CN113597451A - 含有环氧化聚丁二烯的氟橡胶组合物 - Google Patents
含有环氧化聚丁二烯的氟橡胶组合物 Download PDFInfo
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- CN113597451A CN113597451A CN202080022046.7A CN202080022046A CN113597451A CN 113597451 A CN113597451 A CN 113597451A CN 202080022046 A CN202080022046 A CN 202080022046A CN 113597451 A CN113597451 A CN 113597451A
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- Prior art keywords
- fluororubber composition
- epoxidized polybutadiene
- fluororubber
- repeating units
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- 229920001973 fluoroelastomer Polymers 0.000 title claims abstract description 58
- 229920002857 polybutadiene Polymers 0.000 title claims abstract description 47
- 239000005062 Polybutadiene Substances 0.000 title claims abstract description 45
- 239000000203 mixture Substances 0.000 title claims abstract description 40
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- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
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- 238000004073 vulcanization Methods 0.000 description 6
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- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical compound [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
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- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
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- OMZSGWSJDCOLKM-UHFFFAOYSA-N copper(II) sulfide Chemical compound [S-2].[Cu+2] OMZSGWSJDCOLKM-UHFFFAOYSA-N 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
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- 238000007654 immersion Methods 0.000 description 1
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
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- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
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- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 1
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- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
