Polyepoxide Polymer Having Been Reacted To Yield Terminal Ethylenic Unsaturation Patents (Class 525/922)
  • Patent number: 8835012
    Abstract: A coating composition for a food or beverage can that includes an emulsion polymerized latex polymer formed by combining an ethylenically unsaturated monomer component with an aqueous dispersion of a water-dispersible polymer.
    Type: Grant
    Filed: March 13, 2013
    Date of Patent: September 16, 2014
    Assignee: Valspar Sourcing, Inc.
    Inventors: Robert M. O'Brien, Daniel E. Rardon, Rachael Ann Spynda, George K. Bartley, Richard H. Evans
  • Patent number: 8092876
    Abstract: A coating composition for a food or beverage can that includes an emulsion polymerized latex polymer formed by combining an ethylenically unsaturated monomer component with an aqueous dispersion of a water-dispersible polymer.
    Type: Grant
    Filed: July 17, 2009
    Date of Patent: January 10, 2012
    Assignee: Valspar Sourcing, Inc.
    Inventors: Robert M. O'Brien, Daniel E. Rardon, Rachael Ann Spynda, George K. Bartley, III, Richard H. Evans, T. Howard Killilea, Carl Cavallin
  • Patent number: 7678847
    Abstract: The invention teaches an encapsulated curable adhesive composition especially adapted for use as a structural adhesive. The adhesive composition enables formation of a thin layer reactive composition of microcapsules and a two-part curative. The adhesive composition comprises a first population of microcapsules encasing a monomer and a first-part curative comprising an initiator. The adhesive composition further comprises a second-part curative. The second-part curative comprises an activator and a catalyst. At least the activator of the second-part curative is preferably encapsulated in a second population of microcapsules. The catalyst and the second population of microcapsules can be dispersed in a binder material, along with the first population of microcapsules. The first population of microcapsules contain encapsulated within the core a monomer having a Tg 35° C. or less and the first-part curative. The first population microcapsules contain encapsulated within the core a monomer having a Tg 35° C.
    Type: Grant
    Filed: June 13, 2006
    Date of Patent: March 16, 2010
    Assignee: Appleton Papers Inc.
    Inventors: Nianxi Yan, Peggy Dorothy Sands, Sandra Jacqueline Guinebretiere
  • Patent number: 6783809
    Abstract: A photosensitive composition of (a) a compound of formula (Ia) or (Ib) and (b) a bifunctional acrylate or methacrylate.
    Type: Grant
    Filed: September 17, 2001
    Date of Patent: August 31, 2004
    Assignee: Huntsman Advanced Materials Americas Inc.
    Inventors: Bettina Steinmann, Adrian Schulthess, Max Hunziker
  • Patent number: 6774193
    Abstract: Stabilized pre-promoted unsaturated polymer resin systems that include a tertiary aromatic amine cure promoter. The stabilized curable resins systems can include a vinyl ester resin.
    Type: Grant
    Filed: July 17, 2002
    Date of Patent: August 10, 2004
    Assignees: Albemarle Corporation, The University of Southern Mississippi
    Inventors: John Gabriel Santobianco, Robson F. Storey, Rajamani Nagarajan
  • Patent number: 6479596
    Abstract: Novel epoxy acrylates and carboxyl group-containing epoxy acrylates of formulae II and III of the claims that are relatively highmolecular and are chemically crosslinkable can be used in photoresist formulations with the additional use of highly polymerised polymer binders. Such resist formulations are used in particular in the field of printed circuit boards and printing plates, are applicable from aqueous medium, are almost tack-free and have very good edge coverage, especially on conductors.
    Type: Grant
    Filed: May 23, 1996
    Date of Patent: November 12, 2002
    Assignee: Vantico, Inc.
    Inventors: Martin Roth, Roger Salvin, Kurt Meier, Bernhard Sailer, Rolf Wiesendanger
  • Patent number: 6436856
    Abstract: A curable vinyl ester resin composition capable of undergoing B-staging at room temperature comprises (a) an unmodified vinyl ester resin; (b) a reactive diluent consisting of an ethylenically unsaturated monomer; (c) a free-radical curing agent; (d) a B-staging agent comprising a Group II metal oxide or hydroxide, or a mixture thereof; and (e) a thickening agent comprising an ester, a ketone, an aldehyde or a mixture thereof. The thickening agent coacts with the B-staging agent to cause B-staging of the vinyl ester resin at room temperature. The vinyl ester resin composition according to the invention is particularly useful for impregnating a fibrous material such as a woven fabric material. The fibrous material impregnated with the vinyl ester resin composition of the invention has a shelf life of up to 12 months. B-staging is generally reached in about two weeks following mixture of the various components and impregnation of the fibrous material.
    Type: Grant
    Filed: June 14, 2000
    Date of Patent: August 20, 2002
    Assignee: Simex Technologies, Inc.
