Dental restorative materials based on polymerizable azides and alkynes

Patent metadata

Field	Value
Publication number	US-9333150-B2
Application number	US-201314100207-A
Country	US
Kind code	B2
Filing date	Dec 9, 2013
Priority date	Dec 14, 2012
Publication date	May 10, 2016
Grant date	May 10, 2016

Abstract

The invention relates to a dental restorative material on the basis of at least one compound of Formula I

A-[X-Q-(Y-CG) n ] m    Formula I,

wherein CG represents in each case independently an azide group N 3 or an alkyne group selected from the group consisting of —CR 1 R 2 —C≡CH,

with the proviso that the dental restorative material comprises at least one compound of Formula I comprising an azide group and at least one compound of Formula I comprising an alkyne group.

The invention also relates to the use of the dental restorative materials according to the invention for preparing dental composites, preferably composite blanks, which are suitable in particular for mechanical processing by means of computer-aided processing techniques such as milling and grinding processes, and which are suitable above all for preparing dental restoration materials such as inlays, onlays, crowns, bridges or veneering materials.

First claim

The invention claimed is:

1. Dental restorative material which comprises at least one compound of Formula I
A-[X-Q-(Y-CG) n ] m    Formula I,

wherein
A represents —O—, —N═, —NR 3 —, ═N—N═, —NR 3 —N═, ═N—NR 3 —, —NR 3 —NR 3 — or an m-valent alkylene radical, cycloalkylene radical, heterocycloalkylene radical, arylene radical, heteroarylene radical, mixed alkylene-cyclyl radical or cyclyl-O-cyclyl radical, wherein
alkylene represents in each case independently a linear or branched aliphatic C 1 -C 50 radical which can be interrupted by one or more —O—, —S—, —NR 3 —, —CO—O—, —O—CO—, —O—CO—O—, —CO—NR 3 —, —NR 3 —CO—, —O—CO—NR 3 —, —NR 3 —CO—O— or —NR 3 —CO—NR 3 —,
cycloalkylene represents in each case independently a cycloaliphatic C 3 -C 18 radical,
heterocycloalkylene represents in each case independently a heterocycloaliphatic C 3 -C 18 radical,
arylene represents in each case independently an aromatic C 6 -C 18 radical,
heteroarylene represents in each case independently a heteroaromatic C 3 -C 18 radical,
cyclyl represents in each case independently cycloalkylene, heterocycloalkylene, arylene or heteroarylene and
the indicated radicals in each case independently can carry one or more substituents,

CG represents in each case independently an azide group N 3 or an alkyne group selected from the group consisting of —CR 1 R 2 —C≡CH,

with the proviso that the dental restorative material comprises at least one compound of Formula I comprising an azide group and at least one compound of Formula I comprising an alkyne group as described above,

Q in each case independently is missing or represents an (n+1)-valent linear or branched aliphatic C 1 -C 20 alkylene radical which can be interrupted by one or more —O— or —S—, or a phenylene radical, wherein the indicated radicals in each case independently can carry one or more substituents,
R 1 , R 2 and R 3 in each case independently represent H or a C 1 -C 10 alkyl radical,
X and Y in each case independently are missing or represent —O—, —S—, —NR 3 —, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —CO—NR 3 —, —NR 3 —CO—, —O—CO—NR 3 —, —NR 3 —CO—O— or —NR 3 —CO—NR 3 —,
m in each case independently can assume the values 2 to 6 and
n in each case independently can assume the values 1 to 4, and

wherein the dental restorative material further comprises a catalyst for the azide-alkyne cycloaddition and a light-inducible reducing agent and wherein the catalyst is a copper(II) compound.

2. Dental restorative material according to claim 1 , wherein the copper(II) compound is selected from CuSO 4 , CuCl 2 , CuBr 2 , Cu(OH) 2 , Cu(OAc) 2 , CuO, Cu(ClO 4 ) 2 and Cu(NO 3 ) 2 as well as the hydrates and THF adducts thereof.

3. Dental restorative material according to claim 1 , which comprises as light-inducible reducing agent a photoinitiator selected from the group consisting of Norrish type I photoinitiators, titanocenes and α-diketones.

