Reactant Contains At Least One Salt Group, E.g., Quaternary Ammonium Salt, Etc. Patents (Class 528/71)
  • Patent number: 5071578
    Abstract: The present invention concerns magnetic recording media comprising fine, magnetizable pigment or particles dispersed within a binder and supported on a substrate. The invention particularly concerns the nature of the binder polymer and its preparation. The binder polymer is a curable polymer comprising a sulfonated, hydroxy-functional polyurethane polymer. A plurality of SO.sub.3 M groups are pendant from the polyurethane polymer backbone. The SO.sub.3 M groups have an equivalent weight of from about 2,000 to about 100,000. M is selected from the group consisting of H.sup.+, Li.sup.+, Na.sup.+, K.sup.+, NR.sub.4.sup.+ where R can be H.sup.+ or an alkyl group, and mixtures thereof. A plurality of hydrophobic polymer chain segments are incorporated into the polyurethane polymer that comprise residues of a polyol having a molecular weight of at least about 180. The hydrophobic chain segments have a carbon atom to polar functionality of at least about 60.
    Type: Grant
    Filed: October 31, 1989
    Date of Patent: December 10, 1991
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Takatoshi Ohkubo, James G. Carlson
  • Patent number: 5069807
    Abstract: The present invention concerns magnetic concerns magnetic recording media comprising fine, magnetizable pigment or particles dispersed in a binder and supported on a substrate. The invention particularly concerns the nature of the binder. The binder comprises a sulfonated, hydroxy-functional polyurethane polymer having sulfonate and cross-linkable hydroxyl groups pendant from the polyurethane polymer backbone. The hydroxyl groups are pendant from the polyurethane polymer at locally hydrophobic sites. The binder also comprises a sulfonated, hydroxy-functional vinyl chloride copolymer having sulfonate and cross-linkable hydroxyl groups pendant from the vinyl chloride copolymer backbone.
    Type: Grant
    Filed: November 16, 1989
    Date of Patent: December 3, 1991
    Assignee: Minnesota Mining and Manufacturing Co.
    Inventor: Takatoshi Ohkubo
  • Patent number: 5053464
    Abstract: A polyurethane containing a metal phthalocyanine in the main chain is a novel compound and can be divided into two groups; one of which is a linear polymer and the other of which is a cross-linked polymer. This substance is useful as a redox catalyst due to the peculiar properties of the metal phthalocyanine. The polyurethane can be prepared by reacting a metal phthalocyanine polycarboxylic acid with thionyl chloride to obtain a metal phthalocyanine polycarboxylic acid polychloride; synthesizing a metal phthalocyanine polyhydroxy ester from the metal phthalocyanine polycarboxylic acid polychloride and a diol: HO--R.sup.1 --OH through a dehydrochlorination; and then addition-condensation-polymerizing the resulting metal phthalocyanine polyhydroxy ester, a diol: HO--R.sup.2 --OH and a diisocyanate.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: October 1, 1991
    Assignee: Hirofusa Shirai & Nisshinbo Industries, Inc.
    Inventors: Hirofusa Shirai, Naomi Masuda, Tatsuya Hongu, Nobuhisa Tsutsumi
  • Patent number: 5045622
    Abstract: A polycarbonate polyol having a main chain of the formula: ##STR1## wherein R is an aliphatic or alicyclic hydrcarbon group having 4 to 10 carbon atoms, and n is a number of 2.00 to 20.
    Type: Grant
    Filed: June 20, 1989
    Date of Patent: September 3, 1991
    Assignee: Hitachi Maxell, Ltd.
    Inventors: Kenji Kohno, Yoshiyuki Nagataki, Kazushi Miyata, Hiroshi Higashi
  • Patent number: 5039732
    Abstract: Air-drying, water-reducible, acid-functional polyurethanes are obtained by reacting:(i) a fatty amide diol obtained by the reaction of a fatty acid or fatty acid derivative and an N,N-dialkanol amine; and(ii) a diisocyanate; and(iii) an acid-functional compound which also has two active hydrogen groups, other than acid groups, which are reactive with the dissocyanate.
    Type: Grant
    Filed: December 30, 1988
    Date of Patent: August 13, 1991
    Assignee: The Sherwin-Williams Company
    Inventor: Kartar S. Arora
  • Patent number: 5017664
    Abstract: Modified-polyurethane block copolymers and devices formed therefrom demonstrate excellent biocompatibilty and improved physical and mechanical properties. In a preferred embodiment, from about 5 to about 25 percent of urethane hydrogen atoms are replaced with propyl sulfonate and propyl carboxylate groups to provide the modified copolymer.
    Type: Grant
    Filed: April 5, 1989
    Date of Patent: May 21, 1991
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Timothy G. Grasel, Stuart L. Cooper
  • Patent number: 5011885
    Abstract: The present invention is directed to a method for preparing microcapsules which comprises:preparing an aqueous dispersion or emulsion of a hydrophobic oily core material containing a polyvalent isocyanate, a polyvalent isothiocyanate, or an adduct thereof, having an anionic moiety; andforming capsule walls around the droplets of said oily core material.
