Sulfur Containing Patents (Class 522/180)
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Patent number: 6818680Abstract: The invention is directed to the use of multifunctional thiol compounds as adhesion promoters and/or primers to enhance the adhesion of photo or electron beam curable polymers, coatings, adhesives, or sealants to gold, other precious metals, and their alloys. Actinic radiation and electron beam (“EB”) radiation can be used to cure such compositions. The resulting cured compositions are optically clear, low Tg (≦30° C.), high refractive index (>1.50 at 1541 nm), thermally, oxidatively, and hydrolytically stable adhesives and/or coatings for glass and/or metal. The adhesive compositions containing such multifunction thiols can survive, without delamination or separation, testing conditions of 85° C. and 85% relative humidity (“RH”) for a time in excess of 500 hours.Type: GrantFiled: September 23, 2002Date of Patent: November 16, 2004Assignee: Corning IncorporatedInventor: Paul J. Shustack
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Patent number: 6759104Abstract: A photocurable composition, wherein a small amount of an alicyclic skeleton-containing mono(meth) acrylate is incorporated in a combination of an alicyclic skeleton-containing bis(meth)acrylate and a mercapto compound, a cured product obtained by the copolymerization thereof, and a process for producing the cured product.Type: GrantFiled: September 30, 2002Date of Patent: July 6, 2004Assignee: Mitsubishi Chemical CorporationInventors: Seiichiro Hayakawa, Akihiko Sakai, Akira Esaki, Yutaka Tamura
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Patent number: 6716891Abstract: The invention relates to a coating material that can be cured thermally or by actinic radiation and that contains at least one component (a1) with at least two functional groups (a11) which serve for cross-linking, by actinic radiation, and at least one functional group (a12) that can enter into thermal cross-linking reactions with the hydroxyl and/or thiol groups (a21) in component (a2), at least one branched cyclic and/or acyclic C9-C16 alkane (a2)) that is functionalized with at least two hydroxyl or thiol groups (a21) or with at least one hydroxyl and at least one thiol group, and optionally at least one photo initiator (a3), at least one initiator of the thermal cross-linking reaction (a4), at least one reactive diluent that is cured by actinic radiation and/or thermafly, at least one lacquer additive (a6), at least one thermally curable component (a7) and/or at least one organic solvent (a8).Type: GrantFiled: November 16, 2001Date of Patent: April 6, 2004Assignee: BASF Coatings AGInventors: Uwe Meisenburg, Heinz-Peter Rink, Karl-Heinz Joost, Hubert Baumgart
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Patent number: 6713524Abstract: The invention relates to novel reactive polymers of formula wherein the variables are as defined in the claims. The polymers of the invention are useful for the modification of material surfaces and are particularly suitable for providing biomedical articles such as contact lenses with a hydrophilic coating.Type: GrantFiled: March 9, 2001Date of Patent: March 30, 2004Assignee: Novartis AGInventors: Jörg Leukel, Peter Chabrecek, Dieter Lohmann
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Patent number: 6689463Abstract: The present invention relates to a composition for coating optical fibers that includes a UV curable coating composition. The composition includes at least one component having at least one heterocyclic moiety capable of undergoing ring opening polymerization. The composition may also include at least one acrylate functional end group. The acrylate functional group may be on the same component as the heterocyclic moiety or on a second component. The cured composition has a Young's Modulus of at least about 100 MPa.Type: GrantFiled: December 18, 2001Date of Patent: February 10, 2004Assignee: Corning IncorporatedInventors: Kevin Y Chou, Michelle D Fabian, Jun Hou, Gregory F Jacobs, David N Schissel, Huan-Hung Sheng
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Patent number: 6617370Abstract: To provide a method for repairing a coated surface of a vehicle, using an ultraviolet curing resin having excellent quick-drying property, and giving a good finish in a shortened working time, a method for repairing the damage on a coated surface of a vehicle being a depression and/or a depletion of a coating film, which is characterized by comprising the following steps a) to c): a) filling a putty raw material comprising an ultraviolet polymerizing resin composition in an optionally pretreated damage portion and ultraviolet curing the putty raw material to fill the damaged portion with the putty; b) uniformly spray coating, on the coated surface including at least the putty-covered surface after the step a), a primer surfacer raw material comprising an ultraviolet polymerizing resin composition having a viscosity sufficient for spray coating and ultraviolet curing the obtained raw material coating film to form a primer surfacer layer; and c) applying a top coat on the primer surfacer layer obtained in b)Type: GrantFiled: August 23, 2001Date of Patent: September 9, 2003Inventor: Makoto Ueno