    Inventor: Halim Chtourou
  • Patent number: 6369164
    Abstract: An esterified macromonomer within the scope of the general formula: wherein Z is an organic moiety, R1 is hydrogen or a substituted or unsubstituted alkyl having from 1 to 12 carbon atoms, oxyalkyl having from 1 to 12 carbon atoms, alkenyl having from 2 to 12 carbon atoms, cycloalkyl having from 5 to 12 carbon atoms, aryl having from 6 to 12 carbon atoms or aralkyl having from 7 to 12 carbon atoms, each E independently is a hydroxyl group, an organic ester moiety or an inorganic ester containing moiety and at least one E is an ester containing moiety, n and m each independently is an integer from 2 to 12.
    Type: Grant
    Filed: January 3, 1996
    Date of Patent: April 9, 2002
    Assignee: Dentsply G.m.b.H.
    Inventors: Joachim E. Klee, Uwe Walz
  • Patent number: 6359082
    Abstract: The present invention relates to a process for the preparation of epoxy(meth)acrylates by simultaneously reacting 1 equivalent of organic compounds containing epoxide groups with A) 0.8 to 1.2 moles of organic dicarboxylic anhydrides having a molecular weight from 98 to 166 and B) 0.8 to 1.2 OH equivalents of OH group-containing reaction products, which are prepared at a COOH/OH equivalent ratio of 0.6:1 to 0.95:1, of a) (meth)acrylic acid and b) tri- or tetrahydric ether alcohols having a molecular weight of 180 to 1000 and containing at least two ethylene and/or propylene oxide units as part of an ether structure.
    Type: Grant
    Filed: June 18, 1997
    Date of Patent: March 19, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventor: Jürgen Meixner
  • Patent number: 6353061
    Abstract: A &agr;,&ohgr;-methacrylate terminated epoxide-carboxylic acid macromonomer compound formed by reaction of at least one diepoxide, at least one dicarboxylic acid and at least one unsaturated mono-carboxylic acid and having the general formula 1: wherein R is an aromatic moiety formed from a diepoxide R′ is a substituted or unsubstituted aliphatic, araliphatic, cycloaliphatic or aromatic moiety formed from a dicarboxylic acid, R″ is hydrogen, a substituted or unsubstituted aliphatic, araliphatic, aromatic or cycloaliphatic moiety formed from a mono-carboxylic acid, and n is an integer from 1 to 20.
    Type: Grant
    Filed: April 4, 1996
    Date of Patent: March 5, 2002
    Assignee: Dentsply GmbH
    Inventors: Joachim E. Klee, Hans-Heinrich Hörhold, Frank Claussen
  • Patent number: 6329475
    Abstract: The invention is a curable resin composition comprising A) an epoxy vinylester resin or a polyester resin; B) a polymerizable monomer; C) a chelating agent; and D) a copper salt or complex of copper with an alcohol, aldehyde or ketone; and E) an inhibitor comprising alkylated phenolic compound or polyhydroxy aromatic compound. In another aspect it is a resin system comprising I) a resin composition comprising: A) an epoxy vinylester resin or a polyester resin; B) a polymerizable monomer; C) a chelating agent comprising a polar or aromatic ring containing compound; D) a copper salt or a copper complex with an alcohol, ketone or aldehyde; and E) an inhibitor comprising alkylated phenolic compound or a polyhydroxy aromatic hydrocarbon and I) a catalyst system which comprises E) an additional amount of an inhibitor; F) optionally an aliphatic amine, an aromatic amine, or a heterocyclic amine; G) a peroxide or persulphate initiator; and H) a transition metal accelerator.
    Type: Grant
    Filed: February 10, 1995
    Date of Patent: December 11, 2001
    Assignee: The Dow Chemical Company
    Inventor: Paul Patrick Kelly
  • Patent number: 6316552
    Abstract: Compounds of formulae (Ia) and (Ib) wherein the substituents R1 are each independently of the other hydrogen or methyl, R2 is an unsubstituted C1-C20alkyl group or a C1-C20alkyl group which is substituted by one or more than one substituent selected from the group consisting of hydroxy, C6-C14aryl and halogen, an unsubstituted phenyl group or a phenyl group which is substituted by one or more than one substituent selected from the group consisting of C1-C6alkyl, hydroxy or halogen, or is a radical of formula —CH2—OR3, wherein R3 is an unsubstituted C1-C20alkyl group or a C1-C20alkyl group which is substituted by one or more than one substituent selected from the group consisting of hydroxy, C6-C14aryl and halogen, an unsubstituted phenyl group or a phenyl group which is substituted by one or more than one substituent selected from the group consisting of C1-C6alkyl, hydroxy and halogen, or is a C2-C6alkenyl group, a C2-C20acyl group or an unsubstituted cyclohexylcarbonyl group or
    Type: Grant
    Filed: January 13, 2000
    Date of Patent: November 13, 2001
    Assignee: Vantico Inc.
