JP6445736B2 - アルキルベンゼンスルホン酸のアミン塩及び洗剤製剤におけるその使用 - Google Patents
アルキルベンゼンスルホン酸のアミン塩及び洗剤製剤におけるその使用 Download PDFInfo
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- JP6445736B2 JP6445736B2 JP2018503459A JP2018503459A JP6445736B2 JP 6445736 B2 JP6445736 B2 JP 6445736B2 JP 2018503459 A JP2018503459 A JP 2018503459A JP 2018503459 A JP2018503459 A JP 2018503459A JP 6445736 B2 JP6445736 B2 JP 6445736B2
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- amine
- detergent
- surfactant
- alkyl
- surfactants
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- 239000000203 mixture Substances 0.000 title claims description 53
- 238000009472 formulation Methods 0.000 title claims description 42
- 239000003599 detergent Substances 0.000 title claims description 41
- -1 Amine salts Chemical class 0.000 title claims description 24
- 239000004094 surface-active agent Substances 0.000 claims description 41
- 150000001412 amines Chemical class 0.000 claims description 28
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 18
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 18
- 239000003945 anionic surfactant Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- 229930195729 fatty acid Natural products 0.000 claims description 9
- QADXVXGIHZYVQI-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-amine Chemical compound COCC(C)OCC(C)N QADXVXGIHZYVQI-UHFFFAOYSA-N 0.000 claims description 5
- QWCGXANSAOXRFE-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanamine Chemical compound COCCOCCN QWCGXANSAOXRFE-UHFFFAOYSA-N 0.000 claims description 5
- LVFVRCPHJZOLAT-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanamine Chemical compound CCCCOCCOCCN LVFVRCPHJZOLAT-UHFFFAOYSA-N 0.000 claims description 4
- BFBKUYFMLNOLOQ-UHFFFAOYSA-N 2-butoxyethanamine Chemical compound CCCCOCCN BFBKUYFMLNOLOQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- NXMXETCTWNXSFG-UHFFFAOYSA-N 1-methoxypropan-2-amine Chemical compound COCC(C)N NXMXETCTWNXSFG-UHFFFAOYSA-N 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- MFVADXSCIMPPEU-UHFFFAOYSA-N 1-butoxypropan-2-amine Chemical compound CCCCOCC(C)N MFVADXSCIMPPEU-UHFFFAOYSA-N 0.000 claims 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- QJRVOJKLQNSNDB-UHFFFAOYSA-N 4-dodecan-3-ylbenzenesulfonic acid Chemical group CCCCCCCCCC(CC)C1=CC=C(S(O)(=O)=O)C=C1 QJRVOJKLQNSNDB-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000004996 alkyl benzenes Chemical class 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000008051 alkyl sulfates Chemical class 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XRIBIDPMFSLGFS-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropan-1-ol Chemical compound CN(C)C(C)(C)CO XRIBIDPMFSLGFS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000002169 ethanolamines Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- RJCHCFQTUKAYAA-UHFFFAOYSA-N 5-[[2-amino-5-[(4-methoxyphenyl)methyl]-3-methylimidazol-4-yl]methyl]-2-methoxybenzene-1,3-diol Chemical compound C1=CC(OC)=CC=C1CC1=C(CC=2C=C(O)C(OC)=C(O)C=2)N(C)C(=N)N1 RJCHCFQTUKAYAA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/04—Detergent materials or soaps characterised by their shape or physical properties combined with or containing other objects
