CN112020520B - 具有极性基的烯丙基单体共聚物的制造方法 - Google Patents
具有极性基的烯丙基单体共聚物的制造方法 Download PDFInfo
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- CN112020520B CN112020520B CN201980027307.1A CN201980027307A CN112020520B CN 112020520 B CN112020520 B CN 112020520B CN 201980027307 A CN201980027307 A CN 201980027307A CN 112020520 B CN112020520 B CN 112020520B
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- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical compound CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/02—Ethene
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- 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
- C08F218/00—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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/02—Esters of monocarboxylic acids
- C08F218/04—Vinyl esters
- C08F218/10—Vinyl esters of monocarboxylic acids containing three or more carbon atoms
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- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/52—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from boron, aluminium, gallium, indium, thallium or rare earths
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/70—Iron group metals, platinum group metals or compounds thereof
- C08F4/7001—Iron group metals, platinum group metals or compounds thereof the metallic compound containing a multidentate ligand, i.e. a ligand capable of donating two or more pairs of electrons to form a coordinate or ionic bond
- C08F4/7039—Tridentate ligand
- C08F4/7052—Monoanionic ligand
- C08F4/7062—PNO
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- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/70—Iron group metals, platinum group metals or compounds thereof
- C08F4/7095—Cobalt, nickel or compounds thereof
- C08F4/7098—Nickel or compounds thereof
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/72—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44
- C08F4/80—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44 selected from iron group metals or platinum group metals
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- 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
- C08K5/00—Use of organic ingredients
- C08K5/0091—Complexes with metal-heteroatom-bonds
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- 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
- C08K5/00—Use of organic ingredients
- C08K5/55—Boron-containing compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/05—Cyclic compounds having at least one ring containing boron but no carbon in the ring
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- 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
- C08F2410/00—Features related to the catalyst preparation, the catalyst use or to the deactivation of the catalyst
- C08F2410/01—Additive used together with the catalyst, excluding compounds containing Al or B
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Claims (14)
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PCT/JP2019/009072 WO2019207969A1 (ja) | 2018-04-25 | 2019-03-07 | 極性基を有するアリルモノマー共重合体の製造方法 |
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Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1444606A (zh) * | 2000-05-31 | 2003-09-24 | 纳幕尔杜邦公司 | 烯烃聚合催化剂 |
JP2005505649A (ja) * | 2001-10-12 | 2005-02-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | エチレンと様々なノルボルネン誘導体との共重合体 |
CN101023107A (zh) * | 2004-09-16 | 2007-08-22 | Lg化学株式会社 | 用于聚合含有极性官能团的环烯烃的催化剂体系、使用该催化剂体系的聚合方法、通过该方法制备的烯烃聚合物以及包含该烯烃聚合物的光学各向异性膜 |
JP2011231291A (ja) * | 2010-04-30 | 2011-11-17 | Mitsui Chemicals Inc | 非極性−極性オレフィン共重合体の製造方法 |
CN102498137A (zh) * | 2009-08-28 | 2012-06-13 | 国立大学法人东京大学 | 制备含极性基团的烯丙基单体的共聚物的方法 |
WO2013168626A1 (ja) * | 2012-05-11 | 2013-11-14 | 国立大学法人東京大学 | ポリオレフィン類合成用触媒 |
CN104936995A (zh) * | 2013-01-23 | 2015-09-23 | 国立大学法人东京大学 | 制备含极性基团烯烃的聚合物的方法 |
CN107075004A (zh) * | 2014-10-28 | 2017-08-18 | 国立大学法人东京大学 | 含极性基的烯烃系聚合物的制造方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW541318B (en) * | 2000-07-04 | 2003-07-11 | Mitsui Chemicals Inc | Process for producing polar olefin copolymer and polar olefin copolymer obtained thereby |
US8889805B2 (en) | 2010-08-31 | 2014-11-18 | Showa Denko K.K. | Carboxylate metal complex and catalyst for olefin polymerization |
JP6017407B2 (ja) * | 2013-05-13 | 2016-11-02 | 国立大学法人 東京大学 | 重合体及び重合体の製造方法 |
WO2015200849A2 (en) * | 2014-06-27 | 2015-12-30 | The Trustees Of Princeton University | Transition metal catalysts for olefin polymerization |
CN111386288B (zh) * | 2017-11-09 | 2022-11-01 | 国立大学法人东京大学 | 烯烃聚合用催化剂及含有极性基的烯烃系聚合物的制造方法 |
JP7158688B2 (ja) * | 2018-02-20 | 2022-10-24 | 国立大学法人 東京大学 | 極性基含有アリルモノマー共重合体の製造方法 |
-
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Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1444606A (zh) * | 2000-05-31 | 2003-09-24 | 纳幕尔杜邦公司 | 烯烃聚合催化剂 |
JP2004502652A (ja) * | 2000-05-31 | 2004-01-29 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | オレフィン重合用触媒 |
JP2005505649A (ja) * | 2001-10-12 | 2005-02-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | エチレンと様々なノルボルネン誘導体との共重合体 |
CN101023107A (zh) * | 2004-09-16 | 2007-08-22 | Lg化学株式会社 | 用于聚合含有极性官能团的环烯烃的催化剂体系、使用该催化剂体系的聚合方法、通过该方法制备的烯烃聚合物以及包含该烯烃聚合物的光学各向异性膜 |
CN102498137A (zh) * | 2009-08-28 | 2012-06-13 | 国立大学法人东京大学 | 制备含极性基团的烯丙基单体的共聚物的方法 |
JP2011231291A (ja) * | 2010-04-30 | 2011-11-17 | Mitsui Chemicals Inc | 非極性−極性オレフィン共重合体の製造方法 |
WO2013168626A1 (ja) * | 2012-05-11 | 2013-11-14 | 国立大学法人東京大学 | ポリオレフィン類合成用触媒 |
CN104271585A (zh) * | 2012-05-11 | 2015-01-07 | 国立大学法人东京大学 | 聚烯烃类合成用催化剂 |
EP2848623A1 (en) * | 2012-05-11 | 2015-03-18 | The University of Tokyo | Catalyst for synthesizing polyolefins |
CN104936995A (zh) * | 2013-01-23 | 2015-09-23 | 国立大学法人东京大学 | 制备含极性基团烯烃的聚合物的方法 |
CN107075004A (zh) * | 2014-10-28 | 2017-08-18 | 国立大学法人东京大学 | 含极性基的烯烃系聚合物的制造方法 |
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US20210040251A1 (en) | 2021-02-11 |
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US11697698B2 (en) | 2023-07-11 |
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