Benzene Ring Containing Patents (Class 570/127)
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Patent number: 6369279Abstract: Styrene derivatives of formula (1) are novel wherein R1 is hydrogen, C1-20 alkyl, fluoro-substituted C1-20 alkyl, chloro, or trichloromethyl, R2 is a phenol protecting group, p, q and r are integers in the range of 0≦p<5, 0≦q<5, 0<r<5, and 0<p+q<5. Polymers obtained by polymerizing the styrene derivatives are useful as the base polymer of resist compositions.Type: GrantFiled: September 7, 2000Date of Patent: April 9, 2002Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Mutsuo Nakashima, Jun Hatakeyama, Jun Watanabe, Yuji Harada
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Publication number: 20020038858Abstract: Disclosed are liquid crystalline compounds which (i) are characterized in that the compounds have a wide temperature range in which the compounds exhibit a liquid crystal phase, are low in viscosity, and have a negative and high &Dgr;&egr;, (ii) are readily mixed with other various liquid crystal materials even at low temperatures, and (iii) are useful as component of liquid crystal compositions suitable both for TFT type display mode and IPS mode; and liquid crystal composition comprising the liquid crystalline compound; the compounds are expressed by the general formula (1) 1Type: ApplicationFiled: June 16, 1999Publication date: April 4, 2002Inventors: TAKASHI KATO, SHUICHI MATSUI, KAZUTOSHI MIYAZAWA, FUSAYUKI TAKESHITA, ETSUO NAKAGAWA
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Publication number: 20020033472Abstract: Provided are a liquid crystalline compound having a wide liquid crystal phase temperature range, low viscosity, a large elastic constant ratio K33/K11 and excellent solubility at low temperature, a liquid crystal composition using the same and a liquid crystal display.Type: ApplicationFiled: July 6, 2001Publication date: March 21, 2002Applicant: CHISSO CORPORATIONInventors: Takashi Kato, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Etsuo Nakagawa
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Patent number: 6355849Abstract: The subject-matter of the present invention is a process of use in perfluoroalkylation and a reactant for making use of this process. This process is defined in that it comprises a stage in which a material of formula RfH and a base (or a species capable of generating a base) are brought into contact, in a polar and anhydrous medium, with a substrate carrying at least one electrophilic functional group. Application to organic synthesis.Type: GrantFiled: February 17, 2000Date of Patent: March 12, 2002Assignee: Rhodia ChimieInventors: Nicolas Roques, James Russel
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Publication number: 20020028306Abstract: The invention relates to pentafluorosulfuranylbenzene derivatives of the formula I 1Type: ApplicationFiled: June 27, 2001Publication date: March 7, 2002Inventors: Peer Kirsch, Joachim Krause, Michael Heckmeier
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Patent number: 6350875Abstract: The synthesis of asymmetric tetrasubstituted cyclooctatetraenes (“COTs”) and the use of said compounds in organic light emitting diodes is reported, wherein said COTs represent a class of wide gap electron transporters that are readily deposited in vacuum.Type: GrantFiled: March 23, 2001Date of Patent: February 26, 2002Assignee: The University of Southern CaliforniaInventors: William P. Weber, Ping Lu, Mark E. Thompson, Haiping Hong
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Patent number: 6350925Abstract: A synthesis is provided for &agr;,&bgr;-difluoro-&bgr;-halo-ethenyl aromatic compounds such as &agr;,&bgr;,&bgr;-trifluorostyrenes by a process of reacting CFX2CFXI, wherein each X is independently F or Cl, provided that at least one X is Cl and at least one X is F, with an aromatic compound Ar to form (CFX2CFX)n—Ar, wherein n is 1, 2 or 3, and subsequently dechlorohalogenating this product to form (CFX═CF)n—Ar. Novel synthetic intermediate compounds are provided.Type: GrantFiled: July 31, 1998Date of Patent: February 26, 2002Assignee: 3M Innovative Properties CompanyInventor: George Van Dyke Tiers
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Patent number: 6348244Abstract: An object of the present invention is to provide novel liquid crystalline compounds having a negative and extremely large dielectric anisotropy value and a small optical anisotropy value together, to provide liquid crystal compositions comprising the liquid crystalline compound, and to provide liquid crystal display devices fabricated by using the liquid crystal composition; the liquid crystalline compounds have 2,3-difluorophenyl moiety and are expressed by the general formula (1) wherein Ra and Rb each independently represent a straight chain or branched alkyl group having 1 to 10 carbon atoms in which group any methylene group may be replaced by —O—, —CH═CH—, or —C≡C—, but there is not a case wherein —O— continues; ring A1 represents cyclohexane-1,4-diyl not adjacent any methylene group may be replaced by —O—; ring A2 represents 2,3-difluoro-1,4-phenylene in which phenylene hydrogen atoms at 5-position and 6-position mType: GrantFiled: April 24, 2000Date of Patent: February 19, 2002Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Hiroyuki Takeuchi, Yasuhiro Kubo, Fusayuki Takeshita, Etsuo Nakagawa
