Catechol- and Phenolic Hydroxyl-Functionalized Partially Bio-Based (Co)poly(ether sulfone)s with Multifarious Applicability

[Display omitted] •A largely bio-based new bisphenol was designed and synthesized.•(Co)poly(ether sulfone)s containing built-in methoxyl groups (PSU-OMe) were synthesized.•De-blocking of methoxyl groups led to polymers with catechol moieties and phenolic hydroxyl groups (PSU-OH).•PSU-OH was shown to...

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Veröffentlicht in:European polymer journal 2024-11, Vol.220, p.113484, Article 113484
Hauptverfasser: Wale, Apparav K., Jagtap, Ashish S., Pandey, Priyanshi R., Dastager, Syed G., Shelke, Manjusha V., Ambade, Ashootosh V., Wadgaonkar, Prakash P.
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Sprache:eng
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Zusammenfassung:[Display omitted] •A largely bio-based new bisphenol was designed and synthesized.•(Co)poly(ether sulfone)s containing built-in methoxyl groups (PSU-OMe) were synthesized.•De-blocking of methoxyl groups led to polymers with catechol moieties and phenolic hydroxyl groups (PSU-OH).•PSU-OH was shown to act as antioxidant, antimicrobial, redox-active material in zinc-ion batteries and as adhesive. A largely bio-based new bisphenol, namely, 4,4′-((3,4-dimethoxyphenyl)methylene)-bis(2-methoxyphenol) (DMBM) was synthesized by the reaction of veratraldehyde with guaiacol. DMBM and varying compositions of DMBM and bisphenol A were polycondensed with bis(4-fluorophenyl) sulfone to afford reasonably high molecular weight film-forming (co)poly(ether sulfone)s possessing built-in methoxyl groups. T10 and Tg values of (co)poly(ether sulfone)s were in the range 382–478 °C and 171–187 °C, respectively indicating their good thermal stability and the values decreased with increase in mol % incorporation of DMBM. The methoxyl groups present in (co)poly (ether sulfone)s were quantitatively de-blocked resulting in the formation of corresponding polymers possessing pendant catechol moieties and free phenolic hydroxyl groups. By virtue of the presence of these functional moieties, (co)poly(ether sulfone)s are amenable for post-polymerization modifications, and exhibited properties such as antimicrobial (23 mm against Staphylococcus aureus and 18 mm against Escherichia coli)), antioxidant (72 % scavenger of free radicals), adhesive (2.24  MPa lap shear strength) and usefulness as redox-active agent in zinc-ion batteries. These data underscore the promise of DMBM as a versatile monomer of wider utility for the synthesis of functional (co)poly(ether sulfone)s capable of expanding their applicability beyond the conventional ones.
ISSN:0014-3057
DOI:10.1016/j.eurpolymj.2024.113484