- C11D17/041—Compositions releasably affixed on a substrate or incorporated into a dispensing means
- C11D17/042—Water soluble or water disintegrable containers or substrates containing cleaning compositions or additives for cleaning compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
Description
本出願は、参照によりその全体が本明細書に組み込まれる、2015年4月30日に出願された米国仮特許出願第62/155,044号の優先権を主張する。
モノエタノールアミン(MEA):110mLガラス瓶に、56.7gの脱イオン水を入れる。磁気撹拌棒による撹拌下で、3.16gのMEAを完全に可溶化するまで添加する。次いで、終始撹拌下で、直鎖アルキルベンゼンスルホン酸(アルキルは、フェニル環のパラ位において約C10−C13である)(HLAS)を滴下様式で徐々に添加する。添加されるHLASの質量が15.08gとなるまで継続する。全ての成分(HLAS+MEA)が完全に可溶化し、視認され得る微粒子または凝集体が観察されなくなるまで、撹拌を継続する。全界面活性剤濃度は、(3.16+15.08)*100/(3.16+15.08+56.7)=24.3%であると計算される。次いで、溶液のpHを測定するが、この場合pH=8.27である。
上述のような界面活性剤溶液に加えて、2種の溶媒(プロピレングリコール及びグリセロール)、2種の界面活性剤(StepanからのBIOSOFT N25−7、7モルのEOを有する直鎖アルコールエトキシレート及びSTEOL CS270、2モルのEOを有するアルキルエーテルサルフェート)ならびに脂肪酸(CrodaからのPALMERA B1220)を含有する洗剤製剤を調製する。そのような洗剤製剤の典型的な調製例は、以下の通りである。
前項記載のように調製された界面活性剤溶液(2−(2−メトキシエトキシ)−1−アミノエタン(DMアミン)塩、1−(2−メトキシ−1−メチルエトキシ)−2−アミノプロパン(DPMアミン)塩、Na塩、及びMEA塩)の粘度を、Brookfield粘度計で、6s−1から60s−1の間のせん断速度で測定する。データを表1に示す。
この実施例において、約0.6gのPVOHフィルム(M8630、Monosol Inc.から商業的に入手可能)を、6gの20重量%界面活性剤に添加し、手により激しく振盪する。多くの商業的液体洗濯洗剤において一般的に使用されているMEA系界面活性剤では、PVOHフィルムは、界面活性剤/水混合物と相互作用して、「塊」、すなわち完全には可溶化していない複合体を形成する。DMアミン系界面活性剤溶液に関しても同様の挙動が観察された。
この実施例において、バイアル内で1.5gの洗剤製剤を1.5gの脱イオン水に添加し、これを手で激しく振盪する。MEA系界面活性剤を含有する製剤は、粘稠性の凝集体を形成する。一方、2−(2−ブトキシエトキシ)−1−アミノエタン(DBアミン)、2−ブトキシ−1−アミノエタン(EBアミン)、1−(2−メトキシ−1−メチルエトキシ)−2−アミノプロパン(DPMアミン)、または1−メトキシ−2−アミノプロパン(PMアミン)を含有する製剤は、水が添加された場合より低い粘度を示し、均質である。
この実施例において、3gの洗剤製剤を0.6gの10重量%PVOH溶液(PVOHフィルムを水に溶解することにより調製される)に添加する。この実施例は、パウチが水に溶解した際に生じること、すなわちまずPVOHフィルムが水に溶解し、次いで製剤の内容物が洗浄液中に放出されることを動的に模擬している。次いで、製剤成分、水、及び溶解したPVOHの間で相互作用が生じる。
Claims (6)
- 式I:
- R1は、フェニル環の4位にある、請求項1に記載の界面活性剤。
- R1は、直鎖(C10−C13)アルキルである、請求項1または2のいずれか一項に記載の界面活性剤。
- グリコールエーテルアミン化合物は、2−ブトキシ−1−アミノエタン(EBアミン)、2−(2−ブトキシエトキシ)−1−アミノエタン(DBアミン)、2−(2−メトキシエトキシ)−1−アミノエタン(DMアミン)、1−(2−メトキシ−1−メチルエトキシ)−2−アミノプロパン(DPMアミン)、1−メトキシ−2−アミノプロパン(PMアミン)及び1−ブトキシ−2−アミノプロパン(PnBアミン)である、請求項1から3のいずれか一項に記載の界面活性剤。
- 水溶性ポリビニルアルコールパウチ内に封入された、請求項1から4のいずれか一項に記載のアミンで中和されたアニオン性界面活性剤を含有する洗剤製剤を含む、洗剤パック。
- 前記洗剤製剤は、脂肪酸塩、1種以上の追加の界面活性剤、1種以上の溶媒(例えば、プロピレングリコール及びグリセロール)ならびに水をさらに含む、請求項5に記載の洗剤パック。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201562155044P | 2015-04-30 | 2015-04-30 | |
US62/155,044 | 2015-04-30 | ||
PCT/US2016/022845 WO2016175931A1 (en) | 2015-04-30 | 2016-03-17 | Amine salts of alkylbenzene sulfonic acids and their use in detergent formulations |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2018510960A JP2018510960A (ja) | 2018-04-19 |
