Alicyclic Acid Moiety Containing Unsaturation Patents (Class 560/128)
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Patent number: 4375001Abstract: Novel esters, of the general formula ##STR1## wherein R represents C.sub.1-4 -alkyl or C.sub.2-4 -alkenyl and one of the three broken lines represents an additional bond,are disclosed. Also disclosed are novel odorant and/or flavoring compositions containing esters of formula I, a process and intermediates for the manufacture of the esters of formula I and the use of esters of formula I as odorant and/or flavoring substances.Type: GrantFiled: June 4, 1980Date of Patent: February 22, 1983Inventors: Givaudan Corporation, Hanspeter Schenk
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Patent number: 4374263Abstract: The invention relates to an esterification process employing as a heterogeneous catalyst an inorganic oxide, e.g. silica, to which there is bonded by reaction with surface hydroxyl groups a sulphonic acid-functionalized silane.Type: GrantFiled: October 24, 1980Date of Patent: February 15, 1983Assignee: The British Petroleum Company LimitedInventors: Ronald D. Hancock, Robert Mackison
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Patent number: 4369328Abstract: New oxygenated alicyclic compounds of formula ##STR1## (X=OH, alkyl, O-alkyl) are useful as starting materials for the preparation of cyclohexadienic derivatives of formula ##STR2## (X=OH, alkyl, O-alkyl). They are converted into compounds (III) by treating them with an acidic dehydrating agent in the presence of an inert organic solvent.Compounds (I) are manufactured by reacting compounds (II) ##STR3## (X=OH, alkyl, O-alkyl) with an organic peracid.Type: GrantFiled: July 24, 1981Date of Patent: January 18, 1983Assignee: Firmenich SAInventors: Karl-Heinrich Schulte-Elte, Bernard Egger, Bernard Muller
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Patent number: 4340603Abstract: Novel, transient inotropic prodrug forms of the N-(2-phenylethyl)-.omega.-phenylalkylamines, notably of dobutamine, have (i) the structural formula (I): ##STR1## with the proviso that at least one R.sup.1, R.sup.2 or OR.sup.1, when R.sup.7 and/or R.sup.10 is OR.sup.1, must be R.sup.3 COXCH(R.sup.4)-- or R.sup.3 COXCH(R.sup.4)O--, respectively.Type: GrantFiled: August 13, 1980Date of Patent: July 20, 1982Assignee: INTERx Research CorporationInventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4313956Abstract: Novel, transient prodrug forms of the phenolic dihydroxy sympathomimetic amines have (i) the structural formula (I): ##STR1## wherein X is O, S or NR.sup.5 ; n is 1 or 2; R.sup.1 is the monodehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 1, and the didehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 2; R.sup.Type: GrantFiled: December 28, 1979Date of Patent: February 2, 1982Assignee: INTERx Research Corp.Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4311706Abstract: Novel, transient prodrug forms of dopa and dopamine have (i) the structural formula (I): ##STR1## wherein each R is independently selected from the group consisting of hydrogen, R.sup.3 -CO- and ##STR2## wherein X is O, S or NR.sup.6 ; R.sup.1 is hydrogen or --COOR.sup.8 ; R.sup.2 is hydrogen or OR; R.sup.Type: GrantFiled: January 22, 1980Date of Patent: January 19, 1982Assignee: INTERx Research CorporationInventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4293305Abstract: A cycloaliphatic diester of the formula ##STR1## wherein R is straight or branched chain alkyl of 4-20 carbon atoms, polyoxyalkylene of the formula HO(CH.sub.2 CH.sub.2 O).sub.n CH.sub.2 CH.sub.2 --, HO(C.sub.3 H.sub.6 O).sub.n C.sub.6 H.sub.3 --, HO(CH.sub.2 CH.sub.2 O).sub.p (C.sub.3 H.sub.6 O).sub.q C.sub.3 H.sub.6 --, or HO(C.sub.3 H.sub.6 O).sub.p (C.sub.2 H.sub.4 O).sub.q C.sub.2 H.sub.4 -- or phosphated polyoxyalkylene, wherein n is 2-22 and the sum of p+q is n, in combination with a high boiling aromatic ester, is useful in fiber treating and textile processing compositions.Type: GrantFiled: November 3, 1980Date of Patent: October 6, 1981Assignee: Northwestern Laboratories, Inc.Inventor: Robert B. Wilson
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Patent number: 4292187Abstract: A condensation product from aliphatic or cycloaliphatic polyols, aliphatic saturated or once unsaturated hydroxycarboxylic acids and aliphatic or cycloaliphatic saturated or unsaturated monocarboxylic acids is an effective lubricant for the working of metals, optionally in admixture with other lubricating oils and conventional additives.Type: GrantFiled: March 6, 1980Date of Patent: September 29, 1981Assignee: Bayer AktiengesellschaftInventors: Karl-Heinz Hentschel, Rolf Dhein, Wolfgang Schule
