Chalcogen Attached Indirectly To The Polycyclo Ring System By Nonionic Bonding Patents (Class 548/260)
  • Patent number: 5243047
    Abstract: A compound contains a ligand group and at least one group of the general formula --XR.sub.n where X is a linking group which contains at least one hetero-atom, R is a saturated hydrocarbyl group containing at least six carbon atoms or is an unsaturated hydrocarbyl group containing at least three carbon atoms. The ligand group can be a polyhydroxyhydrocarbyl, a triazole, an imidazole, an indazole, a thiazole, an oxazole, a carbamate, an xanthate or a phthalazine. The compounds can be used to improve bonding between a metal and a coating material in contact with the metal surface. The metal may be a tire cord and the coating material rubber or a rubber composition.
    Type: Grant
    Filed: November 16, 1990
    Date of Patent: September 7, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventor: John R. Lawson
  • Patent number: 5237071
    Abstract: A method for preparing 2,2'-methylene-bis-[6-(2H)-benzotriazol-2-yl)-4-hydrocarbyl phenols] is disclosed. According to the process(i) formaldehyde, a dialkylamine and a 4-hydrocarbyl-6-benzotriazolyl phenol as monomer are mixed;(ii) the mixture is heated to a temperature high enough to remove the water produced by the reaction of the mixture;(iii) thereafter an alkaline catalyst is added with heating for several hours;(iv) the phenol compound precipitates when the reaction mixture is neutralized and solvent for the salt product of the neutralization reaction is added in an amount sufficient to permit stirring.The solid product produced is 2,2'-methylene-bis-[6-(2H-benzotriazol-2-yl)-4-hydrocarbyl phenol] having the formula I: ##STR1## in which each R group is an alkyl group of one to twelve carbons or a cycloalkyl group of five to eight carbons and X is chloro or hydrogen.
    Type: Grant
    Filed: January 22, 1991
    Date of Patent: August 17, 1993
    Assignee: Fairmount Chemical Company, Inc.
    Inventors: William E. Leistner, Semyon Moshchitsky, Mahmut Levent
  • Patent number: 5235058
    Abstract: There is disclosed a 3(5)-hydrazinopyrazole compound represented by the following formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, a hydroxyl group, an alkoxy group, or an aryloxy group, R.sub.2 represents a hydrogen atom or an acyl group, X represents an aryloxy group, an alkoxy group, a heterocyclic oxy group, or an azolyl group, M represents a hydrogen ion or a metal ion, Y represents an acid radical, and n is 0 or a positive number.
    Type: Grant
    Filed: September 17, 1991
    Date of Patent: August 10, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Tadahisa Sato, Keizo Kumura
  • Patent number: 5233047
    Abstract: Hydrazide functionalized benzotrialzole and oxanilide ultraviolet absorbers (Formulas I and II) useful for stabilizing coreactive or inert polymeric compositions and novel intermediates (Formula III used to make certain types of compounds of Formula I) are disclosed and have the general formulas: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, X, Y, all substituents thereof, and n are set forth in the Summary of the Invention.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: August 3, 1993
    Assignee: Elf Atochem North America, Inc.
    Inventors: Ronald E. MacLeay, Terry N. Myers
  • Patent number: 5229521
    Abstract: Compounds of formula ##STR1## wherein R.sub.1 is hydrogen alkyl, alkoxy, phenyl, phenylaklyl or halogen, and R.sub.2 is alkyl phenyl, phenylaklyl or cycloalkyl, are prepared by reacting a compound of formula ##STR2## with a compound of formula ##STR3## wherein R.sub.3 and R.sub.4 are alkyl, and formaldehyde, in a one-pot process in the absence of a solvent.
    Type: Grant
    Filed: October 23, 1992
    Date of Patent: July 20, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Reto Luisoli, Werner Stegmann
  • Patent number: 5206378
    Abstract: Ultraviolet light stabilizers are chemically bound to anhydride containing polymers or copolymers. Polymeric stabilizers are prepared by the reaction of primary amino or hydrazido-substituted UV absorbers with some or all of the anhydride groups of the polymer or copolymer to form pendant stabilizer substituted imide or amic acid groups. The polymer bound stabilizers are not lost from the polymer system by volatilization, migration, or extraction, even at high temperature. The polymer stabilizers of this invention may be used as they are or as concentrates to stabilize other polymer systems.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: April 27, 1993
    Assignee: Elf Atochem North America, Inc.
    Inventors: Ronald E. MacLeay, Terry N. Myers
  • Patent number: 5190565
    Abstract: A new class of sulfonated 2-(2'-hydroxyaryl)-2H-benzotriazole compounds and method for using them and other sulfonated hydroxyaryl benzotriazoles on nylon fibers to improve stain resistance and dye lightfastness has been discovered. A process is provided for improving stain resistance of nylon fibers by treatment with sulfonated aromatic-formaldehyde condensate and fluorinated dry soil resist agents.
