Polycyclo Ring System Patents (Class 568/665)
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Patent number: 4900718Abstract: Described is 3-(2-bornyloxy)-2-methyl-1-propanol defined according to the chemical structure: ##STR1## and organoleptic uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, perfumed polymers, cosmetic powders and hair preparations.Type: GrantFiled: July 28, 1989Date of Patent: February 13, 1990Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, William J. Fylak, Joseph A. Mc Ghie, Jordi Castells
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Patent number: 4895987Abstract: Ruthenium-cobalt- or cobalt-containing catalysts which have been promoted with phosphonites or phosphinites effectively catalyze the dealkoxyhydroxymethylation of aldehyde acetals to form glycol monoethers. Methylal, for example, may be reacted with syngas, i.e., CO and H.sub.2, in the presence of these phosphonite- or phosphinite-promoted cobalt or ruthenium- cobalt catalysts to form the monomethyl ether of ethylene glycol. In a like manner acetaldehyde may be converted to the corresponding propylene glycol monoether. The process may advantageously be carried out with high yields and selectivities in the presence of a polar or non-polar organic solvent in combination with the catalyst system of this invention.The invention is also directed to the phosphonite- or phosphonite-promoted cobalt and ruthenium-cobalt catalyst system per se.Type: GrantFiled: June 6, 1986Date of Patent: January 23, 1990Assignee: Sun Refining and Marketing CompanyInventors: D. Michael Duggan, James E. Lyons, Harry K. Myers, Robert E. Ledley
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Patent number: 4874891Abstract: Compounds of the formula: ##STR1## and the pharmaceutically acceptable esters thereof, wherein rings A and B are selected from the group consisting of ##STR2## wherein x represents an aromatic ring, or the presence or absence of 0, 1, or 2 conjugated or unconjugated .pi. bond(s), andwherein x represents the presence or absence of 0, 1, or 2 conjugated or unconjugated .pi. bond(s), andwherein a non-aromatic .pi. bond, if present, may optionally be converted to an epoxide;and wherein the dotted line represents the presence or absence of a .pi. bond,and wherein:R.sup.1 is H, acyl(1-6), or alkyl(1-6);R.sup.2 is H, alkyl(1.varies.6), 2-propynyl, or allenyl;R.sup.3 and R.sup.4 is each independently H or OR.sup.5, wherein R.sup.5 is H, acyl(1-6), or alkyl(1-6); andwherein R.sub.1 and R.sub.2 is each independently H, alkyl(1-6) or is --C.tbd.CR.sub.3, --CH.dbd.CHR.sub.3, or --CH.dbd.C.dbd.CHR.sub.3, wherein R.sub.3 is selected from the group consisting of H, halo, CF.sub.Type: GrantFiled: May 1, 1986Date of Patent: October 17, 1989Assignee: Washington UniversityInventors: Douglas F. Covey, Ricahrd J. Auchus
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Patent number: 4855322Abstract: A compound of the formula ##STR1## wherein Q is CO, CH(OR), CR(OH), or CR (OC)-lower alkyl); R is H, or C.sup.1-2 -alkyl;X is hydroxyalkyl,methoxy-C.sup.2-11 -alkyl, ethoxy-C.sup.2-11 -alkyl or oxo-C.sup.2-11 -alkyl, formyl-C.sup.2-11 -alkyl,carboxy-C.sup.2-11 -alkyl or (C.sub.1-2 -alkyl) oxycarbonyl-C.sup.2-11 -alkyl;c is 1 or 2;p or w are 0, 1 or 2 and the sum of p and w is 1 to 4;and a pharmaceutically acceptable salt thereof.Type: GrantFiled: June 1, 1987Date of Patent: August 8, 1989Assignee: CBD CorporationInventors: Walter J. Kasha, Chantal S. Burnison
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Patent number: 4853151Abstract: Dispirotetradecanes of the formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of each other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,A.sup.1 and A.sup.2 are each independently of each other trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,Z.sup.1 and Z.sup.2 are each independently of each other --C--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,m and n are each 0, 1 or 2,(m+n) 0, 1 or 2,X.sup.1, X.sup.2, X.sup.3 and X.sup.Type: GrantFiled: August 11, 1987Date of Patent: August 1, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankfter HaftungInventors: Fritz Vogtle, Wolfgang Calaminus
