Free Radical Patents (Class 430/916)
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Patent number: 6217984Abstract: An energy sensitive composition comprising a monomeric organometallic complex essentially free of nucleophilic groups and which, upon exposure to energy, bonds to basic reactive sites on a substrate via the metal center, leaving the polymerizable group of the complex unreacted and unrestricted; an energy sensitive composition at least one energy sensitive organometallic group is incorporated in or appended to the backbone of a polymer, such that the resulting coordinatively unsaturated organometallic group or groups bond to basic reactive sites on a substrate, thus forming permanent bonds, and further, the adherent compositions are useful in applications such as adhesion of polymers to substrates, protective coatings, printing plates, durable release coatings, primers, binders, and paints.Type: GrantFiled: May 21, 1992Date of Patent: April 17, 2001Assignee: 3M Innovative Properties CompanyInventors: Wesley J. Bruxvoort, Steven J. Keipert, Fred B. McCormick, Jerry W. Williams, Bradford B. Wright
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Patent number: 6183934Abstract: A negative photosensitive resin composition, which comprises a thermosetting polymer precursor which can be cured through cyclodehydration upon heating, and a photosensitive heat cure accelerator. This photosensitive heat cure accelerator may be, a compound having a protective substituent group which can be eliminated upon irradiation of light, an N-oxide compound which is capable of exhibiting a heat cure accelerating property through a transition of an oxide group thereof upon irradiation of light, or a compound which is capable of exhibiting a heat cure accelerating property through generation of an acid upon irradiation of light. Further, this photosensitive heat cure accelerator may be formed of a combination of a latent heat cure accelerator which is capable of changing into a compound exhibiting a heat cure accelerating property through a reaction with an acid and a photo-acid generating agent which is capable of generating an acid upon irradiation of light.Type: GrantFiled: July 1, 1998Date of Patent: February 6, 2001Assignee: Kabushiki Kaisha ToshibaInventor: Yoshiaki Kawamonzen
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Patent number: 6165686Abstract: Color reversion of photocured products which have been photocured with cationic dyes and quaternary organo borates can be notably suppressed by addition of phenolic compounds, aromatic thiol compounds, amine compounds and/or phosphorous compounds.Type: GrantFiled: May 21, 1998Date of Patent: December 26, 2000Assignee: Showa Denko K.K.Inventors: Hirotoshi Kamata, Toshio Koshikawa, Takeo Watanabe, Shuichi Sugita
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Patent number: 6103453Abstract: A photoinitiator blend, containinga) at least one monoacylphosphine oxide of formula I ##STR1## in which R.sup.1 denotes C.sub.1 -C.sub.18 alkyl; C.sub.1 -C.sub.4 alkyl, C.sub.5 -C.sub.8 cycloalkyl, C.sub.7 -C.sub.9 phenylalkyl, phenyl, naphthyl, biphenyl, all substituted by halogen or C.sub.1 -C.sub.6 alkoxy; phenyl, naphthyl or biphenylyl, all mono- or poly-substituted by halogen, C.sub.1 -C.sub.12 alkyl and/or C.sub.1 -C.sub.12 alkoxy; or a monovalent N--, O--, or S--containing 5-membered or 6-membered heterocyclic radical,R.sup.2 denotes phenyl, naphthyl, biphenylyl; phenyl, naphthyl or biphenylyl, all mono- or poly-substituted by halogen, C.sub.1 -C.sub.12 alkyl and/or C.sub.1 -C.sub.12 alkoxy; a monovalent N--, O--, or S--containing 5-membered or 6-membered heterocyclic radical, C.sub.1 -C.sub.18 alkoxy, phenoxy; phenoxy substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; benzyloxy, cyclohexyloxy or R.sup.2 and R.sup.1 form a ring together with the phosphorus atom,R.sup.Type: GrantFiled: March 17, 1999Date of Patent: August 15, 2000Assignee: BASF AktiengesellschaftInventors: Bernhard Prantl, Erich Beck, Matthias Lokai, Christof Kandzia
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Patent number: 6066435Abstract: A photosensitive composition which is liquid at room temperature and which comprisesa) 18 to 22% by weight of a binder polymer based on a styrene-maleic anhydride halfester copolymer,b) 10 to 15% by weight of at least one photocurable acrylate compound,c) 0.1 to 10% by weight of a photoinitiator, andd) 45 to 70% by weight of a propylene glycol halfester or propylene glycol halfester, the sum of the components a) to d) being 100% by weight,is suitable for the production of photostructured objects, preferably for the production of telephone cards.Type: GrantFiled: May 11, 1998Date of Patent: May 23, 2000Assignee: CIBA Specialty Chemicals Corp.Inventor: Kurt Munk
