New thermosetting coatings using blocked carboxyl groups

Abstract

Characteristics of blocked carboxylic acid compounds obtained by blocking carboxyl groups with alkyl vinyl ethers were studied, and new thermosetting coatings using blocked carboxyl groups and epoxide were also studied. Polybasic carboxylic acids were esterified with alkyl vinyl ethers to obtain blocked carboxylic acids having the hemiacetal ester moieties. Most of blocked carboxylic acids obtained were liquids and showed an excellent solubility in organic solvents and a good compatibility with epoxy resins. Although the blocked carboxylic acids were stable under ambient conditions, they could regenerate the corresponding carboxylic acids accompanied by the elimination of alkyl vinyl ethers by the thermal dissociation. They could be used as noble thermal latent hardeners. Curing of the blocked carboxyl groups and epoxide in the presence of relatively weak Lewis acid proceeded through a sequence of three-step reactions consisting of deblocking of alkyl vinyl ethers, esterification of epoxide, and the addition of alkyl vinyl ether to 2-hydroxyalkyl ester. The main product of the curing system was 2-acetalalkyl ester, but not 2-hydroxylalkyl ester. The new one-package thermosetting coatings using blocked carboxyl groups have been evaluated for use in the practical automotive and coil coatings line production. VOCs reduction, low-toxicity, and cost saving are satisfactory for the application of the systems. And the cured films of the coatings offered advantages in the high durability, the acid resistance and the soil resistance.