Hot Melt Adhesive Patents (Class 526/935)
  • Patent number: 8440308
    Abstract: The method of manufacturing shoes of the present invention comprises a pre-step of heating a following reactive hot-melt adhesive to melt it and providing the melted adhesive on a joining surface of at least one adherend, an ultraviolet treating step of irradiating the adhesive with ultraviolet light having irradiation energy more than 100 mJ/cm2 and less than 1200 mJ/cm2 to polymerize a polyurethane prepolymer, and a joining step of overlaying a joining surface of another adherend on the adhesive to bond both adherends together. The reactive hot-melt adhesive contains a polyurethane prepolymer having an (meth)acryloyl group and an isocyanate group at the end of a molecule, and a photopolymerization initiator. The polyurethane prepolymer includes a non-crystalline polyol and a crystalline polyol, wherein the non-crystalline polyol is contained from 20% by mass to 90% by mass with respect to the whole polyols. The viscosity of the reactive hot-melt adhesive at 80° C. is 300 Pa·s or less.
    Type: Grant
    Filed: January 29, 2008
    Date of Patent: May 14, 2013
    Assignee: Asics Corporation
    Inventors: Kenichi Harano, Tatsuya Amano, Hisao Matsumiya
  • Patent number: 8377508
    Abstract: A solventless laminating adhesive comprising a polyisocyanate component and a polyol component, both of which are free from polyol components exhibiting crystalline properties at ordinary temperatures. The adhesive exhibits an initial viscosity of 500 to 1000 mPa s three minutes after mixing of the polyisocyanate component with the polyol component and a viscosity increase of 100 to 350% based on the initial viscosity 20 minutes after the mixing. In a coater which is provided with a pair of opposed rolls and in which the rolls rotates in the directions contrary to each other at the opposition site, the adhesive is applied to a film passing between the rolls.
    Type: Grant
    Filed: May 12, 2008
    Date of Patent: February 19, 2013
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Takashi Uemura, Shigetoshi Sasano, Yasuhiko Kataoka
  • Patent number: 8357453
    Abstract: The invention relates to moisture-reactive hotmelt adhesive compositions which comprise at least one polyurethane prepolymer P1 being liquid at room temperature containing isocyanate groups and also at least one linear polyurethane P2 being solid at room temperature which comprises polycaprolactone segments, contains hydroxyl groups and has a melt viscosity of 100-300 Pa·s at 170° C. The compositions are notable in particular for a prolonged open time.
    Type: Grant
    Filed: June 29, 2007
    Date of Patent: January 22, 2013
    Assignee: Sika Technology AG
    Inventor: Ukiwo Onuoha
  • Patent number: 8357763
    Abstract: An adhesion promoter for a hot melt adhesive or a pressure sensitive adhesive prepared by admixing a silane composition with an aqueous buffer solution, where the silane composition includes at least two silane compounds. The adhesive is able to bind at very low surface free energy substrates, such as Xerographic prints contaminated by silicone fuser oil. The hot melt adhesive maintains a substantially stable viscosity at temperature ranging from about 100° C. to about 200° C.
    Type: Grant
    Filed: May 2, 2007
    Date of Patent: January 22, 2013
    Assignee: Xerox Corporation
    Inventors: Guiqin Song, Nan-Xing Hu, T. Brian McAneney, Gordon Sisler
  • Patent number: 7914896
    Abstract: A moisture-curable polyurethane hot-melt adhesive containing a urethane prepolymer obtained by reacting a polyol (A) which comprises a polyester polyol (a-1) obtained by reacting a polyol prepared by the addition of bisphenol A with an alkylene oxide with both an aliphatic polycarboxylic acid and an aromatic polycarboxylic acid, a crystalline polyester polyol (a-2), and a polyoxyethylene glycol (a-3) having a number-average molecular weight of 2000 to 25000 with a polyisocyanate (B); and a moisture-permeable film, which are suitable for the production of sport wear, raincoats, shoes, fireman uniforms, military uniforms, and so on.
    Type: Grant
    Filed: June 3, 2008
    Date of Patent: March 29, 2011
    Assignee: DIC Corporation
    Inventors: Yoshinori Kanagawa, Minoru Takahashi
  • Patent number: 7914895
    Abstract: A moisture curable hot melt adhesive composition includes a polyurethane prepolymer, optionally a tackifying resin, and optionally a thermoplastic polymer. The polyurethane prepolymer includes a reaction product of an amorphous polyester polyol, a polyisocyanate, and a crystalline monofunctional alcohol that has a melting point of no less than about 80° C.
