Phenolic Hydroxy Or Metallate Patents (Class 560/75)
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Patent number: 6924314Abstract: Compounds useful for the treatment of various metabolic disorders, such as insulin resistance syndrome, diabetes, hyperlipidemia, fatty liver disease, cachexia, obesity, atherosclerosis and arteriosclerosis, are disclosed.Type: GrantFiled: October 14, 2003Date of Patent: August 2, 2005Assignee: Wellstat Therapeutics CorporationInventors: Shalini Sharma, Reid W. von Borstel
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Patent number: 6887898Abstract: The invention provides methods for treating beta-Amyloid protein-induced disease, pharmaceutical compositions and compounds useful for the same, and the use of these compounds for the manufacture of a medicament for treating the same. More particularly, the invention relates to the use of natural product compounds isolated from turmeric, gingko biloba, and ginger, and synthetic chemical analogues thereof, for the treatment of a beta-Amyloid protein-induced disease.Type: GrantFiled: October 23, 2000Date of Patent: May 3, 2005Inventor: Darrick S. H. L. Kim
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Patent number: 6878843Abstract: A process for the preparation of a compound of formula (I) wherein R1 and R2 are each independently of the other C1-C8alkyl, cyclopentyl or cyclohexyl, m is 1, 2 or 3, preferably 2, n is an integer from 1 to 30, and R3 is an n-valent radical from linear or branched C4-C30alkyl, which is optionally interrupted by one or more oxygen atoms, or (when n=1-12) an n-valent radical from C5-C12cycloalkyl, or a radical R4—[NR5—CmH2m—]p, R4 is hydrogen, an n-valent radical from linear or branched C4-C30alkyl, which is optionally interrupted by one or more —NR5— groups, or (when n=1-12) an n-valent radical from C5-C12cycloalkyl, R5 radicals, each independently of any other(s), are hydrogen or methyl or —CmH2m—, preferably hydrogen, and p corresponds to the number of —[NR5—CmH2m—] groups that gives n —CmH2m— radicals per molecule, by reaction of a compound of formula (II) wherein R is C1-C3alkyl, with a compound of formula (III) R3(OH)n??(III) wherein R3 and n have the definitions given, wherein the reactionType: GrantFiled: June 14, 2001Date of Patent: April 12, 2005Assignee: Ciba Specialty Chemicals Corp.Inventor: Christoph Kleiner
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Publication number: 20040258743Abstract: A class of UVA- and UVB-absorbing esters has been derived by modifying hydroxy triglycerides and other acyltriglycerides with any of a variety of cinnamic acids. The esterification reactions are preferably conducted at elevated temperatures without a catalyst. The resultant agents have the advantage of being synthesized from natural materials, while providing a value-added use for the oil. They are readily formulated into standard UV-absorbing daily-wear cosmetic, hair and skin care, and sunscreen formulations.Type: ApplicationFiled: June 17, 2003Publication date: December 23, 2004Inventors: David L. Compton, Terry A. Isbell, Rogers E. Harry-O'kuru
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Publication number: 20040209949Abstract: The present invention relates to the use of certain resorcinol derivatives as skin lightening agents.Type: ApplicationFiled: May 5, 2004Publication date: October 21, 2004Inventors: Andrew Francis Browning, Eric William Collington, Martin James Procter, Joanna Victoria Geden
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Publication number: 20040209951Abstract: This invention relates to novel resveratrol analogs of the formula given below; wherein R, R1, R2 and R3 are: 1. R=OH, R1=R2=R3=H; 2. R=OH, R1=Br, R2=R3=H; 3. R=R1=OH, R2=R3=H; 4. R=R1=R3=H, R2=3,4,5-trihydroxybenzoyl; 5. R=R1=H, R2=R3=3,4,5-trihydroxybenzoyl; 6. R=R1=R3=H, R2=3,4-dihydroxycinnamoyl; 7. R=R1=R3=H, R2=3,4,5-trihydroxycinnamoyl; 8. R=R1=R3=H, R2=—CH2CH2N(CH3)2; 9. R=R1=R3=H, R2=—COCH2NH2.HCl. These compounds exhibited high antioxidant properties and are useful in food industry and in cosmetics. The compounds may be used in pharmaceutical composition as an antioxidant or free radical scavenger.Type: ApplicationFiled: February 13, 2004Publication date: October 21, 2004Inventors: Ganga Raju Gokaraju, Rama Raju Gokaraju, Venkata Subbaraju Gottumukkala, Venkateswarlu Somepalli
