Specified Rate-affecting Material Is A Metal-containing Organic Compound Patents (Class 522/29)
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Patent number: 5939148Abstract: The present invention provides a visible laser-curable photosensitive composition wherein a photocuring resin having photosensitive group which is crosslinkable or polymerizable upon light exposure, is mixed with a photopolymerization inititor system consisting of a coumarin type pigment of particular structure and a titanocene compound. This composition has an unexpectedly high sensitivity to visible laser.Type: GrantFiled: September 9, 1997Date of Patent: August 17, 1999Assignee: Kansai Paint Co., Ltd.Inventors: Genji Imai, Hideo Kogure
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Patent number: 5922783Abstract: A radiation-curable composition which includes a cyanoacrylate component or a cyanoacrylate-containing formulation; a metallocene component; and a polymerizingly effective amount of a photoinitiator to accelerate the rate of cure is provided.Type: GrantFiled: February 27, 1997Date of Patent: July 13, 1999Assignee: Loctite CorporationInventor: Stan Wojciak
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Patent number: 5879852Abstract: The invention relates to a positive-working radiation-sensitive mixture containing a) a polymeric binder having acid-labile groups and b) a compound which forms a strong acid on irradiation, in which the binder simultaneously contains units of the formulae I, II and IIIR.sup.1 --OH (I),R.sup.1 --O--CO.sub.2 R.sup.2 (II)R.sup.1 --O--CH.sub.2 --CHR.sup.3 --OH (III).The mixture is used to coat radiation-sensitive recording material which can be used to produce printing plates and photoresists.Type: GrantFiled: April 30, 1997Date of Patent: March 9, 1999Assignee: AGFA-Gevaert AGInventors: Mathias Eichhorn, Gerhard Buhr
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Patent number: 5877230Abstract: A method for the anionic photoinitiation of polymerization or crosslinking of a substrate by irradiating a mixture of a substrate and a photoinitiator, where the photoinitiator is an inorganic transition metal complex which releases on irradiation a polymerization initiating substance consisting essentially of an anionically charged nucleophile that initiates the polymerization or crosslinking reaction, under conditions that allow the anion to initiate polymerization. FIG. 3 is plot of percentage polymerization of ethyl .alpha.-cyanoacrylate containing different concentration of Reineckate's anion.Type: GrantFiled: July 25, 1997Date of Patent: March 2, 1999Assignees: University of Georgia Research Foundation, Inc., The University of GeorgiaInventor: Charles R. Kutal
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Patent number: 5866631Abstract: There is provided a dental primer composition capable of obtaining high adhesive strength to both dentin and enamel, as a pretreatment material for a chemically polymerizable adhesive. This composition is a dental primer composition comprising a polymerizable monomer containing an acidic group, water, aryl borate and transition metal compound.Type: GrantFiled: August 22, 1997Date of Patent: February 2, 1999Assignee: Tokuyama CorporationInventors: Hiroyuki Nakagawa, Hideki Ohno
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Patent number: 5863678Abstract: A photopolymerizable composition for a color filter, which comprises a compound having at least one ethylenically unsaturated double bond, a photopolymerization initiator, and a red, green or blue colorant and which, when formed into a coating film having a dried film thickness of at most 1 .mu.m, has an optical density of at least 1.1.Type: GrantFiled: January 17, 1996Date of Patent: January 26, 1999Assignee: Mitsubishi Chemical CorporationInventors: Toshiyuki Urano, Shingo Ikeda, Etsuko Hino, Shin Kawana, Takeshi Ohmori, Koji Mori
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Patent number: 5861443Abstract: Process for the photocatalytic polymerization of a cyclical olefin or at least two different cyclical olefins in the presence of a metal compound as the catalyst, which is characterized in that a photochemical ring-opening metathesis polymerization is carried out in the presence of a catalytic amount of at least one carbene-free, bivalent-cationic ruthenium or osmium compound which contains at least one phosphine group, at least one photolabile ligand, and optionally neutral ligands bonded to the metal atom, a total of 2 or 3 ligands being bonded, and which contains acid ions for balancing the charge. The process can also be carried out by first carrying out the irradiation and ending the polymerization by heating. The process is suitable, for example, for the preparation of thermoplastics shaping compounds and the production of coatings and images in relief.Type: GrantFiled: May 14, 1997Date of Patent: January 19, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Andreas Hafner, Paul Adriaan Van Der Schaaf, Andreas Muhlebach