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Patent number: 6608120Abstract: Compounds of the formula: having two double bonds which are activated so that they will take part in a polymerization reaction, the double bonds being sufficiently close together to ensure that cyclopolymerization will preferentially occur. These compounds are used as monomers which preferentially are cyclopolymerized under the influence of ultraviolet or thermal radiation in the production of network polymers, for example coatings or binders.Type: GrantFiled: January 17, 2001Date of Patent: August 19, 2003Assignee: Qinetiq LimitedInventors: Paul E Milne, Keith M Blackwood, Steven M Kelly, Alan W Hall, John W Goodby
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Patent number: 6596787Abstract: The present invention is directed to low intensity UV curable adhesives formulated using a blend of acrylate oligomers and monomers which are capable of bonding glass, provide improved low-yellowing properties and fast cure speed over current glass bonding adhesives, while maintaining good bond strength lo and durability comparable to, or better than, state-of-the-art glass bonding adhesives.Type: GrantFiled: February 2, 2001Date of Patent: July 22, 2003Assignee: Henkel Loctite CorporationInventors: Susan Levandoski, JoAnn DeMarco
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Publication number: 20030134926Abstract: It is an object of the present invention to provide a compound having a (meth)acryloyl group that is suitably used in various applications, a process for producing such compound simply and under mild conditions, and an useful photo-curable composition and aqueous photo-curable composition comprising such compound.Type: ApplicationFiled: October 31, 2002Publication date: July 17, 2003Applicant: NIPPON SHOKUBAI CO., LTD.Inventors: Akihiko Fukada, Keiji Yurugi, Toshio Awaji, Nobuaki Otsuki
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Patent number: 6593389Abstract: The polyimides of this invention are derived from a Diels-Alder cyclopolymerization of a photochemically generated bisdiene with dienophiles, such as bismaleimides, trismaleimides and mixtures thereof with maleimide end-caps. Irradiation of one or more diketones produces two distinct hydroxy o-quinodimethane (photoenol) intermediates. These intermediates are trapped via a Diels-Alder cycloaddition with appropriate dienophiles, e.g., bismaleimide and/or trismaleimides to give the corresponding polyimides in quantitative yields. When bismaleimides, trismaleimides or mixtures thereof with maleimide end-caps are used as the dienophile, the resulting polyimides have glass transition temperatures (Tg) as high as 300° C. Polyimide films can be prepared by ultraviolet irradiation of high solids content varnishes of the monomers in a small amount of solvent, e.g., cyclohexanone, dimethyl formamide, N-methylpyrollidone and the like.Type: GrantFiled: April 5, 2001Date of Patent: July 15, 2003Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventor: Michael A. Meador
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Patent number: 6579913Abstract: Photoactivatable coating composition comprising at least one photoinitiator and a base-catalysed polymerisable or curable organic material comprising at least one polyisocyanate and at least one compound containing isocyanate reactive groups, wherein the isocyanate reactive groups comprise at least one thiol group and the photoinitiator is a photolatent base. Preference is given to a coating composition wherein the photolatent base is selected from the group of N-substituted 4-(ortho-nitrophenyl) dihydropyridine, a quaternary organo-boron photoinitiator, and an &agr;-amino acetophenone. The composition additionally may comprise an organic acid, a metal complex and/or a metal salt as a cocatalyst and/or a sensitiser selected from the group of thioxanthones, oxazines, rhodamines, and preferably from the group of benzo-phenone and derivatives thereof.Type: GrantFiled: May 24, 2001Date of Patent: June 17, 2003Assignee: Akzo Nobel N.V.Inventors: Huig Klinkenberg, Josephus Christiaan Van Oorschot
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Patent number: 6576684Abstract: Disclosed are compositions from which radically initiated oligomers/polymers having a controlled molecular weight, low polydispersity and a vinyl or dienyl end group are prepared. Further subjects of the invention are a process for controlled radical polymerization, oligomers/polymers obtainable by said process and the use of specific addition fragmentation agents for the polymerization process. The addition fragmentation agents are new in part and these are also subject of the present invention. The addition fragmentation agents are of the formula (Ia), (Ib) or (Ic) where Y is a group which activates the double bond towards Michael addition.Type: GrantFiled: February 15, 2001Date of Patent: June 10, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Vincent Desobry, Peter Murer, Anne Schuwey
