Dental materials with debonding-on-demand properties

Patent metadata

Field	Value
Publication number	US-10213367-B2
Application number	US-201515325142-A
Country	US
Kind code	B2
Filing date	Jul 9, 2015
Priority date	Jul 11, 2014
Publication date	Feb 26, 2019
Grant date	Feb 26, 2019

Abstract

Radically polymerizable dental material, which contains at least one compound of Formula I:

and at least one thermolabile radically polymerizable compound and/or at least one photolabile radically polymerizable compound. The materials are characterized by debonding-on-demand properties.

First claim

The invention claimed is:

1. Radically polymerizable dental material which contains at least one compound of Formula I:

with:
A=H; —CN; a phenyl residue which can carry one or more substituents; or an aliphatic linear or branched C 1 -C 20 alkylene residue which can be interrupted by one or more 1,4-phenylene groups, urethane groups, O or S and which can carry in the terminal position a polymerizable vinyl, (meth)acryloyloxy or (meth)acrylamide group;
R 1 =H, an aliphatic linear or branched C 1 -C 9 alkyl radical, tolyl or phenyl;
L=SO 2 R 3 , wherein R 3 is CH 3 or tolyl;
X=—COO—, —CON(R 10 )— or is absent, wherein the bond to A takes place via O or N and
R 10 =H; or is an aliphatic linear or branched C 1 -C 20 alkylene residue which can be interrupted by one or more O or S and which can carry in the terminal position a polymerizable vinyl, (meth)acryloyloxy, (meth)acrylamide group, —C(═CH 2 )—COOR 11 or —C(═CH 2 )—CO—NR 12 R 13 , wherein R 11-13 in each case independently of each other are a linear or branched C 1-6 residue;
n=an integer from 1 to 6,
and at least one thermolabile radically polymerizable compound and/or at least one photolabile radically polymerizable compound.

2. Dental material according to claim 1 , wherein the variables of Formula I have the following meanings:
A H, —CN, a phenyl residue, an aliphatic linear or branched C 1 -C 15 alkyl residue which can be interrupted by one or more 1,4-phenylene groups, urethane groups or O and which can carry in the terminal position a polymerizable (meth)acryloyloxy group;
R 1 H, phenyl, tolyl, an aliphatic linear C 1 -C 3 alkyl radical;
L SR 2 or SO 2 R 3 , wherein
R 2-3 in each case independently of each other are an aliphatic linear or branched C 1 -C 20 alkylene residue which can be interrupted by O and which can carry in the terminal position a polymerizable (meth)acryloyloxy group or —C(═CH 2 )—COOR 11 , wherein R 11 is a linear or branched C 1-3 radical; or a phenyl residue which can carry one or more substituents;
X —COO— or —CON(R 10 )—, wherein R 10 is methyl, or is absent;
n 1 or 2.

3. Dental material according to claim 2 , wherein the variables of Formula I have the following meanings:
A a saturated, linear aliphatic hydrocarbon residue with 1 to 12 carbon atoms which can be interrupted by one or more 1,4-phenylene groups, urethane groups or O and which can carry a methacryloyloxy group,
X —COO— or —CON(R 10 )—, wherein R 10 is methyl, or is absent;
R 1 H,
n 1 or 2.

4. Dental material according to claim 3 , wherein the variables of Formula I have the following meanings:
A a saturated, linear aliphatic hydrocarbon residue with 6 to 12 carbon atoms which can be interrupted by 1 to 3 O atoms,
X —COO—;
R 1 H,
L SO 2 R 3 , wherein R 3 is CH 3 or tolyl,
n 1 or 2.

5. Dental material according to claim 1 , which contains, as thermolabile radically polymerizable compound, a thermolabile multifunctional (meth)acrylate or (meth)acrylamide and/or, as photolabile radically polymerizable compound, at least one photolabile multifunctional (meth)acrylate or (meth)acrylamide.

