Ambient Cross-linking System Based on the Knoevenagel Condensation Reaction between Acetoacetylated Sucrose and Aromatic Dicarboxaldehydes

Zhiyuan Cao; Fei Gao; Jinze Zhao; Cong Lin; Jiang Zhong; Fengbiao Chen; Yangyang Zhu; Pingping Yi; Liang Shen

doi:10.1021/acsomega.9b03029

Ambient Cross-linking System Based on the Knoevenagel Condensation Reaction between Acetoacetylated Sucrose and Aromatic Dicarboxaldehydes

ACS Omega. 2019 Nov 15;4(24):20724-20731. doi: 10.1021/acsomega.9b03029. eCollection 2019 Dec 10.

Authors

Zhiyuan Cao¹, Fei Gao¹, Jinze Zhao¹, Cong Lin¹, Jiang Zhong¹, Fengbiao Chen¹, Yangyang Zhu¹, Pingping Yi¹, Liang Shen¹

Affiliation

¹ Jiangxi Engineering Laboratory of Waterborne Coating, School of Chemistry and Chemical Engineering, Jiangxi Science and Technology Normal University, Nanchang 330013, Jiangxi, P. R. China.

Abstract

An ambient cross-linking system based on the Knoevenagel condensation reaction between acetoacetylated sucrose and aromatic dicarboxaldehydes was demonstrated. In this study, we use a rheological instrument to measure the gel time to predict and elucidate the likely reaction mechanism of the system, and we prepare films based on the mechanistic results. Acetoacetylated sucrose and 4,4'-biphenyldicarboxaldehyde were used as raw materials, piperidine was used as the catalyst, and nonvolatile dimethyl sulfoxide (DMSO) was used as the solvent. After mixing 4,4'-biphenyldicarboxaldehyde and piperidine for 30 min, the acetoacetylated sucrose was added, thus producing the shortest gel time. Then, the gel was characterized by Fourier transform infrared spectroscopy. In addition, three films were prepared by this approach with different aromatic dicarboxaldehydes, and the properties of the coatings were characterized by differential scanning calorimeter, dynamic mechanical analysis thermogravimetric analysis, and swelling ratio. It was found that these films have high Young's modulus, high glass transition temperatures, high pencil hardnesses, and low swelling ratios.