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Patent number: 6344247Abstract: The present invention provides liquid crystalline compounds having a high voltage holding ratio and a low threshold voltage, little variation of these properties depending on temperature change, high &Dgr;n, and good compatibility with other liquid crystal materials particularly under a low temperature; liquid crystal compositions containing these crystalline compounds; and liquid crystal display devices comprising these liquid crystal compositions.Type: GrantFiled: March 25, 1999Date of Patent: February 5, 2002Assignee: Chisso CorporationInventors: Tomoyuki Kondou, Shuichi Matsui, Kazutoshi Miyazawa, Hiroyuki Takeuchi, Yasuhiro Kubo, Fusayuki Takeshita, Etsuo Nakagawa
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Patent number: 6342572Abstract: The invention pertains to benzocyclobutene resins having flame retardant properties. Such resins have a high glass transition temperature (Tg>250° C.), low moisture absorption, low dielectric constant, good mechanical properties, flame retardancy (meets or exceeds UL94 V-O and/or VTM-O requirements), and can be cast onto a reinforcement to prepare a laminate for use as a substrate for electronic circuitry. The flame resistant compound is reaction product of a halogen containing compound of the formulae R&Parenopenst; DA)n or R&Parenopenst; DA&Parenclosest;n R2 wherein R is a halogen containing aromatic group, a halogen containing aliphatic group or a combination thereof; R2 is hydrogen, an aromatic group, an aliphatic group or an combination of an aromatic group and an aliphatic group which may contain halogen atoms; DA is a Diels-Alder reactive diene or a group that can act as a dienophile in a Diels-Alder reaction; and n is greater than or equal to 1; with a benzocyclobutene compound.Type: GrantFiled: December 28, 1999Date of Patent: January 29, 2002Assignee: Honeywell International Inc.Inventors: Michael W. Wagaman, Thomas F. McCarthy
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Patent number: 6333080Abstract: A liquid crystalline alkenyltolan derivative expressed by the general formula CtH2t−1—G—(CH2)m—A1—B1—(A2—B2)n—(A3—B3)p—A4—X wherein A1, A2, A3, and A4 independently represent a 1,4-cyclohexylene, 1,4-phenylene in which one or two hydrogen atoms may be replaced by a fluorine atom(s), dioxane-2,5-diyl, or pyrimidine-2,5-diyl group; B1, B2, and B3 independently represent a covalent bond, an 1,2-ethylene, 1,2-ethenylene, 1,2-ethynylene, oxymethylene, methylenoxy, carbonyloxy, or 1,4-butylene group provided that at least one of B1, B2, and B3 represents an 1,2-ethynylene group; G represents a covalent bond or an oxygen atom; CtH2t−1 represents an alkenyl group having t carbon atoms; n and p are each 0 or 1; and X represents an alkyl group having 1 to 10 carbon atoms.Type: GrantFiled: May 6, 1999Date of Patent: December 25, 2001Assignee: Chisso CorporationInventors: Norio Tamura, Atsuko Fujita, Shuichi Matsui, Kazutoshi Miyazawa, Norihisa Hachiya, Etsuo Nakagawa
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Patent number: 6333436Abstract: Styrene derivatives of formula (1) are novel wherein R1 is H, F, C1-20 alkyl or fluorinated C1-20 alkyl, R2 in cis or trans conformation is F, C1-20 alkyl or fluorinated C1-20 alkyl, R3 is a phenol protecting group, p, q and r are integers in the range of 0≦p<5, 0≦q<5, 0<r<5, and 0≦p+q<5. Polymers obtained by polymerizing the styrene derivatives are useful as the base polymer of resist compositions.Type: GrantFiled: October 12, 2000Date of Patent: December 25, 2001Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Matsuo Nakashima, Jun Hatakeyama, Jun Watanabe, Yuji Harada
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Publication number: 20010050352Abstract: Compounds of the formula (I) 1Type: ApplicationFiled: May 10, 2001Publication date: December 13, 2001Applicant: Clariant GmbHInventors: Rainer Wingen, Wolfgang Schmidt
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Patent number: 6329529Abstract: Disclosed are a fluorinating agent represented by the general formula (1): wherein R1 to R4 are a substituted or unsubstituted, saturated or unsaturated alkyl group or a substituted or unsubstituted aryl group, and can be the same or different; R1 and R2 or R3 and R4 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms; or R1 and R3 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms, for example: a preparation process of the fluorinating agent and a process for preparing fluorine compounds by reacting various compounds with the fluorinating agent. The invention has also disclosed that the fluorinating agent is very effective for fluorinating oxygen containing functional compounds.Type: GrantFiled: July 31, 1998Date of Patent: December 11, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Hiroshi Sonoda, Kazunari Okada, Akira Takahashi, Kouki Fukumura, Hidetoshi Hayashi, Teruyuki Nagata, Yasuhiro Takano
