Heavy Metal Containing Dnrm Patents (Class 522/81)
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Patent number: 6162841Abstract: New betaketosulfonic derivatives, the process for their preparation, the photopolymerizable systems containing the same and their application as polymerization photoinitiators for inks, and particularly for inks having high content of pigments are described.Type: GrantFiled: March 3, 1998Date of Patent: December 19, 2000Assignee: Lamberti S.p.A.Inventors: Paola Giaroni, Piero Di Battista, Giuseppe Li Bassi
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Patent number: 6159012Abstract: In a first aspect, a method for treating hard tissue that includes: (a) applying to hard tissue a composition that includes a cationically active functional group, a free radically active functional group, and a polymerization initiator capable of initiating free radical polymerization, where the number of moles of cationically active functional groups per gram of composition is no greater than about 0.0075; and (b) exposing the composition to polymerization conditions to form an adhesive bonded to the hard tissue.Type: GrantFiled: September 1, 1999Date of Patent: December 12, 2000Assignee: 3M Innovative Properties CompanyInventors: Joel D. Oxman, Hoa T. Bui, Dwight W. Jacobs
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Patent number: 6150429Abstract: The present invention provides polyester/vinyl dioxolane based coating compositions containing no or essentially no volatile organic components. Oligomers for forming the coating compositions of the present invention are vinyl dioxolane end-capped polyester oligomers.Type: GrantFiled: November 2, 1999Date of Patent: November 21, 2000Assignee: Foster-Miller, Inc.Inventors: Robert F. Kovar, Nese Orbey, Nelson Landrau, William E. Dorogy, Jr., Paul Osenar
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Patent number: 6136881Abstract: A photocuring resin composition for orthodontics is disclosed, comprising:(a) 5.about.50% by weight of a urethane bond-free (meth)acrylate having an average molecular weight of 100.about.300 and having at least one unsaturated double bond;(b) 10.about.60% by weight of a urethane bond-containing (meth)acrylate having an average molecular weight of 300.about.5,000 and having at least one unsaturated double bond;(c) 5.about.30% by weight of a crosslinked polyurethane powder;(d) 10.about.50% by weight of an inorganic filler; and(e) 0.03.about.3% by weight of a photocuring initiator.Type: GrantFiled: September 3, 1998Date of Patent: October 24, 2000Assignee: GC CorporationInventors: Toshihiro Sekiguchi, Shunji Sugano
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Patent number: 6130980Abstract: Provided is a ribbon assembly having the functional capability of providing break-out of ink coated optical glass fibers from said ribbon assembly. The monomers, oligomers and photoinitiator for forming an ink coating on the optical glass fibers contained in the ribbon assembly have been selected to provide an average percentage of reacted acrylate unsaturation which provides a level of adhesion between a matrix material and an ink coating that is less than a level of adhesion between the ink coating and the coated optical glass fiber to provide break-out of the ink coated optical glass fiber from said ribbon assembly. Also provided are ink coating compositions adapted to form ink coatings suitable for use on optical glass fibers contained in the ribbon assembly.Type: GrantFiled: May 5, 1998Date of Patent: October 10, 2000Assignee: DSM N.V.Inventors: Edward J. Murphy, Edward P. Zahora, David M. Szurn
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Patent number: 6126731Abstract: The present invention provides a polymerizable printing ink. The ink includes a polar suspending medium in which a plurality of polymer microspheres are suspended. At least one surfactant is dissolved in the suspending medium, and a monomer is positioned in the ink such that polymerization of the monomer after the application of the ink to a substrate will hold the microspheres in fixed relations to one another. The microspheres have a chemically associated coloring agent to provide the ink with color. The ink may include a polymerization initiator, such as a photoinitiator, to cause the film to polymerize upon the application of a form of energy, such as ultraviolet light. The invention also provides methods for making and using the ink, and for adding a coloring agent to a plurality of polymer microspheres.Type: GrantFiled: August 21, 1998Date of Patent: October 3, 2000Assignee: Idea Development CompanyInventors: Matthias D. Kemeny, Geoffrey V. F. Seaman