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Patent number: 6025112Abstract: A photocurable composition comprises an unsaturated group-containing compound as a base material, a metal arene compound as a photopolymerization initiator and an aniline compound as a photosensitizer. As the photosensitizer aniline compound, any one or both of 2,6-diisopropyl-N,N-dimethylaniline and 2,4,6,N,N-pentamethylaniline is/are used.Type: GrantFiled: February 4, 1997Date of Patent: February 15, 2000Assignee: Brother Kogyo Kabushiki KaishaInventor: Masashi Tsuda
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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: 6013415Abstract: A radiation sensitive composition comprising (A) a colorant, (B) an alkali-soluble resin, (C) a polyfunctional monomer and (D) a photopolymerization initiator. The alkali-soluble resin (B) is a copolymer of (1) a monomer represented by the following formula (1): wherein R.sup.1 is a hydrogen atom or a methyl group, and(2) an ethylenically unsaturated monomer having at least one carboxyl group in the molecule, and optionally (3) a copolymerizable ethylenically unsaturated monomer other than the above monomers (1) and (2). The radiation sensitive composition is useful for producing a color filter for transmission-type or reflection-type color liquid crystal display devices, etc.Type: GrantFiled: December 15, 1998Date of Patent: January 11, 2000Assignee: JSR CorporationInventors: Kouichi Sakurai, Takahiro Iijima, Yukiko Ito, Hiroaki Nemoto
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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: 6004724Abstract: New oximsulfonate compounds of the formulae I or II, ##STR1## wherein m is 0 or 1; x is 1 or 2; R.sub.1 is, for example phenyl, which is unsubstituted or substituted or R.sub.1 is a heteroaryl radical that is unsubstituted or substituted, or, if m is 0, R.sub.1 additionally is C.sub.2 -C.sub.6 alkoxycarbonyl, phenoxycarbonyl or CN; R'.sub.1 is for example C.sub.2 -C.sub.12 alkylene, phenylene; R.sub.2 has for example one of the meanings of R.sub.1 ; n is 1 or 2; R.sub.3 is for example C.sub.1 -C.sub.18 alkyl, R'.sub.3 when x is 1, has one of the meanings given for R.sub.3, or R'.sub.3 in the formula IV and when x is 2 in the formula 1, is for example C.sub.2 -C.sub.12 alkylene, phenylene; R.sub.4 and R.sub.5 are independently of each other for example hydrogen, halogen, C.sub.1 -C.sub.6 alkyl; R.sub.6 is for example hydrogen, phenyl; R.sub.7 and R.sub.8 are independently of each other for example hydrogen or C.sub.1 -C.sub.12 -alkyl; R.sub.9 is for example C.sub.1 -C.sub.12 alkyl; A is S, O, NR.sub.Type: GrantFiled: June 25, 1998Date of Patent: December 21, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Hitoshi Yamato, Hartmut Bleier, Jean-Luc Birbaum, Martin Kunz, Kurt Dietliker, Christoph De Leo, Toshikage Asakura
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Patent number: 5989778Abstract: A layer for protection coating and adhesion of DVD is formed by a photo-curing resin composition which comprises a photo-curing component which is cured by polymerization reaction of a unsaturated group, a photo-polymerization initiator and a phenol-based primary antioxidant, wherein this photo-curing component comprises a bi-functional urethane acrylate, an epoxy acrylate containing a bisphenol A skeleton, and a N-vinyl lactam compound, said polymerization initiator comprising a mono or di-benzoylphosphine oxide compound in an amount of 0.1% by weight or more to less than 5.0% by weight based on the total amount of said photo-curing components, and the viscosity of this resin composition at 25.degree. C. being in the range from 350 to 700 mPa.multidot.s.Type: GrantFiled: June 30, 1998Date of Patent: November 23, 1999Assignee: Sumitomo Chemical Company, LimitedInventor: Shigeo Hozumi
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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: 5952152Abstract: Compounds of the formula I or I' ##STR1## in which R.sub.1 and R.sub.2 independently of one another, for example, are an aromatic hydrocarbon, with the proviso that the aromatic hydrocarbon radical is substituted in at least one o-position, or R.sub.1 and R.sub.2, for example, independently of one another are C.sub.1 -C.sub.20 alkyl, which is substituted by R.sub.9 R.sub.10 R.sub.11 Si; R.sub.2a is, for example, a divalent aromatic hydrocarbon radical; R.sub.3 is C.sub.1 -C.sub.20 alkyl which is substituted by R.sub.9 R.sub.10 R.sub.11 Si or is an aromatic hydrocarbon; R.sub.4 is, for example, C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.12 cycloalkyl or phenyl-C.sub.1 -C.sub.6 alkyl; E is R.sub.14 R.sub.15 R.sub.16 P or R.sub.8 R.sub.8a R.sub.7 N; R.sub.7, R.sub.8 and R.sub.8a and R.sub.9, R.sub.10 and R.sub.11 independently of one another are, for example, C.sub.1 -C.sub.12 alkyl; R.sub.14, R.sub.15 and R.sub.Type: GrantFiled: November 21, 1996Date of Patent: September 14, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