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Patent number: 6569603Abstract: There are disclosed a light-sensitive composition which comprises (A) a polymer having a phenyl group substituted by a vinyl group at a side chain, (B) a photopolymerization initiator and (C) a sensitizer which sensitizes the photo-polymerization initiator, or a light-sensitive composition which comprises (A′) a polymer, the above-mentioned (B) and (C), and (D) a monomer having at least two phenyl groups each of which is substituted by a vinyl group in the molecule of the monomer; and a method of forming a relief image which comprises coating the light-sensitive composition as mentioned above on a support, exposing the composition by exposure or scanning exposure and developing the same to form a relief image on the support.Type: GrantFiled: January 30, 2001Date of Patent: May 27, 2003Assignee: Mitsubishi Paper Mills LimitedInventor: Akira Furukawa
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Patent number: 6552102Abstract: Described are chiral liquid crystalline polymer materials and polymerizable compounds used for preparing them. The polymer materials can serve as a carrier material or are coated onto a carrier material. Also described are methods of making such materials and using them to make pigment flakes used in paints, printing inks, spray paints, cosmetic products, colored plastics, optical elements and security applications.Type: GrantFiled: July 3, 2001Date of Patent: April 22, 2003Assignee: Merck Patent Gesellschaft mit beschränkter HaftungInventors: Eike Poetsch, Gerhard Pfaff, Matthias Kuntz, Stephan Derow, David Coates
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Patent number: 6531522Abstract: The present invention relates to a coating for an optical fiber. The coating includes a monomer. The monomer includes an oxyglycidyl (meth)acrylate component. A coating with the monomeric component has exhibited an excellent polymerization rate. The present invention also relates to methods of making such optical fibers coated in accordance with the invention and the coated glass article.Type: GrantFiled: November 14, 2000Date of Patent: March 11, 2003Assignee: Corning IncorporatedInventor: Michael J. Winningham
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Patent number: 6531180Abstract: To provide a transparent resin which is suitable in the process of producing a coating for electronic materials, a glass having both of the scattering-preventing function and the antireflective function, an adhesive agent, a shock-absorbing material, an ultraviolet-cutting sheet for televisions, a filter for VDTs and a high refractive index primer composition as well as the process for the production of primer-coated lenses using said primer composition, is excellent in a coatability, adhesive property, storage stability, durability, shock resistance and the like, and is particularly excellent in a transparency and adhesive property after curing of the same. A transparent resin having an adhesive property characterized by comprising a cured product of the polymerizing composition which comprises at least one of diallyl phthalate, diallyl isophthalate and diallyl terephthalate, and pentaerythritol tetra(3-mercaptopropionate).Type: GrantFiled: September 6, 2000Date of Patent: March 11, 2003Assignee: Pentax CorporationInventors: Hidenori Takushima, Yasuhiro Sakai
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Patent number: 6528160Abstract: To provide a transparent resin which is suitable in the process of producing a coating for electronic materials, a glass having both of the scattering-preventing function and the antireflective function, an adhesive agent, a shock-absorbing material, an ultraviolet-cutting sheet for televisions, a filter for VDTs and a high refractive index primer composition as well as the process for the production of primer-coated lenses using said primer composition, is excellent in a coatability, adhesive property, storage stability, durability, shock resistance and the like, and is particularly excellent in a transparency and adhesive property after curing of the same. A transparent resin having an adhesive property characterized by comprising a cured product of the polymerizing composition which comprises at least one of diallyl phthalate, diallyl isophthalate and diallyl terephthalate, and pentaerythritol tetra (3-mercaptopropionate).Type: GrantFiled: September 6, 2000Date of Patent: March 4, 2003Assignee: Pentax CorporationInventor: Hidenori Takushima
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Patent number: 6512021Abstract: A photo-curing sealing agent comprising (a)an (meth)acrylate ester having a solubility parameter of 9 to 14, hydrophobic silica, and a photo reaction initiator. This sealing agent has high adhesion property to a cold-rolled steel, a galvanized steel or an aluminum alloy, to which a press oil, a rust-preventing oil or the like adheres.Type: GrantFiled: April 6, 2001Date of Patent: January 28, 2003Assignee: Nichiban Company LimitedInventors: Takanori Sugiki, Yuichi Nishida, Yoshio Kishimoto