    Type: Grant
    Filed: February 1, 1991
    Date of Patent: March 2, 1993
    Assignee: Allied-Signal Inc.
    Inventors: Morris B. Berenbaum, John H. Bonfield, Charles J. Cole, Paul W. Harris, Thomas P. J. Izod, Harry E. Ulmer, Frederick R. Hopf, James T. Yardley, Karen M. Bland
  • Patent number: 5190942
    Abstract: Novel compounds are disclosed having the formula ##STR1## wherein X, Y, R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are as defined herein. These compounds inhibit the action of angiotensin II and are useful, therefore, for example, as antihypertensive agents.
    Type: Grant
    Filed: April 22, 1991
    Date of Patent: March 2, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Michael A. Poss
  • Patent number: 5190574
    Abstract: A herbicidal compound of formula (I): ##STR1## in which the dotted line indicates the presence of two double bonds arranged so as to form a fused hetero-aromatic ring system;Py is an optionally substituted pyrazole ring;W is O or NR.sup.1 ; where R.sup.1 is hydrogen or lower alkyl;X is (CH.sub.2).sub.n, CH.dbd.CH, CH(OR.sup.5)CH.sub.2, COCH.sub.2 ;where n is 0, 1 or 2;R.sup.2 and R.sup.3 are independently selected from H, optionally substituted alkyl, alkenyl or alkynyl, halogen, NR.sup.6 R.sup.7, or R.sup.2 and R.sup.3 together with the carbon to which they are attached form an optionally substituted alkenyl or cycloalkyl group;R.sup.4 is CO.sub.2 R.sup.8, CN, COR.sup.8, CH.sub.2 OR.sup.8, CH(OH)R.sup.8, CH(OR.sup.8)R.sup.9, CSNH.sub.2, COSR.sup.8, CSOR.sup.8, CONHSO.sub.2 R.sup.8, CONR.sup.10 R.sup.11, CONHNR.sup.10 R.sup.11, CONHN.sup.+ R.sup.10 R.sup.11 R.sup.12 R.sup.14-, CO.sub.2.sup.- R.sup.15+ or COON.dbd.CR.sup.10 R.sup.11 ;R.sup.15+ is an agriculturally acceptable cation and R.sup.
    Type: Grant
    Filed: February 7, 1991
    Date of Patent: March 2, 1993
    Assignee: Imperial Chemical Industries plc
    Inventors: David P. J. Pearson, John E. D. Barton, Christopher J. Mathews, David Cartwright, Susan P. Barnett
  • Patent number: 5187289
    Abstract: A method of preparing 2-phenylbenzotriazoles expressed by Formula I: ##STR1## (wherein R.sub.1 denotes a hydrogen or chlorine atom, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxyl group having 1 to 4 carbon atoms, a carboxyl group or a sulfonic acid group; R.sub.2 denotes a hydrogen or chlorine atom, a lower alkyl group having 1 to 4 carbon atoms or a lower alkoxyl group having 1 to 4 carbon atoms; R.sub.3 denotes a hydrogen or chlorine atom, an alkyl group having 1 to 12 carbon atoms, a lower alkoxyl group having 1 to 4 carbon atoms, a phenyl group, a phenyl group substituted by an alkyl group having 1 to 8 carbon atoms, a phenoxy group or a phenylalkyl group with an alkyl part having 1 to 4 carbon atoms; R.sub.4 denotes a hydrogen or chlorine atom, a hydroxyl group or an alkoxyl group having 1 to 4 carbon atoms; and R.sub.
    Type: Grant
    Filed: July 31, 1991
    Date of Patent: February 16, 1993
    Assignee: Chemipro Kasei Kaisha, Ltd.
    Inventors: Naohiko Fukuoka, Kazunobu Kubota, Kunitoshi Iguchi
  • Patent number: 5182403
    Abstract: The present invention relates to 3 indazol substituted 5 Beta amidomethyloxazolidin-2ones, useful as antibacterial agents and to intermediates for their production.
    Type: Grant
    Filed: April 23, 1992
    Date of Patent: January 26, 1993
    Assignee: The Upjohn Company
    Inventor: Steven J. Brickner
  • Patent number: 5166355
    Abstract: A method is described for preparing compounds of Formula I and Formula II: ##STR1## R.sub.1 is an alkyl group of one to twelve carbon atoms or a cycloalkyl group of five to eight carbons, X is chloro or hydrogen, and R.sub.2 is an alkoxy group having one to twelve carbons. In accordance with the method:(a) a bis(dialkylamino)methane is formed, preferably by reacting a dialkylamine of the formula HNR.sub.3 R.sub.4 (wherein R.sub.3 and R.sub.4 are independently alkyl groups having three or more carbons) and a solid formaldehyde material to produce the corresponding bis(dialkylamino)methane,(b) a monomer of Formula III or IV ##STR2## in which R.sub.1 is an alkyl group of one to twelve carbons or a cycloalkyl group of five to eight carbons, X is chloro or hydrogen and R.sub.
