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).

  • Patent number: 4980486
    Abstract: 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: Grant
    Filed: April 3, 1987
    Date of Patent: December 25, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
  • Patent number: 4915480
    Abstract: 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: Grant
    Filed: July 13, 1988
    Date of Patent: April 10, 1990
    Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
  • Patent number: 4783280
    Abstract: 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: Grant
    Filed: May 20, 1987
    Date of Patent: November 8, 1988
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
  • Patent number: 4708441
    Abstract: 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: Grant
    Filed: August 16, 1985
    Date of Patent: November 24, 1987
    Assignee: Hoffman-La Roche Inc.
    Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
  • Patent number: 4630896
    Abstract: 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: Grant
    Filed: May 29, 1984
    Date of Patent: December 23, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Martin Petrzilka, Alois Villiger
  • Patent number: 4550981
    Abstract: 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: Grant
    Filed: September 9, 1983
    Date of Patent: November 5, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
  • Patent number: 4526704
    Abstract: 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: Grant
    Filed: July 11, 1983
    Date of Patent: July 2, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
  • Patent number: 4462923
    Abstract: 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: Grant
    Filed: October 7, 1981
    Date of Patent: July 31, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Arthur Boller, Martin Schadt, Alois Villiger
  • Patent number: 4460770
    Abstract: 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: Grant
    Filed: June 10, 1982
    Date of Patent: July 17, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
  • Patent number: 4439015
    Abstract: 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: Grant
    Filed: January 22, 1982
    Date of Patent: March 27, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Roland Rich, Alois Villiger, Erich Widmer
  • Patent number: 4395350
    Abstract: 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: Grant
    Filed: July 1, 1981
    Date of Patent: July 26, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Arthur Boller, Alfred Germann, Martin Schadt, Alois Villiger
  • Patent number: 4391731
    Abstract: 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: Grant
    Filed: August 3, 1981
    Date of Patent: July 5, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Arthur Boller, Martin Schadt, Alois Villiger
  • Patent number: 4389329
    Abstract: 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: Grant
    Filed: January 30, 1981
    Date of Patent: June 21, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Arthur Boller, Martin Schadt, Alois Villiger
  • Patent number: 4364838
    Abstract: Liquid crystalline mixtures comprising trans-phenyldioxane, phenylpyrimidine and phenylbenzoate compounds which are useful in electro-optical apparatuses are disclosed.
    Type: Grant
    Filed: November 10, 1980
    Date of Patent: December 21, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Arthur Boller, Alfred Germann, Martin Schadt, Alois Villiger
  • Patent number: 4273929
    Abstract: 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: Grant
    Filed: January 29, 1980
    Date of Patent: June 16, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Arthur Boller, Martin Schadt, Alois Villiger