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Patent number: 6127445Abstract: The present invention relates to anionic photoinitiator compounds, compositions containing them, and methods of using them having the structure: ##STR1## wherein X and Y are independently selected from the group consisting of a direct single bond and --C(.dbd.O)--, wherein at least one of X and Y is --C(.dbd.O)--;R.sup.1 and R.sup.2 are independently selected from the group consisting of H and substituted phenyl, wherein both R.sup.1 and R.sup.2 are not H;and wherein neither --X--R.sup.1 nor --Y--R.sup.2 is --C(.dbd.O)H. The anionic photoinitiators have improved storage stability, without loss of photosensitivity, even when stored with polymerizable or crosslinkable monomer, oligomer, or crosslinkable polymer species.Type: GrantFiled: November 3, 1998Date of Patent: October 3, 2000Assignee: The University of Georgia Research Foundation, Inc.Inventors: Charles R. Kutal, Yoshikazu Yamaguchi
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Patent number: 6114404Abstract: The present invention relates to a radiation curable ink formulation which has a tan .delta. of from about 0.5 to about 1.5. The radiation curable ink formulation includes a pigment, a radiation cross-linkable monomer or oligomer, and a rheology modifier. Flat panel color filters which contain a black radiation curable ink formulation and one or more colored radiation curable ink formulations are also disclosed. At least one of the black and colored radiation curable ink formulations has a tan .delta. of from about 0.5 to about 1.5 and includes a pigment, a radiation cross-linkable monomer or oligomer, and a rheology modifier. Methods for manufacturing these flat panel color filters are also disclosed. The radiation curable ink formulations of the present invention have the advantage of permitting clean doctoring.Type: GrantFiled: March 22, 1999Date of Patent: September 5, 2000Assignee: Corning IncorporatedInventors: John S. Deeken, Ronald E. Johnson, Lung-Ming Wu, Khalil M. Moussa
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Active radiation ray curable, solar radiation blocking resin compositions and films coated therewith
Patent number: 6107360Abstract: This invention provides a resin composition which is cured by active radiation rays, shows less absorption in the visible light region, has solar radiation blocking ability and is excellent in scratch resistance, and a film coated with the resin composition. Said resin composition comprises solar radiation absorbable fine particles of a metal oxide such as zinc antimonate anhydride, tin oxide, ATO (antimony doped tin oxide), ITO (tin doped indium oxide) or the like and an active radiation ray polymerizable (meth)acrylate having a (meth)acryloyl group, and a coating obtained therefrom has excellent paint film hardness and scratch resistance.Type: GrantFiled: August 18, 1997Date of Patent: August 22, 2000Assignee: Nippon Kayaku Kabushiki KaishaInventors: Shoichi Kaneko, Hiroshi Sakurai, Kaoru Izumi, Kenichiro Yoshioka -
Patent number: 6099415Abstract: Ultraviolet radiation curing of inks on game balls, golf balls and the like is disclosed. Production inks, logo inks and methods for forming production prints and logos on golf balls, game balls and the like are disclosed. To form an ultraviolet radiation curable water-insoluble production ink, at least an adhesion promoting component is added to an ink base.Type: GrantFiled: March 10, 1998Date of Patent: August 8, 2000Assignee: Acushnet CompanyInventor: Mitchell E. Lutz
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Patent number: 6099783Abstract: A novel method for producing thick composite parts based upon photopolymerizable compositions is disclosed. Also disclosed are novel methods for encapsulation of microelectronic devices based upon novel photopolymerizable compositions. The constituents of the photopolymerizable mixture comprise a monomer or monomers capable of polymerizing by free radical or cationic mechanisms, and a photoinitiator system which possesses an absorbance characteristic which is effectively reduced, or self-eliminating, upon initiation of the polymerization reaction. Parts having thicknesses up to 2 cm and thicker for varying end use applications are made by photopolymerizing such compositions. In addition, using such compositions composite parts can be made using a reinforcement material such as a glass fiber mat present in an amount by weight of from about 5 to about 70%.Type: GrantFiled: August 7, 1998Date of Patent: August 8, 2000Assignee: Board of Trustees Operating Michigan State UniversityInventors: Alec B. Scranton, Bharath Rangarajan, Kiran K. Baikerikar
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Patent number: 6096796Abstract: A photo-curable resin composition capable of providing a three-dimensional object having excellent mechanical strength and high dimensional accuracy when used in a photo-fabrication process. The resin composition is also capable of providing a three-dimensional object with excellent stability in shape and properties in a photo-fabrication process. The photo-curable composition includes:(A) a compound represented by the formula (1) ##STR1## wherein R.sup.1 and R.sup.2 independently represent a hydrogen atom or a methyl group;(B) a compound having a cyclohexene oxide structure;(C) a cationic photo-initiator;(D) an ethylenically unsaturated monomer;(E) a radical photo-initiator; and(F) a polyol having three or more hydroxyl groups.Type: GrantFiled: December 10, 1997Date of Patent: August 1, 2000Assignees: DSM N.V., JSR Corporation, Japan Fine Coatings Co., Ltd.Inventors: Tsuyoshi Watanabe, Tetsuya Yamamura, Akira Takeuchi, Takashi Ukachi