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Patent number: 4291057Abstract: Novel esters of halo-4-alkenoic acid compounds having pesticidal activity and methods of their preparation.Type: GrantFiled: July 2, 1979Date of Patent: September 22, 1981Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4289659Abstract: New oxygenated alicyclic derivatives useful as perfuming and odor modifying agents in the manufacture of perfumes or perfumed products, and as flavoring and taste-modifying agents in the aromatization of foodstuffs in general and imitation flavors for foodstuffs, beverages, animal feeds, pharmaceutical preparations and tobacco products.Novel processes for the preparation of said alicyclic derivatives and compositions of matter relating to mixtures containing same.Type: GrantFiled: May 5, 1980Date of Patent: September 15, 1981Assignee: Firmenich SAInventors: Karl-Heinrich Schulte-Elte, Bruno Willhalm, Fritz Gautschi
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Patent number: 4283420Abstract: The chemical compounds of the invention are useful as the active compound in drugs because of their anticonvulsant and/or antianoxic activity. They have the general formula ##STR1## wherein Z is a hydroxyl group; a group--OM wherein M is an alkali metal atom or an equivalent atom fraction of an alkaline-earth metal or an amino group such as --NH.sub.2, and R is a linear or branched alkyl group containing from 1 to 9 carbon atoms, and optionally substituted by one or more halogen atoms; a linear or branched alkenyl or alkynyl, alkoxyalkyl, or acylalkyl group containing from 2 to 9 carbon atoms and optionally substituted by one or more halogen atoms; an aryl or arylalkyl or aryloxyalkyl group comprising at least one aromatic radical and an alkyl chain having from 1 to 4 carbon atoms.Type: GrantFiled: April 18, 1979Date of Patent: August 11, 1981Assignee: LabazInventors: Charles Pigerol, Jean-Claude Vernieres, Pierre Eymard, Jacques Simiand, Madeleine Broll, Jean-Yves Lacolle
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Patent number: 4283414Abstract: The invention concerns novel pesticidal esters of the pyrethrin or pyrethroid type in which the methylene group bonded to the ester carbonyl and/or ester oxygen bears a fluorine substituent. The compounds of the invention are active against insect pests including flies, moths, aphids and beetles and acarina pests including ticks.Type: GrantFiled: June 8, 1979Date of Patent: August 11, 1981Assignee: ICI Australia LimitedInventors: Donald W. G. Harney, Peter G. Lehman, Joseph C. Rundle
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Patent number: 4276225Abstract: A carboxylic acid ester activated in .alpha.-position by a keto, ester or nitrile group, i.e. of the formula ##STR1## where X is COOR.sup.4, COR.sup.5 or CN, and the several R's can have various meanings but only R.sup.1 and R.sup.2 can be hydrogen, is decarbalkoxylated by heating in the presence of a salt, e.g. sodium chloride, and a phosphorus-containing solvent such as a phospholine oxide, phospholane oxide or phosphetane oxide of the formulas ##STR2## wherein a-k and R can have varied definitions. Water is present either at the outset or end of the reaction before product separation. The reaction proceeds smoothly and in good yields.Type: GrantFiled: August 8, 1977Date of Patent: June 30, 1981Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hellmut Hoffmann
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Patent number: 4264467Abstract: New oxygenated alicyclic derivatives useful as perfuming and odor modifying agents in the manufacture of perfumes or perfumed products, and as flavoring and taste-modifying agents in the aromatization of foodstuffs in general and imitation flavors for foodstuffs, beverages, animal feeds, pharmaceutical preparations and tobacco products.Novel processes for the preparation of said alicyclic derivatives and compositions of matter relating to mixtures containing same.Type: GrantFiled: August 21, 1978Date of Patent: April 28, 1981Assignee: Firmenich SAInventors: Karl-Heinrich Schulte-Elte, Bruno Willhalm, Fritz Gautschl
