Specified Rate-affecting Material Contains Nitrogen Patents (Class 522/65)
  • Patent number: 5854299
    Abstract: Process for the polymerization of cyclic olefins by photochemical ring-opening metathesis polymerization by irradiation, using catalytic amounts of a heat-stable ruthenium or osmium catalyst which has at least one photolabile ligand, the other coordination sites being occupied by non-photolabile ligands.
    Type: Grant
    Filed: March 8, 1996
    Date of Patent: December 29, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Andreas Muhlebach, Paul Bernhard, Andreas Hafner, Thomas Karlen, Martin Andreas Ludi
  • Patent number: 5852067
    Abstract: A near infrared rays-curing putty composition containing (A) a polymerizable ethylenically unsaturated group-containing resin, (B) a polymerizable ethylenically unsaturated compound and (C) a near infrared rays polymerization initiator, said near infrared rays polymerization initiator (C) being a near infrared rays-absorbing cationic dye and a resin powder consisting of gelation polymer fine particles.
    Type: Grant
    Filed: November 15, 1996
    Date of Patent: December 22, 1998
    Assignees: Showa Denko K. K., Kansai Paint Co., Ltd.
    Inventors: Hajime Sukejima, Shinji Tomita, Shuichi Sugita, Kazuhiko Ooga
  • Patent number: 5834532
    Abstract: A curable composition comprising a polymerizable monomer having an acidic group in its molecule and an initiator. The composition has a viscosity in the range of from 100 to 30,000 cP at 37.5.degree. C. and may have additionally contain other polymerizable monomer and/or a filler. The composition is applied to a tooth surface directly or after applying a primer composition. There is also provided the primer composition which comprises a polymerizable monomer having an acidic group and a solvent.
    Type: Grant
    Filed: June 9, 1997
    Date of Patent: November 10, 1998
    Assignee: Sun Medical Co., Ltd.
    Inventors: Takashi Yamamoto, Weiping Zeng, Masami Arata, Tsuyoshi Banba, Harumi Tanaka
  • Patent number: 5811218
    Abstract: An N-aryl-.alpha.-amino acid (I), which is a novel compound, is effective as a photoinitiator. The photoinitiator composition including this photoinitiator is effective for improving photosensitive properties of photosensitive materials containing poly(amic acid) and an addition polymerizable compound used for pattern formation. Further, a photoinitiator composition (A) comprising an N-aryl-.alpha.-amino acid (I) or (I'), a 3-substituted coumarin (II) and/or an azabenzalcyclohexanone (III), or a photoinitiator composition (B) comprising an N-aryl-.alpha.-amino acid (I) or (I'), a 3-substituted coumarin (II) and a titanocene (IV), or a photoinitiator composition (C) comprising a 3-substituted coumarin (II), a titanocene (IV) and an oxime ester (V), is effective for improving photosensitive properties of photosensitive materials containing poly(amic acid) and an addition polymerizable compound used for pattern formation.
    Type: Grant
    Filed: July 17, 1995
    Date of Patent: September 22, 1998
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Makoto Kaji, Yasunori Kojima, Shigeki Katogi, Masataka Nunomura, Hideo Hagiwara, Dai Kawasaki, Mitsumasa Kojima, Hiroshi Suzuki, Hidetaka Satou
  • 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: 5789460
    Abstract: Curable compositions comprising a substance that produces a base when exposed to radiation and a polymer molecule that contains silicon-hydrogen bonds which react with hydroxyl groups under the action of the base to form silicon-oxygen bonds (Si--O) and hydrogen molecules. These compositions cure when exposed to radiation. A pattern can be formed by placing a mask between a coating of the composition and the radiation source during this exposure episode and thereafter dissolving the uncured composition. The compositions have little weight loss during their cure, they can be cured by low intensity radiation, and they yield heat-resistant cured products.
    Type: Grant
    Filed: January 24, 1996
    Date of Patent: August 4, 1998
    Assignee: Dow Corning Asia, Ltd.
    Inventors: Brian Robert Harkness, Mamoru Tachikawa
  • Patent number: 5783639
    Abstract: A resin composition comprising an epoxy group-containing cycloolefin resin and a crosslinking agent is provided. More specifically, a resin composition comprising an epoxy group-containing thermoplastic norbornene resin obtained by introducing epoxy groups into a thermoplastic norbornene resin, and as the crosslinking agent, a curing agent for epoxy resins or a photoreactive substance is provided. The resin composition is suitable for use as an insulating material.
