Silicon compounds derived from furfuryl alcohols and methods of preparation
View Patent ↗Novel silicon compounds containing a siloxane or silane moiety and at least one moiety derived from a furfuryl alcohol, and methods for their synthesis, are provided. The novel compounds may be used as surface modifying agents, surfactants, defoamers, and as monomers for silicone polymerization.
1. A silicon compound or siloxane polymer comprising a siloxane moiety and at least one furfuryl alcohol-derived moiety, wherein the silicon compound has formula (1):
wherein each X is independently a hydrogen, methyl, or hydroxyl group; n is an integer selected from 0 and 1; R 1 is C═O or C(O)NH, m is an integer from one to about six, when m is at least three, one of the internal CH 2 groups may be replaced with an oxygen atom, and R 2 , R 3 , and R 4 are independently a substituted or unsubstituted alkyl group having about one to about four carbon atoms, a substituted or unsubstituted alkoxy group having about one to about four carbon atoms, or a substituted or unsubstituted siloxy group, provided that at least one of R 2 , R 3 , and R 4 is a siloxy group.
2. The compound according to claim 1 , wherein m is three.
3. A silicon compound or siloxane polymer comprising a siloxane moiety and at least one furfuryl alcohol-derived moiety, wherein the furfuryl alcohol is tetrahydrofurfuryl alcohol.
4. The compound according to claim 1 , wherein m=3, n=0, and every X=H.
5. The compound according to claim 1 , having formula (2):
wherein n is an integer selected from 0 and 1; R 1 is C═O or C(O)NH, m is an integer from one to about six, and R 2 , R 3 , and R 4 are independently a substituted or unsubstituted alkyl group having about one to about four carbon atoms, a substituted or unsubstituted alkoxy group having about one to about four carbon atoms, or a substituted or unsubstituted siloxy group, provided that at least one of R 2 , R 3 , and R 4 is a siloxy group.
6. The compound according to claim 1 , wherein the silicon compound is tetrahydrofurfuryloxypropylheptamethyltrisiloxane.
7. A silicon compound or siloxane polymer comprising a siloxane moiety and at least one furfuryl alcohol-derived moiety, wherein the silicon compound has formula (3):
wherein n is an integer selected from 0 and 1; R 1 is C═O or C(O)NH, m is an integer from 1 to about six, and R 2 , R 3 , and R 4 are independently a substituted or unsubstituted alkyl group having about one to about four carbon atoms, a substituted or unsubstituted alkoxy group having about one to about four carbon atoms, or a substituted or unsubstituted siloxy group, provided that at least one of R 2 , R 3 , and R 4 is a siloxy group.
8. A surface modifying reagent comprising a silicon compound according to claim 1 .
9. A surfactant comprising a silicon compound according to claim 1 .
10. A siloxane polymer comprising a siloxane moiety and at least one furfuryl alcohol-derived moiety, wherein the polymer contains a tetrahydrofurfuryloxyalkyl substitution.
11. The compound according to claim 10 , wherein the siloxane polymer is a (tetrahydrofurfuryloxypropyl)methylsiloxane-dimethylsiloxane copolymer.
12. The compound according to claim 10 , wherein the siloxane polymer is selected from the group consisting of a (tetrahydrofurfuryloxypropyl)methylsiloxane-dimethylsiloxane-methylhydrogensiloxane terpolymer and a (tetrahydrofurfuryloxypropyl)methylsiloxane-dimethylsiloxane-methylvinylsiloxane terpolymer.
13. An elastomeric and cross-linked product derived from at least one terpolymer according to claim 12 .
14. The compound according to claim 10 , wherein the siloxane polymer is a siloxane homopolymer or copolymer having a hydride or vinyl terminal group.
15. An elastomeric and cross-linked product derived from the copolymer or homopolymer according to claim 14 .
16. An elastomeric silane formed by the reaction of the polymer according to claim 14 with a hydride- or vinyl-containing siloxane.