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Patent number: 5939238Abstract: The invention provides a negative-acting photoimageable composition comprising A) between about 30 and about 80 wt % based on total weight of A) plus B) of a binder polymer having acid functionality sufficient to render said photoimageable composition developable in alkaline aqueous solution, B) between about 20 and about 70 wt % based on total weight of A) plus B) of an addition-polymerizeable, non-gaseous .alpha.,.beta.-ethylenically unsaturated compound(s) capable of forming a high polymer by free-radical initiated chain-propagating addition polymerization, at least about 50 mole percent of the .alpha.,.beta.-ethylenically unsaturated moieties of B) being methacrylic moieties, and C) between about 0.1 and about 20 wt % based on total weight of A) plus B) of a photoinitiator chemical system, the photoinitiator chemical system comprising between about 0.005 and about 3 wt % relative to total weight of A) plus B) of triphenyphosphine and between about 0.Type: GrantFiled: June 2, 1998Date of Patent: August 17, 1999Assignee: Morton International, Inc.Inventors: Robert Barr, Daniel E. Lundy, Eiji Kosaka, Shigeru Murakami
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Patent number: 5922509Abstract: A negative-acting photoimageable composition useful as a photoresist comprises an acid-functional binder polymer, a photopolymerizable component, and a photoinitiator chemical system, in which the binder polymer has a multi-modal molecular weight distribution used to promote faster photoresist stripping times and a smaller stripped particle size. The combination of faster stripping times and smaller stripped particle size allows for fully aqueous, environmentally friendly, stripping of the photoresist from overplated circuit boards.Type: GrantFiled: March 18, 1998Date of Patent: July 13, 1999Assignee: Morton International, Inc.Inventors: Randall W. Kautz, Robert K. Barr
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Patent number: 5876899Abstract: A method for making an acrylic resin photoresist characterized by polymerization of an acrylic monomer in a solvent that dissolves all monomers and resultant polymers. The use of the solvent permits formation of acrylic resins suitable for use in the preparation of photoresists without recovery from its reaction mixture. Photoresists prepared from such polymers have improved transparency, especially at exposures of 193 mn or less.Type: GrantFiled: September 18, 1996Date of Patent: March 2, 1999Assignee: Shipley Company, L.L.C.Inventors: Charles R. Szmanda, Gary N. Taylor, Robert L. Brainard, Manuel DoCanto
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Patent number: 5866298Abstract: A radiation sensitive composition for color filters comprising (A) a colorant, (B) a binder polymer, (C) a poly-functional monomer, (D) a photopolymerization initiator containing at least one biimidazole compound typified by 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(4-ethoxycarbonylphenyl)-biimid azole and 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and (E) a solvent. The composition can be used for the manufacture of color filters exhibiting excellent photographic sensitivity and superior contrast, while effectively controlling production of residual insoluble material during development process.Type: GrantFiled: November 21, 1996Date of Patent: February 2, 1999Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Satoshi Iwamoto, Yasumi Wanibe, Hiroaki Nemoto, Nobuo Bessho
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Patent number: 5858617Abstract: A photopolymerizable composition and a presensitized planographic printing plate employing the same are disclosed which comprise a compound having an ethylenically unsaturated bond and a dye represented by the following formula (1) or (2): ##STR1##Type: GrantFiled: March 6, 1997Date of Patent: January 12, 1999Assignee: Konica CorporationInventors: Noritaka Nakayama, Mitsunori Matsuura, Shinji Matsumoto
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Patent number: 5858616Abstract: Disclosed are a photosensitive resin composition which comprises:(A) a compound having a carboxyl group;(B) a resin having a carboxyl group;(C) a photopolymerizable unsaturated compound having an ethylenic unsaturated group;(D) a photopolymerization initiator which produces free radical by irradiation of active light; and(E) a phosphor,a photosensitive film and a process for preparing a fluorescent pattern using the same, and a phosphor subjected to surface treatment and a process for preparing the same.Type: GrantFiled: October 11, 1996Date of Patent: January 12, 1999Assignee: Hitachi Chemical Company, Ltd.Inventors: Hiroyuki Tanaka, Hideyasu Tsuiki, Takeshi Nojiri, Koichi Kamijima, Seiji Tai, Seikichi Tanno, Hajime Kakumaru
