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Polymers
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Green Plasticizers for Polymers
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Green Plasticizers for Polymers

A special issue of Polymers (ISSN 2073-4360).

Deadline for manuscript submissions: closed (15 April 2018) | Viewed by 49284

Special Issue Editor

Prof. Dr. Milan Maric

E-Mail Website
Guest Editor
Department of Chemical Engineering, McGill University, Montreal, QC H3A 0G4, Canada
Interests: controlled radical polymerization; nitroxide mediated polymerization; green plasticizers

Special Issue Information

Dear Colleagues,

Plasticizers have long been used to impart flexibility and improve the processing behaviour of many polymers, notably poly(vinylchloride) (PVC).  Despite the improvement in properties in such blends, one the most common group of plasticizers, the phthalates have become increasingly under scrutiny due to concerns regarding toxic metabolites, which can encounter humans via migration from articles, such as blood bags and children’s toys.  Links between phthalates and health issues, such as endrocrine disruption have been reported.  Consequently, industrial and academic attention has shifted towards using plasticizers which do not degrade into non-toxic metabolites, and the thrust into replacement plasticizers has been further shifted towards green plasticizers that not only have favourable leaching properties and degradation into non-toxic products upon disposal, but also are sourced from sustainable building blocks.

Papers are sought for this Special Issue that reflect the state-of-the-art of green plasticizers in polymer formulations.  The scope of this issue ranges from synthesis of green plasticizers, enhancement of physical and rheological properties, migration of plasticizers upon disposal, relationships between plasticizers and human health, and life-cycle-assessment. Particular emphasis will be placed on the design and evaluation of new green plasticizers, using the principles of green chemistry as a sustainability checklist.

Prof. Milan Maric
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Polymers is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Green plasticizers
  • polymers
  • leaching
  • sustainability
  • life cycle assessment
  • phthalates

Published Papers (6 papers)