    Type: Grant
    Filed: October 27, 1989
    Date of Patent: April 30, 1991
    Assignee: The Mead Corporation
    Inventors: Jing-Den Chen, Kerry Kovacs, Margaret T. Thomas, Rong-Chang Liang
  • Patent number: 4978732
    Abstract: Coated supports with ultra-thin, single-layer or multi-layer coating of organic polymer material have been found, in which, as polymer, polyurethanes of the structure ##STR1## are used in which A is the skeleton of an aliphatic, araliphatic or aromatic diol,B is the skeleton of an aliphatic, araliphatic or aromatic diisocyanate,n assumes values from 2 to 150 andat least one of the substituents R.sup.1 to R.sup.4 represents an essentially normal-chain aliphatic radical and the others in each case denote hydrogen, the aliphatic radical having at least 4 carbon atoms and the number of carbon atoms from the terminal methyl group of the aliphatic radical via the skeleton A or B up to the urethane linkage being 6 to 40, and it being further possible for R.sup.1 and R.sup.2 jointly to form an alkylene chain and for R.sup.3 and R.sup.4 jointly to form an alkylene chain. Coated supports of this type may be produced by the Langmuir-Blodgett technique.
    Type: Grant
    Filed: August 1, 1989
    Date of Patent: December 18, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf Wehrmann, Heinrich-Christian Schopper, Dittmar K. Nerger
  • Patent number: 4880883
    Abstract: Modified-polyurethane block copolymers and devices formed therefrom demonstrate excellent biocompatibility and improved physical and mechanical properties. In a preferred embodiment, from about 5 to about 25 percent of urethane hydrogen atoms are replaced with propyl sulfonate and propyl carboxylate groups to provide the modified copolymer.
    Type: Grant
    Filed: June 3, 1987
    Date of Patent: November 14, 1989
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Timothy G. Grasel, Stuart L. Cooper
  • Patent number: 4845181
    Abstract: An organic condensation polymer made by reacting in solution of first compound having at least two anionic carbon sites bonded to each other either directly or through a chain of 1 to 30 carbon atoms, including a bisacetylide or a first compound having an anionic carbon site and a latent anionic carbon site bonded to each other either directly or through a chain of 1 to 30 carbon atoms, such as organometallic cyclopentadienides, with a second compound containing at least two electrophillic carbon sites bonded to each other either directly or through a chain of 1 to 30 carbon atoms, including diesters, dihalides, diamides or dianhydrides of polycarboxylic acids, and diisocyanates.
    Type: Grant
    Filed: September 26, 1988
    Date of Patent: July 4, 1989
    Assignee: President and Fellows of Harvard College
    Inventors: Lawrence B. Kool, George M. Whitesides
  • Patent number: 4831098
    Abstract: An antistatic agent containing a cationic and/or amphoteric, water-soluble or water-dispersible and heat-reactive blocked urethane prepolymer as an essential component, said prepolymer having at least one cationic group and/or at least one amphoteric group in its molecule and having isocyanate groups blocked with a thermally dissociable blocking agent. The antistatic agent is applicable to various materials and can give the antistatic property with the water repellency, which can be kept for a long term, to the materials.
    Type: Grant
    Filed: June 10, 1987
    Date of Patent: May 16, 1989
    Assignee: Dai-ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Akio Watanabe, Toshiaki Doyama
  • Patent number: 4786330
    Abstract: A sizing agent for paper consisting essentially of a latex consisting essentially of at least one diurethane dispersed in an aqueous medium, said diurethane being of the formula: ##STR1## in which: (a) R.sub.1, R.sub.2, R.sub.5 and R.sub.6 are each alkyl radicals and at least one of them possesses a minimum of 7 carbon atoms;(b) R.sub.7 and x represent, respectively, the cationic and anionic portions of the quaternizing agent R.sub.7 x;(c) R.sub.3 and R.sub.4 are selected from C.sub.2 -C.sub.4 alkylene radicals or polyalkoxylated radicals of a degree of polycondensation of between 1 an 4; and(d) Y is ##STR2## The process of making the sizing agent and using it to size paper are also disclosed.
    Type: Grant
    Filed: January 16, 1987
    Date of Patent: November 22, 1988
    Assignee: Atochem
    Inventors: Catherine Beuzelin, Claude Senez
  • Patent number: 4764553
    Abstract: The present invention is directed to water dispersible or soluble polyurethanes containing about 0.5 to 30% by weight, based on the weight of the polyurethanes, of ethylene oxide units present in lateral or terminal polyether chains, characterized in that in addition to these ethylene oxide units the polyurethanes contain, as further hydrophilic centers, about 0.1 to 120 milliequivalents, per 100 g of solids content, of carboxylate groups in the form of built-in structural units corresponding to the general formula ##STR1## wherein R denotes an alkyl group having 1 to 4 carbon atoms and the total quantity of carboxylate groups and ethylene oxide units present in lateral or terminal chains is calculated to ensure the solubility or dispersibility of the polyurethanes in water.The present invention also relates to a process for the preparation of these polyurethanes and to their use for coating substrates.
