Composition of 2-Cyanoacrylate, Lewis Acid Metal Salt and Clathrate

http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 http://ip.com/patent/US6830704 (12) United States Patent Tajima et al. US006830704B2 US 6,830,704 B2 Dec. 14, 2004 (10) Patent N0.: (45) Date of Patent: (54) COMPOSITION OF 2-CYANOACRYLATE, LEWIS ACID METAL SALT AND CLATHRATE (75) Inventors: Seitaro Tajima, Aichi (JP); Mitsuyoshi Sato; Aichi (JP) (73) Assignee: Toagosei Co., Ltd., Tokyo (JP) ( * ) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days. (21) Appl. No.: 10/375,364 (22) Filed: Feb. 28, 2003 (65) Prior Publication Data US 2003/0135016 A1 Jul. 17, 2003 Related U.S. Application Data (63) Continuation of application No. 09/545,609, filed o11 Apr. 7, 2000, now Pat. No. 6,547,985. (30) Foreign Application Priority Data Apr. 7, 1999 (JP) ..................................... .. P. 11—100616 (51) Int. Cl.7 ......................... .. B32B 3/06; C08K 65/02; C08K 71/02; C08K 71/03 (52) U.S. Cl. .............................. .. 252/182.12; 428/341; 428/133; 428/378; 428/447; 428/537.1; 528/396; 528/414; 528/416 (58) Field of Search .................. .. 252/182.12; 428/341, 428/133, 355 CN, 378, 447, 537.1; 528/414, 416, 396 (56) References Cited U.S. PATENT DOCUMENTS 4,171,416 A 10/1979 Motegi et al. ............ .. 526/245 4,980,086 A 12/1990 Hiraiwa et al. ........... .. 252/511 5,290,825 A 3/1994 Lazar ....................... .. 523/176 6,294,629 B1 9/2001 0’Dwyer et al. ......... .. 526/297 6,547,985 B1 * 4/2003 Tajima et al. ........ .. 252/182.12 FOREIGN PATENT DOCUMENTS EP 142327 A1 5/1985 GB 2268503 A 1/1994 JP 55-34165 B4 9/1980 JP 60—115676 A 6/1985 JP 3—167279 A 7/1991 * cited by examiner Primary Examiner—Robert Sellers (74) Attorney, Agent, or Firm—Sughrue Mion, PLLC (57) ABSTRACT A 2-cyanoacrylate composition useful as an adhesive con- tains a Lewis acid metal salt comprising a metal such as aluminum, gallium, indium or thalium, and the conjugate base of an acid such as a monohalo-, dihalo- or trihalo- acetate (e.g. aluminum trifluoroacetate salt). Aclathrate such as a crown ether is also present. 10 Claims, No Drawings US 6,830,704 B2 1 COMPOSITION OF 2-CYANOACRYLATE, LEWIS ACID METAL SALT AND CLATHRATE CROSS-REFERENCE TO RELATED APPI JCATIONS This is a continuation of application Ser. No. 09/545,609 filed Apr. 7, 2000 U.S. Pat. No. 6,547,985; the disclosure of which is incorporated herein by reference. FIELD OF THE INVENTION The present invention relates to a 2-cyanoacrylate com- position having excellent surface curability and clearance curability. BACKGROUND OF THE INVENTION 2-Cyanoacrylate compositions undergo instantaneous anionic polymerization to exhibit a high bonding strength. The compositions are hence widely utilized especially as instantaneous adhesives in various industrial fields. However, it is not satisfactory to use the compositions as potting materials, fillers or instantaneous adhesives because the compositions necessitate a considerably prolonged set- ting time with respect to curability in a relatively wide gap between adherends (hereinafter referred to as “clearance curability”) or curability on a surface of an adherent due to overflowing the composition (hereinafter referred to as “surface curability”). For overcoming the problem, various proposals have been made on the use of surface-treating agents which increase the curing rate of 2-cyanoacrylate compositions. For example, JP-B-62-29471 (the term “JP-B” as used herein means an “examined Japanese patent publication”) discloses a composition comprising an N,N-di(lower alkyl) toluidine, saccharin and ascorbic or isoascorbic acid, and JP-B-62-12279 discloses the use of a specific surfactant. JP-B-60-24826 discloses the use of methylolurea which may have been partly alkoxylated, melamine, or a derivative of either. JP-B-54-19416 and JP-B-51-25441 disclose a technique in which an adherend is treated beforehand with N,N-dimethyl-m-toluidine and with a vinyl ether or vinyl thioether, respectively. JP-B-49-12094 discloses a technique in which an adherend surface is treated with a liquid containing an amine, amide or imide, and JP-B-48-44175 discloses a technique in which an adherend surface is treated with a liquid containing a specific heterocyclic compound. JP-B-47-8718 discloses a technique in which an adherend surface is treated beforehand with a liquid containing dim- ethylaniline or/and tris[1-(2-methyl)aziridiyl]phosphine oxide. Furthermore, JP-A-39-844 (the term “JP-A” as used herein means an “unexamined published Japanese patent application”) discloses a technique in which an adherend surface is treated beforehand with an epoxide or diepoxide. Curing accelerators to be added to 2-cyanoacrylate com- positions have also been investigated in order to improve curability. For example, U.S. Pat. No. 4,171,416 discloses the use of a crown ether compound as a curing accelerator. U.S. Pat. Nos. 4,170,585 and 4,377,490 disclose the use of a polyalkylene glycol derivative having a specific structure and a mixture of an aliphatic or aromatic polyol with an aliphatic or aromatic polyether, respectively, as a curing accelerator. U.S. Pat. Nos. 4,386,193 and 5,589,554 disclose the use of a three- or four-arm polyol podand compound having a specific structure and a compound having cyano and carboxy groups, respectively, as a curing accelerator. 10 15 20 30 35 40 45 55 60 65 2 Furthermore, JP-B-5-72946 and JP-A-7-316505 disclose the use of a calixarene compound and an organotitanium compound, respectively, as a curing accelerator. It has further been attempted to improve surface curability and clearance curability by adding photocurability to a 2-cyanoacrylate composition. For example, JP—A—9—249708 discloses the use as an anionic photopolymerization initiator of a metallocene compound comprising a transition metal of Group VIII of the periodic table and aromatic electron system ligands. JP-A-6-299122 and International Publica- tion WO 93/10483 disclose the use of an aromatic azide compound and an inorganic chromium complex, respectively, as an anionic photopolymerization initiator. Furthermore, JP-A-62-57475 discloses a cyanoacrylate- based adhesive composition containing a free-radical pho- topolymerization initiator. However, the techniques described above each have had one or more disadvantages as will be described below, such as poor applicability, poor storage stability and the necessity of an illuminator. Namely, these techniques have been unsatisfactory because the advantage inherent in 2-cyanoacrylate compositions, that the operation can be completed in a short period of time, is lost. The technique in which a surface-treating agent is used is satisfactory in attaining a shortened operation period because it greatly improves surface curability and clearance curability. However, applicability is considerably impaired because two liquids should be applied. Although the technique in which a curing accelerator is used is effective in improving curability in application to closely spaced adherends, it has been unsatisfactory in surface curability and clearance curability. The technique in which photocurability is added is satis- factory in operation period because it can improve surface curability and clearance curability. However, this technique has been unsatisfactory in that it necessitates a light irradia- tion device and that it is unusable for the bonding of adherends having such a structure that irradiation of the bonding surface with light is impossible. Namely, there has been a desire since long before for a 2-cyanoacrylate composition which is usable as one com- ponent and curable at ambient temperature, and not neces- sitating a light irradiation device or the like and which cures in a short period of time even in the case where it is used as a potting material, or has overflowed, or is applied to a relatively wide gap between adherends. SUMMARY OF THE INVENTION The present invention has been made to overcome the above-described disadvantages in the conventional tech- niques. Accordingly, an object of the present invention is to provide a 2-cyanoacrylate composition having excellent surface curability and clearance curability and being effec- tive in shortening the time required for bonding operation. As a result of intensive investigations to overcome the above-described conventional problems, it has been found that all the above-described problems are overcome and surface curability and clearance curability are greatly improved by containing a Lewis acid metal salt comprising a specific metal and a conjugate base comprising an acid having oxygen, and a compound having clathrating ability into a 2-cyanoacrylate. The present invention has been completed based on this finding. The present invention provides a 2-cyanoacrylate com- position comprising (1) a Lewis acid metal salt which US 6,830,704 B2 3 comprises a n1etal selected from the group consisting of zinc, cadmium, mercury, aluminum, gallium, indium and thallium (hereinafter, the metal is referred to as “specific metal”) and a conjugate base comprising an acid having oxygen, wherein the metal is bonded to the conjugate base through an oxygen atom, and (2) a compound having clathrating ability. In connection with the incorporation of a Lewis acid metal salt into a 2—cyanoacrylate, J P—W—63—500247 (the term “JP-W” as used herein means an “unexamined published PCT application”) discloses a technique in which a metal salt such as FeCl3 or CdCl2 is incorporated as an inhibitor into a 2-cyanoacrylate. However, those metal salts, in which the central atom is directly bonded to halogen atoms, have an exceedingly high acidity and are utterly different from the Lewis acid metal salt used in the present invention, which is intended to improve curing rate. Furthermore, J P-A-62- 89780 discloses a technique in which an electroconductive powder of, e.g., silver, copper, nickel or aluminum is incor- porated into a cyanoacrylate together with a basic substance such as a crown ether. However, those metals used in this technique are solid and remain undissolved in the cyanoacrylate. This technique therefore is utterly different from the invention, in which the metal salt used is soluble in cyanoacrylatcs. DETAILED DESCRIPTION OF THE INVENTION Lcwis Acid Mctal Salt: The Lewis acid metal salt used in the present invention is a metal salt which is capable of accepting an electron pair and contains a specific metal. The Lewis acid metal salt used in the present invention comprises the specific metal and the conjugate base of either a specific organic acid or perchloric acid, wherein the specific metal must be bonded to an oxygen atom of the conjugate base. The conjugate base does not contain any functional group which initiates polymerization of 2—cyanoacrylate, such as amino group or mercapto group. Although the base may be an anhydride or a hydrate, it is a normal salt. Abasic salt is not included in the definition of the Lewis acid metal salt used in the present invention. Preferred examples of the acid used for forming the conjugate base include (1) perchloric acid, (2) an aliphatic carboxylic acid, an aromatic carboxylic acid, an aliphatic sulfonic acid or an aromatic sulfonic acid, and ('3) an aliphatic carboxylic acid, an aromatic carboxylic acid, an aliphatic sulfonic acid or an aromatic sulfonic acid, each being substituted with one or more halogen atoms or one or more cyano or alkyl groups. The conjugate base derived from any of thosc acids is cffcctivc in accomplishing the object of the present invention. Specific examples of the Lewis acid metal salt used in the present invention are listed below, but the metal salt is not limited to those. Lewis Acid Metal Salt Containing Zinc: Examples of the Lewis acid metal salt containing zinc include zinc acetate, zinc monofluoroacetate, zinc difluoroacetate, zinc trifluoroacetate, zinc monochloroacetate, zinc dichloroacetate, zinc trichloroacetate, zinc monobromoacetate, zinc dibromoacetate, zinc tribromoacetate, zinc monoiodoacetate, zinc diiodoacetate, zinc triiodoacetate, zinc cyanoacetate, zinc propionate, zinc U.