Polyoxy Alcohol Moiety Patents (Class 560/112)
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Patent number: 5208366Abstract: An improved process is provided for the preparation of esters of polyhalophthalic acids, polyhalobenzoic acids, and polyhalophthalic anhydride useful as flame retardants for thermoplastic and thermosetting resins, which comprises the reaction of the above acids or anhydride with alcohols in the presence of certain metal and metallorganic compounds as catalysts. Also provided are certain esters per se.Type: GrantFiled: August 19, 1991Date of Patent: May 4, 1993Assignee: Elf Atochem North America, Inc.Inventors: Joseph M. Bohen, Anthony J. Mancuso
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Patent number: 5177249Abstract: The present invention relates to compounds comprising ester groups having at least three ester functions, to processes for the production thereof, and to the use of the products.Compounds having at least three functional ester groups of the general formula: ##STR1## are described, wherein the abbreviations have the following meanings: X=--CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--,Y=bivalent, saturated aliphatic hydrocarbon residue optionally substituted,Z=optionally substituted acyl residue --CO--RR.sub.1 =the residue of an alcohol, or a group from an alkylene-oxide-adduct taking the alcohol function in the ester grouping.n=1 to 3 andm=1 to 3.Type: GrantFiled: November 20, 1990Date of Patent: January 5, 1993Assignee: Chemische Fabrik Stockhausen GmbHInventor: Reinmar Peppmoller
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Patent number: 5162589Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of sodium barium phosphate or potassium barium phosphate. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvent, and chemical intermediates.Type: GrantFiled: June 8, 1992Date of Patent: November 10, 1992Assignee: Shell Oil CompanyInventors: Rudolf J. Wijngaarden, Kees Latjes
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Patent number: 5155228Abstract: A process is described for the improved synthesis of the optically pure C.sub.10 -C.sub.18 fragment of the macrolide structure of the immunosuppressant FK-506. This compound is also useful as an intermediate for preparing FK-506 derivatives.Type: GrantFiled: May 16, 1991Date of Patent: October 13, 1992Assignee: Merck & Co., Inc.Inventors: Todd K. Jones, Sander G. Mills, Richard Desmond
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Patent number: 5155254Abstract: A process for the manufacture of 3-hydroxy-2-alkyl-4-pyrones of formula I is provided. ##STR1## The process comprises cyclizing a compound of formula II, ##STR2## an acidic medium and hydrolyzing the ester formed thereby to produce compound I. R.sup.1 represents methyl or ethyl; R.sup.2 represents lower alkanoyl or optionally substituted benzoyl; R.sup.3 represents --OH or --NR.sup.4 R.sup.5 ; and, R.sup.4 and R.sup.5 may be alike or different and represent lower alkyl. The pyrones of formula I wherein R.sup.1 represents methyl or ethyl are known flavorants and odorants.Type: GrantFiled: July 12, 1991Date of Patent: October 13, 1992Assignee: Givaudan CorporationInventor: Hans-Jakob Wild
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Patent number: 5153342Abstract: Mono- and di-esters of 2,2,4-trimethyl-1,3-pentanediol and benzoic acids are useful plasticizers for vinyl chloride polymers, and other polymers, particularly for imparting improved stain resistance to plasticized compositions. Novel processes for preparing the esters are disclosed.Type: GrantFiled: June 5, 1991Date of Patent: October 6, 1992Assignee: Huls America Inc.Inventor: Eugene P. DiBella
