Patents by Inventor Helmut Zondler
Helmut Zondler has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 4499268Abstract: A novel process for the preparation of isomelamines of the formula I, ##STR1## which is characterized in that an N-cyano-N-(ar or cyclo)alkylcarboxylic acid amide or N-cyano-N-allylcarboxylic acid amide of the formula II or III ##STR2## is reacted with aqueous sodium hydroxide solution, potassium hydroxide solution or ammonia solution or a primary aliphatic or cycloaliphatic amine in a solvent or with a primary aliphatic alcohol in the presence of a catalytic amount of a basic compound in a temperature range from -20.degree. C. to 200.degree. C., at least 3 hydroxyl or amino group equivalents being used per 3 carboxylic acid amide group equivalents.The isomelamines prepared by the process according to the invention are valuable curing agents for epoxide resins.Type: GrantFiled: February 15, 1983Date of Patent: February 12, 1985Assignee: Ciba Geigy CorporationInventors: Friedrich Lohse, Helmut Zondler
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Patent number: 4436892Abstract: Novel imidazolides (N-acylimidazoles) of the formula I ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.12 -alkyl or phenyl, and R.sub.2 is hydrogen, orR.sub.1 is ethyl, and R.sub.2 is methyl, orR.sub.1 is hydrogen, and R.sub.2 is phenyl or methyl, andR.sub.3 is a group of any one of the formulae II-VI ##STR2## wherein X.sub.1 is hydrogen, chlorine or NO.sub.2, and X.sub.2 is hydrogen or NO.sub.2.The imidazolides are suitable as curing agents for polyepoxide compounds.Type: GrantFiled: December 6, 1982Date of Patent: March 13, 1984Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Friedrich Lohse, Roland Moser
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Patent number: 4352913Abstract: (Dimethylaminoalkyl)carboxylic and -carbamic acid esters and (dimethylaminoalkyl) ethers and ureas are compounds which are especially suitable for use as amine curing agents for polyepoxide compounds. They impart longer curing times to the curable mixtures and thus good processing properties, especially when the mixtures are used as adhesives. In addition, the mechanical properties are often improved. Further, these compounds afford advantages when used as curing agents on account of their low volatility.Type: GrantFiled: August 21, 1981Date of Patent: October 5, 1982Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Roland Moser
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Patent number: 4324739Abstract: (Dimethylaminoalkyl)carboxylic and -carbamic acid esters and (dimethylaminoalkyl) ethers and ureas are compounds which are especially suitable for use as amine curing agents for polyepoxide compounds. They impart longer curing times to the curable mixtures and thus good processing properties, especially when the mixtures are used as adhesives. In addition, the mechanical properties are often improved. Further, these compounds afford advantages when used as curing agents on account of their low volatility.Type: GrantFiled: March 31, 1980Date of Patent: April 13, 1982Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Roland Moser
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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: 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: 4163098Abstract: The coating compound according to the invention contains an epoxide resin, a diprimary amine curing agent and as modifier a hydrazone of the formula ##STR1## wherein the radical R.sup.1 -R.sup.4 represent hydrogen or alkyl, provides after curing coatings having a smooth, lustrous and glass-like surface which has a good resistence to chemicals.Type: GrantFiled: August 30, 1978Date of Patent: July 31, 1979Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Wolfgang Schneider
