Phosphoric acid derivatives as flameproofing agents

Claim 1

Flameproofed cellulose containing as a flameproofing agent, a compound of the formula ##STR62## in which each R, independently, is a radical-OR 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 1 , X 2 , Y and Z, independently, is oxygen or sulphur, n is zero or 1, A is a radical ##STR65## each R 1 , independently, is methyl; ethyl or propenyl, each unsubstituted or substituted with up to 3 halogen atoms or with a (C 1-6 )alkoxy group; (C 3-12 )alkyl or (C 4-12 )alkenyl, each unsubstituted or substituted with up to 4 halogen atoms; (C 5-8 )cycloalkyl or (C 5-8 )cycloalkyl-(C 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 1-4 )alkyl, each unsubstituted or substituted aromatically with up to 5 halogen atoms or with up to 3 (C 1-3 )alkyl and/or (C 1-3 )alkoxy groups, each R 2 , independently, is (C 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 1-3 )alkyl and/or (C 1-3 ) alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3, each R 3 , independently, is (C 1-4 )alkyl or hydrogen, or any R 2 and R 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 1-4 )alkyl group, each R 4 and R 5 , independently, is hydrogen, (C 1-4 )alkyl, CH 2 Cl, CH 2 Br or phenyl, 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, each R 6 and R 8 , independently, is hydrogen or (C 1-4 )alkyl, each R 7 , independently, is hydrogen or methyl, R 9 is methyl; ethyl, unsubstituted or substituted with a halogen atom; propyl, unsubstituted or substituted with 1 or 2 halogen atoms; (C 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 1-3 )alkyl and/or (C 1-3 )alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3, R 10 is hydrogen; methyl; ethyl, unsubstituted or substituted with a halogen atom; propyl, unsubstituted or substituted with up to 2 halogen atoms; (C 4-12 )alkyl, unsubstituted or substituted with up to 3 halogen atoms; cyclohexyl; benzyl; or phenyl, or R 9 and R 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 1-4 )alkyl group, with the provisos: 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 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 1 or Y is oxygen, then R 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 1 or Y attached to that same phosphurus atom is sulphur, then both of the moieties R 2 in these radicals (b) are (C 1-4 )alkyl, vii. when n is 1, or when n is zero and R 2 in any radical (b) is (C 1-4 )alkyl, any R 3 , or R 3 in that same radical (b), respectively, is other than hydrogen, viii. at least one of R 4 , R 5 , R 6 , R 7 and R 8 in any radical (c) is other than hydrogen, ix. when 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, each of R 6 , R 7 and R 8 in the same radical (c) is hydrogen, and x. 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 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 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 1 , X 2 , Y and Z, independently, is oxygen or sulphur, n is zero or 1, A is a radical (a) ##STR79## each R 1 , independently, is methyl; ethyl or propenyl, each unsubstituted or substituted with up to 3 halogen atoms or with a (C 1-6 )alkoxy group; (C 3-12 )alkyl or (C 4-12 )alkenyl, each unsubstituted or substituted with up to 4 halogen atoms; (C 5-8 )cycloalkyl or (C 5-8 )cycloalkyl-(C 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 1-4 )alkyl, each unsubstituted or substituted aromatically with up to 5 halogen atoms or with up to 3 (C 1-3 )-alkyl and/or (C 1-3 )alkoxy groups, each R 2 , independently, is (C 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 1-3 )alkyl and/or (C 1-3 ) alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3, each R 3 , independently, is (C 1-4 )alkyl or hydrogen, or any R 2 and R 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 1-4 )alkyl group, each R 4 and R 5 , independently, is hydrogen, (C 1-4 ) alkyl, CH 2 Cl, CH 2 Br or phenyl, 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, each R 6 and R 8 , independently, is hydrogen or (C 1-4 )alkyl, each R 7 , independently, is hydrogen or methyl, R 9 is methyl; ethyl, unsubstituted or substituted with a halogen atom; propyl unsubstituted or substituted with 1 or 2 halogen atoms; (C 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 1-3 ) alkyl and/or (C 1-3 )alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3, R 10 is hydrogen; methyl; ethyl, unsubstituted or substituted with a halogen atom; propyl, unsubstituted or substituted with up to 2 halogen atoms; (C 4-12 )alkyl, unsubstituted or substituted with up to 3 halogen atoms; cyclohexyl; benzyl; or phenyl, or R 9 and R 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 1-4 )alkyl group, with the provisos: 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 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 1 or Y is oxygen, then R 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 1 or Y attached to that same phosphorus atom is sulphur, then both of the moieties R 2 in these radicals (b) are (C 1-4 )alkyl, vii. when n is 1, or when n is zero and R 2 in any radical (b) is (C 1-4 )alkyl, any R 3 , or R 3 in that same radical (b), respectively, is other than hydrogen, viii. at least one of R 4 , R 5 , R 6 , R 7 and R 8 in any radical (c) is other than hydrogen, ix. when 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, each of R 6 , R 7 and R 8 in the same radical (c) is hydrogen, and x. 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 10

