High molecular weight linked esterified propoxylated glycerins useful as gelling or thickening agents

Reference Number: N 04-04

Inventors: Sekula, Bernard C.; Ferenz, Michael R.

USPTO Link: 5516544

Invention Summary

This invention furnishes a reduced calorie fat substitute which is a linked esterified alkoxylated polyol comprised of at least one polycarboxylate linking segment, at least two polyol segments, and at least one C.sub.6 -C.sub.24 monocarboxylic fatty acid-esterified oxyalkylene segment attached to a polyol segment, wherein each polyol segment is connected to a polycarboxylate linking segment either directly or through an oxyalkylene segment. Preferably, the polycarboxylate linking segment(s) has the general structure ##STR1## wherein X is an aliphatic moiety comprised of from 1 to 10 carbon atoms and up to 2 carbon-carbon double bonds or ##STR2## wherein w is 2 or 3 and A represents the hydrocarbyl portion of a dimerized or trimerized fatty acid, the polyol segments have the general structure R--O).sub.n wherein R is a C.sub.3 -C.sub.12 hydrocarbyl group and n is an integer of from 3 to 8, the C.sub.6 -C.sub.24 monocarboxylic acid-esterified oxyalkylene segment(s) has the general structure ##STR3## wherein oxyalkylene is oxyethylene, oxypropylene, or oxybutylene, Z is an integer of from 1 to 10, and R.sup.1 is a C.sub.5 -C.sub.23 hydrocarbyl group, and the optionally present oxyalkylene segment has the general structure -(oxyalkylene.sup.1).sub.y wherein oxyalkylene.sup.1 is oxyethylene, oxypropylene, or oxybutylene and y is an integer of from 1 to 10. It is also highly desirable that the linked esterified alkoxylated polyol contain from 2 to 4 polyol segments and have a molecular weight of from 750 to 6000. Preferably, the number of C.sub.6 -C.sub.24 monocarboxylic fatty acid-esterified segments is at least equal to the number of polyol segments.

The present invention also provides a linked esterified alkoxylated polyol useful as a reduced calorie fat substitute obtainable by esterification of an alkoxylated polyol with at least one C.sub.6 -C.sub.24 monocarboxylic acid entity and at least one polycarboxylic acid entity. In a particularly preferred embodiment, the linked esterified alkoxylated polyol is obtainable by alkoxylation of a polyol having from 3 to 8 hydroxyl groups with from n to 10 n equivalents of a C.sub.2 -C.sub.6 aliphatic epoxide, wherein n is equal to the number of hydroxyl groups on the polyol, to form an alkoxylated polyol and (b) esterification of the alkoxylated polyol with both (i) at least one C.sub.6 -C.sub.24 monocarboxylic acid entity and (ii) a polycarboxylic acid entity selected from dimer or trimer fatty acid entities and dicarboxylic acid entities having the general structure ##STR4## wherein X is is an aliphatic moiety comprised of from 1 to 10 carbon atoms and up to 2 carbon-carbon double bonds and Y is hydroxy, halide, or alkoxy, wherein the amount of C.sub.6 -C.sub.24 monocarboxylic acid acid entity is from 1 to n-1 moles per mole of polyol and the amount of polycarboxylic acid entity is from 1/z to n-1/z moles per mole of polyol, where z is equal to the number of carboxylate functionalities in the polycarboxylic acid entity.