High refractive index siloxanes
View Patent ↗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 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.