Patents by Inventor David M. Glaser
David M. Glaser has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 8829136Abstract: A method of conducting controlled radical polymerization, including: (a) providing a mixture of at least one monomer; at least one monomer solvent; at least one compound metal coordinating capable; and at least one initiator; (b) directing the mixture at a rate over a solid catalyst surface contained in an external chamber to the vessel, the catalyst including a metal or metal compound capable of at least two oxidation states; (c) monitoring the reaction vessel temperature; (d) adjusting the flow rate when the temperature is outside a selected temperature range; and (e) allowing the polymerization to proceed to desired conversion level.Type: GrantFiled: November 16, 2010Date of Patent: September 9, 2014Assignee: Henkel US IP LLCInventors: David M. Glaser, Roderick Coffey, John G. Woods, III, Anthony F. Jacobine
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Patent number: 8609881Abstract: The present invention provides compound(s) selected from the group of compounds represented by structural Formula (I): wherein X, Y and R1 are as described herein, use of such compounds as anaerobic cure accelerators, and compostions including such compounds.Type: GrantFiled: May 7, 2008Date of Patent: December 17, 2013Assignee: Henkel IP US LCCInventors: Andrew Messana, Anthony F. Jacobine, Steven Thomas Nakos, David M. Glaser
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Patent number: 8106141Abstract: Reaction products prepared from reactants including: (a) at least one compound of structural Formula (I): wherein R1 is selected from aryl and heteroaryl; X is selected from a direct bond, —O—, —S—, —NH—, alkylene, cycloalkylene, heterocyclylene, arylene, alkarylene, and heteroarylene; Y is a substituted alkylene group having at least two contiguous carbon atoms and which can be interrupted by one or more —O—, —S—, or —NH— moieties as defined herein, wherein the alkylene group of Y has substituents independently selected from —OH, —NH2, —SH, cycloalkyl, heterocyclyl, aryl, and heteroaryl, or two hydrogen atoms on the same carbon atom of Y are replaced by carbonyl, and wherein at least two substituents of Y are each independently selected from —OH, —NH2, and —SH, as defined herein; and (b) at least one isocyanate functional material.Type: GrantFiled: May 7, 2008Date of Patent: January 31, 2012Assignee: Henkel CorporationInventors: Anthony F. Jacobine, Andrew Messana, David M. Glaser, Steven Thomas Nakos
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Publication number: 20110060157Abstract: A method of conducting controlled radical polymerization, including: (a) providing a mixture of at least one monomer; at least one monomer solvent; at least one compound metal coordinating capable; and at least one initiator; (b) directing the mixture at a rate over a solid catalyst surface contained in an external chamber to the vessel, the catalyst including a metal or metal compound capable of at least two oxidation states; (c) monitoring the reaction vessel temperature; (d) adjusting the flow rate when the temperature is outside a selected temperature range; and (e) allowing the polymerization to proceed to desired conversion level.Type: ApplicationFiled: November 16, 2010Publication date: March 10, 2011Applicant: Henkel CorporationInventors: David M. Glaser, Roderick Coffey, John G. Woods, Anthony F. Jacobine
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Patent number: 7705064Abstract: The present invention is directed to reaction products prepared from at least one Michael addition donor material including two or more active methylene hydrogens; and at least one material capable of reacting with a Michael addition donor, the material having one Michael addition acceptor and at least one functional group selected from the group consisting of hydroxy, hydroxyalkyl, vinyl ether, amino, aminoalkyl, carboxy, carboxyalkyl, cyano, and cyanoalkyl groups; or reaction products prepared from (a) at least one Michael addition donor material comprising at least one Michael Addition donor group selected from the group consisting of cyano functional groups and phosphono functional groups; and (b) at least one material capable of reacting with the at least one Michael addition donor group, the material having at least one Michael addition acceptor, wherein the above reaction products are capable of forming free radicals upon exposure to actinic radiation; as well as compositions, and processes for makingType: GrantFiled: July 23, 2007Date of Patent: April 27, 2010Assignee: Henkel CorporationInventors: Anthony F. Jacobine, John G. Woods, Joel D. Schall, Steven T. Nakos, Andrew D. Messana, David M. Glaser
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Publication number: 20090277356Abstract: The present invention provides products of isocyanate functional material(s) and compound(s) selected from the group of compounds represented by structural Formula (I): wherein X, Y and R1 are as described herein, use of such compounds as anaerobic cure accelerators, and compositions including such compounds.Type: ApplicationFiled: May 7, 2008Publication date: November 12, 2009Applicant: HENKEL CORPORATIONInventors: Anthony F. Jacobine, Andrew Messana, David M. Glaser, Steven Thomas Nakos
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Publication number: 20090278084Abstract: The present invention provides compounds represented by structural Formula (III): wherein X, R1, R2, and R4 are as described herein, reaction products of compounds of Formula (III) and isocyanates, use of such compounds and reaction products as anaerobic cure accelerators, methods of making the same, and compositions including such compounds.Type: ApplicationFiled: May 7, 2008Publication date: November 12, 2009Applicant: HENKEL CORPORATIONInventors: Andrew Messana, Anthony F. Jacobine, Steven Thomas Nakos, David M. Glaser
