Patents by Inventor Richard Buchecker
Richard Buchecker 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: 5888423Abstract: Flourobenzyl ether derivatives of the formula ##STR1## and liquid crystalline mixtures which contain such compounds are prepared and employed in electro-optical display devices.Type: GrantFiled: June 21, 1996Date of Patent: March 30, 1999Assignee: Rolic AgInventors: Richard Buchecker, Alfred Germann
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Patent number: 5852212Abstract: Optically active .alpha.-bromo- or .alpha.-chlorocarboxylic compounds of the formula ##STR1## wherein X is bromine or chlorine;M is hydrogen, NR.sub.4.sup.+1 or a cation of an alkali or alkaline earth metal;R.sup.1 is hydrogen or lower alkyl;n is 0 or 1;R is hydrogen, C.sub.1 -C.sub.20 alkyl, or C.sub.1 -C.sub.20 alkyl substituted in the terminal position with --NR.sup.2.sub.2, --COOR.sup.2, --OR.sup.3, a free or protected --CHO group or a ring A;R.sup.2 is hydrogen or a lower alkyl;R.sup.3 is hydrogen or a protecting group;ring A is an unsubstituted or substituted ring; and* is a center of chirality,are prepared by enantioselectively hydrogenating, in the presence of a ruthenium complex of an optically active diphosphine ligand, a (Z)-.alpha.,.beta.-unsaturated compound of the general formula ##STR2## wherein R, n, X and M are as defined above.Type: GrantFiled: June 12, 1996Date of Patent: December 22, 1998Assignee: Rolic AGInventors: Emil Albin Broger, Richard Buchecker, Yvo Crameri, Teodor Lukac
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Patent number: 5851425Abstract: Compounds of the general formula ##STR1## have a pronounced tendency to form liquid crystalline S (smectic) phases. Thus, optically inactive compounds of the formula I also have a tilted smectic phase, in particular an S.sub.C phase, in addition to a nematic phase. In contrast, many optically active compounds of the formula I additionally have, inter alia, a tilted smectic chiral phase, in particular a chiral S.sub.C phase, in addition to a cholesteric phase. The stated compounds are therefore particularly suitable as components and as dopants, respectively, for the preparation of a very wide range of liquid crystalline mixtures. The class of compounds comprising compounds of the general formula I offers a broad range of novel components and mixtures for optimization and modification of liquid crystalline mixtures.Type: GrantFiled: March 26, 1997Date of Patent: December 22, 1998Assignee: Rolic AGInventors: Richard Buchecker, Willy Friedrichsen, Jurg Funfschilling, Sandra Lupfert
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Patent number: 5800734Abstract: A compound of the formula ##STR1## wherein R is C.sub.1 -C.sub.7 alkyl or C.sub.2 -C.sub.12 alkenyl; rings A and B each independently are 1,4-phenylene,trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl;Z.sup.1 is a single bond or --CH.sub.2 CH.sub.2 --; andZ.sup.2 is a single bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --,--C.tbd.C--, --COO-- or --OOC--; andm, n are 0 or 1, with the proviso that m+n.ltoreq.1;as well as liquid crystalline mixtures which contain such compounds and the use of such compounds and, respectively, mixtures for electro-optical display devices.Type: GrantFiled: March 4, 1996Date of Patent: September 1, 1998Assignee: Rolic AGInventors: Richard Buchecker, Guy Marck
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Patent number: 5681504Abstract: A chiral dopant of the formula ##STR1## wherein ring A is 1,4-phenylene which is optionally substituted with one or more fluorine atoms, chlorine atoms, bromine atoms, cyano groups, or methyl groups, and in which one or two CH groups can be replaced by nitrogen, or is trans-1,4-cyclohexylene;Z is a single covalent bond, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- or --OCH.sub.2 --; X.sup.1,X.sup.2,X.sup.3,X.sup.4 each independently are hydrogen or fluorine;R.sup.1 is hydrogen, is alkyl with 1 to 12 carbon atoms which is optionally substituted with one or more fluorine or chlorine atoms and in which one or two non-adjacent CH.sub.2 groups can be replaced by --0--, is alkenyl with 2 to 12 carbon atoms, which is optionally substituted with one or more fluorine or chlorine atoms and in which one or two non-adjacent CH.sub.2 groups can be replaced by --O--, is a group of the formula ##STR2## and when R.sup.1 is bonded to an aromatic ring, can also be fluorine, chlorine, cyano, CF.sub.3, OCHF.sub.2 or --OCF.sub.3 ;R.Type: GrantFiled: December 5, 1995Date of Patent: October 28, 1997Assignee: Rolic AGInventors: Richard Buchecker, Guy Marck, Martin Schadt
