Abstract
In this work is described the synthesis of a multifunctional thiolated squalene. Thiol-ene coupling reactions were employed to functionalize the six double bonds of squalene, using thiolacetic acid. Hydrolysis of the resulting thioacetates, rendered the corresponding hexathiolated squalene SQ6SH. This compound was further photopolymerized separately with triallyl cyanurate, pentaerythritol triacrylate and diethyleneglycol divinyl ether. Real Time FTIR kinetics revealed that homopolymerization of the ene monomers took place in addition to the thiol-ene photopolymerization. Flexible films were obtained when SQ6SH was photopolymerized in bulk with the above mentioned unsaturated monomers.
Highlights
The search for new biobased raw materials to prepare polymers, has become an important issue due to increasing depletion of oil sources
We have reported the use of vegetable oil [14], sucrose [15,16,17] and isosorbide [18], as starting materials to prepare epoxy monomers for cationic photopolymerization, and allylated carbohydrates to use them as comonomers in thiol-ene photopolymerization
To go further to obtain purely biobased polymers using the thiol-ene photopolymerization technique, we needed to prepare multifunctional thiols derived from natural sources
Summary
The search for new biobased raw materials to prepare polymers, has become an important issue due to increasing depletion of oil sources. Squalene is a triterpenoid found in shark liver, in wheat germ, and in olive oil. It is present in the human body at 5% - 8% w/w in the body fat [9]. It is produced industrially from the olive oil and it has found uses in the cosmetics industry and as skin humectant. Polyunsaturation of this compound make it a very attractive candidate to use it in the preparation of biobased polymers
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