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    ZHOU Yawei, LI Ping, HAN Jinshi, WEI Wei, LI Xiaojie, LIU Xiaoya. Preparation of Detachable UV Curing Adhesive Based on Oxime-Carbamate Bond[J]. Journal of Functional Polymers, 2022, 35(3): 252-260. doi: 10.14133/j.cnki.1008-9357.20210908001
    Citation: ZHOU Yawei, LI Ping, HAN Jinshi, WEI Wei, LI Xiaojie, LIU Xiaoya. Preparation of Detachable UV Curing Adhesive Based on Oxime-Carbamate Bond[J]. Journal of Functional Polymers, 2022, 35(3): 252-260. doi: 10.14133/j.cnki.1008-9357.20210908001

    Preparation of Detachable UV Curing Adhesive Based on Oxime-Carbamate Bond

    • Polyurethane acrylate prepolymer was synthesized from polytetrahydrofuran ether glycol (PTMEG), isoflurone diisocyanate (IPDI), dimethylglyoxime (DMG) and hydroxyethyl acrylate (HEA). The prepolymer was mixed with photoinitiator 2-hydroxy-2-methylpropiophenone (HMPP) and active diluent HEA to prepare ultraviolet (UV) curing adhesive. The structure of polyurethane acrylate prepolymer was characterized by Fourier-transform infrared (FT-IR) spectroscopy and 1H-nuclear magnetic resonance (1H-NMR) spectroscopy. The double bond conversion and gel content of the adhesive under UV irradiation were investigated. The effects of contents of HEA and DMG on the tensile shear strength of the adhesive were also investigated, using toughened glass as a bonding substrate. In addition, the thermo-reversible behavior of oxime-carbamate bond was studied by in-situ variable temperature infrared spectroscopy, self-healing experiment and thermogravimetric analysis. The results show that when the mass fraction of HEA is 30% of UV curing adhesive and the molar ratio of DMG to PTMEG is 1.5∶1, the tensile shear strength of the adhesive can reach 3.72 MPa after UV irradiation for 3 min. The in-situ variable temperature infrared spectroscopy shows that the oxime-carbamate groups of the adhesive can be thermally decomposed to produce ―NCO groups above 120 °C. The self-healing experiments reveal that the scratches on the surface of the adhesive can disappear and be healed after heat treatment at 150 ℃ for 30 min, owing to enhancement of chain segmental motion by thermo-reversibility of oxime-carbamate bond. The TGA curves of the adhesive display a thermal decomposition stage at 160—240 ℃, belonging to the decomposition of oxime carbamate. The thermal reversibility of oxime-carbamate bond gives the adhesive good thermal detachability. The adhesive can be separated from the substrate by heating at 150 ℃ for 3 min. Therefore, the adhesive demonstrates a promising prospect for application in the fields requiring UV rapid curing and thermal disassembly performance.
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