Polymer Prepared From Isocyanate Reactant Has Adhesive Property Patents (Class 528/905)
  • Patent number: 6355760
    Abstract: The invention relates to polyurethane having improved shear strength which are obtained by polycondensation of a mixture of at least one polyol containing one or more polyether grafts and at least one short-chain alcohol with at least one diisocyanate. The invention also relates to the polyurethanes which are in the form of strips whose thickness is between 0.1 and 10 mm. The invention also relates to articles comprising the said polyurethanes.
    Type: Grant
    Filed: September 11, 2000
    Date of Patent: March 12, 2002
    Assignee: Bostik Findley
    Inventors: Eric Papon, Jean-Jacques Villenave, Philippe Tordjeman
  • Patent number: 6353078
    Abstract: The present invention provides an adhesive comprising a polyester polyol or polyurethane polyol possessing structural units represented by the following general formula (I) within its molecular structure, and an organic polyisocyanate in which the isocyanate groups may be protected: wherein R1 and R2 are the same or different and each represents lower alkyl. The adhesive of the present invention exhibits an excellent initial adhesion strength; and provides adhered objects that exhibit an excellent permanent adhesion strength, hot water resistance, flexibility, flexibility at a low temperature, and fatigue resistance, and is useful in adhering plastic, metal, and the like. In addition, the present invention provides a method of mixing the aforementioned components and using the mixture for adhesion, and a use of the mixture of the aforementioned components.
    Type: Grant
    Filed: January 27, 2000
    Date of Patent: March 5, 2002
    Assignee: Kyowa Yuka Co., Ltd.
    Inventors: Shigeru Murata, Masahiko Yasuda, Tetsuya Nakajima
  • Patent number: 6316573
    Abstract: An adhesive paste, free of water, based on a reaction product of a polyisocyanate component and a co-reactant selected from the group consisting of a polyol, a monofunctional fatty derivative component and mixtures thereof, wherein the reaction product contains moisture reactive isocyanate groups.
    Type: Grant
    Filed: August 24, 1998
    Date of Patent: November 13, 2001
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Wolfgang Klauck, Wolfgang Maier
  • Patent number: 6262217
    Abstract: Polyurethane compositions including the reaction product of a polyurethane prepolymer component including (a) at least one isocyanate-terminated polyalkadiene prepared by capping hydroxy-terminated polyalkadiene having a molecular weight from about 1500 to about 5000 grams per mol (g/mol) with isocyanate; and (b) at least one additional isocyanate-terminated polyalkadiene prepared by capping hydroxy-terminated polyalkadiene having a molecular weight from about 500 to about 1500 g/mol with isocyanate with a curative component. The compositions exhibit numerous useful properties, such as low glass transition temperature (Tg) high temperature stability, low viscosity at room and elevated temperatures, flexibility and flat dynamic mechanical properties versus temperature.
    Type: Grant
    Filed: December 15, 1997
    Date of Patent: July 17, 2001
    Assignee: Lord Corporation
    Inventors: Jack N. Tallmadge, Ashish P. Diwanji, Mark A. Weih, Walter C. Wilhem
  • Patent number: 6187892
    Abstract: The present invention relates to a method of making a coated substrate that requires a polyurethane/urea contact adhesive, and the coated substrates produced by this method. This invention requires a) a polyisocyanate with a functionality of less than about 4, b) optionally, a polyol blend consisting of about 95 to 100% polyether polyols with molecular weights from about 1800 to 12000 and average functionality from about 1.5 to about 4 and up to about 5% of chain extenders with molecular weights from about 60 to 400 and average functionality from about 1.5 to about 3, and c) polyethers having at least two isocyanate reactive groups and a molecular weight of from about 1800 to about 12000 and average functionality from about 1.5 to about 4 in which at least 50% of the isocyanate reactive groups are primary and/or secondary amino groups.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: February 13, 2001
    Assignee: Bayer Corporation
    Inventors: Peter H. Markusch, James W. Rosthauser, Robert L. Cline
  • Patent number: 6180744
    Abstract: A composition containing at least one isocyanate terminated polyester obtainable by enzyme catalyzed polyesterification of one or more monomers selected from dicarboxylic acids, diols or polyols and/or hydroxyacids in the presence or absence of an inert organic solvent and a diisocyanate.
    Type: Grant
    Filed: November 13, 1998
    Date of Patent: January 30, 2001
    Assignee: Baxenden Chemicals Limited
    Inventors: Alan Taylor, Julie Anne Thompson
  • Patent number: 6133395
    Abstract: This invention is a one-component moisture curable polyurethane composition containing a urethane prepolymer and at least one silane compound containing an average of at least 1.5 NCO groups, and an average of at least 1.5 hydrolyzable alkoxy groups, selected from the group comprising a silane compounds (B-1) which is prepared by the addition reaction of a secondary aminoalkoxysilane compound and a polyol-based polyisocyanate compound, and a lysine-based silane compound (B-2). The Polyol-based polyisocyanate compound is a reaction product of a polyol more than triol and diisocyanate. The composition of the invention is particularly suitable for bonding glass to other substrates such as, for example, metal, plastics, and painted steel plates without employing a primer. Moreover, the composition has good foaming resistance, as well as good elongation.