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Patent number: 6787663Abstract: A composition of an antioxidant of the formula where R3 is an alkyl group of 2 to 6 carbon atoms, and a dispersant or a detergent, is a useful additive package for lubricant compositions.Type: GrantFiled: October 30, 2002Date of Patent: September 7, 2004Assignee: The Lubrizol CorporationInventors: Paul E. Adams, Thomas J. Wolak
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Publication number: 20040122092Abstract: The present invention relates to novel hydroxyphenylundecane derivatives of the formula (I), 1Type: ApplicationFiled: October 1, 2003Publication date: June 24, 2004Applicant: Aventis Pharma Deutschland GmbHInventors: Cordula Hopmann, Martin Knauf, Mark Bronstrup, Astrid Markus-Erb, Luigi Toti
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Publication number: 20030157035Abstract: A compound of formula I 1Type: ApplicationFiled: December 20, 2001Publication date: August 21, 2003Applicant: EM IndustriesInventor: Ratan K. Chaudhuri
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Patent number: 6559335Abstract: The present invention relates to an improved process for the preparation of 3-aryl-2-hydroxy propanoic acid derivatives of the formula (1) useful as an intermediate for the preparation of many pharmaceutically active compounds.Type: GrantFiled: April 17, 2001Date of Patent: May 6, 2003Assignee: Dr. Reddy's Laboratories LimitedInventors: Potlapally Rajender Kumar, Siripragada Mahender Rao, Kotra Narasimha Murthy, Sirisilla Raju, Mamillapalli Ramabhadra Sarma, Gaddam Om Reddy
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Patent number: 6458523Abstract: New compounds of the formula I are described, wherein n is >1; X is O or NR4; L is a n-valent linking group defined in claim 1 and R1 is H, halogen, C1-C25-alkyl, C3-C25-alkenyl, unsubstituted or by C1-C4-alkyl substituted C5-C8-cycloalkyl; R2 and R3 independently of each other are C1-C4-alkyl, or together with the carbon atom they are bonded to, form a carbocyclic C5-C7 ring, especially C5-C7 cycloalkylene; and m is 1-20, especially 2-4. Compounds of the formula I are active as Dox-scavengers in color photographic material.Type: GrantFiled: January 7, 2002Date of Patent: October 1, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Suruliappa Gowper Jeganathan, Stéphane Biry
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Patent number: 6444278Abstract: The present invention relates to 2,6-di-tert-butylphenols of the formula I in which R, A1 A2, Z1, Z2 m and n are as defined herein, and their use as stabilizers or antioxidants.Type: GrantFiled: October 10, 1997Date of Patent: September 3, 2002Assignee: Merck Patent Gesellschaft Mit Beschraenkter HaftungInventors: Volker Reiffenrath, Joachim Krause
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Patent number: 6444839Abstract: Rosemarinic acid or its concentrate is made from seeds of lamiaceous plants in a predetermined period of germination. The method makes it possible to make the rosemarinic acid in any period through the year. High productivity can be achieved by small production facility since high-density cultivation of germinated seed is possible and a cultivation period is short. An amount of rosemarinic acid is rapidly increased after start of germination, and an increasing amount usually becomes maximum five to eight days after start of cultivation. Power obtained by pulverizing dry germinated seeds contains 3 to 5% of rosemarinic acid and can be used for various purposes. An extract obtained by water soluble alcohol from the powder and a fraction obtained by fractioning the extract by an organic solvent are concentrated containing about 15% and 30% of rosemarinic acid respectively. When each concentrate is processed by column chromatography, isolated 99%-rosemarinic acid is obtained.Type: GrantFiled: June 28, 2000Date of Patent: September 3, 2002Assignee: Salad Cosmo Co., Ltd.Inventor: Takeo Murui
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Patent number: 6436991Abstract: Ferulate compounds derived from extracts from the plant Commiphora wightii are used in compositions and methods for prevention and treatment of abnormal cell growth and proliferation in inflammation, neoplasia and cardiovascular disease.Type: GrantFiled: May 21, 2001Date of Patent: August 20, 2002Assignees: Sabinsa Corporation, Sami Chemicals & Extracts (P) Ltd.Inventors: Muhammed Majeed, Vladimir Badmaev, Rajinder Kumar Bammi, Subbalakshmi Prakash, Sankaran Natarajan
