Specified Rate-affecting Material Is Heterocyclic Patents (Class 522/16)
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Patent number: 6500877Abstract: The present invention discloses an ultraviolet light curable paint composition and method for applying and making such a composition to a substrate. Suitable substrates include glass, metals, and various plastics such as polycarbonates. The disclosed composition does not contain any significant amount of volatile organic solvents that do not become incorporated in the coating or are released to ambient after curing.Type: GrantFiled: September 25, 2000Date of Patent: December 31, 2002Assignee: Krohn Industries, Inc.Inventor: Roy C. Krohn
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Patent number: 6495298Abstract: This invention relates to a photopolymerizable resin composition containing resin component (A) composed of a resin and/or a resin-forming ingredient and a photopolymerization initiator (B) wherein the component (A) comprises an addition-polymerizable compound (A1) having at least two ethylenically unsaturated groups and the photopolymerization initiator (B) comprises a diaminobenzophenone compound (B1), an N-phenylglycine compound (B2), and at least one kind of compound selected from a group of a 3,3′,4,4′-tetra(alkylperoxycarbonyl)benzophenone (B3), 2-methyl-1-[4-(thiomethyl)phenyl]- 2-morpholinopropan-1-one (B4), and a 1,3,5-triazine derivative (B5) containing at least one trihalomethyl group as substituent.Type: GrantFiled: November 29, 2000Date of Patent: December 17, 2002Assignee: Nippon Steel Chemical Co., Ltd.Inventors: Koichi Fujishiro, Manabu Higashi
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Patent number: 6486225Abstract: A photocurable composition comprising (A) 100 parts by weight of a compound having an ethylenically unsaturated group, (B) from 0.001 to 5 parts by weight of a cationic dye having an absorption maximum wavelength in the wavelength region of from 400 to 1,200 nm represented by formula (1: D+·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 31 represents an anion, and (C) from 0.Type: GrantFiled: November 17, 1999Date of Patent: November 26, 2002Assignee: Showa Denko Kabushiki KaishaInventors: Hirotoshi Kamata, Takeo Watanabe, Kazuhiko Ooga, Toshio Koshikawa
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Patent number: 6486227Abstract: The present invention is directed to energy-efficient, photoinitiators having the general formula: wherein Z each independently represent wherein R1, R2, R3, R4, R5, R6, R7, R8 are as defined in claim 1, and wherein R9 represents (R10)2O or (R10)3N; wherein R10 represents H or an alkyl group having from one to eight carbon atoms; and wherein R11 represents H, an alkyl group having from one to eight carbon atoms, a benzyl group or an aralkyl group. The present invention is also directed to a method of generating a reactive species, methods of polymerizing polymerizable materials, methods of curing an unsaturated oligomer/monomer mixture, and methods of laminating using the photoinitiators of the present invention. In addition, the present invention is directed to ink compositions, adhesive compositions and resins, and methods of printing using the above-described photoinitiators.Type: GrantFiled: June 19, 2001Date of Patent: November 26, 2002Assignee: Kimberly-Clark Worldwide, Inc.Inventors: Ronald Sinclair Nohr, John G. MacDonald
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Patent number: 6429235Abstract: An energy-curable polymer-forming composition for making a pressure sensitive adhesive includes an unsaturated oligomer resin and an adhesive promoter which increases the peel strength of the adhesive without reducing its tack. The composition also includes a tackifier and various other optional components such as photoinitiator, chain extender, reactive diluent and the like.Type: GrantFiled: September 15, 1999Date of Patent: August 6, 2002Assignee: Cognis CorporationInventors: Ulrike Varlemann, Ning Chen, Arifin Marzuki, Ramesh Narayan
