Patents Assigned to Loctite
  • Patent number: 5216185
    Abstract: Polymerizable calixarene and oxacalixarene derivates wherein at least one aryl group of the macrocyclic ring has a phenolic side chain of the formula VII: ##STR1## wherein Z is a group containing an acrylate or methacrylate functional group. Linear polymers may be formed from these compounds by free radical polymerization at the (meth)acrylate group. Such compounds and their polymers are capable of sequestering metals.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: June 1, 1993
    Assignee: Loctite Limited
    Inventors: Stephen J. Harris, John Guthrie, Maureen MacManus, Michael A. McKervey
  • Patent number: 5212211
    Abstract: An acryloxy-functional capped silicone formed as a reaction product of:(i) a silyl diacrylate compound of the formula ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, and R.sub.10 are independently selected from hydrogen, halo, and organo radicals; and n is an integer having a value of from 1 to 4; and(ii) a silicone having (A) functionality which is reactive with an acryloxy functionality of the silyl diacrylate compound, and (B) additional functionality imparting (directly or by reaction with a co-reactant) further curability to the silicone by another modality (e.g., moisture curability, heat curability, etc.)The capped polyfunctional silicone may suitably be formulated with (a) an effective amount of a photoinitiator for partial curing of the acryloxy-functional capped silicone under photoinitiating curing conditions, and (b) suitable curatives, initiators, accelerators, etc.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: May 18, 1993
    Assignee: Loctite Corporation
    Inventors: Edward K. Welch, II, Robert P. Cross, David I. Crossan, Hsien-Kun Chu
  • Patent number: 5210216
    Abstract: Calixarene and oxacalixarene derivatives of the formula IV: ##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.15 is H or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof;X is selected from ##STR2## wherein R.sup.7 and R.sup.8 which may be the same or different are H or hydrocarbyl (including a cycloaliphatic ring formed by R.sup.7 and R.sup.8 together), aryl, hydrocarbylaryl or a substituted derivative thereof; R.sup.9 is --OH, --NH.sub.2, --NHC(O)NH.sub.2 or --NHAr, wherein Ar is aryl or a substituted derivative thereof,n' is 0 or 1.Use of the compounds for sequestration of metals is also described.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: May 11, 1993
    Assignee: Loctite (Ireland) Limited
    Inventors: Stephen J. Harris, John Guthrie, Maureen MacManus, Ciaran McArdle, Michael A. McKervey
  • Patent number: 5208281
    Abstract: A combination of free radical retarding agent and an active iodine species selected from the group consisting of molecular iodine, iodide ion, and mixtures thereof provides synergistic stabilization of thiol-ene compositions which cure by addition of thiol groups to olefinic carbon-carbon double bonds. The combination is particularly suitable for thiol-ene formulations employing norbornenyl functional polyenes. A preferred stabilization system employs an N-nitrosoarylhydroxylamine salt and a mixture of an alkali iodide and I.sub.2 in the range of 0.6-1 mole I.sub.2 per equivalent I.sup..crclbar..
    Type: Grant
    Filed: August 16, 1991
    Date of Patent: May 4, 1993
    Assignee: Loctite Corporation
    Inventor: David M. Glaser
  • Patent number: 5200238
    Abstract: A method of forming liquid crystal alignment layers of high tilt angle, said method comprising preparing a polymeric film of a monomer of the formula IV: ##STR1## wherein X and Y are strong electron withdrawing groups, optionally substituted with or containing Si or Ti, and A is --H or --CH.dbd.CH.sub.2 or, provided that X and Y are both --CN, A may be --R.sup.2 or --CH.dbd.CHR.sup.2 wherein R.sup.2 is hydrocarbyl, aryl or alkaryl; exposing said polymeric film to ultraviolet radiation for sufficient period of time to photochemically modify the polymer and, thereafter, subjecting the modified polymer to a heat treatment in the range of 100.degree.-400.degree. C. for at least 5 seconds.
    Type: Grant
    Filed: September 25, 1991
    Date of Patent: April 6, 1993
    Assignee: Loctite (Ireland) Limited
    Inventors: Ciaran B. McArdle, John G. Woods, Anthony F. Jacobine
  • Patent number: 5187048
    Abstract: A photoresist coating for use in microlithography comprises a polymer of a monomer of the formula ##STR1## wherein X and Y are strong electron withdrawing groups and R.sup.4 is H or, providing that X and Y are both --CN, R.sup.4 may be aliphatic hydrocarbyl, aryl or alkaryl. Preferred monomers are of the formula ##STR2## wherein R.sup.7 is a C.sub.1 -C.sub.5 alkyl or C.sub.2 -C.sub.5 alkenyl group, more particularly ethyl 2-cyanopenta-2,4-dienoate or allyl 2-cyanopenta-2,4-dienoate.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.