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Research

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15 pages, 3369 KiB  
Article
The Impact of Plasticizer and Degree of Hydrolysis on Free Volume of Poly(vinyl alcohol) Films
by Rebecca J. Fong, Alexander Robertson, Peter E. Mallon and Richard L. Thompson
Polymers 2018, 10(9), 1036; https://doi.org/10.3390/polym10091036 - 18 Sep 2018
Cited by 38 | Viewed by 10642
Abstract
The effect of plasticizer species and the degree of hydrolysis (DH) on the free volume properties of poly(vinyl alcohol) (PVA) were studied using positron annihilation lifetime spectroscopy. Both glycerol and propylene glycol caused an increase in the free volume cavity radius, although exhibited [...] Read more.
The effect of plasticizer species and the degree of hydrolysis (DH) on the free volume properties of poly(vinyl alcohol) (PVA) were studied using positron annihilation lifetime spectroscopy. Both glycerol and propylene glycol caused an increase in the free volume cavity radius, although exhibited distinct plasticization behavior, with glycerol capable of occupying existing free volume cavities in the PVA to some extent. The influence of water, normally present in PVA film under atmospheric conditions, was also isolated. Water added significantly to the measured free volume cavity radius in both plasticized and pure PVA matrices. Differences in plasticization behavior can be attributed to the functionality of each plasticizing additive and its hydrogen bonding capability. The increase in cavity radii upon plasticizer loading shows a qualitative link between the free volume of voids and the corresponding reduction in Tg and crystallinity. Cavity radius decreases with increasing DH, due to PVA network tightening in the absence of acetate groups. This corresponds well with the higher Tg observed in the resin with the higher DH. DH was also shown to impact the plasticization of PVA with glycerol, indicating that the larger cavities—created by the weaker hydrogen bonding acetate groups—are capable of accommodating glycerol molecules with negligible effect on the cavity dimensions. Full article
(This article belongs to the Special Issue Green Plasticizers for Polymers)
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14 pages, 4489 KiB  
Article
Designing Green Plasticizers: Linear Alkyl Diol Dibenzoate Plasticizers and a Thermally Reversible Plasticizer
by Hanno C. Erythropel, Aurélie Börmann, Jim A. Nicell, Richard L. Leask and Milan Maric
Polymers 2018, 10(6), 646; https://doi.org/10.3390/polym10060646 - 09 Jun 2018
Cited by 14 | Viewed by 7252
Abstract
Several linear alkyl diol dibenzoate compounds, ranging from C3 to C6 in central diol length, were evaluated for their plasticizing effectiveness in blends with poly(vinyl chloride) (PVC). The results were compared to blends of PVC/di(2-ethylhexyl) phthalate (DEHP), the most commonly used commercial plasticizer. [...] Read more.
Several linear alkyl diol dibenzoate compounds, ranging from C3 to C6 in central diol length, were evaluated for their plasticizing effectiveness in blends with poly(vinyl chloride) (PVC). The results were compared to blends of PVC/di(2-ethylhexyl) phthalate (DEHP), the most commonly used commercial plasticizer. DEHP has come under scrutiny, due to its suspected endocrine-disrupting behaviour, and the proposed diol dibenzoates have previously been shown to have the potential to be green, safe candidates for DEHP replacement. The thermal and mechanical properties of PVC/dibenzoate blends were determined, and include glass transition temperature (Tg), the elongation at break, maximum stress, apparent moduli, torsional modulus, and surface hardness. The C3, C5, and C6 dibenzoates performed as well as or better than DEHP, with the exception of torsional modulus, further supporting their use as green plasticizers. For blends with 1,4-butanediol dibenzoate, differential scanning calorimetry and torsional temperature sweeps suggested that the compound partly crystallizes within PVC blends over the course of two days, thereby losing the ability to effectively plasticize PVC. However, upon heating to temperatures above 60 °C, effective plasticization was again observed. 1,4-Butanediol dibenzoate is thereby a reversible heat-activated plasticizer or processing aid with excellent plasticizer properties at mildly elevated temperatures. Full article
(This article belongs to the Special Issue Green Plasticizers for Polymers)
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15 pages, 3538 KiB  
Article
Reactive Energetic Plasticizers Utilizing Cu-Free Azide-Alkyne 1,3-Dipolar Cycloaddition for In-Situ Preparation of Poly(THF-co-GAP)-Based Polyurethane Energetic Binders
by Mingyang Ma and Younghwan Kwon
Polymers 2018, 10(5), 516; https://doi.org/10.3390/polym10050516 - 10 May 2018
Cited by 22 | Viewed by 5172
Abstract
Reactive energetic plasticizers (REPs) coupled with hydroxy-telechelic poly(glycidyl azide-co-tetrahydrofuran) (PGT)-based energetic polyurethane (PU) binders for use in solid propellants and plastic-bonded explosives (PBXs) were investigated. The generation of gem-dinitro REPs along with a terminal alkyne stemmed from a series of [...] Read more.
Reactive energetic plasticizers (REPs) coupled with hydroxy-telechelic poly(glycidyl azide-co-tetrahydrofuran) (PGT)-based energetic polyurethane (PU) binders for use in solid propellants and plastic-bonded explosives (PBXs) were investigated. The generation of gem-dinitro REPs along with a terminal alkyne stemmed from a series of finely designed approaches to not only satisfy common demands as conventional energetic plasticizers, but also to prevent the migration of plasticizers. The miscibility and rheological behavior of a binary mixture of PGT/REP with various REP fractions were quantitatively determined by differential scanning calorimetry (DSC) and rheometer, respectively, highlighting the promising performance of REPs in the formulation process. The kinetics on the distinct reactivity of propargyl vs. 3-butynyl species of REPs towards the azide group of the PGT prepolymer in terms of Cu-free azide-alkyne 1,3-dipolar cycloaddition (1,3-DPCA) was studied by monitoring 1H nuclear magnetic resonance spectroscopy and analyzing the activation energies (Ea) obtained using DSC. The thermal stability of the finally cured energetic binders with the incorporation of REPs indicated that the thermal stability of the REP/PGT-based PUs was maintained independently of the REP content. The tensile strength and modulus of the PUs increased with an increase in the REP content. In addition, the energetic performance and sensitivity of REP and REP triazole species was predicted. Full article
(This article belongs to the Special Issue Green Plasticizers for Polymers)
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16 pages, 7993 KiB  
Article
Evolution of Filament-Shaped Porous Structure in Polycarbonate by Stretching under Carbon Dioxide
by Tomoaki Taguchi, Tomoe Hatakeyama, Ramu Miike and Hiromu Saito
Polymers 2018, 10(2), 148; https://doi.org/10.3390/polym10020148 - 05 Feb 2018
Cited by 1 | Viewed by 3799
Abstract
We found that a filament-shaped porous structure with periodic distance was obtained in polycarbonate for optical disk grade (OD-PC) film by stretching under compressed carbon dioxide (CO2). The evolution of the characteristic porous structure was investigated by in situ observation during [...] Read more.
We found that a filament-shaped porous structure with periodic distance was obtained in polycarbonate for optical disk grade (OD-PC) film by stretching under compressed carbon dioxide (CO2). The evolution of the characteristic porous structure was investigated by in situ observation during the stretching under compressed CO2 and the optical microscopic observation of the stretched specimen. The voids were obtained under high CO2 pressure as in the case of elevated temperature, suggesting that the evolution of the voids was caused by crazing due to chain disentanglement by accelerated molecular motion owing to the plasticization effect of CO2. The filament-shaped voids were initiated at around the yielding point and increased continuously by nucleation in the matrix around the surface of the pre-existing voids. The shape of the voids did not change to an ellipsoidal one during stretching due to suppression of the craze opening by the hydrostatic pressure effect. The stretching of the CO2-absorbed depressurized OD-PC revealed that the initiation of the voids was not only caused by the plasticization effect, but the hydrostatic pressure effect was also required. Full article
(This article belongs to the Special Issue Green Plasticizers for Polymers)
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3939 KiB  
Article
Synthesis and Properties of a Novel Environmental Epoxidized Glycidyl Ester of Ricinoleic Acetic Ester Plasticizer for Poly(vinyl chloride)
by Jie Chen, Ke Li, Yigang Wang, Jinrui Huang, Xiaoan Nie and Jianchun Jiang
Polymers 2017, 9(12), 640; https://doi.org/10.3390/polym9120640 - 29 Nov 2017
Cited by 32 | Viewed by 8548
Abstract
A novel renewable plasticizer based on castor oil, epoxidized glycidyl ester of ricinoleic acetic ester (EGERAE), was synthesized and applied into Poly(vinyl chloride) (PVC) for the first time. Its molecular structure was characterized by FT-IR and 1H NMR. The effects of replacement [...] Read more.
A novel renewable plasticizer based on castor oil, epoxidized glycidyl ester of ricinoleic acetic ester (EGERAE), was synthesized and applied into Poly(vinyl chloride) (PVC) for the first time. Its molecular structure was characterized by FT-IR and 1H NMR. The effects of replacement of petroleum-based commercial plasticizer dioctyl phthalate (DOP) with EGERAE in poly(vinyl chloride) (PVC) films were researched. Thermal stability, dynamic mechanical property and mechanical properties of PVC films were investigated with thermogravimetric analysis (TGA), dynamic mechanical analysis (DMA) and tensile tests. The results indicated that this castor oil-based plasticizer was able to improve the thermal stability of PVC blends when partially of completely substituting for DOP. Furthermore, EGERAE endowed PVC resin with enhanced flexibility. In addition, the exudation, volatility and extraction resistance characteristics of plasticizers were researched. The degradation mechanism and possible interaction between EGERAE and PVC molecules in the plasticized system were also investigated. Full article
(This article belongs to the Special Issue Green Plasticizers for Polymers)
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Review