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Patent number: 5149843Abstract: Conjugated diene compounds of the general formula: ##STR1## which are industrially advantageous intermediates for preparing sarcophytol A useful as an anticarcinogenic promotor or antitumor agent are provided.Type: GrantFiled: June 7, 1991Date of Patent: September 22, 1992Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5136061Abstract: An optically active pentane compound of the general formula (I): ##STR1## wherein R.sub.1 represents a lower alkyl group having 1 to 4 carbon atoms, R.sub.2 represents a lower alkoxycarbonyl group having an alkoxy moiety of 1 to 4 carbon atoms, or a straight-chain or branched alkyl group having 1 to 7 carbon atoms which is unsubstituted or substituted with a hydroxy or protected hydroxy group, A represents a halogen atom, hydroxy, protected hydroxy, or ethynyl group, or a group of the formula ##STR2## B represents a hydrogen atom, hydroxy, protected hydroxy or acyloxy group, D represents a hydrogen atom, or A and B together can form an acetal or epoxy group, A and D together can form an ethylidene group, and B and D together can form a carbon-carbon direct bond, and a chiral central carbon atoms marked with symbols *, # and .thrfore. in said formula (I) alternatively have one of an R-configuration and an S-configuration.Type: GrantFiled: June 13, 1991Date of Patent: August 4, 1992Assignee: Asahi Denka Kogyo K.K.Inventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5124070Abstract: Disclosed are herein optically active ester derivatives represented by the formula (I): ##STR1## (wherein R.sub.1 represents an alkyl group having 3 to 20 carbon atoms; R.sub.2 represents an optically active alkyl or alkoxyalkyl group having 3 to 15 carbon atoms optionally substituted by halogen atoms; Y represents --O--, --COO-- or --OCO--; X represents --COO-- or --OCO--; l represents a number of 1 or 2; k and m each represents a number of 0 or 1; n represents a number of 1 to 6), preparation processes therefor, liquid crystal materials containing such ester derivatives as active ingredient, and a light switching element using said liquid crystal materials as liquid crystal element.Type: GrantFiled: August 28, 1989Date of Patent: June 23, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa, Kiyoshi Imamura
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Patent number: 5118870Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of a xerogel comprising one or more compounds comprising a rare earth element and phorphorus. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: April 23, 1990Date of Patent: June 2, 1992Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 5095134Abstract: This application relates to monomers and homopolymers of diacetylenic ethers having the formula ##STR1## wherein X is alkyl, alkenyl, aryl, alkaryl, aralkyl, aralkenyl, monoalkylamino or dialkylamino and Y is alkyl, alkenyl or ##STR2## where X' is independently selected from the group of X. The invention also relates to the method of preparing and using said alkoxy diacetylenes.Type: GrantFiled: October 23, 1990Date of Patent: March 10, 1992Assignee: ISP Investments Inc.Inventor: Kou-Chang Liu
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Patent number: 5093517Abstract: There is disclosed a method for making compounds such as 3,6,9-trioxaundecane-1,11-bis (3-n-dodecylthiopropionate) which comprises reacting an alkyl thiopropionate with a glycol at temperatures between 50.degree. C. and 180.degree. C. in the presence of a catalytic amount of a dialkyl tin oxide.Type: GrantFiled: March 9, 1987Date of Patent: March 3, 1992Assignee: The Goodyear Tire & Rubber CompanyInventors: Kirkwood S. Cottman, Joseph A. Kuczkowski
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Patent number: 5059719Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more C.sub.2 to C.sub.4 vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more soluble basic compounds of one or more elements of the lanthanum series (atomic numbers 57-71, inclusive). The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates. When the process is applied to the preparation of alkylene oxide, particularly ethylene oxide, adducts of alkanols, particularly primary alkanols in the C.sub.6 to C.sub.24 range, the product is a valuable narrow range nonionic surfactant, characterized by relatively narrow distribution of alkylene oxide adducts.Type: GrantFiled: March 23, 1990Date of Patent: October 22, 1991Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 5057627Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the phosphate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: February 20, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 5057628Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more compounds of one or more of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: February 20, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventors: Charles L. Edwards, Richard A. Kemp