    Type: Grant
    Filed: November 10, 1998
    Date of Patent: October 17, 2000
    Assignee: The Yokohama Rubber Co., Ltd.
    Inventors: Akihiro Miyata, Kazunori Ishikawa, Kiminori Araki
  • Patent number: 6133400
    Abstract: This invention relates to a hot melt moisture cure polyurethane composition which is the reaction product of a polyether polyol formed from a compound selected from the group consisting of ethylene oxide, propylene oxide, 1,2-butylene oxide, 1,4-butylene oxide and mixtures thereof; a low molecular weight polyalkylene glycol having from 3 to 7 carbon atoms; a crystalline polyester polyol having a melting point from about 40.degree. C. to about 120.degree. C.; and at least one polyfinctional isocyanate component wherein said composition has a moisture vapor transmission rate of greater than about 100 g/m.sup.2 /day film thickness of from about 450 to about 500 g/m.sup.2, and hydrolysis resistance.
    Type: Grant
    Filed: January 20, 1999
    Date of Patent: October 17, 2000
    Assignee: H. B. Fuller Licensing, Inc.
    Inventor: Marietta B. Helmeke
  • Patent number: 6130309
    Abstract: An improved polyurethane is prepared by reacting a diol, an organic diisocyanate and a carboxylic acid with a critical selection of the amount of water in the reaction mixture. The polyurethane has improved adhesion, hydrophilicty and strength. The polymer has improved feel, and washability. Solutions of the polymer have low viscosity in aqueous solutions.
    Type: Grant
    Filed: September 20, 1996
    Date of Patent: October 10, 2000
    Assignee: Tyndale Plains-Hunter, Ltd.
    Inventors: Murray H. Reich, Ken Nelson
  • Patent number: 6087463
    Abstract: A reactive hot melt adhesive containing, as the main component, a blocked prepolymer made by reacting a linear prepolymer having isocyanate groups with a blocking agent, said blocked prepolymer having a number average molecular weight of at least 11,000 and a melt viscosity of at least 1,000 poise at a temperature of 110.degree. C.
    Type: Grant
    Filed: November 4, 1998
    Date of Patent: July 11, 2000
    Assignee: Asahi Glass Company Ltd.
    Inventors: Masako Tada, Kaoru Oguro, Josho Kashiwame
  • Patent number: 6087439
    Abstract: The invention relates to aqueous crosslinking polymer dispersions which are characterized in that they consist ofA) 98 to 80 wt. % of a 40 to 60% aqueous alkaline polymer dispersion based on 2-chlorobuta-1,3-diene, with a pH of .gtoreq.9.5 and a chloride content, arising from the elimination of chlorine atoms from the polymer, of .gtoreq.300 ppm, andB) 2 to 20 wt. % of polyisocyanates obtained by the cyclotrimerization of aliphatic and/or cycloaliphatic diisocyanates, containing NCO groups bonded predominantly or exclusively as secondary groups,and to their use for the preparation of water-based adhesives.
    Type: Grant
    Filed: January 29, 1998
    Date of Patent: July 11, 2000
    Assignee: Bayer AG
    Inventors: Otto Ganster, Jorg Buchner, Heinz-Werner Lucas
  • Patent number: 6077925
    Abstract: The present invention relates to a structural adhesive compositions comprising a polyurethane which is obtainable by reacting a polyisocyanate having a functionality in the range of from 2 to 3 and a hydrogenated polybutadiene polyol having a functionality in the range from 1.5 to 2.5 and a 1,2 vinyl content prior to hydrogenation of from 30 to 70% by weight, and wherein the NCO:OH molar ratio is in the range from more than 1.05 up to 1.6.
    Type: Grant
    Filed: August 25, 1998
    Date of Patent: June 20, 2000
    Assignee: Shell Oil Company
    Inventor: Eric-Jack Gerard
  • Patent number: 6022444
    Abstract: Isocyanate prepolymers which are useful as binders are made from a polyisocyanate mixture and a hydroxyl compound having at least about 1 hydroxyl group. The polyisocyanate mixture is made up of from about 50 to about 60% by weight of polyphenyl polymethylene polyisocyanate and from about 40 to about 50% by weight of an isomeric mixture of diphenylmethane diisocyanate (MDI). The isomeric mixture of MDI is made up of from about 4 to about 30% by weight of the 2,4'-isomer and from about 70 to about 96% by weight of the 4,4'-isomer. The binders of the present invention are advantageous in that they may be used in high moisture, low temperature conditions without a catalyst. Reduced MDI emissions are also achieved when the binders of the present invention are used to make composite materials.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: February 8, 2000
    Assignee: Bayer Corporation
    Inventors: Karl W. Haider, John W. Frink, Heber D. Layton, Peter H. Markusch, James W. Rosthauser, Bonnie L. Lawson, Michael A. Joseph
  • Patent number: 5994493
    Abstract: Reactive hotmelt adhesives based on liquid polyether polyols and/or polyester polyols and aromatic diols with at least one diisocyanate have a very low melt viscosity and high early strength. They are particularly suitable for the bonding of substrates of poor thermal conductivity, such as foams and nonwoven materials, and heat-sensitive substrates.
