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Bio-Sourced Epoxy Monomers and Polymers
Published in A. Pizzi, K. L. Mittal, Handbook of Adhesive Technology, 2017
Sylvain Caillol, Bernard Boutevin, Jean-Pierre Pascault
As mentioned in Section 18.2, the reaction of ECH with natural aliphatic polyols, bearing both primary alcohol groups at the end of the chain and secondary alcohol groups within the chain, is not trivial. Indeed, this reaction generates new alcohol groups, being also reactive toward ECH [24]. Unlike the reaction between phenol groups and ECH, the hydroxyl groups resulting from the reaction between the polyols and ECH show reactivity fairly similar to that of the starting polyols. This thus implies multiple addition of ECH on the same alcohol, which is then not able to undergo intracyclization and could also lead to the presence of chlorine atoms. Furthermore, sorbitol is not soluble in water, that is, the reaction medium, and so an excess of ECH is required. This, in fact, reveals that the abovementioned structures provided by the chemical companies are idealized structures, since other by-products containing chlorine atoms are also obtained. It is important to mention that most of these commercial products contain about 10%–20 wt% of Cl. This actually has two consequences: First, the epoxy formulations become harder, and secondly, the resulting epoxy networks may undergo HCl formation. Sorbitol and maltitol have also been converted to multifunctional epoxy monomers through oxidation of allyl [103] or crotonic [104] double bonds, and in this case, there was no remaining chlorine atom. Interest in the production of 1,4:3,6-dianhydrohexitols, especially isosorbide, has been generated by potential industrial applications such as the synthesis of polymers. Isosorbide is obtained from dehydration (∼2 mol) of sorbitol. As already shown by Fenouillot et al. [105], isosorbide is a nontoxic and chiral molecule that also impacts stiffness to polymer chains such as polyesters, polycarbonates, or polyurethanes. Different processes [106–111] allow synthesis of diglycidyl ethers of isosorbide as well as oligoglycidyl ethers of isosorbide. Furthermore, two methods lead to either monomers or oligomers of epoxidized isosorbide by reaction with ECH. The first one, fairly similar to the synthesis of DGEBA, is based on the reaction between diol, ECH, and a strong base in an aqueous medium (Figure 18.11) [104,111,112]. This method often generates epoxy oligomers of isosorbide as well. In this case, the chlorine content remains slightly higher than that of polyphenols but much lower than that of sorbitol. This behavior can be ascribed to a better solubility of isosorbide in the reaction medium.
The future of isosorbide as a fundamental constituent for polycarbonates and polyurethanes
Published in Green Chemistry Letters and Reviews, 2021
Olga Gómez-de-Miranda-Jiménez-de-Aberasturi, Ander Centeno-Pedrazo, Soraya Prieto Fernández, Raquel Rodriguez Alonso, Sandra Medel, Jose María Cuevas, Luciano G. Monsegue, Stefaan De Wildeman, Elena Benedetti, Daniela Klein, Hartmut Henneken, José R. Ochoa-Gómez
Some of these derivatives (nitrates, esters, ethers.) are already employed in industrial processes for the manufacturing of medical vasodilators (5), plasticizers (6), or surfactants (7). Others are also commercially converted into different polymers, such as poly-(ethylene-isosorbide)terephthalate (PEIT), poly(isosorbide oxalate), or poly(isosorbide carbonate) known as DURABIO® (Mitsubishi) and PLANEXT® (Teijin) (8). Moreover, isosorbide is characterized by a high glass transition temperature (Tg), tensile modulus, UV stability, and visible light transmission (6, 9). These are features to make isosorbide a promising renewable candidate to replace non-renewable and toxic bisphenol-A in polycarbonates production. Moreover, isososorbide can also be incorporated in the formulation of a new type of non-isocyanate polyurethanes that can suppose a safer alternative than the traditional ones.
Effect of bio-derived/chemical additives on HMA and WMA compaction and dynamic modulus performance
Published in International Journal of Pavement Engineering, 2021
Joseph H. Podolsky, Conglin Chen, Ashley F. Buss, R. Christopher Williams, Eric W. Cochran
Isosorbide distillation bottoms (IDB) is a co-product from the conversion of sorbitol to isosorbide. Isosorbide is widely produced as it is the main material used in the production of medicines such as those used for treating hydrocephalus, glaucoma, and esophageal varices and in production of biopolymer polyester (Bersot et al.2011, Wang et al. 2013, Kobayashi et al. 2015, Kimer et al. 2016). IDB, CI, and RP are co-products from isosorbide production, and due to the high demand for isosorbide, are easy to obtain. Isosorbide is defined as being a water soluble surface active compound that increases the solubility of organic reactants in a liquid solution (Holmberg et al. 2002, Zhu et al. 2008, Subbarao et al. 2012). Past research has shown that amphiphiles synthesised from isosorbide act as solvo-surfactants (Bauduin et al. 2005, Zhu et al. 2008). Thus, isosorbide derived products have a double effect when used in asphalt for use in HMA production; (1) binder viscosity reduction, and (2) decreased energy at the interface between asphalt binder and aggregates (improved asphalt binder-aggregate bond). EMS, EBS, and ESO have similar properties to both CI and RP, but act as plasticisers, and were thus included in this work to examine how soybean oil derived products would perform.