    Type: Grant
    Filed: February 4, 1991
    Date of Patent: November 24, 1992
    Assignee: Fairmount Chemical Co., Inc.
    Inventors: William E. Leistner, Semyon Moshchitsky, Mahmut Levent
  • Patent number: 5164510
    Abstract: The present invention relates to 5'-indolinyloxazolidin-2-ones (XI) ##STR1## 3-(fused-ring) substituted)phenyl-5.beta.-amidomethyloxazolidin-2-ones (XXI) ##STR2## and 3-(nitrogen substituted)phenyl-5.beta.-amidomethyloxazolidin-2-ones (LV) which are useful as antibacterial agents and the intermediates (VI), (VII) and (VIII) useful for their production.
    Type: Grant
    Filed: February 20, 1991
    Date of Patent: November 17, 1992
    Assignee: The Upjohn Company
    Inventor: Steven J. Brickner
  • Patent number: 5162405
    Abstract: The present invention comprises novel single-functional and mixtures of multi-functional oligomeric performance additive compounds having one or more components of Structure A R1 ? ? ##STR1## (The definitions of R, Z1, Z2, Z3, A1, A2, A3 and y are given in the Summary Section), their uses and polymeric compounds and compositions containing them which have enhanced oxidative stabilities, enhanced ultraviolet (UV) and light stabilites and/or enhanced flame retardance. An example is the bis sulfonic acid bispotassium salt reaction product from an oligomeric caprolactone diol (TONE.RTM. 260), 2-sulfobenzoic acid anhydride and potassium carbonate, and use of this product, at levels up to about 3.0%, in a general purpose bisphenol A polycarbonate resin, to enhance the fire resistance or flame retardance of the polycarbonate resin.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: November 10, 1992
    Assignee: ELF Atochem North America, Inc.
    Inventors: Ronald E. MacLeay, Jose Sanchez, Daryl L. Stein
  • Patent number: 5157046
    Abstract: A method for treating skin disorders in warm-blooded animals, said method comprising administering to said warm-blooded animals an effective amount of an appropriately substituted benzimidazole or benzotriazole which suppresses the metabolism of retinoids. Compositions comprising said compounds and an effective amount of a retinoid.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: October 20, 1992
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Jean P. F. Van Wauwe, Alfons H. M. Raeymaekers
  • Patent number: 5142059
    Abstract: Monosulfonated 2-(2'-hydroxyphenyl)-benzotriazoles of the formula ##STR1## in which R.sub.1 is hydrogen or chlorine and one of R.sub.2 and R.sub.3 is chlorine or lower alkyl and the other is a radical of the formula ##STR2## in which R.sub.4 and R.sub.5 independently of one another are hydrogen or methyl and M is hydrogen, an alkali metal or ammonium.The compounds of the formula (1) are used as UV absorbers for polyamide fibres, wool and mixtures thereof.
    Type: Grant
    Filed: September 7, 1990
    Date of Patent: August 25, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Burdeska, Gerhard Reinert
  • Patent number: 5128267
    Abstract: Naphthotriazolium salts which are chromogenic indicators for reducing substrate, such as NADH or NADPH.
    Type: Grant
    Filed: February 19, 1991
    Date of Patent: July 7, 1992
    Assignee: Miles Inc.
    Inventors: Jurgen Kocher, Meinhard Rolf, Klaus Wehling
  • Patent number: 5104992
    Abstract: A method of preparing 2-phenylbenzotriazoles expressed by Formula I: ##STR1## (wherein R.sub.1 denotes a hydrogen or chlorine atom, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxyl group having 1 to 4 carbon atoms, a carboxyl group or a sulfonic acid group; R.sub.2 denotes a hydrogen or chlorine atom, a lower alkyl group having 1 to 4 carbon atoms or a lower alkoxyl group having 1 to 4 carbon atoms; R.sub.3 denotes a hydrogen or chlorine atom, an alkyl group having 1 to 12 carbon atoms, a lower alkoxy group having 1 to 4 carbon atoms, a phenyl group, a phenyl group substituted by an alkyl group having 1 to 8 carbon atoms, a phenoxy group or a phenylalkyl group with an alkyl part having 1 to 4 carbon atoms; R.sub.4 denotes a hydrogen or chlorine atom, a hydroxyl group or an alkoxyl group having 1 to 4 carbon atoms; and R.sub.
    Type: Grant
    Filed: April 2, 1990
    Date of Patent: April 14, 1992
    Assignee: Chemipro Kasei Kaisha, Ltd.
