1,2-epoxy Containing Reactant Patents (Class 528/297)
  • Patent number: 6180589
    Abstract: The invention provides novel polyether hydroxycarboxylate copolymers which are effective sequestering agents. The polyether hydroxycarboxylate copolymer when used in a cleaning composition enhances or “builds” the cleaning efficiency of the surfactant by inactivating hardness ions. In addition, the polyether hydroxycarboxylate copolymers assist in cleaning by dispersing and suspending soils to prevent the redeposition of soils. The polyether hydroxycarboxylate copolymer has the structure wherein M+ is a cation wherein M is independently selected from hydrogen, ammonia, alkali metals, alkaline earth metals, zinc, copper, organic amines, amino acids, and amino saccharides; R2 and R3 are independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; n is from about 2 to about 100; x1 and x2 are independently 0 or 1; a is from 0 to 99 mole percent; and b is from 100 to 1 mole percent, provided that (a+b) is 100 mole percent.
    Type: Grant
    Filed: January 5, 1999
    Date of Patent: January 30, 2001
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: Klein A. Rodrigues, Allen M. Carrier
  • Patent number: 6133335
    Abstract: The present invention provides compositions comprising epoxy-containing monomers, where the polymerization of the monomers can be influenced by accelerators. The compositions include at least one photo-polymerizable epoxy monomer and an initiation system. The initiation system comprises at least one organo-iron complex salt and at least one accelerator. The epoxy-containing monomers are energy-polymerized to form useful articles or coated articles.
    Type: Grant
    Filed: December 31, 1998
    Date of Patent: October 17, 2000
    Assignee: 3M Innovative Properties Company
    Inventors: Wayne S. Mahoney, Peggy S. Willett, Michael A. Johnson
  • Patent number: 6121408
    Abstract: The powder coating for use in a coating method which includes the steps of mixing and applying two or more powder coatings to a substrate, the powder coating comprising a resin not having thermosetting properties at a temperature of 160.degree. C. or less by itself, and being heat-cured at a temperature of 160.degree. C. or less when used in combination with other powder coatings. The powder coating composition comprising two or more powder coatings, wherein each of the powder coatings comprises a resin not having thermosetting properties at a temperature of 160.degree. C. or less by itself, and being heat-cured at a temperature of 160.degree. C. or less to form a coating film when used in combination with other powder coatings.
    Type: Grant
    Filed: April 7, 1998
    Date of Patent: September 19, 2000
    Assignee: Kao Corporation
    Inventors: Katsutoshi Aoki, Masayuki Maruta, Yukiya Sato, Hisakazu Tajima, Takehiko Tohjo, Yasunori Inagaki, Shingo Tanaka
  • Patent number: 6121389
    Abstract: Compositions, prepared by glycidation of at least one (a) carboxy polyfunctional polyester and at least one (b) .alpha.,.alpha.-branched monocarboxylic acid containing a tertiary carbon atom and from 5 to 12 carbon atoms, or a glydicyl ester thereof, and coating and/or casting compositions comprising them.
    Type: Grant
    Filed: April 6, 1999
    Date of Patent: September 19, 2000
    Assignee: Shell Oil Company
    Inventors: Petrus Gerardus Kooijmans, Eric Johannes Vos, Michael James Watkins
  • Patent number: 6111044
    Abstract: A thermosetting composition which gives a cured product having excellent weatherability, chemical and physical properties, in particular acid resistance and abrasion resistance, at a relatively low temperature, which has superior storage stability, and which can be used as a one component coating material; a coating composition utilizing this thermosetting composition; a method of coating; and a coated article are provided. The thermosetting composition contains a resin having at least one functional group selected from the group consisting of a blocked hydroxyl group, blocked carboxylic acid, and an epoxy group. The thermosetting composition has a blocked hydroxyl group, blocked carboxylic acid, and an epoxy group.
    Type: Grant
    Filed: November 4, 1998
    Date of Patent: August 29, 2000
    Assignees: NOF Corporation, Mazda Motor Corporation
    Inventors: Toshio Yamamoto, Kazuhi Koga, Yoshiaki Marutani, Hiroshi Kubota, Tadamitsu Nakahama, Mika Ohsawa
  • Patent number: 6103834
    Abstract: A process for co-polymerizing unsaturated vegetable oils or fatty acids utilizing the steps of mixing the unsaturated vegetable oil or fatty acid with maleic anhydride in a container. Simultaneously, inert gas is added to the container to provide an oxygen free environment within the container. A sufficient amount of initiator is added to the mixture in the container to produce free radicals for the co-polymerization of the vegetable oil with this fatty acid or the maleic anhydride.
