Nitro Or Nitroso, Bonded Directly To Carbon, Containing Patents (Class 564/441)
  • Patent number: 4950802
    Abstract: A novel method for the preparation of aryl trifluoromethyl ethers which comprises reacting a phenol, a perhalomethane, and an antimony pentahalide. For example, 4-nitrophenol may be reacted with an excess over stoichiometry of both carbon tetrachloride and antimony trifluoride with a catalytic amount of antimony pentachloride to form 4-nitrophenyl trifluoromethyl ether.
    Type: Grant
    Filed: December 9, 1988
    Date of Patent: August 21, 1990
    Assignee: The Dow Chemical Company
    Inventor: Bassam S. Nader
  • Patent number: 4948794
    Abstract: Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein R.sup.1 is C.sub.1-12 -alkyl, which may optionally be substituted by hydroxy, formyl, carboxy, carboxylic esters, amides or amines, C.sub.3-8 -cycloalkyl, aryl, aralkyl; and wherein R.sup.6 is, hydrogen, halogen, CN, CF.sub.3, NO.sub.2, or OR', wherein R' is C.sub.1-4 -alkyl and R.sup.5, R.sup.7 and R.sup.8 is hydrogen, provided R.sup.6 is not CF.sub.3, OCH.sub.3, NO.sub.2, C.sup.1 or Br when R.sup.1 is CH.sub.3 ; orR.sup.6 and R.sup.7 independently are NO.sub.2, halogen, CN, CF.sub.3, or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.5 and R.sup.8 are each hydrogen; orR.sup.5 and R.sup.6 together form a further fused aromatic ring, which may be substituted with halogen, NO.sub.2, CN, CF.sub.3 or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.7 and R.sup.8 independently are hydrogen, halogen, CN, CF.sub.3, NO.sub.2 or OR', wherein R' is C.sub.1-4 -alkyl; orR.sup.7 and R.sup.
    Type: Grant
    Filed: November 8, 1988
    Date of Patent: August 14, 1990
    Assignee: A/S Ferrosan
    Inventors: Tage Honore, Poul Jacobsen, Flemming E. Nielsen, Lars Naerum
  • Patent number: 4941997
    Abstract: The invention relates to compounds of formula I ##STR1## wherein R.sup.1 is C.sub.12 -C.sub.30 alkyl, R.sup.2 is hydrogen or C.sub.1 -C.sub.30 alkyl, R.sup.3 is C.sub.1 14 Calkyl or C.sub.1 -C.sub.3 alkoxy, R.sup.4 may have one of the meanings of R.sup.3 or is halogen, k and n are each independently of the other 0, 1 or 2, and R.sup.5 and R.sup.6 are each independently of the other C.sub.1 -C.sub.4 alkyl, any of which alkyl groups as defined herein may also be partly fluorinated or perfluorinated, with the proviso that R.sup.1 is alkyl of not less than 18 carbon atoms if R.sup.2 is hydrogen or alkyl of less than 12 carbon atoms.From these compounds it is possible to prepare molecular aggregates, especially LB layer systems, which have reversible thermochromic and solvatochromic properties. The invention also relates to intermediates of formula II ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and n are as defined above.
    Type: Grant
    Filed: July 6, 1988
    Date of Patent: July 17, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Gero Decher, Bernd Tieke
  • Patent number: 4921504
    Abstract: The compound 4-(N-ethyl-N-2'-hydroxyethyl)-amino-1-(2"-hydroxyethyl)-amino-2-nitrobenze ne, having the formula: ##STR1## is provided for use as a blue coloring nitro dye in a hair dyeing composition that may be directly applied to hair without the use of oxidation agents.
    Type: Grant
    Filed: September 12, 1988
    Date of Patent: May 1, 1990
    Assignee: Wella Aktiengesellschaft
    Inventors: Thomas Clausen, Eugen Konrad
  • Patent number: 4918236
    Abstract: A compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.m -wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.2 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together are oxo; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms; R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 - C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: April 17, 1990
    Assignee: ICI Americas Inc.
    Inventors: Christopher G. Knudsen, William J. Michaely
  • Patent number: 4910341
    Abstract: The present invention relates to a process for preparing a N,N'-disubstituted nitro-para-phenylenediamine (I) according to the following scheme: ##STR1## X denoting a halogen and R a lower alkyl, lower mono- or polyhydroxyalkyl, lower alkoxyalkyl or lower aminoalkyl group, in which the amino group can be mono- or disubstituted with a lower alkyl or lower mono- or polyhydroxyalkyl group, the nitrogen atom of said amino group being able to form part of a heterocyclic system.The invention also relates to the intermediate oxazolidones of formulae (II) and (III), and the new nitro-para-phenylenediamines in which R denotes a lower alkoxyalkyl, lower polyhydroxyalkyl or lower aminoalkyl group, as well as the dyeing compositions for keratinous fibres containing these new nitro-para-phenylenediamines.