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Patent number: 6387951Abstract: Compounds having Formulas 5 and 6 wherein the symbols have the meaning defined in the specification are inhibitors of the cytochrome P450RAI (retinoic acid inducible) enzyme, and are used for treating diseases responsive to treatment by retinoids.Type: GrantFiled: August 29, 2000Date of Patent: May 14, 2002Assignee: Allergan Sales, Inc.Inventors: Jayasree Vasudevan, Alan T. Johnson, Liming Wang, Dehua Huang, Roshantha A. Chandraratna
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Patent number: 6358431Abstract: A method of imparting a water repellent surface to a hydrophilic substrate which comprises contacting the substrate with a solution or dispersion of a suitable calixarene in a liquid medium.Type: GrantFiled: February 24, 1999Date of Patent: March 19, 2002Assignee: The University of SheffieldInventors: Charles James Matthew Stirling, Frank Davis
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Publication number: 20020022731Abstract: A description is given of a process for the transesterification of carboxylic esters, characterized in that the catalyst used is a tin(IV) compound comprising a radical of the formula 1Type: ApplicationFiled: March 29, 2001Publication date: February 21, 2002Inventors: Benoit Pugin, Benoit Dubuis, Adrian Muller
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Patent number: 6331565Abstract: This invention relates to the new use of dicaffeoylquinic acid derivatives for treating Hepatitis B and diseases associated with retrovirus (such as HIV), the new caffeoylquinic acid derivatives and the composition containing the same.Type: GrantFiled: March 1, 1999Date of Patent: December 18, 2001Assignee: Institute of Radiation Medicine Academy of Military Medical Sciences of the PLAInventors: Junxing Dong, Zhongming Tang, Zhibao Mi, Bingji Wang
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Patent number: 6326510Abstract: The invention relates to novel biaromatic compounds having general formula I and their use in pharmaceutical compositions for use in human and veterinary medicine, in particular for treating dermatological, rheumatic, respiratory, cardiovascular, and ophthalmological disorders, and for use in cosmetic compositions.Type: GrantFiled: January 8, 1999Date of Patent: December 4, 2001Assignee: Centre International de Recherches DermatologiquesInventor: Jean-Michel Bernardon
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Patent number: 6303052Abstract: An antioxidant composition comprising at least one compound having the formula: wherein R1 and R2 are each hydrocarbon groups having from 1 to 8 carbon atoms, a is from 1 to 3, R3 is a linear alkyl group having from 4 to 22 carbon atoms, and R4 is a linear alkyl group having from 6 to 24 carbon atoms.Type: GrantFiled: March 2, 1999Date of Patent: October 16, 2001Assignee: Condea Vista CompanyInventors: Shirley A. Moy, Kurt W. McWilliams
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Patent number: 6291703Abstract: Substituted hydroxyhydrocinnamate esters of the formula (I) where R is alkyl, n is 0 to 2, m is 1 to 4 and A is alkyl, interrupted or uninterrupted alkylene, alkanetriyl or pentaerythrityl, are prepared by continuous transesterification of the corresponding lower alkyl mono-ester with an alkanol or polyol of the formula A-(OH)m. This novel process comprises continuously introducing into and reacting the reactants in a heated distillation column reactor having a reaction zone which contains a solid, heterogeneous transesterification catalyst to form the compound of formula (I) and the corresponding lower alkanol; separating the products so formed based on their difference in volatility; and continuously removing said products from the distillation column at a steady rate, thereby preventing the reaction mixture from reaching chemical equilibrium.Type: GrantFiled: January 28, 1999Date of Patent: September 18, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Robert Anthony Schaerfl, Jr., Michael James Day, Sean Peter Piecuch, Ronald Robert Tellier
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Patent number: 6184411Abstract: The invention is directed to an improved process for the preparation of a compound of formula (I) wherein R is alkyl, n is 0 to 2, m is 1 to 4 and A is alkyl, interrupted or uninterrupted alkylene, alkanetriyl or pentaerythrityl, by transesterifying the corresponding lower alkyl with a higher alkanol of the formula A-(OH)m in the presence of a tin catalyst; wherein the improvement comprises reacting the tin catalyzed transesterification reaction mass with a carboxylic acid or hydrate thereof neat, in the absence of an aqueous medium, until the tin catalyst forms an insoluble derivative, and then separating the insoluble derivative from the reaction mass by filtration without the assistance of a filtration aid. The invention allows for a convenient method by which to remove the residual tin catalyst from the substituted hydroxyphenylcarboxylic acid ester compounds of formula (I).Type: GrantFiled: January 28, 1999Date of Patent: February 6, 2001Assignee: Ciba Specialty Chemicals CorporationInventor: John Richard Ross