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Patent number: 6376569Abstract: A process for the addition of compounds containing silicon-bonded hydrogen to compounds containing aliphatic unsaturation and compositions suitable for said process. The process is activated by actinic radiation and is conducted in the presence of a platinum complex having one cyclopentadienyl group that is eta-bonded to the platinum atom and three aliphatic groups that are sigma-bonded to the platinum atom and a free-radical photoinitiator that is capable of absorbing actinic radiation such that the hydrosilation reaction is initiated upon exposure to actinic radiation. The invention also provides compositions for use in the aforementioned process.Type: GrantFiled: December 13, 1990Date of Patent: April 23, 2002Assignee: 3M Innovative Properties CompanyInventors: Joel D. Oxman, Larry D. Boardman
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Patent number: 6362248Abstract: A photochromic polymerizable composition comprising (a) a polyfunctional (meth)acrylate monomer, (b) at least one kind of chromene compound selected from the group consisting of three kinds of chromene compounds represented by particular structural formulas, and (c) a compound having at least one or more epoxy groups in the molecules. The photochromic polymerizable composition offers a photochromic material that exhibits little initial color and excellent photochromism resistance suited for use as lenses for spectacles.Type: GrantFiled: September 24, 1999Date of Patent: March 26, 2002Assignee: Tokuyama CorporationInventors: Tadashi Hara, Yuichiro Kawabata, Junji Momoda, Hironobu Nagoh
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Patent number: 6342122Abstract: An solvent-based pressure sensitive adhesive (PSA) having improved shear adhesion is composed of an acrylic-based PSA resin, an ethylenically unsaturated polyester, an ultraviolet radiation (UV) photosensitizer, and fugative organic solvent for the acrylic-based PSA resin. The PSA is cured by evaporation of the fugative organic solvent coupled with heat and UV irradiation or UV irradiation alone. Such PSA has improved shear adhesion by dint of the addition of the ethylenically-unsaturated polyester and an ultraviolet radiation (UV) photosensitizer. A method for adhering two substrates using the PSA includes applying the PSA to one or both of substrates. The solvent in the PSA is evaporated from the applied PSA. Finally, the polyester component of the applied PSA is cured by exposure of the applied PSA to ultraviolet (UV) radiation.Type: GrantFiled: August 7, 2000Date of Patent: January 29, 2002Assignee: Ashland Chemical, Inc.Inventors: Daniel Joseph Riley, Raymond Scott Harvey, Harvey Joseph Richards, Peter Albert Yurcick
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Patent number: 6326414Abstract: An ultraviolet-curable adhesive for bonding optical disks, which comprises (A) a radical-polymerizable vinyl compound, (B) an &agr;-hydroxyalkylphenone compound as a photopolymerization initiator, and (C) 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-propane-1-one, and which can provide optical disk products which are small in warping of disks, retain sufficient performances even under high temperature and high humidity and have a good appearance.Type: GrantFiled: February 29, 2000Date of Patent: December 4, 2001Assignee: Nagase Chemtex CorporationInventor: Takafumi Iida
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Patent number: 6323253Abstract: The present invention is directed to silicone formulations which are capable of being rapidly cured to tough elastomeric materials through exposure to UV radiation, and optionally through exposure to moisture as well. The cured products demonstrate high resistance to flammability and combustibility. The flame-retardant components is a combination of hydrated alumina and an organo ligand complex of a transition metal or an organosiloxane ligand complex of a transition metal or a combination thereof.Type: GrantFiled: September 9, 1999Date of Patent: November 27, 2001Assignee: Loctite CorporationInventor: Lester D. Bennington
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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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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: 6228560Abstract: A photosensitive resin composition comprising (A) a binder polymer having carboxyl groups, (B) a photopolymerizable compound having at least one polymerizable ethylenically unsaturated group in the molecule, and (C) a photoinitiator can provide a film excellent in mechanical strength, chemical resistance, flexibility, and suitable for producing a photosensitive element.Type: GrantFiled: December 15, 1999Date of Patent: May 8, 2001Assignee: Hitachi Chemical Company, Ltd.Inventors: Tatsuya Ichikawa, Tatsuo Chiba
