High refractive index siloxanes
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.
1. A silicon-containing material modified with a saturated bridged bicyclic group, wherein the silicon-containing material is a cyclic siloxane comprising at least one silicon atom in the siloxane having a saturated bridged bicyclic group attached thereto, the saturated 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 ; and the silicon-containing material is a cyclic siloxane of formula (2):
where D 1-3 are groups of the formula R 1 R 14 SiO 2/2 , R 13 and R 14 are independently chosen from a bicyclic compound of Formula 1, H, an unsubstituted or substituted monovalent hydrocarbon groups, aromatic groups, alkoxy, mercaptopropyl, isocyanyl, and glycidyl groups, where at least one of the R 13 or R 14 groups is a bicyclic compound of Formula 1, a+b+c is between 3 and 10, and at least one of a, b, or c is greater than zero, and wherein the silicon-containing material has an aromatic content of from about 0.1 weight percent to about 40 weight percent.
2. The silicon-containing material of claim 1 , wherein the bicycle(2,2,1) group of formula 1 is a norbornyl group bonded to a silicon atom.
3. The siloxane of claim 1 , wherein the siloxane is of the formula 2a:
where a is from 0-6, b is 1-6, c is 0-6, R 13 , R 14 , and R 17 are independently chosen from an unsubstituted or substituted monovalent hydrocarbon groups, aromatic groups, alkoxy, mercaptopropyl, isocyanyl, and glycidyl groups; and R 16 is chosen from a norbornyl or a group as described for R 13 , R 14 , and R 17 .
4. The siloxane of claim 3 where a is 0, b is 1-6, c is 0 and R 16 methyl group.
5. The siloxane of claim 3 where a is 0, b is 1-4, c is 1-3, and R 16-17 are methyl groups.
6. The siloxane of claim 3 where a+b+c are between 3-10.
7. The silicon-containing material of claim 1 having a norbornyl content of from about 1 weight percent to about 90 weight percent.
8. The silicon-containing material of claim 1 , wherein the siloxane is substantially free of any aromatic groups.
9. A curable composition comprising a silicon-containing material of claim 1 and a compound that will react with the silicon-containing material.
10. The composition of claim 9 , 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.
11. The composition of claim 9 , wherein the compound that will react with the silicon-containing material is a crosslinker.
12. The composition of claim 11 , wherein the crosslinker is chosen from norbornyl-functional siloxanes, cyclosiloxanes, copolymers thereof, or a combination of two or more thereof.
13. The composition of claim 12 , wherein the cross-linker is of formula 14
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.
14. The curable composition of claim 9 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.
15. The curable composition of claim 14 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.
16. The composition of claim 9 , wherein the curable composition is UV curable, condensation curable, amine curable, thermal curable, or a combination of two or more thereof.
17. A cured article formed from the composition of claim 9 .
18. The cured article of claim 17 having a refractive index of from about 1.42 to about 1.55.
19. The cured article of claim 17 having a transparency of ≥90% of a 1 mm thick sheet.
20. The cured article of claim 17 having a gas permeability of from about 100 to 10000 cm 3 /m 2 .24 h. atm.
21. The cured article of claim 17 , where the articles are used as LED encapsulants, optical waveguides, optical lenses, optical bonding materials, optical adhesives, optical films or sheets, laminated films or sheets, in electronic components, or in combination with semiconductor devices.