Facile synthesis and characterization of activated star-shaped itaconic acid based thermosetting resins (original) (raw)
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Bio-Based Thermosetting Resins for Future Generation: A Review
In this review, thermosetting polymers derived from natural resources are highlighted for future generation with greater sustainability for different applications. Recently, agro-based polymer products are gained popularity since last two decades due to the depletion of fossil reserves and to protect the environment from carbon emissions. This review also designed to explain the various types of agro-based polymer products derived from cardanol, itaconic acid, tannin, sugar (isosorbide), and vegetable oils as important starting materials due to their abundant availability, low price, and unique reactive chemical structure.
European Polymer Journal, 2016
A biobased thermoset resin was synthesized by direct condensation reaction of lactic acid with xylitol followed by the end-functionalization of the hydroxyl groups of branches by methacrylic anhydride. Chemical structures of resins were evaluated and confirmed by 13 C NMR and Fourier-transform infrared spectroscopy (FT-IR). Different techniques were employed for the optimization of the curing process. Techniques including Microscopy, Differential Scanning Calorimetry (DSC) and Dynamic Mechanical Thermal Analysis (DMTA) were employed for characterization of the cured resins. Thermogravimetric analyses (TGA) were also carried out to check the thermal stability of the cured resins. The viscosity of the neat resin was measured at different temperatures and different stress levels. Water adsorption tests were also carried out to check the water absorption properties of cured resins. The glass temperature (Tg) of the resin was 98°C, and the viscosity of the resin was 2.97 Pa s at room temperature which drops to 0.07 Pa s upon increasing the temperature to 85°C. The biobased content of the resin was calculated
A renewable approach to thermosetting resins
Reactive and Functional Polymers, 2013
This is a review of recent developments of thermostable resins derived basically from vegetable oils. Natural vegetable oils have been transformed in polymers following three main routes. The first is the direct polymerization through the double bonds of the fatty acid chain. The cationic copolymerization of soybean oil with styrene, divinylbenzene and different amounts of styrenic monomers containing Si, B and P has been used to produce materials with improved flame retardant properties. The second route is the functionalization of the triglyceride double bonds to introduce readily polymerizable groups: The singlet oxygen photoperoxidation of the allylic positions of high oleic sunflower oil has been used to produce hydroperoxide-containing triglycerides that were dehydrated or reduced to produce respectively enone-and hydroxyl-containing triglycerides. The enone containing derivative has been chemically crosslinked with aromatic diamines through aza-Michael reactions leading to quinoline containing thermosets. The hydroxyl-containing triglycerides have been crosslinked radically prior the introduction of acrylate groups to produce conventional and flame retardant acrylate resins. The third route explored consists of using plant oil-derived chemicals like 10-undecenoic and oleic acids to produce tailor made monomers. Acyclic diene metathesis (ADMET) polymerization has been applied to prepare a set of thermosetting polyesters with flame retardant properties. Moreover thiol-ene ''click'' coupling has been used to prepare carboxylic monomers that have been explored to produce thermosetting polyanhydrides for fast drug delivery systems. A set of tailored polyols from the products of coordinative polymerization of the methyl epoxyoleate and the cationic ring opening polymerization of fatty acid-derived 2oxazolines were also prepared. These polyols have been used to produce different thermosetting polyuretanes with a wide range of properties and characteristics. Finally, some recent research in producing benzoxazine thermosetting resins applying this renewable approach is presented. The benzoxazines based on diphenolic acid, a derivative of levulinic acid, are studied.