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Patent number: 5854299Abstract: Process for the polymerization of cyclic olefins by photochemical ring-opening metathesis polymerization by irradiation, using catalytic amounts of a heat-stable ruthenium or osmium catalyst which has at least one photolabile ligand, the other coordination sites being occupied by non-photolabile ligands.Type: GrantFiled: March 8, 1996Date of Patent: December 29, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Andreas Muhlebach, Paul Bernhard, Andreas Hafner, Thomas Karlen, Martin Andreas Ludi
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Patent number: 5844016Abstract: An improved barrier or drug delivery system which is highly adherent to the surface to which it is applied is disclosed, along with methods for making the barrier. The barrier can be prepared by staining tissue with a photoinitiator, applying a solution containing a polymerizable barrier material solution and a photoinitiator to the tissue, and polymerizing the polymer solution on exposure to light. The resulting polymer adheres strongly to the tissue surface, and also forms a gel in the rest of the applied volume. The polymerizable barrier materials are highly useful for sealing tissue surfaces and junctions against leaks of fluids. The method can be used to adhere preformed barriers to tissue or other surfaces, or to adhere tissue surfaces to each other. Tissue surfaces can be adhered to each other to repair wounds. In addition to photochemical initiators, non-photochemical initiators and combinations of chemical initiators and photochemical initiators can be used.Type: GrantFiled: June 7, 1995Date of Patent: December 1, 1998Assignees: Focal, Inc., The Board of Regents--University of Texas SystemInventors: Amarpreet S. Sawhney, David A. Melanson, Chandrashekar P. Pathak, Jeffrey A. Hubbell, Luis Z. Avila, Mark T. Kieras, Stephen D. Goodrich, Shikha P. Barman, Arthur J. Coury, Ronald S. Rudowsky, Douglas J. K. Weaver
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Patent number: 5837748Abstract: A photopolymerizable composition is disclosed, comprising the following components (i), (ii) and (iii):(i) a compound having at least one addition-polymerizable, ethylenically unsaturated bond;(ii) a compound represented by formula (I): ##STR1## wherein A=represents a substituted or unsubstituted 2(3H)-thiazolylidene or 2-thiazolidinylidene group; --X-- represents --O--, --S--, --NR.sup.2 -- or --CONR.sup.3 --, in which R.sub.1, R.sup.2 and R.sup.3 each independently represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an alkenyl group, a substituted alkenyl group, an alkynyl group or a substituted alkynyl group; and=E represents a substituted or unsubstituted 1,3-dihydro-1-oxo-2H-inden-2-ylidene group; and(iii) a compound which generates an active radical upon light irradiation in the co-presence of component (ii).Type: GrantFiled: August 8, 1997Date of Patent: November 17, 1998Assignee: Fuji Photo Film Co., Ltd.Inventor: Tadahiro Sorori
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Patent number: 5824180Abstract: A method of bonding an artificial nail to a nail with a photocurable cyanoacrylate adhesive or of decorating an artificial nail or a nail using the adhesive. The adhesive comprises (A) an cyanoacrylate monomer, (B) a catalyst selected from the group consisting of a metallocene compound comprising a transition metal of Group VIII of the periodic table and aromatic electron system ligands, and a mixed catalyst consisting of a combination of a cleavage-type photoinitiator and a metallocene compound comprising a transition metal of Group VIII of the periodic table and aromatic electron system ligands, an acetylacetonatoplatinum(II) complex, and a specific metal complex which releases a nucleophilic agent upon light irradiation.Type: GrantFiled: October 30, 1996Date of Patent: October 20, 1998Assignee: Three Bond Co., Ltd.Inventors: Hiroyuki Mikuni, Yuko Nishiyama
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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: 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: 5811505Abstract: An energy-polymerizable composition derived from ingredients comprising: a cyanate ester monomer or oligomer comprising an organic radical bonded through aromatic carbon atoms to at least two --OCN groups; a low molecular weight polyalkylene glycol; and an organometallic compound in which at least one carbon atom of an organic group is bonded to a metal atom. The composition can be cured by at least one of thermal energy, radiation, and accelerated particles, to produce a cured, homogeneous composition.Type: GrantFiled: December 17, 1997Date of Patent: September 22, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventor: Fred B. McCormick
