Isocyanuric acid-modified cyclohexanone–formaldehyde resins for fire-retardant polyurethane

Abstract

Purpose

Cyclohexanone–formaldehyde resin (CFR) was in situ modified with isocyanuric acid (ICA) in the presence of hydrochloric acid or p-toluenesulfonic acid by condensation polymerization. The purpose of this study is to produce isocyanuric acid-modified ketonic resins that have higher melting and decomposition temperature, and to use the produced resin in the production of fire-retardant polyurethane.

Design/methodology/approach

Two methods were used for in situ preparation of ICA-modified CFR in the presence of an acid catalyst. Method I: cyclohexanone, paraformaldehyde and ICA were mixed, and then an acid catalyst was added to form the modified CFR. Method II: ICA and formalin were mixed to produce N, N, N-trihydroxymethyl isocyanurate, and then water was removed under vacuum. The produced N, N, N-trihydroxymethyl isocyanurate solution was mixed with cyclohexanone and paraformaldehyde, then an acid catalyst was slowly added to this mixture to obtain ICA-modified CFR.

Findings

CFR was prepared in the presence of an acid catalyst. The product, CFR, has a dark red colour. The resulting resins have similar physical properties with the resin prepared in the presence of a basic catalyst. The solubility of ICA-modified CFR is much different than CFR in organic solvents.

Research limitations/implications

This study focuses on obtaining an ICA-modified ketonic resin. Cyanuric acid has the form of an enolic structure under a basic condition; therefore, it cannot give a product with formaldehyde under basic conditions. The modification experiments were carried out in acidic conditions.

Practical implications

This study provides technical information for in situ modification of ketonic resin in the presence of acid catalysts. The resins may also promote the adhesive strength of the coating and provide corrosion inhibition on metal surfaces for a coating. The modified resins may also be used in the field of fire-retardant polyurethane applications.

Social implications

These resins may be used for the preparation of non-toxic fire-retardant polyurethane foam. Polyurethane containing ICA-modified resin may exhibit better fire-retardant performance because of the incorporation of ICA molecule into the polyurethane structure.

Originality/value

ICA-modified CFRs have been synthesized in the presence of an acid catalyst, and the ICA-modified resin was used to produce fire-retardant polyurethane.

Citation

Yivlik, Y., Kizilcan, N. and Akar, A. (2020), "Isocyanuric acid-modified cyclohexanone–formaldehyde resins for fire-retardant polyurethane", Pigment & Resin Technology, Vol. 49 No. 2, pp. 119-126. https://doi.org/10.1108/PRT-03-2019-0025