Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...
Reexamination Certificate
2000-03-06
2003-08-26
Seidleck, James J. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Compositions to be polymerized by wave energy wherein said...
C522S014000, C522S015000, C522S031000, C522S100000, C522S148000, C522S908000, C522S162000, C522S169000, C522S168000, C522S170000, C522S182000, C522S183000, C523S109000, C523S115000, C523S116000, C523S118000, C523S300000, C424S049000, C424S052000, C424S053000, C424S056000, C427S508000, C427S516000, C427S517000
Reexamination Certificate
active
06610759
ABSTRACT:
CROSS-REFERENCE TO RELATED APPLICATIONS
Not applicable.
FIELD OF THE INVENTION
This invention relates in general to compositions of matter and, more particularly, to polymerizable adhesive compositions that include a cationically polymerizable component, an acidic component, and an initiator capable of initiating cationic polymerization. These compositions may also include a polyol and/or a free radically polymerizable component. The polymerizable compositions of the present invention are useful for a variety of applications, including use as adhesives for bonding to hard tissue and cationically curable or cured restorative materials.
BACKGROUND OF THE INTVENTION
Dental compositions such as composites, sealants, and cements generally will not bond sufficiently to tooth enamel or dentin unless the enamel or dentin is pretreated with an adhesive layer, etchant, and/or primer. Typically, the tooth is etched with an acidic solution, and optionally, this is followed by application of a (meth)acrylate-based pre-adhesive composition that is polymerized using a redox, chemically or photochemically activated free radical initiator to form a layer of adhesive. The dental composition, which is typically a filled (meth)acrylate-based composition, is then placed over the adhesive and polymerized using a free radical initiator system to form a hard, wear-resistant material. The adhesive, therefore, bonds to both the acid-etched tooth and to the dental composition.
(Meth)acrylate-based dental compositions exhibit a relatively high degree of volumetric shrinkage upon polymerization. Accordingly, cationically curable compositions, and hybrid compositions featuring both cationically and free radically curable components, have been suggested as alternatives. Such compositions, which typically include epoxy resins as the cationically curable component, exhibit less shrinkage upon cure than compositions that are made predominately of (meth)acrylate. If such cationically curable components are to be used, the pre-adhesive used to bond such components may contain a substantial number of cationically curable TID groups. However, pre-adhesive compositions containing relatively large amounts of cationically curable groups that have previously been disclosed do not bond well to hard tissues, such as tooth enamel and dentin, because the hard tissue inhibits polymerization of such materials.
An epoxide/polyol polymeric composition that includes a photoinitiator system comprising an iodonium salt, a visible light sensitizer, and an electron donor compound is disclosed by one of the present inventors, with another, in U.S. Pat. No. 5,998,495 (the '495 patent). The '495 patent further suggests that other cationically polymerizable polymers can be incorporated into the epoxide/polyol polymeric composition. U.S. Pat. No. 6,025,406 (the '406 patent) discloses an epoxide polymeric composition that includes a photoinitiator system comprising an iodonium salt, a visible light sensitizer, and an electron donor compound.
U.S. Pat. No. 5,980,253 discloses treating hard tissues by applying a composition that includes a cationically active functional group, a free radically active functional group, and a polymerization initiator capable of initiating free radical polymerization. However, the disclosure specifies that the amount of cationically active functional group present is no greater than about 0.0075 moles per gram of composition.
PCT Application No. PCT/US97/08534 discloses dental compositions comprising a polymerizable component, an acid reactive filler, a hydrophilic component, a polymerization initiator, and an acid. PCT Application No. PCT/US96/16299 discloses dental compositions comprising a polymerizable component, a fluoride-releasing material, a hydrophilic component, a polymerization initiator, and an acid.
Despite the advances resulting from the above-noted polymeric compositions, a need still exists for cationically polymerizable compositions having adhesive properties to hard tissues. Still further, these adhesive compositions should be able to successfully polymerize on the surface of hard tissue to form a strong bond with the hard tissue, yet at the. same time, they should successfully bond to subsequently applied compositions that include cationically active groups.
SUMMARY OF THE INVENTION
The present invention is directed to an adhesive composition that includes a mixture of a cationically polymerizable component, an acidic component, and an initiator capable of initiating cationic polymerization. Preferably, the initiator comprises an iodonium salt, a visible light sensitizer, and an electron donor compound, wherein the initiator has a photoinduced potential greater than or equal to that of N,N-dimethylaniline in a standard solution of 2.9×10
−5
moles/g diphenyl iodoniun hexafluoroantimonate and 1.5×10
−5
moles/g camphorquinone in 2-butanone. This adhesive composition is cationically polymerizable and is able to bond to hard tissue and cationically curable or cured restorative materials.
Additional novel features and advantages of the invention will be set forth in part in the description which follows, and in part will become apparent to those skilled in the art upon examination of the following, or may be learned from the practice of the invention. The objects and advantages of the invention may be realized and attained by means of the compositions particularly pointed out in the appended claims.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT
The present invention is directed to an adhesive composition comprising a cationically polymerizable component, an acidic component, and an initiator capable of initiating cationic polymerization. These components are mixed to form the adhesive composition. These components may be sold unmixed so that the composition can be made just prior to use. The composition results in a polymerized product when one or more of the cationically polymerizable components in the composition are contacted with the initiator under conditions sufficient to promote polymerization ofthe component. This adhesive composition may also include a compound having a reactive olefinic moiety (an unsaturated aliphatic hydrocarbon functional group), a free radically polymerizable component, a polyol, or combinations thereof.
Any cationically polymerizable component or combinations thereof may be used in the adhesive composition of the present invention. As used herein, a “cationically polymerizable component” refers to a compound having a cationically active functional group. This cationically active functional group is a chemical moiety that is activated in the presence of an initiator capable of initiating cationic polymerization such that it is available for reaction with other compounds bearing cationically active functional groups. Examples of cationically polymerizable components include, but are not limited to, epoxy resins, vinyl ethers, oxetanes, spiroothrocarbonates, spiroorthoesters, and combinations thereof. Spiroorthocarbonates are esters of orthocarboxylic acid and have four oxygen atoms bonded to a single carbon atom, with the carbon atom being common to two ring systems.
Epoxy resins have an oxirane ring, which is polymerizable by ring opening. Epoxy resins include monomeric epoxy compounds and epoxides of the polymeric type and can be aliphatic, cycloaliphatic, aromatic or heterocyclic. Epoxy resins generally have, on the average, at least 1 polymerizable epoxy group per molecule, preferably at least about 1.5 and more preferably at least about 2 polymerizable epoxy groups per molecule. The polymeric epoxides include linear polymers having terminal epoxy groups (e.g., a diglycidyl ether of a polyoxyalkylene glycol), polymers having skeletal oxirane units (e.g., polybutadiene polyepoxide), and polymershaving pendent epoxy groups (e.g., a glycidyl (meth)acrylate polymer or copolymer). The epoxides may be provided by one compound or may be mixtures of compounds containing one, two, or more epoxy groups per molecule. The average
Chappelow Cecil C.
Code James
Eick J. David
Oxman Joel D.
Pinzino Charles S.
Curators of the University of Missouri
McClendon Sanza L
Seidleck James J.
Stinson Morrison & Hecker LLP
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