Patents Assigned to Loctite (Ireland) Ltd.
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Patent number: 5359101Abstract: Anionically polymerizable monomers containing at least one silicon or titanium atom form polymeric photoresists having good dry etch resistance for use in microlithography. The monomers are of the formula ##STR1## wherein A is --H or --CH.dbd.CH.sub.2 ; X is a strong electron withdrawing group;Y is a strong electron withdrawing group containing at least one silicon or titanium atom.Preferably Y is ##STR2## wherein n is 1-5 and R.sup.2, R.sup.3 and R.sup.4 are C.sub.1 -C.sub.10 alkyl. A particularly preferred monomer is 3-trimethylsilylpropyl 2-cyanoacrylate.Methods for applying a resist coating by vapor deposition of these monomers and exposure to radiation are described. A positive or negative tone image can be produced, depending upon the imaging method employed. The imaging layer may be applied over a planarizing layer to form a multilayer photoresist.Type: GrantFiled: October 1, 1991Date of Patent: October 25, 1994Assignee: Loctite Ireland, Ltd.Inventors: John Woods, Pauline Coakley
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Patent number: 5077376Abstract: A latent hardener material for epoxy resins comprising a combination ofHardener (A) which is a reaction product of phthalic anhydride and diethylenetriamine, andHardener (B) which is a reaction product of a polyfunctional epoxy compound, an imidazole compound and a carboxylic acid anhydride.A combination of latent hardeners (A) and (B) can achieve cure of an epoxy resin composition in 15 minutes at 76.degree. C. A one part epoxy resin composition comprising an epoxy resin in admixture with a combination of hardeners (A) and (B) has a good shelf life.Type: GrantFiled: May 21, 1990Date of Patent: December 31, 1991Assignee: Loctite (Ireland) Ltd.Inventor: John Dooley
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Patent number: 5068265Abstract: An anaerobic liquid acrylate sealant composition contains short portions of one or more types of fibre, particularly aramid fibre pulp, as a filler. A particulate filler such as fumed silica and/or micronized polyethylene may also be present. The composition suitably is based on a high proportion of monofunctional acrylate ester monomer, and a polyacrylate plasticiser. The composition is used for sealing joints in pipework where it is desired to seal the joint almost immediately but to allow adjustment of the joint for at least 24 hours.Type: GrantFiled: July 21, 1989Date of Patent: November 26, 1991Assignee: Loctite (Ireland) Ltd.Inventors: Tadhg E. Casey, David P. Melody
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Patent number: 5043415Abstract: The application describes nitrogen-containing an oxacalixarene or calixarene derivative of formula I: ##STR1## wherein m'+m"=0-8n=0-8m'.gtoreq.1/2(m'+M")3.ltoreq.m'+m"+n.ltoreq.8if n=0, m'+m".gtoreq.4R.sup.3 is H, halogen, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof and R.sup.3 may be the same or different on each aryl group;R.sup.1 and R.sup.15 which may be the same or different are H or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof;R.sup.2 is selected from:R.sup.4 which is H, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof, ##STR2## wherein R.sup.5 and R.sup.6 which may be the same or different are H, or hydrocarbyl, aryl, hydrocarbylaryl, or a substituted derivative thereof,-OR.sup.1, wherein R.sup.1 is as defined aboveand R.sup.17 which is a residue of a hydrocarbyl, aryl, or hydrocarbylaryl group or of a substituted derivative thereof providing a bond to another oxacalixarene or calixarene derivative of formula I wherein R.Type: GrantFiled: September 23, 1988Date of Patent: August 27, 1991Assignee: Loctite (Ireland) Ltd.Inventors: Stephen J. Harris, Maureen G. MacManus, John Guthrie
