Patents Examined by Arthur H. Koeckert
  • Patent number: 5373032
    Abstract: This invention relates to alk-1-enyl etherurethanyl block prepolymers which are curable by cationically initiated radiation and which are defined by the formula ##STR1## wherein m has a value of from 1 to 25;A is C.sub.2 to C.sub.12 alkylene, C.sub.6 to C.sub.14 aryl, both groups optionally substituted with lower alkyl, halo lower alkyl, alkyleneoxy, halogen or aryl;R.sub.1 is alkylene containing from 1 to 6 carbon atoms;R.sub.2 is a saturated or unsaturated divalent radical containing from 1 to 14 carbon atoms and is selected from the group of alkylene, alkenylene and arylene, each group optionally substituted with oxygen, halogen, lower alkyl and/or hydroxy;R.sub.3 is hydrogen or C.sub.1 to C.sub.6 alkyl;R.sub.4 is C.sub.1 to C.sub.6 alkylene, C.sub.6 to C.sub.14 arylene, lower alkyl substituted phenylene or xylylene andR.sub.5 is hydrogen or C.sub.1 to C.sub.4 alkyl.
    Type: Grant
    Filed: August 18, 1993
    Date of Patent: December 13, 1994
    Assignee: ISP Investments Inc.
    Inventors: Mark M. Miller, Jeffrey S. Plotkin
  • Patent number: 5371259
    Abstract: Compounds of the formula I are described[R.sup.1 (Fe.sup.II R.sup.2 .sub.a ].sub.q.sup.+an anX.sup.-q (I)in which a is 1 or 2, n is 1 or 2, R.sup.1 is a substituted or unsubstituted .pi.-arene, R.sup.2 is a substituted or unsubstituted .pi.-arene or cyclopentadienyl anion or indenyl anion, q is an integer from 1 to 3, and X is FSO.sup.-.sub.3 or a q-valent anion of an organic sulfonic acid or of a carbocyclic acid; R.sup.1 can also be a polymeric, aromatic ligand. The invetion particularly relates to the compounds of the formula I wherein a is 1 and q is 1 and X.sup.
    Type: Grant
    Filed: April 8, 1993
    Date of Patent: December 6, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Meier, Roger P.-E. Salvin
  • Patent number: 5371115
    Abstract: A hardenable composition containing:a) a material polymerizable by free radical or cationic polymerization,b) at least one iron compound of the formula I ##EQU1## wherein a is 1 or 2 and q is 1, 2 or 3,L is a divalent to heptavalent metal or non-metal,Q is a halogen atom,m is an integer corresponding to the sum of the values of L and q,R.sup.1 is an unsubstituted or substituted .eta..sup.6 -benzene andR.sup.2 is an unsubstituted or substituted cyclopentadienyl anion, andc) at least one sensitizer for the compound of the formula I,and, in the case of materials polymerizable by free radical polymerization, also d) an electron acceptor as an oxidizing agent, which is also advantageously used concomitantly for the material polymerizable by cationic polymerization. The composition is suitable for the production of protective layers and photographic images.
    Type: Grant
    Filed: April 15, 1992
    Date of Patent: December 6, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Meier, Hans Zweifel
  • Patent number: 5368985
    Abstract: Bisacylphosphine sulfides of formula I ##STR1## wherein R.sub.1 is unsubstituted C.sub.1 -C.sub.18 or C.sub.1 -C.sub.8 alkyl which is substituted by phenyl, --CN, C.sub.1 -C.sub.12 alkoxy or halogen, C.sub.2 -C.sub.18 alkenyl, unsubstituted C.sub.5 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.8 cycloalkyl which is substituted by C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or halogen, unsubstituted C.sub.6 -C.sub.12 aryl or C.sub.6 -C.sub.12 aryl which is substituted by halogen, C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.12 alkoxy, or a 5- or 6-membered aromatic heterocyclic radical which contains oxygen, sulfur and/or nitrogen and is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, andR.sub.2 and R.sub.3 are each independently of the other unsubstituted C.sub.1 -C.sub.18 alkyl or C.sub.1 -C.sub.8 alkyl which is substituted by phenyl, halogen or C.sub.1 -C.sub.12 alkoxy, C.sub.2 -C.sub.6 alkenyl, unsubstituted C.sub.5 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: November 29, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Werner Rutsch, Gebhard Hug, Manfred Kohler
  • Patent number: 5364691
    Abstract: This invention relates to radiation curable alk-1-enyloxy carbonate reaction products of a hydroxylated compound having the formula A-ROH and a dialk-1-enyloxy carbonate having the formula ##STR1## wherein R is a polymeric radical selected from the group of polyester, polyacetal, polyurethane, polyether, and polycarbonate, said polymers containing from about 10 to 50 repeating monomer units;A' is a terminating moiety and is hydrogen, lower alkyl or hydroxy;R' is hydrogen or lower alkyl;B is a linear, branched or cyclic divalent radicalhaving from 2 to 12 carbon atoms and is selected from the group of alkylene, mono or poly alkoxylated alkylene, alkenylene, alkynylene, arylene, alkarylene and aralkylene radicals, which radicals are optionally substituted with halo, lower alkyl, cyano, nitro or alkoxy and m has a value of from 1 to 10.