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Publication number: 20090281335Abstract: The present invention provides compound(s) selected from the group of compounds represented by structural Formula (I): wherein X, Y and R1 are as described herein, use of such compounds as anaerobic cure accelerators, and compostions including such compounds.Type: ApplicationFiled: May 7, 2008Publication date: November 12, 2009Applicant: HENKEL CORPORATIONInventors: Andrew Messana, Anthony F. Jacobine, Steven Thomas Nakos, David M. Glaser
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Publication number: 20090030106Abstract: The present invention is directed to reaction products prepared from at least one Michael addition donor material including two or more active methylene hydrogens; and at least one material capable of reacting with a Michael addition donor, the material having one Michael addition acceptor and at least one functional group selected from the group consisting of hydroxy, hydroxyalkyl, vinyl ether, amino, aminoalkyl, carboxy, carboxyalkyl, cyano, and cyanoalkyl groups; or reaction products prepared from (a) at least one Michael addition donor material comprising at least one Michael Addition donor group selected from the group consisting of cyano functional groups and phosphono functional groups; and (b) at least one material capable of reacting with the at least one Michael addition donor group, the material having at least one Michael addition acceptor, wherein the above reaction products are capable of forming free radicals upon exposure to actinic radiation; as well as compositions, and processes for makingType: ApplicationFiled: July 23, 2007Publication date: January 29, 2009Applicant: Henkel CorporationInventors: Anthony F. Jacobine, John G. Woods, Joel D. Schall, Steven T. Nakos, Andrew D. Messana, David M. Glaser
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Publication number: 20090012202Abstract: The present invention is directed to acrylated urethanes including the reaction product of: (1)(a) at least one urethane having at least two isocyanate groups and at least one acrylate group; and (b) at least one alcohol compound having at least two hydroxyl groups; or (2) (a) at least one isocyanate functional urethane which is the reaction product of at least one alcohol compound selected from the group consisting of amino alcohols, thioether alcohols, phosphino alcohols and mixtures thereof and at least one polyisocyanate; and (b) at least one hydroxy-functional material having at least one acrylate group; curable compositions including the same and processes for making the same.Type: ApplicationFiled: July 3, 2007Publication date: January 8, 2009Applicant: Henkel CorporationInventors: Anthony F. Jacobine, John G. Woods, Joel D. Schall, Steven T. Nakos, David M. Glaser
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Patent number: 5558937Abstract: A curable thiol-ene composition specially adapted for use as a primary coating on optical fibers comprises a polythiol and a compound having a plurality of norbornene groups thereon, are characterized in that one of either the compound having the plurality of norbornene groups or the polythiol has a backbone of a poly(tetramethylene oxide), or is an oligomer thereof, and the poly(tetramethylene oxide) has a molecular weight of between 250 and 5,000. The formulations are relatively low viscosity liquids at practical application temperatures and cure substantially completely with very low irradiation fluence. The formulations cure in ambient air. There is no need to exclude oxygen or to control humidity. The formulations of the invention can be cured using low intensity UV lamps which do not generate significant amounts of heat. The cured products have excellent low temperature flexibility, good humidity and water absorbtion resistance and good thermal oxidative stability.Type: GrantFiled: May 3, 1995Date of Patent: September 24, 1996Assignee: Loctite CorporationInventors: John G. Woods, Margaret A. Rakas, Anthony F. Jacobine, Louis M. Alberino, Philip L. Kropp, Donna M. Sutkaitis, David M. Glaser, Steven T. Nakos
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Patent number: 5459175Abstract: A curable thiol-ene composition specially adapted for use as a primary coating on optical fibers comprises a polythiol and a compound having a plurality of norbornene groups thereon, are characterized in that one of either the compound having the plurality of norbornene groups or the polythiol has a backbone of a poly(tetramethylene oxide), or is an oligomer thereof, and the poly(tetramethylene oxide) has a molecular weight of between 250 and 5,000. The formulations are relatively low viscosity liquids at practical application temperatures and cure substantially completely with very low irradiation fluence. The formulations cure in ambient air. There is no need to exclude oxygen or to control humidity. The formulations of the invention can be cured using low intensity UV lamps which do not generate significant amounts of heat. The cured products have excellent low temperature flexibility, good humidity and water absorbtion resistance and good thermal oxidative stability.Type: GrantFiled: June 22, 1993Date of Patent: October 17, 1995Assignee: Loctite CorporationInventors: John G. Woods, Margaret A. Rakas, Anthony F. Jacobine, Louis M. Alberino, Philip L. Kropp, Donna M. Sutkaitis, David M. Glaser, Steven T. Nakos