    Type: Grant
    Filed: January 13, 1997
    Date of Patent: July 21, 1998
    Assignees: Nipon Zeon Co., Ltd., Fujitsu Limited
    Inventors: Hideaki Kataoka, Eiko Yuda, Shigemitsu Kamiya, Masahide Yamamoto, Yoshikatsu Ishizuki, Yasuhiro Yoneda, Daisuke Mizutani, Kishio Yokouchi
  • Patent number: 5776997
    Abstract: Process for the photocatalytic polymerization of a cyclical olefin or at least two different cyclical olefins in the presence of a metal compound as the catalyst, in which a photochemical ring-opening metathesis polymerization is carried out in the presence of a catalytic amount of at least one heat-stable titanium(IV), niobium(V), tantalum(V), molybdenum(VI) or tungsten(VI) compound in which a silylmethyl group and at least one halogen are bonded to the metal. The process can also be carried out by first performing the irradiation and ending the polymerization by heating.The process is suitable, for example, for the production of thermoplastic shaping compounds, coatings and images in relief.
    Type: Grant
    Filed: April 23, 1997
    Date of Patent: July 7, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Andreas Hafner, Andreas Muhlebach, Paul Adriaan Van Der Schaaf
  • Patent number: 5756648
    Abstract: Photosensitive polyimides (Ps-PIM) materials have been synthesized that belong to three families of Ps-PIM materials. Through the use of precursors, various catalytic compositions with differing photosensitivities are provided. The results are Ps-PIM materials having increased photosensitivities at wavelengths longer than approximately 330 to 350 nm and an associated catalytic system that is insensitive to oxygen. A variety of applications, including use in holographic systems, are improved by the present invention.
    Type: Grant
    Filed: October 25, 1995
    Date of Patent: May 26, 1998
    Assignee: Tamarack Storage Devices, Inc.
    Inventor: Chung J. Lee
  • Patent number: 5747172
    Abstract: Silicone release agents comprising propenyl-ether functionalized silicones exhibit a rapid cationic induce photo-cure. Such propenyl-ether functionalized silicones are synthesized by the hydrosilation of various .alpha.-allyloxy-.omega.-(1-propenoxy) alkanes with various linear and cyclic hydrogen functional siloxanes.
    Type: Grant
    Filed: August 30, 1995
    Date of Patent: May 5, 1998
    Assignee: General Electric Company
    Inventor: James V. Crivello
  • Patent number: 5728750
    Abstract: Radiation-curable compositions comprisinga) compounds having at least two carbon-carbon double bonds with which it is possible for primary or secondary amino groups to form adducts in the form of a Michael-analogous addition reaction (referred to in short below as activated double bonds)b) capped amino compounds which on irradiation with high-energy light liberate amino compounds having primary, secondary or primary and secondary amino groups, the overall number of hydrogen atoms bonded in the amino groups (amine hydrogen atoms) being at least 2.
    Type: Grant
    Filed: May 29, 1996
    Date of Patent: March 17, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhold Schwalm, Wolfgang Reich, Lukas Haussling, Erich Beck
  • Patent number: 5728748
    Abstract: A medical implant made of polymeric material having an increased oxidation resistance is formed by a method including the steps of placing a resin powder in a sealed container. A substantial portion of the oxygen is removed from the sealed container by either a vacuum, an oxygen absorbent or by flushing with inert gas. The container is then repressurized with a gas such as nitrogen, argon, helium or neon so that long term storage may be possible. On use, the resin is transferred to a forming device which both melts and forms the resin in an oxygen reduced atmosphere to produce a polymeric raw material such as a rod or bar stock. The medical implant is then formed from this raw material annealed and sealed in an air-tight package in an oxygen reduced atmosphere. The implant is then radiation sterilized and thereafter annealed in the package for a predetermined time and temperature sufficient to form cross-links between any free radicals in neighboring polymeric chains.
    Type: Grant
    Filed: October 16, 1996
    Date of Patent: March 17, 1998
    Assignee: Howmedica Inc.
    Inventors: Deh-Chuan Sun, Casper F. Stark
  • Patent number: 5723511
    Abstract: A process for the preparation of branched thermoplastic resins comprising: heating a mixture of a free radical initiator, at least one first free radical reactive monomer, at least one free radical reactive branching agent compound, and at least one stable free radical agent, to produce a linear or unbranched polymer product with a free radical initator fragment at one end and a covalently bonded stable free radical agent at the other end of the polymerized chain of monomers; and irradiating the unbranched polymer product in the presence of a reactive compound selected from the group consisting of a free radical reactive monomer, a branching agent compound, and mixtures thereof to form a branched polymeric product.