-fluoropropionate, zinc [5-fluoropropionate, zinc oL,oL‘-difluoropropionate, zinc o.,B-difluoropropionate, zinc [3,[3‘-difluoropropionate, zinc 0L-chloropropionate, zinc [3-chloropropionate, zinc oL,oL'- 10 15 20 30 35 40 45 55 60 65 4 dichloropropionate, zinc o.,[3-dichloropropionate, zinc [3,[3'- dichloropropionate, zinc 0.-bromopropionate, zinc [3-bromopropionate, zinc o.,oL‘-dibromopropionate, zinc o.,[3- dibromopropionate, zinc [3,[3'-dibromopropionate, zinc ot-iodopropionate, zinc [3-iodopropionate, zinc oL,o.‘- diiodopropionate, zinc oL,[3-diiodopropionate, zinc [3,[3'- diiodopropionatc, zinc [3,[3,[3-triiodopropionatc, zinc butyrate, zinc isobutyrate, zinc valerate, zinc caproate, zinc heptanoate, zinc caprylate, zinc 2-ethylhexanoate, zinc acrylate, zinc or-fluoroacrylate, zinc [3-fiuoroacrylate, zinc ot-chloroacrylate, zinc [3-chloroacrylate, zinc oL,B- dichloroacrylate, zinc [3,[3‘-dichloroacrylate, zinc (x—bromoacrylate, zinc [3—bromoacrylate, zinc oL,[3— dibromoacrylate, zinc B,[3‘-dibromoacrylate, zinc tribromoacrylate, zinc (1-iodoacrylate, zinc [3-iodoacrylate, zinc cx,[3—diiodoacrylate, zinc [3,[3‘—diiodoacrylate, zinc crotonate, zinc 0.-chlorocrotonate, zinc B-chlorocrotonate, zinc y-chlorocrotonate, zinc cx-bromocrotonate, zinc [3-bromocrotonate, zinc y-bromocrotonate, zinc 0t,B— dichlorocrotonate, zinc u.,[3-dibromocrotonate, zinc y,y,y- trichlorocrotonate, zinc methacrylate, zinc [3-bromomethacrylate, zinc formate, zinc chloroformate, zi11c cyclopentanecarboxylate, zi11c 1-methylcyclopentanecarboxylate, zinc 2-methylcyclopentanecarboxylate, Zinc 3-methylcyclopentanecarboxylate, zinc cyclohexanecarboxylate, zinc 1-methylcyclohexanecarboxylate, zinc 2-mcthylcyclohcxanccarboxylatc, zinc 3-methylcyclohexanecarboxylate, zinc 4-methylcyclohexanecarboxylate, zinc 1,3- dimethylcyclohexanecarboxylate, zinc 2,2- dimethylcyclohexanecarboxylate, zinc 2,4- dimethylcyclohexanecarboxylate, zinc 1—chlorocyclohexanecarboxylate, zinc 2-chlorocyclohexanecarboxylate, zinc 1-bromocyclohexanecarboxylate, zinc 2—bromocyclohexanecarboxylate, zinc 3-bromocyclohexanecarboxylate, zinc 1,2- dibromocyclohexanecarboxylate, zinc cyclohexylacetate, zinc 1 -methylcyclohexylacetate, zinc 2,2- dimethylcyclohexylacetate, zinc 1-cyclohexenecarboxylate, zinc 2-cyclohexenecarboxylate, zinc 3-cyclohexenecarboxylate, zinc cycloheptanecarboxylate, zi11c 1-cycloheptenecarboxylate, zi11c cyclooctanecarboxylate, zinc 2-methylbenzoate, zinc 3-methylbenzo ate, zinc 4-methylbenzo ate, zinc 2-ethylbenzoate, Zinc 3-ethylbenzoate, zinc 4-ethylbenzoate, zinc 2,3 -dimethylbenzoate, zinc 2,4- dimethylbenzoate, zinc 2,5-dimethylbenzoate, zinc 2,6- dimcthylbcnzoatc, zinc 3,4-dimcthylbcnzoatc, zinc 3,5- dimethylbenzoate, zinc 2,3,4-trimethylbenzoate, zinc 2,3,5- trimethylbenzoate, zinc 2,3,6-trimethylbenzoate, zinc 2,4,6- trimethylbenzoate, zinc 3,4,5—trimethylbenzo ate, zinc cuminate, zinc 2,3,4,5-tetramethylbenzoate, zinc 2,3,5 ,6- tetramethylbenzoate, zinc pentamethylbenzoate, zinc 2—chlorobenzo ate, zinc cinnamate, zinc 2—cyanobenzoate, zinc naphthalene- 1 -carboxylate, zinc 2-methylnaphthalene- 1-carboxylate, zinc 4-methylnaphthalene-1-carboxylate, zinc 5-methylnaphthalene-1-carboxylate, zinc 6-methylnaphthalene-1-carboxylate, zinc 7-methylnaphthalene-1-carboxylate, zinc 8-methylnaphthalene-1-carboxylate, zinc naphthalene-2- carboxylate, zinc 1-n1etl1ylnapl1tl1alene-2-carboxylate, zinc 4-methylnaphthalene-2-carboxylate, zinc 5-methylnaphthalene-2-carboxylate, Zinc 6-methylnaphthalene-2-carboxylate, zinc US 6,830,704 B2 5 8-metliylnaphthalene-2-carboxylate, zinc 5-ch1oronaphtha1ene-1-carboxylate, zinc 7-chl0ronaphthalene-1-carboxylate, zinc 8-chloronaphthalene-1-carboxylate, zinc 4-bromonaphthalene-1-carboxylate, zinc 5-bromonaphthalene-1-carboxylate, zinc 7-bromonaphthalcnc-1-carboxylatc, zinc 8-bromonaphthalene-1-carboxylate, zinc 8-iodonaphthalene-1-carboxylate, zinc 1-chloronaphthalene-2-carboxylate, zinc 3-chloronaphthalene-2-carboxylate, zinc 5-chloronaphthalene-2-carboxylate, zinc 5—bromonaphthalene—2—carboXylate, zinc 3-iodonaphthalene-2-carboxylate, zinc benzenesulfonate, zinc 2-toluenesulfonate, zinc 3-toluenesulfonate, zinc 4—toluenesulfonate, zinc o—Xylene—4—sulfonate, zinc m-Xylene-4-sulfonate, zinc p-Xylene-4-sulfonate, zinc 4-fluorobenzenesulfonate, zinc 2-chlorobenzenesulfonate, zinc 3-chlorobenzenesulfonate, zinc 4-chlorobenzenesulfonate, zinc 2,4- dichlorobenzenesulfonate, zinc 2-bromobenzenesulfonate, zinc 3-bromobenzenesulfonate, zinc 4-bromobenzenesulfonate, zinc 2,5- dibromobenzenesulfonate, zinc 3,4- dibromobenzenesulfonate, zinc 2-iodobenzenesulfonate, zinc 3-iodobenzenesulfonate, zinc 4-iodobenzenesulfonate, zinc methanesulfonate, zinc ethanesulfonate, zinc propanesulfonate, zinc butanesulfonate, zinc pcntancsulfonatc, zinc hcxancsulfonatc, zinc heptanesulfonate, zinc octanesulfonate, zinc trifiuoromethanesulfon ate, zinc pentafluoroethanesulfonate, zinc heptafluoropropanesulfonate, zinc perfluorobutanesulfonate, zinc perfluoropentanesulfonate, zinc perfluorohexanesulfonate, zinc perfluorooctanesulfonate, zinc perchlorate, and the anhy- drides and hydrates of those salts. Lewis Acid Metal Salt Containing Cadmium: Examples of the Lewis acid metal salt containing cad- mium include cadmium acetate, cadmium monofluoro acetate, cadmium difluoroacetate, cadmium trifluoroacetate, cadmium monochloro acetate, cadmium dichloro acetate, cadmium trichloroacetate, cadmium monobromoacetate, cadmium dibromoacetate, cadmium tribromoacetate, cadmium monoiodoacetate, cadmium diio do acetate, cadmium triiodo acetate, cadmium cyanoacetate, cadmium propionate, cadmium 0L-fluoropropionate, cadmium [3 -fluoropropionate, cadmium cx.,(x'-difluoropropionate, cadmium cx.,[3 -difluoropropionate, cadmium B ,[3‘-difluoropropionate, cadmium or-chloropropiona te, cadmium [3-chloropropionate, cad- mium (x.,cx‘-dichloropropionate, cadmium cx,[3 - dichloropropionate, cadmium [3,[3‘-dichloropropionate, cad- mium G.-bromopropionate, cadmium B-bromopropionate, cadmium cx,cx.'—dibromopropion ate, cadmium Ot,B — dibromopropionate, cadmium B,B‘-dibromopropionate, cad- mium cx-iodopropionate, cadmium B-iodopropionate, cad- mium oL,oL'—diiodopropionate, cadmium 0., B- diiodopropionate, cadmium [3 , B‘-diiodopropionate, cadmium [3,[3,B -triiodopropionate, cadmium butyrate, cad- mium isobutyrate, cadmium Valerate, cadmium caproate, cadmium hep tano ate, cadmium caprylate, cadmium 2-ethylhexano ate , cadmium acrylate, cadmium 0.-fluoroacrylate, cadmium [3-fluoroacrylate, cadmium cx.-chloroacrylate, cadmium [3-chloroacrylate, cadmium (x,[3- dichloroacrylate, cadmium [5, [5‘-dichloroacrylate, cadmium 0.-bromoacrylate, cadmium [3-bromoacrylate, cadmium oL,[3- dibromoacrylate, cadmium [3 ,[3‘-dibromoacrylate, cadmium 5 10 15 20 30 35 40 45 55 60 65 6 tribromoacrylate, cadmium U.-iodoacrylate, cadmium [3-iodoacrylate, cadmium 0L,|3-diiodoacrylate, cadmium |3,|3’- diiodoacrylate, cadmium crotonate, cadmium on-chlorocrotonate, cadmium [3-chlorocrotonate, cadmium y-chlorocrotonate, cadmium ot-bromocrotonate, cadmium [3-bromocrotonate, cadmium y-bromocrotonate, cadmium oL,[3-dichlorocrotonatc, cadmium cx,[3-dibromocrotonatc, cadmium y,y,y-trichlorocrotonate, cadmium methacrylate, cadmium B-bromomethacrylate, cadmium formate, cad- mium chloroformate, cadmium cyclopentanecarboxylate, cadmium 1-methylcyclopentanecarboxylate, cadmium 2-methylcyclopentanecarboxylate, cadmium 3—methylcyclopentanecarboxylate, cadmium cyclohexanecarboxylate, cadmium 1-methylcyclohexanecarboxylate, cadmium 2—methylcyclohexanecarboxylate, cadmium 3-methylcyclohexanecarboxylate, cadmium 4-methylcyclohexanecarboxylate, cadmium 1,3- dimethylcyclohexanecarboxylate, cadmium 2,2- dimethylcyclohexanecarboxylate, cadmium 2,4- dimethylcycloheXanecarboxylate, cadmium 1-chlorocyclohexanecarboxylate, cadmium 2-chlorocyclohexanecarboxylate, cadmium 1-bromocyclohexanecarboxylate, cadmium 2-bromocyclohexanecarboxylate, cadmium 3-bromocyclohexanecarboXylate, cadmium 1,2- dibromocyclohexanecarboxylate, cadmium cyclohexylacetate, cadmium 1-methylcyclohexylacetate, cadmium 2,2-dimcthylcyclohcxylacctatc, cadmium 1-cyclohexenecarboxylate, cadmium 2-cyclohexenecarboxylate, cadmium 3-cyclohexenecarboxylate, cadmium cycloheptanecarboxylate, cadmium 1-cycloheptenecarboxylate, cadmium cyclooctanecarboxylate, cadmium 2—methylbenzoate, cad- mium 3-methylbenzoate, cadmium 4-methylbenzoate, cad- mium 2-ethylbenzoate, cadmium 3-ethylbenzoate, cadmium 4—ethylbenzoate, cadmium 2,3—dimethylbenzoate, cadmium 2,4-dimethylbenzoate, cadmium 2,5-dimethylbenzoate, cad- mium 2,6-dimethylbenzoate, cadmium 3,4- dimethylbenzoate, cadmium 3,5-dimethylbenzoate, cad- mium 2,3,4-trimethylbenzoate, cadmium 2,3,5- trimethylbenzoate, cadmium 2,3,6-trimethylbenzoate, cadmium 2,4,6-trimethylbenzoate, cadmium 3,4,5- trimethylbenzoate, cadmium cu111inate, cadmium 2,3,4,5- tetramethylbenzoate, cadmium 2,3,5,6-tetramethylbenzoate, cadmium pentamethylbenzoate, cadmium 2-chlorobenzoate, cadmium cinnamate, cadmium 2-cyanobenzoate, cadmium naphthalene-1-carboxylate, cadmium 2-methy1naphthalene- 1-carboxylate, cadmium 4-methylnaphthalene-1- carboxylatc, cadmium 5-mcthylnaphthalcnc-1-carboxylatc, cadmium 6-methylnaphthalene-1-carboxylate, cadmium 7-methylnaphthalene-1-carboxylate, cadmium 8—methylnaphthalene—1—carboXylate, cadmium naphthalene- 2-carboxylate, cadmium 1-methylnaphthalene-2- carboxylate, cadmium 4-methylnaphthalene-2-carboxylate, cadmium 5—methylnaphthalene—2—carboXylate, cadmium 6-methylnaphthalene-2-carboxylate, cadmium 8-methylnaphthalene-2-carboxylate, cadmium 5-chloronaphthalene-1-carboxylate, cadmium 7-chloronaphthalene-1-carboxylate, cadmium 8-chloronaphthalene-1-carboxylate, cadmium 4-brom0naphthalene-1-carboxylate, cadmium 5-bromo11aphthalene-1-carboxylate, cadmium 7-brom0naphthalene-1-carboxylate, cadmium 8-brom0naphthalene-1-carboxylate, cadmium 8-iodonaphthalene-1-carboxylate, cadmium US 6,830,704 B2 7 1 -cl1loro11apl1tl1alene-2-carboxylate, 3-chloronaphthalene-2-carboxylate, 5-chloronaphthalene-2-carboxylate, 5 -bromonaphthalene-2-carboxylate , cadmium 3-iodonaphthalene-2-carboxylate, cadmium benzenesulfonate, cadmium 2-toluenesulfonate, cadmium 3-tolucncsulfonatc, cadmium 4-tolucnesulfonatc, cadmium o-xylene-4-sulfonate, cadmium m-Xylene-4-sulfonate, cad- mium p-Xylene-4-sulfonate, cadmium 4-fluorobenzenesulfonate, cadmium 2-chlorobenzenesulfonate, cadmium 3-chlorobenzenesulfonate, cadmium 4—chlorobenzenesulfonate, cadmium 2,4- dichlorobenzenesulfonate, cadmium 2-bromobenzenesulfonate, cadmium 3—bromobenzenesulfonate, cadmium 4-bromobenzenesulfonate, cadmium 2,5- dibromobenzenesulfonate, cadmium 3,4- dibromobenzenesulfonate, cadmium 2-iodobenzenesulfonate, cadmium 3-iodobenzenesulfonate, cadmium 4-iodobenzenesulfonate, cadmium methanesulfonate, cadmium ethanesulfonate, cadmium prop anesulfonate, cadmium butanesulfonate, cadmium pentanesulfonate, cadmium hexanesulfonate, cadmium heptanesulfonate, cadmium octanesulfonate, cadmium trifluoromethanesulfonate, cadmium pentafluoroethanesulfonate, cadmium heptafluoropropanesulfonate, cadmium pcrfluorobutancsulfonatc, cadmium perfluoropentanesulfonate, cadmium perfluorohexanesulfonate, cadmium perfluorooctanesulfonate, cadmium perchlorate, and the anhydrides and hydrates of those salts. Lewis Acid Metal Salt Containing Mercury: Examples of the Lewis acid metal salt containing mercury include mercury acetate, mercury monofluoroacetate, mer- cury difluoroacetate, mercury trifluoroacetate, mercury monochloro acetate, mercury dichloroacetate, mercury trichloroacetate, mercury monobromo acetate, mercury dibromoacetate, mercury tribromo acetate, mercury monoiodoacetate, mercury diiodoacetate, mercury triiodoacetate, mercury cyanoacetate, mercury propionate, mercury ox-fluoropropionate, mercury [3-fluoropropionate, mercury oL,cx‘-difluoropropionate, mercury (X,B- difluoropropionate, mercury [3,[3'-difluoropropionate, mer- cury ot-chloropropionate, mercury [3-chloropropionate, mer- cury 0.,oL‘-dichloropropionate, mercury oL,|3 - dichloropropionate, mercury [3,[3‘-dichloropropionate, mercury 0.