    Type: Grant
    Filed: October 13, 1998
    Date of Patent: August 15, 2000
    Inventor: Abel M. Espinoza
  • Patent number: 6074758
    Abstract: A poly(hydroxy ester ether) is prepared by reacting a) a diacid containing a hetero moiety of the formula:HO.sub.2 CCH.sub.2 X(RX).sub.y CH.sub.2 CO.sub.2 Hwherein X is selected from the group consisting of --O--, --S--, and NH; y is the whole number 0 or 1; and R is selected from the group consisting of an aromatic moiety and a heterocyclic moiety having from 6 to 30 carbon atoms; andb) a diglycidyl ether generally represented by the formula: ##STR1## wherein R.sup.2 is an aromatic moiety or divalent aliphatic hydrocarbon having 2 to 20 carbon atoms. Films, articles and laminations made from the composition exhibit an oxygen permeability of less than about 8 cc-mil/100 in.sup.2 -24 hour-atmosphere. The present invention is further directed to a miscible blend having the poly(hydroxy ester ether) of the present invention and a second component selected from a saturated polyester of an aromatic diacid, such as PET and PEN.
    Type: Grant
    Filed: November 4, 1999
    Date of Patent: June 13, 2000
    Assignee: Eastman Chemical Company
    Inventor: Robert Boyd Barbee
  • Patent number: 6075099
    Abstract: A curable epoxidized polyester-based composition useful for powder coatings application is provided by epoxidizing a polyester having a melting point of at least 90.degree. C. and a viscosity of at most 50 Poise@ 200.degree. C., where such polyester is a polyester prepared by reacting (I) a tetrahydrophthalic acid or anhydride, (ii) at least one cycloaliphatic polyol, (iii) at least one saturated polycarboxylic acid, and (iv) optionally at least one other alcohol under conditions effective to obtain a solid polyester having a melting point of at least 90.degree. C. Curable coating powder is obtained containing the epoxidized polyester and a solid carboxylic acid curing agent having an acid equivalent weight within the range of from about 100 to about 1500.
    Type: Grant
    Filed: February 6, 1996
    Date of Patent: June 13, 2000
    Assignee: Shell Oil Company
    Inventors: Charles John Stark, Edward John Marx
  • Patent number: 6040009
    Abstract: The present invention is to provide a low solvent content type-coating composition by which the resultant coatings with good scuff resistance or water resistance as well as good chipping resistance are produced, while the content of an organic solvent to be used can be much reduced. The low solvent content type-coating composition comprises a polyester oligomer having a hydroxyl group in an amount of 2.0 to 10.0 moles/Kg-resin, a number average molecular weight (Mn) of 300 to 1500, a weight average molecular weight (Mw) of 300 to 3000, and a ratio of a weight average molecular weight/a number average molecular weight (Mw/Mn) of 1 to 2.0, an amount of a modifying lactone being 31 to 85%, and an aliphatic hydrocarbon group of C4-22 which is not derived from lactones. The present invention is also to provide a process for coating a low solvent content type-coating composition on, for example, a base coating composition by a wet-on-wet coating.
    Type: Grant
    Filed: June 19, 1995
    Date of Patent: March 21, 2000
    Assignee: Mazda Motor Corporation
    Inventors: Yoshiaki Marutani, Takashi Tomita, Tadamitsu Nakahama, Hiroyuki Uemura, Kazuhi Koga, Mika Ohsawa
  • Patent number: 6022907
    Abstract: Novel urethane prepolymers which can be applied onto substrates without using any solvent, processes for producing the same, and pressure-sensitive adhesives using the prepolymers, which are excellent in adhesive strength, holding power and low temperature properties are provided. The urethane prepolymer is represented by the following formula [I] or [II]:d-c-(a-c).sub.k -e [I]ord-c-(a-c).sub.n -(b-c).sub.m -(a-c).sub.1 -e [II]wherein k is from 4 to 100; n and 1 each are from 2 to 50; m is from 1 to 50; a represents a polyester group having a number average molecular weight of 1.times.10.sup.3 to 5.times.10.sup.3 ; b represents a divalent group; c represents an organic isocyanate group; d represents a monool having functional groups; and e is a monool, which is the same as or different from d, having a number average molecular weight of 5.times.10.sup.3 to 5.times.10.sup.5. Such an urethane prepolymer is crosslinked to increase its molecular weight, thereby providing a pressure-sensitive adhesive.
    Type: Grant
    Filed: May 28, 1998
    Date of Patent: February 8, 2000
    Assignees: Kyoeisha Chemical Co., Ltd., Nitto Denko Corporation
    Inventors: Junichi Ikeda, Katsuya Kume
  • Patent number: 5969056
    Abstract: A process for the preparation of an esterification product comprises reacting a polyfunctional organic acid or anhydride and a cyclic organic carbonate compound in the presence of a catalyst to form an esterification product. The catalyst comprises a quaternary ammonium salt and a component selected from the group consisting of a metal, a salt of a metal, and mixtures thereof.
    Type: Grant
    Filed: January 14, 1999
    Date of Patent: October 19, 1999
    Assignee: Reichhold, Inc.