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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: 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: 6162881Abstract: New initiators which are suitable for cationic polymerization have the following structure: ##STR1## such that following apply: R.sup.1 and R.sup.2 are alkyl or cycloalkyl or they, together with the S atom, form a heterocyclic ring,R.sup.3 is H or alkyl,R.sup.4, R.sup.5, R.sup.6, and R.sup.7 are H, alkyl, or alkoxy,X.sup.-- is a non-nucleophilic anion.Reaction resin mixtures with initiators of this type contain, in addition to a cationically polymerizable monomer and/or oligomer, 0.01 to 10% by mass of the initiator.Type: GrantFiled: June 26, 1998Date of Patent: December 19, 2000Assignee: Siemens AktiegesellschaftInventors: Lothar Schon, Wolfgang Rogler, Volker Muhrer, Manfred Fedtke, Andreas Palinsky
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Patent number: 6162576Abstract: A resin composition for stereolithography and a process for producing a three-dimensional object using the same. The resin composition comprises (1) a liquid photohardenable resin composition containing at least one of photo-polymerizable compounds and a photosensitive polymerization initiator, and (2) at least one of radiation energy absorbers in an amount of from 0.001 to 1.0% by weight based on the total amount of the liquid photohardenable resin composition (1).Type: GrantFiled: February 27, 1998Date of Patent: December 19, 2000Assignee: Teijin Seiki Co., Ltd.Inventors: Tsuneo Hagiwara, Yorikazu Tamura
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Patent number: 6140384Abstract: A photopolymerizable composition 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 A.sup.1 and A.sup.2 each represents a carbon atom or a hetero atom, Q.sup.1 represents a nonmetallic atom group necessary for forming a heterocyclic ring together with A.sup.1, A.sup.2 and the carbon atoms adjacent thereto, R.sup.1 and R.sup.2 each represents a hydrogen atom, an alkyl group or an aryl group and R.sup.1 and R.sup.2 may be combined with each other to form a ring, X.sup.1 and X.sup.2 each represents a cyano group or a substituted carbonyl group and X.sup.2 and X.sup.2 may be combined with each other to form a ring, and n represents 0, 1 or 2.Type: GrantFiled: October 1, 1997Date of Patent: October 31, 2000Assignee: Fuji Photo Film Co., Ltd.Inventors: Tadahiro Sorori, Yasuo Okamoto
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Patent number: 6120973Abstract: A radiation sensitive composition comprising (A) a colorant such as carbon black and an organic pigment, (B) an alkali-soluble resin comprising a copolymer of an N-substituted maleimide monomer and other copolymerizable monomer,(C) a polyfunctional monomer, and (D) a photopolymerization initiator.Type: GrantFiled: April 22, 1998Date of Patent: September 19, 2000Assignee: JSR CorporationInventors: Kouji Itano, Shigeru Abe, Yasumi Itano
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Patent number: 6114092Abstract: A photosensitive resin composition for photoresist which is highly sensitive and can directly form an image using a laser is disclosed. Said composition comprises (A) an unsaturated resin having carboxyl group(s) which is obtained by firstly reacting 0.8 to 1.3 moles of an ethylenic unsaturated monocarboxylic acid with 1 mole of an epoxy group of a homopolymer or copolymer of ethylenic unsaturated monomer having an epoxy group to obtain an unsaturated resin which is then reacted with a dibasic acid anhydride, (B) ethylenic unsaturated compound without epoxy group, and (C) photopolymerization initiator.Type: GrantFiled: September 29, 1998Date of Patent: September 5, 2000Assignee: Kansai Paint Co., Ltd.Inventors: Kenji Miyagawa, Kenji Seko
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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: 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: 6060216Abstract: A photosensitive resin composition comprising (A) a binder polymer having carboxyl groups, (B) a photopolymerizable compound having at least one polymerizable ethylenically unsaturated group in the molecule, and (C) a photoinitiator can provide a film excellent in mechanical strength, chemical resistance, flexibility, and suitable for producing a photosensitive element.Type: GrantFiled: January 13, 1998Date of Patent: May 9, 2000Assignee: Hitachi Chemical Co., Ltd.Inventors: Tatsuya Ichikawa, Tatsuo Chiba