    Inventors: Bettina Steinmann, Adrian Schulthess, Max Hunziker
  • Patent number: 6262147
    Abstract: The present invention provides a thermosetting organic solvent type coating capable of forming a cured coating film having a TUKON hardness at 20° C. of 15 or more and the minimum value of dynamic modulus E′ at a frequency of 110 Hz in the temperature range of 150-200° C., of 1×109 dyn/cm2 or more. The cured film formed from the coating, as compared with the cured films formed from conventional organic solvent type coatings used as a top coat for automobile (e.g. an organic solvent type coating containing, as main components, a hydroxyl group-containing acrylic resin and a melamine resin, or a carboxylic-epoxy type coating), is at least equivalent in weatherability, finish appearance, acid resistance, etc. and superior in stain resistance.
    Type: Grant
    Filed: August 26, 1999
    Date of Patent: July 17, 2001
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Satoshi Ikushima, Seiji Wada, Yasumasa Okumura, Haruhiko Aida, Motoshi Yabuta, Yoshiyuki Yukawa, Ken-ichi Hasada
  • Patent number: 6184314
    Abstract: A vinyl ester resin derived from the reaction of about equivalent amounts of an unsaturated monocarboxylic acid and a polyepoxide is stabilized with from 0.01 to 5 weight percent of maleic acid and/or maleic anhydride.
    Type: Grant
    Filed: March 22, 1999
    Date of Patent: February 6, 2001
    Assignee: Swancor Industrial Co., Ltd.
    Inventors: Jan-Yang Tsai, Shih-Wen Yur
  • Patent number: 6043323
    Abstract: Compounds of formulae (Ia) and (Ib) ##STR1## wherein the substituents R.sub.1 are each independently of the other hydrogen or methyl, R.sub.2 is an unsubstituted C.sub.1 -C.sub.20 alkyl group or a C.sub.1 -C.sub.20 alkyl group which is substituted by one or more than one substituent selected from the group consisting of hydroxy, C.sub.6 -C.sub.14 aryl and halogen, an unsubstituted phenyl group or a phenyl group which is substituted by one or more than one substituent selected from the group consisting of C.sub.1 -C.sub.6 alkyl, hydroxy or halogen, or is a radical of formula --CH.sub.2 --OR.sub.3, wherein R.sub.3 is an unsubstituted C.sub.1 -C.sub.20 alkyl group or a C.sub.1 -C.sub.20 alkyl group which is substituted by one or more than one substituent selected from the group consisting of hydroxy, C.sub.6 -C.sub.14 aryl and halogen, an unsubstituted phenyl group or a phenyl group which is substituted by one or more than one substituent selected from the group consisting of C.sub.1 -C.sub.
    Type: Grant
    Filed: November 21, 1994
    Date of Patent: March 28, 2000
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Bettina Steinmann, Adrian Schulthess, Max Hunziker
  • Patent number: 6015848
    Abstract: The present invention provides a thermosetting organic solvent type coating capable of forming a cured coating film having a TUKON hardness at 20.degree. C. of 15 or more and the minimum value of dynamic modulus E' at a frequency of 110 Hz in the temperature range of 150-200.degree. C., of 1.times.1O.sup.9 dyn/cm.sup.2 or more. The cured film formed from the coating, as compared with the cured films formed from conventional organic solvent type coatings used as a top coat for automobile (e.g. an organic solvent type coating containing, as main components, a hydroxyl group-containing acrylic resin and a melamine resin, or a carboxylic-epoxy type coating), is at least equivalent in weatherability, finish appearance, acid resistance, etc. and superior in stain resistance.
    Type: Grant
    Filed: December 5, 1997
    Date of Patent: January 18, 2000
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Satoshi Ikushima, Seiji Wada, Yasumasa Okumura, Haruhiko Aida, Motoshi Yabuta, Yoshiyuki Yukawa, Ken-ichi Hasada
  • Patent number: 5925720
    Abstract: This invention provides a heterotelechelic oligomer or polymer which is represented by formula below: ##STR1## wherein R.sup.1 and R.sup.2 form an acetal, or, combined with each other, denote oxy (.dbd.O),p, m, n and q each denote a certain integer,L is a group which forms an ester, andZ denotes a certain functional group.This invention a so provides a process to produce the above oligomer or polymer by means of living polymeri-zation. Since this oligomer or polymer forms a high- molecular micelle which is stable in an aqueous solvent, said oligomer or polymer will be useful as a carrier for drug delivery.
    Type: Grant
    Filed: December 18, 1997
    Date of Patent: July 20, 1999
    Assignee: Kazunori Kataoka
    Inventors: Kazunori Kataoka, Carmen Scholz, Michihiro Iijima, Takahito Kutsuna, Yukio Nagasaki, Masao Kato, Teruo Okano
  • Patent number: 5876210
    Abstract: The invention concerns a process for preparing a polymer composition, that is free-radical/photochemical and thermal curing epoxide-methacrylate and/or isocyanate-methacrylate adhesives in broadest terms, dental/medical adhesives, and dental restoratives. Furthermore the dual curing epoxide-methacrylate and/or isocyanate-methacrylate adhesives can be used in the optical industry, in optoelectronics and microelectronics, for example for the adhesion of complicated optical components in the combination glass/glass, glass/metal. Advantageous is the small shrinkage during polymerization and the good mechanical properties in combination with the possibility of step-wise or one-step polymerization.