    Type: Grant
    Filed: September 6, 1988
    Date of Patent: March 20, 1990
    Assignee: L'Oreal
    Inventors: Gerard Lang, Alex Junino
  • Patent number: 4900869
    Abstract: A process is disclosed for the production of 4-[ethyl-(2'-hydroxyethyl)-amino]-1-[(2'-hydroxyethyl)-amino]-2-nitrobenze ne, by means of a two-stage technique proceeding from the reaction product of 1,4-diamino-2-nitrobenzene with chloroformic acid chloroethyl ester, or by means of a multiple-stage technique which is based upon an improved process for the production of the pre-stage 4-ethylamino-1-[(2'-hydroxyethyl)-amino]-2-nitrobenzene through sulfuric acid splitting off of 4-(N-ethylarylsulfonamido)-1-[(2'-hydroxyethyl)-amino]-2-nitrobenzene.
    Type: Grant
    Filed: November 6, 1987
    Date of Patent: February 13, 1990
    Assignee: Aktiengesellschaft Wella
    Inventors: Thomas Clausen, Isolde Lowe
  • Patent number: 4888445
    Abstract: The invention relates to a compound of formula ##STR1## in which: X denotes a branched or unbranched alkylene radical containing 2 to 6 carbon atoms, optionally being able to be substituted with one or more hydroxyl radicals;R denotes a hydrogen atom, an alkyl or a mono- or polyhydroxyalkyl radical or an aminoalkyl radical in which the amine group can be mono- or disubstituted with an alkyl radical or with a mono- or polyhydroxyalkyl radical, the nitrogen atom also being able to form part of a heterocyclic system and the alkyl radicals containing 1 to 4 carbon atoms;R' denotes a hydrogen atom or a C.sub.1 to C.sub.4 alkyl radical;Y and Z denote a nitro and/or --NHR.sub.1 radical, R.sub.
    Type: Grant
    Filed: November 10, 1987
    Date of Patent: December 19, 1989
    Assignee: L'Oreal
    Inventors: Alex Junino, Gerard Lang, Nicole Jehanno
  • Patent number: 4874895
    Abstract: The level of the nitrosamines which may be present in the unrefined trifluralin is reduced to a value below 0.5 ppm, by treating the unrefined trifluralin under agitation, at a temperature from 60.degree. to 90.degree. C., for a time between 10 minutes and 4 hours, with an aqueous solution containing from 15 to 50% by weight of hydrobromic acid in a ratio of 0.2 to 0.8 liters per kilogram of unrefined trifluralin, said aqueous solution of hydrobromic acid being added with an amount of sulfamic acid from 0.1 to 3 g per liter of solution and with an amount of bisulfite or an alkali metal corresponding to a content of sulphur dioxide from 0.3 to 1.2 g per liter of said hydrobromic acid aqueous solution.The so obtained refined trifluralin has a content of nitrosamines which is lower than 0.1 ppm.
    Type: Grant
    Filed: February 17, 1989
    Date of Patent: October 17, 1989
    Assignee: Finchimica S.p.A.
    Inventor: Donadello Graziello
  • Patent number: 4863482
    Abstract: A 2-nitro metaphenylenediamine for use in dyeing keratinous fibers, in particular human hair, has the formula: ##STR1## wherein Z represents a --O--, --S-- or --NH-- radical. R.sub.1, R.sub.2 and R.sub.3 may be identical or different and represent a hydrogen atom or an alkyl, hydroxyalkyl, polyhydroxyalkyl, alkoxyalkyl or hydroxyalkoxyalkyl radical or an aminoalkyl radical whose amino radical may be mono- or disubstituted by an alkyl or hydroxyalkyl radical. The alkyl and alkoxy radicals contain 1 to 6 carbon atoms. Cosmetically acceptable salts of this compound may also be used.
    Type: Grant
    Filed: July 26, 1988
    Date of Patent: September 5, 1989
    Assignee: L'Oreal
    Inventors: Alex Junino, Nicole Jehanno, Gerard Lang
  • Patent number: 4857071
    Abstract: The invention encompasses the use of nitroaminobenzaldehydes and nitroaminobenzylimines as hair dyeing agents.
    Type: Grant
    Filed: August 21, 1987
    Date of Patent: August 15, 1989
    Assignee: Clairol, Inc.
    Inventor: James S. Anderson
  • Patent number: 4855292
    Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.2 is 1-pyrrolidinyl which may have 1 to 2 substituents selected from the group consisting of (i) C.sub.1 -C.sub.6 alkyl, (ii) amino-(C.sub.1 -C.sub.6)alkyl, said amino being optionally substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkanoyl, and C.sub.1 -C.sub.6 alkoxycarbonyl, (iii) amino which may be substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl, and C.sub.1 -C.sub.6 alkanoyl, and (iv) 2-oxo-1,3-dioxolenemethylamino which is substituted by C.sub.1 -C.sub.6 alkyl; or 1-piperidinyl which may have 1 to 3 substituents selected from oxo, hydroxy, halogen and C.sub.1 -C.sub.6 alkyl, and R.sup.3 is C.sub.1 -C.sub.