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Patent number: 6090865Abstract: Compounds of formula (I), ##STR1## wherein X is CH, C--CH.sub.3, C--Cl, C--O--C.sub.1 -C.sub.8 alkyl or N; R is C.sub.1 -C.sub.6 alkyl, benzyl, CH.sub.2 COOR.sub.3 or a group (a); R.sub.1 is C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.12 alkyl, halogen, NO.sub.2, benzyloxy or phenyloxy, wherein the phenyl ring in the benzyloxy or phenyloxy group is unsubstituted or substituted by C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.12 alkyl, halogen or CF.sub.3 ; R.sub.2 is C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.12 alkyl, benzyloxy or phenyloxy, wherein the phenyl ring in the benzyloxy or phenyloxy group is unsubstituted or substituted by C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.12 alkyl, halogen or CF.sub.3 ; R.sub.3 is hydrogen, C.sub.1 -C.sub.12 alkyl or benzyl; Y is unsubstituted or C.sub.1 -C.sub.6 alkoxy-substituted C.sub.1 -C.sub.6 alkyl, or Y is C.sub.1 -C.sub.6 alkoxy, halogen, CF.sub.3, NO.sub.2, benzyloxy or phenyloxy, wherein the phenyl ring in the benzyloxy or phenyloxy group is unsubstituted or substituted by C.Type: GrantFiled: October 26, 1998Date of Patent: July 18, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Christopher Curtis Dudman, Allan Francis Cunningham, Martin Kunz
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Patent number: 6071979Abstract: A method of generating reactive species which includes exposing a wavelength specific photoreactor to radiation, in which the wavelength specific photoreactor comprises a wavelength-specific sensitizer associated with one or more reactive species-generating photoinitiators. Also described are methods of polymerizing unsaturated monomers and curing an unsaturated oligomer/monomer mixture.Type: GrantFiled: December 26, 1997Date of Patent: June 6, 2000Assignee: Kimberly-Clark Worldwide, Inc.Inventors: John Gavin MacDonald, Ronald Sinclair Nohr
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Patent number: 6054501Abstract: This invention provides an energy ray curable composition which has excellent curability. The composition contains a cationic polymerizable substance, a photopolymerization initiator comprised of a specified onium salt and a pigment as occasion demands. The curable composition is excellent in curability, and cured paint films obtained therefrom shows excellent glossiness. This composition can be blended in white inks, printing inks, paints, resist inks, wood fillers and the like.Type: GrantFiled: March 9, 1998Date of Patent: April 25, 2000Assignee: Nippon Kayaku Kabushiki KaishaInventors: Nobuo Taniguchi, Minoru Yokoshima
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Patent number: 6048910Abstract: A coating composition which is comprised of an emulsion of a silicone resin, typically a water-insoluble, silanol group-bearing silicone resin dispersed in water, and contains photocatalyst particles, typically titanium oxide forms a hydrophilic film having a water-drop contact angle of no more than 60.degree. when irradiated with UV-containing light. The composition eliminates the use of organic solvents and has excellent dispersion and storage stability. Films obtained by applying this coating composition to the surface of substrates have excellent weathering resistance and antifouling properties due to a self-cleaning effect arising from the photocatalytic action of the particles.Type: GrantFiled: February 5, 1998Date of Patent: April 11, 2000Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masahiro Furuya, Masaaki Yamaya
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Patent number: 6043295Abstract: Photocurable, addition polymerizable compositions contain an epoxy resin and a photoinitiator system containing (a) an epoxy resin and (b) a photoinitiator system comprising: (i) an iodonium salt; (ii) a visible light sensitizer; and (iii) an electron donor compound, wherein the photoinitiator system has a photoinduced potential of at least about 0 mV relative to a standard solution of 2.9.times.10.sup.-5 moles/g diphenyl iodonium hexafluoroantimonate and 1.5.times.10.sup.-5 moles/g camphorquinone in 2-butanone. The compositions cure on exposure to light in the visible spectrum and are useful in a variety of applications, including dental adhesives and composites.Type: GrantFiled: July 28, 1999Date of Patent: March 28, 2000Assignee: 3M Innovative Properties CompanyInventors: Joel D. Oxman, Dwight W. Jacobs
