Epoxy-(meth)acrylate monomers and polymers and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-11667669-B2
Application number	US-201916538989-A
Country	US
Kind code	B2
Filing date	Aug 13, 2019
Priority date	Aug 13, 2018
Publication date	Jun 6, 2023
Grant date	Jun 6, 2023

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.

First claim

What is claimed is:

1. A monomer selected from the group consisting of:
a compound of formula:

wherein each instance of R 3 is independently selected from the group consisting of H, optionally substituted C 1 -C 6 alkyl, and optionally substituted C 1 -C 6 alkoxy;
a compound of formula:

wherein each instance of R 3 is independently selected from the group consisting of H, optionally substituted C 1 -C 6 alkyl, and optionally substituted C 1 -C 6 alkoxy;

2. A composition comprising at least one monomer of claim 1 .

3. The composition of claim 2 , further comprising at least one polymerization initiator.

4. The composition of claim 3 , wherein the at least one polymerization initiator is at least one selected from the group consisting of photoinitiators, thermal initiators, and redox initiators, with or without an accelerator.

5. The composition of claim 2 , further comprising at least one additional compound comprising at least one selected from the group consisting of an epoxide functionality, a methacrylate functionality, a vinyl functionality, an acrylate functionality, an allylic functionality, a cyclic carbonate functionality, a thiol functionality, an amine functionality, an aniline functionality, an anhydride functionality, a carboxylic acid functionality, and an unsaturated polyester.

6. The composition of claim 5 , wherein the at least one additional compound is selected from the group consisting of bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisguaiacol diglycidyl ether, novolac epoxies, glycidyl ethers of hydrogenated bisphenols and epoxides, di(cyclohexane epoxidemethyl)ether, epoxy cyclohexyl methyl-epoxy cyclohexane carboxylate, 4,4′-diaminodicyclohexylmethane (PACM), diethylmethylbenzenediamine, Jeffamine, polyetheramines, amidoamines, aminopolyamide, diethyltriamine, triethylenetetramine, tetraethylenepentamine, diethylaminopropylamine, trimethylhexamethylenediamine, dipropyltriamine piperidine, N-aminopiperidine, menthanediamine, isophoronediamine, diaminodiphenylsulfone, methylene dianiline, oxydianiline, imidazole, dicyandiamide, ethylene glycol dimethacrylate (EGDMA), hexanediol dimethacrylate (HDDMA), methyl methacrylate (MMA), styrene, glycidyl methacrylate, vinyl esters of bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, glycidyl ethers of hydrogenated bisphenols, novalac epoxies, isobornyl acrylate, isosorbide (meth)acrylate, methacrylated lauric acid, lauryl (meth)acrylate, cyclohexyl methacrylate, furfuryl methacrylate, phthalic anhydride, hexahydrophthalic anhydride, nadic anhydride, nadic methyl anhydride, dodecenylsuccinic anhydride, maleic anhydride, tetrahydrophthalic anhydride, pyromellitic anhydride, trimellitic anhydride, benzophenonetetracraboxylic dianahydride, chlorendic anhydride, hexamethylene diisocyanate, isophorone diisocyanate, methylenediphenyl diisocyanate, and bisphenol A cyclic carbonate.

7. A composition comprising at least one monomer of claim 1 , further comprising:
at least one additional first monomer capable of forming with the at least one monomer a first polymer comprising linkages selected from the group consisting of epoxy linkages, epoxy-amine linkages, and any combinations thereof; and
at least one additional second monomer capable of forming with the at least one monomer a second polymer comprising linkages selected from the group consisting of acrylate linkages, methacrylate linkages, vinyl linkages, and any combinations thereof.

8. The composition of claim 2 , wherein the monomer is selected from the group consisting of:

9. The composition of claim 2 , wherein the monomer is selected from the group consisting of:

10. A kit comprising:
a first composition comprising at least one monomer selected from the group consisting of
a compound of formula:

wherein each instance of R 3 is independently selected from the group consisting of H, optionally substituted C 1 -C 6 alkyl, and optionally substituted C 1 -C 6 alkoxy;
a compound of formula:

wherein each instance of R 3 is independently selected from the group consisting of H, optionally substituted C 1 -C 6 alkyl, and optionally substituted C 1 -C 6 alkoxy;

a second composition comprising at least one first additional 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 second additional 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.

Assignees

• Univ Rowan
• Us Army

Inventors

• Bassett Alexander W
• Stanzione Iii Joseph F
• La Scala John J

Classifications

• C08F222/102

  of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate · CPC title

• C07J63/008

  Expansion of ring D by one atom, e.g. D homo steroids · CPC title

• C08F20/32

  containing epoxy radicals · CPC title

• C07D493/04

  Ortho-condensed systems · CPC title

• C07J53/002 Primary

  Carbocyclic rings fused · CPC title