Plural Oxyalkylene Groups Bonded Directly To Each Other Patents (Class 568/601)
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Patent number: 11898114Abstract: The present disclosure relates to a composition that includes a compound having the structure R1O—(CH2O)n—R2 and a cetane number between about 65 and about 100, where n is between 1 and 10, inclusively, R1 includes a first alkyl group, and R2 includes a second alkyl group.Type: GrantFiled: December 9, 2021Date of Patent: February 13, 2024Assignee: Alliance for Sustainable Energy, LLCInventors: Daniel Ruddy, Thomas Dwight Foust, Trenton John Wilke, Anh The To, Andrew Wolf Bartling, Martha Arellano-Trevino
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Patent number: 9745236Abstract: Distillative process for obtaining ditrimethylolpropane from solutions includes separating ditrimethylolpropane from the solution in a first distillation unit into a first tops fraction comprising low-boiling compounds having a lower boiling point than ditrimethylolpropane and a first bottoms fraction; introducing the first bottoms fraction into a second distillation unit having at least 5 theoretical plates, said unit being configured as a thin-film evaporator with a column attachment and drawing off a second tops fraction comprising intermediate-boiling compounds having a lower boiling point than ditrimethylolpropane as well as withdrawing a second bottoms fraction from the second distillation unit and introducing the second bottoms fraction into a third distillation unit having at least 4 theoretical plates, said unit being configured as a thin-film evaporator with a column attachment, such that ditrimethylolpropane is obtained as a third tops fraction and high boilers are removed as a third bottoms fractiType: GrantFiled: October 24, 2012Date of Patent: August 29, 2017Assignee: OXEA GMBHInventors: Guido D. Frey, Norman Nowotny, Kurt Schalapski, Heinz Strutz
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Patent number: 9555123Abstract: A multi-arm polyethylene glycol (I) having different kinds of reactive groups and the uses thereof are disclosed, which is formed by polymerizing ethylene oxide with oligo-pentaerythritol as an initiator, wherein, PEG is same or different and is —(CH2CH2O)m-, the average value of m is an integer of 2-250; l is an integer of 1 or more. The method for producing the multi-arm polyethylene glycol having different kinds of reactive groups, the multi-arm polyethylene glycol active derivatives comprising linking groups X attached to PEG and terminal reactive groups F attached to X, the gels formed by the multi-arm polyethylene glycol active derivatives, the drug conjugates formed by the multi-arm polyethylene glycol active derivatives and drug molecules, and the uses thereof in preparing drugs are also disclosed.Type: GrantFiled: December 23, 2010Date of Patent: January 31, 2017Assignee: JENKEM TECHNOLOGY CO., LTD. TIANJIN BRANCHInventors: Xuan Zhao, Meina Lin
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Patent number: 9266990Abstract: A method for producing polyoxymethylene dimethyl ethers using fluidized bed reactor is provided. The fluidized bed reactor gives high conversion of feedstock during synthesis of polyoxymethylene dimethyl ethers. The product separation process includes pre-rectification, extractive rectification and vacuum rectification in series. In the pre-rectification process, the side-draw fraction PODE2 is recycled into the fluidized bed reactor, thus product distribution and selectivity to target components in the reactor can be improved. The extractive rectification process realizes coupling of neutralization, extraction, recovery of unconverted feedstock and products separation, thus significantly simplifies the process. The method for preparation of polyoxymethylene dimethyl ethers in this invention is simple, and has high conversion of feedstock, low energy cost and high selectivity to products.Type: GrantFiled: January 21, 2015Date of Patent: February 23, 2016Assignees: SHANDONG YUHUANG CHEMICAL CO., LTD., TSINGHUA UNIVERSITYInventors: Jinfu Wang, Yanyan Zheng, Shengwei Wang, Tiefeng Wang, Shuangxi Chen, Cunfu Zhu
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Patent number: 9254335Abstract: A multi-arm polyethylene glycol (I) having different kinds of reactive groups and the uses thereof are disclosed, which is formed by polymerizing ethylene oxide with oligo-pentaerythritol as an initiator, wherein, PEG is same or different and is —(CH2CH2O)m-, the average value of m is an integer of 2-250; l is an integer of 1 or more. The method for producing the multi-arm polyethylene glycol having different kinds of reactive groups, the multi-arm polyethylene glycol active derivatives comprising linking groups X attached to PEG and terminal reactive groups F attached to X, the gels formed by the multi-arm polyethylene glycol active derivatives, the drug conjugates formed by the multi-arm polyethylene glycol active derivatives and drug molecules, and the uses thereof in preparing drugs are also disclosed.Type: GrantFiled: December 23, 2010Date of Patent: February 9, 2016Assignee: JENKEM TECHNOLOGY CO., LTD. TIANJIN BRANCHInventors: Xuan Zhao, Meina Lin