    Type: Grant
    Filed: May 24, 2007
    Date of Patent: March 29, 2011
    Assignee: H.B. Fuller Company
    Inventor: Kevin J. Reid
  • Patent number: 7906581
    Abstract: Methods, apparatuses, and systems for manufacturing a hot melt adhesive containing an adhesion promoter in a continuous mode include supplying a melted, hot melt adhesive to a mixing device at a first predetermined rate while simultaneously supplying an adhesion promoter to the same mixing device at a second predetermined rate to form a homogeneous admixture containing the hot melt adhesive and adhesion promoter. The hot melt adhesive/adhesion promoter mixture is subsequently reacted in at least one tubular reactor at a predetermined temperature for a predetermined residence time to allow the adhesion promoter to chemically bond with the hot melt adhesive and form an adhesive-promoter-treated hot melt adhesive. The adhesion-promoter-treated hot melt adhesive is collected in a product receiver and may be further processed.
    Type: Grant
    Filed: September 5, 2007
    Date of Patent: March 15, 2011
    Assignee: Xerox Corporation
    Inventors: Frank Ping-Hay Lee, Tie Hwee Ng, Sheau Van Kao, Guiqin Song
  • Patent number: 7883652
    Abstract: Polydiorganosiloxane polyoxamide, linear, block copolymers and methods of making the copolymers are provided. The method of making the copolymers involves reacting a diamine with a precursor having at least one polydiorganosiloxane segment and at least two oxalyamino groups. The polydiorganosiloxane polyoxamide block copolymers are of the (AB)n type.
    Type: Grant
    Filed: January 29, 2009
    Date of Patent: February 8, 2011
    Assignee: 3M Innovative Properties Company
    Inventors: Charles M. Leir, Karl E. Benson, Richard G. Hansen, Mark D. Purgett, Albert I. Everaerts, Audrey A. Sherman
  • Patent number: 7704602
    Abstract: An iodine/iodide-containing hot melt coatable adhesive is provided. This adhesive is prepared by mixing iodine and an iodide salt, individually or in combination, with solubilizing liquids. The iodine and iodide salt are combined with a pre-adhesive composition in a hot melt mixer, with an iodine/iodide complexing agent being present in the mixture. The mixture is mixed at a temperature from about 130° C. to about 200° C. and sufficiently to form an iodine/iodide-containing hot melt coatable adhesive. Alternatively, the iodide may be generated in situ. The adhesive so prepared may be packaged for coating on a substrate at a later time, or may be immediately coated to form an adhesive composite. Adhesive composites, particularly surgical incise drapes, are provided incorporating this hot melt coatable adhesive.
    Type: Grant
    Filed: February 8, 2007
    Date of Patent: April 27, 2010
    Assignee: 3M Innovative Properties Company
    Inventors: Danli Wang, Stephen E. Krampe, Zhiming Zhou, Matthew T. Scholz, Michael P. Daniels
  • Patent number: 7410694
    Abstract: The invention relates to an adhesive.
    Type: Grant
    Filed: April 11, 2005
    Date of Patent: August 12, 2008
    Assignee: tesa Aktiengesellschaft
    Inventors: Marc Husemann, Stephan Zollner
  • Patent number: 7235293
    Abstract: A hot melt adhesive is provided that is useful in the production of textiles, such as a tuft carpet, contains a blend of constituents that allows synthetic carpet members to be fully recycled without first separating the adhesive from the carpet members. The adhesive includes (a) from about 5 to about 30 weight % of a copolymer of an alkyl acrylate having from 2 to 18 carbon atoms; (b) from about 5 to about 50 weight % of a wax and desirably a C10 wax; (c) up to about 75 weight % of a filler; and (d) from about 0.1 to about 10 weight % of an aliphatic carboxylic acid having from 8 to 24 carbon atoms.
    Type: Grant
    Filed: June 3, 2004
    Date of Patent: June 26, 2007
    Assignee: Beaulieu Group, LLC
    Inventors: Jeffrey Daniel Daily, Shannon Lee Van Scoy
  • Patent number: 7208541
    Abstract: A hot melt adhesive based on ethylene-2-ethylhexyl acrylate copolymer finds use in packaging applications where high heat resistance, as well as good cold tolerance, is required.
    Type: Grant
    Filed: August 22, 2003
    Date of Patent: April 24, 2007
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: Lie-zhong Gong, Melissa L. Allen, Justin A. Mehaffy, Darshak R. Desai, Dale L. Haner, Tuyet Le
  • Patent number: 7199204
    Abstract: A hot melt adhesive comprising an adhesive polymer and a modified rosin-terpene, preferably a phenol modified rosin terpene. The adhesive is particularly useful in packaging applications.
    Type: Grant
    Filed: May 7, 2002
    Date of Patent: April 3, 2007
    Assignees: National Starch and Chemical Investment Holding Corporation, Arizona Chemical Company
    Inventors: Dale L. Haner, Abhay K. Deshpande, Justin A. Mehaffy, George A. Locko
  • Patent number: 7189793
    Abstract: An iodine/iodide-containing hot melt coatable adhesive is provided. This adhesive is prepared by mixing iodine and an iodide salt, individually or in combination, with solubilizing liquids. The iodine and iodide salt are combined with a pre-adhesive composition in a hot melt mixer, with an iodine/iodide complexing agent being present in the mixture. The mixture is mixed at a temperature from about 130° C. to about 200° C. and sufficiently to form an iodine/iodide-containing hot melt coatable adhesive. Alternatively, the iodide may be generated in situ. The adhesive so prepared may be packaged for coating on a substrate at a later time, or may be immediately coated to form an adhesive composite. Adhesive composites, particularly surgical incise drapes, are provided incorporating this hot melt coatable adhesive.
