Wherein Unsaturated Reactant Contains Only One Free Carboxyl Group Patents (Class 525/531)
  • Patent number: 5998510
    Abstract: This invention relates to low pressure sheet molding compounds and, more particularly, to a composition that is moldable at pressures below about 100 psi, said composition being made by combining: (A) an unsaturated prepolymer resin; (B) a monomeric unsaturated polymerizable material containing a terminal ethylene group; (C) a hydroxy-terminated polyester having a molecular weight in the range of about 500 to about 3000; (D) a polyisocyanate; and (E) a polymerization initiator; the mole ratio of NCO groups from (D) to OH groups from (C) being in the range of about 0.1 to about 10.
    Type: Grant
    Filed: January 30, 1998
    Date of Patent: December 7, 1999
    Assignee: Premix, Inc.
    Inventor: Kurt Ira Butler
  • Patent number: 5985456
    Abstract: A thermally curable adhesive composition that includes a fluxing agent that also acts as an adhesive is provided. The composition includes: (a) a fluxing agent represented by the formula RCOOH, wherein R comprises a moiety having two or more carbon-carbon double bonds wherein in one embodiment, at least one is within an acrylate or methacrylate group, and which may further contain at least one aromatic moiety; (b) optionally, an effective amount of a crosslinkable diluent; (c) optionally, an effective amount of a source of free radical initiators; and (d) optionally, an effective amount of a resin to react with remnant carboxylic acid moieties. By employing an acrylate, methacrylate, or phenol in the structure of the adhesive flux, the cure temperature and moisture absorption characteristics can be significantly improved. The composition can be applied directly onto the surface(s) of devices that are to be joined electrically and mechanically.
    Type: Grant
    Filed: September 9, 1997
    Date of Patent: November 16, 1999
    Assignee: Miguel Albert Capote
    Inventors: Zhiming Zhou, Miguel A. Capote
  • Patent number: 5985043
    Abstract: A thermally curable adhesive composition that includes a fluxing agent that also acts as an adhesive is provided. The composition includes: (a) a fluxing agent represented by the formula RCOOH, wherein R comprises a moiety having two or more carbon--carbon double bonds; (b) optionally, an effective amount of a crosslinkable diluent; (c) optionally, an effective amount of a source of free radical initiators; and (d) optionally, an effective amount of a resin to react with remnant carboxylic acid moieties. The composition can be applied directly onto the surface(s) of devices that are to be joined electrically and mechanically. These devices include, printed circuit substrates, connectors, components, cables, and other electrical devices having metallization patterns to be soldered together by means of a solder-bumped pattern on one or both surfaces. Alternatively, a solder paste, comprising solder powder mixed with the fluxing agent of the present invention can be used.
    Type: Grant
    Filed: July 21, 1997
    Date of Patent: November 16, 1999
    Assignee: Miguel Albert Capote
    Inventors: Zhiming Zhou, Miguel A. Capote
  • Patent number: 5973034
    Abstract: There are provided a resin composition and hardened products thereof for use in resistors, phosphors, conductors, patterns and the like, which can be developed with water or a dilute alkaline aqueous solution, show good pattern accuracy, give small residual organic matter after baking and have excellent adhesiveness. The resin composition which comprises (A) an unsaturated group-containing resin which is an epoxy methacrylate resulting from the reaction of (a) an epoxy resin having at least two epoxy groups in its molecule with (b) a compound having one unsaturated double bond and one carboxyl group in one molecule and (c) a saturated monocarboxylic acid as an optional component, the reaction product epoxy (meth)acrylate being allowed to react with (d) a polybasic acid anhydride as occasion demands, (B) a diluent, (C) a photopolymerization initiator and (D) one or more substances selected from metal powders, metal oxides, metal sulfides or glass.
