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(12) United States Patent (10) Patent No.: US 6,245,933 B1 Malofsky Et Al

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(12) United States Patent (10) Patent No.: US 6,245,933 B1 Malofsky Et Al USOO6245933B1 (12) United States Patent (10) Patent No.: US 6,245,933 B1 Malofsky et al. (45) Date of Patent: Jun. 12, 2001 (54) TRANSESTERIFICATION METHOD FOR 3,975,422 8/1976 Buck. MAKING CYANOACRYLATES 4.012,402 3/1977 Buck. 4,321,180 3/1982 Kimura et al. (75) Inventors: Bernard Malofsky, Bloomfield, CT i. 34: SM s Strahem T. Badejo, Morrisville, 5,359,1012 - - 2 10/1994 Woods etC al..a 5,504,252 4/1996 Klemarczyk. 5,582,834 12/1996 Leung et al.. (73) ASSignee: Closure Medical Corporation, 5,624,669 4/1997 N et al. Raleigh, NC (US) 5,637,752 6/1997 Nakamura et al.. 5,703.267 12/1997 Takahashi et al.. (*) Notice: Subject to any disclaimer, the term of this 6,057,472 5/2000 Sailhan et al. ....................... 558/381 patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days. FOREIGN PATENT DOCUMENTS 726086 4/1980 (SU). (21) Appl. No.: 09/443,298 WO95/33708 12/1995 (WO). (22) Filed: Nov. 19, 1999 * cited by examiner (51) Int. Cl. ..................... C07C 255/23; CO7C 253/30 Primary Examiner Michael G. Ambrose (52) U.S. Cl. .................. 558/381; 558/375; 558/443 ASSistant Examiner Ebenezer Sacket (58) Field of Search ..................................... 558/443, 375, (74) Attorney, Agent, or Firm-Oliff & Berridge, PLC 558/381 f (57) ABSTRACT (56) References Cited An O-cyanoacrylate may be formed by first condensing a U.S. PATENT DOCUMENTS cyanoacetate with paraformaldehyde or formaldehyde; reacting the polymer formed with an alcohol to transesterify 2,721,858 10/1955 Joyner et al.. the polymer; and depolymerizing the polymer to form 2,756,251 7/1956 Joyner et al.. 2,763,677 9/1956 Jeremias. C-cyanoacrylate monomers. 3,559,652 2/1971 Banitt et al. 3,759,264 9/1973 Coover, Jr. et al.. 20 Claims, No Drawings US 6,245,933 B1 1 2 TRANSESTERIFICATION METHOD FOR U.S. Pat. No. 5,637,752 to Nakamura et al. describes MAKING CYANOACRYLATES reaction conditions for the transesterification of a lower alkyl cyanoacetate with an alcohol to form a higher alkyl BACKGROUND OF THE INVENTION cyanoacetate. 1. Field of Invention SU 726,086 describes a process for producing The invention relates to a method for making cyanoacry C-cyanoacrylates by reacting ethyl C-cyanoacrylate mono mer with exceSS alcohol in the presence of an acid or metal lates. chloride catalyst. The process is Simplified and polymeriza 2. Description of Related Art tion of the final product is prevented by conducting the Monomer and polymer adhesives are both used in indus transesterification reaction at 100-140°C. in the presence of trial (including household) and medical applications. Sulfuric or para-toluene Sulfonic acid or Zinc chloride cata Included among these adhesives are 1,1-disubstituted eth lyst. ylene monomers and polymers, Such as C-cyanoacrylates. U.S. Pat. No. 2,756,251 to Joyner et al. describes a Since the discovery of the adhesive properties of Such method for depolymerizing polymeric C-cyanoacrylates. monomers and polymers, they have found wide use due to 15 the Speed with which they cure, the Strength of the resulting bond formed, and their relative ease of use. These charac SUMMARY OF THE INVENTION teristics have made C-cyanoacrylate adhesives the primary The parameters for conducting a condensation reaction of choice for numerous applications Such as bonding plastics, methyl or ethyl cyanoacetate with formaldehyde or rubbers, glass, metals, wood, and, more recently, biological paraformaldehyde to form methyl or ethyl C-cyanoacrylate, tissues. respectively, with maximum yield are well established. Medical applications of 1,1-disubstituted ethylene adhe However, the parameters for the condensation of other Sive compositions, Such as C-cyanoacrylate compositions, cyanoacetates to form other C-cyanoacrylates are not as well include use as an alternate and an adjunct to Surgical Sutures established. In addition, due to Steric considerations, it is and Staples in wound closure as well as for covering and 25 difficult to polymerize higher alkyl cyanoacetates and the protecting Surface wounds Such as lacerations, abrasions, reaction generally results in Smaller oligomers. When crack burns, Stomatitis, Sores, and other Surface wounds. When an ing an oligomer, the last two monomers, which are joined as adhesive is applied, it is usually applied in its monomeric cyanoglutarate, are generally difficult to crack. Thus, if a form, and the resultant polymerization gives rise to the greater number of Smaller oligomers are formed, then more desired adhesive bond. of the Starting material monomers may be lost. As a result, U.S. Pat. No. 5,624,669 to Leung et al. describes a process the final yield of monomers from the overall process may not for making cyanoacrylates. In the method, C.