Click Synthesis of Triazole Polymers Based on Lignin-Derived Metabolic Intermediate and Their Strong Adhesive Properties to Cu Plate

Abstract

2-Pyrone-4,6-dicarboxylic acid (PDC) is a chemically stable metabolic intermediate of lignin that can be produced on a large scale by transforming bacteria. Novel biomass-based polymers based on PDC were synthesized by Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) and fully characterized by nuclear magnetic resonance, infrared spectroscopies, thermal analysis, and tensile lap shear strength measurements. The onset decomposition temperatures of these PDC-based polymers were all above 200 °C. In addition, the PDC-based polymers exhibited strong adhesive properties to various metal plates, with the highest adhesion to a copper plate of 5.73 MPa. Interestingly, this result was in contrast to our previous findings that PDC-based polymers weakly adhere to copper. Furthermore, when bifunctional alkyne and azide monomers were polymerized in situ under hot-press conditions for 1 h, the resulting PDC-based polymer displayed a similar adhesion to a copper plate of 4.18 MPa. The high affinity of the triazole ring to copper ions improved the adhesive ability and selectivity of the PDC-based polymers to copper while still maintaining the strong adhesive ability to other metals, which is conducive to enhancing the versatility of PDC-based polymers as adhesives.

Biodegradable and wood adhesive polyesters based on lignin-derived 2-pyrone-4,6-dicarboxylic acid

“…[11][12][13][14] In addition, various studies have shown that PDC-based polymers have strong adhesive properties to various metallic or non-metallic materials, making it essential to further develop their future as adhesives. [15][16][17][18] Adhesives have an extensive range of applications in furniture, packaging, electronics and construction, and a high number of wood adhesives are inevitably used in the production of wood composites, such as plywood, particle board, and bre board. [19][20][21][22][23] However, most of the wood adhesives used in the production of wood composites are aldehyde-based, such as urea-formaldehyde, phenol-formaldehyde, and melamineformaldehyde resins, [24][25][26] which inevitably release formaldehyde, a carcinogen that has a severe impact on human health during production and use.…”

“…11–14 In addition, various studies have shown that PDC-based polymers have strong adhesive properties to various metallic or non-metallic materials, making it essential to further develop their future as adhesives. 15–18…”

Ionic Conductive Organogels Based on Cellulose and Lignin-Derived Metabolic Intermediates

“…Additionally, unusual short packing can be formed between the PDC molecules due to the strong antiparallel dipolar interactions of the carbonyl moieties of the pyrone ring and the carboxylic acids. PDC is also a promising component of polymeric materials. − Isophthalic acid (IA), which is derived from petroleum and has a weaker acidity (p K a1 = 3.46, p K a2 = 4.46), was used as the control sample due to a chemical structure similar to that of PDC. The organogels could be obtained in 2 min by forming strong hydrogen bonds between cellulose and PDC or IA (Scheme ).…”