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Patent number: 9168503Abstract: The invention relates to a reaction system and process for continuously preparing polymethoxy dimethyl ether (DMM3-8) by a continuous acetalization reaction between an aqueous formaldehyde solution or paraformaldehyde and methanol in the presence of a functionalized acidic ionic liquid as a catalyst. The reaction system of the invention preferably comprises a formaldehyde-concentrating unit, a vacuum-drying unit, an acetalization reaction unit, a product-separating unit and a catalyst-regenerating unit. The process of the invention uses aqueous formaldehyde solution as an initial raw material, which is concentrated in the formaldehyde-concentrating unit to a concentrated formaldehyde of 50˜80 wt. %, and vacuum-dried to paraformaldehyde, or uses paraformaldehyde as raw material directly, then obtains DMM3-8 by an acetalization reaction.Type: GrantFiled: March 18, 2014Date of Patent: October 27, 2015Assignees: Suzhou OST Advanced Materials Co., Ltd., Lanzhou Institute of Chemical Physics, Chinese Academy Of SciencesInventors: Jing Chen, Heyuan Song, Chungu Xia, Meirong Kang
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Patent number: 9169186Abstract: A system and method for producing polyoxymethylene dimethyl ethers (DMMn) using an aqueous formaldehyde solution as the initial reaction material. The process system has a polymerization reaction unit, an acetalation unit, a product separation unit, and a catalyst regeneration unit. Both polymerization and acetalation reaction are conducted in the presence of an ionic liquid as a catalyst, which can achieve the effect that two different reactions may be catalyzed by the same ionic liquid. The present invention employs a simple catalyst system, and achieves the efficient separation of the catalyst, the byproduct water, the product and the reaction materials in a separation manner combining the extraction and the rectification.Type: GrantFiled: December 20, 2012Date of Patent: October 27, 2015Assignee: Lanzhou Institute of Chemicals Physics, Chinese Academy of SciencesInventors: Chungu Xia, Heyuan Song, Jing Chen, Fuxiang Jin, Meirong Kang
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Patent number: 8987521Abstract: It is disclosed a method for preparing polyoxymethylene dimethyl ethers by continuous polymerization and acetalation reactions. The method may include two steps: performing a polymerization reaction of an aqueous formaldehyde solution under catalysis of an ionic liquid IL I to obtain a mixed aqueous solution of trioxymethylene and formaldehyde; and an acetalation reaction of the mixed aqueous solution of trioxymethylene and formaldehyde with methanol is performed under catalysis of an ionic liquid IL II to prepare polyoxymethylene dimethyl ethers. The method may use an aqueous formaldehyde solution as a starting material to prepare polyoxymethylene dimethyl ethers by continuous polymerization and acetalation reactions, achieving a high use ratio of formaldehyde. A film evaporator is used in the invention, realizing a rapid separation and recycling of the light components, with a high separation efficiency. The separation of the catalyst is simple, thereby realizing recycling of the catalyst.Type: GrantFiled: June 20, 2011Date of Patent: March 24, 2015Assignee: Lanzhou Institute of Chemical Physics, Chinese Academy of SciencesInventors: Chungu Xia, Heyuan Song, Jing Chen, Zhen Li
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Publication number: 20140288332Abstract: A polymer includes a linker represented by Formula I ([OR1OCH2OR2OCH2]m), where R1 and R2 are, independently, alkylene, alkenylene, arylene, heteroarylene, or alkylarylalkylene; and the polymer has a weight average molecular weight of about 500 g/mol to about 2,000,000 g/mol, and m is 1 to 1000.Type: ApplicationFiled: June 6, 2014Publication date: September 25, 2014Inventors: William B. Carlson, Gregory D. Phelan
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Patent number: 8816131Abstract: It is related to a method for preparing polyoxymethylene dimethyl ethers by a continuous acetalation reaction of trioxymethylene and methanol or methylal catalyzed by an ionic liquid. The processing apparatus used in the method includes a reaction zone, a separation zone, a catalyst regeneration zone and a product dehydration zone. A manner of circulating tubular reaction is used, resulting in a high external heat exchange efficiency, a simple structure of design and a low investment. A film evaporator is used, realizing a rapid separation and recycling of the light component, with a high separation efficiency. The separation of the catalyst solution from the crude product is simple, thereby realizing the regeneration and recycling of the catalyst.Type: GrantFiled: June 6, 2011Date of Patent: August 26, 2014Assignee: Lanzhou Institute of Chemical Physics, Chinese Academy of SciencesInventors: Jing Chen, Heyuan Song, Chungu Xia, Zhen Li