    Type: Grant
    Filed: June 17, 1996
    Date of Patent: March 3, 1998
    Assignee: Xerox Corporation
    Inventors: Peter M. Kazmaier, Barkev Keoshkerian, Karen A. Moffat, Michael K. Georges, Gordon K. Hamer, Richard P. N. Veregin
  • Patent number: 5721291
    Abstract: The invention relates to a composition based on crosslinkable epoxy-functional organopolysiloxanes. This composition comprises:A. at least 10% by weight of a linear polyorganosiloxane A (POS) of average general formula (II): ##STR1## in which: R.sub.1 is CH.sub.3, R' is an alkylene containing 2 to 50 C, R is an alkyl having from 6 to 26 C, X is R.sub.1, H, --R'-epoxy or hydroxyl, x=40-150, t=3-9, z=0-5 and y=0,B. at least one second crosslinkable epoxy-functional POS (B), B being present in the proportion of at most 90% by weight and corresponding to: B(a) with x=160-1000, t=1-15, z=0-5 and y=0, B(b) with x=0-120, t=10-30, z=0-5 and y=0, or B(c) with x=0-200, t=0-5, z=0-5 and y=10-90,C. and at least one photoinitiator.This composition can be used in the manufacture of protectors for adhesive bodies ("release liners"), papers or plastics or of liner-free self-adhesive labels.
    Type: Grant
    Filed: February 20, 1996
    Date of Patent: February 24, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Eric Gaulle, Christian Priou, Andre Soldat
  • Patent number: 5698369
    Abstract: Disclosed is a photosensitive composition comprising a sulfonimide compound represented by formula (I):R.sub.1 --SO.sub.2 --NR.sub.3 --SO.sub.2 --R.sub.2 (I)wherein R.sub.1, R.sub.2 and R.sub.3 each represents an unsubstituted or substituted aromatic group or an unsubstituted or substituted alkyl group.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: December 16, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Koichi Kawamura, Fumikazu Kobayashi, Tsukasa Yamanaka
  • Patent number: 5693452
    Abstract: A positive chemically amplified resist composition is disclosed, comprising (a) a compound which generates an acid upon irradiation with active light or radiant ray; (b) a resin insoluble in water but soluble in an aqueous alkali solution; and (c) a low molecular acid-decomposable dissolution inhibitor having a molecular weight of 3,000 or less and containing an acid-decomposable alkyl ester group represented by formula (I), and which increases its solubility in an alkali developer by the action of an acid, and having a sodium content and a potassium content each of 30 ppb or less. Also disclosed is a positive chemically amplified resist composition comprising the foregoing compound (a) and (d) a resin having an acid-decomposable alkyl ester group represented by formula (I), and which increases its solubility in an alkali developer by the action of an acid, and having a sodium content and a potassium content each of 30 ppb or less. Still further disclosed are methods for producing the compounds (c) and (d).
    Type: Grant
    Filed: October 26, 1995
    Date of Patent: December 2, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Toru Fujimori
  • Patent number: 5691396
    Abstract: The invention provides a novel polysiloxane compound, typically polyhydroxybenzylsilsesquioxane, having some hydroxyl groups replaced by acetal groups and optionally acid labile groups. The polysiloxane compound is useful as an alkali soluble polymer for positive resist material.
    Type: Grant
    Filed: September 24, 1996
    Date of Patent: November 25, 1997
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Katsuya Takemura, Junji Tsuchiya, Osamu Watanabe, Toshinobu Ishihara
  • Patent number: 5691395
    Abstract: Radiation sensitive compositions, processes for using the compositions, and articles of manufacture comprising the compositions. The photoimageable compositions of the invention comprises a radiation sensitive component, a resin binder and a polybutadiene that comprises one or more internal epoxide groups. In preferred aspects, the compositions of the invention further comprise a crosslinking agent such as a melamine or an epoxidized material, or mixtures thereof.
    Type: Grant
    Filed: July 12, 1994
    Date of Patent: November 25, 1997
    Assignee: Shipley Company Inc.
    Inventors: Philip D. Knudsen, Charles R. Shipley, Daniel Y. Pai
  • Patent number: 5691113
    Abstract: A method for the anionic photoinitiation of a substrate that includes exposing the substrate to an inorganic complex that releases an anionically charged nucleophile on irradiation.
    Type: Grant
    Filed: October 18, 1994
    Date of Patent: November 25, 1997
    Assignee: The University of Georgia Research Foundation, Inc.
    Inventor: Charles R. Kutal
  • Patent number: 5684065
    Abstract: To provide a fluorine-containing resin molded article surface-modified by irradiating, onto a surface thereof, a laser beam having a wavelength of 150 to 370 nm through a basic solution, preferably an aqueous basic solution. The surface-modified fluorine-containing resin molded article is excellent in adhesion to not only organic materials but also metals.
    Type: Grant
    Filed: December 19, 1996
    Date of Patent: November 4, 1997
    Assignee: Daikin Industries, Ltd.