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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: 6046250Abstract: A process for the addition of compounds containing silicon-bonded hydrogen to compounds containing aliphatic unsaturation and compositions suitable for said process. The process is activated by actinic radiation and is conducted in the presence of a platinum complex having one diolefin group that is eta-bonded to the platinum atom and two aryl groups that are sigma-bonded to the platinum atom and a free-radical photoinitiator that is capable of absorbing actinic radiation such that the hydrosilation reaction is initiated upon exposure to actinic radiation. The invention also provides compositions for use in the aforementioned process.Type: GrantFiled: December 13, 1990Date of Patent: April 4, 2000Assignee: 3M Innovative Properties CompanyInventors: Larry D. Boardman, Joel D. Oxman
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Patent number: 6025408Abstract: Novel thioxanthone derivatives and mixtures thereof and methods of making and using the same are disclosed. The novel thioxanthone derivatives can be liquid at room temperature and display highly active photoinitiation and photopolymerization properties.Type: GrantFiled: March 27, 1997Date of Patent: February 15, 2000Assignee: First Chemical CorporationInventors: Eric Lee Williams, Ruicheng Ran, Charles Uriah Pittman, Jr., Joseph Stanton Bowers, Jr., August John Muller
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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: 6007965Abstract: The present invention relates to photopolymerizable compositions comprising an addition-polymerizable compound which has at least one ethylenically unsaturated double bond; a radical-producing agent and a squarylium compound represented by the formula (I): The compositions are highly sensitive to visible and near infrared lights, particularly He-Ne laser, LED, diode laser, etc. having oscillation wavelengths in a wavelength region of 600 nm or more, and thus are useful as materials for holograms, presensitized plate for laser direct process, dry film resists, digital proofs, photosensitive microcapsules.Type: GrantFiled: October 7, 1997Date of Patent: December 28, 1999Inventors: Tsuguo Yamaoka, Kenichi Koseki, Mitsuharu Obara, Ikuo Shimizu, Yukiyoshi Ito, Hitoshi Kawato
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Patent number: 5972562Abstract: A visible radiation-curable solder resist composition which comprises a resin component, a component for promoting photo-polymerization or -crosslinking, and optionally a diluent and any other additives, the resion componebt comprising a novolak resin skeleton and a polyfunctional acrylic monomer and the component for promoting photo-polymerization or -crosslinking comprising a photo-reaction initiator, a sensitizing dye and a heterocyclic compound having at least two endocyclic nitrogen atoms.Type: GrantFiled: March 18, 1997Date of Patent: October 26, 1999Assignee: Fujitsu LimitedInventors: Motoaki Tani, Hiroyuki Machida, Nobuyuki Hayashi
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Patent number: 5965324Abstract: A light sensitive composition and a manufacturing method of a planographic printing plate employing the same are disclosed, the composition comprising a radical generating agent and a dye represented by the following formula (1), (2) or (3): ##STR1##Type: GrantFiled: July 18, 1997Date of Patent: October 12, 1999Assignee: Konica CorporationInventors: Kimihiko Okubo, Noritaka Nakayama
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Patent number: 5962189Abstract: A photosensitive composition can be used to prepare negative-working photosensitive elements such as lithographic printing plates. The composition includes a first photocrosslinkable aromatic resin having photocrosslinkable groups and a number average molecular weight of at least about 1500. Also included is a polymerizable monomer, a photocrosslinkable polyester, a photoinitiator, and an aromatic thiazoline photosensitizer. The photosensitive resins are present at a total weight ratio to the monomer of at least 1.5:1.Type: GrantFiled: December 19, 1996Date of Patent: October 5, 1999Assignee: Kodak Polychrome Graphics LLCInventor: Thap DoMinh
