CA2866565A1 - Amine curable epoxy resin composition - Google Patents
Amine curable epoxy resin composition Download PDFInfo
- Publication number
- CA2866565A1 CA2866565A1 CA2866565A CA2866565A CA2866565A1 CA 2866565 A1 CA2866565 A1 CA 2866565A1 CA 2866565 A CA2866565 A CA 2866565A CA 2866565 A CA2866565 A CA 2866565A CA 2866565 A1 CA2866565 A1 CA 2866565A1
- Authority
- CA
- Canada
- Prior art keywords
- amine
- epoxy resin
- based composition
- curable epoxy
- amine based
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 124
- 150000001412 amines Chemical class 0.000 title claims abstract description 87
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 42
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 42
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims abstract description 29
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims abstract description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000004848 polyfunctional curative Substances 0.000 claims abstract description 15
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims abstract description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 12
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 phenyl ester Chemical class 0.000 claims abstract description 10
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002270 dispersing agent Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 7
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 238000009736 wetting Methods 0.000 claims abstract description 7
- 239000000080 wetting agent Substances 0.000 claims abstract description 7
- 239000013530 defoamer Substances 0.000 claims abstract description 6
- HVRVCYZDRAHSHG-UHFFFAOYSA-N 1,3-bis[[3-(aminomethyl)phenyl]methylamino]propan-2-ol Chemical compound NCC1=CC=CC(CNCC(O)CNCC=2C=C(CN)C=CC=2)=C1 HVRVCYZDRAHSHG-UHFFFAOYSA-N 0.000 claims abstract 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 27
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 15
- 239000004576 sand Substances 0.000 claims description 9
- 239000000377 silicon dioxide Substances 0.000 claims description 9
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- KKBYAQXJYMWYBR-UHFFFAOYSA-N phenyl dodecane-1-sulfonate Chemical group CCCCCCCCCCCCS(=O)(=O)OC1=CC=CC=C1 KKBYAQXJYMWYBR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 229920003319 Araldite® Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 238000007790 scraping Methods 0.000 description 2
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5033—Amines aromatic
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/48—Macromolecular compounds
- C04B41/4853—Epoxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/223—Di-epoxy compounds together with monoepoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/226—Mixtures of di-epoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2012/072130 | 2012-03-09 | ||
| CN2012072130 | 2012-03-09 | ||
| PCT/EP2013/053762 WO2013131776A1 (en) | 2012-03-09 | 2013-02-26 | Amine curable epoxy resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2866565A1 true CA2866565A1 (en) | 2013-09-12 |
Family
ID=47790189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2866565A Abandoned CA2866565A1 (en) | 2012-03-09 | 2013-02-26 | Amine curable epoxy resin composition |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20150025178A1 (https=) |
| EP (1) | EP2822985B1 (https=) |
| JP (1) | JP2015511983A (https=) |
| AU (1) | AU2013229697B2 (https=) |
| BR (1) | BR112014019983A8 (https=) |
| CA (1) | CA2866565A1 (https=) |
| RU (1) | RU2014140671A (https=) |
| WO (1) | WO2013131776A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3546494B1 (en) * | 2016-11-24 | 2021-11-24 | Mitsubishi Gas Chemical Company, Inc. | Curing agent for water-based epoxy resin, water-based epoxy resin composition, and cured product thereof |