    Type: Grant
    Filed: September 30, 1996
    Date of Patent: October 26, 1999
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Satoshi Mori, Minoru Yokoshima
  • Patent number: 5922817
    Abstract: A water-dispersible polymer and a coating composition containing the water-dispersible polymer are disclosed. The water-dispersible polymer is prepared from: (a) an epoxy compound having about two epoxy groups, such as an epoxy resin, (b) a linking compound having (i) conjugated carbon--carbon double bonds or a carbon--carbon triple bond and (ii) a moiety capable of reacting with an epoxy group, such as sorbic acid, and (c) acrylic monomers, at least a portion of which are capable of rendering the polymer water dispersible, such as acrylic acid, wherein the epoxy portion (a) of the polymer is covalently linked to the polymerized acrylic portion (c) by linking compound (b). The coating composition contains the water-dispersible polymer, a fugitive base to solubilize the polymer, a curing agent, and a carrier containing water.
    Type: Grant
    Filed: May 11, 1998
    Date of Patent: July 13, 1999
    Assignee: The Dexter Corporation
    Inventors: Walter R. Pedersen, Joseph Devasia Ponmankal
  • Patent number: 5905103
    Abstract: The invention relates to a process for the preparation of pigment paste resins for cathodically depositable coating compositions, wherein diepoxide compounds which contain polyoxyalkylene structures and alkyl and/or alkylene and/or hydroxyalkyl radicals having more than 3 carbon atoms are first reacted to form epoxy resin/amine adducts and final products with oxazolidine structures are obtained by a partial or complete reaction of secondary amino groups with formaldehyde.
    Type: Grant
    Filed: March 15, 1993
    Date of Patent: May 18, 1999
    Assignee: Vianova Resins, AG
    Inventors: Helmut Honig, Georg Pampouchidis, Willibald Paar, Herbert Matzer, Manfred Valtrovic
  • Patent number: 5889076
    Abstract: A composition that is useful in the preparation of radiation curable coatings is provided. The composition comprises the reaction product of an epoxy component and an acid component comprised of an ethylenically unsaturated carboxylic acid or reactive derivative thereof, reacted in the presence of, or post-reaction blended with, a polyamide based on a polymerized fatty acid. The polyamide preferably has a number average molecular weight of less than about 10,000 g/mole. Also provided is a polymerizable composition comprised of the composition comprised of the reaction product, the polyamide, and a reactive diluent. A method of coating a substrate is also provided which comprises applying to a substrate a composition comprised of the reaction product and the polyamide and exposing said composition to radiation to cure said composition.
    Type: Grant
    Filed: April 23, 1996
    Date of Patent: March 30, 1999
    Assignee: Henkel Corporation
    Inventors: Miguel A. Dones, Theresa M. Miller
  • Patent number: 5883193
    Abstract: A thermosettable adhesive composition that includes a monomeric or partially polymerized composition that includes at least one polymerizable acrylic or methacrylic acid ester of a non-tertiary alcohol, a thermosettable epoxy resin, an amine curative, a silane coupling agent, and a chelating agent.
    Type: Grant
    Filed: July 1, 1997
    Date of Patent: March 16, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Naimul Karim
  • Patent number: 5880171
    Abstract: A polymerizable composition for the production of high quality ophthalmic lenses is disclosed that includes:a) between 20 and 90 weight percent, and preferably, at least 50 weight percent, of urethane, epoxy, or polyester oligomers end terminated with acrylate or methacrylate (or mixtures of acrylate and methacrylate);b) between 5 and 50 to 80 percent, preferably between 10 and 40 percent, by weight of an optional diluent, such as a hydrocarbon diol end terminated with acrylate or methacrylate, or mixtures thereof, or a crosslinkable tri-, tetra-, or poly-acrylate or methacrylate, or mixtures thereof; andc) conventional optional additives, including but not limited to free radical initiators, UV absorbers, mold release agents, stabilizers, dyes, antioxidants, and wetting agents.The invention also includes ophthalmic lenses prepared from this composition and an apparatus for the production of lenses using sequential polymerization.
    Type: Grant
    Filed: January 11, 1995
    Date of Patent: March 9, 1999
    Assignee: 2C Optics, Inc.
    Inventors: Fredric J. Lim, Young C. Bae, David S. Soane
  • 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: 5859155
    Abstract: There is provided an adhesive composition for use in a flexible printed circuit board, comprising:(a) an epoxy resin having substantially at least two epoxy groups per molecule;(b) at least one selected from carboxyl group-containing nitrile rubber and carboxyl group-containing hydrogenated nitrile rubber; and(c) a curing agent which comprises aromatic amine having substantially at least two primary amino groups per molecule (c1) and dicyandiamide (c2), the molar ratio of the aromatic amine (c1) to the dicyandiamide (c2) being 35/65.ltoreq.(c1)/(c2).ltoreq.99/1.