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Patent number: 5026923Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the borate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: May 29, 1990Date of Patent: June 25, 1991Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 5015697Abstract: A process is disclosed for preparing a composition comprising a polybutyl ketone and a hydroxyester of an epoxidized polybutene wherein the epoxide groups of said epoxidized polybutene are at least 70% trisubstituted. Acid compounds are reacted with epoxidized polybutenes to obtain compositions of increased reactivity as compared with polybutyl ketone compounds. These compositions are useful as chemical intermediates to modify such materials as polyesters and polyurethenes, for applications such as coatings, foams, and sealants.Type: GrantFiled: January 31, 1989Date of Patent: May 14, 1991Assignee: Amoco CorporationInventor: Wayne T. Riddick
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Patent number: 5011943Abstract: A process is described for the improved synthesis of the optically pure C.sub.10 -C.sub.24 fragment of the macrolide structure of the immunosuppressant FK-506. This compound is also useful as an intermediate for preparing FK-506 derivatives.Type: GrantFiled: August 28, 1989Date of Patent: April 30, 1991Assignee: Merck Frosst Canada, Inc.Inventor: Zhaoyin Wang
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Patent number: 5006585Abstract: Mono- and di-esters of 2,2,4-trimethyl-1,3-pentanediol and benzoic acids are useful plasticizers for vinyl chloride polymers, and other polymers, particularly for imparting improved stain resistance to plasticized compositions. Novel processes for preparing the esters are disclosed.Type: GrantFiled: September 5, 1989Date of Patent: April 9, 1991Assignee: Huls America Inc.Inventor: Eugene P. DiBella
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Patent number: 5004569Abstract: The invention relates to a process for the production of carboxylic acid esters from carboxylic acids and alcohols which is characterized in that neutral phosphites containing oxetane groups are used as esterification catalysts.Type: GrantFiled: December 6, 1988Date of Patent: April 2, 1991Assignee: Bayer AktiengesellschaftInventors: Helmut-Martin Meier, Klaus Kircher, Klaus Berg
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Patent number: 4983759Abstract: A compound of a 3,5,6-trihydroxyhexanoic acid derivative of the formula: ##STR1## wherein P.sup.1 and P.sup.2 are independently hydrogen atoms or hydroxy-protecting groups, or together form a ring, and R is an alkyl group is effectively prepared by a process comprising steps of:reacting a butyronitrile derivative of the formula: ##STR2## wherein P.sup.1 and P.sup.2 are the same as defined above with an .alpha.-haloacetate of the formula:X--CH.sub.2 --COOR (III)wherein X is a halogen atom, and R is the same as defined above in the presence of a metallic catalyst selected from the group consisting zinc and zinc-copper to form a keto acid derivative of the formula: ##STR3## wherein P.sup.1, P.sup.2 and R are the same as defined above, and then reducing the obtained keto-acid derivative of the formula (IV).Type: GrantFiled: December 20, 1989Date of Patent: January 8, 1991Assignee: Kanegafuchi Chemical Industry Co., Ltd.Inventors: Kenji Inoue, Satomi Takahashi, Keiichi Yonetsu, Noboru Ueyama
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Patent number: 4970333Abstract: The production of esters via the reaction of an epoxide with a carboxylic acid hasbeen shown to give improved activity when a strong base macroporous anion exchange resin having an acrylic backbone is used in place of a styrene-divinylbenzene based anion exchange resin having an equivalent exchange capacity. Excellent results are obtained when acrylic acid and propylene oxide are reacted together in the presence of strong base macroporous anion exchange resins which have an acrylic backbone.Type: GrantFiled: October 29, 1987Date of Patent: November 13, 1990Assignee: The Dow Chemical CompanyInventors: James A. Rabon, Jr., William C. Pike, Clinton J. Boriack