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Patent number: 6150408Abstract: Compounds that are isolatable from cherries and have antioxidant activity, and methods for isolating these compounds are described. In particular, the invention relates to 1-(3',4'-dihydroxycinnamoyl)-cyclopenta-2,3-diol and 1-(3',4'-dihydroxycinnamoyl)-cyclopenta-2,5-diol, which have antioxidant activity. These antioxidant compounds and compositions containing these compounds are useful as food preservatives, dietary supplements, nutraceuticals, and phytoceuticals.Type: GrantFiled: June 10, 1999Date of Patent: November 21, 2000Assignee: Board of Trustees operating Michigan State UniversityInventors: Muraleedharan G. Nair, Haibo Wang, Gale M. Strasburg, Alden M. Booren, James I. Gray
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Patent number: 6136852Abstract: The present invention relates to 3,4-disubstituted phenylethanolaminotetralincarboxylic acid derivatives represented by the general formula: ##STR1## [wherein Q represents a vinylene group or a group represented by the general formula:-A-(CH.sub.2).sub.m --(wherein A represents an oxygen atom or a methylene group; and m is an integer of from 1 to 6); R represents a hydrogen atom or a lower alkyl group; n is an integer of 1 or 2; the carbon atom marked with * represents a carbon atom in R configuration, S configuration or a mixture thereof; and the carbon atom marked with (S) represents a carbon atom in S configuration] and pharmaceutically acceptable salts thereof, which have a selective .beta..sub.2 -adrenergic receptor stimulating effect with relieved burdens on the heart such as tachycardia and are useful as an agent for the prevention of threatened abortion and premature labor, a bronchodilator and an agent for pain remission and promoting stone removal in urolithiasis.Type: GrantFiled: March 8, 1999Date of Patent: October 24, 2000Assignee: Kissei Pharmaceutical Co., Ltd.Inventors: Makio Kitazawa, Kosuke Okazaki, Tetsuro Tamai, Masaru Saito, Nobuyuki Tanaka, Hiroaki Kobayashi, Ken Kikuchi, Hideyuki Muranaka
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Patent number: 6066311Abstract: There is disclosed a novel method of producing caffeic acid in large quantities, comprising the esterification of chlorogenic acid with an esterifying enzyme. Caffeic acid and its derivatives, produced by this method, may be used in sunscreen compositions, the caffeic acid and its derivatives absorbing both uvA and uvB light.Type: GrantFiled: March 14, 1997Date of Patent: May 23, 2000Assignee: Zylepsis LimitedInventors: Peter S. J. Cheetham, Nigel E. Banister
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Patent number: 5981583Abstract: The present invention is drawn to the inhibition of activation of NF-.kappa.B by caffeic acid phenethyl ester (CAPE) and two analogues of CAPE. Tumor necrosis factor (TNF) activation of NF-.kappa.B is completely blocked by CAPE in a dose- and time-dependent manner, as is activation by phorbol ester, ceramide, hydrogen peroxide, and okadaic acid. Additionally, capsaicin (8-methyl-N-vanillyl-6-noneamide) and resiniferatoxin inhibit the activation of NF-.kappa.B induced by different agents.Type: GrantFiled: September 5, 1997Date of Patent: November 9, 1999Assignee: Research Development FoundationInventors: Bharat B. Aggarwal, Dezider Grunberger
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Patent number: 5973072Abstract: The present invention is directed to a polymeric vehicle, the formulated coating composition and a coating binder made from the polymeric vehicle and a method for making the polymeric vehicle where the polymeric vehicle includes a phenolic urethane reactive diluent. The phenolic urethane reactive diluent may be made from a phenolic ester alcohol having at least one aliphatic hydroxyl group.Type: GrantFiled: March 21, 1996Date of Patent: October 26, 1999Assignee: Exxon Chemical Patents, Inc.Inventors: Frank N. Jones, Vijay Swarup, Ramachandran P. Subrayan, Suru Zhang