    Type: Grant
    Filed: May 19, 1997
    Date of Patent: January 12, 1999
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Toshikazu Furihata, Akio Ikeda, Wataru Soejima
  • 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: 5830952
    Abstract: A water-dispersible polymer and a coating composition containing the water-dispersible polymer are disclosed. The water-dispersible polymer is prepared from: (a) an epoxy compound having about two epoxy groups, such as an epoxy resin, (b) a linking compound having (i) conjugated carbon--carbon double bonds or a carbon--carbon triple bond and (ii) a moiety capable of reacting with an epoxy group, such as sorbic acid, and (c) acrylic monomers, at least a portion of which are capable of rendering the polymer water dispersible, such as acrylic acid, wherein the epoxy portion (a) of the polymer is covalently linked to the polymerized acrylic portion (c) by linking compound (b). The coating composition contains the water-dispersible polymer, a fugitive base to solubilize the polymer, a curing agent, and a carrier containing water.
    Type: Grant
    Filed: February 22, 1996
    Date of Patent: November 3, 1998
    Assignee: The Dexter Corporation
    Inventors: Walter R. Pedersen, Joseph Devasia Ponmankal
  • Patent number: 5811497
    Abstract: Disclosed herein is a curing catalyst comprising at least one compound which is a substituted or unsubstituted aromatic or heteroaromatic compound and having any one of groups (I) --O--R.sub.1, (II) --O--CY--R.sub.1, or (III) --O--CY--X--R.sub.1, the groups being directly bonded to the armoatic or heteroaromatic ring, in a number of 1 to 10 wherein R.sub.1 may be the same or different and is a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, X is O or NH and Y is O or S. Furthermore, an epoxy resin composition comprising the curing catalyst is disclosed.
    Type: Grant
    Filed: September 11, 1995
    Date of Patent: September 22, 1998
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shuzi Hayase, Yoshihiko Nakano, Shinji Murai, Yukihiro Mikogami
  • Patent number: 5807910
    Abstract: An adhesive for a flexible printed circuit board and the method of preparing the same where the adhesive displays excellent migration inhibition, moisture adsorption resistance, and superior peeling strength, heat resistance, solvent resistance, chemical resistance, flexibility, and electrical properties. The adhesive is prepared by pre-polymerizing an epoxy resin, a COOH-containing rubber, a filler, and a primary catalyst in a solvent using a tertiary amine as a primary catalyst to form a prepolymer, followed by curing the prepolymer using a curing agent and a curing catalyst. The adhesive is coated on a plastic film, dried and laminated with a copper foil and then cured at an elevated temperature to form a substrate.
    Type: Grant
    Filed: June 23, 1997
    Date of Patent: September 15, 1998
    Assignees: Industrial Technology Research Institute, Mek Tec Corporation
    Inventors: Tseng-Young Tseng, Yeong-Tsyr Hwang, Hsiao-Chian Li
  • Patent number: 5804680
    Abstract: A flame-resistant, UV-curable single-component reactive resin system comprises a phosphorus-containing acrylate, another unsaturated compound which can undergo free radical copolymerization with acrylates and a free radical initiator system.
