Specified Rate-affecting Material Contains Onium Group Patents (Class 522/25)
  • Patent number: 6025017
    Abstract: 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: Grant
    Filed: May 21, 1997
    Date of Patent: February 15, 2000
    Assignee: NCR Corporation
    Inventor: Joseph D. Roth
  • Patent number: 6025406
    Abstract: Photocurable, addition polymerizable compositions contain an epoxy resin and a photoinitiator system containing (a) an epoxy resin and (b) a photoinitiator system comprising: (i) an iodonium salt; (ii) a visible light sensitizer; and (iii) an electron donor compound, wherein the photoinitiator system has a photoinduced potential of at least about 0 mV relative to a standard solution of 2.9.times.10.sup.-5 moles/g diphenyl iodonium hexafluoroantimonate and 1.5.times.10.sup.-5 moles/g camphorquinone in 2-butanone. The compositions cure on exposure to light in the visible spectrum and are useful in a variety of applications, including dental adhesives and composites.
    Type: Grant
    Filed: April 11, 1997
    Date of Patent: February 15, 2000
    Assignee: 3M Innovative Properties Company
    Inventors: Joel D. Oxman, Dwight W. Jacobs
  • 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: 6010820
    Abstract: Provided is a positive photosensitive composition which has high photosensitivity, is capable of giving an excellent resist pattern, and changes little with time after exposure. The positive photosensitive composition comprises (1) a resin having group(s) capable of decomposing by the action of an acid to enhance solubility of the resin in an alkaline developing solution and (2) a compound represented by formula (I), (II) or (III) which is capable of generating a sulfonic acid upon irradiation with actinic rays or a radiation: ##STR1## wherein R.sub.1 to R.sub.5 and R.sub.7 to R.sub.10 each represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a hydroxy group, a halogen atom, or a group represented by --S--R.sub.6, where R.sub.6 represents an alkyl group or an aryl group; X.sup.- represents the anion of a benzenesulfonic, naphthalenesulfonic, or anthracenesulfonic acid as defined in the specification; and m, n, p and q each represents an integer of 1 to 3.
    Type: Grant
    Filed: March 11, 1997
    Date of Patent: January 4, 2000
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Kunihiko Kodama, Kazuya Uenishi, Tsukasa Yamanaka
  • Patent number: 6008265
    Abstract: An ionic compound comprising at least one group A.sup.+ X.sup.-, comprising:a cationic group A.sup.+ selected from the group consisting of biaryliodonium, arylsulfonium, arylacylsulfonium, diazonium and organometallic cations comprising a transition metal complexed with at least one unsaturated cyclic compound comprising 4-12 carbon atoms, said cationic group being part of a polymer chain; whereinX.sup.- is an imide anion, [FSO.sub.2 NSO.sub.2 R'.sub.F ].sup.- or [R.sub.F CH.sub.2 OSO.sub.2 NSO.sub.2 R'.sub.F ].sup.- or [(R.sub.F).sub.2 CHOSO.sub.2 NSO.sub.2 R'.sub.F ].sup.-, or a methylide anion [FSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.-, or a [R.sub.F CH.sub.2 OSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.- or [(R.sub.F).sub.2 CHOSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.31 .
    Type: Grant
    Filed: October 3, 1997
    Date of Patent: December 28, 1999
    Assignees: Hydro-Quebec, Centre National de la Recherche Scientifique
    Inventors: Alain Vallee, Michel Armand, Xavier Ollivrin, Christophe Michot
  • Patent number: 5998495
    Abstract: Photocurable, addition polymerizable compositions contain an epoxy resin and a photoinitiator system containing (a) an epoxy resin, (b) a hydroxyl containing material and (c) a photoinitiator system comprising: (i) an iodonium salt; (ii) a visible light sensitizer; and (iii) an electron donor compound, wherein the photoinitiator system has a photoinduced potential of at least about 100 mV relative to a standard solution of 2.9.times.10.sup.-5 moles/g diphenyl iodonium hexafluoroantimonate and 1.5.times.10.sup.-5 moles/g camphorquinone in 2-butanone. The compositions cure on exposure to light in the visible spectrum and are useful in a variety of applications, including dental adhesives and composites.
