Patents Assigned to Loctite
  • Patent number: 4684538
    Abstract: Silicone urethane compounds, e.g., a polysiloxane urethane (meth)acrylate, obtained as a reaction product of a polysiloxane carbinol, a polyisocyanate, and a polyfunctional compound having at least one functional group which is reactive with an isocyanate group of the polyisocyanate and after reaction therewith provides an ethylenic functional group in the reaction product. The polysiloxane carbinol has a molecular weight of from about 5,000 to about 50,000 and has R'OH end groups wherein R' is linear C.sub.4 -C.sub.20 alkylene. Such carbinol may be obtained as a reaction product of the corresponding hydride-terminated polysiloxane and a linear C.sub.4 -C.sub.20 .omega.-alkenyl alcohol. The hydride-terminated polysiloxane in turn may be obtained as a reaction product of either (i) the corresponding silanol of molecular weight at least 10,000 and a hydridosilane having one or more hydrolyzable groups attached to the silicon atom, or (ii) a cyclosiloxane and a 1,3-dihydrido disiloxane.
    Type: Grant
    Filed: February 21, 1986
    Date of Patent: August 4, 1987
    Assignee: Loctite Corporation
    Inventor: Philip T. Klemarczyk
  • Patent number: 4678100
    Abstract: A material dispensing valve finding particular application in the robotic dispensing of sealants, adhesives, etc. in a desired pattern on a workpiece. The dispensing valve comprises a unique actuating arrangement wherein back to back pancake cylinders are moveably arranged within a housing and, depending upon how the cylinders are actuated, three or four dispense rate positions can be provided. The dispense rate positions of the valve are preferably coordinated with the rate of movement of the robotic system so that the dispense rate is appropriate for the rate of movement.
    Type: Grant
    Filed: June 17, 1985
    Date of Patent: July 7, 1987
    Assignee: Loctite Corporation
    Inventors: William A. Gelinas, Robert N. McDermott
  • Patent number: 4675273
    Abstract: 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: Grant
    Filed: February 10, 1986
    Date of Patent: June 23, 1987
    Assignee: Loctite (Ireland) Limited
    Inventors: John G. Woods, John M. Rooney
  • Patent number: 4675270
    Abstract: 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: Grant
    Filed: February 10, 1986
    Date of Patent: June 23, 1987
    Assignee: Loctite (Ireland) Limited
    Inventors: John G. Woods, John M. Rooney
  • Patent number: 4675346
    Abstract: Compositions of (a) a silicone resin characterized by an intermediate region free of acrylic groups, at least 150 siloxane units long, and terminal acrylic groups; (b) at least 10% of a fumed silica filler; and (c) a photoinitiator, can be cured by UV irradiation to tough elastomeric materials useful in adhesive and sealant applications.
    Type: Grant
    Filed: January 16, 1984
    Date of Patent: June 23, 1987
    Assignee: Loctite Corporation
    Inventors: Samuel Q. S. Lin, Steven T. Nakos
  • Patent number: 4673750
    Abstract: An auto-adhering one-component room temperature vulcanizable silicone sealant utilizes a gylcidoxyalkyl substituted mixed alkoxy-oxime silane as an adhesion promoter. The sealant bonds to a variety of substrates including glass, metal, ceramics; does not require a primer to be applied to the substrate; has a low odor and is non-corrosive to ferrous substrates. The sealant is useful as a formed-in-place gasket material as for example, an internal combustion engine and has good oil resistance for an RTV silicone gasketing material.
    Type: Grant
    Filed: April 27, 1986
    Date of Patent: June 16, 1987
    Assignee: Loctite Corporation
    Inventors: M. Dale Beers, James E. Thompson
  • Patent number: 4668713
    Abstract: 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: Grant
    Filed: December 16, 1985
    Date of Patent: May 26, 1987
    Assignee: Loctite (Ireland) Limited
    Inventors: John Woods, John M. Rooney, Bernard J. Bolger
  • Patent number: 4666953
    Abstract: Polyorganosiloxanes having an average of more than two siloxane repeat units, at least one of which repeat units includes a photoinitiating group bound to the silicon atom thereof, the photoinitiating group having the formula ##STR1## where R.sup.1 and R.sup.2 are the same or different alkyl groups or R.sup.1 and R.sup.2 are alkylene groups linked to each other so that R.sup.1 and R.sup.2 together with the carbon atom to which both are attached comprise a cycloalkyl group, and R.sup.3 is H or hydrocarbyl.Compositions of these polyorganosiloxanes and silicones or organic monomers with free radical curable groups are readily cured by irradiation with UV light.