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Patent number: 5942554Abstract: A method for the formation of a colored polymeric body which comprises subjecting a curable composition containing a color precursor and an onium salt to heat or actinic radiation to cure the composition, wherein the color precursor is converted to its colored form, and a curable composition capable of forming a colored polymeric body, are disclosed.Type: GrantFiled: February 20, 1996Date of Patent: August 24, 1999Assignee: Spectra Group Limited, Inc.Inventors: Yuijin Ren, Wolter Jager, Douglas C. Neckers
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Patent number: 5942371Abstract: Photopolymerisable compositions are described which comprisea) 20 to 80% by weight of a specific film-forming, acid group-containing acrylate of higher molecular weight which is neutralised with ammonia or an amine or an inorganic base, at least 10% by weight of component a) consisting of a acrylate of higher molecular weight which is derived from a reaction product of a polymolecular epoxy resin that is advanced with a bisphenol and an ethylenically unsaturated monocarboxylic acid and after subsequent reaction with a cyclic anhydride of an organic polycarboxylic acid,b) 0.1 to 15% by weight of a photoinitiator,c) 1 to 25% by weight of optional components, andd) water, as well ase) at least one additional optional (meth)acrylate monomer or (meth)acrylate oligomer or a vinyl compound that can be crosslinked with light.The compositions contain no additional polymolecular polymer binders and which can be used as aqueous applicable photoresist compositions, preferably for coating printed circuit boards.Type: GrantFiled: September 13, 1996Date of Patent: August 24, 1999Assignee: Ciba Specialty Chemicals Corp.Inventors: Roger Pierre-Elie Salvin, Martin Roth
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Patent number: 5879837Abstract: A styrylcoumarin compound jointing a styryl group by--(C.dbd.C)n--portion and having --NR.sub.1 R.sub.2 group, wherein n is an integer of 2 to 4, and each R is a proton or an alkyl group having 1 to 10 carbon atoms. A photopolymerizable composition comprises the styrylcoumarin compound as a photosensitizer, a polymerization initiator and a polymerizable compound. A photocrosslinking composition comprises the styrylcoumarin compound as a photosensitizer, a crosslinking agent and a polymerizable compound. A volume phase hologram recording medium which comprises the styrylcoumarin compound, a crosslinking agent and a polymer comprising a carbazole.Type: GrantFiled: October 30, 1997Date of Patent: March 9, 1999Assignee: Canon Kabushiki KaishaInventors: Yoko Yoshinaga, Susumu Matsumura, Naosato Taniguchi, Shin Kobayashi, Toshiyuki Sudo, Hideki Morishima, Tadashi Kaneko
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Patent number: 5849459Abstract: A resin composition for stereolithography and a process for producing a three-dimensional object using the same. The resin composition comprises (1) a liquid photohardenable resin composition containing at least one of photo-polymerizable compounds and a photosensitive polymerization initiator, and (2) at least one of radiation energy absorbers in an amount of from 0.001 to 1.0% by weight based on the total amount of the liquid photohardenable resin composition (1).Type: GrantFiled: November 28, 1995Date of Patent: December 15, 1998Assignee: Teijin Seiki Co., Ltd.Inventors: Tsuneo Hagiwara, Yorikazu Tamura
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Patent number: 5824715Abstract: A marking composition comprising an energy ray curing resin, a leuco dye and a color developer both of which are low in solubility in toluene, which composition is capable of forming a vivid black color on irradiation with laser beams, and a laser marking method for forming a clear-cut black-colored mark by using the above composition.Type: GrantFiled: February 6, 1996Date of Patent: October 20, 1998Assignee: Nippon Kayaku Kabushiki KaishaInventors: Shoiti Hayashihara, Masaru Kudo, Masaki Shinmoto
