Ether Group Patents (Class 522/181)
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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: 5459176Abstract: Abrasion resistant, radiation curable compositions are provided for forming coatings over plastic substrates. Such compositions are particularly provided for forming an abrasion resistant, tintable coating over polycarbonate ophthalmic lenses. Generally, the radiation-curable coating comprises 10 to 50 parts of polyacryloylated alkane polyols containing up to about 20 carbon atoms and an average of at least three O-acryloyl groups; and 20 to 80 parts of polyacryloylated alkoxylated polyols containing up to about 20 carbon atoms and an average of at least three O-[acryloyl-(polyalkylene oxide)] chains, wherein each of the polyalkylene oxide chains comprises from one to 20 alkylene oxide groups.Type: GrantFiled: December 23, 1993Date of Patent: October 17, 1995Assignee: Soane Technologies, Inc.Inventors: Young C. Bae, Thomas B. Ottoboni
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Patent number: 5446073Abstract: Composition containing charge transfer complex from at least one unsaturated compound having an electron donor group and having an electron withdrawing group and being free of any photoinitiating compound is polymerized by being subjected to ultraviolet light.Type: GrantFiled: March 31, 1993Date of Patent: August 29, 1995Assignee: Fusion Systems CorporationInventors: Sonny Jonsson, Per-Erik G. Sundell, William R. Schaeffer
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Low yellow index polymer compositions, polymerisable compositions and lenses using said compositions
Patent number: 5442022Abstract: A polymer composition obtained by polymerisation of a polymerisable composition comprising: at least 50% by weight of a monomer or mixture of monomers having formula I ##STR1## wherein R.sub.1 and R.sub.2, which may be identical or different, represent hydrogen or C.sub.1 -C.sub.6 alkyl, X represents ##STR2## and wherein m+n is between 0 and 10, 0 to 50% by weight of one or more mono- or polyfunctional vinyl, acrylic or methacrylic comonomers (II); 0.5 to 15% by weight with respect to the weight of components (I) and (II) of a compound having formula (III) ##STR3## where R.sub.3 and R.sub.4 represent hydrogen or one of radicals R.sub.3 and R.sub.4 represents a hydrogen atom while the other forms a ring with R.sub.7 ; R.sub.5, R.sub.6 and R.sub.7 are hydrogen or an alkyl group which may be substituted by OH and/or interrupted.Type: GrantFiled: December 21, 1993Date of Patent: August 15, 1995Assignee: Essilor International-Compagnie General D'OptiqueInventors: Gabriel Keita, Joel Renaudineau -
Patent number: 5405366Abstract: This invention relates to a non-stringy adhesive hydrophilic gel comprising an aqueous mixture of a radiation crosslinkable water-soluble polymer, at least one humectant effective to extend the moisture retaining characteristics of the gel and which inhibits the ability of radiant energy to crosslink the water-soluble polymer, a pharmacologically active agent, and a crosslinking promoter effective to counteract the crosslinking inhibitory effect of humectant. The aqueous mixture is exposed to radiant energy effective to provide a non-stringy adhesive cohesive homogeneous hydrophilic gel that has an extended in-use lifetime. The gels can be formed into PATCHES for long term application of the pharmacologically active agent to a patient.Type: GrantFiled: November 12, 1992Date of Patent: April 11, 1995Assignee: Nepera, Inc.Inventors: Adrian S. Fox, Christine A. Czap, Robin R. Wiser
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Patent number: 5393800Abstract: A catalyst system for effecting polymerization in a two-part formulation, which contains an oxygen-containing ethylenically unsaturated monomer, consists of a selected acid, a selected aromatic amine compound, and a transition metal compound; active-oxygen, free-radical catalysts are excluded. Because of the nature of the catalyst system, efficient reaction does not require intimate mixing of the two components of the formulation, which may therefore be applied effectively as fine-droplet sprays from a common, ultrasonically vibrated head.Type: GrantFiled: February 21, 1992Date of Patent: February 28, 1995Assignee: Dymax CorporationInventors: Gary V. Grosclaude, Andrew G. Bachmann
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Patent number: 5385954Abstract: An energy polymerizable composition and process therefore, comprising a cationically polymerizable material and a catalytically effective amount of an ionic salt of an organometallic complex cation as polymerization initiator, said ionic salt of an organometallic complex cation being capable of adding an intermediate strength nucleophile or upon photolysis capable of liberating at least one coordination site, said metal in said organometallic complex cation being selected from elements of Periodic Groups IVB, VB, VIB, VIIB, and VIIIB are disclosed. Certain of the organometallic metallic polymerization initiators are novel cationic salts.Type: GrantFiled: January 27, 1993Date of Patent: January 31, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: Michael C. Palazzotto, William A. Hendrickson
