Polymerizable phosphorus esters

Claim 2

Polymerizaable compounds, comprising an organic ester of one or more acids of phosphorus, the organic radical of said ester containing at least one free-radically polymerizable functional group, wherein said ester contains chlorine or bromine and said organic radical is the residue remaining after removal of one or more hydroxyl hydrogen atoms from BIS-GMA.

Claim 3

Compounds according to claim 1, wherein said acid of phosphorus comprises POCl 3 , C 6 H 5 OP(O)Cl 2 , PCl 3 , or PBr 3 .

Claim 4

Compounds according to claim 1, containing groups of the formula: ##STR11##

Claim 5

Polymerizable compounds, comprising an organic ester of one or more acids of phosphorus, the organic radical of said ester containing at least one free-radically polymerizable functional group, wherein said organic radical is the residue remaining after removal of one or more hydroxyl hydrogen atoms from BIS-GMA, said ester contains chlorine, said acid of phosphorus comprises phosphorus oxychloride, and the weight of said phosphorus oxychloride is about 0.25 to twenty percent of the weight of said BIS-GMA.

Claim 6

Polymerizable compounds, comprising an organic ester of one or more acids of phosphorus, the organic radical of said ester containing at least one free-radically polymerizable functional group, wherein said organic radical is the residue remaining after removal of one or more hydroxyl hydrogen atoms from BIS-GMA, said ester contains chlorine, said acid of phosphorus comprises phosphorus oxychloride, and the weight of said phosphorus oxychloride is about 0.25 to twenty percent of the weight of said BIS-GMA.

Claim 7

Compounds according to claim 4, wherein the weight of said phosphorus oxychloride is about one to 13 percent of the weight of said BIS-GMA.

Claim 8

Compounds according to claim 4, wherein the weight of said phosphorus oxychloride is about one to ten percent of the weight of said BIS-GMA.

Claim 9

Polymerizable compounds, comprising an adduct made by combining BIS-GMA and a chlorine-containing or bromine-containing phosphorus acid.

Claim 10

Polymerizable compounds, comprising an adduct made by combining BIS-GMA and a chlorine-containing or bromine-containing phosphorus acid.

Claim 11

Compounds according to claim 7, wherein said phosphorus acid comprises POCl 3 , C 6 H 5 OP(O)Cl 2 , PCl 3 , or PBr 3 .

Claim 12

Compounds according to claim 7, wherein said phosphorus acid comprises phosphorus oxychloride.

Claim 13

Compounds according to claim 9, wherein said adduct was made from about 0.25 to 20% by weight of said phosphorus oxychloride, based upon the weight of said BIS-GMA.

Claim 14

Compounds according to claim 9, wherein said adduct was made from about one to 13 percent by weight of said phosphorus oxychloride, based on the weight of said BIS-GMA.

Claim 15

Compounds according to claim 9, wherein said adduct was made from about one to ten percent by weight of said phosphorus oxychloride, based on the weight of said BIS-GMA.

Claim 16

Compounds according to claim 7, wherein said phosphorus acid comprises PBr 3 .

Claim 17

Compounds according to claim 7, containing groups of the formulae: ##STR12##

Claim 18

Polymerizable compounds, comprising an organic ester of one or more acids of phosphorus, said ester having chlorine or bromine bonded directly to phosphorus, and the organic radical of said ester containing at least one free-radically polymerizable functional groups, wherein said organic radical is the residue remaining after removal of one or more hydroxyl hydrogen atoms from BIS-GMA.

Claim 19

Polymerizable compounds, comprising an organic ester of one or more acids of phosphorus, said ester having chlorine or bromine bonded directly to phosphorus, and the organic radical of said ester containing at least one free-radically polymerizable functional groups, wherein said organic radical is the residue remaining after removal of one or more hydroxyl hydrogen atoms from BIS-GMA.

Claim 20

Polymerizable compounds, comprising an organic ester of one or more acids of phosphorus, said ester having chlorine or bromine bonded directly to phosphorus, and the organic radical of said ester containing at least one free-radically polymerizable functional groups, wherein said organic radical is the residue remaining after removal of one or more hydroxyl hydrogen atoms from BIS-GMA, phosphorus is doubly bonded to an oxygen atom and is bonded to at least one chlorine atom, and the ratio of said acid of phosphorus to said BIS-GMA is between about 0.025:1 and 1:1.

Claim 21

Polymerizable compounds, comprising an organic ester of one or more acids of phosphorus, said ester having chlorine or bromine bonded directly to phosphorus, and the organic radical of said ester containing at least one free-radically polymerizable functional groups, wherein said organic radical is the residue remaining after removal of one or more hydroxyl hydrogen atoms from BIS-GMA, phosphorus is doubly bonded to an oxygen atom and is bonded to at least one chlorine atom, and the ratio of said acid of phosphorus to said BIS-GMA is between about 0.025:1 and 1:1.

Claim 22

Polymerizable compounds, having the formulae R 5 OPOCl 2 or (R 5 O) 2 POCl where R 5 O is the radical remaining after removal of a hydroxyl hydrogen atom from BIS-GMA.

Claim 23

Polymerizable compounds, having the formulae R 5 OPOCl 2 or (R 5 O) 2 POCl where R 5 O is the radical remaining after removal of a hydroxyl hydrogen atom from BIS-GMA.

Claim 24

Polymerizable compounds, comprising an organic ester of one or more moiety of the formula --OPBr 2 , with the organic radical of said ester containing at least one olefinic group.

Claim 25

Polymerizable compounds, comprising an organic ester of one or more moiety of the formula --OPBr 2 , with the organic radical of said ester containing at least one olefinic group.