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Patent number: 6040357Abstract: Provided is radiation-curable ink composition containing a radiation-curable carrier system containing at least one radiation-curable monomer or oligomer and at least one pigment dispersed in the radiation-curable carrier system in an amount sufficient to provide a color which is visible without magnification. The pigment is substantially insoluble in the radiation-curable carrier system whereby the particulate shape of the pigment is substantially retained in the radiation-curable carrier system. The pigment having a particle size that substantially avoids pigment induced microbending of an optical glass fiber coated with the ink coating.Type: GrantFiled: May 28, 1998Date of Patent: March 21, 2000Assignee: DSM N.V.Inventors: Edward J. Murphy, Jeffrey Classey, David M. Szum
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Patent number: 6037385Abstract: An 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, such as MDI, with an hydroxyl-containing acrylate monomer, such as a pentaerythritol triacrylate. The prepolymer composition contains 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 and a photoinitiator to promote the polymerization of the resin by exposure to radiant energy. The employment of the 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 photocured, unsaturated resin composition.Type: GrantFiled: November 7, 1997Date of Patent: March 14, 2000Assignee: Hehr International Inc.Inventor: Stuart B. Smith
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Patent number: 6031015Abstract: A dental material based on polymerizable monomers is described which contains at least one polymerizable monomer which has liquid crystalline properties. Compared with traditional materials, the dental material displays a lower decrease in volume upon polymerization and, because of its low viscosity, higher filler contents can be achieved.Type: GrantFiled: July 17, 1996Date of Patent: February 29, 2000Assignee: Ivoclar AGInventors: Helmut Ritter, Georg Draheim, Norbert Moszner, Ulrich Salz, Volker Rheinberger
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Patent number: 6022906Abstract: Compounds of the formulae I, II, III and IV ##STR1## wherein Ar for example is a phenyl, biphenyl or benzoylphenyl group, which is unsubstituted or substituted; Ar.sub.1, for example, has the same meanings as Ar; Ar.sub.2 is inter alia phenyl; X may be a direct bond; Y hydrogen, etc.; R.sub.1 and R.sub.2 for example C.sub.1 -C.sub.8 alkyl; R.sub.3 inter alia hydrogen or C.sub.1 -C.sub.12 alkyl; R.sub.4 is inter alia C.sub.1 -C.sub.12 alkyl; or R.sub.3 and R.sub.4 together are C.sub.3 -C.sub.7 alkylene; R.sub.5 is for example C.sub.1 -C.sub.6 alkylene; and Z is a divalent radical; provided that at least one of the radicals Ar, Ar.sub.1, Ar.sub.2, Ar.sub.3, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 or Y is substituted by 1 to 5 SH groups, or provided that Y contains at least one --SS-- group, are photoinitiators for the polymerization of ethylenically unsaturated compounds.Type: GrantFiled: December 1, 1997Date of Patent: February 8, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Masaki Ohwa, Hitoshi Yamoto, Jean-Luc Birbaum, Hiroko Nakashima, Akira Matsumoto, Hidetaka Oka
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Patent number: 6017660Abstract: Photocurable addition-polymerizable compositions containing a free-radically-polymerizable monomer and a photoinitiator system containing i) an arylidonium salt, ii) a sensitizing compound, and iii) an electron donor having an oxidation potential that is greater than zero and less than or equal to that of p-dimethyoxybenzene (1.32 volts vs. S.C.E.). The compositions cure rapidly and deeply under ultraviolet or visible light.Type: GrantFiled: June 9, 1998Date of Patent: January 25, 2000Assignee: 3M Innovative Properties CompanyInventors: Michael C. Palazzotto, F. Andrew Ubel, III, Joel D. Oxman, M. Zaki Ali
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Patent number: 6013339Abstract: This invention relates to a liquid crystal display apparatus formed by sealing a liquid crystal between two substrates having electrodes and an alignment film with a seal material, the production process comprising the steps of attaching two substrates in a vacuum, compressing under atmospheric pressure to provide a uniform cell gap, a temporary hardening process of the seal material by ultraviolet ray irradiation and a main hardening process of the seal material by heating, wherein a radically polymerizable curing resin is used in the liquid crystal seal material. The method provides a liquid crystal display panel having a uniform cell gap, without dislocation of the alighnment between substrates, or discharge of uncured component of a seal material to the liquid crystal, capable of having a seal material firmly attached to the substrates even at panel corner portions, and having an excellent straightness and moisture resistance of the seal material.Type: GrantFiled: December 10, 1997Date of Patent: January 11, 2000Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Satoshi Yamada, Hideki Matsukawa
