Aqueous dental glass ionomer composition

Patent metadata

Field	Value
Publication number	US-10272017-B2
Application number	US-201715486342-A
Country	US
Kind code	B2
Filing date	Apr 13, 2017
Priority date	Apr 15, 2016
Publication date	Apr 30, 2019
Grant date	Apr 30, 2019

Abstract

An aqueous dental glass ionomer composition comprising (A) a reactive particulate glass, (B) a water-soluble polymer comprising acidic groups, which is reactive with the particulate glass in a cement reaction, (C) a water-soluble, hydrolysis-stable monomer having a single polymerizable double bond and optionally a carboxylic acid group or hydroxyl group; (D) a water-soluble, hydrolysis-stable polymerizable crosslinker having at least two polymerizable carbon-carbon double bonds; and (E) a polymerization initiator system.

First claim

The invention claimed is:

1. An aqueous dental glass ionomer composition comprising
(A) a reactive particulate glass,
(B) a water-soluble polymer comprising acidic groups, which is reactive with the particulate glass in a cement reaction,
(C) a water-soluble, hydrolysis-stable monomer having a single polymerizable double bond and optionally a carboxylic acid group or hydroxyl group;
(D) a water-soluble, hydrolysis-stable polymerizable crosslinker having at least two polymerizable carbon-carbon double bonds; and
(E) a polymerization initiator system;
wherein the water-soluble polymer comprising acidic groups according to (B) does not contain polymerizable double bonds; whereby the water-soluble polymer comprising acidic groups does not react with the water-soluble monomer according to (C) or the water-soluble, hydrolysis-stable polymerizable crosslinker according to (D), and wherein the water-soluble polymer comprising acidic groups has a molecular weight M w of from 10 3 to 10 6 Da.

2. The aqueous dental glass ionomer composition according to claim 1 , further comprising by at least one of the following features:
the aqueous dental glass ionomer composition does not comprise a polymerizable polymer having polymerizable double bond(s);
the water-soluble polymer comprising acidic groups according to (A) (B) does not comprise pendant β-dicarbonyl group(s);
the aqueous dental glass ionomer composition does not comprise at least one of the following components: unmodified polyacrylic acid as water-soluble polymer according to (B), acrylic acid as water-soluble monomer according to (C) and/or N,N′-diethyl-1,3-bisacrylamido-propan (BADEP) as crosslinker according to (D).

3. The aqueous dental glass ionomer composition according to claim 1 , wherein the water-soluble, hydrolysis-stable monomer according to (C) has a molecular weight of at most 600 Da, and/or wherein the water-soluble, hydrolysis-stable polymerizable crosslinker according to (D) is a bis(meth)acryl amide.

4. The aqueous dental glass ionomer composition according to claim 1 , further comprising at least one of the following features:
the water-soluble, hydrolysis-stable monomer according to (C) is contained in an amount of from 1 to 10 percent by weight based on the total weight of the aqueous dental glass ionomer composition;
water-soluble, hydrolysis-stable polymerizable crosslinker having at least two polymerizable carbon-carbon double bonds according to (D) is contained in an amount of from 1 to 10 percent by weight based on the total weight of the aqueous dental glass ionomer composition;
the aqueous dental glass ionomer composition according to any one of the preceding claims, which further comprises (E) a non-reactive filler.

5. The aqueous dental glass ionomer composition according to claim 1 , wherein the water-soluble polymer comprising acidic groups is obtainable by polymerizing a mixture containing one or more polymerizable monomers represented by the general formula (1a):

wherein
R 1 is a hydrogen atom, a —COOZ group, a linear C 1-6 or branched or cyclic C 3-8 alkyl group which may be substituted with a COOZ group, or a C 6-10 aryl group which may be substituted with a —COOZ group;
R 2 is a hydrogen atom, a —COOZ group, or a linear C 1 -6 or branched or cyclic C 3-8 alkyl group which may be substituted with a —COOZ group;
A* is a single bond, or a linear C 1-6 or branched or cyclic C 3-8 alkylene group, wherein if the carbon number of the alkylene group is two or more, then the alkylene group may contain 1 to 3 heteroatoms, wherein each heteroatom is located in between two carbon atoms of the alkylene carbon chain, which heteroatoms are selected from an oxygen atom, nitrogen atom, and sulfur atom, and/or which alkylene group may contain, if its carbon number is two or more, in between two carbon atoms of the alkylene carbon chain 1 to 3 groups selected from an amide bond or a urethane bond;
Z which may be the same or different, independently represents a hydrogen atom, a metal ion, a protecting group for a carboxylic acid group, or the Z forms with a further —COOZ group present in the molecule an intramolecular anhydride group.