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Publication number: 20140182620Abstract: An acetal-based composition is described which includes an acetal of formula R—O—CH2—O—R?. R and R? are mutually independent alkyl or alkoxyalkyl substituents with at least three carbon atoms. The composition is useful as a thinner and/or a detergent and/or a stripper. The composition may be used to clean surfaces which are metal, glass or wood and is particularly well adapted for use in the automotive industry. The thinning/cleaning/stripping composition may be stored in a polyethylene container.Type: ApplicationFiled: April 16, 2013Publication date: July 3, 2014Applicant: Woceb bvbaInventor: Bruce Lanhove
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Publication number: 20140114092Abstract: A system and method for producing polyoxymethylene dimethyl ethers (DMMn) using an aqueous formaldehyde solution as the initial reaction material. The process system has a polymerization reaction unit, an acetalation unit, a product separation unit, and a catalyst regeneration unit. Both polymerization and acetalation reaction are conducted in the presence of an ionic liquid as a catalyst, which can achieve the effect that two different reactions may be catalyzed by the same ionic liquid. The present invention employs a simple catalyst system, and achieves the efficient separation of the catalyst, the byproduct water, the product and the reaction materials in a separation manner combining the extraction and the rectification.Type: ApplicationFiled: December 20, 2012Publication date: April 24, 2014Applicant: Lanzhou Institute of Chemical Physics, Chinese Academy of SciencesInventors: Chungu XIA, Heyuan Song, Jing Chen, Fuxiang Jin, Meirong Kang
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Publication number: 20140039214Abstract: A polymer includes a linker represented by Formula I ([OR1OCH2OR2OCH2]m), where R1 and R2 are, independently, alkylene, alkenylene, arylene, heteroarylene, or alkylarylalkylene; and the polymer has a weight average molecular weight of about 500 g/mol to about 2,000,000 g/mol, and m is 1 to 1000.Type: ApplicationFiled: February 7, 2013Publication date: February 6, 2014Applicant: Empire Technology Development LLCInventors: William B. CARLSON, Gregory D. Phelan
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Patent number: 8476477Abstract: A process for preparing polyoxymethylene dimethyl ethers from methanol is disclosed. For example, the process comprises contacting methanol with at least one oxidant in the presence of at least one catalyst wherein the at least one catalyst comprises at least one Group VIB metal component, such as in an amount of from about 0.5 to about 50 wt % (in terms of metal oxide) and at least one Group VIII metal component, such as in an amount of from about 0.2 to about 20 wt % (in terms of metal oxide), and at least one molecular sieve having acidic catalytic activity, such as in an amount of from about 40 to about 95 wt %, based on the total weight of the at least one catalyst for a time sufficient to obtain polyoxymethylene dimethyl ethers.Type: GrantFiled: February 26, 2010Date of Patent: July 2, 2013Assignees: China Petroleum & Chemical Corp., Research Institute of Petroleum Processing, SinopecInventors: Peng Yu, Jingsong Liu, Junfeng Rong, Changzhi Shi, Qiang Fu, Jin Wang, Wei Zhang, Xuhua Zhou
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Publication number: 20110313202Abstract: It is disclosed a method for preparing polyoxymethylene dimethyl ethers by continuous polymerization and acetalation reactions. The method may include two steps: performing a polymerization reaction of an aqueous formaldehyde solution under catalysis of an ionic liquid IL I to obtain a mixed aqueous solution of trioxymethylene and formaldehyde; and an acetalation reaction of the mixed aqueous solution of trioxymethylene and formaldehyde with methanol is performed under catalysis of an ionic liquid IL II to prepare polyoxymethylene dimethyl ethers. The method may use an aqueous formaldehyde solution as a starting material to prepare polyoxymethylene dimethyl ethers by continuous polymerization and acetalation reactions, achieving a high use ratio of formaldehyde. A film evaporator is used in the invention, realizing a rapid separation and recycling of the light components, with a high separation efficiency. The separation of the catalyst is simple, thereby realizing recycling of the catalyst.Type: ApplicationFiled: June 20, 2011Publication date: December 22, 2011Applicant: LANZHOU INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCESInventors: Chungu Xia, Heyuan Song, Jing Chen, Zhen Li
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Publication number: 20110288343Abstract: It is related to a method for preparing polyoxymethylene dimethyl ethers by a continuous acetalation reaction of trioxymethylene and methanol or methylal catalyzed by an ionic liquid. The processing apparatus used in the method includes a reaction zone, a separation zone, a catalyst regeneration zone and a product dehydration zone. A manner of circulating tubular reaction is used, resulting in a high external heat exchange efficiency, a simple structure of design and a low investment. A film evaporator is used, realizing a rapid separation and recycling of the light component, with a high separation efficiency. The separation of the catalyst solution from the crude product is simple, thereby realizing the regeneration and recycling of the catalyst.Type: ApplicationFiled: June 6, 2011Publication date: November 24, 2011Applicant: LANZHOU INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCESInventors: JING CHEN, HEYUAN SONG, CHUNGU XIA, ZHEN LI
