2017
DOI: 10.1016/j.tetlet.2017.05.021
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Synthesis of multi-functional epoxides derived from limonene oxide and its application to the network polymers

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Cited by 16 publications
(24 citation statements)
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“…In contrast to bis‐ trans ‐LO, the reaction of bis‐LO and BPEI 600 yielded no network polymer regardless of the feed ratio due to the low reactivity of cis ‐LO moiety and the low content of multiple trans ‐LO species in a single molecule. The composition of bis‐LO may be statistically regarded as three types as shown in Scheme : both trans ‐LO (approximately 25%), one trans ‐LO and one cis ‐LO (approximately 50%), and both cis ‐LO (approximately 25%) . To investigate the effect of both trans ‐LO moieties in bis‐LO on the polymer yield, both trans ‐LO moieties ranging from 25 to 96% were tested, as shown in Table .…”
Section: Resultsmentioning
confidence: 99%
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“…In contrast to bis‐ trans ‐LO, the reaction of bis‐LO and BPEI 600 yielded no network polymer regardless of the feed ratio due to the low reactivity of cis ‐LO moiety and the low content of multiple trans ‐LO species in a single molecule. The composition of bis‐LO may be statistically regarded as three types as shown in Scheme : both trans ‐LO (approximately 25%), one trans ‐LO and one cis ‐LO (approximately 50%), and both cis ‐LO (approximately 25%) . To investigate the effect of both trans ‐LO moieties in bis‐LO on the polymer yield, both trans ‐LO moieties ranging from 25 to 96% were tested, as shown in Table .…”
Section: Resultsmentioning
confidence: 99%
“…It is well known that the reactivity of nucleophilic attack to cis ‐limonene oxide ( cis ‐LO) by amines is much lower than that to trans ‐limonene oxide ( trans ‐LO) because of the high energetic boat‐like transition state . Recently, a crosslinking reaction of multifunctional epoxides derived from LO composed of cis and trans isomers with branched polyethyleneimine (BPEI) was reported . To the best of our knowledge, no reports on the effect of the difference between cis and trans isomers of LO on properties of resulting network polymers have been published.…”
Section: Introductionmentioning
confidence: 99%
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“…Glycidyl esters of rosin acid oligomers have been cross‐linked with isophorone diamine and shown to lead to epoxy polymers with comparable properties to those obtained with BADGE 14 . Limonene Oxide (LO) has been dimerized with various dithiol compounds via a thiol‐ene reaction, and the resulting products have also been used as epoxy monomer 15–17 . The recent report that limonene can be catalytically epoxidized using oxygen 18 sparked our interest for the use of limonene dioxide (LDO) as biosourced epoxy monomer (Figure 1).…”
Section: Introductionmentioning
confidence: 99%
“…More surprisingly, to the best of our knowledge, only one recent paper described the use of limonene oxide for this application. In fact, Morinaga and Sakamoto [ 22 ] synthesized multifunctional limonene-based epoxides using di-, tri- or tetra-thiols and crosslinked them with branched polyethyleneimine. They observed that a large excess of amine groups was required to obtain satisfactory crosslinking at 100 °C.…”
Section: Introductionmentioning
confidence: 99%