    Type: Grant
    Filed: April 11, 1997
    Date of Patent: December 7, 1999
    Assignee: 3M Innovative Properties Company
    Inventors: Joel D. Oxman, Dwight W. Jacobs
  • Patent number: 5980253
    Abstract: In a first aspect, a method for treating hard tissue that includes: (a) applying to hard tissue a composition that includes a cationically active functional group, a free radically active functional group, and a polymerization initiator capable of initiating free radical polymerization, where the number of moles of cationically active functional groups per gram of composition is no greater than about 0.0075; and (b) exposing the composition to polymerization conditions to form an adhesive bonded to the hard tissue.
    Type: Grant
    Filed: January 12, 1998
    Date of Patent: November 9, 1999
    Assignee: 3M Innovative Properties Company
    Inventors: Joel D. Oxman, Hoa T. Bui, Dwight W. Jacobs
  • Patent number: 5981140
    Abstract: A positive photosensitive composition comprising:a compound represented by formula (I) or (I') and a compound represented by formula (II) as compounds which generate a sulfonic acid upon irradiation with actinic rays or radiation: ##STR1## The substituents in these formulae are as defined in the specification. The positive photosensitive composition has high sensitivity and high resolving power, undergoes neither a decrease in resist pattern line width nor the formation of a T-top resist pattern surface with the lapse of time from exposure to heat treatment, and exhibits less profile deterioration such as residual standing wave and collapse.
    Type: Grant
    Filed: September 17, 1997
    Date of Patent: November 9, 1999
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kenichiro Sato, Kunihiko Kodama, Kazuya Uenishi, Toshiaki Aoai
  • Patent number: 5972563
    Abstract: A liquid, radiation-curable composition which in addition to a liquid, free-radically polymerizable component comprises at least the following additional components: (A) from 40 to 80 percent by weight of a liquid difunctional or more highly functional epoxy resin or of a liquid mixture consisting of difunctional or more highly functional epoxy resins; (B) from 0.1 to 10 percent by weight of a cationic photoinitiator or of a mixture of cationic photoinitiators; and (C) from 0.
    Type: Grant
    Filed: July 28, 1997
    Date of Patent: October 26, 1999
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Bettina Steinmann, Adrian Schulthess
  • Patent number: 5973020
    Abstract: The present invention relates to a photoinitiator composition that can be used to initiate polymerization upon exposure to radiation. The said composition includes both a composition which yields cations upon exposure to actinic radiation, such as an iodonium borate initiator and a stabilizing amino agent. The amino agent is a secondary or tertiary amine having the general formula (VIII), a sterically arranged cyclic amine having the general formula (IX), or an amine consisting of groups that have the general formulas (VIII) and (IX) and that are interconnected. ##STR1## The compositions are particularly useful when used in conjunction with polyorganosiloxane monomers and when exposed to ultraviolet radiation.
    Type: Grant
    Filed: January 6, 1998
    Date of Patent: October 26, 1999
    Assignee: Rhodia Inc.
    Inventors: Stuart R. Kerr, III, Reeshemah L. Beaty
  • 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: 5962546
    Abstract: Compositions containing conductivity enhancers, which are capable of being coated onto a substrate by means of electrostatic assistance. The compositions comprise one or more cationically polymerizable monomer(s), one or more cationic initiator(s), and one or more non-volatile conductivity enhancer(s) having anionic and cationic portions which are soluble in the monomer(s) and which do not interfere with cationic polymerization wherein the anionic portion is a non-coordinating carbon-containing anion. The compositions may further comprise one or more dissociation enhancing agent(s), oligomer(s) or polymer(s), preferably co-reactive, free-radically curable monomer(s), free-radical generating initiator(s), leveling agents, and other additives or adjuvants to impart specific properties to the polymerized composition.
    Type: Grant
    Filed: May 1, 1997
    Date of Patent: October 5, 1999
    Assignee: 3M Innovative Properties Company
    Inventors: Albert I. Everaerts, William M. Lamanna, Albert E. Seaver, George V. D. Tiers
  • Patent number: 5962547
    Abstract: Radiation- or thermally-initiated cationically-curable styrene oxides of the structure ##STR1## are suitable for use in cationically curable adhesive and coating compositions.
