Patents Assigned to Loctite (Ireland) Limited
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Patent number: 5113003Abstract: The silicon-containing phenoxy ethers are of the formula III: ##STR1## wherein R.sup.1 and R.sup.2 which may be the same or different are selected from H, --R.sup.3 --X, aliphatic hydrocarbyl having 1-6 carbon atoms or aryl, or substituted derivatives thereof, provided that not more than one of R.sup.1 and R.sup.2 is H;R.sup.3 is a divalent C.sub.1 -C.sub.30 aliphatic and/or aromatic hydrocarbyl group which may optionally be substituted, or interrupted, by a hetero atom;R.sup.4 and R.sup.5 which may be the same or different are H, ##STR2## or an ortho para directing activating group for aromatic electrophilic substitution, other than an amine;and X is a reactive functional group capable of undergoing an acid-catalyzed electrophilic aromatic substitution reaction with a phenol, for example an aldehyde group. They can be polymerized to produce silicone-modified polymers of the phenol-aldehyde type without the use of free aldehyde.Type: GrantFiled: March 20, 1991Date of Patent: May 12, 1992Assignee: Loctite (Ireland) LimitedInventors: John G. Woods, Pauline Coakley
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Patent number: 5084490Abstract: Styryloxy compounds of the formula IV ##STR1## wherein R.sup.1 and R.sup.2 are H, or one of R.sup.1 and R.sup.2 is H and the other is methyl;R.sup.7 and R.sup.8 (which may be the same or different) are H, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkenyl; or one of R.sup.7 and R.sup.8 may be --OR.sup.6 or C.sub.1 -C.sub.5 alkoxy or C.sub.1 -C.sub.5 alkenyloxy if R.sup.2 is not methyl;R.sup.6 is selected from the group consisting of: ##STR2## where R.sup.10 is C.sub.1 -C.sub.5 alkyl; and R.sup.11, R.sup.12 and R.sup.13, which may be the same or different, are H or C.sub.1 -C.sub.5 alkyl, are described as new low viscosity liquid styryloxy monomers which can be photocured and which form transparent polymers. They have an advantageous effect in a mixture with 4-allyloxystyrene, and this mixture has a synergistic effect in combination with divinyl ethers of a polyalkylene oxide.Type: GrantFiled: December 10, 1990Date of Patent: January 28, 1992Assignee: Loctite (Ireland) LimitedInventors: Ciaran B. McArdle, Joseph Burke, John G. Woods
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Patent number: 4867817Abstract: Chemical compositions such as adhesive, sealing or coating compositions containing one or more microencapsulated ingredients are activated by directly contacting an ultrasonic device (2) to the composition (8) and sonicating the composition to rupture the microcapsules. The method may be carried out in a sonication chamber (1) in which the ultrasonic device (2) is immersed in the composition (8) and from which the composition flows before it sets. Alternatively the ultrasonic energy may be applied to the composition in situ.Type: GrantFiled: February 4, 1987Date of Patent: September 19, 1989Assignee: Loctite (Ireland) LimitedInventors: Brendan J. Kneafsey, John M. Rooney, Conor F. MacAogain
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Patent number: 4695615Abstract: Cyanoacrylate adhesive compositions which employ calixarene compounds as additives give substantially reduced fixture and cure times on de-activating substrates such as wood. The calixarene compounds are preferable employed at levels of about 0.1-2% by weight of the composition.The calixarene compounds particularly useful in this invention may be represented by the formula: ##STR1## where R.sup.3 is H, --CH.sub.2 C(.dbd.O)OH, CH.sub.2 C(.dbd.O)OR.sup.6, --C(.dbd.O)R.sup.8, hydrocarbyl, or trihydrocarbylsilyl or the two R.sup.3 groups together form a divalent hydrocarbyl or oxygen interrupted hydrocarbyl group; R.sup.4 is H or hydrocarbyl; R.sup.5 is hydrocarbyl, hydrocarbyl interrupted by one or more oxygen atoms, or hydrocarbyl substituted with halo, nitro, or oxo groups; R.sup.6 is as defined for R.sup.5 but different therefrom; and R.sup.8 is as defined for R.sup.5 but the same or different therefrom.Type: GrantFiled: January 31, 1986Date of Patent: September 22, 1987Assignee: Loctite (Ireland) LimitedInventors: Raymond G. Leonard, Stephen J. Harris