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Patent number: 5801212Abstract: A photopolymerizable composition comprising an addition-polymerizable compound having at least one ethylenic unsaturated double bond, a specific sensitizing dye represented by the following formula (I), and a titanocene compound: ##STR1## The substituents in formula (I) are defined in the specification.Type: GrantFiled: June 4, 1996Date of Patent: September 1, 1998Assignee: Fuji Photo Film Co., Ltd.Inventors: Yasuo Okamoto, Shunichi Kondo
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Patent number: 5776996Abstract: A photopolymerizable composition is disclosed, comprising i) an addition polymerizable compound having an ethylenically unsaturated double bond, ii) a sensitizing dye represented by the following formula (I) and iii) a titanocene compound: ##STR1## wherein R.sup.1, R.sup.2, R.sup.7 and R.sup.8 each represents a hydrogen atom, an alkyl group, an aryl group or an alkenyl group, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group or an alkoxycarbonyl group, R.sup.1 and R.sup.2 may be combined with each other to form a ring together with the nitrogen atom or R.sup.1 and R.sup.5 or R.sup.2 and R.sup.3 may be combined with each other to form a ring together with the carbon atoms and the nitrogen atom, R.sup.3 and R.sup.4 or R.sup.5 and R.sup.6 may be combined with each other to form a ring together with the two carbon atoms, X.sup.1 represents an oxygen atom or a sulfur atom, and n represents 0, 1 or 2.Type: GrantFiled: February 19, 1997Date of Patent: July 7, 1998Assignee: Fuji Photo Film Co., Ltd.Inventors: Yasuo Okamoto, Tadahiro Sorori
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Patent number: 5776997Abstract: Process for the photocatalytic polymerization of a cyclical olefin or at least two different cyclical olefins in the presence of a metal compound as the catalyst, in which a photochemical ring-opening metathesis polymerization is carried out in the presence of a catalytic amount of at least one heat-stable titanium(IV), niobium(V), tantalum(V), molybdenum(VI) or tungsten(VI) compound in which a silylmethyl group and at least one halogen are bonded to the metal. The process can also be carried out by first performing the irradiation and ending the polymerization by heating.The process is suitable, for example, for the production of thermoplastic shaping compounds, coatings and images in relief.Type: GrantFiled: April 23, 1997Date of Patent: July 7, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Andreas Hafner, Andreas Muhlebach, Paul Adriaan Van Der Schaaf
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Patent number: 5773528Abstract: A photocopolymerizable composition for backsealing a ceramic carrier and process for using the composition is disclosed. The composition comprises: a liquid, multifunctional, bisphenol based epoxy; a liquid, multifunctional hydroxyl containing organic material; a complex onium salt photoinitiator; and, a complex cupric salt initiator. The composition utilizes a strong Bronstead acid for additional deep curing created by iodonium salt thermolysis.Type: GrantFiled: March 19, 1996Date of Patent: June 30, 1998Assignee: International Business Machines CorporationInventors: Julio M. Alvarado, Kathleen L. Covert, Joseph P. Kuczynski
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Patent number: 5773531Abstract: A modified acrylic urethane prepolymer composition and an unsaturated polyester resin composition to which the prepolymer has been added. The prepolymer composition includes an acrylic urethane prepolymer prepared by the reaction of diisocyanate, like MDI, with an hydroxyl-containing acrylate monomer, such as a pentaerythritol triacrylate, which prepolymer composition may contain a styrene monomer and an inhibitor, such as benzoquinone, to retard the reaction of the prepolymer and styrene monomer prior to the addition of the prepolymer composition into the polyester resin composition. The employment of the modified urethane prepolymer composition provides for the reduction in the amount of styrene monomer used in the unsaturated resin composition and also provides for improved chemical and physical properties of the cured, unsaturated resin composition, such as a reduction in glass roll-out when the resin composition is employed with fiberglass.Type: GrantFiled: August 29, 1997Date of Patent: June 30, 1998Assignee: Hehr International Inc.Inventor: Stuart B. Smith
