Specified Rate-affecting Material Contains Sulfur Patents (Class 522/27)
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Patent number: 7341828Abstract: A photopolymerization initiator composition containing a thiol compound having a mercapto group-containing group that has at least one substituent on the carbon atoms on carbon atom(s) at the ?- and/or ?-position with respect to the mercapto group and a photopolymerization initiator; a photosensitive composition containing the composition; and a novel thiol compound for use in these compositions. The photosensitive composition containing the photopolymerizazion initiator composition of the present invention has high sensitivity and excellent storage stability and enables reduction in cost due by increasing productivity.Type: GrantFiled: February 27, 2003Date of Patent: March 11, 2008Assignee: Showa Denko K.K.Inventors: Tsuyoshi Katoh, Hirotoshi Kamata, Mina Onishi
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Patent number: 7329692Abstract: Compositions are provided that that can be used as an initiator system for free radical polymerization reactions. More specifically, the initiator systems include an electron acceptor and an electron donor. The electron donors are arylsulfinate salts having a cation that contains at least one carbon atom and either a positively charged nitrogen atom or a positively charged phosphorus atom. Methods of polymerization are also provided that can be used to prepare polymeric material with the initiator systems. The initiator systems can be thermal initiator systems, photoinitiator systems, or combinations thereof.Type: GrantFiled: January 31, 2006Date of Patent: February 12, 2008Assignee: 3M Innovative Properties CompanyInventors: Rajdeep S. Kalgutkar, Michael C. Palazzotto
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Patent number: 7294723Abstract: Compounds of formula (I): [where: R1 is a direct bond, oxygen, a group >CH2, sulphur, a group >C?O, a group-(CH2)2— or a group-N—Ra, where Ra is hydrogen or alkyl; R3, R4, R5 and R6 are hydrogen or substituents?; R8, R9, R10 and R11 are hydrogen, hydroxy or alkyl; or R9 and R11 are joined to form a fused ring system with the benzene rings to which they are attached; R7 is a direct bond, oxygen or a —CH2-group; p is 0 or 1 ; substituents? are: alkyl, alkoxy, alkenyl, halogen, nitrile, hydroxyl, aryl, aralkyl, aryloxy, aralkyloxy, arylalkenyl, cycloalkyl, carboxy, carboxyalkoxy, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, alkanesulphonyl, arenesulphonyl, alkanoyl or arylcarbonyl; n is 1 to 12; R12 is hydrogen, methyl or ethyl; A is a group —[O(CHR13CHR14)a]y—, —[O(CH2)bCO]y-, or —[O(CH2)bCO](y-1)-[O(CHR13CHR14)a]—, where: one of R13 and R14 is hydrogen and the other is hydrogen, methyl or ethyl; a is 1 to 2 ; b is 4 to 5 ; Q is a residue of a polyhydroxy compound having from 2 to 6 hydroxy groups;Type: GrantFiled: December 10, 2003Date of Patent: November 13, 2007Assignee: Sun Chemical CorporationInventors: Shaun Lawrence Herlihy, Brian Rowatt, Robert Stephen Davidson
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Patent number: 7247660Abstract: The invention concerns dental compositions. Said composition comprises (1) a silicone crosslinkable and/or polymerizable by cation process; (2) an efficient amount of at least an initiator such as onium borate; (3) at least a photosensitizer ; and (4) a dental filler present in the composition in a proportion of at least 10 wt. % relative to the composition total weight. Said dental compositions are useful for making dental prostheses or for dental restoration.Type: GrantFiled: February 18, 2004Date of Patent: July 24, 2007Assignee: Rhodia ChimieInventor: Jean-Marc Frances
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Patent number: 7232850Abstract: A photocurable composition comprising cationically curable compound, an acrylate-containing compound; a hydroxyl-containing compound; a cationic photoinitiator; and a free radical photoinitiator; wherein said composition has less than 0.54 equivalents of cationically curable groups, less than 0.10 equivalents of acrylate groups and less than 0.10 equivalents of hydroxyl groups per 100 grams of said composition.Type: GrantFiled: October 3, 2003Date of Patent: June 19, 2007Assignee: Huntsman Advanced Materials Americas Inc.Inventors: David Johnson, Frank Tran, John Fong, Richard Leyden, Ranjana Patel