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Patent number: 4846998Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 Iin whichR.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --A-- or --A--A.sup.4 --,A is a trans-1,4-cyclohexylene group which can be substituted in the 2-, 3-, 5- and/or 6-position one or more times by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group which each have 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, and which may also be substituted in the 1- and/or 4-position,A.sup.2, A.sup.3 and A.sup.Type: GrantFiled: November 21, 1986Date of Patent: July 11, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Ludwig Pohl, Bernhard Scheuble, Reinhard Hittich, Rudolf Eidenschink, Hans A. Kurmeier, Andreas Wachtler
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Patent number: 4839340Abstract: The invention provides derivatives of bornane-3-spiro-1'-cyclopentane with woody note scent useful as a base component in perfumery formulations which comprises those having a substituting group selected from a methoxyl, ethoxyl, formyloxyl and acetoxyl groups or two of substituting groups being either a hydroxyl group and a methyl group or a hydroxyl group and an ethyl group at the 2-position synthesized by any of the reactions of borane-3-spiro-1'-cyclopentan-2--ol or bornane-3-spiro-1'-cyclopentan-2-one with any of the reagents selected in accordance with the substituting group(s) to be introduced.The invention also provides perfumery compositions containing the above.Type: GrantFiled: June 29, 1988Date of Patent: June 13, 1989Assignee: Kao CorporationInventors: Yoshiaki Fujikura, Tomohito Kitsuki, Manabu Fujita, Nao Toi
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Patent number: 4782192Abstract: Described are organoleptic compounds having the generic structure: ##STR1## wherein R.sub.1 represents hydrogen, methyl or acetyl and wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent the same or different hydrogen, methyl or ethyl.Type: GrantFiled: June 24, 1982Date of Patent: November 1, 1988Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, Joseph A. McGhie, Futoshi Fujioka, Takao Yoshida
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Patent number: 4772411Abstract: Described are ethyl norbornyl alkyl ethers of our invention defined according to the generic structure: ##STR1## wherein R represents C.sub.1 -C.sub.4 lower alkyl and organoleptic uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to bleach compositions, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations. Also described is a process for preparing such ethyl norbornyl alkyl ethers of our invention by means of reaction of compounds defined according to the structure: ##STR2## and/or compounds defined according to the structure: ##STR3## in admixture with compounds having the structure: ##STR4## with hydrogen in the presence of a hydrogenation catalyst.Type: GrantFiled: January 28, 1988Date of Patent: September 20, 1988Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Margo Androulakis, Marie R. Hanna
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Patent number: 4723005Abstract: New anisotropic compounds of the formula (1) are useful in liquid crystal mixtures for electrooptical displays; at least one of the end groups of the compounds (1) is an alkyl group which carries cyano or halogen in a terminal or non-terminal position. This offers advantages for longitudinal polarization and/or cross-polarization of the anisotropic compounds with the aid of the comparatively highly polarizing cyano or halogen substituents, in particular high clear points, low .DELTA..epsilon./.epsilon..perp. values and/or negative .DELTA..epsilon. values.Type: GrantFiled: September 10, 1984Date of Patent: February 2, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4707295Abstract: Bicyclooctane derivatives of the formula IR.sup.1 --A.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 independently of one another are each an alkyl group which has 1-12 C atoms and in which it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by O atoms and/or CO groups and/or --O13 CO groups and/or --CO--O groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 being also --A.sup.3 --R.sup.3,A.sup.1 is a 1,4-cyclohexylene group which is unsubstituted or substituted in the 1-position and/or 2-position and/or 3-position and/or 4-position by alkyl which has in each case 1-5 C atoms and is unsubstituted or substituted or fluorinated, and in which it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by one or two different groupings from the group --O--, --CO--, --CH.dbd.CH--, --S--, --SO-- or --SO.sub.2 --, or is substituted by F, Cl, Br, CN and/or CHO,A.sup.2 is a 1,4-bicyclo[2.2.2] octylene group,--A.sup.3 --R.sup.3 is --Cy--R.sup.Type: GrantFiled: March 24, 1986Date of Patent: November 17, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ludwig Pohl, Bernhard Scheuble, Andreas Wachtler, Reinhard Hittich, Peter Fuss
