US 11,884,779 B2
Ionically modified silicones, compositions, and medical devices formed therefrom
Sukanta Dolai, Bangalore (IN); Shreedhar Bhat, Bangalore (IN); and Meenal Mehra, Bangalore (IN)
Assigned to Momentive Performance Materials Inc., Waterford, NY (US)
Appl. No. 16/482,739
Filed by Momentive Performance Materials Inc., Waterford, NY (US)
PCT Filed Feb. 16, 2018, PCT No. PCT/US2018/018479
§ 371(c)(1), (2) Date Aug. 1, 2019,
PCT Pub. No. WO2018/152395, PCT Pub. Date Aug. 23, 2018.
Claims priority of provisional application 62/459,632, filed on Feb. 16, 2017.
Prior Publication US 2020/0231757 A1, Jul. 23, 2020
Int. Cl. C08G 77/388 (2006.01); A61K 47/69 (2017.01); A61K 9/00 (2006.01); A61K 9/70 (2006.01); A61K 47/34 (2017.01); C08G 77/18 (2006.01); G02B 1/04 (2006.01); A61K 9/06 (2006.01); C08G 77/20 (2006.01); C08G 77/22 (2006.01); C08G 77/392 (2006.01); C09D 183/06 (2006.01); C08F 230/08 (2006.01); C08G 77/04 (2006.01); A61K 45/06 (2006.01); C08G 77/06 (2006.01)
CPC C08G 77/388 (2013.01) [A61K 9/0051 (2013.01); A61K 9/06 (2013.01); A61K 9/7023 (2013.01); A61K 47/34 (2013.01); A61K 47/6903 (2017.08); C08F 230/08 (2013.01); C08G 77/18 (2013.01); C08G 77/20 (2013.01); C08G 77/22 (2013.01); C08G 77/392 (2013.01); C09D 183/06 (2013.01); G02B 1/043 (2013.01); A61K 45/06 (2013.01); C08G 77/045 (2013.01); C08G 77/06 (2013.01); C08G 2210/00 (2013.01)] 28 Claims
 
1. A silicone compound of the Formula (I):

OG Complex Work Unit Chemistry
where R1 is chosen from a chemical bond or a divalent group comprising 1 to 16 carbon atoms optionally containing a heteroatom chosen from oxygen, sulfur, or nitrogen;
R2 is a linear, branched, cyclic, or cage like siloxanyl moiety, or silane moiety having the general structure (a)

OG Complex Work Unit Chemistry
X1 is independently selected from linear or branched alkyl group containing 1-16 carbon atoms, trimethoxy silyl, trimethylsilyloxy, —O[Si(CH3)2O—]n wherein n is an integer chosen from 1 to 9, (CH3)3Si(CH2)oCH2— wherein o is an integer from 0-3, (CH3)3SiCH2CH2Si(CH3)2O—, or (CH3)3Si(CH2CH2Si(CH3)2O)s— wherein s is an integer chosen from 0-200;
X2 is independently selected from a linear or branched alkyl group containing 1-16 carbon atoms, trimethoxy silyl, trimethylsilyloxy, —O[Si(CH3)2O—]n wherein n is an integer chosen from 1 to 9, (CH3)3Si(CH2)oCH2— wherein o is an integer from 0-3, (CH3)3SiCH2CH2Si(CH3)2O—, or (CH3)3Si(CH2CH2Si(CH3)2O)z— wherein z is an integer chosen from 0-200, or —[OSi(CH3)2]mG1, wherein G1 is (CH3)3SiO— and m is an integer from 0 to 400, or a reactive or non-reactive silicone group with the general Formula (b1) or (b2):

OG Complex Work Unit Chemistry
where 1 is an integer chosen from 0-200; and p in Formula (a) is 0 when X2 is of the Formula (b1) or (b2);
X3 and X5 are independently chosen from a C1-C6 alkyl, trimethylsiloxy, (CH3)3SiCH2CH2—, (CH3)3SiCH2CH2Si(CH3)2O—, and —OSi(CH3)2, with the provisos that (i) when X1 or X6 is —O[Si(CH3)2O—]n, then X3 and X5, repectively, is —OSi(CH3)2 and X1 forms a chemical bond with the X3 and X5 forms a chemical bond with X6 correspondingly form a divalent —X1—X3—or X5-X6- group, which is bonded to the silicon atom to form a cyclic polysiloxane ring, and (ii) when X3 and/or X5 is —OSi(CH3)2, then X1 and/or X6 is —O[Si(CH3)2O—]n, and X1 forms a chemical bond with the X3 and/or X5 forms a chemical bond with X6 form a divalent —X1-X3— or X5--X6— group, which is bonded to the silicon atom to form a cyclic polysiloxane ring;
where, X1, X2, X3 optionally can each be —O[Si(R7)O—]n, and interconnected to form a polysilsesquioxane ring as described in formula (b3) and R7 is independently chosen from a linear or branched alkyl or aralkyl group;

OG Complex Work Unit Chemistry
X6, X7, X8 are independently chosen from a linear or branched alkyl group containing 1-16 carbon atoms, alkoxy, trimethylsilyloxy, or —O[Si(CH3)2O—]n, wherein n is an integer chosen from 1 to 9, and wherein X6 and X7, X7 and X8, or X6 and X8 may form a ring;
X4 is an optional connecting group selected independently from dimethylsiloxy, —O[Si(CH3)2O—], or —CH2CH2 (CH3)2SiO-moiety;
p is an integer chosen from 0-10;
G is a bridging unit selected from a linear or branched alkyl group or a carbocyclic group optionally contains hetero atoms;
A is a heteroatom;
I is a zwitterionic moiety; and
Z is a polymerizable group having the general Formula (c):

OG Complex Work Unit Chemistry
wherein R14, R15, and R16 are independently chosen from hydrogen or monovalent hydrocarbon radical with 1-5 carbon atoms; and F is a linker group chosen from aliphatic, cycloaliphatic, or aromatic hydrocarbon radical having 1-16 carbon atoms and optionally containing a heteroatom.