Specified Rate-affecting Material Contains Phosphorous, Arsenic, Antimony Or Nitrogen Patents (Class 522/28)
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Patent number: 6316519Abstract: Synthesis of linear acrylic polymers and copolymers having controlled molecular weight by the photoinitiated free radical polymerization of vinyl monomers in the presence of chain transfer agents to produce polymers useful in coating compositions and the like, including printing inks.Type: GrantFiled: August 19, 1999Date of Patent: November 13, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Charles Thomas Berge, Vincent Desobry
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Patent number: 6306502Abstract: A coating composition forming a abrasion resistant coating comprising (A) an ultraviolet-curable silicone prepared by chemically modifying particulate colloidal silica with a specific silane compound, (B) a monomer mixture comprising a (meth)acrylate having a specific isocyanate skeleton and a urethane poly(meth)acrylate having an alicyclic skeleton, and (C) a photo-polymerization initiator. By using a urethane poly(meth)acrylate having an alicyclic skeleton as part of the component (B) and the component (A) having an enhanced reactivity of chemical modification, the compatibility of the component (A) with the component (B) is improved to give a cured coating with excellent wear resistance, weather resistance and durability.Type: GrantFiled: March 19, 1998Date of Patent: October 23, 2001Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Hiroshi Fukushima, Misao Tamura, Osamu Takemoto, Katsumi Yonekura
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Publication number: 20010012596Abstract: Compounds of the formulae I, II, III, IV and V 1Type: ApplicationFiled: December 12, 2000Publication date: August 9, 2001Inventors: Kazuhiko Kunimoto, Hidetaka Oka, Masaki Ohwa, Junichi Tanabe, Hisatoshi Kura, Jean-Luc Birbaum
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Publication number: 20010011108Abstract: The present invention involves the use of powder coating methods to form coated abrasives. In one embodiment, the powder is in the form of a multiplicity of binder precursor particles comprising a radiation curable component. In other embodiments, the powder comprises at least one metal salt of a fatty acid and optionally an organic component that may be a thermoplastic macromolecule, a radiation curable component, and/or a thermally curable macromolecule. In either embodiment, the powder exists as a solid under the desired dry coating conditions, but is easily melted at relatively low temperatures and then solidified also at reasonably low processing temperatures. The principles of the present invention can be applied to form make coats, size coats, and/or supersize coats, as desired.Type: ApplicationFiled: January 16, 2001Publication date: August 2, 2001Applicant: 3M Innovative Properties CompanyInventors: Ernest L. Thurber, Eric G. Larson, Gregg D. Dahlke, Robert J. DeVoe, Alan R. Kirk, Mark R. Meierotto, Roy Stubbs
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Patent number: 6265459Abstract: Accelerators that can be useful for an energy polymerizable composition comprising a cationically curable material; energy polymerizable compositions comprising at least one cationically curable material and an initiation system therefor, the initiation system comprising at least one organometallic complex salt and at least one accelerator; and a method for curing the compositions. The cured compositions can provide useful articles. The invention also provides compositions of matter comprising an organometallic complex salt and at least one compound selected from the Class 1 and Class 2 compounds disclosed herein.Type: GrantFiled: December 31, 1998Date of Patent: July 24, 2001Assignee: 3M Innovative Properties CompanyInventors: Wayne Scott Mahoney, Peggy Sperl Willett
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Patent number: 6261736Abstract: The pattern forming material of the present invention includes a polymer having a group which generates an acid when the polymer is irradiated with an energy beam or heated and a compound which generates a base when the compound is irradiated with an energy beam. The polymer is a binary polymer or a polymer of a higher degree obtained by polymerizing another group with a compound represented by the following general formula: where R1 indicates a hydrogen atom or an alkyl group, and R2 and R3 independently indicate a hydrogen atom, an alkyl group, a phenyl group or an alkenyl group, or together indicate a cyclic alkyl group, a cyclic alkenyl group, a cyclic alkyl group having a phenyl group or a cyclic alkenyl group having a phenyl group.Type: GrantFiled: October 12, 1999Date of Patent: July 17, 2001Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Masayuki Endo, Masamitsu Shirai, Masahiro Tsunooka
