Method and composition for adhering to tooth structure

Patent metadata

Field	Value
Publication number	US-9427382-B2
Application number	US-90052610-A
Country	US
Kind code	B2
Filing date	Oct 8, 2010
Priority date	Jun 30, 1998
Publication date	Aug 30, 2016
Grant date	Aug 30, 2016

Abstract

A dental adhesive composition has an adhesive component and an activator component. The adhesive composition has a volatile organic solvent component, one or more polymerizable (meth)acrylate compounds optionally containing fillers, and a polymerization photoinitiator. The adhesive component may also be a substantially homogeneous mixture of one or more polymerizable (meth)acrylate compounds and an effective amount of a photoinitiator, without a solvent. The activator component includes an aromatic sulfinate salt and an activator component solvent. A method for adhering a restorative to a dental surface includes preparing the surface for restoration; applying a mixture of an adhesive component and an activator component to the prepared cavity, thereby forming a coated cavity surface; and, applying a direct or indirect dental restorative to the coated cavity surface.

First claim

It is claimed:

1. A dental adhesive composition comprising:
a. from about 5 to about 80 percent by weight of an adhesive component comprising:
(i) at least 35 percent by weight of a volatile organic solvent component;
(ii) at least about 5 percent by weight of three polymerizable (meth)acrylate compounds selected from the group consisting of trimethylolpropane tri(meth)acrylate, diethylene glycol dimethacrylate, and 7,7,9,63,65-hexamethyl-4,13,60,69-tetra-oxo-3,14,19,24,29,34,39,44,49,54,59,70-dodecanaoxa-5,12,61,68-tetra-azadoheptacontane-1,72 diyldimethacrylate;
(iii) an effective amount of a polymerization initiator; and
(iv) optionally a filler component; and

b. from about 20 to about 95 percent by weight of an activator component comprising:
(i) from about 0.1 to about 10 percent by weight of an aromatic sulfinate salt elected from para-toluene sodium sulfinate, para-toluene lithium sulfinate, benzene lithium sulfinate or mixtures thereof, and
(ii) from about 90 to about 99.9 percent by weight of an activator component solvent;

wherein the adhesive component further comprises a multifunctional polymerizable compound having at least three (meth)acrylate moieties and a phosphate moiety;
wherein said adhesive solvent component is selected from the group consisting of ethanol, methanol, isopropanol, dimethyl ketone, ethylmethyl ketone, water, and mixtures thereof;
wherein said activator component solvents is selected from the group consisting of acetone, ethanol, water, dimethyl sulfoxide (DMSO), methylene chloride, chloroform, and mixtures thereof;
wherein said initiator is a photoinitiator that is selected from the group consisting of camphorquinone, diaryliodium metal complex salts, chromophore-substituted halomethyl-s-triazines, phosphine oxide, halomethyl oxadiazoles, and mixtures thereof;
wherein said dental adhesive composition further comprises:
a fluoride release agent; and
a cure additive selected from the group consisting of self-cure and light cure additives and mixtures thereof, such that said additive promotes cure interactions between the composition and a restorative material.

2. A composition as in claim 1 , wherein said three polymerizable (meth)acrylate compound is substantially soluble in said solvent component.

3. A composition as in claim 1 , wherein said initiator is a photoinitiator.

4. A method according to the invention, for adhering a non-amalgam dental restorative to a dental surface, comprises the steps of:
a) preparing the dental surface for restoration;
b) optionally etching the surface with an acid;
c) applying the dental adhesive composition of claim 1 to the prepared surface, thereby forming a coated dental surface; and,
d) applying a non-amalgam dental restorative to the coated dental surface.

5. A method as in claim 4 , wherein the adhesive component of said dental adhesive composition is a substantially homogeneous mixture the three polymerizable (meth)acrylate compounds and an effective amount of a photoinitiator and optionally one or more fillers.

6. A method as in claim 4 , wherein said three polymerizable (meth)acrylate compound are substantially soluble or substantially homogeneously dispersed in adhesive component (a) solvent component.

7. A method as in claim 4 , wherein said step (c) includes applying said dental adhesive composition as a mixture of the adhesive component and the activator component.

8. A method as in claim 4 , wherein said step (c) includes sequentially applying said dental adhesive composition as a mixture of the adhesive component and the activator component.

9. A method according to the invention for adhering an amalgam dental restorative to a dental surface, comprises the steps of:
(a) preparing the surface for restoration;
(b) optionally etching the surface with an acid;
(c) applying the dental adhesive composition of claim 1 to the prepared surface, thereby forming a coated dental surface;
(d) optionally applying a chemically curable dental adhesive to said coated dental surface, wherein the chemically curable adhesive includes an oxidizing agent and a reducing agent; and
(e) applying an amalgam dental restorative to the coated dental surface.

Assignees

• Sang Junjie
• Hammesfahr Paul D
• Dentsply Int Inc

Inventors

• Sang Junjie
• Hammesfahr Paul D

Classifications

• A61K6/887 Primary

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

• A61K6/30

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

• A61K6/847 Primary

  Amalgams · CPC title

• C08L33/04

  Homopolymers or copolymers of esters {(C08L43/04 takes precedence)} · CPC title

• C08L33/00

  Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers · CPC title