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Patent number: 5759721Abstract: A holographic recording medium comprises an acid generator capable of producing an acid upon exposure to actinic radiation; a binder; and at least one monomer or oligomer capable of undergoing cationic polymerization initiated by the acid produced from the acid generator. This recording medium is not subject to the disadvantages (for example, oxygen sensitivity) associated with radical-polymerized prior art holographic recording media.Type: GrantFiled: November 1, 1996Date of Patent: June 2, 1998Assignee: Polaroid CorporationInventors: Pradeep K. Dhal, Michael G. Horner, Richard T. Ingwall, Eric S. Kolb, Parag G. Mehta, Richard A. Minns, Howard G. Schild, David A. Waldman
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Patent number: 5744511Abstract: A visible-ray polymerizable composition comprising:(1) a monomer comprising a (meth)acrylate monomer; and(2) a visible-ray polymerization initiator comprising:(A) a coumarin dye;(B) at least one photo acid generator selected from the group consisting of a halo-alkyl substituted s-triazine derivative and a diphenyliodonium salt compound; and(C) an aryl borate compound.Type: GrantFiled: April 18, 1996Date of Patent: April 28, 1998Assignee: Tokuyama CorporationInventors: Hideki Kazama, Takeshi Satoh, Makoto Oguri
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Patent number: 5731363Abstract: A photopolymerizable composition comprising an addition-polymerizable compound having at least one ethylenic unsaturated double bond, at least one specific sensitizing dye such as the following formula (I), and a titanocene compound: ##STR1## The substituents in formula (I) are defined in the specification.Type: GrantFiled: February 28, 1996Date of Patent: March 24, 1998Assignee: Fuji Photo Film Co., Ltd.Inventors: Yasuo Okamoto, Syunichi Kondo
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Patent number: 5721289Abstract: A curable pressure sensitive adhesive having long shelf stability comprising (a) at least one free radically polymerized polymer; (2) at least one cationically-polymerizable monomer; (3) a photo-activatable catalyst system for the cationically-polymerizable monomer comprising either at least one organometallic complex salt or at least one onium salt; and (4) optionally, a monohydric or polyhydric alcohol, wherein there is essentially no conversion of the cationically-polymerizable monomer of the curable pressure sensitive adhesive when stored in a manner to exclude actinic radiation, and methods of making the same.Type: GrantFiled: October 5, 1995Date of Patent: February 24, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Naimul Karim, Kevin E. Kinzer, Albert I. Everaerts, Leo W. Halm, Steven J. Keipert, Jerry W. Williams
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Patent number: 5721288Abstract: A photopolymerizable composition is described, comprising components (i) a compound having at least one addition-polymerizable ethylenically unsaturated bond, (ii) a compound represented by the following formula (I): ##STR1## and (iii) an activating agent which generates an active radical upon light irradiation in the co-presence of component (ii). The substituents in formula (I) are defined in the specification.Type: GrantFiled: February 9, 1996Date of Patent: February 24, 1998Assignee: Fuji Photo Film Co., Ltd.Inventors: Yoshimasa Aotani, Tadahiro Sorori
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Patent number: 5712321Abstract: The polymerizable acrylate formulation, and method utilizing the same, employ a catalyst system that includes a tertiary aromatic amine compound and an air-curing polyether-ene polymer, in a specified ratio, in combination with an acid ingredient and a transition metal that together form a coordination compound. The formulation cures through bulk, as well as on the surface, in a highly effective manner.Type: GrantFiled: February 1, 1996Date of Patent: January 27, 1998Assignee: Dymax CorporationInventors: Stephen E. Cantor, Brian Bachmann
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Patent number: 5703138Abstract: An acrylate composition, especially useful for producing conformal coatings on circuit board assemblies, includes a photoinitiator and an air-curing system, the latter being comprised of a compound having multiple allyloxy groups in its molecule and a transition metal salt catalyst. The composition is highly stable against auto-induced reaction in the absence of oxygen and at room temperature; it contains no active oxygen catalyst and no nonreactive diluent, and is advantageously formulated as a one-part product.Type: GrantFiled: July 24, 1996Date of Patent: December 30, 1997Assignee: Dymax CorporationInventors: Stephen E. Cantor, Leon Levine
