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4-Traders Homepage  >  Equities  >  Tokyo  >  Ube Industries, Ltd.    4208   JP3158800007

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Ube Industries : Patent Issued for Non-Aqueous Electrolytic Solution, Electrical Storage Device Utilizing Same, and Cyclic Sulfonic Acid Ester Compound (USPTO 9608287)

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04/07/2017 | 12:40am CEST

By a News Reporter-Staff News Editor at Journal of Engineering -- From Alexandria, Virginia, VerticalNews journalists report that a patent by the inventors Abe, Koji (Yamaguchi, JP); Shikita, Shoji (Yamaguchi, JP), filed on April 25, 2012, was published online on March 28, 2017.

The patent's assignee for patent number 9608287 is UBE INDUSTRIES, LTD. (Ube-shi, JP).

News editors obtained the following quote from the background information supplied by the inventors: "In recent years, energy storage devices, especially lithium secondary batteries have been widely used for small-sized electronic devices, such as mobile telephones, notebook-size personal computers and the like, for electric vehicles, as well as for electric power storage. These electronic devices and vehicles may be used in a broad temperature range, for example, at midsummer high temperatures or at frigid low temperatures, and are therefore required to be improved in point of electrochemical characteristics well balanced in a broad temperature range.

"Especially for preventing global warming, it is imperative to reduce CO.sub.2 emissions, and of environment-responsive vehicles with, as mounted thereon, an electrical storage installation that comprises an energy storage device, such as a lithium secondary battery, a capacitor or the like, early popularization of hybrid electric vehicles (HEV), plug-in hybrid electric vehicles (PHEV) and battery electric vehicles (BEV) is desired. Vehicles could take a long travel distance and therefore could be used in regions in a broad temperature range covering from extremely-hot tropical regions to frigid regions. In particular, therefore, it is desired that the electrochemical characteristics of in-car energy storage devices for those vehicles are not worsened even in use thereof in a broad temperature range covering from high temperatures to low temperatures.

"In this specification, the term, lithium secondary battery is used as a concept including a so-called lithium ion secondary battery.

"A lithium secondary battery is mainly constituted of a positive electrode and a negative electrode containing a material capable of absorbing and releasing lithium, and a nonaqueous electrolytic solution containing a lithium salt and a nonaqueous solvent. For the nonaqueous solvent, used are carbonates, such as ethylene carbonate (EC), propylene carbonate (PC), etc.

"As the negative electrode, known are metal lithium, and metal compounds (metal elemental substances, oxides, alloys with lithium, etc.) and carbon materials capable of absorbing and releasing lithium. In particular, a lithium secondary battery using a carbon material capable of absorbing and releasing lithium, such as coke, artificial graphite, natural graphite or the like, has been widely put into practical use.

"For example, it is known that, in a lithium secondary battery using a highly-crystalline carbon material, such as natural graphite, artificial graphite or the like as the negative electrode material therein, the decomposed products or gas generated through reductive decomposition of the solvent in the nonaqueous electrolytic solution on the surface of the negative electrode during charging detracts from the electrochemical reaction favorable for the battery, therefore worsening the cycle properties of the battery. Deposition of the decomposed products of the nonaqueous solvent interferes with smooth absorption and release of lithium by the negative electrode, and therefore the electrochemical characteristics of the battery in use thereof in a broad temperature range may often tend to worsen.

"In addition, it is known that a lithium secondary battery using a lithium metal or its alloy, or a metal elemental substance, such as tin, silicon or the like or its metal oxide as the negative electrode material therein could have a high initial battery capacity but the battery capacity and the battery performance thereof, such as cycle properties may greatly worsen, since the micronized powdering of the material is promoted during cycles thereby bringing about accelerated reductive decomposition of the nonaqueous solvent, as compared with the negative electrode of a carbon material. In addition, the micronized powdering of the negative electrode material and the deposition of the decomposed products of the nonaqueous solvent may interfere with smooth absorption and release of lithium by the negative electrode, and therefore the electrochemical characteristics of the battery in use thereof in a broad temperature range may often tend to worsen.

"On the other hand, it is known that, in a lithium secondary battery using, for example, LiCoO.sub.2, LiMn.sub.2O.sub.4, LiNiO.sub.2, LiFePO.sub.4 or the like as the positive electrode, the nonaqueous solvent in the nonaqueous electrolytic solution locally undergoes partial oxidative decomposition in the interface between the positive electrode material and the nonaqueous electrolytic solution in the charged state and the decomposed products or the gas thereby generated as a result of the partial oxidative decomposition interferes with the electrochemical reaction favorable for the battery, and therefore the electrochemical characteristics of the battery would be thereby also worsened in use in a broad temperature range.

