An efficient process for synthesizing and hydrolyzing a phosphonated methacrylate: Investigation of the adhesive and anticorrosive properties

Abstract

A new phosphonated methacrylate, namely dimethyl(methacryloyloxy)methyl phosphonate (MAPC1), has been synthesized using paraformaldehyde and potassium carbonate according to the Pudovik reaction. The quantitative synthesis of MAPC1 was followed by selective hydrolysis of the ester group with sodium bromide to replace NaI (imparting non‐negligible ecological impact). Pure MAPC1(OH) was obtained in high yield and efficiently copolymerized with MMA. The r1 for MAPC1(OH)) and r2 (for MMA) values are 0.99 and 1.02, respectively, which indicates that the monophosphonic groups are statistically linked to the methacrylate backbone. When blended with PVDF, MMA/MAPC1(OH) copolymers show very good adhesion promoters in both dry and wet conditions and subsequently provide good anticorrosive properties. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 4794–4803, 2008

Humid Bonding with a Water‐Soluble Adhesive Inspired by Mussels and Sandcastle Worms

“…[18][19][20] Phosphorylated proteins are of great importance to control and regulate biomineralization progress in living organisms. [ 21 ] Inspired by these phosphate-containing biomaterials, phosphate functional groups are introduced to polymeric materials to achieve adhesive and anticorrosion properties, [ 22,23 ] and these materials were used for biomedical applications such as dental applications, tissue engineering, and drug delivery. [ 24 ] For instance, surface graft polymerization of a phosphatecontaining monomer onto a polymeric material significantly promotes bonding of the polymer to bone, and the resulting phosphate-containing polymer has a high affi nity for hydroxyapatite (HA).…”

Grafting of phosphonate groups onto PVA by acetalyzation. Evaluation of the anti-corrosive properties for the acetalyzed PVA coatings

“…In the other hands, we have already demonstrated the high capacity of phosphonate group, grafted to a polyacrylate backbone, for promoting adhesion towards metallic surface and hence preventing such surface against corrosion [15,18]. In this paper we have chemically grafted phosphonate group onto PVB in order to increase efficiency of PVB coatings against corrosion.…”

“…From the empirical data presented, it is apparent that the presence of phosphonate group is directly responsible for the excellent adhesion and anticorrosive properties. Furthermore, we have previously demonstrated [15] that phosphonic acid groups show stronger adhesion than the corresponding phosphonate groups. Since PVAP3 contains about 20 mol% of phosphonate groups, the cleavage of these functions would lead to very high performance coatings to efficiently prevent metallic surface against corrosion.…”

“…Commercial anti-corrosion polymer compounds are generally formed from Sipomer Ò or Phosmer Ò monomers, which are phosphate-type (meth)acrylates [5,6]. Polymers with some phosphonate functionality have long been established as excellent adhesives and anti-corrosion compounds, [7][8][9][10][11][12][13][14] and recently there has been investigation into the use of phosphonate-type methacrylates for the same purpose [15]. For instance, Lam et al [16] synthesized a methacrylate terpolymer, bearing phosphonic acid and n-butyl side groups, which was incorporated in a UV acrylate formulation.…”

Phosphonic acid‐containing polysulfones as anticorrosive layers

“…In this respect, most recent works concern the synthesis of acrylate or methacrylate polymers. [12][13][14] Concerning the development of phosphonic acid-containing high-performance polymers, very little work has been reported. 15 Moreover, to the best of our knowledge, such polymers have not been tested as anticorrosion coatings.…”