SILICON COMPOUNDS DERIVED FROM FURFURYL ALCOHOLS AND METHODS OF PREPARATION
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 or silane moiety and at least one furfuryl alcohol-derived moiety.
2 . The compound according to claim 1 , further comprising an alkyl group bridging the siloxane or silane moiety and the furfuryl alcohol-derived moiety.
3 . The compound according to claim 2 , wherein the alkyl group comprises about three carbon atoms.
4 . The compound according to claim 1 , wherein the furfuryl alcohol is tetrahydrofurfuryl alcohol.
5 . The compound according to claim 1 , 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 an alkoxy or siloxy group.
6 . The compound according to claim 5 , wherein m=3, n=0, and every X═H.
7 . 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 an alkoxy or siloxy group.
8 . The compound according to claim 1 , wherein the silicon compound is tetrahydrofurfuryloxypropyltriethoxysilane.
9 . The compound according to claim 1 , wherein the silicon compound is tetrahydrofurfuryloxypropylheptamethyltrisiloxane.
10 . The compound according to claim 1 , 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 an alkoxy or siloxy group.
11 . A surface modifying reagent comprising a silicon compound according to claim 1 .
12 . A surfactant comprising a silicon compound according to claim 1 .
13 . The compound according to claim 1 , wherein the compound is a siloxane polymer containing a tetrahydrofurfuryloxyalkyl substitution.
14 . The compound according to claim 1 , wherein the silicon compound is a (tetrahydrofurfuryloxypropyl)methylsiloxane-dimethylsiloxane copolymer.
15 . The compound according to claim 1 , wherein the silicon compound is selected from the group consisting of a (tetrahydrofurfuryloxypropyl)methylsiloxane-dimethylsiloxane-methylhydrogensiloxane terpolymer and a (tetrahydrofurfuryloxypropyl)methylsiloxane-dimethylsiloxane-methylvinylsiloxane terpolymer.
16 . An elastomeric and cross-linked product derived from at least one terpolymer according to claim 15 .
17 . The compound according to claim 1 , wherein the silicon compound is a siloxane homopolymer or copolymer having a hydride or vinyl terminal group.
18 . An elastomeric and cross-linked product derived from the copolymer or homopolymer according to claim 17 .
19 . An elastomeric silane formed by the reaction of the polymer according to claim 17 with a hydride- or vinyl-containing siloxane.
20 . A method for preparing a silicon compound comprising a siloxane or silane moiety and at least one furfuryl alcohol-derived moiety, the method comprising hydrosilylating a hydride functional silane or siloxane with at least one furfuryl alcohol containing a double bond to yield a hydrolytically stable silicon-to-carbon bond.