Self-dental adhesive composition

Patent metadata

Field	Value
Publication number	US-9254246-B2
Application number	US-46260909-A
Country	US
Kind code	B2
Filing date	Aug 6, 2009
Priority date	Feb 7, 2007
Publication date	Feb 9, 2016
Grant date	Feb 9, 2016

Abstract

Self-adhesive dental restorative composition comprising (i) 10 to 40 percent by weight based on the total weight of the composition of a mixture of hydrolysis-stable polymerizable monomers of the following formula (I): wherein R is a m+n valent organic group having 1 to 20 carbon atoms and optionally 1 to 5 atoms selected from the group of nitrogen, oxygen and sulfur atoms; A independently represents a moiety of the following formula (II): wherein L is a hydrogen atom, a C1-6 alkyl group, a C3-8 cycloalkyl group, a C6-14 aryl group or a group of the following formula (III) wherein R′ is a hydrogen atom, a C1-6 alkyl group, a C3-8 cycloalkyl group, or a C6-14 aryl group; X is O, S, NH or NR″ wherein R″ is a C1-6 alkyl group, a C3-8 cycloalkyl group, a C6-14 aryl group; a is 0 or 1; M is a group of the following formula (IV) wherein Y is O, S, NH or NR′″ wherein R′″ is a C1-6 alkyl group, a C3-8 cycloalkyl group, a C6-14 aryl group; b is an integer of from O to 3; c is O or 1; d is an integer of from O to 3; provided that when b is O, then Y cannot be O; x is 0 or 1; y is 0 or 1; provided that x and y cannot be both 1, and provided that x cannot be 1 when L or a group of formula (III) is a hydrogen atom, and provided that when x is 0 then a is also 0, and provided that when y is 0 then b is greater than 0 or c is 0; B independently represents an acidic group; m is an integer of from 1 to 5; n is an integer of 0 to 3; and m+n is at least 2; (ii) 60 to 90 percent by weight based on the total weight of the composition of a filler; and (iii) an initiator system; wherein the portion of monomers of formula (I) wherein n is greater than 0 is at least 1 percent by weight based on the total weight of the mixture.

First claim

The invention claimed is:

1. Self-adhesive dental restorative composition comprising
(i) 10 to 40 percent by weight based on the total weight of the composition of a mixture of hydrolysis stable polymerizable monomers of the following formula (I):
R(A) m (B) n   (I)

wherein
R is a m+n valent organic group having 1 to 20 carbon atoms and optionally 1 to 5 atoms selected from the group of nitrogen, oxygen and sulfur atoms;
A independently represents a moiety of the following formula (II):

wherein
L is a hydrogen atom, a C 1-6 alkyl group, a C 3-8 cycloalkyl group, a C 6-14 aryl group or a group of the following formula (III):

wherein
R′ is a hydrogen atom, a C 1-6 alkyl group, a C 3-8 cycloalkyl group, or a C 6-14 aryl group;
X is O, S, NH or NR″ wherein R″ is a C 1-6 alkyl group, a C 3-8 cycloalkyl group, or a C 6-14 aryl group;
a is 0 or 1;

M is a group of the following formula (IV)

wherein
Y is O, Si NH or NR′″ wherein R′″ is a C 1-6 alkyl group, a C 3-8 cycloalkyl group, or a C 6-14 aryl group;
b is an integer of from 0 to 3;
c is 0 or 1;
d is an integer of from 0 to 3;
provided that when b is 0, then Y cannot be 0;

x is 0 or 1;
y is 0 or 1;
provided that x and y cannot be both 1, and
provided that x cannot be 1 when L or a group of formula (III) is a hydrogen atom, and
provided that when x is 0 then a is also 0, and
provided that when y is 0 then b is greater than 0 or c is 0;

B independently represents an acidic group;
m is an integer of from 1 to 5;
n is an integer of 0 to 3; and
m+n is at least 2;

(ii) 60 to 90 percent by weight based on the total weight of the composition of a filler;
(iii) an initiator system; and
(iv) a reactive diluent selected from the group consisting of (meth) acrylic acid and itaconic acid;
wherein the portion of monomers of formula (I) with n greater than 0 is at least 1 percent by weight based on the total weight of the mixture.

2. The self-adhesive dental restorative composition according to claim 1 , wherein B is selected from a sulfonic acid group, a phosphoric acid ester group, a phosphonic acid group, and a carboxylic acid group.

3. The self-adhesive dental restorative composition according to claim 1 , wherein R is a m+n valent organic group having 1 to 6 carbon atoms.

