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Wo 2010/008822 A2 (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date 21 January 2010 (21.01.2010) WO 2010/008822 A2 (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A61L 24/06 (2006.01) C09J 4/00 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, (21) International Application Number: CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, PCT/US2009/048234 DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, 23 June 2009 (23.06.2009) KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (25) Filing Language: English NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, (26) Publication Language: English SE, SG, SK, SL, SM, ST, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: 61/132,844 23 June 2008 (23.06.2008) US (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (63) Related by continuation (CON) or continuation-in-part GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, (CIP) to earlier application: ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, US 11/767,565 (CIP) TM), European (AT, BE, BG, CH, CY, CZ, DE, DK, EE, Filed on 25 June 2007 (25.06.2007) ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, SE, SI, SK, TR), (71) Applicant (for all designated States except US): AD- OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, HEZION BIOMEDICAL, LLC [US/US]; One Meridian MR, NE, SN, TD, TG). Boulevard, Suite 1802, Wyomissing, PA 196 10 (US). Declarations under Rule 4.17: (72) Inventors; and (75) Inventors/Applicants (for US only): ZHANG, Sheng — as to applicant's entitlement to apply for and be granted [CN/US]; 1030 Cedar Hills Court, SE, Lenoir, NC 28645 a patent (Rule 4.1 7(H)) (US). RUIZ, Rafael [US/US]; 3706 Rain Valley Drive, Published: Hudson, NC 28638 (US). — without international search report and to be republished (74) Agents: ROSSI, Joseph, D. et al; Stradley Ronon upon receipt of that report (Rule 48.2(g)) Stevens & Young, LLP, 30 Valley Stream Parkway, Malvern, PA 19355-0481 (US). — with information concerning one or more priority claims considered void (Rule 26bis.2(d)) (54) Title: CYANOACRYLATE TISSUE ADHESIVES WITH DESIRABLE PERMEABILITY AND TENSILE STRENGTH (57) Abstract: A sterilized cyanoacrylate adhesive composition including a cyanoacrylate composition and a cure speed enhancer, wherein said sterilized cyanoacrylate adhesive composition does not cure upon sterilization, and wherein the composition when cured to form a film on a patient's tissue has water vapor transmission rate from about 950 to about 3000g/m 2/day. 184714-3003 CYANOACRYLATE TISSUE ADHESIVES WITH DESIRABLE PERMEABILITY AND TENSILE STRENGTH Inventors: Sheng Zhang Hudson, NC 28638 Citizen of the People's Republic of China Rafael Ruiz Sr. Hudson, NC 28638 Citizen of United States of America Assignee: Adhezion Biomedical, LLC. 506 Pine Mountain Road Hudson, NC (US) 184714-3003 CYANOACRYLATE TISSUE ADHESIVES WITH DESIRABLE PERMEABILITY AND TENSILE STRENGTH CROSS-REFERENCE TO RELATED APPLICATIONS [0001 ] This application is a continuation-in-part of, and claims priority under 35 U.S.C. § 120, to U.S. patent application Serial No. 11/767,565, filed on June 25, 2007, and claims priority under 35 U.S.C. § 119(e) to U.S. patent application Serial No. 61/132,844, filed on June 23, 2008, the disclosures of which are incorporated herein by reference in their entirety. BACKGROUND OF THE INVENTION [0002] (1) Field of the Invention [0003] The present invention relates to cyanoacrylate adhesives. In particular, the present invention relates to cyanoacrylate adhesives with an enhanced cure speed for medical use and that, once cured, exhibit improved permeability and mechanical properties such as, for example, wound closure strength, overlap shear strength, peel adhesive strength, and flexibility. [0004] (2) Description of Related Art [0005] Cyanoacrylate compositions have long been known in the art as excellent adhesives. The cyanoacrylate adhesives are liquid monomers that polymerize on contact with tissue surfaces in an exothermic reaction creating a strong yet flexible film. The polymer film is generally formed rapidly. Liquid cyanoacrylate compositions have found application in medicine for closing wounds and incisions, especially in cases where suturing does not provide satisfactory results because of cyanoacrylate's unique ability to bond living tissue and their long-term bond strength. They have found wide applications as industrial and structural adhesives, consumer products for repair of household items and in the hobby sector for assembly and repair. [0006] It is well known that cyanoacrylate adhesive compositions are very sensitive and careful handling is required to prepare their formulations. In order to extend the 184714-3003 applications of cyanoacrylate adhesives, a variety of additives have been incorporated in their formulations including stabilizers, viscosity modifiers, thixotropic