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Patent number: 6506814Abstract: A UV-curable acrylate-thiol-ene insulating coating composition for electrical conductors, a method of manufacturing a UV-curable acrylate-thiol-ene insulating coating composition for electrical conductors. The insulating coating being of about 2.5 &mgr;m to about 500 &mgr;m thickness, which cured coating has a dielectric dissipation factor (60 Hz, 24° C.) of lower than about 0.05.Type: GrantFiled: May 7, 1998Date of Patent: January 14, 2003Assignee: DSM N.V.Inventors: Vadim V. Krongauz, Chau T. M. Ha, Sangeeta Rampuria
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Patent number: 6486230Abstract: The polyesters of this invention are derived from a Diels-Alder cyclopolymerization of a photochemically generated bisdiene with dienophiles, such as di(acrylates), tri(acrylates), di(methacrylates), tri(methacrylates) and mixtures thereof with mono(methacrylates) or mono(acrylate) end-caps. Irradiation of one or more diketones produces two distinct hydroxy o-quinodimethane (photoenol) intermediates. These intermediates are trapped via a Diels-Alder cycloaddition with appropriate dienophiles, e.g., di(acrylates) to give the corresponding in polyesters quantitative yields. When di(acrylates), tri(acrylates) and di and tri(methacrylates) or mixtures thereof with monoacrylate end-caps are used as the dienophile, the resulting polyesters have glass transition temperatures (Tg) as high as 200° C. Polyesters films can be prepared by ultraviolet irradiation of high solids content varnishes of the monomers in a small amount of solvent, e.g., cyclohexanone, dimethyl formamide, N-methylpyrollidone and the like.Type: GrantFiled: April 5, 2001Date of Patent: November 26, 2002Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventor: Michael A. Meador
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Patent number: 6476092Abstract: A photopolymerizable composition which is capable of successfully ensuring both high sensitivity and excellent storage stability is provided as a radical photopolymerization-system composition which is highest in the sensitivity and very promising out of the image-forming techniques. The photopolymerizable composition comprises a polymerizable group-containing compound having a specific structure set forth below wherein X1 and X2 each independently represent a group containing a hetero atom wherein the hetero atom is in the &agr;-position or a halogen atom and a photopolymerization initiator.Type: GrantFiled: September 20, 2000Date of Patent: November 5, 2002Assignee: Fuji Photo Film Co., Ltd.Inventor: Kazuto Kunita
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Patent number: 6447708Abstract: Sulphur product, (P), process for making (P), films, molded articles made therefrom, wherein (P) is obtained by the addition reaction of at least one polythiol (I) with at least one compound of formula (II): in which R1 represents a linear or branched aliphatic residue comprising an ethylenic unsaturation double bond, it being optional for the latter to be that by which R1 is connected to the norbornene ring, it also being optional for the said ring to comprise other substituents chosen from C1-C3 alkyl groups, in proportions corresponding or substantially corresponding to one thiol group of the polythiol or polythiols (I) per mole of the compound or compounds (II), the thiol groups of the compound or compounds (I) adding predominantly to the cyclic double bond of the compound or compounds (II) and, on average, one ethylenic unsaturation of a compound (II) of the two which it carries remaining free; or sulphur product, (P′), obtained by the addition reaction of at least one polythiol (Type: GrantFiled: September 29, 2000Date of Patent: September 10, 2002Assignee: Cray Valley S.A.Inventors: Philippe Thépot, Henri Strub
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Publication number: 20020115808Abstract: Adhesives useful in applying articles, such as tapes, labels, signs, decals, emblems, car moldings, protective or optical films, etc., to surfaces to which articles normally do not adhere well, such as surfaces containing fluorine and polycarbonate, for example. The adhesives include a copolymer of one or more monoethylenically unsaturated alkyl (meth)acrylate monomers, one or more monoethylenically unsaturated secondary or tertiary amide-functional monomers, and optionally one or more acidic monomers.Type: ApplicationFiled: June 11, 1999Publication date: August 22, 2002Inventors: RICHARD L. PELOQUIN, ALBERT I. EVERAERTS, ELLEN O. AELING