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Patent number: 4700008Abstract: There is disclosed a novel 4,8-dimethylbicyclo[3.3.1]nonane derivative represented by the formula [I]: ##STR1## wherein X and Y have the same meanings as defined in the specification. The compound of the present invention has an unique and strong perfume and hence is expected to be useful as perfumery.Type: GrantFiled: November 25, 1983Date of Patent: October 13, 1987Assignee: Mitsubishi Yuka Fine Chemicals Co., Ltd.Inventors: Makoto Takeda, Hiroshi Iwane, Akira Yoshida, Teruo Mori
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Patent number: 4698180Abstract: A perfume composition comprises a perfumery carrier and isobornyl 2-hydroxypropyl ether.Type: GrantFiled: May 23, 1986Date of Patent: October 6, 1987Assignee: Union Camp CorporationInventor: Mark S. Pavlin
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Patent number: 4686289Abstract: New anisotropic compounds with a cross-polarizing substituent have the formula (1) ##STR1## The increase in .epsilon..perp. is achieved by the polarizing group X, preferably the cyano group or a halogen atom, which is not laterally on the ring, as with the known compounds, but is on the bridge, that is to say is part of the main bridge bonding rings A and B to one another. Ring A has the formula (1a) or (1b) given herein and is always cycloaliphatic, while ring B can be identical to ring A or is an aromatic ring of the formula (1c) or (1d) herein. R.sup.1 and R.sup.2 are identical or different end groups of the formula (1e) herein.The radical X on the bridge causes less widening of the molecule than a radical X on a ring, which provides comparatively higher clear points and moreover enables aromatic rings to be omitted from the anisotropic compounds.Type: GrantFiled: February 25, 1986Date of Patent: August 11, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4683083Abstract: The invention concerns1. Mixtures of tricyclo[5.2.1.0.sup.2,6 ]decane derivatives, having principal isomers corresponding to the general formula A, whereinR.sup.1 and R.sup.2 are hydrogen atoms or are a methyl group or a hydrogen atom, one of the substituents being a methyl group and the other a hydrogen atom,R.sup.3 and R.sup.4 are hydrogen atoms or are a methyl group or a hydrogen atom, one of the substituents being a methyl group and the other a hydrogen atom,Y is a tetrahydrofurane system at C-4/C-5 or a substituted oxymethyl group at C-5 and a hydrogen atom at C-4,R.sup.5 is a hydrogen atom or a C.sub.1 -C.sub.6 -acyl-, C.sub.1 -C.sub.6 -alkyl-, C.sub.1 -C.sub.6 -alkenyl-, C.sub.1 -C.sub.4 -alkoxymethyl-, C.sub.1 -C.sub.2 alkoxycarbonyl-, formylmethyl-, or di-C.sub.1 -C.sub.4 -alkoxyethyl-group, andthe broken lines indicate a C--C-single bond and a C--C-double bond or alternatively two C--C-single bonds. ##STR1## 2.Type: GrantFiled: January 10, 1985Date of Patent: July 28, 1987Assignee: Dragoco Gerberding and Co. GmbHInventors: Ernst-Joachim Brunke, Hartmut Struwe
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Patent number: 4668431Abstract: Described are mixtures of hydroxybornyloxybutanes defined according to the generic structure: ##STR1## wherein in the mixture in each of the compounds one of R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is hydrogen as well as methods for augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles by adding thereto an aroma augmenting or enhancing quantity of said mixture of hydroxybornyloxybutanes. The mixture of hydroxybornyloxybutanes of our invention defined according to the structure: ##STR2## is prepared according to the process of reacting camphene having the structure: ##STR3## with 1,3-dihydroxybutane having the structure: ##STR4## in the presence of an acid catalyst such as a Lewis acid or a protonic acid.Type: GrantFiled: March 7, 1986Date of Patent: May 26, 1987Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4627933Abstract: Compounds of the formulaR.sup.1 --Q.sup.1 --(CH.sub.2).sub.m --(COO).sub.n --(CH.sub.2).sub.p --Q.sup.2 --R.sup.2whereinR.sup.1 and R.sup.2 are each independently alkyl or alkoxy each of 1-12 C atoms, F, Cl, Br, CN or --Q.sup.3 --R.sup.3, or one of R.sup.1 and R.sup.2 can also be H;Q.sup.1, Q.sup.2 and Q.sup.3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-bicyclo(2,2,2)-octylene or 1,3-dioxane-2,5-diyl, each of which is unsubstituted or substituted by 1-4 fluorine, chlorine or bromine atoms;R.sup.3 is alkyl or alkoxy each of 1-8 C atoms, H, F, Cl, Br or CN;m is 1, 2, 3, 4, 5 or 6; n is 0 or 1; and p is 0, 1, 2, 3, 4 or 5; the sum of (m+p) being 2, 4 or 6 and the sum of (m+n+p) being at least 3;but with the proviso that Q.sup.3 is unsubstituted 1,4-phenylene or 1,4-phenylene substituted by a fluorine, chlorine or bromine atom, only when n=1 or (m+p)=6 or at least one of R.sup.1 or R.sup.3 is F, Cl or Br or none of R.sup.1 to R.sup.3 is CN or two of the radicals R.sup.1 to R.sup.Type: GrantFiled: July 7, 1983Date of Patent: December 9, 1986Assignees: Merck Patent Gesellschaft mit beschrankter Haftung, The Secretary of State for Defense in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Rudolf Eidenschink, Joachim Krause, Beatrice M. Andrews, George W. Gray, Neil Carr
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Patent number: 4622430Abstract: Pentacyclo[6.3.0.0..sup.2,6.0.sup.3,10.0.sup.5,9 ]undecane and its derivatives are prepared. The compounds find use as antiviral agents.Type: GrantFiled: December 21, 1982Date of Patent: November 11, 1986Assignee: Noristan LimitedInventors: Theodor G. Dekker, Douglas W. Oliver, Friedrich O. Snyckers, Cornelis J. van der Schyf
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Patent number: 4622163Abstract: New anisotropic compounds with a cross-polarizing substituent have the formula (1) ##STR1## The increase in .epsilon..perp. is achieved by the polarizing group X, preferably the cyano group or a halogen atom, which is not laterally on the ring, as with the known compounds, but is on the bridge, that is to say is part of the main bridge bonding rings A and B to one another. Ring A has the formula (1a) or (1b) given herein and is always cycloaliphatic, while ring B can be identical to ring A or is an aromatic ring of the formula (1c) or (1d) herein. R.sup.1 and R.sup.2 are identical or different end groups of the formula (1e) herein. The radical X on the bridge causes less widening of the molecule than a radical X on a ring, which provides comparatively higher clear points and moreover enables aromatic rings to be omitted from the anisotropic compounds.Type: GrantFiled: September 10, 1984Date of Patent: November 11, 1986Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4620041Abstract: Described are ether carbinols defined according to the generic structure: ##STR1## wherein X.sub.1 represents a moiety selected from the group consisting of: ##STR2## and wherein Y.sub.1 represents C.sub.4 or C.sub.5 alkylene; C.sub.4 or C.sub.5 alkenylene or C.sub.4 or C.sub.5 alkynylene; processes for preparing such ether carbinols by means of first reacting allyl ethers with a mixture or carbon monoxide and hydrogen by means of an oxo reaction to produce ether carboxaldehydes and then reducing the thus formed ether carboxaldehydes to ether carbinols; or reacting camphene with appropriate diols; as well as methods for augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes and perfumed articles; foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes; and smoking tobaccos and smoking tobacco articles by adding thereto an aroma or taste augmenting or enhancing quantity of the thus produced ether carbinols.Type: GrantFiled: October 4, 1985Date of Patent: October 28, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4618729Abstract: The ruthenium-cobalt carbonyl metal cluster catalyst Co.sub.2 Ru(CO).sub.11 effectively catalyzes the dealkoxyhydroxymethylation of aldehyde acetals to form glycol monoethers. Methylal, for example, may be reacted with syngas, i.e., CO and H.sub.2, in the presence of this ruthenium-cobalt cluster catalyst to form the monomethyl ether of ethylene glycol.Type: GrantFiled: October 2, 1985Date of Patent: October 21, 1986Assignee: Sun Refining and Marketing CompanyInventors: D. Michael Duggan, James E. Lyons, Harry K. Myers, Jr.