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Patent number: 6005017Abstract: Opaquely pigmented or thick filmed powder coatings for heat sensitive substrates, such as wood, wood composites, for example, medium density fiber board, and plastics, that can be fully cured, especially near the substrate, through the incorporation of a dual cure system in the powder comprising a thermal initiator, such as a peroxide, along with a UV initiator. The UV initiator cures the surface, while the thermal initiator cures at the substrate. Surprisingly, virtually no pregelation occurs during the heated melt and flow out step prior to UV curing. Consequently, the hardened film finish formed on the surface exhibits exceptional smoothness which is comparable to that of traditional UV curable powders. The hardened film finish is also fully cured throughout and exhibits exceptional adhesion to the substrate which cannot be achieved with traditional UV curable powders that have been pigmented.Type: GrantFiled: December 16, 1997Date of Patent: December 21, 1999Assignee: Morton International, Inc.Inventors: Andrew T. Daly, Jeno Muthiah, Richard P. Haley, Joseph J. Kozlowski, Navin B. Shah
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Patent number: 6001533Abstract: A composition for forming a non-conductive light-shielding layer, comprising an alkali-soluble binder, a pigment, a photopolymerizable monomer, a photo-polymerization initiator and a solvent, wherein the pigment comprises fine particles of a double oxide selected from CuMn.sub.2 O.sub.4, and CuMn.sub.2 O.sub.4 in which a part of Mn is substituted with Fe, Co and/or Ni.Type: GrantFiled: March 25, 1997Date of Patent: December 14, 1999Assignee: Dai Nippon Printing Co., Ltd.Inventors: Syunsuke Sega, Toshio Yoshihara, Kyoko Kogo, Junzo Nagashima
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Patent number: 6001203Abstract: This invention relates to a liquid crystal display apparatus formed by sealing a liquid crystal between two substrates having electrodes and an alignment film with a seal material, the production process comprising the steps of attaching two substrates in a vacuum, compressing under atmospheric pressure to provide a uniform cell gap, a temporary hardening process of the seal material by ultraviolet ray irradiation and a main hardening process of the seal material by heating, wherein a radically polymerizable curing resin is used in the liquid crystal seal material. The method provides a liquid crystal display panel having a uniform cell gap, without dislocation of the alighnment between substrates, or discharge of uncured component of a seal material to the liquid crystal, capable of having a seal material firmly attached to the substrates even at panel corner portions, and having an excellent straightness and moisture resistance of the seal material.Type: GrantFiled: December 10, 1997Date of Patent: December 14, 1999Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Satoshi Yamada, Hideki Matsukawa
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Patent number: 5990190Abstract: A photosensitive resin composition for cast molding, which has an ultraviolet transmittance of 0.05-5% as measured at a 1-mm thickness.Type: GrantFiled: July 15, 1997Date of Patent: November 23, 1999Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Shohei Nakamura, Kousi Anai
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Patent number: 5980253Abstract: In a first aspect, a method for treating hard tissue that includes: (a) applying to hard tissue a composition that includes a cationically active functional group, a free radically active functional group, and a polymerization initiator capable of initiating free radical polymerization, where the number of moles of cationically active functional groups per gram of composition is no greater than about 0.0075; and (b) exposing the composition to polymerization conditions to form an adhesive bonded to the hard tissue.Type: GrantFiled: January 12, 1998Date of Patent: November 9, 1999Assignee: 3M Innovative Properties CompanyInventors: Joel D. Oxman, Hoa T. Bui, Dwight W. Jacobs
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Patent number: 5962608Abstract: In one embodiment, the present invention relates to a polymer prepared from a mixture containing a polymerization material and a polycondensation product of a partially hydrolyzed chelated metal oxide precursor. In another embodiment, the present invention relates to a process for making a polymer involving contacting a polymerization material with a metal oxide sol comprising a liquid and a polycondensation product of a partially hydrolyzed chelated metal oxide precursor to form a mixture and at least one of polymerizing and curing the mixture of the polymerization material and the polycondensation product.Type: GrantFiled: February 13, 1998Date of Patent: October 5, 1999Assignee: Reliance Electric Industrial Co.Inventors: Hong-Son Ryang, Young Jin Chung, Joseph T. Snyder, II, An-Min Jason Sung
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Patent number: 5942290Abstract: Molecular complex compounds comprising a mono-, bis- or trisacylphosphine oxide compound with an .alpha.-hydroxy ketone compound are suitable as photoinitiators for the photopolymerization of free-radically polymerizable compounds.Type: GrantFiled: August 21, 1997Date of Patent: August 24, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: David George Leppard, Thomas Lloyd James, Nils Hock, Manfred Kohler, Ronald Salathe
