ethylene terephthalate).pdf

Tertiary Alkanolamines as Solvolytic Agents for Poly(ethylene terephthalate). Evaluation of the Products as Epoxy Resin Hardeners Tadeusz Spychaj,* Ryszard Pilawka, Stanis?awa Spychaj, and Artur Bartkowiak ? Polymer Institute, Technical University of Szczecin, ul. Pulaskiego 10, 70 - 322 Szczecin, Poland Tertiary alkanolamines, i.e., N-methyldiethanolamine, N-ethyldiethanolamine, N-isopropyl- diethanolamine, N-(n-butyl)diethanolamine, N-cyclohexyldiethanolamine, N-isopropanoldietha- nolamine, triethanolamine, triisopropanolamine, N,N′-bis(2-hydroxyethyl)piperazine, N,N,N′,N′- tetra(2-hydroxyethyl)ethylenediamine, and N,N,N′,N′-tetra(2-hydroxyethyl)propylene 1,3-diamine were applied as poly(ethylene terephthalate) (PET) solvolytic agents. Solvolysis (i.e., aminogly- colysis) of PET was performed at 190-220 °C for 90-240 min. PET aminoglycolysates were characterized via hydroxyl number and viscosity measurements, whereas some products were characterized by SEC, HPLC, and FTIR and 1 H NMR spectroscopies. Selected products were tested as epoxy resin hardeners for elevated-temperature curing. Rheometric properties, as well as heats of the cross-linking reactions in the systems containing liquid bisphenol A based epoxy resin and PET aminoglycolysates (with a broad ratio of the latter) were investigated and compared. The accessibility of nitrogen atoms expressed by the substituent molar volume is a key factor determining the chemical activity of PET aminoglycolysates toward epoxy resin polymerization. FTIR measurements revealed that the transesterification reaction of bisesters of terephthalic acid and tertiary alkanolamines with bisphenol A diglycidyl ether derivatives bearing secondary OH groups plays an important role in the formation of the epoxy resin network. Introduction The recycling of waste poly(ethylene terephthalate) (PET) can be carried out in many ways. 1-3 Among the recycling methods, chemical recycling is of great interest because PET is vulnerable to solvo