    Type: Grant
    Filed: March 28, 1985
    Date of Patent: May 19, 1987
    Assignee: Loctite Corporation
    Inventors: Philip Klemarczyk, Steven T. Nakos, Samuel Q. S. Lin
  • Patent number: 4665147
    Abstract: Methacrylated siloxanes are prepared by hydrosilation of beta(allyloxy)ethyl methacrylate using a silicon hydride functional siloxane. Propene elimination is not a significant side reaction of the method. Methacrylated silicones prepared in accordance with the invention are capable of anaerobic cure.
    Type: Grant
    Filed: September 24, 1984
    Date of Patent: May 12, 1987
    Assignee: Loctite Corporation
    Inventors: Qcheng S. Lien, Steven T. Nakos
  • Patent number: 4661190
    Abstract: Apparatus and a process for bonding a core member to a housing member, particularly, in instances in which the members do not mate in a contiguous fashion. The invention includes some manual and some semi-automatic functions, but is largely automated and computer controlled. A conveyor carries an assembly of an initially joined but unbonded core member and housing member along a series of discrete stations. After some preparatory steps in the process, an initial continuous bead of sealant is first applied on one side of the assembly to close off the space between the members and thereby form a cavity between them. The bead is cured, then the assembly is inverted and the cavity is filled with an anaerobic bonding material. A second continuous bead of sealant is then applied on the other side of the assembly to close off the remaining space between the members as well to isolate the bonding material within the cavity.
    Type: Grant
    Filed: June 17, 1985
    Date of Patent: April 28, 1987
    Assignee: Loctite Corporation
    Inventors: William A. Gelinas, Edwin R. Holtz, Dennis J. Argazzi, Robert L. Smigel, Dan W. Wiley
  • Patent number: 4642362
    Abstract: 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: Grant
    Filed: March 28, 1985
    Date of Patent: February 10, 1987
    Assignee: Loctite (Ireland) Limited
    Inventors: Stephen J. Harris, John G. Woods, John M. Rooney
  • Patent number: 4640940
    Abstract: Polyorganosiloxane polymers which include at least one group of the formula: ##STR1## where R.sup.1 is an organo group; R.sup.2 is alkylene or alkenylene; G is a n+1 valent hydrocarbon, oxyhydrocarbon or poly(oxyhydrocarbon) radical in which some or all of the hydrogen atoms may optionally be substituted by halogen atoms; R.sup.3 is H or an organic functional group, particularly polymerizable groups, polymerization accelerating groups or polymerization initiating groups; n is an integer of 2 or more provided that when n is 2 and one of R.sup.3 is H, the other R.sup.3 group is also H; and a is 0, 1 or 2.Additional polyorganosiloxane polymers include at least one group of the formula: ##STR2## where R.sup.4 R.sup.5 are H or a mono valent hydrocarbon group.
    Type: Grant
    Filed: August 13, 1985
    Date of Patent: February 3, 1987
    Assignee: Loctite Corporation
    Inventors: Anthony F. Jacobine, David M. Glaser
  • Patent number: 4640849
    Abstract: 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: Grant
    Filed: January 31, 1986
    Date of Patent: February 3, 1987
    Assignee: Loctite (Ireland) Limited
    Inventors: John G. Woods, John M. Rooney
  • Patent number: 4636539
    Abstract: 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: Grant
    Filed: September 16, 1985
    Date of Patent: January 13, 1987
    Assignee: Loctite (Ireland) Limited
    Inventors: Stephen J. Harris, M. Anthony McKervey, David P. Melody, John Woods, John M. Rooney
  • Patent number: 4632945
    Abstract: An anaerobic sealant material comprises an acrylate or methacrylate monomer, a hydroperoxide or pereseter initiator, an accelerator having --SO.sub.2 NHCO-functionality, and a transition metal co-accelerator gives substantially reduced moisture sensitivity if the transition metal co-accelerator is a combination of a copper salt or complex at the level of 0.5-10 ppm copper and an iron complex or salt at the level of 0.5-60 ppm iron.