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17 pages, 1506 KiB  
Review
How Green is Your Plasticizer?
by Roya Jamarani, Hanno C. Erythropel, James A. Nicell, Richard L. Leask and Milan Marić
Polymers 2018, 10(8), 834; https://doi.org/10.3390/polym10080834 - 28 Jul 2018
Cited by 106 | Viewed by 12620
Abstract
Plasticizers are additives that are used to impart flexibility to polymer blends and improve their processability. Plasticizers are typically not covalently bound to the polymers, allowing them to leach out over time, which results in human exposure and environmental contamination. Phthalates, in particular, [...] Read more.
Plasticizers are additives that are used to impart flexibility to polymer blends and improve their processability. Plasticizers are typically not covalently bound to the polymers, allowing them to leach out over time, which results in human exposure and environmental contamination. Phthalates, in particular, have been the subject of increasing concern due to their established ubiquity in the environment and their suspected negative health effects, including endocrine disrupting and anti-androgenic effects. As there is mounting pressure to find safe replacement compounds, this review addresses the design and experimental elements that should be considered in order for a new or existing plasticizer to be considered green. Specifically, a multi-disciplinary and holistic approach should be taken which includes toxicity testing (both in vitro and in vivo), biodegradation testing (with attention to metabolites), as well as leaching studies. Special consideration should also be given to the design stages of producing a new molecule and the synthetic and scale-up processes should also be optimized. Only by taking a multi-faceted approach can a plasticizer be considered truly green. Full article
(This article belongs to the Special Issue Green Plasticizers for Polymers)
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