Adhesive dental materials with strongly acidic adhesive polymers

Patent metadata

Field	Value
Publication number	US-9833389-B2
Application number	US-201615214823-A
Country	US
Kind code	B2
Filing date	Jul 20, 2016
Priority date	Jul 22, 2015
Publication date	Dec 5, 2017
Grant date	Dec 5, 2017

Abstract

Radically polymerizable dental material which contains at least one radically polymerizable oligomer or polymer with strongly acidic groups, which has a number-average molecular weight of 1,000 to 200,000 g/mol.

First claim

The invention claimed is:

1. Radically polymerizable dental material which comprises
at least one radically polymerizable oligomer or polymer with strongly acidic phosphonic acid groups, which has a number-average molecular weight of 1,000 to 200,000 g/mol and which is prepared by
radical polymerization of at least one polymerizable phosphonate derivative which is selected from 3-(dimethoxy-phosphoryl)propyl (meth)acrylate, 3-[di(trimethylsilyl)-phosphoryl]propyl (meth) acrylate, 2-(dimethoxy-phosphoryl)ethyl (meth)acrylate, 2-[di(trimethylsilyl)-phosphoryl]ethyl (meth)acrylate, 2-[4-(dimethoxyphosphoryl)-2-oxa-butyl]acrylic acid methyl ester and 2-[4-(dimethoxyphosphoryl)-2-oxa-butyl]acrylic acid ethyl ester, followed by releasing the phosphonic acid groups by reaction with water or methanol, or
by radical polymerization of a monomer mixture comprising at least one of said polymerizable phosphonate derivatives and at least one comonomer which is selected from methyl, ethyl, 2-hydroxyethyl, 2-hydroxypropyl, n-butyl, benzyl, tetrahydrofurfuryl, isobornyl (meth)acrylate and 2-acetoacetoxyethyl methacrylate, followed by releasing the phosphonic acid groups by reaction with water or methanol,
and at least one radically polymerizable, acid group-containing monomer.

2. Dental material according to claim 1 in which the radically polymerizable oligomer or polymer has a number-average molecular weight of 1,000 to 100,000 g/mol.

3. Dental material according to claim 1 in which the radically polymerizable oligomer or polymer has at least one polymerizable group which is selected from (meth)acryl, (meth)acrylamide, vinyl and allyl groups.

4. Dental material according to one of claim 3 in which the proportion of polymerizable groups in the polymer in relation to the strongly acidic groups is 60 mol.-%.

5. Dental material according to claim 1 which comprises at least one further radically polymerizable monomer.

6. Dental material according to claim 5 wherein the at least one further radically polymerizable monomer comprises a mono- or polyfunctional (meth)acrylate, a mixture of mono- or polyfunctional (meth)acrylates, or a mixture of mono- and difunctional (meth)acrylates.

7. Dental material according to claim 1 which additionally comprises an initiator for the radical polymerization.

8. Dental material according to claim 7 wherein the initiator comprises a photoinitiator or a photoinitiator in combination with a peroxide or hydroperoxide.

9. Dental material according to claim 1 which additionally comprises at least one organic or inorganic particulate filler or a mixture thereof.

10. Dental material which comprises
a) 0.1 to 30 wt-% of at least one radically polymerizable oligomer or polymer with strongly acidic phosphonic acid groups, which has a number-average molecular weight of 1,000 to 200,000 g/mol and which is prepared by
radical polymerization of at least one polymerizable phosphonate derivative which is selected from 3-(dimethoxy-phosphoryl)propyl(meth)acrylate, 3-[di(trimethylsilyl)-phosphoryl]propyl(meth)acrylate, 2-(dimethoxy-phosphoryl)ethyl (meth)acrylate, 2-[di (trimethylsilyl)-phosphoryl]ethyl (meth)acrylate, 2-[4-(di methoxyphosphoryl)-2-oxa-butyl]acrylic acid methyl ester and 2-[4-(di methoxyphosphoryl)-2-oxa-butyl]acrylic acid ethyl ester, followed by releasing the phosphonic acid groups by reaction with water or methanol, or
by radical polymerization of a monomer mixture comprising at least one of said polymerizable phosphonate derivatives and at least one comonomer which is selected from methyl, ethyl, 2-hydroxyethyl, 2-hydroxypropyl, n-butyl, benzyl, tetrahydrofurfuryl, isobornyl (meth)acrylate and 2-acetoacetoxyethyl methacrylate, followed by releasing the phosphonic acid groups by reaction with water or methanol,
b) 0.01 to 10 wt.-% initiator(s),
c) 1 to 40 wt.-% acidic radically polymerizable monomer(s),
d) 1 to 80 wt.-% radically polymerizable monomer(s), and
e) 0 to 70 wt.-% filler(s) and optionally
f) 0 to 70 wt.-% solvent.