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Patent number: 4968820Abstract: The new compounds produced from a molecular structural element with two chirality centers and at least one mesogenic structural element are defined by the general formula (I) ##STR1## in which the symbols have the following meaning: Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4 = in any two cases (a) hydroxy and MC--CO--O or, independently of each other, MC--CO--O and (b), independently of each other (C.sub.1 -C.sub.10)alkoxy, MC denoting the molecular radical of a mesogenic carboxylic acid after splitting off a COOH group, and it being possible for Y.sup.2 and Y.sup.3, in the case of (C.sub.1 -C.sub.10)alkoxy, also to be jointly part of a dioxolane ring, or Y.sup.1 and Y.sup.4 jointly = 0 as part of a tetrahydrofuran ring, and Y.sup.2 and Y.sup.3 = hydroxy and MC--CO--O or, independently of each other, MC--CO--O. Said esters preferably find application as dopants in twistable liquid crystal phases in which they produce temperature compensation and twisting.Type: GrantFiled: July 11, 1988Date of Patent: November 6, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunter Scherowsky, Manel Gunaratne
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Patent number: 4966726Abstract: The new compounds produced from a molecular structural element with two chirality centers and at least one mesogenic structural element are defined by the general formula (I) ##STR1## in which the symbols have the following meaning: Y.sup.1 =H, (C.sub.1 -C.sub.10)alkyl, MC--CH.sub.2 or MC--CO, MC denoting the molecular radical of a mesogenic carboxylic acid after splitting off a COOH group,Y.sup.2 =(C.sub.1 -C.sub.10)alkyl, MC--CH.sub.2 or MC--CO, it being possible for Y.sup.1 and Y.sup.2 to jointly represent a MC--CH group, which is then part of a dioxolane ring,X=COOR.sup.1, CONH.sub.2, CONR.sup.2 R.sup.3 or C.tbd.N,R.sup.1 =(C.sub.1 -C.sub.10)alkyl or MC--CH.sub.2, andR.sup.2, R.sup.3 =H and (C.sub.1 -C.sub.4)alkyl or, independently of each other, (C.sub.1 -C.sub.4)alkyl.Said esters preferably find application as dopants in twistable liquid crystal phases in which they produce temperature compensation and twisting.Type: GrantFiled: July 18, 1988Date of Patent: October 30, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunter Scherowsky, Manel Gunaratne
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Patent number: 4965376Abstract: 3,9-Dihydroxynonyne and its derivatives protected at the 9-OH function, of the general formula I ##STR1## where R is hydrogen or a conventional alcohol protective group, and processes for the preparation of the compounds I.Type: GrantFiled: April 18, 1989Date of Patent: October 23, 1990Assignee: BASF AktiengesellschaftInventors: Michael Huellmann, Rainer Becker, Gerald Lauterbach, Ernst Buschmann, Heinz Eckhardt, Walter Himmele, Christiane Brueckner
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Patent number: 4960952Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more lanthanum compounds comprising silicate, metasilicate and mixtures thereof. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: August 31, 1989Date of Patent: October 2, 1990Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 4948912Abstract: The present invention comprises a haloacetoxyalkyl ether having the formula: ##STR1## wherein R is H or a C.sub.1 -C.sub.4 substituted or unsubstituted alkyl group, R' is H or a C.sub.1 -C.sub.3 group, and X is chlorine or fluorine; aroyloxymethyl ethers having the formula:R--COOCH.sub.2 --O--CH.sub.2 --OOC--Rwherein the R is p-NO.sub.2 C.sub.6 H.sub.4, halogen substituted C.sub.6 H.sub.4, or other aromatics; the method of making such ethers and monoquaternary salts; and the method of alkylating amines, pyridines, or acetals or pyridine derivatives with such ethers to form quaternary ammonium salts; particularly HI-6, HGG-12, Toxogonin, and SAS-128.Type: GrantFiled: September 8, 1986Date of Patent: August 14, 1990Assignee: Southwest Research InstituteInventors: Robert E. Lyle, Jr., Donald J. Mangold, Nollie F. Swynnerton
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Patent number: 4922001Abstract: Differentiation of the two enantiotopic groups in prochiral glycerol derivatives gives chiral molecules directly, which in turn are easily converted either into the S-series or into the R-series by selective manipulation of the functional groups.Type: GrantFiled: July 20, 1987Date of Patent: May 1, 1990Assignee: Hoechst AktiengesellschaftInventors: Manfred Schneider, Kurt Laumen, Detlef Breitgoff, Dieter Wullbrandt, Merten Schilingmann, Reinhold Keller
