Nitrogen Reactant Having At Least One Amino-nitrogen Atom Contains At Least One Aryl Group Patents (Class 528/124)
  • Patent number: 4412056
    Abstract: The invention relates to polyglycidyl ethers and provides such compounds based on diphenylol C.sub.7 to C.sub.13 alkanes, and their preparation from the appropriate diphenylol alkanes. The polyglycidyl ethers may be cured with known epoxy resin curing agents and may be used as base materials for the preparation of anionic or cationic aqueous thermosetting paint binders.The polyglycidyl ethers exhibit good compatibility with aliphatic hydrocarbon solvents.
    Type: Grant
    Filed: November 10, 1982
    Date of Patent: October 25, 1983
    Assignee: Shell Oil Company
    Inventors: Johan van Gogh, Hermanus Grol
  • Patent number: 4394496
    Abstract: The invention comprises polyglycidyl ethers of tris(hydroxyphenyl)alkanes, their blends with other epoxy compounds and their cured products. The invention also comprises a process wherein the coupling reaction is carried out in the absence of coupling catalysts and solvents and the subsequent dehydrohalogenation is done in the presence of a methylethylketone/toluene mixture or an equivalent solvent. The epoxides of the invention have superior and unexpected high-temperature properties, without sacrificing other properties such as flex strength, flex modulus and the like.
    Type: Grant
    Filed: October 30, 1981
    Date of Patent: July 19, 1983
    Assignee: The Dow Chemical Company
    Inventor: Paul G. Schrader
  • Patent number: 4367299
    Abstract: The process according to the invention is performed by reaction of epoxide resins with primary and/or secondary polyamines with simultaneous quaternizing by means of aromatic and aliphatic polysulfonic esters, halogen-free organic phosphoric esters, or organic compounds which contain at least 1 chlorine or bromine atom, and which are free from -COOH groups and corresponding salt groups. The crosslinked plastics thus obtained are distinguished by an improved electrical conductivity.
    Type: Grant
    Filed: December 8, 1980
    Date of Patent: January 4, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Alfred Renner, Theobald Haug
  • Patent number: 4366108
    Abstract: Liquid polyglycidyl compounds, diethyltoluylenediamine, a curing accelerator and optionally further additives form a liquid matrix system with which fibres and fibre shapes are impregnated by known techniques, particularly by filament winding, pultrusion and injection processes. The components thus produced are for example tubes capable of withstanding pressure and torsional stress.
    Type: Grant
    Filed: July 16, 1981
    Date of Patent: December 28, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Karl Urech, Jurgen Habermeier, Roland Moser
  • Patent number: 4360456
    Abstract: A two component epoxy resin and curing means therefor in mastic compositions, shelf stable, in close side by side relationship, sharing the same environment, capable of ambient temperature curing, to a solid state when mixed in the correct proportions, such stability provided by low vapor pressure active ingredients, and the absence of reactive vapors in the curing means.
    Type: Grant
    Filed: November 13, 1980
    Date of Patent: November 23, 1982
    Assignee: Applied Plastics Co., Inc.
    Inventor: Francis G. Firth
  • Patent number: 4308085
    Abstract: High molecular linear, thermoplastic, epoxide-amine-adducts containing the structural segment ##STR1## are prepared by a solvent-free reaction of equivalent amounts at 20 to 200.degree. C. of N,N'-bis(aralkyl) diamines (for example, N,N'-dibenzyl-ethylenediamine, N,N'-dibenzyl-p-xylylenediamine, N,N'-dibenzyl-4,4'-diamino-diphenylmethane, N,N'-dibenzyl-3,6-dioxa-octanediamine-1,8) with diepoxides (for example, 2,2-bis(4-glycidyloxyphenyl)propane). The polyadducts are soluble and may be processed by thermoplastic methods. The polyaddition process may be conducted for the forming of shaped objects in a form-shaping vessel, for the production of coatings directly upon the surface to be coated and also in the presence of inserted materials and has, due to these characteristics, the nature of a casting system.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: December 29, 1981
    Assignee: Jenoptik Jena GmbH
    Inventors: Hans-Heinrich Horhold, Dieter Klemm, Klaus Bellstedt, Ludwig Haase, Joachim Klee, Klaus Schubert, Helmut Wachs, Rolf Martin
  • Patent number: 4292195
    Abstract: Antioxidant compositions as described which are the reaction products of a mixture of(a) at least one compound selected from compounds having the formula ##STR1## wherein each Ar is an aromatic group, and R and R.sup.1 are each independently hydrogen, alkyl, substituted alkyl, oxyalkylene or --C(O)--R.sup.2 --COOH groups wherein R.sup.2 is an alkylene or alkenylene group, with the proviso that at least one of the R and R.sup.1 groups must be hydrogen or a group containing at least one substituent reactive with an epoxy group, andAr--NH--Ar--O--R.sup.3 (FORMULA II)wherein Ar is as defined above and R.sup.3 is hydrogen, or a substituted alkyl group containing at least one substituent reactive with an epoxy group, or --C(O)--R.sup.2 --COOH wherein R.sup.2 is an alkylene or alkenylene group, and(b) at least one polyepoxide having at least 2 epoxy groups per molecule.