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Publication number: 20100256412Abstract: Provided are fluorinated polyethers and polyether oils and methods of preparation. The preparation involves a catalytic oxidation process of fluorinated vinyl ethers employing free oxygen.Type: ApplicationFiled: August 26, 2008Publication date: October 7, 2010Inventors: Werner Schwertfeger, Klaus Hintzer, Harald Kaspar, Egon Obermaier
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Publication number: 20100121106Abstract: A process for preparing perfluoropolyethers of formula T-O—(RF)z-T???(I) wherein: T, T? are end groups, z=0 or 1; RF is a perfluoro(poly)oxyalkylene chain containing one or more fluorooxyalkylene repeating units selected from the group consisting of (CF2O), —(CF(CF3)O)—, —(CF2CF2O)—, —(CF2CF(CF3)O)—, —(CF(CF3)CF2O)—, —(CF2CF2CF2O)—, —(CF2CF2CF2CF2O)—, and —(CF2)j—CFZ—O— wherein j is an integer from 0 to 3, and Z is a fluorooxyalkylene chain comprising from 1 to 20 repeating units selected from the above reported fluorooxyalkylene units; comprising the reduction of peroxidic perfluoropolyethers comprising one or more of the above defined repeating units by using gaseous hydrogen in the presence of a catalyst comprising one or more metals of the VIII group supported on graphitic materials.Type: ApplicationFiled: April 8, 2008Publication date: May 13, 2010Applicant: SOLVAY SOLEXIS S.P.A.Inventors: Ugo De Patto, Giuseppe Marchionni, Pier Antonio Guarda
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Patent number: 7122693Abstract: The acetaldehyde compounds, 2-thiobenzoylacetaldehyde diethylacetal, 2-benzoyloxyacetaldehyde bis(2-methoxyethyl)acetal, 2-hydroxyacetaldehyde bis( 2-methoxyethyl)acetal, 2-thiobenzoylacetaldehyde bis(2-methoxy-ethyl)acetal, and 2-thioacetaldehyde bis(2-methoxyethyl)acetal, are useful as intermediates in the synthesis of substituted 1,3-oxathiolanes and substituted 1,3-dioxolanes.Type: GrantFiled: July 9, 2004Date of Patent: October 17, 2006Assignee: Shire BioChem Inc.Inventors: Pierette Belleau, executrix of estate, Dilip M. Dixit, Nghe Nguyen-Ba, Bernard Belleau, deceased
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Patent number: 6753402Abstract: Polyester-polyether block copolymers can be prepared by catalytic addition of alkylene oxides onto H-functional initiator substances, using polyester alcohols as H-functional initiator substances and multimetal cyanide compounds as catalysts.Type: GrantFiled: April 10, 2002Date of Patent: June 22, 2004Assignee: BASF AktiengesellschaftInventors: Stephan Bauer, Georg Heinrich Grosch, Gerlinde Tischer, Kathrin Harre, Eva Baum, Thomas Ostrowski, Reinhard Lorenz, Regina Pretzsch, Michael Pcolinski, Stefan Dinsch, Inge Rotermund
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Patent number: 6316396Abstract: The invention relates to amphiphilic compounds of the general formula (I) with at least two hydrophilic and at least two hydrophobic groups based on di, oligo or polyolethers. The amphiphilic compounds of this invention are highly surface active and are suitable as emulsifiers, demulsifiers, detergents, dispersants and hydrotropes for industrial and domestic purposes, e.g. in the fields of metalworking, ore separation, surface treatment, washing and cleaning, cosmetics, medicine and food processing and preparation.Type: GrantFiled: April 9, 1999Date of Patent: November 13, 2001Assignee: RWE-DEA Aktiengesellschaft fuer Mineraloel und ChemieInventors: Klaus Kwetkat, Wolfgang Schröder
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Patent number: 6099937Abstract: Disclosed is a perfluoropolyether (PFPE) lubricant comprising less than about 10 percent PFPE molecules having a molecular weight lower than about 2000 Daltons, and wherein the average molecular weight of the lubricant is greater than about 5000 Daltons. Such a lubricant comprises less than about 15 percent PFPE molecules having a moleuclar weight greater than about 10,000 Daltons. Also disclosed is a thin film magnetic disc comprising a recording surface and a PFPE lubricant in contact with the recording surface. The recording surface of such a thin film magnetic disc can be adapted to magnetically record information via an air bearing read/write head. The recording surface can be smooth. The disc can further comprise a rough-surfaced landing zone inward of the recording surface, wherein the PFPE lubricant is in contact with the landing zone. Also disclosed is a method of lubricating a thin film magnetic disc.Type: GrantFiled: May 11, 1998Date of Patent: August 8, 2000Assignee: Seagate Technology, Inc.Inventors: Jing Gui, Bruno Jacques Marchon
