β-Ketophosphonic acids and dental materials based thereon

Patent metadata

Field	Value
Publication number	US-9783559-B2
Application number	US-201414898665-A
Country	US
Kind code	B2
Filing date	May 27, 2014
Priority date	Jun 20, 2013
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

β-Ketophosphonic acid according to general formula I:

in which A=an aliphatic C 1 -C 18 radical which can be interrupted by —O—, —S—, —CO—O— or —O—CO—C—; n=1, 2, 3 or 4; m=1 or 2; X=absent or a C 1 -C 10 radical which can be interrupted by —O—, —S—, —CO—C—, —O—CO—NH— or —CO—NR 1 —, wherein R 1 is H or C 1 -C 7 -alkyl; and PG=a group which can undergo free radical polymerization. The β-ketophosphonic acids are suitable in particular for the preparation of dental materials.

First claim

The invention claimed is:

1. Dental material comprising
at least one β-Ketophosphonic acid according to general formula I:

 in which
A=an aliphatic C 1 -C 18 radical which can be interrupted by —O—, —S—, —CO—O— or —O—CO—O—,
n=1, 2, 3 or 4,
m=1 or 2,
X=absent or a C 1 -C 10 radical which can be interrupted by —O—, —S—, —CO—O—, —O—CO—NH— or —CO—NR 1 —, wherein R 1 is H or C 1 -C 6 -alkyl, and
PG=a group which can undergo free radical polymerization; and

at least one initiator for free radical polymerization.

2. Dental material according to claim 1 , wherein
A=an aliphatic C 2 -C 15 radical which can be interrupted by —O—,
n=1 or 2,
m=1 or 2,
X=a C 1 -C 4 -alkylene radical or is absent, and
PG=vinyl, allyl, CH 2 ═CR 2 —CO—Y— or R 3 O—CO—C(═CH 2 )—CH 2 —Y—, wherein Y is O or NR 4 or is absent, R 2 is H or CH 3 and R 3 and R 4 independently of each other are each H or C 1 -C 7 -alkyl.

3. Dental material according to claim 2 , wherein
A=a linear aliphatic C 1 -C 10 radical which can be interrupted by 1 or 2 —O—,
n=1,
m=1 or 2,
X=a C 1 -C 2 radical or is absent,
PG=CH 2 ═CR 2 —CO—Y—, wherein Y is O or NR 4 , or R 3 O—CO—C(═CH 2 )—CH 2 —Y—, wherein Y is O, and wherein R 2 is H or CH 3 , R 3 is CH 3 or C 2 H 5 and R 4 is H, CH 3 or C 2 H 5 .

4. Dental material according to claim 1 , which additionally comprises a further monomer which can undergo free radical polymerization.

5. Dental material according to claim 4 , which comprises as further monomer one or more mono- and/or polyfunctional (meth)acrylic acid derivatives and/or (meth)acrylamide derivatives.

6. Dental material according to claim 1 , which additionally comprises at least one solvent.

7. Dental material according to claim 6 , which comprises as solvent water or a mixture of water and a polar organic solvent.

8. Dental material according to claim 1 , which comprises
a) 0.1 to 50 wt.-% of β-ketophosphonic acid of general formula I,
b) 0.01 to 10 wt.-% of initiator,
c) 0 to 80 wt.-% of further monomer,
d) 0 to 80 wt.-% of filler,
e) 0 to 70 wt.-% of solvent.

9. Dental material according to claim 8 for use as an adhesive, which comprises 0 to 20 wt.-% of filler.

10. Dental material according to claim 9 , which comprises
a) 0.1 to 50 wt.-% of polymerizable β-ketophosphonic acids of general formula I,
b) 0.01 to 10 wt.-% of initiator,
c) 0 to 60 wt.-% of non-acid mono- or multifunctional monomers and/or 0 to 60 wt.-% of acid monomers,
d) 0 to 20 wt.-% of filler,
e) 0 to 70 wt.-% of solvent.

11. Dental material according to claim 8 for use as a cement or filling material, which comprises 20 to 80 wt.-% of filler.

12. Dental material according to claim 1 , for intraoral use as an adhesive, filling material or cement.

13. Method of using a dental material comprising extraorally producing dental restorations or repairing dental restorations with the dental material of claim 1 .

14. Dental material according to claim 1 , wherein
A=a linear C 1 -C 10 radical which can be interrupted by 1 or 2 O atoms,
n=1,
m=1 or 2,
X=a C 1 or C 2 radical or is absent, and
PG=vinyl, allyl, CH 2 ═CR 2 —CO—Y— or R 3 O—CO—C(═CH 2 )—CH 2 —Y—, wherein Y is O or NR 4 or is absent, R 2 is H or CH 3 and R 3 and R 4 independently of each other are each H or C 1 -C 7 -alkyl.

15. Dental material according to claim 9 , which comprises
a) 1 to 40 wt.-% of polymerizable β-ketophosphonic acids of general formula I,
b) 0.1 to 3.0 wt.-% of initiator,
c) 0 to 40 wt.-% of non-acid mono- or multifunctional monomers and/or 0 to 30 wt.-% of acid monomers,
d) 0 to 20 wt.-% of filler,
e) 0 to 60 wt.-% of solvent.

16. Dental material according to claim 9 , which comprises
a) 2 to 30 wt.-% of polymerizable β-ketophosphonic acids of general formula I,
b) 0.01 to 10 wt.-% of initiator,
c) 5 to 40 wt.-% of non-acid mono- or multifunctional monomers and/or 0 to 60 wt.-% of acid monomers,
d) 0 to 20 wt.-% of filler,
e) 0 to 50 wt.-% of solvent.

Assignees

• Ivoclar Vivadent Ag

Inventors

• Moszner Norbert
• Catel Yohann
• Bock Thorsten

Classifications

• A61K6/887

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

• C07F9/3808

  Acyclic saturated acids which can have further substituents on alkyl · CPC title

• C08F230/02

  containing phosphorus · CPC title

• C07F9/3826 Primary

  Acyclic unsaturated acids · CPC title

• C08F222/38

  Amides · CPC title