-bromopropionate, mercury B-bromopropionate, mercury cx,ot‘-dibromopropionate, mercury oL,B- dibromopropionatc, mercury [3,[3‘-dibromopropionatc, mer- cury ot-iodopropionate, mercury B-iodopropionate, mercury cx.,cx'-diiodopropionate, mercury cx,[3-diiodopropionate, mer- cury [3,[3‘—diiodopropionate, mercury B,B,B— triiodopropionate, mercury butyrate, mercury isobutyrate, mercury Valerate, mercury caproate, mercury heptanoate, mercury caprylate, mercury 2—ethylheXanoate, mercury acrylate, mercury cx-fluoroacrylate, mercury [3-fluoroacrylate, mercury cx-chloroacrylate, mercury [3-chloroacrylate, mercury o.,[3-dichloroacrylate, mercury [3,[3'-dichloroacrylate, mercury on-bromoacrylate, mercury [3-bromoacrylate, mercury oL,[3-dibromoacrylate, mercury [3,[3‘-dibromoacrylate, mercury tribromoacrylate, mercury cx.-iodoacrylate, mercury [3-iodoacrylate, mercury o.,[3- diiodoacrylate, mercury [5,[5‘-diiodoacrylate, mercury crotonate, mercury 0.-chlorocrotonate, mercury [3-chlorocrotonate, mercury y-chlorocrotonate, mercury cadmium cadmium cadmium 10 15 20 30 35 40 45 55 60 65 8 on-bromocrotonate, mercury B-bromocrotonate, mercury y-bromocrotonate, mercury cx,|3-dichlorocrotonate, mercury oL,[3-dibromocrotonate, mercury y,y,y-trichlorocrotonate, mercury methacrylate, mercury [3-bromomethacrylate, mer- cury formate, mercury chloroformate, mercury cyclopentanecarboxylate, mercury 1-mcthylcyclopcntanccarboxylatc, mcrcury 2-methylcyclopentanecarboxylate, mercury 3-methylcyclopentanecarboxylate, mercury cyclohexanecarboxylate, mercury 1-methylcyclohexanecarboXylate, mercury 2-methylcyclohexanecarboxylate, mercury 3—methylcycloheXanecarboxylate, mercury 4-methylcyclohexanecarboxylate, mercury 1,3- dimethylcyclohexanecarboxylate, mercury 2,2- dimethylcyclohexanecarboxylate, mercury 2,4- dimethylcyclohexanecarboXylate, mercury 1-chlorocyclohexanecarboxylate, mercury 2-chlorocyclohexanecarboxylate, mercury 1-bromocyclohexanecarboxylate, mercury 2-bromocycloheXanecarboxylate, mercury 3-bromocyclohexanecarboxylate, mercury 1,2- dibro1110cyclohexanecarboxylate, mercury cyclohexylacetate, mercury 1-methylcyclohexylacetate, mercury 2,2-dimethylcyclohexylacetate, mercury 1-cyclohexenecarboxylate, mercury 2-cyclohexenecarboxylate, mercury 3-cyclohexenecarboxylate, cyclohcptanccarboxylatc, mcrcury 1-cycloheptenecarboxylate, mercury cyclooctanecarboxylate, mercury 2-methylbenzoate, mer- cury 3-methylbenzoate, mercury 4-methylbenzoate, mer- cury 2-ethylbenzoate, mercury 3-ethylbenzoate, mercury 4-ethylbenzoate, mercury 2,3-dimethylbenzoate, mercury 2,4—dimethylbenzoate, mercury 2,5 —dimethylbenzoate, mer- cury 2,6-dimethylbenzoate, mercury 3,4-dimethylbenzoate, mercury 3,5-dimethylbenzoate, mercury 2,3,4- trimethylbenzoate, mercury 2,3,5—trimethylbenzoate, mer- cury 2,3,6-trimethylbenzoate, mercury 2,4,6- trimethylbenzoate, mercury 3,4,5-trimethylbenzoate, mercury cuminate, mercury 2,3,4,5 -tetramethylbenzoate, mercury 2,3 ,5,6 -tetramethylbenzo ate, mercury pentamethylbenzoate, mercury 2-chlorobenzo ate, mercury cinnamate, mercury 2-cyanobenzoate , mercury naphthalene-1-carboxylate, mercury 2-methylnaphthalene- 1-carboxylate, mercury 4-methylnaphthalene-1-carboxylate, mercury 5 -methylnaphthalene- 1 -carboxylate, mercury 6-methylnaphthalene-1 -carboxylate, mercury 7-methylnaphthalene-1 -carboxylate, mercury 8-methylnaphthalene-1-carboxylate, mercury naphthalene- 2-carboxylatc, mcrcury 1-methylnaphthalcnc-2-carboxylatc, mercury 4-methylnaphthalene-2-carboxylate, mercury l’I1CI'C1]I'y 5-methylnaphthalene-2-carboxylate, mercury 6—methylnaphthalene—2—carboXylate, mercury 8-methylnaphthalene-2-carboxylate, mercury 5-chloronaphthalene-1-carboxylate, mercury 7—chloronaphthalene—1—carboXylate, mercury 8-chloronaphthalene-1-carboxylate, mercury 4-bromonaphthalene-1-carboxylate, mercury 5-bromonaphthalene-1-carboxylate, mercury 7-bromonaphthalene-1-carboxylate, mercury 8-bromonaphthalene-1-carboxylate, mercury 8-iodonaphthalene-1-carboxylate, mercury 1-chloronaphthalene-2-carboxylate, mercury 3-chloronaphthalene-2-carboxylate, mercury 5-chloronaphthalene-2-carboxylate, mercury 5-bromonaphthalene-2-carboxylate, mercury US 6,830,704 B2 9 3-io(lonaphthalene-2-carboxylate, n1ercury benzenesulfonate, mercury 2-toluenesulfonate, mercury 3-toluenesulfonate, mercury 4-toluenesulfonate, mercury o-xylene-4-sulfonate, mercury m-Xylene-4-sulfonate, mer- cury p-xylene-4-sulfonate, mercury 4-fluorobenzenesulfonate, mercury 2-chlorobenzenesulfonate, mercury 3-chlorobenzenesulfonate, mercury 4-chlorobenzenesulfonate, mercury 2,4- dichlorobenzenesulfonate, mercury 2-bromobenzenesulfonate, mercury 3-bromobenzenesulfonate, mercury 4—bromobenzenesulfonate, mercury 2,5- dibromobenzenesulfonate, mercury 3,4- dibromobenzenesulfonate, mercury 2—iodobenzenesulfonate, mercury 3—iodobenzenesulfonate, mercury 4-iodobenzenesulfonate, mercury methanesulfonate, mercury ethanesulfonate, mercury propanesulfonate, mercury butanesulfonate, mercury pentanesulfonate, mercury hex anesulfonale, mercury heptanesulfonate, mercury octane sulfonate, mercury trifluoromethanesulfonate, mercury pentafluoroethanesulfonate, mercury heptafluoropropanesulfonate, mercury perfluorobutanesulfonate, mercury perfluoropentanesulfonate, mercury perfluorohexanesulfonate, mercury perfluorooctanesulfonate, mercury perchlorate, and the anhydrides and hydrates of those salts. Lewis Acid Metal Salt Containing Aluminum: Examples of the I .eWis-acid metal salt containing alumi- num include aluminum acetate, aluminum monofluoroacetate, aluminum difluoroacetate, aluminum trifluoro acetate, aluminum monochloroacetate, aluminum dichloroacetate, aluminum trichloro acetate, aluminum monobromo acetate, aluminum dibromoacetate, aluminum tribromoacetate, aluminum monoiodoacetate, aluminum diiodo acetate, aluminum triiodo acetate, aluminum cyanoacetate , aluminum propion ate, aluminum 0.-fluoropropionate, aluminum [3-fluoropropionate, alumi- num ot,cL'-difluoropropionate, aluminum ot,B - difluoropropionate, alun1ir1un1 [3,[3'-difluoropropionate, alu- minum 0.-chloropropionate, aluminum [3 -chloropropionate, aluminum ot,ot‘-dichloropropionate, aluminum 0.,[3- dichloro pro pionate, aluminum ,[3 '-dichloropropionate, alu- minum (1-bromopropionate, aluminum [3 -bromopropionate, aluminum ot,ct‘-dibromoprop ionate, aluminum oL,[3 - dibromopropionate, aluminum [3,[3‘-dibromopropionate, alu- minum or-iodopropionate, aluminum B-iodopropionate, alu- minu m oL,cx‘-diiodopropionate, aluminum cx,[3 - diiodopropionate, aluminum [3, [3 ‘-diiodopropionate, aluminum B,B ,B -triiodopropionate, aluminum butyrate, alu- minum isobutyrate, aluminum Valerate, aluminum caproate, aluminum heptanoate, aluminum caprylate, aluminum 2-ethylhexanoate , aluminum acrylate , aluminum 0.-fluoroacrylate, aluminum [3 -fluoroacrylate, aluminum cx.—chloroacrylate, aluminum [3 —chloroacrylate, aluminum cx.,B-dichloro acrylate, aluminum [3 ,[3 ‘-dichloro acrylate, alu- minum or-bromoacrylate, aluminum [3 -bromo acrylate, alu- minum 0.,[3 -dibromoacrylate, aluminum B, [3 ' - dibromoacrylate, aluminum tribromoacrylate, aluminum 0.-iodo acrylate, aluminum [3-iodoacrylate, aluminum oL,[3 - diiodoacrylate, aluminum [3 ,[3‘-diiodoacrylate, aluminum crotonate, aluminum on-chlorocroton ate, aluminum [3 -chlorocrotonate, aluminum y-chlorocrotonate, aluminum 0.-bromocrotonate, aluminum [3 -bromocrotonate, aluminum y-bromocrotonate, aluminum or, [3-dichlorocrotonate, alumi- 5 10 15 20 30 35 40 45 55 60 65 10 r1un1 0., [3 -dibromocrotonate, aluminum y ,y,y- trichlorocrotonate, aluminum methacrylate, aluminum [3-bromomethacrylate, aluminum formate, aluminum chloroformate, aluminum cyclopentanecarboxylate, alumi- num 1-methylcyclopentanecarboxylate, aluminum 2-methylcyclopentanecarboxylate, aluminum 3-methylcyclopentanecarboxylate, aluminum aluminum aluminum cyclohexanecarboxylate, 1-methylcyclohexanecarboxylate, 2-methylcyclohexanecarboxylate, aluminum 3-methylcyclohexanecarboxylate, aluminum 4-methylcycloheXanecarboxylate, aluminum 1,3- dimethylcyclohexanecarboxylate, aluminum 2,2- dimethylcyclohexanecarboxylate, aluminum 2,4- dimethylcyclohexanecarboxylate, aluminum 1—chlorocyclohexanecarboxylate, aluminum 2-chlorocyclohexanecarboxylate, aluminum 1-bromocyclohexanecarboxylate, aluminum 2-bromocyclohexanecarboxylate, aluminum 3-bromocyclohexanecarboxylate, aluminum 1,2- dibromocyclohexanecarboxylate, aluminum cyclohexylacetate, aluminum 1-methylcyclohexylacetate, aluminum 2,2-dimethylcyclohexylacetate, aluminum 1-cyclohexenecarboxylate, aluminum 2-cyclohexenecarboxylate, aluminum 3-cyclohexenecarboxylate, aluminum cycloheptanecarboxylate, aluminum 1-cycloheptenecarboxylate, aluminum cyclooctanecarboxylate, aluminum 2-methylbenzoate, alu- minum 3-methylbenzoate, aluminum 4-methylbenzoate, aluminum 2-ethylbenzoate, aluminum 3-ethylbenzoate, alu- minum 4-ethylbenzoate, aluminum 2,3-dimethylbenzoate, aluminum 2,4-dimethylbenzoate, aluminum 2,5- dimethylbenzoate, aluminum 2,6-dimethylbenzoate, alumi- num 3,4—dimethylbenzoate, aluminum 3,5- dimethylbenzoate, aluminum 2,3,4-trimethylbenzoate, aluminum 2,3,5-trimethylbenzoate, aluminum 2,3,6- trimethylbenzoate, aluminum 2,4,6—trimethylbenzoate, alu- minum 3,4,5-trimethylbenzoate, aluminum cuminate, alu- minum 2,3,4,5-tetramethylbenzoate, aluminum 2,3,5,6- tetramethylbenzoate, aluminum pentamethylbenzoate, aluminum 2-chlorobenzoate, aluminum cir1r1an1ate, alumi- num 2-cyanobenzoate, aluminum naphthalene-1- carboxylate, aluminum 2-methylnaphthalene-1-carboxylate, aluminum 4-methylnaphthalene-1-carboxylate, aluminum 5-methylnaphthalene-1-carboxylate, aluminum 6-methylnaphthalene-1-carboxylate, aluminum 7-methylnaphthalene-1-carboxylate, aluminum 8-methylnaphthalene-1-carboxylate, aluminum naphthalene-2-carboxylate, aluminum 