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Patent number: 6417273Abstract: A monomer composition which provides a plastic optical material having high refractive index and Abbe number, a low specific gravity and excellent physical properties, such as dyeing properties, heat resistance, impact resistance and the like. The composition comprises a di(meth)acrylate compound, divinylbenzene and/or divinylbiphenyl, a crosslinking-type isocyanate compound, a polythiol compound having two or more thiol groups, and a thiourethane bonding accelerating compound. The plastic optical material obtained by the reaction of the above composition with a radical polymerization initiator is used as a material for a lens.Type: GrantFiled: January 23, 2001Date of Patent: July 9, 2002Assignee: NOF CorporationInventors: Yasumi Koinuma, Katsuyoshi Tanaka
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Patent number: 6399672Abstract: Radiation curable compositions for coatings, adhesives, inks, and molded articles are disclosed.Type: GrantFiled: June 2, 1999Date of Patent: June 4, 2002Assignee: Sartomer Technologies Co., Inc.Inventors: Gary W. Ceska, James P. Horgan, Thomas W. Hazell, William R. Schaeffer
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Patent number: 6242149Abstract: The fast-curing photosensitive composition capable of being cured by the irradiation with light, comprises a radical-polymerizable unsaturated compound, a photopolymerization initiator, and a thiol-containing compound, whereby the fast-curing photosensitive composition can be adequately cured even with low exposure energy.Type: GrantFiled: December 15, 1998Date of Patent: June 5, 2001Assignee: Brother Kogyo Kabushiki KaishaInventor: Minobu Maeda
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Patent number: 6206550Abstract: An active energy ray-curable composition comprising (A) 20 to 80 parts by weight of a compound represented by the following general formula I: wherein R1 represents hydrogen or methyl, X and Y may be the same or different and represent methyl, chlorine, bromine or iodine, and t and u each independently represent an integer of 0-2, (B) 20 to 80 parts by weight of at least one compound having at least one acryloyl or methacryloyl group in the molecule, or (B-1) 10 to 90 parts by weight of at least one compound having at least two acryloyl or methacryloyl groups in the molecule and (B-2) 1 to 90 parts by weight of at least one monoacrylate or monomethacrylate compound having one acryloyl or methacryloyl group in the molecule, and (C) 0.Type: GrantFiled: February 22, 1999Date of Patent: March 27, 2001Assignee: Mitsubishi Rayon Company Ltd.Inventors: Hiroshi Fukushima, Masao Hamada, Noriji Oishi, Yukichi Konami
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Patent number: 6171675Abstract: An adhesive composition including (a) a polymerizable (meth)acrylate compound having a phosphate group, (b) a thiol compound, (c) a polymerizable compound having a double bond and having no phosphate group, and (d) a photopolymerization initiator. The adhesive composition is suitably used for fabrication of optical discs.Type: GrantFiled: May 20, 1999Date of Patent: January 9, 2001Assignee: Nagase-Ciba Ltd.Inventor: Takafumi Iida
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Patent number: 6153663Abstract: A cross-linkage polymeric casting composition including an effective amount of a divinyl ester monomer of a bicyclic or polycyclic compound, and optionally, a minor amount of a di- or polythio compound. The specification and claims include allylic ethers withing the definition of divinyl ester, for example bisphenol fluorene diglycidyl allylic ether and bisphenol S diallyl ether.Type: GrantFiled: March 31, 1999Date of Patent: November 28, 2000Assignee: Sola International Holding, Ltd.Inventors: Fang Chen, Huan Kiak Toh
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Patent number: 6127447Abstract: A radiation curable coating composition is provided and includes an effective amount of cationic photoinitiator, in combination with a charge transfer complex, the charge transfer complex comprising at least one electron withdrawing reactant component and at least one electron donating reactant component free radically reactive therewith, the electron withdrawing reactant component comprising an unsaturated nitrogen containing compound and the electron donating reactant component comprising an unsaturated compound having at least one vinyl ether group, the electron donating reactant component may be separate from or structurally incorporated within the electron withdrawing reactant component and an effective amount of a cationic photoinitiator. A photopolymerization process employing the composition is also provided.Type: GrantFiled: July 30, 1999Date of Patent: October 3, 2000Assignee: Fusion UV Systems, Inc.Inventors: Mark Mitry, Roger McCartney, Mohamed R. Amin
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Patent number: 6025409Abstract: The invention relates to a coating composition comprising (a) a radiation-curable binder composition comprising an unsaturated compound having at least one maleate, fumerate, itaconate, citraconate or mesaconate group; (b) an unsaturated vinylether compound and a compound which forms a strong exciplex with (a) or (b); that is otherwise free of a photoinitiating compound.Type: GrantFiled: August 28, 1998Date of Patent: February 15, 2000Assignee: DSM N.V.Inventor: Johan F. G. A. Jansen
