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US 4,062,687 AGranted
Phosphoric acid derivatives as flameproofing agents
AssigneeSandoz Ltd.
InventorsClaudine Mauric, Rainer Wolf
Life of this patent
Estimating the term…
Abstract
Flameproofed cellulose includes as a flameproofing agent a compound selected from esters, ester-amides and amides of pyrophosphoric, of mono-, di- and trithiopyrophosphoric, of triphosphoric, and of mono-, di-, tri- and pentathiotriphosphoric acids. Preferred flameproofed cellulose, and other polymeric organic materials include as a flameproofing agent a compound selected from a smaller class of the above compounds.
Claims10
Flameproofed cellulose containing as a flameproofing agent, a compound of the formula ##STR62## in which each R, independently, is a radical-OR.sub.1 (a) or ##STR63## or two moieties R bound to the same phosphorus atom form a radical (c), ##STR64## 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.sub.1, X.sub.2, Y and Z, independently, is oxygen or sulphur,
- n is zero or 1,
- A is a radical ##STR65## each R.sub.1, independently, is methyl;
- ethyl or propenyl, each unsubstituted or substituted with up to 3 halogen atoms or with a (C.sub.1-6)alkoxy group;
- (C.sub.3-12)alkyl or (C.sub.4-12)alkenyl, each unsubstituted or substituted with up to 4 halogen atoms;
- (C.sub.5-8)cycloalkyl or (C.sub.5-8)cycloalkyl-(C.sub.1-4)alkyl, containing 7-9 carbon atoms in toto, each unsubstituted or substituted with 1 or 2 halogen atoms;
- or phenyl or phenyl-(C.sub.1-4)alkyl, each unsubstituted or substituted aromatically with up to 5 halogen atoms or with up to 3 (C.sub.1-3)alkyl and/or (C.sub.1-3)alkoxy groups,
- each R.sub.2, independently, is (C.sub.1-4)alkyl, cyclohexyl or benzyl;
- or phenyl, unsubstituted or substituted with 1 or 2 chlorine atoms of which only one can occupy an ortho-position, with a bromine atom in the para-position, or with up to 2 (C.sub.1-3)alkyl and/or (C.sub.1-3) alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3,
- each R.sub.3, independently, is (C.sub.1-4)alkyl or hydrogen,
- or any R.sub.2 and R.sub.3, independently, together with the nitrogen atom to which they are bound, form a 5- or 6-membered, saturated heterocyclic ring which may contain as a ring member an oxygen or sulphur atom, or a second nitrogen atom to which is bound a (C.sub.1-4)alkyl group,
- each R.sub.4 and R.sub.5, independently, is hydrogen, (C.sub.1-4)alkyl, CH.sub.2 Cl, CH.sub.2 Br or phenyl,
- or any R.sub.4 and R.sub.5, independently, together with the carbon atom to which they are bound, form a cyclohexylidene, cyclohexenylidene or 3,4-dibromocyclohexylidene ring,
- each R.sub.6 and R.sub.8, independently, is hydrogen or (C.sub.1-4)alkyl,
- each R.sub.7, independently, is hydrogen or methyl, R.sub.9 is methyl;
- ethyl, unsubstituted or substituted with a halogen atom;
- propyl, unsubstituted or substituted with 1 or 2 halogen atoms;
- (C.sub.4-12)alkyl, unsubstituted or substituted with up to 3 halogen atoms;
- cyclohexyl;
- benzyl;
- or phenyl, unsubstituted or substituted with 1 or 2 chlorine atoms, or with a bromine atom in the para-position, and/or in both cases with up to 2 (C.sub.1-3)alkyl and/or (C.sub.1-3)alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3,
- R.sub.10 is hydrogen;
- methyl;
- ethyl, unsubstituted or substituted with a halogen atom;
- propyl, unsubstituted or substituted with up to 2 halogen atoms;