    Type: Grant
    Filed: March 5, 1997
    Date of Patent: September 8, 1998
    Assignee: Siemens Aktiengesellschaft
    Inventors: Winfried Plundrich, Ernst Wipfelder
  • Patent number: 5792804
    Abstract: The present invention relates to a process for the preparation of an aqueous coating composition containing a carboxyl-containing epoxy resin having an acid number in the range from 5 to 200 mg of KOH/g and having an epoxide equivalent weight in the range from 1000 to 40,000, optionally crosslinking agents, organic solvents, optionally conventional assistants and additives, and optionally pigments and fillers. The organic binder solution is neutralized using a tertiary amine in the temperature range from 60.degree. C. to 120.degree. C. This is followed by dispersion in water, with the proviso that at least 95% of the epoxide groups of the epoxy resin have been reacted. The aqueous coating compositions prepared by the process are preferably used for coating cans.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: August 11, 1998
    Assignee: BASF Lacke + Farben, AG
    Inventors: Klaus Cibura, Hans Jurgen Figge, Regina Willmer, Holger Herbert Dartmann
  • Patent number: 5780117
    Abstract: Radiation-curable latex compositions having a secondary curing mechanism are disclosed. In these compositions, an anionically stabilized, water-borne dispersion of one or more radiation-curable resins is combined with a low molecular weight compound having at least two reactive functional groups, wherein one reactive functional group comprises an epoxy and the other reactive functional group comprises either an epoxy or a functionality capable of self-condensation after film formation. Also disclosed is a method for providing a cross-linked protective coating on a substrate, wherein a coating of the composition of the present invention is applied to the substrate, the coated substrate is exposed to actinic radiation to effect curing, and then the unexposed or underexposed portions of the coated substrate are allowed to cure at room temperature or greater.
    Type: Grant
    Filed: February 25, 1997
    Date of Patent: July 14, 1998
    Assignee: Rohm and Haas Company
    Inventors: Andrew Joseph Swartz, Kurt Arthur Wood
  • Patent number: 5767175
    Abstract: An aqueous coating composition comprising an acrylic resin-modified epoxy resin (D), which is obtained by the reaction between a mixture of a bisphenol F based epoxy resin (A) and a bisphenol F based phenoxy resin (B) and an acrylic resin having carboxyl functionality (C), said acrylic resin-modified epoxy resin (D) being dispersed into water, preferably by using ammonia or amine, provides a composition with low viscosity, excellent storage stability and excellent application workability. In addition, the coating of the present invention can be applied to an interior surface and the resulting film has a smooth surface, excellent processability, excellent retorting resistant properties, excellent adhesion properties, and excellent corrosion resistant properties.
    Type: Grant
    Filed: February 1, 1996
    Date of Patent: June 16, 1998
    Assignee: Kansai Paint Company, Ltd.
    Inventors: Yasuo Kamekura, Tomokuni Ihara, Kaoru Morita
  • Patent number: 5756829
    Abstract: The present invention relates to a process for the preparation of amine-modified epoxy (meth)acrylates by reacting organic compounds having epoxy groups witha) acrylic and/or methacrylic acid in a carboxyl/epoxide equivalent ratio of 0.8:1 to 0.99:1 andb) basic nitrogen compounds selected from ammonia and (cyclo)aliphatic primary or secondary amines in an NH/epoxide equivalent ratio of 0.01:1 to 0.2:1,such that the epoxy groups originally present are substantially completely reacted and at least 0.01 NH equivalents, per epoxide equivalent, of the basic nitrogen compounds are reacted with the epoxy groups still present after completion of the reaction according to step a).A present invention also relates to the use of the amine-modified epoxy (meth)acrylates obtained from this process as binders in radical-cured coating, putty or sealant compositions or for the preparation of molded articles.
    Type: Grant
    Filed: May 1, 1995
    Date of Patent: May 26, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Meixner, Wolfgang Fischer
  • Patent number: 5741835
    Abstract: A stable aqueous emulsions of epoxy resins are provided using an epoxy-functional polyether having the formula: ##STR1## wherein R.sup.1 is a C.sub.1 -C.sub.15 alkyl, aryl or alkylaryl group, R.sup.2 is a divalent aliphatic group, a divalent cycloaliphatic group, a divalent aryl group, or a divalent arylaliphatic group, R.sup.3 is independently a hydrogen or a C.sub.1 -C.sub.10 alkyl group, R.sup.8 is a divalent aliphatic group optionally containing ether or ester group(s) or together with R.sup.9 or R.sup.10 form a spiro ring optionally containing heteroatoms, and R.sup.9 and R.sup.10 are independently hydrogen or R.sup.9 or R.sup.10 together with R.sup.