    Type: Grant
    Filed: April 28, 2005
    Date of Patent: March 13, 2007
    Assignee: 3M Innovative Properties Company
    Inventors: Danli Wang, Stephen E. Krampe, Zhming Zhou, Matthew T. Scholz, Michael P. Daniels
  • Patent number: 6939936
    Abstract: An iodine/iodide-containing hot melt coatable adhesive is provided. This adhesive is prepared by mixing iodine and an iodide salt, individually or in combination, with solubilizing liquids. The iodine and iodide salt are combined with a pre-adhesive composition in a hot melt mixer, with an iodine/iodide complexing agent being present in the mixture. The mixture is mixed at a temperature from about 130° C. to about 200° C. and sufficiently to form an iodine/iodide-containing hot melt coatable adhesive. Alternatively, the iodide may be generated in situ. The adhesive so prepared may be packaged for coating on a substrate at a later time, or may be immediately coated to form an adhesive composite. Adhesive composites, particularly surgical incise drapes, are provided incorporating this hot melt coatable adhesive.
    Type: Grant
    Filed: April 25, 2002
    Date of Patent: September 6, 2005
    Assignee: 3M Innovative Properties Company
    Inventors: Danli Wang, Stephen E. Krampe, Zhming Zhou, Matthew T. Scholz, Michael P. Daniels
  • Patent number: 6926959
    Abstract: The invention is directed to a radiation curable adhesive composition comprising at least one vinyl modified block copolymer having a first polyvinyl aromatic block and a second polydiene block having vinyl functionality, and at least one tackifier. Optionally, the composition may comprises at least one second block copolymer that has not been vinyl modified, at least one platicizer, and at least one wax. The invention is also directed to a double-faced label formed from the composition and the method of producing said label.
    Type: Grant
    Filed: April 29, 2003
    Date of Patent: August 9, 2005
    Assignee: H. B. Fuller Licensing & Financing, Inc.
    Inventors: Mark S. Kroll, Margarita Acevedo, Janelle C. Cameron, Thomas F. Kauffman, Jeffrey S. Lindquist, Eugene R. Simmons, David B. Malcolm, Kathryn A. Coleman
  • Patent number: 6881442
    Abstract: In a continuous two-stage process for preparing solvent-free polyacrylate hotmelt pressure sensitive adhesives which is gentle on the polymer and redeploys the solvent used in the process the following steps are carried out: polymerizing a self-adhesive pressure sensitive adhesive in solution, the solvent having a low vapor pressure; continuously mixing the polymer solution with antioxidants and preheating the mixture under superatmospheric pressure without boiling it; concentrating the polymer solution to a residual solvent content of less than 0.
    Type: Grant
    Filed: May 13, 2003
    Date of Patent: April 19, 2005
    Assignee: tesa Aktiengesellschaft
    Inventors: Marc Husemann, Stephan Zöllner, Klaus Massow, Frank Henke
  • Publication number: 20040249102
    Abstract: The invention relates to a hotmelt pressure sensitive adhesive (PSA), in particular an acrylic hotmelt PSA, featuring low shrinkback after extrusion coating, to a process for preparing it, and to its use for producing PSA tapes.
    Type: Application
    Filed: March 12, 2004
    Publication date: December 9, 2004
    Applicant: tesa Aktiengesellschaft
    Inventors: Marc Husemann, Stephan Zollner
  • Patent number: 6787244
    Abstract: The present invention describes the use of poly-o-hydroxy amides (PHAs) for adhesively bonding articles or materials, especially components used in the semiconductor industry, such as chips and wafers, a process for adhesively bonding materials, especially chips and/or wafers, chip and/or wafer stacks produced by the process, and adhesive compositions which comprise the poly-o-hydroxy amides of the formula (I).
    Type: Grant
    Filed: July 30, 2002
    Date of Patent: September 7, 2004
    Assignee: Infineon Technologies AG
    Inventors: Recai Sezi, Andreas Walter
  • Patent number: 6670442
    Abstract: Hot melt adhesives are prepared using thermoplastic polyamides derived from polymerized fatty acid components. The adhesives are particularly useful for bonding nonpolar substrates such as poly-&agr;-olefins.