    Type: Grant
    Filed: March 9, 1990
    Date of Patent: November 15, 1994
    Assignee: ISP Investments Inc.
    Inventors: Paul D. Taylor, Kolazi S. Narayanan, Jeffrey S. Plotkin
  • Patent number: 5360836
    Abstract: The subject of the invention is a process for the production of coatings by radiation crosslinking of compositions containing a resin which can be cured by the polymerization of the double bonds >C.dbd.CH.sub.2 and a reactive diluent system containing at least one reactive diluent corresponding to the general formula (I) ##STR1## in which R.sub.1 =H, CH.sub.3,R.sub.2 and R.sub.3 =H, C.sub.1 -C.sub.4 -alkyl chain or form an alkylene ring containing 5 or 6 carbon atoms,R.sub.4 =H, C.sub.1 -C.sub.4 -alkyl chain, phenyl,R.sub.5 =C.sub.1 -C.sub.10 aliphatic chain, C.sub.5 -C.sub.6 alicyclic chain, or C.sub.1 -C.sub.4 alkyl chain substituted with an aryl or aromatic heterocyclic group,or R.sub.4 and R.sub.5 form a 5- or 6-membered ring.One preferred compound (I) is to the acrylate of isopropyl beta-hydroxyethylcarbamate.
    Type: Grant
    Filed: March 22, 1993
    Date of Patent: November 1, 1994
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Francois Chevallier, Sammy Chevalier
  • Patent number: 5358976
    Abstract: Curable norbornene-thiol compositions are stabilized by addition of a non-acidic Nitroso compound.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: October 25, 1994
    Assignee: Loctite (Ireland) Limited
    Inventors: Joseph P. Dowling, Sarah C. Richardson, Killian Quigley
  • Patent number: 5354784
    Abstract: A keto arene-cyclopentadienyl iron complex salt of the formula:[(R.sup.2 CO)(R.sup.1).sub.m C.sub.6 H.sub.5--m Fe.sup.II Cp].sup.+1 A.sup.-1wherein R.sup.1 is an alkyl group, R.sup.2 is an alkyl group or phenyl group, m is an integer of 1 to 5, Cp is an .eta..sup.5 -cyclopentadienyl group and A.sup.-1 is a non-nucleophilic anion, e.g. pentamethylacetophenone-Fe(II)-Cp.sup.+ PF.sub.6.sup.-1 salt or pentamethylbenzophenone-Fe(II)-Cp.sup.+ PF.sub.6.sup.-1 salt, which is useful as a photoinitiator for cationically polymerizable compounds, especially for epoxy resins, and has an improved environmental safety and a high absorptivity, and which can be easily produced by a direct replacement reaction between dicarbonyl-.eta..sup.5 -(2,4-cyclopentadien-1-yl)iron(II) halide and an alkyl substituted keto arene to be replaced for the carbonyl ligands.
    Type: Grant
    Filed: August 10, 1992
    Date of Patent: October 11, 1994
    Assignee: Arakawa Kagaku Kogyo Kabushiki Kaisha
    Inventors: Scott F. Timmons, Hiroshi Sawada, Stephen T. Willinghoff, Robert E. Lyle, Jr., Belinda K. Taylor
  • Patent number: 5350604
    Abstract: A process for cationically polymerizing 1,3-diisopropenylbenzene to produce a polymer which is predominantly a polyindane is disclosed. The resulting polyindanes are novel compounds useful as low dielectric constant coatings. Compositions containing 1,3-diisopropenylbenzene and cationic photoinitiators, and optionally containing a polyindane useful for preparing coatings, are disclosed as are processes for coating substrates using the compositions.