    Type: Grant
    Filed: May 14, 1998
    Date of Patent: October 5, 1999
    Inventors: Nikola A. Nikolic, Rose Ann Schultz
  • Patent number: 5942372
    Abstract: Improved photopolymerization initiator systems are comprised of a spectral sensitizer that sensitizes in the ultraviolet or visible regions of the spectrum and an N-aryl, O-aryl or S-aryl polycarboxylic acid co-initiator. The improved initiator systems are incorporated in photo-polymerizable compositions containing one or more addition-polymerizable ethylenically-unsaturated compounds to form compositions suitable for the preparation of radiation-sensitive layers in lithographic printing plates adapted to be imagewise-exposed with ultraviolet- or visible-light-emitting lasers such as argon-ion lasers and frequency doubled Nd:YAG lasers. Such plates are able to effectively meet the dual requirements of very high photospeed and very good shelf-life required in computer-to-plate systems.
    Type: Grant
    Filed: November 19, 1996
    Date of Patent: August 24, 1999
    Assignee: Kodak Polychrome Graphics, LLC
    Inventors: Paul Richard West, Jeffery Allen Gurney
  • Patent number: 5942554
    Abstract: A method for the formation of a colored polymeric body which comprises subjecting a curable composition containing a color precursor and an onium salt to heat or actinic radiation to cure the composition, wherein the color precursor is converted to its colored form, and a curable composition capable of forming a colored polymeric body, are disclosed.
    Type: Grant
    Filed: February 20, 1996
    Date of Patent: August 24, 1999
    Assignee: Spectra Group Limited, Inc.
    Inventors: Yuijin Ren, Wolter Jager, Douglas C. Neckers
  • Patent number: 5922783
    Abstract: 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: Grant
    Filed: February 27, 1997
    Date of Patent: July 13, 1999
    Assignee: Loctite Corporation
    Inventor: Stan Wojciak
  • Patent number: 5914216
    Abstract: A multilayer circuit board having a resolution in the range of 25-80 .mu.m, and blind via-holes having an aspect ratio in the range of 2.0-0.6 for effecting access between the layers, wherein an insulating layer between said layers having the blind via-holes has a glass transition temperature in the range of 150-220.degree. C., and an epoxy group photosensitive resin composition is used therefor. A photosensitive resin composition having a preferable resolution and heat resistance is obtained. A multilayer circuit board is provided in which the thermal stress generated in the steps of a reflow process, a gold wire bonding process and a repairing process in a bare chip mounting process was reduced, and peeling off of the conductor wiring and deformation of the multilayer circuit board caused by mechanical stresses during the heating processes were suppressed. Accordingly, a decrease in the size and weight of an electronic apparatus is possible.
    Type: Grant
    Filed: July 18, 1997
    Date of Patent: June 22, 1999
    Assignees: Hitachi, Ltd., Hitachi Chemical Company, Ltd.
    Inventors: Satoru Amou, Masao Suzuki, Tokihito Suwa, Mineo Kawamoto, Akio Takahashi, Masanori Nemoto, Hiroyuki Fukai, Mitsuo Yokota, Shiro Kobayashi, Masashi Miyazaki
  • Patent number: 5900346
    Abstract: 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: Grant
    Filed: February 28, 1997
    Date of Patent: May 4, 1999
    Assignee: Shipley Company, L.L.C.
    Inventors: Roger F. Sinta, Juan C. Scaiano, Gary S. Calabrese
  • Patent number: 5882844
    Abstract: A chemically amplified positive resist composition contains (A) an organic solvent, (B) a base resin in the form of a polysiloxane having phenolic hydroxyl groups some of which are protected with alkoxyalkyl groups and having a weight average molecular weight of 2,000-50,000, (C) a photoacid generator, and (D) a vinyl ether group-containing compound. The composition has high sensitivity to actinic radiation, is developable with aqueous base to form a resist pattern, and lends itself to fine patterning.
    Type: Grant
    Filed: April 1, 1997
    Date of Patent: March 16, 1999
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Junji Tsuchiya, Toshinobu Ishihara, Shigehiro Nagura, Katsuya Takemura, Tsuguo Yamaoka
  • Patent number: 5880169
    Abstract: The invention provides a novel sulfonium salt having at least one acid labile group attached to a phenyl group in a molecule and a normal, branched or cyclic C.sub.1 -C.sub.20 alkylsulfonate anion. The novel sulfonium salt is effective for increasing the dissolution contrast between exposed and unexposed areas. Upon exposure, it generates an alkylsulfonic acid which is a weak acid, minimizing the influence of side reaction and deactivation during PEB step. The sulfonium salt is useful in a chemically amplified positive resist composition which lends itself to fine patterning and features high resolution.