    Type: Grant
    Filed: July 23, 1987
    Date of Patent: August 8, 1989
    Assignee: Otsuka Pharmaceutical Company, Limited
    Inventors: Hiraki Ueda, Hisashi Miyamoto, Shinji Aki, Tatsuya Otsuka
  • Patent number: 4845293
    Abstract: A dyeing composition for keratinous fibres comprising a solvent and at least one dye which is a halogenated 2-nitro-aniline of formula: ##STR1## in which Y is a halogen and Z is a NHR.sub.2 group or Y is hydrogen and Z is a halogen and R.sub.1 and R.sub.2, which may be identical or different, are each hydrogen, an alkyl group, a mono- or polyhydroxylated alkyl group, an alkyl group substituted with an alkoxy or hydroxyalkoxy group, or an aminoalkyl group, the amino group of which is optionally substituted with one or two alkyl or hydroxyalkyl groups, and it being possible for the nitrogen atom of the aminoalkyl group to form part of a heterocycle, all the abve alkyl groups or moieties containing from 1 to 6 carbon atoms,or, if the compound of formula (I) contains an amine group which can be salified, a cosmetically acceptable salt thereof.
    Type: Grant
    Filed: February 17, 1987
    Date of Patent: July 4, 1989
    Assignee: L'Oreal
    Inventors: Alex Junino, Gerard Lang, Nicole Jehanno, Jean J. Vandenbosche
  • Patent number: 4845129
    Abstract: The invention discloses certain diaryl substituted cyclopentane and cyclopentene derivatives useful as PAF inhibitors, pharmaceutical compositions containing said compounds as an active ingredient thereof and a method of using such compositions for inhibiting PAF-induced blood platelet aggregation, PAF-mediated broncho-constriction and extravasation, PAF-induced hypotension, PAF-induced ischemic bowel disease and PAF-mediated, endotoxin induced lug injury.
    Type: Grant
    Filed: March 14, 1988
    Date of Patent: July 4, 1989
    Assignee: Sandoz Pharm. Corp.
    Inventors: Robert C. Anderson, William J. Houlihan, Howard C. Smith, Edwin B. Villhauer
  • Patent number: 4837352
    Abstract: An intermediate compound having the structural formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n - wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together can be oxo; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms; R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub. 1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n - wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.
    Type: Grant
    Filed: March 21, 1988
    Date of Patent: June 6, 1989
    Assignee: Stauffer Chemical Company
    Inventor: Christopher G. Knudsen
  • Patent number: 4835314
    Abstract: 2-nitroaniline derivatives of the general formula I: ##STR1## in which R.sup.1 and R.sup.2 represent, independent of one another, hydrogen, an alkyl of 1 to 4 carbon atoms, a monohydroxyalkyl of 2 to 4 carbon atoms or a dihydroxyalkyl of 3 or 4 carbon atoms, provided that R.sup.1 and R.sup.2 do not simultaneously represent alkyl groups of 1 to 4 carbon atoms, and X denotes an alkyl, monohydroxyalkyl, perfluoroalkyl or halogen, for use as an agent in a hair dyeing composition. Also disclosed are new 2-nitroaniline derivatives of the general formula II: ##STR2## in which R.sup.a and R.sup.b denote, independent of one another, ethyl, a monohydroxylalkyl of 2 to 4 carbon atoms or a dihydroxyalkyl of 3 or 4 carbon atoms, when Z is methyl, Cl or Br; or when Z is CH.sub.2 OH or a perfluoroalkyl, R.sup.a denotes hydrogen, a monohydroxyalkyl of 2 to 4 carbon atoms or a dihydroxyalkyl of 3 or 4 carbon atoms, and R.sup.b represents 2-hydroxyethyl or 2,3-dihydroxypropyl.
    Type: Grant
    Filed: December 10, 1987
    Date of Patent: May 30, 1989
    Assignee: Wella Aktiengesellschaft
    Inventors: Eugen Konrad, Thomas Clausen, Hans-Jurgen Braun, Herbert Mager
  • Patent number: 4826982
    Abstract: Quinolonecarboxylic acid derivatives of the following formula, ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently hydrogen atom or lower alkyl group; the hydrates or the pharmaceutically acceptable acid addition or alkali salts thereof are useful as an antibacterial agent.