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Patent number: 6248804Abstract: Radiation curing of inks on game balls, golf balls and the like is disclosed. The radiation used is ultraviolet and/or visible light. Production inks, logo inks and methods for forming production prints and logos on golf balls, game balls and the like are disclosed. To ensure that the ink is sufficiently through-cured, visible light photoinitiators are added to the ink. In addition, co-initiators and ultraviolet light photoinitiators can also be included in the ink. To form a radiation curable water-insoluble production ink, at least an adhesion promoting component is added to an ink base. The adhesion promoting component is sufficient to maintain adhesion of the production ink of at least about 75% of the inked surface to the topcoat and to the surface of the game ball or the golf ball after radiation curing and after coating the production ink with the topcoat. To form radiation curable water-insoluble logo ink, at least a toughening agent is added to an ink base.Type: GrantFiled: January 20, 1998Date of Patent: June 19, 2001Assignee: Acushnet CompanyInventor: Mitchell E. Lutz
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Patent number: 6235807Abstract: A curing process for cationically polymerisable monomers, which comprises applying a composition comprising: (a) at least one cationically polymerisable monomer, (b) as photoinitiator at least one iodonium salt containing an SbF6, PF6 or BF4 anion, (c) one pigment, and (d) at least one sensitiser, to a substrate, irradiating it with light having a wavelength of 200-600 nm and then heat-postcuring it, is distinguished by little yellowing of the cured formulation.Type: GrantFiled: December 14, 1998Date of Patent: May 22, 2001Assignee: Ciba Specialty Chemicals CorporationInventor: Ljubomir Misev
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Patent number: 6231804Abstract: A high molecular weight polyethylene prepared by preliminary polymerization is added at the time of main polymerization of an olefin, for example, propylene, to prepare an olefin (co)polymer composition comprising the above high molecular weight polyethylene finely dispersed as fine particles in the polyolefin, such as polypropylene, and a cross-linked structure is formed in the olefin (co)polymer composition. This process can provide a modified olefin (co)polymer composition improved in the strength in a molten state in terms of melt tension or the like and in crystallization temperature and excellent in moldability such as high-speed producibility, and a molded modified olefin (co)polymer composition excellent in properties such as heat resistance and rigidity.Type: GrantFiled: October 1, 1999Date of Patent: May 15, 2001Assignee: Chisso CorporationInventors: Akira Yamauchi, Shingo Kikukawa, Jun Saito, Hitoshi Sato
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Patent number: 6232359Abstract: Radiation curable ink compositions and coating compositions contain an aliphatic (meth)acrylate functional macromonomer, a reactive acrylate monomer, and a photoinitiator. Ink compositions also contain an effective amount of a colorant or pigment. These inks, when cured by exposure to actinic radiation, have excellent durability, weatherability, and adhesion to acrylate substrates such as polymethylmethacrylate.Type: GrantFiled: October 8, 1999Date of Patent: May 15, 2001Assignee: 3M Innovative Properties CompanyInventor: Paul D. Christian
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Patent number: 6210759Abstract: Single-solution adhesive resin formulations are made of predominantly dimethacrylates or diacrylates containing predominantly) two carboxyl groups and a functionalized methacrylate or acrylate diluent monomer. A novel light-activated initiator can be used for photopolymerization of such adhesives.Type: GrantFiled: March 15, 2000Date of Patent: April 3, 2001Assignee: American Dental Association Health FoundationInventor: Sabine H. Dickens
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Patent number: 6211260Abstract: A photocurable paint composition for road markings is disclosed, comprising (A) a compound having an ethylenically unsaturated group, (B) a filler, (C) a cationic dye represented by formula (1): D+&Circlesolid;A1− (1) (wherein D+ represents a cation having an absorption maximum wavelength in the wavelength region of from 400 to 1,200 nm, and A1− represents an optional anion), (D) a quaternary organic borate-type sensitizer represented by formula (2): (wherein R1, R2, R3 and R4 each independently represents an alkyl group, an aryl group, an aralkyl group, an alkenyl group, an alkynyl group, a silyl group, a heterocyclic group or a halogen atom, and Z+ represents an optional cation) and (E) an ultraviolet radical polymerization initiator capable of generating a radical upon absorption of light at a wavelength of 400 nm or less, or additionally comprising (F) glass beads.Type: GrantFiled: November 4, 1998Date of Patent: April 3, 2001Assignee: Showa Denko K.K.Inventors: Kenichi Nakamura, Hirotoshi Kamata, Toshio Koshikawa, Shuichi Sugita