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Patent number: 4910330Abstract: Hydroxy sulfonic acids in general and isethionic acid (2-hydroxy ethyl sulfonic acid) in particular can be prepared at 99+% purity and good yields by the selective oxidation of a precursor hydroxy mercaptan with hydrogen peroxide. The resulting product is pure enough to be used directly in the synthesis of sulfo-acrylic esters which are finding considerable use as stabilizers in producing vinylidene chloride copolymers used for FDA approved packaging films.Type: GrantFiled: September 25, 1987Date of Patent: March 20, 1990Assignee: Union Oil Company of CaliforniaInventors: Dennis E. McGee, Ted S. Hallen
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Patent number: 4910321Abstract: This invention provides a novel catalyst composed of a complex of an organic acid or its ester and a Lewis acid, preferably boron trichloride that can add olefin monomers to increase the molecular weight of the complex from as low as 200 to in excess of a million, with the complex being active viz., living, until the complex dies, viz., is decomposed or destroyed so that polymers in the liquid or easily liquefiable range of 300 to about 20,000 can be made or those more difficult to be liquefied or unliquefiable, viz., those of over 10,000 up to 100,000 or in some cases 500,000 and then those in the range of the elastomers, or moldable or extrudable plastics range having very high molecular weights, generally in excess of 100,000 up to in excess of 500,000 and having useful end groups such as the halogens and specifically chloride, allyl, acryl or methacryl, acetate or formate to name some of the more useful ones.Type: GrantFiled: February 16, 1988Date of Patent: March 20, 1990Assignee: University of AkronInventors: Joseph P. Kennedy, Rudolf Faust
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Patent number: 4877898Abstract: A process for the one step esterification of aldehydes and alcohols comprises the steps of combining an aldehyde with an alcohol, in the presence of oxygen and in contact with a catalyst having the general formulaPdTe.sub.a Zn.sub.d E.sub.ewhereE is one or more metals from the group consisting of group IA, IIA, IVA, VIIB or VIII metals, As or Sb; anda, d and e are from about 0 to 3 with the proviso that at least d or e.noteq.0.Type: GrantFiled: June 12, 1986Date of Patent: October 31, 1989Assignee: The Standard Oil CompanyInventors: Christos Paparizos, Wilfrid G. Shaw, James L. Callahan
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Patent number: 4866200Abstract: Disclosed is a process for the co-production of aromatic carboxylic esters and alkyl iodides by the carbonylation of aromatic iodides in the presence of an alkanol and a palladium catalyst.Type: GrantFiled: August 4, 1988Date of Patent: September 12, 1989Assignee: Eastman Kodak CompanyInventors: Mark Rule, Thomas H. Larkins, Jr., Donald W. Lane, Guy R. Steinmetz
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Patent number: 4851564Abstract: Disclosed is a process for the co-production of aromatic carboxylates and alkyl iodides by the carbonylation of aromatic iodides in the presence of an alkanol and a rhodium catalyst.Type: GrantFiled: February 22, 1988Date of Patent: July 25, 1989Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule
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Patent number: 4847406Abstract: Disclosed is a process for the co-production of aromatic carboxylates and alkyl iodides by the carbonylation of aromatic iodides in the presence of an alkanol and a ruthenium catalyst.Type: GrantFiled: January 12, 1987Date of Patent: July 11, 1989Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule
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Patent number: 4843171Abstract: 1,1-Dialkoxy-2-methyl-4,4-diacyloxy-2-butenes having the general structure: ##STR1## in which R.sub.1 represents alkyl substituents having from 1 to 5 carbon atoms, or both R.sub.1 substituents together represent a single ethylene or propylene substituent, or a single C.sub.1 -C.sub.2 alkyl substituent, and R.sub.2 represents alkyl substituents having from 1 to 5 carbon atoms, or cycloalkyl substituent having from 5 to 7 carbon atoms, or aromatic substituents (preferably phenyl substituents). These new compounds are useful as building blocks in the synthesis of terpenes and carotenoids.Type: GrantFiled: July 1, 1987Date of Patent: June 27, 1989Assignee: BASF AktiengesellschaftInventors: Bernhard Schulz, Rolf Fischer