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Patent number: 5700856Abstract: A peroxide-generating composition for use in curing an unsaturated polyester resin and to the cured unsaturated polyester resin composition so prepared, particularly unsaturated polyester resin compositions containing inert filler materials used prepare a cast or molded product. The peroxide-generating composition comprises an allyl alcohol alkanoate, such as allyl alcohol propoxylate, which in the presence of a metal salt promoter, such as cobalt carboxylate, either with the allyl alcohol alkanoate or separately as a prepromoter in the unsaturated polyester resin composition provides for the generation from the allyl alcohol alkanoate of a peroxide to effect the in situ cure of the unsaturated polyester resin composition.Type: GrantFiled: April 10, 1996Date of Patent: December 23, 1997Assignee: Hehr International Inc.Inventor: Stuart B. Smith
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Patent number: 5700849Abstract: A photopolymerizable composition is disclosed, which comprises an addition-polymerizable compound having at least one ethylenically unsaturated double bond, a sensitizing dye represented by the following formula (I): ##STR1## wherein the all symbols are defined in the disclosure, and a titanocene compound.Type: GrantFiled: February 23, 1996Date of Patent: December 23, 1997Assignee: Fuji Photo Film Co., Ltd.Inventors: Syunichi Kondo, Kazuo Fujita
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Patent number: 5693688Abstract: The present invention relates to initiators of cationic polymerization and/or crosslinking, under photochemical and/or thermal activation and/or activation by a beam of electrons, of monomers and/or polymers containing organofunctional groups.These initiators give good performance with the majority of monomers/polymers, including in particular functional polyorganosiloxanes, which are crosslinkable cationically and under UV.The subject of the invention is also compositions based on at least one cationically crosslinkable polyorganosiloxane and on at least one initiator, as defined above.Application: paper anti-adhesion.Type: GrantFiled: September 15, 1995Date of Patent: December 2, 1997Assignee: Rhone-Poulenc ChimieInventor: Christian Priou
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Patent number: 5691394Abstract: A photopolymerizable composition is disclosed, comprising an addition polymerizable compound having at least one ethylenically unsaturated double bond, a sensitizing dye represented by formula (I) and a titanocene compound. The photopolymerizable composition exhibits high sensitivity to active light rays over a wide region of from ultraviolet light to visible light.Type: GrantFiled: February 7, 1996Date of Patent: November 25, 1997Assignee: Fuji Photo Film Co., Ltd.Inventor: Syunichi Kondo
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Patent number: 5677362Abstract: An acrylate encapsulation formulation reacts at a high rate of speed, when exposed to radiation inclusive of wavelengths in the ultraviolet and the visible range, to initially produce a relatively thick skin and to ultimately cure to a relatively low-stress deposit having good physical definition and surface properties. The method entails exposure of the formulation, on an object, to radiation for initialing photopolymerization and thermal polymerization, and the apparatus includes closely juxtaposed actinic radiation and thermal energy sources.Type: GrantFiled: November 4, 1996Date of Patent: October 14, 1997Assignee: Dymax CorporationInventors: Andrew G. Bachmann, Stephen E. Cantor
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Patent number: 5672637Abstract: The present invention provides an energy polymerizable composition comprising at least one epoxy monomer or at least one vinyl ether monomer and an initiation system therefor, the initiation system comprising at least one organometallic complex salt and at least one stabilizing additive. The cured composition provides useful articles or coated articles.Type: GrantFiled: November 3, 1995Date of Patent: September 30, 1997Assignee: Minnesota Mining and Manufacturing CompanyInventors: Wayne S. Mahoney, Michael C. Palazzotto