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Patent number: 6329027Abstract: Provided are liquid crystalline compounds having excellent physical properties and being excellent in miscibility with other liquid crystal materials; liquid crystal compositions comprising the crystalline compound; and liquid crystal display device fabricated by using the liquid crystal composition; the liquid crystalline compounds being specific chlorobenzene derivatives expressed by the general formula (1) Ra—A1—Z1—A2&Parenopenst;Z2—A3&Parenclosest;m&Parenopenst;Z3—A4&Parenclosest;nRb (1) wherein Ra, Rb, A1 to A4, Z1 to Z3, m, and n are herein defined.Type: GrantFiled: May 28, 1999Date of Patent: December 11, 2001Assignee: Chisso CorporationInventors: Tomoyuki Kondo, Shuichi Matsui, Kazutoshi Miyazawa, Hiroyuki Takeuchi, Fusayuki Takeshita, Etsuo Nakagawa
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Patent number: 6326066Abstract: 1,4-disubstituted 2,6-difluorobenzene compound of formula I wherein R is an alkyl or alkenyl radical, A1 and A2 are independently (a) a trans-1,4-cyclohexylene radical in which a CH2 group may be replaced by -O- and/or -S, (b) a 1,4-phenylene radical in which a CH group may be replaced by N, (c) 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, Z1 and Z2 are —CO—O—, —O—CO—, —CH2O—,—OCH2—, —CH2CH2—, —CH═CH—,—C≡C—or a single bond m and n are 0, 1, 2 or 3, (m+n) is 1, 2 or 3, X is R or F, Cl, CF3, —OCF3, or —OCHF2, —OCF5, —CN or —NCS with the provisos that at least one of the radicals A1 and A2 present in the molecule is and at least one of Z1 or Z2 is —COO—, are suitable as components of liquid-Type: GrantFiled: February 28, 2000Date of Patent: December 4, 2001Assignee: Merck Patent Gesellschaft mit Reschankter HaftungInventors: Eike Poetsch, Volker Meyer, Volker Reiffenrath, Andreas Wachtler, Ulrich Finkenzeller, Hans Adolf Kurmeier, Reinhard Hittich, Bernhard Rieger, David Coates, Simon Greenfield, Robert William Clemitson
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Patent number: 6319570Abstract: The invention is to provide liquid crystalline compounds which have a low viscosity, high negative dielectric anisotropy, high resistivity, and high voltage holding ratio, and are stable against heat and ultraviolet light; to provide liquid crystal compositions comprising the liquid crystalline compound; and to provide liquid crystal display devices using the liquid crystal composition therein; the liquid crystalline compound is expressed by the general formula (1) wherein R1 and Y1 represent an alkyl group having 1 to 20 carbon atoms; X1, X2, and X3 independently represent single bond, 1,2-ethylene group, vinylene group, —COO—, —CF2O—, or —OCF2—; ring A1, ring A2, ring A3, and ring A4 independently represent trans-1,4-cycloliexylene, or 1,4-phenylene hydrogen atom on the ring may be replaced by fluorine atom or chlorine atom provided that at least one of ring A2, ring A3, and ring A4 represents 2,3-difluoro-1,4-phenylene; m and n are 0 or 1, and eaType: GrantFiled: June 19, 2000Date of Patent: November 20, 2001Assignee: Chisso CorporationInventors: Tugumiti Andou, Shuichi Matsui, Kazutoshi Miyazawa, Hiroyuki Takeuchi, Yasuyuki Koizumi, Yasuko Sekiguchi, Etsuo Nakagawa, Fusayuki Takeshita
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Patent number: 6312618Abstract: A new class of asymmetric polar diphenyldiacetylene liquid crystal compounds and method for preparation are disclosed. The new class of liquid crystal compounds comprises the basic structure: Wherein R1 is an alkenyl group having the general formula (C2H2n−1), X is a cyano group, a fluoro group, CF3, OCF3, or a chloro group, Y1 is unsubstituted, a fluoro group, a chloro group or a methyl group, Y2 is unsubstituted, a fluoro group, a chloro group, or a methyl group, Z1 is unsubstituted, a fluoro group, or a methyl group, and Z2 is unsubstituted, a fluoro group, or a methyl group. The compounds disclosed exhibit high birefringence, low rotational viscosity, and have unexpectedly broad nematic ranges. Also disclosed are eutectic mixtures comprising at least one polar diphenyldiacetylene having the general structure described above. The eutectic mixtures also have unexpectedly broad nematic ranges.Type: GrantFiled: April 3, 2000Date of Patent: November 6, 2001Assignee: HRL LaboratoriesInventors: Shin-Tson Wu, Mary E. Neubert
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Patent number: 6297405Abstract: A process for the preparation of aromatic aldehydes containing fluorine, and more particularly, to a formylation process for fluorinated aromatic derivatives through the reaction of fluorinated benzenes with carbon monoxide and aluminum chloride at a relatively low pressure, a low temperature, and in the presence of at most a catalytic amount of an acid (such as aqueous hydrochloric acid) is herein disclosed. The resultant fluorinated benzaldehydes are useful as precursors to the formation of a number of different compounds, such as dyestuffs, flavorings, fragrances, herbicidal compounds, nucleating agents, polymer additives, and the like. The inventive method provides a very cost effective and safe procedure for producing such fluorinated benzaldehydes in very high yields. The particular novel multi-substituted benzaldehydes are also encompassed within this invention.Type: GrantFiled: September 1, 2000Date of Patent: October 2, 2001Assignee: Milliken & CompanyInventors: John David O. Anderson, Walter Scrivens
