Dentin and enamel adhesives

Claim 2

polymerizable compounds comprising an organic ester of one or more acids of phosphorus, the organic radical of said ester containing at least one polymerizable functional group, characterized in that said ester has chlorine or bromine bonded directly to phosphorus.

Claim 3

Compounds according to Claim 1, further characterized in that said compounds have the formulae: wherein: m is 1 to 3, m' and m" are zero or 1 and are the same or different, n is 1 to 4, 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, p', and p" are zero or 1 and are the same or different, m + n + 2p = 3 or 5, m' + m" + n' + 2p' = 3 or 5, m' + m" + n" + 2p" = 3 or 5, R 1 is a monovalent, olefinic organic radical which can be straight chain, branched, or cyclic, can contain skeletal hetero atoms, and 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, Br, or R 4 , where R 4 is an aliphatic or oxyaliphatic radical having 1 to 12 carbon atoms, and each X is the same as or different from other X , with the proviso that at least one X is Cl or Br.

Claim 4

Compounds according to Claim 2, further characterized in that said compounds have the formula: wherein m + n = 3.

Claim 5

Compounds according to Claim 2, further characterized in that said compounds have the formula: wherein m' + m" + n' = 3 and m' + m" + n" = 3.

Claim 6

Compounds according to Claim 2, further characterized in that R l is an alkenyl, alkenoxy, cycloalkenyl, aralkenyl, or alkenaryl radical having 2 to 40 carbon atoms.

Claim 7

Compounds according to Claim 2, further characterized in that R 2 and R 3 are alkenylidene, oxyalkenylidene, cycloalkenylidene, arylenealkenylidene, or alkenylidenearylidene radicals, having 2 to 40 carbon atoms.

Claim 8

Compounds according to any preceeding claim, further characterized in that said organic radical is the residue remaining after removal of one or more hydroxyl hydrogen atoms from BIS-GMA.

Claim 9

Compounds according to Claim 7, further characterized in that phosphorus is doubly bonded to an oxygen atom, is bonded to at least one chlorine atom, and the ratio of said phosphorus to said BIS-GMA is between 0.025:1 and 1:1.

Claim 10

Compounds according to any preceeding claim, further characterized in that said compounds contain or -OPBr 2 moieties.

Claim 11

A method for repairing or veneering hard dental tissue, without the necessity for acid etching said tissue, comprising the steps of: (a) applying to said tissue a polymerizable composition comprising a polymerizable compound, a free radical initiator or light activatable catalyst, a tertiary amine, and a sulfur compound in the +2 or +4 oxidation state, and (b) causing said composition to harden on said tissue, characterized in that said polymerizable compound is a compound according to Claim 1.