Cationic Polymerization of (3‐Aminopropyl)‐tris‐furfuryloxysilane Derivatives—a New Strategy for Complex Hybrid Material Synthesis. Issue 11 (30th April 2019)

• Record Type: Journal Article
• Authors: Uhlig, Daniel; Seifert, Andreas; Schreiter, Katja; Rüffer, Tobias; Lang, Heinrich; Thielbeer, Frank; Stoll, Ragnar; Müller, Philipp; Spange, Stefan
• Is Part Of: Macromolecular chemistry and physics. Volume 220:Issue 11(2019)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2019-04-30
• Subjects: interpenetrating network -- polyfurfuryl alcohol -- substituted ureas -- twin polymerization; Polymers -- Periodicals; Polymerization -- Periodicals; Synthetic products -- Periodicals; Macromolecules -- Periodicals; 547.7
• DOI: 10.1002/macp.201900050
• Languages: English
• ISSNs: 1022-1352

Abstract

Abstract: The trifunctional (3‐aminopropyl)‐ tris ‐furfuryloxysilane monomer (1 ) is able to undergo both twin polymerization and reaction with electrophilic compounds such as isocyanates.1 can be readily synthesized from 3‐aminopropyptrimethoxysilane (APTMS) and furfuryl alcohol (FA). The reaction of1 with three different aromatic isocyanates, namely phenyl isocyanate, diphenylmethane‐4, 4′‐diisocyanate (MDI), and a prepolymer consisting of MDI end‐capped polytetramethylene ether glycole (PTMEG), to the corresponding substituted urea derivatives is presented. Three urea derivatives 1‐phenyl‐3‐(3‐ tris ‐furfuryloxysilyl)propylurea (2 ), diphenylmethan‐4, 4′‐ bis [3( tris‐ furfuryloxysilyl)propyl]urea (3 ), bis [3( tris‐ furfuryloxysilyl)‐propyl]urea‐capped PTMEG‐MDI‐prepolymer (4 ) as well as1 were polymerized to multicomponent organic/inorganic hybrid materials in a one step procedure using methane sulfonic acid as catalyst. The simultaneous formations of poly furfuryl alcohol and polysiloxane networks within the hybrid material are proven by means of solid‐state NMR spectroscopic measurements. The homogeneous distribution of silicon within the solidified hybrid materials is analyzed by scanning electron microscopy, energy dispersive X‐ray spectroscopy, and high‐angle annular dark field‐scanning transmission electron microscopy (HAADF)‐STEM. Homogeneous nanostructured hybrid materials with silicon cluster sizes in the range of 2 nm have been obtained by polymerization of the urea derivatives2, 3, and4 . Abstract : The 3‐aminopropyl‐ tris ‐furfuryloxysilane moiety is presented as an appropriate building block for hybrid material synthesis. The amino functionality allows the conversion with isocyanates and isocyanate containing prepolymers to different urea derivatives. These urea derivatives are able to undergo twin polymerization to obtain nanostructured hybrid materials consisting of polyfurfuryl alcohol and polyalkylsiloxane in one reaction step.