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Patent number: 4675270Abstract: A method for imaging vapor deposited photoresists of cyanoacrylates or related anionically polymerizable monomers without the use of solvent development. This method consists of treating the substrate with a compound which releases acid when exposed to high-energy radiation. In certain cases when the surface of the substrate is slightly acidic or neutral, it is necessary to activate the surface with a basic liquid or vapor which must be chosen so as not to react with the radiation-sensitive acid precursor. The substrate is exposed to actinic or ionizing radiation through a mask or to steered high-energy beams. Finally, the substrate is exposed to a vapor of cyanoacrylate monomer which condenses and polymerizes on the unirradiated regions forming a relief image.Type: GrantFiled: February 10, 1986Date of Patent: June 23, 1987Assignee: Loctite (Ireland) LimitedInventors: John G. Woods, John M. Rooney
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Patent number: 4675273Abstract: A method for applying a polymeric resist coating of very high molecular weight to a suitable substrate without the necessity of elaborate purification steps and for ensuring adequate coverage of raised regions in three-dimensionally patterned substrates. The method comprises exposing the substrate to be coated to the vapor of an anionically polymerizable monomer of the formula:CHR.dbd.CXYwhere X and Y are strong electron withdrawing groups and R si H or, provided that X and Y are both --CN, C.sub.1 -C.sub.4 alkyl for sufficient time to deposit a polymerizable coating thereon. Particularly preferred monomers are 2-cyanoacrylate esters. The monomer condenses and polymerizes on the surface of the substrate to give a highly uniform high molecular weight polymeric coating which is useful as a resist coating in lithographic processes employing plasma or acid etch techniques.Type: GrantFiled: February 10, 1986Date of Patent: June 23, 1987Assignee: Loctite (Ireland) LimitedInventors: John G. Woods, John M. Rooney
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Patent number: 4668713Abstract: Compositions useful as UV curable conformal coatings are mixtures, substantially free of isocyanate condensation catalyst, of the following constituents:(i) a compound having two or more alkenyl or alkynyl groups;(ii) a compound having two or more mercapto groups;(iii) a compound having two or more isocyanate groups; and(iv) a free radical photoinitiator.The composition cures by a secondary mechanism in shadow areas and has a long pot life, for example 8-24 hours.Type: GrantFiled: December 16, 1985Date of Patent: May 26, 1987Assignee: Loctite (Ireland) LimitedInventors: John Woods, John M. Rooney, Bernard J. Bolger
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Patent number: 4642362Abstract: A linear or cross-linked polymer selected from polythioethers, polyethers, styrenic polymers, polyacrylates, and polyorganosiloxanes having a plurality of calixarene groups bound thereon, the calixarene groups having the formula ##STR1## where the R.sup.1 groups are the same or different H or hydrocarbyl groups; the R.sup.2 groups are H, hydrocarbyl, --CH.sub.2 C(.dbd.O)OR.sup.3, --CH.sub.2 C(.dbd.O)R.sup.3, or --C(.dbd.O)NHR.sup.3, R.sup.3 is hydrocarbyl or substituted hydrocarbyl; n is an integer of 1-8, m is an integer of 0-7 and n+m is 4-8.Type: GrantFiled: March 28, 1985Date of Patent: February 10, 1987Assignee: Loctite (Ireland) LimitedInventors: Stephen J. Harris, John G. Woods, John M. Rooney
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Patent number: 4640849Abstract: Polyfunctional cationically polymerizable styryloxy compounds of the formula ##STR1## where R.sup.1 is H or methyl; R.sup.2 is hydrocarbyl, hydrocarbyl interrupted by ether oxygen atoms, or halo substituted hydrocarbyl; R.sup.3 is H, lower alkyl, or alkoxy; G is any multivalent organic or inorganic radical free of amino or aliphatic thiol groups; and n is an integer of two or more.Type: GrantFiled: January 31, 1986Date of Patent: February 3, 1987Assignee: Loctite (Ireland) LimitedInventors: John G. Woods, John M. Rooney