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Patent number: 5459173Abstract: Stable thiol-ene compositions are provided which comprise a polythiol, a polyene and a stabilizer system comprising an alkenyl substituted phenolic compound having a formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are independently selected from the group consisting of H, OR, a C.sub.1 -C.sub.8 alkyl, substituted alkyl, alkenyl or substituted alkenyl, a C.sub.6 -C.sub.20 aryl or substituted aryl, or a cyano group; R.sup.4 is H, R, OR, halogen, COR, COOR, or SR; R.sup.5 is OH, OR, OCOR, OCOOR, OCONHR, or OTMS; R is a C.sub.1 -C.sub.6 alkyl, a cycloalkyl, or a C.sub.6 -C.sub.20 caryl or substituted aryl; x and y are 1, 2, or 3; z is 0, 1, or 2; and x+y+z=2, 3, or 4; or a formula: ##STR2## where x, y, z, w, R.sup.1 R.sup.2 R.sup.3, R.sup.4 and R.sup.5 are defined as above, except that x+y+z=2-6, and R.sup.6 is CH.sub.2, C(CH.sub.3).sub.2, O, S, or SO.sub.Type: GrantFiled: June 22, 1993Date of Patent: October 17, 1995Assignee: Loctite CorporationInventors: David M. Glaser, Anthony F. Jacobine, Paul J. Grabek
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Patent number: 5399624Abstract: A treatment method for polyene resins used in thiol-ene formulations, especially norbornene resins, significantly stabilizes thiol-ene compositions made from batches of polyene resin which otherwise give compositions with poor dark stability. The treatment comprises contacting the polyene with an amphoteric treating agent selected from the group consisting of silicated magnesium oxide, basic aluminum oxide, silica gel, magnesium oxide, magnesium hydroxide, calcium oxide, calcium hydroxide, barium oxide, and barium hydroxide, and then separating the resin from the treating agent prior to mixture with a polythiol to form a thiol-ene composition. The treatment method significantly reduces ionic content in polyene resins, particularly chloride ion but also sodium and potassium ions. Consequently, treatment is also beneficial with polyene resins which do not produce substantial dark stability problems.Type: GrantFiled: April 30, 1993Date of Patent: March 21, 1995Assignee: Loctite CorporationInventors: David M. Glaser, Anthony F. Jacobine, Paul J. Grabek
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Patent number: 5371181Abstract: A treatment method for polythiol compounds used in thiol-ene formulations, especially formulations employing norbornene resins, significantly improves cure speed retention on aging of thiol-ene formulations which include hydroxylamine salts, such as N-nitrosoarylhydroxylamine aluminum salts, as shelf-life stabilizers. The treatment comprises contacting the polythiol with an amphoteric treating agent selected from the group consisting of silicated magnesium oxide, magnesium oxide, magnesium hydroxide, calcium oxide, calcium hydroxide, barium oxide, and barium hydroxide, and then separating the resin from the treating agent prior to mixture with a polyene to form a thiol-ene composition. In formulations employing phenolic compounds having an alkenyl group in conjugation with the phenyl group thereof as shelf-life co-stabilizers the treatment method also significantly enhances the shelf-life stability of the formulation compared to formulations made from untreated polythiol.Type: GrantFiled: June 22, 1993Date of Patent: December 6, 1994Assignee: Loctite CorporationInventors: David M. Glaser, Anthony F. Jacobine, Paul J. Grabek
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Patent number: 5266670Abstract: A process comprising the steps of:1) reacting a norbornene compound of the formula: ##STR1## where R is H or methyl, R.sup.1 is a direct bond or --C(.dbd.O)O-- and R.sup.2 is vinyl, ethynyl, allyl or propargyl, with a silicon hydride functional compound in the presence of hydrosilation catalyst at a temperature of at least 60 degrees; and2) recovering a product which consists essentially of the addition products of the silicon hydride functional compound to the R.sup.2 group of the norbornene compound and which is substantially free of addition products of the silicon hydride functional compound to the internal ring double bond of the norbornene compound.The products of this process can be used to produce norbornene functional prepolymers which are useful in cureable silicone formulations based on thiolene or hydrosilation cure chemistry.Type: GrantFiled: February 24, 1989Date of Patent: November 30, 1993Assignee: Loctite CorporationInventors: Steven T. Nakos, Anthony F. Jacobine, David M. Glaser
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Patent number: 5208281Abstract: 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: GrantFiled: August 16, 1991Date of Patent: May 4, 1993Assignee: Loctite CorporationInventor: David M. Glaser
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Patent number: 5171816Abstract: 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: GrantFiled: January 31, 1991Date of Patent: December 15, 1992Assignee: Loctite CorporationInventors: Anthony F. Jacobine, Steven T. Nakos, David M. Glaser
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Patent number: 5167882Abstract: 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: GrantFiled: February 5, 1991Date of Patent: December 1, 1992Assignee: Loctite CorporationInventors: Anthony F. Jacobine, Margaret A. Rakas, David M. Glaser
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Patent number: 5034490Abstract: 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 silicone atoms thereof, where R is H or methyl, R.sup.1 is a direct bond of --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: GrantFiled: February 24, 1989Date of Patent: July 23, 1991Assignee: Loctite CorporationInventors: Anthony F. Jacobine, David M. Glaser, Steven T. Nakos