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Patent number: 5817376Abstract: Compositions containing conductivity enhancers, which are capable of being coated onto a substrate by means of electrostatic assistance. The compositions comprise one or more free-radically curable monomer(s), and one or more non-volatile conductivity enhancer(s), having cationic and anionic portions, which are soluble in the monomer(s) and which do not interfere with free-radical polymerization, wherein said anionic portion is a non-coordinating organophilic carbon-containing anion. The compositions may further comprise one or more initiator(s), one or more dissociation enhancing agent(s), cross-linking agent(s), cationically polymerizable monomer(s), cationic initiator(s), leveling agents, oligomer(s) or polymer(s), preferably co-reactive, and other additives or adjuvants to impart specific properties to the cured coating.Type: GrantFiled: March 26, 1996Date of Patent: October 6, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Albert I. Everaerts, William M. Lamanna, Albert E. Seaver, George V. Tiers
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Patent number: 5811199Abstract: A method of generating reactive species which includes exposing a photoreactor composition to radiation, in which the photoreactor composition comprises a wavelength-specific sensitizer associated with a reactive species-generating photoinitiator. Also described are methods of polymerizing unsaturated monomers and curing an unsaturated oligomer/monomer mixture.Type: GrantFiled: June 5, 1995Date of Patent: September 22, 1998Assignee: Kimberly-Clark Worldwide, Inc.Inventors: John Gavin MacDonald, Ronald Sinclair Nohr
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Patent number: 5811218Abstract: An N-aryl-.alpha.-amino acid (I), which is a novel compound, is effective as a photoinitiator. The photoinitiator composition including this photoinitiator is effective for improving photosensitive properties of photosensitive materials containing poly(amic acid) and an addition polymerizable compound used for pattern formation. Further, a photoinitiator composition (A) comprising an N-aryl-.alpha.-amino acid (I) or (I'), a 3-substituted coumarin (II) and/or an azabenzalcyclohexanone (III), or a photoinitiator composition (B) comprising an N-aryl-.alpha.-amino acid (I) or (I'), a 3-substituted coumarin (II) and a titanocene (IV), or a photoinitiator composition (C) comprising a 3-substituted coumarin (II), a titanocene (IV) and an oxime ester (V), is effective for improving photosensitive properties of photosensitive materials containing poly(amic acid) and an addition polymerizable compound used for pattern formation.Type: GrantFiled: July 17, 1995Date of Patent: September 22, 1998Assignee: Hitachi Chemical Company, Ltd.Inventors: Makoto Kaji, Yasunori Kojima, Shigeki Katogi, Masataka Nunomura, Hideo Hagiwara, Dai Kawasaki, Mitsumasa Kojima, Hiroshi Suzuki, Hidetaka Satou
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Patent number: 5804680Abstract: A flame-resistant, UV-curable single-component reactive resin system comprises a phosphorus-containing acrylate, another unsaturated compound which can undergo free radical copolymerization with acrylates and a free radical initiator system.Type: GrantFiled: March 5, 1997Date of Patent: September 8, 1998Assignee: Siemens AktiengesellschaftInventors: Winfried Plundrich, Ernst Wipfelder
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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: 5798015Abstract: A method of generating reactive species which includes exposing a photoreactor composition to radiation, in which the photoreactor composition comprises a wavelength-specific sensitizer associated with a reactive species-generating photoinitiator. Also described are methods of polymerizing unsaturated monomers and curing an unsaturated oligomer/monomer mixture.Type: GrantFiled: June 5, 1995Date of Patent: August 25, 1998Assignee: Kimberly-Clark Worldwide, Inc.Inventors: Ronald Sinclair Nohr, John Gavin MacDonald
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Patent number: 5792589Abstract: A radiation sensitive composition containing a fluorescent substance dispersed therein, comprising (A) the fluorescent substance, (B) an organic polymer binder, (C) at least one optically crosslinkable compound selected from optically crosslinkable monomers and oligomers, and (D) an optically radical-generating agent which comprises (a) a 2,4,5-triaryl imidazole dimer, (b) an amino group-containing benzophenone photosensitizer, and (c) a thiol compound represented by the following formula (1): ##STR1## wherein Z is --O--, --S--, --NH-- or --CONH--. This radiation sensitive composition can provide a fluorescent screen having a larger film thickness and a higher display brightness and hence, will greatly contribute to increases in the size and precision of a fluorescent display device such as a plasma display panel.Type: GrantFiled: February 4, 1997Date of Patent: August 11, 1998Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Tadahiko Udagawa, Hideaki Masuko, Hiroaki Nemoto, Nobuo Bessho