    Type: Grant
    Filed: December 3, 1996
    Date of Patent: November 30, 1999
    Assignee: Henkel Kommanditgeesellschaft auf Aktien
    Inventor: Michael Krebs
  • Patent number: 5932680
    Abstract: The hot-melt adhesive of the invention includesA) at least one polyurethane prepolymer ofa) at least one polyisocyanate, in particular, toluene diisocyanate and/or MDI,b) at least one polyalkylene glycol at a concentration of more than 10% by weight based on total hot-melt adhesive, in particular, polypropylene glycol,c) at least one polyester glycol, preferably of at least two polyester glycols having different glass transition temperature, andB) optional additives such asd) a resin, particularly a hydrocarbon resin, ande) a stabilizer, particularly toluenesulfonyl isocyanate.Preferably, the hot-melt adhesive has a melt viscosity ranging from 10 to 300 Pa.s at 130.degree. C. The PU pre-polymer has only one single Tg in the DSC diagram. The hot-melt adhesive is notable for its high creep resistance with similarly high initial and final strength.
    Type: Grant
    Filed: October 30, 1996
    Date of Patent: August 3, 1999
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventor: Roland Heider
  • Patent number: 5883217
    Abstract: The present invention relates to polyurethane hot melt adhesive that are hardened by the action of moisture and which contain at least one reaction product from a component that contains NCO groups and an essentially linear hydroxypolyester, hydroxypolyether, and/or hydroxypolyetherester component. In addition, the present invention relates to a procedure for manufacturing a material that is permeable to water only in vapor form, this being in the form of a fiber material, in particular in the form of a web, which is joined to a polyurethane film, in which the fiber material is coated with a polyurethane material and subsequently the polyurethane material is hardened to form a water-vapor permeable film. The present invention also relates to a material that is permeable to water only in vapor form and which is in the form of a fiber material, in particular in the form of a web, that is bonded to a polyurethane film.
    Type: Grant
    Filed: June 24, 1997
    Date of Patent: March 16, 1999
    Assignee: H. B. Fuller Company
    Inventors: Harald Werenicz, Franz Maitz, Walter Nussbaumer, Ludwig Stingl, Franz Peter-Schmitz
  • Patent number: 5874173
    Abstract: Heat-curing, solvent-free one-component adhesives which are based on polyurethanes and which do not give off elimination products, and which are derived from A) a hardener component consisting of polyaddition products containing hydroxyl and uretdione groups, B) a binder component comprising 1,2-epoxide compounds having more than one 1,2-epoxide group and one or more hydroxyl groups in the molecule, C) catalysts for polymerizing epoxide groups, optionally D) further hydroxyl-containing compounds and optionally E) auxiliaries and additives known from adhesives technology; a process for preparing these compounds and to their use as heat-curing, one-component, solvent-free, thermally stable and solvent-resistant polyurethane (PU) adhesives which do not give off elimination products.
    Type: Grant
    Filed: July 11, 1997
    Date of Patent: February 23, 1999
    Assignee: Huels Aktiengesllschaft
    Inventor: Andreas Wenning
  • Patent number: 5872182
    Abstract: A water-based sulfonated polyurethane composition and footwear manufactured using the composition as as an adhesive, coating and primer. The sulfonated polyurethane is a reaction product ofa) at least one polyisocyanate;b) at least one alkylene diol;c) at least one sulfonated polyester polyol wherein the sulfo groups thereof are present as alkali metal salts; andd) at least one dihydroxy carboxylic acid, or salt thereof. The composition may also be modified to include a dispersed polymer or copolymer of an ethylenically unsaturated monomer. Such mofified compositions may be obtained by preparing the sulfonated polyurethane in the presence of an ethylenically unsaturated monomer and subsequently subjecting the mixture to free-radical polymerization conditions.
    Type: Grant
    Filed: November 21, 1995
    Date of Patent: February 16, 1999
    Assignee: H. B. Fuller Licensing & Financing, Inc.
    Inventors: Youlu Duan, Sonja Stammler, Jillian H. Ierien, Brian L. Marty
  • Patent number: 5872203
    Abstract: A 100% solids polyurethane adhesive composition for bonding polymeric roofing materials to roof-deck substrates is provided which includes two components. The first component comprises a monomeric or polymeric diisocyanate, or a polyurethane prepolymer formed by the reaction of the monomeric or polymeric diisocyanate with a polyol. The second component comprises a polyol selected from the group consisting of a polyether or polyester polyol, an alkanolamine diol, a hydroxyl-terminated homopolymer of polybutadiene, and mixtures thereof. The first and second components are combined such that the ratio of isocyanate groups in the first component to the ratio of hydroxyl groups in the second component is from about 0.5:1 to 1.5:1.
