GB1055306A - A process for the preparation of substantially linear polyaddition products containing repeating urea groups - Google Patents

Abstract

Diamine-N-carboxylic acids and diamine-N-sulphinic acids are prepared by reacting diamines or their solutions in polar organic solvents with CO2 or SO2 respectively. It is believed that these acids are N-mono-substituted acids or N,N1-di-substituted acids or a mixture of both. Diamines specified are: ethylene diamine, 1, 2 and 1,3-propylene diamine, 1,4-butylene diamine, 1,6-hexane diamine, decane 1,10-diamine, 2 - methyl - hexane 1: 6-diamine, 3-methhexane 1: 6-diamine, cyclohexane 1,3- or NN1 dimethyl-ethylene diamine, 1,4-N,N1-dimethylhexane diamine, piperazine, 2,5-dimethylpiperazine, xylylene diamines, g ,g 1-diaminopropylether, 1,4-phenylene bis-(p-amino-propylether), g ,g 1 - diaminopropyl methylamine. Examples describe the reaction of (1) CO2 with ethylene diamine and of SO2 with ethylene diamine, (2) CO2 with cyclohexane 1,4-diamine, (3) CO2 with piperazine hexahydrate, (4) CO2 with g : g 1-diaminopropylmethylamine, (7) CO2 with hydrazine hydrate and 1,6-hexane diamine, (8) CO2 with carbodihydrazide and bis-(3-amino-propyl)-methyl amine.ALSO:A process for the production of linear polyureas containing groups of the formula <FORM:1055306/C3/1> (in which R is alkylene, cycloalkylene or aralkylene which may be interrupted by hetero atoms; and R1 is a hydrogen atom or is a hydrocarbon radical which together with R forms a closed ring) which comprises reacting an isocyanate-modified dihydroxyl compound containing terminal -NCO groups (and having a M.W. of at least 500 before modification with the diisocyanate), at -20 DEG C. to +60 DEG C. with a diamine -N- carboxylic acid and/or diamine -N- sulphinic acid suspended or dissolved in a polar solvent. The dihydroxyl compound may be a polyester, polyester amide, polyester ether, polyether, polycarbonate, polythioether or polyacetal. Conventional diisocyanates are listed. The reaction between the dihydroxyl compound and the diisocyanate may be performed in the melt or in solution in an organic solvent. The N-sulphinic acid or N-carboxylic acid may be obtained by reaction of SO2 or CO2 with an organic diamine. In a typical Example (5) a polyester derived from adipic acid, hexane-1,6-diol and 2,2-dimethylpropane-1,3-diol was reacted with diphenylmethane 4,41-diisocyanate in chlorobenzene and added to a suspension of the adduct of g ,g 1-di-(amino-propyl) methylamine in dimethylformamide and the product cast on to a glass plate.