    Type: Grant
    Filed: July 17, 1997
    Date of Patent: April 21, 1998
    Assignee: Shell Oil Company
    Inventor: Charles John Stark
  • 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: 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: 5712363
    Abstract: The present invention relates to coating compositions including a particular class of oligomeric sterically hindered polyamines as replacements for traditional blocked and unblocked polyamine crosslinkers. The use of these oligomeric sterically hindered polyamine crosslinkers resultss in a desirable pot life/cure speed relationship not generally available with traditional unblocked polyamine crosslinkers, as well as a lower VOC and often better appearance characteristics than generally available with the traditional blocked varieties.
    Type: Grant
    Filed: August 28, 1995
    Date of Patent: January 27, 1998
    Assignee: Akzo Nobel NV
    Inventors: Arie Noomen, Thomas Mezger, Klaus Hobel, Keimpe Jan van den Berg
  • 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: 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: 5663247
    Abstract: A hyperbranched macromolecule of polyester type comprising a central monomeric or polymeric nucleus and at least one generation of a branching chain extender having at least three reactive sites of which at least one is a hydroxyl or hydroxyalkyl substituted hydroxyl group and at least one is a carboxyl or terminal epoxide group. The nucleus is an epoxide compound having at least one reactive epoxide group. Optionally, the macromolecule comprises at least one generation consisting of at least one spacing chain extender having two reactive sites of which one is a hydroxyl or hydroxyalkyl substituted hydroxyl group and one is a carboxyl or terminal epoxide group. The macromolecule may be terminated by means of at least one chain stopper.
    Type: Grant
    Filed: October 24, 1995
    Date of Patent: September 2, 1997
    Assignee: Perstorp AB
    Inventors: Kent Sorensen, Bo Pettersson
  • Patent number: 5656703
    Abstract: A curable coating composition comprises a composition containing an epoxy resin and a poly(meth)arylate wherein an adhesive improving amount of a metal di(meth)acrylate such as zinc diacrylate and a polyamine curing agent is added.
    Type: Grant
    Filed: June 9, 1995
    Date of Patent: August 12, 1997
    Assignee: Sartomer Company
    Inventors: C. Richard Costin, Gary W. Ceska, Michael A. Bailey
  • Patent number: 5654081
    Abstract: In a method of producing an integrated circuit assembly, an IC device is metallurgically bonded to a supporting substrate. The mounting of the IC device to the substrate also includes a polymeric underfill body adhesively bonding the IC device to the substrate. The polymeric underfill body is formed of a curable underfill composition comprising epoxy resin, anhydride curing agent for the epoxy resin, amine catalyst and a minor amount of an additional component selected from alkyl-substituted imidazole and phenyl-substituted imidazole. Such additional component may act as a catalyst, as used with an amine catalyst known catalyst for the polymerization reaction of the epoxy resin with the anhydride curing agent, may act as a co-catalyst. The polymeric underfill body has improved glass transition temperature values and improved coefficient of thermal expansion values to provide good thermal stress cycling life for the integrated circuit assembly.
    Type: Grant
    Filed: July 5, 1995
    Date of Patent: August 5, 1997
    Assignee: Ford Motor Company
    Inventor: Michael G. Todd
  • Patent number: 5623031
    Abstract: A modified liquid epoxy resin composition is provided by reacting a crystalline epoxy resin, from about 3 to about 20 parts by weight, based on the epoxy resin, of a compound having two or more phenolic hydroxyl groups and/or carboxyl groups in one molecule and from about 3 to about 20 parts by weight of a compound having one phenolic hydroxyl group or carboxyl group in one molecule. The crystalline epoxy resin is preferably selected from various glycidylethers of biphenol compounds. The modified liquid epoxy resin composition has a low viscosity and good liquid stability at low temperatures, resulting in cured resins having excellent heat resistance and water resistance.