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Patent number: 5039753Abstract: Polymers comprising a polymer backbone having pendant or terminal betadiketone groups which contain at least one trifluoromethyl group. The betadiketone groups may be selected from trifluorocetoacetate groups (general formula I); ##STR1## hexafluoroacetylacetone groups (general formula II); ##STR2## or trifluoro-2,4-pentanedione groups (general formula III); ##STR3## where indicates the polymer backbone, R is an alkyl, substituted alkyl, aryl or substituted aryl group and R.sup.1 is hydrogen, alkyl or substituted alkyl. Neither the R group nor the R.sup.1 group should contain any group which is sufficiently basic to initiate cyanoacrylate polymerization or any group sufficiently acidic to interfere with chain transfer.Type: GrantFiled: October 20, 1988Date of Patent: August 13, 1991Assignee: Loctite (Ireland) LtdInventors: John G. Woods, John Rooney, Bernard Ryan, David Phelan
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Patent number: 5021512Abstract: Curable thiol/ene compositions comprise:(1) a multifunctional styryloxy monomer having one or more of the following structures ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are selected from vinyl (--CH.dbd.CH.sub.2), 1-propenyl (--CH.dbd.CH--CH.sub.3), isopropenyl ##STR2## hydrogen, lower alkyl or alkoxy, provided that at least one of R.sup.1, R.sup.2 and R.sup.3 must be vinyl, 1-propenyl or isopropenyl;n is an integer .gtoreq.1;if n=1, then R.sup.4 is a monovalent hydrocarbon radical containing one free-radically copolymerizable alkenyl or cycloalkenyl group,if n.gtoreq.2, R.sup.4 is a multivalent hydrocarbon radical which may contain a maximum of one free-radically copolymerizable alkenyl or cycloalkenyl group;R.sup.5 is a divalent hydrocarbon radical; or a carbon atom which is part of a cyclic group in the radical G; or a radical of formula ##STR3## where R.sup.Type: GrantFiled: May 4, 1989Date of Patent: June 4, 1991Assignee: Loctite (Ireland) Ltd.Inventors: John G. Woods, John M. Rooney
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Patent number: 4957960Abstract: An encapsulating composition for electronic devices comprises a curable material such as a silicone resin and an ion scavenger compound selected from certain calixarene or oxacalixarene compounds in which at least half of the phenolic groups have been substituted by specific groups and certain silacrown compounds. Exemplary ion scavenger compounds include ##STR1## the tetraethyl acetate of 7, 13, 19, 25-tetra-tertbutyl-27, 28, 29, 30-tetrahydroxy-2,3-dihomo-3-oxacalix-4-arene and 1,1-dimethasila-17-crown-6.Type: GrantFiled: January 30, 1990Date of Patent: September 18, 1990Assignee: Loctite (Ireland) Ltd.Inventors: Stephen J. Harris, John G. Woods, John M. Rooney, Marueen G. MacManus, John Guthrie
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Patent number: 4933407Abstract: Oxacalixarenes of general formula I: ##STR1## wherein m=0-7 and n=1-8 with the proviso that m+n.ltoreq.8;R is hydrogen, halogen, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof, and R may be the same or different on each aryl group; andR' is hydrocarbyl, aryl, hydrocarbylaryl, hydrocarbyloxy, aryloxy or hydrocarbylaryloxy or a substituted derivative thereof.The invention also provides a method of preparing oxacalixarenes of formula I, and cyanoacrylate adhesive compositions including as accelerator an oxacalixarene of formula I.Type: GrantFiled: July 21, 1989Date of Patent: June 12, 1990Assignee: Loctite (Ireland) Ltd.Inventors: Stephen J. Harris, Maureen G. MacManus
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Patent number: 4912183Abstract: A free radical polymerization process comprises bringing together(a) a monomeric material such as an acrylic monomer in a relatively low polarity medium(b) a free radical source or initiator such as a metallic salt initiator or activator normally soluble only in high polarity media such as water and(c) a calixarene derivative of the formula I: ##STR1## wherein m+n=4, 6 or 8 n=an integer greater than or equal to 1/2 (m+n)wherein m+n=4,6 or 8n=an integer greater than or equal to 1/2 (m+n)R=hydrocarbyl, hydrocarbyloxy, substituted hydrocarbyl, substituted hydrocarbyloxy, aryl, hydrocarbylaryl, aryloxy, hydrocarbylaryloxy, substituted aryl, substituted hydrocarbylaryl, substituted aryloxy, or substituted hydrocarbylaryloxy;R'=H, hydrocarbyl, aryl, hydrocarbylaryl, substituted hydrocarbyl, substituted aryl, or substituted hydrocarbylaryl;R"=H, hydrocarbyl or substituted hydrocarbyl.Type: GrantFiled: April 6, 1988Date of Patent: March 27, 1990Assignee: Loctite (Ireland) Ltd.Inventors: Brendan Kneafsey, John M. Rooney, Stephen J. Harris