    Type: Grant
    Filed: June 21, 2001
    Date of Patent: December 30, 2003
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Angela Rossini, Francesco Meda
  • Patent number: 6590063
    Abstract: Copolyamides, consisting of polycondensation products of the following components: caprolactam 10 to 45 mol-%, laurolactam 30 to 55 mol-%, at least 2 dicarboxylic acids 20 to 50 mol-% of the following compounds, aliphatic &agr;,&ohgr;-dicarboxylic acids with 6 up to 14 C atoms inclusively, terephthalic acid, isophthalic acid and 2,6-naphthalene dicarboxylic acid, wherein the content of aromatic dicarboxylic acids is lower than 10 mol-%, with reference to the allover amount of the above-mentioned components, which add up to 100 mol-%, a diamine mixture in an amount that is equimolar to that of the dicarboxylic acids, chosen from the group of the following substances, hexamethylene diamine, piperazine and/or 2-methyl-1,5-diaminopentane, wherein the molar content of hexa-methylene diamine is between 75 and 95 mol-% with reference to the diamine mixture. The copolyamides according to the invention are used for the production of mono- and multifilaments, fibers, films and nets.
    Type: Grant
    Filed: May 9, 2001
    Date of Patent: July 8, 2003
    Assignee: EMS-Chemie AG
    Inventors: Gerhard Poessnecker, Jürgen Spindler, Eberhard Kinkelin
  • Patent number: 6579915
    Abstract: The invention is directed to a radiation curable adhesive composition comprising at least one vinyl modified block copolymer having a first polyvinyl aromatic block and a second polydiene block having vinyl functionality, and at least one tackifier. Optionally, the composition may comprises at least one second block copolymer that has not been vinyl modified, at least one platicizer, and at least one wax. The invention is also directed to a double-faced label formed from the composition and the method of producing said label.
    Type: Grant
    Filed: January 29, 2001
    Date of Patent: June 17, 2003
    Assignee: H.B. Fuller Licensing & Financing Inc.
    Inventors: Mark S. Kroll, Margarita Acevedo, Janelle C. Cameron, Thomas F. Kauffman, Jeffrey S. Lindquist, Eugene R. Simmons, David B. Malcolm, Kathryn A. Coleman
  • Patent number: 6528615
    Abstract: The present invention relates to copolymers containing polyamide blocks and polyether blocks based on ethoxylated primary amines, these copolymers having a melting point of between 80° C. and 135° C. and an MFI (melt flow index) of between 5 and 80 g/10 min (2.16 kg-150° C.). The invention also relates to adhesives of the HMA (or hot melt adhesive) type consisting of the above copolymers containing polyamide blocks and polyether blocks.
    Type: Grant
    Filed: March 26, 2001
    Date of Patent: March 4, 2003
    Assignee: Atofina
    Inventors: Hermann Hilgers, Reinhard Linemann
  • Patent number: 6359107
    Abstract: A composition of and method for making high performance imide resins that are processable by resin transfer molding (RTM) and resin infusion (RI) techniques were developed. Materials with a combination of properties, making them particularly useful for the fabrication of composite parts via RTM and/or RI processes, were prepared, characterized and fabricated into moldings and carbon fiber reinforced composites and their mechanical properties were determined. These materials are particularly useful for the fabrication of structural composite components for aerospace applications. The method for making high performance resins for RTM and RI processes is a multi-faceted approach. It involves the preparation of a mixture of products from a combination of aromatic diamines and aromatic dianhydrides at relatively low calculated molecular weights (i.e. high stoichiometric offsets) and endcapping with latent reactive groups.
    Type: Grant
    Filed: May 18, 2000
    Date of Patent: March 19, 2002
    Assignee: The United States of America as represented by the Administrator, National Aeronautics and Space Administration
    Inventors: John W. Connell, Joseph G. Smith, Paul M. Hergenrother
  • Patent number: 6307008
    Abstract: A polymide useful as an adhesive for semiconductor assemblies having excellent thermal resistance and adhesive strength at high temperatures.
    Type: Grant
    Filed: February 25, 2000
    Date of Patent: October 23, 2001
    Assignee: Saehan Industries Corporation
    Inventors: Kyung Rok Lee, Soon Sik Kim, Kyeong Ho Chang, Jeong Min Kweon
  • Patent number: 6235818
    Abstract: A hot melt adhesive composition exhibiting excellent adhesive strength and which is useful as an adhesive for styrene resins contains (B) tackifier and (C) ethylene/C3-C20 &agr;-olefin/aromatic vinyl compound random copolymer and, in some embodiments also (A) base polymer, such as polyolefin, polar group-containing polymer and aromatic vinyl compound/conjugated diene copolymer. A low molecular weight polyolefin may also be included in all embodiments. The randon copolymer (C) may be prepared by polymerizing the &agr;-olefin and aromatic vinyl compound in the presence of a metallocene containing catalyst. In addition to excellent adhesive strength the hot melt adhesives have improved workability.