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 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 1 , X 2 , Y and Z, independently, is oxygen or sulphur, n is zero or 1, A is a radical (a) ##STR79## each R 1 , independently, is methyl; ethyl or propenyl, each unsubstituted or substituted with up to 3 halogen atoms or with a (C 1-6 )alkoxy group; (C 3-12 )alkyl or (C 4-12 )alkenyl, each unsubstituted or substituted with up to 4 halogen atoms; (C 5-8 )cycloalkyl or (C 5-8 )cycloalkyl-(C 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 1-4 )alkyl, each unsubstituted or substituted aromatically with up to 5 halogen atoms or with up to 3 (C 1-3 )-alkyl and/or (C 1-3 )alkoxy groups, each R 2 , independently, is (C 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 1-3 )alkyl and/or (C 1-3 ) alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3, each R 3 , independently, is (C 1-4 )alkyl or hydrogen, or any R 2 and R 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 1-4 )alkyl group, each R 4 and R 5 , independently, is hydrogen, (C 1-4 ) alkyl, CH 2 Cl, CH 2 Br or phenyl, 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, each R 6 and R 8 , independently, is hydrogen or (C 1-4 )alkyl, each R 7 , independently, is hydrogen or methyl, R 9 is methyl; ethyl, unsubstituted or substituted with a halogen atom; propyl unsubstituted or substituted with 1 or 2 halogen atoms; (C 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 1-3 ) alkyl and/or (C 1-3 )alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3, R 10 is hydrogen; methyl; ethyl, unsubstituted or substituted with a halogen atom; propyl, unsubstituted or substituted with up to 2 halogen atoms; (C 4-12 )alkyl, unsubstituted or substituted with up to 3 halogen atoms; cyclohexyl; benzyl; or phenyl, or R 9 and R 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 1-4 )alkyl group, with the provisos: 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 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 1 or Y is oxygen, then R 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 1 or Y attached to that same phosphorus atom is sulphur, then both of the moieties R 2 in these radicals (b) are (C 1-4 )alkyl, vii. when n is 1, or when n is zero and R 2 in any radical (b) is (C 1-4 )alkyl, any R 3 , or R 3 in that same radical (b), respectively, is other than hydrogen, viii. at least one of R 4 , R 5 , R 6 , R 7 and R 8 in any radical (c) is other than hydrogen, ix. when 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, each of R 6 , R 7 and R 8 in the same radical (c) is hydrogen, and x. 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 12