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Patent number: 5948922Abstract: Compounds containing two cyclic hydrocarbon moieties which are substituted to provide crosslinking functionality and which are linked to each other by secondary or tertiary oxycarbonyl containing moiety are basis for compositions which are cured to provide cured thermosets for encapsulation and underfill for electronic components that are thermally decomposable to allow repair, replacement, recovery or recycling of operative electronic components from assemblies that are inoperative.Type: GrantFiled: February 20, 1997Date of Patent: September 7, 1999Assignee: Cornell Research Foundation, Inc.Inventors: Christopher K. Ober, Hilmar Koerner
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Patent number: 5945448Abstract: The present invention relates to a composition for treating or preventing brain edemas which comprises containing an endothelin antagonist as an active ingredient, for example, the compound of the following formula (I): ##STR1## or pharmaceutically acceptable salts or hydrates thereof, bosentan, cyclo?D-aspartyl-L-?3-(4-phenylpiperazin-1-ylcarbonyl)!-alanyl-L-aspartyl- D-?2-(2-thienyl)!glycyl-L-leucyl-D-tryptophyl!disodium or cyclo ?D-Asp-L-Pro-D-Val-L-Leu-D-Trp!.Furthermore, the present invention provides a method for treating or preventing brain edemas, which comprises administering an effective amount of an endothelin antagonist and use of an endothelin antagonist for the manufacture of a medicament for treating or preventing brain edemas.An endothelin antagonist exhibits an inhibitory effect, on all brain edemas regardless of the onset mechanism and thus is highly useful in the treatment or prevention of brain edemas.Type: GrantFiled: October 10, 1997Date of Patent: August 31, 1999Assignee: Shionogi & Co., Ltd.Inventors: Mitsuyoshi Ninomiya, Yoshiyuki Matsuo
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Patent number: 5892097Abstract: The transesterification of substituted lower alkyl hydroxyhydrocinnamates with a higher alcohol or a polyol is greatly facilitated by the use of a trace amount of a tin catalyst. In many cases, the amount of the catalyst is so small that it is unnecessary to remove it from the final product by distillation of said product.Type: GrantFiled: May 22, 1997Date of Patent: April 6, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: John R. Ross, Michael E. Schultz, Benoit Dubuis, Peter Kung
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Patent number: 5739377Abstract: Compounds of formula (I): ##STR1## wherein: R.sup.1 represents an alkyl group having from 1 to 6 carbon atoms;R.sup.2 represents an alkyl group having from 8 to 24 carbon atoms;EO represents an ethyleneoxy group;PO represents a propyleneoxy group;k is 0 or an integer from 1 to 10; andm is an integer from 1 to 4;provided that the total of (k+m) is greater than 1 and not greater than 10;are useful as antioxidant stabilizers for polymeric materials.Type: GrantFiled: April 7, 1995Date of Patent: April 14, 1998Assignee: Sankyo Company, LimitedInventors: Hisayu Ohsawa, Tomoyuki Kurumada, Takaaki Yamazaki, Satoru Naito, Kohtaro Kanetaki
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Patent number: 5721103Abstract: Novel trienoic compounds having activity for retinoic acid receptors and retinoid X receptors are provided. Also provided are pharmaceutical compositions incorporating such compounds and methods for their use.Type: GrantFiled: June 7, 1995Date of Patent: February 24, 1998Assignee: Ligand Pharmaceuticals IncorporatedInventors: Marcus F. Boehm, Lin Zhang, Youssef L. Bennani, Alex M. Nadzan
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Patent number: 5713966Abstract: Polyalkyl hydroxyaromatic esters having the formula: ##STR1## or a fuel-soluble salt thereof; where R.sub.1 and R.sub.2 are independently hydrogen, hydroxy, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; R.sub.3 is a polyalkyl group having a weight average molecular weight in the range of about 450 to 5,000; and x is an integer from 0 to 10.The polyalkyl hydroxyaromatic esters of formula I are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: April 16, 1996Date of Patent: February 3, 1998Assignee: Chevron Chemical CompanyInventor: Richard E. Cherpeck
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Patent number: 5696281Abstract: The present invention relates to novel liquid phenolic antioxidants, to organic materials stabilized with said compounds against thermal, oxidalive and/or actinic degradation, and to the use of said novel compounds as stabilizers.Type: GrantFiled: June 20, 1995Date of Patent: December 9, 1997Assignee: Ciba Specialty Chemicals CorporationInventor: Samuel Evans
