Closed-loop thermoset polymers with improved processibility and tunable degradation
The disclosed technology provides a vitrimeric poly(diketoenamine) network comprising: a plurality of multifunctional triketone dimers; a plurality of multifunctional amine species containing primary or secondary amine groups, but no tertiary amine groups; and optionally, one or more amine-reactive groups. The disclosed technology also provides a method of making a vitrimeric polymer network, comprising: obtaining multifunctional triketone dimers; obtaining a multifunctional imine compound, with imine groups blocking amine groups; mixing the multifunctional triketone dimers with the multifunctional imine compound, thereby forming a polymer precursor mixture; applying the polymer precursor mixture onto a substrate; and allowing the multifunctional imine compound to undergo hydrolysis with water, unblocking the amine functional groups and generating a multifunctional amine compound. The multifunctional amine compound reacts with the multifunctional triketone dimers to form a vitrimeric polymer network. The vitrimeric polymer network may be depolymerized back to monomers, which may be repolymerized in a closed-loop system.
1. A vitrimeric-polymer packaged composition comprising:
(a) a multifunctional triketone dimer;
(b) a multifunctional imine compound, wherein imine functional groups block amine functional groups;
(c) optionally, an amine-reactive compound; and
(d) optionally, one or more additives or fillers.
2. The vitrimeric-polymer packaged composition of claim 1 , wherein all components are separated within a package.
3. The vitrimeric-polymer packaged composition of claim 1 , wherein all components are blended together within a package.
4. The vitrimeric-polymer packaged composition of claim 1 , wherein said multifunctional triketone dimer has the structure:
wherein R contains from 1 to 50 carbon atoms;
wherein R is a linear hydrocarbon group, a branched hydrocarbon group, a cyclic hydrocarbon group, or a combination thereof; and
wherein R contains carbon-carbon single bonds, carbon-carbon aromatic bonds, carbon-carbon double bonds, carbon-carbon triple bonds, or a combination thereof.
5. The vitrimeric-polymer packaged composition of claim 4 , wherein said R is a linear hydrocarbon group, and wherein R contains from 4 to 12 carbon atoms.
6. The vitrimeric-polymer packaged composition of claim 4 , wherein said R is selected from benzene, naphthalene, or anthracene.
7. The vitrimeric-polymer packaged composition of claim 4 , wherein said R is a branched hydrocarbon group.
8. The vitrimeric-polymer packaged composition of claim 1 , wherein said multifunctional imine compound does not contain a tertiary amine group.
9. The vitrimeric-polymer packaged composition of claim 1 , wherein said imine functional group blocks amine functional groups contained in the following structure:
wherein R contains from 1 to 20 carbon atoms;
wherein R is a linear hydrocarbon group, a branched hydrocarbon group, a cyclic hydrocarbon group, or a combination thereof, and
wherein R contains carbon-carbon single bonds, carbon-carbon aromatic bonds, carbon-carbon double bonds, carbon-carbon triple bonds, or a combination thereof.
10. The vitrimeric-polymer packaged composition of claim 9 , wherein said multifunctional imine compound is MIBK-blocked 4-(aminomethyl)octane-1,8-diamine: