Dental primer formulation

Patent metadata

Field	Value
Publication number	US-9974716-B2
Application number	US-201414775986-A
Country	US
Kind code	B2
Filing date	Feb 19, 2014
Priority date	Mar 15, 2013
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

Primer formulation which contains (1) at least one alkoxysilane monomer of the general formula R 1 n Si(OR 2 ) 4-n (I), wherein R 1 stands for an organic residue which contains at least one ethylenically unsaturated, polymerizable group, R 2 stands for a C 1 -C 8 alkylorganic residue and n is 1, 2 or 3, wherein the residues R 1 and R 2 can each be the same or different; (2) at least one polyhydrogen fluoride salt of the general formula (R 9 ) + (H x-1 F x ) − z (II), wherein R 9 stands for a metal cation from the series of the alkali, alkaline earth or transition metals or for an ammonium ion of the formula (R 5 )(R 6 )(R 7 )(R 8 )N + , in which R 5 R 6 R 7 and R 8 each independently of each other stand for H or C 1 to C 12 alkyl, C 3 to C 12 alkenyl or C 6 -C 12 aryl residues, wherein R 5 , R 6 , R 7 and R 8 can be the same or different, and wherein two of these residues can be bound together to form a heterocycle together with the nitrogen atom and wherein three of the residues and the nitrogen atom can together form a pyridinium ion, x is an integer from 2 to 5, preferably 2 to 4, in particular 3, z corresponds to the valence of the cationic residue R 9 , (3) organic solvent, and (4) water.

First claim

The invention claimed is:

1. Primer formulation comprising
(1) at least one alkoxysilane monomer of the general formula (I)
R 1 n Si(OR 2 ) 4-n   (I),

in which
R 1 stands for an organic residue which contains at least one ethylenically unsaturated, polymerizable group,
R 2 stands for a C 1 -C 8 alkylorganic residue and
n is 1, 2 or 3,

wherein the residues R 1 and R 2 can each be the same or different;
(2) at least one polyhydrogen fluoride salt of the general formula (II)
(R 9 ) + (H x-1 F x ) − z   (II),

in which
R 9 stands for a metal cation from the series of the alkali, alkaline earth or transition metals or for an ammonium ion of the formula (R 5 )(R 6 )(R 7 )(R 8 )N + , in which R 5 , R 6 , R 7 and R 8 each independently of each other stand for H or C 1 - to C 26 alkyl, C 3 to C 26 alkenyl or C 6 -C 26 aryl residues, wherein R 5 , R 6 , R 7 and R 8 can be the same or different, and wherein two of these residues can be bound together to form a heterocycle together with the nitrogen atom and wherein three of the residues and the nitrogen atom can together form a pyridinium ion,
x is an integer from 2 to 5,
z corresponds to the valence of the cationic residue R 9 ,
(3) organic solvent, and
(4) water,

wherein the primer formulation is for use in dentistry.

2. Primer formulation according to claim 1 , in which at least one or all variables have one of the following meanings:
Formula (I):
R 1 =a residue with the following formula:

in which
R 1a =H or phenyl;
R 1b =H or methyl;
R 1c is absent or is C 1 -C 16 alkyl;
X is absent or is —CO—O— or —CO—NH—, wherein X is absent when R 1c is absent;

R 2 =H or C 1 to C 2 alkyl and
n=1 or 2,

wherein the residues R 1 and R 2 can each be the same or different;
Formula (II)
x=an integer from 2 to 4,
z=1
R 9 =an ammonium ion of the formula (R 5 )(R 6 )(R 7 )(R 8 )N + , wherein R 5 , R 6 , R 7 and R 8 independently of each other mean H, C 1 -C 4 alkyl.

3. Primer formulation according to claim 2 , wherein in Formula (I):
R 1a =H;
R 1b =methyl;
R 1c =C 1 -C 3 alkyl;
X=—CO—O— or —CO—NH—
R 1 and R 2 are the same;

in Formula (II)
x=3,
R 5 , R 6 , R 7 and R 8 are the same.

4. Primer formulation according to claim 2 , wherein in Formula (II)
R 5 =R 6 =R 7 =R 8 =butyl.

5. Primer formulation according to claim 1 , which as solvent contains an alcohol, a ketone, an ester or a mixture thereof.

6. Primer formulation according to claim 5 , which comprises an alcohol which is selected from one or more of methanol, ethanol, n-propanol, propanol, and t-butanol.

7. Primer formulation according to claim 5 , which comprises a ketone which is selected from one or more of acetone, methyl ethyl ketone.

