METHOD FOR MAKING ALKOXY-SILOXANE POLYETHER CARBOXYLATES TERMINATED WITH FUNCTIONAL OLEFIN GROUPS

Abstract

A resin that may be used, for example, in dental impression materials, and a method of making the resin. The resin comprises an alkoxy-siloxane polyester or polyether carboxylate backbone functionalized with at least two cycloolefin groups capable of undergoing a metathesis reaction. The method of making the resin comprises reacting a hydride terminated siloxane with a polyether or polyester diol containing propylene oxide and ethylene oxide fragments, and a cycloolefinic group functionalized hydroxyalkyl carboxylic acid ester, in the presence of a Group 3 or 13 catalyst.

Description

Claims

1. A resin comprising an alkoxy-siloxane polyester or polyether carboxylate backbone functionalized with at least two cycloolefin groups capable of undergoing a metathesis reaction, and having the formula:

2. The resin of claim 1 wherein D is a cycloolefinic residue selected from the group consisting of norbornenyl, norbornenylethyl, cyclopentenyl, 7-oxanorbornenyl, norbornadienyl, and 7-oxanorbornadienyl.

3. The resin of claim 1 wherein PE is a polyether containing propylene oxide (PO) and ethylene oxide (EO) fragments, z is about 16, q=0 or 1 and

4. The resin of claim 1 wherein PE is a polyether containing propylene oxide (PO) and ethylene oxide (EO) fragments, z=1-50, q=0-1 and

5. The resin of claim 1 further comprising a siloxane carboxylate backbone functionalized with at least two cycloolefin groups capable of undergoing a metathesis reaction, and being at least one of: a pendant structure having the following formula:

6. The resin of claim 5 wherein E is a cycloolefinic residue selected from the group consisting of norbornenyl, norbornenylethyl, cyclopentenyl, 7-oxanorbornenyl, norbornadienyl, and 7-oxanorbornadienyl.

7. The resin of claim 6 wherein D is a cycloolefinic residue selected from the group consisting of norbornenyl, norbornenylethyl, cyclopentenyl, 7-oxanorbornenyl, norbornadienyl, and 7-oxanorbornadienyl.

8. The resin of claim 7 wherein PE is a polyether containing propylene oxide (PO) and ethylene oxide (EO) fragments, z=1-50, q=0-1 and

9. A method of making a cycloolefinic functionalized alkoxy-siloxane polyester or polyether carboxylate, comprising reacting a hydride terminated siloxane with: (a) a polyether or polyester diol containing propylene oxide and ethylene oxide fragments, and(b) a cycloolefinic group functionalized hydroxyalkyl carboxylic acid ester, in the presence of a Group 3 or 13 catalyst.

10. The method of claim 9 wherein the catalyst is tris(pentafluoro-triphenyl)borane.

11. The method of claim 9 wherein (b) is hydroxypropyl norbornenecarboxylate.