2,2,1-bicyclo Patents (Class 560/120)
  • Patent number: 6531627
    Abstract: An ester compound of the following formula (1) is provided. R1 is H, methyl or CH2CO2R3, R2 is H, methyl or CO2R3, R3 is C1-C15 alkyl, R4 is branched or cyclic, tertiary C5-C20 alkyl group, Z is a divalent C1-C10 hydrocarbon group, and k is 0 or 1. A resist composition comprising as the base resin a polymer resulting from the ester compound is sensitive to high-energy radiation, has excellent sensitivity, resolution, and etching resistance, and is suited for micropatterning using electron beams or deep-UV.
    Type: Grant
    Filed: April 26, 2001
    Date of Patent: March 11, 2003
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Koji Hasegawa, Takeru Watanabe, Takeshi Kinsho, Mutsuo Nakashima, Seiichiro Tachibana, Jun Hatakeyama
  • Patent number: 6524765
    Abstract: A polymer comprising units of formula (1-1) or (1-2) and having a weight average molecular weight of 1,000 to 500,000 is provided. R1 is an acid labile group, R2 is H or straight or branched C1-4 alkyl, Z is a tetravalent C2-10 hydrocarbon group, and k=0 or 1. A resist composition comprising the polymer as a base resin has significantly improved sensitivity, resolution and etching resistance and is very useful in microfabrication.
    Type: Grant
    Filed: November 14, 2000
    Date of Patent: February 25, 2003
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Takeru Watanabe, Jun Hatakeyama, Takeshi Kinsho, Koji Hasegawa, Seiichiro Tachibana
  • Patent number: 6521781
    Abstract: A 2-hydrocarbyl-2-adamantyl acrylate compound represented by the following Formula 6: is produced easily and stably with high yields by reacting a 2-adamantanone compound represented by the following Formula 1: with at least one organometallic compound represented by the following Formula 2 or 3: R1MgX  (2) R1Li  (3) and at least one acrylic compound represented by the following Formula 4 or 5: wherein, R1, R2, R3, X, Y and n in the above formulae being as defined in the disclosure.
    Type: Grant
    Filed: December 6, 2001
    Date of Patent: February 18, 2003
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Minoru Kakuda, Yoshihisa Arai, Kikuo Furukawa, Takehiko Isobe
  • Patent number: 6469197
    Abstract: It is an object of the present invention to provide a negative photoresist composition for lithography, using short-wavelength light such as ArF excimer laser beam as a light source. The negative photoresist composition of the present invention is a negative photoresist composition comprising at least a polymer having a unit represented by the general formula (1) a crosslinking agent and a photo-acid generating agent, and the crosslinking agent is capable of crosslinking the polymer in the presence of an acid catalyst, whereby the polymer is insolubilized in a developer. Since the negative resist composition of the present invention is insolubilized in the developer by an action of an acid produced from the photo-acid generating agent at the exposed portion, a negative pattern can be obtained.
    Type: Grant
    Filed: September 25, 2000
    Date of Patent: October 22, 2002
    Assignee: NEC Corporation
    Inventors: Katsumi Maeda, Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
  • Patent number: 6465551
    Abstract: Compounds and compositions comprising specific metal salts of bicyclo[2.2.1 ]heptane dicarboxylate salts in order to provide highly desirable properties within polyolefin articles are provided. The inventive salts and derivatives thereof are useful as nucleating and/or clarifying agents for such polyolefin, provide excellent crystallization temperatures, stiffness, and calcium stearate compatibility within target polyolefin. Also, such compounds exhibit very low hygroscopicity and therefore excellent shelf stability as powdered or granular formulations. Polyolefin additive compositions and methods of producing polyolefin with such compounds are also contemplated within this invention.
    Type: Grant
    Filed: March 24, 2001
    Date of Patent: October 15, 2002
    Assignee: Milliken & Company
    Inventors: Xiaodong Edward Zhao, Darin L. Dotson
  • Patent number: 6433215
    Abstract: A novel tricyclodecanyl (meth)acrylate compound and a method of producing the same are provided. The compound is 8-alkyl-8-tricyclodecanyl (meth)acrylate represented by formula (1): wherein R1 is methyl or ethyl and R2 is hydrogen or methyl.
    Type: Grant
    Filed: March 1, 2000
    Date of Patent: August 13, 2002
    Assignee: Chem Search Corp.
