Polyols, phosphorus and nitrogen, a process for their preparation and their applications

摘要

1,183,471. Phosphorus - containing polyols. UGINE KUHLMANN S.A. 13 Feb., 1967 [14 Feb., 1966; 7 Nov., 1966], No. 6802/67. Heading C2C. [Also in Divisions C3, C4 and C5] The invention comprises phosphorus-containing polyols of the general formula wherein R 1 and R 2 which may be the same or different are alkyl, cycloalkyl, alkaryl, aryl, aralkyl or hydroxypolyalkoxyalkyl groups, all of which may be substituted, or are alkane phosphonic ester groups of the general formula in which R 3 and R 4 which may be the same or different are hydrogen atoms or monovalent organic radicals, Y is an alkylene group of the formula -CH(R)-CH 2 - in which R is H or an alkyl or haloalkyl group and may be different in each of the several Y groups and n is from 1 to 10. The substituents on the R 1 and/or R 2 groups may be one or more halogen atoms or one or more of the groups of the formula wherein the symbols are as defined above. The products may be obtained by reacting an alkylene oxide of the formula or a mixture of such alkylene oxides with an aminoalkane phosphonic acid of the general formula in which the symbols are as defined above except that R 1 and R 2 may additionally be hydrogen atoms. The oxyalkylation may be effected without solvent in an autoclave (if desired in the presence of some of the polyol products) or it may be carried out in the presence of a solvent or diluent and is most preferably effected at 50-130‹ C. The oxyalkylation may be completed by the use of a condensation catalyst such as BF 3 or its complexes, e.g. its ether complex. The products are useful in the production of flame-resistant polyurethanes and may be incorporated in heat transfer fluids, hydraulic fluids or lubricants. The aminoalkane phosphonic acids of Formula II may be obtained (a) by condensing together preferably in aqueous medium and in the presence of halide ions, (i) orthophosphorous acid or an ester thereof, (ii) an aldehyde or ketone, and (iii) ammonia or a primary or secondary amine or polyamine, the phosphonic acid ester produced in the case when a phosphorous acid ester is used being subsequently hydrolysed, or (b) by condensing together in aqueous medium: (i) PCl 3 , (ii) an aldehyde or ketone, and (iii) ammonia or a primary or secondary amine and examples are given for the production of amino - tri-(methane phosphonic acid).