    Inventors: Hiroyuki Hiraoka, Shinji Tamaru, Osamu Tanaka
  • Patent number: 5650477
    Abstract: Liquid reactive thermosetting compositions comprising:A) At least one polyepoxide or a mixture of one or more polyepoxides with at least one monoepoxide, of an aliphatic, cycloaliphatic or mixed nature;B) at least one anhydride of a di- or polycarboxylic acid of an aliphatic, cycloaliphatic or mixed nature;C) at least one catalyst capable of promoting the rapid polymerization of the mixture A+B under microwave irradiation and having general formula (I):N.tbd.C--CH.sub.2 --CH(Z)--(O).sub.r --Y.sup.+ NR.sub.1 R.sub.2 R.sub.3 X.sup.-.
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: July 22, 1997
    Assignee: Enichem S.p.A.
    Inventors: Fabrizio Parodi, Renata Gerbelli, Mark DeMeuse
  • Patent number: 5644004
    Abstract: A novel and safe ethylenically unsaturated peroxyester composition derived from an ethylenically unsaturated dicarboxylic acid is provided, as well as processes for making and using the composition. The peroxyester composition comprises about 0.04 to about 0.70 mole fraction of a first component compound having a formula I: ##STR1## about 0.32 to about 0.50 mole fraction of a second component compound having a formula II: ##STR2## about 0.04 to about 0.70 mole fraction of a third component compound having a formula III: ##STR3## wherein Q is an unsaturated ethylene divalent radical and R.sup.1 and R.sup.2 are organic substituents. Polymeric-peroxides are prepared via polymerizing the peroxyester compositions. The peroxyester compositions are also used for curing unsaturated polyester resins and for initiating polymerization of ethylenically unsaturated monomers.
    Type: Grant
    Filed: January 25, 1995
    Date of Patent: July 1, 1997
    Assignee: Elf Atochem North America, Inc.
    Inventor: Jose Sanchez
  • Patent number: 5627010
    Abstract: A radiation sensitive composition, process for using said composition, and substrates coated with said composition. The photoimageable composition comprises a photobase generator compound, a resin binder and a material capable of crosslinking in the presence of base. In preferred aspects, the invention provides a negative-acting, aqueous developable photoimageable composition comprising a photobase generator compound, a resin binder which preferably is a phenolic polymer, a crosslinking agent that comprises one or more active groups that will undergo base-initiated crosslinking, and a curing agent.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: May 6, 1997
    Assignee: Shipley Company, L.L.C.
    Inventors: Daniel Y. Pai, Stephen S. Rodriguez, Kevin J. Cheetham, Gary S. Calabrese, Roger F. Sinta
  • Patent number: 5602191
    Abstract: Radiation-curable acrylates are prepared by a process in which the hydroxy compound is reacted with acrylic acid or methacrylic acid in a first stage and, in a second stage, the reaction product of the first stage is reacted with an epoxide compound in the presence of, as a catalyst, a quaternary ammonium or phosphonium compound of the general formula ##STR1## where X.sup.- is an opposite ion and R.sup.1 to R.sup.4 independently of one another are each C.sub.1 -C.sub.18 -alkyl which may be substituted by one or two phenyl groups or are each C.sub.6 -C.sub.12 -aryl which may be substituted by one or two C.sub.1 -C.sub.6 -alkyl groups.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: February 11, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Reich, Erich Beck, Edmund Keil, Ulrich Erhardt, Adolf Nuber
  • Patent number: 5558971
    Abstract: A resist material comprising (a) a terpolymer, (b) a photoacid generator, and (c) a solvent has high light sensitivity, heat resistance, adhesiveness, resolution, etc., and is suitable for forming a pattern of rectangular shape.
    Type: Grant
    Filed: March 21, 1995
    Date of Patent: September 24, 1996
    Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.
    Inventors: Fumiyoshi Urano, Takaai Negishi, Akiko Katsuyama, Masayuki Endo
  • Patent number: 5514728
    Abstract: Salts having a cationic portion of either a mono-, polyvent metal center, onium salts or organometallic salts and a nonnucleophilic anion are useful as catalysts and initiators that may be photochemically or thermally-activated, and polymerizable compositions containing such catalysts and initiator salts and at least one of a cationic or free-radical addition polymerizable monomers, or catalyzed step-growth polymerizable monomers.