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Patent number: 4252738Abstract: 1,2-Halohydrincarboxylic acid esters of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are identical or different and represent hydrogen, cyano and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxycarbonyl, acyloxy, alkoxy and aryloxy, and furthermoreR.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4, or R.sup.1 and R.sup.3 and/or R.sup.2 and R.sup.4 can be linked, forming a ring with the carbon atoms to which they are bonded;R.sup.5 represents hydrogen and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxy and alkoxycarbonyl andX represents fluorine, chlorine, bromine and iodine; a process for preparing such 1,2-halohydrincarboxylic acid esters by reacting a cyclobutane-cis-1,2-diol of the formula ##STR2## with an orthoester of the formula ##STR3## wherein R.sup.1 -R.sup.5 have the previously ascribed significance and R.sup.6 -R.sup.Type: GrantFiled: March 17, 1978Date of Patent: February 24, 1981Assignee: Bayer AktiengesellschaftInventors: Willy Hartmann, Hans-Georg Heine
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Patent number: 4249015Abstract: Carboxylic acids and/or esters are prepared by converting the ##STR1## moiety in a 1-substituted 2,2-trihaloethanol, or derivative wherein X represents halogen and R is hydrogen or an acyl group to an organic acid and/or ester grouping of the formula ##STR2## wherein R' is hydrogen or alkyl of 1 to 6 carbon atoms, in the process which comprises reacting the 1-substituted 2,2,2-trihaloethanol or acylated derivative with molecular oxygen in the presence of a catalyst comprising a complex of a transition metal having an atomic number from 21-30, 39-48 or 57-80 and at least one molecule of a ligand containing trivalent nitrogen, phosphorus, arsenic or antimony. This reaction is carried out in a reaction medium comprising an alcohol or aqueous alcohol having 1 to 6 carbon atoms optionally containing an alkali metal, said alcoholic solvent also serving as a reactant source when carboxylic acid esters are formed.Type: GrantFiled: January 26, 1979Date of Patent: February 3, 1981Assignee: Shell Oil CompanyInventors: John A. Schofield, John E. Hawes
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Patent number: 4219665Abstract: Polycarboxylic acid-2-hydroxyalkyl esters of the formula ##STR1## wherein A is an aliphatic, cycloaliphatic, or aromatic radical which is optionally substituted or interrupted by heteroatoms, and/or optionally substituted by hydroxyl groups, R.sub.1 is hydrogen or an alkyl radical having 1 to 12 carbon atoms, and R.sub.2 is an alkyl radical having 10 to 22 carbon atoms, n.gtoreq.0 and m.gtoreq.2, with the proviso that m.gtoreq.n and the total of n+m.gtoreq.3, and their use as emulsifying agents and cosmetic emulsions containing them.Type: GrantFiled: June 30, 1978Date of Patent: August 26, 1980Assignee: Henkel Kommanditgesellschaft auf Aktien (Henkel KGaA)Inventors: Ulrich Zeidler, Fanny Scheuermann
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Patent number: 4216224Abstract: Compositions and methods for treating the symptoms of psoriasis consisting of topical application of a solution, gel, lotion, cream or ointment containing as a principal active ingredient one or more retinoyl compounds is disclosed. The active ingredient consists of one or more compounds which are retinoyl esters of a hydroxy acid, a hydroxy amide, or a hydroxy acid ester, or a retinoyl carbamic or thiocarbamic acid derivative. The composition of this invention may include a single member of the above active ingredients present in a total amount of from 0.01 to 5% by weight of the total composition, or a plurality thereof present in a preferred concentration of from 0.02 to 2% by weight of the total composition.Type: GrantFiled: September 22, 1978Date of Patent: August 5, 1980Inventors: Ruey J. Yu, Eugene J. Van Scott
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Patent number: 4168387Abstract: This invention concerns a method for the preparation of polyphenolic esters for use as built-in antioxidants.Type: GrantFiled: August 6, 1975Date of Patent: September 18, 1979Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 4163111Abstract: A 2-cyclopentenone derivative represented by the formula ##STR1## wherein R.sub.1 and R.sub.2 are lower straight-chain or branched-chain alkyl, alkenyl or aralkyl, and R.sub.4 is 2-pentenyl or 2-pentynyl, and process for preparing the same.Type: GrantFiled: June 8, 1978Date of Patent: July 31, 1979Assignee: Otsuka Kagaku Yakuhim Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Yuichi Kobayashi
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Patent number: 4123404Abstract: Water-thinnable, di- or polyesters and water-insoluble coatings which are particularly suitable as wood finishes and which are made by reaction of the di- or polyesters with water-soluble aminoplast resins are described. The ester resin intermediates are made by reacting a triol having a carbon/oxygen ratio of about 5:3 to about 7:3 with a polycarboxylic acid selected from lower molecular weight polycarboxylic acids so that the resulting ester resin is water-thinnable. The ratio of triol to polycarboxylic acid is varied to produce either the diester or the polyester.Type: GrantFiled: July 25, 1977Date of Patent: October 31, 1978Assignee: Whittaker CorporationInventor: Edward A. Lasher