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Patent number: 6207726Abstract: A photocurable prepreg composition which is characterized by easy control of a B stage state of a thermosetting resin such as an unsaturated polyester resin or an epoxy acrylate resin, excellent storage stability, and remarkable curability after being shaped; as well as a production method therefor. A photocurable prepreg composition which contains an unsaturated polyester resin and/or an epoxy acrylate resin; at least two photopolymerization initiators with photosensitivity in different wavelength ranges; and an inorganic or an organic fiber-reinforcing material and/or filler, and which composition is treated with light of a specific wavelength such that at least one photopolymerization initiator and radical-polymerizable unsaturated groups remain partially in said resin; a production method therefor; and formed articles produced therefrom.Type: GrantFiled: February 11, 1999Date of Patent: March 27, 2001Assignees: Showa Denko Kabushiki Kaisha, Showa Highpolymer Co., Ltd.Inventors: Kazuo Ohtani, Tomio Yamamoto, Hidetake Sendai, Shuichi Sugita, Hirotoshi Kamata, Takeo Watanabe
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Patent number: 6207727Abstract: A photoinitiator mixture comprising a) at least one acyl- or diacylphosphine oxide of the formula I and b) at least one benzophenone derivative of the formulaType: GrantFiled: December 30, 1998Date of Patent: March 27, 2001Assignee: BASF AktiengesellschaftInventors: Erich Beck, Christof Kandzia, Bernhard Prantl, Matthias Lokai, Peter Enenkel, Edmund Keil, Klaus Menzel
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Patent number: 6191191Abstract: A polymerizable composition for dental use, containing monomer (a) with a polymerizable olefinic unsaturated group, acylphosphine oxide (b), organic peroxide (c), tertiary amine (d) and aromatic sulfinic acid and/or a salt thereof (e). The polymerizable composition for dental use exerts excellent curability by any of photo-polymerization and chemical polymerization, having a good color for dental use, with less color change between prior to and after polymerization, and excellent light resistance, producing a cured product with a smaller thickness of the unpolymerized layer on the surface, having larger curing depth and excellent adhesion to teeth and metals and the like and great color fastness in hot water and in darkness. By taking advantages of these excellent properties, the polymerizable composition can effectively be used for utilities, for example as a bonding agent, a composite resin, an adhesive agent, a primer and an opaque primer and the like, for dental use.Type: GrantFiled: February 9, 1999Date of Patent: February 20, 2001Assignee: Kuraray Co., Ltd.Inventors: Miho Harada, Kenichi Hino
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Patent number: 6171759Abstract: A photocurable composition containing at least a radical polymerizable unsaturated group-bearing compound, a metal allene compound, a squalilium dye, and N,N-dimethylaniline. The photocurable composition is polymerized and cured by generation of radicals upon receipt of low energy of visible light having long wavelengths or near infrared light.Type: GrantFiled: February 28, 1995Date of Patent: January 9, 2001Assignee: Brother Kogyo Kabushiki KaishaInventor: Kouji Inaishi
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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: 6146789Abstract: In a battery in which a metallic battery case for accommodating electricity-generating elements also serves as an electrode, a visible-light or near-infrared-light curing resin is used for providing a coating to insulate an end face and a peripheral edge portion of an opening portion of the battery case or a gap between a positive electrode and a negative electrode. The visible-light or near-infrared-light curing resin excels in a depth-curing characteristic as compared with a conventional ultraviolet curing resin, and cures well even up to a portion such as an insulating seal of a battery where a light-receiving port is light and the light is difficult to reach. Hence, the visible-light or near-infrared-light curing resin is prevented from becoming peeled off and provides a reliable insulting characteristic.Type: GrantFiled: February 16, 2000Date of Patent: November 14, 2000Assignee: Three Bond Co., Ltd.Inventors: Kenichi Horie, Katsuhiko Kishi, Teiji Okayama, Mutsuhiro Maeda