    Type: Grant
    Filed: January 11, 1996
    Date of Patent: April 22, 1997
    Assignee: Shell Oil Company
    Inventors: Tetsuro Imura, Yasuyuki Murata, Yoshinori Nakanishi
  • 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: 5612424
    Abstract: A fiber-reinforced resin composition, which comprises:an epoxy resin having at least two epoxy groups in the molecule,a polymerizable unsaturated group-containing epoxy compound of the following general formula [I], ##STR1## wherein R.sup.1 is H or CH.sub.3, R.sup.2 is an alkylene group having 1 to 20 carbon atoms, and n is an integer of 0 to 20,a liquid carboxylic acid anhydride containing a monofunctional carboxylic acid anhydride and/or a polyfunctional carboxylic acid anhydride obtained by reacting a lower aliphatic polyhydric alcohol with a trimellitic acid or a derivative thereof,a curing promoter,a radical polymerization initiator, anda fiber,the glass transition temperature (Tg, .degree.C.) and breaking strain (E, %) of a cured product of said composition satisfying the following formulae:Tg.gtoreq.-17E+240E.gtoreq.4, andTg.gtoreq.125.
    Type: Grant
    Filed: August 18, 1994
    Date of Patent: March 18, 1997
    Assignee: Mitsubishi Chemical Industries, Ltd.
    Inventors: Shoichi Sato, Tohru Imanara, Takao Uematsu
  • Patent number: 5612394
    Abstract: Aqueous epoxy resin dispersion comprising (A) an epoxy resin which is a condensation product of (A-1) from 50 to 95% by weight, preferably from 55 to 85% by weight, of one or more epoxide compounds having at least two epoxide groups per molecule and an epoxide equivalent mass of from 100 to 2000 g/mol, (A-2) from 5 to 50% by weight, preferably from 15 to 45% by weight, of an aromatic polyol; and (A-3) from 0 to 25% by weight, preferably from 0 to 10% by weight, of modifying compounds containing at least two epoxide-reactive groups; (B) a dispersant comprising (B-1) a condensation product of a polyol having a weight-average molecular mass (M.sub.
    Type: Grant
    Filed: June 2, 1994
    Date of Patent: March 18, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Armin Pfeil, Michael Hoenel, Paul Oberressl, Dieter Dreischhoff, Stefan Petri
  • Patent number: 5593730
    Abstract: Powder coating composition which comprises a hybrid polymer system in granular form of a polymer A formable from monomer(s) by aqueous suspension polymerisation and a polymer B, different to A, which polymer system has been obtained using a process which comprises dissolving polymer B in monomeric material to be used in the formation of polymer A, polymerising the monomer(s) to form polymer A using an aqueous suspension polymerisation process, and removing the aqueous phase to form a hybrid of the polymers A and B in granular form, and wherein polymer A and polymer B bear functional groups for imparting curability to the hybrid polymer system, and wherein further the hybrid polymer system has a number average molecular weight within the range of from 1500 to 15,000.
    Type: Grant
    Filed: January 13, 1995
    Date of Patent: January 14, 1997
    Assignee: Zeneca Limited
    Inventors: Rajasingham Satgurunathan, David C. Hinde, John C. Padget, Stephen G. Yeates
  • Patent number: 5589554
    Abstract: An adhesive composition is here disclosed which comprises a 2-cyanoacrylate and at least one of compounds (a) and (b):(a) an addition reaction product of an epoxy group and a compound having a cyano group and a carboxylic acid group in its molecule, and(b) a compound having a cyano group and a carboxylic acid group in its molecule. A process for preparing the adhesive composition is also disclosed herein. According to the present invention, the 2-cyanoacrylate-based adhesive composition can be obtained which is excellent in storage stability and hardening properties of thick films and which has a high hardening rate and remarkably improved surface hardening properties of the adhesive composition itself bulged from between adherends. Particularly, the 2-cyanoacrylate bulged from between the adherends can harden rapidly, so that the vaporization of the 2-cyanoacrylate can be minimized.
    Type: Grant
    Filed: September 16, 1994
    Date of Patent: December 31, 1996
    Assignee: Three Bond Co., Ltd.
    Inventor: Soichiro Hiraoka
  • 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: 5574079
    Abstract: The present invention relates to water-borne thermoplastic polyhydroxyether resins having narrow polydispersity (M.sub.w /M.sub.n <4.0 and M.sub.n >7,000 <12,000), and the use of such resins in water-borne coating compositions.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: November 12, 1996
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Robert F. Eaton, Robert N. Johnson
  • Patent number: 5567747
    Abstract: The invention relates to a water-based oxidizing printing ink especially suited for flexographic printing. The ink comprises an epoxy ester resin, an inorganic and/or organic pigment, a drier, a cyclodextrin and water. Preferably, the ink also includes a drier activator such as 2,2'-bipyridyl and a wax.