    Inventor: Hyun-jin Jung
  • Patent number: 6426171
    Abstract: The present invention provides novel bicyclic photoresist monomers, and photoresist copolymer derived from the same. The bicyclic photoresist monomers of the present invention are represented by the formula: where m, n, R, V and B are those defined herein. The photoresist composition comprising the photoresist copolymer of the present invention has excellent etching resistance and heat resistance, and remarkably enhanced PED stability (post exposure delay stability).
    Type: Grant
    Filed: July 28, 2000
    Date of Patent: July 30, 2002
    Assignee: Hyundai Electronics Industries Co., Ltd.
    Inventors: Min Ho Jung, Jae Chang Jung, Geun Su Lee, Ki Ho Baik
  • Patent number: 6410748
    Abstract: A monomer represented by the following general formula (m-1): wherein R is a group having an alicyclic skeleton, R2s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group, X1 is a bivalent organic group containing a heteroatom, j is an integer of 0 to 3, and R1 is a group selected from the following groups, a monovalent organic group having Si (R1-1), and —(X2)k—R4—(X3)m—C(R6)3  (R1-2), wherein X2 and X3 are a bivalent organic group containing a heteroatom, k and m are an integer of 0 to 3, R4 is a bivalent alkyl group, R6s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group.
    Type: Grant
    Filed: May 3, 2001
    Date of Patent: June 25, 2002
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Naomi Shida, Toru Ushirogouchi, Koji Asakawa, Takeshi Okino, Shuji Hayase, Yoshihiko Nakano, Makoto Nakase
  • Patent number: 6376700
    Abstract: An alicyclic compound of the formula (1) is disclosed: wherein R1 and R2 each independently is a hydroxyl group, a C1-8 hydroxyalkyl group, or a C3-8 hydroxycycloalkyl group; R3, R4 and R5 each independently is a hydrogen, a C1-8 hydroxyalkyl group, a C1-6 carboxylic acid or a C3-8 carboxylic acid ester; k is an integer of 0, 1, 2, 3, 4, 5 or 6. The compound of the formula (1) can be applied to dissolution inhibitors for preparing positive photoresist composition.
    Type: Grant
    Filed: June 30, 2000
    Date of Patent: April 23, 2002
    Assignee: Everlight USA, Inc.
    Inventors: Shang-Wern Chang, Yen-Cheng Li, Shang-Ho Lin, Wen-Chieh Wang
  • Patent number: 6368770
    Abstract: The present invention provides a novel photoresist monomer, photoresist copolymer derived from the same, and the photoresist composition comprising the same. In particular, the present invention provides a photoresist monomer of the formula: wherein, A, A′, X, m and n are those defined herein. The photoresist composition of the present invention has an excellent etching and heat resistance, and enhances the resolution and profile of the photoresist film.
    Type: Grant
    Filed: July 21, 2000
    Date of Patent: April 9, 2002
    Assignee: Hyundai Electronics Industries Co. Ltd.
    Inventors: Min Ho Jung, Jae Chang Jung, Geun Su Lee, Ki Ho Baik
  • Patent number: 6369194
    Abstract: The invention relates to compounds of formula where R is a structural diversity element selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, peptidyl, heteroatom-substituted alkyl, cycloalkyl, and amines; and Nu is a structural diversity element derived from a nucleophile, NuH, selected from the group consisting of amines, amino acids, peptide, water, hydrogen sulfide, alcohols, and thiols. The invention also relates to arrays and combinatorial libraries of such compounds, and to a method of preparing such compounds.
    Type: Grant
    Filed: November 9, 1998
    Date of Patent: April 9, 2002
    Assignee: Yale University
    Inventor: Harry H. Wasserman
  • Patent number: 6358675
    Abstract: The polymers of the invention are characterized by having at least one pendent ester group having a tertiary carbon atom attached to the ester oxygen atom in which at least one substituent of the tertiary carbon atom comprises at least one silicon atom. The polymer compositions of the present invention are useful as resist materials for lithography, in particular as the imaging layer or as the top imaging layer in a bilayer resist scheme for use in the manufacture of integrated circuits. The silicon-containing tertiary alcohols and esters of the present invention enable the preparation of polymers with relatively high silicon content.
