Role of Amines in Adhesion of Polybutadiene to Glass Substrates. II. Reactions of Amines with Trimethoxysilanol and/or Fumed Silica

Abstract

Abstract This paper is part of a larger investigation of the role of amines in the adhesion of polybutadiene to glass substrates. It describes near infrared, infrared and nuclear magnetic resonance spectroscopy studies of the interaction of amines with silanol groups usually under ambient conditions but sometimes when heated in air. Additional supporting evidence was obtained from gas liquid chromatography, mass spectrometry and elemental analyses. In order to assure a sufficiently high concentration of silanol groups, triethylsilanol and fused silica were used as models for the glass surface. The mechanism of interaction of aliphatic amines and of the aminosilane was different from that of aromatic amines. Most notably, reaction of aliphatic amines with carbon dioxide in the air and/or dissolved/adsorbed in/on the silanol occurred almost instantaneously, whereas the corresponding reaction of the aromatic amines with carbon dioxide was not observed under the experimental conditions used. The carbamates formed underwent further reactions much more rapidly than either the simple aromatic amines or the unmodified aliphatic amines.