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Patent number: 6008265Abstract: An ionic compound comprising at least one group A.sup.+ X.sup.-, comprising:a cationic group A.sup.+ selected from the group consisting of biaryliodonium, arylsulfonium, arylacylsulfonium, diazonium and organometallic cations comprising a transition metal complexed with at least one unsaturated cyclic compound comprising 4-12 carbon atoms, said cationic group being part of a polymer chain; whereinX.sup.- is an imide anion, [FSO.sub.2 NSO.sub.2 R'.sub.F ].sup.- or [R.sub.F CH.sub.2 OSO.sub.2 NSO.sub.2 R'.sub.F ].sup.- or [(R.sub.F).sub.2 CHOSO.sub.2 NSO.sub.2 R'.sub.F ].sup.-, or a methylide anion [FSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.-, or a [R.sub.F CH.sub.2 OSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.- or [(R.sub.F).sub.2 CHOSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.31 .Type: GrantFiled: October 3, 1997Date of Patent: December 28, 1999Assignees: Hydro-Quebec, Centre National de la Recherche ScientifiqueInventors: Alain Vallee, Michel Armand, Xavier Ollivrin, Christophe Michot
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Patent number: 5973021Abstract: Organosiloxane compositions that cure in the presence of ultraviolet radiation comprise a alkenyl-substituted fluorinated polyorganosiloxane, a mercaptoalkyl-substituted fluorinated polyorganosiloxane and a photoinitiator. The cured compositions are particularly useful as coating and encapsulants to protect electronic devices that are exposed to hydrocarbon fuels.Type: GrantFiled: December 17, 1997Date of Patent: October 26, 1999Assignee: Dow Corning CorporationInventors: James Anderson Beck, Myron Timothy Maxson, Bernard VanWert
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Patent number: 5969867Abstract: An active energy ray-curable composition comprising(A) 20 to 80 parts by weight of a compound represented by the following general formula I: ##STR1## wherein R.sup.1 represents hydrogen or methyl, X and Y may be the same or different and represent methyl, chlorine, bromine or iodine, and t and u each independently represent an integer of 0-2,(B) 20 to 80 parts by weight of at least one compound having at least one acryloyl or methacryloyl group in the molecule, or (B-1) 10 to 90 parts by weight of at least one compound having at least two acryloyl or methacryloyl groups in the molecule and (B-2) 1 to 90 parts by weight of at least one monoacrylate or monomethacrylate compound having one acryloyl or methacryloyl group in the molecule, and(C) 0.Type: GrantFiled: June 14, 1996Date of Patent: October 19, 1999Assignee: Mitsubishi Rayon Company Ltd.Inventors: Hiroshi Fukushima, Masao Hamada, Noriji Oishi, Yukichi Konami
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Patent number: 5945464Abstract: The ultraviolet-curable, resin-forming composition which comprises a polycarbonic acid ester such as diethylene glycol bis(allyl carbonate), a polythiol such as pentaerythritol tetrakis(3-mercaptopropionate) and an ultraviolet curing agent. The resin-forming composition can be photopolymerized in an atmospheric condition, and the thus produced resin has an elongated durability as well as excellent properties with regard to a transparency, heat resistance, adhesion property, resistance to shock, dyeing property and others.Type: GrantFiled: August 13, 1997Date of Patent: August 31, 1999Assignee: Asahi Kogaku Kogyo Kabushiki KaishaInventors: Hidenori Takushima, Kouji Futaki
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Patent number: 5908876Abstract: Disclosed are: (1) an optical resin composition comprising Component A: a thiourethane prepolymer compound prepared by reacting a polythiol compound having at least 3 functional groups and an intramolecular sulfide bond, with a polyisocyanate compound in a molar ratio of --SH to --NCO ranging from 3.0 to 7.0 Component B: at least one (meth)acrylate compound having at least 2 functional groups; and Component C: a compound radically polymerizable with Components A and B, in 10 to 50% by weight, 35 to 70% by weight, and 5 to 30% by weight, respectively; (2) a preparation process for an optical resin by photopolymerization; (3) an optical resin; and (4) a prepolymer suitable for Component A. The composition is a novel, rapidly polymerizable composition for an optical resin. Furthermore, a resin prepared by curing the composition not only has a high refractive index and a high Abbe number, but also is excellent in transparency and optical homogeneity.Type: GrantFiled: April 7, 1997Date of Patent: June 1, 1999Assignee: Mitsui Chemicals, Inc.Inventors: Kenichi Fujii, Nobuya Kawauchi, Toshiyuki Suzuki, Seiichi Kobayashi, Masao Imai
