Free Radical Patents (Class 430/916)
  • Patent number: 6217984
    Abstract: 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: Grant
    Filed: May 21, 1992
    Date of Patent: April 17, 2001
    Assignee: 3M Innovative Properties Company
    Inventors: Wesley J. Bruxvoort, Steven J. Keipert, Fred B. McCormick, Jerry W. Williams, Bradford B. Wright
  • Patent number: 6183934
    Abstract: 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: Grant
    Filed: July 1, 1998
    Date of Patent: February 6, 2001
    Assignee: Kabushiki Kaisha Toshiba
    Inventor: Yoshiaki Kawamonzen
  • Patent number: 6165686
    Abstract: 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: Grant
    Filed: May 21, 1998
    Date of Patent: December 26, 2000
    Assignee: Showa Denko K.K.
    Inventors: Hirotoshi Kamata, Toshio Koshikawa, Takeo Watanabe, Shuichi Sugita
  • Patent number: 6103453
    Abstract: 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: Grant
    Filed: March 17, 1999
    Date of Patent: August 15, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Prantl, Erich Beck, Matthias Lokai, Christof Kandzia
  • Patent number: 6066435
    Abstract: 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: Grant
    Filed: May 11, 1998
    Date of Patent: May 23, 2000
    Assignee: CIBA Specialty Chemicals Corp.
    Inventor: Kurt Munk
  • Patent number: 6025112
    Abstract: 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: Grant
    Filed: February 4, 1997
    Date of Patent: February 15, 2000
    Assignee: Brother Kogyo Kabushiki Kaisha
    Inventor: Masashi Tsuda
  • Patent number: 6017660
    Abstract: 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: Grant
    Filed: June 9, 1998
    Date of Patent: January 25, 2000
    Assignee: 3M Innovative Properties Company
    Inventors: Michael C. Palazzotto, F. Andrew Ubel, III, Joel D. Oxman, M. Zaki Ali
  • Patent number: 6013415
    Abstract: 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: Grant
    Filed: December 15, 1998
    Date of Patent: January 11, 2000
    Assignee: JSR Corporation
    Inventors: Kouichi Sakurai, Takahiro Iijima, Yukiko Ito, Hiroaki Nemoto
  • Patent number: 6007965
    Abstract: 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: Grant
    Filed: October 7, 1997
    Date of Patent: December 28, 1999
    Inventors: Tsuguo Yamaoka, Kenichi Koseki, Mitsuharu Obara, Ikuo Shimizu, Yukiyoshi Ito, Hitoshi Kawato
  • Patent number: 6004724
    Abstract: 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: Grant
    Filed: June 25, 1998
    Date of Patent: December 21, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Hitoshi Yamato, Hartmut Bleier, Jean-Luc Birbaum, Martin Kunz, Kurt Dietliker, Christoph De Leo, Toshikage Asakura
  • Patent number: 5989778
    Abstract: 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: Grant
    Filed: June 30, 1998
    Date of Patent: November 23, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Shigeo Hozumi
  • Patent number: 5965324
    Abstract: 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: Grant
    Filed: July 18, 1997
    Date of Patent: October 12, 1999
    Assignee: Konica Corporation
    Inventors: Kimihiko Okubo, Noritaka Nakayama
  • Patent number: 5952152
    Abstract: 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: Grant
    Filed: November 21, 1996
    Date of Patent: September 14, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
  • Patent number: 5939238
    Abstract: 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: Grant
    Filed: June 2, 1998
    Date of Patent: August 17, 1999
    Assignee: Morton International, Inc.
    Inventors: Robert Barr, Daniel E. Lundy, Eiji Kosaka, Shigeru Murakami
  • Patent number: 5922509
    Abstract: 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: Grant
    Filed: March 18, 1998
    Date of Patent: July 13, 1999
    Assignee: Morton International, Inc.
    Inventors: Randall W. Kautz, Robert K. Barr
  • Patent number: 5876899
    Abstract: 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: Grant
    Filed: September 18, 1996
    Date of Patent: March 2, 1999
    Assignee: Shipley Company, L.L.C.