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Patent number: 6254941Abstract: The present invention provides liquid crystalline compounds having a very high voltage holding ratio, very little variation of these properties depending on temperature, high &Dgr;n, and good compatibility in the other liquid crystal materials particularly under a low temperature, liquid crystal compositions containing these crystalline compounds, and liquid crystal display devices constituted by using the liquid crystal compositions.Type: GrantFiled: March 25, 1999Date of Patent: July 3, 2001Assignee: Chisso CorporationInventors: Tomoyuki Kondou, Shuichi Matsui, Kazutoshi Miyazawa, Hiroyuki Takeuchi, Yasuhiro Kubo, Fusayuki Takeshita, Etsuo Nakagawa
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Patent number: 6248260Abstract: Provided are liquid crystalline compounds which are excellent in the miscibility with existing liquid crystalline compounds even at low temperatures and are electrically and chemically stable while having a high voltage holding ratio and a high &Dgr;∈; liquid crystal compositions comprising the compound; and liquid crystal display devices fabricated by using the composition; the liquid crystalline compounds are expressed by the general formula (1)Type: GrantFiled: July 28, 1999Date of Patent: June 19, 2001Assignee: Chisso CorporationInventors: Yasuhiro Haseba, Kazutoshi Miyazawa, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Fusayuki Takeshita, Etsuo Nakagawa
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Patent number: 6242654Abstract: A preparation process of a fluorine substituted aromatic compound comprising reacting an alkali metal or alkali earth metal salt of an aromatic compound having a hydroxy group with an organic fluorinating agent is disclosed. As a representative fluorinating agent, a bis-dialkylamino-difluoromethane compound, for example, 2,2′-difluoro-1,3-dimethylimidazolidine, is exemplified. According to the process, an industrially useful fluorinated aromatic compound, for example, a fluorobenzene, a fluorine substituted benzophenone, a fluorine substituted diarylsulfone can be prepared with ease in economy without specific equipment.Type: GrantFiled: December 21, 1999Date of Patent: June 5, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Kenichi Goto, Kouki Fukumura, Hiroshi Sonoda, Junko Naruse, Hidetoshi Hayashi, Hideaki Oikawa
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Patent number: 6242645Abstract: Diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating agents are disclosed.Type: GrantFiled: March 23, 2000Date of Patent: June 5, 2001Assignee: Air Products and Chemicals, Inc.Inventors: Gauri Sankar Lal, Guido Peter Pez, Reno Joseph Pesaresi, Jr., Robert George Syvret
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Patent number: 6222078Abstract: Disclosed is a method of making an &agr;-chloro-&agr;,&agr;-difluoro aromatic compound. An &agr;,&agr;,&agr;-trichloro aromatic compound having the general formula where Y is C or N, R is halogen, R′, amino, NHR′, NR′2, OR′, OCF3, or nitro, R′ is alkyl from C1 to C10, n is 1, 2, or 3, and m is 0 to 5, is reacted with about 0.7 to about 1.4 equivalents of hydrogen fluoride per chlorine to be replaced, in the presence of about 0.001 to about 1.5 wt %, based on wt % of said &agr;,&agr;,&agr;-trichloro aromatic compound, of a catalyst selected from the group consisting of oxides of Ti, Zr, V, Nb, Ta, Mn, Re, Fe, Ru, Os, Al, Ga, In, Ge, Sn, Sb, and Bi, MoOqXr, (M)pMos+tO3s+4t, (M)pVO3, (M)pVO5, WOqXr, (M)pWs+tO3s+4t, and mixtures thereof, where M is a cation, X is amine, phosphine, carboxylate, or ketone, p is the negative of the valence of the anion times the inverse of the valence of M, q is 0 to 3, r is 0 to 6, and s is 0 to 4, and t is 1 to 5.Type: GrantFiled: December 10, 1998Date of Patent: April 24, 2001Assignee: Occidental Chemical CorporationInventors: Sanjay Mandal, Kevin R. Benson, James Franc
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Patent number: 6222064Abstract: A fluorination method of oxygen and halogen sites with diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating reagents is disclosed.Type: GrantFiled: January 14, 2000Date of Patent: April 24, 2001Assignee: Air Products and Chemicals, Inc.Inventors: Gauri Sankar Lal, Guido Peter Pez
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Patent number: 6210761Abstract: The present invention is to provide liquid crystalline compounds which exhibit a negative dielectric anisotropy value, have an extremely high voltage holding ratio and a low threshold voltage, are remarkably small in their dependency on temperature, hardly exhibit smectic phase, and are excellent in miscibility with other liquid crystal materials; to provide liquid crystal compositions comprising the liquid crystalline compound; and to provide liquid crystal display devices fabricated by using the liquid crystal composition; the liquid crystalline compounds are expressed by the following general formula (1) wherein Ra, Rb, Y1 to Y6, Z1 and Z2 are herein defined.Type: GrantFiled: May 28, 1999Date of Patent: April 3, 2001Assignee: Chisso CorporationInventors: Tomoyuki Kondo, Shuichi Matsui, Kazutoshi Miyazawa, Hiroyuki Takeuchi, Fusayuki Takeshita, Etsuo Nakagawa