    Inventor: Hildeberto Nava
  • Patent number: 5962621
    Abstract: A process for preparing a thermoplastic hydroxy-functionalized polyester comprises contacting a dicarboxylic acid or a mixture of dicarboxylic acids with a diepoxide in a given solvent in the presence of an end-capping agent and a catalyst under conditions sufficient to form the hydroxy-functionalized polyesters or polyethers.
    Type: Grant
    Filed: April 28, 1998
    Date of Patent: October 5, 1999
    Assignee: The Dow Chemical Company
    Inventors: John M. Beckerdite, Shari L. Kram, Ramki Subramania, Jerry E. White, Michael N. Mang
  • Patent number: 5952452
    Abstract: A high solids coating composition comprising a branched hydroxy-functional polyester oligomer and a curing agent; and the oligomer itself containing at least 20% by weight of the binder of at least one of the following tertiary acid ester end groups: ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are independently selected from CH.sub.3 and CH.sub.2 OH; the composition being suitable as an automobile clearcoat or pigmented topcoat.
    Type: Grant
    Filed: July 16, 1997
    Date of Patent: September 14, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Armand Aerts, Anne DeMarre, Jozef Huybrechts, G. Todd Palmer
  • Patent number: 5952436
    Abstract: A general approach to making water-resistant polyetherester resins and thermosets is disclosed. In one aspect, an unsaturated polyetherester resin prepared by inserting a carboxylic acid derivative into a polyether is co-cured with a vinyl monomer and a di- or polyisocyanate to give a water-resistant, thermoset that has excellent dimensional stability, flexibility, and strength properties. Processes for making low-viscosity resins that give thermosets with good water resistance are also described. In one process, an unsaturated polyetherester resin intermediate reacts with a mono-functional isocyanate or fatty alcohol to produce an easy-to-formulate, low-viscosity, low-molecular-weight capped resin.
    Type: Grant
    Filed: January 13, 1998
    Date of Patent: September 14, 1999
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Gangfeng Cai, Jeffrey A. Klang, Lau S. Yang
  • Patent number: 5945483
    Abstract: There are disclosed a high solids content resin composition excellent in solubility in an organic solvent, comprising an acrylic oligomer having a blocked hydroxyl group, a curing agent having a reactivity with a hydroxyl group and a dissociation or curing catalyst, and a high solids content type paint using the resin composition. There are also disclosed a coating process and a baking process comprising coating and baking the resin composition or the paint while rotating a material to be coated at an appropriate speed. The resin composition and the paint of the present invention have substantially no sagging and solvent popping. Further, the thus obtained paint film have improved smoothness, solvent resistance, weather resistance and resistance to scratching.
    Type: Grant
    Filed: September 29, 1997
    Date of Patent: August 31, 1999
    Assignees: Dainippon Ink and Chemicals, Inc., Mazda Motor Corporation
    Inventors: Goro Iwamura, Shigeki Matsui, Ichiro Azuma, Yoshiaki Marutani, Hiroyuki Uemura, Shinji Sasaki, Kazuhi Koga
  • Patent number: 5932682
    Abstract: A cleavable epoxy resin composition suitable for encapsulating electronic chips and a method for making the composition comprises the cured reaction product of a diepoxide; a cyclic dicarboxylic anhydride curing agent mixture; a 1,3-diaza compound having two nitrogen atoms present with one nitrogen atom doubly bonded to the central carbon and singly bonded to one other carbon, and the other nitrogen atom singly bonded to the central carbon and singly bonded to another carbon and singly bonded to a hydrogen. The 1,3-diaza compound serves either as the sole catalyst or in combination with a tertiary amine catalyst different from the diaza compound. The composition may include an optional hydroxy functional compound capable of reacting with the cyclic anhydrides to form a half ester thereby initiating the reaction between the diepoxide and the cyclic dicarboxylic anhydride curing agent. The resin can be used for the encapsulation of electronic parts, but can be removed by a solvent.
    Type: Grant
    Filed: December 19, 1995
    Date of Patent: August 3, 1999
    Assignee: International Business Machines Corporation
    Inventors: Stephen Leslie Buchwalter, Joseph Paul Kuczynski, John Gregory Stephanie
  • Patent number: 5932666
    Abstract: This invention is a thermoplastic saturated polyester low profile additive (low profile additive) useful in sheet molding compounds for parts, especially vehicle parts. The additive has a major component derived from aromatic compounds such as terephthalic acid including recycled polyethylene terephthalate. Asymmetrical glycols are an important ingredient and can be used to digest recycled PET to make oligomeric glycols which are reacted with acids having fewer than 12 carbon atoms to make one of the low profile additives of this invention.
    Type: Grant
    Filed: March 25, 1998
    Date of Patent: August 3, 1999
    Assignee: Ashland Inc.
    Inventor: Dennis Herbert Fisher
  • Patent number: 5907025
    Abstract: Esterification reactions conducted in the presence of Lewis acids, including the reactions between aromatic carboxylic acids and alcohols and between epoxides and carboxylic acids, may be conducted with the use as the catalyst of a hexaalkylguanidinium or .alpha.,.omega.-bis(pentaalkylguanidinium)alkane salt such as hexaethyiguanidinium chloride or bromide.
