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(12) United States Patent (10) Patent No.: US 6,995,227 B2 Ryan Et Al

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(12) United States Patent (10) Patent No.: US 6,995,227 B2 Ryan Et Al USOO6995227B2 (12) United States Patent (10) Patent No.: US 6,995,227 B2 Ryan et al. (45) Date of Patent: Feb. 7, 2006 (54) ACTIVATOR COMPOSITIONS FOR 3,654,340 A 4/1972 Banitt ..................... 260/465.4 CYANOACRYLATE ADHESIVES 3,836,377 A * 9/1974 Delahunty .................. 526/205 3.869.435 A * 3/1975 Trivette, Jr. ....... ... 525/341 (75) Inventors: Bernard Ryan, Dublin (IE); Hanns 3.2Y- - - 2 A 3.E. GSINCOC Sh alC a I... i. Botanis pit 8.is A. 5,314,562 A 5/1994 McDonnell et al. ........ 156/314 McCann, s Dublin (IE) s 5,749.956. A 5/1998 Fisher et al............ 106/287.28 FOREIGN PATENT DOCUMENTS (73) Assignee: Loctite R&D Limited, Dublin (IE) DE 278O33 4/1990 * Y NotOtice: Subjubject to anyy disclaimer,disclai theh term off thisthi EP O 151521 A2 1/1985 patent is extended or adjusted under 35 EP O 259 O16 A1 8/1987 EP O 271 675 A2 10/1987 U.S.C. 154(b) by 0 days. GB 123O 560 A 5/1971 (21) Appl. No.: 10/276,287 JP 62 O18485 4/1987 WO WO 82/0O829 3/1982 (22) PCT Filed: May 11, 2001 WO WO 83/02450 7/1983 WO WO OO/39229 7/2000 (86) PCT No.: PCT/IE01/00063 S371 (c)(1), * cited by examiner (2), (4) Date: Mar. 31, 2003 Primary Examiner William K. Cheung (87) PCT Pub. No.: WO01/85861 (74) Attorney, Agent, or Firm-Steven C. Bauman PCT Pub. Date: Nov. 15, 2001 (57) ABSTRACT (65) Prior Publication Data An activator composition for the accelerated hardening of cyanoacrylate adhesives, wherein the activator comprises a US 2003/0191248 A1 Oct. 9, 2003 member Selected from the group consisting of aromatic (30) Foreign Application Priority Data heterocyclic compounds having at least one N hetero atom in the ring(s) Such as pyridines, quinolines and pyrimidines May 12, 2000 (IE) ............................................ 2OOOO367 and Substituted on the ring(s) with at least one electron Apr. 27, 2001 (IE) ............................................ 2001.0422 withdrawing group which decreases the base Strength of the (51) Int. Cl. Substituted compound compared to the corresponding C08F 3/42 (2006.01) unsubstituted compound, mixtures of any of the foregoing with each other, and/or with N,N-dimethyl-p-toluidine, and (52) U.S. Cl. ................... 526/297; 260/33.4; 260/33.64; mixtures of any of the foregoing and/or N,N-dimethyl-p- 260/78.4; 106/287; 526/318 toluidine with an organic compound containing the Struc (58) Field of Classification Search ................. 526/297, tural element, -N=C-S-S-, such as dibenzothiazyl 526/318; 260/33.4, 33.64, 78.4; 106/287 disulfide. 6,6'dithiodinicotinic acid, 2,2'-dipyridyl disulfide, See application file for complete Search history. and bis(4-t-butyl-1-isopropyl-2-imidazolyl)disulfide. An activator composition may comprise a Solution of one or (56) References Cited more activators in a Solvent mixture which comprises a Volatile hydrocarbon and a cyclic ketone. U.S. PATENT DOCUMENTS 3.254,111 A 5/1966 Hawkins et al. ......... 260/465.4 47 Claims, No Drawings US 6,995,227 B2 1 2 ACTIVATOR COMPOSITIONS FOR readily evaporated, leaving the activator on the Substrate/ CYANOACRYLATE ADHESIVES part or the adhesive. Japanese Patent Application No. JP-A-62 022 877 pro poses the use of Solutions of lower fatty amines, aromatic FIELD OF THE INVENTION amines, dimethylamine and the like. Japanese Patent Appli This invention relates to activator compositions, particu cation No.JP-A-03 207 778 proposes the use of solutions of larly well Suited for accelerating the hardening of aliphatic, alicyclic and, especially, tertiary aromatic amines, cyanoacrylate adhesives. The invention also relates to novel particular examples which are mentioned are N,N- mixtures of chemical compounds and to the use of the dimethylbenzylamine, N-methylmorpholine and N,N- activator compositions and the novel mixtures for the accel diethyltoluidine. erated hardening of cyanoacrylate adhesives. The invention Japanese Patent Application No. 59-66471 discloses a further relates to a process for the accelerated bonding of hardening accelerator for use with cyanoacrylate adhesives Substrates using cyanoacrylate adhesives. comprising an amine compound, with a boiling point of between 50° C. and 250 C., together with a deodorizer and BRIEF DESCRIPTION OF RELATED 15 a Solvent. Examples of Suitable amines are triethyl amine, TECHNOLOGY diethyl amine, butyl amine, isopropylamine, tributyl amine, N,N-dimethyl aniline, N,N-diethyl aniline, N,N-dimethyl Adhesive compositions based upon cyanoacrylate esters p-toluidine, N,N-dimethyl-m-toluidine N,N-dimethyl-o- are well known and have found extensive use, because of toluidine, dimethylbenzyl amine, pyridine, picoline, Vinyl their rapid cure Speed, excellent long-term bond strength, pyridine, ethanolamine, propanolamine and ethylene and applicability to a wide variety of Substrates. They diamine. generally harden after only a few Seconds, after which