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Patent number: 6200654Abstract: 1,4-disubstituted 2,6-difluorobenzene compound of formula I wherein R is an alkyl or alkenyl radical, A1 and A2, in each case independently of one another, are (a) a trans-1,4-cyclohexylene radical in which a CH2 group may be replaced by —O— and/or —S, (b) a 1,4-phenylene radical in which a CH group may be replaced by N, (c) 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, Z1 and Z2 are —CO—O—, —O—CO—, —CH2—O—, —OCH2—, —CH2CH2—, —CH═CH—, —C≡C— or a single bond m and n are 0, 1, 2 or 3, (m+n) is 1, 2 or 3, X is R or F, Cl, CF3, —OCF3, or —OCHF2, —OCF5, —CN or —NCS with the proviso that at least one of the radicals A1 and A2 present in the molecule is are suitable as components of liquid-cType: GrantFiled: August 25, 1997Date of Patent: March 13, 2001Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Eike Poetsch, Volker Meyer, Volker Reiffenrath, Andreas Wachtler, Ulrich Finkenzeller, Hans Adolf Kurmeier, Reinhard Hittich, Bernhard Rieger, David Coates, Simon Greenfield, Robert William Clemitson
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Patent number: 6194620Abstract: Dichloro-tetrafluoro-[2,2]-paracyclophane (formula I), which is a novel compound useful as a material for forming a coating film by chemical vapor deposition, and a process for manufacturing thereof and poly-&agr;&agr;-difluoro-chloro-para-xylylene film prepared therefrom are disclosed. Dichloro-tetrafluoro-[2,2]-paracyclophane is manufactured by chlorinating tetrafluoro-[2,2]-paracyclophane. The film to be formed by chemical vapor deposition of dichloro-tetrafluoro-[2,2]-paracyclophane has remarkably improved thermostability, as compared with the conventional products and is expected to be applied in various fields.Type: GrantFiled: January 27, 1997Date of Patent: February 27, 2001Assignee: Daisan Kasei Kabushiki KaishaInventor: Hiroshi Maruyama
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Patent number: 6184425Abstract: The present invention relates to a process for preparing fluorine-containing compounds by reacting a compound which contains fluorine-exchangeable halogen with a fluoride or a mixture of fluorides with the formula I MeF (I), in which Me is an alkaline earth metal ion, NH4+-ion or alkali metal ion, in the presence of a compound or a mixture of compounds of the formula (II) in which A1, A2, A3, A4, A5, A6, A7, A8 independently of one another are identical or different and are a straight-chain or branched alkyl or alkenyl having 1 to 12 carbon atoms, cycloalkyl having 4 to 8 carbon atoms, an aryl having 6 to 12 carbon atoms, or an aralkyl having 7 to 12 carbon atoms, or A1 A2, A3A4, A5A6, and A7A8 independently of one another are identical or different and are connected to one another directly or by way of O or N—A9 to form a ring having 3 to 7 ring members, A9 is an alkyl having 1 to 4 carbon atoms and B− is a monovalent acid radical or the equivalent of a polyvalType: GrantFiled: July 7, 1999Date of Patent: February 6, 2001Assignee: Aventis Research & Technologies GmbH & Co.Inventors: Alexander Kolomeitsev, Sergej Pasenok
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Patent number: 6174459Abstract: A difluorophenyl derivative compound having characteristics of a liquid crystal represented by the following general formula (1), a liquid crystal composition and a liquid crystal display device in which the composition is used: wherein R0 is an alkyl group or an alkenyl group having 1 to 15 carbon atoms, and an optional methylene group in the alkyl group or the alkenyl group may be substituted by an oxygen atom; A1 and A2 are each a trans-1,4-cyclohexylene group, or one group selected from the group consisting of a 1,4-phenylene group, a pyrimidine-2,5-diyl group, a pyridine-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dithian-2,5-diyl group and a tetrahydrothiopyran-2,5-diyl in which one or more hydrogen atoms on a six-membered ring may be substituted by halogen atoms; Z1 and Z2 are each —(CH2)4—, —(CH2)3O—, —O(CH2)3— or a single bond; and X1 and X2 are each H, F, Cl or Br.Type: GrantFiled: February 4, 1999Date of Patent: January 16, 2001Assignee: Chisso CorporationInventors: Takashi Kato, Shuichi Matsui, Kazutoshi Miyazawa, Yasusuke Hisatsune, Etsuo Nakagawa
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Patent number: 6171664Abstract: The invention relates to tolan derivatives of the formula I in which R1, R2, A, Z, L1, L2, L3, L4, L5, L6, Q, m and n are as defined herein.Type: GrantFiled: June 17, 1999Date of Patent: January 9, 2001Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Matthias Bremer, Detlef Pauluth, Harald Hirschmann
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Patent number: 6159392Abstract: 5,7-Difluoro-1,2,3,4-tetrahydronaphthalene derivatives of the formula (I)R.sup.1 (-A.sup.1 -M.sup.1).sub.a (-A.sup.2 -M.sup.2).sub.b -B(-M.sup.3 -A.sup.3).sub.c (-M.sup.4 -A.sup.4).sub.d -R.sup.2 (I)in whichB isand ##STR1## R.sup.1 (-A.sup.1 -M.sup.1).sub.a (-A.sup.2 -M.sup.2) and (-M.sup.3 -A.sup.3).sub.c (-M.sup.4 -A.sup.4)R.sup.2 denote mesogenic radicals are suitable as components of liquid-crystal mixtures, in particular ferroelectric.Type: GrantFiled: August 20, 1999Date of Patent: December 12, 2000Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Wolfgang Schmidt, Javier Manero
