Patents by Inventor Hans-Samuel Bien
Hans-Samuel Bien 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: 4299966Abstract: 4,4',7,7'-Tetrachlorothioindigo can be obtained in a form directly suitable for use as a pigment if the oxidation of 3-hydroxy-4,7-dichloro-1-thionaphthene is performed in an alkaline medium in the presence of oxygen or an oxygen-containing gas.Type: GrantFiled: June 27, 1980Date of Patent: November 10, 1981Assignee: Bayer AktiengesellschaftInventors: Hans-Samuel Bien, Werner Beinert, Klaus Wunderlich
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Patent number: 4220779Abstract: Quinoline derivatives, especially those of the formula ##STR1## wherein X represents halogen, nitro or CF.sub.3,Z represents hydrogen, alkyl or aryl,Y represents hydrogen, OH, CN, COR or SO.sub.3 H,R represents alkyl, alkoxy or aryl andn represents an integer from 0 to 4,are obtained in high yields when corresponding aromatic orthodichloromethyl isocyanates are converted by hydrolysis and decarboxylation into the corresponding ortho-aminoaldehydes and these are subjected to a condensation reaction with carbonyl compounds containing an active .alpha.-methylene group.The process products are starting materials for dyestuffs, insecticides and others.Type: GrantFiled: June 30, 1978Date of Patent: September 2, 1980Assignee: Bayer AktiengesellschaftInventors: Volker Ehrig, Hans-Samuel Bien, deceased, Erich Klauke, Detlef-Ingo Schutze
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Patent number: 4206306Abstract: Reactive dyestuffs are disclosed having the formula ##STR1## in which D is the radical of an organic nonanthraquinoid dyestuff; R is hydrogen or lower alkyl; R.sub.1 is amino or substituted amino with substituents attached by a single bond, optionally etherified hydroxy, optionally etherified mercapto or an optionally substituted hydrocarbon radical; Q is an alkylene, aralkylene, arylene, --CO-- or --SO-- which is directly linked to a carbon atom of the ring of the dyestuff D; n is the number 0 or 1 and F is a fluoro substituent. The group --N(R) is directly linked to a carbon atom of the triazine ring and on the other side, the group --N(R) is linked to a carbon atom of the ring of the dyestuff D either directly (if n=0) or (if n=1) via one of the bridge members mentioned above. These dyestuffs are primarily suitable for dyeing of textile materials containing hydroxyl or nitrogen such as natural and regenerated cellulose, wood, silk, polyamide and polyurethane.Type: GrantFiled: January 23, 1978Date of Patent: June 3, 1980Assignee: Bayer AktiengesellschaftInventors: Hans-Samuel Bien, Erich Klauke, Klaus Wunderlich
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Patent number: 4179450Abstract: The invention relates to a novel process for the preparation of 1-acylamino-5(8)-chloroanthraquinones, which are starting materials for the preparation of vat dyes. It is characterized in that 1,5(8)-dichloroanthraquinones is reacted with ammonia at temperatures of 190.degree. to 240.degree. C., the amino groups in the reaction mixture are completely acylated and the more sparingly soluble diacylaminoanthraquinone is separated off from the more readily soluble monoacylaminochloroanthraquinone.The new process yields reaction products which are purer and cheaper than those which are obtained by conventional methods. Moreover there are smaller waste water problems.Type: GrantFiled: May 5, 1977Date of Patent: December 18, 1979Assignee: Bayer AktiengesellschaftInventors: Detlef-Ingo Schutze, Hans-Samuel Bien, deceased, Petra Bien, heir, Daniel Bien, heir
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Patent number: 4162946Abstract: A process for concentrating at least one of (a) individual halogenoanthraquinones (b) binary mixtures of di-halogenoanthraquinones and (c) binary mixtures of trihalogenoanthraquinones, from a mixture containing at least two halogenoanthraquinones, comprising subjecting said mixture containing at least two halogenoanthraquinones to fractional vacuum distillation in a heated rectification column having an efficiency corresponding to about 20 to 50 theoretical stages with an absolute pressure at the top of about 0.5 to 50 mm Hg and a reflux to take-off ratio of about 5/1 to 50/1.Type: GrantFiled: September 1, 1977Date of Patent: July 31, 1979Assignee: Bayer AktiengesellschaftInventors: Bernd Thelen, Norbert Majer, Reinold Schmitz, Hans-Samuel Bien
