Industrial & Engineering Chemistry Research, Vol.43, No.4, 862-874, 2004
Tertiary alkanolamines as solvolytic agents for poly(ethylene terephthalate). Evaluation of the products as epoxy resin hardeners
Tertiary alkanolamines, i.e., N-methyldiethanolamine, N-ethyldiethanolamine, N-isopropyl-diethanolamine, N-(n-butyl)diethanolamine, N-cyclohexyldiethanolamine, N-isopropanoldiethanolamine, 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., aminoglycolysis) of PET was performed at 190-220degreesC 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 H-1 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 tereplithalic 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.