    Type: Grant
    Filed: December 1, 1987
    Date of Patent: August 16, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Mosbach, Josef Pedain, Klaus Noll
  • Patent number: 4746717
    Abstract: An isocyanate-terminated sulfocompound is the reaction product of a polyisocyanate and a sulfopolyol or sulfopolyamine which is the reaction product of one mole of a sulfodicarboxylic acid and about two moles of an aliphatic polyol or polyamine having two or more hydroxyl or amino groups attached to a linear chain and having a molecular weight of up to 2000. The sulfocompound can be reacted with ethylenically-unsaturated alcohols, water, polyamines, or polyols, to give ethylenically-unsaturated sulfocompounds, sulfopolyureas or sulfopolyurethanes.
    Type: Grant
    Filed: January 22, 1987
    Date of Patent: May 24, 1988
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Wayne K. Larson
  • Patent number: 4745152
    Abstract: A transparent coating for windows or other transparent substrates made of glass or synthetic resin, consisting of a flexible elastic polyurethane, serves as a shatterproofing coating for substrates made of silicate glass or as a coating improving the scratch resistance of substrates made of synthetic resin. To reduce or prevent the formation of a deposit of moisture on the surface of the coating, the polyol component of the reaction mixture for preparing a coating pursuant to the invention consists of a difunctional sulfonated polyether polyol containing approximately 1 to 10% of OH groups by weight and a trifunctional polyol containing approximately 8 to 12% of OH groups by weight and having an average molecular weight of approximately 400 to approximately 1000 g/mole.
    Type: Grant
    Filed: February 20, 1987
    Date of Patent: May 17, 1988
    Assignee: Saint-Gobain Vitrage
    Inventors: Juergen Fock, Gunter Hahn, Gerhard Holzer, Helmer Radisch
  • Patent number: 4743673
    Abstract: Hydrophilic polyurethane polymers having carboxy groups in the polymer backbone are prepared by reacting a polyol component, an ester of a carboxylic acid and a polyisocyanate to form a polyurethane intermediate. The intermediate is then saponified and the saponified product neutralized to form free carboxy groups. The water absorption of the intermediates and saponified polymers is above 10% and the polyurethanes may range from rigid solids to gel-like, high water absorptive polymers. Neutralization of the carboxy group with ammonium hydroxide produces a water soluble polyurethane which becomes water insoluble when the ammonia is driven off. The carboxy groups introduced into the polymeric chain provide reactive sites for attachment of various side-groups and also allow for various curing procedures.
    Type: Grant
    Filed: December 19, 1986
    Date of Patent: May 10, 1988
    Assignee: Tyndale Plains-Hunter, Ltd.
    Inventors: Christian W. Johnston, John M. Teffenhart
  • Patent number: 4742100
    Abstract: Salts generally act as reinforcing compounds in polyurethane compositions. Salts containing a free-amine function generally increase the low-strain moduli more than salts which lack such free-amine functions or are neutral. The salts are generally formed by reacting a basic nitrogen function compound such as a monoamine or a diamine with a mono or a dicarboxylic acid.
    Type: Grant
    Filed: March 16, 1987
    Date of Patent: May 3, 1988
    Assignee: The Firestone Tire & Rubber Company
    Inventors: Edward L. Kay, Kenneth B. Roskos
  • Patent number: 4734480
    Abstract: A radiation curable resin which is a polyurethane acrylate having (meth)acryloyloxy groups at the terminal end of the molecule and in the molecular chain thereof, and containing metal sulfonate groups in the molecule in a ratio of 3.0 to 1,500 equivalent/10.sup.6 g of the resin, said polyurethane acrylate being obtained by reaction of(1) a copolyester having hydroxyl groups at both terminal ends of the molecule and containing metal sulfonate groups therein,(2) a diisocyanate,(3) a compound (A) having at least one (meth)acryloyloxy group and two hydroxyl groups,(4) a compound (B) having at least one (meth)acryloyloxy group and one hydroxyl group, and optionally(5) a polyol other than the above (1) or (3). the radiation curable resin containing a compound (C) having at least one carboxylic acid group and two hydroxyl groups in addition to the above components (1) to (5) is also disclosed.
