Chalcogen Attached Indirectly To The Polycyclo Ring System By Nonionic Bonding Patents (Class 548/260)
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Patent number: 5243047Abstract: 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: GrantFiled: November 16, 1990Date of Patent: September 7, 1993Assignee: Imperial Chemical Industries PLCInventor: John R. Lawson
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Patent number: 5237071Abstract: 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: GrantFiled: January 22, 1991Date of Patent: August 17, 1993Assignee: Fairmount Chemical Company, Inc.Inventors: William E. Leistner, Semyon Moshchitsky, Mahmut Levent
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Patent number: 5235058Abstract: 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: GrantFiled: September 17, 1991Date of Patent: August 10, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Tadahisa Sato, Keizo Kumura
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Patent number: 5233047Abstract: 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: GrantFiled: May 1, 1991Date of Patent: August 3, 1993Assignee: Elf Atochem North America, Inc.Inventors: Ronald E. MacLeay, Terry N. Myers
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Patent number: 5229521Abstract: 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: GrantFiled: October 23, 1992Date of Patent: July 20, 1993Assignee: Ciba-Geigy CorporationInventors: Reto Luisoli, Werner Stegmann
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Patent number: 5206378Abstract: 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: GrantFiled: November 14, 1991Date of Patent: April 27, 1993Assignee: Elf Atochem North America, Inc.Inventors: Ronald E. MacLeay, Terry N. Myers
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Patent number: 5190565Abstract: 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: GrantFiled: February 1, 1991Date of Patent: March 2, 1993Assignee: 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
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Patent number: 5190942Abstract: 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: GrantFiled: April 22, 1991Date of Patent: March 2, 1993Assignee: E. R. Squibb & Sons, Inc.Inventor: Michael A. Poss
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Patent number: 5190574Abstract: 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: GrantFiled: February 7, 1991Date of Patent: March 2, 1993Assignee: Imperial Chemical Industries plcInventors: David P. J. Pearson, John E. D. Barton, Christopher J. Mathews, David Cartwright, Susan P. Barnett
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Patent number: 5187289Abstract: 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: GrantFiled: July 31, 1991Date of Patent: February 16, 1993Assignee: Chemipro Kasei Kaisha, Ltd.Inventors: Naohiko Fukuoka, Kazunobu Kubota, Kunitoshi Iguchi
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Patent number: 5182403Abstract: The present invention relates to 3 indazol substituted 5 Beta amidomethyloxazolidin-2ones, useful as antibacterial agents and to intermediates for their production.Type: GrantFiled: April 23, 1992Date of Patent: January 26, 1993Assignee: The Upjohn CompanyInventor: Steven J. Brickner
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Patent number: 5166355Abstract: 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: GrantFiled: February 4, 1991Date of Patent: November 24, 1992Assignee: Fairmount Chemical Co., Inc.Inventors: William E. Leistner, Semyon Moshchitsky, Mahmut Levent
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Patent number: 5164510Abstract: 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: GrantFiled: February 20, 1991Date of Patent: November 17, 1992Assignee: The Upjohn CompanyInventor: Steven J. Brickner
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Patent number: 5162405Abstract: 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: GrantFiled: March 22, 1991Date of Patent: November 10, 1992Assignee: ELF Atochem North America, Inc.Inventors: Ronald E. MacLeay, Jose Sanchez, Daryl L. Stein
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Patent number: 5157046Abstract: 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: GrantFiled: November 13, 1989Date of Patent: October 20, 1992Assignee: Janssen Pharmaceutica N.V.Inventors: Jean P. F. Van Wauwe, Alfons H. M. Raeymaekers
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Patent number: 5142059Abstract: 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: GrantFiled: September 7, 1990Date of Patent: August 25, 1992Assignee: Ciba-Geigy CorporationInventors: Kurt Burdeska, Gerhard Reinert