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Patent number: 5834157Abstract: Compounds of the formula ##STR1## are suitable as photoinitiators in free-radical-polymerizable mixtures and are notable for a reduced tendency to diffusion and sublimation than comparable known compounds.Type: GrantFiled: December 23, 1996Date of Patent: November 10, 1998Assignee: Agfa-Gevaert AGInventors: Siegfried Scheler, deceased, Klaus-Peter Bergmann, Gerhard Buhr
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Patent number: 5800965Abstract: A photopolymerizable composition for a photosensitive lithographic printing plate, comprising (A) addition-polymerizable ethylenically unsaturated bond-containing monomers, (B) a photopolymerization initiator system and (C) a polymer binder having carboxyl groups in its molecule, wherein the addition-polymerizable ethylenically unsaturated bond-containing monomers (A) contain a specific monomer which is a phosphoric acid ester compound (A-1) having at least one (meth)acryloyl group and/or a compound (A-2) of the following formula ##STR1## wherein R.sup.1 is a hydrogen atom or a methyl group, X is a C.sub.1-6 alkylene group which may be branched and may be substituted by halogen, and m is an integer of at least 2, and the polymer binder (C) having carboxyl groups in its molecule, is a compound having at least a part of the carboxyl groups reacted with an alicyclic epoxy group-containing unsaturated compound.Type: GrantFiled: December 26, 1996Date of Patent: September 1, 1998Assignee: Mitsubishi Chemical CorporationInventors: Shigeo Tsuji, Hideaki Okamoto
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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: 5773190Abstract: Disclosed herein is a resist composition comprising in admixture (a) 100 parts by weight of an alkali-soluble phenolic resin, (b) 0.2-50 parts by weight of a compound which forms an acid upon exposure to active rays and consists of a specific halogen-containing aromatic compound, (c) 0.01-50 parts by weight of a compound which crosslinks the alkali-soluble phenolic resin in the presence of the acid formed from the compound (b), and (d) sufficient solvent to dissolve the foregoing composition components.Type: GrantFiled: February 10, 1997Date of Patent: June 30, 1998Assignee: Nippon Zeon Co., Ltd.Inventors: Masayuki Oie, Hideyuki Tanaka, Nobunori Abe
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Patent number: 5773194Abstract: A light sensitive composition comprising (a) a vinyl type polymer having a unit represented by the following Formula (1) and a carboxyl group, (b) a monomer, oligomer or polymer containing at least one polymerizable double bond in its molecule, (c) a photopolymerization initiator and (d) a polymerization inhibitor capable of trapping a radical, ##STR1##Type: GrantFiled: August 29, 1996Date of Patent: June 30, 1998Assignee: Konica CorporationInventors: Ryoji Hattori, Tatsuichi Maehashi, Takaaki Kuroki, Sota Kawakami
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Patent number: 5767169Abstract: A photopolymerizable composition comprising (a) at least one ethylenically unsaturated photopolymerizable compound, and (b) alkoxyphenyl-substituted bisacylphosphine oxides of the formula I ##STR1## in which R.sub.1 and R.sub.2 are identical or different and are a radical of the formula II ##STR2## in which R.sub.4 and R.sub.5 independently of one another are C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.12 alkoxy, andR.sub.6, R.sub.7 and R.sub.8 independently of one another are hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or halogen,R.sub.3 is a radical of the formula III ##STR3## in which R.sub.9 is C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl, naphthyl, phenyl-C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.12 alkenyl, --CF.sub.3 or ##STR4## or R.sub.9 is a radical of the formula IV or V ##STR5## in which X is for example C.sub.1 -C.sub.16 alkylene, C.sub.4 -C.sub.12 alkenylene or is xylylene,R.sub.10 is for example hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.Type: GrantFiled: February 14, 1996Date of Patent: June 16, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: David George Leppard, Manfred Kohler
