WO2014002503A1 - (メタ)アクリル樹脂組成物の製造方法 - Google Patents
(メタ)アクリル樹脂組成物の製造方法 Download PDFInfo
- Publication number
- WO2014002503A1 WO2014002503A1 PCT/JP2013/004036 JP2013004036W WO2014002503A1 WO 2014002503 A1 WO2014002503 A1 WO 2014002503A1 JP 2013004036 W JP2013004036 W JP 2013004036W WO 2014002503 A1 WO2014002503 A1 WO 2014002503A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- tank reactor
- acrylic resin
- meth
- reaction
- monomer mixture
- Prior art date
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- 229920006037 cross link polymer Polymers 0.000 description 1
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 1
- PTWJGGCOPUFTFL-UHFFFAOYSA-N cyclohexane;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.C1CCCCC1 PTWJGGCOPUFTFL-UHFFFAOYSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- SKEQOTBKQUCUGK-UHFFFAOYSA-N o-(2-hydroxyethyl) propanethioate Chemical compound CCC(=S)OCCO SKEQOTBKQUCUGK-UHFFFAOYSA-N 0.000 description 1
- XVKLLVZBGMGICC-UHFFFAOYSA-N o-[3-propanethioyloxy-2,2-bis(propanethioyloxymethyl)propyl] propanethioate Chemical compound CCC(=S)OCC(COC(=S)CC)(COC(=S)CC)COC(=S)CC XVKLLVZBGMGICC-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/01—Processes of polymerisation characterised by special features of the polymerisation apparatus used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/02—Polymerisation in bulk
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F6/00—Post-polymerisation treatments
- C08F6/001—Removal of residual monomers by physical means
- C08F6/005—Removal of residual monomers by physical means from solid polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F6/00—Post-polymerisation treatments
- C08F6/26—Treatment of polymers prepared in bulk also solid polymers or polymer melts
- C08F6/28—Purification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
- C08L33/12—Homopolymers or copolymers of methyl methacrylate
Definitions
- the present invention includes the following embodiments.
- Two or more reaction raw materials comprising a monomer mixture containing 80 to 100% by weight of methyl methacrylate and 20 to 0% by weight of an acrylic acid alkyl ester, a chain transfer agent, and a radical polymerization initiator
- the shape of the supply port may be the shape of the cut end of the circular tube itself, or may be a shape such that the reaction raw material is widely dispersed on the liquid surface in the reaction tank.
- the complete mixing time ( ⁇ M [hr]) of the tank reactor is equal to the half-life ( ⁇ 1/2 [hr]) of the radical polymerization initiator at the temperature in the tank reactor.
- a time of a numerical value larger than a numerical value preferably a time of a numerical value larger than a numerical value of 1.2 times the half-life. That is, the relationship ⁇ M > ⁇ 1/2 , preferably the relationship ⁇ M > 1.2 ⁇ ⁇ 1/2 is satisfied.
- the complete mixing time is one of indexes indicating the mixing characteristics of the reaction vessel.
- n ⁇ ⁇ M -Re indicating the relationship between n ⁇ ⁇ M (the dimensionless mixing number [n is the number of revolutions of the stirring blade [1 / sec]]) and Re (Reynolds number: an index representing the turbulent state of the liquid) It is obtained from the “curve”.
- the complete mixing time and the n ⁇ ⁇ M -Re curve are described in, for example, Non-Patent Document 2, Patent Document 4, and Patent Document 5.
- the ultraviolet absorber is a compound having an ability to absorb ultraviolet rays.
- the ultraviolet absorber is a compound that is said to have a function of mainly converting light energy into heat energy.
- Examples of the ultraviolet absorber include benzophenones, benzotriazoles, triazines, benzoates, salicylates, cyanoacrylates, succinic anilides, malonic esters, formamidines, and the like. These can be used alone or in combination of two or more.
