Perfluoroalkyl monoesters of anhydride 2,3,4,5-tetrahydrofurantetracarboxylic acid

Abstract

This invention describes new perfluoroalkyl substituted esters, diesters and polyesters which contain at least one cyclic 5-membered anhydride group or two carboxy groups, as well as half amides and half esters thereof; their synthesis and their use as surface-active reactants in polycondensate resin systems.The anhydrides are synthesized by reaction of perfluoroalkyl substituted alcohols or diols with dianhydrides or an anhydrides-acid chloride and have the general structure ##STR1## wherein: Q is the tetra-radical rest of a tri- or tetracarboxylic acid, which contains at least one 1,2-dicarboxy grouping,X is hydrogen or COOH,R.sub.f is perfluoroalkyl or perfluoroalkoxyperfluoroalkyl group of 4 to 18 carbon atoms,A is 1 or 2,A is hydrogen or ##STR2## wherein: m is an integer from 0 to 5, and R.sup.3 is the residue of a R.sub.f substituted alcohol or diol.

Description

The present invention pertains to perfluoroalkyl substituted anhydrides of the general formula ##STR3## where Q is derived from 2,3,4,5-tetrahydrofurantetracarboxylic acid, which are useful in making surface active reactants, for which the essential material constituting a disclosure thereof is incorporated by reference from Ser. No. 646,689, filed Jan. 5, 1976, now U.S. Pat. No. 4,058,537.

Claims

1. A compound of formula I ##STR4## wherein Q is the tetraradical rest of 2,3,4,5-tetrahydrofurantetracarboxylic acid;

X is carboxy;

R.sub.f is perfluoroalkyl of 6 to 18 carbon atoms;

A is 1 or 2;

A is hydrogen or group II; ##STR5## m is an integer from 0 to 2; Q.sub.1 is the same as Q, and

R.sup.3 is the residue of an R.sub.f substituted aliphatic alcohol or diol of the structure ##STR6##

HO--R.sup.2 --S--R.sup.1 --R.sub.f

where R.sup.1 is a branched or straight chain alkylene of 1 to 12 carbon atoms, alkylenethioalkylene of 4 to 12 carbon atoms, alkyleneoxyalkylene elen of 4 to 12 carbon atoms or alkyleneiminoalkylene of 4 to 12 carbon atoms where the nitrogen atom contains as the third substituent hydrogen or alkyl of 1 to 6 carbon atoms; and

R.sup.2 is straight or branched chain alkylene of 1 to 12 carbon atoms or an alkylenepolyoxyalkylene of the formula C.sub.n H.sub.2n (OC.sub.k H.sub.2k).sub.r where n is 1 to 12, k is 2 to 6 and r is 1 to 40.

2. A compound according to claim 1 of formula I wherein Q is the tetraradical rest of 2,3,4,5-tetrahydrofurantetracarboxylic acid; X is carboxy; R.sub.f is perfluoroalkyl of 6 to 18 carbon atoms; a is 1 or 2; A is group II ##STR7## m is 0; Q.sub.1 is the same as Q and R.sup.3 is the residue of an R.sub.f substituted aliphatic alcohol or diol of the structure ##STR8## where R.sup.1 is a branched or straight chain alkylene of 1 to 4 carbon atoms; and

R.sup.2 is a branched or straight chain alkylene of 1 to 4 carbon atoms or alkylenepolyoxyalkylene of the formula C.sub.n H.sub.2n (OC.sub.k H.sub.2k).sub.r where n is 1 to 4, k is 2 to 4 and r is 1 to 20.

3. A compound according to claim 2 wherein R.sup.1 is ethylene, and R.sup.2 is methylene or methylenepolyoxyalkylene of the formula CH.sub.2 (OC.sub.k H.sub.2k).sub.r where k is 2 and r is 1 to 20.

4. A compound according to claim 1 of the structure ##STR9## where R.sub.f is perfluoroalkyl of 6 to 18 carbon atoms.

5. A compound according to claim 1 of the structure ##STR10## where R.sub.f is perfluoroalkyl of 6 to 18 carbon atoms.

6. A compound according to claim 1 of the structure ##STR11## where R.sub.f is perfluoroalkyl of 6 to 18 carbon atoms.

7. A compound according to claim 1 of the structure ##STR12## where R.sub.f is perfluoroalkyl of 6 to 18 carbon atoms.