    Inventors: Naohiko Fukuoka, Kazunobu Kubota, Kunitoshi Iguchi
  • Patent number: 5099027
    Abstract: Polymerizable ethylenically unsaturated monomers comprising the reaction product of a 1,2-epoxy group-containing polymerizable ethylenically unsaturated monomer and a 2(2-hydroxyphenyl)2H-benzotriazole compound of the structure: ##STR1## where X is=to H, OR and NR.sub.2 where R=alkyl; Z'=H and C.sub.2 H.sub.4 OH; Z and Y=H when Z'=C.sub.2 H.sub.4 OH; when Z'=H, Y and Z=OH or Y=H and Z.times.OH are disclosed. The monomers are useful in preparing free radical initiated addition polymers. Polymers can also be prepared by first preparing a free radical initiated addition polymer derived from a 1,2-epoxy group-containing polymerizable ethylenically unsaturated monomer and subsequently reacting the polymer with the benzotriazole compound. Both types of polymer contain permanent polymer-bound ultraviolet light stabilizers and are useful as binders for exterior coatings, as resins for the manufacture of optical lenses, and as components for sunscreens and suntanning lotions.
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: March 24, 1992
    Assignee: PPG Industries, Inc.
    Inventors: Otto Vogl, Chongli Zhang
  • Patent number: 5097041
    Abstract: There is disclosed a process in which a melt of a 2-aryl-2H-benzotriazole containing colored contaminants, or a solution thereof in an organic nonpolar solvent, is purified by treatment with a strongly acidic synthetic cationic exchange resin.
    Type: Grant
    Filed: October 11, 1990
    Date of Patent: March 17, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Ariane Higel, Sebastian Staubli, Daniel Thibaut, Hans Horisberger
  • Patent number: 5095062
    Abstract: Liquid substituted, 2H-benzotriazole mixtures are prepared by alkylation with concomitant dealkylation, fragmentation and realkylation of 2-(2-hydroxy-5-alkylphenyl)-2H-benzotriazoles or of 2-(2-hydroxy-3,5-dialkylphenyl)-2H-benzotriazoles with straight or branched alkenes of 8 to 30 carbon atoms in the presence of an acid catalyst at 100.degree.-200.degree. C. The liquid mixtures exhibit outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the processing of stabilized compositions at elevated temperatures.
    Type: Grant
    Filed: September 5, 1990
    Date of Patent: March 10, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Roland A. E. Winter, Robert E. Detiefsen, Werner Stegmann, Reto Luisoli, David Leppard
  • Patent number: 5081258
    Abstract: A hydroxyphenyl-benzotriazole bisurea UV light stabilizer for organic polymers and a process for making it are provided. The stabilizer is particularly useful for spandex polymer yarns that are subjected to solvent scouring. A preferred stabilizer of the invention is a bisurea formed by reacting methylene-bis(4-phenylisocyanate) with 2-[2-hydroxy-3-(1,1-dimethylethyl)-5-(N-aminoethyl)propionamid-phenyl]-2H- benzotriazole.
    Type: Grant
    Filed: May 5, 1989
    Date of Patent: January 14, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Akitsugu Kawaguchi
  • Patent number: 5071995
    Abstract: Provided are 2-hydroxyphenylbenzotriazol compounds with excellent ultraviolet absorbability and high thermal stability. They can be used as ultraviolet absorber for any polymer.
    Type: Grant
    Filed: September 29, 1989
    Date of Patent: December 10, 1991
    Assignee: Kuraray Co., Ltd.
    Inventors: Tsugunori Kashimura, Tsutomu Miura, Keiji Matsumura
  • Patent number: 5066656
    Abstract: (6,7-dihydro-5H-pyrrolo[1,2-c]imidazolyl-5-yl)- and (5,6,7,8-tetrahydroimidazo[1,5-a]pyridinyl-5-yl) substituted 1H-benzotriazole derivatives, compositions containing the same and methods of treating estrogen dependent disorders.
    Type: Grant
    Filed: September 10, 1990
    Date of Patent: November 19, 1991
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Michael N. Greco, Marcel A. C. Janssen
  • Patent number: 5055587
    Abstract: A process for preparing a 1H-pyrazolo[5,1-C]-1,2,4-triazole compound represented by the following general formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a substituent group, R.sup.2 represents an alkyl group, an aryl group or a heterocyclic ring group, and X represents a hydrogen atom or a substituent group,which process comprises reacting either an imidic acid ester represented by the following general formula (II): ##STR2## wherein R.sup.2 is as defined above, R.sup.3 represents an alkyl group, and Y represents an acid radical, or an orthoester represented by the following general formula (III):R.sup.2 --C(OR.sup.3).sub.3 (III)wherein R.sup.2 and R.sup.3 are as defined above, with a 5-hydroazino-1H-pyrazole compound represented by the following general formula (IV): ##STR3## wherein R.sup.1 and X are as defined above, Y' represents an acid radical, and n represents O or a positive integer necessary to neutralize the intramolecular electric charge.
