Silanes and silicones with distinct hydrophilic and oleophobic substitution
View Patent ↗The invention relates to silicon compounds having formula (I): (RfCH 2 CH 2 ) 2-n [R(OCH 2 CHR′) m OR″] n SiX 2 (I). In formula (I), Rf is a linear or branched perfluorinated hydrocarbon having 4 or more carbon atoms, R is a methyl or ethyl group, R′ is H or CH 3 , m is an integer of 1 to about 24, R″ is a hydrocarbon bridge having 1 to about 11 carbon atoms, n is an integer from 0 to 2, and X is H, Cl or an alkoxy group. The inventive materials may be used to produce siloxanes or silicones by hydrolytic condensation and have utility in surface modification.
1. A silicon compound having formula (I):
(RfCH 2 CH 2 ) 2-n [R(OCH 2 CHR′) m OR″] n SiX 2 (I)
wherein Rf is a linear or branched perfluorinated hydrocarbon having 4 or more carbon atoms, R is a methyl or ethyl group, R′ is H or CH 3 , m is an integer of 1 to about 24, R″ is a hydrocarbon bridge having 1 to about 11 carbon atoms, n is an integer from 0 to 2, and X is H, Cl or an alkoxy group.
2. The silicon compound according to claim 1 , wherein Rf has 4 to about 10 carbon atoms.
3. The silicon compound according to claim 1 , wherein m is an integer of about 2 to about 6.
4. The silicon compound according to claim 1 , wherein R″ is CH 2 CH 2 CH 2 .
5. The silicon compound according to claim 1 , wherein X is Cl, OCH 3 , or OC 2 H 5 .
6. A polymeric siloxane compound formed by hydrolytic condensation of the silicon compound according to claim 1 .
7. The silicon compound according to claim 1 , wherein the compound is a bis[(methoxypolyethyleneoxy)alkyl]dichlorosilane.
8. The silicon compound according to claim 7 , having formula [R(OCH 2 CHR′) m OR″] 2 SiX 2 .
9. A polymeric siloxane compound formed by hydrolytic condensation of the silicon compound according to claim 7 .
10. The silicon compound according to claim 1 , wherein the compound is a bis(perfluoroalkyl)dichlorosilane.
11. The silicon compound according to claim 10 , having formula (RfCH 2 CH 2 ) 2 SiX 2 .
12. A polymeric siloxane compound formed by hydrolytic condensation of the silicon compound according to claim 10 .
13. The silicon compound according to claim 1 , wherein the compound is a (tridecafluorooctyl)(methoxypolyethyleneoxypropyl)dichlorosilane.
14. The silicon compound according to claim 1 , wherein the compound is a (tridecafluorooctyl)(methoxypolyethyleneoxypropyl)dimethoxysilane having about 6 to 8 ethylene oxide units.
15. The silicon compound according to claim 1 , wherein the compound is a bis(methoxytriethyleneoxypropyl)dichlorosilane.
16. The silicon compound according to claim 1 , wherein the compound is a bis(methoxytriethyleneoxypropyl)dimethoxysilane.
17. The silicon compound according to claim 1 , wherein the compound is a bis(nonafluorohexyl)dichlorosilane.
18. A [(methoxy(polyethyleneoxy)alkyl]hydridodichlorosilane.
19. The silane according to claim 18 , having formula [R(OCH 2 CHR′) m OR″]SiHX 2 , wherein R is a methyl or ethyl group, R′ is H or CH 3 , m is an integer of 1 to about 24, R″ is a hydrocarbon bridge having 1 to about 11 carbon atoms, and X is H, Cl or an alkoxy group.
20. The silane according to claim 18 , wherein the silane is a methoxytriethyleneoxypropylhydridodichlorosilane.
21. A siloxane polymer having formula (II):
(CH 3 ) 3 SiO[(RfCH 2 CH 2 ) 2 [R(OCH 2 CHR′) m OR″] p SiO]SiMe 3 (II)
wherein Rf is a linear or branched perfluorinated hydrocarbon having 4 or more carbon atoms, R is a methyl or ethyl group, R′ is H or CH 3 , m is an integer of 1 to about 24, R″ is a hydrocarbon bridge having 1 to about 11 carbon atoms, and p is an integer from 0 to 100.