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Patent number: 6864040Abstract: The present invention relates to IR-sensitive compositions containing an initator system comprising: (a) at least one compound capable of absorbing IR radiation selected from triarylamine dyes, thiazolium dyes, indolium dyes, oxazolium dyes, cyanine dyes, polyaniline dyes, polypyrrole dyes, polythiophene dyes and phthalocyanine pigments (b) at least one compound capable of producing radicals selected from polyhaloalkyl-substituted compounds (c) at least one polycarboxylic acid represented by the following formula I wherein Y is selected from the group consisting of O, S and NR7, each of R4, R5 and R6 is independently selected from the group consisting of hydrogen, C1-C4 alkyl, aryl which is optionally substituted, —COOH and NR8CH2COOH, R7 is selected from the group consisting of hydrogen, C1-C6 alkyl, —CH2CH2OH, and C1-C5 alkyl substituted with -COOH, R8 is selected from the group consisting of —CH2COOH, —CH2OH and —(CH2)2N(CH2COOH)2 and r is 0, 1, 2 or 3 with the proviso that at least one of R4, R5, RType: GrantFiled: April 11, 2001Date of Patent: March 8, 2005Assignee: Kodak Polychrome Graphics LLCInventors: Ursula Müller, Tobias Wittig, Hans-Joachim Timpe
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Patent number: 6844373Abstract: A radiation-curable composition having a reduced surface energy and including a reactive dye containing at least one radiation-curable substituent and at least one fluorine-containing substituent. The reactive dye may include any anthraquinone, methine, azo, azine, or xanthene dye adapted to contain at least one radiation-curable substituent and at least one fluorine-containing substituent. The radiation-curable substituent may include (meth)acrylate, styrene, vinyl ether, vinyl ester, N-substituted acrylamide, N-vinyl amide, maleate ester, and fumarate ester.Type: GrantFiled: May 28, 2002Date of Patent: January 18, 2005Assignee: AlcatelInventor: Michael B. Purvis
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Patent number: 6750266Abstract: A multiphoton-activatable, photoreactive composition comprises: (a) at least one reactive species that is capable of undergoing an acid- or radical-initiated chemical reaction; (b) a photochemically-effective amount of a multiphoton photosensitizer comprising at least one multiphoton up-converting inorganic phosphor; and (c) a photochemically-effective amount of a one-photon photoinitiator system that is capable of being photosensitized by the multiphoton photosensitizer.Type: GrantFiled: December 28, 2001Date of Patent: June 15, 2004Assignee: 3M Innovative Properties CompanyInventors: James G. Bentsen, Robert J. DeVoe, Michael C. Palazzotto
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Patent number: 6747071Abstract: The invention concerns dental compositions. Said composition comprises (1) a silicon crosslinkable and/or polymerizable by cation process; (2) an efficient amount of at least an initiator such as onium borate; (3) at least a photosensitizer; and (4) a dental filler present in the composition in a proportion of at least 10 wt. % relative to the composition total weight. Said dental compositions are useful for making dental prostheses or for dental restoration.Type: GrantFiled: June 25, 2001Date of Patent: June 8, 2004Assignee: Rhodia ChimieInventor: Jean-Marc Frances
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Patent number: 6726795Abstract: A radiation-curable composition which includes a cyanoacrylate component or a cyanoacrylate-containing formulation; a metallocene component; and a polymerizingly effective amount of a photoinitiator to accelerate the rate of cure is provided.Type: GrantFiled: February 20, 2002Date of Patent: April 27, 2004Inventors: Stan Wojciak, Shabbir Attarwala