4. The self-adhesive dental restorative composition according to claim 1 , wherein n is 0, and wherein A is a moiety of formula (II) wherein L is a hydrogen atom, a C 1-5 alkyl group, a C 3-8 cycloalkyl group, or a C 5-14 aryl group, and x is 0.

5. The self-adhesive dental restorative composition according to claim 4 , wherein A is a moiety of formula (II) wherein y is 1, and wherein M is a moiety of formula (IV) wherein Y is NH or NR′″ wherein R′″ is a C 1-6 alkyl group, a C 3-8 cycloalkyl group, or a C 6-14 aryl group, b is 0, c is 1, and d is an integer of from 0 to 3.

6. The self-adhesive dental restorative composition according to claim 1 , wherein n is 0, and wherein A is a moiety of formula (II) wherein x is 1.

7. The self-adhesive dental restorative composition according to claim 6 , wherein L is a group of formula (III) wherein R′ is a C 1-6 alkyl group, a C 3-8 cycloalkyl group, or a C 6-14 aryl group, X is O, S, NH or NR″ wherein R″ is a C 1-6 alkyl group, a C 3-8 cycloalkyl group, or a C 6-14 aryl group, and a is 1.

8. The self-adhesive dental restorative composition according to claim 1 , wherein n is greater than 0, and wherein A is a moiety of formula (II) wherein L is a hydrogen atom, a C 1-6 alkyl group, a C 3-8 cycloalkyl group, or a C 6-14 aryl group, and x is 0.

9. The self-adhesive dental restorative composition according to claim 8 , wherein A is a moiety of formula (II) wherein y is 0, L is a hydrogen atom, and M is a group of formula (IV) wherein Y is 0, b and c are 1, and d is an integer of from 0 to 3.

10. The self-adhesive dental restorative composition according to claim 8 , wherein A is a moiety of formula (II) wherein y is 0, L is a hydrogen atom, and M is a group of formula (IV) wherein Y is NH or NR″ wherein R″ is a C 1-6 alkyl group, a C 3-8 cycloalkyl group, or a C 6-14 aryl group, b is 0, c is 1, and d is an integer of from 0 to 3.

11. The self-adhesive dental restorative composition according to claim 1 , wherein the filler is an inorganic filler comprising a barium alumoborosilicate glass, a strontium alumino sodium fluoro phosphorosilicate glass, La 2 O 3 , ZrO 2 , BiPO 4 , CaWO 4 , BaWO 4 , SrF 2 , and/or Bi 2 O 3 .

12. The self-adhesive dental restorative composition according to claim 1 , further comprising water.

13. The self-adhesive dental restorative composition according to claim 1 , wherein the molecular weight of the compound of formula (I) is in the range of from 100 to 1000.

14. The self-adhesive dental restorative composition according to claim 1 , which has a flexural strength of at least 90 MPa, a compressive strength of at least 300 MPa, and an adhesion to dentine of at least 3 MPa.

15. The self-adhesive dental restorative composition according to claim 1 , which is a one-part composition.

16. The self-adhesive dental restorative composition according to claim 1 , which is a self-adhesive dental composite, a filler containing self-adhesive sealer or a self-adhesive cement.

17. A process for the preparation of a self-adhesive dental restorative composition comprising the step of mixing
(i) 10 to 40 percent by weight based on the total weight of the composition of a mixture of hydrolysis-stable polymerizable monomers of the following formula (I):
R(A) m (B) n   (I)

wherein
R is a m+n valent organic group having 1 to 20 carbon atoms and optionally 1 to 5 atoms selected from the group of nitrogen, oxygen and sulfur atoms;
A independently represents a moiety of the following formula (II):

wherein
L is a hydrogen atom, a C 1-6 alkyl group, a C 3-8 cycloalkyl group, a C 6-14 aryl group or a group of the following formula (III)

wherein
R′ is a hydrogen atom, a C 1-6 alkyl group, a C 3-8 cycloalkyl group, or a C 6-14 aryl group;
X is O, S, NH or NR″ wherein R″ is a C 1-6 alkyl group, a C 3-8 cycloalkyl group, or a C 6-14 aryl group;
a is 0 or 1;

M is a group of the following formula (IV)

Assignees

• Klee Joachim
• Lehmann Uwe
• Glaner Anja
• Dentsply Int Inc

Inventors

• Klee Joachim
• Lehmann Uwe
• Glaner Anja

Classifications

• A61K6/20

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

• A61K6/71 Primary

  Fillers · CPC title

• A61K6/887

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

• A61K6/0017

  Human Necessities · mapped topic

• A61K6/083

  Human Necessities · mapped topic