    Inventors: Charles R. Szmanda, Gary N. Taylor, Robert L. Brainard, Manuel DoCanto
  • Patent number: 5866298
    Abstract: 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: Grant
    Filed: November 21, 1996
    Date of Patent: February 2, 1999
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Satoshi Iwamoto, Yasumi Wanibe, Hiroaki Nemoto, Nobuo Bessho
  • Patent number: 5858617
    Abstract: 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: Grant
    Filed: March 6, 1997
    Date of Patent: January 12, 1999
    Assignee: Konica Corporation
    Inventors: Noritaka Nakayama, Mitsunori Matsuura, Shinji Matsumoto
  • Patent number: 5858616
    Abstract: 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: Grant
    Filed: October 11, 1996
    Date of Patent: January 12, 1999
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Hiroyuki Tanaka, Hideyasu Tsuiki, Takeshi Nojiri, Koichi Kamijima, Seiji Tai, Seikichi Tanno, Hajime Kakumaru
  • Patent number: 5834157
    Abstract: 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: Grant
    Filed: December 23, 1996
    Date of Patent: November 10, 1998
    Assignee: Agfa-Gevaert AG
    Inventors: Siegfried Scheler, deceased, Klaus-Peter Bergmann, Gerhard Buhr
  • Patent number: 5800965
    Abstract: 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: Grant
    Filed: December 26, 1996
    Date of Patent: September 1, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Shigeo Tsuji, Hideaki Okamoto
  • Patent number: 5792589
    Abstract: 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: Grant
    Filed: February 4, 1997
    Date of Patent: August 11, 1998
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Tadahiko Udagawa, Hideaki Masuko, Hiroaki Nemoto, Nobuo Bessho
  • Patent number: 5773190
    Abstract: 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: Grant
    Filed: February 10, 1997
    Date of Patent: June 30, 1998
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Masayuki Oie, Hideyuki Tanaka, Nobunori Abe
  • Patent number: 5773194
    Abstract: 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: Grant
    Filed: August 29, 1996
    Date of Patent: June 30, 1998
    Assignee: Konica Corporation
    Inventors: Ryoji Hattori, Tatsuichi Maehashi, Takaaki Kuroki, Sota Kawakami
  • Patent number: 5767169
    Abstract: 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: Grant
    Filed: February 14, 1996
    Date of Patent: June 16, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: David George Leppard, Manfred Kohler
  • Patent number: 5756255
    Abstract: 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: Grant
    Filed: November 12, 1996
    Date of Patent: May 26, 1998
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Mitsuru Sato, Katsumi Oomori, Kiyoshi Ishikawa, Etsuko Iguchi, Toshimasa Nakayama
  • Patent number: 5756258
    Abstract: 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: Grant
    Filed: February 10, 1995
    Date of Patent: May 26, 1998
    Assignee: Kyowa Hakko Co., Ltd.
    Inventors: Tsuguo Yamaoka, Kenichi Koseki, Mitsuharu Obara, Ikuo Shimizu, Yukiyoshi Ito, Hitoshi Kawato
  • Patent number: 5685754
    Abstract: 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: Grant
    Filed: May 19, 1995
    Date of Patent: November 11, 1997
    Assignee: Kimberly-Clark Corporation
    Inventors: Ronald Sinclair Nohr, John Gavin MacDonald
  • Patent number: 5645974
    Abstract: 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: Grant
    Filed: April 22, 1996
    Date of Patent: July 8, 1997
    Assignees: Tokyo Ohka Kogyo, K.K., Ciba-Geigy Corporation
    Inventors: Katsuyuki Ohta, Toshiya Takagi, Toshimi Aoyama
  • Patent number: 5609992
    Abstract: 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: Grant
    Filed: October 27, 1995
    Date of Patent: March 11, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Tadahiro Sorori, Yasuo Okamoto, Syunichi Kondo, Hiromichi Kurita
  • Patent number: 5607817
    Abstract: 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: Grant
    Filed: August 18, 1994
    Date of Patent: March 4, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hideki Nagasaka, Masaaki Tsuchiyama, Toshiyuki Urano
  • Patent number: 5554465
    Abstract: 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: Grant
    Filed: May 23, 1995
    Date of Patent: September 10, 1996
    Assignee: Matsushita Electronics Corporation
    Inventor: Hisashi Watanabe
  • Patent number: 5547808
    Abstract: 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: Grant
    Filed: September 9, 1994
    Date of Patent: August 20, 1996
    Assignee: Matsushita Electronics Corporation
    Inventor: Hisashi Watanabe
  • Patent number: 5543262
    Abstract: 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: Grant
    Filed: February 24, 1995
    Date of Patent: August 6, 1996
    Assignee: International Paper Company
    Inventors: Maria T. Sypek, John R. Delude, Paul A. Perron
  • Patent number: 5541038
    Abstract: 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: Grant
    Filed: April 5, 1995
    Date of Patent: July 30, 1996
    Assignees: Ciba-Geigy Corporation, Tokyo Ohka Kogyo, K.K.