    Type: Grant
    Filed: May 27, 1997
    Date of Patent: May 25, 1999
    Assignee: General Electric Company
    Inventor: Daniel Joseph Brunelle
  • Patent number: 5880251
    Abstract: An improved two-stage process for the preparation of polyester resins is provided which involves an initial reaction of a dicarboxylic acid such as isophthalic acid with an alkylene oxide such as ethylene or propylene oxide in the presence of a catalyst to form an oligoester reaction mixture, followed by a second stage reaction between the oligoester reaction mixture and a dibasic acid or anhydride; a first-stage catalyst is employed which has a thermal decomposition temperature substantially at or below the second-stage reaction temperature. The most preferred first-stage catalyst is benzyltriethylammonium chloride.
    Type: Grant
    Filed: June 18, 1997
    Date of Patent: March 9, 1999
    Assignee: Cook Composites & Polymers Co.
    Inventors: Chih-Pin Hsu, Ming-Yang Zhao, L. Scott Crump
  • Patent number: 5869191
    Abstract: Linear, tertiary carboxyl functional polyester resins obtainable by reaction ofa) at least one compound A.sub.1, comprising the reaction product of(i) a glycidylester of a mixture of certain highly branched saturated monocarboxylic acids isomers, and(ii) a mixture of said highly branched saturated monocarboxylic acids;b) at least one aromatic or cycloaliphatic dicarboxylic acid compound B;c) optionally at least one dihydroxymonocarboxylic acid compound C; andd) optionally at least one diol compound D; in a certain molar ratio of compounds A.sub.1 :B:C:D, at a temperature of from 100.degree. to 225.degree. C., until essentially all the non-tertiary carboxyl groups as initially present in the reaction mixture have been reacted.
    Type: Grant
    Filed: November 24, 1997
    Date of Patent: February 9, 1999
    Assignee: Shell Oil Company
    Inventors: Ronald Petrus Clemons Van Gaalen, Petrus Gerardus Kooijmans, Eric Johannes Vos
  • Patent number: 5840829
    Abstract: An adhesive is provided for bonding cyanate ester composite parts together which is also plateable with metal once chemically etched. The adhesive comprises a polymeric matrix and a filler of cyanate ester polymer. The polymeric matrix comprises at least one polyepoxide resin and a curing agent, while the cyanate ester polymer filler is present in the adhesive as a powder. In practice, the present adhesive is applied to the surface of cyanate ester composite articles to be bonded and is allowed to cure at room temperature. Thereafter, the surface of the assembly is chemically etched and then plated with metal. The present adhesive enable the complete coverage of the cyanate ester composite assembly with the plated metal, including the adhesive bondlines.
    Type: Grant
    Filed: November 25, 1997
    Date of Patent: November 24, 1998
    Assignee: Hughes Electronics Corporation
    Inventors: Ralph D. Hermansen, Brian M. Punsly, Wai-Cheng Seetoo
  • Patent number: 5834118
    Abstract: Hyperbranched polyester of a polyol with 3 to 10 reactive hydroxyl groups, preferably of equivalent reactivity, and an aromatic polycarboxylic anhydride with 2 to 4 carboxyl groups, preferably 3 carboxyl groups, each hydroxyl group of the polyol forming an ester linkage with one anhydride group of the polycarboxylic anhydride, and further glycidyl (meth)acrylate or allyl glycidyl ether forming ester linkages with the remaining carboxyl groups of the anhydride and free hydroxyl groups. Further in the hyperbranched polyester (meth)acrylic anhydride and/or an aliphatic carboxylic anhydride form ester linkages with the free hydroxyl groups. The invention also comprises a process for the production of hyperbranched polyesters and such polyesters obtainable by the process. The hyperbranched polyesters can be used as resins, curable by UV irradiation, for the production of coatings, adhesives, laminates, foils and thin films and fibre-reinforced composites.
    Type: Grant
    Filed: May 9, 1997
    Date of Patent: November 10, 1998
    Assignee: Neste Oy of Keilaniemi
    Inventors: Bengt R.ang.nby, Shi Wenfang
  • Patent number: 5789527
    Abstract: Provided are a polyester resin for use in a toner binder which is excellent in terms of offset resistance and low-temperature fixability, which keeps triboelectric charge stability even in an environment of a high temperature and a high humidity, which has excellent durability, and which is used in a toner that gives vivid image characteristics, a process for producing the same, and a toner using the same. The polyester resin for use in the toner binder is formed by linking at least a part of the crosslinked low-molecular polyesters through a dicarboxylic acid used as a linking agent.
    Type: Grant
    Filed: June 5, 1996
    Date of Patent: August 4, 1998
    Assignees: Tomoegawa Paper Co., Ltd., Unitika, Ltd.