    Type: Grant
    Filed: November 1, 1996
    Date of Patent: March 9, 1999
    Assignees: Shin-Etsu Chemical Co., Ltd., Nippon Telegraph and Telephone Corp.
    Inventors: Yoichi Osawa, Satoshi Watanabe, Katsuya Takemura, Shigehiro Nagura, Akinobu Tanaka, Yoshio Kawai
  • 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: 5858614
    Abstract: A photosensitive composition for volume hologram recording used for recording an interference fringe produced by the interference of laser beams or lights having excellent coherence as a fringe having a different refractive index, the composition comprising:(a) a radical polymerizable compound having a 9,9-diarylfluorene skeleton, which is liquid at a normal temperature;(b) a compound having compatibility with the component (a), which is selected from the group consisting of a cationic polymerizable compound, a radical polymerizable compound having no 9,9-diarylfluorene skeleton and a plasticizer; and(c) a radical photopolymerization initiator which is sensitive to laser beam having a specific wavelength or light having a specific wavelength and excellent coherence to polymerize the component (a);wherein an average refractive index of the component (a) is larger than that of the component (b).
    Type: Grant
    Filed: October 9, 1996
    Date of Patent: January 12, 1999
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Akihiko Sato, Masami Kawabata, Iwao Sumiyoshi
  • Patent number: 5855837
    Abstract: A novel method for producing thick composite parts based upon photopolymerizable compositions is disclosed. The constituents of the photopolymerizable mixture comprise a monomer or monomers capable of polymerizing by free radical or cationic mechanisms, and a photoinitiator system which possesses an absorbance characteristic which is effectively reduced, or self-eliminating, upon initiation of the polymerization reaction. Parts having thicknesses up to 2 cm and thicker for varying end use applications are made by photopolymerizing such compositions. In addition, using such compositions composite parts can be made using a reinforcement material such as a glass fiber mat present in an amount by weight of from about 5 to about 70%.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: January 5, 1999
    Assignee: Michigan State University
    Inventors: Alec B. Scranton, Bharath Rangarajan, Lindsay S. Coons
  • Patent number: 5856373
    Abstract: A visible-light photopolymerizable composition comprising a) a cationically polymerizable epoxy resin, b) a hydroxyl-containing material c) an aryliodonium salt and d) a visible light sensitizer that is an alpha-dicarbonyl compound having an extinction coefficient less than about 1000. Particularly preferred compositions of the present invention are dental materials.
    Type: Grant
    Filed: October 3, 1997
    Date of Patent: January 5, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: David A. Kaisaki, Sumita B. Mitra, William J. Schultz, Robert J. DeVoe
  • Patent number: 5854298
    Abstract: The present invention relates to a hybrid cure mechanism developed to polymerize highly filled/loaded, optically opaque, acrylate polymeric material compositions by radiant energy. The hybrid cure mechanism, when incorporated into a resinous composition, can be utilized to repair surface coatings on high performance aircraft where an extended composition pot life or application life and rapid cure capability combined with an acceptable shelf life stability are required. More specifically, the present invention relates to an electrically conductive resinous paint or gap filler for a suitably prepared composite or metallic surface. The composition also has applications on a production line of high performance aircraft.
    Type: Grant
    Filed: September 29, 1997
    Date of Patent: December 29, 1998
    Assignee: Lockheed Martin Corporation
    Inventors: Stephanie D. McNay, Dustin B. Martin, Thomas L. Marino, Douglas C. Neckers
  • Patent number: 5846689
    Abstract: 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: Grant
    Filed: September 9, 1996
    Date of Patent: December 8, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhold Schwalm, Dirk Funhoff, Horst Binder
  • Patent number: 5837748
    Abstract: 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: Grant
    Filed: August 8, 1997
    Date of Patent: November 17, 1998
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Tadahiro Sorori
  • Patent number: 5807905
    Abstract: 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: Grant
    Filed: November 21, 1996
    Date of Patent: September 15, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
  • Patent number: 5801212
    Abstract: A photopolymerizable composition comprising an addition-polymerizable compound having at least one ethylenic unsaturated double bond, a specific sensitizing dye represented by the following formula (I), and a titanocene compound: ##STR1## The substituents in formula (I) are defined in the specification.