    Type: Grant
    Filed: May 31, 1985
    Date of Patent: December 30, 1986
    Assignee: Loctite Corporation
    Inventors: Maria L. Garcia, Bernard M. Malofsky
  • Patent number: 4632944
    Abstract: A polymerizable fluid for sealing and locking engineering parts contains components which allow 2 mechanisms of polymerization, the first of the mechanisms being initiatable by radiation such as ultraviolet light, and an opacifier such as a powder dispersed in the fluid, the opacifier rendering the fluid opaque to the radiation. A coating of the fluid is applied to one of the engineering parts and the coating is exposed to the radiation which initiates the first of said polymerization mechanisms, so that polymerization occurs only in a surface layer of the coating to form a dry tack free crust thereon. Due to the presence of the opacifier, the radiation is obstructed from passing beyond the surface layer and the subcutaneous fluid is unaffected by the radiation. The second polymerization mechanism, suitably a free radical addition polymerization of known type, is initiatable when two engineering parts are assembled together.
    Type: Grant
    Filed: October 15, 1982
    Date of Patent: December 30, 1986
    Assignee: Loctite Corporation
    Inventor: William H. Thompson
  • Patent number: 4622348
    Abstract: Products formed from chlorosulfonyl isocyanate either by sequentially reaction of a hydroxy functional compound followed by reaction of the sulfonyl chloride group with a primary or secondary amine, or by reaction of chlorosulfonyl isocyanate with an excess of primary or secondary amine, are cure accelerators for acrylic compositions. Depending on the choice of alcohol or amine, the accelerator may be functionalized so that it is bound or bindable to an organic or silicone polymer backbone or contains other desirable functionality such as peroxy, photosensitizer, or acrylic groups.
    Type: Grant
    Filed: November 27, 1984
    Date of Patent: November 11, 1986
    Assignee: Loctite Corporation
    Inventors: Anthony F. Jacobine, David M. Glaser
  • Patent number: 4622414
    Abstract: Additive compounds useful as accelerators in storage stable cyanoacrylate adhesive formulations have 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 compounds may be effectively employed at levels of between about 0.1% and 1% by weight of a cyanoacrylate adhesive composition.
    Type: Grant
    Filed: December 3, 1984
    Date of Patent: November 11, 1986
    Assignee: Loctite Limited
    Inventor: M. Anthony McKervey
  • Patent number: 4604295
    Abstract: Compounds represented by the formula: ##STR1## wherein R.sup.1 is alkyl, aralkyl, alkoxyalkyl, alkenyl, alkynyl, carboxyalkyl or carboxyaryl;R.sup.2 is any group which does not cause spontaneous decomposition of the peroxy group; andx and y are integers between 0 and 4 with x+y great than or equal to 1, are disclosed.The inventive compounds are useful as visible and UV photoinitiators and as thermal or chemical initiators for curing compositions of ethylenically unsaturated monomers and prepolymers.
    Type: Grant
    Filed: December 22, 1983
    Date of Patent: August 5, 1986
    Assignee: Loctite Corporation
    Inventor: Robert W. R. Humphreys
  • Patent number: RE32240
    Abstract: A self-emulsifying anaerobic-curing composition is disclosed. The composition is rendered self-emulsifying by incorporating certain anionic and/or nonionic surfactants in a concentration range of about 0.25 to about 10.0 percent. The preferred anionics comprise the petroleum sulfonates and the sodium alkyl or alkylaryl sulfonates. The preferred nonionics comprise the ethoxylated alkyl alcohols, the ethoxylated alkyl phenols, and the polyoxyethylene/polyoxypropylene glycols. Any anaerobic monomer or monomer mixture in which the surfactant is soluble and compatible with the cure system may be used.These self-emulsifiable compositions have the advantage of being readily removed from surfaces by washing with water, which makes them especially useful in impregnation processes where uncured resin must be removed from areas which are difficult to wash, such as small, blind holes.
    Type: Grant
    Filed: February 8, 1980
    Date of Patent: September 2, 1986
    Assignee: Loctite Corporation
    Inventor: JoAnn DeMarco