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Journal of Materials Chemistry B Vol -2

Journal of Materials Chemistry B Vol -1

Polyglycidol-based metal adhesion promoters

Content Provider	Royal Society of Chemistry (RSC)
Author	Moeller, M. Piermattei, A. Keul, H. Kuehne, A. J. C. Keul, H. A. Koehler, J. Dirks, T. Qiu, J.
Copyright Year	2015
Abstract	Hydrophilic adhesion promoters that facilitate intimate binding between metals and polymers are an important class of materials with a wide variety of applications in biomedical coatings. Currently, non-poly(meth-)acrylate based hydrophilic polymeric adhesives are unavailable. Here, we report the preparation of such adhesion-promoters based on linear polyglycidol for biomedical applications. The adhesion promoting polymer is prepared from partly phosphonoethylated polyglycidol in three steps. First, the remaining hydroxyl groups of the polyglycidol backbone are reacted with acryloyl chloride; secondly, the phosphonate groups are chemoselectively dealkylated using bromotrimethylsilane. Finally, the bis(trimethylsilyl)phosphonate intermediate is converted to the phosphonic acid through ethanolysis. The reaction conditions of each synthetic step are optimized individually and the products are characterized by 1H, 31P NMR and SEC analysis. The optimized reaction conditions are applied to establish a straightforward one-pot reaction, resulting in an ethanolic formulation of the adhesion promoter, which can be used immediately for the coating application. Special attention is paid to the stability of the intermediates, the chemoselectivity of the reactions and the shelf-life of the product. 1H NMR spectroscopy reveals hydrolytic instability of the product under ambient conditions; however, the polymers are sufficiently stable in dry ethanol for at least 14 days. The combination of this hydrophilic polymer with acrylate and phosphonic acid groups constitutes a versatile platform technology for the preparation of thin primer coatings on metal substrates for biomedical applications. The phosphonic acid residues assure strong binding to stainless steel wires and the acrylates can be addressed by UV light to enable crosslinking, thus improving mechanical stability and adhesion between the substrate and a biomedical hydrogel coating. The quality of the adhesion promotion to stainless steel wires is verified by using a lubricious, hydrogel top coat and by evaluating friction and wear resistance of this total coating system. Constant values for friction and wear are obtained, proving the applicability of phosphonic acid-functionalized polyglycidols as metal adhesion promoters for biomedical applications.
Starting Page	804
Ending Page	813
Page Count	10
File Format	HTM / HTML PDF
ISSN	2050750X
Volume Number	3
Issue Number	5
Journal	Journal of Materials Chemistry B
DOI	10.1039/c4tb01719f
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	SEC Meth- Acrylic acid Hydrophile Polymer Hydroxy group Acryloyl chloride Phosphonate Trimethylsilyl Carboxylic acid Nuclear magnetic resonance U.S. Securities and Exchange Commission One-pot synthesis Chemoselectivity Ethanol Stainless steel Gel
Content Type	Text
Resource Type	Article
Subject	Chemistry Medicine Materials Science Biomedical Engineering

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