Spirocyclic boron compounds, a process for their manufacture and their use as a flame-retardant additive

Claim 2

A spirocyclic boron compound of the formula ##STR7## wherein R 1 and R 2 , which may be the same or different, each are dihalogeno alkylene, having 2 to 6 carbon atoms, a halogen-substituted bis-methyleno-bicycloheptene-radical, tetrahalogeno-o,o'-phenylene, tetrachloro-o,o'-biphenylene, tetrabromo-o,o'-biphenylene or a group of the formula ##STR8## in which Hal is chlorine or bromine and m is the integer 3 or 4, and Z + is alkali metal ion, an equivalent of an alkaline earth metal, a guanidinium or hydrazinium ion or an ion of the formula ##STR9## wherein R 3 , R 4 , R 5 and R 6 , which may be the same or different, each are hydrogen, alkyl with 1 to 8 carbon atoms, cycloalkyl with 5 or 6 carbon atoms or phenyl, whereby in the case where one of the radicals R 3 , R 4 , R 5 or R 6 is phenyl, the other ones have a meaning other than phenyl.

Claim 3

A spirocyclic boron compound as claimed in claim 1 having the formula ##STR10## in which X is dihalogenoethylene or 1,3-dihalogeno-propylen-2,2-, whereby halogen is selected from the group consisting of chlorine, bromine and iodine and Z + is, alkali metal ion, an equivalent of an alkaline metal earth, a guanidinium or hydrazinium ion or an ion of the formula ##STR11## wherein R 3 , R 4 , R 5 and R 6 , which may be the same or different each are hydrogen, alkyl with 1 to 8 carbon atoms, cycloalkyl with 5 or 6 carbon atoms or phenyl, whereby in the case where one of the radicals R 3 , R 4 , R 5 or R 6 is phenyl, the other ones have a meaning other than phenyl.

Claim 4

A spirocycic boron compound as claimed in claim 1 having the formula ##STR12## in which Hal is bromine or chlorine and Z + is alkali metal ion, an equivalent of, a guanidinium or hydrazinium ion or an ion of the formula ##STR13## wherein R 3 , R 4 , R 5 and R 6 , which may be the same or different each are hydrogen, alkyl with 1 to 8 carbon atoms, cycloalkyl with 5 or 6 carbon atoms or phenyl, whereby in the case where one of the radicals R 3 , R 4 , R 5 or R 6 is phenyl, the other ones have a meaning other than phenyl.

Claim 5

A spirocyclic boron compound as claimed in claim 1 of the formula ##STR14## in which Hal is chlorine or bromine and Z + is alkali metal ion, an equivalent of an alkaline metal earth, a guanidinium or hydrazinium ion or an ion of the formula ##STR15## wherein R 3 , R 4 , R 5 and R 6 , which may be the same or different each are hydrogen, alkyl with 1 to 8 carbon atoms, cycloalkyl with 5 or 6 carbon atoms or phenyl, whereby in the case where one of the radicals R 3 , R 4 , R 5 or R 6 is phenyl, the other ones have a meaning other than phenyl.

Claim 6

A spirocyclic boron compound as claimed in claim 1 of the formula ##STR16## in which Hal is chlorine or bromine and Z + is alkali metal ion, an equivalent of an alkaline earth metal, a guanidinium or hydrazinium ion or an ion of the formula ##STR17## wherein R 3 , R 4 , R 5 and R 6 , which may be the same or different each are hydrogen, alkyl with 1 to 8 carbon atoms, cycloalkyl with 5 or carbon atoms or phenyl, whereby in the case where one of the radicals R 3 , R 4 , R 5 or R 6 is phenyl, the other ones have a meaning other than phenyl.

Claim 7

A spirocyclic compound as claimed in claim 1 of the formula ##STR18## in which Hal is bromine or chlorine and Z + is alkali metal ion, an equivalent of an alkaline earth metal, a guanidinium or hydrazinium ion or an ion of the formula ##STR19## wherein R 3 , R 4 , R 5 and R 6 , which may be the same or different each are hydrogen, alkyl with 1 to 8 carbon atoms, cycloalkyl with 5 or 6 carbon atoms or phenyl, whereby in the case where one of the radicals R 3 , R 4 , R 5 or R 6 is phenyl, the other ones have a meaning other than phenyl.