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Patent number: 5672393Abstract: An acrylate encapsulation formulation reacts at a high rate of speed, when exposed to radiation inclusive of wave-lengths in the ultraviolet and the visible range, to initially produce a relatively thick skin and to ultimately cure to a relatively low-stress deposit having good physical definition and surface properties. The method entails exposure of the formulation, on an object, to radiation for initialing photopolymerization and thermal polymerization, and the apparatus includes closely juxtaposed actinic radiation and thermal energy sources.Type: GrantFiled: November 4, 1996Date of Patent: September 30, 1997Assignee: Dymax CorporationInventors: Andrew G. Bachmann, Stephen E. Cantor
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Patent number: 5667574Abstract: A starch-based composition for preparing an environment degradable .alpha.-olefinic polymer molding material, which includes 95-99 wt % of starch, 0.2-0.8 wt % of a titanate coupling agent having the following formula (I), 0-2 wt % of paraffin and 0-2 wt % of fatty acid: ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen, or R.sub.1 and R.sub.2 together are .dbd.O.Type: GrantFiled: November 6, 1996Date of Patent: September 16, 1997Assignee: Chi May Co., Ltd.Inventor: Yuan Qing Zhang
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Patent number: 5639802Abstract: The present invention relates to a novel class of compounds which absorb light at wavelengths greater than 350 nm and are useful as fluorescers or as photoinitiators. The present invention provides compounds of the formulas (I) and (II) and their equivalents (the nomenclature of the compounds used herein is based on the numbering of positions as shown in formula (I)): ##STR1## where: when W is .dbd.O, W.sup.1 is hydrogen or --OR.sup.9 and when W is .dbd.NR.sup.+.sub.2, W is hydrogen or --NR.sub.2, A is hydrogen, alkenyl, alkyl or an election withdrawing group, and the remaining groups are as defined in the disclosure.Type: GrantFiled: November 23, 1993Date of Patent: June 17, 1997Assignee: Spectra Group Limited, Inc.Inventors: Douglas C. Neckers, Yubai Bi
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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: 5554664Abstract: An energy-sensitive (e.g., thermal, radiation or photosensitive) initiator, curative, and/or catalytic salt that has an anion comprising a tris-(highly fluorinated alkylsulfonyl)methide, tris-(fluorinated arylsulfonyl)methide, bis-(highly fluorinated alkyl)sulfonyl imide, bis-(fluorinated aryl)sulfonyl imide, mixed aryl- and alkylsulfonyl imides and methides and any combinations thereof, has improved solubility in organic solvents, exhibit minimal corrosiveness when coatings and adhesives are prepared using the initiator, curative and/or catalytic salts, generates a highly reactive initiator, curative, and/or catalyst upon activation by energy.Type: GrantFiled: November 17, 1995Date of Patent: September 10, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: William M. Lamanna, Michael C. Palazzotto, Wayne S. Mahoney, Michael A. Kropp
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Patent number: 5543262Abstract: A light sensitive composition which is capable of photopolymerization which includes a photopolymerizable compound a free radical generating component and a benzanthrone or substituted benzanthrone which substantially prevents photopolymerization when the light sensitive composition is exposed to actinic radiation below a threshold amount but permits photopolymerization when the light sensitive composition is exposed to actinic radiation above a threshold amount. This achieves a gate effect which eliminates or decreases unwanted partial exposure in the nonimage areas and hence improves reproduction quality.Type: GrantFiled: February 24, 1995Date of Patent: August 6, 1996Assignee: International Paper CompanyInventors: Maria T. Sypek, John R. Delude, Paul A. Perron
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Patent number: 5541235Abstract: A cationic dye in a ketone solvent, wherein the cationic dye has a counterion which comprises a linear, branched or cyclic highly fluorinated alkylsulfonyl methide or highly fluorinated alkyl sulfonyl imide.Type: GrantFiled: March 6, 1995Date of Patent: July 30, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Stanley C. Busman, William M. Lamanna
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Patent number: 5539012Abstract: Resin compositions useful for filament winding applications comprising an epoxy component including at least one polyepoxide resin curable by heat, an olefinicially unsaturated monomer component including at least one polyolefinically unsaturated monomer curable by actinic radiation, a cyanate ester component including at least one cyanate ester compound having at least two cyanate functional groups per molecule, at least one organic peroxide, at least one photoinitiator, and a heat activated curing agent for epoxides. The compositions have a viscosity less than about 2000 centipoise (cps) and are capable of retaining this viscosity for at least about 6 months at about ambient temperature. The resins are capable of being immobilized by actinic radiation exposure and further heat cured without substantial resin drip. One or more organic peroxides are employed, selected from the group of organic peroxides having 10 hour decomposition half-lives at temperatures of from about 50.degree. C. to less than about 104.Type: GrantFiled: August 18, 1993Date of Patent: July 23, 1996Assignee: Loctite CorporationInventors: Philip T. Klemarczyk, Yoshihisa Okamoto
