Patent GB-842420-A (GB)
Title: Process for the production of compounds containing at least one isocyanuric acid ring
Filed: 1956-12-18
Abstract: A process for the production of compounds containing at least one isocyanuric acid ring comprises heating a monomeric organic mono-isocyanate and/or a polyisocyanate in the presence of a tertiary amine and a carbamic acid ester which is mono-substituted on the nitrogen atom, the tertiary amine being employed in an amount which contains from 0,0001% to 2% by weight of tertiary nitrogen, based on the weight of the compound containing the isocyanate group(s) and the carbamic acid ester in an amount of less than 0,3 mol. per isocyanate equivalent.  From organic mono-isocyanates products with only one isocyanuric acid ring are obtained.  Monomeric polyisocyanates give products with two or more isocyanuric acid rings and having a molecular weight of up to 100,000.  A list of aliphatic, cycloaliphatic, araliphatic and aromatic mono-di- and trisocyanates is given.  As substituents some contain alkyl, nitro, chloro and methoxy groups.  Tertiary amines suitable are dimethyl aniline, hexahydrodimethyl aniline, alkyl morpholines, permethylated diethylene triamine or trithylene tetramine, dialkyl piperazines, urethanes consisting of the reaction product of N,N- dialkyl aminoethanol with phenyl or cyclohexyl isocyanate or of N-alkyl ethanolamines and phenyl or cyclohexyl isocyanate, N,N-dialkylethanolamines, N-alkyl ethanolamines and trialkylamines. The carbamic acid esters may be added as such or be formed in situ in the reaction mixture from mono- or polyisocyanates and aliphatic araliphatic, hydro-aromatic or aromatic mono- or polyhydroxy compounds which can contain hetero atoms or double or triple bonds. The reaction is stopped by adding compounds with acid reaction or which form quaternary compounds with the tertiary amine.  Examples of the preparation of high molecular weight products are given in which the starting compounds are hexamethylene diisocyanate, toluylene diisocyanate and naphthalene -1,5-diisocyanate.ALSO:A process for the production of compounds containing at least one isocyanuric acid ring comprises heating a monomeric organic monoisocyanate and/or a polyisocyanate in the presence of a tertiary amine and a carbamic acid ester which is mono-substituted on the nitrogen atom, the tertiary amine being employed in an amount which contains from 0,001% to 2% by weight of tertiary nitrogen based on the weight of the compound containing the isocyanate group(s) and the carbamic acid ester in an amount of less than 0,3 mol. per isocyanate equivalent. From organic monoisocyanates products with only one isocyanuric acid ring are obtained.  Monomeric polyisocyanates give products with two or more isocyanuric rings and having a molecular weight of up to 100,000.  A list of aliphatic, cycloaliphatic, araliphatic and aromatic mono-, di- and triisocyanates is given.  As substitutents some contain alkyl, nitro, chloro and methoxy groups.  Tertiary amines suitable are dimethyl aniline, hexahydrodimethylaniline, alkyl morpholines, permethylated diethylene triamine or triethylene tetramine, dialkyl piperazines, urethanes consisting of the reaction products of N,N-dialkylaminoethanol with phenyl or cyclohexyl isocyanate or of N-alkyl ethanolamines and phenyl or cyclohexyl isocyanate, N,N-dialkylethanolamines, N-alkylethanolamines and trialkylamines.  The carbamic esters may be added as such or be formed in situ in the reaction mixture, from mono- or polyisocyanates and aliphatic, araliphatic, hydroaromatic or aromatic mono- or polyhydroxy compounds which can contain hetero atoms or double or triple bonds.  The reaction is stopped by adding compounds with acid reaction or which form quaternary compounds with the tertiary amine. Examples employ as starting materials phenyl, tolyl, p-ethoxyphenyl, p-chlorophenyl and p-nitrophenyl isocyanates, and hexamethylene, toluylene and naphthalane -1,5- diisocyanates.