    Type: Grant
    Filed: May 16, 1977
    Date of Patent: September 29, 1981
    Assignee: The B. F. Goodrich Company
    Inventor: Roger E. Morris
  • Patent number: 4291146
    Abstract: Heat-curable mixtures of one or more epoxide compounds, which, on average, have more than one epoxide group in the molecule, and one or more .beta.-aminocrotonic acid derivatives, such as .beta.-aminocrotononitrile, .beta.-aminocrotonamide or .beta.-aminocrotonic acid esters, and also, if desired, a polyamine or polycarboxylic acid anhydride or a maleimide. The novel curable mixtures are distinguished by outstanding stability on storage, can be processed easily and give moulded materials with good mechanical properties.
    Type: Grant
    Filed: October 29, 1979
    Date of Patent: September 22, 1981
    Assignee: Ciba-Geigy Corporation
    Inventor: Theobald Haug
  • Patent number: 4269751
    Abstract: A two component epoxy resin and curing means therefor in mastic compositions, shelf stable, in close side by side relationship, sharing the same environment, capable of ambient temperature curing, to a solid state when mixed in the correct proportions, such stability provided by low vapor pressure active ingredients, and the absence of reactive vapors in the curing means.
    Type: Grant
    Filed: March 9, 1979
    Date of Patent: May 26, 1981
    Assignee: Applied Plastics Co., Inc.
    Inventor: Francis G. Firth
  • Patent number: 4252936
    Abstract: Primary diamines of the formula ##STR1## wherein R is a straight chain saturated hydrocarbon of 2 to 4 carbons, a disubstituted benzene ring, or disubstituted dibenzo methane for use as a curing agent for epoxy resins. These curing agents can be used to form epoxy resin mixtures useful in filament winding and pre-impregnated fiber molding and in formulating film adhesives, powder coatings and molding powders. The epoxy mixtures form for such uses as room temperature non-reacting, intermediate stable state which has a latent cross-linking capability.
    Type: Grant
    Filed: January 24, 1979
    Date of Patent: February 24, 1981
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: James A. Rinde, Herbert A. Newey
  • Patent number: 4201854
    Abstract: Curable mixtures of polyepoxide compounds which contain an amine curing agent have longer curing times, and thus, in particular, good workability when used as adhesives, when N,N-dimethylethylenediamine derivatives or N,N-dimethyl-1,3-propylenediamine derivatives are used as the curing agents. The mechanical properties are also frequently improved.
    Type: Grant
    Filed: September 28, 1978
    Date of Patent: May 6, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Helmut Zondler, Hans Lehmann
  • Patent number: 4193905
    Abstract: Curable mixtures comprising a polyepoxide compound having on average more than one epoxide group per molecule and a 1,3-diaminopropane of the formula ##STR1## wherein R.sup.1 denotes hydrogen and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each denote an alkyl having 1 to 12 C atoms, a phenyl or a heterocyclic 5-membered or 6-membered radical, or wherein R.sup.1 and R.sup.2 together with the C atom in the .alpha.-position of the propylenediamine from a substituted or unsubstituted aliphatic 5-membered or 6-membered ring having at most 12 C atoms and R.sup.3 and R.sup.4 together with the two C atoms in the .alpha.-position and the .beta.-position of the propylenediamine form a substituted or unsubstituted aliphatic or N-heterocyclic 5-membered or 6-membered ring having at most 12 C atoms, said mixtures containing 0.5 to 1.5 equivalents of active hydrogen atoms, bonded to nitrogen, in the 1,3-diaminopropane per 1 equivalent of epoxide groups in the epoxide compound.
    Type: Grant
    Filed: December 2, 1977
    Date of Patent: March 18, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Thaddeus Audykowski, Roland Moser
  • Patent number: 4183869
    Abstract: Novel thermosetting oligomers are formed by reacting epoxy prepolymers with aminoarylacetylenes. When heated to 170.degree. C. or above, these oligomers undergo acetylenic polymerization to form resins which exhibit superior thermal and hydrolytic stability when compared to conventionally cured epoxy resins.
    Type: Grant
    Filed: August 4, 1978
    Date of Patent: January 15, 1980
    Assignee: Hughes Aircraft Company
    Inventor: Norman Bilow
  • Patent number: 4182832
    Abstract: 1,4-Diaminobutanes of the formula ##STR1## in which R.sup.1 is H or --CH.sub.3 and R.sup.2 and R.sup.3 independently of one another are each a radical of the formula ##STR2## in which A is alkyl having 1 to 3 C atoms, --OCH.sub.3, --N(CH.sub.3).sub.2, --Cl or --Br and R.sup.2 also is alkyl having 1 to 3 C atoms, are prepared according to the invention by catalytically hydrogenating succinic acid dinitrile of the formula ##STR3## in the presence of acetic anhydride and hydrolyzing the N,N'-diacetyl-1,4-diaminobutanes thus obtained to diamines of the formula I, which are valuable curing agents for epoxide resins.
