Synthesis of novel moisture‐curable polyurethanes end‐capped with trialkoxysilane and their application to one‐component adhesives

Novel silane endcappers and novel polyurethanes end‐capped with trimethoxysilane (silylated polyurethanes) were developed as water‐curable materials in which the curing reaction occurred under humid conditions in the presence of dioctyltin diversatate as a curing catalyst. A variety of amine‐terminated trimethoxysilane compounds were synthesized by the Michael addition reaction of commercially available 3‐aminopropyltrimethoxysilane with acrylates, and the resulting silane endcappers were used to react with isocyanate‐terminated polyurethanes, providing the silylated polyurethanes. The moisture‐curable silylated polyurethanes were used for the preparation of novel one‐component and solvent‐free adhesives. The evaluated properties were the curing speed, the tensile shear bond strength, and the adherence to some substrates. The longer alkyl chains of the silane endcappers derived from various acrylates led to a slower curing speed, lower tensile strength at break, and longer elongation at break of the silylated polyurethanes. The tensile shear bond strength of the silylated polyurethane‐based adhesive decreased with decreasing the trimethoxysilane end‐capping ratio, whereas an increase in the adherence was observed. The adherence to the acrylic substrate was improved by changes in the main‐chain structure of the polyurethane based on the composition of poly(propylene oxide) and poly(ethylene oxide). © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 2689–2704, 2007