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 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 1 , X 2 , Y and Z, independently, is oxygen or sulphur, n is zero or 1, A is a radical (a) ##STR83## each R 1 , independently, is methyl; ethyl or propenyl, each unsubstituted or substituted with up to 3 halogen atoms or with a (C 1-6 )alkoxy group; (C 3-12 )alkyl or (C 4-12 )alkenyl, each unsubstituted or substituted with up to 4 halogen atoms; (C 5-8 )cycloalkyl or (C 5-8 )cycloalkyl-(C 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 1-4 )alkyl, each unsubstituted or substituted aromatically with up to 5 halogen atoms or with up to 3 (C 1-3 )-alkyl and/or (C 1-3 )alkoxy groups, each R 2 , independently, is (C 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 1-3 )alkyl and/or (C 1-3 )-alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3, each R 3 , independently, is (C 1-4 )alkyl or hydrogen, or any R 2 and R 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 1-4 )alkyl group, each R 4 and R 5 , independently, is hydrogen, (C 1-4 )-alkyl, CH 2 Cl, CH 2 Br or phenyl, 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, each R 6 and R 8 , independently, is hydrogen or (C 1-4 )alkyl, each R 7 , independently, is hydrogen or methyl, R 9 is methyl; ethyl, unsubstituted or substituted with a halogen atom; propyl unsubstituted or substituted with 1 or 2 halogen atoms; (C 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 1-3 )-alkyl and/or (C 1-3 )alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3, R 10 is hydrogen; methyl; ethyl, unsubstituted or substituted with a halogen atom; propyl, unsubstituted or substituted with up to 2 halogen atoms; (C 4-12 )alkyl, unsubstituted or substituted with up to 3 halogen atoms; cyclohexyl; benzyl; or phenyl, or R 9 and R 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 1-4 )alkyl group, with the provisos: 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 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 1 or Y is oxygen, then R 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 1 and Y attached to that same phosphorus atom is sulphur, then both of the moieties R 2 in these radicals (b) are (C 1-4 )alkyl, vii. when n is 1, or when n is zero and R 2 in any radical (b) is (C 1-4 )alkyl, any R 3 , or R 3 in that same radical (b), respectively, is other than hydrogen, viii. at least one of R 4 , R 5 , R 6 , R 7 and R 8 in any radical (c) is other than hydrogen, ix. when 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, each of R 6 , R 7 and R 8 in the same radical (c) is hydrogen, and x. 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 13

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 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 1 , X 2 , Y and Z, independently, is oxygen or sulphur, n is zero or 1, A is a radical (a) ##STR83## each R 1 , independently, is methyl; ethyl or propenyl, each unsubstituted or substituted with up to 3 halogen atoms or with a (C 1-6 )alkoxy group; (C 3-12 )alkyl or (C 4-12 )alkenyl, each unsubstituted or substituted with up to 4 halogen atoms; (C 5-8 )cycloalkyl or (C 5-8 )cycloalkyl-(C 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 1-4 )alkyl, each unsubstituted or substituted aromatically with up to 5 halogen atoms or with up to 3 (C 1-3 )-alkyl and/or (C 1-3 )alkoxy groups, each R 2 , independently, is (C 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 1-3 )alkyl and/or (C 1-3 )-alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3, each R 3 , independently, is (C 1-4 )alkyl or hydrogen, or any R 2 and R 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 1-4 )alkyl group, each R 4 and R 5 , independently, is hydrogen, (C 1-4 )-alkyl, CH 2 Cl, CH 2 Br or phenyl, 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, each R 6 and R 8 , independently, is hydrogen or (C 1-4 )alkyl, each R 7 , independently, is hydrogen or methyl, R 9 is methyl; ethyl, unsubstituted or substituted with a halogen atom; propyl unsubstituted or substituted with 1 or 2 halogen atoms; (C 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 1-3 )-alkyl and/or (C 1-3 )alkoxy groups, the aggregate of the carbon atoms thereof not exceeding 3, R 10 is hydrogen; methyl; ethyl, unsubstituted or substituted with a halogen atom; propyl, unsubstituted or substituted with up to 2 halogen atoms; (C 4-12 )alkyl, unsubstituted or substituted with up to 3 halogen atoms; cyclohexyl; benzyl; or phenyl, or R 9 and R 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 1-4 )alkyl group, with the provisos: 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 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 1 or Y is oxygen, then R 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 1 and Y attached to that same phosphorus atom is sulphur, then both of the moieties R 2 in these radicals (b) are (C 1-4 )alkyl, vii. when n is 1, or when n is zero and R 2 in any radical (b) is (C 1-4 )alkyl, any R 3 , or R 3 in that same radical (b), respectively, is other than hydrogen, viii. at least one of R 4 , R 5 , R 6 , R 7 and R 8 in any radical (c) is other than hydrogen, ix. when 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, each of R 6 , R 7 and R 8 in the same radical (c) is hydrogen, and x. 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.