    Type: Grant
    Filed: July 23, 1993
    Date of Patent: May 7, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: William M. Lamanna, Michael C. Palazzotto, Robert J. DeVoe, Fred B. McCormick, Jeffrey M. Olofson, Allen R. Siedle, Peggy S. Willett
  • Patent number: 5496678
    Abstract: A photosensitive composition which comprises, as essential components:(A) a polymer having carboxyl group(s) and hydroxyphenyl group(s), or (A') a polymer having carboxyl group(s) and (A") a polymer having hydroxyphenyl group(s),(B) a compound having at least two vinyl ether groups in the molecule, and(C) a compound which generates an acid when irradiated with an actinic ray, and which is useful as a positive type photoresist having high resolution and excellent formability of fine image pattern, a material for printing, etc.; and a process for pattern formation using said composition.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: March 5, 1996
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Genji Imai, Naozumi Iwasawa, Tsuguo Yamaoka
  • Patent number: 5489664
    Abstract: Crosslinkable liquid composition based on organic isocyanates and epoxy compounds, comprising the following components:(A) an organic polyisocyanate;(B) a polyepoxide or mixture of a polyepoxide and a monoepoxide; and(C) a catalyst constituted by at least one cyanoderivative containing a quaternary nitrogen atom,which composition can be polymerized at temperatures of 40.degree. C. or higher, by a process comprising exposure thereof to a non-ionizing electromagnetic radiation having a frequency comprised in the microwave range of frequencies, to obtain a solid material endowed with an excellent combination of physical, chemical and mechanical properties.
    Type: Grant
    Filed: November 4, 1994
    Date of Patent: February 6, 1996
    Assignees: Enichem S.p.A., Eniricerche S.p.A.
    Inventors: Fabrizio Parodi, Renata Gerbelli, Mark De Meuse
  • Patent number: 5480918
    Abstract: A novel initiator for photopolymerization is provided, which can polymerize cationically polymerizable organic material by only irradiating at wavelength of 200-500 nm without specific sensitizer and/or post-curing even when it is used at comparatively small amount, whereby the obtained cured product has good physical properties and electric properties. The initiator for photopolymerization of cationically polymerizable organic material according to the present invention comprises a composite obtainable from a reaction between (a) charge transfer complex consisting of biscyclopentadienyl iron derivative and quinoid and (b) at least one salt selected from a group consisting of tetrafluoroborates, hexafluorophosphates and hexafluoroantimonates.
    Type: Grant
    Filed: October 14, 1994
    Date of Patent: January 2, 1996
    Assignee: Autex, Inc.
    Inventor: Yusuke Sasaki
  • Patent number: 5468785
    Abstract: The invention relates to the use of cobaloximes and related cobalt(II) complexes which have essentially planar equatorially coordinated ligands and a pair of axially coordinated ligands which have at least one carbon-cobalt bond, as photoinitiators for free radical polymerizations. By selection of the appropriate cobaloximes and related complexes, it is possible to prepare polymers which have useful terminal functionality at both the head and the tail ends of the growing polymer chain. The process also teaches the photochemical polymerization and copolymerizations whereby the alkyl cobaloximes and related compounds, which are used as the photoinitiators, have alkyl groups, which may in essence, be polymers with carbon-cobalt chain ends, thereby allowing grafting reactions to occur to the polymer backbone.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: November 21, 1995
    Assignee: University of Akron
    Inventors: Michael P. Greuel, Labros D. Arvanitopoulos, H. James Harwood
  • Patent number: 5468589
    Abstract: A resist composition comprising (a) a polymer having at least repeating units of the formulae: ##STR1## (b) a photoacid generator and (c) a solvent, has high sensitivity to light, excellent heat resistance, adhesiveness to a substrate and suitable for pattern formation with high resolution.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: November 21, 1995
    Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.
    Inventors: Fumiyoshi Urano, Hirotoshi Fujie, Keiji Oono, Takaaki Negishi
  • Patent number: 5459173
    Abstract: Stable thiol-ene compositions are provided which comprise a polythiol, a polyene and a stabilizer system comprising an alkenyl substituted phenolic compound having a formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are independently selected from the group consisting of H, OR, a C.sub.1 -C.sub.8 alkyl, substituted alkyl, alkenyl or substituted alkenyl, a C.sub.6 -C.sub.20 aryl or substituted aryl, or a cyano group; R.sup.4 is H, R, OR, halogen, COR, COOR, or SR; R.sup.5 is OH, OR, OCOR, OCOOR, OCONHR, or OTMS; R is a C.sub.1 -C.sub.6 alkyl, a cycloalkyl, or a C.sub.6 -C.sub.20 caryl or substituted aryl; x and y are 1, 2, or 3; z is 0, 1, or 2; and x+y+z=2, 3, or 4; or a formula: ##STR2## where x, y, z, w, R.sup.1 R.sup.2 R.sup.3, R.sup.4 and R.sup.5 are defined as above, except that x+y+z=2-6, and R.sup.6 is CH.sub.2, C(CH.sub.3).sub.2, O, S, or SO.sub.