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Patent number: 6002049Abstract: Latexes are thickened by compounds of the formula ##STR1## wherein R.sup.1 is an aliphatic, substituted aliphatic, aromatic, or substituted aromatic radical having a valence of from 2 to 8; each of B.sub.1 -B.sub.8 is independently an ester, amide, amine, ether, sulfide, disulfide, thiocarbamate, urea, thiourea, urethane, sulfate, phosphate, carbonyl, methylene, thioamide, carbonate, or imide linkage; each of X.sup.1 -X.sup.8 is independently --A.sub.1 --R.sup.2 --A.sub.2 -- or --A.sub.1 -- wherein each of A.sub.1 and A.sub.2 is independently an ester, amide, amine, ether, sulfide, disulfide, urethane, thiocarbamate, urea, thiourea, sulfate, phosphate, carbonyl, methylene, thioamide, carbonate, or imide linkage and R.sup.2 is a divalent aliphatic, substituted aliphatic, aromatic, or substituted aromatic radical with the proviso that only one of B.sub.1 -B.sub.8 is urethane and that when one of B.sub.1 -B.sub.8 is urethane, one of A.sub.1 and A.sub.Type: GrantFiled: June 12, 1997Date of Patent: December 14, 1999Assignee: Henkel CorporationInventors: Michael S. Wiggins, Reuben H. Grinstein, Stephen A. Fischer
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Patent number: 5936106Abstract: An process for forming a product which may be in a liquid phase is disclosed wherein a first reactant, preferably a liquid reactant, is directly fed into a reaction zone containing mixing elements and which comprises a first compartment of a reactor. A second reactant, which is maintained at a higher pressure, is fed into a second compartment of the reactor separated from the first compartment by a porous wall. The second reactant passes through this porous wall into the reaction zone to react with the first reactant. The process thereby controls rates of the reactions and the exothermic heats generated by the reactions. Pulsatile flow in one or both reaction compartments improves mixing. An evaporator for a portion of the product improves product quality and permits higher reaction temperatures in the reactor.Type: GrantFiled: December 6, 1996Date of Patent: August 10, 1999Assignee: SRI InternationalInventors: William J. Asher, Daryl L. Roberts, Jerry L. Jones, Douglas E. Gottschlich
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Patent number: 5728895Abstract: Latexes are thickened by compounds of the formula ##STR1## wherein R.sup.1 is an aliphatic, substituted aliphatic, aromatic, or substituted aromatic radical having a valence of from 2 to 8; each of B.sub.1 -B.sub.8 is independently an ester, amide, amine, ether, sulfide, disulfide, thiocarbamate, urea, thiourea, urethane, sulfate, phosphate, carbonyl, methylene, thioamide, carbonate, or imide linkage; each of X.sup.1 -X.sup.8 is independently -A.sub.1 -R.sup.2 -A.sub.2 - or -A.sub.1 - wherein each of A.sub.1 and A.sub.2 is independently an ester, amide, amine, ether, sulfide, disulfide, urethane, thiocarbamate, urea, thiourea, sulfate, phosphate, carbonyl, methylene, thioamide, carbonate, or imide linkage and R.sup.2 is a divalent aliphatic, substituted aliphatic, aromatic, or substituted aromatic radical with the proviso that only one of B.sub.1 -B.sub.8 is urethane and that when one of B.sub.1 -B.sub.8 is urethane, one of A.sub.1 and A.sub.Type: GrantFiled: October 9, 1996Date of Patent: March 17, 1998Assignee: Henkel CorporationInventors: Michael S. Wiggins, Reuben Grinstein, Stephen A. Fischer
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Patent number: 5726276Abstract: The present invention provides a process for preparing a thermally very stable polyacetal copolymer having very small unstable terminals even at a high polymerization yield, by the copolymerization of trioxane as the principal monomer with a comonomer copolymerizable therewith, wherein an isopolyacid or an acidic salt thereof is used as a polymerization catalyst; the catalyst can simply be deactivated in a small amount of a deactivator solution after the polymerization; and a washing step is not required. The copolymerization is effected with an isopolyacid or an acidic salt thereof used as a polymerization catalyst until the remaining monomers account for at most 10% by weight of all the fed monomers, and a solution containing a deactivator for the above catalyst is added in an amount of 0.01 to 10% by weight based on the resulting crude polymer to deactivate the catalyst, followed by subjecting the crude polymer intact to a heat-melting treatment without washing it.Type: GrantFiled: October 1, 1996Date of Patent: March 10, 1998Assignee: Polyplastics Co., Ltd.Inventors: Akira Nakai, Eiji Masuda, Kaoru Yamamoto
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Patent number: 5719194Abstract: Use of perfluoropolyethers with non reactive terminals or compositions thereof for the prevention and/or the treatment of topical vital infections, in particular of Herpes Simplex I and II and of Herpes Zoster.Type: GrantFiled: June 7, 1996Date of Patent: February 17, 1998Assignee: Ausimont S.p.A.Inventors: Morris A. Mann, Giovanni Pantini
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Patent number: 5583240Abstract: An exothermic process for forming a product which may be in a liquid phase is disclosed wherein a first reactant, preferably a liquid reactant, is directly fed into a reaction zone containing mixing elements and which comprises a first compartment of a reactor. A second reactant, which is maintained at a higher pressure, is fed into a second compartment of the reactor separated from the first compartment by a porous wall. The second reactant passes through this porous wall into the reaction zone to react with the first reactant. The process thereby controls rates of the reactions and the exothermic heats generated by the reactions. Pulsatile flow in one or both reaction compartments improves mixing. An evaporator for a portion of the product improves product quality and permits higher reaction temperatures in the reactor.Type: GrantFiled: March 2, 1994Date of Patent: December 10, 1996Assignee: SRI InternationalInventors: William J. Asher, Daryl L. Roberts, Jerry L. Jones, Douglas E. Gottschlich