    Type: Grant
    Filed: June 11, 1987
    Date of Patent: March 29, 1988
    Assignees: Toyo Boseki Kabushiki Kaisha, Sony Corporation
    Inventors: Nobukazu Kotera, Yasuo Yoshinaka, Shinpei Yamamoto, Hideyuki Ohashi, Yoshinobu Ninomiya, Kiyokazu Oiyama
  • Patent number: 4729925
    Abstract: Herein are disclosed polyurethane elastomers comprising a charge-control agent of the formula: ##STR1## The elastomers are useful in making shaped articles.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: March 8, 1988
    Assignee: Eastman Kodak Company
    Inventors: Tsang J. Chen, Donald A. Upson, Paul D. Yacobucci
  • Patent number: 4722966
    Abstract: A storage-stabile, radiation-hardenable, NCO-free aqueous emulsions based on ionic urethane-urea acrylates is disclosed. The emulsions are made up of partially acrylated cycloaliphatic polyisocyanates which have been acrylated by a hydroxyalkyl acrylate (to the extent of 10-60 equivalent-% NCO). These products are then reacted with polyhydroxy compounds (to the extent of 20-75 equivalent-% NCO), and then with sodium salts of aminocarboxylic acids (to the extent of 5-15 equivalent-% NCO), and finally they are reacted with water and/or aliphatic diamines (said aliphatic diamines in amounts corresponding to 1-5 equivalent-% NCO).
    Type: Grant
    Filed: July 18, 1986
    Date of Patent: February 2, 1988
    Assignee: Huls Aktiengesellschaft
    Inventor: Werner Flakus
  • Patent number: 4689386
    Abstract: A polyurethane reaction product of a di- or polyisocyanate and a diol or polyol having at least two hydroxyl groups capable of reacting with an isocyanate group and having the residue of at least one further hydroxyl group present in the form of a phosphorus acid ester group of formula (I), wherein n is 0 or 1, m is 2, 3, or 4 and each R independently is an alkyl group of 1 to 4 carbons optionally with a diol or polyol which does not contain a group of formula I is useful in biocompatible, particularly haemocompatible devices for use in methods of medical treatment.
    Type: Grant
    Filed: August 7, 1986
    Date of Patent: August 25, 1987
    Assignee: Biocompatibles Ltd.
    Inventors: Dennis Chapman, Gregorio P. Valencia
  • Patent number: 4683280
    Abstract: There is disclosed acrylate-terminated oligomers which are radiation-curable and which can be pigmented with magnetizable power to cure on electron beam exposure to provide superior magnetic recording structures. These oligomers include sulfonic acid groups which improve pigment wetting and which can be included in amide-containing compounds.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: July 28, 1987
    Assignees: DeSoto, Inc., Japan Synthetic Rubber Co., Ltd.
    Inventors: Takashi Ukachi, Keiichi Bessho, Atsushi Kumano, Yoshio Matsumura, Robert E. Ansel
  • Patent number: 4670330
    Abstract: There are provided moisture-permeable, antistatic, and oil-resistant work gloves made of film of water-insoluble, hydrophilic polyurethane resin having hydrophilic groups and/or hydrophilic segments in the main chains and/or side chains. They are produced by applying an organic solvent solution of water-insoluble, hydrophilic polyurethane resin having hydrophilic groups and/or hydrophilic segments in the main chains and/or side chains, to the surface of a glove form or the surface of a glove form on which is put a glove substrate, drying the applied solution, and stripping the deposit film from the form.
    Type: Grant
    Filed: September 4, 1985
    Date of Patent: June 2, 1987
    Assignee: Dia Rubber Company, Ltd.
    Inventor: Seihei Ishiwata
  • Patent number: 4666967
    Abstract: The invention provides polyurethanes and polyisocyanurate having incorporated therein a flame retardant amount of a salt formed by reaction between dimethyl methyl phosphonate, monomethyl methyl phosphonate or methyl phosphonic acid, and a compound of the general formula (I). ##STR1## in which X is O, S or NH, R.sup.1 is H, alkyl with 1 to 4 carbon atoms, alkenyl of up to 4 carbon atoms, CN, CONH.sub.2 or NH.sub.2, R.sup.2 is H, alkyl with 1 to 4 carbon atoms or alkenyl of up to 4 carbon atoms or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached form a heterocyclic ring of up to 6 carbon atoms which may optionally contain another hetero atom and R is H, an alkyl group with 1 to 8 carbon atoms, an aryl group with 6 to 10 carbon atoms, a cycloalkyl group with 5 to 12 carbon atoms or a heterocyclic group with up to 9 ring carbon atoms, or, together with R.sup.1 forms an alkylene chain of 3 to 10 carbon atoms, or R is a group NHR.sup.3 wherein R.sup.
    Type: Grant
    Filed: January 22, 1986
    Date of Patent: May 19, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Norman Richardson, deceased, Brian G. Clubley, Richard J. Dellar
  • Patent number: 4647647
    Abstract: Addition compounds suitable as dispersing agents, obtainable by the reaction of polyisocyanates having an average functionality of from 2.5 to 6 with monohydroxyl compounds, reaction of the resulting reaction product with compounds of the formula IIG--(E).sub.n IIwherein E stands for --OH, --NH.sub.2 and/or --NHR (wherein R represents an alkyl group with 1 to 4 carbon atoms) and n stands for 2 or 3, and G represents an aliphatic, cycloaliphatic and/or aromatic group, and further reaction of the reaction product thus obtained with compounds of the formula IIIZ--Q IIIwherein Q stands for --OH, --NH.sub.2, --NHR (wherein R stands for an alkyl group having 1 to 4 carbon atoms) or --SH, and Z denotes a group having at least one basic group containing nitrogen. The invention also relates to processes for the preparation of these addition compounds, their use, and pulverulent or fibrous solids which are coated with these dispersing agents and are to be incorporated in liquid systems.
