Phosphonic acid derivatives as flameproofing agents

Claim 1

A flameproofed polymeric organic material other than cellulose containing, as a flameproofing agent, a compound of the formula ##STR65## in which each R', independently, is a radical --OR 1 ' (a') or ##STR66## or two moieties R' bound to the same phosphorus atom form a radical (c') ##STR67## and each of the other two moieties R', independently, is a radical (a') or (b'), or the other two moieties R' bound to the same phosphorus atom form a second radical (c'), independent from the first radical (c'), each of X 1 , x 2 , y and Z, independently, is oxygen or sulphur, n is zero or 1, each R 1 ', independently, is ethyl, unsubstituted or substituted by a halo substituent; (C 3-6 ) alkyl, unsubstituted or substituted by 1 to 3 halo substituents; (C 3-6 ) alkenyl, unsubstituted or substituted by 1 or 2 halo substituents; cyclohexyl; phenyl, unsubstituted or substituted by 1 to 3 chloro substituents, by a bromo substituent in the para-position or by 1 to 3 methyl substituents; or benzyl, unsubstituted or substituted by 1 to 3 chloro substituents or by a bromo substituent in the para-position; each R 2 ', independently, is (C 1-3 ) alkyl; or phenyl, unsubstituted or substituted by a chloro substituent, by a bromo substituent in the para-position or by a methyl substituent; each R 3 ', independently, is (C 1-3 ) alkyl or hydrogen; each R 4 ' and R 5 ', independently, is (C 1-4 ) alkyl; CH 2 Cl or CH 2 Br; or any R 4 ' and R 5 ', independently, together with the carbon atom to which they are bound, form a cyclohexylidene, cyclohexenylidene or 3,4-dibromocyclohexylidene ring; R 9 ' is (C 1-4 ) alkyl; cyclohexyl; benzyl or phenyl; R 10 ' is hydrogen; (C 1-4 ) alkyl; cyclohexyl; benzyl or phenyl; or R 9 ' and R 10 ', together with the nitrogen atom to which they are bound, form a piperidino or morpholino ring, with the provisos that: (i) when one or more of X 1 , X 2 and Y is oxygen, then Z can only be oxygen, (ii) when X 1 and Y are both oxygen, then each moiety R', independently, is a radical (b'), (iii) when Z is oxygen and n is zero, only one radical (c') can be present in the molecule, (iv) when X 1 or Y is oxygen, then R 2 ' is any radical (b') bound to that same phosphorus atom is other than alkyl, (v) when two radicals (b') are attached to a phosphorus atom, and X 1 or Y attached to that same phosphorus atom is sulphur, then both of the moieties R 2 ' in these radicals (b') are (C 1-3 ) alkyl, (vi) when one of the moieties R 2 ' and R 3 ' bound to the same nitrogen atom in a radical (b') is ethyl or propyl, the other must be ethyl or propyl, (vii) when n is 1, or when n is zero and R 2 ' in any radical (b') is (C 1-3 ) alkyl, any R 3 ', or R 3 ' in that same radical (b'), respectively, is other than hydrogen, and (viii) when each of X 1 and Y is oxygen, each of R 4 ' and R 5 ', independently, in any radical (c') is CH 2 Cl or CH 2 Br or both R 4 ' and R 5 ', together with the carbon atom to which they are bound form one of the rings indicated above.