Claim 26

Polymerizable compounds, comprising an organic ester of one or more acids of phosphorus, said ester having chlorine or bromine bonded directly to phosphorus, and the organic radical of said ester containing at least one olefinic group, said compounds having the formula: ##STR13## wherein m+n=3 m' and m" are zero or 1 and are the same or different, n' and n" are zero to 4 and are the same or different, with the proviso that n' and n" are not both zero, p' and p" are zero or 1 and are the same or different, m'+m"+n'+2p'=3 or 5, m'+m"+n"+2p"=3 or 5, R 1 is a monovalent, olefinic radical which can be straight chain, branched, or cyclic, can contain skeletal hetero atoms, can be unsubstituted or substituted with non-interfering moieties, R 2 and R 3 are divalent, olefinic organic radicals which can be straight chain, branched, or cyclic, can contain skeletal hetero atoms, can be unsubstituted or substituted with non-interfering moieties, and are the same or different, and X is Cl or Br, and each X is the same as or different from other X.

Claim 27

Polymerizable compounds, comprising an organic ester of one or more acids of phosphorus, said ester having chlorine or bromine bonded directly to phosphorus, and the organic radical of said ester containing at least one olefinic group, said compounds having the formula: ##STR13## wherein m+n=3 m' and m" are zero or 1 and are the same or different, n' and n" are zero to 4 and are the same or different, with the proviso that n' and n" are not both zero, p' and p" are zero or 1 and are the same or different, m'+m"+n'+2p'=3 or 5, m'+m"+n"+2p"=3 or 5, R 1 is a monovalent, olefinic radical which can be straight chain, branched, or cyclic, can contain skeletal hetero atoms, can be unsubstituted or substituted with non-interfering moieties, R 2 and R 3 are divalent, olefinic organic radicals which can be straight chain, branched, or cyclic, can contain skeletal hetero atoms, can be unsubstituted or substituted with non-interfering moieties, and are the same or different, and X is Cl or Br, and each X is the same as or different from other X.

Claim 28

Polymerizable compounds, comprising an organic ester of one or more acids of phosphorus, said ester having chlorine or bromine bonded directly to phosphorus, and the organic radical of said ester containing at least one olefinic group, said compounds having the formula: (R.sup.1 --O).sub.m --P--Br).sub.n wherein m+n=3, and R 1 is a monovalent, olefinic radical which can be straight chain, branched, or cyclic, can contain skeletal hetero atoms, and can be unsubstituted or substituted with non-interfering moieties.

Claim 29

Polymerizable compounds, comprising an organic ester of one or more acids of phosphorus, said ester having chlorine or bromine bonded directly to phosphorus, and the organic radical of said ester containing at least one olefinic group, said compounds having the formula: (R.sup.1 --O).sub.m --P--Br).sub.n wherein m+n=3, and R 1 is a monovalent, olefinic radical which can be straight chain, branched, or cyclic, can contain skeletal hetero atoms, and can be unsubstituted or substituted with non-interfering moieties.

Claim 30

Polymerizable compounds, comprising an organic ester of one or more acids of phosphorus, said ester having chlorine or bromine bonded directly to phosphorus, and the organic radical of said ester containing at least one olefinic group, said compounds having the formula: ##STR14## wherein m' and m" are zero or 1 and are the same or different, n' and n" are zero to 4 and are the same or different with the proviso that n' and n" are not both zero, p' and p" are zero or 1 and are the same or different, m'+m"+n'+2p'=3 or 5, m'+m"+n"+2p"=3 or 5, R 2 and R 3 are alkenylidene, oxyalkenylidene, cycloalkenylidene, arylenealkenylidene, or alkenylidenearylidene radicals, having 2 to 40 carbon atoms, and X is Cl or Br, and each X is the same as or different from other X.

Claim 31

Polymerizable compounds, comprising an organic ester of one or more acids of phosphorus, said ester having chlorine or bromine bonded directly to phosphorus, and the organic radical of said ester containing at least one olefinic group, said compounds having the formula: ##STR14## wherein m' and m" are zero or 1 and are the same or different, n' and n" are zero to 4 and are the same or different with the proviso that n' and n" are not both zero, p' and p" are zero or 1 and are the same or different, m'+m"+n'+2p'=3 or 5, m'+m"+n"+2p"=3 or 5, R 2 and R 3 are alkenylidene, oxyalkenylidene, cycloalkenylidene, arylenealkenylidene, or alkenylidenearylidene radicals, having 2 to 40 carbon atoms, and X is Cl or Br, and each X is the same as or different from other X.

Claim 32

Polymerizable compounds, comprising an organic ester of one or more acids of phosphorus, said ester having chlorine bonded directly to phosphorus, and the organic radical of said ester containing at least one olefinic group, said compounds having the formula: ##STR15## wherein m' and m" are zero or 1 and are the same or different, n' and n" are zero to 4 and the same or different, with the proviso that n' and n" are not both zero, m'+m"+n'=3, m'+m"+n"=3, and R 2 and R 3 are divalent, olefinic organic radicals which can be straight chain, branched, or cyclic, can contain skeletal hetero atoms, can be unsubstituted or substituted with non-interfering moieties, and are the same or different.

Claim 33

Polymerizable compounds, comprising an organic ester of one or more acids of phosphorus, said ester having chlorine bonded directly to phosphorus, and the organic radical of said ester containing at least one olefinic group, said compounds having the formula: ##STR15## wherein m' and m" are zero or 1 and are the same or different, n' and n" are zero to 4 and the same or different, with the proviso that n' and n" are not both zero, m'+m"+n'=3, m'+m"+n"=3, and R 2 and R 3 are divalent, olefinic organic radicals which can be straight chain, branched, or cyclic, can contain skeletal hetero atoms, can be unsubstituted or substituted with non-interfering moieties, and are the same or different.