    Type: Grant
    Filed: November 21, 1996
    Date of Patent: March 2, 1999
    Assignee: Dentsply G.m.b.H.
    Inventors: Joachim E. Klee, Walter Leube
  • Patent number: 5861466
    Abstract: Vinyl ester resins processed until low epoxy values are reached are storage stable for two weeks at 54.degree. C. (130.degree. F.). Adding a copper salt inhibitor also provides two weeks storage stability at 54.degree. C. (130.degree. F.). A synergistic effect is observed if both low epoxy values are reached and copper naphthenate inhibitor is used, extending shelf life stability to two months at 54.degree. C. (130.degree. F.).
    Type: Grant
    Filed: April 1, 1997
    Date of Patent: January 19, 1999
    Assignee: Ashland Inc.
    Inventor: Danny G. Hartinger
  • Patent number: 5854313
    Abstract: Fine particles of high heat resistant polymer obtained by emulsion polymerization or seeded polymerization of at least one epoxy ester (C) having two or more unsaturated bonds in one molecule and at least one reactive monomer (D) having at least one unsaturated double bond in one molecule, in the absence of a water-insoluble inorganic material as a dispersion stabilizer, the epoxy ester (C) being obtained by adding at least one unsaturated monobasic acid (B) to at least one epoxide (A-1) having at least one glycidyl group and one monocyclic hydrocarbon group in one molecule, and/or at least one epoxide (A-2) having at least one cycloaliphatic epoxy group in one molecule. The fine polymer particles have excellent heat resistance and solvent resistance, and an aqueous or alcoholic dispersion of such fine polymer particles is produced therefrom.
    Type: Grant
    Filed: April 21, 1997
    Date of Patent: December 29, 1998
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yoshimasa Omori, Hiroya Okumura, Takashi Shibata
  • Patent number: 5843221
    Abstract: A sprayable, high solids, low-volatiles composition is provided which may be used as a coating on a variety of substrates. The sprayable filler composition comprises a first filler/glazing component formed from a mixture of a resin, a filler, a mixture of thixotropic clays, a phosphosilicate, and a first organic solvent. The coating also has a second organic solvent component as well as a second catalyst component. The coating as applied to a substrate has a thickness of up to 6 mils without sagging, running or cracking.
    Type: Grant
    Filed: August 4, 1997
    Date of Patent: December 1, 1998
    Assignee: Illinois Tool Works, Inc.
    Inventor: David Michael Parish
  • Patent number: 5726219
    Abstract: The present invention provides a rein composition comprising the following components (a), (b), (c), (d) and (e) as essential components; and an excellent multilayer printed circuit board obtained by using the resin composition:(a) a polyfunctional epoxy resin having an epoxy equivalent of 120-500,(b) a modified phenol novolac obtained by reacting 20-60 mole % of the phenolic hydroxyl groups of a phenol novolac obtained by condensing a phenol compound with formaldehyde in the presence of an acidic catalyst, with a glycidyl group-containing acrylate or methacrylate,(c) an epoxy acrylate or epoxy methacrylate compound,(d) a diluent consisting of a polyfunctional monomer having a plurality of photosensitive functional groups or a polyfunctional monomer having a photosensitive functional group and a heat-sensitive functional group, or a diluent consisting of a combination of the two monomers, and(e) a photopolymerization initiator.
    Type: Grant
    Filed: March 4, 1997
    Date of Patent: March 10, 1998
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Takeshi Hosomi, Hiroshi Hayai, Takayuki Baba
  • Patent number: 5726255
    Abstract: The present invention relates epoxy(meth)acrylates which are substantially free from epoxide groups and are the reaction products of organic compounds containing epoxide groups and having a number average molecular weight (M.sub.n) of 130 to 1000 withI) compounds containing carboxyl and ester groups at an equivalent ratio of carboxyl groups to epoxide groups of 0.7:1.0 to 1.0:1.0, wherein compounds I) are reaction products ofA) organic dicarboxylic acids or dicarboxylic acid anhydrides having a molecular weight of 98 to 164 withB) reaction products containing alcoholic hydroxyl groups and prepared at a COOH/OH equivalent ratio of 0.6 to 0.95 froma) (meth)acrylic acid andb) tri- or tetrahydric ether alcohols having a molecular weight of 180 to 1000, which contain at least two ethylene oxide units --CH.sub.2 --CH.sub.2 --O-- as part of one or more ether structures and which contain up to 20 mole %, based on the total moles of alkylene oxide units, of propylene oxide units, --CH.sub.2 --CH(CH.sub.