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Patent number: 5385958Abstract: A multi-part composition is provided which is suitable for use as an adhesive, a potting compound, a coating or a sealant. It consists of a polymerizable acrylate formulation and an activating formulation, the latter usually comprising an amine-aldehyde condensation product diluted with a liquid vinyl ether; liquid epoxides may also be included as diluents in the activating formulation.Type: GrantFiled: March 5, 1993Date of Patent: January 31, 1995Assignee: Dymax CorporationInventors: Andrew G. Bachmann, Stephen E. Cantor
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Patent number: 5364691Abstract: This invention relates to radiation curable alk-1-enyloxy carbonate reaction products of a hydroxylated compound having the formula A-ROH and a dialk-1-enyloxy carbonate having the formula ##STR1## wherein R is a polymeric radical selected from the group of polyester, polyacetal, polyurethane, polyether, and polycarbonate, said polymers containing from about 10 to 50 repeating monomer units;A' is a terminating moiety and is hydrogen, lower alkyl or hydroxy;R' is hydrogen or lower alkyl;B is a linear, branched or cyclic divalent radicalhaving from 2 to 12 carbon atoms and is selected from the group of alkylene, mono or poly alkoxylated alkylene, alkenylene, alkynylene, arylene, alkarylene and aralkylene radicals, which radicals are optionally substituted with halo, lower alkyl, cyano, nitro or alkoxy and m has a value of from 1 to 10.Type: GrantFiled: March 9, 1990Date of Patent: November 15, 1994Assignee: ISP Investments Inc.Inventors: Paul D. Taylor, Kolazi S. Narayanan, Jeffrey S. Plotkin
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Patent number: 5358978Abstract: This invention relates to alkenyl ether polycarbonates having the formula ##STR1## wherein A is selected from the group consisting of lower alkyl and R'HC.dbd.CHOR--, R and R" are each independently a divalent radical having from 2 to 20 carbon atoms and are selected from the group of alkylene, mono- or poly- alkoxylated alkylene, alkenylene, alkynylene, arylene, alkarylene and aralkylene radicals, which radicals are optionally substituted with halo, alkyl, cyano, nitro or alkoxy; R' is hydrogen or lower alkyl; (n) has a value of from 1 to 10 and (m) has a value of from 0 to 10; with the proviso that R" contains at least 3 carbon atoms when m is zero. The invention also concerns the preparation and use of said alkenyl ether polycarbonates.Type: GrantFiled: February 3, 1993Date of Patent: October 25, 1994Assignee: ISP Investments Inc.Inventors: Jeffrey S. Plotkin, Fulvio J. Vara, James A. Dougherty, Paul D. Taylor, Kolazi S. Narayanan
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Patent number: 5354784Abstract: A keto arene-cyclopentadienyl iron complex salt of the formula:[(R.sup.2 CO)(R.sup.1).sub.m C.sub.6 H.sub.5--m Fe.sup.II Cp].sup.+1 A.sup.-1wherein R.sup.1 is an alkyl group, R.sup.2 is an alkyl group or phenyl group, m is an integer of 1 to 5, Cp is an .eta..sup.5 -cyclopentadienyl group and A.sup.-1 is a non-nucleophilic anion, e.g. pentamethylacetophenone-Fe(II)-Cp.sup.+ PF.sub.6.sup.-1 salt or pentamethylbenzophenone-Fe(II)-Cp.sup.+ PF.sub.6.sup.-1 salt, which is useful as a photoinitiator for cationically polymerizable compounds, especially for epoxy resins, and has an improved environmental safety and a high absorptivity, and which can be easily produced by a direct replacement reaction between dicarbonyl-.eta..sup.5 -(2,4-cyclopentadien-1-yl)iron(II) halide and an alkyl substituted keto arene to be replaced for the carbonyl ligands.Type: GrantFiled: August 10, 1992Date of Patent: October 11, 1994Assignee: Arakawa Kagaku Kogyo Kabushiki KaishaInventors: Scott F. Timmons, Hiroshi Sawada, Stephen T. Willinghoff, Robert E. Lyle, Jr., Belinda K. Taylor
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Patent number: 5352713Abstract: A radiation curable coating composition comprising acrylate oligomers and monomers, vinyl ether monomers, and a free radical photoinitiator. The vinyl ether monomers replace N-vinyl-pyrrolidone or other undesirable reactive diluents while retaining or modifying the properties of coatings using such diluents.Type: GrantFiled: April 1, 1992Date of Patent: October 4, 1994Assignee: Allied-Signal Inc.Inventors: James R. Snyder, George D. Green, John J. Krajewski