    Type: Grant
    Filed: July 29, 1999
    Date of Patent: May 22, 2001
    Assignee: Mitsui Chemicals
    Inventors: Kenichi Morizono, Keiji Okada, Suguru Tokita
  • Patent number: 6150017
    Abstract: Pressure-sensitive hotmelt adhesive composition based on non-thermoplastic elastomers, obtained bya) preparing, as the preliminary batch, a composition comprising the elastomers and one or more of the following additives such as fillers, anti-ageing agents, plasticizers and tackifier resins in an intensively shearing, intensively cooling mixer and without solvent, the composition having a final temperature of from 100.degree. C. to 160.degree. C.,b) mixing and homogenizing the preliminary batch in a second mixer with one or more of the following additives such as fillers, anti-ageing agents, plasticizers and tackifier resins, without solvent, the composition having a final temperature of from 100.degree. C. to 160.degree. C.,where the total residence time of the composition at temperatures over 100.degree. C. does not exceed a figure of 6 minutes, so that the resulting hotmelt adhesive composition has a viscosity of more than 900 Pa*s, in particular from 900 Pa*s to 1200 Pa*s, at 130.degree. C.
    Type: Grant
    Filed: January 14, 1998
    Date of Patent: November 21, 2000
    Assignee: Beiersdorf AG
    Inventors: Axel Burmeister, Heiko Leydecker, Jochen Stahr
  • Patent number: 5973106
    Abstract: Disclosed are a hot-melting acrylonitrile (AN) polymer composition comprising a non-volatile component modified from AN alone or a AN monomer composition through chemical reaction, an AN polymer and water, a method for producing the composition, and a method for producing a shaped article of AN polymer by melting the composition under heat followed by shaping the melt. The composition and the shaped article do not contain toxic AN and AN monomer mixture.
    Type: Grant
    Filed: August 12, 1997
    Date of Patent: October 26, 1999
    Assignee: Japan Exlan Company Limited
    Inventors: Hirotaka Shiota, Ryosuke Nishida, Takahisa Kida, Noriyuki Kohara, Yoshihiro Watanabe, Ryuichi Kasahara
  • Patent number: 5866676
    Abstract: Polyimide copolymers were prepared by reacting different ratios of 3,4'-oxydianiline (ODA) and 1,3-bis(3-aminophenoxy)benzene (APB) with 3,3',4,4'-biphenylcarboxylic dianhydride (BPDA) and endcapping with an effective amount of a non-reactive endcapper. Within a narrow ratio of diamines, from .sup..about. 50% ODA/50% APB to .sup..about. 95% ODA/5% APB, the copolyimides prepared with BPDA have a unique combination of properties that make them very attractive for various applications. This unique combination of properties includes low pressure processing (200 psi and below), long term melt stability (several hours at 390.degree. C.), improved toughness, improved solvent resistance, improved adhesive properties, and improved composite mechanical properties.
    Type: Grant
    Filed: February 14, 1995
    Date of Patent: February 2, 1999
    Assignee: The United States of America as represented by the United States National Aeronautics and Space Administration
    Inventor: Brian J. Jensen
  • Patent number: 5773509
    Abstract: A heat resistant resin composition comprising, as the main components,(A) 100 parts by weight of an organic solvent-soluble polyimide resin having a glass transition temperature of 350.degree. C. or less,(B) 5 to 100 parts by weight of an epoxy compound having at least two epoxy groups in one molecule, and(C) 0.1 to 20 parts by weight of a compound having an active hydrogen group which can react with the epoxy compound (B),a heat resistant film adhesive comprising, as the main components, the above components (A), (B) and (C), and a process for producing a heat resistant film adhesive by casting a solution of the above heat resistant resin composition on one side or both sides of a support.
    Type: Grant
    Filed: March 7, 1995
    Date of Patent: June 30, 1998
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Tatsuhiro Yoshida, Keizo Takahama, Syusaku Okamyo
  • Patent number: 5770676
    Abstract: In the process of the present invention, a non-polar, aprotic solvent is removed from an oligomer/polymer solution by freeze-drying in order to produce IPNs and semi-IPNs. By thermally quenching the solution to a solid in a short length of time, the size of the minor constituent-rich regions is greatly reduced as they are excluded along with the major constituent from the regions of crystallizing solvent. The use of this process sequence of controlling phase morphology provides IPNs and semi-IPNs with improved fracture toughness, microcracking resistance, and other physical-mechanical properties as compared to IPNs and semi-IPNs formed when the solvent is evaporated rather than sublimed.
    Type: Grant
    Filed: April 10, 1996
    Date of Patent: June 23, 1998
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Ruth H. Pater, Marion G. Hansen
  • Patent number: 5760168
    Abstract: Controlled molecular weight phenylethynyl terminated imide oligomers (PETIs) have been prepared by the cyclodehydration of precursor phenylethynyl terminated amic acid oligomers. Amino terminated amic acid oligomers are prepared from the reaction of dianhydride(s) with an excess of diamine(s) and subsequently endcapped with phenylethynyl phthalic anhydride(s) (PEPA). The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide under nitrogen at room temperature. The amic acid oligomers are subsequently cyclodehydrated either thermally or chemically to the corresponding imide oligomers. Direct preparation of PETIs from the reaction of dianhydride(s) with an excess of diamine(s) and endcapped with phenylethynyl phthalic anhydride(s) has been performed in m-cresol. Phenylethynyl phthalic anhydrides are synthesized by the palladium catalyzed reaction of phenylacetylene with bromo substituted phthalic anhydrides in triethylamine.