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Patent number: 4593142Abstract: Catalysts comprising mixtures of HF and metal alkoxides and mixed metal alkoxides produce a sharply peaked alkoxylation distribution during the alkoxylation of organic materials.Type: GrantFiled: February 21, 1984Date of Patent: June 3, 1986Assignee: Vista Chemical CompanyInventor: Kang Yang
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Patent number: 4593143Abstract: Described are the hydroxyalkoxy norbornyl ethers or mixtures of same having the structure: ##STR1## wherein one of R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is hydrogen and wherein one of the dashed lines represents a carbon-carbon bond and the other of the dashed lines represents no bond as well as methods for augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles by adding thereto an aroma augmenting or enhancing quantity of at least one of said hydroxyalkoxy norbornyl ethers.Type: GrantFiled: August 31, 1984Date of Patent: June 3, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4590302Abstract: The invention relates to new terpene ethers of the formula ##STR1## in which R denotes a cyclic or bicyclic radical or an alkyl radical which is substituted by cyclic, bicyclic or tricyclic radicals, optionally via an oxygen bridge. The compounds are prepared by reaction of camphene with alcohols R--OH, in which R represents one of the above-mentioned radicals. The new ethers are used in the field of aroma substances and solvents, and as intermediates for plant protection agents, agents for combating pests and medicaments.Type: GrantFiled: July 25, 1984Date of Patent: May 20, 1986Assignee: Hoechst AktiengesellschaftInventors: Franz Scheidl, Manfred Gscheidmeier
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Patent number: 4564694Abstract: A colorless liquid crystalline compound having at least one 6-membered ring and non-cyclic end groups in the molecular skelton, said 6-membered containing two or more carbon atoms, at least one of which is directly bonded to a methylene group of a non-cyclic group having an alkoxy group at another end has a wide mesomorphic range. When said colorless liquid crystalline compound is mixed with a liquid crystal composition, the resulting mixture also has an enlarge mesomorphic range and in almost all cases has a reduced viscosity.Type: GrantFiled: February 24, 1982Date of Patent: January 14, 1986Assignees: Hitachi, Ltd., Kanto Chemical Co., Inc.Inventors: Yoichi Hirai, Tsunenori Fujii, Kaoru Koto, Kenji Suzuki, Masahiro Yoshida, Hisashi Okawa, Yoshiaki Okabe, Teruo Kitamura, Hisao Yokokura, Shintaroo Hattori, Akio Mukoh, Mikio Sato
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Patent number: 4544497Abstract: Liquid crystal compositions are described which comprise a mixture of compounds and which includes at least one additive compound characterized in that the composition includes one or more additive compounds of Formula I as follows: ##STR1## wherein R.sub.1 represents an alkyl group, R.sub.2 represents an alkyl or alkoxy group or hydrogen and ##STR2## represents a 1,4-disubstituted bicyclo(2,2,2)octane ring. The preparation and properties of novel compounds of Formula I are also described. These liquid crystal compositions are useful in display devices such as digital calculators and word displays.Type: GrantFiled: January 25, 1984Date of Patent: October 1, 1985Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Hilal M. Abdullah, Jennifer Constant, George W. Gray, Damien G. McDonnell, Kenneth J. Toyne
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Patent number: 4544775Abstract: Described are ether carbinols defined according to the generic structure: ##STR1## wherein X.sub.1 represents a moiety selected from the group consisting of: ##STR2## and wherein Y.sub.1 represents C.sub.4 or C.sub.5 alkylene; C.sub.4 or C.sub.5 alkenylene or C.sub.4 or C.sub.5 alkynylene; processes for preparing such ether carbinols by means of first reacting allyl ethers with a mixture of carbon monoxide and hydrogen by means of an oxo reaction to produce ether carboxaldehydes and then reducing the thus formed ether carboxaldehydes to ether carbinols; or reacting camphene with appropriate diols; as well as methods for augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes and perfumed articles; foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes; and smoking tobaccos and smoking tobacco articles by adding thereto an aroma or taste augmenting or enhancing quantity of the thus produced ether carbinols.Type: GrantFiled: August 24, 1984Date of Patent: October 1, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4539142Abstract: Described is the 4-(2-bornyloxy)-2-butyn-1-ol of our invention defined according to the structure: ##STR1## as well as methods for augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles by adding thereto an aroma augmenting or enhancing quantity of the 4-(2-bornyloxy)-2-butyn-1-ol of our invention.Type: GrantFiled: April 26, 1984Date of Patent: September 3, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4535148Abstract: Polyglycidyl ethers of tricyclodecane are provided which are useful as monomers in the production of cured epoxy resins. Also provided are polyallyl ethers of tricyclodecane which are novel intermediates in the preparation of the polyglycidyl ethers and a method of preparing the polyglycidyl ethers of this invention which uses the novel intermediates.Type: GrantFiled: August 1, 1984Date of Patent: August 13, 1985Assignee: Henkel CorporationInventors: Elizabeth J. Gladfelter, Edgar R. Rogier, Edward D. DiDomenico
