Improving thermal and mechanical properties of biomass-based polymers using structurally ordered polyesters from ricinoleic acid and 4-hydroxycinnamic acids

Abstract

The synthesis of structurally ordered polyesters derived from ricinoleic acid and 4-hydroxycinnamic acids improves the thermal and mechanical properties.

Substituent Effects on Thermal and Mechanical Properties of Resorcinol‐Based Semiaromatic Polyesters

“…This can be explained by the increase in their free volume due to the introduction of soft segments into the polymer backbone. [ 24,36,38 ] P(R‐Gl) exhibited lower T g than P(2MR‐Ad), even though P(R‐Gl) has the shortest dicarboxylic acid in the polymers containing resorcinol units. A similar trend was observed in poly(alkylene terephthalate)s, and the polymers with diols containing even numbers of methylene groups exhibited higher T g than the corresponding polymers with odd counterparts.…”

“…Finally, the polycondensation of 2MR with adipic acid using N , N’ ‐diisopropylcarbodiimide (DIC) and 4‐(dimethylamino)pyridinium p ‐toluenesulfonate (DPTS) was performed as a milder method. [ 34–36 ] After a 20 h reaction, a colorless polymer with a high M n of 41.2 kg mol −1 and a narrow molecular weight distribution ( M w / M n ) of 1.5 could be successfully synthesized in a yield of 71.7%. Therefore, this polycondensation method was applied to synthesize other resorcinol‐based semiaromatic polyesters ( Scheme and Table 1 ), and twelve kinds of the polyesters were successfully prepared in yields of 50.6 to 71.7%.…”

“…This is because the introduction of methyl substituents into resorcinol caused the restriction in the rotational flexibility of polymer chains. [ 36,37 ] Besides, the T g of the polyesters with the same resorcinol unit except P(R‐Gl) declined as the dicarboxylic acid unit became longer (P(R‐Ad) > P(R‐Pi), P(2MR‐Gl) > P(2MR‐Ad) > P(2MR‐Pi), P(5MR‐Gl) > P(5MR‐Ad) > P(5MR‐Ad), P(25MR‐Gl) > P(25MR‐Ad) > P(25MR‐Pi)). This can be explained by the increase in their free volume due to the introduction of soft segments into the polymer backbone.…”

Recommendations for replacing PET on packaging, fiber, and film materials with biobased counterparts

“…202,203,[211][212][213] For example, the polymer obtained with dimethyl succinate (Scheme 4 ( 7)) exhibited a T g similar to PET (68 °C) and a storage modulus of 5.1 GPa. 202 Scheme 4 Representative multitude of vanillin-(1, 197 2, 198 3 & 4, 199 5, 200 6, 201 7, 202 8 203 ), vanillic acid-(9, 204-206 10, 204,207 11, 208 12, 205,209 13, 209 14, 210 15, 211,212 16, 213 17, 208 18 214 ), and ferulic acid-(19, 215 20, 216 21, 217 22, 218 Mankar et al designed a spiro-diol vanillin-based monomer, whose synthesis remarkably produced lower GHG emissions than biobased 1,3-propanediol and afforded a transparent material after polymerization (Scheme 4 ( 8)). 203 Finally, it is noteworthy that polymer 16 from Scheme 4 exhibited better mechanical properties than PET.…”

“…Besides vanillin, other lignin-derived monomers have been studied for the preparation of thermoplastics, though to a lesser extent. 215,216,218,220,[225][226][227][228][229][230]…”