Patent GB-1083409-A (GB)
Title: Heterocyclic phosphorus-containing compounds
IPC: C08G18/79
Filed: 1965-06-30
Abstract: A polymeric material contains as additive a compound of the formula <FORM:1083409/C3/1> wherein CnH2n represents an alkylene group containing from 1 to 12 carbon atoms, at least one and not more than three adjacent carbon atoms in the alkylene radical forming a chain one end of which is attached to Y and the other end of which is attached to N, thereby completing the heterocyclic ring; R1 is a hydrocarbenyl radical containing from 1 to 18 carbon atoms or a halo-, nitro-, C1- 8-alkoxy-, C1- 8-alkyl-mercapto- or cyano-substituted hydrocarbyl radical containing from 1 to 18 carbon atoms; R11 is hydrogen, a hydrocarbyl radical containing from 1 to 18 carbon atoms or the radical -CONHR111, wherein R111 represents a hydrocarbyl radical containing from 1 to 18 carbon atoms; and Y is -O- or -NR11- wherein R11 has the significance defined above and wherein R11 may be the same as or different from R11 in the group -NR11-.  The additives may be used to improve the fire-retarding properties of polyurethane foams by adding them to the mixes used in the production of such foams or, in the cases of those compounds in which R11 is hydrogen and Y is -NH-, by incorporating them into the polyurethanes by adding them to the reaction mixture of polyisocyanate and polyol from which the polyurethanes are prepared. Also, the additives are useful for the stabilization of polymeric materials, e.g. polyvinyl chloride and copolymers thereof, towards ultra-violet radiation. For this purpose they may be blended into the mixture containing the polyvinyl compounds, plasticizer and other conventional adjuvants.ALSO:Novel compounds of the formula <FORM:1083409/C2/1> wherein CnH2n is an alkylene group containing from 1 to 12 carbon atoms, at least one and not more than 3 adjacent carbon atoms in the alkylene radical forming a chain one end of which is attached to Y and the other end of which is attached to N thereby completing the heterocyclic ring; R1 is a hydrocarbyl radical containing from 1 to 18 carbon atoms or a halo-, nitro-, C1- 8-alkoxy-, C1- 8-alkylmercapto- or cyano-substituted hydrocarbyl containing from 1 to 18 carbon atoms; R11 is hydrogen, a hydrocarbyl radical containing from 1 to 18 carbon atoms or the radical -CONHR111 wherein R111 represents a hydrocarbyl radical containing from 1 to 18 carbon atoms; and Y is -O- or -NR11- wherein R11 has the significance defined above and wherein R11 may be the same or different from R11 in the group -NR11-, are prepared by reacting diamines or alkanol amines of the formula HYCnH2nNHR11 with phosphonic dihalides of the formula R1POHal2, wherein Hal represent s halogen, in the presence of an acid accept t and an inert organic solvent at reaction temperatures up to 100 DEG  C.  The said acceptor may be a tertiary amine, e.g. pyridine, a tri-alkylamine, an N-alkyl piperidine, an N-alkylmorpholine or an N-dialkylaniline, or an inorganic base, e.g. an alkali-metal carbonate or hydroxide, and specified inert solvents are hydrocarbons and halogenated hydrocarbons. The compounds are useful as fire retardants, e.g. by addition to foam mixers used in the production of polyurethane foams (see Division C3), and as stabilizers of polymeric materials (see Division C3).