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Patent number: 5516813Abstract: A balancing compound comprising an epoxy resin, a photoinitiator in an effective amount to cure the resin at ambient temperatures upon the application of ultraviolet light (10 nm to 400 nm) of less than 40 watts per square centimeter in less than about 30 seconds, and a filler in an effective amount to give the compound a specific gravity above 1.1.Type: GrantFiled: October 18, 1994Date of Patent: May 14, 1996Inventor: Donn R. Starkey
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Patent number: 5498641Abstract: A photopolymerizable composition comprising at least an addition polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator system, which system comprises (a) a sensitizer of the formula (I): ##STR1## wherein each of R.sup.1 to R.sup.6 is hydrogen, halogen, alkyl, aryl, aralkyl, acyl, alkoxycarbonyl, optionally substituted hydrocarbon ring, optionally substituted heterocyclic residue or --SO.sub.3 --R.sup.8, wherein R.sup.8 is hydrogen, alkyl, aryl, aralkyl, alkali metal, or quaternary ammonium, R.sup.7 is hydrogen, alkyl, aryl, aralkyl, optionally substituted hydrocarbon ring, or optionally substituted heterocyclic group, each of X.sup.1 and X.sup.2 is halogen, alkyl, aryl, aralkyl, optionally substituted hydrocarbon ring, or optionally substituted heterocyclic group, and (b) a titanocene compound.Type: GrantFiled: April 8, 1994Date of Patent: March 12, 1996Assignee: Mitsubishi Chemical CorporationInventors: Toshiyuki Urano, Hideki Nagasaka, Masaaki Tsuchiyama, Hiroshi Ide
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Patent number: 5494944Abstract: A hardenable composition containing:a) a material polymerizable by free radical or cationic polymerization,b) at least one iron compound of the formula I ##EQU1## wherein a is 1 or 2 and q is 1, 2 or 3,L is a divalent to heptavalent metal or non-metal,Q is a halogen atom,m is an integer corresponding to the sum of the values of L and q,R.sup.1 is an unsubstituted or substituted .eta..sup.6 -benzene andR.sup.2 is an unsubstituted or substituted cyclopentadienyl anion, andc) at least one sensitizer for the compound of the formula I,and, in the case of materials polymerizable by free radical polymerization, also d) an electron acceptor as an oxidizing agent, which is also advantageously used concomitantly for the material polymerizable by cationic polymerization. The composition is suitable for the production of protective layers and photographic images.Type: GrantFiled: August 18, 1994Date of Patent: February 27, 1996Assignee: Ciba-Geigy CorporationInventors: Kurt Meier, Hans Zweifel
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Patent number: 5494943Abstract: The present invention provides an energy polymerizable composition comprising at least one epoxy monomer or at least one vinyl ether monomer and an initiation system therefor, the initiation system comprising at least one organometallic complex salt and at least one stabilizing additive. The cured composition provides useful articles or coated articles.Type: GrantFiled: June 16, 1993Date of Patent: February 27, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Wayne S. Mahoney, Michael C. Palazzotto
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Patent number: 5468785Abstract: The invention relates to the use of cobaloximes and related cobalt(II) complexes which have essentially planar equatorially coordinated ligands and a pair of axially coordinated ligands which have at least one carbon-cobalt bond, as photoinitiators for free radical polymerizations. By selection of the appropriate cobaloximes and related complexes, it is possible to prepare polymers which have useful terminal functionality at both the head and the tail ends of the growing polymer chain. The process also teaches the photochemical polymerization and copolymerizations whereby the alkyl cobaloximes and related compounds, which are used as the photoinitiators, have alkyl groups, which may in essence, be polymers with carbon-cobalt chain ends, thereby allowing grafting reactions to occur to the polymer backbone.Type: GrantFiled: April 15, 1994Date of Patent: November 21, 1995Assignee: University of AkronInventors: Michael P. Greuel, Labros D. Arvanitopoulos, H. James Harwood