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Patent number: 4521634Abstract: Described are ether carbinols defined according to the generic structure: ##STR1## wherein X.sub.1 represents a moiety selected from the group consisting of: ##STR2## and wherein Y.sub.1 represents C.sub.4 or C.sub.5 alkylene or C.sub.4 or C.sub.5 alkenylene or C.sub.4 or C.sub.5 alkynylene; processes for preparing such ether carbinols by means of first reacting allyl ethers with a mixture of carbon monoxide and hydrogen by means of an oxoreaction to produce ether carboxaldehydes and then reducing the thus formed ether carboxaldehydes to ether carbinols; or reacting camphene with appropriate diols; as well as methods for augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes and perfumed articles; foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes; and smoking tobaccos and smoking tobacco articles by adding thereto an aroma or taste augmenting or enhancing quantity of the thus produced ether carbinols.Type: GrantFiled: January 26, 1984Date of Patent: June 4, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4519943Abstract: Described are 5-alkoxybicyclo[2.2.1]heptane-2-oxypropane derivatives defined according to the structure: ##STR1## (wherein R represents C.sub.1 -C.sub.3 alkyl and wherein Z represents one of the moieties, carbinol having the structure: ##STR2## or carboxaldehyde having the structure: ##STR3## and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes or perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders, hair preparations, perfumed polymers and the like).Type: GrantFiled: September 26, 1983Date of Patent: May 28, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber, Patrick Whelan, Marie R. Hanna
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Patent number: 4497830Abstract: Compounds of Formula I ##STR1## wherein X is oxygen or CH.sub.2 ;A is CH.sub.2 --CH.sub.2, trans-CH.dbd.CH or C.tbd.C;W is free or functionally modified hydroxymethylene or free or functionally modified ##STR2## and the OH groups may be in the .alpha.- or the .beta.-position; D is straight chain or branched, saturated or unsaturated hydrocarbon aliphatic of from 1 to 10 carbon atoms, which may be substituted by fluorine;E is C.tbd.C or CR.sub.3 .dbd.CR.sub.4, R.sub.3 and R.sub.4 being different and being hydrogen or alkyl of 1 to 5 carbon atoms;R.sub.1 is free or functionally modified hydroxy; andR.sub.2 is alkyl, cycloalkyl, optionally substituted aryl or heterocyclic,have valuable pharmacological properties, e.g., hypotensive and bronchodilatory characteristics. They can furthermore be used for prophylaxis and therapy of coronary infarct and as a treatment for stroke. They are produced by means of reduction of the corresponding 1-carbonic acid derivatives.Type: GrantFiled: May 24, 1982Date of Patent: February 5, 1985Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Gerda Mannesmann, Bob Nieuweboer
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Patent number: 4493846Abstract: A compound of the formula ##STR1## wherein X.sup.1 is a free or esterified carboxyl group, a hydroxymethyl group, a cyano group, a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7-membered saturated heterocyclic group) or a group of the formula: ##STR3## (R.sup.a and R.sup.b are each as defined above), Y is an ethylene group or a vinylene group, R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sub.1 and R.sub.2, when taken together, means a single linkage to form a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.Type: GrantFiled: March 13, 1981Date of Patent: January 15, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Keiichi Ono, Akihiko Sugie, Hajime Kawakami, Shunsuke Sami, Atsuyuki Kojima, Junki Katsube
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Patent number: 4478743Abstract: Described is a compound having the structure: ##STR1## a norbornyl oxyacetaldehyde, prepared by oxidizing the norbornyl oxyethanol compound having the structure: ##STR2## using air or oxygen and a silver or copper chromite catalyst; and organoleptic uses of such oxidation product in the field of perfumery, colognes and perfumed articles (e.g. perfumed plastics, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions or drier-added fabric softener articles).Type: GrantFiled: February 23, 1984Date of Patent: October 23, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Robert P. Belko, Richard M. Boden, Marie R. Hanna