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Patent number: 4113663Abstract: The 2-ethyl-6,6-dimethyl-2-cyclohexene-1-carboxylic acid ethyl ester possesses uniquely-desirable olfactory properties.Type: GrantFiled: October 4, 1976Date of Patent: September 12, 1978Assignee: Givaudan CorporationInventor: Hanspeter Schenk
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Patent number: 4113968Abstract: When 1-halogeno-3-alkene-2-ol is reacted with an ortho-carboxylic ester and/or a ketene acetal, a .gamma.-halogeno-.delta.-unsaturated-carboxylic ester is obtained as a main reaction product. When this intermediate is treated with a basic substance, a substituted cyclopropane-carboxylic ester is formed. This ester can be used as an insecticide or an agricultural chemical as it is or after the alcohol residue of the ester has been converted to other alcohol residue.Type: GrantFiled: September 26, 1975Date of Patent: September 12, 1978Assignee: Kuraray Co., Ltd.Inventors: Fumio Mori, Yoshiaki Omura, Takashi Nishida, Kazuo Itoi
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Patent number: 4113726Abstract: Compounds are provided having the structure ##STR1## wherein n is 1 or 2, n.sup.1 is 0, 1 or 2 and n.sup.2 is 0, 1, 2 or 3, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be the same or different and can be hydrogen, lower alkyl, halolower alkyl, acyl, lower alkoxy-carbonyl ##STR2## amido ##STR3## or lower alkoxyalkylene, R can be lower alkoxy, lower alkyl or cycloalkyl, R.sub.8 can be hydrogen, lower alkyl, cycloalkyl, hydroxy, dialkylaminoalkyl or R.sub.9 O(CH.sub.2)q-. X is a single bond or a straight or branched bivalent aliphatic radical and Y is ##STR4## These compounds are useful in the treatment of hypertension.Type: GrantFiled: February 28, 1974Date of Patent: September 12, 1978Assignee: E. R. Squibb & Sons, Inc.Inventors: Frederic Peter Hauck, Christopher Michael Cimarusti
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Patent number: 4104043Abstract: A new series of substituted esters of 3-hydroxyindone compounds have been found to have exceptional miticidal and herbicidal activity.Type: GrantFiled: December 12, 1972Date of Patent: August 1, 1978Assignee: Union Carbide CorporationInventors: John A. Durden, Jr., Anthony A. Sousa, John F. Stephen
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Patent number: 4100046Abstract: Polymerizable reaction product mixtures containing cycloalkenylcarbonyloxy compounds are produced by the reaction of a conjugated diene with (i) an acrylate or methacrylate ester of an expoxidized long chain unsaturated fatty oil or (ii) an acrylate or methacrylate of an epoxidized long chain unsaturated fatty acid or ester thereof. The reaction product mixtures obtained are useful per se and in formulations as inks or coatings that can be cured by exposure to radiation or heat.Type: GrantFiled: November 25, 1975Date of Patent: July 11, 1978Assignee: Union Carbide CorporationInventors: Leonard Edward Hodakowski, Claiborn Lee Osborn
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Patent number: 4091006Abstract: A new series of substituted esters of 3-hydroxyindone compounds have been found to have exceptional miticidal and herbicidal activity.Type: GrantFiled: October 1, 1975Date of Patent: May 23, 1978Assignee: Union Carbide CorporationInventors: John A. Durden, Jr., Anthony A. Sousa, John F. Stephen
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Patent number: 4062968Abstract: Substituted acetate compounds represented by the formula ##STR1## which are useful as pesticides and pesticidal composition containing the substituted acetate compounds as active ingredients, as well as processes for preparing the compounds and the compositions are disclosed.Type: GrantFiled: July 16, 1975Date of Patent: December 13, 1977Assignee: Sumitomo Chemical Company, LimitedInventors: Keimei Fujimoto, Nobuo Ohno, Yoshitoshi Okuno, Toshio Mizutani, Isao Ohno, Masachika Hirano, Nobushige Itaya, Takashi Matsuo
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Patent number: 4058666Abstract: Novel aliphatic di- and tri-olefinic acids, esters, thio S-acids, S-thioates, ketones and amides, intermediates therefor, and the control of insects therewith.Type: GrantFiled: April 30, 1976Date of Patent: November 15, 1977Assignee: Zoecon CorporationInventors: Clive A. Henrick, Jeffery N. Labovitz