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Patent number: 6673457Abstract: The invention discloses a novel radiation-curable silicone-based release coating composition capable of giving a cured release coating film on a substrate such as a plastic resin film exhibiting excellent adhesion to a variety of substrate materials and excellent releasability. The radiation-curable releasing silicone composition of the invention comprises (A) an aromatic compound having, in a molecule, at least two cationically polymerizable organopolysiloxanyl groups such as epoxy-substituted organopolysiloxanyl groups as the silicone ingredient and (B) a photopolymerization initiator which is an onium salt compound such as diaryliodonium salt compounds.Type: GrantFiled: December 12, 2001Date of Patent: January 6, 2004Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masatoshi Takahashi, Masahiko Ogawa
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Patent number: 6653399Abstract: A water absorbent material, comprising, as a main component, a water absorbent resin which has a structure in which a anhydropolyamino acid having an ethylenically unsaturated double bond is grafted with polysaccharides, wherein at least a portion of the anhydropolyamino acid is hydrolyzed and crosslinked, has high water absorbency and high biodegradability even if the anhydropolyamino acid has a low molecular weight.Type: GrantFiled: February 26, 2002Date of Patent: November 25, 2003Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Hisakazu Tanaka, Shigeki Ideguchi, Yoshiki Hasegawa
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Patent number: 6635195Abstract: A process for polymerizing/curing a photopolymerizable monomer composition comprising at least one diepisulfide monomer which comprises the steps of: a) mixing to the monomer composition an effective amount of a cationic photopolymerization initiator, and b) irradiating the mixture of a) with an ultraviolet radiation to at least partially cationically photopolymerize the monomer composition.Type: GrantFiled: February 4, 2000Date of Patent: October 21, 2003Assignee: Essilor International Compagnie Generale d'OptiqueInventors: Sirisoma Wanigatunga, Yassin Turshani
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Publication number: 20030118939Abstract: The present invention provides an IR-sensitive composition, which includes: a polymeric binder; and a free radical polymerizable system consisting of: at least one component selected from unsaturated free radical polymerizable monomers, oligomers which are free radical polymerizable and polymers containing C═C bonds in the backbone and/or in the side chain groups; and an initiator system, which includes: (a) at least one compound capable of absorbing IR radiation; (b) at least one compound capable of producing radicals; and (c) at least one carboxylic co-initiator, provided that the total acid number of the polymeric binder is 70 mg KOH/g or less. The present invention further provides a printing plate precursor, a process for preparing the printing plate and a method of producing an image.Type: ApplicationFiled: November 9, 2001Publication date: June 26, 2003Applicant: KODAK POLYCHROME GRAPHICS, L.L.C.Inventors: Heidi Munnelly, Paul West
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Patent number: 6569603Abstract: There are disclosed a light-sensitive composition which comprises (A) a polymer having a phenyl group substituted by a vinyl group at a side chain, (B) a photopolymerization initiator and (C) a sensitizer which sensitizes the photo-polymerization initiator, or a light-sensitive composition which comprises (A′) a polymer, the above-mentioned (B) and (C), and (D) a monomer having at least two phenyl groups each of which is substituted by a vinyl group in the molecule of the monomer; and a method of forming a relief image which comprises coating the light-sensitive composition as mentioned above on a support, exposing the composition by exposure or scanning exposure and developing the same to form a relief image on the support.Type: GrantFiled: January 30, 2001Date of Patent: May 27, 2003Assignee: Mitsubishi Paper Mills LimitedInventor: Akira Furukawa
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Patent number: 6515038Abstract: A polymer used in a chemically amplified resist is represented by the following formula: wherein R1, R3 and R5 are each independently selected from the group consisting of —H, and —CH3; R2 is selected from the group consisting of t-butyl, tetrahydropyranyl, and 1-alkoxyethyl; R4 is selected from the group consisting of —H, —CH3, t-butyl, tetrahydropyranyl, and 1-alkoxyethyl; x is an integer ranging from 1 to 4; and wherein l, m, and n are selected such that l/(l+m+n) ranges from 0.1 to 0.5, m/(l+m+n) ranges from 0.01 to 0.5, and (l+m)/(l+m+n) ranges from 0.1 to 0.7.Type: GrantFiled: July 26, 2001Date of Patent: February 4, 2003Assignee: Samsung Electronics Co., Ltd.Inventor: Sang-jun Choi