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Patent number: 4841094Abstract: Organic compounds having functional groups such as aromatic ester, thioester, or carbonate groups are prepared by reacting an organometallic reactant where the metal is gallium, indium, thallium arsenic, antimony, or bismuth, with a suitable second reactant. For example, the ester ##STR1## can be prepared by reacting an organometallic derivative of hydroquinone with p-phenoxybenzoyl chloride.Type: GrantFiled: July 29, 1988Date of Patent: June 20, 1989Assignee: Raychem LimitedInventor: Ian D. H. Towle
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Patent number: 4837357Abstract: 2,2-Disubstituted 3-chloropropionic esters I ##STR1## where R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -oxaalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -oxaalkenyl, aryl or C.sub.7 -C.sub.12 -aralkyl or R.sup.1 -C-R.sup.2 is 5-, 6- or 7-membered ring, R.sup.3 is C.sub.2 -C.sub.6 -oxaalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -oxaalkenyl or C.sub.7 -C.sub.12 -aralkyl, are prepared by converting 2,2-disubstituted 3-hydroxypropanals II ##STR2## into the esterdiol III ##STR3## reacting this esterdiol III in the presence of a transesterification catalyst with an alcohol R.sup.3 OH to give the 3-hydroxyester IV ##STR4## reacting the hydroxyester IV with a stoichiometric or greater than stoichiometric amount of the thionyl chloride and thermally decomposing the product to give the chloropropionic ester I.Type: GrantFiled: October 21, 1987Date of Patent: June 6, 1989Assignee: BASF AktiengesellschaftInventors: Franz Merger, Peter Hettinger
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Patent number: 4829099Abstract: Metabolically-acceptable, surgical adhesives are prepared from polyisocyanates having the structral formula: ##STR1## wherein R is a polyvalent aliphatic radical of about 1 to 10 carbon atoms or a polyvalent aromatic radical of 6 to about 24 carbon atoms;A is C, S or P;Z is O or S;Y is 1 when A is C or P, and 2 when A is S;n is 1 or 2;p is at least 1;q is 0 or 1, with the proviso that when A is carbon or sulfur, q is 0;r is 0 or 1, with the proviso that when A is carbon or sulfur, r is 0;X is a residue of an organic compound having active hydrogen-containing groups; andX' is a residue of an organic compound having at least 1 active hydrogen-containing group.Type: GrantFiled: July 17, 1987Date of Patent: May 9, 1989Assignee: Bioresearch, Inc.Inventors: William D. Fuller, Robert K. Blair, Murray Goodman
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Patent number: 4812582Abstract: This invention pertains to a new method for killing and controlling worms (Helminths), new formulations for killing and controlling worms in animals, new chemical compounds, and a new synthesis of northern hemisphere intermediates for the synthesis of milbemycin and avermectin macrolides.Type: GrantFiled: May 6, 1987Date of Patent: March 14, 1989Assignee: The Upjohn CompanyInventor: Stephen J. Nelson
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Patent number: 4801740Abstract: Polymerizable monomer compounds selected from the group having the formulae: ##STR1## whereinR is hydrogen or methyl;X is fluoro, chloro, bromo, iodo, hydroxyl, perfluoroalkylsulfonoxy of one to three carbon atoms, perfluoroacyloxy of one to three carbon atoms, benzoyloxy, or trichloroacetoxy;Y is trichloroacetyl, perfluoroacyl of the formula ##STR2## trialkylsilyl of the formula [CH.sub.3 (CH.sub.2).sub.m ].sub.3 Si-- or hydrogen,wherein n is zero to six; and m is zero to three, with the proviso that when Y in Formula I or II is hydrogen, X is selected from fluoro, chloro, bromo, iodo in Formulas I and II, and additionally from hydroxyl in Formula I, are disclosed. Polymers and copolymers of the invention are useful for preparing hydrogel processed articles such as contact lenses, and when dissolved in solvents they can be coated onto articles and then hydrolyzed to provide hydrogel coatings.Type: GrantFiled: February 13, 1987Date of Patent: January 31, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventor: W. James Hammar