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Patent number: 5756255Abstract: Proposed is a novel undercoating composition used in the photolithographic patterning of a photoresist layer by intervening between the substrate surface and the photoresist layer to decrease the adverse influences of the reflecting light from the substrate surface. The undercoating composition of the invention comprises (a) a melamine compound substituted by methylol groups and/or alkoxymethyl groups and (b) a polyhydroxy benzophenone compound, diphenyl sulfone compound or diphenyl sulfoxide compound, optionally, with admixture of (c) an alkali-insoluble resin of a (meth)acrylic acid ester.Type: GrantFiled: November 12, 1996Date of Patent: May 26, 1998Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Mitsuru Sato, Katsumi Oomori, Kiyoshi Ishikawa, Etsuko Iguchi, Toshimasa Nakayama
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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: 5685754Abstract: A polymer coated fiber, a polymer-coated web, and a method of coating a fiber or a web. The fiber or web is coated with a composition comprising an admixture of unsaturated polymerizable material and a photoreactor, and the composition on the fiber or web is irradiated with an amount of radiation sufficient to cure the composition and form a coating on the fiber or web. The photoreactor comprises a wavelength-specific sensitizer covalently bonded to a reactive species-generating photoinitiator. Suitable wavelength-specific sensitizers have a molar extinction coefficient greater than about 5000 liters per mole per cm at an absorption maximum and resulting photoreactors have a quantum yield of greater than about 0.5 at an absorption maximum.Type: GrantFiled: May 19, 1995Date of Patent: November 11, 1997Assignee: Kimberly-Clark CorporationInventors: Ronald Sinclair Nohr, John Gavin MacDonald
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Patent number: 5645974Abstract: Compositions comprising a linear base polymer, an ethylenically unsaturated addition-polymerizable compound and a combination of (A) a 1-benzoyl-1-amino-substituted-1-benzylalkane with (B) an .alpha.-phenyl-.alpha.,.alpha.-dialkoxyacetophenone as photopolymerization initiator are suitable for the production of thick-film printing plates.Type: GrantFiled: April 22, 1996Date of Patent: July 8, 1997Assignees: Tokyo Ohka Kogyo, K.K., Ciba-Geigy CorporationInventors: Katsuyuki Ohta, Toshiya Takagi, Toshimi Aoyama
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Patent number: 5609992Abstract: A photopolymerizable composition is disclosed, comprising (i) a compound having at least one addition-polymerizable, ethylenically unsaturated bond; (ii) a compound represented by formula (IA) or (IB): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 each independently represents a hydrogen atom, a halogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, a hydroxyl group, a substituted oxy group, a mercapto group, a substituted thio group, an amino group, a substituted amino group, a substituted carbonyl group, a sulfo group, a sulfonato group, a substituted sulfinyl group, a substituted sulfonyl group, a phosphono group, a substituted phosphono group, a phosphonato group, a substituted phosphonato group, a cyano group or a nitro group or R.sup.1 and R.sup.2, R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.9 and R.sup.10, R.sup.10 and R.sup.11 or R.sup.11 and R.sup.Type: GrantFiled: October 27, 1995Date of Patent: March 11, 1997Assignee: Fuji Photo Film Co., Ltd.Inventors: Tadahiro Sorori, Yasuo Okamoto, Syunichi Kondo, Hiromichi Kurita
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Patent number: 5607817Abstract: A photopolymerizable composition comprising an addition polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator system, wherein the photopolymerization initiator system comprises:(a) a sensitizer of the formula (I) ##STR1## wherein -A is ##STR2## wherein each of R.sup.1 and R.sup.2 is a hydrogen atom, an alkyl group, an aryl group or a halogen atom, each of R.sup.3 and R.sup.4 is an alkyl group which may have substituents, each of R.sup.5 to R.sup.8 is a hydrogen atom, an alkyl group or an alkoxy group, or R.sup.3 and R.sup.4, R.sup.3 and R.sup.5 and/or R.sup.4 and R.sup.6 bond to each other to form a ring structure, and n is 0, 1 or 2; and each of X.sup.1 and X.sup.Type: GrantFiled: August 18, 1994Date of Patent: March 4, 1997Assignee: Mitsubishi Chemical CorporationInventors: Hideki Nagasaka, Masaaki Tsuchiyama, Toshiyuki Urano
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Patent number: 5554465Abstract: The present invention provides a composition having sensitivity to light or radiation. The composition comprises a polymer having a siloxane-bond structure which undergoes polymerization reaction when irridiated with light or radiation, and a sensitizing agent. The present invention also provides a process for forming a pattern, preparing a photomask and a semiconductor device by using the composition of the present invention.Type: GrantFiled: May 23, 1995Date of Patent: September 10, 1996Assignee: Matsushita Electronics CorporationInventor: Hisashi Watanabe
