IP Library › Granted Patent US 12,104,019
Granted Patent B2
US 12,104,019 · App. 17/601,723 · Granted Oct 1, 2024

Bridged frustrated Lewis pairs as thermal trigger for reactions between Si—H and alpha-beta unsaturated esters

Inventors: Marc-Andre Courtemanche (Midland, MI); Eun Sil Jang (Columbus, OH); Yanhu Wei (Midland, MI)
Assignee: Dow Silicones Corporation
C08G77/06C07F7/1804C08G77/12C08G77/20
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Quick Facts
Patent No.
US 12,104,019
App. No.
17/601,723
Granted
Oct 1, 2024
Kind
B2
Abstract

A composition contains an alpha-beta unsaturated ester, a silyl hydride, and a Bridged Frustrated Lewis Pair.

Claims (27)

1. A composition comprising a mixture of silyl hydride, alpha-beta unsaturated esters, and a Bridged Frustrated Lewis Pair.

2. The composition of claim 1 , wherein the Bridged Frustrated Lewis Pair comprises:

(a) a Lewis acid selected from a group consisting of aluminum alkyls, aluminum aryls, fluorinated aryl borane, boron halides, aluminum halides, gallium alkyls, gallium aryls, gallium halides, silylium cations and phosphonium cations;

(b) a Lewis base selected from a group consisting of molecules having the following structures: PR 3 , P(NR 2 ) 3 , NR 3 , N(SiR 3 )xR 3-x , RC(NR)N, P(N—R)R 3 guanidines, amidines, phosphazenes, and

and

where R is in each occurrence independently selected from a group consisting of hydrogen, alkyl, substituted alkyl, aryl and substituted aryl; and

(c) a bridging molecule connecting the Lewis acid and Lewis base, the bridging molecule selected from a group consisting of carbon dioxide, H 2 , nitriles, alkenes, alkynes, esters, esters and aldehydes.

3. The composition of claim 2 , wherein the Lewis acid is a fluorinated aryl borane.

4. The composition of claim 2 , wherein the Lewis base is selected from a group consisting of PR 3 , NR 3 , guanidines, amidines and phosphazenes.

5. The composition of claim 2 , wherein the bridging molecule is selected from a group consisting of carbon dioxide, nitrile, H 2 , alkynes and alkenes.

6. The composition of claim 2 , wherein the Lewis acid is a fluorinated aryl borane, the Lewis base is selected from a group consisting of PR 3 and NR 3 and the bridging molecule is selected from a group consisting of carbon dioxide and nitriles; where R is in each occurrence independently selected from a group consisting of hydrogen, alkyl, substituted alkyl, aryl and substituted aryl.

7. The composition of claim 1 , wherein the composition is free of transition metals.

8. The composition of claim 1 , wherein the alpha-beta ester is one or a combination of more than one (meth)acrylate.

9. A chemical reaction process comprising the steps of:

(a) providing a composition comprising a mixture of silyl hydride, alpha-beta unsaturated esters, and a Bridged Frustrated Lewis Pair; and

(b) heating the composition to a temperature sufficient to dissociate Lewis acid from the Bridged Frustrated Lewis Pair.

10. The process of claim 9 , wherein step (a) comprises mixing together a Bridged Frustrated Lewis Pair, a silyl hydride and an alpha-beta ester.

11. The process of claim 9 , wherein after step (a) and prior to step (b) the composition is applied to a substrate or placed in a mold.

12. The process of claim 10 , wherein after step (a) and prior to step (b) the composition is applied to a substrate or placed in a mold.

13. The composition of claim 3 , wherein the Lewis base is selected from a group consisting of PR 3 , NR 3 , guanidines, amidines and phosphazenes.

14. The composition of claim 3 , wherein the bridging molecule is selected from a group consisting of carbon dioxide, nitrile, H 2 , alkynes and alkenes.

15. The composition of claim 4 , wherein the bridging molecule is selected from a group consisting of carbon dioxide, nitrile, H 2 , alkynes and alkenes.

16. The composition of claim 2 , wherein the composition is free of transition metals.

17. The composition of claim 4 , wherein the composition is free of transition metals.

18. The composition of claim 5 , wherein the composition is free of transition metals.

19. The composition of claim 6 , wherein the composition is free of transition metals.

20. The composition of claim 2 , wherein the alpha-beta ester is one or a combination of more than one (meth)acrylate.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 15, 2024
From: COURTEMANCHE, MARC-ANDRE; JANG, EUN SIL; WEI, YANHU
To: DOW SILICONES CORPORATION
Reel/Frame 068291/0641 →
Continuity (2)
Provisional Application 62856773 · Jun 4, 2019
Related Publication 20220169795A1 · Jun 2, 2022
Cited By (1)
US 12,247,105