovery problems, of potentialthe global threats hygienic to human requirements health by for phthalate plastic plasticizersadditives are and increasing environmental. The pollution use of n problems,on‐phthalate the globalplasticizer hygienic alternatives requirements has been for gradually plastic additives introduced are increasing. [8–10]. The use of non-phthalate plasticizer alternatives has been gradually introduced [8–10]. 2. Plasticizer Derived from Biomass Resources 2. Plasticizer Derived from Biomass Resources 2.1. Biomass Based Epoxidized Plasticizer 2.1. Biomass Based Epoxidized Plasticizer Epoxidized plasticizer is a kind of environmentally-friendly plasticizer used in plastics industry, rubberEpoxidized industry, plasticizerand coatings is aand kind new of environmentally-friendlypolymer materials [11,12]. plasticizer Compared used with in other plastics plasticizers, industry, rubberthe epoxy industry, group andin the coatings epoxidized and new plasticizer polymer structure materials could [11,12 absorb]. Compared and neutralize with other the plasticizers, hydrogen thechloride epoxy released group inby the PVC epoxidized during plasticizerlight or thermal structure de couldgradation, absorb which and neutralizerestricts or the delay hydrogens the chloridecontinuous released decomposition by PVC during of PVC light, endow or thermals PVC degradation, products with which good restricts light and or delaysthermal the stability continuous and decompositionextends their service of PVC, life. endows Besides, PVC it has products been approved with good for light food and packaging thermal stability and medical and extends equipment their servicematerials life. in Besides, many cou it hasntries been and approved regions fordue food to the packaging extremely and low medical toxicity equipment of epoxidized materials plasti incizers many, countrieswhich has andmade regions its production due to the and extremely price grow low in toxicityrecent years. of epoxidized Biomass-based plasticizers, epoxidized which plasticizers has made itsmainly production include and epoxidized price grow vegetable in recent oils, years. epoxidized Biomass-based fatty acid epoxidized esters and plasticizers epoxy group mainly containing include epoxidizedcardanol derivatives vegetable.oils, Currently, epoxidized vegetable fatty acid oils esters and e andpoxidized epoxy group fatty containingacid esters cardanolhave been derivatives. used on Currently,the market vegetable [13,14]. oils and epoxidized fatty acid esters have been used on the market [13,14]. Epoxidized soybeansoybean oil oil (ESO) (ESO) is a collectionis a collection of organic of compoundsorganic compounds obtained fromobtained the epoxidation from the ofepoxidation soybean oil of thatsoybean have oil been tha widelyt have usedbeen aswidely plasticizers used as and plasticizers heat stabilizers and heat of PVC stabilizers materials. of PVC The chemicalmaterials. structure The chemical of ESO structure is shown of inESO Figure is shown1. Ferrer in Figure et al. found 1. Ferrer that et formulations al. found that based formulati on PVCons withbased different on PVC amounts with different of ESO amounts (from 30 of to 50ESO wt (from %) increased 30 to 50 compatibility wt %) increased and improvedcompatibility thermal and stabilityimproved [15 thermal]. Park etstability al. investigated [15]. Park the et al performances. investigated of the epoxy perform resinsances plasticized of epoxy with resins ESO plasticized [16]. They foundwith ESO that [16]. the They thermal found stability that the and ther glassmal transitionstability and temperature glass transition of epoxy temperature resins reduced of epoxy with resins the additionreduced with of ESO. the addition This phenomenon of ESO. This occurs phenomenon due to the occurs decreased due to density the decreased of the epoxydensity network. of the epoxy The additionnetwork. ofThe ESO addition causes theof ESO increase causes of stress the increase intensity of factor stress along intensity with thefactor flexural along strength. with the Zhao flexural et al. investigatedstrength. Zhao the et plasticizing al. investigated effect the of ESOplasticizing on polybutylene effect of ESO succinate on polybut (PBS)ylene [17]. The succinate results (PBS) show [17] that. ESOThe results efficiently show improves that ESO elongation efficiently atimprove break ofs elongation PBS. The elongationat break of atPBS. break The reaches elongation a maximum at break valuereaches when a maximum the content value of ESOwhen is the 5 wt content % of PBS, of ESO 15 times is 5 wt more % thanof PBS the, 15 elongation times more of purethan PBS.the Moreover,elongation ESOof pure enhances PBS. Moreover, the elongation ESO aten breakhances of the poly(lactic elongation acid) at break (PLA) of by p 63%.oly(lactic Xu et acid) al. studied (PLA) theby 63%. performances Xu et al. studied of PLA the plasticized performances with ESOof PLA [18 ].plasticized The results with show ESO that [18]. 9 wt The % results ESO increased show that the 9 elongationwt % ESO increase at breakd of the PLA elongation by about at 63%. break PLA of PLA blends by containingabout 63%. 6PLA wt %blends ESO showcontaining
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