    Inventors: Kikumi Nakamichi, Kouta Tanahashi, Tomoko Kubota, Naomi Sasaki, Hideki Kurebayashi, Haruo Okutani, Kazue Nakadera
  • Patent number: 5789528
    Abstract: The preparation of polyesters and copolyesters, titanium dioxide precipitates and/or titanium dioxide/silicon dioxide coprecipitates having a composition of TiO.sub.2 :SiO.sub.2 >90:10 mol/mol and/or titanium dioxide/zirconium dioxide coprecipitates having a composition of TiO.sub.2 :ZrO.sub.2 >95:5 mol/mol, which have been obtained by hydrolytic precipitation of the corresponding metal alcoholates formed from mono- or polyhydric alcohols, are proposed as polycondensation catalysts. They offer increased safety for the ecosystem and have a higher catalytic activity than Sb.sub.2 O.sub.3, so that the preferred amount used is only 10 to 100 ppm, based on the esters or oligoesters to be subjected to polycondensation. Their storage stability is good if the catalysts have a water content of from 0 to about 15 weight percent, preferably from 0 to about 5 weight percent based upon the hydrated precipitate or coprecipitate, as determined by Karl Fischer titration.
    Type: Grant
    Filed: March 13, 1997
    Date of Patent: August 4, 1998
    Assignee: Akzo Nobel NV
    Inventors: Michael Martl, Thomas Mezger, Bernard Kuhn, Gerriet Oberlein, Klaus Haferland, Bertram Boehringer, Ulrich Berger
  • Patent number: 5780558
    Abstract: A low-cost way to modulate the reactivity and acid number of polyetherester thermoset resins is disclosed. "Beginning" and "end" methods for making dicyclopentadiene (DCPD)-modified polyetherester resins are described. The "beginning" method comprises first heating a polyether, DCPD, a diol, an insertion catalyst, and a carboxylic acid derivative to produce a mixture that contains the polyether and a DCPD-diol diester adduct. Increasing the temperature causes insertion of the DCPD-diol diester into the polyether to give a DCPD polyetherester resin. The "end" method reacts a polyetherester resin made by insertion with DCPD to give a DCPD polyetherester resin. Compared with DCPD polyester resins, those of the invention give more flexible thermosets. Compared with unmodified polyetherester resins, the DCPD polyetherester resins offer formulators more control over curing, which eliminates mold distortion and shrinking or cracking of thermoset parts.
    Type: Grant
    Filed: September 25, 1997
    Date of Patent: July 14, 1998
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Jeffrey A. Klang, Lau S. Yang
  • Patent number: 5780581
    Abstract: An adhesive is provided for bonding cyanate ester composite parts together which is also plateable with metal once chemically etched. The adhesive comprises a polymeric matrix and a filler of cyanate ester polymer. The polymeric matrix comprises at least one polyepoxide resin and a curing agent, while the cyanate ester polymer filler is present in the adhesive as a powder. In practice, the present adhesive is applied to the surface of cyanate ester composite articles to be bonded and is allowed to cure at room temperature. Thereafter, the surface of the assembly is chemically etched and then plated with metal. The present adhesive enable the complete coverage of the cyanate ester composite assembly with the plated metal, including the adhesive bondlines.
    Type: Grant
    Filed: October 27, 1995
    Date of Patent: July 14, 1998
    Assignee: Hughes Aircraft Company
    Inventors: Ralph D. Hermansen, Brian M. Punsly, Wai-Cheng Seetoo
  • Patent number: 5770662
    Abstract: A composition of matter comprising a resin obtained by a process comprising reacting at an elevated temperature an epoxidized ester of an unsaturated fatty acid with an aliphatic alcohol with a resin acid is provided. The equivalent ratio of epoxy groups of said epoxidized ester to carboxyl groups of said resin acid is in the range from 1.5:1 to 0.01:1. The resin is useful as a tackifier for adhesives and has a reduced tendency to crystallize.
    Type: Grant
    Filed: September 18, 1996
    Date of Patent: June 23, 1998
    Assignee: Henkel Kommanditgesellschaft Auf Aktien (Henkel KGaA)
    Inventors: Ulrich Eicken, Manfred Gorzinski, Paul Birnbrich, Thomas Tamcke
  • Patent number: 5744570
    Abstract: Claimed is a copolyether amide having a melting point in the range of 180.degree. to 260.degree. C., incorporating at least 10 wt. % and not more than 30 wt. % of ethylene oxide groups, and composed of 30 to 60 wt. % of polyamide segments and 70 to 40 wt. % of segments derived from a (cyclo)aliphatic or aromatic dicarboxylic acid or a dimeric fatty acid and a polyoxyalkylene diamine derived from a polyoxyalkylene group having a molecular weight of 600 to 6000 and an atomic ratio of carbon to oxygen of 2.0 to 4.3. Also claimed is a non-porous, waterproof film having a water vapour permeability of at least 1000 g/m.sup.2 day determined at 30.degree. C. and 50% RH in accordance with ASTM E96-66 which is based on a the use of these films in rainwear, shoes, tents, chairs, as mattress covers and understating, for medical purpose garments, and for the manufacture of dressings.