    Type: Grant
    Filed: June 4, 1996
    Date of Patent: September 1, 1998
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasuo Okamoto, Shunichi Kondo
  • Patent number: 5798396
    Abstract: The present invention is directed to sulfonium salt-containing compounds represented by a following general formula; ##STR1## wherein R.sub.1 is alkyl containing from 1 to 18 carbon atoms, hydroxy, alkoxy containing from 1 to 18 carbon atoms, alkylcarbonyloxy containing from 1 to 18 carbon atoms or halogen, n is any of 0, 1, 2 or 3, however, each of R.sub.1 may be different from the others when n is 2 or more, R.sub.2 is alkyl containing from 1 to 6 carbon atoms, R.sub.3 and R.sub.4 are each independently hydrogen or alkyl containing from 1 to 6 carbon atoms, R.sub.5 and R.sub.6 are each independently hydrogen, alkyl containing from 1 to 6 carbon atoms, hydroxy, alkoxy containing from 1 to 6 carbon atoms, alkylcarbonyloxy containing from 1 to 18 carbon atoms or aromatic carbonyloxy, and R.sub.7 is alkyl containing from 4 to 20 carbon atoms or a group represented by a following formula; ##STR2## wherein R.sub.
    Type: Grant
    Filed: September 4, 1996
    Date of Patent: August 25, 1998
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Eiji Takahashi, Hiroo Muramoto
  • Patent number: 5773528
    Abstract: 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: Grant
    Filed: March 19, 1996
    Date of Patent: June 30, 1998
    Assignee: International Business Machines Corporation
    Inventors: Julio M. Alvarado, Kathleen L. Covert, Joseph P. Kuczynski
  • Patent number: 5770345
    Abstract: 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: Grant
    Filed: July 16, 1996
    Date of Patent: June 23, 1998
    Assignee: International Business Machines Corporation
    Inventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
  • Patent number: 5759721
    Abstract: A holographic recording medium comprises an acid generator capable of producing an acid upon exposure to actinic radiation; a binder; and at least one monomer or oligomer capable of undergoing cationic polymerization initiated by the acid produced from the acid generator. This recording medium is not subject to the disadvantages (for example, oxygen sensitivity) associated with radical-polymerized prior art holographic recording media.
    Type: Grant
    Filed: November 1, 1996
    Date of Patent: June 2, 1998
    Assignee: Polaroid Corporation
    Inventors: Pradeep K. Dhal, Michael G. Horner, Richard T. Ingwall, Eric S. Kolb, Parag G. Mehta, Richard A. Minns, Howard G. Schild, David A. Waldman
  • Patent number: 5753412
    Abstract: 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: Grant
    Filed: June 5, 1996
    Date of Patent: May 19, 1998
    Assignee: International Business Machines Corporation
    Inventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
  • Patent number: 5750587
    Abstract: The present invention relates to a radiation curable silicone release coating composition comprising (A) an alicyclic epoxy-functional silicone graft copolymer, (B) an organic compound having at least 2 alicyclic epoxy groups, and (C) a photocuring catalyst. The compositions of this invention are highly adhesive to a variety of substrates, have excellent coatability, and the release resistance values of films having the composition of this invention cured thereon can be adjusted over a wide range of values.
    Type: Grant
    Filed: April 24, 1996
    Date of Patent: May 12, 1998
    Assignee: Dow Corning Toray Silicone Co., Ltd.
    Inventors: Ryuko Manzouji, Tadashi Okawa
  • Patent number: 5744511
    Abstract: A visible-ray polymerizable composition comprising:(1) a monomer comprising a (meth)acrylate monomer; and(2) a visible-ray polymerization initiator comprising:(A) a coumarin dye;(B) at least one photo acid generator selected from the group consisting of a halo-alkyl substituted s-triazine derivative and a diphenyliodonium salt compound; and(C) an aryl borate compound.
    Type: Grant
    Filed: April 18, 1996
    Date of Patent: April 28, 1998
    Assignee: Tokuyama Corporation
    Inventors: Hideki Kazama, Takeshi Satoh, Makoto Oguri
  • Patent number: 5739174
    Abstract: A photocurable composition comrpising: (a) a photopolymerizable silane or siloxane containing epoxycylohexyl group(s), (b) a photoinitiator, and (c) a photosensitizer, wherein the photosensitizer comprises at least one material selected from the group consisting of sulfolene, sulfolene derivatives, isatin and isatin derivatives.