6. The aqueous dental glass ionomer composition according to claim 5 , wherein the mixture further comprises a copolymerizable monomer represented by the general formula (2):

wherein
R 3 is a hydrogen atom or a linear C 1-6 or branched or cyclic C 3-8 alkyl group which may be substituted with a —COOZ′ group;
X is a protected hydroxyl or amino group, or a hydrocarbon group having 1 to 20 carbon atoms, which is substituted by a hydroxyl and/or amino group which may carry a protecting group, wherein the hydrocarbon group may contain 1 to 6 heteroatoms, which heteroatoms are selected from an oxygen atom, nitrogen atom, and sulfur atom, and/or which hydrocarbon group may contain a group selected from an amide bond or a urethane bond and which hydrocarbon group may further be substituted by up to 6 groups selected from —COOZ′, amino groups and thiol groups;
Y is a hydrogen atom, a —COOZ′ group, or a hydrocarbon group having 1 to 20 carbon atoms, wherein the hydrocarbon group may contain 1 to 6 heteroatoms, which heteroatoms are selected from an oxygen atom, nitrogen atom, and sulfur atom, and/or which hydrocarbon group may contain a group selected from an amide bond or a urethane bond and which hydrocarbon group may further be substituted by up to 6 groups selected from —COOZ′, amino groups, hydroxyl groups and thiol groups;
Z′ which may be the same or different, independently represents a hydrogen atom, a metal ion, a protecting group for a carboxylic acid group, or the Z′ forms with a further —COOZ′ group present in the molecule an intramolecular anhydride group.

7. The aqueous dental glass ionomer composition according to claim 1 , wherein the water-soluble, hydrolysis-stable monomer according to (C) is a compound represented by the general formula (3):

wherein
A # is a single bond or a linear C 1-15 or branched or cyclic C 3-15 alkylene group, wherein if the carbon number of the alkylene group is two or more, then the alkylene group may contain 1 to 3 heteroatoms, wherein each heteroatom is located in between two carbon atoms of the alkylene carbon chain, which heteroatoms are selected from an oxygen atom, nitrogen atom, and sulfur atom, and/or which alkylene group may contain, if its carbon number is two or more, in between two carbon atoms of the alkylene carbon chain 1 to 3 groups selected from an amide bond or a urethane bond; preferably, A # is a single bond or a linear C 1-6 or branched or cyclic C 3-5 alkylene group;
R 4 is a hydrogen atom, a —COOZ # group, or a linear C 1-6 or branched or cyclic C 3-8 alkyl group which may be substituted with a —COOZ # group;
R 5 represents a hydrogen atom, —COOM, a linear C 1 to C 18 or branched C 3 to C 18 alkyl group which may be substituted with a CM cycloalkyl group, a C 8-14 aryl or C 3-14 heteroaryl group, —OM*, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M, a C 3 to C 18 cycloalkyl group which may be substituted with a C 1-16 alkyl group, a C 8-14 aryl or C 3-14 heteroaryl group, —OM*, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M, or a C 5 to C 18 aryl or C 3 to C 18 heteroaryl group which may be substituted with —OM*, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M,
G # is —O

Assignees

• Dentsply Sirona Inc

Inventors

• Renn Caroline
• Elsner Oliver
• Szillat Florian
• Klee Joachim
• Weber Christoph
• Walz Uwe
• Scheufler Christian
• Lichkus Andrew
• Jin Xiaoming

Classifications

• A61K6/62 Primary

  Photochemical radical initiators · CPC title

• A61K6/77

  Glass · CPC title

• A61K6/889 Primary

  Polycarboxylate cements; Glass ionomer cements · CPC title

• A61K6/887

  Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• A61K6/0052

  Human Necessities · mapped topic