    Type: Grant
    Filed: August 16, 1996
    Date of Patent: April 28, 1998
    Assignee: Akzo Nobel NV
    Inventor: Bert Gebben
  • Patent number: 5731391
    Abstract: A fluid which comprises an olefin-terminated polyester an unmodified polyester and a polymerized .alpha.-olefin is provided which facilitates the separation of blood into light and heavy phases via centrifugation in a blood collection vessel. The fluid is useful as a component of a partitioning composition formulated to have appropriate specific gravity to be positioned intermediate the light and heavy blood phases during centrifugation. A partitioning composition including a fluid of the invention provides a particular advantage in blood collection vessels used in therapeutic drug monitoring, due to the relatively low affinity between the fluid component of the composition and commonly monitored classes of drugs.
    Type: Grant
    Filed: September 27, 1996
    Date of Patent: March 24, 1998
    Assignee: Henkel Corporation
    Inventors: William L. O'Brien, Alan C. Kilbarger
  • 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: 5710234
    Abstract: Ortho spiroesters of excellent heat resistance and low volume shrinkage during curing are disclosed. Resin compositions of excellent heat resistance and low curing shrinkage containing these ortho spiroesters are also provided. These photosensitive or heat-curable resin compositions are formulated from photo- or heat-polymerizable compounds containing ethylenic double bonds and carboxyl groups, photopolymerization initiators and sensitizers, or polymerization initiators which generate radicals by heat, and said ortho spiroesters. These resin compositions have low curing shrinkage and are useful for applications requiring dimensional accuracy such as molding materials, encapsulants, adhesives and coatings and also for the preparation of image-forming materials such as protective films for color filters, inks and electrically insulating spacers for touch panels.
    Type: Grant
    Filed: January 19, 1996
    Date of Patent: January 20, 1998
    Assignees: Nippon Steel Chemical Co., Ltd., Nippon Steel Corporation
    Inventors: Koichi Fujishiro, Masaya Furukawa, Kazuhiro Watanabe, Takero Teramoto
  • Patent number: 5696225
    Abstract: A process for making high-performance polyetherester resins and thermosets is disclosed. A polyether polyol reacts with a dicarboxylic acid or anhydride in the presence of an insertion catalyst to produce an acid-terminated polyetherester resin. Reaction of this resin reacts with a primary diol or a diepoxy compound gives a chain-extended polyetherester resin that can be cured with a vinyl monomer to produce a high-performance polyetherester thermoset. Properties of the thermosets rival or exceed those of more expensive high-performance iso and vinyl ester resins.
    Type: Grant
    Filed: February 28, 1996
    Date of Patent: December 9, 1997
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Gangfeng Cai, Jeffrey A. Klang, Lau S. Yang
  • Patent number: 5677395
    Abstract: Polymeric vehicles with liquid crystalline-like properties, solvent dispersible polymeric vehicles, formulated coating compositions with liquid crystalline-like properties and a method for imparting liquid crystalline properties to a coating binder are described. The materials with liquid crystalline-like properties lack structural segments previously regarded as mesogenic.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: October 14, 1997
    Assignee: North Dakota State University
    Inventors: Frank N. Jones, Cong Du, Ganghui Teng, Adel F. Dimian, Daozhang Wang
  • Patent number: 5668244
    Abstract: A liquid polyester obtained by reacting a cyclic acid anhydride (A) containing at least 10 mol % of one of specific cyclic acid anhydrides with an epoxy compound (B) in a cyclic acid anhydride (A):epoxy compound (B) molar ratio of 10:8-10:12, can be applied with a conventionally generally used film-forming machine such as a roll coater or a printing machine, can easily give a film-forming material such as a solvent-free coating composition or ink and a curable liquid resin for use as an adhesive, is a low-temperature curing liquid polyester useful as a compatibilizer, a surface-tension modifier, a pigment dispersing agent and a metal chelating agent, and is curable in air in the presence of a relatively small amount of a catalyst.
    Type: Grant
    Filed: June 16, 1995
    Date of Patent: September 16, 1997
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Miki Kawashima, Takeo Yamaguchi, Kunio Horiuchi, Hiromi Uchida
  • Patent number: 5637356
    Abstract: Polyesters are formed from diols and dibasic carboxylic acids at an OH/COOH ratio to provide --OH termination, and then end-capped with tribasic carboxylic acids. A major portion of the dibasic carboxylic acids used to form the polyesters have the formula: ##STR1## where x=8-32, y=0-8, x+y=8-32. The polyesters are used as support resins for forming acrylic resin emulsions. The polyester/acrylic acid emulsions are useful, for example, as textile size.
    Type: Grant
    Filed: March 5, 1996
    Date of Patent: June 10, 1997
    Assignee: Morton International, Inc.
