Dental restorative materials based on polymerizable azides and alkynes

Patent metadata

Field	Value
Publication number	US-9522100-B2
Application number	US-201414569894-A
Country	US
Kind code	B2
Filing date	Dec 15, 2014
Priority date	Dec 15, 2013
Publication date	Dec 20, 2016
Grant date	Dec 20, 2016

Abstract

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

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 or I′

wherein
A represents in each case independently an (m+1)-valent phenylene radical,
R 1 represents in each case independently an aliphatic linear or branched C 1 -C 20 alkyl radical which can be interrupted by —O— or —S—, a phenyl radical which can carry one or more substituents that are selected independently of each other from the group consisting of CH 3 , C 2 H 5 , OH and OCH 3 , or R 3 ,
R 2 represents in each case independently H, an aliphatic linear or branched C 1 -C 20 alkyl radical which can be interrupted by —O— or —S—, or a phenyl radical which can carry one or more substituents that are selected independently of each other from the group consisting of CH 3 , C 2 H 5 , OH and OCH 3 ,
R 3 represents in each case independently —Z—Y—R 2 or —Z—C(═O)—≡-A(R 4 ) m ,
R 4 represents in each case independently —≡—C(═O)—R 3 ,
R 5 represents in each case independently phenyl or R 6 ,
R 6 represents in each case independently —C(═O)—X—R 2 or —C(═O)—X—Z(R 7 )m,
R 7 represents in each case independently —X—C(═O)—≡—R 6 ,
X represents in each case independently O, S, NH or CH 2 , wherein X is missing when R 5 represents phenyl,
Y represents in each case independently —C(O)—O—, —O—C(O)—, O or S,
Z represents an (m+1)-valent aliphatic linear or branched C 1 -C 20 alkylene radical which can be interrupted by —O— or —S—, or a phenylene radical which can carry one or more substituents that are preferably selected independently of each other from the group consisting of CH 3 , C 2 H 5 , OH and OCH 3 , and
m in each case independently can assume the values 1 to 5.

2. Dental restorative material according to claim 1 , wherein in the Formulae I and I′ in each case independently of each other
A represents in each case independently an (m+1)-valent phenylene radical,
R 1 represents in each case independently an aliphatic linear or branched C 1 -C 10 alkyl radical, which can be interrupted by —O— or —S—, or R 3 ,
R 2 represents in each case independently H, an aliphatic linear or branched C 1 -C 10 alkyl radical, which can be interrupted by —O— or —S—,
R 3 represents in each case independently —Z—Y—R 2 or —Z—C(═O)—≡-A(R 4 ) m ,
R 4 represents in each case independently —≡—C(═O)—R 3 ,
R 5 represents in each case independently phenyl or R 6 ,
R 6 represents in each case independently —C(═O)—X—R 2 or —C(═O)—X—Z(R 7 ) m ,
R 7 represents in each case independently —X—C(═O)—≡—R 6 ,
X represents in each case independently O, S, NH or CH 2 , wherein X is missing when R 5 represents phenyl,
Y represents in each case independently —C(O)—O— or —O—C(O)—,
Z represents an (m+1)-valent aliphatic linear or branched C 1 -C 10 alkylene radical, which can be interrupted by —O— or —S—, or a phenylene radical which can carry one or more substituents that are preferably selected independently of each other from the group consisting of CH 3 , C 2 H 5 , OH and OCH 3 , and
m in each case independently can assume the values 1, 2 or 3.

3. Dental restorative material according to claim 1 , which comprises at least one compound of one of Formulae IA to ID

wherein
R 1 represents in each case independently an aliphatic linear or branched C 1 -C 20 alkyl radical which can be interrupted by —O— or —S—, or a phenyl radical which can carry one or more substituents that are selected independently of each other from the group consisting of CH 3 , C 2 H 5 , OH and OCH 3 ,
R 2 represents in each case independently H, an aliphatic linear or branched C 1 -C 20 alkyl radical which can be interrupted by —O— or —S—, or a phenyl radical which can carry one or more substituents that are selected independently of each other from the group consisting of CH 3 , C 2 H 5 , OH and OCH 3 ,
X represents in each case independently O, S, NH or CH 2 ,
Y represents in each case independently —C(O)—O—, —O—C(O)—, O or S,
Z represents an aliphatic linear or branched C 1 -C 20 alkylene radical which can be interrupted by —O— or —S—, or a phenylene radical which can carry one or more substituents that are preferably selected independently of each other from the group consisting of CH 3 , C 2 H 5 , OH and OCH 3 ,
m in each case independently can assume the values 1 to 5, and
n in each case independently can assume the values 2 to 10.

4. Dental restorative material according to claim 3 , wherein in the Formulae IA to ID in each case independently of each other
R 1 represents in each case independently an aliphatic linear or branched C 1 -C 10 alkyl radical, which can be interrupted by —O— or —S—,
R 2 represents in each case independently H, an aliphatic linear or branched C 1 -C 10 alkyl radical, which can be interrupted by —O— or —S—,
X represents in each case independently O, S, NH or CH 2 ,
Y represents in each case independently —C(O)—O— or —O—C(O)—,
Z represents an aliphatic linear or branched C 1 -C 10 alkylene radical, which can be interrupted by —O— or —S—, or a phenylene radical which can carry one or more substituents that are preferably selected independently of each other from the group consisting of CH 3 , C 2 H 5 , OH and OCH 3 ,
m in each case independently can assume the values 1, 2 or 3, and
n in each case independently can assume the values 3 to 8.

5. Dental restorative material according to claim 1 , which further comprises at least one azide of Formula II
A-[X-Q-(Y—N 3 ) n ] m    Formula II

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 selected from C 1 -C 5 alkyl, OH, OCH 3 and OCOCH 3 ,

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 selected from CH 3 , C 2 H 5 , OCH 3 and OCOCH 3 ,
R 3 in each case independently represents 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.

6. Dental restorative material according to c

Assignees

• Ivoclar Vivadent Ag

Inventors

• Moszner Norbert
• Burtscher Peter
• Schubert Ulrich S
• Hager Martin
• Happ Bobby
• Sandmann Benedict

Classifications

• A61K6/891 Primary

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

• C07D251/54 Primary

  Three nitrogen atoms · CPC title

• A61K6/30

  Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives · CPC title

• C08G63/52

  Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation · CPC title

• C07D493/10

  Spiro-condensed systems · CPC title