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Patent number: 5929130Abstract: Photocurable resin compositions capable of producing plastic molds with improved durability by stereolithography in the presence of a photoinitiator includes unsaturated urethane of a specified kind, vinyl monomer of a specified kind, a filler and salt of phosphoric acid ester of specified kinds at a specified ratio.Type: GrantFiled: June 28, 1996Date of Patent: July 27, 1999Assignee: Takemoto Yushi Kabushiki Kaisha & Teijin Seiki Co., Ltd.Inventors: Toshiharu Suzuki, Tatsuhiko Ozaki, Hirokazu Matsueda, Yorikazu Tamura, Tsuneo Hagiwara
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Patent number: 5919834Abstract: Disclosed are UV-cured heat transfer labels prepared from a mixture containing at least one thermoplastic resin, at least one material for solvating the thermoplastic resin, the solvating material being either a solvent or liquid monomer, and at least one photo-initiable material which initiates curing of the composition.Type: GrantFiled: September 29, 1997Date of Patent: July 6, 1999Assignee: Illinois Tool Works Inc.Inventors: Myron H. Downs, James D. Singelyn, Bruce W. Downs
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Patent number: 5916713Abstract: The present invention provides a polymerizable composition for a color filter, which comprises a (meth)acrylate copolymer containing alicyclic (meth)acryloyl groups in its side chains, a compound having at least one ethylenically unsaturated double bond, a photopolymerization initiator and a colorant, a color filter obtained by coating the composition on a glass substrate, followed by exposure and development; and a method for producing a color filter, which comprises coating the composition on a glass substrate, followed by exposure and development.The polymerizable composition of the present invention is highly sensitive and excellent in chemical resistance. Accordingly, according to the present invention, it is possible to produce a color filter of a high quality without a protective layer such as an oxygen-shielding film.Type: GrantFiled: September 25, 1996Date of Patent: June 29, 1999Assignee: Mitsubishi Chemical CorporationInventors: Tameichi Ochiai, Ryuichiro Takasaki, Noriko Endou, Yuzuru Chika
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Patent number: 5908875Abstract: A method of preparing a radiant energy cured polyester resin composition which contains a modified acrylic urethane prepolymer, a styrene monomer, and a photoinitiator. The polyester resin composition is cured by exposure to radiant energy alone or with peroxide curing agents.Type: GrantFiled: April 20, 1998Date of Patent: June 1, 1999Assignee: Hehr International Inc.Inventor: Stuart B. Smith
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Patent number: 5898041Abstract: This invention relates to a liquid crystal display apparatus formed by sealing a liquid crystal between two substrates having electrodes and an alignment film with a seal material, the production process comprising the steps of attaching two substrates in a vacuum, compressing under atmospheric pressure to provide a uniform cell gap, a temporary hardening process of the seal material by ultraviolet ray irradiation and a main hardening process of the seal material by heating, wherein a radically polymerizable curing resin is used in the liquid crystal seal material. The method provides a liquid crystal display panel having a uniform cell gap, without dislocation of the alighnment between substrates, or discharge of uncured component of a seal material to the liquid crystal, capable of having a seal material firmly attached to the substrates even at panel corner portions, and having an excellent straightness and moisture resistance of the seal material.Type: GrantFiled: February 28, 1996Date of Patent: April 27, 1999Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Satoshi Yamada, Hideki Matsukawa
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Patent number: 5886063Abstract: The invention relates to compositions of ionization-setting maleic resins and their use for manufacture of composite materials with a fibrous reinforcement. These compositions comprise a maleic resin and a reactive diluent made up of at lest one compound chosen from among dipentaerythritol pentacrylate and hydroxyethyl methacrylate, the total quantity of reactive diluent being between 10 and 70 parts by weight per 100 parts by weight of maleic resin. They may also comprise a plasticizer such as bis-allylic resin. With these compositions it is possible to obtain composite materials set by ionization without additional post heat treatment.Type: GrantFiled: February 27, 1997Date of Patent: March 23, 1999Assignee: Aerospatiale Societe Nationale IndustrielleInventors: Frederic Alexandre Lionel Boursereau, Patrice Dourthe
