US 11,702,433 B2
Functionalized F-POSS monomer compositions and uses thereof
John C. Warner, Wilmington, MA (US); Jean R. Loebelenz, Essex, MA (US); Srinivasa Rao Cheruku, Lexington, MA (US); Thomas Woodrow Gero, Stow, MA (US); and Perry L. Catchings, Sr., Roxbury, MA (US)
Assigned to NBD NANOTECHNOLOGIES, INC., Lexington, MA (US)
Filed by NBD Nanotechnologies, Inc., Lexington, MA (US)
Filed on Oct. 14, 2019, as Appl. No. 16/601,022.
Application 16/601,022 is a division of application No. 15/705,089, filed on Sep. 14, 2017, granted, now 10,442,823.
Application 15/705,089 is a continuation in part of application No. 15/230,697, filed on Aug. 8, 2016, granted, now 10,208,070, issued on Feb. 19, 2019.
Application 15/230,697 is a continuation in part of application No. 15/065,289, filed on Mar. 9, 2016, granted, now 10,174,059, issued on Jan. 8, 2019.
Application 15/230,697 is a continuation of application No. 14/876,911, filed on Oct. 7, 2015, granted, now 9,409,933, issued on Aug. 9, 2016.
Claims priority of provisional application 62/130,170, filed on Mar. 9, 2015.
Claims priority of provisional application 62/060,622, filed on Oct. 7, 2014.
Prior Publication US 2020/0040016 A1, Feb. 6, 2020
Int. Cl. C08G 77/24 (2006.01); C07F 7/21 (2006.01); C09D 7/62 (2018.01); C08G 77/04 (2006.01); C08L 83/04 (2006.01); C08K 5/549 (2006.01); C09D 183/08 (2006.01)
CPC C07F 7/21 (2013.01) [C08G 77/045 (2013.01); C08G 77/24 (2013.01); C08K 5/549 (2013.01); C08L 83/04 (2013.01); C09D 7/62 (2018.01); C09D 183/08 (2013.01)] 15 Claims
 
1. An article comprising a synthetic blend copolymer prepared by polymerization of a compound having a formula I

OG Complex Work Unit Chemistry
wherein,
R1 is a long chain fluorinated alkyl that is a straight chain or a branched chain alkyl group having 5 to 12 carbon atoms in a longest continuous chain of carbon atoms as counted from a point of attachment of the longest continuous chain of carbon atoms to a silicon atom at any apex of a silicon-oxide core, where at least one hydrogen atom in the straight chain or the branched chain alkyl group is replaced by a fluorine atom;
R2 is selected from the group consisting of C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C6-C10 aryl, C3-C8 cycloalkyl, 5-7 membered heterocyclic and 5-7 membered heteroaryl, wherein each hydrogen atom in R2 is independently optionally substituted by an R3;
R3 is —OC(O)R4 or —OC(O)OR4;
R4 is methyl, wherein each hydrogen atom in R4 is independently optionally substituted by an R6;
each R6 is independently selected from the group consisting of halo, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C6-C10 aryl, C3-C8 cycloalkyl, 5-7 membered heterocyclic, 5-7 membered heteroaryl, —NCO, —OR7, —NR7R8, —OC(O)R7, —C(O)OR7, —C(O)R7, —OC(O)OR7, —C(O)NR7R8, —OC(O)NR7R8, —NR7C(O)R8, —NR7C(O)OR8 and —NR7C(O)NR7R8, and when R6 is C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C6-C10 aryl, C3-C8 cycloalkyl, 5-7 membered heterocyclic or 5-7 membered heteroaryl, each hydrogen atom in R6 is independently optionally substituted by an R9;
each R7 and R8 is independently selected from the group consisting of hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C6-C10 aryl, C3-C8 cycloalkyl, 5-7 membered heterocyclic and 5-7 membered heteroaryl, wherein each hydrogen atom in R7 and R8 is independently optionally substituted by one or more R9;
each R9 is independently selected from the group consisting of hydrogen, halo, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C6-C10 aryl, C3-C8 cycloalkyl, 5-7 membered heterocyclic, 5-7 membered heteroaryl, —NCO, —OR10, —NR10R11, —OC(O)R10, —C(O)OR10, —C(O)R10, OC(O)OR10, —C(O)NR10R11, —OC(O)NR10R11, —NR10C(O)R11, —NR10C(O)OR11 and NR10C(O)NR10R11, and when R9 is C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C6-C10 aryl, C3-C8 cycloalkyl, 5-7 membered heterocyclic, C3-C8 cycloalkyl or 5-7 membered heteroaryl, each hydrogen in R9 is independently optionally substituted by a moiety selected from the group consisting of halo, —NCO, —OR10, —NR10R11, —OC(O)R10, —C(O)OR10, —C(O)R10, OC(O)OR10, C(O)NR10R11, —OC(O)NR10R11, —NR10C(O)R11, —NR10C(O)OR11 and NR10C(O)NR10R11;
each R10 and R11 is independently selected from the group consisting of H, C1-C8 alkyl, C2-C8 alkenyl and C2-C8 alkynyl, and when R10 or R11 are C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl, each hydrogen atom in R10 and R11 is independently optionally substituted by a fluorine atom;
n is an integer from 1 to 7; and,
each R10 and R11 is independently covalently attached at a silicon atom,
with at least one monomer; wherein the compound of the formula I is prepared by a process comprising:
(a) contacting a compound of the formula R1Si(ORA)3 with a compound of the formula R2Si(ORA)3, in the presence of a base, wherein —ORA is a C1-C8 alkoxy, and the —ORA on R1Si(ORA)3 and R2Si(ORA)3 can be the same or different.