    Type: Grant
    Filed: March 15, 1996
    Date of Patent: March 10, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Meixner, Wolfgang Fischer
  • Patent number: 5702820
    Abstract: There is disclosed a photo-imaging resist ink containing (A) an unsaturated group-containing polycarboxylic acid resin which is a reaction product of (c) succinic anhydride with an additive reaction product of (a) an epoxy resin with (b) an unsaturated group-containing monocarboxylic acid, wherein (a) the epoxy resin is represented by the following formula (1): ##STR1## wherein M stands for ##STR2## n is at least 1 on the average; and m is 1 to n on the average. The resist ink is excellent in developability and photosensitivity, while the cured product thereof is excellent in flex resistance and folding resistance, and well satisfactory in adhesion, pencil hardness, solvent resistance, acid resistance, heat resistance, etc.
    Type: Grant
    Filed: June 10, 1996
    Date of Patent: December 30, 1997
    Assignees: Nippon Kayaku Kabushiki Kaisha, Nippon Polytech Corp.
    Inventors: Minoru Yokoshima, Tetsuo Ohkubo, Kazunori Sasahara, Yoneji Sato, Yoko Baba
  • Patent number: 5684082
    Abstract: There is disclosed a method for adhering rubber to reinforcing materials which comprises embedding a textile fiber or metal reinforcing material in a vulcanizable rubber composition comprising rubber, a vulcanizing agent, reinforcement, a methylene donor, a methylene acceptor and a maleic anhydride functionalized triblock copolymer having polystyrene endblocks and poly-(ethylene/butylene) midblocks.
    Type: Grant
    Filed: February 27, 1997
    Date of Patent: November 4, 1997
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Thomas Joseph Segatta
  • Patent number: 5677398
    Abstract: Disclosed are an epoxy acrylate resin of the general formula (1) ##STR1## and an acid-modified epoxy acrylate resin obtained by reacting the epoxy acrylate resin with a carboxylic acid or an anhydride thereof, as well as curable resin compositions containing such a resin and the cured products thereof.
    Type: Grant
    Filed: April 3, 1996
    Date of Patent: October 14, 1997
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Toshihiro Motoshima, Akio Karasawa, Keisuke Takuma, Akihiro Yamaguchi
  • Patent number: 5614581
    Abstract: A thermosetting in-mold coating for molded fiber-reinforced plastic parts is disclosed. The binder for the thermosetting coating is comprised of least one polymerizable epoxy-based oligomer having at least two acrylate groups and at least one copolymerizable ethylenically unsaturated monomer. The coating includes graphite and titanium dioxide which results in the gray color. The coating composition has good flow and coverage during molding, good adhesion, uniform color, good surface quality, and good paintability. The coating composition includes enough carbon black so that a 1.0 mil thick coating has a Ransburg conductivity meter reading of at least 165 units.
    Type: Grant
    Filed: October 18, 1995
    Date of Patent: March 25, 1997
    Assignee: GenCorp Inc.
    Inventors: David S. Cobbledick, Donald F. Reichenbach
  • Patent number: 5610206
    Abstract: A high molecular weight compound having a number average molecular weight of 5,000 to 30,000 formed from a styrenic or acrylic monomer chain and a rubber chain which are attached as block or graft polymers. A photopolymerizable resin composition includes a copolymer having a number average molecular weight of 5,000 to 30,000. The copolymer has a styrenic or acrylic monomer chain and a rubber chain attached in block or graft form.
    Type: Grant
    Filed: December 12, 1994
    Date of Patent: March 11, 1997
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hirokazu Komuro, Hiromichi Noguchi, Takahiro Mori
  • Patent number: 5576399
    Abstract: Novel epoxy acrylates and carboxyl group-containing epoxy acrylates of formulae II and III of the claims that are relatively highmolecular and are chemically crosslinkable can be used in photoresist formulations with the additional use of highly polymerized polymer binders. Such resist formulations are used in particular in the field of printed circuit boards and printing plates, are applicable from aqueous medium, are almost tack-free and have very good edge coverage, especially on conductors.
    Type: Grant
    Filed: June 28, 1994
    Date of Patent: November 19, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Roth, Roger Salvin, Kurt Meier, Bernhard Sailer, Rolf Wiesendanger
  • Patent number: 5554703
    Abstract: Nitrogenous multiacrylic monomers having the formula (I) are produced by reacting at least one diamine having the formula H.sub.2 N--R--NH.sub.2 with at least one polyepoxide resin and at least one (meth)acrylic epoxide. Application in the production of polymers for use in the preparation of varnishes, adhesives, films and composite materials.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: September 10, 1996
    Assignee: Cray Valley S.A.