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Patent number: 6150571Abstract: A method for preparing 2,4-Dichloro-3,5-dimethylfluorobenzene, wherein the 2,4-Dichloro-3,5-dimethylfluorobenzene can be prepared in highisomeric selectivities when 3,5-dimethylfluorobenzene is chlorinated in the presence of Friedel-Crafts catalysts and a sulfur-containing co-catalyst.The invention is also directed to an intermediary for preparing a pharmaceutically-active compound including 4-dichloro-3,5-dimethyl fluorobenzene.Type: GrantFiled: March 4, 1999Date of Patent: November 21, 2000Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Robert Horst Bloodworth, Karsten Von Dem Bruch
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Patent number: 6118031Abstract: The invention relates to a process for preparing substituted arylpyrazoles of the general formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R .sup.4 are each as defined in the description, and to novel intermediates for preparing these arylpyrazoles.Type: GrantFiled: August 6, 1999Date of Patent: September 12, 2000Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Thomas Himmler, Albrecht Marhold
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Patent number: 6117361Abstract: A compound represented by the following general formula (1) is provided. This has broader temperature range of nematic phase, lower viscosity and higher miscibility with other liquid crystal compounds at low temperature than those of conventional liquid crystal compounds, and the compounds have high chemical stability. ##STR1## wherein H.sub.1 to H.sub.8 represent independently a hydrogen atom or a halogen atom, provided that at least one of them is a halogen atom; R.sub.1 represents a moiety which is an alkyl group having 2 to 20 carbon atoms provided that one or more methylene groups (--CH.sub.2 --) which are not successive in the alkyl group are replaced with an oxygen atom (--O--) in the form of ether; Y.sub.1 represents an alkyl group having 1 to 20 carbon atoms, and one or more methylene groups in Y.sub.1 independently may be replaced with an oxygen atom, a sulfur atom, a dihydroxysilyl group, a dimethylsililene group, --CH.dbd.CH-- or --C.tbd.C--; X.sub.1 to X.sub.Type: GrantFiled: August 31, 1998Date of Patent: September 12, 2000Assignee: Chisso Corp.Inventors: Koichi Shibata, Tomoyuki Kondo, Shuichi Matsui, Kazutoshi Miyazawa, Norihisa Hachiya, Etsuo Nakagawa
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Patent number: 6114590Abstract: Polyhalogenated benzotrifluorides can be reacted with chlorides from the series of Friedel-Crafts catalysts to give the corresponding benzotrichlorides, which can be hydrolysed by water in the presence of iron(III) chloride to give the corresponding benzoyl chlorides. These are suitable as intermediate products for the preparation of active compounds for medicaments and feed additives.Type: GrantFiled: April 17, 1997Date of Patent: September 5, 2000Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Peter Andres
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Patent number: 6114589Abstract: The invention relates to a process for the preparation of fluorinated compoundsAz.sub.x ArF.sub.w Cl.sub.(y-w) R.sub.z (1)in which Az is a radical --F, --Cl, --Br, --NO.sub.2, --CN, --CF.sub.3, --CCl.sub.3, --CHO, --CO(C.sub.n H.sub.2n+1), --COX or --SO.sub.2 X, where X is F, Cl or Br, x is an integer from 1 to 3, Ar is a phenyl radical, pyridyl radical or naphthyl, w is an integer from 1 to y, y is an integer from 1 to 5, R is H, an alkyl radical or an alkoxy radical having from 1 to 10 carbon atoms, z is an integer from 1 to 5, (x+y+z) is the number of all substitutable valences on the radical Ar, which comprises reacting a compoundAz.sub.x ArCl.sub.y R.sub.z (2),with an alkali metal fluoride in the presence of a component a) or a mixture of component a) and at least one of components b), c), d) and/or e), component a) being one or more quaternary ammonium compounds which contain one or more radicals --(C.sub.m H.sub.2m O)R.sup.Type: GrantFiled: October 13, 1998Date of Patent: September 5, 2000Assignee: Clariant GmbHInventors: Thomas Schach, Thomas Wessel, Maren Gutermuth
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Patent number: 6080886Abstract: A fluorination method of oxygen and halogen sites with diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating reagents is disclosed.Type: GrantFiled: September 29, 1997Date of Patent: June 27, 2000Assignee: Air Products and Chemicals, Inc.Inventors: Gauri Sankar Lal, Guido Peter Pez
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Patent number: 6057006Abstract: The invention relates to fluorocyclohexane derivatives of the formula I ##STR1## in which R.sup.1, Z.sup.1, Z.sup.2, L.sup.1, L.sup.2, L.sup.3 and X are as defined as below:X is alkyl or alkoxy having 1 to 10 carbon atoms which is unsubstituted or substituted by halogen, alkenyl or alkenyloxy having 2 to 10 carbon atoms which is unsubstituted or substituted by --CN, --CF.sub.3 or --F, or is --CN, --F, --OCHF.sub.2, --OCF.sub.3, --OCHFCF.sub.3 or --OCF.sub.2 CF.sub.3,L.sup.1, L.sup.2 and L.sup.3 are each, independently of one another, H or F,R.sup.1 is H, an alkyl or alkenyl radical having 1-12 carbon atoms which is unsubstituted, monosubstituted by CN or CF.sub.3 or substituted by halogen, where one or more non-adjacent CH.sub.2 groups in these radicals may also, in each case independently of one another, be replaced by --O--, --S--, --CO--, --.diamond.--, --CO--O--, --O--CO-- or --O--CO--O--,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.2 O--, --O--, --O--CH.sub.Type: GrantFiled: June 4, 1998Date of Patent: May 2, 2000Assignee: Merck Patent GesellschaftInventors: Peer Kirsch, Kazuaki Tarumi, Joachim Krause