    Type: Grant
    Filed: September 25, 1995
    Date of Patent: February 16, 1999
    Assignee: ADCO Products, Inc.
    Inventors: Wei-Jian Wen, Brian Jonathan Briddell, Kathleen Louise Lamb
  • Patent number: 5869593
    Abstract: This invention relates to a hot melt moisture cure polyurethane composition which is the reaction product of a) a polyether polyol formed from a compound selected from the group consisting of ethylene oxide, propylene oxide, 1,2-butylene oxide, 1,4-butylene oxide and mixtures thereof; b) a crystalline polyester polyol having a melting point from about 40.degree. C. to about 120.degree. C.; and c) and at least one polyfunctional isocyanate component.
    Type: Grant
    Filed: April 27, 1998
    Date of Patent: February 9, 1999
    Assignee: H. B. Fuller Licensing & Financing, Inc.
    Inventors: Marietta B. Helmeke, John M. Zimmel, Franz Maitz
  • Patent number: 5824743
    Abstract: An adhesive for solvent-free use consists of at least one polyurethane containing --OH or --NCO end groups modified by a (meth)acrylate- or vinyl- homo- or copolymer which may contain hydroxy functions, in which the polyurethane is the product of the reaction between a polyether polyol or dialcohol and/or a polyester polyol with an isocyanate monomer containing 1 to 4 --NCO groups and/or a polyisocyanate and/or a polyurethane prepolymer containing NCO end groups or --OH end groups.
    Type: Grant
    Filed: May 14, 1996
    Date of Patent: October 20, 1998
    Assignee: Morton International, GmbH
    Inventors: Gerhard Krawczyk, Volker Dreja
  • Patent number: 5719252
    Abstract: This invention relates to a low-viscosity two-component unfilled polyurethane adhesive having a urethane content of from 10 to 18 percent by weight, based on the weight of nonfilled polyurethane polymer, based on(a) a low-viscosity isocyanate component comprising an organic polyisocyanate in a quantity sufficient to provide an isocyanate index of about 100 to about 150; and(b) a low-viscosity phase-stable curative component comprising(i) 5 to 50 equivalent percent of a polyether polyol and/or a polyether terminated by aromatic amino groups having an equivalent weight greater than 500,(ii) 30 to 95 equivalent percent of 2-methyl-1,3-propanediol, and(iii) 0 to 35 equivalent percent of a chain extender and/or crosslinker other than 2-methyl-1,3-propanediol, with the proviso that the equivalent ratio of component (b)(iii) to component (b)(ii) is no more than about 0.6.
    Type: Grant
    Filed: December 18, 1996
    Date of Patent: February 17, 1998
    Assignee: Bayer Corporation
    Inventors: Jeffrey F. Dormish, Douglas Vanboxmeer
  • Patent number: 5717030
    Abstract: A medical device which is a surgically implantable device coated with an adjunctive polymer system. The adjunctive polymer system forms a solid matrix when introduced into a human or animal body. The adjunctive polymer system can contain a drug or a medicament which is released over time from the solid matrix. The adjunctive polymer system contacts body tissue into which the surgically implantable device is implanted.
    Type: Grant
    Filed: December 6, 1996
    Date of Patent: February 10, 1998
    Assignee: Atrix Laboratories, Inc.
    Inventors: Richard L. Dunn, Gerald L. Yewey, Jeffrey L. Southard, John E. Urheim
  • Patent number: 5717005
    Abstract: Chlorhexidine gluconate-containing adhesives have dispersed therein solid chlorhexidiene particles which will pass through a 125 .mu.m sieve and at least about 30% of the total volume of particles has a size of not less than 5 .mu.m. The adhesive may be a vinyl ether adhesive and may be coated upon a backing layer such as a hydrophilic polyurethane to produce products suitable for use as wound dressings, IV dressing or incise drapes. The chlorhexidine gluconate may be obtained as a freeze-dried solid and added directly, in suspension, to the adhesive mass without further milling.
    Type: Grant
    Filed: December 20, 1993
    Date of Patent: February 10, 1998
    Assignee: Smith & Nephew PLC
    Inventor: Mark Christopher Richardson
  • Patent number: 5707647
    Abstract: A medical device which is a surgically implantable device coated with an adjunctive polymer system. The adjunctive polymer system forms a solid matrix when introduced into a human or animal body. The adjunctive polymer system can contain a drug or a medicament which is released over time from the solid matrix. The adjunctive polymer system contacts body tissue into which the surgically implantable device is implanted.
    Type: Grant
    Filed: November 14, 1996
    Date of Patent: January 13, 1998
    Assignee: Atrix Laboratories, Inc.
    Inventors: Richard L. Dunn, Gerald L. Yewey, Jeffrey L. Southard, John E. Urheim
  • Patent number: 5705547
    Abstract: A one-part, moisture-cure urethane adhesive composition contains between 1 and 10 phr .gamma.-butyrolactone which acts as a moisture diffusion agent, thereby promoting a more rapid cure.