    Type: Grant
    Filed: December 24, 1984
    Date of Patent: March 3, 1987
    Assignee: BYK-Chemie GmbH
    Inventors: Karlheinz Haubennestel, Peter Kramp
  • Patent number: 4622378
    Abstract: Water-soluble zwitterionic polymers having clay soil removal/anti-redeposition properties, which comprise a polymer backbone, at least 2 M groups and at least one L-X group, wherein M is a cationic group attached to or integral with the backbone and contains an N+ positively charged center; X is an anionic group or a mixture of anionic and nonionic groups; and L is a hydrophilic chain connecting groups M and X or connecting X to the polymer backbone. L also contains the polyoxyalkylene moiety --[(R'O).sub.m (CH.sub.2 CH.sub.2 O).sub.n ]--, wherein R' is C.sub.3 -C.sub.4 alkylene or hydroxyalkylene, m and n are numbers such that the moiety --(CH.sub.2 CH.sub.2 O).sub.n -- comprises at least about 50% by weight of said polyoxyalkylene moiety, and n is at least about 3. These zwitterionic polymers are useful in detergent compositions at from about 0.05 to about 95% by weight.
    Type: Grant
    Filed: February 15, 1985
    Date of Patent: November 11, 1986
    Assignee: The Procter & Gamble Company
    Inventor: Eugene P. Gosselink
  • Patent number: 4619985
    Abstract: The present invention is directed to a process for the production of suspensions of finely-divided polyisocyanates which are obtainable by the surface reaction with from 0.1 to 25 equivalent percent of reactive group per NCO of stabilizers in relatively high molecular weight polyols and/or relatively high molecular weight polyamines having molecular weights from 400 to 6,000 optionally with addition of lower molecular weight polyols and/or aromatic amines having molecular weights of from 60 to 399, which are characterized in that unreacted quantities of stabilizers in the suspension are subsequently partially or completely deactivated by addition of substances having an acylating and/or neutralizing and/or alkylating effect and/or adsorbing effect as "deactivators". In particular, mono- and/or polyisocyanates are used as "deactivators".
    Type: Grant
    Filed: May 8, 1985
    Date of Patent: October 28, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinrich Hess, Gerhard Grogler, Richard Kopp, James M. Barnes
  • Patent number: 4617341
    Abstract: A sizing agent for the paper industry comprising a cationic oligourethane latex; said urethane having the formula: ##STR1## in which R.sub.2 is an alkylene radical containing a C.sub.2 -C.sub.6 radical or a polyoxyalkylenic radical of a degree of polycondensation of 1 to 4,R.sub.3 is an alkyl radical containing at least 7 carbon atoms, andR.sub.4 and X represent the remainder of the quaternizing agent R.sub.4 Xwith(a) R.sub.1 representing ##STR2## R.sub.5 being an aliphatic radical containing C.sub.4 as a maximum and n varying from 1 to 3; or(b) R.sub.1 representing ##STR3## R.sub.5 being ##STR4## in which R.sub.2, R.sub.3, R.sub.4 and X having the preceding definitions and n varying from 2 to 6; and the method of making the oligourethane latex.
    Type: Grant
    Filed: May 20, 1985
    Date of Patent: October 14, 1986
    Assignee: Atochem
    Inventors: Antoine Laine, Claude Senez
  • Patent number: 4595709
    Abstract: Polyaddition products containing urethane groups are produced by reacting an isocyanate group containing distillation residue with a compound having a molecular weight less than 600 containing at least two alcoholic hydroxyl groups. The distillation residue is obtained in the commercial production of tolylene diisocyanate. The distillation residue and hydroxyl compound are reacted in amounts such that the NCO/OH equivalent ratio is less than 1.5:1. The polyaddition reaction is carried out at a temperature in the range of 50.degree. to 220.degree. C. The reaction is carried out in a reaction screw extruder preferably having self-cleaning screw geometry. The polyaddition products are useful as molding compositions, reactive fillers and starting materials in the production of flame-resistant polyurethane plastics.
    Type: Grant
    Filed: April 2, 1981
    Date of Patent: June 17, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventor: Artur Reischl
  • Patent number: 4590255
    Abstract: A process for making metal salt (ionomers) of carboxylic acid-containing mono- and polyether polyol addition products by (1) reacting maleic acid, fumaric acid, itaconic acid, or mixtures thereof with at least one polyhydroxy-containing mono- or polyether compound (e.g. a polyether diol or triol) in the presence of a peroxy-type free radical initiator to form a carboxylic acid group-containing addition product and (2) neutralizing said addition product with a sufficient amount of metal ions selected from the group consisting of metals from Groups 1a, 2a, 8, 1b and 2b of the Periodic Table to convert at least about 10% of the carboxylic acid groups to ionomeric salt groups. These ionomers may be then changed into useful polyurethane elastomers by reaction with organic polyisocyanates.