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Patent number: 5667721Abstract: Liquid crystalline compounds having two dioxane rings, the dipole moments of which are unidirectional. These are compounds of the general formula ##STR1## wherein A and B each independently is cyclic or acyclic hydrophobic residues; andn is 0, 1 or 2.as well as liquid crystalline mixtures which contain such compounds and the use of such compounds and, respectively, mixtures for electro-optical display devices.Type: GrantFiled: February 21, 1996Date of Patent: September 16, 1997Assignee: Rolic AGInventors: Richard Buchecker, Guy Marck, Alois Villiger
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Patent number: 5662829Abstract: Compounds of the following formula are useful as liquid crystals: ##STR1## wherein R is a C.sub.1 -C.sub.12 alkyl or a C.sub.2 -C.sub.12 alkenyl;A is a single bond or trans-1,4-cydohexylene;Z.sup.1 and Z.sup.2 are independently a single bond or --CH.sub.2 CH.sub.2 --, except Z.sup.1 and Z.sup.2 cannot simultaneously be --CH.sub.2 CH.sub.2 --;ring B is trans-1,4-cyclohexylene or 1,4-phenylene; andn is 0 or 1,Liquid crystalline mixtures which contain such compounds are especially useful in electro-optical indicating devices.Type: GrantFiled: February 23, 1996Date of Patent: September 2, 1997Assignee: Rolic AGInventors: Richard Buchecker, Guy Marck
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Patent number: 5582767Abstract: The invention relates to liquid crystalline, multiply-substituted fluorinated tolane derivatives, their preparation, liquid crystalline mixtures which comprise such compounds and the use of these compounds and mixtures for electro-optical purposes.Type: GrantFiled: November 8, 1993Date of Patent: December 10, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Martin Schadt
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Patent number: 5518653Abstract: Optically active compounds of the formula ##STR1## wherein n stands for the number 0 or 1; Z.sup.1 is a single covalent bond or --CH.sub.2 CH.sub.2 --; Z.sup.2 is a single covalent bond, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, --COO-- or --OOC--; rings A.sup.1 and A.sup.2 each independently represent trans-1,4-cyclohexylene or optionally halogen-, cyano- and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; R.sup.2 is a group R.sup.4 or a group of the formula ##STR2## R.sup.4 is cyano, halogen, --OCY.sup.1 F.sub.2, --CY.sup.1 F.sub.2 or an alkyl group in which optionally one >CH--CH< is replaced by >C.dbd.C< and/or optionally one methylene group or two non-adjacent methylene groups is/are replaced by --O--, --COO-- and/or --OOC-- and/or optionally one methylene group is replaced by --CHY.sup.2 --; Y.sup.1 is hydrogen or fluorine; Y.sup.2 is halogen, cyano or methyl; R.sup.1 and R.sup.Type: GrantFiled: January 12, 1995Date of Patent: May 21, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Jurg Funfschilling, Martin Schadt
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Patent number: 5498367Abstract: A chiral dopant of the formula ##STR1## wherein ring A is 1,4-phenylene which is optionally substituted with one or more fluorine atoms, chlorine atoms, bromine atoms, cyano groups, or methyl groups, and in which one or two CH groups can be replaced by nitrogen, or is trans-1,4-cyclohexylene;Z is a single covalent bond, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- or --OCH.sub.2 --;X.sup.1,X.sup.2,X.sup.3,X.sup.4 each independently are hydrogen or fluorine;R.sup.1 is hydrogen, is alkyl with 1 to 12 carbon atoms which is optionally substituted with one or more fluorine or chlorine atoms and in which one or two non-adjacent CH.sub.2 groups can be replaced by --O--, is alkenyl with 2 to 12 carbon atoms, which is optionally substituted with one or more fluorine or chlorine atoms and in which one or two non-adjacent CH.sub.2 groups can be replaced by --O--, is a group of the formula ##STR2## and when R.sup.1 is bonded to an aromatic ring, can also be fluorine, chlorine, cyano, CF.sub.3, OCHF.sub.2 or --OCF.sub.3 ;R.sup.Type: GrantFiled: February 17, 1995Date of Patent: March 12, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Guy Marck, Martin Schadt