    Type: Grant
    Filed: December 9, 1992
    Date of Patent: September 27, 1994
    Assignee: Rensselaer Polytechnic Institute
    Inventor: James V. Crivello
  • Patent number: 5342658
    Abstract: The present invention relates to an ultraviolet light curable coating composition having a shorter curing time and an excellent abrasion resistance, which comprises:(A) an aqueous-alcoholic base resin dispersion containing, based on the weight of the total solids present in the base resin dispersion,(a) 5 to 75% by weight of a colloidal silica and(b) 25 to 95% by weight of a partial condensate of a silanol of formula:R SI(OH).sub.3whereinR is a C.sub.1-6 alkyl, C.sub.6-20 aryl or hydroxy group; and(B) an ultraviolet light curable catalyst of formulaAr.sub.3 S.sup.+ MX.sub.n.sup.-whereinAr.sub.3 is a triphenyl, tri(4-methoxy)phenyl, tri(3,5-dimethyl-4-hydroxyphenyl), diphenyl-2,5-dimethylphenyl or tri(4-methyl) phenyl group; andMX.sub.n.sup.- is a metallic halide anion.
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: August 30, 1994
    Assignee: Lucky Limited
    Inventors: Young J. Hong, Jin B. Kim, Jong K. Yeo
  • Patent number: 5342860
    Abstract: This invention relates to alk-1-enyl ether-polyester block prepolymers which are curable by cationically initiated radiation and which are defined by the formula ##STR1## wherein m has a value of from 1 to 25;A is C.sub.2 to C.sub.12 alkylene, C.sub.6 to C.sub.14 aryl, both groups optionally substituted with lower alkyl, halo lower alkyl, alkyleneoxy, halogen or aryl;R.sub.1 is alkylene containing from 1 to 6 carbon atoms;R.sub.2 is a saturated or unsaturated divalent radical containing from 1 to 14 carbon atoms and is selected from the group of alkylene, alkenylene and arylene, each group optionally substituted with oxygen, halogen, lower alkyl and/or hydroxy;R.sub.3 is hydrogen or C.sub.1 to C.sub.6 alkyl;R.sub.4 is C.sub.1 to C.sub.6 alkylene, C.sub.6 to C.sub.14 arylene, lower alkyl substituted phenylene or xylylene andR.sub.5 and R.sub.6 are independently hydrogen or C.sub.1 to C.sub.4 alkyl.
    Type: Grant
    Filed: August 18, 1993
    Date of Patent: August 30, 1994
    Assignee: ISP Investments Inc.
    Inventors: Jeffrey S. Plotkin, Mark M. Miller
  • Patent number: 5322762
    Abstract: A highly stable photopolymerizable composition which is highly photosensitive to visible light, which can be hardened using a visible light laser, such as an argon laser, which provides excellent contrast between non-irradiated portions and the substrate under red light, and, moreover, which provides excellent contrast between the portions irradiated by the laser and the portions not irradiated. The photopolymerizable composition consists of 100 parts by weight of a resin which is hardenable under visible light having an irradiation energy mainly consisting of light rays in the 400 nm to 700 nm visible light region; 0.02 to 0.5 parts by weight of at least one dye selected from the group consisting of Victoria Pure Blue, anthraquinone dyes, monoazo dyes, and merocyanine dyes, these dyes having maximum absorption wavelengths from 550 to 700 nm; 0.1 to 5 parts by weight of the leuco dye 4,4'-(phenylmethylene bis[N,N-diethylbenzene amine]; and 0.1 to 5 parts by weight of tribromomethylphenyl sulphone.
    Type: Grant
    Filed: April 13, 1993
    Date of Patent: June 21, 1994
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Kenji Kushi, Chiho Tokuhara
  • Patent number: 5321053
    Abstract: A dental composition comprising a vinyl monomer containing at least one acidic group in the molecule thereof and an initiator capable of photopolymerizing said monomer by visible light, characterized in that said initiator consisting essentially of:(a) a photosensitizer selected from an .alpha.-diketone, a quinone and a derivative thereof, and,(b) an accelerator selected from a compound containing at least one mercapto group in the molecule thereof is provided by the present invention.
    Type: Grant
    Filed: February 6, 1990
    Date of Patent: June 14, 1994
    Assignee: Kuraray Co., Ltd.
    Inventors: Kenichi Hino, Junichi Yamauchi, Koji Nishida
  • Patent number: 5314929
    Abstract: The present invention relates to a rapidly curable, silicone-free release coating composition comprising (a) between about 50 and about 95 wt. % of a vinyl ether having the formula C.sub.n H.sub.2n+1 O--CH.dbd.CH.sub.2 wherein n has a value of from 8 to 20, optionally containing a cationically polymerizable comonomer; (b) between about 5 and about 50 wt. % of a multifunctional vinyl ether monomer and (c) between about 0.1 and about 10 wt. % of an onium salt photoinitiator.
    Type: Grant
    Filed: August 10, 1992
    Date of Patent: May 24, 1994
    Assignee: ISP Investments Inc.