1-methylnaphthalene-2-carboxylate, aluminum 4-methylnaphthalene-2-carboxylate, aluminum 5-methylnaphthalene-2-carboxylate, aluminum 6—methylnaphthalene—2—carboXylate, aluminum 8-methylnaphthalene-2-carboxylate, aluminum 5-chloronaphthalene-1-carboxylate, aluminum 7—chloronaphthalene—1—carboXylate, aluminum 8-chloronaphthalene-1-carboxylate, aluminum 4-bromonaphthalene-1-carboxylate, aluminum 5-bromonaphthalene-1-carboxylate, aluminum 7-bromonaphlhalene-1-carboxylale, aluminum 8-bromonaphthalene-1-carboxylate, aluminum 8-iodonaphthalene-1-carboxylate, aluminum 1-chloronaphthalene-2-carboxylate, aluminum 3-chloronaphthalene-2-carboxylate, aluminum 5-chloronaphthalene-2-carboxylate, aluminum 5-bromonaphthalene-2-carboxylate, aluminum US 6,830,704 B2 11 3-iodonaphthalene-2-carboxylate, aluminum benzenesulfonate, aluminum 2-toluenesulfonate, aluminum 3-toluenesulfonate, aluminum 4-toluenesulfonate, alumi- num o-Xylene-4-sulfonate, aluminum m-Xylene-4-sulfonate, aluminum p-Xylene-4-sulfonate, aluminum 4-fluorobenzenesulfonate, aluminum 2-chlorobcnzcncsulfonatc, aluminum 3-chlorobenzenesulfonate, aluminum 4-chlorobenzenesulfonate, aluminum 2,4- dichlorobenzenesulfonate, aluminum 2-bromobenzenesulfonate, aluminum 3-bromobenzenesulfonate, aluminum 4—bromobenzenesulfonate, aluminum 2,5- dibromobenzenesulfonate, aluminum 3,4- dibromobenzenesulfonate, aluminum 2—iodobenzenesulfonate, aluminum 3-iodobenzenesulfonate, aluminum 4-iodobenzenesulfonate, aluminum methanesulfonate, alu- minum ethanesulfonate, aluminum propanesulfonate, alumi- num butanesulfonate, aluminum pentanesulfonate, alumi- num hexanesulfonate, aluminum heptanesulfonate , aluminum octanesulfonate, aluminum trifluoromethanesulfonate, aluminum pentafluoroethanesulfonate, aluminum heptafluoropropanesulfonate, aluminum perfluorobutanesulfonate, aluminum perfluoropentanesulfonate, aluminum perfluorohexanesulfonate, aluminum pcrfluorooctanesulfonatc, aluminum pcrchloratc, and thc anhydrides and hydrates of those salts. Lewis Acid Metal Salt Containing Gallium: Examples of the Lewis acid metal salt containing gallium include gallium acetate, gallium monofluoroacetate, gallium difluo ro acetate, gallium trifluoroacetate, gallium monochloroacetate, gallium dichloro acetate, gallium trichloro acetate, gallium monobromoacetate, gallium dibromoacetate, gallium tribromoacetate, gallium monoiodoacetate, gallium diiodoacetate , gallium triiodoacetate, gallium cyanoacetate, gallium propionate, gallium 0.-fluoropropionate, gallium [3-fluoropropionate, gallium cL,cL' -difluoropropionate, gallium (x, [3- difluoropropionate, gallium [3,[3'-difluoropropionate, gallium 0.-chloropropionate, gallium [5 -chloropropionate, gallium cx.,cx'-dichloropropionate, gallium 0t,B-dichloropropionate, gallium [3, B‘-dichloropropionate, gallium 0.-bromopropionate, gallium [3-bromopropionate, gallium oL,0.'-dibromopropionate, gallium oL,[3-dibromopropionate, gallium [3,[3‘-dibromopropionate, gallium cx-iodopropionate, gallium B-iodopropionate, gallium cx,0L‘-diiodopropionate, gallium oL,[3-diiodopropionate, gallium B,B'- diiodopropionatc, gallium [3,[3,[3-triiodopropionatc, gallium butyrate, gallium isobutyrate, gallium Valerate, gallium caproate, gallium heptanoate, gallium caprylate, gallium 2—ethylheXanoate, gallium acrylate, gallium 0.-fluoroacrylate, gallium B-fluoroacrylate, gallium 0.-chloro acrylate, gallium [3-chloroacrylate, gallium 0t,[3 - dichloroacrylate, gallium [3,[3‘—dichloroacrylate, gallium 0.-bromoacrylate, gallium [3-bromoacrylate, gallium (X.,[3 - dibromoacrylate, gallium [3 , B‘-dibromoacrylate, gallium tribromoacrylate, gallium 0.-iodoacrylate, gallium [3 -iodoacrylate, gallium u.,B-diiodo acrylate, gallium [3, B'- diiodoacrylate , gallium crotonate, gallium 0.-chlorocrotonate, gallium [3-chlorocrotonate, gallium y-chlorocrotonate, gallium 0'.-bromocrotonate, gallium [5 -bromocrotonate, gallium y-bromocrotonate, gallium 0t,[5 - dichlorocrotonate, gallium o.,B-dibromocrotonate, gallium y,y,y-trichlorocrotonate, gallium methacrylate, gallium 10 15 20 30 35 40 45 55 60 65 12 [3-bromomethacrylate, gallium formate, gallium chloroformate, gallium cyclopentanecarboxylate, gallium 1-methylcyclopentanecarboxylate, gallium 2-methylcyclopentanecarboxylate, gallium 3-methylcyclopentanecarboxylate, gallium cyclohexanecarboxylate, gallium 1-mcthylcyclohcXanccarboxylatc, gallium 2-methylcyclohexanecarboxylate, gallium 3-methylcyclohexanecarboxylate, gallium 4-methylcyclohexanecarboxylate, dimethylcyclohexanecarboxylate, dimethylcyclohexanecarboxylate, gallium 1,3- gallium 2,2- gallium 2,4- dimethylcyclohexanecarboxylate, gallium 1-chlorocyclohexanecarboxylate, gallium 2-chlorocyclohexanecarboxylate, gallium 1—bromocyclohexanecarboxylate, gallium 2-bromocycloheXanecarboxylate, gallium 3-bromocyclohexanecarboxylate, gallium 1,2- dibromocyclohexanecarboxylate, gallium cyclohexylacelate, gallium 1-methylcyclohexylacetate, gal- lium 2,2-dimethylcyclohexylacetate, gallium 1-cyclohexenecarboxylate, gallium 2-cyclohexenecarboxylate, gallium 3-cyclohexenecarboxylate, gallium cycloheptanecarboxylate, gallium 1-cycloheptenecarboxylate, gallium cyclooctanecarboxylate, gallium 2-methylbenzo ate, gallium 3-methylbenzo ate, gallium 4-methylbenzoate, gallium 2-cthylbenzoate, gallium 3-cthylbcnzoatc, gallium 4-ethylbenzo ate, gallium 2,3-dimethylbenzoate, gallium 2,4-dimethylbenzoate, gallium 2,5-dimethylben zoate, gal- lium 2,6-dimethylbenzoate, gallium 3,4-dimethylbenzoate, gallium 3,5-dimethylbenzoate, gallium 2,3,4- trimethylbenzoate, gallium 2,3,5-trimethylbenzoate, gallium 2,3,6—trimethylbenzoate, gallium 2,4,6—trimethylbenzoate, gallium 3,4,5 -trimethylbenzoate, gallium cuminate, gallium 2,3,4,5-tetramethylbenzoate, gallium 2,3,5,6- tetramethylbenzoate, gallium pentamethylbenzo ate, gallium 2-chlorobenzoate , gallium cinnamate, gallium 2-cyanobenzoate, gallium naphthalene-1-carboxylate, gal- lium 2-methylnaphthalene- 1 -carboxylate , gallium 4-metl1ylnapl1tl1alene-1-carboxylate, gallium 5-methylnaphthalene-1-carboxylate, gallium 6-methylnaphthalene-1-carboxylate, gallium 7-methylnaphthalene-1-carboxylate, gallium 8-methylnaphthalene-1-carboxylate, gallium naphthalene-2- carboxylate, gallium 1-methylnaphthalene-2-carboxylate, gallium 4-methylnaphthalene-2-carboxylate, gallium 5-methylnaphthalene-2-carboxylate, gallium 6-methylnaphthalene-2-carboxylate, gallium 8-mcthylnaphthalcne-2-carboxylatc, gallium 5-chloronaphthalene-l-carboxylate, gallium 7-chloronaphthalene-1-carboxylate, gallium 8—chloronaphthalene—1—carboXylate, gallium 4-bromonaphthalene-1-carboxylate, gallium 5-bromonaphthalene-1-carboxylate, gallium 7—bromonaphthalene—1—carboxylate, gallium 8-bromonaphthalene-1-carboxylate, gallium 8-iodonaphthalene-1-carboxylate, gallium 1-chloronaphthalene-2-carboxylate, gallium 3-chloronaphthalene-2-carboxylate, gallium 5-chloronaphthalene-2-carboxylate, gallium 5-bromonaphthalene-2-carboxylate, gallium 3-iodonaphthalene-2-carboxylate, gallium benzenesulfonate, gallium 2-toluenesulfonate, gallium 3-toluenesulfonate, gallium 4-toluenesulfonate, gallium o-Xylene-4-sulfonate, gallium m-Xylene-4-sulfonate, gal- US 6,830,704 B2 13 lium p-Xylene-4-sulfonate, gallium 4-fluorobenzenesulfonate, gallium 2-chlorobenzenesulfonate, gallium 3-chlorobenzenesulfonate, gallium 4-Chlorobenzenesulfonate, gallium 2,4- dichlorobenzenesulfonate, gallium 2-bromobcnzcncsulfonatc, gallium 3-bromobenzenesulfonate, gallium 4-bromobenzenesulfonate, gallium 2,5- dibromobenzenesulfonate, gallium 3,4- dibromobenzenesulfonate, gallium 2-iodobenzenesulfonate, gallium 3-iodobenzenesulfonate, gallium 4—iodobenzenesulfonate, gallium methanesulfonate, gallium ethanesulfonate , gallium prop anesulfonate, gallium butanesulfonate, gallium pent anesulfonate , gallium hexanesulfon ate, gallium heptanesulfonate, gallium octanesulfonate, gallium trifluoromethanesulfonate, gallium pentafluoroethanesulfonate, gallium heptafluoropropanesulfonate, gallium perlluorobutanesulfonate, gallium perfluoropentanesulfonate, gallium perfluorohexanesulfonate, gallium perfluorooctanesulfonate, gallium perchlorate, and the anhy- drides and hydrates of those salts. Lewis Acid Metal Salt Containing Indium: Examples of the Lewis acid metal salt containing indium include indium monofluoroacetate, indium difluoroacetate, indium trifluoroacetate, indium monochloroacetate, indium dichloroacctate, indium trichloroacctatc, indium monobromoacetate, indium dibromoacetate, indium tribromoacetate, indium monoiodoacetate, indium diiodoacetate, indium triiodoacetate, indium cyanoacetate, indium propionate, indium 0.-fluoropropionate, indium [3-fluoropropionate, indium oL,oL‘-difluoropropionate, indium o.,[3—difluoropropionate, indium [3,[3‘—difluoropropionate, indium 0.-chloropropionate, indium [3-chloropropionate, indium oL,o.'-dichloropropionate, indium (1,6- dichloropropionate, indium [3,[3'—dichloropropionate, indium 0.-bromopropionate, indium [3-bromopropionate, indium o.,oL'-dibromopropionate, indium oL,[3-dibromopropionate, indium [3,[3‘-dibromopropionate, indium ot-iodopropionate, indium [3-iodopropionate, indium cx.,o'.'-diiodopropionate, indium oL,[5-diiodopropionate, indium [5,[5'- diiodopropionate, indium [3,[3,[3-triiodopropionate, indium butyrate, indium isobutyrate, indium Valerate, indium caproate, indium heptanoate, indium caprylate, indium 2-ethylhexanoate, indium acrylate, indium ot-fluoroacrylate, indium B-fluoroacrylate, indium cx-chloroacrylate, indium B-Chloroacrylate, indium o.,B-dichloroacrylate, indium B,B‘- dichloroacrylate, indium or-bromoacrylate, indium [3-bromoacrylate, indium cx.,B-dibromoacrylate, indium [3,[3'- dibromoacrylate, indium tribromoacrylate, indium 0.-iodoacrylate, indium B-iodoacrylate, indium o.,[3- diiodoacrylate, indium [3,B‘—diiodoacrylate, indium crotonate, indium 0.-Chlorocrotonate, indium [3-chlorocrotonate, indium Y-chlorocrotonate, indium o.