    Type: Grant
    Filed: October 15, 1996
    Date of Patent: January 6, 1998
    Assignee: Morton International, Inc.
    Inventors: James L. Richards, Larry F. Brinkman
  • Patent number: 5698656
    Abstract: A moisture-curing urethane adhesive composition of a urethane prepolymer resulting from the reaction of a mixture of a polyether diol and a polyether triol with a diisocyanate compound, and a polyurethane compound resulting from the reaction of a mixture of a polyester polyol and a polypropyleneether polyol with a hexamethylene diisocyanate compound with addition of a monoalcohol. A modified moisture-curing urethane adhesive composition of a urethane prepolymer resulting from the reaction of a mixture of a polyether diol and a polyether triol with a diisocyanate compound, a first polyurethane compound resulting from the reaction of a copolymeric polyol consisting of propylene oxide and .epsilon.-caprolactone with a hexamethylene diisocyanate compound with addition of a monoalcohol, and a second polyurethane compound resulting from the reaction of a polyester polyol with a hexamethylene diisocyanate compound with addition of a monoalcohol.
    Type: Grant
    Filed: November 7, 1995
    Date of Patent: December 16, 1997
    Assignee: The Yokohama Rubber Co., Ltd.
    Inventors: Yoshinobu Ohashi, Hideyuki Matsuda, Eiji Nishi, Tsuyoshi Nishida
  • Patent number: 5656688
    Abstract: A compound of the formula ##STR1## where A is an n-valent organic radical and n is an integer greater than 1.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: August 12, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Bauer, Karl Haeberle, Roland Baumstark, Kaspar Bott
  • Patent number: 5656712
    Abstract: A two-component polyurethane sealant composition comprising a diisocyanate-based prepolymer as a first component and a polyol composition as a second component reactable with said first component, when said two components are admixed, to form a thermoset curable polyurethane, said polyol composition comprising a polyol capable of reacting with said diisocyanate-based prepolymer to form a polyurethane a catalyst, comprising a mixture of cobalt and vanadium alkanoates and a ketimine, and the method of making an architectural seal utilizing the same.
    Type: Grant
    Filed: May 2, 1995
    Date of Patent: August 12, 1997
    Inventor: Thomas C. Mirossay
  • Patent number: 5652300
    Abstract: A self-emulsifiable polyisocyanate mixture which is of a non-yellowing type, is not deteriorated in weather resistance, has a high hardness and is quick-drying and which is obtained from a specific, NCO-terminated modified HDI and has introduced thereinto a specific, NCO-terminated modified IPDI or a specific, NCO-terminated modified TDI, and an aqueous coating or adhesive composition comprising the above self-emulsifiable polyisocyanate mixture.
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: July 29, 1997
    Assignee: Nippon Polyurethane Industry Co., Ltd.
    Inventors: Yukihiro Morikawa, Shin Konishi, Kouichi Uehara
  • Patent number: 5637639
    Abstract: A process for preparing poly(urethane/urea) prepolymers and aqueous poly(urethane/urea) dispersions (PUDs) therefrom, the poly(urethane/urea) polymers having high heat resistance and good water resistance. The method employs a water soluble volatile organic solvent, such as acetone, at a level of 0.1-5%, based on final dispersion weight, a level which does not require removal for purposes of flash point considerations.
    Type: Grant
    Filed: September 15, 1995
    Date of Patent: June 10, 1997
    Assignee: H.B. Fuller Licensing and Financing, Inc.
    Inventors: Youlu Duan, Sonja Stammler
  • Patent number: 5631341
    Abstract: A self-emulsifiable polyisocyanate mixture having a hexamethylene diisocyanate monomer content of not more than 1.0% by weight and an average NCO functionality of 2.0 to 3.7 obtained by subjecting hexamethylene diisocyanate to urethanation with a branched dihydric alcohol having overall 4 to 35 carbon atoms, of which 2 to 33 carbon atoms are a total number of the carbon atoms possessed by one or more branches, a hydrophilic surfactant having one or more active hydrogen atoms capable of reacting with NCO group and 3 to 90 alkylene oxide units, an aliphatic compound having one or more active hydrogen atoms capable of reacting with NCO group and 8 or more carbon atoms and an unbranched glycol having 1 to 10 carbon atoms; uretdione-forming reaction; and isocyanurate-forming reaction.
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: May 20, 1997
    Assignee: Nippon Polyurethane Industry Co., Ltd.
    Inventors: Takeshi Morishima, Shin Konishi, Shinjiro Hama
  • Patent number: 5618904
    Abstract: Described herein is a one-part hot melt adhesive comprising the reaction product of: (a) a polyester polyol with an equivalent weight in the range of from about 250 to about 3,000; (b) a polyisocyanate; and (c) at least about 1 weight percent hydroquinone bis (2-hydroxyethyl) ether; wherein the isocyanate content of the resulting product is at least about 0.5 percent. Also described is a one-part hot melt adhesive comprising the reaction product of: (a) a polyether polyol; (b) a polyisocyanate; and (c) hydroquinone bis (2-hydroxyethyl) ether; wherein the isocyanate content of the resulting product is at least about 0.5 percent. It has been discovered that the compositions of the invention provide adhesives with increased resistance to softening at high temperatures (e.g., above about 70.degree. C.) after curing.