2017
, for sharing their expertise on star-shaped thermosets. To Nima Esmaeili from University of Bolton, UK, for his consultants and guidance on thermomechanical and characterization aspects of my project. To Dr. Gary Anderson for his smart insights on thermomechanical properties and statistical analysis of my work. To Dr. Halaweish for helping me with the NMR analysis. To Dr. Bishnu Karki for her insights and valuable time. To Dr. Tylor Johnson, for his advices, and help throughout lots of my projects. To my dear friends, Sepehr Nesaei and Samaneh Amiri. To Dr. Reza Ahmadi and Dr. Forough Jahandideh of university of Alberta for their kind help. I would particularly thank Dr. Asma Rashki of Tehran University of Medical Sciences, for critical evaluation of biomedical part of my dissertation. I also want to extend my deepest gratitude to Zari Alishiri and Dr. Ali Salehnia for their unconditional love, supports and help throughout these past three years. I extend my sincere appreciation to the entire faculty and staff in the department of Agricultural and Biosystems Engineering at South Dakota State University for their kind help and supports. Lastly and most importantly, I would like to express gratitude to my parents for making me feel unconditionally supported in every step I have taken. v
Journal of Applied Polymer Science, 2010
A new biobased polyester resin was developed for thermoset composite applications. The resin is potentially inexpensive and can be produced industrially by relatively simple means. The resin consists of star-shaped methacrylated oligomers of lactic acid (LA). LA oligomers were synthesized in a two-step process: in the first step, oligomers of LA were polymerized by direct condensation of LA. In the second step, the oligomers were end-functionalized by methacrylic anhydride. The resin was characterized by differential scanning calorimetry, Raman spectroscopy, NMR, rubber process analyzer, and TOF-SIMS. Tests show that the resin can be crosslinked into a rigid network within a couple of minutes upon thermal initiation. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2010
Progress in Organic Coatings, 2004
Thermosetting resins with semi-crystalline grafts have been synthesized. An amorphous resin with epoxide groups was first functionalized with hydroxyl groups using 2,2-bis(methylol) propionic acid, bis-MPA in bulk at 155 • C. Functionalization with bis-MPA was monitored using FT-IR, FT-Raman and SEC. The reaction was complete in 30 min. Grafts of poly(ε-caprolactone) were then grown from the hydroxyl functional resin and end capped with methacrylate groups. The polymerization of ε-caprolactone, performed in bulk at 110 • C using Sn(Oct) 2 , was characterized using 1 H NMR and SEC. The obtained molecular weights agreed well with theoretical values. The final end capping was performed using methacrylic anhydride, and monitored with SEC and 1 H NMR, which indicated full substitution. Two combs were synthesized with different arm lengths, DP 10 and 20, and the obtained M w were close to calculated values. The complex viscosity was measured from low to high temperature for the crystalline resins, the amorphous resin and blends thereof. Rheological data show a rapid decrease in viscosity within a temperature change of 10-15 • C for the crystalline resins while the amorphous resin exhibited a slow softening. The blends exhibited a behavior in-between that of the crystalline and the amorphous resin. Films were prepared from the pure resins and the blends. The films were cured using UV irradiation. The comb architecture of these resins has advantages such as crystallinity, high molecular weight and low viscosity, facilitating leveling and resulting in smooth films. The final film properties varied with the ratio of crystalline to amorphous resin, where increase in the amount of crystalline resin correlated with increased the flexibility.
Journal of Applied Polymer Science, 2007
Thermoset materials obtained from styrene/vinyl ester resins of different molecular weights modified with poly(methyl methacrylate) (PMMA) were prepared and studied. Scanning electron microscopy and transmission electron microscopy micrographs of the fracture surfaces allowed the determination of a two-phase morphology of the modified networks. Depending on the molecular weight of the vinyl ester oligomer, the initial content of the PMMA additive, and the selected curing temperature, different morphologies were obtained, including the dispersion of thermoplastic-rich particles in a thermoset-rich matrix, cocontinuous structures, and the dispersion of thermoset-rich particles in a thermoplasticrich matrix (phase-inverted structure). Density measure-ments were performed to determine the effect of the PMMA-modifier concentration and curing temperature on the volume shrinkage of the final materials. The development of cocontinuous or thermoplastic-rich matrices was not too effective in controlling the volume shrinkage of the studied vinyl ester systems. The evaluation of the dynamic mechanical behavior, flexural modulus, compressive yield stress, and fracture toughness showed that the addition of PMMA increased the fracture resistance without significantly compromising the thermal or mechanical properties of the vinyl ester networks.
Fundamental thermo-mechanical property modeling of triglyceride-based thermosetting resins
Journal of Applied Polymer Science, 2012
The glass transition temperature (T g) of acrylated triglycerides was clearly a function of the level of acrylation of triglyceride-based polymers and was modeled using simple empirical relationships. We began by calculating the distribution of unsaturation sites in plant oils. We assumed a binomial distribution of chemical functionality that was added to these unsaturation sites to calculate the distribution of epoxides, acrylates, and reacted acrylates to predict the crosslink density, thermal softening, and dynamic mechanical behavior. The glass transition temperatures of n-acrylated triglycerides were used as the relaxation temperatures of acrylated oils with a broad distribution of functionality for prediction of the modulus as a function of temperature. Essentially, the percent drop in the elastic modulus is equal to the percentage of n-acrylated triglycerides in the acrylated oil with T g less than that of the ambient temperature. The tan (d) was also accurately predicted based on the percentage change of n-functional triglycerides as the temperature changes from one relaxation temperature to the next. V
Macromolecular Chemistry and Physics, 2012
A well-defi ned multiarm star copolymer, hyperbranched poly(glycidol)-b -poly(methyl methacrylate) (PGOH-b -PMMA), is used as a modifi er in the curing of diglycidylether of bisphenol A (DGEBA) using 1-methyl imidazole (1MI) as anionic initiator. The effect of the polymer topology on the curing and gelation processes is studied. The addition of the PGOH-b -PMMA to the resin leaves the complex viscosity unaltered. The addition of the modifi er decreases the shrinkage after gelation compared to that measured in the curing of the neat resin. By DMTA a single relaxation process in the pure DGEBA and modifi ed thermoset is found. The addition of the star-like modifi er led to an improvement on the mechanical characteristics such as the impact strength and microhardness in comparison to the neat material.