    Type: Grant
    Filed: September 2, 1986
    Date of Patent: May 2, 1989
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Kuniyoshi Masuzawa, Seigo Suzue, Keiji Hirai, Takayoshi Ishizaki
  • Patent number: 4797129
    Abstract: A dye composition for keratinous fibres comprising a solvent and at least one dye which is a compound of formula: ##STR1## in which R.sub.1 and R.sub.2 are each, independently of each other, hydrogen, an alkyl group, a mono- or polyhydroxylated alkyl group, an alkyl group substituted by an alkoxy or hydroxyalkoxy group, or an aminoalkyl group, the amino group of which is optionally substituted with one or two alkyl or hydroxyalkyl groups, and it being possible for the nitrogen atom also to form part of a heterocyclic ring, all the abovementioned alkyl groups or moieties containing from 1 to 6 carbon atoms, or, of the compound of formula (I) contains an amino group which can be salified, a cosmetically acceptable salt thereof.
    Type: Grant
    Filed: February 17, 1987
    Date of Patent: January 10, 1989
    Assignee: L'Oreal
    Inventors: Alex Junino, Gerard Lang, Nicole Jehanno, Jean J. Vandenbosche
  • Patent number: 4783213
    Abstract: Compounds of the formula ##STR1## wherein X is oxy, thio, sulfinyl or sulfonyl;R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, or phenyl;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.
    Type: Grant
    Filed: August 20, 1987
    Date of Patent: November 8, 1988
    Assignee: Stauffer Chemical Company
    Inventor: David L. Lee
  • Patent number: 4781751
    Abstract: Compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, halogen, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl, with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.5 is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is halogen, cyano, nitro, trifluoromethyl, --C(O)--OR.sup.f wherein R.sup.f is C.sub.1 -C.sub.4 alkyl, or --C(O)NR.sub.2.sup.b wherein R.sup.b is hydrogen or C.sub.1 -C.sub.2 alkyl;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.
    Type: Grant
    Filed: October 2, 1987
    Date of Patent: November 1, 1988
    Assignee: Stauffer Chemical Company
    Inventor: Hsiao-Ling M. Chin
  • Patent number: 4780569
    Abstract: Compounds of the formula ##STR1## wherein R is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.n - wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n - wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)- wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.sup.c)C(O)R.sup.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: October 25, 1988
    Assignee: Stauffer Chemical Company
    Inventor: David L. Lee
  • Patent number: 4775411
    Abstract: A compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n - wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or C.sup.3 and R.sup.4 are oxo; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; and R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n - wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: October 4, 1988
    Assignee: Stauffer Chemica Company
    Inventor: Christopher G. Knudsen
  • Patent number: 4767447
    Abstract: Compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy or difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are C.sub.2 -C.sub.5 alkylene;R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.
    Type: Grant
    Filed: September 12, 1986
    Date of Patent: August 30, 1988
    Assignee: Stauffer Chemical Company
    Inventors: David L. Lee, William J. Michaely
  • Patent number: 4766243
    Abstract: A process for the electrophilic ring fluorination of aromatic compounds which comprises reacting a fluorinating agent from the group consisting of CF.sub.3 OF and CF.sub.2 (OF).sub.2 with an aromatic compound of the formula ##STR1## where X is selected from the group consisting of ##STR2## and ##STR3## and Y is selected from the group consisting of --H, --CF.sub.3, --CN, --NO.sub.2, --Cl, and CH.sub.3.
    Type: Grant
    Filed: August 10, 1984
    Date of Patent: August 23, 1988
    Assignee: Occidental Chemical Corporation
    Inventor: Michael J. Fifolt
  • Patent number: 4749379
    Abstract: New nitroaminophenols, the process for preparation thereof and their use in dyeing keratinous fibres, and new intermediate nitroaminobenzenes and their use in dyeing keratinous fibres.The invention relates to a nitroaminophenol of formula: ##STR1## in which Z denotes --CH.sub.2 W, W denoting H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl, (C.sub.1 -C.sub.3), alkoxy(C.sub.1 -C.sub.6)alkyl or (C.sub.1 -C.sub.3)hydroxyalkoxy(C.sub.1 -C.sub.6)-alkyl and R denotes H, (C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 hy-droxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl or (C.sub.1 -C.sub.3)-alkoxy(C.sub.1 -C.sub.6)alkyl, and the process for preparation thereof, and the intermediate compound of formula: ##STR2## in which R' denotes C.sub.1 -C.sub.6 hydroxyalkyl, C.sup.2 -C.sub.6 polyhydroxyalkyl or (C.sub.1 -C.sub.3)alkoxy(C.sub.1 -C.sub.6)alkyl and the process for preparation thereof.