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Patent number: 5128267Abstract: Naphthotriazolium salts which are chromogenic indicators for reducing substrate, such as NADH or NADPH.Type: GrantFiled: February 19, 1991Date of Patent: July 7, 1992Assignee: Miles Inc.Inventors: Jurgen Kocher, Meinhard Rolf, Klaus Wehling
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Patent number: 5104992Abstract: 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: GrantFiled: April 2, 1990Date of Patent: April 14, 1992Assignee: Chemipro Kasei Kaisha, Ltd.Inventors: Naohiko Fukuoka, Kazunobu Kubota, Kunitoshi Iguchi
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Patent number: 5099027Abstract: 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: GrantFiled: September 15, 1988Date of Patent: March 24, 1992Assignee: PPG Industries, Inc.Inventors: Otto Vogl, Chongli Zhang
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Patent number: 5097041Abstract: 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: GrantFiled: October 11, 1990Date of Patent: March 17, 1992Assignee: Ciba-Geigy CorporationInventors: Ariane Higel, Sebastian Staubli, Daniel Thibaut, Hans Horisberger
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Patent number: 5095062Abstract: 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: GrantFiled: September 5, 1990Date of Patent: March 10, 1992Assignee: Ciba-Geigy CorporationInventors: Roland A. E. Winter, Robert E. Detiefsen, Werner Stegmann, Reto Luisoli, David Leppard
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Patent number: 5081258Abstract: 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: GrantFiled: May 5, 1989Date of Patent: January 14, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Akitsugu Kawaguchi
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Patent number: 5071995Abstract: Provided are 2-hydroxyphenylbenzotriazol compounds with excellent ultraviolet absorbability and high thermal stability. They can be used as ultraviolet absorber for any polymer.Type: GrantFiled: September 29, 1989Date of Patent: December 10, 1991Assignee: Kuraray Co., Ltd.Inventors: Tsugunori Kashimura, Tsutomu Miura, Keiji Matsumura
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Patent number: 5066656Abstract: (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: GrantFiled: September 10, 1990Date of Patent: November 19, 1991Assignee: Janssen Pharmaceutica N.V.Inventors: Michael N. Greco, Marcel A. C. Janssen
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Patent number: 5055587Abstract: 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: GrantFiled: March 15, 1989Date of Patent: October 8, 1991Assignee: Fuji Photo Film Co., Ltd.Inventor: Yuki Mizukawa
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Patent number: 5043469Abstract: 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: GrantFiled: April 13, 1990Date of Patent: August 27, 1991Assignee: Eastman Kodak CompanyInventors: Philip T. S. Lau, Danny R. Thompson
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Patent number: 5039689Abstract: 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: GrantFiled: November 8, 1989Date of Patent: August 13, 1991Assignee: Burroughs Wellcome Co.Inventor: Susan M. Daluge
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Patent number: 5032498Abstract: 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: GrantFiled: August 21, 1990Date of Patent: July 16, 1991Assignee: Ciba-Geigy CorporationInventors: Jean Rody, Mario Slongo
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Patent number: 5030731Abstract: 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: GrantFiled: October 24, 1989Date of Patent: July 9, 1991Assignee: Ciba-Geigy CorporationInventors: Mario Slongo, Manfred Rembold
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Patent number: 5006662Abstract: 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: GrantFiled: October 19, 1989Date of Patent: April 9, 1991Assignee: Ciba-Geigy Corp.Inventors: Richard B. Lund, Glenn W. Brown
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Patent number: 5003076Abstract: 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: GrantFiled: September 26, 1989Date of Patent: March 26, 1991Assignee: Shionogi & Co., Ltd.Inventors: Shigeru Narita, Takayasu Kitagawa
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Patent number: 4999433Abstract: 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: GrantFiled: September 26, 1989Date of Patent: March 12, 1991Assignee: Ciba-Geigy CorporationInventors: Helmut Prestel, Klaus Muller
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Patent number: 4990623Abstract: 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: GrantFiled: July 24, 1989Date of Patent: February 5, 1991Inventors: 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