    Type: Grant
    Filed: December 29, 1993
    Date of Patent: April 8, 1997
    Assignee: Essex Specialty Products Inc.
    Inventors: Brian Martin, Julie A. Muehlfeld
  • Patent number: 5610232
    Abstract: Aqueous dispersion adhesives of anionic polyurethanes which have high heat resistance and low activation temperature, even when employed without addition of a crosslinker. The polyurethane is the reaction product of an isocyanate terminated polyurethane prepolymer, and water. The polyurethane prepolymer is the reaction product of a polyol component and a diisocyanate component, the polyol component including:a sulfonated polyester polyol,a hydroxy carboxylic acid of the formula:(HO).sub.x R(COOH).sub.ywherein (R) represents a straight or branched, hydrocarbon radical containing 1 to 12 carbon atoms, and x and y represent values from 1 to 3, and optionally,a low molecular weight aliphatic diol having a molecular weight of from 60 to 400a non-sulfonated polyol,and the diisocyanate component being selected from the group consisting of aromatic diisocyanates, isopherone diisocyanate, hexamethylene diisocyanate and mixtures thereof.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 11, 1997
    Assignee: H.B. Fuller Licensing & Financing, Inc.
    Inventors: Youlu Duan, Sonja Stammler, Scott Rhein, Lowell Lindquist
  • Patent number: 5608028
    Abstract: An adhesive material is provided which is particularly suitable for potting a sensing element within a container. The adhesive material is characterized by mechanical and physical properties which enable the adhesive material to maintain its adhesive and structural integrity under intense thermal cycling conditions, so as to exclude foreign elements from the sensing element when potted within a container with the potting material. The adhesive material can be formulated so as to be sufficiently adherent for use with containers formed from materials such as polybutylene terephthalate, polyethylene terephthalate, and E-coated steel, by including additions of a flexibilized polyol/polyepoxide epoxy novolac in an amount of up to about 15 parts by weight.
    Type: Grant
    Filed: February 2, 1994
    Date of Patent: March 4, 1997
    Assignees: Delco Electronics Corp., Hughes Aircraft
    Inventors: Henry M. Sanftleben, Ralph D. Hermansen
  • Patent number: 5608000
    Abstract: Aqueous dispersion adhesives of anionic polyurethanes which have high heat resistance and low activation temperature, even when employed without addition of a crosslinker. The polyurethane is the reaction product of an isocyanate terminated polyurethane prepolymer, and a chain extender. The polyurethane prepolymer is the reaction product of a polyol component and a diisocyanate component, the polyol component including:a sulfonated polyester polyol,a hydroxy carboxylic acid of the formula:(HO).sub.x R(COOH).sub.ywherein (R) represents a straight or branched, hydrocarbon radical containing 1 to 12 carbon atoms, and x and y represent values from 1 to 3, anda low molecular weight aliphatic diol having a molecular weight of from 60 to 400.
    Type: Grant
    Filed: September 9, 1994
    Date of Patent: March 4, 1997
    Assignee: H. B. Fuller Licensing & Financing, Inc.
    Inventors: Youlu Duan, Sonja Stammler
  • Patent number: 5606003
    Abstract: A two-component urethane adhesive is disclosed which requires no primer or pretreatment of the substrate. The adhesive in cured form has superior paint adhesion and can withstand high temperature bake cycles without substantial losses in adhesion to the substrate. The adhesive differs from prior adhesives in that essentially all of the high molecular weight polyols in the prepolymer component are the reaction product grafting reactions of acrylonitrile onto polypropylene polyols.
    Type: Grant
    Filed: September 1, 1994
    Date of Patent: February 25, 1997
    Assignee: GenCorp Inc.
    Inventors: Chia L. Wang, Arden E. Schmucker, Fred V. Sandels, Richard H. Harshbarger, Robert L. Spencer
  • Patent number: 5599895
    Abstract: The hot-melt adhesive of the invention includesA) at least one polyurethane prepolymer ofa) at least one polyisocyanate, in particular, toluene diisocyanate and/or MDI,b) at least one polyalkylene glycol at a concentration of more than 10% by weight based on total hot-melt adhesive, in particular, polypropylene glycol,c) at least one polyester glycol, preferably of at least two polyester glycols having different glass transition temperature, andB) optional additives such asd) a resin, particularly a hydrocarbon resin, ande) a stabilizer, particularly toluenesulfonyl isocyanate.Preferably, the hot-melt adhesive has a melt viscosity ranging from 10 to 300 Pa.s at 130.degree. C. The PU prepolymer has only one single Tg in the DSC diagram. The hot-melt adhesive is notable for its high creep resistance with similarly high initial and final strength.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: February 4, 1997
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventor: Roland Heider
  • Patent number: 5591820
    Abstract: Pressure-sensitive adhesives which possess absorptivity and/or permeability properties to remove transepidermal water loss and/or other bodily fluids that come into contact with the adhesive, in combination with a fine balance of cohesion and adhesion properties, can be formulated by controlling the crosslinking of a polyurethane polymer having excess hydroxyl functionality, a glass transition temperature of less than about 0.degree. C., a moisture absorption of at least about 20% of its weight and/or a moisture vapor transmission rate of at least about 300 grams/meter.sup.2 /24 hours measured at 37.degree. C. and a 90% relative humidity gradient. Adhesives of these polymers possess a peel adhesion to human skin of between about 0.3 and 4 newtons/cm width of the polymer or adhesive.
