Nitrogen Reactant Having At Least One Amino-nitrogen Atom Contains At Least One Aryl Group Patents (Class 528/124)
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Patent number: 4412056Abstract: 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: GrantFiled: November 10, 1982Date of Patent: October 25, 1983Assignee: Shell Oil CompanyInventors: Johan van Gogh, Hermanus Grol
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Patent number: 4394496Abstract: 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: GrantFiled: October 30, 1981Date of Patent: July 19, 1983Assignee: The Dow Chemical CompanyInventor: Paul G. Schrader
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Patent number: 4367299Abstract: 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: GrantFiled: December 8, 1980Date of Patent: January 4, 1983Assignee: Ciba-Geigy CorporationInventors: Alfred Renner, Theobald Haug
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Patent number: 4366108Abstract: 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: GrantFiled: July 16, 1981Date of Patent: December 28, 1982Assignee: Ciba-Geigy CorporationInventors: Karl Urech, Jurgen Habermeier, Roland Moser
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Patent number: 4360456Abstract: 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: GrantFiled: November 13, 1980Date of Patent: November 23, 1982Assignee: Applied Plastics Co., Inc.Inventor: Francis G. Firth
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Patent number: 4308085Abstract: 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: GrantFiled: July 28, 1980Date of Patent: December 29, 1981Assignee: Jenoptik Jena GmbHInventors: Hans-Heinrich Horhold, Dieter Klemm, Klaus Bellstedt, Ludwig Haase, Joachim Klee, Klaus Schubert, Helmut Wachs, Rolf Martin
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Patent number: 4292195Abstract: 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: GrantFiled: May 16, 1977Date of Patent: September 29, 1981Assignee: The B. F. Goodrich CompanyInventor: Roger E. Morris
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Patent number: 4291146Abstract: 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: GrantFiled: October 29, 1979Date of Patent: September 22, 1981Assignee: Ciba-Geigy CorporationInventor: Theobald Haug
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Patent number: 4269751Abstract: 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: GrantFiled: March 9, 1979Date of Patent: May 26, 1981Assignee: Applied Plastics Co., Inc.Inventor: Francis G. Firth
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Patent number: 4252936Abstract: 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: GrantFiled: January 24, 1979Date of Patent: February 24, 1981Assignee: The United States of America as represented by the United States Department of EnergyInventors: James A. Rinde, Herbert A. Newey
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Patent number: 4201854Abstract: 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: GrantFiled: September 28, 1978Date of Patent: May 6, 1980Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Hans Lehmann
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Patent number: 4193905Abstract: 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: GrantFiled: December 2, 1977Date of Patent: March 18, 1980Assignee: Ciba-Geigy CorporationInventors: Thaddeus Audykowski, Roland Moser
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Patent number: 4183869Abstract: 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: GrantFiled: August 4, 1978Date of Patent: January 15, 1980Assignee: Hughes Aircraft CompanyInventor: Norman Bilow
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Patent number: 4182832Abstract: 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: GrantFiled: October 11, 1978Date of Patent: January 8, 1980Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Roland Moser, Thaddeus Audykowski
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Patent number: 4178427Abstract: 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: GrantFiled: February 6, 1978Date of Patent: December 11, 1979Assignee: Texaco Development Corp.Inventors: Harold G. Waddill, Heinz Schulze
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Patent number: 4168364Abstract: 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: GrantFiled: August 15, 1978Date of Patent: September 18, 1979Assignee: Ciba-Geigy CorporationInventors: Raymond Seltzer, Joseph F. DiPrima, William S. Durrell
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Patent number: 4153621Abstract: 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: GrantFiled: September 1, 1977Date of Patent: May 8, 1979Assignee: ICI Americas Inc.Inventor: Ludwig A. Hartmann
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Patent number: 4122069Abstract: 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: GrantFiled: April 11, 1977Date of Patent: October 24, 1978Assignee: Texaco Development CorporationInventor: Lee G. Meyer
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Patent number: 4108922Abstract: 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: GrantFiled: October 11, 1972Date of Patent: August 22, 1978Assignee: Allied Chemical CorporationInventors: Lamberto Crescentini, Gene Clyde Weedon, Rodney Lee Wells
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Patent number: 4107230Abstract: 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: GrantFiled: May 8, 1974Date of Patent: August 15, 1978Assignee: Tenneco Chemicals, Inc.Inventors: Roy G. Turnbo, David C. Purpi
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Patent number: 4101459Abstract: To accelerate the curing of epoxide resins by aromatic, heterocyclic, or cycloaliphatic polyamines there are employed salts of trifluoromethanesulfonic acid.Type: GrantFiled: October 20, 1976Date of Patent: July 18, 1978Assignee: Ciba-Geigy CorporationInventor: Christopher Michael Andrews