Processes Involving An Ethylenically Unsaturated Polyester Derived From A Polycarboxylic Acid Or Derivative And Polyol, Condensate Or Solid Polymer Thereof; Or Compositions Therefore Patents (Class 522/104)
  • Patent number: 6008268
    Abstract: A method of generating reactive species which includes exposing a photoreactor composition to radiation, in which the photoreactor composition comprises a wavelength-specific sensitizer associated with one or more reactive species-generating photoinitiators. Also described are methods of polymerizing unsaturated monomers and curing an unsaturated oligomer/monomer mixture.
    Type: Grant
    Filed: January 22, 1998
    Date of Patent: December 28, 1999
    Assignee: Kimberly-Clark Worldwide, Inc.
    Inventors: Ronald Sinclair Nohr, John Gavin MacDonald
  • Patent number: 6001892
    Abstract: A liquid, radiation curable composition is disclosed that includes a reactive diluent to lower initial application viscosity without substantial reduction of cure rate. The composition of the present invention comprises: (a) an unsaturated polyester polymer; (b) a non-polymerized, cocurable polyfunctional vinyl ether component; and (c) a reactive diluent which is an unsaturated dioic acid ester having the following structural formula: ##STR1## wherein at least one of R.sup.1 and R.sup.2 is a group that includes an oxygen with a carbon adlacent thereto and an abstractable hydrogen attached to the carbon.
    Type: Grant
    Filed: February 16, 1996
    Date of Patent: December 14, 1999
    Assignee: PPG Industries Oho, Inc.
    Inventors: Alan B. Weissberg, Edward E. McEntire, Charles B. Friedlander
  • Patent number: 6001891
    Abstract: A biodegradable aliphatic polyester elastomer which has rubber-like elasticity, hardness of 80 or less in accordance with ASTM D 676-58T, and elastic modulus from 1.times.10.sup.5 Pa to 1.times.10.sup.8 Pa at 25.degree. C., and decomposes with ease in the natural environment, under composting conditions or under hydrolysis conditions. The biodegradable aliphatic elastomer can be obtained by crosslinking aliphatic polyester containing aliphatic unsaturated polybasic acid as a polymer constituting ingredient and having a weight average molecular weight of 15,000 or more.
    Type: Grant
    Filed: May 29, 1997
    Date of Patent: December 14, 1999
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Chojiro Higuchi, Masatoshi Takagi, Takeshi Kashima, Masanobu Ajioka, Yuji Terado
  • Patent number: 5942556
    Abstract: Disclosed is a radiation curable composition which includes: (a) an unsaturated ester compound, and (b) a pulverizable vinyl ether compound. The unsaturated ester compound is characterized as having a plurality of unsaturated ester groups per molecule. The pulverizable vinyl ether compound is characterized as including at least one of the following: (a) a compound having an average of greater than 1.0 reactive vinyl ether groups per molecule, and (b) a vinyl ether-containing group bonded to the unsaturated ester compound such that there is an average of at least 1.0 reactive vinyl ether group per molecule. The unsaturated ester compound, the vinyl ether compound and/or a mixture thereof is treated with a reducing agent so as to decompose destabilizing agents present therein that would initiate premature polymerization of the vinyl ether compound.
    Type: Grant
    Filed: November 27, 1996
    Date of Patent: August 24, 1999
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Charles B. Friedlander, Ronald R. Ambrose, David A. Diehl, Alan B. Weissberg, Carolyn A. Novak
  • Patent number: 5922473
    Abstract: Opaquely pigmented or thick filmed powder coatings for heat sensitive substrates, such as wood, wood composites, for example, medium density fiber board, and plastics, that can be fully cured, especially near the substrate, through the incorporation of a dual cure system in the powder comprising a thermal initiator, such as a peroxide, along with a UV initiator. The UV initiator cures the surface, while the thermal initiator cures at the substrate. Surprisingly, virtually no pregelation occurs during the heated melt and flow out step prior to UV curing. Consequently, the hardened film finish formed on the surface exhibits exceptional smoothness which is comparable to that of traditional UV curable powders. The hardened film finish is also fully cured throughout and exhibits exceptional adhesion to the substrate which cannot be achieved with traditional UV curable powders that have been pigmented.
    Type: Grant
    Filed: December 26, 1996
    Date of Patent: July 13, 1999
    Assignee: Morton International, Inc.