    Type: Grant
    Filed: April 11, 1986
    Date of Patent: June 7, 1988
    Assignee: L'Oreal
    Inventors: Alex Junino, Gerard Lang, Alain Genet
  • Patent number: 4740622
    Abstract: New 3-amino-4-nitrophenols, the process for preparation thereof and their use in dyeing keratinous fibres, and new intermediate 4,5-dinitrophenols.The present invention relates to a 3-amino-4-nitrophenol of formula: ##STR1## where Z denotes --CH.sub.2 --W, W denoting hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl, (C.sub.1 -C.sub.3)alkoxy(C.sub.1 -C.sub.6)alkyl or (C.sub.1 -C.sub.3)hydroxyalkoxy(C.sub.1 -C.sub.6)alkyl and R denotes hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl or (C.sub.1 -C.sub.3)alkoxy(C.sub.1 -C.sub.6)alkyl, the process for preparation thereof and the intermediate compound of formula: ##STR2## in which Z' denotes CH.sub.2 --W, W denoting C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl, (C.sub.1 -C.sub.3)alkoxy-(C.sub.1 -C.sub.6)alkyl or (C.sub.1 -C.sub.3)hydroxyalcoxy(C.sub.1 -C.sub.6)alkyl.
    Type: Grant
    Filed: April 11, 1986
    Date of Patent: April 26, 1988
    Assignee: L'Oreal
    Inventors: Alex Junino, Gerard Lang, Alain Genet
  • Patent number: 4736067
    Abstract: New dimethyl derivatives of 3-nitro-4-aminoaniline, process for their preparation, and their use for dyeing keratinic fibres.The invention relates to dimethyl derivatives of 3-nitro-4-aminoaniline of formula: ##STR1## in which CH.sub.3 is in position 2 or 5 of the benzene ring and R.sub.1 and R.sub.2 denote independently of each other a hydrogen atom, a lower alkyl group, a lower mono- or polyhydroxyalkyl or a lower aminoalkyl group in which the amino group is optionally mono- or disubstituted by a lower alkyl radical or by a lower mono- or polyhydroxyalkyl radical, it being understood that the two symbols R.sub.1 and R.sub.2 can be simultaneously other than hydrogen only when the mobile CH.sub.3 radical is in position 5, or cosmetically acceptable salts of these compounds, as well as the process for preparing them and their use in dye compositions, in particular for hair, equally for direct coloring and for coloring by an oxidation route.
    Type: Grant
    Filed: September 6, 1984
    Date of Patent: April 5, 1988
    Assignee: L'Oreal
    Inventors: Andree Bugaut, Alain Genet, Jean Cotteret, Alex Junino
  • Patent number: 4728653
    Abstract: A series of novel heterocyclic-substituted 2-(1H)-quinolone compounds have been prepared, including the 3,4-dihydro derivatives thereof, wherein the heterocyclic ring moiety is a pyrrolyl, imidazolyl, pyrazolyl, triazolyl or tetrazolyl group attached by a nitrogen atom of said group to the 5-, 6-, 7- or 8-positions of the quinolone ring. These particular compounds are useful in therapy as highly potent inotropic agents and therefore, are of value in the treatment of various cardiac conditions. Preferred member compounds include 6-(2,4-dimethylimidazol-1-yl)-8-methyl-2-(1H)-quinolone, 6-(2,4-dimethyl-5-nitroimadazol-1-yl)-8-methyl-2-(1H)-quinolone, 8-methyl-6-(tetrazol-1-yl)-2-(1H)-quinolone, 8-methyl-6-(1,2,4-triazol-4-yl)-2-(1H)-quinolone, and 6-(4-cyano-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone, respectively. Methods for preparing these compounds from known starting materials are provided.
    Type: Grant
    Filed: March 26, 1986
    Date of Patent: March 1, 1988
    Assignee: Pfizer Inc.
    Inventors: Simon F. Campbell, David A. Roberts
  • Patent number: 4727192
    Abstract: The invention relates to a compound of formula ##STR1## in which: X denotes a branched or unbranched alkylene radical containing 2 to 6 carbon atoms, optionally being able to be substituted with one or more hydroxyl radicals;R denotes a hydrogen atom, an alkyl or a mono- or polyhydroxyalkyl radical or an aminoalkyl radical in which the amine group can be mono- or disubstituted with an alkyl radical or with a mono- or polyhydroxyalkyl radical, the nitrogen atom also being able to form part of a heterocyclic system and the alkyl radicals containing 1 to 4 carbon atoms;R' denotes a hydrogen atom or a C.sub.1 to C.sub.4 alkyl radical;Y and Z denote a nitro and/or --NHR.sub.1 radical, R.sub.