    Type: Grant
    Filed: September 30, 1999
    Date of Patent: March 19, 2002
    Assignee: 3M Innovative Properties Company
    Inventors: Larry D. Boardman, Carl R. Kessel
  • Patent number: 6348296
    Abstract: The present invention relates to a copolymer resin for a photoresist used with ultra-short wavelength light source such as KrF or ArF, a process for preparation thereof, and a photoresist comprising said resin. By introducing 2,3-di-t-butyl-5-norbornene-2,3-dicarboxylate unit into the structure of a norbornene-maleic anhydride copolymer, the copolymer resin according to the present invention is easily prepared by conventional radical polymerization, has high transparency at 193 nm wavelength, provides increased etching resistance, prevents the top loss phenomenon, exhibits enhanced adhesive strength due to increasing protection ratio in the copolymer resin, and shows excellent resolution.
    Type: Grant
    Filed: December 30, 1998
    Date of Patent: February 19, 2002
    Assignee: Hyundai Electronics Industries Co., Ltd.
    Inventors: Min Ho Jung, Cha Won Koh, Hyung Gi Kim
  • Publication number: 20020019560
    Abstract: The present invention is directed to photoresist cross-linkers selected from the group consisting of a cross-linker monomer represented by following Chemical Formula 1, and homopolymers and copolymers thereof. Such cross-linkers are suitable for use in photolithography processes employing KrF(248nm), ArF(193nm), E-beam, ion-beam or EUV light sources.
    Type: Application
    Filed: September 11, 2001
    Publication date: February 14, 2002
    Inventors: Keun Kyu Kong, Jae Chang Jung, Myoung Soo Kim, Hyoung Gi Kim, Hyeong Soo Kim, Ki Ho Baik
  • Publication number: 20020007031
    Abstract: An ester compound of the following formula (1) is provided.
    Type: Application
    Filed: April 26, 2001
    Publication date: January 17, 2002
    Applicant: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Koji Hasegawa, Takeru Watanabe, Takeshi Kinsho, Mutsuo Nakashima, Seiichiro Tachibana, Jun Hatakeyama
  • Publication number: 20010051742
    Abstract: Ester compounds of formula (1) are useful as monomers to form base resins for use in chemically amplified resist compositions adapted for micropatterning lithography.
    Type: Application
    Filed: April 26, 2001
    Publication date: December 13, 2001
    Applicant: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Takeru Watanabe, Takeshi Kinsho, Mutsuo Nakashima, Seiichiro Tachibana, Tsunehiro Nishi, Jun Hatakeyama
  • Publication number: 20010051741
    Abstract: Ester compounds of formula (1) are useful as monomers to form base resins for use in chemically amplified resist compositions adapted for micropatterning lithography.
    Type: Application
    Filed: April 26, 2001
    Publication date: December 13, 2001
    Applicant: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeru Watanabe, Koji Hasegawa, Takeshi Kinsho, Mutsuo Nakashima, Seiichiro Tachibana, Tsunehiro Nishi, Jun Hatakeyama
  • Patent number: 6313327
    Abstract: This invention relates to novel carboxylic acid derivatives represented by the following formula I and their synthesis: wherein, R1 is an hydrogen atom, an alkyl group or an alkoxy group of 1 to 20 carbon atoms in a linear, branched or cyclic form; R2 is a carboxy group of 1 to 40 carbon atoms in a linear, branched or cyclic form which is unsubstituted, or substituted into a hydroxy group, an ester group and an ether group. The novel carboxylic acid derivatives are more easily decomposed by acid than t-butyl ester compounds but are not dissolved in basic aqueous solution. According to this invention, carboxylic acid is under condensation with halogen compounds designed to prepare a larger monomolecular compound compared to the conventional method. Further, the condensed site is easily decomposed by acid but is extremely insoluble by basic aqueous solution.
    Type: Grant
    Filed: October 25, 1999
    Date of Patent: November 6, 2001
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Dong Seoul Seo, Joo Hyeon Park, Jae Young Kim, Seong Ju Kim
  • Publication number: 20010031420
    Abstract: The present invention provides photoresist monomers, photoresist polymers derived from the same, processes for producing such photoresist polymers, photoresist compositions comprising such polymers, and processes for producing a photoresist pattern using such photoresist compositions.