"As in the above, the decomposed products and the gas generated through decomposition of the nonaqueous electrolytic solution on the positive electrode or the negative electrode may interfere with the movement of lithium ions or may swell the battery, and the battery performance is thereby worsened. Despite the situation, electronic appliances equipped with lithium secondary batteries therein are offering more and more an increasing range of functions and are being in a stream of further increase in power consumption. With that, the capacity of lithium secondary batteries is being much increased, and the space volume for the nonaqueous electrolytic solution in the battery is decreased by increasing the density of the electrode and by reducing the useless space volume in the battery. Accordingly, the situation is that even decomposition of only a small amount of the nonaqueous electrolytic solution may worsen the electrochemical characteristics of the battery in use thereof in a broad temperature range.

"PTL 1 proposes a nonaqueous electrolytic solution containing a hydroxypropane sultone and suggests that the hydroxy group of the hydroxypropane sultone adsorbs to lithium metal before discharge and during charge and discharge to thereby form a dense and stable surface film on the negative electrode and the cycle properties are thereby improved."

As a supplement to the background information on this patent, VerticalNews correspondents also obtained the inventors' summary information for this patent: "Technical Problem

"An object of the present invention is to provide a nonaqueous electrolytic solution capable of improving electrochemical characteristics in a broad temperature range, an energy storage device using it, and a cyclic sulfonic acid ester compound.

"Solution to Problem

"The present inventors have investigated in detail the performance of the nonaqueous electrolytic solutions in the above-mentioned prior art. As a result, in the nonaqueous electrolytic solution of the above-mentioned patent literature, the hydroxy group of the hydroxypropane sulfone is readily reduced, and therefore the nonaqueous electrolytic solution would be excessively decomposed during high-temperature storage in a charged state therefore causing self-discharge and increasing the resistance of the negative electrode, and in fact, therefore, the nonaqueous electrolytic solution could not exhibit a sufficient effect for the problem of improving the electrochemical characteristics of batteries in a broad temperature range, such as low-temperature discharge characteristics thereof after high-temperature storage, etc.

"Given the situation, the present inventors have assiduously studied for the purpose of solving the above-mentioned problems, and have found that, when at least one specific cyclic sulfonic acid ester compound is added to a nonaqueous electrolytic solution of an electrolyte salt dissolved in a nonaqueous solvent, then the electrochemical characteristics of energy storage devices in a broad temperature range, especially the electrochemical characteristics of lithium batteries can be improved, and have completed the present invention.

"Specifically, the present invention provides the following (1) to (3):

"(1) A nonaqueous electrolytic solution of an electrolyte salt dissolved in a nonaqueous solvent, which comprises at least one cyclic sulfonic acid ester compound represented by the following general formula (I):

"##STR00002## (In the formula, R.sup.1 and R.sup.2 may be the same or different, each representing a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms in which at least one hydrogen atom may be substituted with a halogen atom, or a halogen atom; L represents a divalent hydrocarbon group of an alkylene group having 2 or 3 carbon atoms in which at least one hydrogen atom is substituted with OR.sup.3, or a divalent hydrocarbon group of an alkylene group having 2 or 3 carbon atoms in which at least one methylene (CH.sub.2) group is substituted with a group C(.dbd.O); R.sup.3 represents a formyl group, an alkylcarbonyl group having from 2 to 7 carbon atoms, an alkenylcarbonyl group having from 3 to 7 carbon atoms, an alkynylcarbonyl group having from 3 to 7 carbon atoms, an arylcarbonyl group having from 7 to 13 carbon atoms, an alkoxycarbonyl group having from 2 to 7 carbon atoms, an alkenyloxycarbonyl group having from 3 to 7 carbon atoms, an alkynyloxycarbonyl group having from 4 to 7 carbon atoms, an aryloxycarbonyl group having from 7 to 13 carbon atoms, a 2,2-dioxide-1,2-oxathiolan-4-yloxycarbonyl group, a 2,2-dioxide-1,2-oxathian-4-yloxycarbonyl group, an alkanesulfonyl group having from 1 to 6 carbon atoms, an arylsulfonyl group having from 6 to 12 carbon atoms, a dialkylphosphoryl group having from 2 to 12 carbon atoms, an alkoxy(alkyl)phosphoryl group having from 2 to 12 carbon atoms, a dialkoxyphosphoryl group having from 2 to 12 carbon atoms, a group --S(O)--OR.sup.4 or a group --C(O)CH.sub.2P(O)(OR.sup.5).sub.2; R.sup.4 represents an alkyl group having from 1 to 6 carbon atoms, a 2,2-dioxide-1,2-oxathiolan-4-yl group, or a 2,2-dioxide-1,2-oxathian-4-yl group; R.sup.5 represents an alkyl group having from 1 to 6 carbon atoms. Further, in R.sup.3, at least one hydrogen atom may be substituted with a halogen atom, and L may be further substituted with any of an alkyl group having from 1 to 6 carbon atoms, a haloalkyl group having from 1 to 6 carbon atoms or a halogen atom.)