—bromocrotonate, indium [3—bromocrotonate, indium y-bromocrotonate, indium oL,B-dichlorocrotonate, indium o.,[3-dibromocrotonate, indium y,y,y-trichlorocrotonate, indium methacrylate, indium y-bromomethacrylate, indium formate, indium chloroformale, indium Cyclopentanecarboxylate, indium 1-methylcyclopentanecarboxylate, indium 2-methylcyclopentanecarboxylate, indium 3-methylcyclopentaneCarboxylate, indium cyclohexanecarboxylate, indium 1-methylcyclohexanecarboxylate, indium 10 15 20 30 35 40 45 55 60 65 14 2-methylcyclohexanecarboxylate, indium 3-methylcyclohexaneCarboxylate, indium 4-methylcyclohexanecarboxylate, indium 1,3- dimethylcyclohexanecarboxylate, indium 2,2- dimethylcyclohexanecarboxylate, indium 2,4- dimethylcyclohexanecarboxylate, indium 1-chlorocyclohcxanecarboxylate, indium 2-chlorocyclohexanecarboxylate, indium 1-bromocyclohexanecarboxylate, indium 2-bromocyclohexanecarboxylate, indium 3-bromocyclohexanecarboxylate, indium 1,2- dibromocyclohexanecarboxylate, indium cyclohexylacetate, indium 1—methylcyclohexylacetate, indium 2,2- dimethylcyclohexylacetate, indium 1-cyclohexenecarboxylate, indium 2—cycloheXenecarboXylate, indium 3-cyclohexenecarboxylate, indium cycloheptanecarboxylate, indium 1-cycloheptenecarboxylate, indium cyclooctanecarboxylate, indium 2-methylbenzoate, indium 3-methylbenzoale, indium 4-methylbenzoate, indium 2-ethylbenzoate, indium 3-ethylbenzoate, indium 4-ethylbenzo ate, indium 2,3- di111ethylbenzoate, indium 2,4-dimethylbenzoate, indium 2,5-dimethylbenzo ate, indium 2,6-dimethylbenzoate, indium 3,4-dimethylbenzoate, indium 3,5- dimethylbenzoate, indium 2,3,4-trimethylbenzoate, indium 2,3,5 -trimethylbenzo ate, indium 2,3,6-trimethylbenzo ate, indium 2,4,6-trimethylbenzoate, indium 3,4,5- trimethylbenzoatc, indium cuminatc, indium 2,3,4,5- tetramethylbenzoate, indium 2,3,5,6-tetramethylbenzoate, indium pentamethylben zoate, indium 2-chlorobenzoate, indium cinnamate, indium 2-cyanobenzo ate, indium naphthalene-1-carboxylate, indium 2-methylnaphthalene-1 - carboxylate, indium 4-methylnaphthalene-1-carboxylate, indium 5—methylnaphthalene— 1 —carboXylate, indium 6-methylnaphthalene-1 -carboxylate, indium 7-methylnaphthalene-1 -carboxylate, indium 8—methylnaphthalene—1 —carboXylate, indium naphthalene—2— carboxylate, indium 1-methylnaphthalene-2-carboxylate, indium 4-methylnaphthalene-2-carboxylate, indium 5-methylnaphthalene-2-carboxylate, indium 6-methylnaphthalene-2-carboxylate, indium 8-methylnaphthalene-2-carboxylate, indium 5-chloronaphthalene-1-carboxylate, indium 7-chloronaphthalene-1-carboxylate, indium 8-chloronaphthalene-1-carboxylate, indium 4-bromonaphthalene-1-carboxylate, indium 5-bromonaphthalene-1-carboxylate, indium 7-bromonaphthalene-1-carboxylate, indium 8-bromonaphthalene-1-carboxylate, indium 8-iodonaphthalcne-1-carboxylatc, indium 1-chloronaphthalene-2-Carboxylate, indium 3-chloronaphthalene-2-carboxylate, indium 5—chloronaphthalene—2—carboXylate, indium 5-bromonaphthalene-2-carboxylate, indium 3-iodonaphthalene-2-carboxylate, indium benzenesulfonate, indium 2—toluenesulfonate, indium 3—toluenesulfonate, indium 4-toluenesulfonate, indium o -Xylene-4-sulfonate, indium m-xylene-4-sulfonate, indium p -Xylene-4-sulfonate, indium 4-fluorobenzenesulfonate, indium 2-chlorobenzenesulfonale, indium 3-chlorobenzenesulfonate, indium 4-chlorobenzenesulfonate, indium 2,4- dichlorobenzenesulfonate, indium 2-bromobenzenesulfonate, indium 3-bromobenzenesulfonate, indium 4-bromobenzenesulfonate, indium 2,5- US 6,830,704 B2 15 dibromobenzenesulfonate, indium 3,4- dibromobenzenesulfonate, indium 2-iodobenzenesulfonate, indium 3-iodobenzenesulfonate, indium 4-iodobenzenesulfonate, indium methanesulfonate, indium ethanesulfonate, indium propanesulfonate, indium butanesulfonate, indium pentanesulfonate, indium hcxancsulfonatc, indium hcptancsulfonatc, indium octanesulfonate, indium trifluoromethanesulfonate, indium pentafluoroethanesulfonate, indium heptafluoropropanesulfonate, indium perfluorobutanesulfonate, indium perfluoropentanesulfonate, indium perfluorohexanesulfonate, indium perfluorooctanesulfonate, indium perchlorate, and the anhydrides and hydrates of these salts. Lewis Acid Metal Salt Containing Thallium: Examples of the Lewis acid metal salt containing thallium include thallium acetate, thallium monofluoroacetate, thal- lium difluoroacetate, thallium trifluoroacetate, thallium monochloroace tate, thallium dichloroacetate, thallium trichloroacetate, thallium monobromoacetate, thallium dibromo acetate, thallium tribromo acetate, thallium monoiodo acetate, thallium diiodoacetate, thallium triiodoacetate, thallium cyanoacetate, thallium propionate, thallium ot-fluoropropionate, thallium [3-fluoropropionate, thallium ot,ot‘-difluoropropionate, thallium ot,[3- difluoropropionate, thallium [3,[3‘-difluoropropionate, thal- li11m CL-chloropropionate, thallium [3-chloropropionate, thal- lium oL,ot‘-dichloropropionatc, thallium cx,B- dichloropropionate, thallium B,B‘-dichloropropionate, thallium ot-bromopropionate, thallium B-bromopropionate, thallium ot,cx‘-dibromopropionate, thallium ot,[3- dibromopropionate, thallium [3,[3'-dibromopropionate, thal- lium 0.-iodopropionate, thallium [3-iodopropionate, thallium o.,o.'—diiodopropionate, thallium oL,[3—diiodopropionate, thal- lium [3,[3‘-diiodopropionate, thallium [3,B,B- triiodopropionate, thallium butyrate, thallium isobutyrate, thallium Valerate, thallium caproate, thallium heptanoate, thallium caprylate, thallium 2-ethylhexanoate, thallium acrylate , thallium cx-fluoroacrylate , thallium [3-fluoroacrylate, thallium cx-chloroacrylate, thallium [3-chloroacrylate, thallium (x,[3-dichloroacrylate, thallium [5,[5'-dichloroacrylate, thallium ot-bromoacrylate, thallium [3-bromoacrylate, thallium ot,[3-dibromoacrylate, thallium [3,[3'-dibromoacrylate, thallium tribromoacrylate, thallium 0.-iodoacrylate, thallium [3-iodoacrylate, thallium cx,|3- diiodoacrylate, thallium [3,[3‘-diiodoacrylate, thallium crotonate, thallium cx-chlorocrotonate, thallium B-chlorocrotonate, thallium y-chlorocrotonate, thallium ot-bromocrotonate, thallium [3-bromocrotonate, thallium y-bromocrotonatc, thallium cx.,[3-dichlorocrotonatc, thallium o.,[3-dibromocrotonate, thallium y,y,y-trichlorocrotonate, thallium methacrylate, thallium [3-bromomethacrylate, thal- lium formate, thallium chloroformate, thallium cyclopentanecarboxylate, thallium 1 -methylcyclopentanecarboxylate, thallium 2—methylcyclopentanecarboxylate, thallium 3-methylcyclopentanecarboxylate, thallium cyclohexanecarboxylate, thallium 1-methylcyclohexanecarboxylate, thallium 2-methylcyclohexanecarboxylate, thallium 3-methylcyclohexanecarboxylate, thallium 4-methylcyclohexanecarboxylate, thallium 1,3- dimethylcycloheXanecarboxylate, thallium 2,2- dimethylcycloheXanecarboxylate, thallium 2,4- dimethylcyclohexanecarboxylate, thallium 1-chlorocyclohexanecarboxylate, thallium 10 15 20 30 35 40 45 55 60 65 16 2-chlorocyclohexanecarboxylate, 1-bromocyclohexanecarboxylate, 2-bromocyclohexanecarboxylate, 3-bromocyclohexanecarboxylate, thallium 1,2- dibromocyclohexanecarboxylate, thallium cyclohexylacetate, thallium 1-methylcyclohexylacetate, thallium 2,2-dimcthylcyclohcxylacctatc, thallium 1-cyclohexenecarboxylate, thallium 2-cyclohexenecarboxylate, thallium 3-cyclohexenecarboxylate, thallium cycloheptanecarboxylate, thallium 1-cycloheptenecarboxylate, thallium cyclooctanecarboxylate, thallium 2—methylbenzoate, thal- lium 3-methylbenzoate, thallium 4-methylbenzoate, thal- lium 2-ethylbenzoate, thallium 3-ethylbenzoate, thallium 4—ethylbenzoate, thallium 2,3—dimethylbenzoate, thallium 2,4-dimethylbenzoate, thallium 2,5-dimethylbenzoate, thal- lium 2,6-dimethylbenzoate, thallium 3,4-dimethylbenzoate, thallium 3,5-dimethylbenzoate, thallium 2,3,4- trimethylbenzoate, thallium 2,3,5-trimethylbenzoate, thal- lium 2,3,6-trimethylbenzoate, thallium 2,4,6- trimethylbenzoate, thallium 3,4,5-trimethylbenzoate, thallium cuminate, thallium 2,3,4,5-tetramethylbenzoate, thallium 2,3,5,6-tetramethylbenzo ate, thallium pentamethylbenzoate, thallium 2-chlorobenzoate, thallium cinnamate , thallium 2-cyanobenzo ate, thallium naphthalene-1-carboxylate, thallium 2-methylnaphthalene- 1-carboxyla te, thallium 4-methylnaphthalene-1-carboxylate, thallium 5-mcthylnaphthalcnc-1-carboxylatc, thallium 6-methylnaphthalene-l -carboxylate, thallium 7-methylnaphthalene-l -carboxylate, thallium 8-methylnaphthalene-1-carboxylate, thallium naphthalene- 2-carboxylate, thallium 1-methylnaphthalene-2-carboxylate, thallium 4-methylnaphthalene-2-carboxylate, thallium 5—methylnaphthalene—2—carboXylate, thallium thallium thallium thallium 6-methylnaphthalene-2-carboxylate, thallium 8-methylnaphthalene-2-carboxylate, thallium 5—chloronaphthalene—1—carboXylate, thallium 7-chloronaphthalene-1-carboxylate, thallium 8-chloronaphthalene-1-carboxylate, thallium thallium thallium thallium thallium thallium thallium thallium thallium 4-bromonaphthalene-1-carboxylate, 5-bromonapl1thalene-1-carboxylate, 7-bromonaphthalene-1-carboxylate, 8-bromonaphthalene-1-carboxylate, 8-iodonaphthalene-1-carboxylate, 1-chloronaphthalene-2-carboxylate, 3-chloronaphthalene-2-carboxylate, 5-chloronaphthalene-2-carboxylate, 5-bromonaphthalene-2-carboxylate, thallium 3-iodonaphthalene-2-carboxylate, thallium bcnzcncsulfonatc, thallium 2-tolucncsulfonatc, thallium 3-toluenesulfonate, thallium 4-toluenesulfonate, thallium o-Xylene-4-sulfonate, thallium m-Xylene-4-sulfonate, thal- lium p—Xylene—4—sulfonate, thallium 4-fluorobenzenesulfonate, thallium 2-chlorobenzenesulfonate, thallium 3—chlorobenzenesulfonate, thallium 4-chlorobenzenesulfonate, thallium 2,4- dichlorobenzenesulfonate, thallium 2-bromobenzenesulfonate, thallium 3-bromobenzenesulfonate, thallium 4-bromobenzenesulfonate, thallium 2,5- dibromobenzenesulfonate, thallium 3,4- (libromobenzenesulfonate, thallium 2-iodobenzenesulfonate, thallium 3-iodobenzenesulfonate, thallium 4-iodobenzenesulfonate, thallium methanesulfonate, thallium ethanesulfonate, thallium US 6,830,704 B2 17 propanesulfonate, thallium butanesulfonate, thallium pentanesulfonate, thallium hexanesulfonate, thallium heptanesulfonate, thallium octanesulfonate, thallium trifiuoromethanesulfonate, thallium pentafluoroethanesulfonate, thallium heptafiuoropropanesulfonate, thallium pcrfiuorobutancsulfonatc, thallium perfiuoropentanesulfonate, thallium perfluorohexanesulfonate, thallium perfiuorooctanesulfonate, thallium perchlorate, and the anhydrides and hydrates of those salts. Of the Lewis acid metal salts enumerated above,for example the metal salts hereinafter easily commercially available include zinc acetate, zinc p-toluenesulfonate, zinc trifluoroacetate, zinc trifluoromethanesulfonate, zinc perchlorate, zinc benzenesulfonate, zinc butyrate, zinc formate, zinc propionate, zinc acrylate, zinc methacrylate, zinc 2-ethylhexanoate, cadmium acetate, cadmium formate, cadmium perchlorate, mercury acetate, mercury formate, mercury perchlorate, aluminum acetate, aluminum formate, aluminum perchlorate, aluminum acrylate, aluminum methacrylate, gallium acetate, gallium perchlorate, gallium trifluoroacetate, indium perchlorate, indium trifluoroacetate, thallium acetate, thallium formate, thallium perchlorate and thallium trifluoroacetate. The other Lewis acid metal salts can also be synthesized according to conventional processes. Examples of the synthesis techniques include (1) reaction of a metal oxide with an acid or acid anhydride, (2) reaction of a hydroxide with an acid or acid anhydride, (3) reaction of a carbonate with an acid or acid anhydride, (4) reaction of a metal halide with an acid or acid anhydride, reaction of metal with an acid and (6) reaction of a metal alkoxide with an acid or acid anhydride. The 2-cyanoacrylate composition of the present invention may contain only one Lewis acid metal salt or may contain a mixture of two or more Lewis acid metal salts. Preferred Lewis acid metal salts are salts of halogenoacetic acids with specific metals because those salts are especially effective in improving the clearance curability and surface curability of the 2-cyanoacrylate composition of the present invention. More preferred Lewis acid metal salts are salts of trihalo- genoacetic acids with specific metals. Most preferred Lewis acid metal salts are zinc trifluoroacetate, cadmium trifluoroacetate, mercury trifiuoro acetate, aluminum trifluoroacetate, gallium trifluoroacetate, indium trifluoroac- etate and thallium trifluoroacetate. The preferred range of the amount of the Lewis acid metal salt in the composition according to the present invention is from 0.1 ppm by weight to 1% by weight based on the weight of the 2-cyanoacrylate. If its amount is less than 0.1 ppm by weight, ability to accelerate the curing of