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Patent number: 4115378Abstract: Reactive dyestuffs are disclosed having the formula ##STR1## in which D is the radical of an organic nonanthraquinoid dyestuff; R is hydrogen or a lower alkyl; R.sub.1 is amino or substrated amino with substituents attached by a single bond, optionally etherified hydroxy, optionally etherified mercapto or an optionally substituted hydrocarbon radical; Q is an alkylene, aralkylene, arylene, --CO-- or --SO-- which is directly linked to a carbon atom of the ring of the dyestuff D; n is the number 0 or 1 and F is a fluoro substituent. The group --N(R) is directly linked to a carbon atom of the triazine ring and on the other side, the group --N(R) is linked to a carbon atom of the ring of the dyestuff D either directly (if n = 0) or (if n = 1) via one of the bridge members mentioned above. These dyestuffs are primarily suitable for dyeing of textile materials containing hydroxyl or nitrogen such as natural and regenerated cellulose, wood silk, polyamide and polyurethane.Type: GrantFiled: June 8, 1971Date of Patent: September 19, 1978Assignee: Bayer AktiengesellschaftInventors: Hans-Samuel Bien, Erich Klauke, Klaus Wunderlich
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Patent number: 4105662Abstract: Reactive dyestuffs of the formula ##STR1## WHEREIN R.sub.1, R.sub.2, R.sub.3, X, Y and Z have the meaning given in the description and their use for the dyeing and printing of materials which contain hydroxyl groups and materials which contain N, such as cotton, wool and the like, by the customary processes.Type: GrantFiled: March 9, 1977Date of Patent: August 8, 1978Assignee: Bayer AktiengesellschaftInventors: Klaus von Oertzen, Hans Samuel Bien, deceased, by Gabriele Bien, legal representative
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Patent number: 4104284Abstract: Process for dyeing and printing synthetic fibre materials using compounds of the formula ##STR1## in which R represents an optionally substituted phenyl radical, as well as special new dyestuffs within the above formula.Type: GrantFiled: June 11, 1976Date of Patent: August 1, 1978Assignee: Bayer AktiengesellschaftInventors: Walter Hohmann, Helmut Herzog, Hans-Samuel Bien
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Patent number: 4102924Abstract: Process for the preparation of diaryl compounds of the formula ##STR1## by reacting of acylamino-aryl-compounds of the formula ##STR2## WITH ARYL COMPOUNDS OF THE FORMULA ##STR3## IN THE PRESENCE OF METALLIC COPPER OR ITS MIXTURE WITH COPPER SALTS, OPTIONALLY IN THE PRESENCE OF CATALYSTS, IN A SOLVENT WHICH IS INERT UNDER THE REACTION CONDITIONS, AT TEMPERATURES OF 20.degree. TO 200.degree. C. In the formulae A and B represent an aromatic ring system, R represents acyl and X represents a nitro, nitrile, carboxylic ester, acyl or --NH--R group.Type: GrantFiled: October 7, 1975Date of Patent: July 25, 1978Assignee: Bayer AktiengesellschaftInventors: Walter Kalk, Hans Samuel Bien, Karl Heinz Schundehutte
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Patent number: 4101551Abstract: The invention relates to water-insoluble quinophthalone dyestuffs of the formula ##STR1## in which T represents W--Ar or ##STR2## and Ar denotes aryl,W denotes oxygen, sulphur or N--R,R denotes hydrogen or alkyl,A denotes alkylene, O R.sub.1 denotes alkyl or aryl,R.sub.2 denotes hydrogen or alkyl,X denotes halogen, alkyl, alkoxy, nitro or acylamino,Y denotes hydrogen or halogen,Z denotes hydrogen, alkyl or halogen andn denotes a number from 0 to 3The new dyestuffs and their mixtures are distinguished by good affinity to polyester fibres and good general fastness properties.Type: GrantFiled: July 2, 1976Date of Patent: July 18, 1978Assignee: Bayer AktiengesellschaftInventors: Manfred Groll, Hans-Samuel Bien, deceased