    Inventors: Katsuyuki Ohta, Toshiya Takagi, Toshimi Aoyama
  • Patent number: 5470662
    Abstract: 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: Grant
    Filed: October 25, 1994
    Date of Patent: November 28, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Andrew M. Weber, Aleksander Beresniewicz
  • Patent number: 5413863
    Abstract: 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: Grant
    Filed: November 4, 1993
    Date of Patent: May 9, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Andrew M. Weber, Aleksander Beresniewicz
  • Patent number: 5384238
    Abstract: 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 during
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: January 24, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Richard J. Ellis, Ranjan C. Patel, Robert J. D. Nairne
  • Patent number: 5378579
    Abstract: 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: Grant
    Filed: July 8, 1992
    Date of Patent: January 3, 1995
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Seiji Arimatsu, Takakazu Hase, Yoshifumi Ichinose
  • Patent number: 5378585
    Abstract: 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: Grant
    Filed: October 13, 1993
    Date of Patent: January 3, 1995
    Assignee: Matsushita Electronics Corporation
    Inventor: Hisashi Watanabe
  • Patent number: 5376503
    Abstract: 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: Grant
    Filed: November 24, 1992
    Date of Patent: December 27, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Jay D. Audett, Kenneth O. McElrath
  • Patent number: 5352556
    Abstract: 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: Grant
    Filed: March 23, 1993
    Date of Patent: October 4, 1994
    Assignee: Xerox Corporation
    Inventors: 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
  • Patent number: 5334484
    Abstract: 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: Grant
    Filed: June 15, 1992
    Date of Patent: August 2, 1994
    Assignees: Hitachi Chemical Co., Ltd., Asahi Denka Kogyo Kabushiki Kaisha
    Inventors: Yoshitaka Minami, Hajime Kakumaru, Naohiro Kubota, Nobuhide Tominaga, Koji Ishizaki
  • Patent number: 5273862
    Abstract: 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: Grant
    Filed: July 17, 1992
    Date of Patent: December 28, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudolf Zertani, Dieter Mohr
  • Patent number: 5230986
    Abstract: 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: Grant
    Filed: February 1, 1991
    Date of Patent: July 27, 1993
    Assignee: StereoGraphics Limited Partnership
    Inventor: Douglas C. Neckers
  • Patent number: 5229252
    Abstract: 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: Grant
    Filed: October 21, 1991
    Date of Patent: July 20, 1993
    Assignee: Morton International, Inc.
    Inventors: Kathy M. Flynn, Vinai M. Tara, Kathleen L. Nelson
  • Patent number: 5221595
    Abstract: 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: Grant
    Filed: March 27, 1991
    Date of Patent: June 22, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Juergen Lingnau, Hans-Dieter Frommeld
  • Patent number: 5219700
    Abstract: 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: Grant
    Filed: March 24, 1992
    Date of Patent: June 15, 1993
    Assignees: Mitsubishi Kasei Corporation, Konica Corporation
    Inventors: Hideyuki Nakai, Kiyoshi Goto, Hiroshi Tomiyasu, Yoshiko Fujita
  • Patent number: 5217845
    Abstract: 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: Grant
    Filed: September 26, 1991
    Date of Patent: June 8, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Steppan, Hans-Dieter Frommeld
  • Patent number: 5215860
    Abstract: 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: Grant
    Filed: August 19, 1988
    Date of Patent: June 1, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Fred B. McCormick, Katherine A. Brown-Wensley, Robert J. DeVoe