Acrylic Triblock Copolymers Incorporating Isosorbide for Pressure Sensitive Adhesives

Abstract

A new monomer acetylated acrylic isosorbide (AAI) was prepared in two steps using common reagents without the need for column chromatography. Free radical polymerization of AAI afforded poly­(acetylated acrylic isosorbide) (PAAI), which exhibited a glass transition temperature (T g) = 95 °C and good thermal stability (T d, 5% weight loss; N2 = 331 °C, air = 291 °C). A series of ABA triblock copolymers with either poly­(n-butyl acrylate) (PnBA) or poly­(2-ethylhexyl acrylate) (PEHA) as the low T g midblocks and PAAI as the high T g end blocks were prepared using Reversible Addition–Fragmentation chain Transfer (RAFT) polymerization. The triblock copolymers ranging from 8–24 wt % PAAI were evaluated as pressure sensitive adhesives by 180° peel, loop tack, and static shear testing. While the PAAI-PEHA-PAAI series exhibited poor adhesive qualities, the PAAI-PnBA-PAAI series of triblock copolymers demonstrated peel forces up to 2.9 N cm–1, tack forces up to 3.2 N cm–1, and no shear failure up to 10 000 min. Dynamic mechanical analysis indicated that PAAI-PEHA-PAAI lacked the dissipative qualities needed to form an adhesive bond with the substrate, while the PAAI-PnBA-PAAI series exhibited a dynamic mechanical response consistent with related high performing PSAs.

Sustainable isosorbide-based transparent pressure-sensitive adhesives for optically clear adhesive and their adhesion performance

“…This different stereoisomer structure leads to different reactivity of each hydroxyl group in the endo ‐ and exo ‐form, because of the intramolecular hydrogen bonding between the endo ‐form hydroxyl group and oxygen atom in the bicyclic ether core . A few synthetic methods to introduce methacrylate into isosorbide using methacrylic anhydride with the stoichiometric equivalent of an NH 3 base, or methacryloyl chloride with an equivalent of Et 3 N have been reported in the literature . Meanwhile, in an attempt to obtain enantioselective product of ISA bearing one free hydroxyl group through a one‐pot reaction, we carefully synthesized ISA at low temperature and with slow dropwise rate controlled by a syringe pump.…”

Mono-acrylated isosorbide as a bio-based monomer for the improvement of thermal and mechanical properties of poly(methyl methacrylate)

“…Comparing with the direct use as a diol and cross-linking monomer, mono-vinyl isosorbide derivatives have been reported only in a few works of literature. [26][27][28][29][30][31][32] These mono-vinyl isosorbide monomers are especially useful and could nd important applications in the construction of polymers with designed architectures through chain-growth polymerizations. For example, Beghdadi et al 31 reported that the substitution of the vinyl triazole moiety at either the endo-or exo-position had a signicant effect on the glass transition temperature T g and solubility of the polymer.…”

Highly efficient reversible addition-fragmentation chain-transfer polymerization in ethanol/water via flow chemistry

“…For RAFT polymerization, utilization of specific chain‐transfer agent (CTA) which can form a dormant species during the polymerization process allows production of polymer products with controlled molecular weight and narrow molar mass dispersity ( Đ ). With proper CTAs, synthesis of homopolymers, block copolymers and polymers with various architectures, such as star, macrocycle, hyperbranch and comb, can be achieved . Until now, most of RAFT polymerizations were performed with batch to batch reaction on a relatively small scale.…”