agents, plasticizers, biocompatible agents, and polymerization activators. [0007] Cyanoacrylate polymerization is usually considered as the result of an anionic initiation with water being a sufficiently strong base. In spite of the relatively fast cure speed of cyanoacrylate adhesives, polymerization enhancers have to be incorporated for specific applications. First, the cure speed would be drastically dropped if cyanoacrylate adhesives were applied to acidic substrates such as wood and paper. In this case, the cyanoacrylate adhesives with a faster cure time would offer an option. In addition, a relatively large amount of cyanoacrylate applied in certain cases will result in the slower hardening throughout the adhesives. [0008] In order to enhance the polymerization rate for such applications, a number of efforts have been made by applying accelerators through different methods. For example, a two component system has been used by packaging the cyanoacrylate adhesive and the accelerator separately. The cure speed of cyanoacrylate adhesives is improved. The disadvantage of this method is that the accurate measurement and mixing two components homogeneously are very difficult tasks to achieve since only a tiny amount of accelerators is generally required. [0009] As an example, U.S. Pat. No. 5,928,61 1 to Leung discloses an applicator tip for dispensing a polymerizable material, in which a polymerization accelerator was included. The accelerator initiates polymerization when the polymerizable material is dispensed through the applicator tip. Suitable accelerators include detergent compositions; surfactants, amines, urea, phosphines, alcohols, inorganic bases and salts, sulfur compounds, polymeric cyclic ethers, crown ethers, calixarenes, cyclic and acyclic carbonates, organometallics, and radical. The polymerizable material may also contain an initiator which is inactive until activated by a catalyst in the applicator tip. Initiators activated by stimulation such as heat and/or light are also suitable if the tip and/or applicator is appropriately subjected to such stimulation. [001 0] U.S. Pat. Application No. 2005019643 1 to Narang et al. discloses an applicator tip for an applicator for applying a polymerizable monomelic adhesive 184714-3003 composition that can include a bioactive material, a flavorant, a polymerization initiator, and/or a polymerization rate modifier. It has been discovered that the use of methanol, alone or as a component of a mixture of low boiling point solvents, to apply a polymerization accelerator to an applicator tip used to dispense monomer-containing adhesive compositions, provides an unexpectedly superior distribution profile of the material on, and within, the applicator tip. Applicator tips according to their invention can control the setting time of the polymerized or cross-linked adhesive, extend the shelf life of the monomer and control the flow properties of applied cyanoacrylate adhesives. [001 1] U.S. Pat. No. 4,460,759 to Narang discloses two-component adhesive compositions. One component contains the cyanoacrylate monomer and the second component contains a weakly acidic or weakly basic ionic accelerator consisting of a cation having a pKa of at least 10 and a nucleophilic anion. [0012] Another approach to enhance the cure speed of cyanoacrylate adhesive is to apply the diluted solutions of the accelerators in low-boiling point solvents to the cyanoacrylate adhesives. The accelerator solutions can be added to the substrate in advance or applied when the cyanoacrylate adhesive is still liquid. Japanese Patent Application No. JP-A-03 207 778 discloses the use of solutions of aliphatic, alicyclic and, especially, tertiary aromatic amines as the activators for the curing of cyanoacrylate adhesives. Specific examples included N,N-dimethylbenzylamine, N- methylmorpholine and N,N-diethyltoluidine. Japanese Patent Application No. JP-A- 62 022 877 suggested the use of solutions of lower fatty amines, aromatic amines, and dimethylamine for the same purpose. [0013] British Patent Specification No. 1 230 560 described cyanoacrylate adhesive compositions containing certain substituted heterocyclic compounds as accelerators. The compositions may be presented in a two-part form, the first part comprising the cyanoacrylate adhesive and the second part comprising at least one of the substituted heterocyclic compounds, preferably dissolved in an organic solvent. The heterocyclic compound is invariably present in one part of a two-part composition because iminoethylene-substituted triazines and pyrimido-pyrimidines accelerate the polymerization so rapidly that they must be kept apart from the cyanoacrylate 184714-3003 composition before use. An effective adhesive bond is obtained. However it is not concerned with an activator which is able to initiate polymerization throughout a layer of adhesive.
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