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Patent number: 4151229Abstract: The invention relates to a process for the manufacture of aminoalkyl-phosphonic acid esters by catalytic hydrogenation of cyanoalkylphosphonic acid esters. After having separated the catalyst and solvents, in general the crude product is distilled.The esters which can be obtained by the process of this invention are of importance as intermediate products, because all reactions of amines can be carried out with these products. They can also be used as additives for amine curing agents for epoxide resins in order to achieve flame-retarding properties.Type: GrantFiled: May 2, 1975Date of Patent: April 24, 1979Assignee: Ciba-Geigy CorporationInventor: Helmut Zondler
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Patent number: 4150229Abstract: 2,5-di-(.omega.-aminoalkyl-1')-pyrazines are obtained by catalytic hydrogenation of nitro compounds of the formula ##STR1## They are suitable as hardeners for epoxides or for the manufacture of polyamides.Type: GrantFiled: December 27, 1977Date of Patent: April 17, 1979Assignee: Ciba-Geigy CorporationInventors: Srinivasachari Rajappa, Helmut Zondler
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Patent number: 4129556Abstract: Curable mixtures containing (a) a polyepoxide compound having on average more than one epoxide group per molecule and (b) a diamine which contains hydroxyl groups and has the general formula Ia or Ib ##STR1## IN WHICH R is an alkyl radical having 2 to 16 C atoms, an aralkylene radical having 7 to 12 C atoms, an arylene radical having 6 to 16 C atoms, a cycloaliphatic radical having 6 to 12 C atoms or a radical containing at least one N, O or S atom in chains or cyclic groups, and R.sub.1 is a hydrogen atom, a halogen atom or an alkyl group having 1 to 4 C atoms and in which, in formula Ia, the two OH groups are in the orthoposition or para-position relative to the methylene group, there being, in the mixtures, 0.5 to 1.5 equivalents of active hydrogen atoms, which are bonded to nitrogen and oxygen in the diamine containing hydroxyl groups, per 1 equivalent of epoxide groups.Type: GrantFiled: December 2, 1977Date of Patent: December 12, 1978Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Roland Moser
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Patent number: 4122128Abstract: A storable, rapidly hardening epoxy resin adhesive consisting ofA. a polyglycidyl compound having a softening temperature between 40.degree. and 90.degree. C,b. a 2,5-di-(.omega.-aminoalkyl-1')-pyrazine of the formula ##STR1## wherein n is an integer from 3 to 6, and C. A COPOLYMER OF ETHYLENE, ACRYLIC ACID AND ACRYLATE HAVING A MELTING RANGE FROM 70.degree. TO 110.degree. C, said epoxy resin adhesive contains, per 1 equivalent of glycidyl groups, 0.5 to 1.5 equivalents of hydrogen atoms bonded to nitrogen of the 2,5-di(.omega.-aminoalkyl-1')-pyrazine and, per 100 parts by weight of the polyglycidyl compound, contains 3 to 20 parts by weight of the copolymer of ethylene, acrylic acid and acrylate.Type: GrantFiled: December 27, 1977Date of Patent: October 24, 1978Assignee: Ciba-Geigy CorporationInventors: Hans Lehmann, Helmut Zondler
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Patent number: 4117038Abstract: A storable, rapidly hardening epoxy resin adhesive consisting essentially ofA. a polyglycidyl compound having a softening temperature between 40.degree. and 90.degree. C,b. a salt of 1 mole of ethylenediamine, 1 mole of bisphenol A and 2 g of N,N-dimethyl-1,3-diaminopropane,C. an ABS graft polymer andD. a copolymer of ethylene, acrylic acid and acrylate having a melting range from 70.degree. to 110.degree. C,said adhesive comprises, per 1 equivalent of glycidyl groups, 0.5 to 1.5 equivalents of hydrogen atoms bonded to nitrogen of ethylenediamine and of N,N-dimethyl-1,3-diaminopropane, and per 100 parts of the polyglycidyl compound contains 3 to 30 parts by weight of the ABS graft polymer and 3 to 20 parts by weight of the copolymer of ethylene, acrylic acid and acrylate, and said adhesive is in the form of a fine heterogeneous powder.Type: GrantFiled: December 27, 1977Date of Patent: September 26, 1978Assignee: Ciba-Geigy CorporationInventors: Hans Lehmann, Helmut Zondler