    Type: Grant
    Filed: July 18, 1995
    Date of Patent: October 22, 1996
    Assignee: Sun Chemical Corporation
    Inventors: Anthony R. Cappuccio, Athanasios P. Rizopoulos
  • Patent number: 5539064
    Abstract: A resist ink composition developable with a diluted, alkaline solution, which exhibits high dispersion stability itself, can form a pattern with excellent resolution, even in the case of a low exposure amount, and can produce a cured resist film excellent in solvent resistance for high-performance printed circuits and which comprises an ultraviolet-curable resin obtained by copolymerizing (a) from 5 to 50% by weight of an ethylenically unsaturated monomer of a general formula: ##STR1## wherein R.sub.1 represents a hydrogen atom or a methyl group; R.sub.2 represents a hydrogen atom or an alkyl group; n represent an integer of from 1 to 4, and/or glycerol mono(meth)acrylate, (b) from 10 to 90% by weight or glycidyl (meth)acrylate and (c) from 0 to 80% by weight of other ethylenically unsaturated monomers capable of copolymerizing with these (a) and (b), followed by reacting the resulting copolymer with from 0.7 to 1.
    Type: Grant
    Filed: September 12, 1995
    Date of Patent: July 23, 1996
    Assignee: Goo Chemical Industries Co., Ltd.
    Inventors: Soichi Hashimoto, Satoshi Miyayama, Toshiaki Nishimura, Toshikazu Oda
  • Patent number: 5536775
    Abstract: Amine curable compositions containing a partially acrylated epoxy resin useful for forming protective and/or decorative coatings on a variety of substrates, particularly flooring substrates.
    Type: Grant
    Filed: November 4, 1994
    Date of Patent: July 16, 1996
    Assignee: Sandoz Ltd.
    Inventors: Benedict S. Curatolo, Frank V. Apicella, Jr., Thomas W. Richardson, Sr.
  • Patent number: 5523337
    Abstract: Hydroxy-terminated telechelic rubber polymers and block copolymers of flexible polymers with unsaturated polyester resins improve the elongation and flexural elongation of in-mold coating compositions for fiber reinforced plastics (FRP). An FRP in-mold coating composition based upon vinyl ester resin, ethylenically unsaturated monomers, and at least one of telechelic hydroxy terminated flexible polymers and the block copolymers of functionally terminated flexible polymers with unsaturated polyester polymers are described.
    Type: Grant
    Filed: October 27, 1994
    Date of Patent: June 4, 1996
    Assignee: GenCorp Inc.
    Inventors: Krishna G. Banerjee, I. Glen Hargis, Earl G. Melby, Douglas S. McBain
  • 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: 5512607
    Abstract: This invention provides a photosensitive resin composition which can be developed using water and can form a resist layer having superior hardness, adhesion and water resistance.The photosensitive resin composition of the present invention is characterized by containing an unsaturated epoxyester compound prepared by esterifying some of the epoxy side groups of an unsaturated epoxyester compound, and then reacting the remained epoxy groups of the epoxyester compound with a tertiary amine and acid component, such as phosphoric acid, a monoester of phosphoric acid or a diester of phosphoric acid or combination thereof, to convert the epoxy groups into quaternary ammonium salt groups having phosphate anions.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: April 30, 1996
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Keiichi Kinashi, Hiroshi Samukawa, Reiko Chiba
  • Patent number: 5491184
    Abstract: ABA block copolymers having saturated polyester midblocks "B" and unsaturated polyester condensation end blocks A of molecular weight from about 100 to 500 or 600 are described which increase the flexural strain to failure of unsaturated polyester or vinyl ester resins. These ABA block copolymers are generally compatible with unsaturated polyester resins and increase flexural strain by a different mechanism than used by incompatible rubbery polymers. These ABA block copolymers are compatible with the unsaturated polyester compositions and do not phase separate.
    Type: Grant
    Filed: October 26, 1994
    Date of Patent: February 13, 1996
    Assignee: GenCorp. Inc.