    Inventors: Ronald J. Kerr, John P. Petrovich, Stephen J. Walker, J. Alvin Binkley
  • Patent number: 5616681
    Abstract: A method for producing an aliphatic polyester having a biodegradability and a higher melting point than conventional aliphatic polyester by suppressing a volatile component generated by side reaction or decomposition reaction with industrially good efficiency and economically in a relatively short period of time, the method enabling a polymerization at vacuum which permits a use of general vacuum pump. The aliphatic polyester can be obtained, for example, by a ring-opening copolymerization of a cyclic acid anhydride with a cyclic ether in a presence of a zirconium compound. The aliphatic polyester also can be obtained by performing a polymerization of raw materials of the aliphatic polyester so as to have a degree of viscosity in the range of 10-10,000 poise when 0.1-30 hours elapsed after the reaction started at reaction temperature of the reaction system under conditions of reaction temperature in the range of 180.degree. C. to 280.degree. C. and reaction pressure in the range of 0.3 mmHg to 3.0 mmHg.
    Type: Grant
    Filed: October 31, 1995
    Date of Patent: April 1, 1997
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Hiroshi Itoh, Yoshinobu Yamamoto, Koji Fukuhara, Masahiro Shiroshima, Hiroya Kobayashi
  • Patent number: 5612445
    Abstract: The epoxidation of alkyds containing anhydrides or diacids with cycloaliphatic unsaturation results in epoxy resins which cure rapidly in UV light to produce uniform films without the use of flow modifiers. The fatty acid portion of the alkyd functions as an internal plasticizer. Crosslinking occurs through oxirane rings in both the anhydride and fatty acid moieties of the alkyd to produce hard, but not brittle films. Excellent water resistance is obtained without thermal post curing.
    Type: Grant
    Filed: February 15, 1995
    Date of Patent: March 18, 1997
    Assignee: Arizona Chemical Co.
    Inventor: Raymond H. Jones
  • Patent number: 5608016
    Abstract: The invention relates to salts of pyromellitic acid which comprise 1 mol of pyromellitic acid and 0.5 to 2 mol of a guanidine of the following composition: ##STR1## in which R, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different radicals from the group consisting of hydrogen, alkyl, cycloalkyl and aromatic hydrocarbon residues having 1 to 8 carbon atoms, and R.sup.1 and R.sup.2 and R.sup.3 and R.sup.4 may form a joint ring which may contain an oxygen atom as heteroatom. Also claimed are the preparation of the salts and their use for matt epoxide and hybrid powder coatings.
    Type: Grant
    Filed: April 3, 1996
    Date of Patent: March 4, 1997
    Assignee: Huels Aktiengesellschaft
    Inventors: Rainer Gras, Elmar Wolf
  • Patent number: 5602211
    Abstract: Adducts containing mesogenic or rodlike moieties are prepared by reacting (1) at least one compound containing an average of more than one vicinal epoxide group per molecule with (2) at least one compound containing an average of more than one reactive hydrogen atom per molecule; with the proviso that at least one member of components (1) and (2) contains a mesogenic or rodlike moiety. These compounds are useful as curing agents for epoxy resins.
    Type: Grant
    Filed: January 18, 1995
    Date of Patent: February 11, 1997
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • 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: 5583187
    Abstract: Hot melt adhesive compositions, particularly biodegradable hot melt adhesives are prepared from 10 to 90% by weight of a thermoplastic methylol polyester prepared from the reaction of at least one dicarboxylic acid with a diglycidyl ether, a diglycidyl ester or a combination thereof; 0 to 90% by weight of a compatible tackifier; 0 to 80% by weight of a compatible plasticizer; 0 to 50% by weight of a compatible wax diluent and 0 to 3% by weight of a stabilizer.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: December 10, 1996
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: Matthew L. Sharak, Charles W. Paul, Dilip Ray-Chaudhuri
  • Patent number: 5569408
    Abstract: Water-soluble, biologically decomposable carbonic acid polyesters having the general formula (I): ##STR1## in which R.sub.1 represents a straight- or branched-chain, saturated or monounsaturated alkyl residue having from 6 to 22 carbon atoms;R.sub.2 represents a hydrogen or methyl group;R.sub.3 represents hydrogen or the group: ##STR2## n is an integer between 0 and 10; m is an integer between 5 and 16, andz is an integer between 1 and 3 are disclosed.The use of these compounds for preparation and lubricating agents for synthetic fibers is also disclosed.