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Patent number: 5486310Abstract: Optically active compounds of the formula ##STR1## wherein rings A, B and C each independently are unsubstituted or each are 1,4-phenylene substituted with at least one of halogen-, cyano-, methyl- or methoxy in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; R.sup.1 is a radical of an optically active terpene alcohol after cleavage of the hydroxy group or a group --(CH.sub.2).sub.m --C*HX.sup.1 --R.sup.3 ; R.sup.2 is a radical of an optically active terpene alcohol after cleavage of the hydroxy group or a group --(CH.sub.2).sub.n --C*HX.sup.2 --R.sup.4 ; m and n each independently stand for the number 0 or 1: C* denotes a chiral carbon atom; X.sup.1 and X.sup.2 each independently are fluorine, chlorine, cyano, methyl or methoxy; R.sup.3 and R.sup.4 each independently denote a group R, phenyl or phenyl substituted with R, with the proviso that R.sup.3 is different from X.sup.1 and R.sup.4 is different from X.sup.Type: GrantFiled: February 18, 1994Date of Patent: January 23, 1996Assignees: Hoffmann-La Roche Inc., Niopic Moscow Research and Production AssociationInventors: Richard Buchecker, Nina I. Chernova, Alexander V. Ivaschenko, Marina V. Loseva, Olga S. Petrashevich, Evgeniy P. Pozhidaev, Arnold Z. Rabinovich, Martin Schadt
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Patent number: 5478497Abstract: Compounds of the formula ##STR1## wherein rings A, B and C, Z.sup.1, Z.sup.2, Z.sup.3, R.sup.1, R.sup.2 and R.sup.3 are defined in the specification, their manufacture, liquid crystalline mixtures which contain such compounds and the use of these compounds for electro-optical purposes.Type: GrantFiled: February 1, 1995Date of Patent: December 26, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Martin Schadt, Alois Villiger
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Patent number: 5454974Abstract: Compounds of the formula ##STR1## wherein X.sup.1 denotes fluorine or chlorine and X.sup.2 denotes hydrogen, fluorine or chlorine; R.sup.1 is 3E-alkenyl, 4-alkenyl, 2E-alkenyloxy or 3-alkenyloxy; n stands for the number 0 or 1; one of the groups Y.sup.1 and Y.sup.2 is a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- or --OCH.sub.2 -- and the other of the groups Y.sup.1 and Y.sup.2 is a single covalent bond; and rings A.sup.1 and A.sup.2 each individually are substituted or unsubstituted trans-1,4-cyclohexylene, in which optionally 2 non-adjacent CH.sub.2 groups are replaced by oxygen, or substituted or unsubstituted 1,4-phenylene, in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; with the proviso that X.sup.2 denotes fluorine or chlorine and/or Y.sup.1 or Y.sup.2 denotes --CH.sub.2 O-- or --OCH.sub.2 -- when simultaneously X.sup.1 is fluorine and R.sup.1 is 3E-alkenyl,and their use for liquid crystalline mixtures and electro-optical purposes.Type: GrantFiled: January 6, 1994Date of Patent: October 3, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Arthur Boller, Richard Buchecker, Martin Schadt, Alois Villiger
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Patent number: 5447658Abstract: Compounds of the general formula ##STR1## wherein R.sup.1 represents vinyl or straight-chain alkenyl with 3 to 7 carbon atoms,the manufacture of such compounds, liquid crystalline mixtures which contain such compounds as well as the use of such compounds for electro-optical purposes.Type: GrantFiled: June 17, 1994Date of Patent: September 5, 1995Assignees: Hoffman-La Roche Inc., Dainipppon Ink and Chemicals, Inc.Inventors: Richard Buchecker, Teodor Lukac, Martin Schadt, Haruyoshi Takatsu, Alois Villiger
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Patent number: 5413734Abstract: Compounds of the formula ##STR1## wherein ring A is trans-1,4-cyclohexylene, 1,4-phenylene, pyrimidine-2,5-diyl or trans-1,3-dioxane-2,5-diyl; n is either 0 or 1; ring B stands for 1,4-phenylene or trans-1,4-cyclohexylene; and R.sup.1 is 3E-alkenyl or on a saturated ring also 1E-alkenyl, their manufacture, liquid crystalline mixtures which contain these compounds as well as their use for electro-optical purposes.Type: GrantFiled: May 27, 1994Date of Patent: May 9, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Martin Schadt
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Patent number: 5399689Abstract: The present invention is concerned with novel chlorophenylalkoxyalkyl compounds of the general formula ##STR1## wherein R denotes an alkyl residue with 1 to 12 carbon atoms; n is a whole number of 2 to 7, ring A denotes trans-1,4-cyclohexylene or 1,4-phenylene; m is either 0 or 1; ring B is trans-1,4-cyclohexylene, 1,4-phenylene in which optionally one CH group or two non-adjacent CH groups is/are replaced by nitrogen or, when m stands for 1, also trans-1,3-dioxane-2,5-diyl; Y.sup.1 and Y.sup.2 each independently represent a single covalent bond or --CH.sub.2 CH.sub.2 --; and X denotes hydrogen, fluorine or chlorine, their manufacture, liquid crystalline mixtures which contain these compounds, their production and use for electro-optical purposes.Type: GrantFiled: February 11, 1993Date of Patent: March 21, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Martin Schadt, Haruyoshi Takatsu