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Patent number: 4791097Abstract: A method is provided for modifying foam in an aqueous surfactant composition. The method comprises admixing with the aqueous surfactant composition a foam modifying amount of a composition of the formula: ##STR1## wherein R is: (a) a branched or linear alkyl of 20 to 28 carbon atoms; or(b) ##STR2## wherein n is 9-16 and R.sub.1 is a branched or linear alkyl of 3 to 22 carbon atoms.Certain of these benzoate esters are novel, in particular: ##STR3## wherein R.sub.2 and R.sub.3 are each, independently, an alkyl of 4 to 16 carbon atoms, and the total number of carbon atoms in R.sub.2 and R.sub.3 is at least 12 carbon atoms. Preferably, R.sub.2 and R.sub.3 are each C.sub.8 H.sub.17, i.e. octyldodecyl benzoate ester.Additional novel benzoate esters used as foam enhancers have the formula: ##STR4## wherein n is 12 to 16 and R.sub.1 is a branched or linear alkyl of 3 to 22 carbon atoms. Particularly preferred esters are when n is 14, R.sub.1 is C.sub.18 H.sub.37 and R.sub.1 is C.sub.4 H.sub.9.Type: GrantFiled: March 9, 1987Date of Patent: December 13, 1988Assignee: Finetex, Inc.Inventors: Ismail Walele, Herman Brown, Michael Esposito
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Patent number: 4780565Abstract: Alkylene glycol ether carboxylates are produced by reacting at elevated temperature an alkylene oxide and a carboxylate ester in the presence as catalyst of a [bis(trihydrocarbylphosphine)iminium].sub.2 MO.sub.4 compound wherein M is either molybdenum or tungsten.Type: GrantFiled: March 4, 1987Date of Patent: October 25, 1988Assignee: BP Chemicals LimitedInventor: John E. Hamlin
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Patent number: 4777282Abstract: Organic compounds having functional groups such as aromatic ester, thioester, or carbonate groups are prepared by reacting an organo- germanium, tin, or lead reactant with a suitable second reactant. For example, the ester ##STR1## is prepared by reacting the bis-tri-n-butyl tin derivative of hydroquinone with p-phenoxybenzoyl chloride.Type: GrantFiled: June 3, 1986Date of Patent: October 11, 1988Assignee: Raychem LimitedInventor: Ian D. H. Towle
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Patent number: 4729839Abstract: A method for preparing a water soluble lubricating additive having the generic structural formula: ##STR1## wherein R.sub.1 is an alkyl, cycloalkyl, aryl, alkaryl or aralkyl group having from 1 to 34 carbon atoms; R.sub.2, R.sub.3 and R.sub.4 are independent alkylene groups having from 2 to 30 carbon atoms; x is either 1 or 2; y is either 0 or 1 when x=1 and is 0 when x=2; m is either 0 or 1 and n=2 to 30 is disclosed, wherein a sulfur-containing alcohol is initially reacted with an organic carboxylic acid to produce an alkylmercapto ester which is then further reacted with an alkylene oxide to produce the lubricating additive. The water-soluble lubricating additives produced in this manner are useful as lubricating additives for water-based fluids used in metalworking operations.Type: GrantFiled: May 29, 1986Date of Patent: March 8, 1988Assignee: Phillips Petroleum CompanyInventors: Alexander Schuettenberg, Howard F. Efner, Merlin R. Lindstrom, Rex L. Bobsein, Benedict R. Bonazza, Melvin D. Herd
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Patent number: 4720572Abstract: A process for the preparation of a 4-acyloxy-3-oxo-butyric acid ester of the formula ##STR1## in which R.sup.1 is alkyl with up to 4 C atoms, andR.sup.2 is alkyl with up to 4 C atoms and optionally substituted by halogen, hydroxyl, alkoxy or phenyl, or is aryl,which comprises reacting a 4-halogenobutyric acid ester of the formula ##STR2## in which X is chlorine or bromine, with a carboxylic acid of the formula ##STR3## in the presence of acid-trapping agent in an organic solvent at a temperature of between 0.degree. and 170.degree. C.Type: GrantFiled: November 15, 1985Date of Patent: January 19, 1988Assignee: Bayer AktiengesellschaftInventor: Mathias Stubbe