thc 2-cyanoacrylate is poor, and if its amount is more than 1% by weight, there is the possibility that storage stability of the 2-cyanoacrylate is greatly impaired. The more preferred range of the amount of the Lewis acid metal salt is from 1 to 500 ppm by weight. Where two or more Lewis acid metal salts are used, the concentration range is for the total amount of the Lewis acid metal salts used. Compound Having Clathrating Ability: The compound having clathrating ability used in the present invention is a compound which is capable of includ- ing inorganic cations such as metal ions or hydronium ions or organic cations such as primary ammonium ions to thereby activate the counter anions and l1as conventionally been known as a curing accelerator for 2-cyanoacrylate compositions. Preferred examples of the compound are poly(alkylene oxide)s and derivatives thereof, crown ethers, 10 15 20 30 35 40 45 55 60 65 18 silacrown ethers, Calixarenes, cyclodextrins and derivatives thereof, and pyrogallol-based cyclic compounds, because those compounds are effective in accomplishing the object of the present invention. Poly(Alkylene Oxide)s and Derivatives Thereof: Examples of the poly(alkylene oxide)s and derivatives thereof are disclosed in, c.g., JP-B-60-37836, JP-B-1-43790, JP-A-63-128088, JP-A-3-167279, U.S. Pat. No. 4,386,193 and U.S. Pat. No. 4,424,327. Preferred examples of the poly(alkylene oxide)s include diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, polypropylene glycol, poly-1,3- propylene glycol, poly(trimethylene oxide), poly (tetramethylene oxide), polyepichlorohydrin, poly(1,3-bis (chloromethyl)butylene oxide), polytetramethylene glycol, poly(1,3—dioxolane), poly(2,2—bis(chloromethyl)propylene oxide), ethylene oxide/propylene oxide block copolymers, polyglycerols such as diglycerol, triglycerol or tetraglycerol, formaldehyde condensates, acetaldehyde condensates, triox- ane polymers and various poly(alkylene oxide)s commer- cially available as polyols for curing polyether type ure- thanes. The poly(alkylene oxide) derivatives are represented by the esters of the poly (alkylene oxide)s enumerated above with acids and the ethers of the poly(alkylene oxide)s with hydroxy compounds. Although those compounds are preferred, the poly(alkylene oxide) derivatives are not par- ticularly limited to those. Other examples thereof include compounds having a poly(alkylene oxidc) structure in the molecule, such as ones having various substituents at the molecular ends and ones having other kinds of bonds in the poly(alkylene oxide). Examples of the acids capable of forming the esters include acetic acid, propionic acid, butyric acid, isobutyric acid, pivalic acid, pentanoic acid, n—hexanoic acid, 2-methylpentanoic acid, n-octanoic acid, n-decanoic acid, lauric acid, palmitic acid, stearic acid, oleic acid, cyclohexy- lcarboxylic acid, cyclopentylcarboxylic acid, cyclopropyl— carboxylic acid, acrylic acid, methacrylic acid, maleic acid, itaconic acid, naphthenic acid, benzoic acid, [3-naphthylcarboxylic acid, p-toluenesulfonic acid, furancar- boxylic acid, p-chlorobenzoic acid, monocliloroacetic acid, cyanoacetic acid, adipic acid, sebacic acid, butanetetracar- boxylic acid, aconitic acid, propane-1,2,3-tricarboxylic acid, citric acid, o-pl1tl1alic acid, isophthalic acid, trimellitic acid and pyromellitic acid. Specific examples of the poly(alkylene oxide) esters include polyethylene glycol monoalkyl esters, polyethylene glycol diesters or polypropylene glycol diesters (e.g., acetate, trifluoroacetate, laurate, stearate, oleate, acrylate and mcthacrylatc), bisphcnol A/poly(alkylene oxidc) adducts (examples of the alkylene include ethylene and propylene; the same applies hereinafter), hydrogenated bisphenol A/poly(alkylene oxide) adducts, trimethylolpropane/poly(alkylene oxide) adducts, glycerol/ poly(alkylene oxide) adducts, polyoxyethylene-sorbitan esters, polyoxyethylene-sorbitan tetraoleate, adipic acid/ poly(alkylene oxide) adducts, trimellitic acid/poly(alkylene oxide) adducts, isocyanate compound/poly(alkylene oxide) adducts, phosphoric acid/poly(alkylene oxide) adducts, silicic acid/poly(alkylene oxide) adducts and polyoxyalky- lene polyphosphates. Examples of the hydroxyl group-containing compounds capable of forming the ethers include methanol, ethanol, propanol, isobutanol, hexanol, cyclohexanol, 2-ethyloctanol, decanol, lauryl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, phenol, on-naphthol, [3-naphthol, US 6,830,704 B2 19 cresol, t-butylphenol, octylphenol, nonylphenol, p-chlorophenol, resol, bisphenol A, 2-chloroethanol, ethyl- ene cyanohydrin, trifluoroethanol, benzyl alcohol, 1,4- butanediol, 1,6-hexanediol, glycerol, sorbitol, hydrogenated bisphenol A and trimethylolpropane. Specific examples of the poly(alkylene oxide) ethers include diethylene glycol monoalkyl ethers, diethylene gly- col dialkyl ethers, polyethylene glycol monoalkyl ethers (examples of the alkyls include methyl, ethyl, propyl, butyl, lauryl, cetyl, stearyl, oleyl and perfluoroalkyls), polyethyl- ene glycol monoaryl ethers, polyethylene glycol dialkyl ethers, polypropylene glycol dialkyl ethers (examples of the alkyls include methyl, ethyl, propyl, and butyl), and poly- ethylene glycol diaryl ethers (examples of the aryls include phenyl, octylphenyl and nonylphenyl). Crown Ethers: Examples of the crown ethers include those already disclosed in, e.g., JP-B-55-2236 and JP-A-3-167279. Pre- ferred examples thereof include 15-crown-O-5, 18-crown- O-6, benzo-12-crown-O-4, benzo-15-crown-O-5, benzo-18- crown-O-6, dibenzo-18-crown-O-6, benzo-15-crown-O-5, dibenzo—24—crown—O—8, dibenzo—30—crown—O—10, tribenzo— 18-crown-O-6, asym-dibenzo-22-crown-O-6, dibenzo-14- crown-O-4, dicyclohexyl-24-crown-O-8, cyclohexyl-12- crown-O-4, 1,2-decalyl-15-crown-O-5, 1,2-naphtho-15- crown-O-5, 3,4,5-naphthyl-16-crown-O-5, 1,2- methylbenzo—18—crown—O—6, 1,2—tert—butyl—18—crown—O—6, 1,2-vinylbenzo-15-crown-O-5 and 1,2-benzo-1,4-benzo-5- oxygen-20-crown-7. Silacrown Ethers: Examples of the silacrown ethers are disclosed in, e.g., J P-A-60-1 68775. The examples include dimethylsila- l 1 - crown-O -4, d imethylsila- 14-crown-O -5 and dimethylsila - 17-crow11-O-6. Calixarenes: Examples of the Calixarenes are disclosed in, e.g., JP-A- 60-179482, JP-A-62-235379 and JP-A-63-88152. The examples include compounds represented by formula (1): (1) R2 wherein R1 represents alkyl, alkoxy, substituted alkyl or substituted alkoxy, R2 represents H or alkyl, and n is 4, 6 or 8. Cyclodextrins: Examples of the cyclodextrins are disclosed in, e.g., JP-W-5-505835. The examples include (1-, [3- and/or y-cyclodextrins represented by formula (2): 10 15 20 30 35 40 45 55 60 65 20 (2) OR6 0R3 O OR2 wherein R2, R3 and R6 which may be the same or different each represent hydrogen atom, alkyl group, alkylene group, cycloalkyl group, alkylaryl group, acyl group, trialkylsilyl group or urethane group, provided that all of R2, R3 and R6 are not hydrogen atom; and n is 6, 7 or 8). Pyrogallol-Based Cyclic Compounds: Examples of the pyrogallol-based cyclic compounds include compounds represented by formula (3), which are disclosed in Japanese Patent Application No. 10-375121. Preferred examples thereof include 3,4,5,10,11,12,17,18,19, 24,25,26,-dodecaethoxycarbomethoxy-C-1,C-8,C-15,C-22- tetramethyl[14]—metacyclophane. (3) where Y’s each represent hydrogen atom, OH or OR (wherein R is a substituent not initiating polymerization of 2-cyanoacrylate), provided that at least one of the Y’s is OR and at least one of the remaining Y’s is OH or OR; n is an even number of 4 or larger; R1 represents hydrogen atom or methyl group; and R2 represents a substituent not initiating polymerization of 2-cyanoacrylate. Such compounds having clathrating ability according to the present invention may be used alone or as a mixture of two or more thereof to the 2-cyanoacrylate. Of those compounds having clathrating ability, crown ethers are generally preferable because those have high effect to improve the clearance curability and surface cur- ability of the 2-cyanoacrylate composition. Specific examples of the preferred compounds having high effect to improve the clearance curability and surface curability of the 2-cyanoacrylate composition are polyethylene glycol, poly- ethylene glycol monoacrylate, polyethylene glycol diacrylate, polyethylene glycol monomethacrylate, polyeth- ylene glycol dimethacrylate, 18-crown-O-6, benzo-18- crown-O-6, 4-tert-butylCalix[4]arene-0,0',0",0"'-tetraacetic acid tctracthyl ester and 3,4,5,10,11,12,17,18,19,24,25,26,- dodecaethoxycarbomethoxy-C-1,C-8,C-l5,C-22- tetramethyl[14]-metacyclophane. The amount of the compound having clathrating ability added is preferably from 10 ppm by weight to 10% by weight, more preferably from 100 ppm by weight to 1% by weight, based on the weight of the 2-cyanoacrylate compo- sition. If its amount is less than 10 ppm by weight, it is difficult to impart sufficient rapid-curing properties to the 2-cyanoacrylate composition, and if its amount is more than 10% by weight, storage stability of the composition consid- erably lowers. Where two or more compounds having clath- rating ability are used, its concentration range is for the total amount of those compounds used. US 6,830,704 B2 21 2-Cyanoacrylate: 'lhe 2-cyanoacrylate serving as the main component of the 2-cyanoacrylate composition of the present invention is one ordinarily used in cyanoacrylate-based adhesives a11d the like. Examples of the 2-cyanoacrylate include methyl 2-cyanoacrylate, ethyl 2-cyanoacrylate, propyl 2-cyanoacrylate, isopropyl 2-cyanoacrylate, butyl 2-cyanoacrylate, isobutyl 2-cyanoacrylate, amyl 2-cyanoacrylate, hexyl 2-cyanoacrylate, cyclohexyl 2-cyanoacrylate, octyl 2-cyanoacrylate, 2-ethylhexyl 2-cyanoacrylate, allyl 2-cyanoacrylate, propargyl 2-cyanoacrylate, phenyl 2-cyanoacrylate, benzyl 2-cyanoacrylate, methoxyethyl 2-cyanoacrylate, ethoxy- ethyl 2-cyanoacrylate, tetrahydrofurfuryl 2-cyanoacrylate, 2—chloroethyl 2-cyanoacrylate, 3—chloropropyl 2-cyanoacrylate, 2-chlorobutyl 2-cyanoacrylate, 2,2,2- trifluoroethyl 2-cyanoacrylate and hexafiuoroisopropyl 2-cyanoacrylate. Those 2-cyanoacrylates may be used alone or as a mixture of two or more thereof in the 2-cyanoacrylate composition of the present invention. Of those 2-cyanoacrylates, the 2-cyanoaerylic esters with lower alkyls having 1 to 4 carbon atoms are advantageous in that use of such 2-cyanoacrylates provides high effect to enhance the surface curability and clearance curability, the improvement of which is the object of the present invention. Other Ingredients: T'he 2-cyanoacrylate composition of the present invention comprises a Lewis acid metal salt, a compound having clathrating ability and a 2-cyanoacrylate as essential ingre- dients. However, one or more of ingredients such as a stabilizer for anionic polymerization, a stabilizer for radical polymerization, a thickener, a curing accelerator, a plasti- cizer and a thixotropic agent may be added to the compo- sition according to need when the composition is used as an adhesive, a potting material or a filler. Examples of the stabilizer for anionic polymerization include sulfurous acid gas, nitrogen monoxide, hydrogen fluoride, sulfone compounds, BF3/ether complexes, BF3/ acetic acid complex, BF3/methanol