the U.S. Pat. No. 3,260,637 of von Bramer discloses the use joined parts exhibit at least a certain degree of initial of a range of organic amines (excluding primary amines) as Strength. accelerators for cyanoacrylate adhesives, particularly for use It is known that certain cyanoacrylate (CA) adhesives 25 on metallic and non-metallic Substrates. typically harden by an anionic polymerisation reaction. If N,N-dimethyl-p-toluidine has been widely used as an the adhesive is conventionally applied in a relatively thick accelerator for the accelerated hardening of cyanoacrylate layer in the joint gap or relatively large amounts of adhesive adhesives. A crucial disadvantage of the use of that Sub are applied So that relatively large drops of adhesive pro stance is the short duration of the Surface activation, which trude from between the parts to be joined, rapid hardening does not permit long waiting times between application of throughout the adhesive may rarely be achieved, i.e. cure the accelerator Solution beforehand to the Substrates to be through-gap or cure-through-volume (CTV) performance bonded and the Subsequent bonding process. In addition, the may be unsatisfactory. use of N,N-dimethyl-p-toluidine in some countries often With certain Substrates, particularly Substrates having 35 times involves rigorous regulatory labelling requirements. acidic Surfaces, Such as wood or paper, the polymerisation Basicity of an accelerator Substance is not a Sufficient reaction may be retarded, oftentimes to an unmanageable criterion for identifying Solutions which are acceptable in extent. Moreover, unless the adhesive is gelled or rendered practice in terms of application technology. Many thixotropic by appropriate additives to confer Such Substances, Such as alkylamines, 1,2-di-(4-pyridyl-ethane), properties, the wood or paper Substrates, due to their 4,4'-dipyridyl disulfide, 3-(3-hydroxypropyl)pyridine, 1,2- porosity, tend to draw the adhesive out of the joint gap by 40 bis(diphenylphosphino)-ethane, pyridazine, methylpy capillary action before hardening has taken place in the gap. ridazine or 4,4'-dipyridyl, are So basic or nucleophilic that Heretofore efforts have been made to accelerate the Spontaneous Superficial hardening takes place at the adhe polymerisation of Such CA adhesives by means of certain Sive interface (shock hardening) before the activator is able additives. Addition of accelerators directly to the adhesive 45 to initiate polymerisation throughout the liquid adhesive formulation is possible to only a very limited extent, layer by convection and diffusion. The result is that an often however, Since Substances having a basic or nucleophilic cloudy polymerisation occurs at the surface only. With other action, which would normally bring about a pronounced compounds, Such as oxazoles, the basicity is evidently too acceleration of the polymerisation of the cyanoacrylate low, and the hardening is often too slow for practical adhesive, are generally used at the expense of the Storage 50 purposes. stability of Such formulations. German Patent DE-A-22 61 261 proposes accelerator Addition of Such accelerators shortly before application of Substances containing the Structural element-N=C-S-, the adhesive results in Virtually a two-component System. including 2,4-dimethylthiazole. However, that compound However, Such method has the disadvantage that the work has a very high volatility, So that activator Solutions based ing life is limited after the activator has been mixed in. In 55 thereon are unsuitable for application beforehand Since the addition, with the Small amounts of activator that are active ingredient also evaporates off with the Solvent. required, the necessary accuracy of metering and homoge It is desired to find new activator compositions for use neity of mixing are difficult to achieve. Moreover, use of with cyanoacrylate adhesives, which activator compositions Such a two-component System is often seen as cumberSome have a pronounced accelerating action and low volatility, So to the end user, and Sometimes only modestly improves the 60 that application beforehand is also possible. It is also desired intended result. to find activators which are Subject to regulatory labelling Activators are also used in the form of a dilute Solution requirements less rigorous than is N,N-dimethyl-p-toluidine which is either applied beforehand onto a Substrate or part currently. which is to be bonded, and/or is applied onto the adhesive European Patent Specification No. 0271 675 A2 of Three where it is still liquid after the substrates have been joined. 65 Bond Co. Ltd. describes a primer for CA resin compositions The Solvents used for Such dilute Solutions of activators are for use in bonding non-polar or highly crystallized resins generally low-boiling organic Solvents, So that they may be Such as polyolefins, polyethyleneterephthalates, nylons, US 6,995,227 B2 3 4 fluorine-containing resins, soft PVC films etc. The primer Activator Solutions are often applied by Spraying.
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