Flavored cyanoacrylate compositions

Details Flavored cyanoacrylate compositions Flavored cyanoacrylate compositions

1999-06-30

2002-03-05

Jones, Dameron L. (Department: 1619)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Biocides; animal or insect repellents or attractants

C424S400000, C424S401000, C424S049000, C424S078310, C424S078350

Reexamination Certificate

active

06352704

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of Invention
The invention relates to flavored monomer and polymer adhesive and sealant compositions, and to their production and use.
2. Description of Related Art
Monomer and polymer adhesives are used in both industrial (including household) and medical applications. Included among these adhesives are the 1, 1-disubstituted ethylene monomers and polymers, such as the &agr;-cyanoacrylates. Since the discovery of the adhesive properties of such monomers and polymers, they have found wide use due to the speed with which they cure, the strength of the resulting bond formed, and their relative ease of use. These characteristics have made the &agr;-cyanoacrylate adhesives the primary choice for numerous applications such as bonding plastics, rubbers, glass, metals, wood, and, more recently, biological tissues.
It is known that monomeric forms of &agr;-cyanoacrylates are extremely reactive, polymerizing rapidly in the presence of even minute amounts of an initiator, including moisture present in the air or on moist surfaces such as animal tissue. Monomers of &agr;-cyanoacrylates are anionically polymerizable or free radical polymerizable, or polymerizable by zwitterions or ion pairs to form polymers. Once polymerization has been initiated, the cure rate can be very rapid.
Medical applications of 1,1-disubstituted ethylene adhesive compositions include use as an alternate and an adjunct to surgical sutures and staples in wound closure as well as for covering and protecting surface wounds such as lacerations, abrasions, bums, stomatitis, sores, and other open surface wounds. When an adhesive is applied, it is usually applied in its monomeric form, and the resultant polymerization gives rise to the desired adhesive bond. When the monomeric form is too fluid at ordinary temperatures, it must be controlled in order to prevent undue escape of the adhesive from any given area to which the adhesive is applied. Additionally, sufficient time must be allowed for the monomeric material to polymerize and thus to bring about the desired bonding action.
It is generally known to add perfumes to &agr;-cyanoacrylates adhesive compositions to control the smell of the compositions. See U.S. Pat. Nos. 4,171,416; 4,321,180; 4,582,648; 5,306,490; 5,480,935; 5,554,365; 5,665,817; 5,730,994; and 5,807,563, all of which disclose adding perfumes to adhesive compositions.
Additionally, U.S. Pat. No. 3,966,902 to Chromecek discloses that polymer complexes composed at least in part of a polymer containing hydrophilic functional groups or a precursor monomer and containing aluminum, zinc or zirconium metal bound in complex form can be prepared. See col. 1, lines 57-62. A portion of the monomer having complex forming groups can be replaced by a monomer that does not contain any complex forming group, such as cyanoacrylates. See col. 2, line 66-col. 3, line 5. The polymer complexes are then prepared by reacting the monomer with an aluminum salt prior to polymerization. See col. 3, line 66-col. 4, line 1. The polymer complexes may incorporate an antiperspirant, a pesticide, a medicine, or a fragrance. See col. 7, line 64- col. 8, line 2. Various formulations of the polymer complexes can incorporate a flavoring or sweetening agent such as natural anise flavor, a fragrance such as oil of orchids perfume essence and the like. See col. 7, line 64-col. 8, line 2. Specific examples of flavors also include peppermint, vanilla and rum. See Example 16. The formulations of complex polymers and an active agent can be applied to various surfaces including plastic, paper, glass, wood, skin and the like. See col. 8, lines 18-22.
Cyanoacrylate compositions for use in medical applications should often be sterile. However, not all medical applications require that the composition be sterile.
For example, it is not necessary for cyanoacrylate compositions for use in the mouth or for use on surface skin to be sterilized prior to application. However, when an additive is to be present in an &agr;-cyanoacrylate composition and the composition is to be sterilized, the additive should be added prior to sterilization. In this manner, the additive can be sterilized as well, and the risk of the additive compromising the sterility is avoided.
Regardless of the type and number of additives, sterilization of &agr;-cyanoacrylate adhesive compositions is often difficult to achieve. For example, widely practiced methods of sterilization, such as dry and moist heat sterilization, ionizing radiation, exposure to gas, and sterile filtration, are often not suitable for use with monomeric cyanoacrylate compositions. Problems arise due to polymerization of the monomer during the sterilization process. In many cases, sterilization-induced polymerization is so severe that the resulting product is unusable. Furthermore, sterilization is more difficult to achieve where other additives are included in the monomeric composition, particularly where the additives may themselves facilitate polymerization.
Methods currently used to package and sterilize &agr;-cyanoacrylate monomer compositions have been developed with the recognition that, to improve efficiency and productivity, the packaging and sterilizing steps should be performed in rapid succession. However, these methods do not provide the desired viscosity of the adhesive compositions. For example, U.S. Pat. No. 5,530,037 to McDonnell et al. discloses that the composition of a sterilized adhesive would be very limited because necessary additives could not be conveniently added and mixed in a controlled fashion.
A need exists for flavored monomer cyanoacrylate adhesive compositions, for medical uses, without sacrificing the performance of the adhesive. The need also exists for a sterile, flavored monomeric adhesive composition that does not require pre-treatment of the flavoring additive prior to its combination with the monomeric adhesive.
SUMMARY OF THE INVENTION
The present invention provides flavored monomeric adhesive compositions comprising a monomer and a flavoring additive, including sterile compositions, and methods of making such compositions. Production of the flavored monomeric composition comprises mixing a flavoring additive with an adhesive-forming monomer such as a 1,1-disubstituted ethylene monomer. Production of the sterile, flavored composition includes placing a mixture of a polymerizable monomer and a flavoring additive in a container, sealing the container and sterilizing the container and the mixture. The flavoring additive is preferably soluble in the monomer at room temperature. A use of the flavored monomeric adhesive composition comprises applying the flavored monomeric adhesive composition to the inside of the mouth, and allowing the monomeric adhesive composition to polymerize.


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