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Patent number: 4908399Abstract: An encapsulating composition for electronic devices comprises a curable material such as an epoxy resin and an ion scavenger compound selected from certain calixarene or oxycalixarene compounds in which at least half of the phenolic groups have been substituted by specific groups and certain silacrown compounds. Exemplary ion scavenger compounds include ##STR1## the tetraethyl acetate of 7, 13, 19, 25-tetra-tertbutyl-27, 28, 29, 30-tetrahydroxy-2,3-dihomo-3-oxacalix-4-arene and 1,1-dimethasila-17-crown-6.Type: GrantFiled: November 14, 1988Date of Patent: March 13, 1990Assignee: Loctite (Ireland) Ltd.Inventors: Stephen J. Harris, Maureen G. MacManus, John Guthrie
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Patent number: 4869772Abstract: In a process for priming a non-polar substrate such as a polyolefin for bonding with a cyanoacrylate adhesive, the use of an adhesion-promoting primer comprising at least one diazabicyclo or triazabicyclo compound selected from1,5-diazabicyclo[4.3.0]non-5-ene having the formula: ##STR1## 1,8-diazabicyclo[5.4.0]undec-7-ene having the formula: ##STR2## and 1,5,7-triazabicyclo[4.4.0]dec-5-ene having the formula: ##STR3## The primer also contains a solvent.Type: GrantFiled: June 14, 1988Date of Patent: September 26, 1989Assignee: Loctite (Ireland) Ltd.Inventors: Patrick F. McDonnell, Brendan J. Kneafsey
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Patent number: 4855461Abstract: Oxacalixarenes of general formula I: ##STR1## wherein m=0-7 and n=1-8 with the proviso that m+n.ltoreq.8;R is hydrogen, halogen, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof, and R may be the same or different on each aryl group; andR' is hydrocarbyl, aryl, hydrocarbylaryl, hydrocarbyloxy, aryloxy or hydrocarbylaryloxy or a substituted derivative thereof.The invention also provides a method of preparing oxacalixarenes of formula I, and cyanoacrylate adhesive compositions including as accelerator an oxacalixarene of formula I.Type: GrantFiled: January 20, 1988Date of Patent: August 8, 1989Assignee: Loctite (Ireland) Ltd.Inventor: Stephen J. Harris
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Patent number: 4732956Abstract: Polyfunctional cationically polymerizable styryloxy compound of the formula ##STR1## where R.sup.1 and R.sup.2 are H, or one of R.sup.1 and R.sup.2 are H and the other is methyl; R.sup.3 and R.sup.4 are H, lower alkyl, or alkoxy if R.sup.2 is not methyl; R.sup.5 is a divalent hydrocarbon radical; G is any multivalent organic or inorganic radical free of amino, aliphatic hydroxyl, aliphatic thiol or other groups which interfere with cationic polymerization; and n is an integer of two or more.Type: GrantFiled: September 24, 1985Date of Patent: March 22, 1988Assignee: Loctite (Ireland) Ltd.Inventors: John Woods, John Rooney, Stephen J. Harris
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Patent number: 4718966Abstract: Cyanoacrylate adhesive compositions which employ calixarene compounds as accelerators 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.Type: GrantFiled: October 2, 1986Date of Patent: January 12, 1988Assignee: Loctite (Ireland) Ltd.Inventors: Stephen J. Harris, M. Anthony McKervey, David P. Melody, John Woods, John M. Rooney