    Type: Grant
    Filed: January 30, 1984
    Date of Patent: May 20, 1986
    Assignee: Olin Corporation
    Inventors: James M. O'Connor, Richard L. Frentzel
  • Patent number: 4579930
    Abstract: The invention relates to a solvent-free hotmelt adhesive based on polyester polyurethanes which are suitable for the production of composite structures and, in particular, laminated parts for the interior finishing of motor vehicles. The hotmelt adhesive is based on polyester polyurethanes which are obtained by reacting organic polyester polyols and low molecular weight diols as chain-extending agents and which are modified by the incorporation of carboxyl and sulfonate groups. In addition to these modified polyester polyurethanes, the hotmelt adhesive may also contain unmodified polyester polyurethanes and crosslinking agents. The hotmelt adhesive is preferably in the form of a film or an in situ coating on a substrate. The hotmelt adhesive is produced by known processes of the type normally used for producing the known, unmodified polyester polyurethanes.
    Type: Grant
    Filed: March 7, 1985
    Date of Patent: April 1, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Kramer, Horst Muller-Albrecht
  • Patent number: 4569981
    Abstract: The present invention relates to water-dispersible plastics precursors which are solid at temperatures below about 40.degree. C. The plastics precursors are based on isocyanate-terminated prepolymers which have been hydrophilically modified with ionic groups and/or ethylene oxide units and which contain specified amounts of isocyanate groups and --NH-- groups.The present invention also relates to processes for preparing aqueous dispersions from the solid plastics precursors and to using the plastics precursors for cross-linking dispersed plastics containing isocyanate-reactive groups.
    Type: Grant
    Filed: July 6, 1981
    Date of Patent: February 11, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Wenzel, Dieter Dieterich
  • Patent number: 4503198
    Abstract: The electron radiation curable resin of this invention is an oligopolyester-urethane resin having urethane bonds at both terminals of a polyester moiety, or a polyester-polyurethane resin wherein polyester moieties are chain-extended through urethane bonds. The resin has a molecular weight of about 1,000 to 50,000, and has a double bond at each terminal of the molecule and contains in the molecure about 0.2 to 30 mol % of carboxylic acid component having a metal sulfonate group based on the total carboxylic acid component.This electron radiation curable resin is suitable as a binder for a magnetic paint for producing magnetic recording medium such as magnetic tape, and can provide a magnetic recording medium having excellent dispersibility, durability, and solvent resistance.
    Type: Grant
    Filed: April 18, 1983
    Date of Patent: March 5, 1985
    Assignee: Sony Corporation
    Inventors: Seiichi Miyai, Kaoru Nakajima, Masashi Somezawa
  • Patent number: 4469857
    Abstract: A two-component system for producing a flowable to plastic synthetic resin composition comprising, as the first component, a combination of a polyisocyanate and an enamine, and the second component comprising a carrier compound having water aggregated thereto.
    Type: Grant
    Filed: June 17, 1983
    Date of Patent: September 4, 1984
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Gunther John
  • Patent number: 4456744
    Abstract: Disclosed is a composition for polyurethane resins which is ordinarily of two-package type and curable at ambient temperature and which comprises an isocyanate component having oxadiazinetrione ring as a curing agent and a polyol component, having in the molecule, at least one of a tertiary amino group, a quaternary ammonium group and a salt-formed carboxyl group as a main component. The composition has excellent curability and provides cured products excellent in adhesiveness and physical properties.
    Type: Grant
    Filed: November 29, 1982
    Date of Patent: June 26, 1984
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yoshio Kamatani, Michio Tanaka, Kyuya Yamazaki, Kenichi Nishino
  • Patent number: 4451635
    Abstract: Polyurethane quaternary ammonium salts are obtained by heating a solution of a polyurethane resin characterized by having present in the polymer backbone hydroxyl groups and at least one substituent selected from the group consisting of carboxylate radicals and carboxyl radicals dissolved in a water-miscible organic solvent for the resin at a temperature above 64.degree. C. and below the decomposition temperature of said polyurethane resin with an organic chloride for a period of time; adding a strong base to the reaction mixture and continuing to heat said mixture to form a polyurethane quaternary ammonium hydroxide in solution; and precipitating the polyurethane quaternary ammonium hydroxide by pouring the reaction mixture into an excess of water.
    Type: Grant
    Filed: March 8, 1982
    Date of Patent: May 29, 1984
    Assignee: Tyndale Plains-Hunter, Ltd.
    Inventors: Francis E. Gould, Christian W. Johnston
  • Patent number: 4433017
    Abstract: A thermally reactive water-soluble urethane prepolymer having a plurality of masked isocyanate groups capable of regenerating free isocyanate groups at an elevated temperature, said urethane prepolymer having the formula: ##STR1## wherein A is an organic bridging group having a valency from 3 to 5,X is the residue of an active hydrogen compound having 2 to 4 active hydrogen atoms with removal of said active hydrogen atoms,Y is a masking group for isocyanate group,Z is the residue of a compound having at least one active hydrogen atom and at least one ionizable group with removal of said active hydrogen atom,a is an integer from 2 to 4, andb and c are such that the sum of b+c equals 2 to 4 and the products of ab and ac are at least 2 and at least 1, respectively.