    Type: Grant
    Filed: October 21, 1996
    Date of Patent: June 2, 1998
    Assignee: The United States of America as represented by the Administrator of the National Aeuonautics and Space Administration
    Inventors: Paul M. Hergenrother, Joesph G. Smith, Jr.
  • Patent number: 5741883
    Abstract: Tough, soluble, aromatic, thermoplastic copolyimides were prepared by reacting 4,4'-oxydiphthalic anhydride, 3,4,3',4'-biphenyltetracarboxylic dianhydride and 3,4'-oxydianiline. These copolyimides were found to be soluble in common amide solvents such as N,N'-dimethyl acetamide, N-methylpyrrolidinone, and dimethylformamide allowing them to be applied as the fully imidized copolymer and to be used to prepare a wide range of articles.
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: April 21, 1998
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Robert G. Bryant
  • Patent number: 5739263
    Abstract: The present invention provides a film adhesive comprising, as the main constituent, a polyimide resin having a glass transition temperature of 350.degree. C. or lower and soluble in organic solvents, which polyimide resin is obtained by reacting at least one of the following acid components (A) and (B)(A) 4,4'-oxydiphthalic acid dianhydride(B) 3,3',4,4'-biphenyltetracarboxylic acid dianhydride and/or 3,3',4,4'-benzophenonetetracarboxylic acid dianhydridewith at least one of the following amine components (C) and (D)(C) a siloxane compound represented by the following general formula (1) and/or 2,2-bis(4-(4-amino-phenoxy)phenyl)propane ##STR1## wherein R.sub.1 and R.sub.2 are each a bivalent aliphatic (C.sub.1-4) or aromatic group; R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each a mono-valent aliphatic or aromatic group; and k is an integer of 1-20,(D) bis(aminophenoxy)benzene and/or dimethylphenylene-diamineto give rise to ring closure of imide, as well as a process for producing said film adhesive.
    Type: Grant
    Filed: January 28, 1994
    Date of Patent: April 14, 1998
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Tatsuhiro Yoshida, Yoshitaka Okugawa, Toshio Suzuki, Toshiro Takeda, Yushi Sakamoto, Takuya Tochimoto
  • Patent number: 5672677
    Abstract: A polyamide hot melt adhesive is provided. It comprises the polyamide condensation product of substantially equivalent quantities of (a) an acid component consisting essentially of one or more polymeric fatty acids and one or more dicarboxylic acids and (b) an amine component consisting essentially of (i) two or more non-cyclic aliphatic diamines and (ii) one or more amine-terminated polyglycol diamines. The amine component is substantially free of piperazine-containing polyamines. The adhesive has an open time of at least 120 seconds. Preferred non-cyclic aliphatic diamines are ethylenediamine and 1,6-diaminohexane, preferably present in about equimolar amounts. The composition may further comprise an aromatic sulfonamide plasticizer. The adhesive is particularly useful for spraying applications.
    Type: Grant
    Filed: January 12, 1996
    Date of Patent: September 30, 1997
    Assignee: The Dexter Corporation
    Inventors: Paul L. Morganelli, Douglas E. Frost
  • Patent number: 5652308
    Abstract: Novel tackifier resins having a M.sub.n of 5,000 or less and a T.sub.g of 0.degree. C. or above are produced by combining a metallocene catalyst with an alpha-olefin and a cyclic monomer. New adhesives are produced by blending the novel tackifier with a base polymer.
    Type: Grant
    Filed: July 21, 1995
    Date of Patent: July 29, 1997
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Natalie Ann Merrill, James McLeod Farley, Martha Hetzel Robertson, Charles Lewis Sims, Richard Byron Pannell, Angelo Anthony Montagna
  • Patent number: 5644022
    Abstract: Polyimide copolymers were prepared by reacting different ratios of 3,4'-oxydianiline (ODA) and 1,3-bis(3-aminophenoxy)benzene (APB) with 3,3',4,4'-biphenylcarboxylic dianhydride (BPDA), and terminating with an effective amount of a reactive endcapper. The reactive endcappers employed include 4-phenylethynyl phthalic anhydride (PEPA), 3-aminophenoxy-4'-phenylethynylbenzophenone (3-APEB), maleic anhydride (MA) and nadic anhydride (5-norbornene-2,3-dicarboxylic anhydride) (NA). Within a relatively narrow ratio of diamines, from .sup..about. 50% ODA/50% APB to .sup..about. 95% ODA/5% APB, the copolyimides prepared with BPDA and terminated with reactive endgroups have a unique combination of properties that make them very attractive for a number of applications. This unique combination of properties includes low pressure processing (200 psi and below), long term melt stability (several hours at 300.degree. C.