    Type: Grant
    Filed: May 9, 1995
    Date of Patent: January 7, 1997
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Agis Kydonieus, Ladislav Bastar, Kishore Shah, Khosrow Jamshidi, Tak-lung Chang, Sheng-hung Kuo
  • Patent number: 5569733
    Abstract: A composition which is the reaction product of (i) a material having the structure ##STR1## where R.sub.1 is an organic radical having 6 to 25 carbon atoms; R.sub.2 is alkylene having 1 to 4 carbon atoms; R.sub.3 and R.sub.4 are independently alkyl having 1 to 4 carbon atoms and n is 2-4 and (ii) an acidic hydrogen-containing compound. The compositions are useful as catalyst in induction curable adhesive compositions.
    Type: Grant
    Filed: March 31, 1994
    Date of Patent: October 29, 1996
    Assignee: PPG Industries, Inc.
    Inventors: Karen D. Donnelly, Joseph M. Makhlouf
  • Patent number: 5548056
    Abstract: This invention is a method of making a laminated untreated fiberglass reinforced polyester substrates and a cured polyureaurethane adhesive composition. The prepolymer component of the adhesive is the reaction product of a slowly reacting polyisocyanate and a polyol.
    Type: Grant
    Filed: October 31, 1994
    Date of Patent: August 20, 1996
    Assignee: Ashland Inc.
    Inventor: Daniel A. Chung
  • Patent number: 5508371
    Abstract: The present invention relates to polyurethane fusion adhesives that are hardened by the action of moisture and which contain at least one reaction product from a component that contains NCO groups and an essentially linear hydroxypolyester, hydroxypolyether, and/or hydroxypolyetherester component. In addition, the present invention relates to a procedure for manufacturing a material that is permeable to water only in vapor form, this being in the form of a fiber material, in particular in the form of a web, which is joined to a polyurethane film, in which the fiber material is coated with a polyurethane material and subsequently the polyurethane material is hardened to form a water-vapor permeable film. The present invention also relates to a material that is permeable to water only in vapor form and which is in the form of a fiber material, in particular in the form of a web, that is bonded to a polyurethane film.
    Type: Grant
    Filed: June 30, 1992
    Date of Patent: April 16, 1996
    Assignee: H. B. Fuller Licensing & Financing, Inc.
    Inventors: Harald Werenicz, Franz Maitz, Walter Nussbaumer, Ludwig Stingl, Franz P. Schmitz
  • Patent number: 5502149
    Abstract: The present invention provides a curing agent comprising a polyisocyanate compound obtained from hexamethylene diisocyanate and containing not more than 0.5% by weight of hexamethylene diisocyanate monomer, 21 to 60% weight of uretidine dione dimer and 11 to 40% by weight of isocyanurate cyclic trimer, the uretidine dione dimer and the isocyanurate cyclic trimer being prepared from a product obtained by urethane modification of 0.5 to 15 mole % by mole of total isocyanate groups of the hexamethylene diisocyanate by a dihydric alcohol having at least two hydroxyl groups and a branched hydrocarbon group having 4 to 35 carbon atoms in the molecule, which the side chain hydrocarbon groups in the branched hydrocarbon group have 2 to 33 carbon atoms in total. The curing agent has a low viscosity and a good compatibility with a solvent, and can provides a polyurethane paint or adhesive composition having good curing property, drying property, adhesion strength and weathering resistance.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: March 26, 1996
    Assignee: Nippon Polyurethane Industry Co., Ltd.
    Inventors: Mitsuhiro Yoshida, Susumu Sato, Hisashi Nanno
  • Patent number: 5486547
    Abstract: A sheet material, coated with a surgical adhesive comprising an NCO-terminated urethane prepolymer, is used for bonding of tissues, with improved handleability.Surgical instruments, comprising a non-adherent material towards an NCO-terminated urethane prepolymer, are used for application of surgical adhesive. Such instruments, comprising a rod tapered so that the tip can be partly inserted into blood vessel, are suitable for anastomosis of blood vessel.
    Type: Grant
    Filed: November 3, 1994
    Date of Patent: January 23, 1996
    Assignee: Sanyo Chemical Industries, Ltd.