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Patent number: 5342860Abstract: This invention relates to alk-1-enyl ether-polyester block prepolymers which are curable by cationically initiated radiation and which are defined by the formula ##STR1## wherein m has a value of from 1 to 25;A is C.sub.2 to C.sub.12 alkylene, C.sub.6 to C.sub.14 aryl, both groups optionally substituted with lower alkyl, halo lower alkyl, alkyleneoxy, halogen or aryl;R.sub.1 is alkylene containing from 1 to 6 carbon atoms;R.sub.2 is a saturated or unsaturated divalent radical containing from 1 to 14 carbon atoms and is selected from the group of alkylene, alkenylene and arylene, each group optionally substituted with oxygen, halogen, lower alkyl and/or hydroxy;R.sub.3 is hydrogen or C.sub.1 to C.sub.6 alkyl;R.sub.4 is C.sub.1 to C.sub.6 alkylene, C.sub.6 to C.sub.14 arylene, lower alkyl substituted phenylene or xylylene andR.sub.5 and R.sub.6 are independently hydrogen or C.sub.1 to C.sub.4 alkyl.Type: GrantFiled: August 18, 1993Date of Patent: August 30, 1994Assignee: ISP Investments Inc.Inventors: Jeffrey S. Plotkin, Mark M. Miller
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Patent number: 5340653Abstract: A free-radical radiation curable composition comprising:a) at least one compound containing one to six vinyl ether groups; andb) at least one compound containing a urethane backbone with one to six maleate and/or fumarate end groups,wherein the ratio of vinyl ether groups to maleate and/or fumarate groups is in the range of about 1 to about 1:5.Type: GrantFiled: May 26, 1992Date of Patent: August 23, 1994Assignee: Stamicarbon B.V.Inventors: Gerry K. Noren, John J. Krajewski, Sami A. Shama, John M. Zimmerman, Danny C. Thompson, John T. Vandeberg
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Patent number: 5334455Abstract: A free-radical radiation curable composition comprising:a) at least one compound containing from one to about six vinyl ether groups; andb) at least one product obtainable by the reaction of a half-ester of maleic and/or fumaric acid with an epoxy functionalized compound,wherein the ratio of vinyl ether groups to maleate and/or fumarate groups is in the range of about 5:1 to about 1:5.Type: GrantFiled: May 26, 1992Date of Patent: August 2, 1994Assignee: Stamicarbon B.V.Inventors: Gerry K. Noren, John J. Krajewski, Sami A. Shama, John M. Zimmerman, Danny C. Thompson, John T. Vandeberg
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Patent number: 5334456Abstract: A free-radical radiation curable composition comprising:a) at least one compound containing from one to about six vinyl ether groups; andb) at least one compound containing a saturated backbone and at least one maleate or fumarate end group per molecule,wherein the ratio of vinyl ether groups to maleate or fumarate groups in the composition is in the range of about 5:1 to about 1:5.Type: GrantFiled: May 26, 1992Date of Patent: August 2, 1994Assignee: Stamicarbon B.V.Inventors: Gerry K. Noren, John J. Krajewski, Sami A. Shama, John M. Zimmerman, Danny C. Thompson, John T. Vandeberg
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Patent number: 5314929Abstract: The present invention relates to a rapidly curable, silicone-free release coating composition comprising (a) between about 50 and about 95 wt. % of a vinyl ether having the formula C.sub.n H.sub.2n+1 O--CH.dbd.CH.sub.2 wherein n has a value of from 8 to 20, optionally containing a cationically polymerizable comonomer; (b) between about 5 and about 50 wt. % of a multifunctional vinyl ether monomer and (c) between about 0.1 and about 10 wt. % of an onium salt photoinitiator.Type: GrantFiled: August 10, 1992Date of Patent: May 24, 1994Assignee: ISP Investments Inc.Inventors: James V. Crivello, James A. Dougherty
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Patent number: 5308886Abstract: A photosetting resin comprising a liquid monomer composition and a photopolymerization initiator, the monomer composition containing a compound represented by the following formula (1) and a compound represented by the following formula (2) in a weight ratio within the range from 97:3 to 50:50: ##STR1## (wherein R.sub.1 is H or CH.sub.3, and 0.ltoreq.m.sub.1 +m.sub.2 .ltoreq.4) ##STR2## (wherein R.sub.2 is H or CH.sub.3, and 5.ltoreq.n.sub.1 +n.sub.2 .ltoreq.12).This photosetting resin can provide a cured resin which is excellent in both strength and toughness.Type: GrantFiled: January 28, 1992Date of Patent: May 3, 1994Assignee: Japan Institute of Advanced DentistryInventors: Eiichi Masuhara, Shigeo Komiya, Takeyuki Sawamoto
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Patent number: 5288376Abstract: A perfluorooligoether iodide is prepared by exposing a perfluoropolyether carboxylic iodide to UV light.Type: GrantFiled: February 16, 1993Date of Patent: February 22, 1994Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masayuki Oyama, Noriyuki Koike, Toshio Takago