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Patent number: 6133335Abstract: The present invention provides compositions comprising epoxy-containing monomers, where the polymerization of the monomers can be influenced by accelerators. The compositions include at least one photo-polymerizable epoxy monomer and an initiation system. The initiation system comprises at least one organo-iron complex salt and at least one accelerator. The epoxy-containing monomers are energy-polymerized to form useful articles or coated articles.Type: GrantFiled: December 31, 1998Date of Patent: October 17, 2000Assignee: 3M Innovative Properties CompanyInventors: Wayne S. Mahoney, Peggy S. Willett, Michael A. Johnson
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Patent number: 6124371Abstract: The invention relates to a composition comprising polymerizable material and an anionic photocatalyst. The photocatalyst is a photolabile compound able to liberate a strong base having a pK.sub.a .gtoreq.12. The catalyst can be illustrated by the structural formula Z-A wherein Z is a photolabile group and A is a strong base, for example, a nitrogen containing compound such as, a secondary amine, a guanidine or amidine and Z is covalently bound to A.Type: GrantFiled: August 21, 1998Date of Patent: September 26, 2000Assignee: DSM N.V.Inventors: Dirk A. W. Stanssens, Johan F. G. A. Jansen
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Patent number: 6120977Abstract: An exposure technique which accomplishes high transparency and the prevention of influence of reflected light in the ultraviolet region of KrF excimer laser light, the technique being capable of decreasing reflected light by employing a base polymer having high transparency in the ultraviolet region and by employing a bleaching agent in combination with a photo acid generator, the bleaching agent being capable of preventing the formation of eaves in an upper portion of a resist pattern.Type: GrantFiled: April 3, 1996Date of Patent: September 19, 2000Assignee: Fujitsu LimitedInventors: Yuko Kaimoto, Satoshi Takechi, Akira Oikawa
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Patent number: 6114406Abstract: A UV-curable ink jet composition comprises a polyfunctional alkoxylated or polyalkoxylated acrylate monomer (80% to 95% by weight), a photoinitiator (e.g. from 1 to 15% by weight) and preferably a colorant (e.g. 1% to 10% by weight).Type: GrantFiled: December 3, 1998Date of Patent: September 5, 2000Assignee: Coates Brothers PLCInventors: Nigel Antony Caiger, Hartley David Selman
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Patent number: 6114408Abstract: Single-solution adhesive resin formulations are made of predominantly dimethacrylates or diacrylates containing (predominantly) two carboxy groups and a functionalized methacrylate or acrylate diluent monomer. A novel light-activated initiator can be used for photopolymerization of such adhesives.Type: GrantFiled: February 6, 1998Date of Patent: September 5, 2000Assignee: American Dental Association Health FoundationInventor: Sabine Dickens
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Patent number: 6110987Abstract: A photocurable composition comprising an ultraviolet radical polymerization initiator, a cationic dye with absorptions in the visible light region, a quaternary boron salt and optionally a polymerization accelerator, is irradiated with ultraviolet light and visible light either simultaneously or separately, to achieve adequate hardening in air of both the surface and the interior of the cured product, and to provide a cured product with an excellent appearance and without production of coloring substances derived from the polymerization initiator.Type: GrantFiled: July 11, 1997Date of Patent: August 29, 2000Assignee: Showa Denko K.K.Inventors: Hirotoshi Kamata, Toshio Koshikawa, Takeo Watanabe, Kazuhiko Ooga, Shuichi Sugita
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Patent number: 6106761Abstract: The invention relates to a process for heating polymer material, including irradiation of said polymer material with infrared radiation. In accordance with the process according to the invention the infrared radiation has wave lengths which substantially are not equal to the absorption peaks of the polymer material in respect of infrared radiation.Type: GrantFiled: March 20, 1998Date of Patent: August 22, 2000Assignee: Wirsbo Bruks ABInventors: Michael Sjoberg, Jan Rydberg, Jyri Jarvenkyla