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Patent number: 6512020Abstract: Compounds of formula I, II and III, wherein wherein R1 is for example hydrogen, C1-C12alkyl, C3-C30cycloalkyl, C2-C12alkenyl, C4-C8cycloalkenyl, phenyl, which is unsubstituted or substituted, naphthyl, anthracyl or phenanthryl, unsubstituted or substituted, heteroaryl radical which is unsubstituted or substituted; wherein all radicals R1 with the exception of hydrogen can additionally be substituted by a group having a —O—C-bond or a —O—Si-bond which cleaves upon the action of an acid; R′1 is for example phenylene, naphthylene, diphenylene or oxydiphenylene, wherein these radicals are unsubstituted or substituted; R2 is halogen or C1-C10haloalkyl; R3 is for example C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, wherein the groups are unsubstituted or substituted, or R3 is e.g.Type: GrantFiled: March 28, 2001Date of Patent: January 28, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Toshikage Asakura, Hitoshi Yamato, Masaki Ohwa, Jean-Luc Birbaum, Kurt Dietliker, Junichi Tanabe
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Patent number: 6511789Abstract: Reducing inhibition of the photochemical crosslinking by including in the photosensitive polyimide precursor composition a metal inhibitor selected from 1H-tetrazole, 1,2-cyclohexenediamine tetraacetic acid hydrate and 5-mercaptobenzimidazole.Type: GrantFiled: June 20, 2001Date of Patent: January 28, 2003Assignee: Arch Specialty Chemicals, Inc.Inventors: Ahmad Naiini, Donald Racicot, Andrew J. Roza, William D. Weber, Pamela J. Waterson
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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: 6482868Abstract: 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: June 26, 2000Date of Patent: November 19, 2002Assignee: 3M Innovative Properties CompanyInventors: Wayne Scott Mahoney, Peggy Sperl Willett
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Patent number: 6426373Abstract: Among other things, a photopolymerizing one-component dental material is prepared, containing: 1) 80-10 weight-% of at least one polyfunctional urethane methacrylate and/or at least one polyfunctional urethane acrylate, 2) 10-30 weight-% of at least one polyfunctional acrylate resin, 3) 10-30 weight-% of at least one reactive thinner, 4) 0-20 weight-% of bis-GMA and/or at least one ethoxylated bisphenol-A-dimethacrylate, 5) 0-10 weight-% of at least one filler, 6) 0-1 weight-% of at least one photoinitiator, and. 7) 0-1 weight-% of at least one color pigment.Type: GrantFiled: August 12, 1999Date of Patent: July 30, 2002Assignee: Heraeus Kulzer GmbH & Co. KGInventors: Frank Stange, Albert Erdrich, Novica Savic, Teresa Puchalska
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Patent number: 6423378Abstract: The invention concerns the use of cross-linkable silicone compositions for fast, economical and simple impregnation and/or varnishing of flat joints (e.g. cylinder head gaskets). More precisely it concerns the use of silicone compositions cross-linkable under UV radiation, by cationic process and in the presence of specific phoinitiators selected among onium borates or organometallic complexes, of which the borate counter-anions contain at least a boron bound to at least a substituted phenyl (Me, F). The silicone liquid precursor is a polydimethylsiloxane (PDMS) substituted by cross-linking functional groups, by cationic process (Gfp) under UV of the epoxy of vinyloxy type. These Gfp are present at the rate of 0.15 to 2.0 pr kg of PDMS. The invention also relates to the method for impregnating/varnishing flat joints (e.g. cylinder head gaskets) using the specific PDMS composition+photoinitiator of borate type as well as the treated joints and the composition themselves.Type: GrantFiled: August 30, 1999Date of Patent: July 23, 2002Assignee: Rhodia ChimieInventors: Marie-Christine Cotting, Gérard Joubert, Olivier Loubet