    Type: Application
    Filed: February 15, 2001
    Publication date: October 18, 2001
    Inventors: Geun Su Lee, Jae Chang Jung, Min Ho Jung, Ki Ho Baik
  • Patent number: 6284429
    Abstract: A novel ester compound having an exo-form 2-alkylbicyclo[2.2.1]heptan-2-yl group as the protective group is provided as well as a polymer comprising units of the ester compound. The polymer is used as a base resin to formulate a resist composition having a higher sensitivity, resolution and etching resistance than conventional resist compositions.
    Type: Grant
    Filed: February 24, 2000
    Date of Patent: September 4, 2001
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeshi Kinsho, Tsunehiro Nishi, Hideshi Kurihara, Mutsuo Nakashima, Koji Hasegawa, Takeru Watanabe
  • Patent number: 6222061
    Abstract: A novel norbornene carboxylate compound and a method of producing the same are provided. The norbornene carboxylate compound is 2-alkyl-2-adamantyl 5-norbornene-2-carboxylate represented by formula (1): wherein R is methyl or ethyl.
    Type: Grant
    Filed: March 1, 2000
    Date of Patent: April 24, 2001
    Assignee: Chem Search Corp.
    Inventor: Hyun-jin Jung
  • Patent number: 6200731
    Abstract: The present invention discloses a cross-linking monomer for a photoresist polymer represented by following Chemical Formula 1: <Chemical Formula 1> wherein, V represents CH2, CH2CH2, oxygen or sulfur; Y is selected from the group consisting of straight or branched C1-10 alkyl, oxygen, and straight or branched C1-10 ether; R′ and R″ individually represent H or CH3; i is a number of 1 to 5; and n is a number of 0 to 3; and a process for preparing a photoresist copolymer comprising the same.
    Type: Grant
    Filed: December 16, 1999
    Date of Patent: March 13, 2001
    Assignee: Hyundai Electronics Industries Co., Ltd.
    Inventors: Geun Su Lee, Cha Won Koh, Jae Chang Jung, Min Ho Jung, Ki Ho Baik
  • Patent number: 6187393
    Abstract: Compounds of formula (I) are provided which are particularly useful in super twisted nematic devices, where n may be 0-5; m may be 0-5; p may be 1-9; q may be 1, 1, or 2; A1, A2 are independently chosen from 1-4, -disubstituted benzene, 2,5-disubstituted pyrimidine, or 2,5-disubstituted pyridine, trans- 1,4-disubstituted cyclohexane, trans- 2,5-disubstitued dioxane. The aromatic rings may be laterally substituted with F, Cl, Br or CN; Z1 may be O, COO, OOC; Z2, Z3 are independent chosen from a direct bond, COO, OOC, C2H4, CH2O, OCH2, or -c≡c-, provided that when Z1 is O and m is 1, 3 or 5 the carbon—carbon double bond configuration is E; provided that when Z1 is O and m is 2 or 4 the carbon—carbon double bond configuration is Z; provided that when Z1 is COO or OOC and m is 0, 2 or 4 the carbon—carbon double bond configuration is E; and provided that when Z1 is COO or OOC and m is 1, 3 or 5 the carbon—carbon double bond configuration is Z.
    Type: Grant
    Filed: March 19, 1999
    Date of Patent: February 13, 2001
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Warren L. Duffy, Stephen M Kelly, John W Goodby
  • Patent number: 6180818
    Abstract: A silver halide photographic material is disclosed, comprising a support having thereon at least one light-sensitive silver halide emulsion layer, wherein said silver halide photographic material contains a compound by formula (IA), or which contains at least one hydroxamic acid compound having a bicyclo ring as a partial structure and represented by formula (IB).
    Type: Grant
    Filed: November 3, 1999
    Date of Patent: January 30, 2001
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hisashi Mikoshiba, Hiroo Takizawa, Junichiro Hosokawa, Yoshio Ishii, Keiji Mihayashi, Masakazu Morigaki, Mamoru Sakurazawa
  • Patent number: 6153785
    Abstract: A novel norbornene carboxylate compound and a method of producing the same are provided. The norbornene carboxylate compound is 8-alkyl-8-tricyclodecanyl 5-norbornene-2-carboxylate represented by formula (1): ##STR1## wherein R is methyl or ethyl.
    Type: Grant
    Filed: March 1, 2000
    Date of Patent: November 28, 2000
    Assignee: Chem Search Corp.