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Patent number: 6043397Abstract: A method for the production of a fluorine-containing aromatic compound is provided which allows the relevant reaction to proceed in a standard reaction vessel such as, for example, a glass vessel at room temperature under an ambient pressure without requiring provision of such special devices as have been necessary heretofore or adoption of harsh reaction conditions. This method comprises causing an aromatic compound (A) having a cyclic skeletal part of 6 to 16 carbon atoms containing a plurality of --C(.dbd.O)X groups, wherein X stands for a hydrogen atom, a halogen atom, or an alkyl group of 1 to 10 carbon atoms, and having the remaining hydrogen atoms unsubstituted or partly or wholly substituted with at least one species of halogen atom to react with a compound (B) represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 independently stand for an alkyl group of 1 to 6 carbon atoms or a phenyl group.Type: GrantFiled: August 25, 1998Date of Patent: March 28, 2000Assignee: Nippon Shokubai Co., Ltd.Inventors: Seiichi Teshima, Yoshinobu Asako
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Patent number: 6017467Abstract: A propiolonitrile derivative of formula (I) ##STR1## wherein n1 and n2 each independently stand for 0 or 1; A1, A2 and A3 each independently represent a 1,4-phenylene, a 1,4-phenylene substituted by one or more fluorine atoms, a trans-1,4-cyclohexylene, a 1,3-dioxane-2,5-diyl or a 1,3-pyrimidine-2,5-diyl; Z1, Z2 and Z3 each independently represent a single bond, ethylene, ethenylene, ethynylene, carbonyloxy, oxycarbonyl, methyleneoxy, oxymethylene, 1,4-butylene or 1,4-butenylene; R represents a saturated, aliphatic hydrocarbyl radical of 1-10 carbons, an unsaturated, aliphatic hydrocarbyl radical of 2-10 carbons, a saturated or unsaturated, aliphatic hydrocarbyl radical of 1-10 carbons containing one or more ether linkages (--O--) in the chain and a saturated or unsaturated, fluoro-substituted aliphatic hydrocarbyl radical of 1-10 carbons containing one or more fluorine atoms in the chain; X1 and X2 each independently represent H, F or Cl;provided that at least one of X1 and X2 is F or Cl, when both n1 and n2Type: GrantFiled: June 13, 1997Date of Patent: January 25, 2000Assignee: Chisso CorporationInventors: Atsuko Fujita, Shuichi Matsui, Hiroyuki Takeuchi, Kazutoshi Miyazawa, Norio Tamura, Norihisa Hachiya, Etsuo Nakagawa
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Patent number: 5981789Abstract: Disclosed is a method of preparing an aromatic compound having the general formula ##STR1## where R is CF.sub.3, OCF.sub.3, OC.sub.2 F.sub.5, CN, NCO, or COCl, m is 0, 1, or 2, n is 0, 1, or 2, q is 1 or 2, and q+m+n is an integer from 1 to 5. A vapor is prepared of a substrate having the general formula ##STR2## and a chlorinating agent. The mixture is reacted at a temperature above the boiling point of the substrate but below its decomposition temperature. The amount of chlorinating agent is about 0.5 to about 2 times the amount stoichiometrically required to replace the nitro groups on the substrate with chlorine. Unreacted substrate and partially reacted substrate are condensed from the product mixture and are recycled. The substrate is preferably in contact with the chlorinating agent before it is vaporized.Type: GrantFiled: December 30, 1998Date of Patent: November 9, 1999Assignee: Occidental Chemical CorporationInventors: John Hickey, Robert L. Bell, George Piotrowski
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Patent number: 5981422Abstract: Stoichiometric and catalytic chemical transformations may be carried out in solution using novel fluorous multiphase systems (FMS). The term "fluorous" is defined as a carbon-fluorine bond rich organic molecule which is generated by replacing hydrogen atoms bonded to carbon atoms with fluorine. The novel complexes suitable for use as fluorous catalysts and reagents in the present invention contain sufficient number of fluorous moieties to render them preferentially soluble in the appropriate fluorous solvent without impairing the ability of the catalyst or reagent to be effective or participate in the corresponding reaction.Type: GrantFiled: August 26, 1997Date of Patent: November 9, 1999Assignee: Exxon Research and Engineering Co.Inventors: Istvan Tamas Horvath, Jozsef Rabai
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Patent number: 5968963Abstract: Certain compounds have been synthesized and found to be effective inhibitors of phospholipase A.sub.2 (PLA.sub.2), and thereby useful in the treatment of intestinal cholesterol absorption and the disease states arising therefrom, such as hypercholesterolemia and coronary artery disease.Type: GrantFiled: March 4, 1996Date of Patent: October 19, 1999Assignee: Warner-Lambert CompanyInventor: Reynold Homan