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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: 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: 6211262Abstract: A corrosion resistant coating for metal surfaces curable with actinic radiation. The blend uses acrylate resin, photoinitiator and a corrosion preventing agent such as a metal surface passivator, overbased calcium sulfonate/calcium carbonate, a barrier pigment, or a combination of two or more of these agents.Type: GrantFiled: April 20, 1999Date of Patent: April 3, 2001Assignee: Spectra Group Limited, Inc.Inventors: Alexandre Mejiritski, Thomas Marino, Violeta Lungu, Dustin Martin, Douglas Neckers
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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: 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: 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: 6087066Abstract: This invention relates to polyvinyl acetals containing the units A, B, C and D, whereinA is present in an amount of 0.5 to 20 wt.-% and is of the formula ##STR1## B is present in an amount of 15 to 35 wt.-% and is of the formula ##STR2## C is present in an amount of 10 to 50 wt.-% and is of the formula ##STR3## wherein R.sup.1 is an alkyl group with up to 4 carbons, which is optionally substituted by an acid group, or a phenyl group, to which an acid group is attached, wherein the phenyl group optionally comprises 1 to 2 further substituents selected from halos, amino, methoxy, ethoxy, methyl and ethyl groups, or is a group X--NR.sup.6 --CO--Y--COOH, wherein X is an aliphatic, aromatic or araliphatic spacer group, R.sup.6 is hydrogen or an aliphatic, aromatic or araliphatic moiety and Y is a saturated or unsaturated chain- or ring-shaped spacer group, and this unit C may be contained several times with various moieties R.sup.1 independent of one another, and D is present in an amount of 25 to 70 wt.Type: GrantFiled: October 14, 1999Date of Patent: July 11, 2000Assignee: Kodak Polychrome Graphics LLCInventors: Harald Baumann, Celin Savariar-Hauck, Hans-Joachim Timpe
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Patent number: 6071980Abstract: Exposing to visible light atom transfer radical polymerizations of vinyl monomers that use transition metal compounds often results in faster polymerizations and/or the need for less transition metal compound. Disclosed is a process for the polymerization of vinyl monomers by atom transfer radical polymerization using a first compound containing a transition metal and a second compound capable of radically transferring an atom or group to said first compound, wherein the improvement comprises, irradiating with visible light with an intensity of at least about 5 mW/cm.sup.2 a liquid in which said polymerization is taking place. The polymers made are useful for molding resins and coatings.Type: GrantFiled: August 18, 1998Date of Patent: June 6, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Zhibin Guan, Bruce Edmund Smart
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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: 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: 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: 5985950Abstract: 1,2-Disulfones are particularly suitable as thermally and photochemically activatable latent acid catalysts for binder systems which contain at least one acid-curable component.Type: GrantFiled: January 21, 1998Date of Patent: November 16, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Ekkehard Bartmann, Jorg Ohngemach
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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: 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: 5900346Abstract: The present invention relates to novel compositions that contain an activator system that comprises a photoactivator, acid generator and chain extender. Methods and articles of manufacture that comprise such compositions are also provided. In a preferred aspect, the compositions are photoimageable.Type: GrantFiled: February 28, 1997Date of Patent: May 4, 1999Assignee: Shipley Company, L.L.C.Inventors: Roger F. Sinta, Juan C. Scaiano, Gary S. Calabrese
