Acid-Cleavable Aromatic Polymers for the Fabrication of Closed-Loop Recyclable Plastics with High Mechanical Strength and Excellent Chemical Resistance.

Although closed-loop recycling of dynamic covalent bond-based plastics does not require catalysts, their mechanical strength and chemical stability remain a major concern. In this study, closed-loop recyclable poly(aryl imine) (PAI) plastics with high mechanical strength and excellent chemical resistance are fabricated by copolymerizing aromatic amines and aromatic aldehydes through dynamic imine bonds. The resulting PAI plastic with a tensile strength of 58.2 MPa exhibits excellent chemical resistance and mechanical stability in acidic and basic aqueous solutions and various organic solvents. The PAI plastics can be depolymerized in a mixed solvent of tetrahydrofuran (THF)/HCl aqueous solution through the dissociation of imine bonds, and the monomers can be facilely recovered with high purity and isolated yields due to the solubility difference between the aromatic amines and aromatic aldehydes in selective solvents. The efficient closed-loop recycling of the PAI plastic can also be realized through monomer conversion because the hydrolysis of the aromatic aldehydes generates aromatic amines. The recovered monomers can be used to re-fabricate original PAI plastics. This PAI plastic can be selectively recovered from complicated mixed polymer waste streams due to the mild depolymerization conditions of the PAI plastic and its high stability in most organic solvents.