    Inventors: Takehisa Matsuda, Tetsuo Itoh, Tohru Tani
  • Patent number: 5468831
    Abstract: A one-package primerless structural adhesive is disclosed that is particularly well suited for adhering one or more substrates of fiber-reinforced plastics. This adhesive uses dicyandiamide, its substituted derivatives, or melamine as the principal curative. A polyisocyanate prepolymer is made from various polyols reacted with polyisocyanates. In the absence of moisture, the curative and polyisocyanate can coexist in a single package without reacting for periods of time in excess of four months. Upon heating the adhesive to 150.degree. C., it cures in about five minutes or less, forming an initial structural bond that after heat aging is often stronger than the cohesive strength of the fiber reinforced substrate.
    Type: Grant
    Filed: December 21, 1993
    Date of Patent: November 21, 1995
    Assignee: GenCorp Inc.
    Inventors: Gerd M. Lenke, H. William Cocain
  • Patent number: 5457141
    Abstract: A sheet material, coated with a surgical adhesive comprising an NCO-terminated urethane prepolymer, is used for bonding of tissues, with improved handleability.Surgical instruments, comprising a non-adherent material towards an NCO-terminated urethane prepolymer, are used for application of surgical adhesive. Such instruments, comprising a rod tapered so that the tip can be partly inserted into blood vessel, are suitable for anastomosis of blood vessel.
    Type: Grant
    Filed: September 28, 1993
    Date of Patent: October 10, 1995
    Assignee: Sanyo Chemical Industries, Ltd.
    Inventors: Takehisa Matsuda, Tetsuo Itoh, Tohru Tani
  • Patent number: 5410011
    Abstract: A one-component type polyurethane adhesive: comprising, as a main component, a polyurethane precursor prepared by reaction of a polyisocyanate component (a) containing one or more polyisocyanate compounds (a-1) mention below and optionally one or more polyisocyanates (a-2) mention below with an active hydrogen compound (b) having a molecular weight of from 18 to 20,000 and having two or more active hydrogen groups in the molecule, at an equivalent ratio of the active hydrogen group of the active hydrogen compound component (b) to the isocyanate group of the polyisocyanate component (a) of more than 1.0; the polyurethane precursor containing a uretdione group and the active hydrogen group at an equivalent ratio of the uretdione group to the active hydrogen groups of from 0.25 to 1.0,(a-1): a polyisocyanate compound having at least a uretdione group in the molecule thereof, and(a-2): a polyisocyanate having two or more isocyanate groups in the molecule thereof.
    Type: Grant
    Filed: August 19, 1993
    Date of Patent: April 25, 1995
    Assignees: Inoac Corp., Nippon Polyurethane Industry Co., Ltd.
    Inventors: Shin Konishi, Shinji Hirayama, Takao Hidai, Yukihiro Morikawa, Koichi Uehara, Sadako Hashimoto
  • Patent number: 5410010
    Abstract: A class of cross-linked fluorinated polyurethanes, which can be used for protecting and reinforcing coatings on films, sheets, laminates and similar thin structures made of cellulose, graphite, mica, kaolin, leather etc. as well as for adhesive and reinforcing material in multi-layer structures made of films, sheets, laminates and similar thin structures made of graphite, mica, kaolin, etc. These polyurethanes can be obtained starting from the following components:(A) a polyisocyanate consisting of a perfluoropolyether chain bound to the --NCO terminal groups through an aromatic or cycloaliphatic radical; and(B) a polyol consisting of a perfluoropolyether chain bound to the --OH terminal groups through an aromatic or cycloaliphatic radical.
    Type: Grant
    Filed: July 29, 1992
    Date of Patent: April 25, 1995
    Assignee: Ausimont S.p.A.
    Inventors: Claudio Tonelli, Giovanni Simeone
  • Patent number: 5382647
    Abstract: A polyurethane friable sealing compound free of solvent and plasticizer having a shore A hardness of below 40 and consisting essentially of a polyol component and an isocyanate component. The polyol component is selected from modified triglycerides obtained by partial ring opening of epoxidized triglycerides of a fatty acid mixture containing olefinically unsaturated fatty acids and monohydric or polyhydric alcohols. The isocyanate component is selected from polyfunctional aromatic and aliphatic isocyanates, wherein the OH:NCO equivalent ratio is from 1:0.1 to 1:1.15.
    Type: Grant
    Filed: April 16, 1993
    Date of Patent: January 17, 1995
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Peter Daute, Roland Gruetzmacher, Rainer Hoefer, Gerhard Stoll
  • Patent number: RE37386
    Abstract: A two component type polyurethane adhesive is provided for fiberglass reinforced plastics which requires no cleaning, preparation or treatment of the surface, and the like. The curative component is a nitrogen-free liquid polyether or polyester in an amount such that in association with a urethane prepolymer component containing free NCO groups, the ratio of the free NCO groups in the prepolymer component to the OH groups in said curative component is at least 1.2 and desirably at least 1.35. Such high NCO/OH ratios have unexpectedly been found to provide good adhesion and especially good humidity adhesion and peel strength adhesion to fiberglass reinforced plastics or metal surfaces which are free from any surface treatment.
    Type: Grant
    Filed: January 8, 1993
    Date of Patent: September 18, 2001
    Inventors: Earl G. Melby, H. William Cocain