6. Dental material according to claim 1 , which contains, as the thermolabile radically polymerizable compound, a monomer which is selected from polyfunctional (meth)acrylates or (meth)acrylamides with at least one thermolabile group between two (meth)acryl or (meth)acrylamide groups, the Diels-Alder adduct from furfuryl methacrylate and N-(3-(methacryloyloxy)propyl)-maleimide, the reaction products of N-hydroxy-(meth)acrylamide with di- or triisocyanates, hexamethylene-1,6-diisocyanate (HDI), 2,2,4-trimethylhexamethylene-1,6-diisocyanate or the HDI trimer, products which can be obtained by the stoichiometric reaction of di- or triisocyanates with 1-hydroxymethylacrylic acid esters, 1-hydroxymethylacrylic acid ethyl ester, with β-keto ester (meth)acrylates or 2-acetoacetoxyethyl methacrylate, thermolabile cross-linking monomers which release gas, the esterification products of azobis(4-cyanovaleric acid) with hydroxyalkyl (meth)acrylates, hydroxyethyl (meth)acrylate, hydroxylpropyl (meth)acrylate, N-(hydroxyalkyl)(meth)acrylamides, N-(5-hydroxypentyl)methacrylamide or N-methyl-N-(2-hydroxyethyl)acrylamide.

7. Dental material according to claim 1 , which contains, as the photolabile radically polymerizable compound, a monomer with a photolabile group which is selected from benzoin ethers, oxyalkylphenylacetophenones, dialkyloxyacetophenones, benzoyl diphenylphosphine oxides, dibenzoyl phenylphosphine oxides, dialkyl benzoyl and dialkyl dibenzoyl germanium derivatives.

8. Dental material according to claim 1 , which contains, as the photolabile radically polymerizable compound, a monomer with one photolabile group and two polymerizable (meth)acrylate groups, bis-(4-methacryloyloxybenzoyldiethyl germanium, bis-{4-[2-(methacryloyloxy)diethylcarbamoyloxybenzoyl}diethyl germanium, bis-[3-(methacryloyloxymethyl)-2,4,6-trimethylbenzoyl]-phenylphosphine oxide or methacrylic acid 2-[2-(4-{2-methyl-2-[2-(methacryloyloxy)ethylcarbamoyloxy]-propionyl}-phenoxy)-ethoxycarbonylamino]ethyl ester.

9. Dental material according to claim 1 , which additionally contains at least one multifunctional (meth)acrylate or a mixture of mono- and multifunctional (meth)acrylates.

10. Dental material according to claim 1 , which additionally contains at least one radically polymerizable, acid-group-containing monomer.

11. Dental material according to claim 1 , which additionally contains at least one initiator for the radical polymerization.

12. Dental material according to claim 1 , which additionally contains an initiator(s), wherein the dental material comprises
0.5 to 60 wt.-% of at least one compound of general formula I,
0.01 to 5.0 wt.-% initiator(s) for the radical polymerization, and
1 to 60 wt.-% difunctional thermo- and/or photolabile (meth)acrylate(s), in each case relative to the total mass of the dental material.

13. Dental material according to claim 12 , which may additionally contain a monofunctional (meth)acrylate(s), a filler(s), an expanding additive(s), a radiation-to-heat converter(s), a solvent(s) and other additive(s), and further contains a multifunctional (meth)acrylate(s), and has the following composition:
(a) 1 to 80 wt.-% multifunctional (meth)acrylate(s),
(b) 0.01 to 5.0 wt.-% wt.-% initiator(s),
(c) 0.5 to 60 wt.-% of at least one compound of general formula I,
(d) 0 to 50 wt. % monofunctional (meth)acrylate(s),
(e) 1 to 60 wt.-% difunctional thermo- and/or photolabile (meth)acrylate(s),
(f) 0 to 80 wt.-% filler(s),
(g) 0 to 40 wt.-% expanding additive(s) and/or radiation-to-heat converters,
(h) 0 to 60 wt.-% solvent(s) and
(i) 0 to 5 wt.-% other additive(s),
in each case relative to the total mass of the dental material.

14. Dental material according to claim 11 , wherein the initiator comprises a photoinitiator.

15. Dental material according to claim 12 , which contains
1.0 to 50 wt.-% of at least one compound of general formula I,
0.1 to 5.0 wt.-% initiator(s) for the radical polymerization, and
5 to 50 wt.-% difunctional thermo- and/or photolabile (meth)acrylate(s), in each case relative to the total mass of the dental material.

16. Dental material according to claim 12 , which contains
1.0 to 40 wt.-% of at least one compound of general formula I
0.1 to 3.0 wt.-% initiator(s) for the radical polymerization, and
5 to 40 wt.

Assignees

• Ivoclar Vivadent Ag
• Univ Wien Tech

Inventors

• Moszner Norbert
• Rist Kai
• Lamparth Iris
• Burtscher Peter
• Gorsche Christian
• Liska Robert

Classifications

• A61K6/887 Primary

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

• A61K6/76

  comprising silicon-containing compounds · CPC title