    Inventors: Jean-Pierre Pascault, Florence Rolly, Mohamed Taha, Christelle Titier
  • Patent number: 5516860
    Abstract: Radiation-curable acrylates are prepared by a process in which, in a 1st stage, a hydroxy compound is reacted with acrylic acid or methacrylic acid and, in or before a 2nd stage, the reaction product of the 1st stage is then reacted with an epoxy compound and compounds having one or more primary or secondary amino groups are added in the 2nd stage and the reaction in the 2nd stage is continued, after the addition of these compounds, until the acid number of the reaction mixture has decreased by at least 3 mg KOH/g of reaction mixture from the time of the addition of these compounds.
    Type: Grant
    Filed: May 1, 1995
    Date of Patent: May 14, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Reich, Ulrich Jager, Erich Beck, Edmund Keil, Ulrich Erhardt, Adolf Nuber
  • Patent number: 5510428
    Abstract: Compositions (I), (II) and (III) comprising compounds having vinyl groups as side chains and epoxidized compositions (XI), (XII) and (XIII) thereof, which can be prepared by the various reaction combinations of (a) with (b) or (b)+(c), and or (d), where(a) is at least one compound having at least one vinyl group and one epoxy group in the molecule; (b) is at least one of a polybasic compound, an anhydride thereof, a polymer having carboxylic groups at terminals and a polymer having carboxylic groups as side chains; (c) is at least one organic compound having at least one active hydrogen atom; and (d) is at east one of an unsaturated monocarboxylic compound or an unsaturated monocarboxylic ester having a hydroxyl group.
    Type: Grant
    Filed: November 21, 1994
    Date of Patent: April 23, 1996
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yoshiyuki Harano, Sozo Namai, Katsuyuki Maeda, Takaaki Murai
  • Patent number: 5476752
    Abstract: An active energy ray-curing resin composition comprises:(i) a linear polymer having a glass transition temperature of 50.degree. C. or higher and a weight average molecular weight of about 3.0.times.10.sup.4 or higher;(ii) a monomer having an ethylenically unsaturated bond;(iii) an epoxy resin comprising at least one compound having one or more epoxy groups in the molecule; and(iv) a polymerization initiator capable of generating a Lewis acid by irradiation with an active energy ray.
    Type: Grant
    Filed: April 3, 1995
    Date of Patent: December 19, 1995
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata
  • Patent number: 5434225
    Abstract: An epoxy resin adhesive, sealing or coating composition containing as a curing agent an addition product of A) at least one member of the group consisting of primary amines and secondary amines and B) at least one ester having a formula selected from the group consisting of ##STR1## wherein m is 0 or 1, n is an integer from 3 to 25, 0 is an integer from 1 to 20, p is an integer from 1 to 10, R.sub.1 is selected from the group consisting of furyl, phenyl and hydrogen, R.sub.2 is hydrogen or methyl R.sub.3 is ##STR2## R.sub.5 is methylene or --CH.sub.2 --CH--CH.sub.2 --R.sub.6 --CH.sub.2 --. R.sub.6 is selected from the group consisting of ##STR3## R.sub.7 is selected from the group consisting of methylene, ##STR4## and R.sub.8 and R.sub.9 are individually ethylene or propylene.
    Type: Grant
    Filed: December 6, 1994
    Date of Patent: July 18, 1995
    Assignee: Rutgerswerke AG
    Inventors: Alfred Mathes, Ulrich Grundke, Bert Meier, Jurgen Zehrfeld
  • Patent number: 5416173
    Abstract: An amine reacted acrylated epoxy resin blend that is particularly suitable for impregnating a fiber material and at least initial curing by exposure to ionizing radiation. These epoxy resins are basically produced by combining epoxy resins, including esterified epoxy resins, with stoichiometric quantities of aliphatic or cyclo aliphatic polyamines. The resins can be used to impregnate fibers which are exposed to ionizing radiation such as an electron beam or ultraviolet light and immediately formed into a structure, such as by filament winding. A short exposure to the ionizing radiation produces a stress-free, self supporting structure that can be fully cured through simple heating without elaborate tooling, vacuum bagging, autoclaves or the like.
    Type: Grant
    Filed: July 15, 1994
    Date of Patent: May 16, 1995
    Assignee: Martin Marietta Corporation
    Inventors: John Gagliani, Ronald K. Giesy
  • Patent number: 5395900
    Abstract: An acrylated epoxy resin based on bisphenol-S having a formula as follows ##STR1## wherein ph is phenylene or halophenylene; R.sub.1 is C.sub.2 -C.sub.4 alkylene;R.sub.2 is --CH.sub.2 CH(OH)CH.sub.2 --;R.sub.3 is acryloyl or methacryloyl;m is 0-4 integer, n is 0-4 integer and k is 0-5 integer.
    Type: Grant
    Filed: September 27, 1993
    Date of Patent: March 7, 1995
    Assignee: National Science Council
    Inventors: Der-Jan Liaw, Wen-Chang Shen
  • Patent number: 5393850
    Abstract: Vinyl ester resins of the type already having reactive liquid polymers reacted into the backbone of the resins, are cured in the presence of a reactive liquid polymer additive admixed with the prereacted vinyl ester resin. Heating of the system during cure causes the reactive liquid polymer additive to miscibilize with the vinyl ester base resin. The vinyl ester resin modified in the manner described above shows a significant enhancement in toughness as measured by fracture energy over unmodified counterparts or counterparts modified by known methods of adduction or admixing alone.