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Patent number: 4636539Abstract: Cyanoacrylate adhesive compositions which employ calixarene compounds as additives give substantially reduced fixture and cure times on de-activating substrates such as wood. The calixarene compounds are preferably employed at levels of about 0.1-1% by weight of the composition. The calixarene compounds particularly useful in this invention may be represented by the formula: ##STR1## where R.sup.1 is alkyl, alkoxy, substituted alkyl or substituted alkoxy; R.sup.2 is H or alkyl; and n=4, 6, or 8.The compositions are further characterized by a thickener component, which may suitably be selected from various polymers such as poly(methyl methacrylate), methacrylate type copolymers, acrylic rubbers, polyvinyl acetate and poly(.alpha.-cyanoacrylate) or silicas treated with polydialkylsiloxanes or trialkylsilanes.Type: GrantFiled: September 16, 1985Date of Patent: January 13, 1987Assignee: Loctite (Ireland) LimitedInventors: Stephen J. Harris, M. Anthony McKervey, David P. Melody, John Woods, John M. Rooney
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Patent number: 4525553Abstract: Ferricenium salts of the formula: ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different H or alkyl groups or a linkage to a polymeric backbone: M is a metal or metalloid; X is a halide and n is an integer, induce polymerization of acrylic monomer/peroxy initiator systems. Above a certain minimum concentration, however, gel time of the composition increases with additional ferricenium salt. This property is especially useful for controlling pot life of an activated acrylic composition.Type: GrantFiled: February 21, 1984Date of Patent: June 25, 1985Assignee: Loctite (Ireland) LimitedInventors: John M. Rooney, Paul Conway
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Patent number: 4497916Abstract: An improved sealing or adhesive composition comprising a stable slurry of solid meltable wax-like particles dispersed in a liquid adhesive or sealant composition, such as an anaerobic adhesive of sealant, which may be caused to cure at a time later than the time of application. The composition may be applied to threaded bolts or other articles by pumping the slurry through a heated applicator head to dispense homogeneous liquid on the article which hardens on cooling to a non-mobile setable coating.Type: GrantFiled: August 22, 1983Date of Patent: February 5, 1985Assignee: Loctite (Ireland) LimitedInventors: Bernard Cooke, Peter Wrobel
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Patent number: 4451615Abstract: A structurally toughened heat resistant adhesive composition comprising a solution of polyisoprene elastomer in polymerizable acrylate ester monomers. The adhesive composition also contains an adhesion promoter, a cross-linking agent, a free-radical generator and a free-radical accelerator. The adhesive compositions are generally used as two-part systems, and yield bonds with improved heat and solvent resistant properties. The polymerizable acrylate ester monomers may be monofunctional or a combination of mono- and polyfunctional monomers. Among the useful classes of monomers are alkyl and cycloalkyl acrylates, alkyl and cycloalkyl methacrylates, alkoxy acrylates and methacrylates, alkylene diacrylates and dimethacrylates. A few of the preferred monomers are methyl methacrylate, lauryl methacrylate, isobornyl methacrylate, and tetrahydrofurfuryl methacrylate.Type: GrantFiled: March 16, 1983Date of Patent: May 29, 1984Assignee: Loctite (Ireland) LimitedInventor: Ronald S. Charnock
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Patent number: 4442267Abstract: A structurally toughened heat resistant adhesive composition comprising a solution of a polyacrylic elastomer in polymerizable acrylate ester monomers. The adhesive composition also contains an adhesion promoter, a cross-linking agent, a free-radical generator and a free-radical accelerator. The adhesive compositions are generally used as two-part systems, and yield bonds with improved heat and solvent resistant properties. The polymerizable acrylate ester monomers may be monofunctional or a combination of mono- and polyfunctional monomers. Among the useful classes of monomers are alkyl and cycloalkyl acrylates, alkyl and cycloalkyl methacrylates, alkoxy acrylates and methacrylates, alkylene diacrylates and dimethacrylates. A few of the preferred monomers are methyl methacrylates, lauryl methacrylates, isobornyl methacrylates, and tetrahydrofurfuryl methacrylates.Type: GrantFiled: March 17, 1983Date of Patent: April 10, 1984Assignee: Loctite (Ireland) LimitedInventor: Ronald S. Charnock