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Patent number: 6099123Abstract: Unsaturated polyester resin-based ophthalmic lens compositions that are modified for unexpected improvement in speed of manufacture while maintaining uniform, low optical distortion and/or improved tint speed by the addition to the polyester composition of at least one photoinitiator, preferably having at least some activity at a wavelength above about 380 nm so that a UV-absorbing compound can be included in the polyester lens composition, and the polyester resin composition is photocured to gelation in about 7 minutes or less, e.g., using a light intensity of at least about 300 microwatts/cm.sup.2, more preferably at least about 500 microwatts/cm.sup.2, most preferably at least about 1,000 microwatts/cm.sup.2.Type: GrantFiled: September 4, 1997Date of Patent: August 8, 2000Assignee: Signet Armorlite, Inc.Inventors: Thomas J. Engardio, Philip D. Dalsin
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Patent number: 6100314Abstract: The invention relates to an adhesive system for fixing dental restorative materials to hard dental substance constitutingi) a component which contains at least one activator which is a constituent of a chemical initiator system, and contains at least one ethylenically unsaturated compound which is capable of polymerization,ii) a component which contains at least one ethylenically unsaturated compound which is capable of polymerization but otherwise contains no further activator, which is able to start chemical curing with the activator from component i), andiii) a dental restorative material which contains at least one activator which, together with the activator from i), is able to start a polymerization reaction, or a cement for fixing dental restorative materials that have already cured, which contains at least one activator which, together with the activator from component i), is able to start radical polymerization.Type: GrantFiled: May 8, 1998Date of Patent: August 8, 2000Assignee: ESPE Dental AGInventor: Klaus-Peter Stefan
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Patent number: 6096794Abstract: Dye compounds of the formula ##STR1## wherein X is for example CH, C--CH.sub.3 or .sup.+ NOR L.sup.- ; R is inter alia C.sub.1 -C.sub.6 alkyl; R.sub.1 is for example C.sub.1 -C.sub.8 alkoxy or C.sub.1 -C.sub.12 alkyl; s is 0 to 4; R.sub.2 is for example hydrogen; Ar is for example a group ##STR2## Y inter alia is C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy; r in the formula (A) is 0 to 5, in the formulae (B) and (E) is 0 to 9 and in the formula (D) is 0 to 7; and L is an anion;in combination with an electron donor compound, especially a borate compound, are suitable as photoinitiators for the photopolymerization of radically polymerizable compositions.Type: GrantFiled: October 26, 1998Date of Patent: August 1, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Allan Francis Cunningham, Martin Kunz
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Patent number: 6090736Abstract: A photocatalytic powder for environmental clarification, comprising finely divided titanium dioxide particles having a coating of porous calcium phosphate formed on at least part of the surface of each titanium dioxide particle, wherein an anionic surface active agent is present at least on the interface between said coating of porous calcium phosphate and the titanium dioxide particle. This photocatalytic powder is produced by dispersing finely divided titanium dioxide particles in an aqueous slurry containing an anionic surface active agent, and then forming a coating of porous calcium phosphate on at least part of the surface of each titanium dioxide particle. This photocatalytic powder is used, for example, by supporting it in an organic polymer shaped article.Type: GrantFiled: December 28, 1998Date of Patent: July 18, 2000Assignees: Agency of Industrial Science and Technology, Showa Denko Kabushiki Kaisha, Hiroshi Taoda, Toru NonamiInventors: Hiroshi Taoda, Toru Nonami, Katsura Ito, Hiroyuki Hagihara
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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: 6084035Abstract: A resin composition for powder coating, comprising(A) a carboxyl group-containing resin having a number average molecular weight of 1000 to 20000, an acid value of 5 to 200 and a glass transition temperature of 30 to 120.degree. C.,(B) bis(.beta.-methylglycidyl)terephthalate of the formula (1): ##STR1## as a curing agent, and (D) at least one compound selected from the group consisting of amines having the linkage of the formula (2): ##STR2## in the molecule, a triarylphosphines and onium salts as a ring-opening polymerization inhibitor, the equivalent ratio of (.beta.-methylglycidyl group of the component (B))/(carboxyl group of the component (A)) being 0.5 to 3.0. The composition can give a product of curing excellent in impact resistance, weathering resistance and so on.Type: GrantFiled: November 4, 1998Date of Patent: July 4, 2000Assignee: Nissan Chemical Industries, Ltd.Inventors: Satoru Miyake, Hisao Ikeda, Toshinari Koda, Motohiko Hidaka
