Epoxy-(meth)acrylate monomers and polymers and methods of making and using the same
AssigneesRowan University, The United States of America as represented by the Secretary of the Army
InventorsALEXANDER W. BASSETT, JOSEPH F. STANZIONE, III, JOHN J. LA SCALA
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Abstract
The present invention relates to the unexpected discovery of novel monomer compounds capable of crosslinking interpenetrating polymer networks (IPNs). In certain embodiments, the monomer compounds of the invention each comprise at least one methacrylate functionality capable of forming polymeric bonds with other methacrylate and vinyl functionalities, and at least one epoxide functionality capable of forming polymeric bonds with epoxide functionalities, amine functionalities, and/or reactive oxygen species.
Claims20
A monomer of Formula (I), Formula (II), or Formula (III):
- wherein:
- R1 is
- Reis
- each instance of R3 is independently selected from the group consisting of H, optionally substituted C1-C6 alkyl, and optionally substituted C1-C6 alkoxy;
- each instance of R4 is independently selected from the group consisting of H and CH3;
- each instance of L is independently selected from the group consisting of a bond, C1-C10 alkylene and C1-C10 alkenylene;
- and
- m is 1, 2, 3, 4 or 5, and
- n is 1, 2, 3, 4 or 5, such that (m+n) is equal to or less than 6;
- and
- one of R5 and R6 is
- and the other is
A composition comprising an interpenetrating polymer network of Formula (IV), Formula (VA), Formula (VB) or Formula (VI):
- wherein:
- each instance of R3 is independently selected from the group consisting of H, optionally substituted C1-C6 alkyl, and optionally substituted C1-C6 alkoxy;
- each instance of R4 is independently selected from the group consisting of H and CH3;
- each instance of L is independently selected from the group consisting of a bond, C1-C10 alkylene and C1-C10 alkenylene;
- and
- m is 1, 2, 3, 4 or 5;
- n is 1, 2, 3, 4 or 5, such that (m+n) is equal to or less than 6;
- X1 is a first polymer comprising linkages selected from the group consisting of epoxy linkages, epoxy-amine linkages, epoxy-(meth)acrylate linkages, and any combinations thereof;
- and
- X2 and X2′ are independently a second polymer comprising linkages selected from the group consisting of (meth)acrylate linkages, vinyl linkages, and allyl linkages, and any combination thereof.
A kit comprising:
- a first composition comprising at least one monomer selected from the group consisting of a monomer of Formula (IA), a monomer of Formula (II) and a monomer of Formula (III):
- wherein:
- R1 is
- Reis
- each instance of R3 is independently selected from the group consisting of H, optionally substituted C1-C6 alkyl, and optionally substituted C1-C6 alkoxy;
- each instance of R4 is independently selected from the group consisting of H and CH3;
- each instance of L is independently selected from the group consisting of a bond, C1-C10 alkylene and C1-C10 alkenylene;
- and
- m is 1, 2, 3, 4 or 5, and
- n is 1, 2, 3, 4 or 5, such that (m+n) is equal to or less than 6;
- and
- one of R5 and R6 is and the other is
- a second composition comprising at least one monomer capable of forming with the at least one monomer in the first composition a first polymer comprising linkages selected from the group consisting of epoxy linkages, epoxy-amine linkages and any combinations thereof;
- a third composition comprising at least one monomer capable of forming with the at least one monomer in the first composition a second polymer comprising linkages selected from the group consisting of methacrylate linkages, vinyl linkages, any combination thereof;
- and
- instructional material for forming an interpenetrating polymer network using the compositions of the kit.
Dependencies are inferred from the claim text.