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Patent number: 4058622Abstract: Substituted acetate compounds represented by the formula ##STR1## which are useful as pesticides and pesticidal compositions containing the substituted acetate compounds as active ingredients, as well as processes for preparing the compounds and the compositions are disclosed.Type: GrantFiled: March 12, 1975Date of Patent: November 15, 1977Assignee: Sumitomo Chemical Company, LimitedInventors: Keimei Fujimoto, Nobuo Ohno, Yoshitoshi Okuno, Toshio Mizutani, Isao Ohno, Masachika Hirano, Nobushige Itaya, Takashi Matsuo
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Patent number: 4058392Abstract: New N,N'-tetrasubstituted ureas of the formula ##STR1## in which X is oxygen, sulfur or an NR.sup.5 -- or SO.sub.2 --group,R is alkyl or an optionally substituted aryl group, or an optionally substituted aralkyl group,R.sup.1 and R.sup.4 are individually optionally substituted hydrocarbyl which may contain oxygen or sulfur,R.sup.2 is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy or cycloalkyl,R.sup.3 is alkyl, which may optionally be substituted by halogen, or is alkenyl, orR.sup.2 and R.sup.3 conjointly form an alkylene bridge, which can be interrupted by a hetero-atom, such as O, or N-alkyl group and which forms a heterocyclic ring with the adjoining nitrogen atom,R.sup.1 and R.sup.Type: GrantFiled: September 10, 1973Date of Patent: November 15, 1977Assignee: Bayer AktiengesellschaftInventors: Rudolf Thomas, Wolfgang Kramer, Ludwig Eue, Carl Metzger, Gerhard Jager
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Patent number: 4056552Abstract: A series of mono, bi and tricarbocyclic compounds, most of which have olefinic unsaturation in the ring, which may or may not have substituents thereon. While the bi and tricyclic rings may be unsubstituted, these compounds which have olefinic unsaturation, particularly multiple olefinic unsaturation, are polymerizable and copolymerizable in known polymerization systems. They are particularly good crosslinking agents. These compounds are further useful in the sense that they can be cleaved oxidatively, to corresponding carboxylic acids, aldehydes and/or alcohols which have known utility in the plasticizer and detergent arts. The compounds which do not have olefinic unsaturation can also be oxidatively cleaved to produce oxygenated, e.g., acid, alcohol or aldehyde, compounds having known utility.Type: GrantFiled: April 4, 1975Date of Patent: November 1, 1977Assignee: Studiengesellschaft Kohle m.b.H.Inventors: Gunther Wilke, Paul Heimbach
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Patent number: 4052435Abstract: A series of mono, bi and tricarbocyclic compounds, most of which have olefinic unsaturation in the ring, which may or may not have substituents thereon. While the bi and tricyclic rings may be unsubstituted, these compounds which have olefinic unsaturation, particularly multiple olefinic unsaturation, are polymerizable and copolymerizable in known polymerization systems. They are particularly good crosslinking agents. These compounds are further useful in the sense that they can be cleaved oxidatively, to corresponding carboxylic acids, aldehydes and/or alcohols which have known utility in the plasticizer and detergent arts. The compounds which do not have olefinic unsaturation can also be oxidatively cleaved to produce oxygenated, e.g., acid, alcohol or aldehyde, compounds having known utility.Type: GrantFiled: November 1, 1976Date of Patent: October 4, 1977Assignee: Studiengesellschaft Kohle m.b.H.Inventors: Gunther Wilke, Paul Heimbach
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Patent number: 4048141Abstract: Certain phosphorus-containing compounds are described herein which are novel latent catalysts for promoting the reaction between vicinal epoxides and phenols and/or carboxylic acids (or anhydrides). Precatalyzed epoxy resins are easily prepared using such catalysts.Type: GrantFiled: January 19, 1976Date of Patent: September 13, 1977Assignee: The Dow Chemical CompanyInventors: George A. Doorakian, Dennis L. Schmidt, Martin C. Cornell, III
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Patent number: 4048214Abstract: Cyclocooligomerization of at least one conjugated diene and an alkyl acrylate in the presence of a non-carbonyl containing, zero-valent nickel complex compound catalyst to form an olefinically unsaturated alicyclic ring compound having the non-hydrocarbon functional group pendent from the ring.Type: GrantFiled: August 15, 1975Date of Patent: September 13, 1977Assignee: Studiengesellschaft Kohle m.b.H.Inventors: Gunther Wilke, Paul Heimbach