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Patent number: 6080450Abstract: The use of a phosphine oxide photoinitiator enables the effective curing of a polymerizable acrylate formulation despite the incorporation of a high concentration of a fluorescing agent, thereby facilitating, and enhancing the efficiency of, evaluation of the cured deposit utilizing its fluorescent response.Type: GrantFiled: February 10, 1997Date of Patent: June 27, 2000Assignee: Dymax CorporationInventor: Stephen E. Cantor
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Patent number: 6075065Abstract: The invention provides a photocurable resin composition which inhibits the deactivation of a bisacylphosphine oxide-series photopolymerization initiator and is useful for coating optical fibers. The photocurable resin composition comprises (A) a polyurethane (meth)acrylate oligomer, (B) an ethylenically unsaturated compound, (C) a bisacylphosphine oxide-series photopolymerization initiator, and (D) a tertiary amine and no tin component. Incorporation of the component (D) inhibits the decomposition and deactivation of the component (C). The component (A) may contain an aliphatic C.sub.14-40 polyol (hydrogenated dimerdiol, 12-hydroxystearyl alcohol) as a polyol component. This resin composition is used for a primary coating of a glass fiber or an indirect coating of an optical fiber through the primary layer, the coating layer being cured by light irradiation to provide an optical fiber coated with the resin composition.Type: GrantFiled: December 4, 1997Date of Patent: June 13, 2000Assignees: Takeda Chemical Industries, Ltd., Shin-Etsu Chemical Co., Ltd.Inventors: Kyuya Yamazaki, Mitsuhiro Nishimura, Takashi Uemura, Akira Yamamoto, Shouhei Kozakai, Masatoshi Asano
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Patent number: 6057078Abstract: Compounds of the formula I ##STR1## in which n and o are a number from 0 to 50, m is a number from 1 to 50, u and v are 0 or 1, and at least one of the indices u and v is 1, R.sub.1, R.sub.2, R.sub.2a, R.sub.3 and R.sub.4 independently of one another are, for example, aromatic hydrocarbons, R.sub.5, if n and o are 0, is for example C.sub.1 -C.sub.12 alkyl and, if n and/or o are greater than 0, or if n and o are 0 and at the same time only one index u or v is 1, R.sub.5 may additionally, for example, be an aromatic hydrocarbon, at least one of the radicals R.sub.1, R.sub.2, R.sub.2a, R.sub.3, R.sub.4 and R.sub.5 being an aromatic hydrocarbon radical which is sterically hindered ortho to the boron atom, X is, for example, C.sub.1 -C.sub.20 alkylene, phenylene, biphenylene, etc., and Z is a radical which is able to form positive ions, are suitable as photoinitiators, both the compounds per se and their combination with dyes or other electron acceptors.Type: GrantFiled: July 23, 1998Date of Patent: May 2, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
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Patent number: 6054251Abstract: The present invention provides a visible laser-curable resist composition which contains at least one radical-protecting compound selected from a phosphorous acid ester compound and an aromatic compound having N,N-dimethylamino group bonded to the carbon atom forming the aromatic ring and which is free from the hindrance of curing caused by deactivation of radical by oxygen and has excellent curability, and a process for formation of a resist pattern using the above composition.Type: GrantFiled: September 25, 1997Date of Patent: April 25, 2000Assignee: Kansai Paint Co., Ltd.Inventors: Genji Imai, Hideo Kogure
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Patent number: 6045953Abstract: A photosensitive recording material comprising an alicyclic, solvent-soluble, thermosetting epoxy oligomer capable of cationic polymerization, the oligomer being of a specified structure, an aliphatic monomer having at least one ethylenically unsaturated bond, the monomer being liquid at normal temperature and pressure, having a boiling point of 100.degree. C. or above at normal pressure and being capable of radical polymerization, a photoinitiator selected from the group consisting of i) a first photoinitiator capable of simultaneously generating a radical species that activates radical polymerization and a Br.o slashed.nsted acid or Lewis acid that activates cationic polymerization, upon exposure to actinic radiation, and ii) a second photoinitiator comprised of a radical polymerization photoinitiator capable of generating a radical species that activates radical polymerization upon exposure to actinic radiation and a cationic polymerization photoinitiator capable of generating a Br.o slashed.Type: GrantFiled: May 6, 1997Date of Patent: April 4, 2000Assignee: Toppan Printing Co., Ltd.Inventors: Yasushi Ohe, Hiromitsu Ito, Niro Watanabe
