High refractive index siloxanes

Patent metadata

Field	Value
Publication number	US-9963469-B2
Application number	US-201414774871-A
Country	US
Kind code	B2
Filing date	Mar 14, 2014
Priority date	Mar 14, 2013
Publication date	May 8, 2018
Grant date	May 8, 2018

Abstract

A polymer material comprising a constraint bicyclic bridged structure such as bicyclo(2,2,1) ring system, most preferably a norbornyl group, pendant to a siloxane backbone. The bridged bicyclic-containing materials can exhibit good refractive index, transparency, gas permeability, and/or other properties making them suitable for use in a variety of applications.

First claim

What is claimed is:

1. A silicon-containing material modified with a saturated bridged bicyclic group, wherein the silicon-containing material is a siloxane of the formula:

R 11 -R 14 are independently chosen from hydrogen, hydroxyl, or a group containing 1-30 carbon atoms chosen from a linear or branched alkyl group, a cycloalkyl group, a linear or branched alkoxy group, an alkylvinyl group (including allyl), a branched or linear alkenyl group, a cycloalkenyl group, a linear or branched alkynyl group, an aryl group, a substituted aryl group, a polynuclear aromatic group, an amide, an amino-group, a propyl-mercapto group, an silyloxy group, an epoxy-containing group, a glycidyl-containing group, an acryloyl group, an isocyanyl group, a carbonyl group, a is from 0-1000, b is from 0-500, d is from 0-100, where at least b and d are positive integers; R 10 is hydrogen or a vinyl group; R 19 is phenyl or a monovalent hydrocarbon; and R 16 is chosen from a monovalent hydrocarbon group or a bicyclic group of Formula 1:

where R 1 -R 7 are independently chosen from H, a C1-C12 alkyl, —CO 2 R′, and —(CH 2 ) n —B; n is 0-12; B is OR′, SR′, NR 1 R 2 ; R′ is a C1-C12 alkyl; and A is chosen from CH 2 , NR′, S, SO, or SO 2 .

2. The silicon-containing material of claim 1 wherein the R 16 group is a bridged bicyclic group is a bicyclo(2,2,1) group of formula (1):

where R 1 -R 7 are independently chosen from H, a C1-C12 alkyl, —CO 2 R′, and —(CH 2 ) n —B; n is 0-12; B is OR′, SR′, NR 1 R 2 ; R′ is a C1-C12 alkyl; and A is from CH 2 , NR′, S, SO, or SO 2 .

3. The silicon-containing material of claim 2 , wherein the bicycle(2,2,1) group of formula 1 is a norbornyl group bonded to a silicon atom.

4. The siloxane of claim 1 where R 10 is hydrogen.

5. The siloxane of claim 1 where R 10 a is vinyl group.

6. The silicon-containing material of claim 1 having a norbornyl content of from about 1 weight percent to about 90 weight percent.

7. The silicon-containing material of claim 1 having an aromatic content of from about 0.1 weight percent to about 40 weight percent.

8. A curable composition comprising the silicon-containing material of claim 1 and a compound that will react with the silicon-containing material.

9. The composition of claim 8 , wherein the compound that will react with the silicon-containing material is a second silicon-containing material modified with a saturated bridged bicyclic group, the second silicon-containing material being the same or different than the silicon-containing material.

10. The composition of claim 8 , wherein the compound that will react with the silicon-containing material is a crosslinker.

11. The composition of claim 10 , wherein the crosslinker is chosen from norbornyl-functional siloxanes, cyclosiloxanes, copolymers thereof, or a combination of two or more thereof.

12. The composition of claim 11 , wherein the cross-linker is of formula

where R 13 , R 14 , and R 16 are independently chosen from an unsubstituted or substituted monovalent hydrocarbon groups, aromatic groups, alkoxy, mercaptopropyl, isocyanyl, glycidyl groups, or a combination of two or more thereof; a is 0 to 4, b is 1 to 4, b″ is 1 to 6, and n is 0-6.

13. The curable composition of claim 8 further comprising an antioxidant, a thermal stabilizer, a UV stabilizer, an adhesion promoter, a metal catalyst, an inhibitor, a filler, an initiator, or a combination of two or more thereof.

14. The curable composition of claim 13 comprising a platinum group metal catalyst, a ruthenium group metal catalyst, or a combination thereof, the catalyst being present in a concentration of about 1 to about 100 ppm.

15. The composition of claim 8 , wherein the curable composition is UV curable, condensation curable, amine curable, thermal curable, or a combination of two or more thereof.

16. A cured article formed from the composition of claim 8 .

17. The cured article of claim 16 having a refractive index of from about 1.42 to about 1.55.

18. The cured article of claim 16 having a transparency of ≥90% of a 1 mm thick sheet.

19. The cured article of claim 16 having a gas permeability of from about 100 to 10000 cm 3 /m 2 ·24 h·atm.

20. The cured article of claim 16 , where the article is a LED encapsulant, an optical waveguide, an optical lense, an optical bonding material, an optical adhesive, an optical film or sheet, a laminated film or sheet employed in an electronic components or in combination with a semiconductor device.

21. A personal care composition containing a composition comprising the silicon-containing material of claim 1 .

22. The personal care composition of claim 21 wherein the composition comprising the silicon-containing material is an additive in a color cosmetic formulation.

Assignees

• Momentive Performance Mat Inc
• Momentive Performance Mat Inc

Inventors

• Srivastava Rajiv
• Dukes Douglas M

Classifications

• C08G77/12

  containing silicon bound to hydrogen · CPC title

• C07F7/0838 Primary

  Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21) · CPC title

• C08G77/398

  containing boron or metal atoms · CPC title

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title

• C08G77/14

  containing silicon bound to oxygen-containing groups · CPC title