- benzotriazoles or ultraviolet absorbers having a maximum molar extinction coefficient ⁇ max at a wavelength of 380 to 450 nm of 1200 dm 3 ⁇ mol ⁇ 1 cm ⁇ 1 or less are preferable.
- an ultraviolet absorber having a maximum molar extinction coefficient ⁇ max at a wavelength of 380 to 450 nm of 1200 dm 3 ⁇ mol ⁇ 1 cm ⁇ 1 or less, 2-ethyl-2′-ethoxy-oxalanilide (manufactured by Clariant Japan, Inc .; Trade name Sundeyuboa VSU).
- benzotriazoles are preferably used from the viewpoint of suppressing resin degradation due to ultraviolet irradiation.
- the polymer processing aid is a compound that exhibits an effect on thickness accuracy and thinning when a (meth) acrylic resin composition is molded.
- the polymer processing aid is polymer particles having a particle diameter of 0.05 to 0.5 ⁇ m, which can be usually produced by an emulsion polymerization method.
- the polymer particles may be single layer particles composed of polymers having a single composition ratio and single intrinsic viscosity, or multilayer particles composed of two or more kinds of polymers having different composition ratios or intrinsic viscosities. May be.
- additives may be added at the reaction raw material stage, may be added at the reaction product stage, or may be added at the stage of the (meth) acrylic resin composition obtained after devolatilization. Good.
- the complete mixing time was 45 seconds, the stirring power was 2.6 kW / m 3 , the Reynolds number was 209, the power number was 6, and the dimensionless mixing number was 150.
- P V ⁇ ⁇ ⁇ I ⁇ ⁇ 1/2 was 0.5.
- the rotation speed of the stirring blade was changed to 100 rpm and the polymerization conversion rate was confirmed after 4 hours, it was determined that the polymerization conversion rate could be controlled by the stirring rotation speed because it changed by 2% or more.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2014522435A JP6014668B2 (ja) | 2012-06-29 | 2013-06-28 | (メタ)アクリル樹脂組成物の製造方法 |
EP13809577.3A EP2868671A4 (en) | 2012-06-29 | 2013-06-28 | PREPARATION METHOD FOR (METH) ACRYLIC RESIN COMPOSITION |
SG11201408760SA SG11201408760SA (en) | 2012-06-29 | 2013-06-28 | Manufacturing method for (meth)acrylic resin composition |
CN201380034943.XA CN104411730B (zh) | 2012-06-29 | 2013-06-28 | (甲基)丙烯酸类树脂组合物的制造方法 |
KR1020157002163A KR102005135B1 (ko) | 2012-06-29 | 2013-06-28 | (메트)아크릴 수지 조성물의 제조 방법 |
IN11138DEN2014 IN2014DN11138A (forum.php) | 2012-06-29 | 2013-06-28 | |
US14/411,735 US20150158963A1 (en) | 2012-06-29 | 2013-06-28 | Method for producing (meth)acrylic resin composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012-147996 | 2012-06-29 | ||
JP2012147996 | 2012-06-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2014002503A1 true WO2014002503A1 (ja) | 2014-01-03 |
Family
ID=49782690
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2013/004036 WO2014002503A1 (ja) | 2012-06-29 | 2013-06-28 | (メタ)アクリル樹脂組成物の製造方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US20150158963A1 (forum.php) |