    Inventors: James V. Crivello, James A. Dougherty
  • Patent number: 5304456
    Abstract: A negative photoresist composition containing an alkali-soluble resin which is obtainable through a condensation reaction of an aldehyde with a phenol compound containing a compound of the general formula: ##STR1## wherein R.sup.1 to R.sup.9 are independently a hydrogen atom, an alkyl group, an alkenyl group, an alkylcarbonyl group, a halogen atom or a hydroxyl group, provided that at least one of R.sup.1 to R.sup.9 is a hydroxyl group and, at the ortho- or para-position to the hydroxyl group, at least two hydrogen atoms are present; a cross linking agent; and a photo-acid generator, and a negative photoresist composition comprising an alkali-soluble resin, a cross linking agent and a photo-acid generator having a trifluoromethanesulfonic acid ester group, which can increase resolution and contrast of a photoresist pattern.
    Type: Grant
    Filed: January 29, 1992
    Date of Patent: April 19, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yuji Ueda, Hiromi Ueki, Naoki Takeyama, Takehiro Kusumoto
  • Patent number: 5294517
    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: January 27, 1993
    Date of Patent: March 15, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Fred B. McCormick, Katherine A. Brown-Wensley, Robert J. DeVoe
  • Patent number: 5294688
    Abstract: The invention relates to UV-crosslinkable copolymers built up fromA) from 99.5 to 75% by weight of olefinically unsaturated monomers,B) from 0.5 to 25% by weight of unsaturated compounds of the formula I ##STR1## and C) from 0.01 to 10% by weight of copolymerizable, olefinically unsaturated acetophenone and/or benzophenone derivatives containing no phenyl group having a free hydroxyl group in the ortho-position to the carbonyl group, whereX is O, S or NR.sup.1 andR is unsubstituted or substituted C.sub.2 - to C.sub.6 -alkylene, andR.sup.1 is C.sub.1 - to C.sub.8 -alkyl or phenyl.The copolymers according to the invention are suitable, after crosslinking, as coating agents, impregnants or adhesives and in particular as contact adhesives.
    Type: Grant
    Filed: November 16, 1992
    Date of Patent: March 15, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Rehmer, Gerhard Auchter, Andreas Boettcher, Lothar Franz, Helmut Jaeger
  • Patent number: 5286603
    Abstract: A radiation sensitive plate comprises a substrate coated with a photopolymerisable composition. The composition comprises a polymerisable compound containing ethylenic unsaturation, a perester photoinitiator and optionally an optical sensitiser. The substrate may be a sheet of grained and anodised aluminum and the plate is useful in the production of lithographic printing plates.
    Type: Grant
    Filed: June 3, 1992
    Date of Patent: February 15, 1994
    Assignee: Vickers PLC
    Inventors: John R. Wade, Rodney M. Potts, Michael J. Pratt
  • Patent number: 5284736
    Abstract: A flame-resistant, photo-curing resin composition of the present invention consists of:(a) 35 to 65 parts by weight of an acrylic thermoplastic polymer, the acrylic thermoplastic polymer being 15 to 30% by weight copolymerized with at least one of monomer containing an alpha, beta-unsaturated carboxyl group,(b) 5 to 30 parts by weight of a bromine-substituted monomer represented by a general formula [I]: ##STR1## wherein R.sub.1 is H or CH.sub.3,A is ##STR2## wherein R.sub.2 is an alkylene group containing two or three carbon atoms,n is an integer between 1 and 4, andX.sub.1, X.sub.2, and X.sub.3 are Br or H, under a condition that at least two of the X.sub.1, X.sub.2, and X.sub.3 are Br,(c) 0 to 10 parts by weight of antimony trioxide particles with an average diameter of 0.1 .mu.m or smaller,(d) 20 to 50 parts by weight of a vinyl monomer, excluding component (b), and(e) 0.
    Type: Grant
    Filed: December 2, 1991
    Date of Patent: February 8, 1994
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Kenji Kushi, Ken-ichi Inukai
  • Patent number: 5283265
    Abstract: A photopolymerizable rubber being obtained by copolymerizing four compounds consisting of a dienic liquid rubber having hydroxyl groups, an ethylenically unsaturated monomer having hydroxyl groups, a dihydric alcohol having a molecular weight of less than 2,000 and a diisocyanate compound. The photocured product of this composition has higher tensile strength and elongation than that of the prior photopolymerizable rubbers.
    Type: Grant
    Filed: April 18, 1988
    Date of Patent: February 1, 1994
    Assignee: Hayakawa Rubber Company Limited
    Inventors: Tetsuya Kimura, Syuno Suto, Fujii Toshihiro, Toshihiro Fujii, Kimio Mori, Tsuguo Yamaoka