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Patent number: 5571870Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: May 10, 1994Date of Patent: November 5, 1996Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5545712Abstract: An alkali metal compound such as metallic cesium, cesium hydroxide, cesium hydroxide monohydrate, metallic rubidium, rubidium hydroxide or rubidium hydroxide monohydrate is used as a catalyst, crude polyoxyalkylene polyol containing the catalyst is neutralized with a mineral acid or an organic acid, an aqueous solution layer containing an alkali metal salt is brought into contact with an anion exchange resin to adsorb mineral acid anion or organic acid anion, the alkali metal compound catalyst is recovered, alkylene oxide undergoes ring-opening addition polymerization on an active hydrogen compound in the presence of the recovered alkali metal compound catalyst to prepare polyoxyalkylene polyol, the catalyst is thereafter separated, recovered and reused, and such recycle of the alkali metal compound catalyst provides an economical process.Type: GrantFiled: August 23, 1995Date of Patent: August 13, 1996Assignee: Mitsu Toatsu Chemicals, Inc.Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
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Patent number: 5468840Abstract: An alkali metal compound such as metallic cesium, cesium hydroxide, cesium hydroxide monohydrate, metallic rubidium, rubidium hydroxide or rubidium hydroxide monohydrate is used as a catalyst, crude polyoxyalkylene polyol containing the catalyst is neutralized with a mineral acid or an organic acid, an aqueous solution layer containing an alkali metal salt is brought into contact with an anion exchange resin to adsorb mineral acid anion or organic acid anion, the alkali metal compound catalyst is recovered. alkylene oxide undergoes ring-opening addition polymerization on an active hydrogen compound in the presence of the recovered alkali metal compound catalyst to prepare polyoxyalkylene polyol, the catalyst is thereafter separated, recovered and reused, and such recycle of the alkali metal compound catalyst provides an economical process.Type: GrantFiled: August 29, 1994Date of Patent: November 21, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
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Patent number: 5446206Abstract: This invention relates to perfluoropolyethers having neutral end groups by a process based on the photooxidation of C.sub.3 F.sub.6 and/or C.sub.2 F.sub.4, thereby obtaining controlled molecular weight products having perfluoroalkyl or perfluorochloroalkyl neutral end groups, with high yields of useful products.Type: GrantFiled: July 25, 1994Date of Patent: August 29, 1995Assignee: Ausimont S.r.l.Inventors: Giuseppe Marchionni, Anna Staccione
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Patent number: 5362919Abstract: A liquid phase process for making perfluorinated organic substances which comprises directly contacting in a temperature-controlled reactor a diluted solution or dispersion of a perfluorinateable, organic substance in a liquid, inert medium with a stoichiometric excess of fluorine gas, optionally diluted with an inert gas, to perfluorinate said organic substance at a temperature and a flow rate of inert gas (if used) sufficient to volatilize the resulting by-product hydrogen fluoride, removing said hydrogen fluoride from the reactor as it is produced, and separately removing from the reactor the resultant solution or dispersion of perfluorinated organic substance.Type: GrantFiled: March 31, 1993Date of Patent: November 8, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Michael G. Costello, George G. I. Moore
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Patent number: 5319147Abstract: Perfluoropolyoxyalkylenes containing acid and/or ketonic groups are neutralized by reacting same in the liquid phase with elemental fluorine at temperatures of from -20.degree. to +150.degree. C. in the presence of a supported catalyst consisting of fluorides of Ag, Pb, Co, Ni, Cu, Mn, V, Cr, or Fe.In a preferred embodiment, a mixture of fluorides of the above mentioned metals and of fluorides, or fluoride precursors, of an alkali and/or alkaline-earth metal is used as catalyst, optionally supported on a suitable carrier.Type: GrantFiled: December 22, 1992Date of Patent: June 7, 1994Assignee: Ausimont S.p.A.Inventors: Giuseppe Marchionni, Ugo De Patto
