Patents by Inventor Alois Villiger
Alois Villiger 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: 4980486Abstract: This invention concerns compounds of the formula: ##STR1## wherein X is a single covalent bond, --CH.sub.2 CH.sub.2 --, 1,4-phenylene, a 2,5-disubstituted pyrimidine ring or a group of the formula: ##STR2## ring A is trans-1,4-cyclohexylene or, when X is a single covalent bond, ring A may also be 1,4-phenylene, a 2,5-disubstituted pyrimidine ring or a trans-2,5-disubstituted m-dioxane ring; andR.sup.1 is straight-chain trans-1-alkenyl having 2 to 12 carbon atoms or straight-chain trans-3-alkenyl having 4 to 12 carbon atoms or, when X is --CH.sub.2 CH.sub.2 --, R.sup.1 may also be 1,4-phenylene, a 2,5-disubstituted pyrimidine ring or a group of formula IA or when ring A is a 2,5-disubstituted pyrimidine ring of a trans-2,5-disubstituted m-dioxane ring, R.sup.1 may also be straight-chain alkyl with 1 to 12 carbon atoms; and one of the benzene rings may have a lateral fluorine substituent;their manufacture, and liquid crystalline mixtures and electro-optical device containing same.Type: GrantFiled: April 3, 1987Date of Patent: December 25, 1990Assignee: Hoffmann-La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
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Patent number: 4915480Abstract: This invention concerns compounds of the formula: ##STR1## wherein X is a single covalent bond, --CH.sub.2 CH.sub.2 --, 1,4-phenylene, a 2,5-disubstituted pyrimidine ring or a group of the formula: ##STR2## ring A is trans-1,4-cyclohexylene or, when X is a single covalent bond, ring A may also be 1,4-phenylene, a 2,5-disubstituted pyrimidine ring or a trans-2,5-disubstituted m-dioxane ring; andR.sup.1 is straight-chain trans-1-alkenyl having 2 to 12 carbon atoms or straight-chain trans-3-alkenyl having 4 to 12 carbon atoms or, when X is --CH.sub.2 CH.sub.2 --, R.sup.1 may also be 1,4-phenylene, a 2,5-disubstituted pyrimidine ring or a group of formula IA or when ring A is a 2,5-disubstituted pyrimidine ring or a trans-2, 5-disubstituted m-dioxane ring, R.sup.1 may also be straight-chain alkyl with 1 to 12 carbon atoms; and one of the benzene rings may have a lateral fluorine substituent;their manufacture, and liquid crystalline mixtures and electro-optical devices containing same.Type: GrantFiled: July 13, 1988Date of Patent: April 10, 1990Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
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Patent number: 4783280Abstract: There is described a liquid crystalline mixture for electro-optical devices which are operated according to the two-frequency matrix addressing procedure. The mixture consists of three components A, B and C, each of which contains one or more compounds. Component A has a viscosity of at most about 40 cp, a clearing point of at least about 40.degree. C. and a dielectric anisotropy between about -2 and about +1. Component B has a dielectric anisotropy below about -2 both above and below the cross-over frequency of the total mixture and component C has a dielectric anisotropy above about +10, a clearing point of at least about 100.degree. C. and there is a cross-over frequency in the total mixture of at most about 15 kHz at 20.degree. C. Novel compounds for such mixtures and their manufacture and use are also described. The novel mixtures make possible especially high multiplex rates and short response times.Type: GrantFiled: May 20, 1987Date of Patent: November 8, 1988Assignee: Hoffmann-La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
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Patent number: 4708441Abstract: Compounds of the formula ##STR1## wherein X.sup.2 is a single covalent bond or --COO--; X.sup.1 is a single covalent bond, --COO--, --CH.sub.2 CH.sub.2 -- or when X.sup.2 is --COO--, X.sup.1 also can be p--C.sub.6 H.sub.4 --, p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4, p--C.sub.6 H.sub.4 --COO-- or --COO--p--C.sub.6 H.sub.4 ; ring A is a benzene ring or trans-1,4-cyclohexylene; ring B is a benzene ring or when X.sup.2 is --COO-- and X.sup.1 is a single covalent bond, --COO-- or --CH.sub.2 CH.sub.2 --, ring B also can be trans-1,4-cyclohexylene; Z.sup.1, Z.sup.2 and Z.sup.3 individually are hydrogen or when positioned on a benzene ring which is not linked directly with a further ring via a single covalent bond, Z.sup.1, Z.sup.2 and Z.sup.3 also can be halogen, cyano or methyl; Y.sup.2 is cyano, nitro, 2,2-dicyanovinyl or when Y.sup.1 is hydrogen Y.sup.2 also can be 2,2-dicyano-1-methylvinyl; Y.sup.1 is halogen, cyano, C.sub.1 -C.sub.3 -alkyl or, when X.sup.Type: GrantFiled: August 16, 1985Date of Patent: November 24, 1987Assignee: Hoffman-La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