    Type: Grant
    Filed: May 17, 1996
    Date of Patent: April 14, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Fujio Hara
  • Patent number: 5731363
    Abstract: A photopolymerizable composition comprising an addition-polymerizable compound having at least one ethylenic unsaturated double bond, at least one specific sensitizing dye such as the following formula (I), and a titanocene compound: ##STR1## The substituents in formula (I) are defined in the specification.
    Type: Grant
    Filed: February 28, 1996
    Date of Patent: March 24, 1998
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasuo Okamoto, Syunichi Kondo
  • Patent number: 5731364
    Abstract: The invention provides positive- and negative-acting a photoresist compositions that contain a photoacid generator component that includes multiple aryl sulfonium compounds. Specifically, the photoactive component contains at least one multiple cation aryl sulfonium compound, preferably a di-cation compound. The photoactive component of the resists of the invention can be conveniently prepared and provide a deep UV sensitive resist with excellent microlithographic properties.
    Type: Grant
    Filed: January 24, 1996
    Date of Patent: March 24, 1998
    Assignee: Shipley Company, L.L.C.
    Inventors: Roger F. Sinta, James F. Cameron, Timothy G. Adams, Martha M. Rajaratnam, Michael F. Cronin
  • Patent number: 5721289
    Abstract: A curable pressure sensitive adhesive having long shelf stability comprising (a) at least one free radically polymerized polymer; (2) at least one cationically-polymerizable monomer; (3) a photo-activatable catalyst system for the cationically-polymerizable monomer comprising either at least one organometallic complex salt or at least one onium salt; and (4) optionally, a monohydric or polyhydric alcohol, wherein there is essentially no conversion of the cationically-polymerizable monomer of the curable pressure sensitive adhesive when stored in a manner to exclude actinic radiation, and methods of making the same.
    Type: Grant
    Filed: October 5, 1995
    Date of Patent: February 24, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Naimul Karim, Kevin E. Kinzer, Albert I. Everaerts, Leo W. Halm, Steven J. Keipert, Jerry W. Williams
  • Patent number: 5703137
    Abstract: The present invention relates to initiators for the polymerization and/or crosslinking, cationically and under photochemical and/or thermal activation and/or activation by a beam of electrons, of monomers and/or polymers containing organofunctional groups.The said initiators are of the type comprising an onium salt of an element from groups 15 to 17 of the Periodic Table (Chem & Eng News, Vol 63, N5, 26, of 4 Feb. 1985) and they are characterized in that they contain at least one polymerization and/or crosslinking accelerator chosen from .alpha.-hydroxylated carboxylic acid esters such as, for example, lactic acid esters. Another subject of the invention is compositions based on at least one cationically crosslinkable polyorganosiloxane and on at least one initiator.
    Type: Grant
    Filed: March 14, 1996
    Date of Patent: December 30, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventors: Christian Priou, Stuart Kerr, III
  • Patent number: 5700849
    Abstract: 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): ##STR1## wherein the all symbols are defined in the disclosure, and a titanocene compound.
    Type: Grant
    Filed: February 23, 1996
    Date of Patent: December 23, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Syunichi Kondo, Kazuo Fujita
  • Patent number: 5693688
    Abstract: The present invention relates to initiators of cationic polymerization and/or crosslinking, under photochemical and/or thermal activation and/or activation by a beam of electrons, of monomers and/or polymers containing organofunctional groups.These initiators give good performance with the majority of monomers/polymers, including in particular functional polyorganosiloxanes, which are crosslinkable cationically and under UV.The subject of the invention is also compositions based on at least one cationically crosslinkable polyorganosiloxane and on at least one initiator, as defined above.Application: paper anti-adhesion.
    Type: Grant
    Filed: September 15, 1995
    Date of Patent: December 2, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventor: Christian Priou
  • Patent number: 5691394
    Abstract: A photopolymerizable composition is disclosed, comprising an addition polymerizable compound having at least one ethylenically unsaturated double bond, a sensitizing dye represented by formula (I) and a titanocene compound. The photopolymerizable composition exhibits high sensitivity to active light rays over a wide region of from ultraviolet light to visible light.
    Type: Grant
    Filed: February 7, 1996
    Date of Patent: November 25, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Syunichi Kondo
  • Patent number: 5691100
    Abstract: A material for the formation of a pattern is provided which has a wide exposure latitude and is less liable to cause a dimensional change of a pattern with a change in exposure. The material comprises (A) a compound having a capability of producing an acid upon irradiation with an active beam, (B) a compound capable of producing a base or increasing its basicity, (C) a compound having at least one bond clearable with an acid and/or (D) a compound insoluble in water but soluble in an aqueous alkaline solution.