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Patent number: 5290912Abstract: The present invention has an object of producing a polyoxyalkylene compound by ring-opening polymerization of an alkylene oxide to a certain specific highly hydrophobic initiator. The present invention provides a process for producing a polyoxyalkylene compound, characterized in that the polyoxyalkylene compound is produced by ring-opening polymerization of an alkylene oxide, in the presence of a plural metal cyanide complex catalyst, with an initiator selected from an organopolysiloxane compound having an active hydrogen-containing functional group to which an alkylene oxide is reactive, and a fluorine-containing compound having such an active hydrogen-containing functional group and a fluorinated hydrocarbon group.Type: GrantFiled: January 10, 1992Date of Patent: March 1, 1994Assignee: Asahi Glass Company Ltd.Inventors: Takashi Watabe, Hiromitsu Takeyasu, Shigeyuki Kozawa
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Patent number: 5254744Abstract: Oligomeric formal diols are prepared by coupling segments of poly(tetramethylene ether) glycols, each having a molecular weight of 650-3000, with formaldehyde in the presence of a granular acidic catalyst, to yield poly(tetramethylene ether) formal glycols of 1,400-12,000 molecular weight.Oligomeric formal diols of a second type can also be prepared by coupling with formaldehyde segments of poly(tetramethylene ether) glycols mixed with segments of other polymeric glycols, as for example polyethylene oxide glycol of 200 molecular weight, to yield poly(ether formal) glycols of substantially higher molecular weight than either of the starting polyether glycols, and having properties significantly different from the parent polyether glycols that may affect the performance as soft or elastomeric segments of derived polyurethanes, polyetheresters, and polyureas.Type: GrantFiled: February 28, 1992Date of Patent: October 19, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: John F. Neumer
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Patent number: 5206443Abstract: Alkanediol bisacetals useful as surface-active substances for industrial purposes, in particular in washing and cleaning agents, have the formula I ##STR1## where R.sup.1 is alkyl or alkenyl of from 6 to 30 carbon atoms,A is 1,2-alkylene of from 2 to 4 carbon atoms,m is from 0 to 50,within each of the pairs R.sup.1, A and m the meanings being identical or different, andn is from 2 to 20.Type: GrantFiled: April 20, 1992Date of Patent: April 27, 1993Assignee: BASF AktiengesellschaftInventors: Richard Baur, Helmut Guembel, Alfred Oftring, Johannes Perner, Gerhard Wolf
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Patent number: 5202501Abstract: Perfluoropolyethers containing high concentrations of difluoromethylene oxide units in the polymer chain are disclosed.Type: GrantFiled: August 27, 1991Date of Patent: April 13, 1993Assignee: Exfluor Research CorporationInventors: Richard J. Lagow, Thomas R. Bierschenk, Timothy J. Juhlke
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Patent number: 5191127Abstract: This invention provides glyoxal derivatives and a method for making these derivatives. A particularly useful derivative, 1-chloro-1,2,2-trialkoxyethane, and a facile method for making these alpha-halo ethers are provided. The alpha-halo ethers are valuable intermediates in the manufacture of a variety of commercial compounds.Type: GrantFiled: August 13, 1991Date of Patent: March 2, 1993Assignee: Loyola University of ChicagoInventor: James H. Babler
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Patent number: 5162590Abstract: Vinyl polyether alcohols of formula I ##STR1## (R=C.sub.1 -C.sub.25 -alkyl, C.sub.2 -C.sub.25 -alkenyl or alkylaryl having a total of not more than 20 carbon atoms,A=1,2-alkylene having from 2 to 4 carbon atoms and n=1 to 20).These compounds serve as intermediates in the preparation of polyether sulfonates of formula III ##STR2## (M=hydrogen, alkali metal or ammonium). The vinyl polyether alcohols of formula I are useful as surface-active compounds for inclusion in surface-active compositions.Type: GrantFiled: February 7, 1991Date of Patent: November 10, 1992Assignee: BASF AktiengesellschaftInventors: Martin Fischer, Richard Baur, Paul Diessel
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Patent number: 5143589Abstract: Perfluoropolyethers having an acid end group of the type of acyl fluoride (or chloride) or a carboxylic group or derivatives thereof, the other end group being a perfluoroalkyl containing one or two halogen atoms different from fluorine, are prepared by photooxidation of C.sub.3 F.sub.6 and/or C.sub.2 F.sub.4, in the presence of a fully halogenated ethylene containing 1 to 4, preferably 1 or 2 atoms of halogen different from fluorine, and by the subsequent thermal of photochemical decomposition treatment of the peroxide groups which are present in the photooxidation product.Type: GrantFiled: January 29, 1991Date of Patent: September 1, 1992Assignee: Ausimont S.r.L.Inventors: Giuseppe Marchionni, Anna Staccione
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Patent number: 5032305Abstract: A lubricant composition for refrigerators using Flon 134a comprises at least 80 percent by weight of a specific type of polyoxethylene glycol dialkyl ether having a kinematic viscosity of 6 to 500 cSt at 40 degree centigrade.Type: GrantFiled: April 13, 1990Date of Patent: July 16, 1991Assignee: Asahi Denka Kogyo K.K.Inventors: Tamiji Kamakura, Yuzi Baba, Kimiyoshi Namiwa