    Inventors: Jeno Muthiah, Andrew T. Daly, Richard P. Haley, Joseph J. Kozlowski
  • Patent number: 5902646
    Abstract: This invention relates to coating media based on one or more styrene-free, unsaturated polyester resins, which containA) one or more unsaturated polyesters obtainable by the reaction ofa) 0.5 to 1.0 mole of at least one alpha,beta-ethylenically unsaturated dicarboxylic acid or the anhydride thereof,b) 0 to 0.5 mole of at least one aromatic, aliphatic and/or cycloaliphatic saturated dicarboxylic acid or the anhydride thereof,c) 0.4 to 0.8 mole of at least one aliphatic saturated dihydric alcohol,d) 0.5 to 1.2 mole of at least one hydroxy-functional allyl ether,B) one or more polyglycol diacrylates of general formula ##STR1## where n=2-5 and m=2-5, particularly dipropylene glycol diacrylate, C) one or more initiators, andoptionally one or more organic solvents, one or more pigments and/or extenders, as well as accelerators, catalysts and/or customary lacquer additives.
    Type: Grant
    Filed: December 5, 1996
    Date of Patent: May 11, 1999
    Assignee: Herberts GmbH
    Inventors: Heinz Dietholf Becker, Gerhard Bremer, Werner Stephan
  • Patent number: 5900473
    Abstract: The present invention discloses radiation curable pressure-sensitive adhesives comprising the reaction product of a blend of at least two hydroxy polyesters having different Tgs, and at least one prepolymer functionalized with (Meth) acrylates, isocyanates and mixtures thereof. The present invention further discloses a blend of at least two hydroxy polyesters wherein at least one of the hydroxy polyesters has a Tg of less than -35.degree. C., and at least one of the other hydroxy polyesters has a Tg of greater than about -35.degree. C.
    Type: Grant
    Filed: June 2, 1998
    Date of Patent: May 4, 1999
    Assignee: H.B. Fuller Licensing & Financing, Inc.
    Inventors: Margarita Acevedo, Hans F. Huber
  • Patent number: 5880170
    Abstract: A photopolymerizable composition comprising:(I) a photopolymerizable oligomer represented by the following formula (1), ##STR1## and/or by the following formula (2), ##STR2## wherein R.sup.1 is a hydrogen atom or a methyl group, R.sup.2 and R.sup.3 are organic groups, X is oxygen or sulfur, n is a number of not smaller than 1, and m is a number of not smaller than 2,or a combination of the above photopolymerizable oligomer and other ethylenically unsaturated monomer which is copolymerizable therewith; and(II) a catalytic amount of a photo-initiator, as well as a transparent cured product thereof. The product obtained by curing the photopolymerizable composition exhibits excellent properties and, particularly, excellent surface precision.
    Type: Grant
    Filed: March 12, 1997
    Date of Patent: March 9, 1999
    Assignee: Tokuyama Corporation
    Inventors: Satoshi Imura, Toshihiro Nishitake
  • Patent number: 5859084
    Abstract: A process for the preparation of a radiation-curable acrylate composition, wherein to compounds A containing at least 2 acrylic groups there are added benzophenone derivatives which are not copolymerizable by free-radical copolymerization and which contain at least one primary or secondary amino group or a hydroxyl group or a mercapto group.
    Type: Grant
    Filed: July 15, 1996
    Date of Patent: January 12, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Jochen Schroder, Wolfgang Reich, Erich Beck, Martin Fischer, Wolfram Weiss
  • Patent number: 5805358
    Abstract: UV-curable Fresnel lens resin compositions ?1a! comprising a (meth)acrylate containing hydroxyl group and aromatic ring (A1), a urethane group-containing (meth)acrylate (A2) comprising an aromatic diol, an aromatic ring-containing monofunctional (meth)acrylate (A3), and a photopolymerization initiator (B) and ?1b! comprising (A1), a mono- or di(meth)acrylate monomer (A4), and (B), further supplemented with a polyester (C1) comprising an aromatic diol and a phosphate (C2) for the formation of a Fresnel lens on a sheet or plate made of a methyl methacrylate (co)polymer; a Fresnel lens formed by UV cure of composition ?1a! or ?1b!; and a rear projection screen including a sheet or plate carrying said Fresnel lens. The Fresnel lens has high refractive index, antistatic properties and is satisfactory in adhesion to a sheet or plate.
    Type: Grant
    Filed: July 29, 1996
    Date of Patent: September 8, 1998
    Assignees: Sanyo Chemical Industries, Ltd., Dainippon Printing Co., Ltd.