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Patent number: 4416921Abstract: A composition of matter which is useful in a process for impregnating and sealing of porous articles, the composition comprising:(a) an azonitrile;(b) a polymerizable acrylic monomer;(c) a substituted, sterically-hindered phenol; and(d) a metal ion chelator.Type: GrantFiled: July 17, 1981Date of Patent: November 22, 1983Assignee: Loctite (Ireland) LimitedInventor: David J. Dunn
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Patent number: 4414275Abstract: A flexible adhesive tape comprising a thermoplastic support film etched on one side with a suitable etchant or etching method, said etched side being coated with a polyvinylformal pre-coat, and further coated with a photo-sensitive adhesive composition comprising,(i) at least one polymerizable acrylate ester monomer;(ii) a photo-initiator;(iii) optionally a film former;and the other side of said thermoplastic support film being coated with a release agent.These tape are useful as protective coatings, and adhere to a variety of surfaces, particularly high surface energy materials.Type: GrantFiled: July 13, 1981Date of Patent: November 8, 1983Assignee: Loctite (Ireland) LimitedInventor: John Woods
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Patent number: 4105715Abstract: A cyanoacrylate adhesive composition in thixotropic paste form is made by mixing a liquid cyanoacrylate ester with powdered organic fillers selected from (i) polycarbonates, (ii) polyvinylidene fluorides, (iii) polyethylenes, and (iv) acrylic block copolymer resins containing saturated elastomer segments. Concentration of the filler is about 5 to 100 parts by weight. Particle size of the filler is about 2 to 200 microns.Type: GrantFiled: July 11, 1977Date of Patent: August 8, 1978Assignee: Loctite (Ireland) LimitedInventor: Edward R. Gleave
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Patent number: 4102945Abstract: A cyanoacrylate adhesive composition thickened by a copolymer or terpolymer resin capable of being dissolved or solvated by the cyanoacrylate monomer exhibits significantly improved peel strength. Storage stability is also enhanced. Preferred thickeners are acrylonitrile-butadiene-styrene terpolymers, methacrylate-butadiene-styrene terpolymers, and vinylidene chloride-acrylonitrile copolymers. Preferred monomers are methyl and ethyl cyanoacrylates.Type: GrantFiled: July 11, 1977Date of Patent: July 25, 1978Assignee: Loctite (Ireland) LimitedInventor: Edward Roger Gleave
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Patent number: 4100141Abstract: Stabilized, curable compositions formed from known free radical-polymerizable monomers (e.g., acrylates, stryene, etc.), and free radical initiators (e.g., peroxides, hydroperoxides, ultraviolet-sensitive compounds) by dissolving therein compounds containing the combination of allyl, lower alkoxyl and hydroxyl groups. All the groups may be present in one molecule, or the allyl group may occur in a separate molecule. Concentration of each compound may be in the range of about 0.01 to about 5 percent by weight of the total composition.Type: GrantFiled: July 2, 1976Date of Patent: July 11, 1978Assignee: Loctite (Ireland) LimitedInventor: Denis Joseph O'Sullivan
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Patent number: 4043982Abstract: This invention relates to polymerizable compositions, which serve as adhesives, sealants, potting compounds, etc., the primary components of which are an acyl peroxide initiator, an arylamine polymerization accelerator, and a polymerizable acrylate-isocyanate monomer.Type: GrantFiled: July 30, 1975Date of Patent: August 23, 1977Assignee: Loctite (Ireland) LimitedInventors: Denis J. O'Sullivan, Bernard J. Bolger, T. Eisert Casey