Loctite Corporation

Henkel Corporation

Henkel Loctite Corporation

Henkel US IP Lcc

Henkel IP US Lcc

Henkel IP Holding Gmbh

David M Glaser

Anthony Francis Jacobine

Steven Thomas Nakos

John Gregory Woods

Andrew D Messana

Margaret A Rakas

Paul J Grabek

Philip L Kropp

Donna M Sutkaitis

Louis M Alberino

John G Woods

John M Rooney

Joel D Schall

Paul J Clark

Roderick Coffey

Walter J Steinkraus

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.

Apparatus and methods for controlled radical polymerization

The present invention provides compound(s) selected from the group of compounds represented by structural Formula (I): wherein X, Y and Rare as described herein, use of such compounds as anaerobic cure accelerators, and compostions including such compounds.

Cure accelerators for anaerobic curable compositions

Reaction products prepared from reactants including: (a) at least one compound of structural Formula (I): wherein Ris selected from aryl and heteroaryl; X is selected from a direct bond, &#x2014;O&#x2014;, &#x2014;S&#x2014;, &#x2014;NH&#x2014;, 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 &#x2014;O&#x2014;, &#x2014;S&#x2014;, or &#x2014;NH&#x2014; moieties as defined herein, wherein the alkylene group of Y has substituents independently selected from &#x2014;OH, &#x2014;NH, &#x2014;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 &#x2014;OH, &#x2014;NH, and &#x2014;SH, as defined herein; and (b) at least one isocyanate functional material.

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 making and using the same.

Photosensitive compounds, photopolymerizable compositions including the same, and methods of making and using the same

An alkoxylate adduct of a polyol. The polyol is an amorphous diol having a melting point above about 100&deg; C. The alkoxylate is propylene oxide, butylene oxide, a mixture of propylene oxide and butylene oxide or a mixture of one or both of propylene oxide and butylene oxide with up to 50 mole % of ethylene oxide. The first polyol has an average of from about 1 to about 5 units of alkoxylate per mole of said amorphous diol. The adduct is useful in preparing urethane (meth)acrylate capped resins and compositions thereof. Resins prepared from such adducts have better manufacturing and solubility properties while retaining similar physical properties to resins prepared from the unadducted diol. The adduct may be for instance a propoxylate of hydrogenated bisphenol A having an average of from 1.5 to 3.5 moles of PO per mole of hydrogenated bisphenol A.

Liquified polyols, urethane acrylate resins prepared therewith and curable compositions employing such resins

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. The formulations may be applied to optical fibers using conventional techniques and cured with UV-vis or EB irradiation.

Optical fiber primary coatings and fibers coated therewith

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.2 ; and one or more compounds selected from the group consisting of a free radical scavenger, a hindered phenolic antioxidant and a hydroxylamine derivative.

Stabilizer system for thiol-ene and thiol-nene compositions

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. Reduction of the ionic content of the resin is desirable to produce cured thiolene polymers with low electrical conductivity and low corrosiveness.

High purity resins for thiol-ene polymerizations and method for

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.

Thiol-ene compositions with improved cure speed retention

Selective monohydrosilation of vinyl and ethynyl functional norbornenes

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..

Stabilization of thiolene compositions

A composition cureable to a solid crosslinked polyorganosiloxane comprises:

Curable norbornenyl functional silicone formulations

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:

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New Britain, CT, United States of America

David M Glaser