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Patent number: 4630896Abstract: Compounds of the formula: ##STR1## wherein one of X.sup.1 and X.sup.2 is --CH.sub.2 CH.sub.2 -- and the other is --CH.sub.2 CH.sub.2 -- or a single covalent bond,ring A is 1,4-phenylene or trans-1,4-cyclohexylene, andR.sup.1 is straight-chain C.sub.1 -C.sub.12 -alkyl or when positioned on a 1,4-phenylene ring R.sup.1 may also be straight chain C.sub.1 -C.sub.12 -alkoxy.Type: GrantFiled: May 29, 1984Date of Patent: December 23, 1986Assignee: Hoffmann-La Roche Inc.Inventors: Martin Petrzilka, Alois Villiger
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Patent number: 4550981Abstract: Compounds of the formula ##STR1## wherein X.sup.2 is a single covalent bond or --COO--; X.sup.1 is a single covalent bond, --COO--, --CH.sub.2 CH.sub.2 -- or when X.sup.2 is --COO--, X.sup.1 also can be p--C.sub.6 H.sub.4 --, p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4, p--C.sub.6 H.sub.4 --COO-- or --COO--p--C.sub.6 H.sub.4 ; ring A is a benzene ring or trans-1,4-cyclohexylene; ring B is a benzene ring or when X.sup.2 is --COO-- and X.sup.1 is a single covalent bond, --COO-- or --CH.sub.2 CH.sub.2 --, ring B also can be trans-1,4-cyclohexylene; Z.sup.1, Z.sup.2 and Z.sup.3 individually are hydrogen or when positioned on a benzene ring which is not linked directly with a further ring via a single covalent bond, Z.sup.1, Z.sup.2 and Z.sup.3 also can be halogen, cyano or methyl; Y.sup.2 is cyano, nitro, 2,2-dicyanovinyl or when Y.sup.1 is hydrogen Y.sup.2 also can be 2,2-dicyano-1-methylvinyl; Y.sup.1 is halogen, cyano, C.sub.1 -C.sub.3 -alkyl or, when X.sup.Type: GrantFiled: September 9, 1983Date of Patent: November 5, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
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Patent number: 4526704Abstract: Compounds of the formula ##STR1## wherein n is 0 or 1; one of X.sup.1 and X.sup.2 is --COO-- or --OOC-- and the other is a single covalent bond or --CH.sub.2 CH.sub.2 --; X.sup.3 and X.sup.4 individually are a single covalent bond or --CH.sub.2 CH.sub.2 --, with the proviso that at most one of X.sup.1, X.sup.2, X.sup.3 and X.sup.4 is --CH.sub.2 CH.sub.2 --; rings A.sup.1 and A.sup.5 individually are a group of the formula ##STR2## or trans-1,4-cyclohexylene; rings A.sup.2, A.sup.3 and A.sup.4 individually are a group of formula II or, when ring A.sup.2, A.sup.3 or A.sup.4 is not linked with at least one of the other two of these rings by a single covalent bond then such ring also can be trans-1,4-cyclohexylene, with the proviso that at least one of rings A.sup.1 through A.sup.5 is a group of formula II; Y is hydrogen, or when Y is attached to a ring of formula II which is not linked with another ring via a single covalent bond, Y also can be fluorine, chlorine or methyl; and R.sup.1 and R.sup.Type: GrantFiled: July 11, 1983Date of Patent: July 2, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
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Patent number: 4462923Abstract: Pyrimidines of the formula: ##STR1## wherein Y is nitrogen and Z is .dbd.CH--, or Z is nitrogen and Y is .dbd.CH--; R.sup.1 is alkyl and R.sup.2 is cyano, alkyl, p-alkylphenyl or trans-4-alkylcyclohexyl; where each alkyl denotes either a straight chain alkyl group of 1 to 12 carbon atoms or a branched chain alkyl group of the formula C.sub.2 H.sub.5 --CH(CH.sub.3)--(CH.sub.2).sub.n, n is 1, 2 or 3; with the proviso that the compound contains at most only one of said branched chain alkyl group and with the further proviso that the sum of the carbon atoms in all of the alkyl groups within the compound is at most 14are described. Liquid crystalline mixtures comprising Compound I as well as their use in electro-optical devices also are disclosed.Type: GrantFiled: October 7, 1981Date of Patent: July 31, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Arthur Boller, Martin Schadt, Alois Villiger
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Patent number: 4460770Abstract: There is described a liquid crystalline mixture for electro-optical devices which are operated according to the two-frequency matrix addressing procedure. The mixture consists of three components A, B and C, each of which contains one or more compounds. Component A has a viscosity of at most about 40 cp, a clearing point of at least about 40.degree. C. and a dielectric anisotropy between about -2 and about +1. Component B has a dielectric anisotropy below about -2 and component C has a dielectric anisotropy above about +10, a clearing point of at least about 100.degree. C. and there is a cross-over frequency in the total mixture of at most about 15 kHz at 20.degree. C.Novel compounds for such mixtures and their manufacture and use are also described.The novel mixtures make possible especially high multiplex rates and short response times.Type: GrantFiled: June 10, 1982Date of Patent: July 17, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