    Inventors: Tsutomu Yamashita, Michiharu Okubo, Makoto Honda, Futoshi Osawa
  • Patent number: 5780525
    Abstract: A process for providing a metal oxide-containing coating on a compatible substrate, the coating being transparent to a photocuring source output and upon cure being resistant to electrical stress. The process of the invention comprises a) preparing a precursor composition comprising a mixture of a stabilizer and a metal oxide sol precursor material; b) combining the stabilizer/metal oxide sol precursor material mixture with a photocurable base resin without high shear mixing to achieve a homogeneous, transparent composition; c) coating the substrate material with the transparent composition; and d) photocuring the coated substrate bearing the transparent composition, wherein the cured coating is homogenous and transparent and remains transparent in the use state, thereby rendering the coating corona resistant. This invention further relates to the coated substrate.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: July 14, 1998
    Assignee: Reliance Electric Industrial Company
    Inventors: Hong-Son Ryang, An-Min J. Sung, Joseph T. Snyder, II
  • Patent number: 5780526
    Abstract: An ultraviolet-curing liquid undercoating composition for use in metallizing FRP, which is a one-component type, has an unlimited pot life, and is excellent in adhesion and heat resistance. The composition comprises 20 to 80 parts by weight of a compound(s) containing at least two (meth)acryloyl groups in its molecule, 80 to 20 parts by weight of oil-modified alkyd resin(s), and 2 to 15 parts by weight of a sensitizer, optionally further 5 to 20 parts by weight of an amino resin based on 100 parts by weight in total of the above compound and the above alkyd resin(s). It is suited for the undercoating of an automotive reflector.
    Type: Grant
    Filed: November 14, 1996
    Date of Patent: July 14, 1998
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Sakae Matsui, Hiroyuki Nakamura, Shizuo Kudo, Hiroaki Konse
  • Patent number: 5744248
    Abstract: The present invention relates to coating compositions, which are curable by radiation and containI) 0 to 95 parts by weight of at least one binder curable by radiation and containing maleate, fumarate and/or acryloyl groups other than those of component II),II) 5 to 100 parts by weight of a mixture ofA) 20 to 80 parts by weight of at least one polyester resin prepared from fatty acids, provided that at least 20 wt. % of component A) is a fatty acid having a number average molecular weight of 112 to 400 andB) 20 to 80 parts by weight of compounds containing (meth)acryloyl groups, having a viscosity at 23.degree. C. of 10 to 1,000 mPa.s and having a number average molecular weight of 170 to 1,000,wherein the sum of the parts by weight of components I) and II) adds up to 100, based on the weight of components I) and II), and the sum of the parts by weight of components A) and B) adds up to 100, based on the weight of components A) and B).
    Type: Grant
    Filed: January 28, 1997
    Date of Patent: April 28, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Meixner, Wolfgang Fischer, Manfred Muller, Gunter Ruf
  • Patent number: 5736589
    Abstract: Absorbable polymers and blends of acrylated poly(alkylene diglycolate)s and aliphatic polyesters based on lactone monomers such as lactide, glycolide, e-caprolactone, p-dioxanone, and trimethylene carbonate are described. The polymers and blends exhibit a broad range of properties, useful in a variety of medical devices.
    Type: Grant
    Filed: July 30, 1996
    Date of Patent: April 7, 1998
    Assignee: Ethicon, Inc.
    Inventors: Kevin Cooper, Angelo Scopelianos
  • Patent number: 5721076
    Abstract: This invention relates to alkali-developable photosensitive or thermosetting resin compositions obtained by mixing (A) polymerizable unsaturated compounds having main structural units represented by the following general formulas (1) and (2) ##STR1## ?wherein R.sub.1, and R.sub.2 designate hydrogen, alkyl group with 1 to 5 carbon atoms or halogen, R.sub.3 designates hydrogen or methyl group, X designates --CO--, --SO.sub.2 --, --C(CF.sub.3).sub.2 --, --Si(CH.sub.3).sub.2 --, --CH.sub.2 --, --C(CH.sub.3).sub.2 --, --O--, ##STR2## or direct linkage, Y designate acid anhydride residue, Z designates acid dianhydride residue and the mole ratio of the structural units (m/n) is from 1/99 to 90/10 and showing an inherent viscosity (.eta..sub.inh) of 0.1 dl/g or more as determined on a solution of 0.5 g of said compounds in 100 ml of N-methylpyrrolidone at 30.degree. C.
    Type: Grant
    Filed: February 27, 1995
    Date of Patent: February 24, 1998
    Assignees: Nippon Steel Corporation, Nippon Steel Chemical Co., Ltd.
    Inventors: Kazuhiro Watanabe, Takero Teramoto, Kohki Inada
  • Patent number: 5717032
    Abstract: A filming composition comprises an acryl emulsion having a molecular weight of 1.5.about.2.5 million and a decomposition starting temperature of 200.degree..about.250.degree. C., as a main component. The composition has a tendency to decompose at low temperature and can be completely decomposed and removed during frit sealing, without the need for separate baking or complex equipment. A screen having good characteristics can be obtained through an advantageous method.