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- 238000010998 test method Methods 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
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- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
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- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
-
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Abstract
本发明的课题在于提供耐水性、耐酸性优异、安全性高的新型氟橡胶组合物。本发明的氟橡胶组合物中，相对于氟橡胶100重量份，含有环氧化聚丁二烯0.1～50重量份。作为氟橡胶，可以举出偏氟乙烯－六氟丙烯共聚物(FKM)、四氟乙烯－丙烯系共聚物(FEPM)、四氟乙烯－全氟烷基乙烯基醚系共聚物(FFKM)等。本发明的氟橡胶组合物还可以含有硫化剂等。
Description
技术领域
本发明涉及含有环氧化聚丁二烯的氟橡胶组合物。
本申请主张基于2019年3月26日申请的日本专利申请第2019－59141号的优先权，将其内容引用在此。
背景技术
氟橡胶的耐热性、耐化学药品性、耐油性、耐候性等优异，因此被用于汽车部件材料、电子部件材料等各种用途中。在对氟橡胶进行硫化时，为了中和所产生的氢氟酸，大多配合了吸酸剂。
在专利文献1中，提出了将液态聚丁二烯的环氧化物作为有效成分的含卤素聚合物用热稳定剂。此外，专利文献2中提出了一种氯磺化聚烯烃组合物，其中，相对于100重量份氯磺化聚烯烃，含有脂肪族缩水甘油醚、环氧化聚丁二烯或环氧化油3～50重量份。
现有技术文献：
专利文献1：日本特开昭57－158260号公报
专利文献2：日本特开2017－88872号公报
发明内容
发明所要解决的课题
一直以来，作为卤化橡胶的吸酸剂使用的一氧化铅被担忧具有毒性。因此，近年来，将氧化镁等作为吸酸剂使用。但是，若在氟橡胶中配合氧化镁，则存在耐水性、耐酸性变差的问题。因此，期望耐水性、耐酸性优异、安全性高的新型氟橡胶组合物。
用于解决课题的手段
本发明人等为了解决上述课题反复进行了深入研究，结果发现了一种相对于氟橡胶100重量份，含有环氧化聚丁二烯0.1～50重量份的氟橡胶组合物，从而完成了本发明。
即，本发明涉及以下的发明。
(1)一种氟橡胶组合物，其中，相对于氟橡胶100重量份，含有环氧化聚丁二烯0.1～50重量份。
(2)根据(1)所述的氟橡胶组合物，其中，氟橡胶为选自偏氟乙烯－六氟丙烯共聚物(FKM)、四氟乙烯－丙烯系共聚物(FEPM)、四氟乙烯－全氟烷基乙烯基醚系共聚物(FFKM)中的至少1种。
(3)根据(1)或(2)所述的氟橡胶组合物，其中，还包含硫化剂。
(4)根据(1)～(3)中任一项所述的氟橡胶组合物，其中，环氧化聚丁二烯是由式(I)、式(II)、式(III)和式(IV)所示的重复单元构成的环氧化聚丁二烯。
[化1]
(5)根据(4)所述的氟橡胶组合物，其中，环氧化聚丁二烯中的全部重复单元中，式(I)和式(II)所示的重复单元的合计比例为75～99摩尔％。
(6)根据(4)或(5)所述的氟橡胶组合物，其中，环氧化聚丁二烯中的全部重复单元中，式(I)和式(III)所示的重复单元的合计比例为1～90摩尔％。
(7)根据(6)所述的氟橡胶组合物，其中，环氧化聚丁二烯中的全部重复单元中，式(I)和式(III)所示的重复单元的合计比例为1～40摩尔％。
(8)根据(1)～(7)中任一项所述的氟橡胶组合物，其中，环氧化聚丁二烯的数均分子量(Mn)为500～10,000。
(9)一种成型物，其是将(1)～(8)中任一项所述的氟橡胶组合物成型而成的。
发明效果
本发明的氟橡胶组合物的耐水性、耐酸性优异，安全性也高。
具体实施方式
本发明的氟橡胶组合物含有氟橡胶和环氧化聚丁二烯。氟橡胶组合物中的环氧化聚丁二烯的含量没有特别限定，相对于氟橡胶100重量份，可以将环氧化聚丁二烯的含量设为0.1～50重量份、0.1～40重量份、0.1～30重量份、0.1～20重量份、0.1～10重量份、或1～10重量份。在氟橡胶组合物中，环氧化聚丁二烯作为吸酸剂发挥功能，但也可以发挥其他功能。