8. Primer formulation according to claim 5 , which comprises an ester which is ethyl acetate.

9. Primer formulation according to claim 1 , which contains no free hydrofluoric acid (HF).

10. Primer formulation according to claim 1 , which additionally contains at least one phosphoric or pyrophosphoric acid ester monomer of Formula (III):
O═P(OR 3 ) m (OR 4 ) 3-m   (III),

in which
R 3 stands for an organic residue which contains at least one ethylenically unsaturated, polymerizable group,
R 4 stands for H, SiR 3 , P(═O)(OR 14 ) 2 or C 1 to C 16 alkyl, wherein R 14 stands for H, SiR′ 3 or C 1 to C 16 alkyl and wherein R and R′ are each independently of each other C 1 to C 4 alkyl, and
m is 1 or 2,

wherein the residues R 3 and R 4 can each be the same or different, and/or
at least one phosphoric or polyphosphoric acid monomer of the general formula (IIIa):
R 11 [P(═O)(OR 10 ) 2 ] n   (IIIa)

in which
R 11 stands for an organic residue which contains at least one ethylenically unsaturated, polymerizable group,
R 10 stands for a residue selected from H, SiR″ 3 or C 1 to C 16 alkyl, wherein R″ is C 1 to C 4 alkyl, and
n is 1, 2, 3 or 4.

11. Primer formulation according to claim 1 , which additionally contains at least one additive, which is selected from wetting agents, detergents, non-ionic, anionic and/or cationic surfactants, antifoaming agents, stabilizers, antimicrobial additives, fragrances, colorants, preservatives, polymeric thickeners, thixotropic agents and rheology modifiers.

12. Primer formulation according to claim 11 , comprising a detergent selected from one or more of non-ionic, anionic and/or cationic surfactants.

13. Primer formulation according to claim 11 , comprising a polymeric thickener selected from one or more of polyvinyl compounds, polymethacrylates, polyacrylates, polyethers, polyamines, polysilicates, and polysaccharides.

14. Primer formulation according to claim 1 , which additionally contains an alkoxysilane of the general formula (Ia),
(OR 13 ) 3 SiR 12 Si(OR 13 ) 3   (Ia),

in which
R 12 stands for C 1 -C 12 alkylene, C 1 -C 12 heteroalkylene or C 6 -C 12 arylene,
R 13 each independently stands for H or C 1 to C 8 alkyl

wherein the residues R 13 can each be the same or different.

15. Primer formulation according to claim 1 , which contains
(1) 0.05 to 25.0 wt. % of alkoxysilane monomer (I);
(2) 1.0 to 25.0 wt. % of polyhydrogen fluoride salt (II);
(3) 25 to 98.5 wt. % of organic solvent;
(4) 25 to 98.5 wt. % water;
each based on the total weight of the composition.

16. Primer formulation according to claim 15 , which additionally contains
0.005 to 2.5 wt. % of the alkoxysilane (Ia); and/or
0.05 to 25.0 wt. % of phosphoric acid ester monomer (III) and/or
0.05 to 25.0 wt. % of phosphonic acid monomer (IIIa); and/or
0.001 to 10% of additives,
each based on the total weight of the composition.

17. Primer formulation according to claim 15 , which contains
(1) 0.2 to 10.0 wt. % of alkoxysilane monomer (I);
(2) 2.0 to 15.0 wt. % polyhydrogen fluoride salt (II);
(3) 35 to 75 wt. % of organic solvent;
(4) 25 to 98.5 wt. % water;
each based on the total weight of the composition.

18. Primer formulation according to claim 15 , which contains
(1) 0.5 to 5.0 wt. % of alkoxysilane monomer (I);
(2) 5.0 to 10.0 wt. % of polyhydrogen fluoride salt (II);
(3) 45 to 55 wt. % of organic solvent;
(4) 40 to 75 wt. % water;
each based on the total weight of the composition.

19. Primer formulation according to claim 15 , which additionally contains
0.02 to 1.0 wt. % of the alkoxysilane (Ia); and/or
0.2 to 10.0 wt. % of phosphoric acid ester monomer (III) and/or
0.2 to 10.0 wt. % of phosphonic acid monomer (IIIa); and/or
0.1 to 7.5% of additives,
each based on the total weight of the composition.

20. Primer formulation according to claim 15 , which additionally contains
0.05 to 0.5 wt. % of the alkoxysilane (Ia); and/or
0.5 to 5.0 wt. % of phosphoric acid ester monomer (III) and/or
0.5 to 5.0 wt. % of phosphonic acid monomer (IIIa); and/or
1.0 to 5% of additives,
each based on the total weight of the composition.

21. Primer formulation according to claim 1 , wherein x is an integer from 2 to to 4.

22. Primer formulation according to claim 1 , wherein x is 3.

23. Method of use of a primer formulation according to claim 1 comprising applyi

Assignees

• Ivoclar Vivadent Ag

Inventors

• Catel Delphine
• Bock Thorsten
• Salz Ulrich

Classifications

• A61K6/40 Primary

  Primers (for dental adhesives A61K6/30) · CPC title

• A61K6/60 Primary

  comprising organic or organo-metallic additives · CPC title

• A61K6/0029 Primary

  Human Necessities · mapped topic

• A61K6/0047

  Human Necessities · mapped topic