    Type: Grant
    Filed: February 14, 1995
    Date of Patent: July 1, 1997
    Assignee: The United States of America as represented by the Admninistrator of the National Aeronautics and Space Administration
    Inventor: Brian J. Jensen
  • Patent number: 5637670
    Abstract: Novel molecular weight controlled and endcapped polybenzimidazoles (PBI) are prepared by the aromatic nucleophilic displacement reaction of di(hydroxyphenylbenzimidazole) monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The PBI are endcapped with mono(hydroxyphenyl)benzimidazoles. The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide using alkali metal bases such as potassium carbonate at elevated temperatures under nitrogen. Mono(hydroxyphenyl)benzimidazoles are synthesized by reacting phenyl-4-hydroxybenzoate with aromatic (o-diamine)s in diphenylsulfone. Molecular weight controlled and endcapped PBI of new chemical structures are prepared that exhibit a favorable combination of physical and mechanical properties.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: June 10, 1997
    Assignee: The United States of America as represented by the Administrator, National Aeronautics and Space Administration
    Inventors: John W. Connell, Paul M. Hergenrother, Joseph G. Smith, Jr.
  • Patent number: 5606014
    Abstract: Controlled molecular weight imide oligomers and co-oligomers containing pendent phenylethynyl groups (PEPIs) and endcapped with nonreactive or phenylethynyl groups have been prepared by the cyclodehydration of the precursor amide acid oligomers or co-oligomers containing pendent phenylethynyl groups and endcapped with nonreactive or phenylethynyl groups. The amine terminated amide acid oligomers or co-oligomers are prepared from the reaction of dianhydride(s) with an excess of diamine(s) and diamine containing pendent phenylethynyl groups and subsequently endcapped with a phenylethynyl phthalic anhydride or monofunctional anhydride. The anhydride terminated amide acid oligomers and co-oligomers are prepared from the reaction of diamine(s) and diamine containing pendent phenylethynyl group(s) with an excess of dianhydride(s) and subsequently endcapped with a phenylethynyl amine or monofunctional amine. The polymerizations are carried out in polar aprotic solvents such as under nitrogen at room temperature.
    Type: Grant
    Filed: August 4, 1995
    Date of Patent: February 25, 1997
    Assignee: The United States of America as represented by the United States National Aeronautics and Space Administration
    Inventors: John W. Connell, Joseph G. Smith, Jr., Paul M. Hergenrother
  • Patent number: 5502157
    Abstract: A copolyimide was prepared by reacting 3,4'-oxydianiline (3,4'-ODA) with a dianhydride blend comprising, based on the total amount of the dianhydride blend, about 67 to 80 mole percent of 4,4'-oxydiphthalic anhydride (ODPA) and about 20 to 33 mole percent of 3,3',4,4'-benzophenonetetracarboxylic dianhydride (BTDA). The copolyimide may be endcapped with up to about 10 mole percent of a monofunctional aromatic anhydride and has unbalanced stoichiometry such that a molar deficit in the dianhydride blend is compensated with twice the molar amount of the monofunctional aromatic anhydride. The copolyimide was used to prepare composites, films and adhesives. The film and adhesive properties were significantly better than those of LaRC.TM.-IA.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: March 26, 1996
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Alice C. Chang, Terry L. St. Clair
  • Patent number: 5478916
    Abstract: A solvent resistant copolyimide was prepared by reacting 4,4'-oxydiphthalic anhydride with a diaimine blend comprising, based on the total amount of the diamine blend, about 75 to 90 mole percent of 3,4'-oxydianiline and about 10 to 25 mole percent p-phenylene diamine. The solvent resistant copolyimide had a higher glass transition temperature when cured at 350.degree. , 371.degree. and 400.degree. C. than LaRC.TM.-IA. The composite prepared from the copolyimide had similar mechanical properties to LaRC.TM.-IA. Films prepared from the copolyimide were resistant to immediate breakage when exposed to solvents such as dimethylacetamide and chloroform. The adhesive properties of the copolyimide were maintained even after testing at 23.degree., 150.degree., 177.degree. and 204.degree. C.
    Type: Grant
    Filed: September 1, 1994
    Date of Patent: December 26, 1995
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Alice C. Chang, Terry L. St. Clair
  • Patent number: 5459230
    Abstract: The use of copolyamides as melt adhesive for heat sealing is disclosed. At least three monomer components are copolymerized in the copolyamide. These monomer components are selected from the following group: an equimolar mixture of adipic acid and hexamethylenediamine (6,6 salt), lauric acid lactam, 11-aminoundecanoic acid, an equimolar mixture of azelaic acid and hexamethylenediamine (6,9 salt), an equimolar mixture of sebacic acid and hexamethylenediamine (6,10 salt) and an equimolar mixture of dodecane dicarboxylic acid and hexamethylenediamine (6,12 salt), the melting point of the copolyamide being lower than 140.degree. C. and at least 10% by weight of lauric acid lactam and/or 11-aminoundecanoic acid being copolymerized.