11. Dental material according to claim 10 which comprises
a) 1 to 30 wt.-% of at least one acidic polymer,
b) 0.1 to 3.0 wt.-% initiator(s),
c) 2 to 30 wt.-% acidic radically polymerizable monomer(s),
d) 1 to 60 wt.-% radically polymerizable monomer(s), and
e) 0 to 20 wt.-% filler(s) (adhesive) or 10 to 70 wt. % filler(s) (adhesive cement) and optionally
f) 0 to 60 wt.-% solvent.

12. Dental material according to claim 10 which comprises
a) 2 to 20 wt.-% of at least one acidic polymer,
b) 0.5 to 3.0 wt.-% initiator(s),
c) 5 to 20 wt.-% acidic radically polymerizable monomer(s),
d) 5 to 50 wt.-% radically polymerizable monomer(s), and
e) 0 to 20 wt.-% filler(s) (adhesive) or 10 to 70 wt. % filler(s) (adhesive cement) and optionally
f) 0 to 50 wt.-% solvent.

13. Dental material according to claim 10 for use as adhesive or adhesive coating material which comprises
a) 0.1 to 30 wt.-% at least one acidic polymer,
b) 0.01 to 10 wt.-% initiator(s),
c) 1 to 30 wt.-% acidic radically polymerizable monomer(s),
d) 1 to 80 wt.-% radically polymerizable monomer(s),
e) 0 to 20 wt.-% filler(s), and
f) 0 to 70 wt.-% solvent.

14. Dental material according to claim 10 for use as adhesive or adhesive coating material which comprises
a) 1 to 30 wt.-% at least one acidic polymer,
b) 0.1 to 3.0 wt.-% initiator(s),
c) 2 to 30 wt.-% acidic radically polymerizable monomer(s),
d) 1 to 60 wt.-% radically polymerizable monomer(s),
e) 0 to 20 wt.-% filler(s), and
f) 5 to 60 wt.-% solvent.

15. Dental material according to claim 10 for use as adhesive or adhesive coating material which comprises
a) 2 to 20 wt.-% at least one acidic polymer,
b) 0.5 to 3.0 wt.-% initiator(s),
c) 5 to 20 wt.-% acidic radically polymerizable monomer(s),
d) 5 to 50 wt.-% radically polymerizable monomer(s),
e) 0 to 20 wt.-% filler(s), and
f) 10 to 50 wt.-% solvent.

16. Dental material according to claim 10 for use as adhesive composite cement or filling composite which comprises
a) 0.1 to 30 wt.-% of at least one acidic polymer,
b) 0.01 to 10 wt.-% initiator(s),
c) 1 to 30 wt.-% acidic radically polymerizable monomer(s),
d) 0 to 60 wt.-% radically polymerizable monomer(s), and
e) 10 to 70 wt.-% filler(s).

17. Dental material according to claim 10 for use as adhesive composite cement or filling composite which comprises
a) 1 to 30 wt.-% of at least one acidic polymer,
b) 0.1 to 3.0 wt.-% initiator(s),
c) 2 to 20 wt.-% acidic radically polymerizable monomer(s),
d) 0 to 50 wt.-% radically polymerizable monomer(s), and
e) 20 to 70 wt.-% filler(s).

18. Dental material according to claim 10 for use as adhesive composite cement or filling composite which comprises
a) 2 to 20 wt.-% of at least one acidic polymer,
b) 0.5 to 3.0 wt.-% initiator(s),
c) 2 to 15 wt.-% acidic radically polymerizable monomer(s),
e) 40 to 70 wt.-% filler(s).

19. Dental material according to claim 10 for intraoral use to restore damaged teeth, for intraoral therapeutic use as dental adhesive, coating material, filling composite or cement.

Assignees

• Ivoclar Vivadent Ag

Inventors

• Moszner Norbert
• Bock Thorsten
• Catel Yohann
• Pospiech Doris
• Starke Sandra
• Voit Brigitte

Classifications

• A61K6/76

  comprising silicon-containing compounds · CPC title

• A61K6/889 Primary

  Polycarboxylate cements; Glass ionomer cements · CPC title

• A61K6/30

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

• A61K6/62 Primary

  Photochemical radical initiators · CPC title

• A61K6/20

  Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish · CPC title