本发明的氟橡胶组合物中所含的氟橡胶只要是分子中具有氟原子的橡胶就没有特别限定。作为氟橡胶，具体而言，可以举出偏氟乙烯－六氟丙烯共聚物(FKM)、四氟乙烯－丙烯系共聚物(FEPM)、四氟乙烯－全氟烷基乙烯基醚系共聚物(FFKM)等。这些氟橡胶可以单独使用1种或组合使用2种以上。作为氟橡胶，可以使用市售品。
本发明的氟橡胶组合物中所含的环氧化聚丁二烯只要是对聚丁二烯进行环氧改性而得到的物质就没有特别限定。环氧化聚丁二烯可以是将高分子链末端进行环氧改性而得到的物质，也可以是将主链的双键进行环氧化而得到的物质。环氧化聚丁二烯中的环氧基通过与氟化氢反应，由此作为吸酸剂发挥功能。
作为主链的双键被环氧化而成的环氧化聚丁二烯，可以举出包含式(I)、式(II)、式(III)及式(IV)所示的重复单元的环氧化聚丁二烯。环氧化聚丁二烯中的全部重复单元中，式(I)及式(II)所表示的重复单元的合计比例优选为75～99摩尔％。此外，环氧化聚丁二烯中的全部重复单元中，式(I)和式(III)所示的重复单元的合计比例可以选择1～90摩尔％、1～80摩尔％、1～70摩尔％、1～60摩尔％、1～50摩尔％、1～40摩尔％、5～40摩尔％、10～40摩尔％等范围。
环氧化聚丁二烯的分子量没有特别限定，数均分子量(Mn)优选为500～10,000。需要说明的是，重均分子量及数均分子量是基于标准聚苯乙烯的分子量对利用以四氢呋喃为溶剂的凝胶渗透色谱(GPC)测定的数据进行换算而得到的值。
作为环氧化聚丁二烯，可以使用市售品。作为市售品的环氧化聚丁二烯，可以举出NISSO－PB(注册商标)JP－100(日本曹达株式会社制)、NISSO－PB(注册商标)JP－200(日本曹达株式会社制)、Epolead(注册商标)PB3600(株式会社Daicel制)、4700(株式会社Daicel制)、ADEKA Sizer(注册商标)BF－1000(ADEKA制)、Ricon657(Cray Valley公司制)等。这些环氧化聚丁二烯可以单独使用1种或组合使用2种以上。上述环氧化聚丁二烯中，优选NISSO－PB(注册商标)JP－100(日本曹达株式会社制)、NISSO－PB(注册商标)JP－200(日本曹达株式会社制)。
作为制造本发明的氟橡胶组合物的方法，没有特别限定。例如，可以举出在氟橡胶中添加环氧化聚丁二烯后，利用混炼机进行混炼的方法。
本发明的氟橡胶组合物可以含有氟橡胶和环氧化聚丁二烯以外的其它成分。作为其他成分，可以举出增塑剂、填充剂、强化剂、抗老化剂、润滑剂、加工助剂、硫化剂、硫化促进剂等。
作为增塑剂，可以举出邻苯二甲酸衍生物、磷酸衍生物、癸二酸衍生物、季戊四醇、低分子量氟橡胶等。更具体而言，可以举出邻苯二甲酸二烷基酯、癸二酸二烷基酯、季戊四醇等。
作为填充剂，可以举出氧化钛、氧化铝、氧化锌等金属氧化物；氢氧化镁、氢氧化铝等金属氢氧化物；碳酸镁、碳酸铝、碳酸钙、碳酸钡等碳酸盐；硅酸镁、硅酸钙、硅酸铝等硅酸盐；硫酸铝、硫酸钙、硫酸钡等硫酸盐；二硫化钼、硫化铁、硫化铜等金属硫化物；硅藻土、石棉、重拓扑(硫化锌/硫化钡)、石墨、碳黑、氟化碳、氟化钙、焦碳、石英微粉、锌白、滑石、云母粉末、钙硅石、碳纤维、芳族聚酰胺纤维、各种晶须、玻璃纤维、有机强化剂、有机填充剂、聚四氟乙烯等含氟热塑性树脂；云母、二氧化硅、硅藻土、粘土等。
作为强化剂，可以举出碳黑、高岭土粘土、滑石、云母、碳酸钙、二氧化硅等。
作为抗老化剂，可以举出芳香族仲胺系的抗老化剂、胺·酮系的抗老化剂、巯基苯并咪唑系的抗老化剂、双酚类的抗老化剂、单酚类的抗老化剂、硫代双酚系的抗老化剂、氢醌系的抗老化剂、镍盐系的抗老化剂、硫代尿素系的抗老化剂、硫醚系的抗老化剂、磷系的抗老化剂。
作为润滑剂，可以举出聚甘油脂肪酸酯、磷酸酯、脂肪酸酯、脂肪酸酰胺、高级脂肪酸等。
作为加工助剂，可以举出硬脂酸、油酸、棕榈酸、月桂酸等高级脂肪酸、硬脂酸钠、硬脂酸锌等高级脂肪酸盐、脂肪族醇、乙二醇、甘油、二乙二醇等聚二醇、硬脂基胺等脂肪族胺、硅酮系油、硅酮系聚合物、低分子量聚乙烯、磷酸酯类、松香、(卤化)二烷基胺、表面活性剂、砜化合物、氟系助剂、有机胺化合物等。
作为硫化剂，可以举出2,2－双(4－羟基苯基)丙烷[双酚A]、2,2－双(4－羟基苯基)六氟丙烷、2,2－双(4－羟基苯基)全氟丙烷[双酚AF]、对苯二酚、邻苯二酚、间苯二酚、4,4’－二羟基联苯、4,4’－二羟基二苯基甲烷、4,4’－二羟基二苯砜、2,2－双(4－羟基苯基)丁烷等多羟基芳香族化合物或它们的碱金属盐或碱土金属盐等多元醇系硫化剂。
作为硫化促进剂，可以举出氢氧化钙、N－8－苄基－1,8－二氮杂双环[5.4.0]十一碳－7－烯氯化铵等季铵盐、季鏻盐等。
本发明的氟橡胶组合物可以通过一般的氟橡胶的成型方法进行成型。
实施例
以下，使用实施例对本发明进行更详细的说明，但本发明并不限定于实施例的范围。
将实施例及比较例中使用的物质示于表1。
[表1]
*1制造例1中制造的环氧化聚丁二烯
制造例1