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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: 5856373Abstract: A visible-light photopolymerizable composition comprising a) a cationically polymerizable epoxy resin, b) a hydroxyl-containing material c) an aryliodonium salt and d) a visible light sensitizer that is an alpha-dicarbonyl compound having an extinction coefficient less than about 1000. Particularly preferred compositions of the present invention are dental materials.Type: GrantFiled: October 3, 1997Date of Patent: January 5, 1999Assignee: Minnesota Mining and Manufacturing CompanyInventors: David A. Kaisaki, Sumita B. Mitra, William J. Schultz, Robert J. DeVoe
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Patent number: 5854298Abstract: The present invention relates to a hybrid cure mechanism developed to polymerize highly filled/loaded, optically opaque, acrylate polymeric material compositions by radiant energy. The hybrid cure mechanism, when incorporated into a resinous composition, can be utilized to repair surface coatings on high performance aircraft where an extended composition pot life or application life and rapid cure capability combined with an acceptable shelf life stability are required. More specifically, the present invention relates to an electrically conductive resinous paint or gap filler for a suitably prepared composite or metallic surface. The composition also has applications on a production line of high performance aircraft.Type: GrantFiled: September 29, 1997Date of Patent: December 29, 1998Assignee: Lockheed Martin CorporationInventors: Stephanie D. McNay, Dustin B. Martin, Thomas L. Marino, Douglas C. Neckers
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Patent number: 5852067Abstract: A near infrared rays-curing putty composition containing (A) a polymerizable ethylenically unsaturated group-containing resin, (B) a polymerizable ethylenically unsaturated compound and (C) a near infrared rays polymerization initiator, said near infrared rays polymerization initiator (C) being a near infrared rays-absorbing cationic dye and a resin powder consisting of gelation polymer fine particles.Type: GrantFiled: November 15, 1996Date of Patent: December 22, 1998Assignees: Showa Denko K. K., Kansai Paint Co., Ltd.Inventors: Hajime Sukejima, Shinji Tomita, Shuichi Sugita, Kazuhiko Ooga
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Patent number: 5852129Abstract: A method for producing a hydroxyl-terminated (meth) acrylic polymer which comprises converting a halogen atom in a terminal structure of the general formula (1)--CH.sub.2 --C(R.sup.1)(CO.sub.2 R.sup.2)(X) (1)wherein R.sup.1 is hydrogen or methyl, R.sup.2 is alkyl containing 1 to 20 carbon atoms, aryl containing 6 to 20 carbon atoms or aralkyl containing 7 to 20 carbon atoms, and X is chlorine, bromine or iodine, of a (meth)acrylic polymer obtained by polymerizing a (meth)acrylic monomer using an organic halide or a halogenated sulfonyl compound as an initiator and, as a catalyst, a metal complex with a central metal selected from the elements belonging to the groups 8, 9, 10 and 11 in the periodic table, into a hydroxyl-containing substituent.The present invention can provide, in an easy and simple manner, a (meth)acrylic polymer which is hydroxyl-terminated at both ends in a high proportion and which has been difficult to produce in the prior art. It can give a cured product with good curing characteristics.Type: GrantFiled: November 28, 1997Date of Patent: December 22, 1998Assignee: Kaneka CorporationInventors: Masato Kusakabe, Kenichi Kitano, Yoshiki Nakagawa
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Patent number: 5847015Abstract: A radiation-sensitive composition which comprises (A) a binder polymer which is a copolymer comprising (A-1) a monomer containing an alcoholic hydroxyl group, (A-2) a macromonomer, and (A-3) other monomer copolymerizable with the above monomers; (B) a pigment, and (C) a radiation-sensitive compound. This radiation-sensitive composition is suited as a color-dispersed composition for a color filter which does not cause surface soiling and which has an excellent adhesion of a formed pixel to a glass substrate.Type: GrantFiled: January 13, 1997Date of Patent: December 8, 1998Assignee: JSR CorporationInventors: Yusuke Tajima, Nobuo Bessho, Hiroaki Nemoto, Fumine Shitani
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Patent number: 5837750Abstract: Provided is a radiation-curable, glass optical fiber coating composition which when suitably cured exhibits resistance to attack from hydrocarbon gel cable filing material. The composition containsabout 10 to about 90% by weight of a first radiation-curable oligomer;from 0 to about 40% by weight of a reactive diluent;from 0 to about 40% by weight of a photoinitiator;from 0 to about 10% by weight of a pigment; andabout 10 to about 90% by weight of a second radiation-curable oligomer according to the following formula:R.sup.1 -L.sup.1 -C.sup.1 -L.sup.2 -R.sup.2 (1)where:R.sup.1 and R.sup.2, independently, each represent a radiation-curable functional group;L.sup.1 and L.sup.2, independently, each represent an alkyleneoxy chain having from about 2 to about 40 carbon atoms, wherein L.sup.1 and L.sup.2 are linked to C.sup.1 through an oxygen atomC.sup.1 comprises a hydrocarbon having from about 5 to about 40 carbon atoms and containing at least one cyclic group.Type: GrantFiled: March 12, 1996Date of Patent: November 17, 1998Assignee: DSM N.V.Inventors: David M. Szum, Timothy E. Bishop, Steven R. Schmid
