Premium
Hydroxymethylation and polycondensation reactions in urea–formaldehyde resin synthesis
Author(s) -
Christjanson Peep,
Pehk Tõnis,
Siimer Kadri
Publication year - 2006
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.23782
Subject(s) - condensation polymer , methylene , hydroxymethyl , formaldehyde , urea formaldehyde , catalysis , ether , polymer chemistry , aqueous solution , chemistry , urea , condensation reaction , organic chemistry , nuclear chemistry , adhesive , layer (electronics)
Formaldehyde–urea (F/U) reaction products with molar ratios of 1.8, 2.1, and 2.4 were synthesized at pH 8.3, and the last one also at pH 4.5 using 45% formaldehyde aqueous solution. For obtaining the resin, the synthesis of F/U 2.1 was continued by acid‐catalyzed condensation at pH 4.5 and posttreatment with second part of U (F/U 1.05/1) at 70°C and pH 8.3. The products were analyzed using 13 C‐NMR spectrometry. Higher excess of F increases the dihydroxymethyl content on account of smaller dimethylene ether content. Certain 13 C chemical shifts in carbonyl and methylene region of spectra were assigned to trishydroxymethylurea, being the main trisubstituted urea compound in hydroxymethylated product. Acid catalyst promotes the formation of methylene groups by polycondensation of hydroxymethyl groups, against the background of similar content of dimethylene ethers in both catalytic conditions. The ratio of linear/branched chains is emphasized in characterizing the resin structure. Higher hydroxymethyl content in acid‐catalyzed polycondensation is an advantage of three‐step synthesis technology. The amount of binding methylene and dimethylene ether groups linked only to secondary amino groups can be increased by transhydroxymethylation with subsequent polycondensation in posttreatment with U in suitable reaction conditions. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 100: 1673–1680, 2006