    Inventor: Hyun-jin Jung
  • Patent number: 6147249
    Abstract: A novel ester compound having an alkylcycloalkyl or alkylcycloalkenyl group as the protective group is provided as well as a polymer comprising units of the ester compound. The polymer is used as a base resin to formulate a resist composition having a higher sensitivity, resolution and etching resistance than conventional resist compositions.
    Type: Grant
    Filed: May 10, 1999
    Date of Patent: November 14, 2000
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeru Watanabe, Takeshi Kinsho, Tsunehiro Nishi, Mutsuo Nakashima, Koji Hasegawa, Jun Hatakeyama
  • Patent number: 6114570
    Abstract: A silver halide photographic material is disclosed, comprising a support having thereon at least one light-sensitive silver halide emulsion layer, wherein said silver halide photographic material contains a compound by formula (IA), or which contains at least one hydroxamic acid compound having a bicyclo ring as a partial structure and represented by formula (IB).
    Type: Grant
    Filed: September 2, 1998
    Date of Patent: September 5, 2000
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hisashi Mikoshiba, Hiroo Takizawa, Junichiro Hosokawa, Yoshio Ishii, Keiji Mihayashi, Masakazu Morigaki, Mamoru Sakurazawa
  • Patent number: 6083501
    Abstract: A drug for prevention and therapy of diseases caused by fibrinoid formation or thrombus formation, as well as a model animal of fibrinoid formation or thrombus formation in the lung is disclosed. The drug for preventing and treating diseases caused by fibrinoid formation or thrombus formation in the lung according to the present invention comprises an inhibitor of interleukin 6 as an effective ingredient. The model animal of the diseases caused by fibrinoid formation or thrombus formation in the lung is a rat in which fibrinoid formation or thrombus formation actually occurs by induction with interleukin 6.
    Type: Grant
    Filed: March 14, 1996
    Date of Patent: July 4, 2000
    Assignee: Toray Industries, Inc.
    Inventors: Masayuki Miyata, Reiji Kasukawa, Masanobu Naruto, Nobutaka Ida, Yu-ichiro Sato, Katsuaki Kojima, Nobuo Ida
  • Patent number: 6057460
    Abstract: Polymerizable hybrid monomers with norbornenyl or norbornadienyl groups are described which can be radically cured at room temperature and are suitable in particular for use in the dental field.
    Type: Grant
    Filed: February 21, 1997
    Date of Patent: May 2, 2000
    Assignee: Ivoclar AG
    Inventors: Norbert Moszner, Volker Rheinberger, Frank Zeuner
  • Patent number: 6020370
    Abstract: Bridged cyclic amino acids of formula ##STR1## are disclosed and are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain and neuropathological disorders. Processes for the preparation and intermediates useful in the preparation are also disclosed.
    Type: Grant
    Filed: May 19, 1998
    Date of Patent: February 1, 2000
    Assignee: Warner-Lambert Company
    Inventors: David Christopher Horwell, Justin S. Bryans, Clare O. Kneen, Andrew I. Morrell, Giles S. Ratcliffe
  • Patent number: 5783724
    Abstract: Described are allyl esters of 2-norbornane acrylic acids and 2-norbornylidene propionic acids defined according to the generic structure: ##STR1## wherein the wavy line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein one of the dashed lines is carbon-carbon single bond and the other of the dashed lines is a carbon-carbon double bond; and wherein R represents methyl or hydrogen; as well as methods for augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles.
    Type: Grant
    Filed: March 6, 1997
    Date of Patent: July 21, 1998
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Wilhelmus Johannes Wiegers, Marie R. Hanna
  • Patent number: 5741925
    Abstract: Vinyl naphthenate monomer mixtures are prepared by transvinylation of naphthenic acid in the presence of a catalyst of a palladium carboxylate complexed with one or more aryl N-containing ligands and distilling the resulting vinyl naphthenate monomers in the presence of the catalyst at pot temperatures exceeding 80.degree. C. The catalyst is stable and can be re-used over several transvinylation reaction runs.