    Type: Grant
    Filed: December 13, 1985
    Date of Patent: February 23, 1988
    Assignee: L'Oreal
    Inventors: Alex Junino, Gerard Lang, Nicole Jehanno
  • Patent number: 4724263
    Abstract: Compounds of the formula ##STR1## wherein R is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.m --wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are methyl or ethyl;R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)--wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: February 9, 1988
    Assignee: Stauffer Chemical Company
    Inventor: Charles G. Carter
  • Patent number: 4704474
    Abstract: New 1,4-diamino-5-chloro-2-nitrobenzene derivatives are disclosed of the formula I ##STR1## Wherein R.sup.1 and R.sup.2 are the same or different and are each hydrogen, 2-hydroxyethyl or 2,3-dihydroxypropyl, with the proviso, that at least one of said R.sup.1 and R.sup.2 is 2,3-dihydroxypropyl, along with processes for their production, as well as hair coloring compositions containing the same and methods of coloring hair. The compounds are red- to violet-coloring direct dyes, and are readily soluble in water, with favorable toxicological characteristics.
    Type: Grant
    Filed: February 26, 1986
    Date of Patent: November 3, 1987
    Assignee: Wella Aktiengesellschaft
    Inventors: Eugen Konrad, Thomas Clausen
  • Patent number: 4700003
    Abstract: New compounds having the formula I are described: ##STR1## wherein R and R.sup.1, independently are H, halogen, a straight- or branched-chain alkyl having 1 to 8 carbon atoms or a residue having the formula II: ##STR2## wherein R.sup.2 and R.sup.3 are the same or different and each is H or straight- or branched-chain alkyl having 1 to 4 carbon atoms and R.sup.4 is H, halogen or straight- or branched-chain alkyl having 1 to 4 carbon atoms; provided that at least one of R and R.sup.1 is a residue of formula II, and that when R is a residue of formula II wherein R.sup.2, R.sup.3, and R.sup.4 and H, R.sup.1 may not be ethyl or n-propyl.Processes for producing the new compounds are also disclosed.Compounds of formula I are useful as intermediates for valuable dispersion dyestuffs.
    Type: Grant
    Filed: December 18, 1985
    Date of Patent: October 13, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Frederick H. Howell
  • Patent number: 4681621
    Abstract: Compounds of the formula ##STR1## wherein R is halogen, preferably chlorine or bromine; C.sub.1 -C.sub.4 alkoxy, preferably methoxy; nitro; cyano; --S(O).sub.n R' wherein n is the integer 0, 1 or 2, preferably 2 and R' is C.sub.1 -C.sub.4 alkyl, preferably methyl; or R is C.sub.1 -C.sub.4 alkyl or methyl and most preferably R is chlorine, bromine, methoxy, nitro, methyl or CF.sub.3 ; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or ##STR2## wherein R.sup.a is C.sub.1 -C.sub.4 alkyl; R.sup.1 and R.sup.2 together are alkylene having 3 to 6 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; and R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) OCF.sub.3 ; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1, or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.
    Type: Grant
    Filed: December 3, 1985
    Date of Patent: July 21, 1987
    Assignee: Stauffer Chemical Company
    Inventors: David L. Lee, William J. Michaely
  • Patent number: 4675445
    Abstract: A process for eliminating N-nitrosamines, particularly N,N-dialkyl-N-nitrosamines and N-alkyl-N-aryl-N-nitrosamines from N-nitrosamine containing compositions through the addition of organic carboxylic acid halides. The process eliminates N-nitroso compounds without rearrangement to C-nitroso compounds.
    Type: Grant
    Filed: November 12, 1985
    Date of Patent: June 23, 1987
    Assignee: BASF Corporation
    Inventors: Pauls Davis, Donald C. Mente
  • Patent number: 4666453
    Abstract: The invention relates to compounds of formula ##STR1## in which X denotes a halogen atom, and R and R' denote a hydrogen atom, an alkyl, polyhydroxyalkyl, hydroxyalkoxyalkyl or alkoxyalkyl radical or an aminoalkyl radical optionally substituted on the nitrogen atom provided that at least one of the groups R and R' is a polyhydroxyalkyl, alkoxyalkyl or hydroxyalkoxyalkyl radical, and to dye compositions for keratinic fibres in which they are employed, to the preparation process and to intermediates.
    Type: Grant
    Filed: June 10, 1986
    Date of Patent: May 19, 1987
    Assignee: L'Oreal
    Inventors: Alex Junino, Gerard Lang, Ginette Jeanminet
  • Patent number: 4638090
    Abstract: Processes for the preparation of nitrosamine-free N,N-disubstituted nitroaromatic amines by degradation of their nitrosamine components formed during their preparation, and by stabilization of the products against renewed formation of nitrosamines, by treating the amines in liquid or molten form with a sulfonic acid, where necessary in the presence of inert organic solvents or diluents.
