Dental cement composition

A process for the preparation of a water-soluble hydrolysis-stable polymerizable compound of the following formula (1),

• AXn (1)
• wherein
• A is a linker group containing at least n nitrogen atoms and optionally one or more acidic groups,
• X are moieties containing a polymerizable double bond and forming an amide bond with a nitrogen atom of A, which X may be the same or different and are represented by the following formula (2)
• wherein
• R1 and R2 are independent from each other and represent a hydrogen atom, a C1-6 alkyl group or a group —(CH2)m—Z, wherein Z is selected from the group consisting of COOM, OPO3M2, PO3M2, and SO3M, wherein M is independently a hydrogen atom or a metal atom, wherein M is a hydrogen atom or a metal atom, and m is an integer of from 0 to 6;
• L is a bond or a C1-6 alkylene group;
• and
• n is an integer of at least 1;
• provided that at least one X cannot be a (meth)acryl group;
• which comprises
• (i) a step of an addition or condensation reaction of a mixture containing a diamine and a compound having at least two carboxylic acid groups or an anhydride thereof, optionally in the presence of a compound of the following formula (5) for obtaining a polyamide:
• wherein Y is a leaving group or Y forms an intramolecular anhydride group together with a carboxyl group present in R1 or R2 and the adjacent carbonyl group;
• and
• (ii) step of introducing moieties of the formula (2) by reacting the polyamide obtained in step (i) with a compound of formula (5) wherein Y is a leaving group;
• or
• (iii) a step of reacting a mixture containing a diamine and a compound of formula (5) for obtaining an amide;
• and
• (iv) a step of an addition or condensation reaction of a mixture containing the amide obtained in (iii) and a compound having at least two carboxylic acid groups or an anhydride thereof for obtaining the water-soluble hydrolysis-stable polymerizable compound of formula (1).

A hydrolysis-stable polymerizable compound of the following formula (1a),

• AXn (1a)
• wherein
• A is a linker group containing at least n nitrogen atoms and optionally one or more acidic groups,
• X are moieties containing a polymerizable double bond and forming an amide bond with a nitrogen atom of A, wherein the X, which may be the same or different, are represented by the following formula (2a)
• wherein
• R1 and R2 are independent from each other and represent a hydrogen atom, a C1-6 alkyl group or a group —(CH2)m—Z, wherein Z is selected from the group consisting of COOM, OPO3M2, PO3M2, and SO3M, wherein M is independently a hydrogen atom or a metal atom, and m is an integer of from 0 to 6, provided that at least one X cannot be a (meth)acryl group;
• L is a bond or a C1-6 alkylene group;
• and
• n is an integer of at least 2.

A dental composition comprising

• a water-soluble hydrolysis-stable polymerizable compound of the following formula (1),
• AXn (1)
• wherein
• A is a linker group containing at least n nitrogen atoms and optionally one or more acidic groups,
• X are moieties containing a polymerizable double bond and forming an amide bond with a nitrogen atom of A, which X may be the same or different and are represented by the following formula (2)
• wherein
• R1 and R2 are independent from each other and represent a hydrogen atom, a C1-6 alkyl group or a group —(CH2)m—Z, wherein Z is selected from the group consisting of COOM, OPO3M2, PO3M2, and SO3M, wherein M is independently a hydrogen atom or a metal atom, and m is an integer of from 0 to 6,
• L is a bond or a C1-6 alkylene group;
• and
• n is an integer of at least 1;
• provided that at least one X cannot be a (meth)acryl group.

A dental composition comprising

• (i) a water-soluble hydrolysis-stable polymerizable compound of the following formula (1),
• AXn (1)
• wherein
• A is a linker group containing at least n nitrogen atoms and optionally one or more acidic groups,
• X is a moiety containing a polymerizable double bond and forming an amide bond with a nitrogen atom of A, which X may be the same or different and are represented by the following formula (2)
• wherein
• R1 and R2 are independent from each other and represent a hydrogen atom, a C1-6 alkyl group or a group —(CH2)m—Z, wherein Z is selected from the group consisting of COOM, OPO3M2, PO3M2, and SO3M, wherein M is independently a hydrogen atom or a metal atom, and m is an integer of from 0 to 6;
• L is a bond or a C1-6 alkylene group;
• and
• n is an integer of at least 1;
• provided that at least one X cannot be a (meth)acryl group, and
• (ii) an initiator system;
• and optionally
• (iii) a particulate filler.