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Patent number: 5284651Abstract: Physiologically active, non-toxic, non-teratogenic and non-mutagenic huminates produced by oxidation of polyvalent phenols in aqueous alkaline medium at a reaction temperature under 40.degree. C., the pH value of the reaction medium always being over 9.0 during the oxidation and the supply of oxidant being proportioned so that the content of the quinones corresponding to the polyvalent phenols is always less than 0.5%, based on the polyvalent phenols used, and that the oxidation reaction is stopped when the quinone concentration decreases despite oxidant supply.Type: GrantFiled: October 14, 1992Date of Patent: February 8, 1994Assignee: Rutgerswerke Aktiengesellschaft AGInventors: Urs N. Riede, Bernhard Seubert
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Patent number: 5262450Abstract: A radiation curable composition is provided herein which comprises suitably about 50-90 parts, preferably about 60-80 parts, by weight, of a multifunctional acrylate monomer, suitably with 3-6 acrylate groups, preferably pentaerythritol triacrylate or trimethylolpropane triacrylate, about 10-50 parts by weight, preferably about 20-40 parts, by weight, of a divinyl ether monomer having both a hydrophobic backbone and an abrasion-resistant moiety, which is preferably the divinylether of cyclohexane dimethanol, and a radiation curing initiator, suitably a cationic initiator, and preferably, in combination with a free radical initiator.Type: GrantFiled: December 28, 1990Date of Patent: November 16, 1993Assignee: ISP Investments Inc.Inventors: Fulvio J. Vara, James A. Dougherty, Geoffrey J. Wilkins
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Patent number: 5242955Abstract: A composition comprising alicyclic polyether compounds represented by the formula (I): ##STR1## containing structural units A having an ether bond derived from an alicyclic epoxy group and one (meth)acrylic group, and n is an integer of from 1 to 100, R.sup.1 is a radical of an organic compound having L active hydrogens or HO--, from n1 to nL is an integer of from 1 to 100, respectively, the total is 1 to 100, L is an integer of from 1 to 100, which is the number of active hydrogen in said organic compound.Curable resin compositions can be prepared by the addition of a photo-polymerizable initiator.Type: GrantFiled: October 29, 1991Date of Patent: September 7, 1993Assignee: Daicel Chemical Industries, Ltd.Inventors: Yoshiyuki Harano, Sozo Namai
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Patent number: 5200437Abstract: This invention relates to coating compositions containing the alk-1-enyl ether reaction product of a hydroxylated compound, an alk-1-enyloxy oxirane and from 0 to 95% of an alkyl epoxide.Type: GrantFiled: January 6, 1992Date of Patent: April 6, 1993Assignee: ISP Investments Inc.Inventors: James A. Dougherty, Fulvio J. Vara, Jeffrey S. Plotkin, Paul D. Taylor, Kolazi S. Narayanan
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Patent number: 5198509Abstract: A composition comprising a lactone-modified alicyclic compound (I), or an epoxidized lactone-modified alicyclic compound (II) of the following formulae: ##STR1## wherein R is an alkyl group, an aromatic group or an alkenyl group having carbon number of from 1 to 30, Y.sup.1 is at least one of the structural groups; ##STR2## Y.sup.2 is at least one of the structural group; ##STR3## X is the structural group; ##STR4## R.sup.a and R.sup.b each independently is hydrogen or a methyl group, c and c' represent a number of from 4 to 8, from n1 to nL represents 0 or a number of more than 0, respectively, and n1+n2+n3+. . . +nL corresponds to the total mole numbers of a lactone introduced into one molecule.These compositions can be made into a heat-curable composition, a photo-curable composition, a polymerizable composition and another photo-curable composition.Type: GrantFiled: June 8, 1992Date of Patent: March 30, 1993Assignee: Daicel Chemical Industries, Ltd.Inventors: Takaaki Fujiwa, Shin Takemoto, Tomohisa Isobe, Yoshiyuki Harano
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Patent number: 5190992Abstract: A photocurable resin composition for glass lamination, consisting essentially of a radical polymerizable monomer having at least one repeating units of ethylene oxide in its molecule and terminated with allyl, acrylate or methacrylate groups, and a photopolymerization initiator, a cured product of which has a volume resistivity of less than 5.times.10.sup.9 .OMEGA..multidot.cm. Addition of a polythiol provides an ene/thiol cure.Type: GrantFiled: October 1, 1991Date of Patent: March 2, 1993Assignee: Denki Kagaku Kogyo Kabushiki KaishaInventors: Toshiyuki Kato, Syunzi Ito, Tsunehiko Shimizui
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Patent number: 5179188Abstract: Fluorinated polyether compositions having reactive end gorups, such as ##STR1## can be crosslinked to produce cured films useful as dielectrics for microelectronic applications. Other reactive end groups such as allyl, benzocyclobutyl, N-phenylmaleimido, alkynylphenyyl, styryl, allylphenyl, cyanophenyl, and triazenophenyl are also suitable.Type: GrantFiled: April 22, 1991Date of Patent: January 12, 1993Assignee: Raychem CorporationInventors: Frank W. Mercer, Timothy D. Goodman, Aldrich N. K. Lau, Lanchi P. Vo
