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J. Lubczak, W. Bukowski, D. Nicpoń

Addition of oxiranes to hydroxymethyl derivatives of melamine. Part VI. Preparation of s-triazine ring containing polyetherols by the reaction of N ,N ,N ',N ',N " -pentakia (hyd –roxymethyl)melamine with propylene oxide in aqueous solutions

Polimery 1998, No 6, 358

DOI: dx.doi.org/10.14314/polimery.1998.358


Propylene oxide (PO) was added to N,N,N',N',N"-pentakis(hydroxymethyl) melamine (PHMM) over triethylamine as catalyst. Disadvantageous side reactions of PO with water yield 1,2-propanediol and consecutive addition products, e.g ., 4-oxaheptane-2,6-diol, 2-methyl-3-oxahexane-1,5-diol, and 5-methyl-4,7-dioxadecane-2,9-diol, as well as formaldehyde that dissociated from N-hydroxymethyl groups; and they also included partial condensation of hydroxymethyl and amine groups. Classical analysis (gravimetry, determination of CH2O ) and instrumental methods (1H-NMR, GC) were used to determine the functional groups in the reaction products and the percentage of by-products (Tables 3, 4). Under suitably selected reaction conditions (pressure reactor, 50°C, 11 h, 400 cc H2O/mol PHMM, PO:PHMM = 15:1 by moles), the content of by-products was reduced from 50 to 20% of the final product weight. The s-triazine polyetherol thus synthesized lent itself to prepare polyurethane foams endowed with thermal resistance as good as that of the PUR foams obtained from s-triazine polyetherols prepared by other well-known methods.

Keywords: synthesis of s-triazine polyetherol in aqueous solution, mechanizm of reaction of N,N,N',N',N"-pentakis(hydroxymethyl)melamine with propylene oxide, 1H-NMR and GC analyses of reaction products, control of byproducts content

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