Application of MALDI-TOF, 1H NMR and 13C NMR to follow the progress of the synthesis of high molecular weight epoxies from hydroxylated soybean oil and bisphenol A based epoxy resin

2019 ◽  
Vol 73 ◽  
pp. 200-207 ◽  
Author(s):  
A. Sienkiewicz ◽  
P. Czub
Materials ◽  
2021 ◽  
Vol 14 (22) ◽  
pp. 6770
Author(s):  
Anna Sienkiewicz ◽  
Piotr Czub

The research undertaken in this work is one of the examples of the engineering of modern polymer materials. This manuscript presents studies on the gelation process which might occur during the synthesis of epoxy resin using the modified vegetable oil via the epoxy fusion process conducted in bulk. Based on obtained results we determined rheological parameters related to the properties of reacting mixture during the polyaddition process, especially before and after occurring the phenomenon of gelation (via (1) theoretical determination of the gel point using the degree of conversion of reactants before occurring the gelation process of reacting mixture and (2) experimentally—the dynamic mechanical properties such as storage modulus, G′; loss modulus, G″; and loss tangent, tg δ). Theoretical investigations show that for both systems: epoxidized soybean oil and bisphenol A (ESBO_BPA), as well as the hydroxylated soybean oil and low molecular weight epoxy resin (SMEG_EPR), theoretical values of the degree of conversion at the gel point are characterized by similar values (ESBO_BPA: xgel-theoretical = 0.620, xgel-theoretical = 0.620 and SMEG_EPR: xgel-theoretical = 0.614, xgel-experiment = 0.630, respectively), while the one determined based on the initial assumptions are greater than the above-mentioned (ESBO_BPA: xgel-assumed = 0.696 and SMEG_EPR: xgel-assumed = 0.667). Moreover, experimental studies in the viscoelastic fluid stage showed that the SMEG_EPR system is characterized by lower values of G′ and G″, which indicates lower elasticity and lower viscosity than the epoxidized derivative. It was found that alike during the conventional polyaddition reaction, both systems initially are homogeneous liquids of increasing viscosity. Wherein gradual increase in viscosity of the reaction mixture is related to the fusion of oligomer molecules and the formation of higher molecular weight products. In the critical stage of the process, known as the gelation point, the reaction mixture converts into the solid form, containing an insoluble cross-linked polymer.


1980 ◽  
Vol 6 (2) ◽  
pp. 144-144 ◽  
Author(s):  
F. Bokelund ◽  
S. Fregert ◽  
L. Trulsson

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4347
Author(s):  
You-Ran Jang ◽  
Kyoungwon Cho ◽  
Se Won Kim ◽  
Susan B. Altenbach ◽  
Sun-Hyung Lim ◽  
...  

Because high-molecular-weight glutenin subunits (HMW-GS) are important contributors to wheat end-use quality, there is a need for high-throughput identification of HMW-GS in wheat genetic resources and breeding lines. We developed an optimized method using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) to distinguish individual HMW-GS by considering the effects of the alkylating reagent in protein extraction, solvent components, dissolving volume, and matrix II components. Using the optimized method, 18 of 22 HMW-GS were successfully identified in standard wheat cultivars by differences in molecular weights or by their associations with other tightly linked subunits. Interestingly, 1Bx7 subunits were divided into 1Bx7 group 1 and 1Bx7 group 2 proteins with molecular weights of about 82,400 and 83,000 Da, respectively. Cultivars containing the 1Bx7 group 2 proteins were distinguished from those containing 1Bx7OE using well-known DNA markers. HMW-GS 1Ax2* and 1Bx6 and 1By8 and 1By8*, which are difficult to distinguish due to very similar molecular weights, were easily identified using RP-HPLC. To validate the method, HMW-GS from 38 Korean wheat varieties previously evaluated by SDS-PAGE combined with RP-HPLC were analyzed by MALDI-TOF-MS. The optimized MALDI-TOF-MS method will be a rapid, high-throughput tool for selecting lines containing desirable HMW-GS for breeding efforts.


2012 ◽  
Vol 229-231 ◽  
pp. 297-302 ◽  
Author(s):  
Mochamad Chalid ◽  
Hans J. Heeres ◽  
Antonius A. Broekhuis

The ring opening of -valerolactone (GVL) with amine compounds was reported as a promising molecular engineering tool to synthesize precursors for new bio-based polymers such as polyurethanes (PUs). Experimental work on the synthesis of polymers based on GVL/1,2-ethanolamine and GVL/1,2-diaminoethane adducts, and di-isocyanates (1,4-phenylene-di-isocyanate (PDI) 2,4-toluene-di-isocyanate (TDI) and hexamethylene-di-isocyanate (HDI)) is described. The polymers were characterized by FTIR, 1H-NMR, 13C-NMR, elemental analysis and GPC. The best polymerization results were obtained using TEA as the catalyst, DMA as the solvent and a temperature of 140°C for the reaction of the GVL/1,2-aminoethanol adduct with TDI. A polymer with a molecular weight (Mw) of 156 KDalton was produced in 97% yield.


2006 ◽  
Vol 11-12 ◽  
pp. 379-382 ◽  
Author(s):  
Ya Feng Li ◽  
Jue Cheng

Thiirane is usually synthesized by epoxy resin, and there are considerable content of epoxy mixed in thiirane because of the poor yields. In this article, a novel separation method was used to get pure episulfide compound and epoxy compound from thiirane/epoxy resin synthesized in our lab. Furthermore, the perfect 1H NMR spectra of pure episulfide compound and epoxide compound were obtained. The quantitative analysis of content of epoxy groups in thiirane/epoxy resin was performed by using FTIR and was testified by 1H NMR. It was found that the analytical results of the conversion of epoxy groups by the two methods above coincided with each other well.


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