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Patent number: 5866627Abstract: New photosensitive polyamic acid precursors are disclosed which have the formula: ##STR1## where Z is a tetravalent organic radical which contains at least one aromatic ring, Z' is a divalent organic radical which contains at least one aromatic ring, and R* is a photo polymerizable group. Particularly preferred compounds include BPDA-PDA and BPDA-ODA polyamic acid precursors. The precursor compositions within the practice of this invention are i-line, g-line, and i-/g-line active and show good photoresolution. The films formed exhibit excellent self-adhesion and adhesion to glass ceramic and silicon wafer substrates have low internal stress, a very low degree of solvent swelling, high thermal stability, and excellent mechanical properties such as high modulus/tensile strength and high elongation at break.Type: GrantFiled: June 30, 1997Date of Patent: February 2, 1999Assignee: International Business Machines CorporationInventors: George Czornyj, Moonhor Ree, Willi Volksen, Dominic Changwon Yang
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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: 5846689Abstract: A positive-working radiation-sensitive mixture essentially consists of(a) at least one polymer which contains acid-labile groups and is insoluble in water but becomes soluble in aqueous alkaline solutions as a result of the action of acid,(b) at least one organic compound which produces an acid under the action of actinic radiation and(c) at least one further organic compound differing from (b), where the polymer (a) contains incorporated units of the formulae (I), (II) and (III) ##STR1## and the organic compound (b) is a sulfonium salt of the formula (IV) ##STR2## The radiation-sensitive mixture is suitable for the production of relief structures having improved contrast.Type: GrantFiled: September 9, 1996Date of Patent: December 8, 1998Assignee: BASF AktiengesellschaftInventors: Reinhold Schwalm, Dirk Funhoff, Horst Binder
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Patent number: 5837748Abstract: A photopolymerizable composition is disclosed, comprising the following components (i), (ii) and (iii):(i) a compound having at least one addition-polymerizable, ethylenically unsaturated bond;(ii) a compound represented by formula (I): ##STR1## wherein A=represents a substituted or unsubstituted 2(3H)-thiazolylidene or 2-thiazolidinylidene group; --X-- represents --O--, --S--, --NR.sup.2 -- or --CONR.sup.3 --, in which R.sub.1, R.sup.2 and R.sup.3 each independently represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an alkenyl group, a substituted alkenyl group, an alkynyl group or a substituted alkynyl group; and=E represents a substituted or unsubstituted 1,3-dihydro-1-oxo-2H-inden-2-ylidene group; and(iii) a compound which generates an active radical upon light irradiation in the co-presence of component (ii).Type: GrantFiled: August 8, 1997Date of Patent: November 17, 1998Assignee: Fuji Photo Film Co., Ltd.Inventor: Tadahiro Sorori
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Patent number: 5773528Abstract: A photocopolymerizable composition for backsealing a ceramic carrier and process for using the composition is disclosed. The composition comprises: a liquid, multifunctional, bisphenol based epoxy; a liquid, multifunctional hydroxyl containing organic material; a complex onium salt photoinitiator; and, a complex cupric salt initiator. The composition utilizes a strong Bronstead acid for additional deep curing created by iodonium salt thermolysis.Type: GrantFiled: March 19, 1996Date of Patent: June 30, 1998Assignee: International Business Machines CorporationInventors: Julio M. Alvarado, Kathleen L. Covert, Joseph P. Kuczynski
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Patent number: 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: 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: 5747172Abstract: Silicone release agents comprising propenyl-ether functionalized silicones exhibit a rapid cationic induce photo-cure. Such propenyl-ether functionalized silicones are synthesized by the hydrosilation of various .alpha.-allyloxy-.omega.-(1-propenoxy) alkanes with various linear and cyclic hydrogen functional siloxanes.Type: GrantFiled: August 30, 1995Date of Patent: May 5, 1998Assignee: General Electric CompanyInventor: James V. Crivello
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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