    Type: Grant
    Filed: March 10, 1995
    Date of Patent: February 10, 1998
    Assignee: Samsung Display Devices Co., Ltd.
    Inventors: Hyeon-sang Kim, Jong-ho Oh
  • Patent number: 5707782
    Abstract: Photosensitive, dielectric insulating, crosslinkable copolyester films used as dielectric and as photoresist films for microelectronics circuits which are also suitable for use in producing MCM-L packages. In various embodiments of the invention there is provided photosensitive, dielectric insulating, crosslinkable copolyester film forming mixtures for coating onto microelectronics substrate surfaces, a photosensitive oligomer for producing the crosslinkable copolyesters and MCM-L products produced using the crosslinked copolyesters.
    Type: Grant
    Filed: March 1, 1996
    Date of Patent: January 13, 1998
    Assignee: The Board of Trustees of the University of Illinois
    Inventors: James Economy, Lizabeth A. Schneggenburger, Fang Shi
  • Patent number: 5700856
    Abstract: A peroxide-generating composition for use in curing an unsaturated polyester resin and to the cured unsaturated polyester resin composition so prepared, particularly unsaturated polyester resin compositions containing inert filler materials used prepare a cast or molded product. The peroxide-generating composition comprises an allyl alcohol alkanoate, such as allyl alcohol propoxylate, which in the presence of a metal salt promoter, such as cobalt carboxylate, either with the allyl alcohol alkanoate or separately as a prepromoter in the unsaturated polyester resin composition provides for the generation from the allyl alcohol alkanoate of a peroxide to effect the in situ cure of the unsaturated polyester resin composition.
    Type: Grant
    Filed: April 10, 1996
    Date of Patent: December 23, 1997
    Assignee: Hehr International Inc.
    Inventor: Stuart B. Smith
  • Patent number: 5696178
    Abstract: Absorbable polymers and blends of acrylated poly(alkylene diglycolate)s and aliphatic polyesters based on lactone monomers such as lactide, glycolide, e-caprolactone, p-dioxanone, and trimethylene carbonate are described. The polymers and blends exhibit a broad range of properties, useful in a variety of medical devices.
    Type: Grant
    Filed: July 22, 1996
    Date of Patent: December 9, 1997
    Assignee: Ethicon, Inc.
    Inventors: Kevin Cooper, Angelo Scopelianos
  • Patent number: 5691053
    Abstract: A coating material and coating process for color coating articles, such as motor vehicle bodies, and coated articles produced therewith. The coating contains a paint vehicle composed of at least one curable liquid-crystal polymer (LCP), the colored appearance of the coating being determined by mesogens of the paint vehicle which exhibit an interference effect, the mesogens automatically aligning themselves substantially perpendicular to the surface of the article during application of the coating material and adopting a chiral-nematic configuration in which they form a helix having a pitch length which can be influenced by heat within a specified temperature range. The liquid-crystal polymers are such that they are not crosslinked by heat and also such that the temperature level at which the pitch length of the helix can be influenced is above the temperature at which the color coated article is used.
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: November 25, 1997
    Assignee: Daimler-Benz AG
    Inventors: Michael Gailberger, Anne Barth, Hans Ruetger Kricheldorf, Volkmar Vill, Mihai Gurau, Matthias Berghahn
  • Patent number: 5679719
    Abstract: Resin compositions useful for filament winding applications comprising an epoxy component including at least one polyepoxide resin curable by heat, an olefinicially unsaturated monomer component including at least one polyolefinically unsaturated monomer curable by actinic radiation, at least one photoinitiator which is not a peroxide, at least one organic peroxide, and a heat activated curing agent for epoxides. The compositions have a viscosity less than about 2000 centipoise (cps) and are capable of retaining this viscosity for at least about 2 hours at a temperature of from about ambient temperature to about 60.degree. C. The resins are capable of being immobilized by actinic radiation exposure and further heat cured without substantial resin drip. One or more organic peroxides are employed, selected from the group of organic peroxides having 10 hour decomposition half lives at temperatures of from about 50.degree. C. to less than about 104.degree. C.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 21, 1997
    Assignee: Loctite Corporation
    Inventors: Philip T. Klemarczyk, Yoshihisa Okamoto, James P. Moran, Jr., Susan Levandoski, Veronica Hanlon
  • 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: 5639560
    Abstract: A radiation-curable powder composition for use as varnish or paint which comprises at least one crystalline polyester containing end methacrylyl groups comprising the reaction products of glycidyl methacrylate and of a crystalline polyester containing end carboxyl groups is described. The said crystalline polyester containing end carboxyl groups is either(a) a polyester which is the reaction product of(1) an acid constituent which contains (a.1.1) 85 to 100 mol % of terephthalic acid or of 1,4-cyclohexanedicarboxylic acid and (a.1.2) 0 to 15 mol % of at least one other aliphatic, cycloaliphatic or aromatic di- or polycarboxylic acid having from 4 to 14 carbon atoms, and(2) an alcohol constituent which contains (a.2.1) 85 to 100 mol % of a saturated, straight-chain, aliphatic diol having from 2 to 12 carbon atoms and (a.2.