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Patent number: 5145884Abstract: An ultraviolet-hardenable adhesive for bonding a non-water swellable, ophthalmic-lens to a support member, in producing a non-water swellable ophthalmic lens, the adhesive containing at least one photopolymerizing monomer, and at least one photoinitiator, the at least one photopolymerizing monomer being selected from the group consisting of acrylates or methacrylates represented by following general formulas (I) and (II): ##STR1## wherein R.sub.1 is hydrogen or methyl,R.sub.2 is hydrogen or methyl,R.sub.3 is hydrogen or methyl,m is a positive integer from 2 to 20, andn is a positive integer from 1 to 5.A method of bonding a lens blank to a support member with an adhesive, and a processing of manufacturing a lens using an adhesive, are also disclosed.Type: GrantFiled: August 16, 1990Date of Patent: September 8, 1992Assignee: Menicon Co., Ltd.Inventors: Yasuyoshi Yamamoto, Yuzo Kaga, Toshiharu Yoshikawa, Akira Moribe
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Patent number: 5141970Abstract: 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: GrantFiled: December 10, 1990Date of Patent: August 25, 1992Assignee: Loctite (Ireland) LimitedInventors: Ciaran B. McArdle, Joseph Burke, John G. Woods, Edward K. Welch, II
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Patent number: 5139872Abstract: Optical fiber coatings may be prepared from compositions containing a vinyl ether oligomer prepared by reacting an hydroxyl-terminated polyester or polyether, a diisocyanate, and a hydroxy monovinyl ether, with mono or multifunctional vinyl ether terminated monomers, which may be derived from esters or alcohols.Type: GrantFiled: August 29, 1990Date of Patent: August 18, 1992Assignee: Allied-Signal Inc.Inventors: Stephen C. Lapin, Alvin C. Levy
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Patent number: 5106885Abstract: What is provided herein are radiation curable compositions containing(a) multifunctional vinyl ether monomers having the formula:X--R.sub.1 --Y.sub.1 --R.sub.2 --Y.sub.2).sub.n CH.dbd.CH.sub.2 ].sub.mwhereX is a 5-8 membered ring, saturated or unsaturated;R.sub.1 is a direct bond or C.sub.1 -C.sub.10 straight or branched chain alkylene;Y.sub.1 and Y.sub.2 are independently oxygen or sulfur;R.sub.2 is C.sub.2 -C.sub.10 straight or branched chain alkylene;n is 0-10; andm is 3-5;(b) a cationic initiator, and, optionally,(c) a polymerizable vinyl ether, epoxide, or acrylate oligomer.Type: GrantFiled: November 3, 1989Date of Patent: April 21, 1992Assignee: ISP Investments Inc.Inventors: Kou-Chang Liu, Fulvio J. Vara, James A. Dougherty
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Patent number: 5098806Abstract: Rapid changes in absorption are made within the volume of a photosensitive transparent member that absorbs incident radiation to prevent the photocopy of a document, the original transparency being restored after discontinuance of the incident radiation.Type: GrantFiled: September 22, 1989Date of Patent: March 24, 1992Assignee: Board of Regents, The University of Texas SystemInventor: Jean J. Robillard
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Patent number: 5089536Abstract: An energy polymerizable composition and process therefore, comprising a cationically polymerizable material and a catalytically effective amount of an ionic salt of an organometallic complex cation as polymerization initiator, said ionic salt of an organometallic complex cation being capable of adding an intermediate strength nucleophile or upon photolysis capable of liberating at least one coordination site, said metal in said organometallic complex cation being selected from elements of Periodic Groups IVB, VB, VIB, VIIB, and VIIIB are disclosed. Certain of the organometallic metallic polymerization initiators are novel cationic salts.Type: GrantFiled: November 22, 1982Date of Patent: February 18, 1992Assignee: Minnesota Mining and Manufacturing CompanyInventor: Michael C. Palazzotto
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Patent number: 5084490Abstract: 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: GrantFiled: December 10, 1990Date of Patent: January 28, 1992Assignee: Loctite (Ireland) LimitedInventors: Ciaran B. McArdle, Joseph Burke, John G. Woods
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Patent number: 5082874Abstract: This invention relates to aryloxy polyvinyl ethers having the formula ##STR1## wherein R is a radical having from 2 to 20 carbon atoms and is selected from the group of alkylene, alkyleneoxy alkylene, polyalkyleneoxy alkylene, arylene, alkarylene, alkarylalkylene and aralkylene; X is oxygen or sulfur; A is branched or linear alkylene having from 1 to 20 carbon atoms; B is halo or lower alkyl; n has a value of from 1 to 6 and p has a value of from 0 to 4. The invention also relates to the preparation and use of said aryloxy divinyl ethers.Type: GrantFiled: February 6, 1990Date of Patent: January 21, 1992Assignee: ISP Investments Inc.Inventors: Kou-Chang Liu, Fulvio J. Vara, James A. Dougherty