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Patent number: 5025093Abstract: A method of breaking down perfluoropolyethers into lower molecular weight fragments by pyrolysis is disclosed. The perfluoropolyethers are pyrolyzed generally at above about 350.degree. C. Volatile lower molecular weight components are condensed and collected. Various molecular weight fractions and collected. Various molecular weight fractions can be obtained by taking appropriate distillation cuts.Type: GrantFiled: January 5, 1990Date of Patent: June 18, 1991Assignee: Exfluor Research CorporationInventors: Richard J. Lagow, Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu M. Kawa
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Patent number: 5000830Abstract: Improved process for producing perfluoropolyethers prevailingly constituted by repeating units--CF.sub.2 CF.sub.2 O--and ##STR1## with perfluoroalkyl terminal groups, wiith a mutual ratio of the above C.sub.3 /C.sub.2 units comprised within the range of from 0.2 to 6, endowed with an optimum combination of chemical-physical properties, prepared by means of a process of photo-oxidation of C.sub.3 F.sub.6 +C.sub.2 F.sub.4, under controlled conditions.Type: GrantFiled: May 17, 1989Date of Patent: March 19, 1991Assignee: Ausimont S.r.l.Inventors: Giuseppe Marchionni, Ugo De Patto
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Patent number: 4996368Abstract: The invention relates to a process for the stabilization and purification of perfluoropolyethers of the general formulae (I) or (II) ##STR1## in which R=--F or --C.sub.a F.sub.2a+1R'=--F or --C.sub.b F.sub.2b+1n,m=0,1, . . . or 12, n being identical with or different from m, 1.ltoreq.n+m.ltoreq.15a,b=1,2, . . . or 10, a being identical with or different from b ##STR2## in which R"=--C.sub.f F.sub.2f+1R"'=--C.sub.g F.sub.2g+1X=--F or --CF.sub.3c,d,e=integers such that the molecular weight of the perfluoropolyether is between 200 and 2000, where c, d and e may be identical or different and the units [C.sub.3 F.sub.6 O].sub.c, [C.sub.2 F.sub.4 O].sub.d, and [CFXO].sub.e may be randomly distributed along the molecular chain of the perfluoropolyether,or of mixtures of perfluoropolyethers of this type. The process comprises heating the perfluoropolyethers or mixtures thereof to 150.degree.-360.degree. C.Type: GrantFiled: January 29, 1990Date of Patent: February 26, 1991Assignee: Hoechst AktiengesellschaftInventor: Thomas Gries
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Patent number: 4992595Abstract: Compounds of the formula ##STR1## where R.sub.1 denotes a group of the formula ##STR2## R.sub.2 denotes C.sub.1 -C.sub.4 -alkyl, R.sub.3 denotes hydrogen or methyl, n denotes a number from 5 to 100, m denotes an integer from 0 to 4 and x denotes the number of free valences of the particular R.sub.1 radical, a process for the preparation thereof, and the use thereof as fiber spin finishes.Type: GrantFiled: November 23, 1988Date of Patent: February 12, 1991Assignee: Hoechst AktiengesellschaftInventors: Rolf Kleber, Siegfried Billenstein, Lothar Jaeckel, Ignaz Wimmer
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Patent number: 4980485Abstract: Optically active periplanone-B is manufactured through oxidizing (1RS, 4S, 5E)-isopropyl-7-methylene-5-cyclodecene-1-ol. The oxidized product is regioselectively enolized and then sulfenylated. The sulfenylated product is oxidized and then subjected to decomposition of the sulfoxide. The decomposed product is epoxidated, and the epoxidated product is converted into an enolate which is then oxidized. The oxidized product is oxidized and then regio- and stereoselectively epoxidated to obtain optically active periplanone-B.Type: GrantFiled: September 26, 1989Date of Patent: December 25, 1990Assignee: Japan Tobacco Inc.Inventors: Kenji Mori, Takeshi Kitahara, Koshi Koseki
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Patent number: 4894484Abstract: A method of breaking down perfluoropolyethers into lower molecular weight fragments by pyrolysis is disclosed. The perfluoropolyethers are pyrolyzed generally at above about 350.degree. C. Volatile lower molecular weight components are condensed and collected. Various molecular weight fractions can be obtained by taking appropriate distillation cuts.Type: GrantFiled: September 3, 1987Date of Patent: January 16, 1990Assignee: Exfluor Research CorporationInventors: Richard J. Lagow, Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu M. Kawa
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Patent number: 4847427Abstract: An improvement in a process for neutralizing perfluorinated carboxylic acids to make fluorocarbon polyethers in which the acid is heated with fluorine in the presence of a metal fluoride.Type: GrantFiled: April 13, 1988Date of Patent: July 11, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Mario J. Nappa
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Patent number: 4827042Abstract: Perfluoropolyethers containing high concentrations of difluoromethylene oxide units in the polymer chain are disclosed.Type: GrantFiled: September 2, 1987Date of Patent: May 2, 1989Assignee: ExFluor Research CorporationInventors: Richard J. Lagow, Thomas R. Bierschenk, Timothy J. Juhlke