Fluorinated siloxanes and methods for their preparation
View Patent ↗Fluorinated siloxane compositions, and methods of making and using the fluorinated siloxanes are disclosed. The polymers described herein may exhibit self-healing properties, a low dielectric constant, and a low refractive index. In some embodiments, a method of making a siloxane compound may involve contacting a silicon metal with a fluorinated compound to form a dichlorosilane compound, hydrolyzing the dichlorosilane compound to form a fluorinated tetrasiloxane compound, and contacting the fluorinated tetrasiloxane compound with a metal catalyst to form a fluorinated cyclic siloxane (D4) compound.
1. A compound of formula I:
wherein
each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently, —CF 2 H, —CF 2 —C(═O)—F, —C 6 F 5 , —CF═CF 2 , —CF 2 —CF═CF 2 , or
2. The compound of claim 1 , wherein R 1 is, one of, —CF 2 H or —CF 2 —C(═O)—F.
3. The compound of claim 1 , wherein R 2 is, one of, —CF 2 H or —CF 2 —C(═O)—F.
4. The compound of claim 1 , wherein R 3 is, one of, —CF 2 H or —CF 2 —C(═O)—F.
5. The compound of claim 1 , wherein R 4 is, one of, —CF 2 H or —CF 2 —C(═O)—F.
6. The compound of claim 1 , wherein R 5 is, one of, —CF 2 H or —CF 2 —C(═O)—F.
7. The compound of claim 1 , wherein R 6 is, one of, —CF 2 H or —CF 2 —C(═O)—F.
8. The compound of claim 1 , wherein R 7 is, one of, —CF 2 H or —CF 2 —C(═O)—F.
9. The compound of claim 1 , wherein R 8 is, one of, —CF 2 H or —CF 2 —C(═O)—F.
10. The compound of claim 1 , wherein: each of R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R 6 , R 7 , and R 8 is, independently, —CF 2 H.
11. The compound of claim 1 , wherein each of R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R 6 , R 7 , and R 8 is, independently, —CF 2 —C(═O)—F.
12. The compound of claim 1 , wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently, —C 6 F 5 .
13. The compound of claim 1 , wherein each of R 1 ,R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently, —CF═CF 2 .
14. The compound of claim 1 , wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently, —CF 2 —CF═CF 2 .
15. The compound of claim 1 , wherein each of R 1 ,R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently,
16. An optical waveguide structure comprising:
a light transmitting core material having a first refractive index; and
a cladding material partially contacting or entirely surrounding the light transmitting core material, wherein the cladding material has a second refractive index lower than the first refractive index of the light transmitting core material, and wherein the light transmitting core material comprises one or more compounds according to formula I:
wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently, —CF 2 H, —CF 2 —C(═O)—F, —C 6 F 5 , —CF═CF 2 , —CF 2 —CF═CF 2 , or
17. A method of making a siloxane compound of formula I:
wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently, —CF 2 H, —CF 2 —C(═O)—F, —C 6 F 5 , —CF═CF 2 , —CF 2 —CF═CF 2 , or
the method comprising:
contacting a silicon metal with a fluorinated compound to form a dichlorosilane compound;
hydrolyzing the dichlorosilane compound to form a fluorinated tetrasiloxane compound with hydroxyl groups; and
contacting the fluorinated tetrasiloxane compound with hydroxyl groups with a metal catalyst to form a fluorinated cyclic siloxane (D4) compound of formula I.
18. The method of claim 17 , wherein contacting the silicon metal comprises contacting with trifluorochloromethane, difluorochloromethane, fluorinated phenyldiazonium chloride, fluorinated vinylchloride, fluorinated allylchloride, fluorinated epichlorohydrin, or any combination thereof.
19. The method of claim 17 , wherein hydrolyzing the dichlorosilane compound comprises controlled hydrolysis of the dichlorosilane compound.
20. The method of claim 17 , wherein contacting the fluorinated tetrasiloxane compound comprises contacting with oxides of Li, K, Ba, Ca, Na, Mg, Al, Mn, Zn, Cr, or any combination thereof.
21. The optical waveguide structure of claim 16 , wherein the light transmitting core material comprises the compound of formula I, wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently, —CF 2 H, or —CF 2 —C(═O)—F.
22. The optical waveguide structure of claim 16 , wherein the light transmitting core material comprises the compound of formula I, wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently —CF 2 H.
23. The optical waveguide structure of claim 16 , wherein the light transmitting core material comprises the compound of formula I, wherein each of R 1 ,R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently, —CF 2 H.
24. The optical waveguide structure of claim 16 , wherein the light transmitting core material comprises the compound of formula I, wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently, —CF 2 —C(═O)—F.
25. The optical waveguide structure of claim 16 , wherein the light transmitting core material comprises the compound of formula I, wherein each of R 1, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently, —C 6 F 5.
26. The optical waveguide structure of claim 16 , wherein the light transmitting core material comprises the compound of formula I, wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently, —CF═CF 2.
27. The optical waveguide structure of claim 16 , wherein the light transmitting core material comprises the compound of formula I, wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently, —CF 2 —CF═CF 2 .
28. The optical waveguide structure of claim 16 , wherein the light transmitting core material comprises the compound of formula I, wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is, independently,