β-Ketophosphonic acid according to general formula I: ##STR00001##
in which A=an aliphatic C.sub.1-C.sub.18 radical which can be interrupted by —O—, —S—, —CO—O— or —O—CO—C—; n=1, 2, 3 or 4; m=1 or 2; X=absent or a C.sub.1-C.sub.10 radical which can be interrupted by —O—, —S—, —CO—C—, —O—CO—NH— or —CO—NR.sup.1—, wherein R.sup.1 is H or C.sub.1-C.sub.7-alkyl; and PG=a group which can undergo free radical polymerization. The β-ketophosphonic acids are suitable in particular for the preparation of dental materials.

Acidic monomer according to Formula I:

##STR00001##

in which A is a linear or branched aliphatic C.sub.1-C.sub.18-hydrocarbon group, which can be interrupted by one or more —O—, —S—, —CO—O—, —O—CO—NH—, —HN—CO—NH— or —CO—NR.sup.1—; R.sup.1 is H or a C.sub.1-C.sub.6 alkyl group; X is absent or is a linear or branched aliphatic C.sub.1-C.sub.10 hydrocarbon group, which can be interrupted by one or more —O—, —S—, —CO—O—, —O—CO—NH—, —HN—CO—NH— or —CO—NR.sup.2—; R.sup.2 is H or a C.sub.1-C.sub.6 alkyl group; PG is a radically polymerizable group, preferably vinyl, allyl, CH.sub.2═CR.sup.3—CO—Y— or R.sup.4O—CO—C(═CH.sub.2)—CH.sub.2—Y—; Y═O or NR.sup.5 or is absent; R.sup.3 is H or CH.sub.3; R.sup.4 is H or a C.sub.1-C.sub.7 alkyl group; R.sup.5 is H or a C.sub.1-C.sub.7 alkyl group; n is 1, 2, 3 or 4; m=1 or 2; p=1, 2 or 3; and q=1, 2 or 3. The monomers are particularly suitable as components of dental material.

One embodiment of the present invention relates to a dental composition including a (meth)acrylate, an ultraviolet absorber, and a fluorescent agent, wherein the ultraviolet absorber has free of a maximum absorption wavelength in a range of greater than 320 nm and less than or equal to 500 nm.

One embodiment of the present invention relates to a dental composition including a (meth)acrylate, an ultraviolet absorber, and a fluorescent agent, wherein the ultraviolet absorber has free of a maximum absorption wavelength in a range of greater than 320 nm and less than or equal to 500 nm.

A one-part self-etching, self-priming dental adhesive having a pH of at most 2, which comprises an aqueous mixture containing (i) one or more polymerizable monomers optionally containing an acidic group, (ii) optionally one or more organic or inorganic acids, (iii) a polymerization initiator, and (iv) a thermal polymerisation inhibitor of the following formula (I): ##STR00001##  wherein R′.sub.1 represents a hydrogen atom, or a saturated hydrocarbon group having 1 to 18 carbon atoms. R′.sub.2, which may be the same or different if more than one R′.sub.2 is present, independently represent a saturated hydrocarbon group having 1 to 18 carbon atoms, and c represents an integer of from 1 to 4.

A one-part self-etching, self-priming dental adhesive having a pH of at most 2, which comprises an aqueous mixture containing (i) one or more polymerizable monomers optionally containing an acidic group, (ii) optionally one or more organic or inorganic acids, (iii) a polymerization initiator, and (iv) a thermal polymerisation inhibitor of the following formula (I): ##STR00001##  wherein R′.sub.1 represents a hydrogen atom, or a saturated hydrocarbon group having 1 to 18 carbon atoms. R′.sub.2, which may be the same or different if more than one R′.sub.2 is present, independently represent a saturated hydrocarbon group having 1 to 18 carbon atoms, and c represents an integer of from 1 to 4.

A compound has at least three functionalities, including a first functionality (a) that is a sulfonate group or a sulfate group of the formula —(O).sub.d—SO.sub.3M with d=0 or 1 and with M=hydrogen or a monovalent metal cation or a corresponding portion of a multivalent metal cation; a second functionality (b) that is a (meth)acryl residue; and a third functionality (c) that is a carboxylic acid function and/or a thioether group. When the compound is free of silicon, the sulfonate or sulfate group and the (meth)acryl residue are separated from each other by a hydrocarbon-containing residue having a carbon chain. The carbon chain is interrupted by S or NH, or the carbon chain contains a linking group, selected from C(O)NH, NHC(O), NR.sup.8C(O), NHC(O)O, NR.sup.8C(O)O, NHC(O)NH, C(O)NHC(O) and —C(O)S—, wherein R.sup.8 is alkyl or alkenyl or a (meth)acryl group.

A compound has at least three functionalities, including a first functionality (a) that is a sulfonate group or a sulfate group of the formula —(O).sub.d—SO.sub.3M with d=0 or 1 and with M=hydrogen or a monovalent metal cation or a corresponding portion of a multivalent metal cation; a second functionality (b) that is a (meth)acryl residue; and a third functionality (c) that is a carboxylic acid function and/or a thioether group. When the compound is free of silicon, the sulfonate or sulfate group and the (meth)acryl residue are separated from each other by a hydrocarbon-containing residue having a carbon chain. The carbon chain is interrupted by S or NH, or the carbon chain contains a linking group, selected from C(O)NH, NHC(O), NR.sup.8C(O), NHC(O)O, NR.sup.8C(O)O, NHC(O)NH, C(O)NHC(O) and —C(O)S—, wherein R.sup.8 is alkyl or alkenyl or a (meth)acryl group.

Described herein are compositions composed of a radiopaque agent and a cyanoacrylate monomer. These compositions cure in situ when administered to a subject and, thus, have numerous biomedical applications. The presence of the radiopaque agent allows the practitioner to visualize the compositions during and immediately after administration to the subject. The compositions are non-toxic and shelf-stable, and can be sterilized to prevent microbial growth. The compositions can be pre-mixed prior to sale and distribution, reducing the need for special training in their use.

Described herein are compositions composed of a radiopaque agent and a cyanoacrylate monomer. These compositions cure in situ when administered to a subject and, thus, have numerous biomedical applications. The presence of the radiopaque agent allows the practitioner to visualize the compositions during and immediately after administration to the subject. The compositions are non-toxic and shelf-stable, and can be sterilized to prevent microbial growth. The compositions can be pre-mixed prior to sale and distribution, reducing the need for special training in their use.