4. Dental restorative material which comprises at least one compound of Formula I
A-[X-Q-(Y-CG) n ] m    Formula I,

wherein
A represents —O—, —N═, —NR 3 —, ═N—N═, —NR 3 —N═, ═N—NR 3 —, —NR 3 —NR 3 — or an m-valent alkylene radical, cycloalkylene radical, heterocycloalkylene radical, arylene radical, heteroarylene radical, mixed alkylene-cyclyl radical or cyclyl-O-cyclyl radical, wherein
alkylene represents in each case independently a linear or branched aliphatic C 1 -C 50 radical which can be interrupted by one or more —O—, —S—, —NR 3 —, —CO—O—, —O—CO—, —O—CO—O—, —CO—NR 3 —, —NR 3 —CO—, —O—CO—NR 3 —, —NR 3 —CO—O— or —NR 3 —CO—NR 3 —,
cycloalkylene represents in each case independently a cycloaliphatic C 3 -C 18 radical,
heterocycloalkylene represents in each case independently a heterocycloaliphatic C 3 -C 18 radical,
arylene represents in each case independently an aromatic C 6 -C 18 radical,
heteroarylene represents in each case independently a heteroaromatic C 3 -C 18 radical,
cyclyl represents in each case independently cycloalkylene, heterocycloalkylene, arylene or heteroarylene and
the indicated radicals in each case independently can carry one or more substituents,

CG represents in each case independently an azide group N 3 or an alkyne group selected from the group consisting of —CR 1 R 2 —C≡CH,

with the proviso that the dental restorative material comprises at least one compound of Formula I comprising an azide group and at least one compound of Formula I comprising an alkyne group as described above,

Q in each case independently is missing or represents an (n+1)-valent linear or branched aliphatic C 1 -C 20 alkylene radical which can be interrupted by one or more —O— or —S—, or a phenylene radical, wherein the indicated radicals in each case independently can carry one or more substituents,
R 1 , R 2 and R 3 in each case independently represent H or a C 1 -C 10 alkyl radical,
X and Y in each case independently are missing or represent —O—, —S—, —NR 3 —, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —CO—NR 3 —, —NR 3 —CO—, —O—CO—NR 3 —, —NR 3 —CO—O— or —NR 3 —CO—NR 3 —,
m in each case independently can assume the values 2 to 6 and
n in each case independently can assume the values 1 to 4,
and wherein the dental restorative material further which comprises one or more radically polymerizable monomers.

5. Dental restorative material according to claim 4 , which comprises
methyl-, ethyl-, hydroxyethyl-, butyl-, benzyl-, tetrahydrofurfuryl- or isobornyl(meth)acrylate, p-cumyl-phenoxyethylene glycol methacrylate (CMP-1E), bisphenol-A-di(meth)acrylate, Bis-GMA, ethoxylated or propoxylated bisphenol-A-dimethacrylate, UDMA, di-, tri- or tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tetra-(meth)acrylate, glycerol di- or tri(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate (D 3 MA), 1,12-dodecanediol di(meth)acrylate,
and/or
one or more N-mono- or -disubstituted acrylamides, N-ethylacrylamide, N,N-dimethacrylamide, N-(2-hydroxyethyl)acrylamide, N-methyl-N-(2-hydroxyethyl)acrylamide, one or more N-monosubstituted methacrylamides, N-ethylmethacrylamide, N-(2-hydroxyethyl)methacrylamide, N-vinylpyrrolidone, one or more cross-linking allyl ethers,
and/or
one or more cross-linking pyrrolidones, 1,6-bis(3-vinyl-2-pyrrolidonyl)-hexane, one or more cross-linking bisacrylamides, methylene or ethylene bisacrylamide, one or more cross-linking bis(meth)acrylamides, N,N′-diethyl-1,3-bis(acrylamido)-propane, 1,3-bis(methacrylamido)-propane, 1,4-bis(acrylamido)-butane, 1,4-bis(acryloyl)-piperazine,
or a mixture thereof.

6. Dental restorative material which comprises at least one compound of Formula I
A-[X-Q-(Y-CG) n ] m    Formula I,

wherein
A represents —O—, —N═, —NR 3 —, ═N—N═, —NR 3 —N═, ═N—NR 3 —, —NR 3 —NR 3 — or an m-valent alkylene radical, cycloalkylene radical, heterocycloalkylene radical, arylene radical, heteroarylene radical, mixed alkylene-cyclyl radical or cyclyl-O-cyclyl radical, wherein
alkylene represents in each case independently a linear or branched aliphatic C 1 -C 50 radical which can be interrupted by one or more —O—, —S—, —NR 3 —, —CO—O—, —O—CO—, —O—CO—O—, —CO—NR 3 —, —NR 3 —CO—, —O—CO—NR 3 —, —NR 3 —CO—O— or —NR 3 —CO—NR 3 —,
cycloalkylene represents in each case independently a cycloaliphatic C 3 -C 18 radical,
heterocycloalkylene represents in each case independently a heterocycloaliphatic C 3 -C 18 radical,
arylene represent

Assignees

• Ivoclar Vivadent Ag

Inventors

• Moszner Norbert
• Burtscher Peter
• Fischer Urs Karl
• Hirt Thomas
• Schubert Ulrich S
• Hager Martin
• Happ Bobby
• Sandmann Benedict

Classifications

• C07D403/14 Primary

  containing three or more hetero rings · CPC title

• A61K6/891 Primary

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

• A61K6/087 Primary

  Human Necessities · mapped topic