    Type: Grant
    Filed: January 6, 1993
    Date of Patent: February 28, 1995
    Assignee: The B. F. Goodrich Company
    Inventors: Alan R. Siebert, C. Dale Guiley
  • Patent number: 5371117
    Abstract: A sprayable, high solids, low-volatiles filler composition is provided which may be used as a coating on a variety of substrates. The sprayable filler composition comprises a first filler/glazing component formed from a mixture of a resin, a filler, a mixture of thixotropic clays, activated fumed silica, hollow glass microspheres, and a ketone solvent. The sprayable filler composition has a second catalyst component. The glazing/filler component is blended with the catalyst component, preferably either internally or externally of the spray nozzle, and the resultant sprayable filler composition is sprayed onto a substrate. The resulting cured coating provides a sandable surface which is corrosion resistant.
    Type: Grant
    Filed: November 30, 1993
    Date of Patent: December 6, 1994
    Assignee: Fibre Glass-Evercoat Company, Inc.
    Inventors: David M. Parish, Kenneth E. Lewis
  • Patent number: 5336716
    Abstract: The invention relates to paints comprising(i) a resin (A) which contains hydroxyl groups and .alpha.,.beta.-unsaturated carbonyl groups or a mixture of such resins, and/or(ii) a mixture consisting ofa) a hydroxyl-containing resin (B) or a mixture of such resins andb) a crosslinking agent (C) which contains .alpha.,.beta.-unsaturated carbonyl groups or a mixture of such crosslinking agents and(iii) a catalyst (D) which catalyzes the reaction of hydroxyl groups with .alpha.,.beta.-unsaturated carbonyl groups or a mixture of such catalysts.The invention is characterized in that the catalyst (D) is a Bronsted acid.
    Type: Grant
    Filed: February 25, 1993
    Date of Patent: August 9, 1994
    Assignee: BASF Lacke + Farben Aktiengesellschaft
    Inventors: Elisabeth Kappes, Ulrich Poth
  • Patent number: 5326795
    Abstract: Storage stable thermosettable ethylenically unsaturated resins containing at least one 1,4-naphthoquinone substituted on the 2 or 3 or both the 2 and 3 positions. The reactivity of these storage stable resins with curing agents is not unacceptably reduced by the presence of the stabilizer. The compositions are useful in the preparation of laminates or composites and in filament winding pultrusion, braiding and resin transfer molding applications.
    Type: Grant
    Filed: October 20, 1993
    Date of Patent: July 5, 1994
    Assignee: The Dow Chemical Company
    Inventor: Paul L. Wykowski
  • Patent number: 5319060
    Abstract: A method of preparing an unsaturated ester resin having improved storage stability is disclosed. An epoxy compound and polymerizable unsaturated monocarboxylic acid are reacted in the presence of a trivalent organic phosphorous catalyst. The catalyst is subsequently deactivated by oxidation. The resin may then be reacted with an acid anhydride.
    Type: Grant
    Filed: June 22, 1993
    Date of Patent: June 7, 1994
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Katsue Nishikawa, Yoshichi Hagiwara
  • Patent number: 5298543
    Abstract: Curable compositions from storage stable thermosettable ethylenically unsaturated resins containing at least one 1,4-naphthoquinone substituted on the 2 or 3 or both the 2 and 3 positions. The reactivity of these storage stable resins with curing agents is not unacceptably reduced by the presence of the stabilizer. The curable compositions are useful in the preparation of laminates or composites and in filament winding pultrusion, braiding and resin transfer molding applications.
    Type: Grant
    Filed: July 28, 1993
    Date of Patent: March 29, 1994
    Assignee: The Dow Chemical Company
    Inventor: Paul L. Wykowski
  • Patent number: 5288360
    Abstract: An adhesive resin composition comprising a polymer of a radically polymerizable epoxy resin (I) and a monomer (c), the radically polymerizable epoxy resin (I) being a reaction product between an epoxy resin (a) and a radically polymerizable monomer (b) having a function group reactive to epoxy group or hydroxyl group in said epoxy resin (a), having an equivalent ratio (b)/(a)=0.01.about.0.9 and said monomer (c) being copolymerizable with said radically polymerizable epoxy resin (I) and containing alkyl (meth)acrylate and/or a fluorine-containing unsaturated monomer serving as an indispensable component. The adhesive resin composition has an excellent adhesion between fluorine-contained resins and metal substrates.
    Type: Grant
    Filed: October 9, 1992
    Date of Patent: February 22, 1994
    Assignee: Mitsubishi Petrochemical Company, Ltd.