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Patent number: 4691048Abstract: The invention concerns a process for reducing carbonylation of an aldehyde wherein the aldehyde is used as hemiacetalester, the reaction being conducted in the presence of a catalyst consisting of a cobalt carbonyl complex.The hemiacetal-ester may be formed in situ by reacting an acetal with an anhydride of acid.The process preferentially yields alkylene-glycol mono-esters, free of esterified, for a ratio H.sub.2 /CO ranging from 1:1 to 3:1 and preferentially 2-alkoxy aldehydes, for a ratio H.sub.2 /CO ranging from 0.1:1 to 0.5:1.Type: GrantFiled: May 10, 1985Date of Patent: September 1, 1987Assignee: Institut Francais du PetroleInventors: Francois Hugues, Dominique Commereuc, Yves Chauvin
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Patent number: 4677181Abstract: The present invention is directed to polyhydroxyl compounds containing both ether and ester groups, having an average hydroxyl functionality of 2 to 6 and an average hydroxyl number of about 100 to 600, based on the esterification product of (i) polyether polyols having an average hydroxyl functionality of 3 to 8 and an average hydroxyl number of about 200 to 1000 with (ii) about 5 to 70 equivalent %, based on the hydroxyl group of component (i) and the carboxyl group of component (ii), of organic monocarboxylic acids. The present invention is also directed to the use of the polyhydroxyl compounds as synthesis components in the production of polyurethane plastics materials by the isocyanate-polyaddition process, particularly their use as the polyol component in two-component polyurethane coating agents and/or polyurethane casting systems which are solvent-free or have a low solvent content.Type: GrantFiled: July 21, 1986Date of Patent: June 30, 1987Assignee: Bayer AktiengesellschaftInventors: Peter Hohlein, Alois Fehlbier, Hermann Gruber
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Patent number: 4665223Abstract: A process for the production of 1-alkoxyalkyl esters comprises reacting an unsaturated ester with an alcohol in the presence of a Lewis base containing catalyst. The Lewis base containing catalyst is preferably (i) an amidine, or (ii) a Lewis base and an epoxide or (iii) a trivalent organophosphorus compound in the presence of an activated alkene or alkyne. The process can be used to prepare, for example, 1-methoxyethyl acetate from vinyl acetate and methanol under mild conditions.Type: GrantFiled: January 15, 1985Date of Patent: May 12, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4664851Abstract: Process for the co-production of carboxylic acids of the general formula R.sup.1 --COOH and R.sup.2 --COOH and carboxylic acid esters of the general formula R.sup.1 --COOCH.sub.2 R.sup.2 and R.sup.2 --COOCH.sub.2 R.sup.1 from carboxylic acid esters of the general formula R.sup.1 --COOR.sup.2 and/or ethers of the general formula R.sup.3 OR.sup.4 (R.sup.1, R.sup.2, R.sup.3, R.sup.4 representing (substituted) alkyl or (substituted) aryl, alkaryl or aralkyl, R.sup.1 also representing H), carbon monoxide and hydrogen at elevated temperature and pressure in the presence of a ruthenium compound, a further Group VIII metal compound, and a compound R.sup.5 Hal or R.sup.5 COHal where R.sup.5 has one of the meanings given for R.sup.2 and Hal is iodine or bromine, the reaction mixture being substantially free from other transistion metal or Group II metal iodides or bromides, and containing a trivalent nitrogen compound containing a group ##STR1## (X=O or S), such as an amide, a carbamate, a urea or a derivative thereof.Type: GrantFiled: July 19, 1982Date of Patent: May 12, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4661619Abstract: Carboxylic acids and/or esters thereof are produced by reacting either a benzylic or an aromatic mercaptan with carbon monoxide and either water or an aqueous alcohol at elevated temperature, suitably in the range from 100.degree. to 300.degree. C., in the presence as catalyst of a cobalt carbonyl, the product using water as the reactant being a carboxylic acid and using aqueous alcohol as the reactant a carboxylic acid ester, mixtures of acids and esters being formed using aqueous alcohols having high water concentrations.Type: GrantFiled: November 29, 1984Date of Patent: April 28, 1987Assignee: The British Petroleum Company p.l.c.Inventors: Howard Alper, Sang C. Shim, David J. H. Smith