    Type: Grant
    Filed: June 22, 1993
    Date of Patent: October 17, 1995
    Assignee: Loctite Corporation
    Inventors: David M. Glaser, Anthony F. Jacobine, Paul J. Grabek
  • Patent number: 5429846
    Abstract: The present invention provides a photo-setting conductive coating composition which is used as an antistatic material constituting articles wherein static electrification must be avoided, such as storage vessels for semi-conductor wafers, electronic/electric parts, floor/wall coverings for a production factory of semi-conductors, etc.The photo-setting conductive coating composition comprising 100 parts by weight of an antimony oxide-containing tin oxide powder (a) having a particle size of 0.01 to 0.4 .mu.m, 10 to 100 parts by weight of a (meth)acrylate compound (b) having at least two (meth)acryloyl groups in a molecule, 10 to 100 parts by weight of an acetal resin (c) having a residual hydroxyl group of 20 to 80 molar %, 0.1 to 10 parts by weight of a photopolymerization initiator (d) and 100 to 1000 parts by weight of an organic solvent (e).
    Type: Grant
    Filed: October 25, 1994
    Date of Patent: July 4, 1995
    Assignee: Sekisui Chemical Co., Ltd.
    Inventors: Toshiya Sugimoto, Minoru Suezaki, Kouji Maruyama
  • Patent number: 5420173
    Abstract: A novel and safe ethylenically unsaturated peroxyester composition derived from an ethylenically unsaturated dicarboxylic acid is provided, as well as processes for making and using the composition. The peroxyester composition comprises about 0.04 to about 0.70 mole fraction of a first component compound having a formula I: ##STR1## about 0.32 to about 0.50 mole fraction of a second component compound having a formula II: ##STR2## about 0.04 to about 0.70 mole fraction of a third component compound having a formula III: ##STR3## wherein Q is an unsaturated ethylene divalent radical and R.sup.1 and R.sup.2 are organic substituents. Polymeric-peroxides are prepared via polymerizing the peroxyester compositions. The peroxyester compositions are also used for curing unsaturated polyester resins and for initiating polymerization of ethylenically unsaturated monomers.
    Type: Grant
    Filed: March 30, 1994
    Date of Patent: May 30, 1995
    Inventor: Jose Sanchez
  • Patent number: 5418113
    Abstract: A photosensitive resin composition comprises (a) a polyvinylcarbazole type polymer, (b) a halogen-containing compound and (c) or least one compound selected from the group consisting of a triarylhydrazyl, a triarylcarbonium type coloring matter having at least one carbazolyl group, and a reaction product of a styryl base with a halogenated carbon. A method of preparing a volume type hologram member comprises the steps of: subjecting a photosensitive material having a photosensitive layer comprising the photosensitive resin composition to exposure using a laser beam to form an interference pattern; and subjecting the photosensitive material thus exposed to light to development processing using a solvent.
    Type: Grant
    Filed: March 3, 1993
    Date of Patent: May 23, 1995
    Assignee: Canon Kabushiki Kaisha
    Inventors: Yoko Yoshinaga, Naosato Taniguchi, Hiroyoshi Kishi, Tetsuro Kuwayama, Nobuo Kushibiki
  • Patent number: 5409764
    Abstract: A curable adhesive composition comprising an unsaturated polyester oligomer (A) of any of the following formulae (I) to (IV), obtained by reacting a compound (a) having a hydroxyl group and/or an amino group, a cyclic acid anhydride (b) and an epoxide (c) having an ethylenically unsaturated group, and an adhesive polymer (B), ##STR1## wherein: R.sub.1 is a divalent organic moiety having 1 to 40 carbon atoms,R.sub.2 is a divalent organic moiety having 1 to 10 carbon atoms,R.sub.3 is hydrogen or methyl,R.sub.4 is a monovalent organic moiety having 1 to 40 carbon atoms,R.sub.5 is a monovalent organic moiety having 1 to 40 carbon atoms,R.sub.6 is hydrogen or a monovalent organic moiety having 1 to 10 carbon atoms, andn is an integer of 2 or greater.
    Type: Grant
    Filed: September 23, 1994
    Date of Patent: April 25, 1995
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Tsukasa Otsuki, Masato Yanagi, Toshikazu Onikubo, Kouichi Iibuchi
  • Patent number: 5403695
    Abstract: Disclosed herein is a resist for forming patterns, which is greatly sensitive to ultraviolet rays an ionizing radiation, and which can therefore form a high-resolution resist pattern if exposed to ultra violet rays or an unionizing radiation. Hence, the resist is useful in a method of manufacturing semicon ductor devices having high integration densities. The resist comprises tert-butoxycarbonyl methoxypolyhydroxy styrene and an o-quinonediazide compound.