    Inventors: Douglas S. McBain, Earl G. Melby, Kevin P. LaJudice
  • Patent number: 5486580
    Abstract: The present invention discloses novolacs and thermosets thereof containing mesogenic moieties. Certain of said novolacs and thermosets thereof exhibit nonlinear optical properties upon orientation.
    Type: Grant
    Filed: November 2, 1994
    Date of Patent: January 23, 1996
    Assignee: The Dow Chemical Company
    Inventors: Mark D. Newsham, Jimmy D. Earls, Robert E. Hefner, Jr.
  • Patent number: 5468784
    Abstract: Disclosed is a photopolymerizable resin composition suitable for forming a solder mask layer, for example, on a printed circuit board. The photopolymerizable resin composition of the invention can be prepared in the form of an aqueous solution and is developable with water as the developer liquid so that the problems and disadvantages inherent in the use of organic solvents can be completely solved. The composition comprises, in addition to a photopolymerization initiator and a polyenic compound as a reactive diluent, a unique prepolymer as a resinous ingredient which is a copolymer of, for example, an alkyl (meth)acrylate and glycidyl (meth)acrylate modified at the epoxy groups in the copolymer partly by the reaction with (meth)acrylic acid and partly by the reaction with an onium group-containing compound, e.g. a quaternary ammonium compound, to impart solubility in water.
    Type: Grant
    Filed: February 23, 1994
    Date of Patent: November 21, 1995
    Assignee: Tamura Kaken Corporation
    Inventors: Makoto Yanagawa, Hiroshi Yamamoto
  • Patent number: 5466764
    Abstract: There are here disclosed an adhesive composition obtained by adding a fluorine-containing carboxylic acid epoxy adduct to a 2-cyanoacrylate, and a process for preparing the adhesive composition. This 2-cyanoacrylate-based adhesive composition is excellent in storage stability and particularly excellent in adhesive force and impact resistance and has a high hardening rate. In particular, the adhesive strength of the 2-cyanoacrylate-based adhesive composition can be remarkably increased without lowering the hardening rate, and so the 2-cyanoacrylate-based adhesive composition can exert a sufficient resistance to impact and the like at the time of the adhesion of metals, rubbers, plastics and lumbers and the reliability of adherends can be improved.
    Type: Grant
    Filed: September 16, 1994
    Date of Patent: November 14, 1995
    Assignee: Three Bond Co., Ltd.
    Inventor: Soichiro Hiraoka
  • Patent number: 5457168
    Abstract: There is disclosed a solid composition of polyglycidyl compounds having a molecular weight of less than 1500, which composition consists of one or more than one solid polyglycidyl compound and altogether not less than 5% by weight of one or of a mixture of more than one polyglycidyl compound, which compound or mixture is normally in liquid form, said amount being based on the total amount of all polyglycidyl compounds in the composition, which composition contains the said solid polyglycidyl compounds or at least part of the said solid polyglycidyl compounds in form of one or a mixture of more than one solid mixed phase, which solid mixed phase or mixture of more than one solid mixed phase essentially comprises the total amount of the polyglycidyl compounds which are normally in liquid form as additional component or components.
    Type: Grant
    Filed: February 13, 1995
    Date of Patent: October 10, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Jacques-Alain Cotting, Philippe-Guilhaume Gottis
  • Patent number: 5447798
    Abstract: A concrete article having a mixture layer comprising concrete and a polysulfide-modified epoxy resin as an intermediate layer between a concrete body and a cured layer of a polysulfide-modified epoxy resin, which concrete article is excellent in corrosion resistance, durability and workability, and shows good adhesion to the concrete body and to the cured layer of the polysulfide-modified epoxy resin. This concrete article can be produced by applying a coating composition containing the polysulfide-modified epoxy resin to the concrete body in an uncured state.
    Type: Grant
    Filed: June 22, 1993
    Date of Patent: September 5, 1995
    Assignees: Toray Industries, Inc., Toray Thiokol Co., Ltd.
    Inventors: Tadami Kamaishi, Hideaki Tanisugi, Keiichi Minami, Akio Takahashi, Takashi Taniguchi, Hiroyoshi Kuramoto