    Type: Grant
    Filed: March 15, 1989
    Date of Patent: October 8, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Yuki Mizukawa
  • Patent number: 5043469
    Abstract: Process for the introduction of functional or functionalizable substituents para to the amino group in 2-aminophenols and 3-aminophenols. The process proceeds in one step, with substitution occurring selectively at the position para to the amino group. Consequently, the reaction is surprisingly straightforward, with very little or no contamination by isomeric by-products. The process comprises reaction of (a) an aminophenol having an open para position to the amino function, with (b) an unhindered non-enolizable aldehyde, and (c) a thiol or sulfinic acid which acts as a nucleophile. In preferred embodiments, the process is conducted at a temperature of from about 50.degree. C. to about 100.degree. C., and in the presence of a polar solvent. The reaction is promoted by an acid having sufficient acidity to protonate the amino group of the aminophenol. Preferably, the acid promoter is a mineral acid, and it is present in an amount at least substantially equivalent to the amount of aminophenol reactant.
    Type: Grant
    Filed: April 13, 1990
    Date of Patent: August 27, 1991
    Assignee: Eastman Kodak Company
    Inventors: Philip T. S. Lau, Danny R. Thompson
  • Patent number: 5039689
    Abstract: The present invention relates to the use of a compound of formula (I) ##STR1## wherein R representsa hydrogen atom; a C.sub.1-4 alkyl group;a group COR.sup.1 wherein R.sup.1 represents amino or C.sub.1-4 alkoxy; ora group --CH.sub.2 R.sup.2 wherein R.sup.2 represents a halogen atom (e.g. chlorine or bromine), C.sub.1-4 alkylthio, or azido,X and Y each independently represent --CH-- or --N; andZ represents --CR.sup.3, wherein R.sup.3 is hydrogen or C.sub.1-4 alkyl, or Z represents --N--;or a physiologically acceptable salt, ester or other physiologically functional derivative thereof,for the manufacture of a medicament for the treatment and/or prophylaxis of a parasitic infection in a mammal, and to certain novel compounds of formula (I), pharmaceutical compositions containing them and processes for their preparation.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: August 13, 1991
    Assignee: Burroughs Wellcome Co.
    Inventor: Susan M. Daluge
  • Patent number: 5032498
    Abstract: The novel UV-absorbers are compounds of the formula ##STR1## in which R.sup.1 is, for example, hydrogen, n is one of the numbers 1 or 2 and R.sup.2 is an appropriate monovalent or divalent radical, for example --OH or --O-CH.sub.2 CH.sub.2 --O--. The UV-absorbers are used in particular for stabilising and improving lacquers and photographic material.
    Type: Grant
    Filed: August 21, 1990
    Date of Patent: July 16, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean Rody, Mario Slongo
  • Patent number: 5030731
    Abstract: Blocked benzotriazoles of the formula I or II ##STR1## wherein x is 1 or 2, R.sup.1 in the case of x=1 and in the formula II is an acyl group of the formula --CO--R.sup.5, a sulfonyl group of the formula --SO.sub.2 --R.sup.6, a phosphoryl group of the formula --P(O).sub.r (R.sup.14)(R.sup.15), and in the case of x=2 is --CO-- or a diacyl group of the formula --CO--CO-- or --CO--R.sup.7 --CO--, and R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.14 and R.sup.15 have the meanings defined in claim 1, are crypto light stabilizers which can be activated by short-wave irradiation. Their use in coating materials is of interest in cases in which light stabilizers containing the free OH compounds have disadvantages with regard to their application.
    Type: Grant
    Filed: October 24, 1989
    Date of Patent: July 9, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Mario Slongo, Manfred Rembold
  • Patent number: 5006662
    Abstract: 2-(stilbyl-4")-(naphtho-1',2':4,5)-1,2,3-triazole-2"-sulfonic acid is obtained by diazotizing p-aminostilbene sulfonic acid, coupling the resulting diazonium salt with Tobias acid and then oxidizing the resulting monoazo sodium salt to close the ring and form the naphthotriazolyl moiety, and, more particularly, by performing the ring-closure oxidation step in a solution of the monoazo compound in a mixture of 2-butoxyethanol and water with pressurized air by contacting said solution in the presence of a copper salt catalyst at temperatures in the range 105.degree.-160.degree. C. and at pressures in the range 10-80 psig, for a time sufficient to effect ring-closure.
    Type: Grant
    Filed: October 19, 1989
    Date of Patent: April 9, 1991
    Assignee: Ciba-Geigy Corp.
    Inventors: Richard B. Lund, Glenn W. Brown
  • Patent number: 5003076
    Abstract: Novel fluorescent chiral derivatization reagent containing a compound of the formula: ##STR1## being useful for the determination of carboxylic acid enantiomers with high sensitivity, which are easily and well separated in a form of their consequent diastereomeric amides.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: March 26, 1991
    Assignee: Shionogi & Co., Ltd.
