IP Library Granted Patent US 7,625,991
Granted Patent B2
US 7,625,991 · App. 11/677,380 · Granted Dec 1, 2009

Method for making alkoxy-siloxane polyether carboxylates terminated with functional olefin groups

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Quick Facts
Patent No.
US 7,625,991
App. No.
11/677,380
Granted
Dec 1, 2009
Kind
B2
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.

Claims (23)

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:

wherein:

PE is a polyether or polyester fragment,

z=1-500,

q=0-10,

Q is a linear, branched, cyclic or polycyclic organic residue optionally containing siloxane groups (Si-O-Si) and optionally containing heteroatoms selected from the group consisting of B, N, O, Si, P, and S, and

D is a cycloolefinic residue and is different than Q.

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:

a terminated structure having the following formula:

a cyclic structure having the following formula:

where m 1-50, n=0-200, p=0-200, x=3-6 and E is a cycloolefinic residue.

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.

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Apr 9, 2021
From: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
To: KERR CORPORATION
Reel/Frame 055886/0185 →
SECURITY INTEREST Recorded May 8, 2020
From: KERR CORPORATION
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 052611/0362 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 5, 2007
From: ANGELETAKIS, CHRISTOS; STENDER, MATTHIAS
To: KERR CORPORATION
Reel/Frame 018956/0290 →