    Type: Grant
    Filed: August 28, 1991
    Date of Patent: February 16, 1993
    Assignee: Loctite (Ireland) Limited
    Inventors: John Woods, John Guthrie, Pauline Coakley
  • Patent number: 5182315
    Abstract: A silicone composition comprising:(a) a first silane of the formula: ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, and R.sub.10 are independently selected from hydrogen, halo, and organo radicals; andn is an integer having a value of from 1 to 4;(b) a second silane of the formula: ##STR2## wherein: R.sub.11 and R.sub.16 are non-polymerizable groups and are independently selected from halo and organo radicals;R.sub.12, R.sub.13, R.sub.14, and R.sub.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: January 26, 1993
    Assignee: Loctite Corporation
    Inventors: Hsien-Kun Chu, Robert P. Cross, David I. Crossan
  • Patent number: 5182360
    Abstract: Tris(norbornenyl) isocyanurate compounds of the formula: ##STR1## wherein R.sup.1 is either H or methyl group, are prepared from the base-catalyzed trimerization of norbornenyl isocyanate. Tris(norbornenyl) isocyanurate is suitable for use as a crosslinker in thiol-ene formulations containing a difunctional thiol oligomer or in systems containing norbornene-difunctional oligomers and polyfunctional thiols, producing improved high temperature properties for the cured compositions.
    Type: Grant
    Filed: October 17, 1991
    Date of Patent: January 26, 1993
    Assignee: Loctite Corporation
    Inventors: Anthony F. Jacobine, Steven T. Nakos
  • Patent number: 5179134
    Abstract: An acryloxy-functional capped silicone formed as a reaction product of:(i) a silyl diacrylate compound of the formula: ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, and R.sub.10 are independently selected from hydrogen, halo, and organo radicals; andn is an integer having a value of from 1 to 4; and(ii) a silicone having at least one functionality which is reactive with an acryloxy functionality of the silyl diacrylate compound to yield the acryloxy-functional capped silicone.The capped silicone may suitably be formulated with an effective amount of a photoinitiator for curing of the acryloxy-functional capped silicone under photoinitiating curing conditions. The silicone functionality which is reactive with the acryloxy functionality of the silyl diacrylate compound may be --OH, or other labile hydrogen-containing substituent. Preferably, the silicone is a hydroxy-terminated linear polydiorganosiloxane.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: January 12, 1993
    Assignee: Loctite Corporation
    Inventors: Hsien-Kun Chu, Robert P. Cross, David I. Crossan
  • Patent number: 5171816
    Abstract: A composition cureable to a solid crosslinked polyorganosiloxane comprises:a) a norbornene functional silicone prepolymer having a plurality of groups of the formula: ##STR1## bound to silicon atoms thereof, where R is H or methyl, R.sup.1 is a direct bond or --C(.dbd.O)O-- and R.sup.4 is ethylene, ethenylene, propylene or propenylene,b) a coreactive silicone prepolymer selected from SiH functional silicones, and alkylthiol functional silicones, said polyorganosiloxanes (a) and (b) being present in an equivalent ratio of between 2:1 and 1:2 norbornene to silicon hydride or alkyl thiol groups, andc) an effective amount of a hydrosilation or thiol-ene cure catalyst, respectively.
    Type: Grant
    Filed: January 31, 1991
    Date of Patent: December 15, 1992
    Assignee: Loctite Corporation
    Inventors: Anthony F. Jacobine, Steven T. Nakos, David M. Glaser
  • Patent number: 5167882
    Abstract: An improved stereolithography method for building a three-dimensional article including the steps of patternwise curing successive layers of a bath of curable liquid resin formulation until the article has been completely built up, removing the article from the liquid resin bath and then post-curing the article, wherein the liquid resin is a "thiol/nene" formulation including:(a) a first compound having a plurality of norbornene groups thereon;(b) a second compound having a plurality of thiol groups therein; and(c) a free radical photoinitiator,the total functionality of the formulation being greater than 4.
    Type: Grant
    Filed: February 5, 1991
    Date of Patent: December 1, 1992
    Assignee: Loctite Corporation
    Inventors: Anthony F. Jacobine, Margaret A. Rakas, David M. Glaser
  • Patent number: 5149441
    Abstract: A method of treating wastewater including a heat-curable (meth)acrylic monomer-containing composition, at temperature below that necessary to effect heat-curing of the composition. The wastewater may be produced by aqueous washing of porous parts impregnated with a sealant composition containing such monomer. The monomer-containing wastewater is (1) adjusted in pH to a value in the range of from about 8 to about 10, and (2) contacted with an effective amount of a reducing agent which is polymerizingly effective for the monomer, to yield corresponding polymer from the monomer. The wastewater is mixed with a cationic flocculating agent in sufficient quantity to flocculate the polymer in the wastewater, and the resulting wastewater is physically separated to recover a monomer- and polymer-reduced wastewater effluent which may be discharged to receiving waters.