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Patent number: 5547808Abstract: The present invention provides a composition having sensitivity to light or radiation. The composition comprises a polymer having a siloxane-bond structure which undergoes polymerization reaction when irridiated with light or radiation, and a sensitizing agent. The present invention also provides a process for forming a pattern, preparing a photomask and a semiconductor device by using the composition of the present invention.Type: GrantFiled: September 9, 1994Date of Patent: August 20, 1996Assignee: Matsushita Electronics CorporationInventor: Hisashi Watanabe
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Patent number: 5543262Abstract: A light sensitive composition which is capable of photopolymerization which includes a photopolymerizable compound a free radical generating component and a benzanthrone or substituted benzanthrone which substantially prevents photopolymerization when the light sensitive composition is exposed to actinic radiation below a threshold amount but permits photopolymerization when the light sensitive composition is exposed to actinic radiation above a threshold amount. This achieves a gate effect which eliminates or decreases unwanted partial exposure in the nonimage areas and hence improves reproduction quality.Type: GrantFiled: February 24, 1995Date of Patent: August 6, 1996Assignee: International Paper CompanyInventors: Maria T. Sypek, John R. Delude, Paul A. Perron
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Patent number: 5541038Abstract: Compositions comprising a linear base polymer, an ethylenically unsaturated addition-polymerizable compound and a combination of (A) a 1-benzoyl-1-amino-substituted-1-benzylalkane with (B) an .alpha.-phenyl-.alpha.,.alpha.-dialkoxyacetophenone as photopolymerization initiator are suitable for the production of thick-film printing plates.Type: GrantFiled: April 5, 1995Date of Patent: July 30, 1996Assignees: Ciba-Geigy Corporation, Tokyo Ohka Kogyo, K.K.Inventors: Katsuyuki Ohta, Toshiya Takagi, Toshimi Aoyama
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Patent number: 5470662Abstract: Holographic films contain a copolymer binder having the following formula:(M).sub.w (VAc).sub.x (VOH).sub.y (CTFE).sub.zwherein M is a fluoromonomer; VAc is vinyl acetate; VOH is vinyl alcohol; and CTFE is chlorotrifluoroethylene; and wherein w, x, y, and z are percentages by weight; w is 5 to 22%, x is 50 to 75%, y is 3 to 8%, and z is 15 to 30% with the copolymer containing 3-35% by weight fluorine. These imaged films are particularly suited for lamination to glass in head-up display applications.Type: GrantFiled: October 25, 1994Date of Patent: November 28, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Andrew M. Weber, Aleksander Beresniewicz
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Patent number: 5413863Abstract: Holographic films are disclosed that contain a binder having the following formula:(M).sub.w (VAc).sub.x (VOH).sub.y (VOS).sub.zwherein M is a fluoromonomer; VAc is vinyl acetate; VOH is vinyl alcohol; and VOS is vinyl trimethylsilyl ether; and wherein w, x, y, and z are percentages by weight; w is 5 to 30, x is 40 to 80, y is 0 to 20, and z is 2 to 30; said copolymers containing 3 to 23% by weight fluorine. These imaged films are particularly suited for lamination to glass in head-up display applications.Type: GrantFiled: November 4, 1993Date of Patent: May 9, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Andrew M. Weber, Aleksander Beresniewicz
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Patent number: 5384238Abstract: Positive-acting photothermographic elements suitable for use at contact speeds comprising a base layer having at least two layers thereon, which layers define a photosensitive medium comprising a photocurable composition, a reducible silver source, and a reducing system for silver ion comprising one or more components including a compound capable of reducing silver ion to silver metal, such that the reducible silver source and at least one component of the reducing system for silver ion are present in separate layers, wherein exposure of the element to actinic radiation causes curing of the photocurable composition in the exposed area(s), said curing preventing the reducing system from interacting with the reducible silver source during thermal processing and in which the photocurable composition comprises a free radical curable resin and a photoinitiator therefor having an absorbance to radiation in the wavelength range of 340 to 440 nm, which photoinitiator upon exposure to said actinic radiation or duringType: GrantFiled: January 21, 1994Date of Patent: January 24, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: Richard J. Ellis, Ranjan C. Patel, Robert J. D. Nairne