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Patent number: 5905099Abstract: A heat-activatable adhesive comprising an acrylic copolymer, which copolymer comprises a monomer consisting of an acrylate or methacrylate ester of a non-tertiary alkyl alcohol having a Tg of about 0.degree. C. or lower; a monomer consisting of an acrylate or methacrylate ester of an alcohol having a Tg of at least about 5.degree. C.; and a functional monomer. Selected embodiments include a retroreflective article comprising a film having a substantially flat surface and a structured surface, the structured surface comprising a plurality of precisely shaped projections, a colored layer disposed on the structured surface and adhered thereto in a plurality of discrete locations, and a heat-activatable adhesive layer disposed on the colored layer.Type: GrantFiled: November 6, 1995Date of Patent: May 18, 1999Assignee: Minnesota Mining and Manufacturing CompanyInventors: Albert I. Everaerts, Yoshinori Araki, Michiru Hata
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Patent number: 5876805Abstract: Visible light cured polymerizable thiol-ene compositions comprising at least one monomer or oligomer having a plurality of free-radically polymerizable ethylenically unsaturated groups, at least one compound having a plurality of thiol groups, at least one acyl phosphine oxide photoinitiator and optional adjuvants, such as stabilizers, pigments, fillers, and polymerization inhibitors are disclosed. The polymerized compositions are useful, as protective coatings, or anti-chip coatings or as repair putties on exterior coated substrates such as plastics, wood and metal, especially for the automotive and marine industries.Type: GrantFiled: October 16, 1997Date of Patent: March 2, 1999Assignee: Minnesota Mining & Manufacturing Co.Inventor: Brian W. Ostlie
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Patent number: 5837751Abstract: Norbornenyl functional azlactone compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are independently monovalent hydrocarbon groups or R.sup.1 and R.sup.2, together with the carbon atom to which they are attached comprise a cyclic hydrocarbon group, are prepared by Diels-Alder addition of cyclopentadiene to vinyl azlactones. The norbornenyl azlactones are useful for preparing norbornenyl functional resins by azlactone ring opening reactions. The resulting resins may be employed as polyene components of curable thiol-ene formulations.Type: GrantFiled: November 28, 1990Date of Patent: November 17, 1998Assignee: Loctite CorporationInventors: Anthony F. Jacobine, Steven T. Nakos
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Patent number: 5821278Abstract: Process for the photocatalytic polymerization of a cyclic olefin or at least two different cyclic olefins in the presence of a metal compound as catalyst, which comprises carrying out a photochemical ring-opening metathesis polymerization in the presence of a catalytic amount of at least one heat-stable niobium(V) or tantalum(V) compound which contains at least two methyl groups or two monosubstituted methyl groups bound to the metal, the substituent containing no hydrogen atom in the .alpha.-position.The process can also be carried out by first performing the irradiation and completing the polymerization by heating. The process is suitable, for example, for the preparation of thermoplastic molding materials, coatings and relief images.Type: GrantFiled: May 22, 1997Date of Patent: October 13, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Paul Adriaan Van Der Schaaf, Andreas Hafner, Andreas Muhlebach
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Patent number: 5821280Abstract: A process for producing a conductive composition for a biological electrode wherein casting or injection is preformed while maintaining the flowability of the feedstock solution to thereby enable the molding of the solid gel into a desired shape. A process for producing a conductive gel composition for a biological electrode having a function of electrically and physically connecting a living body to an electrode element and comprising at least the following components:(1) a radical-polymerizable unsaturated compound;(2) an acid reacting with NaOH or KOH to thereby give a reaction product which is a moisturizer serving as a plasticizer and having a function of supplementing and promoting the physiological humidifying function of the horny layer;(3) water;(4) NaOH and/or KOH;(5) a photopolymerization or light polymerization initiator; and(6) a crosslinking agent.Type: GrantFiled: July 26, 1996Date of Patent: October 13, 1998Assignee: Nihon Kohden CorporationInventors: Shin Suda, Toru Kurata, Toshihiro Fukai, Kenichiro Maeda
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Patent number: 5821276Abstract: A printing ink for radiation curing, e.g. by UV radiation or an electron beam, comprises a mixture of a polymerizable composition, a pigment or a dye and a titanium or zirconium compound which is an alkoxide of an unsaturated alcohol, said polymerizable composition comprising at least one unsaturated monomer and, optionally, at least one prepolymer and being polymerizable by exposure to radiation. The titanium or zirconium compound acts as an adhesion promoter for the ink.Type: GrantFiled: July 23, 1996Date of Patent: October 13, 1998Assignee: Tioxide Specialties LimitedInventor: Robert Hume Duncan