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Patent number: 4460793Abstract: A process for the production of a monochloromethyl ketone of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 each independently is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkinyl or aryl radical, orR.sup.1 and R.sup.2 together with the carbon atom to which they are attached form an optionally substituted carbocyclic ring,comprising reacting a 1,1-dichloroalkene of the formula ##STR2## with a phenolate of the formula ##STR3## in which R.sup.4 each independently is a halogen atom, a nitro group, or an optionally substituted alkyl, alkoxy or aryl radical,n is 0, 1, 2 or 3, andM is one equivalent of an alkali metal ion or alkaline earth metal ion,thereby to obtain a phenyl ether intermediate, and then subjecting the phenyl ether intermediate to an acid hydrolysis. The products are useful as intermediates in the synthesis of fungicides.Type: GrantFiled: December 11, 1981Date of Patent: July 17, 1984Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt, Gerhard Jager
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Patent number: 4450307Abstract: New hydroxy-containing alkyl-substituted bicycloalkane ether compositions useful in the preparation of valuable detergent and lubricating compositions are obtained by reacting an alkyl-substituted 2-norbornene with a polyhydric alcohol in the presence of an acidic catalyst.Type: GrantFiled: June 25, 1981Date of Patent: May 22, 1984Assignee: Texaco Inc.Inventors: Philip H. Moss, Edward C. Y. Nieh
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Patent number: 4443633Abstract: Described are hydrocarbyloxy alkanals defined according to the generic structure: ##STR1## wherein R.sub.1 represents one of the moieties: ##STR2## and R.sub.2 represents hydrogen or methyl prepared according to the process of first reacting an allyl alcohol defined according to the structure: ##STR3## with a hydrocarbon or hydrocarbyl halide defined according to the structureR.sub.1 '--Xhaving an electrophilic center wherein R.sub.1 ' is saturated or unsaturated hydrocarbyl and X represents halogen or hydrogen with the provisos that:R.sub.1 ' is saturated hydrocarbyl when X is halogen andR.sub.1 ' is unsaturated hydrocarbyl when X is hydrogen.Also described are organoleptic uses of such hydrocarbyloxy alkanals in the field of perfumery, colognes and perfumed articles, (e.g. perfumed plastics, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions or drier-added fabric softener articles).Type: GrantFiled: April 6, 1982Date of Patent: April 17, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, William L. Schreiber, Futoshi Fujioka, Patrick Chant, Lambert Dekker
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Patent number: 4439354Abstract: Described are compounds having the generic structure: ##STR1## wherein R.sub.1 represents hydrogen, methyl or acetyl and wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent the same or different hydrogen, methyl or ethyl; a process for preparing same using compounds designed according to the generic structure: ##STR2## and organoleptic uses thereof in perfumes, colognes and perfumed articles.Type: GrantFiled: October 13, 1981Date of Patent: March 27, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, Joseph A. McGhie, Futoshi Fujioka, Takao Yoshida
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Patent number: 4436934Abstract: New organopalladium reactions involving the addition of pi-allylpalladium compounds to strained bicyclic alkenes, and subsequent chain extension reactions employing the chemistry of organopalladium compounds are disclosed. By these techniques a large number of bicyclic prostaglandin analogs are prepared, which are useful as inhibitors of arachidonic acid induced platelet aggregation, and are specific inhibitors of thromboxane synthetase.Type: GrantFiled: December 28, 1981Date of Patent: March 13, 1984Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 4434073Abstract: Perhydrophenanthrene derivatives of formula I ##STR1## wherein R.sub.1 is alkyl of 1-10 C atoms and R.sub.2 is alkyl, alkoxy or alkanoyloxy each of 1-10 C atoms, H, Br, Cl or CN, have an extremely low optical anisotropy and are particularly suitable as components of liquid-crystalline dielectrics.Type: GrantFiled: December 8, 1982Date of Patent: February 28, 1984Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Wolfgang Sucrow, Hans-R/u/ diger Murawski, Hermann Minas, Horst Stegemeyer
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Patent number: 4426505Abstract: New polymers are disclosed comprising recurring units of the formula ##STR1## wherein R is hydrogen or lower alkyl containing from 1 to 5 carbon atoms, L is a divalent linking group, and each X is independently chloro or bromo. The polymers are capable of providing a relatively high index of refraction in combination with a relatively high Abbe number and can be utilized as raw materials in the manufacture of plastic optical articles or elements such as lenses or prisms and in the manufacture of optical films and coatings.Type: GrantFiled: February 25, 1982Date of Patent: January 17, 1984Assignee: Polaroid CorporationInventor: Richard A. Minns
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Patent number: 4410515Abstract: A synthetic compound which is biologically active in maintaining calcium and phosphorous metabolism in animals, of the formula I ##STR1## wherein the double bond between positions C-22 and C-23 is single or double; R.sup.2 is hydrogen, CH.sub.3 or CH.sub.2 CH.sub.3 ; X is selected from the group consisting of hydrogen and --OR.sup.1, where R.sup.1 is hydrogen or a straight or branched chain glycosidic residue containing 1-20 glycosidic units per residue; with the proviso that at least one of the R.sup.1 is a glycosidic residue.Type: GrantFiled: April 1, 1981Date of Patent: October 18, 1983Assignee: Massachusetts General HospitalInventors: Sally A. Holick, Michael F. Holick