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Patent number: 5070117Abstract: An aromatic vinyl ether of the formula: ##STR1## wherein: R.sup.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.8, R.sub.9, and R.sup.10 are independently selected from hydrogen, halogen, and C.sub.1 -C.sub.8 alkyl radicals;R.sub.3 and R.sub.7 are independently selected from C.sub.1 -C.sub.8 alkylene radicals; andR.sub.11 and R.sub.12 are independently selected from allyl and methallyl.Also disclosed are various other aromatic vinyl ether compounds, chain-extended derivatives thereof, and liquid vinyl ether blends, and a method of making the aromatic vinyl ether compounds at high yield. The aromatic vinyl ether compounds, chain-extended vinyl derivatives, and/or liquid vinyl ether blends of the invention may be employed as vinyl ether components together with cationic photoinitiators, to provide cationically polymerizable vinyl ether compositions having utility in applications such as coatings, adhesives, and sealants.Type: GrantFiled: November 19, 1990Date of Patent: December 3, 1991Assignee: Loctite CorporationInventors: Philip T. Klemarczyk, Yoshihisa Okamoto
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Patent number: 5055357Abstract: This invention realtes to a radiation curable cross linkable composition containing (a) from about 0.1 to about 5 wt. % of an initiator containing at least 25% cationic initiator, (b) from about 0 to about 60 wt. % of a polymerizable vinyl ether, expoxide, vinyloxy alkyl urethane or acrylate and (c) from about 35 to about 99.9 wt. % of a polyfunctional alkenyl ether having the formulaA[(CH.sub.2 O).sub.m (Z).sub.r CH.dbd.CHR].sub.nwherein A is a carbon atom, --OCH.dbd.CHR or [C.sub.1 to C.sub.10 alkyl].sub.4-n ; R is C.sub.1 to C.sub.6 alkyl; Z is C.sub.2 to C.sub.8 alkyleneoxy; r has a value of from 0 to 6; m has a value of from 0 to 1 and at least one of r and m has a positive value; n has a value of from 1 to 4, with the proviso that m is 0 and n is one when A is --OCH.dbd.CHR, n has a value of 2 or 3 when A is [C.sub.1 to C.sub.10 alkyl].sub.4-n and n has a value of 4 when A is carbon.Type: GrantFiled: March 18, 1991Date of Patent: October 8, 1991Assignee: Isp Investments Inc.Inventors: Jeffrey S. Plotkin, James A. Dougherty, Fulvio J. Vara, Paul D. Taylor
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Patent number: 5045572Abstract: This invention relates to a radiation curable crosslinkable composition containing (a) from about 0.1 to about 5 wt. % of an initiator containing at least 25% cationic initiator, (b) from about 0 to about 60 wt. % of a polymerizable vinyl ether, epoxide, vinyloxy alkyl urethane or acrylate and (c) from about 35 to about 99.9% wt. % of a polyfunctional alkenyl ether having the formulaA[(CH.sub.2 O).sub.m (Z).sub.r CH.dbd.CHR].sub.nwherein A is a carbon atom, --OCH.dbd.CHR or [C.sub.1 to C.sub.10 alkyl].sub.4-n ; R is C.sub.1 to C.sub.6 alkyl; Z is C.sub.2 to C.sub.8 alkyleneoxy; r has a value of from 0 to 6; m has a value of from 0 to 1 and at least one of r and m has a positive value; n has a value of from 1 to 4, with the proviso that m is 0 and n is one when A is --OCH.dbd.CHR, n has a value of 2 or 3 when A is [C.sub.1 to C.sub.10 alkyl].sub.4-n and n has a value of 4 when A is carbon.Type: GrantFiled: January 26, 1990Date of Patent: September 3, 1991Assignee: GAF Chemicals CorporationInventors: Jeffrey S. Plotkin, James A. Dougherty, Fulvio J. Vara, Paul D. Taylor
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Patent number: 5036112Abstract: This invention relates to a cross-linkable, cationic radiation curable composition comprising (a) a non-volatile vinyl ether, epoxide, acrylate or an oligomer thereof (b) a cationic photoinitiator and (c) a divinyl ether polyacetal oligomer having the formula ##STR1## wherein n has a value of from 1 to 50;X is uniformly sulfur or oxygen;R is C.sub.2 to C.sub.4 alkeneoxy alkylene, poly(alkyleneoxy) alkylene, or a branched, linear or cyclic C.sub.2 to C.sub.20 alkylene andR' is phenylene, diphenylene methane, diphenylene propane, xylylene, tolylene, or a branched, linear or cyclic C.sub.2 to C.sub.20 alkylene optionally substituted with an ether, ester, carbonate, carbamate, C.sub.2 to C.sub.4 alkyleneoxy alkylene or poly(C.sub.2 to C.sub.4 alkyleneoxy) alkylene radical. The invention also relates to the composition cured on a substrate.Type: GrantFiled: January 26, 1990Date of Patent: July 30, 1991Assignee: GAF Chemicals CorporationInventors: James A. Dougherty, Jeffrey S. Plotkin, Fulvio J. Vara, Kolazi S. Narayanan
