Bifunctional Poly(alkyleneoxides) with Aminoalkyl and Unsaturated Termini and Derivatives Thereof
A heterofunctional poly(alkyleneoxide) according to the invention contains a first polymer terminus containing a protected, unprotected, or derivatized amine or aminoalkyl functionality and a second polymer terminus containing an unsaturated functionality. Reaction products, derivatives, and methods of making these materials are also described.
1 . A heterofunctional poly(alkyleneoxide) having first and second polymer termini, wherein the first polymer terminus comprises a protected, unprotected, or derivatized aminoalkyl functionality and the second polymer terminus comprises an unsaturated functionality.
2 . The poly(alkyleneoxide) according to claim 1 , wherein the aminoalkyl functionality is a silylated amine functional group.
3 . The poly(alkyleneoxide) according to claim 1 , wherein the alkyleneoxide is selected from an ethylene oxide, a propylene oxide, a butylene oxide, a hexafluoropropylene oxide, and a glycidyl ether of a silicone.
4 . The poly(alkyleneoxide) according to claim 1 , comprising an α-amine or α-aminoalkyl terminus and an ω-allyl terminus.
5 . The poly(alkyleneoxide) according to claim 4 , wherein the aminoalkyl terminus is a silylated amine functional group.
6 . The poly(alkyleneoxide) according to claim 1 , comprising an α-amine or α-aminoalkyl terminus and an ω-vinylbenzyl terminus.
7 . The poly(alkyleneoxide) according to claim 7 , wherein the aminoalkyl terminus is a silylated amine functional group.
8 . The poly(alkyleneoxide) according to claim 1 , comprising an a N,N-bis(trimethylsilyl)amine terminus and an ω-allyl terminus.
9 . The poly(alkyleneoxide) according to claim 1 , comprising an a N,N-bis(trimethylsilyl)amine terminus and an ω-vinylbenzyl terminus.
10 . A copolymer of the poly(alkyleneoxide) according to claim 1 with an unsaturated monomer.
11 . A composition formed by the hydrosilylation of the poly(alkyleneoxide) according to claim 1 with a siloxane.
12 . An amide reaction product of a composition according to claim 11 with an acid chloride.
13 . A substituted urea product of a composition according to claim 1 with an isocyanate.
14 . The reaction product according to claim 12 , wherein the amide is an acrylamide, methacrylamide, or alkylamide functional macromer.
15 . A method of producing a heterofunctional poly(alkyleneoxide) according to claim 1 , wherein the first polymer terminus comprises a protected aminoalkyl functionality, the method comprising polymerizing an alkylene oxide with a metal hexaalkyldisilazane to form a polymer and reacting the polymer with an unsaturated halide.
16 . A method of producing a heterofunctional poly(alkyleneoxide) according to claim 1 , wherein the first polymer terminus comprises an unprotected aminoalkyl functionality, the method comprising polymerizing an alkylene oxide with a metal hexaalkyldisilazane to form a polymer, reacting the polymer with an unsaturated halide to yield a poly(alkyleneoxide) having a protected aminoalkyl terminus, and adding water or an alcohol to deblock the protecting group.
17 . A composition formed by the hydrosilylation of a poly(alkyleneoxide) according to claim 1 with a silane.
18 . The poly(alkyleneoxide) according to claim 1 , wherein the derivatized aminoalkyl functionality is an amide or N-substituted urea.
19 . The poly(alkyleneoxide) according to claim 1 , wherein the poly(alkyleneoxide) is α-bis(trimethylsilylaminoethyl)-ω-allyl terminated polyethylene oxide.
20 . The poly(alkyleneoxide) according to claim 1 , wherein the poly(alkyleneoxide) is α-bis(trimethylsilylaminoethyl)-ω-vinylbenzyl terminated polyethylene oxide.
21 . The poly(alkyleneoxide) according to claim 1 , wherein the poly(alkyleneoxide) is α-aminoalkyl-ω-allyl terminated polyethylene oxide.
22 . The poly(alkyleneoxide) according to claim 1 , wherein the poly(alkyleneoxide) is α-bis(trimethylsilylamino)-ω-vinylbenzyl terminated polyethylene oxide.
23 . The poly(alkyleneoxide) according to claim 1 , wherein the poly(alkyleneoxide) is α-bis(trimethylsilylaminoalkyl)-ω-allyl terminated polyethylene oxide.
24 . The poly(alkyleneoxide) according to claim 1 , wherein the poly(alkyleneoxide) is α-(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane) terminated polyethylene oxide.
25 . The poly(alkyleneoxide) according to claim 1 , wherein the poly(alkyleneoxide) is bis(methylphenylvinylsilyl)-protected-α-amino-ω-allyl terminated polyethylene oxide.
26 . The poly(alkyleneoxide) according to claim 1 , wherein the poly(alkyleneoxide) is α-amino-ω-allyl terminated polyethylene oxide.
27 . The poly(alkyleneoxide) according to claim 1 , wherein the poly(alkyleneoxide) is bis(ethyldimethylsilyl)-protected-α-amino-ω-allyl terminated polyethylene oxide.
28 . The poly(alkyleneoxide) according to claim 1 , wherein the poly(alkyleneoxide) is bis(trimethylsilyl)-protected-α-amino-ω-allyl terminated polyethylene oxide.
29 . The poly(alkyleneoxide) according to claim 1 , wherein the poly(alkyleneoxide) is α-dodecanoylamide-ω-allyl terminated polyethylene oxide.
30 . The composition according to claim 17 , wherein the composition is α-dodecanoylamide-ω-(triethoxysilyl)propyl terminated polyethylene oxide.
31 . The composition according to claim 17 , wherein the composition is α-amino-ω-(triethoxysilyl)propyl-terminated polyethylene oxide.
32 . The composition according to claim 11 , wherein the composition is 1-butyl-9-aminoethoxy(polyethyleneoxy)propyl decamethylpentasiloxane.
33 . The composition according to claim 11 , wherein the composition is 1-butyl-n-methacrylamidoethoxy(polyethyleneoxy)propyl decamethylpentasiloxane.