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Patent number: 4076736Abstract: In the reaction of a nitroanthraquinone with ammonia in a solvent at elevated temperature to produce the corresponding aminoanthraquinone, the improvement which comprises effecting the reaction in the presence of an ammonium halide. Advantageously, the nitroanthraquinone is an .alpha.-nitroanthraquinone, the ammonium halide is at least one of ammonium chloride and ammonium bromide, and the solvent comprises at least one member selected from the group consisting of water, nitrobenzene, a glycol, an acid amide and sulfolane.Type: GrantFiled: June 4, 1976Date of Patent: February 28, 1978Assignee: Bayer AktiengesellschaftInventors: Karl-Julius Reubke, Hans-Samuel Bien, deceased, Gabriele Bien, Dorothee Bien
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Patent number: 4065446Abstract: Dyestuffs are disclosed having the formula ##STR1## in which W is a reactive radical;D is the radical of an organic dyestuff;X.sub.1 is hydrogen or alkyl;X.sub.2 and X.sub.3 are hydrogen, alkyl, cycloalkyl, aralkyl or aryl; or X.sub.2 and X.sub.3 together are alkylene;Alkylene is C.sub.1 -C.sub.6 -alkylene or cycloalkylene; and n is 0 or 1.The dyestuffs are used in the dyeing of textile materials containing hydroxyl groups and nitrogen, especially natural and regenerated cellulose, wool, silk, synthetic polyamide fibers and synthetic polyurethane. The dyeings obtained are, in general, distinguished by good to very good fastness properties, especially by excellent wet fastness.Type: GrantFiled: March 24, 1972Date of Patent: December 27, 1977Assignee: Bayer AktiengesellschaftInventors: Hans-Samuel Bien, Wolfgang Harms
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Patent number: 4056544Abstract: Compounds of the formula ##STR1## wherein R represents cycloalkyl or the ##STR2## group wherein R.sub.1 and R.sub.2 denote alkyl and Y denotes hydrogen, chlorine, bromine, amino, alkylamino, cycloalkylamino, aralkylamino, arylamino, acylamino or arylmercapto, with the proviso that the nitro group is in the 5- or 8-position of the anthraquinone nucleus if Y denotes hydrogenAs well as their production and their use for the dyeing of synthetic fibres.Type: GrantFiled: February 15, 1974Date of Patent: November 1, 1977Assignee: Bayer AktiengesellschaftInventors: Walter Hohmann, Helmut Herzog, Hans-Samuel Bien
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Patent number: 4045457Abstract: The invention relates to a process for the preparation of water-insoluble chlorine-containing diaminodihydroxyanthraquinone dyestuffs. The process consists in that 2,8-dichloro-1,5-dinitroanthraquinone and/or 2,5-dichloro-1,8-dinitroanthraquinone is warmed with sulphur in concentrated sulphuric acid having a maximum SO.sub.3 content of 20% - possibly in the presence of boric acid - the resulting compounds are, if appropriate, post-halogenated and/or alkylated, preferably in the same reaction batch.The main advantage of this process is that it starts from 1,6- and/or 1,7-dichloroanthraquinone, for which there was hitherto no industrial use, but which unavoidably also arise during the synthesis 1,5- and 1,8-dichloroanthraquinones.Type: GrantFiled: October 20, 1975Date of Patent: August 30, 1977Assignee: Bayer AktiengesellschaftInventors: Gunter Gehrke, Reinold Schmitz, Hans-Samuel Bien, Helmut Herzog