    Type: Grant
    Filed: April 30, 1992
    Date of Patent: April 4, 1995
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Rumiko Hayase, Yasunobu Onishi, Hirokazu Niki, Naohiko Oyasato, Yoshihito Kobayashi, Shuzi Hayase
  • Patent number: 5376691
    Abstract: The invention describes a material for making temporary crowns and bridges that comprises two pastes and can be mixed in a static mixer/application in one cycle without the incorporation of bubbles, and can be easily pressed out. The polymers produced from this are aesthetically pleasing and remarkably break-resistant. Their polymerization-related shrinkage proves to be extremely low. Their radiopaqueness meets clinical requirements.
    Type: Grant
    Filed: March 1, 1993
    Date of Patent: December 27, 1994
    Assignee: Ernst Muhlbaner KG
    Inventors: Ulrich May, Jurgen Engelbrecht, Ernst Muhlbauer, Edgar Lein
  • Patent number: 5372908
    Abstract: A photosensitive composition comprises a polysilane having a repeating unit represented by formula (1) and a compound which generates an acid upon exposure to light: ##STR1## wherein each of R.sup.1 and R.sup.2 independently represents a hydrogen atom, a substituted or nonsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or nonsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or nonsubstituted aralkyl group having 7 to 22 carbon atoms. This photosensitive composition exhibits a high-sensitivity, and can be formed into a polysilane film pattern having a high-resolution, when it is subjected to exposure to Deep UV light, an EB, an X-ray, or the like, hard baking, and development under appropriate conditions. When an aromatic ring substituted by a hydroxyl group, a substituted or nonsubstituted alkoxyl group, or a substituted or nonsubstituted siloxyl group is introduced in one of side chains R.sup.1 and R.sup.
    Type: Grant
    Filed: July 8, 1992
    Date of Patent: December 13, 1994
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shuji Hayase, Yoshihiko Nakano, Yukihiro Mikogami
  • Patent number: 5371116
    Abstract: Vulcanizable organopolysiloxane compositions comprise a hydroxy-terminated organopolysiloxane, an acrylic or methacryllc functional alkoxy silane, a divalent tin compound, an alkoxy-.alpha.-silyl ester, a photopolymerization initiator, and a curing catalyst whereby the composition is cured by UV irradiation and/or by the action of moisture in air. The composition has good shelf stability and can yield rubber elastomers having good physical properties.
    Type: Grant
    Filed: July 13, 1993
    Date of Patent: December 6, 1994
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takafumi Sakamoto, Masatoshi Arai, Kei Miyoshi
  • Patent number: 5366846
    Abstract: Radiation sensitive compositions, processes for using the compositions, and articles of manufacture comprising the compositions. The photoimageable compositions of the invention comprises a radiation sensitive component, a resin binder and a polybutadiene that comprises one or more internal epoxide groups. In preferred aspects, the compositions of the invention further comprise a crosslinking agent such as a melamine or an epoxidized material, or mixtures thereof.
    Type: Grant
    Filed: June 28, 1993
    Date of Patent: November 22, 1994
    Assignee: Shipley Company Inc.
    Inventors: Philip D. Knudsen, Charles R. Shipley, Daniel Y. Pai
  • Patent number: 5350660
    Abstract: A resist material comprising (a) a polymer having a monomer unit having a special functional group, a monomer unit having a phenolic hydroxyl group, and if necessary a third monomer unit, (b) a photoacid generator, and (c) a solvent can provide a resist film excellent in heat resistance and adhesiveness to a substrate when exposed to light with 300 nm or less such as deep UV light, KrF excimer laser light, etc., and is suitable for forming ultrafine patterns.
    Type: Grant
    Filed: January 28, 1991
    Date of Patent: September 27, 1994
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Fumiyoshi Urano, Masaaki Nakahata, Hirotoshi Fujie, Keiji Oono
  • Patent number: 5340701
    Abstract: Fluorine-free titanocene compounds of the formula I or II ##STR1## in which both R.sub.1 radicals are preferably, independently of one another, cyclopentadienyl.sup..crclbar., which is unsubstituted or substituted by alkyl,alkoxy or --Si(R.sub.2).sub.3, and both R.sub.2 radicals are, in particular, alkyl, ##STR2## Z is --NR.sub.10 --, --0-- or --S--, Y is Cl, Br, I, CN, SCN, --O--CO--CH.sub.3, --O--CO--phenyl or --O--SO.sub.2 --CH.sub.3,n is 1 or 2,m is 0 or 1, where the sum of n and m must be 2,R.sub.3, R.sub.4 and R.sub.5 are in particular, independently of one another, hydrogen, Cl, alkyl, cycloalkyl, adamantyl, phenyl, pyrryl or biphenylyl, where these radicals are unsubstituted or substituted by alkyl, Cl, alkylthio, --NR.sub.8 R.sub.9, phenyl, phenylthio or C.sub.1 -C.sub.10 alkoxy, or R.sub.3, R.sub.4 and R.sub.5 are alkenyl, alkoxy, cycloalkoxy, phenoxy, benzyloxy, tetrahydrofurfuryloxy, alkylthio, cycloalkylthio, benzylthio or phenylthio, where R.sub.3 and R.sub.