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Patent number: 5968410Abstract: The invention relates to fluorocyclohexane derivatives of the formula I ##STR1## in which R.sup.1, R.sup.2, y.sup.1, y.sup.2, X.sup.1, X.sup.2, A.sup.1, Z.sup.1, Z.sup.2, Z.sup.3, n, m, p and q are as defined above.Type: GrantFiled: July 29, 1998Date of Patent: October 19, 1999Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Peer Kirsch, Joachim Krause, Kazuaki Tarumi
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Patent number: 5886242Abstract: The invention relates to chiral compounds containing at least one divalent or polyvalent chiral group, at least one polymerizable group, at least one spacer and at least one mesogenic group, and to their use as polymerizable, chiral dopes for the preparation of cholesteric networks.The novel compounds are suitable for use in electro-optical displays or as chiral dopes for nematic or cholesteric liquid crystals in order to produce layers which reflect in colors.Type: GrantFiled: January 12, 1998Date of Patent: March 23, 1999Assignee: BASF AktiengesellschaftInventors: Karl-Heinz Etzbach, Paul Delavier, Karl Siemensmeyer, Gerhard Wagenblast, Lothar Laupichler, Volkmar Vill
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Patent number: 5858270Abstract: In order to provide novel compounds which are useful as liquid crystal materials for low voltages in several liquid crystal displays, have a large dielectric anisotropy, and are low in viscosity; and to improve characteristics of liquid crystal compositions, difluorooxymethane derivatives expressed by the following general formula (I) and liquid crystal compositions containing the compound are proposed ##STR1## wherein each of l, m, and n is 0 or 1, rings A.sub.1 to A.sub.3 independently represent six-membered rings such as trans-1,4-cyclohexylene and 1,4-phenylene, Z.sub.1 to Z.sub.3 independently represent a bonding group such as covalent bond and --CH.sub.2 CH.sub.2 --, L.sub.1 to L.sub.4 independently represent hydrogen atom or halogen atom, and X represents a group such as halogen atom and OCF3.They are useful as liquid crystal materials for low voltages in several modes such as active matrix mode and STN mode.Type: GrantFiled: January 30, 1997Date of Patent: January 12, 1999Assignee: Chisso CorporationInventors: Shuichi Matsui, Kazutoshi Miyazawa, Noriyuki Ohnishi, Yasuhiro Haseba, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
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Patent number: 5849962Abstract: A process for the preparation of octafluoro-?2,2!paracyclophane includes contacting a reactant selected from the group consisting of 1,4-bis(bromodifluoromethyl)benzene (dibromide), 1,4-bis(chlorodifluoromethyl)benzene (dichloride), and 1,4-bis(iododifluoromethyl)benzene (diiodide) with trimethylsilyltributyltin (TMSTBT) (a reducing agent) and fluoride ions in a refluxing solution of hexamethylphosphoramide (HMPA) or dimethylsulfoxide (DMSO) in tetrahydrofuran (THF) at conditions effective to promote a reaction product comprising octafluoro-?2,2!paracyclophane.Type: GrantFiled: November 26, 1997Date of Patent: December 15, 1998Assignee: Specialty Coating Systems, Inc.Inventors: William R. Dolbier, Jr., Xiao X. Rong
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Patent number: 5841004Abstract: A novel 3-substituted .alpha.,.beta.-dibromoethylbenzene of formula (I): ##STR1## wherein X represents a halogen atom or a trihalomethyl group, which is useful as an intermediate for pharmaceuticals or agricultural chemicals, is prepared by a simple and high yield process which comprises reacting a 3-substituted .alpha.-bromoethylbenzene represented by formula (II): ##STR2## wherein X is as defined above, or a 3-substituted ethylbenzene represented by formula (III): ##STR3## wherein X is as defined above, with bromine in the presence of a quaternary ammonium salt.Type: GrantFiled: July 17, 1996Date of Patent: November 24, 1998Assignee: Mitsubishi Chemical CorporationInventors: Ken Tanaka, Manabu Katsurada, Akemi Hosokawa
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Patent number: 5833879Abstract: A novel liquid crystalline compound having a sufficiently large .DELTA.n, a superior, low temperature compatibility with other liquid crystals and a chemical stability; a liquid crystal composition containing the above compound; and a display element using the above liquid crystal composition are provided,which liquid crystalline compound is expressed by the formula (1): ##STR1## wherein R.sub.1 is an alkyl group or alkoxy group of 1 to 10C, cyano group or a halogen atom; R.sub.2 is an alkyl group of 1 to 5C wherein one methylene group (--CH.sub.2 --) may be replaced by oxygen atom; X.sub.1 and X.sub.2 each independently are hydrogen atom or a halogen atom; A and B each independently are single bond, 1,4-phenylene ring or 1,4-cyclohexylene ring which may be substituted by halogen atom may be; and p is 1 to 5.Type: GrantFiled: February 12, 1996Date of Patent: November 10, 1998Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Shuichi Matsui, Yasuko Sekiguchi, Etsuo Nakagawa