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Patent number: 5378579Abstract: A photopolymerizable composition comprising(A) an addition-polymerizable compound having an ethylenically unsaturated double bond,(B) a compound of the formula: ##STR1## [wherein R.sup.1 is a substituted or nonsubstituted phenyl group, R.sup.2 and R.sup.3 are the same or different and indicate a hydrogen atom or a C.sub.1-4 alkyl group, R.sup.4 in an alkylene group which may have at least one substituent selected from alkyl, hydroxyl and oxo (.dbd.O) on a main chain, or which may contain at least one member selected from an oxygen atom and a cycloalkylene group in a main chain, R.sup.5 is a hydrogen atom or a methyl group, and a and b are independently 0 or 1],(C) a light absorbing compound, and(D) a film-forming polymer having alkaline solubility or alkaline swelling characteristic is disclosed. There is also disclosed a photosensitive lithographic printing plate comprising the photopolymerizable composition.Type: GrantFiled: July 8, 1992Date of Patent: January 3, 1995Assignee: Nippon Paint Co., Ltd.Inventors: Seiji Arimatsu, Takakazu Hase, Yoshifumi Ichinose
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Patent number: 5378585Abstract: The present invention provides a composition having sensitivity to light or radiation. The composition comprises a polymer having a siloxane-bond structure which undergoes polymerization reaction when irridiated with light or radiation, and a sensitizing agent. The present invention also provides a process for forming a pattern, preparing a photomask and a semiconductor device by using the composition of the present invention.Type: GrantFiled: October 13, 1993Date of Patent: January 3, 1995Assignee: Matsushita Electronics CorporationInventor: Hisashi Watanabe
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Patent number: 5376503Abstract: A lithographic coating and method of framing a lithographic image are disclosed. The method comprises coating at least a portion of a surface of an article with a radiation-crosslinkable polymer, and exposing the coated surface to a pattern of radiation to crosslink the polymer in a lithographic image. The functionalized polymer is a copolymer of an isoolefin of 4 to 7 carbon atoms and para-alkylstyrene, wherein the para-alkylstyrene is functionalized with a radiation reactive group at the para-alkyl group of the para-alkylstyrene.Type: GrantFiled: November 24, 1992Date of Patent: December 27, 1994Assignee: Exxon Chemical Patents Inc.Inventors: Jay D. Audett, Kenneth O. McElrath
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Patent number: 5352556Abstract: A low melt toner resin with low minimum fix temperature and wide fusing latitude contains a linear portion and a cross-linked portion containing high density cross-linked microgel particles, but substantially no low density cross-linked polymer. The resin may be formed by reactive melt mixing.Type: GrantFiled: March 23, 1993Date of Patent: October 4, 1994Assignee: Xerox CorporationInventors: Hadi K. Mahabadi, Enno E. Agur, Gerald R. Allison, Michael S. Hawkins, Stephan Drappel, Maria N. V. McDougall, Bernard Grushkin, Thomas R. Hoffend, Angelo J. Barbetta
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Patent number: 5334484Abstract: A photopolymerizable composition comprising: (a) 100 parts by weight of a compound having at least one ethylenically unsaturated group, (b) 0 to 400 parts by weight of a thermoplastic organic polymer and (c) 0.01 to 20 parts by weight of a photoinitiator, characterized in that an acridine compound of the following general formula (I) is used as the photoinitiator: ##STR1## wherein R represents an alkylene, oxadialkylene or thiodialkylene group having 2 to 20 carbon atoms,and a photopolymerizable element comprising a layer of the photopolymerizable composition formed on a support.Type: GrantFiled: June 15, 1992Date of Patent: August 2, 1994Assignees: Hitachi Chemical Co., Ltd., Asahi Denka Kogyo Kabushiki KaishaInventors: Yoshitaka Minami, Hajime Kakumaru, Naohiro Kubota, Nobuhide Tominaga, Koji Ishizaki
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Patent number: 5273862Abstract: A photopolymerizable recording material is diclosed comprising a base material, a photopolymerizable layer and a cover layer which comprises a water-soluble polymer which is substantially impermeable to atmospheric oxygen, and a polymer which binds atmospheric oxygen and is virtually completely soluble in water at 20.degree. C. The material displays reduced sensitivity to atmospheric oxygen, even on prolonged storage and at elevated ambient temperatures and elevated atmospheric humidity.Type: GrantFiled: July 17, 1992Date of Patent: December 28, 1993Assignee: Hoechst AktiengesellschaftInventors: Rudolf Zertani, Dieter Mohr