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Patent number: 5741831Abstract: Transparent polymer composition comprising:a component A comprising:at least 10% by weight of a monomer or of a mixture of monomers (I), containing at least one thioacrylate or thiomethacrylate function;0 to 90% by weight of one or more monomers (II) which are copolymerizable by a radical route, preferably mono- or polyfunctional vinyl, acrylic or methacrylic; anda component B comprising, relative to the weight of the component A:0.1 to 15% by weight of one or more monomers (III) containing an ethylenic unsaturation which does not contribute to an aromatic system and having a carbon bearing a free hydroxyl group in an .alpha. position relative to the ethylenic unsaturation.Application to the manufacture of ophthalmic lenses.Type: GrantFiled: May 23, 1996Date of Patent: April 21, 1998Assignee: Essilor International - Compagnie Generale d'OptiqueInventors: Gabriel Keita, Peiqi Jiang
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Patent number: 5728749Abstract: This photopolymerizable composition includes an grafted reactive telomer containing trifluoroethyl methacrylate units, a reactive diluent and a photopolymerization initiator. It gives hydrophobic transparent coatings.Type: GrantFiled: November 30, 1995Date of Patent: March 17, 1998Assignee: Elf Atochem S.A.Inventors: Didier Vanhoye, Elsa Ballot, Robert Legros, Olivier Loubet, Bernard Boutevin, Bruno Ameduri
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Patent number: 5700576Abstract: A coating agent for producing scratch-resistant coatings on plastic articles, which comprises:(1) 1-30 wt. % of a prepolymer, as a thickener (IP thickener), which prepolymer is bound in the composition of the coating by polymerization;(2) 20-80 wt. % of multifunctional acrylates, multifunctional methacrylates or mixtures thereof;(3) 5-75 wt. % of a thinner;(4) 0.01-10 wt. % of a UV-initiator;(5) 0-20 wt. % of customary additives; wherein the prepolymer (1) is obtained by radical polymerization of:(a) 90-99 wt. % of C.sub.1 -C.sub.8 -alkyl esters of acrylic- or methacrylic acid; and(b) 1-10 wt. % of a sulfur-containing regulator having at least three thiol groups. The coating system is distinguished by high scratch-resistance and good weatherability.Type: GrantFiled: March 4, 1996Date of Patent: December 23, 1997Assignee: Roehm GmbH Chemische FabrikInventors: Manfred Brehm, Rolf Neeb, Wolfgang Scharnke, Volker Kerscher
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Patent number: 5629354Abstract: Improved photopolymerization initiator systems are comprised of a spectral sensitizer that sensitizes in the ultraviolet or visible regions of the spectrum and an N-aryl, O-aryl or S-aryl polycarboxylic acid co-initiator. The improved initiator systems are incorporated in photo-polymerizable compositions containing one or more addition-polymerizable ethylenically-unsaturated compounds to form compositions suitable for the preparation of radiation-sensitive layers in lithographic printing plates adapted to be imagewise-exposed with ultraviolet- or visible-light-emitting lasers such as argon-ion lasers and frequency doubled Nd:YAG lasers. Such plates are able to effectively meet the dual requirements of very high photospeed and very good shelf-life required in computer-to-plate systems.Type: GrantFiled: February 28, 1995Date of Patent: May 13, 1997Assignee: Eastman Kodak CompanyInventors: Paul R. West, Jeffery A. Gurney
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Patent number: 5612390Abstract: A thiol methacrylate or acrylate compound represented by the formula (1) or (2), ##STR1## wherein R.sup.1 is H or CH.sub.3 and X is selected from: ##STR2## wherein R.sup.1 is H or CH.sub.3 and m is an integer of 1 to 4. The thiol methacrylate or acrylate compound gives a resin having a high refractive index, a large Abbe number, and a good hardness and heat resistance, and giving little or no smell at processing.Type: GrantFiled: June 7, 1995Date of Patent: March 18, 1997Assignee: Toray Industries, Inc.Inventors: Yuichiro Iguchi, Michio Kimura, Koichiro Oka
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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: 5556709Abstract: A photocurable resin composition for glass lamination, consisting essentially of a radical polymerizable monomer having at least two repeating units of ethylene oxide in its molecule and a photopolymerization initiator, a cured product of which has a volume resistivity of less than 5.times.10.sup.9 .OMEGA..cm.Type: GrantFiled: June 1, 1995Date of Patent: September 17, 1996Assignee: Denki Kagaku Kogyo Kabushiki KaishaInventors: Toshiyuki Kato, Syunzi Ito, Tsunehiko Shimizui
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Patent number: 5532286Abstract: A photopolymerizable composition comprising a crosslinking agent, a UV sensitive photopolymerization initiator and a thioether compound having a vinyl ester or vinyl amide component; wherein the crosslinking agent and the thioether may be the same compound.Type: GrantFiled: March 16, 1995Date of Patent: July 2, 1996Assignee: Eastman Kodak CompanyInventors: Elizabeth G. Burns, Susan A. Visser, Jeffrey F. Taylor