Aqueous dental glass ionomer composition

Patent metadata

Field	Value
Publication number	US-10610462-B2
Application number	US-201715486335-A
Country	US
Kind code	B2
Filing date	Apr 13, 2017
Priority date	Apr 15, 2016
Publication date	Apr 7, 2020
Grant date	Apr 7, 2020

Abstract

The present disclosure relates to an aqueous dental glass ionomer composition comprising a reactive particulate glass, a water-soluble, polymerizable polymer which is reactive with the particulate glass in a cement reaction, a hydrolysis-stable, water-soluble monomer having a single polymerizable double bond and optionally a carboxylic acid group or hydroxyl group; and a polymerization initiator system, wherein the polymerizable polymer is obtainable by a process comprising a step of polymerizing a mixture comprising a first polymerizable monomer comprising at least one optionally protected carboxylic acid group and a first polymerizable organic moiety, and optionally a second copolymerizable monomer comprising one or more optionally protected primary and/or secondary hydroxyl and/or amino group(s) and a second polymerizable organic moiety, for obtaining an water-soluble polymer; a step of coupling to the water-soluble polymer a compound having a polymerizable moiety and a functional group reactive with an optionally protected carboxylic acid group of repeating units derived from the first polymerizable monomer or an optionally protected hydroxyl and/or amino group of repeating units derived from the second copolymerizable monomer in the water-soluble polymer obtained in step a), wherein the optionally protected carboxylic acid group and the optionally protected hydroxyl and/or amine group are deprotected, so that polymerizable pendant groups are linked to the backbone by ester groups, urethane groups and/or amide groups, and, optionally, a step of deprotecting the protected carboxylic acid group for obtaining a polymerizable polymer.

First claim

The invention claimed is:

1. An aqueous dental glass ionomer composition comprising
(A) a reactive particulate glass,
(B) a water-soluble, polymerizable polymer comprising acidic groups, which is reactive with the particulate glass in a cement reaction, whereby the polymerizable polymer has a polymer backbone and pendant groups having one or more polymerizable carbon-carbon double bonds, wherein the polymerizable polymer is obtained by a process comprising
a) a step of polymerizing a mixture comprising
(i) a first polymerizable monomer comprising at least one optionally protected carboxylic acid group and a first polymerizable organic moiety, and optionally
(ii) a second copolymerizable monomer comprising one or more optionally protected primary and/or secondary hydroxyl and/or amino group(s) and a second polymerizable organic moiety,

for obtaining a water-soluble polymer;
b) a step of coupling to the water-soluble polymer a compound having a polymerizable moiety and a functional group reactive with an optionally protected carboxylic acid group of repeating units derived from the first polymerizable monomer or an optionally protected hydroxyl and/or amino group of repeating units derived from the second copolymerizable monomer in the water-soluble polymer obtained in step a), wherein the optionally protected carboxylic acid group and the optionally protected hydroxyl or amine group are deprotected, so that polymerizable pendant groups are linked to the backbone by ester groups, urethane groups and/or amide groups,
and, optionally, a step of deprotecting the protected carboxylic acid group after step a) or step b), for obtaining a polymerizable polymer;

(C) a hydrolysis-stable, water-soluble monomer having a single polymerizable double bond and optionally a carboxylic acid group or hydroxyl group; said monomer is a compound represented by the general formula (5):

wherein
A ◯ is a single bond, or a linear C 1-6 or branched C 3-8 alkylene group which is bonded to the carbon-carbon double bond in formula (5) via a single bond or a carbonyl group (—CO—), 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;
R ◯ 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 10 represents a hydrogen atom, —COOM, a linear C 1-18 or branched C 3-18 alkyl group which may be substituted with a C 3-6 cycloalkyl group, a C 6-14 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 6-14 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 —OH or a tertiary amino group —NR 11 R* 11 , wherein R 11 and R* 11 independently represent a hydrogen atom, a linear C 1-18 or branched C 3-18 alkyl group which may be substituted with a C 3-6 cycloalkyl group, a C 6-14 aryl or C 3-14 heteroaryl group, —OM*, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M, a C 3-18 cycloalkyl group which may be substituted with a C 1-16 alkyl group, a C 6-14 aryl or C 3-14 heteroaryl group, —OM*, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M, or a C 5-18 aryl or C 3-18 heteroaryl group which may be substituted with —OM*, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M, wherein R 11 and R* 11 may cooperatively form a ring in which R 11 and R* 11 may be linked by a C—C bond or a functional group which may be selected from the group consisting of an ether group, a thioether group, an amine group and an amide group, with the proviso that R 11 and R* 11 cannot both be a hydrogen atom,
m is an integer in a range from 1 to 10,
M* of any one R 10 , R 11 and R* 11 , which M* are independent from each other, each represent a hydrogen atom or a hydroxyl-protecting group, and
M of any one R 10 , R 11 and R* 11 , which M are independent from each other, each represent a hydrogen atom, a carboxyl-protecting group or a metal atom; and
(D) a polymerization initiator system;
wherein the hydrolysis-stable, water-soluble monomer according to (C) does not contain an ester group.

2. The aqueous dental glass ionomer composition according to claim 1 , further comprising at least one of the following features:
the aqueous dental glass ionomer composition does not comprise a non-polymerizable polymer having no polymerizable carbon-carbon double bond(s);
the hydrolysis-stable, water-soluble monomer according to (C) has a molecular weight of at most 600 Da.

3. The aqueous dental glass ionomer composition according to claim 1 , further comprising at least one of the following features:
the hydrolysis-stable, water-soluble 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;
the aqueous dental glass ionomer composition according to claim 1 , which further comprises (E) a non-reactive filler;
the aqueous dental glass ionomer composition according to claim 1 , wherein the molar ratio of first polymerizable monomer to second copolymerizable monomer in the mixture copolymerized in step a) (mol first polymerizable monomer/mol second copolymerizable monomer) is in the range of from 100:1 to 100:50.

4. The aqueous dental glass ionomer composition according to claim 1 , wherein the first polymerizable monomer is represented by a general formula (1):

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.

5. The aqueous dental glass ionomer composition according to claim 1 , wherein the second copolymerizable monomer is represented by a general formula (2):

wherein
R 3 is a hydrogen atom, or a linear C 1-6 or branch

Assignees

• Dentsply Sirona Inc

Inventors

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

Classifications

• A61K6/889 Primary

  Polycarboxylate cements; Glass ionomer cements · CPC title

• C08L33/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C08L33/00

  Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers · CPC title

• C08L33/08

  Homopolymers or copolymers of acrylic acid esters · CPC title