JP6445736B2 true JP6445736B2 (ja) | 2018-12-26 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2018503459A Active JP6445736B2 (ja) | 2015-04-30 | 2016-03-17 | アルキルベンゼンスルホン酸のアミン塩及び洗剤製剤におけるその使用 |
Country Status (7)
Country | Link |
---|---|
US (1) | US10351800B2 (ja) |
EP (1) | EP3289055B1 (ja) |
JP (1) | JP6445736B2 (ja) |
CN (1) | CN107532114B (ja) |
AU (1) | AU2016254859B2 (ja) |
BR (1) | BR112017022577B1 (ja) |
WO (1) | WO2016175931A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP7492504B2 (ja) * | 2018-09-28 | 2024-05-29 | ダウ グローバル テクノロジーズ エルエルシー | アルキルエーテルアミン泡制御化合物および食材の加工方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000034494A (ja) * | 1998-07-21 | 2000-02-02 | Kao Corp | シート状洗濯用品 |
BR0012199A (pt) * | 1999-06-30 | 2002-04-02 | Huntsman Spec Chem Corp | Misturas surfactantes concentradas |
CA2433837C (en) | 2001-01-19 | 2010-04-20 | Reckitt Benckiser N.V. | Liquid detergent composition comprising alkyl benzene sulfonic acid and an alkanolamine |
ES2379947T3 (es) | 2001-01-31 | 2012-05-07 | The Procter & Gamble Company | Procedimiento para fabricar bolsas |
US20060275566A1 (en) | 2005-06-01 | 2006-12-07 | De Buzzaccarini Francesco | Water-soluble, liquid-containing pouch |
KR101752684B1 (ko) * | 2008-10-21 | 2017-07-04 | 엔테그리스, 아이엔씨. | 구리 세척 및 보호 조성물 |
JP5934112B2 (ja) | 2010-01-29 | 2016-06-15 | モノソル リミテッド ライアビリティ カンパニー | Pvohポリマーのブレンド材を有する改良された水溶性フィルムおよびそれで作られたパケット |
DE102012201502A1 (de) * | 2012-02-02 | 2013-08-08 | Henkel Ag & Co. Kgaa | Wasserarmes, flüssiges Waschmittel mit erhöhter Fettlösekraft |
EP2864439B1 (en) | 2012-06-25 | 2017-03-08 | Dow Global Technologies LLC | Glycol ether amines for use as clay and shale inhibition agents for the drilling industry |
-
2016
- 2016-03-17 US US15/548,962 patent/US10351800B2/en active Active
- 2016-03-17 WO PCT/US2016/022845 patent/WO2016175931A1/en active Application Filing
- 2016-03-17 JP JP2018503459A patent/JP6445736B2/ja active Active
- 2016-03-17 EP EP16716088.6A patent/EP3289055B1/en active Active
- 2016-03-17 BR BR112017022577-8A patent/BR112017022577B1/pt active IP Right Grant
- 2016-03-17 CN CN201680022127.0A patent/CN107532114B/zh active Active
- 2016-03-17 AU AU2016254859A patent/AU2016254859B2/en not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
AU2016254859B2 (en) | 2018-09-27 |
BR112017022577A2 (pt) | 2018-07-17 |
AU2016254859A1 (en) | 2017-11-30 |
CN107532114A (zh) | 2018-01-02 |
EP3289055B1 (en) | 2019-02-20 |
JP2018510960A (ja) | 2018-04-19 |
BR112017022577B1 (pt) | 2022-03-15 |
EP3289055A1 (en) | 2018-03-07 |
WO2016175931A1 (en) | 2016-11-03 |
CN107532114B (zh) | 2020-09-04 |
US20180066209A1 (en) | 2018-03-08 |
US10351800B2 (en) | 2019-07-16 |
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