Claim 8

A spirocyclic compound as claimed in claim 1 of the formula ##STR20## in which X is dihalogenoethylene or 1,3-dihalogenopropylene-2,2, whereby halogeno is selected from the group consisting of chlorine, bromine and iodine, Hal is bromine or chlorine and Z + is alkali metal ion, an equivalent of an alkaline earth metal, a guanidinium or hydrazinium ion or an ion of the formula ##STR21## wherein R 3 , R 4 , R 5 and R 6 , which may be the same or different each are hydrogen, alkyl with 1 to 8 carbon atoms, cycloalkyl with 5 or 6 carbon atoms or phenyl, whereby in the case where one of the radicals R 3 , R 4 , R 5 or R 6 is phenyl, the other ones have a meaning other than phenyl.

Claim 9

A compound as claimed in claim 2, said compound being a salt of Bis-[2,2-bis-(bromomethyl)-1,3-propane-diolato]-borate(1-) with guanidine, sodium-hydroxide, ammonia, triethylamine or diethylamine.

Claim 10

A compound as claimed n claim 3, said compound being a salt of Bis-(tetrabromopyrocatecholato)-borate(1) with tetraethylammoniumhydroxide, triethylammoniumhydroxide, diethylammoniumhydroxide, diisobutylammonium hydroxide, ammoniumhydroxide, sodium hydroxide, cyclohexylammonium hydroxide, n-hexylammoniumhydroxide or dimethylphenylammoniumhydroxide.

Claim 11

A compound according to claim 2, said compound being guanidine bis-(2,3-dibromo-1,4-butanediolato)-borate(1-)

Claim 12

A compound according to claim 2, said compound being sodium bis-[2,2-bis-(bromomethyl)-1,3-propanediolato]-borate(1-)

Claim 13

A compound according to claim 3, said compound being triethylammonium bis-(tetrabromopyrocatecholato)-borate(1-)

Claim 14

A compound according to claim 3, said compound being diethylammonium bis-(tetrabromopyrocatecholato)-borate(1-)

Claim 15

A compound according to claim 4, said compound being guanidine bis-[(3,3',5,5'-tetrabromo-1,1'-biphenyl)-2,2'-diolato-O,O']-borate(1-)

Claim 16

A compound according to claim 5, said compound being triethylammonium bis-[1,2,3,4,7,7-hexachloro-bicyclo(2,2,1)hept-2-ene-5,6-bis-methanolato]-borate(1-)

Claim 17

A flame retarding agent which comprises a spirocyclic boron compound of the formula ##STR22## wherein R 1 and R 2 , which may be the same or different, each are dihalogeno alkylene, having 2 to 6 carbon atoms, a halogen-substituted bis-methyleno-bicycloheptene-radical, tetrahalogeno-o,o'-phenylene, tetrachloro-o,o'-biphenylene, tetrabromo-o,o'-biphenylene or a group of the formula ##STR23## in which Hal is chlorine or bromine and m is the integer 3 or 4, and Z + is alkali metal ion, an equivalent of an alkaline earth metal, a guanidinium or hydrazinium ion or an ion of the formula ##STR24## wherein R 3 , R 4 , R 5 and R 6 , which may be the same or different, each are hydrogen, alkyl with 1 to 8 carbon atoms, cycloalkyl with 5 or 6 carbon atoms or phenyl, whereby in the case where one of the radicals R 3 , R 4 , R 5 or R 6 is phenyl, the other ones have a meaning other than phenyl and Sb 2 O 3 as synergistic agent.

Claim 18

A flame retarding agent which comprises a spirocyclic boron compound of the formula ##STR22## wherein R 1 and R 2 , which may be the same or different, each are dihalogeno alkylene, having 2 to 6 carbon atoms, a halogen-substituted bis-methyleno-bicycloheptene-radical, tetrahalogeno-o,o'-phenylene, tetrachloro-o,o'-biphenylene, tetrabromo-o,o'-biphenylene or a group of the formula ##STR23## in which Hal is chlorine or bromine and m is the integer 3 or 4, and Z + is alkali metal ion, an equivalent of an alkaline earth metal, a guanidinium or hydrazinium ion or an ion of the formula ##STR24## wherein R 3 , R 4 , R 5 and R 6 , which may be the same or different, each are hydrogen, alkyl with 1 to 8 carbon atoms, cycloalkyl with 5 or 6 carbon atoms or phenyl, whereby in the case where one of the radicals R 3 , R 4 , R 5 or R 6 is phenyl, the other ones have a meaning other than phenyl and Sb 2 O 3 as synergistic agent.