    Type: Grant
    Filed: April 22, 1996
    Date of Patent: June 17, 1997
    Assignee: U C B S.A.
    Inventors: Luc Moens, Jean-Marie Loutz, Daniel Maetens, Patrick Loosen, Marc Van Kerckhove
  • Patent number: 5635545
    Abstract: Thermoplastic molding compositions are made from a mixture of thermoplastic material (for example, polycaprolactone), a free-radically polymerizable resin (for example, a urethane diacrylate oligomer), and free-radical initiator (for example, a visible-light cure photoinitiator). The mixture is solid at 38.degree. C., has a melting or softening point that comfortably can be withstood by oral tissues, and can be imprinted with a heat-stable custom shape memory and semi-thermoplastic properties by shaping the composition to a desired shape and then causing or permitting the resin to undergo polymerization.
    Type: Grant
    Filed: February 13, 1995
    Date of Patent: June 3, 1997
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Joel D. Oxman, Lani S. Kangas, F. Andrew Ubel, III
  • Patent number: 5616630
    Abstract: An ester/urethane acrylate hybrid oligomer which is the reaction product of an acrylate/hydroxy-functional polyester, an isocyanate compound, and a hydroxy-functional acrylate compound. The acrylate/hydroxy-functional polyester is prepared by reacting a polyester polyol and an acrylate compound. The polyester backbone of the oligomer has both ester and urethane linkages to the terminal acrylate functionality. This hybrid nature of the polyester backbone provides an oligomer which can be utilized at low viscosity to facilitate processing while maintaining effective stain resistance and flexibility.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: April 1, 1997
    Assignee: Lord Corporation
    Inventor: Richard E. Heinze
  • Patent number: 5596669
    Abstract: Provided is a radiation curable coating composition suitable for coating optical glass fiber, having a viscosity in the range of about 10 mPas to 10,000 mPas made of about 20 to about 99.9 weight % of at least one of a thermoplastic non-crosslinking polymer and an ethylenically-unsaturated oligomeric compound; optionally, from 0 to about 60 weight % of an ethylenically-unsaturated diluent, optionally, from 0 to about 60 weight % of a multifunctional ethylenically-unsaturated compound, and optionally, from 0 to about 10 weight % of a photoinitiator, provided that if the thermoplastic non-crosslinking polymer is present and no ethylenically-unsaturated oligomeric compound is present, then the ethylenically-unsaturated diluent is present in an amount up to about 60 weight % and the multifunctional ethylenically-unsaturated compound is present in an amount up to about 60 weight %. The composition provides a tack-free handeable fiber after radiation cure and is fugitive upon thermolysis.
    Type: Grant
    Filed: April 21, 1995
    Date of Patent: January 21, 1997
    Assignee: DSM N.V.
    Inventors: Edward J. Murphy, Stephen C. Lapin, Gerry K. Noren
  • Patent number: 5591786
    Abstract: Thermoplastic molding compositions are made from a mixture of thermoplastic material (for example, polycaprolactone), a free-radically polymerizable resin (for example, a urethane diacrylate oligomer), and free-radical initiator (for example, a visible-light cure photoinitiator). The mixture is solid at 38.degree. C., has a melting or softening point that comfortably can be withstood by oral tissues, and can be imprinted with a heat-stable custom shape memory and semi-thermoplastic properties by shaping the composition to a desired shape and then causing or permitting the resin to undergo polymerization.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: January 7, 1997
    Assignee: Minnesota Mining And Manufacturing Company
    Inventors: Joel D. Oxman, F. Andrew Ubel, III, Lani S. Kangas
  • Patent number: 5585414
    Abstract: Resin compositions useful for filament winding applications comprising an epoxy component including at least one polyepoxide resin curable by heat, an olefinicially unsaturated monomer component including at least one polyolefinically unsaturated monomer curable by actinic radiation, at least one photoinitiator, at least one organic peroxide, and a heat activated curing agent for epoxides. The compositions have a viscosity less than about 2000 centipoise (cps) and are capable of retaining this viscosity for at least about 2 hours at a temperature of from about ambient temperature to about 60.degree. C. The resins are capable of being immobilized by actinic radiation exposure and further heat cured without substantial resin drip. One or more organic peroxides are employed, selected from the group of organic peroxides having 10 hour decomposition half lives at temperatures of from about 50.degree. C. to less than about 104.degree. C.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: December 17, 1996
    Assignee: Loctite Corporation
    Inventors: Philip T. Klemarczyk, Yoshihisa Okamoto, James P. Moran, Jr.
