Novel Rubbers from Cationic Copolymerization of Soybean Oils and Dicyclopentadiene. 1. Synthesis and Characterization

Abstract

Novel thermosetting copolymers, ranging from tough and ductile to very soft rubbers, have been prepared by the cationic copolymerization of regular (SOY) and 100% conjugated soybean oils (C(100)SOY) with dicyclopentadiene (DCP) catalyzed by Norway fish oil (NFO)-modified and SOY- and C(100)SOY-diluted boron trifluoride diethyl etherate (BFE). The gelation time of the reactions varies from 4 to 991 min at 110 degrees C. The yields of the bulk copolymers are essentially quantitative, while the yields of the cross-linked copolymers remaining after Soxhlet extraction with methylene chloride range from 69% to 88%, depending on the monomer stoichiometry and the catalyst used. (1)H NMR spectroscopy and Soxhlet extraction data indicate that these copolymers consist of a cross-linked soybean oil-DCP network plasticized by certain amounts of methylene chloride-soluble linear or less cross-linked soybean oil-DCP copolymers, unreacted oil, and some low molecular weight hydrolyzed oil. The molecular weights of these soluble fractions are in the range from 400 to 10,000 g/mol based on polystyrene standards. The bulk copolymers have glass transition temperatures ranging from -22.6 to 56.6 degrees C, while their tan delta peak values range from 0.7 to 1.2. Thermogravimetric analysis (TGA) indicates that these soybean oil-DCP copolymers are thermally stable below 200 degrees C, with 10% and 50% weight loss temperatures ranging from 280 to 372 degrees C and 470-554 degrees C, respectively. These properties suggest that these biobased thermosets may prove useful alternatives to current petroleum-based plastics and find widespread utility.

Preparation and properties of tung oil‐based composites using spent germ as a natural filler

“…The T max value also decreased, but to a lesser extent. As the amount of DVB increases (entries [14][15][16], the T 50 and T max values are most affected and no trend is observed for the T 10 values. The T 50 values increase from 416 to 4308C and the T max values increase from 425 to 4418C when the DVB increases from 10 to 25 wt %.…”

Monomers and polymers from plant oils via click chemistry reactions

“…59 However, thiol addition to C@C bonds of naturally occurring unsaturated triglyceride is a priori a straightforward and attractive way to functionalize these products with reactive groups with higher aptitude to be polymerized. Aside from the highly efficiency demonstrated by the thiol-ene addition in polymer/ materials chemistry as well as in traditional (bio)organic synthesis, functional group tolerance is probably its most outstanding characteristic.…”

Desenvolvimento de novas combinações monômero - catalisador para a produção de polímeros via ROMP

“…Através da introdução de grupos funcionais nestes locais reativos, o óleo vegetal pode ser utilizado como plataforma para materiais poliméricos, por diferentes mecanismos como por exemplo, polímeros feitos a partir do óleo de soja [18,19] . [20] .…”

“…Wang et al preparou uma série de polióis a partir do óleo de soja epoxidado (ESBO) utilizando 1,2-etanodiol e 1,2-propanodiol para abrir os anéis epoxidado; o efeito do número de OH nesses polióis sobre as propriedades térmicas e mecânicas do molde final da poliuretana foram estudados [18,25] .…”

“…Olefinas tais como norborneno apresentam alta tensão anelar tornando o processo de ROMP termodinamicamente favorável. Monômeros derivados de norborneno têm sido amplamente utilizados para produzir diversos grupos pendentes nas cadeias de polímeros [18,26,33] .…”