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Patent number: 4393247Abstract: Described are the compounds having the structures: ##STR1## wherein R represents hydroxy ethyl or methoxy ethyl, and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes, and perfumed articles (including fabric softener compositions, fabric softener articles, hair conditioners, floor waxes, solid or liquid anionic, cationic nonionic or zwitterionic detergents, and deodorant compositions and deodorant articles), as well as processes for preparing such compounds.Type: GrantFiled: December 29, 1981Date of Patent: July 12, 1983Assignee: International Flavors & Fragrances Inc.Inventor: Mark A. Sprecker
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Patent number: 4375004Abstract: Described are the compounds having the structures: ##STR1## wherein R represents isopropyl as well as a process for preparing such compounds.Type: GrantFiled: October 22, 1981Date of Patent: February 22, 1983Assignee: International Flavors & Fragrances Inc.Inventor: Mark A. Sprecker
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Patent number: 4365096Abstract: Alkyl-substituted bicycloalkyl ether compositions useful in the preparation of synthetic lubricant compositions are obtained by reacting an alkyl-substituted 2-norbornene with a monohydric alcohol in the presence of an acidic catalyst.Type: GrantFiled: June 25, 1981Date of Patent: December 21, 1982Assignee: Texaco Inc.Inventor: Edward C. Y. Nieh
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Patent number: 4357360Abstract: Described in the use for augmenting or enhancing the aroma or taste of foodstuffs of compounds defined according to the generic structure: ##STR1## wherein R.sub.1 represents hydrogen, methyl or acetyl and wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are the same or different and each represents hydrogen, methyl or ethyl.Type: GrantFiled: October 13, 1981Date of Patent: November 2, 1982Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, Joseph A. McGhie, Futoshi Fujioka, Takao Yoshida
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Patent number: 4354043Abstract: Described is a compound having the structure: ##STR1## a norbornyl oxyacetaldehyde, prepared by oxidizing the norbornyl oxyethanol compound having the structure: ##STR2## using air or oxygen and a silver or copper chromite catalyst; and organoleptic uses of such oxidation product in the field of perfumery, colognes and perfumed articles (e.g. perfumed plastics, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions or drier-added fabric softener articles).Type: GrantFiled: September 17, 1981Date of Patent: October 12, 1982Assignee: International Flavors & Fragrances Inc.Inventors: Robert P. Belko, Richard M. Boden, Marie R. Hanna
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Patent number: 4351949Abstract: New organopalladium reactions involving the addition of pi-allylpalladium compounds to strained bicyclic alkenes, and subsequent chain extension reactions employing the chemistry of organopalladium compounds are disclosed. By these techniques a large number of bicyclic prostaglandin analogs are prepared, which are useful as inhibitors of arachidonic acid induced platelet aggregation, and are specific inhibitors of thromboxane synthetase.Type: GrantFiled: February 5, 1981Date of Patent: September 28, 1982Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 4351965Abstract: Described are the compounds having the structures: ##STR1## wherein R represents C.sub.3 -C.sub.6 alkyl; aralkyl; hydroxy alkyl; and alkoxy alkyl, and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes, and perfumed articles (including fabric softener compositions, fabric softener articles, hair conditioners, floor waxes, solid or liquid anionic, cationic nonionic or zwitterionic detergents, and deodorant compositions and deodorant articles), as well as processes for preparing such compounds.Type: GrantFiled: September 25, 1981Date of Patent: September 28, 1982Assignee: International Flavors & Fragrances Inc.Inventor: Mark A. Sprecker
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Patent number: 4346245Abstract: Described are substituted tricyclodecane derivatives having the generic structure: ##STR1## wherein Y is a moiety having a structure selected from the group consisting of: ##STR2## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 and R.sub.2 represent hydrogen or methyl with the proviso that one of R.sub.1 and R.sub.2 is hydrogen and the other of R.sub.1 and R.sub.2 is methyl; wherein R.sub.3 is hydrogen, C.sub.1 -C.sub.3 acyl, C.sub.3 or C.sub.4 alkyl or C.sub.3 or C.sub.4 alkenyl; wherein R.sub.4, R.sub.5 and R.sub.6 represent hydrogen or methyl with the additional proviso that one of R.sub.4, R.sub.5 and R.sub.6 is methyl and the other two of R.sub.4, R.sub.5 and R.sub.6 is hydrogen.Type: GrantFiled: September 25, 1981Date of Patent: August 24, 1982Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, John B. Hall