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Patent number: 5399292Abstract: Fluoro-substituted phenyl-cyclohexylacetylenes have the formula: ##STR1## wherein R signifies alkyl, alkoxy, alkenyl or alkenyloxy with 1 or, respectively, 2 to 12 carbon atoms in which one CH.sub.2 group can be replaced by oxygen and/or one or more hydrogen atoms can be replaced by fluorine atoms, with the proviso that two oxygen atoms are not directly adjacent;A.sup.1 represents 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl;A.sup.2 signifies trans-1,4-cyclohexylene or 1,4-phenylene which is optionally substituted with fluorine;Z.sup.1 signifies a single covalent bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O-- or, when ring A.sup.1 represents a saturated ring, also the trans form of --CH.dbd.CH(CH.sub.2).sub.2 -- or --CH.dbd.CHCH.sub.2 O--;Z.sup.2 signifies a single covalent bond, --CH.sub.2 --CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.Type: GrantFiled: May 2, 1994Date of Patent: March 21, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Martin Schadt
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Patent number: 5372746Abstract: Compounds of the general formula ##STR1## wherein ring A represents 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl;Z signifies a single covalent bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O-- or, where ring A represents a saturated ring, also the trans form of --CH.dbd.CH(CH.sub.2).sub.2 -- or --CH.dbd.CHCH.sub.2 O--;X signifies fluorine, chlorine, cyano, --CF.sub.3, --OCF.sub.3 or --OCHF.sub.2 ;Y.sup.1, Y.sup.2 each independently signify fluorine or hydrogen; andR signifies alkyl, alkoxy, alkenyl or alkenyloxy with 1 or, respectively, 2 to 12 carbon atoms in which one CH.sub.2 group or two non-adjacent CH.sub.Type: GrantFiled: November 17, 1992Date of Patent: December 13, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Martin Schadt
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Patent number: 5360577Abstract: Optically active compounds of the general formula ##STR1## wherein n stands for the number 0 or 1; R.sup.3 denotes a group R.sup.4 or a group of the general formula ##STR2## A.sup.1, A.sup.2 and A.sup.3 each independently represent 1,4-phenylene, which is unsubstituted or mono- or multiply-substituted with halogen, cyano and/or methyl and in which, where it is unsubstituted, 1 or 2 CH groups is/are optionally replaced by nitrogen, trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diyl, bycyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, tetralin-2,6-diyl or trans-decalin-2,6-diyl; Z.sup.1 and Z.sup.4 each independently signify a single covalent bond or --CH.sub.2 CH.sub.2 --; Z.sup.2 and Z.sup.3 each independently denote a single covalent bond, --CH.sub.2 CH.sub.2 --, --COO--, --OOC--, --CH.sub.2 O--, --OCH.sub.2 --, --C.tbd.C--, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.3 O--, --O(CH.sub.2).sub.3 -- or the trans form of --CH.dbd.CH--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --CH.dbd.CH--, --CH.dbd.CH--CH.sub.Type: GrantFiled: September 17, 1992Date of Patent: November 1, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Stephen Kelly
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Patent number: 5356563Abstract: Optically active compounds of the formula ##STR1## wherein m stands for the number 1 and R.sup.2 is an unsubstituted or halogen-substituted alkyl or alkenyl group in which optionally one methylene group is replaced by oxygen and/or optionally one methylene group is replaced by an ester group --COO-- or --OOC--; or m stands for the number 0 or 1 and R.sup.2 denotes a group of the formula ##STR2## R.sup.1 and R.sup.3 each independently represent an alkyl or alkenyl group in which optionally one methylene group is replaced by oxygen; Z.sup.1, Z.sup.2 and Z.sup.3 each independently are a single covalent bond, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --COO-- or --OOC--; n stands for the number 0 or 1; rings A.sup.1 and A.sup.2 each independently are unsubstituted or halogen, cyano and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; and C.sup.* denotes a chiral carbon atom; with the proviso that simultaneously R.sup.Type: GrantFiled: June 9, 1993Date of Patent: October 18, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Stephen Kelly, Frans Leenhouts