EP (1) | EP2868671A4 (forum.php) |
JP (1) | JP6014668B2 (forum.php) |
KR (1) | KR102005135B1 (forum.php) |
CN (1) | CN104411730B (forum.php) |
IN (1) | IN2014DN11138A (forum.php) |
MY (1) | MY178431A (forum.php) |
SG (1) | SG11201408760SA (forum.php) |
TW (1) | TWI573807B (forum.php) |
WO (1) | WO2014002503A1 (forum.php) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104926984A (zh) * | 2015-07-14 | 2015-09-23 | 苏州双象光学材料有限公司 | 高分子量改性聚甲基丙烯酸甲酯的制备方法 |
WO2016031849A1 (ja) * | 2014-08-26 | 2016-03-03 | 株式会社クラレ | (メタ)アクリル樹脂組成物の製造方法 |
JP2017019946A (ja) * | 2015-07-13 | 2017-01-26 | 東亞合成株式会社 | アクリル酸系重合体塩水溶液の製造方法 |
KR20170040186A (ko) * | 2014-08-06 | 2017-04-12 | 주식회사 쿠라레 | (메트)아크릴 수지 조성물의 제조 방법 |
EP3103819A4 (en) * | 2014-02-06 | 2017-10-04 | Kuraray Co., Ltd. | Production method of (meth)acrylic resin composition |
JP2020510120A (ja) * | 2017-09-29 | 2020-04-02 | エルジー・ケム・リミテッド | 炭素繊維製造用(メタ)アクリロニトリル系重合体の製造方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20190033752A (ko) | 2017-09-22 | 2019-04-01 | 성균관대학교산학협력단 | 차량의 주행 데이터를 이용하여 운전자의 이상상태를 판단하기 위한 시스템 |
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Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3103819A4 (en) * | 2014-02-06 | 2017-10-04 | Kuraray Co., Ltd. | Production method of (meth)acrylic resin composition |
US9920142B2 (en) | 2014-02-06 | 2018-03-20 | Kuraray Co., Ltd. | Production method of (meth)acrylic resin composition |
KR20170040186A (ko) * | 2014-08-06 | 2017-04-12 | 주식회사 쿠라레 | (메트)아크릴 수지 조성물의 제조 방법 |
EP3178854A4 (en) * | 2014-08-06 | 2018-03-07 | Kuraray Co., Ltd. | Method for producing (meth)acrylic resin composition |
US10030081B2 (en) | 2014-08-06 | 2018-07-24 | Kuraray Co., Ltd. | Method for producing (meth)acrylic resin composition |
KR102394029B1 (ko) | 2014-08-06 | 2022-05-03 | 주식회사 쿠라레 | (메트)아크릴 수지 조성물의 제조 방법 |
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JPWO2016031849A1 (ja) * | 2014-08-26 | 2017-06-08 | 株式会社クラレ | (メタ)アクリル樹脂組成物の製造方法 |
JP2017019946A (ja) * | 2015-07-13 | 2017-01-26 | 東亞合成株式会社 | アクリル酸系重合体塩水溶液の製造方法 |
CN104926984A (zh) * | 2015-07-14 | 2015-09-23 | 苏州双象光学材料有限公司 | 高分子量改性聚甲基丙烯酸甲酯的制备方法 |
JP2020510120A (ja) * | 2017-09-29 | 2020-04-02 | エルジー・ケム・リミテッド | 炭素繊維製造用(メタ)アクリロニトリル系重合体の製造方法 |
US11046792B2 (en) | 2017-09-29 | 2021-06-29 | Lg Chem, Ltd. | Method of preparing (meth)acrylonitrile-based polymer for preparing carbon fiber |
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IN2014DN11138A (forum.php) | 2015-09-25 |
KR20150027814A (ko) | 2015-03-12 |
CN104411730A (zh) | 2015-03-11 |
TWI573807B (zh) | 2017-03-11 |
MY178431A (en) | 2020-10-13 |
EP2868671A1 (en) | 2015-05-06 |
JPWO2014002503A1 (ja) | 2016-05-30 |
US20150158963A1 (en) | 2015-06-11 |
TW201412781A (zh) | 2014-04-01 |
EP2868671A4 (en) | 2016-04-27 |
SG11201408760SA (en) | 2015-01-29 |
CN104411730B (zh) | 2016-03-02 |
KR102005135B1 (ko) | 2019-07-29 |
JP6014668B2 (ja) | 2016-10-25 |
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