complex, methane- sulfonic acid, p-toluenesulfonic acid and scandium trifluo- romethanesulfonate. The amount of the stabilizer added is preferably from 1 ppm by weight to 1% by weight based on the weight of the 2-cyanoacrylate composition. Examples of the stabilizer for radical polymerization include hydroquinone, hydroquinone monomethyl ether, catechol and pyrogallol. The amount of the stabilizer added is preferably from 1 ppm by weight to 1% by weight based on the weight of 2-cyanoacrylate composition. Examples of the thickener include poly(methyl methacrylate), copolymers of methyl methacrylate and an acrylic ester, copolymers of methyl methacrylate and another methacrylic ester and cellulose derivatives. The amount of the thickener added is preferably from 0.1 to 20% by weight based on the weight of the 2-cyanoacrylate composition. Examples of the plasticizer include dioctyl phthalate and dibutyl phthalate. The amount of the plasticizer added is preferably from 0.01 to 30% by weight based on the weight of the 2-cyanoacrylate composition. Examples of the thixotropic agent include hydrophobic silica. The amount of the thixotropic agent added is prefer- ably from 0.1 to 20% by weight based on the weight of the 2-cyanoacrylate composition. Ingredients other than the above-described ingredients may further be added according to purposes. Examples of 10 15 20 30 35 40 45 55 60 65 22 such further ingredients include adhesion promoters, dyes, perfumes, fillers, crosslinking agents, tougheners and organic solvents. When the 2-cyanoacrylate composition of the present invention is used as a potting material, a filler or a instan- taneous adhesive, it can cure in a short period of time even in a relatively wide gap between adherends or on a surface onto which the composition has overflowed. Although the reasons for this effect have not been elucidated, the follow- ing is presumed. The Lewis acid metal salt according to the present invention forms a complex with a 2-cyanoacrylate and thus lowers the B-position electron density in the 2-cyanoacrylate to thereby enable the anionic polymeriza- tion to proceed more readily. However, when the Lewis acid metal salt is used alone, such a use alone has no effect because the salt itself is an acidic substance. The metal salt hence functions to accelerate the curing only when it is used in combination with a compound having clathrating ability. The present invention will be explained in more detail by reference to the following Examples and Comparative Examples, but the invention should not be construed as being limited to those Examples. The following evaluation method was used. Clearance Setting 'l‘ime (Clearance Curability): Apolyethylene plate having a recess having a diameter of 6 mm and a depth of 0.5 mm was used as a base after a few drops of DOP (dioctyl phthalate) were dropped into the recess in order to prevent adhesive leakage through a gap at the bottom of a test piece. A cylindrical test piece made of aluminum which weighed 100 g and had a hole having a diameter of 6.95 mm and a depth of 20 mm was placed on this polyethylene plate. A cylindrical pin made of aluminum having a diameter of 6.55 mm and a height of 40 mm was placed in the hole so as not to be in contact with the inner wall of the test piece. A 2-cyanoacrylate composition was poured into the space between the test piece and the pin. After allowing to stand those for a given period of time, the pin was held and lifted up. The time required for the test piece to be lifted up together with the pin was taken as the clearance setting time. The 2-cyanoacrylate composition according to the present invention is widely used as a cyanoacrylate instantaneous adhesive to adhere various materials such as glasses, metals, plastics, rubbers, woods, potteries, papers and woven fabrics in various industrial fields such as electronic a11d electric fields, automobile fields and wood processing fields; medi- cal fields, leisure fields and general household fields. Further, the 2-cyanoacrylate composition is used as pot- ting materials or fillers in mainly electronic and electric fields. For example, the 2-cyanoacrylate composition is used to adhere a part and a main body or adhere at least two parts to form an article. Further, the 2-cyanoacrylate composition is used to fill depressions on a surface and then cure the same to form an article. EXAMPLE 1 Aluminum acetate and 18-crown-O-6 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This com- position was subjected to the evaluation. The results obtained are shown in Table 1. EXAMPLE 2 Aluminum formate and 18-crown-O-6 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts US 6,830,704 B2 23 thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This com- position was subjected to the evaluation. The results obtained are shown in Table 1. EXAMPLE 3 Al11min11m benzoate and 18-crown-O-6 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This com- 10 position was subjected to the evaluation. The results obtained are shown in Table 1. SYNTHESIS EXAMPLE 1 15 (Synthesis of Aluminum Monochloroacetate) The target compound was synthesized by the method described in P. K. Bhattacharya et al., Indian Journal of Chemistry, Vol.28A (September 1989), p.779. In dry ben- zene was dissolved 1.62 g (0.01 mol) of aluminum triiso- propoxide. While stirring the resulting solution at room tcmpcraturc, 19 g (0.20 mol) of monochloroacctic acid was added dropwise thereto. This addition resulted in a tempera- ture increase. After completion of the dropwise addition, the resulting mixture was heated to 100 to 120° C. and refluxed for 18 hours, and then cooled to room temperature. The solvent, by-product isopropyl monochloroacetate and monochloroacetic acid remaining unreacted were distilled off under vacuum to obtain a white powder, which was subjected to elemental analysis and infrared spectrometry. As a result, this powder was found to be nearly pure aluminum monochloroacetate. 20 30 EXAMPLE 4 Aluminum monochloroacetate and 18-crown-O-6 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This com- position was subjected to the evaluation. The results obtained are shown in Table 1. 35 40 SYNTHESIS EXAMPLE 2 (Synthesis of Aluminum Dichloroacetate) Aluminum dichloroacetate was synthesized according to Synthesis Example 1. 45 EXAMPLE 5 Aluminum dichloroacetate and 18-crown-O-6 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This com- position was subjected to the evaluation. The results obtained are shown in Table 1. SYNTHESIS EXAMPI .E 3 55 (Synthesis of Aluminum Trichloroacetate) Aluminum trichloroacetate was synthesized according to Synthesis Example 1. EXAMPLE 6 60 Aluminum trichloroacetate and 18-crown-O-6 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This com- position was subjected to the evaluation. The results obtained are shown in Table 1. 65 24 SYNTHESIS EXAMPLE 4 (Synthesis of Aluminum Methanesulfonate) Aluminum methanesulfonate was synthesized according to Synthesis Example 1. EXAMPLE 7 Aluminum methanesulfonate and 18-crown-O-6 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This com- position was subjected to the evaluation. The results obtained are shown in Table 1. SYNTIIESIS EXAMPLE 5 (Synthesis of Aluminum Trifluoroacetate) Aluminum trifluoroacetate was synthesized according to Synthesis Example 1. EXAMPLE 8 Aluminum trifluoroacetate and 18-crown-O-6 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This c0111- position was subjected to the evaluation. The results obtained are shown in Table 1. EXAMPLE 9 Aluminum trifluoroacetate and 4-tert—butylCalix[4]arene— 0,0‘,0",0"‘-tetraacetic acid tetraethyl ester were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm by weight and 1% by weight, respectively, to prepare an adhesive composition. This com- position was subjected to the evaluation. The results obtained are shown in Table 1. EXAMPLE 10 Aluminum trifluoroacetate and 3,4,5,10,11,12,17,18,19, 24,25,26-dodecaethoxycarbomethoxy-C-1,C-8,C-15,C-22- tetramethyl[14]-metacyclophane were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm by weight and 1% by weight, respectively, to prepare an adhesive composition. This composition was subjected to the evaluation. The results obtained are shown in Table 1. SYNTHESIS EXAMPLE 6 (Synthesis of Gallium Trifluoroacetate) The target compound was synthesized by the method described in Peter Sartori et al., Journal of Fluorine Chemistry, 1 (1971/72), p.463. In a round bottom flask from which moisture had been completely eliminated was placed 1.76 g (0.01 mol) of gallium chloride. 20 cc (0.25 mol) of trifluoroacetic acid was gradually added dropwise to the flask. Immediately upon initiation of the dropwise addition, a white fume generated and heat generation occurred. After completion of the dropwise addition, the reaction mixture was stirred and heated for further 140 hours at 60 to 70° C. The reaction mixture was then cooled to room temperature and the volatile ingredients were completely distilled off under vacuum to obtain a light-yellow powder, which was subjected to elemental analysis and infrared spectrometry. As a result, this powder was found to be nearly pure gallium trifluoroacetate. EXAMPLE 11 Gallium trifluoro acetate and 18-crown-O-6 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts US 6,830,704 B2 25 thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This com- position was subjected to the evaluation. The results obtained are shown in Table 1. SYNTHESIS EXAMPLE 7 (Synthesis of Indium Trifluoroacetate) The target compound was synthesized by the method described in Peter Sartori et al., Journal of Fluorine Chemistry, 1 (1971/72), p.463. In a round-bottomed flask fro111 which moisture had been completely eliminated was placed 1.15 g (0.01 mol) of indium. 