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Patent number: 4041053Abstract: The invention relates to the preparation of partially known anthraquinone compounds of the formula ##STR1## wherein Z.sub.1 represents an optionally substituted hydrocarbon radical,Z.sub.2 represents hydrogen or alkyl, one X represents a chlorine atom and the other X denotes a hydrogen atom, by subjecting technical chloroanthraquinone mixtures to a fractional vacuum distillation and reacting the 1,6(1,7)-dichloranthraquinone fraction thereby obtained with amines of the formula HNZ.sub.1 Z.sub.2.Moreover the invention relates to novel compounds of the above formula wherein Z.sub.2 is H and Z.sub.1 is alkyl, alkenyl, aralkyl or cycloalkyl. They are good dyestuffs for synthetic fibres or dyestuff intermediates.Type: GrantFiled: March 24, 1976Date of Patent: August 9, 1977Assignee: Bayer AktiengesellschaftInventors: Helmut Herzog, Hans-Samuel Bien, Walter Hohmann
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Patent number: 4036862Abstract: The invention relates to mixtures of water-insoluble anthraquinone dyestuffs of the formula ##STR1## in which A and B are amino or hydroxylR is alkyleneX is a direct bond, oxygen, sulphur or iminoAr is arylD.sub.1 and D.sub.2 are hydrogen or halogen,Hal represents chlorine or preferably bromine andn represents on average a number from 0.1 to 2.5.The preferred variant for the preparation of the dyestuffs (wherein Hal represents bromine) is characterized in that anthraquinone compounds of the formula ##STR2## are brominated on the aryl radical Ar. The dyestuffs are outstanding suitable for the dyeing of polyester fibers.Type: GrantFiled: September 30, 1975Date of Patent: July 19, 1977Assignee: Bayer AktiengesellschaftInventors: Volker Hederich, Hans-Samuel Bien, Gunter Gehrke
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Patent number: 4024144Abstract: Polycyclic dyestuffs free from sulphonic acid groups of the formula ##STR1## in which A denotes an arylene radical andB--so.sub.2 --or denotes an arylene radical substituted by an aryloxysulphonyl group,Are suitable for dyeing organic materials, especially for dyeing and printing hydrophobic fibre materials and for bulk-dyeing synthetic materials.Type: GrantFiled: May 19, 1975Date of Patent: May 17, 1977Assignee: Bayer AktiengesellschaftInventors: Manfred Groll, Volker Hederich, Hans-Samuel Bien
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Patent number: 4007164Abstract: Reactive dyestuffs of the formula ##STR1## in which D is the radical of an organic dyestuff, e.g. an azo dyestuff; R is hydrogen or lower alkyl; O is a bridge member, e.g. --SO.sub.2 --; n is the number 0 or 1; R.sub.1 is hydrogen or a substituent; R.sub.2 is hydrogen, optionaly substituted alkyl, alkenyl, aralkyl or aryl; and F is fluoro; are disclosed. These dyestuffs are suitable for dyeing textile materials containing hydroxyl groups or nitrogen, e.g. cellulose and wool. The dyeings have excellent fastness properties especially wet processing fastness.Type: GrantFiled: March 30, 1971Date of Patent: February 8, 1977Assignee: Bayer AktiengesellschaftInventors: Hans-Samuel Bien, Erich Klauke
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Patent number: 4006171Abstract: A process for the preparation of a chloroanthraquinone or a bromoanthraquinone comprising treating a molten mixture of at least one nitroanthraquinone and diluent with halogen at a temperature of about 180 to 300.degree. C, the diluent being present in at least about 10% by weight of the mixture and comprising at least one chloroanthraquinone or bromoanthraquinone. The diluent may correspond to the halogenoanthraquinone obtained from the nitroanthraquinone by replacement of the nitro group. A portion of the product can be recycled as diluent for further reaction.Type: GrantFiled: October 24, 1975Date of Patent: February 1, 1977Assignee: Bayer AktiengesellschaftInventors: Norbert Majer, Hans-Samuel Bien, Helmut Judat, Armin Lieberam
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Patent number: 4000167Abstract: Compounds of the formula ##SPC1##In which R represents an alkyl, alkenyl, cycloalkyl or aralkyl radical, one X represents a nitro group and the other X represents hydrogen and their mixtures. They are very suitable for the dyeing of synthetic fibres, such as fibres of polyesters.Type: GrantFiled: January 8, 1974Date of Patent: December 28, 1976Assignee: Bayer AktiengesellschaftInventors: Walter Hohmann, Helmut Herzog, Hans-Samuel Bien