    Type: Grant
    Filed: December 12, 1984
    Date of Patent: January 20, 1987
    Assignee: Hoechst Aktiengesellschat
    Inventors: Rudolf Heinrich, Konrad Albrecht
  • Patent number: 4613698
    Abstract: Process for the preparation of 6-chloro-2,4-dinitroaniline by chlorination of 2,4-dinitroaniline with sodium hypochlorite in water using acid, which comprises carrying out the chlorination in the presence of a mineral acid or strong organic acid at a pH value .ltoreq.0 and in the presence of a dispersing agent at temperatures of about 40.degree. to 50.degree. C. and, when the chlorination has ended, either (a) filtering the resulting acid aqueous dispersion hot and washing the filtered reaction product with hot aqueous alkali solution, or (b) initially rendering the resulting acid aqueous dispersion alkaline with aqueous alkali solution and then filtering the mixture hot and subsequently washing the filtered reaction product with hot dilute mineral acid.
    Type: Grant
    Filed: February 27, 1985
    Date of Patent: September 23, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Otto Arndt, Theodor Papenfuhs
  • Patent number: 4612396
    Abstract: A process for the preparation of pure 2-ethylamino-4-nitro-1-alkoxybenzenes of the formula (1) ##STR1## in which R denotes an alkyl(C.sub.1 -C.sub.4) or alkoxy(C.sub.1 -C.sub.4)-alkyl(C.sub.1 -C.sub.4) group, which comprises N-monoalkylation of 2-amino-4-nitro-1-alkoxybenzenes of the formula (2) ##STR2## in which R has the abovementioned meaning, using a slight excess of diethyl sulfate in non-polar, organic solvents in the absence of water at temperatures of about 40.degree. to about 120.degree. C.
    Type: Grant
    Filed: June 18, 1985
    Date of Patent: September 16, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Koller, Theodor Papenfuhs
  • Patent number: 4605767
    Abstract: Process for the preparation of 2,6-dichloro-4-nitroaniline by chlorination of 4-nitroaniline with chlorine bleaching liquor in water using acids, which comprises chlorinating 1 mole of 4-nitroaniline in 3-6 moles of hydrochloric acid (HCl) or nitric acid (HNO.sub.3) in the form of a dilute, aqueous acid in the presence of a dispersing agent which is stable under the reaction conditions, the chlorination initially being carried out at 5.degree. to 10.degree. C. and then at 15.degree.-20.degree. C. and, finally, after 90-95% of the 2-chloro-4-nitroaniline intermediately formed has been converted into 2,6-dichloro-4-nitroaniline, the temperature of the aqueous suspension being increased from 15.degree.-20.degree. C. to 70.degree. C., without further addition of chlorine bleaching liquor, and then by post-chlorinating, by renewed addition of chlorine bleaching liquor, at temperatures between 20.degree. and 70.degree. C., bringing the pH of the aqueous suspension to 9.
    Type: Grant
    Filed: May 16, 1985
    Date of Patent: August 12, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Otto Arndt, Theodor Papenfuhs
  • Patent number: 4600797
    Abstract: Process for the preparation of a nitroaminobenzene by nitrating an aminobenzene which is protected at the nitrogen wherein the nitration is carried out by the simultaneous combination of nitric acid and the aminobenzene to be nitrated, in the presence of inert solvents such as methylene chloride.
    Type: Grant
    Filed: February 18, 1983
    Date of Patent: July 15, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventor: Willi Schossler
  • Patent number: 4599450
    Abstract: Acid nitro dyestuffs are prepared by treating aminonitrodiphenylaminesulfonic acids with an oxidizing agent in an aqueous medium, the oxidizing agent employed being a manganese-(VI) or manganese-(VII) compound and the reaction being carried out at a pH higher than 5 and at a temperature between 20.degree. and 100.degree. C. The dyestuffs thus obtainable dye even fresh full-grained chrome leather in full shades.
    Type: Grant
    Filed: May 10, 1984
    Date of Patent: July 8, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hasso Hertel
  • Patent number: 4591359
    Abstract: Acid nitrodyestuffs are prepared by treating aminonitrodiphenylaminesulfonic acids with an oxidizing agent in an aqueous medium, the oxidizing agent being hypochlorous acid or its alkali metal or alkaline earth metal salts and the reaction taking place at above pH 4 and at a temperature between 0.degree. and 100.degree. C. The dyestuffs thus obtainable dye even fresh full chrome grained leather in deep shades.
    Type: Grant
    Filed: August 23, 1984
    Date of Patent: May 27, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hasso Hertel
  • Patent number: 4588410
    Abstract: 2-hydroxy-4-aminobenzene are disclosed, useful as oxidative hair coloring substances. These are of the formula ##STR1## wherein R is hydrogen, methyl or hydroxyethel.
    Type: Grant
    Filed: July 18, 1983
    Date of Patent: May 13, 1986
    Assignee: Wella Aktiengesellschaft
    Inventors: Eugen Konrad, Hans-Jurgen Braun, Herbert Mager
  • Patent number: 4581178
    Abstract: Low valent transition metal complexes containing small cone angle phosphine or arsine ligands efficiently catalyze addition of aldehydes to compounds or groups having a C--H bond activated by a nitro or nitrile group, to provide nitroalcohols or cyanohydrins, respectively.