    Inventors: Shigeru Narita, Takayasu Kitagawa
  • Patent number: 4999433
    Abstract: Hologenated 2-(2-hydroxyphenyl)-2H-benzotriazoles of the formula ##STR1## in which X is halogen, R.sub.1 is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl or phenyl-C.sub.1 -C.sub.4 alkyl and R.sub.2 is C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl, phenyl-C.sub.1 -C.sub.4 alkyl or a group --C.sub.n H.sub.2n --COOR.sub.3, in which n is 0 to 4 and R.sub.3 is hydrogen or C.sub.1 -C.sub.12 alkyl, can be prepared particularly advantageously by catalytic hydrogenation of a corresponding o-nitroazo compound in the presence of a hydrogenation catalyst consisting of 0.1 to 3% of Pt on a support and of an organic amine.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: March 12, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Helmut Prestel, Klaus Muller
  • Patent number: 4990623
    Abstract: A new class of sulfonated 2-(2'-hydroxyaryl)-2H-benzotriazole compounds and method for using them and other sulfonated hydroxyaryl benzotriazoles on nylon fibers to improve stain resistance and dye lightfastness has been discovered. A process is provided for improving stain resistance of nylon fibers by treatment with sulfonated aromatic-formaldehyde condensate and fluorinated dry soil resist agents.
    Type: Grant
    Filed: July 24, 1989
    Date of Patent: February 5, 1991
    Inventors: Morris B. Berenbaum, John H. Bonfield, Charles J. Cole, Paul W. Harris, Thomas P. J. Izod, Harry E. Ulmer, Frederick R. Hopf, James T. Yardley, Karen M. Bland
  • Patent number: 4978787
    Abstract: A compound of the formula: ##STR1## wherein R is a C.sub.1 -C.sub.5 alkyl group, a C.sub.3 -C.sub.5 alkenyl group, a C.sub.3 -C.sub.5 alkynyl group or a C.sub.3 -C.sub.7 cycloalkyl group, which is useful as a herbicide.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: December 18, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toru Haga, Eiki Nagano, Ryo Sato, Kouichi Morita
  • Patent number: 4973701
    Abstract: Liquid substituted 2H-benzotriazole mixtures are prepared by alkylation with concomitant dealkylation, fragmentation and realkylation of 2-(2-hydroxy-5-alkylphenyl)-2H-benzotriazoles or of 2-(2-hydroxy-3,5-dialkylphenyl)-2H-benzotriazoles with straight or branched alkenes of 8 to 30 carbon atoms in the presence of an acid catalyst at 100.degree.-200.degree. C. The liquid mixtures exhibit outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the processing of stabilized compositions at elevated temperatures.
    Type: Grant
    Filed: April 11, 1988
    Date of Patent: November 27, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Roland A. E. Winter, Werner Stegmann, Reto Luisoli, David Leppard, Roland A. E. Winter, Robert E. Detlefsen
  • Patent number: 4952707
    Abstract: Chemiluminescent 1,2-dioxetane compounds are disclosed in which the molecule is stabilized at the 3-position on the dioxetane ring against decomposition prior to the molecule's coming in contact with a labile group-removing substance (e.g., an enzyme that will cleave the labile group to cause the molecule to decompose to form at least one light-emitting fluorophore) and substituted at the 4-position on the dioxetane ring with a fused polycyclic ring-containing fluorophore moiety bearing a labile ring substituent whose point of attachment to the fused polycyclic ring, in relation to this ring's point(s) of attachment to the dioxetane ring, is such that the total number of ring atoms separating these points of attachment, including the ring atoms at the points of attachment, is an odd whole number. These odd pattern substituted compounds decompose to emit light of greater intensity and of a different wavelength than that emitted by the corresponding even pattern substituted isomers.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: August 28, 1990
  • Patent number: 4943574
    Abstract: (1H-azol-1-ylmethyl)substituted benzotriazole derivatives, compositions containing the same, and methods of treating estrogen dependent disorders.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: July 24, 1990
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Alfons H. M. Raeymaekers, Eddy J. E. Freyne, Josephu L. H. Van Gelder, Marc G. Venet
  • Patent number: 4943637
    Abstract: This invention relates to a method for preparing a 2-phenylbenzotriazole of formula I, ##STR1## (wherein R.sub.1 represents hydrogen or chlorine atom, a lower alkyl group having a carbon number of 1 to 4, a lower alkoxy group having a carbon number of 1 to 4, carboxyl group, or sulfonic acid group; R.sub.2 represents hydrogen or chlorine atom, a lower alkyl group having a carbon number of 1 to 4, or a lower alkoxy group having a carbon number of 1 to 4; R.sub.3 represents hydrogen or chlorine atom, an alkyl group having a carbon number of 1 to 12, a lower alkoxyl group having a carbon number of 1 to 4, phenyl group, a phenyl group substituted with an alkyl group having a carbon number of 1 to 8, phenoxy group, or a phenylalkyl group, the alkyl part of which has a carbon number of 1 to 4; R.sub.4 represents hydrogen or chlorine atom, hydroxyl group, or a lower alkoxy group having a carbon number of 1 to 4; and R.sub.
    Type: Grant
    Filed: August 12, 1988
    Date of Patent: July 24, 1990
    Assignee: Chemipro Kasei Kaisha, Ltd.