    Type: Grant
    Filed: January 13, 1997
    Date of Patent: April 21, 1998
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Chung-Ling Mao, Francis Joseph Waller, Kenneth Merle Kem
  • Patent number: 5698514
    Abstract: Described are allyl esters of 2-norbornane acrylic acids and 2-norbornylidene propionic acids defined according to the generic structure: ##STR1## wherein the wavy line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein one of the dashed lines is carbon-carbon single bond and the other of the dashed lines is a carbon-carbon double bond; and wherein R represents methyl or hydrogen; as well as methods for augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: December 16, 1997
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Wilhelmus Johannes Wiegers, Marie R. Hanna
  • Patent number: 5659070
    Abstract: A process for preparing alkyl 5-oxo-6-heptenoates of the formula I ##STR1## where X and Y are hydrogen or methyl, and R.sup.1 is C.sub.1 -C.sub.8 -alkyl, byA) reacting 5-acetyl-2-norbornene with a dialkyl carbonate [CO(OR.sup.2).sub.2, where R.sup.2 is C.sub.1 -C.sub.4 -alkyl,] in the presence of a base to give an alkyl 3-(2-norbornen-5-yl)-3-oxopropionate II,B) reacting the ester II on the presence of a base with an unsaturated compound of the formula III ##STR2## where Z is CN or CO.sub.2 R.sup.3, where R.sup.3 is C.sub.1 -C.sub.4 -alkyl, and hydrolyzing the product of the reaction of compound II with compound III to a 5-(2-norbornen-5-yl)-5-oxopentanoic acid of the formula IV,C) esterifying the acid IV to give a 5-(2-norbornen-5-yl)-5-oxopentanoic ester of the formula V, andD) converting the ester V by thermal cleavage into an alkyl 5-oxo-6-heptenoate I.
    Type: Grant
    Filed: February 1, 1996
    Date of Patent: August 19, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ebel, Matthias Eiermann, Thomas Papkalla
  • Patent number: 5616780
    Abstract: The novel compounds of the formula I ##STR1## in which A is a group of the formula IIa or IIb, ##STR2## Y is oxygen, methylene, ethylidene or a >C.dbd.C(CH.sub.3).sub.2 group, Z is nitrogen, ##STR3## R.sub.1 and R.sub.2 are, for example C.sub.1 -C.sub.5 alkyl, R.sub.3 and R.sub.4 are, for example, hydrogen or methyl, and R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13 and R.sub.14 are, for example, hydrogen, are suitable for stabilizing organic material against oxidative, thermal or light-induced degradation.
    Type: Grant
    Filed: January 31, 1996
    Date of Patent: April 1, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Rita Pitteloud, Bernard Gilg
  • Patent number: 5591854
    Abstract: A process of enantioselective synthesis of seven-membered carbocycles in the presence of di-rhodium(II) tetracarboxylate catalysts.
    Type: Grant
    Filed: October 14, 1994
    Date of Patent: January 7, 1997
    Assignee: Wake Forest University
    Inventor: Huw M. L. Davies
  • Patent number: 5532386
    Abstract: A process for preparing compounds of the formula I ##STR1## where: Y inter alia is ##STR2## where R.sup.3 is hydrogen or a C.sub.1 -C.sub.10 - hydrocarbon radical. R.sup.1 and R.sup.2, inter alia, are each, independently of one another, hydrogen, a C.sub.1 -C.sub.20 -hydrocarbon radical which optionally carries inert substituents or heteroaryl, wherein a compound of the formula II ##STR3## where Z is ##STR4## is reacted in the presence of catalytic amounts of a carbonic ester and of a nitrogenous base at from 100.degree. to 250.degree. C. under a pressure of from 0.01 to 100 bar.
