Thermally re-mendable cross-linked polymers
View Patent ↗Thermally re-mendable cross-linked polymeric materials that can be repeatedly mended or repaired by simple thermal treatment. The polymeric materials are made by polymerizing furan monomers and maleimide monomers via the Diels-Alder (DA) reaction wherein the furan monomers have at least three furan moieties and the maleimide monomers have at least three maleimide moieties. The intermonomer linkages that form between the furan and maleimide monomers are thermally reversible and do not require the addition of catalysts, additional monomer or special surface treatments.
1. A composition of matter that is made by a process comprising the steps of:
mixing furan monomers with maleimide monomers to form a pre-polymer mixture wherein said furan monomers comprise at least four furan moieties and said maleimide monomers comprise at least three maleimide moieties; and
curing said pre-polymer mixture for a sufficient time and at a sufficient temperature to form thermally reversible covalent bonds between said furan moieties and said maleimide moieties to thereby provide said composition of matter.
2. A composition of matter according to claim 1 wherein said maleimide monomers comprise at least four maleimide moieties.
3. A composition of matter according to claim 1 or 2 wherein said furan monomers are selected from the group consisting of monomers having the formula
where R 1 is a straight or branched oxygen, nitrogen or sulfur containing carbon compound having from 2 to 20 carbon atoms;
where R F is
4. A composition of matter according to claim 1 wherein said maleimide monomers are selected from the group of monomers having the formula
where R 2 is C or N, R 3 is a straight or branched carbon compound having from 2 to 20 carbon atoms and which may or may not contain oxygen or other heteroatoms and where X is from 3 to 6;
where R M is
5. A composition of matter according to claim 3 wherein said maleimide monomers are selected from the group consisting of monomers having the formula
where R 2 is C or N, R 3 is a straight or branched carbon compound having from 2 to 20 carbon atoms and which may or may not contain oxygen or other heretoatoms and where X is from 3 to 6;
where R M is
6. A composition of matter according to claim 5 wherein said furan monomers have the formula
and said maleimide monomers have the formula
7. A method for making a composition of matter comprising the steps of:
mixing furan monomers with maleimide monomers to form a pre-polymer mixture wherein said furan monomers comprise at least four furan moieties and said maleimide monomers comprise at least three maleimide moieties and wherein said furan moieties are capable of forming thermally reversible covalent bonds with said maleimide moieties; and
curing said pre-polymer mixture for a sufficient time and at a sufficient temperature to form thermally reversible covalent bonds between said furan moieties and said maleimide moieties to thereby provide said conposition of matter.
8. A method for making a composition of matter according to claim 7 wherein said maleimide monomers comprise at least four maleimide moieties;
9. A method for making a composition of matter according to claim 7 or 8 wherein said furan monomers are selected from the group consisting of monomers having the formula
where R 1 is a straight or branched oxygen, nitrogen or sulfur containing carbon compound having from 2 to 20 carbon atoms;
where R F is
10. A method for making a composition of matter according to claim 7 wherein said maleimide monomers are selected from the group consisting of monomer having the formula
where R 2 is C or N, R 3 is a straight or branched carbon compound having from 2 to 20 carbon atoms and which may or may not contain oxygen or other heteroatoms and where X is from 3 to 6;
where R M is
11. A method for making a composition of matter according to claim 9 wherein said maleimide monomers are selected from the group consisting of monomers having the formula
where R 2 is C or N, R 3 is a straight or branched carbon compound having from 2 to 20 carbon atoms and which may or may not contain oxygen or other heteroatoms and where X is from 3 to 6;
where R M is
12. A method for making a composition of matter according to claim 11 wherein said furan monomers have the formula
and said maleimide monomers have the formula