    Inventors: Shuichi Seino, Tomizo Fujino
  • Patent number: 4942248
    Abstract: Tertiary-butyl and tertiary-amyl esters of 1H-benzotriazole-1-carboxylic acids are useful blocking agents for blocking the amino or imino groups of amino acids. The six-membered ring of the blocking agent may be unsubstituted or substituted with one or more minor substituents.
    Type: Grant
    Filed: December 1, 1988
    Date of Patent: July 17, 1990
    Assignee: PPG Industries, Inc.
    Inventor: Paul M. Novy
  • Patent number: 4940812
    Abstract: Process for the introduction of functional or functionalizable substituents para to the amino group in 2-aminophenols and 3-aminophenols. The process proceeds in one step, with substitution occurring selectively at the position para to the amino group. Consequently, the reaction is surprisingly straightforward, with very little or no contamination by isomeric by-products. The process comprises reaction of (a) an aminophenol having an open para position to the amino function, with (b) an unhindered non-enolizble aldehyde, and (c) a thiol or sulfinic acid which acts as a nucleophile. In preferred embodiments, the process is conducted at a temperature of from about 50.degree. C. to about 100.degree. C., and in the presence of a polar solvent. The reaction is promoted by an acid having sufficient acidity to protonate the amino group of the aminophenol. Preferably, the acid promoter is a mineral acid, and it is present in an amount at least substantially equivalent to the amount of aminophenol reactant.
    Type: Grant
    Filed: July 17, 1989
    Date of Patent: July 10, 1990
    Assignee: Eastman Kodak Company
    Inventors: Philip T. S. Lau, Danny R. Thompson
  • Patent number: 4937348
    Abstract: A process is provided for preparing 2,2'-methylene-bis-(4-hydrocarbyl-6-benzotriazolyl-phenols) having formula III: ##STR1## wherein: R is selected from the group consisting of alkyl having from one to about twelve carbon atoms; arylalkyl having from seven to about fourteen carbon atoms and cycloalkyl having from three to about twelve carbon atoms;X is selected from the group consisting of hydrogen, halogen, alkyl having from one to about twelve carbon atoms, aryl having from six to ten carbon atoms, arylalkyl having from seven to about sixteen carbon atoms, alkoxy having from one to about twelve carbon atoms, aryloxy having from six to ten carbon atoms; and arylalkoxy having from seven to about sixteen carbon atoms;R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen; alkyl having from one to about six carbon atoms, and R.sub.1 and R.sub.2 taken together to form a four to six member heterocyclic ring including a nitrogen atom; provided, that at least one of R.sub.1 and R.sub.
    Type: Grant
    Filed: December 29, 1987
    Date of Patent: June 26, 1990
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventor: Naohiro Kubota
  • Patent number: 4937349
    Abstract: There is disclosed a process for the preparation of 3-[2'H-benzotriazol-(2')-yl]-4-hydroxybenzenesulfonic acids and salts thereof of formula ##STR1## wherein R is hydrogen or chlorine,R.sub.1 is branched or straight chain C.sub.1 -C.sub.12 alkyl or phenyl-C.sub.1 -C.sub.3 alkyl, andM is hydrogen sodium or potassium,which process comprises sulfonating a 2-(2'-hydroxy-5'-tert-butylphenyl)-benzotriazole of formula ##STR2## wherein R and R.sub.1 are as defined above, and neutralizing the final product to pH 7. In the sulfonation, the tert-butyl group is replaced by the --SO.sub.3 H group with elimination of isobutylene.
    Type: Grant
    Filed: October 19, 1988
    Date of Patent: June 26, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Burdeska, Otto R. Gottel
  • Patent number: 4921966
    Abstract: A process for the preparation of a mixture of 2-(2-hydroxyphenyl)benzotriazole which is liquid at room temperature by alkylating 2-(2-hydroxy-5-methylphenyl)benzotriazole with a C.sub.8 -C.sub.14 .alpha.-olefin in the melt at elevated temperature, in the presence of sulfonic acid as catalyst, comprising using not less than 0.5 mol of the acid catalyst and 1.5-3 mol of .alpha.-olefin per mol of 2-(2-hydroxy-5-methylphenyl)benzotriazole, carrying out the alkylation in the temperature range from 165.degree. to 190.degree. C., separating the crude product phase upper phase) from the sulfonic acid phase, and working up said crude product phase by distillation by means of a thin-film evaporator, a thin-film evaporator fitted with a distillation column, or a short path distillation apparatus.
    Type: Grant
    Filed: December 14, 1988
    Date of Patent: May 1, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Werner Stegmann, Reto Luisoli
  • Patent number: 4904800
    Abstract: A compound of the formula: ##STR1## wherein R is a C.sub.1 -C.sub.5 alkyl group, a C.sub.3 -C.sub.5 alkenyl group, a C.sub.3 -C.sub.5 alkynyl group or a C.sub.3 -C.sub.7 cycloalkyl group, which is useful as a herbicide.