    Type: Grant
    Filed: March 1, 1995
    Date of Patent: July 2, 1996
    Assignee: BASF Aktiengesellschaft
    Inventor: Rolf Fischer
  • Patent number: 5434267
    Abstract: Process for the preparation of compounds of the formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, X and n have the meaning given in the description, by reacting acetates with carbon monoxide in the presence of a basic auxiliary, followed by alkylation. The products are intermediates for fungicidal acrylates.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: July 18, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Kraus, Alexander Klausener, Hans-Joachim Diehr
  • Patent number: 5391571
    Abstract: The compounds of the formula: ##STR1## in which R.sup.1 is alkyl of 4 or more carbon atoms, cycloalkyl, 1-adamantyl, 2-adamantyl, 3-noradamantyl, 3-methyl-1-adamantyl, 1-fluorenyl, 9-fluorenyl, cycloalkylalkyl, phenyl, substituted phenyl, alkyl, alkoxy, halo, nitro, cyano or trifluoromethyl, phenylalkyl or substituted phenylalkyl, where the substituent on the benzene ring is alkyl, alkoxy, halo, nitro, cyano, trifluoromethyl or phenyl; R.sup.2 is hydrogen, alkyl or R.sup.1 taken with R.sup.2 and the nitrogen atom to which they are attached form a heterocyclic moiety of the formula: ##STR2## wherein ##STR3## in which R.sup.7 is hydrogen, alkyl, hydroxy, alkanoyloxy, hydroxyalkyl, hydroxycarbonyl, alkoxycarbonyl, phenyl or substituted phenyl, in which the substituent is alkyl, alkoxy, halo, nitro, cyano, haloalkyl, perhaloalkyl or dialkylaminoalkyl; R.sup.8 is hydrogen or alkyl or R.sup.7 and R.sup.8 taken together are polymethylene; R.sup.
    Type: Grant
    Filed: May 13, 1993
    Date of Patent: February 21, 1995
    Assignee: American Home Products Corporation
    Inventors: Richard E. Mewshaw, Thomas J. Commons, Donald P. Strike
  • Patent number: 5268489
    Abstract: Unsaturated cycloaliphatic esters like higher hydrocarbyl, functionally substituted or polyunsaturated cyclohex-3-ene carboxylates, made directly by cycloaddition of dienes with dienophillic (meth/eth)acrylates, and their derivatives like epoxides and urethanes, provide useful thermal and radiation curable coatings, inks, sealants, adhesives, solvents, acid scavengers, and intermediates for other uses.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: December 7, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Joseph V. Koleske, John N. Argyropoulos, Oliver W. Smith
  • Patent number: 5266728
    Abstract: The present invention provides a method for producing optically active 3-substituted-2-norbornanones which are useful as starting materials for several kinds of physiologically active materials, and to their intermediates, optically active 2-hydroxy-2-norbornanecarboxylic acid and to a method for producing these intermediates.
    Type: Grant
    Filed: August 19, 1992
    Date of Patent: November 30, 1993
    Assignee: Chisso Corporation
    Inventors: Naoyuki Yoshida, Teruyo Sugiura, Kazutoshi Miyazawa, Yasuyuki Koizumi
  • Patent number: 5248748
    Abstract: Disclosed is a diacetylene compound comprising, as structural units, (a) at least one member selected from diacetylene group-containing organic groups of the formulae (I) and (II):R.sup.I --C.tbd.C--C.tbd.C--R.sup.II -- (I)and--R.sup.III --C.tbd.C--C.tbd.C--R.sup.IV -- (II)wherein R.sup.I is hydrogen or a (C1-16) monovalent organic group, and R.sup.II, R.sup.III and R.sup.IV are a (C1-13) divalent organic group,(b) at least one organic group having at least one carbon-to-carbon double bond, and (c) at least one connecting group connecting the units (a) and (b) , which connecting group is selected from amide, imide, ester, ether, amino, imino, urethane, sulfonyl and carbonyl bonds. A cured shaped article made of this compound exhibits isotropically a high elastic modulus and has excellent mechanical properties.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: September 28, 1993
    Assignee: Dir. General of Agency of Industrial Science and Technology
    Inventors: Katsuyuki Nakamura, Satoru Yamazaki, Jinichiro Kato, Kensaku Tokushige
  • Patent number: 5241104
    Abstract: Optically active mono-esters of dicarboxylic acid of the formula III: ##STR1## being useful as intermediates for preparing optically active natural products or medicines; asymmetric synthesis process for preparing thereof being characterized by the reaction of an acid anhydride with an (R)- or (S)-arylacetic acid derivative; and the key substances therefor are also claimed.
    Type: Grant
    Filed: June 23, 1992
    Date of Patent: August 31, 1993
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Takaharu Matsuura
  • Patent number: 5175341
    Abstract: Optically active mono-esters of dicarboxylic acid of the formula III: ##STR1## being useful as intermediates for preparing optically active natural products or medicines; asymmetric synthesis process for preparing thereof being characterized by the reaction of an acid anhydride with an (R)- or (S)-arylacetic acid derivative; and the key substances therefor are also claimed.