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Patent number: 6025017Abstract: A coating formulation suitable for use in preparing thermal transfer ribbons is provided which is curable by UV radiation or visible light. The coating formulation forms thermal transfer layers that produce printed images when used in a thermal transfer printer. The coating formulation comprises a photoreactive monomer or oligomer, a photoinitiator and a sensible material. Also provided are printers which use these ribbons and processes for preparing them.Type: GrantFiled: May 21, 1997Date of Patent: February 15, 2000Assignee: NCR CorporationInventor: Joseph D. Roth
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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: 6004725Abstract: A negative acting photoimageable composition comprisesA) between about 30 and about 70 wt %, based on total weight of A) plus B), of a organic binder polymers having sufficient acid functionality to render said photoimageable composition developable in alkaline aqueous solution,A) comprising between about 3 and about 65 wt % relative to total of A) plus B) a binder polymer A') having a weight average molecular weight between about 5000 and about 40,000 and a T.sub.g of between about 40 and about 100, and 5 to 67 wt % relative to total of A) plus B) a binder polymer A") having a weight average molecular weight between about 41,000 and about 200,000 and a T.sub.g of between about 40 and about 100,B) between about 30 and about 60 wt %, based on total weight of A) plus B), of .alpha.,.beta.-ethylenically unsaturated compounds, said component B) comprisingB') an isocyanate trimer having tri-.alpha.,.beta.Type: GrantFiled: July 17, 1998Date of Patent: December 21, 1999Assignee: Morton International, Inc.Inventors: Robert Barr, Daniel E. Lundy, Eiji Kosaka, Shigeru Murakami
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Patent number: 5994033Abstract: A screen printing stencil made from a composition comprising polyhydroxy compounds having a plurality of 1,2- or 1,3-diol groups along a polymer backbone, the diol groups grafted thereto a compound of formula (I) (where A is an arylene or an alkylene group; X is an oxygen atom, a sulfur atom, a carbon-carbon bond, or a group of formula (a), (b) or (c); R is a hydrogen atom or a methyl group; R.sup.1 is a (C.sub.1 -C.sub.4) alkyl group; m is an integer of from 1 to 8; n is an integer of from 1 to 3; and p is 1 or 2); or an acetal of the polyhydroxy, compound with ethylene glycol.Type: GrantFiled: June 2, 1999Date of Patent: November 30, 1999Assignee: Sericol LimitedInventors: Robert S. Davidson, Stuart J. Palmer, Julie E. Pratt, Stephen P. Wilson
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Patent number: 5990188Abstract: The present invention provides the discovery of an improved radiation curable coating composition comprising at least one acrylic monomer, a photoinitiator, and an ultraviolet light absorber selected from triazine or a dibenzoyl resorcinol derivative or a mixture thereof, the dibenzoyl resorcinol derivative having the formula ##STR1## where Ar and Ar' are independently substituted or unsubstituted monocyclic or polycyclic aryl groups and R' is H or a linear or branched alkyl chain having less than about 10 carbons bearing a --Si(OR.sup.2).sub.3, where R.sup.2 is a C.sub.1 to C.sub.6 alkyl group.Type: GrantFiled: August 15, 1996Date of Patent: November 23, 1999Assignee: General Electric CompanyInventors: Gautam Ambalal Patel, James Edward Pickett, Gregory Ronald Gillette, George Frederic Medford
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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: 5981113Abstract: Radiation curable ink compositions and coating compositions contain an aliphatic (meth)acrylate functional macromonomer, a reactive acrylate monomer, and a photoinitiator. Ink compositions also contain an effective amount of a colorant or pigment. These inks, when cured by exposure to actinic radiation, have excellent durability, weatherability, and adhesion to acrylate substrates such as polymethylmethacrylate.Type: GrantFiled: December 17, 1996Date of Patent: November 9, 1999Assignee: 3M Innovative Properties CompanyInventor: Paul D. Christian
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Patent number: 5977199Abstract: The invention describes a dental composition, delivery system and method for making temporary crowns and bridges in which the composition comprises two free-radical polymerizable pastes, one a catalyst paste and the other a base paste, wherein the catalyst paste comprises at least one polymerizable monomer, at least one polymerization initiator which is a peroxide oxidizing agent, at least one first polymerization inhibitor and a filler, and wherein the base paste comprises at least one polymerizable monomer, at least one polymerization accelerator, at least one second polymerization inhibitor, at least one non-polymerizable plasticizer and a filler. These catalyst and base pastes are stored in a dual cartridge from which they can be dispensed with a dispenser, preferably in a 1:1 volume ratio, and can be mixed in a static mixer to form a moldable polymerizing material, which is then applied to a prepared area of one or more teeth in a patient's mouth to form a crown or a bridge.Type: GrantFiled: February 17, 1998Date of Patent: November 2, 1999Assignee: The Kerr CorporationInventor: Xiaoyi Xie