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Patent number: 5789459Abstract: A surface-coated vessel or a surface-coated product having a hard coating layer is obtained, by coating a substrate of, for example, resin product with a resin composition for hard coating which comprises(a) a poly?(meth)acryloyloxyalkyl! (iso)cyanurate represented by the following general formula (1) or (2): ##STR1## wherein X.sup.1, X.sup.2 and X.sup.3 are each an acryloyl group, methacryloyl group, hydrogen atom or an alkyl group, with a proviso that at least two of them are (meth)acryloyl groups, and R.sup.1, R.sup.2 and R.sup.3 are each an oxyalkylene group or a polyoxyalkylene group;(b) a poly(meth)acrylated polyoxyalkane polyol;(c) a photopolymerization initiator consisting of 2-methyl-1-?4-(methylthio)phenyl!-2-morpholino-1-propanone;(d) a photopolymerization initiator based on thioxanthone;(e) a UV-absorber based on monohydroxybenzophenone;(f) an organic solvent.Type: GrantFiled: August 22, 1997Date of Patent: August 4, 1998Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Hajime Inagaki, Koji Yoshii
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Patent number: 5770345Abstract: The sensitivity of a photoresist to actinic light is improved by the addition of certain dyes. The photoresist includes a polymer matrix, a photosensitive acid generator and at least one compound selected from the group consisting of dyes containing at least one heterosulphur atom such as 2,2.sup.1,5.sup.1,2"-terthiophene and its derivatives; thianthrene and its derivatives, and 4,6-diphenylthieno(3,4-d)-1,3-dioxol-2-one-5,5-dioxide; phenylsulfone and its derivatives; and 4,5-diphenyl-1,3-dioxol-2-one; 3,4-bis(acetoxymethyl)furan; chelidonic acid and its derivatives; and 5,7,12,14-pentacenetetrone. Resist images on a substrate are formed from the compositions.Type: GrantFiled: July 16, 1996Date of Patent: June 23, 1998Assignee: International Business Machines CorporationInventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
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Patent number: 5756258Abstract: The present invention relates to photopolymerizable compositions comprising an addition-polymerizable compound which has at least one ethylenically unsaturated double bond; a radical-producing agent and a squarylium compound represented by the formula (I): ##STR1## The compositions are highly sensitive to visible and near infrared lights, particularly He-Ne laser, LED, diode laser, etc. having oscillation wavelengths in a wavelength region of 600 nm or more, and thus are useful as materials for holograms, presentized plates for laser direct process, dry film resists, digital proofs, photosensitive microcapsules.Type: GrantFiled: February 10, 1995Date of Patent: May 26, 1998Assignee: Kyowa Hakko Co., Ltd.Inventors: Tsuguo Yamaoka, Kenichi Koseki, Mitsuharu Obara, Ikuo Shimizu, Yukiyoshi Ito, Hitoshi Kawato
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Patent number: 5753412Abstract: The sensitivity of a photoresist to actinic light is improved by the addition of certain dyes. The photoresist includes a polymer matrix, a photosensitive acid generator and at least one compound selected from the group consisting of dyes containing at least one heterosulphur atom such as 2,2.sup.1,5.sup.1,2"-terthiophene and its derivatives; thianthrene and its derivatives, and 4,6-diphenylthieno(3,4-d)-1,3-dioxol-2-one-5,5-dioxide; phenylsulfone and its derivatives; and 4,5-diphenyl-l,3-dioxol-2-one; 3,4-bis(acetoxymethyl)furan; chelidonic acid and its derivatives; and 5,7,12,14-pentacenetetrone. Resist images on a substrate are formed from the compositions.Type: GrantFiled: June 5, 1996Date of Patent: May 19, 1998Assignee: International Business Machines CorporationInventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
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Patent number: RE37962Abstract: 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): wherein the all symbols are defined in the disclosure, and a titanocene compound.Type: GrantFiled: July 21, 2000Date of Patent: January 7, 2003Assignee: Fuji Photo Film Co., Ltd.Inventors: Syunichi Kondo, Kazuo Fujita