    Type: Grant
    Filed: June 20, 1991
    Date of Patent: December 29, 1992
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Takaharu Matsuura
  • Patent number: 5077309
    Abstract: Novel compounds have the formula (I) ##STR1## where ##STR2## represents one of the divalent cyclic groups ##STR3## the letters a and b indicating in each case the points of attachment of the substituents R.sup.1 and CV(R.sup.2)-NV'R, respectively; R.sup.1 is a group --(CH.sub.2).sub.b --(A).sub.a --(CH.sub.2).sub.c --B--CH.sub.2 --CO.sub.2 R' in which A and B are each separately oxygen or sulphur, a is 0, b is 0 and c is an integer from 3 to 10, or a is 1, b is 0 or an integer from 1 to 7 and c is an integer from 2 to 9 with the sum of b and c being from 2 to 9, and CO.sub.2 R' is a carboxy group or an amide, ester or salt derivative thereof; V and V' either each separately is hydrogen or together are the second bond of a carbon-nitrogen double bond; R.sup.2 is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by an aromatic group directly or through an oxygen or sulphur atom; and R is a group --OR.sup.3, --OR.sup.4, --D--R.sup.3, --N.dbd. R.sup.5 or --NW.G.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: December 31, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 5047575
    Abstract: Compounds, and a process for their preparation, have the formula ##STR1## or corresponding salts thereof wherein R represents a group of the formula ##STR2## wherein R.sub.1 represents oxazolinyl, --C.tbd.N, --CH.sub.2 OR.sub.2 or ##STR3## These compounds in the form of pharmaceutical or cosmetic compositions are useful for the treatment of keratinization disorders.
    Type: Grant
    Filed: October 14, 1988
    Date of Patent: September 10, 1991
    Assignee: L'Oreal
    Inventors: Guy Solladie, Serge Forestier, Gerard Lang
  • Patent number: 5047574
    Abstract: Optically active mono-esters of dicarboxylic acid of the formula III: ##STR1## being useful as intermediates for preparing optically active natural products or medicines; asymmetric synthesis process for preparing thereof being characterized by the reaction of an acid anhydride with an (R)- or (S)-arylacetic acid derivative; and the key substances therefor are also claimed.
    Type: Grant
    Filed: December 12, 1989
    Date of Patent: September 10, 1991
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Takaharu Matsuura
  • Patent number: 5043451
    Abstract: There are provided compounds of the formula: ##STR1## wherein R.sub.1 is a hydrogen or C.sub.1 -C.sub.5 alkyl; R.sub.2 is an C.sub.1 -C.sub.10 alkyl, aryl, aralkyl, or pyridyl, where the aryl, aralkyl, or pyridyl are unsubstituted or are substituted by C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, nitro, hydroxy, carboxy, amino, C.sub.1 -C.sub.5 alkylamino, C.sub.1 -C.sub.5 dialkylamino whose two alkyl groups may be different from each other, C.sub.2 -C.sub.3 alkanoylamino, or halogen and X is an C.sub.1 -C.sub.7 alkylene, C.sub.2 -C.sub.7 alkenylene, --CH(F)CH.dbd.CH(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 --S--(CH.sub.2).sub.2 --, --CH.sub.2).sub.2 --S--(CH.sub.2).sub.3 --, --C.sub.6 H.sub.4 --O--CH.sub.2 --or --CH.sub.2 CH.dbd.CH--m--C.sub.6 H.sub.4 --, or their pharmaceutically acceptable salts. The compounds are useful as antithrombotic, anti-vasoconstricting and anti-bronchoconstricting drugs.
    Type: Grant
    Filed: April 27, 1990
    Date of Patent: August 27, 1991
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Fumihiko Watanabe, Tadadiko Tsushima, Kenji Kawada, Susumu Kamata
  • Patent number: 4957940
    Abstract: Certain bicyclo [2.2.1] heptane and bicyclo [2.2.2] octane substituted tetrahydro-2H-pyran-2-ones and the corresponding ring-opened acids derived therefrom are potent inhibitors of the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase) and are useful as hypocholesterolemic and hypolipidemic agents.
    Type: Grant
    Filed: November 21, 1989
    Date of Patent: September 18, 1990
    Assignee: Warner-Lambert Company
    Inventor: Bruce D. Roth
  • Patent number: 4898977
    Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.
    Type: Grant
    Filed: August 13, 1987
    Date of Patent: February 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Herold, Christof Angst