    Type: Grant
    Filed: April 14, 1988
    Date of Patent: February 27, 1990
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Toru Haga, Eiki Nagano, Ryo Sato, Kouichi Morita
  • Patent number: 4902787
    Abstract: A method of producing a UV lightfast disperse dyestuff comprising selecting a disperse dyestuff having predetermined chromophoric groups, selecting a photostabilizer compound, designing a hybrid disperse dye molecular structure which contains the chromophoric groups of the selected disperse dyestuff and also contains the molecular structural features of the selected photostabilizer compound, and synthesizing the thus designed hybrid disperse dyestuff molecule. Such a method produces a hybrid dye molecule which is a UV lightfast analog of a disperse dyestuff having predetermined chromophoric groups, said hybrid dye molecule containing in its molecular structure the chromophoric groups of the selected disperse dyestuff and also containing the molecular structural features of a photostabilizer compound.
    Type: Grant
    Filed: April 21, 1988
    Date of Patent: February 20, 1990
    Assignee: North Carolina State University
    Inventor: Harold S. Freeman
  • Patent number: 4898944
    Abstract: Precursors for the preparation of fiber-reactive triphendioxazine dyestuffs correspond to the general formulas: ##STR1## in which Y' is a vinyl, a beta-hydroxyethyl or an ethyl group which contains in the beta-position a substituent which can be eliminated by an alkali;T is an optionally substituted alkyl (e.g.
    Type: Grant
    Filed: October 27, 1988
    Date of Patent: February 6, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunther Schwaiger, Hartmut Springer, Walter Helmling
  • Patent number: 4895954
    Abstract: Water-soluble triphendioxazine compounds which have fiber-reactive properties as dyestuffs, which afford deep and fast dyeings on fiber materials, such as wool and, in particular, cellulose, and which correspond to the formula (1) ##STR1## in which: n is the number 0 or 1;Y is the vinyl group or an ethyl group containing, in .beta.-position, a substituent which can be eliminated by means of an alkali;Q.sup.1 and Q.sup.2 both represent a benzotriazole radical which can also be additionally substituted in the benzene nucleus by alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogen, carboxy or sulfo;B is --O--, --S--, --NH-- or --N(R')-- wherein R' is optionally substituted alkyl having 1 to 6 carbon atoms;W.sup.1 and W.sup.2 both represent a divalent, optionally substituted aliphatic, cycloaliphatic, aliphatic-cycloaliphatic, araliphatic or aromatic-carbocyclic radical, it being possible for the aliphatic radicals to be interrupted by hetero groups --O--, --S--, --SO.sub.
    Type: Grant
    Filed: October 28, 1988
    Date of Patent: January 23, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunther Schwaiger, Hartmut Springer, Walter Helmling
  • Patent number: 4859726
    Abstract: Disclosed are bis-benzotriazolylphenol compounds having the formula ##STR1## wherein R.sup.1 and R.sup.2 each is a 2-benzotriazolyl radical;R.sup.3 and R.sup.4 each is hydrogen, alkyl, aralkyl, alkoxy, aryl, carboxy, alkoxycarbonyl or halogen; andA is 1,3- or 1,4-phenylene.Also disclosed ae synthetic polymeric materials stabilized with one of the above compounds.
    Type: Grant
    Filed: October 24, 1988
    Date of Patent: August 22, 1989
    Assignee: Eastman Kodak Company
    Inventors: Richard H. S. Wang, Garry L. Myers
  • Patent number: 4853471
    Abstract: The novel UV-absorbers are compounds of the formula ##STR1## in which R.sup.1 is, for example, hydrogen, n is one of the numbers 1 or 2 and R.sup.2 is an appropriate monovalent or divalent radical, for example --OH or --O--CH.sub.2 CH.sub.2 --O--. The UV-absorbers are used in particular for stabilising and improving lacquers and photographic material.
    Type: Grant
    Filed: November 12, 1987
    Date of Patent: August 1, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean Rody, Mario Slongo
  • Patent number: 4851542
    Abstract: N.sub.1 -substituted 1H-benzotriazole hydroxyethyl sulfone compounds, a process for their preparation and their use for the preparation of dyestuffs. Compounds of the general formula ##STR1## in which R is hydrogen or alkyl which has 1 to 6 carbon atoms and can be substituted by hydroxy, sulfo, carboxy, phosphono and/or cyano, W denotes a divalent, optionally substituted aliphatic radical, (C.sub.5 -C.sub.10)-cycloaliphatic radical which is optionally substituted by alkyl, aliphatic-(C.sub.5 -C.sub.8)-cycloaliphatic radical which is optionally substituted by alkyl, optionally substituted araliphatic radical or optionally substituted aromatic carbocyclic radical, it being possible for the aliphatic radicals in W to be interrupted by hetero groups of the formulae --O--, --S--, --SO.sub.
    Type: Grant
    Filed: July 23, 1987
    Date of Patent: July 25, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunther Schwaiger, Hartmut Springer