| JP7177580B2 (ja) * | 2016-11-24 | 2022-11-24 | 三菱瓦斯化学株式会社 | エポキシ樹脂硬化剤、エポキシ樹脂組成物及びその硬化物 |
| JP6829417B2 (ja) * | 2017-03-01 | 2021-02-10 | 住友大阪セメント株式会社 | コンクリート構造物床版補修用プライマー及び当該プライマーを用いたコンクリート構造物床版補修工法 |
| JP7276331B2 (ja) * | 2018-05-24 | 2023-05-18 | 三菱瓦斯化学株式会社 | 水系エポキシ樹脂用硬化剤、水系エポキシ樹脂組成物及びその硬化物 |
| EP3889200B1 (en) | 2018-11-26 | 2023-09-20 | Mitsubishi Gas Chemical Company, Inc. | Aqueous epoxy resin composition and cured product of same |
| DE112019007547T5 (de) * | 2019-07-16 | 2022-03-31 | Mitsubishi Electric Corporation | Isolierlackzusammensetzung, spule für eine rotierende maschine sowie rotierende maschine |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58152845A (ja) * | 1982-03-08 | 1983-09-10 | Mitsubishi Gas Chem Co Inc | 新規なポリアミン |
| JPS58204022A (ja) * | 1982-05-25 | 1983-11-28 | Mitsubishi Gas Chem Co Inc | エポキシ樹脂硬化剤 |
| NL8303268A (nl) * | 1983-09-23 | 1985-04-16 | Philips Nv | Werkwijze ter vervaardiging van een halfgeleiderinrichting en halfgeleiderinrichting vervaardigd door toepassing van een dergelijke werkwijze. |
| DE19504528A1 (de) * | 1994-02-17 | 1995-08-24 | Sandoz Ag | Mit Aminen aushärtbare Kompositionen |
| US5798398A (en) * | 1996-10-18 | 1998-08-25 | Henkel Corporation | Epoxy curing agent comprising a metaxylylenediamine-epichlorohydrin adduct |
| DE19726263C2 (de) * | 1997-06-20 | 2003-02-27 | Reaku Hobein Gmbh | Zweikomponenten-Beschichtungsmittel auf Epoxidharz-Basis für zementgebundene Untergründe sowie dessen Verwendung |
| TW539661B (en) * | 2000-09-12 | 2003-07-01 | Mitsubishi Gas Chemical Co | Amino compound and process for producing the same |
| EP1375554B1 (en) * | 2002-06-18 | 2007-09-19 | Mitsubishi Gas Chemical Company, Inc. | Amino composition and process for producing the same |
| JP2004018711A (ja) * | 2002-06-18 | 2004-01-22 | Mitsubishi Gas Chem Co Inc | エポキシ樹脂組成物のポットライフ調節方法 |
| JP4449350B2 (ja) * | 2002-06-18 | 2010-04-14 | 三菱瓦斯化学株式会社 | アミノ組成物およびその製造方法 |
| JP2004059643A (ja) * | 2002-07-25 | 2004-02-26 | Mitsubishi Gas Chem Co Inc | プリプレグ及び積層板 |
| JP4310614B2 (ja) * | 2002-08-07 | 2009-08-12 | 三菱瓦斯化学株式会社 | ポリアミノ系エポキシ樹脂硬化剤およびエポキシ樹脂組成物 |
| JP2008503627A (ja) * | 2004-06-21 | 2008-02-07 | ハンツマン・アドヴァンスト・マテリアルズ・（スイッツランド）・ゲーエムベーハー | エポキシ樹脂用硬化剤 |
| KR20100059818A (ko) * | 2007-07-26 | 2010-06-04 | 헨켈 코포레이션 | 경화성 에폭시 수지계 접착제 조성물 |
| CN101671515B (zh) * | 2009-09-01 | 2011-12-14 | 中国人民解放军海军后勤技术装备研究所 | 混凝土结构钢筋防腐涂料及其制备方法 |
| JP2011219654A (ja) * | 2010-04-12 | 2011-11-04 | Kaneka Corp | 硬化性組成物 |
| US20120171423A1 (en) * | 2011-12-23 | 2012-07-05 | Haines Jay A | Surface coating compositions and methods |
-
2013
- 2013-02-26 JP JP2014560304A patent/JP2015511983A/ja active Pending
- 2013-02-26 CA CA2866565A patent/CA2866565A1/en not_active Abandoned
- 2013-02-26 WO PCT/EP2013/053762 patent/WO2013131776A1/en not_active Ceased
- 2013-02-26 BR BR112014019983A patent/BR112014019983A8/pt not_active IP Right Cessation
- 2013-02-26 AU AU2013229697A patent/AU2013229697B2/en not_active Ceased
- 2013-02-26 US US14/383,189 patent/US20150025178A1/en not_active Abandoned
- 2013-02-26 EP EP13707342.5A patent/EP2822985B1/en not_active Not-in-force
- 2013-02-26 RU RU2014140671A patent/RU2014140671A/ru not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2014140671A (ru) | 2016-04-27 |
| US20150025178A1 (en) | 2015-01-22 |
| AU2013229697A1 (en) | 2014-09-25 |
| JP2015511983A (ja) | 2015-04-23 |
| BR112014019983A2 (https=) | 2017-06-20 |
| BR112014019983A8 (pt) | 2017-07-11 |
| WO2013131776A1 (en) | 2013-09-12 |
| EP2822985B1 (en) | 2016-11-30 |
| EP2822985A1 (en) | 2015-01-14 |
| AU2013229697B2 (en) | 2015-12-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20190226 |