    Inventors: Kazuhide Hayama, Kazuyuki Hata, Keizo Abe, Takahiro Ozu
  • Patent number: 5281678
    Abstract: A method of preparing an unsaturated ester resin having improved storage stability is disclosed. An epoxy compound and polymerizable unsaturated monocarboxylic acid are reacted in the presence of a trivalent organic phosphorous catalyst. The catalyst is subsequently deactivated by oxidation. The resin may then be reacted with an acid anhydride.
    Type: Grant
    Filed: November 19, 1991
    Date of Patent: January 25, 1994
    Assignee: W. R. Grace & Co.
    Inventors: Katsue Nishikawa, Yoshichi Hagiwara
  • Patent number: 5272197
    Abstract: Thermosettable ethylenically unsaturated resins are rendered storage stable by the addition of at least one 1,4-naphthoquinone substituted on the 2 or 3 or both the 2 and 3 positions. The reactivity of these storage stable resins with curing agents is not unacceptably reduced by the presence of the stabilizer.
    Type: Grant
    Filed: April 1, 1992
    Date of Patent: December 21, 1993
    Assignee: The Dow Chemical Company
    Inventor: Paul L. Wykowski
  • Patent number: 5242996
    Abstract: A modified epoxy resin or compound of the formula: ##STR1## wherein A is the backbone reside of a glycidyl ether epoxy resin with removal of the glycidyloxy groups; R.sup.1 and R.sup.2 are independently a hydrogen atom or C.sub.1 -C.sub.12 alkyl; R.sup.3 is a glycidyl group; and n is an integer of greater than 1. A method for producing the modified epoxy resin is also disclosed.
    Type: Grant
    Filed: May 22, 1991
    Date of Patent: September 7, 1993
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Mitsuo Yamada, Kei Aoki, Ryuzo Mizuguchi
  • Patent number: 5235008
    Abstract: Polymer modified adducts are prepared by (A) reacting (1) an epoxy resin having an average of more than one vicinal epoxide group with (2) a compound containing an average of two or more hydrogen atoms reactive with an epoxide group; and (B) partially vinylizing reacting the product from step (A); and (C) polymerizing the partially vinylized product from step (B) with (3) a polymerizable ethylenically unsaturated monomer; with the proviso that at least one of the components (1), (2) or (3) contain one or more rodlike mesogenic moieties. These adducts are useful as epoxy resin curing agents.
    Type: Grant
    Filed: August 3, 1990
    Date of Patent: August 10, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5213875
    Abstract: Resin compositions comprising 20 to 50% by weight, based on total composition weight, of a first resin which comprises an acrylate-epoxy oligomer having a molecular weight of from 2000 to 5000; from 2 to 10% of a second resin which comprises an acrylate-urethane oligomer; up to 50% of a third resin which comprises a second acrylate-epoxy oligomer, where from 1 to 5% of the epoxy is an epoxy novolac; from 10 to 40% of a liquid acrylate; from 2 to 20% of a liquid diacrylate having an ether linkage; from 5 to 25% of a liquid alkylene diacrylate; and from 1 to 5% of a UV photoinitiator. The compositions also preferably includes from 0.05 to 1% of a flow control agent. The compositions are applied to substrates such as printed wiring boards and cured with ultraviolet light to form a conformal coating on the substrate.
    Type: Grant
    Filed: September 7, 1988
    Date of Patent: May 25, 1993
    Assignee: Westinghouse Electric Corp.
    Inventors: Wei-Fang A. Su, Anthony P. Barrett
  • Patent number: 5204386
    Abstract: A thixoropic adhesive composition exhibiing good sag resistance is prepared comprising a mixture of a polymer-modified epoxy resin and a rheological control agent. The polymer-modified epoxy resin is preferably a dispersion of acrylic elastomer in an epoxy resin in which the acrylic elastomer particles have added hydroxyl functionality which interacts favorably with rheological control agents, such as fumed silica. Acrylic epoxy resin dispersions containing added hydroxyl functionality give improved rheological control.
    Type: Grant
    Filed: June 9, 1992
    Date of Patent: April 20, 1993
    Assignee: The Dow Chemical Company
    Inventors: Yasemin Ersun-Hallsby, Dwight K. Hoffman, Gerald C. Kolb, Gene D. Rose
  • Patent number: RE37448
    Abstract: The present invention relates epoxy(meth)acrylates which are substantially free from epoxide groups and are the reaction products of organic compounds containing epoxide groups and having a number average molecular weight (Mn) of 130 to 1000 with I) compounds containing carboxyl and ester groups at an equivalent ratio of carboxyl groups to epoxide groups of 0.7:1.0 to 1.0:1.0, wherein compounds I) are reaction products of A) organic dicarboxylic acids or dicarboxylic acid anhydrides having a molecular weight of 98 to 164 with B) reaction products containing alcoholic hydroxyl groups and prepared at a COOH/OH equivalent ratio of 0.6 to 0.
    Type: Grant
    Filed: March 8, 2000
    Date of Patent: November 13, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Juergen Meixner, Wolfgang Fischer