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Patent number: 5230986Abstract: A Photohardenable composition consisting essentially of a free radical polymerizable compound, an electron donating coinitiator, and a benzospiropyran, wherein the benzospiropyran undergoes ring opening to form a merocyanine upon exposure to a actinic radiation or heat and exposure to a second 296 radiation causes the composition to harden.Type: GrantFiled: February 1, 1991Date of Patent: July 27, 1993Assignee: StereoGraphics Limited PartnershipInventor: Douglas C. Neckers
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Patent number: 5229252Abstract: A photoimageable composition for forming a solder mask has a photopolymerizable acrylate chemical system which renders exposed portions insolvable to alkaline aqueous developers and an epoxy chemical system which hardens the composition after exposure and development. The acrylate chemical system comprises acrylate monomers, epoxy-acrylate oligomers and a photoinitiator. The epoxy chemical system comprises an epoxy resin and a curative therefore. The composition further comprises a cross-linking agent which is reactive with hydroxyl groups of the acrylate and epoxy chemical systems.Type: GrantFiled: October 21, 1991Date of Patent: July 20, 1993Assignee: Morton International, Inc.Inventors: Kathy M. Flynn, Vinai M. Tara, Kathleen L. Nelson
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Patent number: 5221595Abstract: A photopolymerizable mixture is disclosed that contains a polymer binder, a polymerizable compound having at least one terminal ethylene double bond and a boiling point above 100.degree. C. at normal pressure, a hexaarylbisimidazole and a 1,3-diarylpyrazoline or a 1-aryl-3-aralkenyl-pyrazoline. The mixture is suitable for the preparation of printing plates and photoresists and is distinguished by high photosensitivity and low sensitivity towards acid solutions.Type: GrantFiled: March 27, 1991Date of Patent: June 22, 1993Assignee: Hoechst AktiengesellschaftInventors: Juergen Lingnau, Hans-Dieter Frommeld
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Patent number: 5219700Abstract: A photosensitive composition comprising (a) a 1,2-naphthoquinone-2-diazido-4-sulfonic acid ester compound, (b) alkali-soluble resin, (c) a halomethyloxadiazole compound which releases halogen free radicals by irradiation with actinic rays and (a) a dye which interacts withthe decomposition product of said halomethyloxydiazole compound and discolors or develops color. The composition exhibits excellent development latitude, light safety, visible-on-exposure characteristic and printing resistance.Type: GrantFiled: March 24, 1992Date of Patent: June 15, 1993Assignees: Mitsubishi Kasei Corporation, Konica CorporationInventors: Hideyuki Nakai, Kiyoshi Goto, Hiroshi Tomiyasu, Yoshiko Fujita
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Patent number: 5217845Abstract: A photopolymerizable mixture is described which contains a polymeric binder, a polymerizable compound and an acridine compound of the general formula I ##STR1## as photoinitiator, in which R.sup.1 denotes an optionally substituted alkyl or acyl group,R.sup.2, R.sup.3 are identical or different and denoteand R.sup.4 hydrogen or halogen atoms or optionally substituted alkyl or acyl groups,R.sup.5, R.sup.6 are identical or different and denoteand R.sup.7 hydrogen or halogen atoms or optionally substituted alkyl, aryl or acyl groups, or groups of the formula II ##STR2## The photoinitiators yield a mixture having high photosensitivity and have a lower tendency to diffusion than the known 9-phenylacridine.Type: GrantFiled: September 26, 1991Date of Patent: June 8, 1993Assignee: Hoechst AktiengesellschaftInventors: Hartmut Steppan, Hans-Dieter Frommeld
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Patent number: 5215860Abstract: Energy polymerizable compositions comprising at least one cyanate monomer and as curing agent an organometallic compound are disclosed. The compositions are useful in applications requiring high performance, such as high temperature performance; in composites, particularly structural composities; structural adhesives; tooling for structural composities; electronic applications such as printed wiring boards and semiconductor encapsulants; graphic arts; injection molding and prepregs; and high performance binders.Type: GrantFiled: August 19, 1988Date of Patent: June 1, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: Fred B. McCormick, Katherine A. Brown-Wensley, Robert J. DeVoe