Poly(methacrylic acid)-l-polyisobutylene amphiphilic conetworks by using an ethoxyethyl-protected comonomer: Synthesis, protecting group removal in the cross-linked state, and characterization

Gergely Kali, B. Iván

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

A series of poly(methacrylic acid)-l-polyisobutylene anionic amphiphilic conetworks with hydrophobic polyisobutylene (PIB) content between 33% and 70% (w/w) is synthesized by the macromonomer method using a new approach by applying ethoxyethyl-protected methacrylic acid (EEMA) comonomer. To remove the protecting group after copolymerization of EEMA with PIB-dimethacrylate, acidic hydrolysis and thermal treatment are attempted, and the success of the deprotection is monitored by different techniques. Comparing the two protective group removal steps, it is found that, in contrast to homopolymers of EEMA, the acidic hydrolysis is more favorable than the thermal deprotection due to anhydride formation during the latter process in the conetworks. Distinct glass transitions are obtained by differential scanning calorimetry (DSC) indicating phase separation in the resulting conetworks. The swelling ability of the obtained conetworks in polar and nonpolar solvents proves the amphiphilic nature of these materials. Due to the polyacidic component of the conetworks, their water swollen gels have pH-sensitive, intelligent swelling behavior in aqueous media. Because of the relatively high stability of EEMA, the applied protection-deprotection strategy can be easily utilized in several other designed polymer syntheses. Covalently bonding hydrophilic and hydrophobic polymer chains in a single conetwork is always a challenge. Here, an elegant solution for this difficult synthetic problem is offered by utilizing a simple protecting-deprotecting strategy not yet investigated for conetwork synthesis.

Original languageEnglish
Pages (from-to)605-613
Number of pages9
JournalMacromolecular Chemistry and Physics
Volume216
Issue number6
DOIs
Publication statusPublished - Mar 1 2015

Fingerprint

polyisobutylene
acids
Acids
synthesis
swelling
Swelling
hydrolysis
Hydrolysis
Polymers
Anhydrides
polymers
copolymerization
anhydrides
Homopolymerization
Phase separation
Copolymerization
Glass transition
Differential scanning calorimetry
heat measurement
Gels

Keywords

  • amphiphilic conetworks
  • gels
  • intelligent polymers
  • methacrylic acid
  • protection-deprotection strategies

ASJC Scopus subject areas

  • Materials Chemistry
  • Polymers and Plastics
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Condensed Matter Physics

Cite this

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abstract = "A series of poly(methacrylic acid)-l-polyisobutylene anionic amphiphilic conetworks with hydrophobic polyisobutylene (PIB) content between 33{\%} and 70{\%} (w/w) is synthesized by the macromonomer method using a new approach by applying ethoxyethyl-protected methacrylic acid (EEMA) comonomer. To remove the protecting group after copolymerization of EEMA with PIB-dimethacrylate, acidic hydrolysis and thermal treatment are attempted, and the success of the deprotection is monitored by different techniques. Comparing the two protective group removal steps, it is found that, in contrast to homopolymers of EEMA, the acidic hydrolysis is more favorable than the thermal deprotection due to anhydride formation during the latter process in the conetworks. Distinct glass transitions are obtained by differential scanning calorimetry (DSC) indicating phase separation in the resulting conetworks. The swelling ability of the obtained conetworks in polar and nonpolar solvents proves the amphiphilic nature of these materials. Due to the polyacidic component of the conetworks, their water swollen gels have pH-sensitive, intelligent swelling behavior in aqueous media. Because of the relatively high stability of EEMA, the applied protection-deprotection strategy can be easily utilized in several other designed polymer syntheses. Covalently bonding hydrophilic and hydrophobic polymer chains in a single conetwork is always a challenge. Here, an elegant solution for this difficult synthetic problem is offered by utilizing a simple protecting-deprotecting strategy not yet investigated for conetwork synthesis.",
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