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Patent number: 5686633Abstract: Inks, particularly inks for ink jet printing, contain at least one compound of the formula I ##STR1## as a stabilizer. The symbols R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.3 ' and R.sub.4 ' are as defined in claim 1. The compounds are in part novel and are suitable for use as light stabilizers for organic materials.Type: GrantFiled: December 31, 1991Date of Patent: November 11, 1997Assignee: Ciba Specialty Chemicals CorporationInventors: Eric Vieira, Hugh Stephen Laver
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Patent number: 5659067Abstract: A description is given of a process for the preparation of 2,5-bis(1,1-dimethyl-4-hexyloxycarbonylbutyl)hydroquinone by reacting 5-methyl-4-hexenoic acid (m)ethyl ester, which is obtainable by reacting 2-hydroxy-2-methyl-3-butene with tri(m)ethyl orthoacetate in the presence of an acid catalyst, with hydroquinone according to Friedel-Crafts, and transesterifying the resulting 2,5-bis(1,1-dimethyl-4-(m)ethoxycarbonylbutyl)-hydroquinone product direct with hexanol in a one-pot process.Type: GrantFiled: September 12, 1996Date of Patent: August 19, 1997Assignee: Ciba-Geigy CorporationInventor: Reinhard Sommerlade
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Patent number: 5654338Abstract: Optically active .alpha.-(hydroxyphenoxy)-alkanecarboxylic acids or derivatives thereof, for example D-2-(4-hydroxyphenoxy)propionic acid or lower alkyl ester thereof, are prepared by (a) saponifying an alkyl ester of an optically active .alpha.-halogeno-alkanecarboxylic acid, in an alcoholic solvent medium, by reacting same with an aqueous solution of an alkali metal hydroxide, thereby providing a solution of an alkali metal salt of an optically active .alpha.-halogeno-alkanecarboxylic acid, (b) next reacting the step (a) solution thus provided with a dihydroxybenzene or salt thereof, in the presence of an alkali metal hydroxide and in an alcoholic solvent medium, and thence (c) recovering the optically active .alpha.-(hydroxyphenoxy)-alkanecarboxylic acid or derivative thereof from the medium of reaction.Type: GrantFiled: April 25, 1995Date of Patent: August 5, 1997Assignee: Rhone-Poulenc ChimieInventor: Pascal Metivier
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Patent number: 5637756Abstract: A cosmetic or dermatological composition with a depigmenting action comprises derivatives of 2,5-dihydroxyphenylcarboxylic acids, their homologs, and their salts, with the derivatives having the following structural formula: ##STR1## wherein: R.sub.1 represents OR.sub.5, OH, or ##STR2## R.sub.5 is a linear or branched C.sub.1 -C.sub.20 alkyl radical, a linear or branched C.sub.2 -C.sub.20 alkenyl radical, or a C.sub.1 -C.sub.20 alkyl radical substituted by one or more hydroxy or alkoxy groups; r' and r", identical or different, represent a hydrogen atom, a C.sub.1 -C.sub.20 alkyl radical, a C.sub.2 -C.sub.6 hydroxyalkyl radical, or a C.sub.3 -C.sub.6 polyhydroxyalkyl, or r' and r" taken together, with the nitrogen atom, form a heterocycle;the number of carbon atoms in the --(CH.sub.2).sub.n --COR.sub.1 chain is less than or equal to 21;R.sub.2 and R.sub.3, identical or different, represent a hydrogen atom, a linear or branched C.sub.1 -C.sub.4 alkyl radical, or a C.sub.1 -C.sub.4 alkoxy; R.sub.Type: GrantFiled: May 18, 1995Date of Patent: June 10, 1997Assignee: L'OrealInventors: Alex Junino, Alain Lagrange, Quang L. N'Guyen, Marie-Alix Bourboulon
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Patent number: 5629422Abstract: New compounds of the formula I are described which are active, for example, as antioxidants, and also a process for their preparation: ##STR1## R.sub.1 and R.sub.2 are independently of one another C.sub.1 -C.sub.20 alkyl, allyl, methallyl, unsubstituted or C.sub.1 -C.sub.8 alkyl-substituted C.sub.5 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.8 cycloalkenyl, phenyl or C.sub.7 -C.sub.9 phenylalkyl, A is a direct bond, --CH.sub.2 --, --(CH.sub.2).sub.2 -- or --CH.sub.2 --CH(CH.sub.3)--, E is --(CH.sub.2).sub.2 --, --CHR.sub.6 --CH.sub.2 -- or --CH.sub.2 CHR.sub.6 --, n is 1, 2 or 3, R.sub.3 is C.sub.1 -C.sub.18 alkyl or is C.sub.1 -C.sub.18 alkyl which is interrupted by --O-- or --S--, unsubstituted or C.sub.1 -C.sub.8 alkyl-substituted C.sub.5 -C.sub.12 cycloalkyl, phenyl, naphthyl, C.sub.7 -C.sub.9 phenylalkyl, C.sub.7 -C.sub.18 alkylphenyl or is of the formula ##STR2## R.sub.4 is phenyl, naphthyl, C.sub.7 -C.sub.9 phenylalkyl, C.sub.7 -C.sub.18 alkylphenyl or is a radical of the formula ##STR3## or NR.sub.3 R.sub.Type: GrantFiled: November 22, 1994Date of Patent: May 13, 1997Assignee: Ciba Geigy CorporationInventor: Hugo Camenzind
