Dental adhesive

Patent metadata

Field	Value
Publication number	US-9775786-B2
Application number	US-201414580893-A
Country	US
Kind code	B2
Filing date	Dec 23, 2014
Priority date	Oct 20, 2005
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

A one-part self-etching, self-priming dental adhesive having a pH of at most 2, which comprises an aqueous mixture containing
(i) one or more polymerizable monomers optionally containing an acidic group, (ii) optionally one or more organic or inorganic acids, (iii) a polymerization initiator, and (iv) a thermal polymerisation inhibitor of the following formula (I):

 wherein
R′ 1 represents
a hydrogen atom, or a saturated hydrocarbon group having 1 to 18 carbon atoms.
R′ 2 , which may be the same or different if more than one R′ 2 is present, independently represent
a saturated hydrocarbon group having 1 to 18 carbon atoms, and
c represents an integer of from 1 to 4.

First claim

The invention claimed is:

1. A dental adhesive having a pH of at most 2, comprising an aqueous mixture containing:
(i) one or more polymerizable monomers selected from the group consisting of N,N′-bisacrylamido-N,N′-diethyl-1,3-propane, 3,(4), 8, (9)-bis(acrylamido methyl)tricyclo-5.2.1.0 2,6 decane, ethyl 2-[12-dihydrogen phosphoryl-12,2-dioxamidecyl]acrylate, 2-Acrylamido-2-methyl-propane-sulfonic acid, and acrylic acid;
(ii) optionally one or more organic or inorganic acids;
(iii) a polymerization initiator selected from the group consisting of camphor quinone, bis(2,4,6-trimethylbenzoyl)-phenyl phosphine oxide, and dimethylamino benzoic acid ethyl ester; and
(iv) a thermal polymerization inhibitor selected from the group consisting of tert.-butyl hydroquinone (TBHQ) and tert.-butyl hydroxyanisole (BHA);
wherein the thermal polymerization inhibitor is present at a concentration such that the dental adhesive has a thermal stability at storage for at least 10 days at 60° C.; and
wherein the dental adhesive is one-part self-etching and self-priming.

2. The dental adhesive according to claim 1 , wherein the thermal polymerization inhibitor is tert.-butyl hydroquinone (TBHQ).

3. The dental adhesive according to claim 1 , wherein the thermal polymerization inhibitor is contained in an amount of from 0.01 to 0.5 mol %.

4. The dental adhesive according to claim 1 , wherein the aqueous mixture further contains an organic water soluble solvent selected from the group consisting of alcohols and ketones.

5. The dental adhesive according to claim 1 , which contains the one or more polymerizable monomers in an amount of from 5 to 90 wt. %.

6. The dental adhesive according to claim 1 , which further contains an inorganic filler, an organic filler, or both.

7. The dental adhesive according to claim 1 , wherein the aqueous mixture further contains an organic water soluble solvent selected from the group consisting of ethanol, propanol, butanol, acetone, and methyl ethyl ketone.

8. The dental adhesive according to claim 1 , wherein the polymerization initiator is camphor quinone.

9. The dental adhesive according to claim 1 , wherein the thermal polymerization inhibitor is tert.-butyl hydroxyanisole (BHA).

10. The dental adhesive according to claim 1 , wherein the concentration of the thermal polymerization inhibitor is less than or equal to about 0.147 mol %.

11. A method of using a thermal polymerization inhibitor, the method comprising:
mixing the thermal polymerization inhibitor in an aqueous mixture to form a dental adhesive, the thermal polymerization inhibitor being selected from the group consisting of tert.-butyl hydroquinone (TBHQ) and tert.-butyl hydroxyanisole (BHA), the thermal polymerization inhibitor being present at a concentration such that the dental adhesive has a thermal stability at storage for at least 10 days at 60° C., the aqueous mixture containing:
(i) one or more polymerizable monomers selected from the group consisting of N,N′-bisacrylamido-N,N′-diethyl-1,3-propane, 3, (4),8, (9)-bis(acrylamido methyl)tricyclo-5.2.1.0 2,6 decane, ethyl 2-[12-dihydrogen phosphoryl-12,2-dioxamidecyl]acrylate, 2-Acrylamido-2-methyl-propane-sulfonic acid, and acrylic acid;
(ii) optionally one or more organic or inorganic acids, and
(iii) a polymerization initiator selected from the group consisting of camphor quinone, bis(2,4,6-trimethylbenzoyl)-phenyl phosphine oxide, and dimethylamino benzoic acid ethyl ester; and

wherein the dental adhesive is one-part self-etching, self-priming and has a pH of at most 2.

12. The method according to claim 11 , wherein the concentration of the thermal polymerization inhibitor is less than or equal to about 0.147 mol %.

Assignees

• Dentsply Int Inc

Inventors

• Klee Joachim E
• Lehmann Uwe

Classifications

• A61K6/40 Primary

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

• A61K6/30

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

• A61K6/0029 Primary

  Human Necessities · mapped topic

• A61K6/0023

  Human Necessities · mapped topic

• C08L43/02

  Homopolymers or copolymers of monomers containing phosphorus · CPC title