Polyhydroxy ketal ester adducts, methods of manufacture and uses thereof

A method for the manufacture of a polyhydroxy ketal adduct I

• wherein
• G is a C2-32 alkylene, C2-32 alkenylene, C4-8 cycloalkylene, C5-8 cycloalkenylene, C6-12 arylene, or C2-32 —(R12O)qR12_wherein each R12 is methylene, ethylene, 1,3-propylene, or 1,2-propylene and q=1-31, wherein G has a valence of t, wherein t=2-12,
• each R2 is independently C1-6 alkyl,
• each R3, R4, and R6 is each independently hydrogen, C1-6 alkyl, —OR8 wherein R8 is C1-4 alkyl, or —C(O)R9 wherein R9 is C1-4 alkyl,
• each R7 is independently C1-6 alkylene, or C1-6 alkylene substituted with one —OR8 group wherein R8 is C1-3 alkyl, or —C(O)R9 wherein R9 is C1-2 alkyl,
• each a is independently=0-3,
• each b is independently=0-1,
• each m is independently=1-50,
• p=0-11,
• q-n=0-10, and
• n=1-12, provided that p+n≧2, q≧n, and p+(q-n)+n=t, wherein t=2-12, and is the valence of G,
• the method comprising
• (a) esterifying a polyol II,
• G-[OH]t II
• with a compound III
• wherein G in formula II is the same as G in formula I, t in formula II has the same value as the valence of G in formula I, R2 and a in formula III are the same as the R2 and a in formula I, L is hydroxy, halide, —OC(═O)R11, or —OR11 wherein R11 is a C1-3 alkyl, wherein the molar ratio of the compound III to the polyol II is greater than or equal to about 1.5:1;
• in the presence of an esterification catalyst, wherein the esterification catalyst is about 2 to 20,000 parts per million relative to the sum of the weights of the polyol II and the compound III, to form a ketocarboxylic ester IV
• wherein R2, a, p, and q in formula (IV) are the same as R2, a, p, and q in formula I;
• and
• (b) ketalizing ketocarboxylic ester IV with a polyol V
• in the presence of a ketalization catalyst, to provide the polyhydroxy ketal adduct I,
• wherein R3, R4, R6, R7, and b in formula V are the same as R3, R4, R6, R7, and b in formula I, and wherein the ketocarboxylic ester IV and the polyol V are provided in amounts such that the molar ratio of the polyol V to the ketocarboxylic ester IV is greater than or equal to about 2.