"(2) An energy storage device comprising a positive electrode, a negative electrode, and a nonaqueous electrolytic solution of an electrolyte salt dissolved in a nonaqueous solvent, wherein the nonaqueous electrolytic solution is the nonaqueous electrolytic solution of the above (1).

"(3) A cyclic sulfonic acid ester compound represented by the following general formula (II):

"##STR00003## (In the formula, R.sup.1 and R.sup.2 may be the same or different, each representing a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms in which at least one hydrogen atom may be substituted with a halogen atom, or a halogen atom; L.sup.1 represents a divalent hydrocarbon group of an alkylene group having 2 or 3 carbon atoms in which at least one hydrogen atom is substituted with OR.sup.6, or a divalent hydrocarbon group of an alkylene group having 2 or 3 carbon atoms in which at least one methylene (CH.sub.2) group is substituted with a group C(.dbd.O); R.sup.6 represents a formyl group, an alkenylcarbonyl group having from 3 to 7 carbon atoms, an alkynylcarbonyl group having from 3 to 7 carbon atoms, an alkoxycarbonyl group having from 2 to 7 carbon atoms, an alkenyloxycarbonyl group having from 3 to 7 carbon atoms, an alkynyloxycarbonyl group having from 4 to 7 carbon atoms, an aryloxycarbonyl group having from 7 to 13 carbon atoms, a 2,2-dioxide-1,2-oxathiolan-4-yloxycarbonyl group, a 2,2-dioxide-1,2-oxathian-4-yloxycarbonyl group, a dialkylphosphoryl group having from 2 to 12 carbon atoms, an alkoxy(alkyl)phosphoryl group having from 2 to 12 carbon atoms, a dialkoxyphosphoryl group having from 2 to 12 carbon atoms, a group --S(O)--OR.sup.4 or a group --C(O)CH.sub.2P(O)(OR.sup.5).sub.2; R.sup.4 represents an alkyl group having from 1 to 6 carbon atoms, a 2,2-dioxide-1,2-oxathiolan-4-yl group, or a 2,2-dioxide-1,2-oxathian-4-yl group; R.sup.5 represents an alkyl group having from 1 to 6 carbon atoms. Further, in R.sup.6, at least one hydrogen atom may be substituted with a halogen atom, and L.sup.1 may be further substituted with any of an alkyl group having from 1 to 6 carbon atoms, a haloalkyl group having from 1 to 6 carbon atoms or a halogen atom. However, when L.sup.1 is a divalent hydrocarbon group of an alkylene group having 2 or 3 carbon atoms in which at least one methylene (CH.sub.2) group is substituted with a group (C.dbd.O), then R.sup.1 and R.sup.2 are hydrogen atoms.)

"Advantageous Effects of Invention

"According to the present invention, there are provided a nonaqueous electrolytic solution capable of improving the electrochemical characteristics of energy storage devices in a broad temperature range, especially the low-temperature discharge characteristics thereof after high-temperature storage, an energy storage device, such as lithium batteries and others using the nonaqueous electrolytic solution, and a specific cyclic sulfonic acid ester compound."

For additional information on this patent, see: Abe, Koji; Shikita, Shoji. Non-Aqueous Electrolytic Solution, Electrical Storage Device Utilizing Same, and Cyclic Sulfonic Acid Ester Compound. U.S. Patent Number 9608287, filed April 25, 2012, and published online on March 28, 2017. Patent URL: http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=9608287.PN.&OS=PN/9608287RS=PN/9608287

Keywords for this news article include: Gases, Elements, Graphite, Hydrogen, Minerals, Hydrocarbons, Sulfur Acids, Sulfonic Acids, Electrochemicals, UBE INDUSTRIES LTD, Inorganic Chemicals.

Our reports deliver fact-based news of research and discoveries from around the world. Copyright 2017, NewsRx LLC

(c) 2017 NewsRx LLC, source Science Newsletters

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Sales 2018 644 150 M
EBIT 2018 -
Net income 2018 24 171 M
Debt 2018 127 650 M
Yield 2018 2,47%
P/E ratio 2018 11,03
P/E ratio 2019 9,83
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