- (C.sub.4-12)alkyl, unsubstituted or substituted with up to 3 halogen atoms;
- cyclohexyl;
- benzyl;
- or phenyl,
- or R.sub.9 and R.sub.10, together with the nitrogen atom to which they are bound, form a 5- or 6-membered, saturated heterocyclic ring which may contain as a ring member an oxygen or sulphur atom, or a second nitrogen atom, to which is bound a (C.sub.1-4)alkyl group,
- with the provisos:
- i. when one or more of X.sub.1, X.sub.2 and Y is oxygen, then Z can only be oxygen,
- ii. when X.sub.1 and Y are both oxygen, then up to 2 only of the moieties R can be a radical (a),
- iii. when there are more than 2 radicals (a) in the molecule, up to 2 of them only can be methoxy,
- iv. when Z is oxygen and n is zero, only one radical (c) can be present in the molecule,
- v. when X.sub.1 or Y is oxygen, then R.sub.2 in any radical (b) attached to that same phosphorus atom as the oxygen atom is other than alkyl,
- vi. when two radicals (b) are attached to a phosphorus atom and X.sub.1 or Y attached to that same phosphurus atom is sulphur, then both of the moieties R.sub.2 in these radicals (b) are (C.sub.1-4)alkyl,
- vii. when n is 1, or when n is zero and R.sub.2 in any radical (b) is (C.sub.1-4)alkyl, any R.sub.3, or R.sub.3 in that same radical (b), respectively, is other than hydrogen,
- viii. at least one of R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 in any radical (c) is other than hydrogen,
- ix. when each of R.sub.4 and R.sub.5, independently, in any radical (c) is CH.sub.2 Cl or CH.sub.2 Br or both R.sub.4 and R.sub.5, together with the carbon atom to which they are bound form one of the rings indicated above, each of R.sub.6, R.sub.7 and R.sub.8 in the same radical (c) is hydrogen,
- and x. when each of X.sub.1 and Y is oxygen, each of R.sub.4 and R.sub.5, independently, in any radical (c) is CH.sub.2 Cl or CH.sub.2 Br or both R.sub.4 and R.sub.5, together with the carbon atom to which they are bound, form one of the rings indicated above.
38 more elements
A method of producing flameproofed regenerated cellulose comprising regenerating cellulose from its solution containing a flameproofing effective amount of a compound of the formula ##STR76## in which each R, independently, is a radical --OR.sub.1 (a) or ##STR77## or two moieties R bound to the same phosphorus atom form a radical (c), ##STR78## 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.sub.1, X.sub.2, Y and Z, independently, is oxygen or sulphur, n is zero or 1, A is a radical (a) ##STR79## each R.sub.1, independently, is methyl;
- ethyl or propenyl, each unsubstituted or substituted with up to 3 halogen atoms or with a (C.sub.1-6)alkoxy group;
- (C.sub.3-12)alkyl or (C.sub.4-12)alkenyl, each unsubstituted or substituted with up to 4 halogen atoms;
- (C.sub.5-8)cycloalkyl or (C.sub.5-8)cycloalkyl-(C.sub.1-4)alkyl, containing 7-9 carbon atoms in toto, each unsubstituted or substituted with 1 or 2 halogen atoms;
- or phenyl or phenyl-(C.sub.1-4)alkyl, each unsubstituted or substituted aromatically with up to 5 halogen atoms or with up to 3 (C.sub.1-3)-alkyl and/or (C.sub.1-3)alkoxy groups,
- each R.sub.2, independently, is (C.sub.1-4)alkyl, cyclohexyl or benzyl;
- or phenyl, unsubstituted or substituted with 1 or 2 chlorine atoms of which only one can occupy in ortho-position, with a bromine atom in the para-position, or with up to 2 (C.sub.1-3)alkyl and/or (C.sub.1-3) alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3,