    Type: Grant
    Filed: September 14, 1982
    Date of Patent: February 21, 1984
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Sumio Goto, Takeshi Doi, Kazuo Sato
  • Patent number: 4421869
    Abstract: Polyurethane foams with excellent physical properties can be obtained by using a partial salt between N,N-dimethylaminopropane-1,3-diamine (DMAPA) and phenol.
    Type: Grant
    Filed: October 21, 1982
    Date of Patent: December 20, 1983
    Assignee: Abbott Laboratories
    Inventors: Francis W. Arbir, Daniel S. Raden, Kenneth W. Narducy
  • Patent number: 4419461
    Abstract: Polyurethane foams with excellent physical properties can be obtained by using a partial salt between N,N-dimethylaminopropane-1,3-diamine (DMAPA) and a branched octanoic acid.
    Type: Grant
    Filed: October 21, 1982
    Date of Patent: December 6, 1983
    Assignee: Abbott Laboratories
    Inventors: Francis W. Arbir, Daniel S. Raden, Kenneth W. Narducy, Francois M. Casati
  • Patent number: 4408008
    Abstract: The present invention relates to a process for the preparation of stable, colloidal, aqueous dispersions of cross-linked urea-urethanes which comprises reacting(a) an aqueously dispersed, substantially linear, isocyanate-terminated prepolymer having a molecular weight of up to about 25,000 and containing(i) about 0 to 120 milliequivalents of ionic groups per 100 grams of prepolymer, and(ii) about 0.35 to 10% by weight, based on the weight of the prepolymer, of lateral and/or terminal, hydrophilic ethylene oxide units wherein components (i) and (ii) are present in an amount sufficient to provide a stable dispersion of the prepolymer in the aqueous medium, with(b) polyfunctional amine chain extenders having an average functionality between about 2.2 and 6.0.The present invention additionally relates to the aqueous dispersions produced by the above process and to the films, coatings or adhesives produced from these dispersions.
    Type: Grant
    Filed: July 24, 1981
    Date of Patent: October 4, 1983
    Assignee: Mobay Chemical Corporation
    Inventor: Peter Markusch
  • Patent number: 4403050
    Abstract: Cathodically depositable, aqueous coating compositions comprising the reaction product of (A) polycondensates having free hydroxyl groups with a hydroxyl number of at least 40 mg KOH/g, and an average maximum molecular weight of 5000; and (B) a compound having an average of from about 0.8 to 1.5 free isocyanate groups and at least one basic aliphatically bound nitrogen atom. Optionally, there can be included in the reaction product a compound having from about 0.8 to 1.5 free isocyanate groups and from 1 to 3 ethylenically unsaturated double bonds. The coating compositions cure at relatively low temperatures and relatively short curing times to provide films having excellent resistance to water, chemicals, and corrosion.
    Type: Grant
    Filed: December 19, 1977
    Date of Patent: September 6, 1983
    Assignee: Vianova Kunstharz, A. G.
    Inventors: Georgios Pampouchidis, Wolfgang Daimer, Heiner Verdino
  • Patent number: 4389509
    Abstract: Cathodically depositable, aqueous coating compositions comprising the reaction product of (A) diene polymers containing free hydroxyl groups with a hydroxyl number of at least 40 mg KOH/g and an average maximum molecular weight of 4000; and (B) a compound having an average of from about 0.8 to 1.5 free isocyanate groups and at least one basic aliphatically bound nitrogen atom. Optionally, there can be included in the reaction product a compound having from about 0.8 to 1.5 free isocyanate groups and from 1 to 3 ethylenically unsaturated double bonds. The coating compositions cure at relatively low temperatures and relatively short curing times to provide films having excellent resistance to water, chemicals, and corrosion.
    Type: Grant
    Filed: December 19, 1977
    Date of Patent: June 21, 1983
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Georgios Pampouchidis, Wolfgang Daimer, Heiner Verdino
  • Patent number: 4380593
    Abstract: Optionally-foamed intumescent compositions obtained by reacting(a) polyisocyanates with(b) phosphorus-containing condensation products having at least 2 hydroxyl groups and obtained by condensing primary or secondary monoamines and/or polyamines optionally containing OH-groups, carbonyl compounds and dialkyl phosphites, optionally followed by alkoxylation, and(c) more than bifunctional polyethers having an average OH-number of from 150 to 500 which have been obtained by the addition of alkylene oxides, of which from 50 to 100% by weight consist of ethylene oxide, with low molecular weight starters, and(d) cyanuric acid and/or cyanuric acid derivatives, and(e) optionally water and(f) optionally other organic compounds containing isocyanate-reactive hydrogen atoms,are used, for example, as cavity-filling, gap-sealing or coating materials.