    Type: Grant
    Filed: March 29, 1996
    Date of Patent: November 25, 1997
    Assignee: Hoechst Japan Limited
    Inventors: Takanori Kudo, Seiya Masuda, Yoshiaki Kinoshita, Klaus Przybilla, Natsumi Endo, Natsumi Suehiro, Hiroshi Okazaki
  • Patent number: 5691111
    Abstract: The invention provides a photosensitive resin composition useful as a photoresist of chemical amplification type for deep UV lithography such as ArF excimer laser lithography. The resin composition contains, as an acid generator, an alkylsulfonium salt of the general formula (I), wherein R.sup.1 is a C.sub.7 to C.sub.12 alkyl having a bridged alicyclic structure or a C.sub.5 to C.sub.7 monocyclic alkyl, R.sup.2 is an alkyl, R.sup.3 is a C.sub.5 to C.sub.7 .beta.-oxomonocyclic alkyl or a C.sub.7 to C.sub.10 bridged cyclic alkyl having oxo group at the .beta.-position. The general formula (I) is inclusive of novel alkylsulfonium salts in which R.sup.1 is norbornyl group, adamantyl group or cyclohexyl group, R.sup.2 is methyl group and R.sup.3 is .beta.-oxocyclohexyl group or .beta.-oxonorbornane-2-yl group.
    Type: Grant
    Filed: July 13, 1995
    Date of Patent: November 25, 1997
    Assignee: NEC Corporation
    Inventors: Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
  • Patent number: 5672637
    Abstract: The present invention provides an energy polymerizable composition comprising at least one epoxy monomer or at least one vinyl ether monomer and an initiation system therefor, the initiation system comprising at least one organometallic complex salt and at least one stabilizing additive. The cured composition provides useful articles or coated articles.
    Type: Grant
    Filed: November 3, 1995
    Date of Patent: September 30, 1997
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Wayne S. Mahoney, Michael C. Palazzotto
  • Patent number: 5665791
    Abstract: Novel photosensitive polymer films are provided that include (1) a polymer carrier having .dbd.N--C(.dbd.O)-- groups; (2) an initiation system for photo polymerization; (3) polymerizable compounds; and (4) other chemicals as appropriate. The photosensitive polymer films demonstrate short pump times, short DRAW times, short fix times, and reduced noise levels equal to one-third to one-fifth the noise level of prior photosensitive polymer films.
    Type: Grant
    Filed: September 21, 1995
    Date of Patent: September 9, 1997
    Assignee: Tamarack Storage Devices, Inc.
    Inventors: Chung J. Lee, Jahja I. Trisnadi
  • Patent number: 5665494
    Abstract: Disclosed is a photosensitive composition for volume hologram recording which is used for recording an interference fringe produced by a laser beam or a light having excellent coherence, as fringes having different refractive index. The composition comprising:(a) a cationic polymerizable compound which is liquid at ambient temperature;(b) a radical polymerizable compound;(c) a radical photopolymerization initiator composition sensitized by a laser beam or a light having excellent coherence which has a specific wavelength to polymerize the ingredient (b); and(d) a cationic photopolymerization initiator composition which shows low photosensitivity to the light having a specific wavelength and is sensitized by a light having the other wavelength to polymerize the ingredient (a), wherein an average refractive index of the ingredient (a) is smaller than that of the ingredient (b). A process for producing the photosensitive composition is also disclosed.
    Type: Grant
    Filed: October 24, 1994
    Date of Patent: September 9, 1997
    Assignee: Nippon Paint Company, Ltd.
    Inventors: Masami Kawabata, Akihiko Sato, Iwao Sumiyoshi
  • Patent number: 5658708
    Abstract: An image recording material is disclosed, comprising a radiant ray-absorbing material, a compound having at least two enol ether groups represented by formula (I) and an alkali-soluble resin: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 maybe the same or different, each represents a hydrogen atom, an alkyl group or an aryl group, or any two of them may form a saturated or unsaturated olefinic ring by combining with each other; and a method for preparing the above image recording material is disclosed.
    Type: Grant
    Filed: February 8, 1996
    Date of Patent: August 19, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Syunichi Kondo