JP5065011B2 - フッ素化ポリエーテルポリアミンおよびフッ素化ポリエーテルポリアミンを製造する方法 - Google Patents
フッ素化ポリエーテルポリアミンおよびフッ素化ポリエーテルポリアミンを製造する方法 Download PDFInfo
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- JP5065011B2 JP5065011B2 JP2007511370A JP2007511370A JP5065011B2 JP 5065011 B2 JP5065011 B2 JP 5065011B2 JP 2007511370 A JP2007511370 A JP 2007511370A JP 2007511370 A JP2007511370 A JP 2007511370A JP 5065011 B2 JP5065011 B2 JP 5065011B2
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- Prior art keywords
- carbon atoms
- group
- independently
- independently represents
- polyamine
- 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.)
- Expired - Fee Related
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- 229920000570 polyether Polymers 0.000 title claims abstract description 31
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 25
- 229920000768 polyamine Polymers 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000000203 mixture Substances 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 72
- 150000001408 amides Chemical class 0.000 claims description 33
- 125000002947 alkylene group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 14
- 239000006185 dispersion Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 16
- 239000007859 condensation product Substances 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 238000004566 IR spectroscopy Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- -1 methoxy, ethoxy, isopropoxy Chemical group 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 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 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000006242 amine protecting group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005406 washing 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/024—Polyamines containing oxygen in the form of ether bonds in the main chain
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyamides (AREA)
- Polyethers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/840,969 US7288619B2 (en) | 2004-05-07 | 2004-05-07 | Fluorinated polyether polyamine and method of making the same |
| US10/840,969 | 2004-05-07 | ||
| PCT/US2005/010907 WO2005113644A1 (en) | 2004-05-07 | 2005-03-31 | Fluorinated polyether polyamine and method of making the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007536395A JP2007536395A (ja) | 2007-12-13 |
| JP2007536395A5 JP2007536395A5 (https=) | 2008-05-01 |
| JP5065011B2 true JP5065011B2 (ja) | 2012-10-31 |
Family
ID=34964196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007511370A Expired - Fee Related JP5065011B2 (ja) | 2004-05-07 | 2005-03-31 | フッ素化ポリエーテルポリアミンおよびフッ素化ポリエーテルポリアミンを製造する方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7288619B2 (https=) |
| EP (1) | EP1742987B1 (https=) |
| JP (1) | JP5065011B2 (https=) |
| CN (1) | CN100532427C (https=) |
| AT (1) | ATE485330T1 (https=) |
| DE (1) | DE602005024251D1 (https=) |
| WO (1) | WO2005113644A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7342080B2 (en) * | 2004-05-07 | 2008-03-11 | 3M Innovative Properties Company | Polymerizable compositions, methods of making the same, and composite articles therefrom |
| EP2519529B1 (en) * | 2009-12-30 | 2015-10-21 | 3M Innovative Properties Company | Moisture-curable siloxane-containing and fluorocarbon-containing compounds and polymers formed therefrom |
| CN102770478B (zh) | 2009-12-30 | 2014-03-12 | 3M创新有限公司 | 具有全氟聚醚链段和多个氨基乙二酰胺基的共聚物 |
| US11492318B2 (en) | 2017-05-19 | 2022-11-08 | Etna-Tec, Ltd. | Methods for making functionalized fluorinated monomers, fluorinated monomers, and compositions for making the same |
| WO2019241186A1 (en) | 2018-06-12 | 2019-12-19 | 3M Innovative Properties Company | Fluoropolymer coating compositions comprising amine curing agents, coated substrates and related methods |
| US11866602B2 (en) | 2018-06-12 | 2024-01-09 | 3M Innovative Properties Company | Fluoropolymer compositions comprising fluorinated additives, coated substrates and methods |
| WO2021088198A1 (en) | 2019-11-04 | 2021-05-14 | 3M Innovative Properties Company | Electronic telecommunications articles comprising crosslinked fluoropolymers and methods |
| WO2021090111A1 (en) | 2019-11-04 | 2021-05-14 | 3M Innovative Properties Company | Fluoropolymer compositions comprising a curing agent with ethylenically unsaturated and electron donor groups, and substrates coated therewith |
| US20240218202A1 (en) | 2021-05-05 | 2024-07-04 | 3M Innovative Properties Company | Electronic telecommunications articles and compositions comprising fluorinated curing agents |
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| US6452038B1 (en) * | 2000-06-28 | 2002-09-17 | 3M Innovative Properties Company | Fluoroalkyloxy dispersant |
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| US6803109B2 (en) * | 2001-03-09 | 2004-10-12 | 3M Innovative Properties Company | Water-and oil-repellency imparting urethane oligomers comprising perfluoroalkyl moieties |
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| US7342080B2 (en) | 2004-05-07 | 2008-03-11 | 3M Innovative Properties Company | Polymerizable compositions, methods of making the same, and composite articles therefrom |
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2004
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- 2005-03-31 WO PCT/US2005/010907 patent/WO2005113644A1/en not_active Ceased
- 2005-03-31 DE DE602005024251T patent/DE602005024251D1/de not_active Expired - Lifetime
- 2005-03-31 EP EP05730920A patent/EP1742987B1/en not_active Expired - Lifetime
- 2005-03-31 CN CNB2005800145762A patent/CN100532427C/zh not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| DE602005024251D1 (de) | 2010-12-02 |
| JP2007536395A (ja) | 2007-12-13 |
| CN1950428A (zh) | 2007-04-18 |
| WO2005113644A1 (en) | 2005-12-01 |
| CN100532427C (zh) | 2009-08-26 |
| US20050250928A1 (en) | 2005-11-10 |
| EP1742987B1 (en) | 2010-10-20 |
| EP1742987A1 (en) | 2007-01-17 |
| ATE485330T1 (de) | 2010-11-15 |
| US7288619B2 (en) | 2007-10-30 |
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