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Patent number: 4113669Abstract: 2-Oxo-2-alkoxy-5-dialkylphosphono-1,2-oxaphospholanes of the formula ##STR1## in which R.sub.1 to R.sub.7 are hydrocarbon radicals can be prepared from .alpha.,.beta.-unsaturated ketones and 2 or more moles of a dialkyl phosphite. Obviously .gamma.-ketophosphonates are intermediates of this reaction, as these compounds react with 1 or more moles of dialkyl phosphite in yielding the oxaphospholanes too. Both reactions are promoted by alkaline catalysts.The new oxaphospholane derivatives are considerably stable against thermal decomposition. They are compatible with polymeric materials and can be used as flame protecting agent for plastics and resins, for example, in polyurethane foams.Type: GrantFiled: June 13, 1977Date of Patent: September 12, 1978Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Emil Saladin, Rudolf Kirchmayr
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Patent number: 4045518Abstract: 2-Oxo-2-alkoxy-5-dialkylphosphono-1,2-oxaphospholanes of the formula ##STR1## in which R.sub.1 to R.sub.7 are hydrocarbon radicals can be prepared from .alpha.,.beta.-unsaturated ketones and 2 or more moles of a dialkyl phosphite. Obviously .alpha.-ketophosphonates are intermediates of this reaction, as these compounds react with 1 or more moles of dialkyl phosphite in yielding the oxaphospholanes too. Both reactions are promoted by alkaline catalysts.The new oxaphospholane derivatives are considerably stable against thermal decomposition. They are compatible with polymeric materials and can be used as flame protecting agent for plastics and resins, for example, in polyurethane foams.Type: GrantFiled: September 22, 1975Date of Patent: August 30, 1977Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Emil Saladin, Rudolf Kirchmayr
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Patent number: 3971792Abstract: The new compound 4-amino-3-aminomethylpiperidine is manufactured by hydrogenating 4-amino-3-cyano-1,2,5,6-tetrahydropyridine under pressure and in the presence of ammonia and a hydrogenation catalyst. The 4-amino-3-cyano-1,2,5,6-tetrahydropyridine used as the starting substance can be obtained by cyclization of bis-cyanoethylenated ammonia. The new compound 4-amino-3-aminomethylpiperidine represents a valuable curing agent for epoxide resins, and advantageously 0.5 to 1.3 equivalents of nitrogen-bonded active hydrogen atoms of the 4-amino-3-aminomethylpiperidine are used per 1 equivalent of epoxide groups of the polyepoxide compound.Type: GrantFiled: June 10, 1974Date of Patent: July 27, 1976Assignee: Ciba-Geigy AGInventors: Helmut Zondler, Wolfgang Pfleiderer
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Patent number: 3957820Abstract: The invention relates to 3-amino-4-aminomethyl-pyrrolidines which contain, in the 1-position of the heterocyclic ring, organic radicals as substituents, and in which also the H-atom in the 2-position of the heterocyclic ring can be substituted by an organic radical. The invention also relates to the preparation of these pyrrolidines by catalytic hydrogenation of the corresponding 3-amino-4-cyano-3-pyrrolines. Hydrogenation is preferably performed in the presence of NH.sub.3. The amines according to the invention are suitable as curing agents for epoxide resins, as reactants for isocyanates, and as starting substances for polyamides.Type: GrantFiled: July 17, 1974Date of Patent: May 18, 1976Assignee: Ciba-Geigy CorporationInventor: Helmut Zondler
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Patent number: 3945953Abstract: .omega.,.omega.'-bis-[4-amino-3-aminomethyl-piperidyl-(1)]-alkanes of the general formula ##SPC1##Wherein n is a number from 2 to 6, are prepared by hydrogenating, a .omega.,.omega.'-bis-[4-amino-3-cyano-1,2,5,6-tetrahydro-pyridyl-(1)]-alka ne at temperatures from 20.degree. to 280.degree.C. These polyamines are valuable hardeners for epoxide resins. They are also of interest as intermediates for organic syntheses.Type: GrantFiled: August 23, 1974Date of Patent: March 23, 1976Assignee: Ciba-Geigy CorporationInventor: Helmut Zondler