-cyanoacrylates be as ideal as with methyl or ethylcyanoacetates. Therefore, are prepared by condensing a cyanoacetate and either form it is advantageous to form C-cyanoacrylates other than aldehyde or paraformaldehyde in the presence of a catalyst methyl and ethyl C-cyanoacrylates using processes that do at a molar ratio of 0.5-1.5:1 to obtain a condensate, depo 35 not require the condensation of cyanoacetates other than lymerizing the condensation reaction mixture either directly methyl and ethyl cyanoacetates. or after removal of the condensation catalyst to yield crude The present invention provides a proceSS for forming cyanoacrylate; and distilling the crude cyanoacrylate to form C-cyanoacrylates, particularly C-cyanoacrylates of formula a high purity cyanoacrylate. In order to prepare a particular (I) where R' is a carbon containing organic group other than C-cyanoacrylate, the 669 patent discloses making a corre 40 a methyl or ethyl group: sponding cyanoacetate by esterifying cyanoacetic acid with the corresponding alcohol or by transesterifying an alkyl (I) cyanoacetate with the corresponding alcohol before the CN O cyanoacetate undergoes the condensation reaction with the formaldehyde or paraformaldehyde. 45 CH=C-C-OR1. U.S. Pat. No. 4,364,876 to Kimura et al. describes reac tion conditions for forming C-cyanoacrylates by the method The process comprises reacting a particular cyanoacetate, described in the 669 patent. particularly methyl or ethylcyanoacetate, with paraformal U.S. Pat. No. 2,721,858 to Joyner et al. and U.S. Pat. No. 50 dehyde or any other convenient form of formaldehyde to 2,763,677 to Jeremias et al. also describe reaction conditions prepare an O-cyanoacrylate oligomer or polymer. The for forming C-cyanoacrylates from the corresponding cyanoacrylate oligomer or polymer condensation product is cyanoacetate. then transesterified with an alcohol to form a different AS used herein the terms “corresponding” or “corre cyanoacrylate oligomer or polymer before undergoing a Sponds' with reference to a cyanoacetate and an 55 depolymerization to form the target C.-cyanoacrylate. The C-cyanoacrylate means that the same R group is attached to process may be demonstrated in the following reaction oxygen of the carboxyl group in the two compounds. Thus, methylcyanoacetate corresponds to methyl C-cyanoacrylate. Scheme: The term “corresponding alcohol, as used herein, refers to CN O an alcohol having the same R group attached to the hydroxyl 60 formaldehyde group as the corresponding cyanoacetate or C-cyanoacrylate 1) incH-6-OR2 + O condensation has attached to the oxygen of the carboxy group. Thus, paraformaldehyde methyl alcohol corresponds to methylcyanoacetate and to methyl C-cyanoacrylate. in In all of the above mentioned references, the cyanoacetate 65 that undergoes the condensation reaction corresponds to the -ectorOEC-OR2 C-cyanoacrylate that is obtained. US 6,245,933 B1 3 4 -continued Xylenes, carbon tetrachloride and ethylbenzene. During the CN condensation reaction, the Solution may be heated to the azeotropic point. By Such heating, the water may be Selec 2) CH-C--- nROH transesterification tively removed from the reaction medium. OEC-OR2 In an embodiment of the present invention, the conden sation reaction is conducted in the presence of one or more CN basic condensation catalysts. However, one or more acidic - (-CH-C----n ROH condensation catalysts may alternatively be used. Basic catalysts that may be used include, but are not limited to, O=C-OR pyridine, alkali metal or alkaline earth hydroxide, carbonate CN CN O or bicarbonates, Such as Sodium hydroxide, potassium deploymerization | hydroxide, Sodium carbonate, Sodium bicarbonate; metal 3) - (-CH2-g-g- nCH=C-C-OR alcoholates, Such as Sodium methoxide and potassium t-butoxide, trialkylamines, Such as triethylamine; dialkylamines, Such as dimethylamine; alkylamines, Such as 15 methylamine, and primary and Secondary amines, Such as In this reaction scheme, R and R both represent any carbon piperidine, as well as Salts of the various amines. Acidic containing organic group as long as they are different from catalysts that may be used include, but are not limited to, one another. Preferably, n is from 2 to 100. acetic acid, piperidine hydrochloride and Lewis acids, Such Although an embodiment of the invention is directed to a as Zinc chloride or titanium tetrachloride. In addition to more process in which R is a methyl or ethyl group and R' is a traditional acid and basic catalysts, the condensation reac group other than a methyl or ethyl group, the present tion can be conducted in the presence of an acidic or basic invention is not limited to such an embodiment. Thus, R ion-exchange resin, such as an acidic or basic DOWEX may be a group other than a methyl or ethyl group and/or R' ion-exchange resin manufactured and Sold by Dow may be a methyl or ethyl group. Chemical, Midland, Mich. By conducting the transesterification reaction after the 25 condensation reaction, better yield can be obtained. In The cyanoacrylate oligomer or polymer condensation particular, by using lower alkyl cyanoacetates, longer oli product is then transesterified with an alcohol to form a gomers or polymerS may be obtained, which results in different cyanoacrylate oligomer or polymer.
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