    Type: Grant
    Filed: October 11, 1978
    Date of Patent: January 8, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Helmut Zondler, Roland Moser, Thaddeus Audykowski
  • Patent number: 4178427
    Abstract: An improved curable epoxy resin composition of a vicinalpolyepoxide and an effective amount of a novel polyether urea curing agent is disclosed. The improved curable epoxy resins which are useful as coatings, castings, sealants, and adhesives show improved tensile shear strength, flexural strength, and ultimate elongation. The novel polyether urea curing agents of the instant invention are characterized by terminal primary amino groups and are formed by reaction of polyoxyalkylenepolyamines with urea, urea forming compounds, or bifunctional isocyanates.A preferred curing agent includes a mixture of a novel polyether urea formed by reaction of a polyoxypropylenepolyamine having a molecular weight of from about 200-2000 and an effective amount of urea; and another known epoxy resin curing agent such as polyoxyalkylenepolyamine in ratios of from about 5:1 to 1:5 by weight.
    Type: Grant
    Filed: February 6, 1978
    Date of Patent: December 11, 1979
    Assignee: Texaco Development Corp.
    Inventors: Harold G. Waddill, Heinz Schulze
  • Patent number: 4168364
    Abstract: Curable compositions are prepared comprising an epoxide compound or a mixture of epoxide compounds having an average of at least two epoxide groups per molecule, and as a curing agent, a cyanamide of an organic primary amine or a mixture of cyanamides of organic primary amines having an average of more than one cyanamide moiety per molecule. Such compositions are useful in molding, casting, laminating and coating applications.
    Type: Grant
    Filed: August 15, 1978
    Date of Patent: September 18, 1979
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond Seltzer, Joseph F. DiPrima, William S. Durrell
  • Patent number: 4153621
    Abstract: Glycidyl ethers prepared from the reaction of 3,3',5,5'-tetraalkyl-4,4'-dihydroxybiphenyl and halohydrin form upon curing resins having high heat distortion temperatures. The ethers have utility in the manufacture of powder coatings, adhesive compositions, laminates and molding compositions.
    Type: Grant
    Filed: September 1, 1977
    Date of Patent: May 8, 1979
    Assignee: ICI Americas Inc.
    Inventor: Ludwig A. Hartmann
  • Patent number: 4122069
    Abstract: The adhesion properties of amine-cured epoxy resins are unexpectedly enhanced by addition of certain di-hydroxyalkyl carbamate terminated polyether additives. The adhesively superior epoxy resin composition comprises a vicinal polyepoxide, a curing amount of an amine curing agent, and an effective amount of a polyether dicarbamate having terminal hydroxyalkyl carbamate groups and a molecular weight of from about 2000 to about 3000.
    Type: Grant
    Filed: April 11, 1977
    Date of Patent: October 24, 1978
    Assignee: Texaco Development Corporation
    Inventor: Lee G. Meyer
  • Patent number: 4108922
    Abstract: A new composition has been found comprising an antistatic fiber selected from the group consisting of polyamide, polyester, polyurea, polyurethane, or polysulfonamide, said fiber containing between about one percent and about twelve percent by weight of at least one compound having a molecular weight above 1500 selected from the group consisting of compounds represented by the formulas: ##STR1## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently selected from nonovalent hydrocarbon radicals having 1 to 20 carbon atoms derived from aliphatic, aromatic, cycloaliphatic, aromaticaliphatic, heterocyclic hydrocarbons or --(C.sub.r H.sub.2r O).sub.m (C.sub.p H.sub.2p O).sub.q --H; R.sub.5 is at least one of the alkylene difunctional radicals having 2 to 15 carbon atoms and a radical selected from ##STR2## R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are independently selected from R.sub.1, R.sub.2, R.sub.3, R.sub.4, H or another monovalent hydrocarbon radical having 1 to 20 carbon atoms as defined for R.sub.
    Type: Grant
    Filed: October 11, 1972
    Date of Patent: August 22, 1978
    Assignee: Allied Chemical Corporation
    Inventors: Lamberto Crescentini, Gene Clyde Weedon, Rodney Lee Wells
  • Patent number: 4107230
    Abstract: 1,1,2,3,4,4-Hexabromobutene-2 is used to impart flame-retardance to epoxy resins, polyesters, and other thermosetting organic polymers that are normally susceptible to burning.
    Type: Grant
    Filed: May 8, 1974
    Date of Patent: August 15, 1978
    Assignee: Tenneco Chemicals, Inc.
    Inventors: Roy G. Turnbo, David C. Purpi
  • Patent number: 4101459
    Abstract: To accelerate the curing of epoxide resins by aromatic, heterocyclic, or cycloaliphatic polyamines there are employed salts of trifluoromethanesulfonic acid.
    Type: Grant
    Filed: October 20, 1976
    Date of Patent: July 18, 1978
    Assignee: Ciba-Geigy Corporation
    Inventor: Christopher Michael Andrews