    Type: Grant
    Filed: February 28, 1985
    Date of Patent: April 8, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: David Milstein
  • Patent number: 4575378
    Abstract: The invention relates to new 3-nitro-4-aminophenols of the formula (I) ##STR1## in which R denotes hydrogen or halogen, preferably chlorine or bromine, and R' denotes hydrogen or alkyl, hydroxyalkyl, dihydroxyalkyl or halogenohydroxyalkyl which has 1 to 6 carbon atoms and is straight-chain or branched, with the proviso that, if R is hydrogen, R' does not denote hydrogen, methyl or .beta.-hydroxyethyl.Processes for their preparation: (a) by reacting corresponding 3-nitro-4-aminophenols with certain halogenoalkyl chloroformates and subsequent basic treatment of the process products, or (b) by reacting corresponding 4-halogeno-3-nitrophenols with certain amines, and the intermediate products obtained and coloring agents for keratinic fibres, preferably for human hair, which contain at least one compound of the formula (I).
    Type: Grant
    Filed: January 19, 1984
    Date of Patent: March 11, 1986
    Assignee: Hans Schwarzkopf GmbH
    Inventors: Winfried Seidel, Thomas Oelschlager, Wolfgang Schlenther
  • Patent number: 4551264
    Abstract: New polyhalogenoaromatic compounds of Formula I ##STR1## wherein Y and Z are each independently alkyl, alkoxy or alkanoyl each of 1 to 12 C atoms, --COOR.sup.1, --O--CO--R.sup.1, CN, NO.sub.2, NH.sub.2 or OH;Q is one or two identical or different radicals selected from Ph, Cy, 1,4-bicyclo[2,2,2]octylene or 1,3-dioxane-2,5-diyl;X.sup.1 to X.sup.4 are each independently H, F, Cl or Br;R.sup.1 is alkyl of 1 to 4 C atoms, Ph--R.sup.2 or Cy--R.sup.2 ;R.sup.2 is alkyl or alkoxy each of 1-12 C atoms or CN;Ph is 1,4-phenylene; and Cy is 1,4-cyclohexylene,can be used as components of liquid-crystal dielectrics.
    Type: Grant
    Filed: March 14, 1983
    Date of Patent: November 5, 1985
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rudolf Eidenschink, Michael Romer, Georg Weber
  • Patent number: 4540522
    Abstract: This invention pertains to processes for the preparation of nuclear substituted benzylic halides such as ortho-amino benzyl chlorides by reaction of substituted benzyl sulfoxides with nonoxidizing acid halides.
    Type: Grant
    Filed: October 7, 1983
    Date of Patent: September 10, 1985
    Assignee: Monsanto Company
    Inventors: John P. Chupp, Terry M. Balthazor
  • Patent number: 4540817
    Abstract: A process for the preparation of 5-amino-2,4-dimethylacetanilide by reduction of 5-nitro-2,4-dimethylacetanilide with hydrogen is disclosed characterized in that a crude mixture containing 5-nitro-2,4-dimethylacetanilide in admixture with at least one of its position isomers is hydrogenated in a water-miscible organic solvent which optionally contains water. The 5-amino-2,4-dimethylacetanilide is separated off from the reaction mixture by means of crystallization employing a mixture of water-miscible organic solvent and water.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: September 10, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Behre, Heinz U. Blank, Alfred Seyberlich, Ferdinand Hagedorn
  • Patent number: 4537992
    Abstract: A method for removal of nitrosoamine impurities from herbicides comprising contacting a nitrosoamine containing herbicide homogeneously with 0.001% to 1.0% of a compound having the formula: ##STR1## where X equals chlorine or bromine,R.sup.1 equals lower alkyl, anda equals zero or 1; provided that when a equals 1, then:R equals X.sub.n H.sub.(3-n) C(CH.sub.2).sub.p --, or ##STR2## or R.sup.2 COX, where R.sup.2 is selected from alkylene, alkenylene, alkynylene groups having 1 to 5 carbon atoms,n equals 1 to 3, andp equals zero, 1 or 2; and provided that when a equals zero, then:R equals aminophenyl,for a sufficient length of time to remove at least a substantial amount of the nitrosoamine.
    Type: Grant
    Filed: February 9, 1984
    Date of Patent: August 27, 1985
    Assignee: Agan Chemical Manufacturers, Ltd.
    Inventors: Michael Pikarski, Julian Gabe, Edmund Dykman
  • Patent number: 4531013
    Abstract: A new compound 2,6-diamino-1,4,5,8-tetranitronaphthalene is disclosed and a method of preparation thereof. The new compound is useful as a high energy, high density explosive.
    Type: Grant
    Filed: August 3, 1984
    Date of Patent: July 23, 1985
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Albert A. De Fusco, Arnold T. Nielsen