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A green solvent-to-polymer upgrading approach to water-soluble LCST poly(N-substituted lactamide acrylate)s

cc by (c) Pala, Marc et al, 2022 http://creativecommons.org/licenses/by/3.0/es/ info:eu-repo/semantics/openAccess ;ISSN: 1463-9270 ;EISSN: 1463-9270 ;DOI: 10.1039/d2gc02780a

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  • Title:
    A green solvent-to-polymer upgrading approach to water-soluble LCST poly(N-substituted lactamide acrylate)s
  • Author: Pala, Marc ; El Khannaji, Hafssa ; Garay Sarmiento, Manuela ; Carlos Ronda, Juan ; Cádiz, Virginia ; Galià, Marina ; Percec, Virgil ; Rodriguez Emmenegger, César ; Lligadas, Gerard
  • Subjects: Biocompatibilitat ; Biocompatibility ; Polimerització ; Polymerization
  • Description: We report a green solvent-to-polymer upgrading transformation of chemicals of the lactic acid portfolio into water-soluble lower critical solution temperature (LCST)-type acrylic polymers. Aqueous Cu(0)-mediated living radical polymerization (SET-LRP) was utilized for the rapid synthesis of N-substituted lactamide-type homo and random acrylic copolymers under mild conditions. A particularly unique aspect of this work is that the water-soluble monomers and the SET-LRP initiator used to produce the corresponding polymers were synthesized from biorenewable and non-toxic solvents, namely natural ethyl lactate and BASF's Agnique (R) AMD 3L (N,N-dimethyl lactamide, DML). The pre-disproportionation of Cu(I) Br in the presence of tris[2-(dimethylamino)ethyl]amine (Me6TREN) in water generated nascent Cu(0) and Cu(II) complexes that facilitated the fast polymerization of N-tetrahydrofurfuryl lactamide and N,N-dimethyl lactamide acrylate monomers (THFLA and DMLA, respectively) up to near-quantitative conversion with excellent control over molecular weight (5000 < M-n < 83 000) and dispersity (1.05 < D < 1.16). Interestingly, poly(THFLA) showed a degree of polymerization and concentration dependent LCST behavior, which can be fine-tuned (T-cp = 12-62 degrees C) through random copolymerization with the more hydrophilic DMLA monomer. Finally, covalent cross-linking of these polymers resulted in a new family of thermo-responsive hydrogels with excellent biocompatibility and tunable swelling and LCST transition. These illustrate the versatility of these neoteric green polymers in the preparation of smart and biocompatible soft materials.
  • Creation Date: 2022-10
  • Language: English
  • Identifier: ISSN: 1463-9270
    EISSN: 1463-9270
    DOI: 10.1039/d2gc02780a
  • Source: Diposit Digital de la Universitat de Barcelona
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