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Patent number: 4699966Abstract: 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(=O)OR.sup.3, --CH.sub.2 C(=O)R.sup.3, or --C(=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: June 4, 1986Date of Patent: October 13, 1987Assignee: Loctite (Ireland) Ltd.Inventors: Stephen J. Harris, John G. Woods, John M. Rooney
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Patent number: 4575544Abstract: A curable composition of a vinyl ether resin and at least one ferricenium salt 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 polymer backbone; M is a metal or metalloid; X is a halide; and n is an integer equal to 1 plus the valency of M.Type: GrantFiled: April 16, 1984Date of Patent: March 11, 1986Assignee: Loctite (Ireland) Ltd.Inventors: John M. Rooney, Paul Conway
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Patent number: 4574142Abstract: Elastomer toughened two-part acrylic monomer adhesives which employ styrene-butadiene block copolymer rubbers as the elastomer have improved heat resistance properties at temperatures typical of industrial paint bake ovens. The adhesives include: in one part an acrylic monomer, at least 33% by weight of the rubber dissolved in the monomer, and a free radical catalyst system free of organic sulfonyl chloride; and in the other part a polymerization activator such as an amine-aldehyde condensation product.Type: GrantFiled: October 11, 1984Date of Patent: March 4, 1986Assignee: Loctite (Ireland) Ltd.Inventor: Ronald S. Charnock
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Patent number: 4543397Abstract: Polyfunctional cationically polymerizable styryloxy compound of the formula ##STR1## where R.sup.1 and R.sup.2 are H, or one of R.sup.1 and R.sup.2 are H and the other is methyl; R.sup.3 and R.sup.4 are H, lower alkyl, or alkoxy if R.sup.2 is not methyl; R.sup.5 is a divalent hydrocarbon radical; G is any multivalent organic or inorganic radical free of amino, aliphatic hydroxyl, aliphatic thiol or other groups which interfere with cationic polymerization; and n is an integer of two or more.Type: GrantFiled: December 4, 1984Date of Patent: September 24, 1985Assignee: Loctite (Ireland) Ltd.Inventors: John Woods, John M. Rooney, Stephen J. Harris
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Patent number: 4533446Abstract: An anaerobic adhesive composition activatable by ultraviolet or visible radiation is disclosed which forms strong bonds with lapped surfaces and which is comprised of (a) an anaerobically polymerizable acrylate ester monomer, (b) a compound which decomposes upon exposure to ultraviolet or visible light radiation to release a strong acid, (c) a peroxy free radical initiator capable of initiating the polymerization of the monomer upon substantial exclusion of oxygen and (d) an activator of anaerobic polymerization which, in the presence of a strong acid, reacts with the peroxide initiator to produce free radicals to catalyze the anaerobic polymerization of the monomer.Type: GrantFiled: July 20, 1983Date of Patent: August 6, 1985Assignee: Loctite (Ireland) Ltd.Inventors: Paul Conway, David P. Melody, John Woods, J. Eisirt Casey, Bernard J. Bolger, Francis R. Martin
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Patent number: 4525232Abstract: Polymerization of acid activated compositions of acrylic monomers, peroxy initiators and ferrocene derivatives is inhibited by addition of 0.5-20% of a vinyl ether monomer. Bulk compositions activated by addition of a strong acid can be provided with a desired polymerization induction time directly related to the concentration of the vinyl ether. Compositions containing compounds which decompose to a strong acid upon exposure to actinic radiation, thereby activating polymerization, have increased shelf lives when vinyl ethers are included therein. The use of vinyl ether monomers having a functionality of two or more also provides increased adhesive bond strength after curing.Type: GrantFiled: April 16, 1984Date of Patent: June 25, 1985Assignee: Loctite (Ireland) Ltd.Inventors: John M. Rooney, John Woods, Paul Conway