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Patent number: 5563291Abstract: There is disclosed a process for the preparation of compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other C.sub.1 -C.sub.8 alkyl or cyclopentyl or cyclohexyl,m is 0, 1, 2 or 3,n is 1 or 2, andR.sub.3, depending on the value of n, is C.sub.4 -C.sub.20 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.2 -C.sub.4 alkylene, or C.sub.4 -C.sub.12 alkylene which is interrupted by oxygen,by reaction of a compound of formula II ##STR2## wherein R is methyl or ethyl, with a compound of formula IIIR.sub.3 (OH).sub.n (III)which reaction is carried out in the presence of magnesium acetate as catalyst.Type: GrantFiled: March 7, 1995Date of Patent: October 8, 1996Assignee: Ciba-Geigy CorporationInventor: Christoph Kleiner
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Patent number: 5536874Abstract: There is provided a process for preparing an arylacetic acid or arylpropionic acid divative from an arylcarbinol which comprises the step of subjecting said arylcarbinol to suitable carbonylation conditions for a sufficient period of time and under suitable pressure and temperature to form said acid derivative, with the proviso that said carbonylation conditions include conducting the reaction in a two-phase system wherein one phase is an aqueous medium which contains (1) a catalyst which is a water-soluble metal complex consisting essentially of a Group VIII metal and a hydrophilic ligand such as palladium complexed with trisulfonated triphenylphosphine, and (2) optionally an acid, and wherein the second phase comprises said arylcarbinol.Type: GrantFiled: November 30, 1994Date of Patent: July 16, 1996Assignee: Hoechst Celanese CorporationInventors: Roger A. Sheldon, Leendert Maat, Georgios Papadogianakis
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Patent number: 5498795Abstract: Compounds of the formula ##STR1## wherein R.sub.1 -R.sub.3 and R.sub.5 independently are hydrogen, lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons, lower alkyl substituted cycloalkyl of 3 to 15 carbons; R.sub.4 is lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons or lower alkyl substituted cycloalkyl of 3 to 15 carbons; X is S or O; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, imidazolyl and oxazolyl, said groups being substituted with the R.sub.5 group defined above; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.Type: GrantFiled: December 29, 1994Date of Patent: March 12, 1996Assignee: Allergan, Inc.Inventors: Tae K. Song, Roshantha A. Chandraratna
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Patent number: 5481023Abstract: There is disclosed a process for the preparation of compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other C.sub.1 --C.sub.8 alkyl, m is 0, 1, 2 or 3, n is 1 or 2, and A, if n 32 1, is OR.sub.3, and R.sub.3 is C.sub.4 -C.sub.20 alkyl or C.sub.5 -C.sub.12 cycloalkyl, or A, if n=2, has the formula --O--C.sub.x H.sub.2x --O-- or --O--(CH.sub.2 CH.sub.2 O).sub.a CH.sub.2 CH.sub.2 O--, x is a number from 2 to 8 and a is a number from 1 to 12, by reacting a compound of formula II ##STR2## with a compound of formula III ##STR3## the reaction being carded out in the presence of an aluminium trialcoholate or triphenolate as catalyst.Type: GrantFiled: September 30, 1993Date of Patent: January 2, 1996Assignee: Ciba-Geigy CorporationInventors: Christoph Kleiner, Samuel Evans, Ralf Schmitt
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Patent number: 5457226Abstract: A novel process for the manufacture of a cinnamic acid derivative of the formula ##STR1## wherein R.sup.1 signifies hydrogen or C.sub.1-8 -alkyl and R.sup.2 signifies hydrogen, C.sub.1-10 -alkyl, C.sub.1-10 -hydroxyalkyl or C.sub.1-4 -alkoxy-C.sub.1-10 -alkyl, is described in which a 4-R.sup.1 O-halobenzene is reacted with acrylic add or an acrylic acid ester CH.sub.2 .dbd.CHCOOR.sup.2 using a heterogeneous palladium catalyst in the presence of the alkanoic acid ammonium salt formed from a C.sub.2-5 -alkanoic acid and an aliphatic mono-, di- or trialkylamine or heterocyclic amine. In the case of the manufacture of the cinnamic acid derivative I in which R.sup.2 signifies hydrogen, the reaction can be carried out in the presence of the amine in place of the alkanoic acid ammonium salt. A further aspect of the described invention comprises reacting the 4-R.sup.1 O-iodobenzene with the product of the Michael addition of an acrylic acid ester CH.sub.2 .dbd.CHCOOR.sup.2', wherein R.sup.Type: GrantFiled: April 28, 1994Date of Patent: October 10, 1995Assignee: Givaudan-Roure CorporationInventor: Peter Gygax