39 cc (0.50 mol) of trifluoroacetic acid was gradually added dropwise to the flask. This mixture was stirred at room temperature for 3 days. As a result, the indium ingot had disappeared and a white precipitate had generated. The volatile ingredients were completely distilled off under vacuum to obtain a white powder, which was subjected to elemental analysis and infrared spectrometry. As a result, this powder was found to be nearly pure indium trifluoroacetate. EXAMPLE 12 Indium trifluoroacetate and 18-crown-O-6 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This com- position was subjected to the evaluation. The results obtained are shown in Table 1. EXAMPLE 13 Thallium trifluoroacetate and 18-crown-O-6 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This com- position was subjected to the evaluation. The results obtained are shown in Table 1. EXAMPLE 14 Thallium trifluoroacetate and PEG 1,000 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 2,000 ppm by weight, respectively, to prepare an adhesive composition. This com- position was subjected to the evaluation. The results obtained are shown in Table 1. EXAMPLE 15 Thallium trifluoroacetate and PEG 1,000 dimethacrylate were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 2,000 ppm by weight, respectively, to prepare an adhesive composition. This composition was subjected to the evaluation. The results obtained are shown in Table 1. EXAMPLE 16 Zinc trifluoromethanesulfonate hydrate and 18-crown- O—6 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This composition was subjected to the evaluation. The results obtained are shown in Table 1. EXAMPLE 17 Zinc trifluoromethanesulfonate hydrate and PEG 1,000 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 2,000 ppm by 10 15 20 30 35 40 45 55 60 65 26 weight, respectively, to prepare an adhesive composition. This composition was subjected to the evaluation. The results obtained are shown in Table 1. EXAMPLE 18 Zinc trifluoromethanesulfonate hydrate and PEG 1,000 dimethacrylate were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 2,000 ppm by weight, respectively, to prepare an adhesive composition. This composition was subjected to the evalu- ation. The results obtained are shown in Table 1. EXAMPLE 19 Cadmium acetate and 18-crown-O-6 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This com- position was subjected to the evaluation. The results obtained are shown in Table 1. EXAMPI .E 20 Mercury trifluoroacetate and 18-crown-O-6 were mixed with ethyl 2-cyanoacrylate in amounts such that the amounnts thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This com- position was subjected to the evaluation. The results obtained are shown in Table 1. EXAMPLE 21 Aluminum trifluoroacetate and PEG 1,000 dimethacrylate were mixed with isopropyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 2,000 ppm by weight, respectively, to prepare an adhesive composition. This composition was subjected to the evaluation. The results obtained are shown in Table 1. EXAMPLE 22 Aluminum trifluoroacetate and 18-crown-O-6 were mixed with isopropyl 2-cyanoacrylate in amounts such that the amounts thereof became 10 ppm and 500 ppm by weight, respectively, to prepare an adhesive composition. This C0111- position was subjected to the evaluation. The results obtained are shown in Table 1. COMPARATIVE EXAMPLE 1 An adhesive composition was prepared with ethyl 2-cyanoacrylate which does not contain a Lewis acid metal salt and a host compound capable of forming a clathrate compound with a metal as a guest. This composition was subjected to the evaluation. The results obtained are shown in Table 1. COMPARATIVE EXAMPLE 2 An adhesive composition was prepared with isopropyl 2-cyanoacrylate which does not contain a Lewis acid metal salt and a host compound capable of forming a clathrate compound with a metal as a guest. This composition was subjected to the evaluation. The results obtained are shown in Table 1. COMPARATIVE EXAMPI .E 3 PEG 1,000 was mixed with ethyl 2-cyanoacrylate in an amount such that the amount thereof became 2,000 ppm by US 6,830,704 B2 27 weight to prepare an adhesive composition. This composi- tion was subjected to the evaluation. The results obtained are shown in Table 1. COMPARATIVE EXAMPLE 4 PEG 1,000 dimethacrylate was mixed with ethyl 2-cyanoacrylate in an amount such that the amount thereof became 2,000 ppm by weight to prepare an adhesive com- position. This composition was subjected to the evaluation. The results obtained are shown in Table 1. COMPARATIVE EXAMPLE 5 PEG 1,000 dimethacrylate was mixed with isopropyl 2-cyanoacrylate in an amount such that the amount thereof became 2,000 ppm by weight to prepare an adhesive com- position. This composition was subjected to the evaluation. The results obtained are shown in Table 1. COMPARATIVE EXAMPLE 6 18-Crown-O-6 was mixed with isopropyl 2-cyanoacrylate in an amount such that the amount thereof became 500 ppm by weight to prepare an adhesive composition. This com- position was subjected to the evaluation. The results obtained are shown in Table 1. COMPARATIVE EXAMPLE 7 18-Crown-O-6 was mixed with ethyl 2-cyanoacrylate in an amount such that the amount thereof became 500 ppm by weight to prepare an adhesive composition. This composi- tion was subjected to the evaluation. The results obtained are shown in Table 1. COMPARATIVE EXAMPLE 8 4-tert-ButylCalix[4]arene-0,0‘,0",0‘"-tetraacetic acid tet- raethyl ester was mixed with ethyl 2-cyanoacrylate in an amount such that the amount thereof became 1% by weight to prepare an adhesive composition. This composition was subjected to the evaluation. The results obtained are shown in Table 1. COMPARATIVE EXAMPLE 9 3,4,5,10,11,12,17,18,19,24,25,26— Dodecaethoxycarbomethoxy-C-1 ,C-8,C-15,C-22- tetramethyl[14]-metacyclophane was mixed with ethyl 2-cyanoacrylate in an amount such that the amount thereof became 1% by weight to prepare an adhesive composition. This composition was subjected to the evaluation. The results obtained are shown in Table 1. COMPARAII VE EXAMPLE 10 Aluminum trifluoroacetate was mixed with ethyl 2-cyanoacrylate in an amount such that the amount thereof became 10 ppm by weight to prepare an adhesive compo- sition. This composition was subjected to the evaluation. The results obtained are shown in Table 1. COMPARATIVE EXAMPLE 11 Thallium trifluoroacetate was mixed with ethyl 2-cyanoacrylate in an amount such that the amount thereof became 10 ppm by weight to prepare an adhesive compo- sition. This composition was subjected to the evaluation. The results obtained are shown in Table 1. 10 15 20 30 35 40 45 55 60 65 28 TABLE 1 Setting time min min min min min min min min min min min min min min min min min min min min min min min (‘D >—t -4 >—t an an Ix) >—t >—t N U) >—| O 45-\DO\l\l\]CJ4>-G'\LI\L»JU\LI\O0-P-Px\D\1\l\lOO\l\l min >—t \l min >—| 00 min 16 min 15 min 13 min 17 min 15 min min 38 min 0 O umUmuwqmiuniuniuniuniuniumuguuuuuuuuuuuuuuuuuuuuuu .>-: N .—» »- < (‘D to APPLICATION EXAMPLE 1 In producing input and output leading wires by adhering PVC coated wire and a PVC-made connector, there is 0.2 mm clearance between the wire and a socket on the con- nector portion. When the conventional 2-cyanoacrylate adhesive (viscosity: 100 mP~s) was used to adhere those, the assembly was required to be allowed to stand for at least 2 minutes. Thus, this adhering operation could not be put on the production line. On the other hand, when the adhesive comprising the 2-cyanoacrylate composition of the present invention was used, the adhesive set for 60 seconds. Thus, the adhering operation could be put on the production line, and working efficiency was greatly improved. The adhesives used are as follows. Conventional 2-cyanoacrylate adhesive: Main component: Ethyl-2-cyanoacrylate 18-Crown-O-6: 100 ppm Thickener: PMMA, 2% 2-Cyanoacrylate composition of the present invention: Main component: Ethyl-2-cyanoacrylate Aluminum trifluoroacetate: 50 ppm 18-Crow-O-6: 100 ppm Thickener: PMMA (polymethyl methacrylate), 2% US 6,830,704 B2 29 APPLICATION EXAMPLE 2 In adhering PVC-made break hose and a urethane-made fixture, there is 0.5 mm clearance therebetween. When those was adhered using the conventional 2-Cyanoacrylate adhesive, it took about 20 minutes or more. Thus, produc- tivity was poor. On the other hand, when the adhesive comprising the 2-Cyanoacrylate composition of the present invention was used, the adhesive set for about 8 minutes. Thus, working efliciency was greatly improved. The adhesives used are as follows. Conventional 2-Cyanoacrylate adhesive: Main component: Ethyl-2-cyanoacrylate 18-Crown-O-6: 200 ppm Thickener: PMMA, 2% 2-Cyanoacrylate composition of the present invention: Main component: Ethyl-2-cyanoacrylate Aluminum trifiuoroacetate: 40 ppm 18-Crown-O-6: 200 ppm Thickener: PMMA, 2% APPLICATION EXAMPLE 3 In filling and adhering a space (0.2 mm clearance) between tenon and joggle on a wood plate without using a nail, use of the conventional gel-like 2-Cyanoacrylate adhe- sive required 30 minutes or more. Thus, productivity was poor On the other hand, when the adhesive comprising the 2-Cyanoacrylate composition of the present invention was used, the adhesive set for about 10 minutes. Thus, working efliciency was greatly improved. The adhesives used are as follows. Conventional 2-Cyanoacrylate adhesive: Main component: Ethyl-2-cyanoacrylate PEG 1000: 2,000 ppm Thickener: PMMA, 1% Ilydrophobic silica: 5% 2-Cyanoacrylate composition of the present invention: Main component: Ethyl-2-cyanoacrylate PEG 1000: 2,000 ppm Thickener: PMMA, 1% Aluminum trifiuoroacetate: 70 ppm Hydrophobic silica: 5% As described above, the 2-Cyanoacrylate composition of the present invention has excellent clearance curability and surface curability. The composition can hence be used in a wider range of industrial and domestic applications. In particular, since the composition can bond adherends to each other in a short period of time even when the gap therebe- tween is relatively wide, it is free from the problem of sufficiently cleaning or polishing adherend surfaces before- hand. As a result, the time required for bonding operation is 10 15 20 30 35 40 45 30 considerably shortened and the operating efficiency is greatly increased. Even where the composition is used by general consumers having a poor knowledge about bonding, it can be easily applied because there is no need of paying attention to the gap or to an overfiowed part of the compo- sition during the bonding operation. Therefore, the compo- sition has remarkable effects on various industries. What is claimed is: 1. A 2-Cyanoacrylate composition comprising: (1) aluminum trifiuoroacetate salt, and (2) a compound having clathrating ability. 2. The 2-Cyanoacrylate composition as claimed in claim 1, wherein the compound having clathrating ability is one selected from the group consisting of poly(alkylene oXide)s and derivatives thereof, crown ethers, silacrown ethers, Calixarenes, cyclodextrins and derivatives thereof, and pyrogallol-based cyclic compounds. 3. The 2-Cyanoacrylate composition as claimed in claim 1, wherein the amount of aluminum trifluoroacetate salt is 0.1 ppm by weight to 1% by weight based on the weight of the 2-Cyanoacrylate. 4. The 2-Cyanoacrylate composition as claimed in claim 1, wherein the amount of aluminum trifiuoroacetate salt is 1 to 500 ppm by weight based on the weight of the 2-Cyanoacrylate. 5. The 2-Cyanoacrylate composition as claimed in claim 1, wherein said compound having clathrating ability is a crown ether. 6. The 2-Cyanoacrylate composition as claimed in claim 1, wherein said compound having clathrating ability is selected from the group consisting of polyethylene glycol, polyeth- ylene glycol monoacrylate, polyethylene glycol diacrylate, polyethylene glycol niononiethacrylate, polyethylene glycol dimethacrylate, 18-crown-O-6, benzo-18-crown-O-6, 4-tert- butylCaliX[4]arene-0,0',0",0'"-tetraacetic acid tetraethyl ester and 3,4,5,10,11,12,17,18,19,24,25,26,- dodecaethoxycarbomethoXy-C-1,C-8,C-15,C-22- tetramethyl [14]-metacyclophane. 7. The 2-Cyanoacrylate composition as claimed in claim 1, wherein the amount of the compound having clathrating ability is 10 ppm by weight to 10% by weight based on the weight of the 2-cyanoacrylatc composition. 8. The 2-Cyanoacrylate composition as claimed in claim 1, wherein the amount of the compound having clathrating ability is 100 ppm by weight to 1% by weight based on the weight of the 2-Cyanoacrylate composition. 9. An article comprising a part and a main body, adhered using the 2-Cyanoacrylate composition as claimed in claim 1. 10. An article having depressed portion on the surface thereof, said depressed portions being filled and adhered with the 2-Cyanoacrylate composition as claimed in claim 1. * * >I< * >!<