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Esters of maleinized fatty compounds as plasticizers
Author(s) -
Biermann Ursula,
Jungbauer Anton,
Metzger Jürgen O.
Publication year - 2012
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201100136
Subject(s) - chemistry , adduct , maleic anhydride , phthalate , plasticizer , organic chemistry , cyclohexane , methanol , tricarboxylic acid , polymer , citric acid cycle , copolymer , enzyme
Some plant oil derived cyclohexane tricarboxylic acid triesters were synthesized and suggested as potential plasticizers based mainly on renewable feedstock. Methyl calendulate 1 and α‐eleostearate 2 obtained from calendula oil and tung oil, respectively, as well as methyl oleate 3 were used as starting material. Reactions with maleic anhydride gave the corresponding Diels–Alder adducts 4 and 5 and ene adduct 6 , which were converted by ring‐opening reactions with various alcohols to the respective tricarboxylic acid triesters. Especially the cyclohexane tricarboxylic trimethyl triester 9 derived from Diels–Alder adduct 5 showed excellent absorption properties by PVC, superior to bis (2‐ethylhexyl)phthalate (DEHP). Moreover, the commercially available Diels–Alder adduct of CLA 7 (Admergin acid®) was ring‐opened with methanol showing an absorption by PVC that was still higher compared to triester 9 although the viscosity was significantly higher.