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Patent number: 5449518Abstract: A cosmetic or dermatological composition with a depigmenting action comprises derivatives of 2,5-dihydroxyphenylcarboxylic acids, their homologs, and their salts, with the derivatives having the following structural formula: ##STR1## wherein: R.sub.1 represents OR.sub.5, or ##STR2## R.sub.5 is a hydrogen atom, a linear or branched C.sub.1 -C.sub.20 alkyl radical, a linear or branched C.sub.2 -C.sub.20 alkenyl radical, or a C.sub.1 -C.sub.20 alkyl radical substituted by one or more hydroxy or alkoxy groups; r' and r", identical or different, represent a hydrogen atom, a C.sub.1 -C.sub.20 alkyl radical, a C.sub.2 -C.sub.6 hydroxyalkyl radical, or a C.sub.3 -C.sub.6 polyhydroxyalkyl, or r' and r" taken together, with the nitrogen atom, form a heterocycle; the number of carbon atoms in the --(CH.sub.2).sub.n --COR.sub.1 chain is less than or equal to 21;R.sub.2 and R.sub.3, identical or different, represent a hydrogen atom, a linear or branched C.sub.1 -C.sub.4 alkyl radical, or a C.sub.1 -C.sub.4 alkoxy; R.sub.Type: GrantFiled: July 17, 1992Date of Patent: September 12, 1995Assignee: L'OrealInventors: Alex Junino, Alain Lagrange, Quang L. N'Guyen, Marie-Alix Bourboulon
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Patent number: 5434302Abstract: The present process is directed to preparing optically active 2-aryl alkyl aldehydes by various processes through the use of an optically active amine, (-)-2'-amino-3-phenyl propane. The aldehyde formed can then be oxidized to produce the corresponding acid.Type: GrantFiled: February 18, 1994Date of Patent: July 18, 1995Inventor: H. Henrich Paradies
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Patent number: 5414108Abstract: The subject matter of the invention is a process for the preparation of carboxylic acids and derivatives of them of the general formula ##STR1## wherein R means hydrogen, or a C.sub.1-4 alkyl or a (C.sub.1-5 alkoxy)carbonyl group,R.sub.1 is as defined in claim 1,R.sub.7 stands for hydrogen or a C.sub.1-7 alkyl group andR.sub.8 means hydrogen or a carboxyl group.Type: GrantFiled: August 11, 1992Date of Patent: May 9, 1995Assignee: Biogal GyogyszergrarInventors: Gyorgy Toth, Janos Balint, Klara Elek nee Herczik, Zsuzsanna Moricz nee Garai, Eva Mudra nee Kantor
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Patent number: 5319127Abstract: Disclosed are a class of phenolic-hydrazide compounds of diverse structure which are useful as stabilizers for polyolefins. The phenolic-hydrazide compounds inhibit oxidative degradation of polyolefins which is attributable to heat and/or ultraviolet light and is promoted or accelerated by metals, e.g., copper, in contact with the polyolefin.Type: GrantFiled: September 23, 1993Date of Patent: June 7, 1994Assignee: Eastman Chemical CompanyInventors: Richard H. S. Wang, Ping P. Shang, Daniel A. Jervis
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Patent number: 5310773Abstract: Perfluoroalkyl substituted neopentyl alcohols can be reacted with substituted hydroxphenylalkanoic esters to form perfluoroalkyl containing hydroxyphenylalkanoic ester antioxidants. The perfluoroalkyl substituted hindered hydroxyphenyl alkanoates are stablizers which confer superior processing stability to polymers processed at elevated temperatures such as polypropylene, as well as protecting said polymers from thermal and oxidative degradation.Type: GrantFiled: June 4, 1992Date of Patent: May 10, 1994Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Eduard K. Kleiner
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Patent number: 5302744Abstract: Disclosed are a class of phenolic-hydrazide compounds of diverse structure which are useful as stabilizers for polyolefins. The phenolic-hydrazide compounds inhibit oxidative degradation of polyolefins which is attributable to heat and/or ultraviolet light and is promoted or accelerated by metals, e.g., copper, in contact with the polyolefin.Type: GrantFiled: March 27, 1992Date of Patent: April 12, 1994Assignee: Eastman Kodak CompanyInventors: Richard H. S. Wang, Ping P. Shang, Daniel A. Jervis