    Type: Grant
    Filed: October 27, 1993
    Date of Patent: October 29, 1996
    Assignee: Chemische Fabrik Stockhausen GmbH
    Inventors: Reinmar Peppmoller, Bernhard Goossens, Karl Winck
  • Patent number: 5567781
    Abstract: A liquid coating composition particularly adapted for coating cans. The composition comprises a curable, hydroxyl functional block copolymer which is the reaction product of a 1,2-epoxy resin and a carboxyl functional polyester resin, and a hydroxyl-reactive crosslinking agent providing desirably at least 2.0 equivalents of hydroxyl reactive functional groups per hydroxyl equivalent of the block copolymer. The block copolymer desirably has a number average molecular weight in the range of 7000 to 30,000. Also disclosed is a method for formulating a coating composition utilizing craze resistance testing over an aging period to enable the choice of the quantity of curing agent to be used in the coating composition.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 22, 1996
    Assignee: The Valspar Corporation
    Inventors: Phillip C. Martino, Kenneth G. Davis
  • Patent number: 5560934
    Abstract: A cleavable epoxy resin composition suitable for encapsulating electronic chips comprising the cured reaction product of a diepoxide containing a cyclic anhydride curing agent and an amine promoter.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 1, 1996
    Assignee: International Business Machines Corporation
    Inventors: Ali Afzali-Ardakani, Stephen L. Buchwalter, Jeffrey D. Gelorme, Laura L. Kosbar, Bert H. Newman, Frank L. Pompeo
  • Patent number: 5554701
    Abstract: This invention provides weatherable thermosetting powder coatings based on an all-aliphatic polyester comprised of residues of 1,2-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, or 1,4-cyclohexanedicarboxylic acid and 2,6-decahydronaphthalene dimethanol. The polyester may be predominantly hydroxyl or carboxyl functional. Coating compositions prepared therefrom provide coatings which exhibit superior weatherability.
    Type: Grant
    Filed: March 24, 1995
    Date of Patent: September 10, 1996
    Assignee: Eastman Chemical Company
    Inventors: Yeong-Ho Chang, Robert B. Barbee, Brian S. Phillips
  • Patent number: 5552478
    Abstract: This invention is a thermoplastic saturated polyester low profile additive (low profile additive) useful in sheet molding compounds for parts, especially vehicle parts, the additive has a major component derived from aromatic compounds such as terephthalic acid including recycled polyethylene terephthalate. Asymmetrical glycols are an important ingredient and can be used to digest recycled PET to make oligomeric glycols which are reacted with acids having fewer than 12 carbon atoms to make one of the low profile additives of this invention.
    Type: Grant
    Filed: February 2, 1996
    Date of Patent: September 3, 1996
    Assignee: Ashland Inc.
    Inventor: Dennis H. Fisher
  • Patent number: 5548059
    Abstract: Unsaturated linear polymers have repeating units of a reaction product of a first monomer, a second monomer, a third monomer and optionally a fourth monomer. The linear polymers have a glass transition temperature ranging from about 52.degree. C. to about 61.degree. C. The first monomer should have a weight average molecular weight less than 200. The second monomer may be a dicarboxylic acid or diester which is different than the third monomer. A concentration of second residues of the polymer, derived from the second monomer, ranges from about 3 wt. % to about 15 wt. %, based on the total weight of the polymer. The third monomer is an aromatic dicarboxylic acid or an ester thereof. In the polymer, a concentration of third residues, derived from the third monomer, ranges from about 40 wt. % to about 55 wt. %, based on the total weight of the polymer. The fourth monomer is a diol having a higher molecular weight than the first monomer.
    Type: Grant
    Filed: January 3, 1995
    Date of Patent: August 20, 1996
    Assignee: Xerox Corporation
    Inventors: Robert D. Bayley, Carol A. Fox, Thomas R. Hoffend, Hadi K. Mahabadi, Enno E. Agur, Guerino Sacripante, Michael S. Hawkins
  • Patent number: 5543475
    Abstract: Polymeric vehicles with liquid crystalline-like properties, solvent dispersible polymeric vehicles, formulated coating compositions with liquid crystalline-like properties and a method for imparting liquid crystalline properties to a coating binder are described. The materials with liquid crystalline-like properties lack structural segments previously regarded as mesogenic.
    Type: Grant
    Filed: September 13, 1993
    Date of Patent: August 6, 1996
    Assignee: North Dakota State University
    Inventors: Frank N. Jones, Cong Du, Ganghui Teng, Adel F. Dimian, Daozhang Wang
  • Patent number: 5543464
    Abstract: Coating powder compositions are formulated with epoxy-functional acrylic resins, and as curatives 5 to 50 phr poly-carboxylic functional polyesters and 5 to 40 phr poly-carboxylic functional crystalline curatives.
    Type: Grant
    Filed: December 8, 1995
    Date of Patent: August 6, 1996
    Assignee: Morton International, Inc.
    Inventors: Owen H. Decker, Charles P. Tarnoski
  • Patent number: 5543476
    Abstract: Polymeric vehicles with liquid crystalline-like properties, solvent dispersible polymeric vehicles, formulated coating compositions with liquid crystalline-like properties and a method for imparting liquid crystalline properties to a coating binder are described. The materials with liquid crystalline-like properties lack structural segments previously regarded as mesogenic.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: August 6, 1996
    Assignee: North Dakota State University
    Inventors: Frank N. Jones, Cong Du, Ganghui Teng, Adel F. Dimian, Daozhang Wang