Claim 8

A method of producing a flameproofed polymeric organic material, other than cellulose, comprising treating the polymeric organic material, directly or indirectly, with a flameproofing effective amount of a compound of the formula ##STR75## in which each R', independently, is a radical --OR 1 ' (a') or ##STR76## or two moieties R' bound to the same phosphorus atom form a radical (c') ##STR77## and each of the other two moieties R', independently, is a radical (a') or (b'), or the other two moieties R' bound to the same phosphorus atom form a second radical (c'), independent from the first radical (c'), each of X 1 , x 2 , y and Z, independently, is oxygen or sulphur, n is zero or 1, each R 1 ', independently, is ethyl, unsubstituted or substituted by a halo substituent; (C 3-6 ) alkyl, unsubstituted or substituted by 1 to 3 halo substituents; (C 3-6 ) alkenyl, unsubstituted or substituted by 1 or 2 halo substituents; cyclohexyl; phenyl, unsubstituted or substituted by 1 to 3 chloro substituents, by a bromo substituent in the para-position or by 1 to 3 methyl substituents; or benzyl, unsubstituted or substituted by 1 to 3 chloro substituents or by a bromo substituent in the para-position; each R 2 ', independently, is (C 1-3 ) alkyl; or phenyl, unsubstituted or substituted by a chloro substituent, by a bromo substituent in the para-position or by a methyl substituent; each R 3 ', independently, is (C 1-3 ) alkyl or hydrogen; each R 4 ' and R 5 ', independently, is (C 1-4 ) alkyl; CH 2 Cl or CH 2 Br; or any R 4 ' and R 5 ', independently, together with the carbon atom to which they are bound, form a cyclohexylidene, cyclohexenylidene or 3,4-dibromocyclohexylidene ring; R 9 ' is (C 1-4 ) alkyl; cyclohexyl; benzyl or phenyl; R 10 ' is hydrogen; (C 1-4 ) alkyl; cyclohexyl; benzyl or phenyl; or R 9 ' and R 10 ', together with the nitrogen atom to which they are bound, form a piperidino or morpholino ring, with the provisos that: (i) when one or more of X 1 , X 2 and Y is oxygen, then Z can only be oxygen, (ii) when X 1 and Y are both oxygen, then each moiety R', independently, is a radical (b'), (iii) when Z is oxygen and n is zero, only one radical (c') can be present in the molecule, (iv) when X 1 or Y is oxygen, then R 2 ' in any radical (b') bound to that same phosphorus atom is other than alkyl, (v) when two radicals (b') are attached to a phosphorus atom and X 1 and Y attached to that same phosphorus atom is sulphur, then both of the moieties R 2 ' in these radicals (b') are (C 1-3 ) alkyl, (vi) when one of the moieties R 2 ' and R 3 ' bound to the same nitrogen atom in a radical (b') is ethyl or propyl, the other must be ethyl or propyl, (vii) when n is 1, or when n is zero and R 2 ' in any radical (b') is (C 1-3 ) alkyl, any R 3 ', or R 3 ' in that same radical (b'), respectively, is other than hydrogen, and (viii) when each of X 1 and Y is oxygen, each of R 4 ' and R 5 ', independently, in any radical (c') is CH 2 Cl or CH 2 Br or both R 4 ' and R 5 ', together with the carbon atom to which they are bound form one of the rings indicated above.

Claim 9

A method of producing a flameproofed polymeric organic material, other than cellulose, comprising treating the polymeric organic material, directly or indirectly, with a flameproofing effective amount of a compound of the formula ##STR75## in which each R', independently, is a radical --OR 1 ' (a') or ##STR76## or two moieties R' bound to the same phosphorus atom form a radical (c') ##STR77## and each of the other two moieties R', independently, is a radical (a') or (b'), or the other two moieties R' bound to the same phosphorus atom form a second radical (c'), independent from the first radical (c'), each of X 1 , x 2 , y and Z, independently, is oxygen or sulphur, n is zero or 1, each R 1 ', independently, is ethyl, unsubstituted or substituted by a halo substituent; (C 3-6 ) alkyl, unsubstituted or substituted by 1 to 3 halo substituents; (C 3-6 ) alkenyl, unsubstituted or substituted by 1 or 2 halo substituents; cyclohexyl; phenyl, unsubstituted or substituted by 1 to 3 chloro substituents, by a bromo substituent in the para-position or by 1 to 3 methyl substituents; or benzyl, unsubstituted or substituted by 1 to 3 chloro substituents or by a bromo substituent in the para-position; each R 2 ', independently, is (C 1-3 ) alkyl; or phenyl, unsubstituted or substituted by a chloro substituent, by a bromo substituent in the para-position or by a methyl substituent; each R 3 ', independently, is (C 1-3 ) alkyl or hydrogen; each R 4 ' and R 5 ', independently, is (C 1-4 ) alkyl; CH 2 Cl or CH 2 Br; or any R 4 ' and R 5 ', independently, together with the carbon atom to which they are bound, form a cyclohexylidene, cyclohexenylidene or 3,4-dibromocyclohexylidene ring; R 9 ' is (C 1-4 ) alkyl; cyclohexyl; benzyl or phenyl; R 10 ' is hydrogen; (C 1-4 ) alkyl; cyclohexyl; benzyl or phenyl; or R 9 ' and R 10 ', together with the nitrogen atom to which they are bound, form a piperidino or morpholino ring, with the provisos that: (i) when one or more of X 1 , X 2 and Y is oxygen, then Z can only be oxygen, (ii) when X 1 and Y are both oxygen, then each moiety R', independently, is a radical (b'), (iii) when Z is oxygen and n is zero, only one radical (c') can be present in the molecule, (iv) when X 1 or Y is oxygen, then R 2 ' in any radical (b') bound to that same phosphorus atom is other than alkyl, (v) when two radicals (b') are attached to a phosphorus atom and X 1 and Y attached to that same phosphorus atom is sulphur, then both of the moieties R 2 ' in these radicals (b') are (C 1-3 ) alkyl, (vi) when one of the moieties R 2 ' and R 3 ' bound to the same nitrogen atom in a radical (b') is ethyl or propyl, the other must be ethyl or propyl, (vii) when n is 1, or when n is zero and R 2 ' in any radical (b') is (C 1-3 ) alkyl, any R 3 ', or R 3 ' in that same radical (b'), respectively, is other than hydrogen, and (viii) when each of X 1 and Y is oxygen, each of R 4 ' and R 5 ', independently, in any radical (c') is CH 2 Cl or CH 2 Br or both R 4 ' and R 5 ', together with the carbon atom to which they are bound form one of the rings indicated above.