    Type: Grant
    Filed: February 24, 1982
    Date of Patent: April 19, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wulf von Bonin, Gottfried Zaby
  • Patent number: 4373053
    Abstract: A color deepening agent comprises an aqueous resin composition obtained by polymerizing a monomer having a polymerizable unsaturated bond, in the presence of a polyurethane emulsion having a thermosetting reactivity, the refractive index of a dry film of said aqueous resin composition being lower than 1.50.
    Type: Grant
    Filed: July 21, 1981
    Date of Patent: February 8, 1983
    Assignee: Kao Soap Co., Ltd.
    Inventors: Toshio Sato, Sho Suzuki, Hidemasa Ohmura
  • Patent number: 4373043
    Abstract: A color deepening agent comprises (a) an aqueous resin composition obtained by polymerizing a monomer having a polymerizable unsaturated bond, in the presence of a polyurethane emulsion having a thermosetting reactivity, the refractive index of a dry film of said aqueous resin composition being lower than 1.50, and (b) at least one compound selected from the group consisting of silicon compounds and fluorine compounds.
    Type: Grant
    Filed: July 22, 1981
    Date of Patent: February 8, 1983
    Assignee: Kao Soap Co., Ltd.
    Inventors: Kazuhisa Yagi, Sho Suzuki, Norihiko Nakashima
  • Patent number: 4367295
    Abstract: The present invention relates to intumescent compositions, which may be foamed, and which are obtained by reacting:(1) polyisocyanates with(2) phosphorus-containing condensation products having at least one hydroxyl group obtainable by condensing (i) primary or secondary aliphatic, cycloaliphatic, aromatic, araliphatic or heterocyclic monoamines and/or polyamines, which mono- or polyamines may contain OH-groups; (ii) carbonyl compounds; and, (iii) dialkyl phosphites, and(3) polyesters containing hydroxyl groups and having OH-numbers of from 140 to 300, obtained by reacting polycarboxylic acids containing from 2 to 10 carbon atoms with at least 2 polyols selected from two different groups of the following three:(a) hydroxyl compounds containing more than three OH groups and having molecular weights of up to 200,(b) hydroxyl compounds containing three OH groups and having molecular weights of up to 150,(c) hydroxyl compounds containing two OH-groups and having molecular weights of up to 80, with the proviso tha
    Type: Grant
    Filed: June 23, 1981
    Date of Patent: January 4, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventor: Wulf von Bonin
  • Patent number: 4346192
    Abstract: An oxidated silicon compound will react with a substituted organic compound in the presence of an alkali compound to produce organic alkali metal silicate products which may be used as molding powders, as adhesives, as coating agents and be reacted with polyisocyanates to produce insulating foams.
    Type: Grant
    Filed: December 7, 1981
    Date of Patent: August 24, 1982
    Inventor: David H. Blount
  • Patent number: 4346180
    Abstract: An oxidated silicon compound will react with a substituted organic compound in the presence of an alkali compound to produce organic alkali metal silicate products which may be used as molding powders, as adhesives, as coating agents and be reacted with polyisocyanates to produce insulating foams.
    Type: Grant
    Filed: December 10, 1981
    Date of Patent: August 24, 1982
    Inventor: David H. Blount
  • Patent number: 4339566
    Abstract: A water-dispersible urethane acrylate binding agent which comprises a reaction product of: (A) 1 gram equivalent NCO of a di- or tri-isocyanate; (B) from 0 to 0.7 gram equivalent OH of a polyol, free of organically bound sulphur; (C) from 0.1 to 0.7 gram equivalent OH of a hydroxy-(C.sub.2 -C.sub.6 alkyl)-acrylate; and (D) from 0.01 to 0.5 gram equivalent NH of an amino sulphonic acid or an alkali metal or an alkaline earth metal salt thereof having from 1 to 4 amino groups per sulphonic acid group; the ratio of NCO group: NCO-reactive groups being from 1:1 to 1:1.2 which are prepared by reacting components (A), (B), (C), and (D) in a ratio of NCO groups:NCO-reactive groups of from 1:1 to 1:1.2 at a temperature of from 20.degree. to 100.degree. C.
    Type: Grant
    Filed: September 2, 1980
    Date of Patent: July 13, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans J. Rosenkranz, Hellmut Striegler, Otto Bendszus
  • Patent number: 4338412
    Abstract: The present invention is directed to intumescent compositions, which may be foamed, obtained by reacting:(1) polyisocyanates,(2) phosphorus-containing condensation products having at least one hydroxyl group and obtained by condensing (i) primary or secondary aliphatic, cycloaliphatic, aromatic, araliphatic or heterocyclic monoamines and/or polyamines, which mono- and polyamines may contain OH groups, (ii) carbonyl compounds, and (iii) dialkyl phosphites,(3) aromatic hydroxy carboxylic acids or salts thereof, and(4) optionally, water and/or additional organic compounds containing isocyanate-reactive hydrogen atoms.
    Type: Grant
    Filed: June 23, 1981
    Date of Patent: July 6, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventor: Wulf von Bonin