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Patent number: 5976763Abstract: In accordance with the present invention, there are provided highly sensitive, water-developable photoreactive resin compositions useful for the preparation of printing plates. Due to the high sensitivity of invention resin compositions, they are particularly useful for preparation of digitally imaged printing plates. Printing plates prepared employing invention compositions are characterized as having excellent exposure sensitivity, the capability of rapidly curing upon exposure, excellent retention of fine details, and excellent colorless performance. Moreover, printing plates prepared employing invention compositions have good clarity and flexibility, excellent washout properties, and retain such properties over extended periods of storage. Once photopolymerized, printing plates of the invention have excellent physical properties, enabling their use in many very demanding flexographic applications.Type: GrantFiled: March 5, 1997Date of Patent: November 2, 1999Inventors: David H. Roberts, Mitch G. Male
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Patent number: 5976735Abstract: There is described a lithographic plate which comprises a base coated with a photopolymerisable composition which comprises a polymeric binder, at least one free-radically polymerisable ethylenically unsaturated compound and as the photoinitiator combination a metallocene compound, N-phenyl glycine or a substituted N-phenyl glycine or an N-phenyl glycine derivative together with a third component which is a substance which helps in the reaction initiation but also increases the sensitivity of the photopolymerisable composition to a desired region of the spectrum.Type: GrantFiled: March 21, 1996Date of Patent: November 2, 1999Assignee: Kodak Polychrome Graphics LLCInventors: Alan Stanley Victor Monk, Peter Andrew Reath Bennett, Christopher David McCullogh, Geoffrey Horne
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Patent number: 5973022Abstract: The invention provides dental composition system having curable liquid which is useful alone as a light curable composition and which is useful by mixing with a powder in preselected proportions to form dual cure compositions. The composition system is useful as bonding agent, cement, liner, base, restorative, pit and fissure sealants, and/or core build-up material, having improved adhesion to dentin. After storing the powder and the liquid in separate containers for at least two weeks and then mixing a portion of the powder and a portion of the liquid to form a mixture, the polymerizable compound polymerizes within 20 minutes of the mixing to form a first polymeric material having a flexural strength of at least 50 MPa, and an expansion in water at 37.degree. C. after 90 days of less than 1 percent by volume.Type: GrantFiled: November 1, 1996Date of Patent: October 26, 1999Assignee: DENTSPLY Research & Development Corp.Inventors: Kewang Lu, Paul D. Hammesfahr
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Patent number: 5962546Abstract: Compositions containing conductivity enhancers, which are capable of being coated onto a substrate by means of electrostatic assistance. The compositions comprise one or more cationically polymerizable monomer(s), one or more cationic initiator(s), and one or more non-volatile conductivity enhancer(s) having anionic and cationic portions which are soluble in the monomer(s) and which do not interfere with cationic polymerization wherein the anionic portion is a non-coordinating carbon-containing anion. The compositions may further comprise one or more dissociation enhancing agent(s), oligomer(s) or polymer(s), preferably co-reactive, free-radically curable monomer(s), free-radical generating initiator(s), leveling agents, and other additives or adjuvants to impart specific properties to the polymerized composition.Type: GrantFiled: May 1, 1997Date of Patent: October 5, 1999Assignee: 3M Innovative Properties CompanyInventors: Albert I. Everaerts, William M. Lamanna, Albert E. Seaver, George V. D. Tiers
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Patent number: 5942372Abstract: 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: November 19, 1996Date of Patent: August 24, 1999Assignee: Kodak Polychrome Graphics, LLCInventors: Paul Richard West, Jeffery Allen Gurney
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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