    Type: Grant
    Filed: May 27, 1994
    Date of Patent: October 17, 1995
    Assignee: Elf Autochem Deutschland GmbH
    Inventors: Eduard de Jong, Karl-Heinz Hapelt
  • Patent number: 5412059
    Abstract: Novel molecular weight controlled and endcapped polybenzimidazoles (PBI) are prepared by the aromatic nucleophilic displacement reaction of di(hydroxyphenylbenzimidazole) monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The PBI are endcapped with mono(hydroxyphenyl)benzimidazoles. The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide using alkali metal bases such as potassium carbonate at elevated temperatures under nitrogen. Mono(hydroxyphenyl)benzimidazoles are synthesized by reacting phenyl-4-hydroxybenzoate with aromatic (o-diamine)s in diphenylsulfone. Molecular weight controlled and endcapped PBI of new chemical structures are prepared that exhibit a favorable combination of physical and mechanical properties.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: May 2, 1995
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: John W. Connell, Paul M. Hergenrother, Joseph G. Smith, Jr.
  • Patent number: 5412066
    Abstract: Four phenylethynyl amine compounds--3 and 4-aminophenoxy-4'-phenylethynylbenzophenone, and 3 and 4-amino-4'-phenylethynylbenzophenone--were readily prepared and were used to endcap imide oligomers. Phenylethynyl-terminated amide acid oligomers and phenylethynyl-terminated imide oligomers with various molecular weights and compositions were prepared and characterized. These oligomers were cured at 300.degree. C. to 400.degree. C. to provide crosslinked polyimides with excellent solvent resistance, high strength and modulus and good high temperature properties. Adhesive panels, composites, films and moldings from these phenylethynyl terminated imide oligomers gave excellent mechanical performance.
    Type: Grant
    Filed: March 3, 1994
    Date of Patent: May 2, 1995
    Assignee: Ther United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Paul M. Hergenrother, Robert G. Bryant, Brian J. Jensen, Stephen J. Havens
  • Patent number: 5371168
    Abstract: Amorphous polyimide powder which has recurring structural units of the formula (I): ##STR1## as a fundamental skeleton, is blocked at the polymer chain end with dicarboxylic anhydride represented by the formula (II) ##STR2## wherein Z is a divalent radical having from 6 to 27 carbon atoms and selected from the group consisting of a monoaromatic radical, condensed polyaromatic radical and noncondensed aromatic radical connected to each other with a direct bond or a bridge member, and essentially has no reactive radical at the polymer chain end, preparation process of the amorphous polyimide powder, heat-resistant adhesive comprising the polyimide, and bonding method using the adhesive.
    Type: Grant
    Filed: June 5, 1992
    Date of Patent: December 6, 1994
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Wataru Yamashita, Shoji Tamai, Akihiro Yamaguchi
  • Patent number: 5346982
    Abstract: A polyimide-based heat-resistant adhesive having excellent peel strength and heat resistance comprising polyimide composed of 10 to 99% by mole of structural units having the formula (1) and 1 to 90% by mole of structural units having the formula (2) or comprising polyamic acid precursor which corresponds to the polyimide.
    Type: Grant
    Filed: June 7, 1993
    Date of Patent: September 13, 1994
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Shoji Tamai, Katsuaki Iiyama, Akihiro Yamaguchi
  • Patent number: 5262479
    Abstract: Improved plasticizer resistant pressure sensitive hot melt adhesive compositions are prepared by incorporating in the adhesive polymer, tackifying resin and oil 5 to 70% by weight of the adhesive of a core shell modifier comprising a crosslinked rubbery core and a glassy thermoplastic polymer shell, the core being crosslinked by the presence therein of up to 5% by weight of a polyunsaturated monomer having two or more non-conjugated sites of unsaturation of unequal reactivity.
    Type: Grant
    Filed: November 24, 1992
    Date of Patent: November 16, 1993
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventor: Singa D. Tobing
  • Patent number: 4937138
    Abstract: A hot melt adhesive, a laminar structure, and non-woven article fabricated from a blend comprising:from about 50 percent by weight to about 5 percent by weight of a butene-1 homopolymer or copolymer;from about 50 percent by weight to about 95 percent by weight of a tackifying resin;from a 0.01 to about 1 phr of a nucleating agent;up to about 1 part per hundred (phr) of a stabilizer;up to about 30 phr of a plasticizer; andup to about 30 phr of a wax.
    Type: Grant
    Filed: February 29, 1988
    Date of Patent: June 26, 1990
    Assignee: Shell Oil Company
    Inventor: Simon Mostert
  • Patent number: 4554304
    Abstract: Hot melt adhesives with long open time good bonding to cold metals are made of blends of a maleic anhydride modified copolymer of butene-1 and ethylene, an aliphatic, substantially non-polar resin, a antioxidizing agent and, optionally, microcrystalline wax, a block copolymer and atactic polypropylene.
    Type: Grant
    Filed: May 31, 1984
    Date of Patent: November 19, 1985
    Assignee: Shell Oil Company
    Inventors: David R. Hansen, William H. Korcz