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Patent number: 5021467Abstract: Disclosed herein are i) a resin composition comprising (A) a di-(meth)acrylic acid ester of a carbonate diol having an average molecular weight of 500 to 3000 or of an addition compound of the carbonate diol with an .epsilon.-caprolactone, (B) a monoethylenically unsaturated monomer and optionally, (C) an initiator of photopolymerization, ii) a di-(meth)acrylic acid ester of an addition compound of a carbonate diol having an average molecular weight of 500 to 3000 with an .epsilon.-caprolactone and iii) a di(meth)acrylic acid ester represented by the formula: ##STR1## wherein R.sup.1 represents an alkylene group having 4 to 10 carbon atoms, R.sup.2 represents a hydrogen atom or a methyl group, the mean values of a and b are 0 to 5, respectively, the mean sum of a plus b is 0.5 to 5 and the mean value of l is 1 to 10.Type: GrantFiled: February 25, 1988Date of Patent: June 4, 1991Assignee: Nippon Kayaku Kabushiki KaishaInventors: Minoru Yokoshima, Tetsuo Ohkubo, Masayuki Kiyomoto
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Patent number: 4985470Abstract: A photopolymerizable composition which comprises an addition-polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator system, characterized in that said photopolymerization initiator system essentially consists of:(a) a p-dialkylaminostyrene derivative or p-dialkylaminophenylbutadiene derivative represented by the general formula ##STR1## wherein R.sup.1 and R.sup.2 independently represent an alkyl group; Y represents a divalent atom or atomic group selected from the group consisting of --O--, --S-- and --CH.dbd.Type: GrantFiled: June 30, 1986Date of Patent: January 15, 1991Assignee: Mitsubishi Kasei CorporationInventors: Hideki Nagasaka, Noriaki Takahashi
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Patent number: 4960673Abstract: Photopolymerizable laminates suitable for producing flexible and resilient printing plates carry on a dimensionally stable base at least one intermediate layer and on top thereof a photopolymerizable layer which consists essentially of a mixture of a water-soluble copolymer or derivative of polyvinyl alcohol, a specific copolymerizable mono-functional (meth)acrylate, a photoinitiator and a thermal polymerization inhibitor.Type: GrantFiled: March 17, 1989Date of Patent: October 2, 1990Assignee: BASF AktiengesellschaftInventors: Erich Beck, Bernd Bronstert, Wolfgang Huemmer, Dieter Littmann
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Patent number: 4957946Abstract: The invention relates to mixtures containing:(a) cationically polymerizable compound and(b) a compound of the formula I[R.sup.1 (FE.sup.II R.sup.2).sub.a ].sub.q.sup..sym.an an X.sup..crclbar.(I)in which a is 1 or 2, n is 1 or 2, R.sup.1 is a substituted or unsubstituted .pi.-arene, R.sup.2 is a substituted or unsubstituted .pi.-arene or cyclopentadienyl anion or indenyl anion, q is an integer from 1 to 3 and X is FSO.sub.3.sup.- or a q-valent anion of an organic sulfonic acid or of a carobxylic acid; R.sup.1 can also be a polymeric, aromatic ligand. The invention also relates to the novel compounds of the formula I. The curable mixtures can be processed in particular for the production of coatings having a good resistance to heat.Type: GrantFiled: June 3, 1988Date of Patent: September 18, 1990Assignee: Ciga-Geigy CorporationInventors: Kurt Meier, Roger P. Salvin
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Patent number: 4957947Abstract: A radiation-curable composition useful in forming an abrasion-resistant antistatic layer is comprised of a salt, such as an alkali metal fluoroborate, dissolved in a mixture of (1) a poly(alkylene glycol)diacrylate and (2) an acrylic monomer containing at least three acrylic ester groups. The composition can be coated in the form of a thin layer and cured by suitable means, such as an electron beam accelerator or a source of ultraviolet radiation, to form an antistatic layer of particular utility as a component of a photographic material.Type: GrantFiled: June 17, 1988Date of Patent: September 18, 1990Assignee: Eastman Kodak CompanyInventors: Janglin Chen, Billy R. Dotson
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Patent number: 4932750Abstract: Radiation-curable coating compositions particularly adapted for the single coat coating of optical fibers are disclosed. These comprise (1) from 65% to 85% of a diethylenic-terminated polyurethane, which may contain urea groups, the polyurethane being based on a diisocyanate having an average molecular weight of from 400 to 5000; and (2) from 5% to 25% of an ether of a C.sub.2 -C.sub.4 alkylene glycol monoester of a monoethylenically unsaturated monocarboxylic acid, the ether being selected from the group consisting of ethoxyethyl, dicyclopentenyl, phenyl, and mixtures thereof. Ethoxyethoxyethyl acrylate is particularly preferred. A triacrylate ester, such as trimethylol propane triacrylate, is also desirably present.Type: GrantFiled: December 9, 1982Date of Patent: June 12, 1990Assignee: DeSoto, Inc.Inventors: Robert E. Ansel, Orvid R. Cutler, Jr.