    Type: Grant
    Filed: October 18, 1991
    Date of Patent: September 22, 1992
    Assignee: Loctite Corporation
    Inventors: Edward K. Welch, II, Frederick F. Newberth, III
  • Patent number: 5141970
    Abstract: A method of forming high-temperature resistant polymers by a 2 step curing process comprising(a) curing a polymerizable composition at least one aromatic compound having alpha and/or beta instruction which is not substantially reactive under the curing condition of step a, particularly allyl or properyl, and(b) heating the cured composition of step a in the presence of acid to form a crosslinked resin.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: August 25, 1992
    Assignee: Loctite (Ireland) Limited
    Inventors: Ciaran B. McArdle, Joseph Burke, John G. Woods, Edward K. Welch, II
  • Patent number: 5135663
    Abstract: A method of treating wastewater containing (meth)acrylic monomer, such as is produced by aqueous washing of porous parts impregnated with a sealant composition containing such monomer. The monomer-containing wastewater is (1) adjusted in pH to a value in the range of from about 8 to about 10, and (2) contacted with an effective amount of a reducing agent which is polymerizingly effective for the monomer, to yield corresponding polymer from the monomer. The wastewater is mixed with a cationic flocculating agent in sufficient quantity to flocculate the polymer in the wastewater, and the resulting wastewater is physically separated to recover a monomer- and polymer-reduced wastewater effluent which may be discharged to receiving waters.
    Type: Grant
    Filed: October 18, 1991
    Date of Patent: August 4, 1992
    Assignee: Loctite Corporation
    Inventors: Frederick F. Newberth, III, Albert J. Henrikson, Lawrence B. Joffee, Calliope Artavanis-Tsakonas, Edward K. Welch, II
  • Patent number: 5126416
    Abstract: (Meth)acrylic ester formulations employing peroxy initiators have accelerated cure rates when the substrates to which they are applied, or the compositions themselves, include nitrite, borate, silicate or carbonate salts. The compositions should be free of acids having a PKa of 6 or less unless the composition also includes a transition metal compound.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: June 30, 1992
    Assignee: Loctite Corporation
    Inventor: Darchun B. Yang
  • Patent number: 5116558
    Abstract: A method of forming a gasket in situ between two components which includes injecting into a groove in at least one of said components a curable composition including:one or more free-radical polymerizable vinyl esters, and ingredients of a rapid free-radical cure system therefor,the cure system being inactivated prior to injection of the composition,and the composition having a viscosity at 25.degree. C. in the range from 200 to 500,000 mPas;and permitting the composition to cure.The composition can be a two part composition wherein the first part contains a prepolymer, monomer and activator and the second part a prepolymer, monomer and activator. The composition can also include two expansion reactants, each in a separate part of the composition prior to injection, which react to form a gas in situ in the composition. The gasketing composition is suitable for use in engines and other machines e.g. in industrial manufacturing plants.
    Type: Grant
    Filed: June 28, 1990
    Date of Patent: May 26, 1992
    Assignee: Loctite (Ireland) Limited
    Inventors: Peter Wrobel, James Houlihan
  • Patent number: 5113003
    Abstract: 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: Grant
    Filed: March 20, 1991
    Date of Patent: May 12, 1992
    Assignee: Loctite (Ireland) Limited
    Inventors: John G. Woods, Pauline Coakley
  • Patent number: 5096963
    Abstract: Polymerizable compositions comprising a liquid polymerizable continuous phase and a non-liquid, non-polymerizable dispersed discontinuous phase are stabilized against density drift of the discontinuous phase by forming in-situ, throughout and within said polymerizable composition a crystalline matrix of sufficient density to effectively inhibit density drift.
    Type: Grant
    Filed: February 9, 1989
    Date of Patent: March 17, 1992
    Assignee: Loctite Corporation
    Inventor: Stephen E. Blain
  • Patent number: 5084490
    Abstract: 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: Grant
    Filed: December 10, 1990
    Date of Patent: January 28, 1992
    Assignee: Loctite (Ireland) Limited
    Inventors: Ciaran B. McArdle, Joseph Burke, John G. Woods
  • Patent number: 5079098
    Abstract: The invention relates to a quaternary ammonium salt primer for bonding surfaces with cyanoacrylate adhesives, and to a method of bonding surfaces using such quaternary ammonium compounds, particularly surfaces characterized by low surface energy values, such as polyolefins and rubber-modified polyolefins. A preferred quaternary salt is tetra n-butyl ammonium fluoride. Preferred solvents for the quaternary ammonium salt are non-aqueous, low surface tension organic solvents.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: January 7, 1992
    Assignee: Loctite Corporation
    Inventor: Ju C. Liu