  • Patent number: 5569725
    Abstract: A class of unsaturated resins which are suitable for use in radiation curable coatings has been developed. The resins comprise N-vinyl-N-acyl oligomers made by reacting a secondary N-vinylamide with a polyisocyanate monomer which is reacted with at least one mono- or polyhydric alcohol to form a urethane linkage.
    Type: Grant
    Filed: October 14, 1994
    Date of Patent: October 29, 1996
    Assignee: Air Products and Chemicals, Inc.
    Inventors: W. Eamon Carroll, Walter L. Renz, Andrew F. Nordquist, Robert K. Pinschmidt, Jr.
  • Patent number: 5565499
    Abstract: Resin compositions useful for filament winding applications comprising an epoxy component including at least one polyepoxide resin curable by heat, an olefinicially unsaturated monomer component including at least one polyolefinically unsaturated monomer curable by actinic radiation, at least one photoinitiator, at least one organic peroxide, and a heat activated curing agent for epoxides. The compositions have a viscosity less than about 2000 centipoise (cps) and are capable of retaining this viscosity for at least about 2 hours at a temperature of from about ambient temperature to about 60.degree. C. The resins are capable of being immobilized by actinic radiation exposure and further heat cured without substantial resin drip. One or more organic peroxides are employed, selected from the group of organic peroxides having 10 hour decomposition half lives at temperatures of from about 50.degree. C. to less than about 104.degree. C.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: October 15, 1996
    Assignee: Loctite Corporation
    Inventors: Philip T. Klemarczyk, Yoshihisa Okamoto, James P. Moran, Jr.
  • Patent number: 5565501
    Abstract: The present invention provides a composition comprising (a) a carboxyl-group containing multifunctional acrylate; (b) a multifunctional acrylate having three or more acryloyl groups in the molecule; (c) an organic solvent; and optionally, (d) a photopolymerization initiator, (e) a colloidal metal oxide and (f) an acrylic resin is provided. This composition is applied to a plastic substrate and then irradiated with active energy rays, thereby forming a hard-coating layer having good adhesiveness to the substrate, transparency and hardwearing properties.
    Type: Grant
    Filed: April 17, 1995
    Date of Patent: October 15, 1996
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Noritaka Hosokawa, Kazuhide Hayama
  • Patent number: 5502085
    Abstract: A photopolymerized acrylic pressure-sensitive adhesive having excellent heat-resistance, an adhesive sheet using the adhesive, and methods for producing the adhesive and the adhesive sheet, are disclosed. The pressure-sensitive adhesive sheet having excellent heat resistance comprising a photopolymerization product of a composition comprising;a) 100 parts by weight of monomers comprising from 70 to 100% by weight of a (meth)acrylic acid alkyl ester having from 2 to 14 carbon atoms in the alkyl moiety, and from 30 to 0% by weight of a monoethylenically unsaturated monomer copolymerizable with the (meth)acrylic acid alkyl ester,b) from 0.02 to 20 parts by weight of a radical chain inhibitor,c) up to 5 parts by weight of a polyfunctional (meth)acrylate as a crosslinking agent, andd) from 0.01 to 5 parts by weight of a photopolymerization initiator.
    Type: Grant
    Filed: August 1, 1994
    Date of Patent: March 26, 1996
    Assignee: Nitto Denko Corporation
    Inventors: Masahiro Ohura, Takao Yoshikawa, Yasuyuki Tokunaga, Takaaki Moriyama, Tetsuo Inoue
  • Patent number: 5446073
    Abstract: Composition containing charge transfer complex from at least one unsaturated compound having an electron donor group and having an electron withdrawing group and being free of any photoinitiating compound is polymerized by being subjected to ultraviolet light.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: August 29, 1995
    Assignee: Fusion Systems Corporation
    Inventors: Sonny Jonsson, Per-Erik G. Sundell, William R. Schaeffer
  • 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: 5416126
    Abstract: A composition which is cured upon exposure to ultraviolet light in the absence of solvent is disclosed. The liquid composition is prepared by combining a liquid maleate polyester and at least one of a vinyl compound and an allyl functional compound. A photoinitiator is then added to the polymerizable liquid composition. A substrate is impregnated with the polymerizable liquid composition and exposed to actinic energy of a sufficient dosage for a sufficient amount of time to polymerize the composition to a sufficient degree to impart useful properties to the substrate. The composition can be used as a binder for fiberglass insulation, in the manufacture of transparent or semi-transparent paper and to manufacture paper for use in photocopy machines.