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Patent number: 4929403Abstract: A process for rapidly forming a flexible mold for finely detailed objects from a radiatively curable molding composition includes coating at least a portion of the surface of a three-dimensional object with a fluid molding composition. The coating is cured by exposing the fluid coating to radiative energy to form an elastic, flexible layer of cured molding composition on the object. The coating and curing steps can be repeated to build up the flexible mold until a predetermined minimum has been attained. The cured molding composition is removed from the object, and is suitable for immediate use as a mold to cast duplicate reproductions of the object.Type: GrantFiled: July 25, 1989Date of Patent: May 29, 1990Inventor: Edwin F. Audsley
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Patent number: 4921923Abstract: Oligomeric condensation products of certain diketones and phenols can be end-capped with a vinylbenzyl moiety and certain other moieties, especially alkyl groups, to afford thermosetting resins particularly valuable in making laminated circuit boards. Resins prepared by the reaction of 1 molar proportion of diacetylbenzene with from 3.5 to 4.0 molar proportions of phenol and end-capped with from 50 to 100% vinylbenzyl groups with the remainder being alkyls of 1 through 11 carbon atoms are particularly useful.Type: GrantFiled: November 18, 1988Date of Patent: May 1, 1990Assignee: Allied Signal Inc.Inventors: Joseph J. Zupancic, Jean M. J. Frechet, Andrew M. Zweig, Jeffrey P. Conrad
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Patent number: 4918115Abstract: Compositions comprising an oligomer which (a) on average comprises at least one in-chain residue of the general formula ##STR1## wherein Ar.sup.1 is an aromatic group, R.sup.1 is hydrogen or a hydrocarbyl group, X is a group which activates Ar.sup.1 to electrophilic attack, and Y.sup.1 is an organic residue bearing a carboxyl substituent; ad (b) has one or more pendant and/or terminal acyloxymethyl groups are described. They may be used in dental, electronic and electrical applications.Type: GrantFiled: February 5, 1988Date of Patent: April 17, 1990Assignee: Imperial Chemical Industries PLCInventors: Michael E. B. Jones, John G. Carey
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Patent number: 4906675Abstract: An active energy ray-curable composition substantially comprising at least one of (meth)acrylates and oligomers thereof represented by the following general formula (I) ##STR1## wherein R represents a hydrogen atom or a methyl group, X represents an alkylene group in which at least one hydrogen atom may be replaced by a hydroxyl group, m is 0 or an integer of 1 to 4, Y represents a hydrocarbon group having a cyclic hydrocarbon moiety therein, and n is 1 or 2. The composition is useful as an adhesive, particularly as one in the production of optical discs.Type: GrantFiled: February 10, 1987Date of Patent: March 6, 1990Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Hajime Inagaki, Kenji Yamane
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Patent number: 4886843Abstract: The compositions of this invention posses both calcium hydroxide cement characteristics and light cure characteristics and hence strong bonds are likely to form with both the tooth and conventional filling materials. There is less likelihood that a filling may fall out of a cavity.The present invention provides a two component composition which comprises a first component comprising an ethylenically polymerizable compound which contains both a salicylate group and at least one acrylate, alkacrylate, acrylamide or alkacrylamide group and second component comprising calcium hydroxide or a suitable precursor to calcium hydroxide.Type: GrantFiled: January 25, 1988Date of Patent: December 12, 1989Assignee: Imperial Chemical Industries PlcInventor: Ian G. Walton
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Patent number: 4879318Abstract: A method for making a plastic lens and a plastic lens made thereby. The method comprises disposing a liquid monomer or a monomer mixture and a photosensitive initiator into a mold cavity and directing ultraviolet light to act on the lens forming material in the cavity to produce a lens therefrom. The liquid monomer mixture may include one or more of diethylene glycol bis(allyl)-carbonate, bisphenol A diallyl carbonate, 1,6 hexanedioldimethacrylate, trimethylol propane triacrylate, tetraethylene glycol diacrylate, tripropylene glycol diacrylate, tetrahydrofurfurylmethacrylate, tetrahydrofurfuryl acrylate and styrene. The photosensitive initiator may be selected from the group of 2-hydroxy-2-methyl-1- phenyl-propan-1-one and 1-hydroxycyclohexyl phenyl ketone.Type: GrantFiled: November 18, 1988Date of Patent: November 7, 1989Assignee: Ophthalmic Research Group International, Inc.Inventors: N. Thornton Lipscomb, Omar M. Buazza