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Patent number: 4978787Abstract: 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: GrantFiled: September 11, 1989Date of Patent: December 18, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Toru Haga, Eiki Nagano, Ryo Sato, Kouichi Morita
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Patent number: 4973701Abstract: 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: GrantFiled: April 11, 1988Date of Patent: November 27, 1990Assignee: Ciba-Geigy CorporationInventors: Roland A. E. Winter, Werner Stegmann, Reto Luisoli, David Leppard, Roland A. E. Winter, Robert E. Detlefsen
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Patent number: 4952707Abstract: 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: GrantFiled: June 30, 1988Date of Patent: August 28, 1990
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Patent number: 4943574Abstract: (1H-azol-1-ylmethyl)substituted benzotriazole derivatives, compositions containing the same, and methods of treating estrogen dependent disorders.Type: GrantFiled: September 28, 1989Date of Patent: July 24, 1990Assignee: Janssen Pharmaceutica N.V.Inventors: Alfons H. M. Raeymaekers, Eddy J. E. Freyne, Josephu L. H. Van Gelder, Marc G. Venet
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Patent number: 4943637Abstract: 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: GrantFiled: August 12, 1988Date of Patent: July 24, 1990Assignee: Chemipro Kasei Kaisha, Ltd.Inventors: Shuichi Seino, Tomizo Fujino
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Patent number: 4942248Abstract: 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: GrantFiled: December 1, 1988Date of Patent: July 17, 1990Assignee: PPG Industries, Inc.Inventor: Paul M. Novy
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Patent number: 4940812Abstract: 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: GrantFiled: July 17, 1989Date of Patent: July 10, 1990Assignee: Eastman Kodak CompanyInventors: Philip T. S. Lau, Danny R. Thompson
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Patent number: 4937348Abstract: 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: GrantFiled: December 29, 1987Date of Patent: June 26, 1990Assignee: Adeka Argus Chemical Co., Ltd.Inventor: Naohiro Kubota
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Patent number: 4937349Abstract: 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: GrantFiled: October 19, 1988Date of Patent: June 26, 1990Assignee: Ciba-Geigy CorporationInventors: Kurt Burdeska, Otto R. Gottel
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Patent number: 4921966Abstract: 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: GrantFiled: December 14, 1988Date of Patent: May 1, 1990Assignee: Ciba-Geigy CorporationInventors: Werner Stegmann, Reto Luisoli
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Patent number: 4904800Abstract: 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: GrantFiled: April 14, 1988Date of Patent: February 27, 1990Assignee: Sumitomo Chemical Company LimitedInventors: Toru Haga, Eiki Nagano, Ryo Sato, Kouichi Morita
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Patent number: 4902787Abstract: 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: GrantFiled: April 21, 1988Date of Patent: February 20, 1990Assignee: North Carolina State UniversityInventor: Harold S. Freeman
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Patent number: 4898944Abstract: 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: GrantFiled: October 27, 1988Date of Patent: February 6, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunther Schwaiger, Hartmut Springer, Walter Helmling
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Patent number: 4895954Abstract: 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: GrantFiled: October 28, 1988Date of Patent: January 23, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunther Schwaiger, Hartmut Springer, Walter Helmling
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Patent number: 4859726Abstract: 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: GrantFiled: October 24, 1988Date of Patent: August 22, 1989Assignee: Eastman Kodak CompanyInventors: Richard H. S. Wang, Garry L. Myers
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Patent number: 4853471Abstract: 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: GrantFiled: November 12, 1987Date of Patent: August 1, 1989Assignee: Ciba-Geigy CorporationInventors: Jean Rody, Mario Slongo
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Patent number: 4851542Abstract: 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: GrantFiled: July 23, 1987Date of Patent: July 25, 1989Assignee: Hoechst AktiengesellschaftInventors: Gunther Schwaiger, Hartmut Springer