参考远藤刚编、高分子的合成(上)、第一版、讲谈社、2010，以碱金属作为引发剂合成1,4－PB(1,4－聚丁二烯)。Mn约为2000、1,2－乙烯基率约为20％。使用日本特开昭51－36448号公报所示的方法将得到的1,4－PB环氧化，得到环氧当量约为230的环氧化1,4－PB。
实施例1
用辊机将FKM 100重量份、环氧化聚丁二烯A3重量份、氢氧化钙6重量份、碳黑20重量份混炼，得到氟橡胶组合物。将得到的氟橡胶组合物在170℃下加压硫化12分钟，进一步在230℃、24小时烘箱中加热，由此进行二次硫化，得到硫化物。对于得到的硫化物，实施拉伸试验、撕裂试验、耐水性试验、耐氯水性试验、耐酸性试验。将这些结果示于表2。
实施例2
使用环氧化聚丁二烯B 3重量份代替环氧化聚丁二烯A，除此以外，与实施例1同样地得到硫化物。对于得到的硫化物，实施拉伸试验、撕裂试验、耐水性试验、耐氯水性试验、耐酸性试验。将这些结果示于表2。
对比例1
使用氧化镁3重量份代替环氧化聚丁二烯A，在170℃下加压硫化15分钟，除此以外，与实施例1同样地得到硫化物。对于得到的硫化物，实施拉伸试验、撕裂试验、耐水性试验、耐氯水性试验、耐酸性试验。将这些结果示于表3。
对比例2
使用一氧化铅5重量份代替环氧化聚丁二烯A，在170℃下加压硫化15分钟，除此以外，与实施例1同样地得到硫化物。对于得到的硫化物，实施拉伸试验、撕裂试验、耐水性试验、耐氯水性试验、耐酸性试验。将这些结果示于表3。
试验方法
“拉伸试验”
依据JISK6251：2010“硫化橡胶及热塑性橡胶－拉伸特性的求法”，测定拉伸强度和切断时伸长率。
“撕裂试验”
依据JISK6252：2007“硫化橡胶及热塑性橡胶－撕裂强度的求法”，测定撕裂强度。
“耐水性和耐酸性试验”
依据JISK6258：2010“硫化橡胶及热塑性橡胶－耐液性的求法”，测定在水、600ppm氯水、10％硝酸、20％盐酸中浸渍80℃、168小时后的体积变化率。
[表2]
[表3]
Claims (9)
1.一种氟橡胶组合物，其特征在于，
相对于氟橡胶100重量份，含有环氧化聚丁二烯0.1～50重量份。
2.如权利要求1所述的氟橡胶组合物，其特征在于，
氟橡胶为选自偏氟乙烯－六氟丙烯共聚物(FKM)、四氟乙烯－丙烯系共聚物(FEPM)、四氟乙烯－全氟烷基乙烯基醚系共聚物(FFKM)中的至少1种。
3.如权利要求1或2所述的氟橡胶组合物，其特征在于，
其中进一步含有硫化剂。
4.如权利要求1～3中任一项所述的氟橡胶组合物，其特征在于，
环氧化聚丁二烯是包含式(I)、式(II)、式(III)和式(IV)所示的重复单元的环氧化聚丁二烯，
5.如权利要求4所述的氟橡胶组合物，其特征在于，
环氧化聚丁二烯中的全部重复单元中，式(I)和式(II)所示的重复单元的合计比例为75～99摩尔％。
6.如权利要求4或5所述的氟橡胶组合物，其特征在于，
环氧化聚丁二烯中的全部重复单元中，式(I)和式(III)所示的重复单元的合计比例为1～90摩尔％。
7.如权利要求6所述的氟橡胶组合物，其特征在于，
环氧化聚丁二烯中的全部重复单元中，式(I)和式(III)所示的重复单元的合计比例为1～40摩尔％。
8.如权利要求1～7中任一项所述的氟橡胶组合物，其特征在于，
环氧化聚丁二烯的数均分子量(Mn)为500～10,000。
9.一种成型物，其特征在于，
其是将权利要求1～8中任一项所述的氟橡胶组合物成型而成的。
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| PCT/JP2020/011987 WO2020196158A1 (ja) | 2019-03-26 | 2020-03-18 | エポキシ化ポリブタジエンを含有するフッ素ゴム組成物 |
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| JPWO2020196158A1 (zh) | 2020-10-01 |
| EP3950826A1 (en) | 2022-02-09 |
| KR20210130759A (ko) | 2021-11-01 |
| EP3950826A4 (en) | 2022-12-28 |
| TW202039673A (zh) | 2020-11-01 |
| US20220162438A1 (en) | 2022-05-26 |
| CA3134255C (en) | 2023-08-29 |
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| JP7241167B2 (ja) | 2023-03-16 |
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