    Type: Grant
    Filed: February 17, 1993
    Date of Patent: May 16, 1995
    Assignee: DSM N.V.
    Inventors: Edward J. Murphy, Edward P. Zahora, Sami A. Shama
  • Patent number: 5409740
    Abstract: A method of forming a fiber bundle which is useful as an industrial thread. The fiber bundle is prepared by integrating individual fiber filaments into a fiber bundle, applying a dual-cure adhesive material to the fiber bundle and initiating polymerization of the dual-cure adhesive material. The dual-cure adhesive material is a combination of a radiation-curable material and a moisture-curable material. The radiation-curable material contains an acrylourethane oligomer and a reactive diluent system, while the moisture-curable material contains a polyisocyanate or an isocyanate-functional urethane prepolymer. The use of a dual-cure material results in a synergistic curing process so as to form a durable and flexible industrial thread or fiber.
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: April 25, 1995
    Assignee: Lord Corporation
    Inventor: Bill L. Brann
  • Patent number: 5409965
    Abstract: An active energy ray-curing abrasion resistant coating composition is provided by incorporating following components: (a) a carboxylate-containing polyfunctional acrylate obtained by reacting a tetracarboxylic dianhydride and a hydroxyl group-containing polyfunctional acrylate having hydroxyl group(s) and at least three acryloyl groups and then neutralizing the reaction product; (b) a polyfunctional acrylate having at least three acryloyl groups; (c) an organic solvent; and (d) a photopolymerization initiator. The composition may comprise in addition to the components (e) a silica sol in an organic solvent as a dispersion medium. The composition may further comprise in addition to the components (f) an acrylic resin. Such composition is an active energy ray-curing abrasion-resistant coating composition which forms a film having excellent adhesion to a plastic sustrate, transparency, abrasion resistance and antistatic properties.
    Type: Grant
    Filed: July 26, 1994
    Date of Patent: April 25, 1995
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Noritaka Hosokawa, Kazuhide Hayama
  • Patent number: 5407972
    Abstract: A photocurable composition comprising the reaction products of hydroxy terminated liquid sulfide or polysulfide oligomers with photocurable ethylenically unsaturated compounds. The products provide improved sealants for air and marine vehicles.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: April 18, 1995
    Assignee: Sunrez Corp.
    Inventors: W. Novis Smith, Mark Livesay
  • Patent number: 5405657
    Abstract: A process for the production of flexible impregnated protective, auxiliary and insulating materials on a fibre basis for electrical purposes by the application of an impregnating agent to the material to be impregnated, followed by curing, characterised in that a solvent-free impregnating mass containing one or more olefinically unsaturated, radically polymerisable polyesters, which contain one or more radically polymerisable monomers as reactive diluents, one or more plasticizing agents and optionally one or more peroxide-free radical initiators is applied to the material to be impregnated and curing is then carried out with high energy radiation and optionally by further heating.
    Type: Grant
    Filed: November 2, 1993
    Date of Patent: April 11, 1995
    Assignee: Herberts G.m.b.H.
    Inventors: Udo Bastian, Rainer Krause, Gerhard Kiessling
  • Patent number: 5401602
    Abstract: Low fix temperature toner resins are fabricated by a reactive melt mixing process wherein polymer resins are cross-linked at high temperature and high shear. The resins are particularly suitable for high speed fusing, show excellent offset resistance and wide fusing latitude and superior vinyl offset properties.
    Type: Grant
    Filed: March 23, 1993
    Date of Patent: March 28, 1995
    Assignee: Xerox Corporation
    Inventors: Hadi K. Mahabadi, Enno E. Agur, Gerald R. Allison, Michael S. Hawkins, Stephan Drappel, Maria N. V. McDougall, Bernard Grushkin, Thomas R. Hoffend, Angelo J. Barbetta
  • Patent number: 5397671
    Abstract: A reactive melt mixing process for preparing toner resin, comprising: melting a reactive base resin, thereby forming a polymer melt; adding to said polymer melt a free radical initiator compound and optionally a vinyl monomer compound to form a second melt; and heating and mixing under high shear said second melt with optional addition of a vinyl monomer compound to form a partially crosslinked and partially gelled toner resin.