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Patent number: 5462797Abstract: The present invention provides a pressure-sensitive adhesive composition and a method for producing the same. The pressure-sensitive adhesive composition is produced by the combination of at least one free-radically photopolymerizable monomer and at least one set of polyurethane precursors, and a suitable photoinitiation system consisting of at least one salt of a cationic organometallic complex, an additional free-radical photo initiator and the application of sufficient energy to photopolymerize same by sequential exposure to visible electromagnetic radiation and then to ultraviolet electromagnetic radiation.Type: GrantFiled: February 8, 1994Date of Patent: October 31, 1995Assignee: Minneapolis Mining and Manufacturing CompanyInventors: Jerry W. Williams, Robert J. DeVoe, Thomas P. Klun, George F. Vesley, Patrick G. Zimmerman
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Patent number: 5459173Abstract: Stable thiol-ene compositions are provided which comprise a polythiol, a polyene and a stabilizer system comprising an alkenyl substituted phenolic compound having a formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are independently selected from the group consisting of H, OR, a C.sub.1 -C.sub.8 alkyl, substituted alkyl, alkenyl or substituted alkenyl, a C.sub.6 -C.sub.20 aryl or substituted aryl, or a cyano group; R.sup.4 is H, R, OR, halogen, COR, COOR, or SR; R.sup.5 is OH, OR, OCOR, OCOOR, OCONHR, or OTMS; R is a C.sub.1 -C.sub.6 alkyl, a cycloalkyl, or a C.sub.6 -C.sub.20 caryl or substituted aryl; x and y are 1, 2, or 3; z is 0, 1, or 2; and x+y+z=2, 3, or 4; or a formula: ##STR2## where x, y, z, w, R.sup.1 R.sup.2 R.sup.3, R.sup.4 and R.sup.5 are defined as above, except that x+y+z=2-6, and R.sup.6 is CH.sub.2, C(CH.sub.3).sub.2, O, S, or SO.sub.Type: GrantFiled: June 22, 1993Date of Patent: October 17, 1995Assignee: Loctite CorporationInventors: David M. Glaser, Anthony F. Jacobine, Paul J. Grabek
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Patent number: 5453450Abstract: A stabilized heat curable adhesive prepared from a formulation comprised of (1) at least one free radically polymerizable monomer; (2) at least one epoxy function monomer; (3) at least one free radical polymerization photoinitiator; (4) a thermally-initiated cationic catalyst system comprising (a) at least one salt of an organometallic cation, (b) at least one stabilizing additive; (5) optionally, at least one alcohol-containing material; and (6) optionally, adjuvants.Type: GrantFiled: June 16, 1993Date of Patent: September 26, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: Kevin E. Kinzer, Wayne S. Mahoney, Michael C. Palazzotto
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Patent number: 5445855Abstract: An active energy ray-curable composition comprising (A) an epoxy resin, (B) a compound selected from the group consisting of sulfonium salts and cyclopentadienyl iron compounds, (C) a compound selected from the group consisting of acrylates, methacrylates and oligomers thereof, and (D) an organic peroxide, and optionally (E) a rubber component. The composition is useful for an adhesive layer of an optical recording medium.Type: GrantFiled: August 5, 1993Date of Patent: August 29, 1995Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Suguru Tokita, Kenji Yamane, Hajime Inagaki, Masayoshi Kurisu
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Patent number: 5439746Abstract: Disclosed is an epoxy resin-based composite material formed by coating or impregnating a sheet-like reinforcement with an epoxy resin composition, followed by curing the resin composition. The epoxy resin composition comprises a compound having at least one epoxy group, a compound having an active hydrogen, a silicon compound having or generating hydroxy group bonded to silicon atom, and an organometallic compound. The epoxy resin may further comprise a maleimide compound or a powdery and granular material and a short fiber. The composite material ensures the properties of the epoxy resin material in terms of the mechanical strength, corrosion resistance, heat resistance and electrical properties. Besides, the composite material exhibits excellent crack resistance and impact resistance. Further, the epoxy resin composition contained in the composite material exhibits sufficient curing characteristics and, thus, the operation for forming the composite material is facilitated.Type: GrantFiled: March 18, 1994Date of Patent: August 8, 1995Assignee: Kabushiki Kaisha ToshibaInventor: Shuichi Suzuki