- each R.sub.3, independently, is (C.sub.1-4)alkyl or hydrogen,
- or any R.sub.2 and R.sub.3, independently, together with the nitrogen atom to which they are bound, form a 5- or 6-membered, saturated heterocyclic ring which may contain as a ring member an oxygen or sulphur atom, or a second nitrogen atom to which is bound a (C.sub.1-4)alkyl group,
- each R.sub.4 and R.sub.5, independently, is hydrogen, (C.sub.1-4) alkyl, CH.sub.2 Cl, CH.sub.2 Br or phenyl,
- or any R.sub.4 and R.sub.5, independently, together with the carbon atom to which they are bound, form a cyclohexylidene, cyclohexenylidene or 3,4-dibromocyclohexylidene ring,
- each R.sub.6 and R.sub.8, independently, is hydrogen or (C.sub.1-4)alkyl,
- each R.sub.7, independently, is hydrogen or methyl, R.sub.9 is methyl;
- ethyl, unsubstituted or substituted with a halogen atom;
- propyl unsubstituted or substituted with 1 or 2 halogen atoms;
- (C.sub.4-12)alkyl, unsubstituted or substituted with up to 3 halogen atoms;
- cyclohexyl;
- benzyl;
- or phenyl, unsubstituted or substituted with 1 or 2 chlorine atoms, or with a bromine atom in the para-position, and/or in both cases with up to 2 (C.sub.1-3) alkyl and/or (C.sub.1-3)alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3,
- R.sub.10 is hydrogen;
- methyl;
- ethyl, unsubstituted or substituted with a halogen atom;
- propyl, unsubstituted or substituted with up to 2 halogen atoms;
- (C.sub.4-12)alkyl, unsubstituted or substituted with up to 3 halogen atoms;
- cyclohexyl;
- benzyl;
- or phenyl,
- or R.sub.9 and R.sub.10, together with the nitrogen atom to which they are bound, form a 5- or 6- membered, saturated heterocyclic ring which may contain as a ring member an oxygen or sulphur atom, or a second nitrogen atom, to which is bound a (C.sub.1-4)alkyl group,
- with the provisos:
- i. when one or more of X.sub.1, X.sub.2 and Y is oxygen, then Z can only be oxygen,
- ii. when X.sub.1 and Y are both oxygen, then up to 2 only of the moieties R can be a radical (a),
- iii. when there are more than 2 radicals (a) in the molecule, up to 2 of them only can be methoxy,
- iv. when Z is oxygen and n is zero, only one radical (c) can be present in the molecule,
- v. when X.sub.1 or Y is oxygen, then R.sub.2 in any radical (b) attached to that same phosphorus atom as the oxygen atom is other than alkyl,
- vi. when two radicals (b) are attached to a phosphorus atom and X.sub.1 or Y attached to that same phosphorus atom is sulphur, then both of the moieties R.sub.2 in these radicals (b) are (C.sub.1-4)alkyl,
- vii. when n is 1, or when n is zero and R.sub.2 in any radical (b) is (C.sub.1-4)alkyl, any R.sub.3, or R.sub.3 in that same radical (b), respectively, is other than hydrogen,
- viii. at least one of R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 in any radical (c) is other than hydrogen,
- ix. when each of R.sub.4 and R.sub.5, independently, in any radical (c) is CH.sub.2 Cl or CH.sub.2 Br or both R.sub.4 and R.sub.5, together with the carbon atom to which they are bound form one of the rings indicated above, each of R.sub.6, R.sub.7 and R.sub.8 in the same radical (c) is hydrogen,
- and x. when each of X.sub.1 and Y is oxygen, each of R.sub.4 and R.sub.5, independently, in any radical (c) is CH.sub.2 Cl or CH.sub.2 Br or both R.sub.4 and R.sub.5, together with the carbon atom to which they are bound, form one of the rings indicated above.