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Patent number: 4439015Abstract: Disubstituted ethanes of the formula ##STR1## wherein R.sup.2 is --R.sup.3, --OR.sup.3, --CO--R.sup.3, --CO--OR.sup.3 or O--CO--R.sup.3, R.sup.1 and R.sup.3 each are straight-chain alkyl of 1 to 12 carbon atoms and n is 1 or 2,are described. Liquid crystalline mixtures comprising Compound I as well as their use in electro-optical devices also are disclosed.Type: GrantFiled: January 22, 1982Date of Patent: March 27, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Roland Rich, Alois Villiger, Erich Widmer
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Patent number: 4395350Abstract: Liquid crystal mixtures containing a coloring substance which comprise about 5 to about 40 weight % of trans-p-[5-(4-alkylcyclohexyl)-2-pyrimidinyl]benzonitriles, about 10 to about 60 weight % of trans-4-alkylcyclohexane carboxylic acid phenyl esters and about 0.1 to about 15 weight % of one or more coloring substances of the formula ##STR1## wherein m stands for the number 1 and X is alkoxy and Y is nitro; or m stands for the number 1 or 2; and X is p-alkoxyphenyl and Y is nitro or dialkylamino, or X is alkoxy and Y is -p-nitrophenyl or -(dialkylamino)phenyl; or m stands for the number 2, and X is alkoxy and Y is alkoxy, nitro or dialkylamino, or both X and Y are dialkylamino; and wherein the alkoxy denotes a straight-chain group containing 1 to 12 carbon atoms and the alkyl groups in the dialkylamino each denote a straight-chain alkyl group containing 1 to 4 carbon atoms are described.Type: GrantFiled: July 1, 1981Date of Patent: July 26, 1983Assignee: Hoffmann-La Roche Inc.Inventors: Arthur Boller, Alfred Germann, Martin Schadt, Alois Villiger
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Patent number: 4391731Abstract: Compounds of the formula ##STR1## wherein ring A is saturated or aromatic and a saturated ring A which may be present is trans-linked with the second ring; R.sup.1 is a straight-chain alkyl or alkoxy group containing 1 to 11 carbon atoms; R.sup.2 is cyano, a straight-chain alkyl group containing 1 to 11 carbon atoms, an ester group of the formula ##STR2## or, when ring A is saturated, additionally a straight-chain alkoxy group containing 1 to 11 carbon atoms; in the ester group of formula II ring B is either aromatic and X is oxygen or sulfur and R.sup.3 is cyano or a straight-chain alkyl or alkoxy group containing 1 to 10 carbon atoms, or ring B is a trans-1,4-disubstituted cyclohexane ring and X is oxygen and R.sup.3 is cyano or a straight-chain alkyl group containing 1 to 10 carbon atoms; and the total number of carbon atoms in the alkyl and/or alkoxy groups amounts to at most 12, are described. The compounds of formula I are useful in liquid crystal mixtures.Type: GrantFiled: August 3, 1981Date of Patent: July 5, 1983Assignee: Hoffmann-La Roche Inc.Inventors: Arthur Boller, Martin Schadt, Alois Villiger
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Patent number: 4389329Abstract: Pyrimidine derivatives of the formula ##STR1## wherein at least one of rings A and B is a trans-1,4-disubstituted cyclohexane ring and the other, optionally, may be aromatic and R is straight-chain alkyl or alkoxy of 1 to 10 carbon atoms or a branched-chain alkyl group of the formula C.sub.2 H.sub.5 --CH(CH.sub.3)--(CH.sub.2).sub.n -- wherein n is 1, 2 or 3, are described. Processes for the preparation of the compounds of formula I as well as their uses in liquid crystalline mixtures are also described.Type: GrantFiled: January 30, 1981Date of Patent: June 21, 1983Assignee: Hoffmann-La Roche Inc.Inventors: Arthur Boller, Martin Schadt, Alois Villiger
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Patent number: 4364838Abstract: Liquid crystalline mixtures comprising trans-phenyldioxane, phenylpyrimidine and phenylbenzoate compounds which are useful in electro-optical apparatuses are disclosed.Type: GrantFiled: November 10, 1980Date of Patent: December 21, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Arthur Boller, Alfred Germann, Martin Schadt, Alois Villiger
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Patent number: 4273929Abstract: Pyrimidine derivatives of the formula ##STR1## wherein at least one of rings A and B is a trans-1,4-disubstituted cyclohexane ring and the other, optionally, may be aromatic and R is straight-chain alkyl or alkoxy of 1 to 10 carbon atoms or a branched-chain alkyl group of the formulas C.sub.2 H.sub.5 --CH(CH.sub.3)--(CH.sub.2).sub.n --wherein n is 1, 2 or 3, are described. Processes for the preparation of the compounds of formula I as well as their uses in liquid crystalline mixtures are also described.Type: GrantFiled: January 29, 1980Date of Patent: June 16, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Arthur Boller, Martin Schadt, Alois Villiger