    Type: Grant
    Filed: February 10, 1994
    Date of Patent: March 14, 1995
    Assignee: Xerox Corporation
    Inventors: Robert D. Bayley, Carol A. Fox, Thomas R. Hoffend
  • Patent number: 5376494
    Abstract: Low fix temperature toner resins are fabricated by a reactive melt mixing process wherein polymer resins are cross-linked at high temperature and high shear. The resins are particularly suitable for high speed fusing, show excellent offset resistance and wide fusing latitude and superior vinyl offset properties.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: December 27, 1994
    Assignee: Xerox Corporation
    Inventors: Hadi K. Mahabadi, Enno E. Agur, Gerald R. Allison, Michael S. Hawkins, Stephan Drappel, Maria N. V. McDougall, Bernard Grushkin, Thomas R. Hoffend, Angelo J. Barbetta
  • Patent number: 5369139
    Abstract: Radiation and peroxide-curable oligomeric emulsions are prepared by mixing water, an .alpha.,.beta.-ethylenically unsaturated oligomer (e.g. an unsaturated polyester), a reactive, nonionic surfactant containing allyl unsaturation, and a metallic salt drier under high shear agitation until a stable emulsion is formed. Coatings prepared from these emulsions are tack and mar free and demonstrate good resistance to organic solvents and water.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: November 29, 1994
    Assignee: Cook Composites and Polymers Company
    Inventors: Rudolph H. Boeckeler, Delano R. Eslinger
  • Patent number: 5352556
    Abstract: A low melt toner resin with low minimum fix temperature and wide fusing latitude contains a linear portion and a cross-linked portion containing high density cross-linked microgel particles, but substantially no low density cross-linked polymer. The resin may be formed by reactive melt mixing.
    Type: Grant
    Filed: March 23, 1993
    Date of Patent: October 4, 1994
    Assignee: Xerox Corporation
    Inventors: Hadi K. Mahabadi, Enno E. Agur, Gerald R. Allison, Michael S. Hawkins, Stephan Drappel, Maria N. V. McDougall, Bernard Grushkin, Thomas R. Hoffend, Angelo J. Barbetta
  • Patent number: 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: 5326822
    Abstract: A heat-curable molding material consists of an unsaturated polyester, monomers, a propylene polymer, free radical initiators and conventional additives and assistants, the propylene polymer being dispersed in the form of solid, round particles having a smooth surface and a mean diameter of from 1 to 200 .mu.m in the polyester resin.
    Type: Grant
    Filed: June 26, 1992
    Date of Patent: July 5, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Anton Hesse, Walter Heckmann, Harald Kroeger, Bernd L. Marczinke, Volker Warzelhan
  • Patent number: 5281569
    Abstract: A desensitizing ink for printing by wet or dry offset, flexographic or typographic printing is disclosed and claimed. This ink contains at least one desensitizing agent, at least one ink binder which is polymerizable or crosslinkable by UV light or electron beam radiations and, if necessary, an initiator system. Thus, the drying time of the printings is greatly reduced. The ink is free from vaporizable ink solvents.
    Type: Grant
    Filed: February 25, 1992
    Date of Patent: January 25, 1994
    Assignee: SICPA International S.A.
    Inventors: Albert Amon, Laszlo K. Boksanyi
  • Patent number: 5236967
    Abstract: An optical molding composition is used for casting and does not cause irritation to the skin or possess a bad smell. This composition comprises1. an actinic radiation-curable, radical-polymerizable organic compound comprising(1) one or more polythiol compounds and(2) one or more polyene compounds each having at least two actinic radiation-reactive carbon-to-carbon double bonds in the molecule, and2. an actinic radiation-sensitive radical polymerization initiator.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: August 17, 1993
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Kazuo Ohkawa, Seiichi Saito
  • Patent number: 5229252
    Abstract: A photoimageable composition for forming a solder mask has a photopolymerizable acrylate chemical system which renders exposed portions insolvable to alkaline aqueous developers and an epoxy chemical system which hardens the composition after exposure and development. The acrylate chemical system comprises acrylate monomers, epoxy-acrylate oligomers and a photoinitiator. The epoxy chemical system comprises an epoxy resin and a curative therefore. The composition further comprises a cross-linking agent which is reactive with hydroxyl groups of the acrylate and epoxy chemical systems.
    Type: Grant
    Filed: October 21, 1991
    Date of Patent: July 20, 1993
    Assignee: Morton International, Inc.
    Inventors: Kathy M. Flynn, Vinai M. Tara, Kathleen L. Nelson
  • Patent number: RE35135
    Abstract: Disclosed is a photocurable composition comprising (a) a radical-polymerizable monomer, (b) an .alpha.-ketocarbonyl compound and (c) a derivative of mercaptobenzimidazole, mercaptobenzothiazole or mercaptobenzoxazole or an aromatic amine nucleus-substituted with an electron-attractive group. This composition has a high photocuring speed at a temperature close to normal temperature and gives a cured product excellent in various physical properties. This composition is valuable as a dental adhesive or resin.
    Type: Grant
    Filed: March 15, 1994
    Date of Patent: December 26, 1995
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Takeshi Sakashita, Takayuki Nakano