36 more elements
A method of producing flameproofed natural cellulose comprising coating the natural cellulose with a flame-proofing-effective amount of a compound of the formula ##STR80## in which each R, independently, is a radical --OR.sub.1 (a) or ##STR81## or two moieties R bound to the same phosphorus atom form a radical (c), ##STR82## 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.sub.1, X.sub.2, Y and Z, independently, is oxygen or sulphur, n is zero or 1, A is a radical (a) ##STR83## each R.sub.1, independently, is methyl;
- ethyl or propenyl, each unsubstituted or substituted with up to 3 halogen atoms or with a (C.sub.1-6)alkoxy group;
- (C.sub.3-12)alkyl or (C.sub.4-12)alkenyl, each unsubstituted or substituted with up to 4 halogen atoms;
- (C.sub.5-8)cycloalkyl or (C.sub.5-8)cycloalkyl-(C.sub.1-4)alkyl, containing 7-9 carbon atoms in toto, each unsubstituted or substituted with 1 or 2 halogen atoms;
- or phenyl or phenyl-(C.sub.1-4)alkyl, each unsubstituted or substituted aromatically with up to 5 halogen atoms or with up to 3 (C.sub.1-3)-alkyl and/or (C.sub.1-3)alkoxy groups,
- each R.sub.2, independently, is (C.sub.1-4)alkyl, cyclohexyl or benzyl;
- or phenyl, unsubstituted or substituted with 1 or 2 chlorine atoms of which only one can occupy an ortho-position, with a bromine atom in the para-position, or with up to 2 (C.sub.1-3)alkyl and/or (C.sub.1-3)-alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3,
- each R.sub.3, independently, is (C.sub.1-4)alkyl or hydrogen,
- or any R.sub.2 and R.sub.3, independently, together with the nitrogen atom to which they are bound form a 5- or 6-membered, saturated heterocyclic ring which may contain as a ring member an oxygen or sulphur atom, or a second nitrogen atom to which is bound a (C.sub.1-4)alkyl group,
- each R.sub.4 and R.sub.5, independently, is hydrogen, (C.sub.1-4)-alkyl, CH.sub.2 Cl, CH.sub.2 Br or phenyl,
- or any R.sub.4 and R.sub.5, independently, together with the carbon atom to which they are bound, form a cyclohexylidene, cyclohexenylidene or 3,4-dibromocyclohexylidene ring,
- each R.sub.6 and R.sub.8, independently, is hydrogen or (C.sub.1-4)alkyl,
- each R.sub.7, independently, is hydrogen or methyl, R.sub.9 is methyl;
- ethyl, unsubstituted or substituted with a halogen atom;
- propyl unsubstituted or substituted with 1 or 2 halogen atoms;
- (C.sub.4-12)alkyl, unsubstituted or substituted with up to 3 halogen atoms;
- cyclohexyl;
- benzyl;
- or phenyl, unsubstituted or substituted with 1 or 2 chlorine atoms, or with a bromine atom in the para-position, and/or in both cases with up to 2 (C.sub.1-3)-alkyl and/or (C.sub.1-3)alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3,
- R.sub.10 is hydrogen;
- methyl;
- ethyl, unsubstituted or substituted with a halogen atom;
- propyl, unsubstituted or substituted with up to 2 halogen atoms;
- (C.sub.4-12)alkyl, unsubstituted or substituted with up to 3 halogen atoms;
- cyclohexyl;
- benzyl;
- or phenyl,
- or R.sub.9 and R.sub.10, together with the nitrogen atom to which they are bound, form a 5- or 6-membered, saturated heterocyclic ring which may contain as a ring member an oxygen or sulphur atom, or a second nitrogen atom, to which is bound a (C.sub.1-4)alkyl group,
- with the provisos:
- i. when one or more of X.sub.1, X.sub.2 and Y is oxygen, then Z can only be oxygen,
- ii. when X.sub.1 and Y are both oxygen, then up to 2 only of the moieties R can be a radical (a),
- iii. when there are more than 2 radicals (a) in the molecule, up to 2 of them only can be methoxy,
- iv. when Z is oxygen and n is zero, only one radical (c) can be present in the molecule,
- v. when X.sub.1 or Y is oxygen, then R.sub.2 in any radical (b) attached to that same phosphorus atom as the oxygen atom is other than alkyl,
- vi. when two radicals (b) are attached to a phosphorus atom and X.sub.1 and Y attached to that same phosphorus atom is sulphur, then both of the moieties R.sub.2 in these radicals (b) are (C.sub.1-4)alkyl,
- vii. when n is 1, or when n is zero and R.sub.2 in any radical (b) is (C.sub.1-4)alkyl, any R.sub.3, or R.sub.3 in that same radical (b), respectively, is other than hydrogen,
- viii. at least one of R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 in any radical (c) is other than hydrogen,
- ix. when each of R.sub.4 and R.sub.5, independently, in any radical (c) is CH.sub.2 Cl or CH.sub.2 Br or both R.sub.4 and R.sub.5, together with the carbon atom to which they are bound form one of the rings indicated above, each of R.sub.6, R.sub.7 and R.sub.8 in the same radical (c) is hydrogen,
- and x. when each of X.sub.1 and Y is oxygen, each of R.sub.4 and R.sub.5, independently, in any radical (c) is CH.sub.2 Cl or CH.sub.2 Br or both R.sub.4 and R.sub.5, together with the carbon atom to which they are bound, form one of the rings indicated above.
36 more elements
Dependencies are inferred from the claim text.