Adhesive bonding and miscellaneous chemical manufacture – Methods – Surface bonding and/or assembly therefor
Reexamination Certificate
2000-09-08
2003-08-19
Page, Thurman K. (Department: 1615)
Adhesive bonding and miscellaneous chemical manufacture
Methods
Surface bonding and/or assembly therefor
C424S078030, C424S078060, C424S078020, C156S325000, C156S326000, C156S329000, C523S212000
Reexamination Certificate
active
06607631
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of Invention
The present invention relates to adhesive compositions, more particularly to polymerizable monomeric adhesive compositions providing reduced coefficients of friction in the polymerized adhesive product. The present invention is also related to methods of making and using such adhesive compositions.
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 (including human) 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 or an adjunct to surgical sutures and/or staples in wound closure, as well as for covering and protecting surface wounds such as lacerations, abrasions, burns, stomatitis, sores, minor cuts and scrapes, and other wounds. When an adhesive is applied to surfaces to be joined, it is usually applied in its monomeric form, and the resultant polymerization gives rise to the desired adhesive bond.
U.S. Pat. No. 5,928,611 to Leung discloses an applicator tip, and adhesive compositions useful therewith, having a polymerization or cross-linking initiator or accelerator disposed on or in a solid support in the applicator tip. The adhesive composition includes polymerizable monomers such as 1,1-disubstituted ethylene monomers and additives, such as polymerization inhibitors or stabilizers, viscosity modifiers, free radical scavengers, pH modifiers, other monomers, formaldehyde scavengers, colorants, lubricants, release or transfer agents, surfactants, defoamants, and plasticizers.
U.S. Pat. No. 5,928,611 to Clark et al. likewise discloses biocompatible cyanoacrylate adhesive compositions that include a polymerizable cyanoacrylate monomer, plasticizing agent, an acidic stabilizing agent and an initiator. The adhesive composition can also include various additives.
Other adhesive compositions are disclosed in, for example, U.S. Pat. Nos. 5,514,371, 5,514,372, 5,575,997, 5,624,669, and 5,582,834 to Leung et al. The adhesive composition can include various additives.
Although the various adhesive compositions have exhibited remarkable success and have found wide-spread use, several disadvantages have been noted with the materials. In particular, a film formed of the adhesive compositions, such as would be applied over a surface to bond adjoining pieces or over a wound or abrasion, sometimes has drawbacks in terms of the coefficient of friction of the film, and the tendency of the film to attract and retain dirt and lint. Both of these drawbacks are particularly evident in the medical field.
For example, when adhesive compositions are used to form polymer films in the medical field, reduced friction and reduced dirt attraction are particularly desired. Reduced friction is desired, for example, to reduce frictional rubbing of the adhesive film by adjoining surfaces such as clothing, bed sheets, prostheses, casts, bandages, and the like. Likewise, reduced dirt attraction is desired to improve the appearance, and perceived cleanliness, of the applied adhesive film.
Furthermore, it is desired in areas of the medical field to provide an adhesive composition that is easier to remove from the application site. While high degrees of adhesion are important in many uses, some uses require that the adhesion be balanced against a need to remove the adhesive without damaging the underlying tissue or skin or other substrate. For example, polymer adhesive films formed from many adhesive compositions are difficult or painful to remove, even from healthy and unbroken skin. However, where the skin or tissue surfaces are injured, removal of the polymeric film therefrom can be painful, and may cause further skin or tissue injury. A polymer adhesive film that is more easily removed, while still retaining its adhesion properties, would be very helpful and desired.
SUMMARY OF THE INVENTION
The present invention overcomes the above-described drawbacks by providing adhesive compositions that include friction reducing or slip enhancing agents. The friction reducing agents provide one or more advantageous benefits to the formed polymeric film. In particular, the friction reducing agents provide one or more of reduced coefficient of friction in the resultant formed polymer film, increased ease of removal of the film, and reduced dirt and lint attraction and retention on the surface of the polymer film. The present invention thereby provides adhesive compositions with increased utility, particularly in the medical field.
In particular, embodiments of the present invention provides a polymerizable monomer adhesive composition, comprising:
a 1,1-disubstituted ethylene monomer; and
at least one slip additive,
wherein said slip additive causes a polymer film formed from said monomer to have a lower coefficient of friction than in an absence of said slip additive.
In embodiments, the present invention provides a two-phase polymerizable monomeric adhesive composition, comprising:
a first phase comprising a 1,1-disubstituted ethylene monomer; and
a second phase comprising a friction reducing agent,
wherein said second phase is soluble in said first phase but said second phase is insoluble or substantially insoluble in a polymer formed from said first phase.
In embodiments, the present invention provides a two-phase polymeric adhesive composition, comprising:
a first phase comprising a polymer formed from a 1,1-disubstituted ethylene monomer; and
a second phase comprising a friction reducing agent,
wherein said second phase is soluble in said 1,1-disubstituted ethylene monomer but is insoluble or substantially insoluble in said polymer.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
Above and other objects of the present invention are achieved by including in the adhesive composition at least one slip additive or friction reducing agent. The slip additive or friction reducing agent is preferably solubilized in both the monomer composition as well as the resulting polymer composition, although solubility in both compositions is not required. In fact, benefits are also provided where the slip additive or friction reducing agent is solubilized in the monomer, but is not soluble (i.e., insoluble) or substantially insoluble in the resulting polymer.
Accordingly, in embodiments of the present invention, the friction reducing agent can be, for example, homogeneously dispersed in the resulting polymer film, or it can form a second phase that is insoluble or substantially insoluble in the polymer. When homogeneously dispersed in the polymer, the friction reducing agent can be, for example, chemically bonded into the polymer network, or it can be homogeneously dispersed without chemical bonding into the polymer network. Likewise, where the friction reducing agent is not soluble or substantially insoluble in the resulting polymer, it can be initially either homogeneously dispersed or not in the polymer network, although it may elute from the polymer network and/or form a distinct second phase either immediately or over time. By “substantially insolub
Badejo Ibraheem T.
D'Alessio Keith R.
Hickey Timothy P.
Jonn Jerry
Knotts Michelle
Closure Medical Corporation
Fubara Blessing
Oliff & Berridg,e PLC
Page Thurman K.
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