    Type: Grant
    Filed: April 6, 1993
    Date of Patent: August 23, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Vincent Desobry
  • Patent number: 5340898
    Abstract: Cationically crosslinkable polyorganosiloxane compositions, well suited for providing antiadhesive coatings on a wide variety of shaped substrates via the photochemical/electron beam crosslinking thereof, include a catalytically effective amount of an onium borate of an element of Groups 15 to 17 of the Periodic Table, the anionic borate moiety of which onium borate having the formula:[BX.sub.a R.sub.b ].sup.-in which a and b are integers ranging from 0 to 4 and a+b=4; the symbols X are each a halogen atom when a ranges up to 3 and an OH functional group when a ranges up to 2; and the symbols R, which may be identical or different, are each a phenyl radical substituted by at least one electron-withdrawing substituent or by at least two halogen atoms, or an aryl radical containing at least two aromatic ring members, or such aryl radical bearing at least one electron-withdrawing substituent.
    Type: Grant
    Filed: March 23, 1993
    Date of Patent: August 23, 1994
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jacques Cavezzan, Christian Priou
  • Patent number: 5331020
    Abstract: Organosilicon compounds with a siloxane portion and groups of the general formula --OR'OCH.dbd.CHR" (i) linked via an Si--O--C bond, wherein R' is a divalent hydrocarbon radical or a group --R.degree.--(OR.degree.).sub.n --, wherein R.degree. is alkylene and n is from 1 to 12, R" is H or alkyl are useful in radiation curable compositions, in which they are mixed with an initiator. The compositions are particularly useful in UV radiation curable relase coatings.
    Type: Grant
    Filed: August 16, 1993
    Date of Patent: July 19, 1994
    Assignee: Dow Corning Limited
    Inventors: Scott S. D. Brown, Peter C. Hupfield, Peter Y. K. Lo, Richard G. Taylor
  • Patent number: 5314983
    Abstract: Mixtures of polyisocyanates and epoxides are cured by microwave irradiation, optionally with microwave or thermal post-curing to produce cured polymer articles having good chemical, electrical and mechanical properties.
    Type: Grant
    Filed: November 9, 1992
    Date of Patent: May 24, 1994
    Assignee: Enichem S.p.A.
    Inventors: Mark T. DeMeuse, Fabrizio Parodi
  • Patent number: 5310862
    Abstract: A photosensitive polyimide precursor composition containing as main ingredients a poly(amic acid) wherein at least one molecular end is esterified with an alcohol, a compound containing carbon-carbon unsaturation having photoreactivity, and a photopolymerization initiator.The photosensitive polyimide precursor composition of the present invention can be prepared without the formation of any harmful by-product. When film formed from this composition is masked for patterning and then subjected to exposure and development using a developer, the amount of exposed portion dissolved in the developer until unexposed portion is dissolved off by the developer, is small and so it is possible to obtain a thick pattern. Further, by heat-treating this pattern, there can be obtained a thick polyimide pattern.
    Type: Grant
    Filed: August 6, 1992
    Date of Patent: May 10, 1994
    Assignee: Toray Industries, Inc.
    Inventors: Hideshi Nomura, Masuichi Eguchi, Masaya Asano
  • Patent number: 5242491
    Abstract: Novel gel compositions are provided which exhibit a drastic discontinuous volume change when exposed to or shielded from light energy.
    Type: Grant
    Filed: January 30, 1992
    Date of Patent: September 7, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: Akira Mamada, Toyoichi Tanaka, Dawan Kungwatchakun, Masahiro Irie
  • Patent number: 5217843
    Abstract: A positive radiation-sensitive mixture is disclosed which contains a compound which forms an acid under the action of high-energy radiation, and an acid-cleavable compound, wherein the compound which forms an acid contains aliphatically bound halogen (chlorine or bromine) and has a pK.sub.a value of less than about 12 or is a derivative of a compound having such a pK.sub.a value which can be converted into the free compound by acid catalysis. A positive recording material and a process for recording high-energy radiation using the material are also disclosed. The mixture, and in particular the recording material produced therefrom, has relatively high sensitivity and improved resolution and, in addition, does not exhibit image fogging after development.
    Type: Grant
    Filed: March 12, 1990
    Date of Patent: June 8, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralph Dammel, Juergen Lingnau, Georg Pawlowski, Juergen Theis
  • 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