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Patent number: 5837746Abstract: Compounds of the formulaRG--A--INwherein IN is a photoinitiator basic structure A is a spacer group and RG is a functional reactive group can be employed as coreactive photoinitiators for photo-polymerization of systems containing ethylenically unsaturated compounds.Type: GrantFiled: June 23, 1997Date of Patent: November 17, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Manfred Kohler, Jorg Ohngemach, Eike Poetsch, Rudolf Eidenschink, Gerhard Greber, Dieter Dorsch, Jurgen Gehlhaus, Konrad Dorfner, Hans Ludwig Hirsch
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Patent number: 5830927Abstract: Aqueous based printing ink compositions adapted for use in gravure and flexographic printing on hydrophobic substrates are prepared by combining a low-viscosity resin emulsion having an average particle diameter of less than about 0.5 microns and comprised of hydrophobic, moisture resistant, adherent resin forming components with a pigment paste containing a water-soluble polymer. The printing inks are substantially devoid of volatile organic solvent.Type: GrantFiled: August 5, 1997Date of Patent: November 3, 1998Assignee: Lehigh UniversityInventors: John W. Vanderhoff, Philippe Huwart
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Patent number: 5824717Abstract: The invention relates to peroxide- or radiation-curable copolymer containing compositions and to the resulting radiation- or peroxide- cured compositions. The compositions may optionally contain a reinforcing filler. Copolymers employed in the compositions are acrylate modified copolymers of an isoolefin of 4 to 7 carbon atoms and para-alkylstyrene comonomers. Since the percentage of extractables from the cured composition is negligible, the cured compositions are suitable for use in the manufacture of a variety of high purity rubber goods used in the pharmaceutical and health care industries. In addition, the compositions may be employed as condenser packings and as food contact materials or wire cable insulation materials. Further, the cured composition may be employed in the manufacture of high purity hoses.Type: GrantFiled: June 7, 1995Date of Patent: October 20, 1998Assignee: Exxon Chemical Patents Inc.Inventors: Natalie Ann Merrill, Hsien-Chang Wang, Anthony Jay Dias
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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: 5821279Abstract: A radiation curable filling material is used for a process of manufacturing a printed circuit board having plated landless through-holes. The material is filled in the through-holes and solidified in the through-holes via a photo polymerization to protect plated through-hole interior from an etching solution. The composition comprises a hydrophthalic acid monoester compound as a component (A); a catalyst for promoting photo polymerization of a vinyl group in the mono ester as a component (B); a highly transparent rosin having a Hazen color tone of 300 or less for the improvement of filling material transmission by radiation as a component (C), a powder of extender as a competent (D). The photo polymerization reaction occurs at the vinyl group of the hydrophthalic mono ester with the presence of the catalyst for promoting the photo polymerization. The rate of the reaction is enhanced by adding a vinyl compound such as an acrylate.Type: GrantFiled: April 25, 1996Date of Patent: October 13, 1998Assignee: Goo Chemical Co., Ltd.Inventors: Katsuo Doi, Satoshi Miyayama, Toshikazu Oda
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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: 5798397Abstract: Provided is a composition curable by active energy rays, comprising a cationic polyacryloyl compound having two or more acryloyl groups and one or more cation groups in a molecule, represented by any of General Formulae (1) to (6) ##STR1## wherein Z.sub.1 to Z.sub.6 represent independently a residue derived from a polyhydric alcohol or a polyepoxide,K.sub.1 represents independently a radical of the formula ##STR2## K.sub.2 represents a radical of the formula ##STR3## R.sub.1 represents independently a radical of the formula ##STR4## wherein R.sub.3 is independently H-- or CH.sub.3 --, and R.sub.2 represents independently a radical of the formulaCH.sub.2 .dbd.CHCOO--, or CH.sub.2 .dbd.C(CH.sub.3)COO--.Type: GrantFiled: December 24, 1996Date of Patent: August 25, 1998Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Makiko Kimura, Masato Katayama, Akio Kashiwazaki, Yoshie Nakata, Yuko Nishioka