KR102526826B1 - 함불소 에테르 조성물, 코팅액 및 물품 - Google Patents
함불소 에테르 조성물, 코팅액 및 물품 Download PDFInfo
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- KR102526826B1 KR102526826B1 KR1020197022850A KR20197022850A KR102526826B1 KR 102526826 B1 KR102526826 B1 KR 102526826B1 KR 1020197022850 A KR1020197022850 A KR 1020197022850A KR 20197022850 A KR20197022850 A KR 20197022850A KR 102526826 B1 KR102526826 B1 KR 102526826B1
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- fluorine
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- containing ether
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- 238000010896 thin film analysis Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
- C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
- C09D171/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Combustion & Propulsion (AREA)
- Paints Or Removers (AREA)
- Polyethers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
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| JPJP-P-2017-050558 | 2017-03-15 | ||
| JP2017050558 | 2017-03-15 | ||
| PCT/JP2018/007781 WO2018168497A1 (ja) | 2017-03-15 | 2018-03-01 | 含フッ素エーテル組成物、コーティング液および物品 |
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|---|---|
| KR20190125297A KR20190125297A (ko) | 2019-11-06 |
| KR102526826B1 true KR102526826B1 (ko) | 2023-04-27 |
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| KR (1) | KR102526826B1 (enExample) |
| CN (1) | CN110402271B (enExample) |
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| WO (1) | WO2018168497A1 (enExample) |
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| WO2018151055A1 (ja) * | 2017-02-14 | 2018-08-23 | Ａｇｃ株式会社 | 含フッ素エーテル組成物、コーティング液および物品 |
| KR102526826B1 (ko) * | 2017-03-15 | 2023-04-27 | 에이지씨 가부시키가이샤 | 함불소 에테르 조성물, 코팅액 및 물품 |
| EP3705529A4 (en) * | 2017-10-31 | 2021-09-01 | Daikin Industries, Ltd. | CURING COMPOSITION |
| WO2019088126A1 (ja) * | 2017-10-31 | 2019-05-09 | ダイキン工業株式会社 | 硬化性組成物 |
| JP7007599B2 (ja) * | 2017-10-31 | 2022-01-24 | ダイキン工業株式会社 | 硬化性組成物 |
| JP7257268B2 (ja) * | 2019-06-11 | 2023-04-13 | 日本ペイント・サーフケミカルズ株式会社 | 親水化処理剤および親水皮膜の形成方法 |
| CN114206986B (zh) | 2019-08-02 | 2024-07-26 | 大金工业株式会社 | 表面处理剂 |
| KR20220151662A (ko) * | 2020-03-09 | 2022-11-15 | 에이지씨 가부시키가이샤 | 함불소 에테르 화합물 및 그 제조 방법, 화합물 및 그 제조 방법, 함불소 에테르 조성물, 코팅액, 그리고 물품 및 그 제조 방법 |
| JP7750291B2 (ja) | 2021-08-05 | 2025-10-07 | 信越化学工業株式会社 | 撥水撥油表面層を有する物品 |
| CN117794741A (zh) | 2021-08-05 | 2024-03-29 | 信越化学工业株式会社 | 具有拒水拒油表面层的物品 |
| KR20240095305A (ko) * | 2021-11-12 | 2024-06-25 | 에이지씨 가부시키가이샤 | 조성물, 표면 처리제, 코팅액, 물품, 및 물품의 제조 방법 |
| JPWO2023132276A1 (enExample) * | 2022-01-05 | 2023-07-13 | ||
| WO2023204026A1 (ja) | 2022-04-19 | 2023-10-26 | 信越化学工業株式会社 | 撥水撥油物品の製造方法及び撥水撥油物品における水及び油の除去性改善方法 |
| JPWO2024111491A1 (enExample) * | 2022-11-21 | 2024-05-30 | ||
| WO2024210068A1 (ja) * | 2023-04-06 | 2024-10-10 | Ａｇｃ株式会社 | 物品及び物品の製造方法 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000144121A (ja) | 1998-11-09 | 2000-05-26 | Ikuo Narisawa | 表面処理剤、これを用いた水滴滑落性基材及びその製造方法 |
| JP2006206765A (ja) | 2005-01-28 | 2006-08-10 | Asahi Glass Co Ltd | 撥水性組成物、撥水層を有する基材、その製造方法および輸送機器用物品 |
| JP2014218639A (ja) | 2012-11-05 | 2014-11-20 | ダイキン工業株式会社 | パーフルオロ（ポリ）エーテル基含有シラン化合物 |
| JP2015221888A (ja) | 2014-04-30 | 2015-12-10 | ダイキン工業株式会社 | パーフルオロ（ポリ）エーテル基含有シラン化合物 |
| JP2016017176A (ja) * | 2014-07-11 | 2016-02-01 | ダイキン工業株式会社 | 表面処理剤 |
| CN109890896B (zh) | 2016-10-31 | 2021-09-17 | Ａｇｃ株式会社 | 含氟醚组合物、涂布液以及物品 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009008380A1 (ja) * | 2007-07-06 | 2009-01-15 | Asahi Glass Company, Limited | 表面処理剤、物品、および新規含フッ素エーテル化合物 |
| WO2013146110A1 (ja) | 2012-03-29 | 2013-10-03 | ダイキン工業株式会社 | 表面処理組成物およびそれを使用して得られる物品 |
| WO2015087902A1 (ja) * | 2013-12-13 | 2015-06-18 | 旭硝子株式会社 | 含フッ素エーテル組成物、その製造方法、コーティング液、表面処理層を有する基材およびその製造方法 |
| EP3085749B1 (en) * | 2015-04-20 | 2017-06-28 | Shin-Etsu Chemical Co., Ltd. | Fluoropolyether-containing polymer-modified silane, surface treating agent, and treated article |
| CN107922445B (zh) * | 2015-09-01 | 2020-07-28 | Ａｇｃ株式会社 | 含氟醚化合物、含氟醚组合物、涂布液和物品 |
| KR102526826B1 (ko) * | 2017-03-15 | 2023-04-27 | 에이지씨 가부시키가이샤 | 함불소 에테르 조성물, 코팅액 및 물품 |
-
2018
- 2018-03-01 KR KR1020197022850A patent/KR102526826B1/ko active Active
- 2018-03-01 JP JP2019505865A patent/JP6617853B2/ja active Active
- 2018-03-01 WO PCT/JP2018/007781 patent/WO2018168497A1/ja not_active Ceased
- 2018-03-01 CN CN201880017366.6A patent/CN110402271B/zh active Active
- 2018-03-06 TW TW107107431A patent/TWI831741B/zh active
- 2018-03-06 TW TW113101068A patent/TWI875427B/zh active
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2019
- 2019-11-08 JP JP2019203296A patent/JP6969599B2/ja active Active
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2021
- 2021-10-12 JP JP2021167508A patent/JP7243783B2/ja active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000144121A (ja) | 1998-11-09 | 2000-05-26 | Ikuo Narisawa | 表面処理剤、これを用いた水滴滑落性基材及びその製造方法 |
| JP2006206765A (ja) | 2005-01-28 | 2006-08-10 | Asahi Glass Co Ltd | 撥水性組成物、撥水層を有する基材、その製造方法および輸送機器用物品 |
| JP2014218639A (ja) | 2012-11-05 | 2014-11-20 | ダイキン工業株式会社 | パーフルオロ（ポリ）エーテル基含有シラン化合物 |
| JP5761305B2 (ja) | 2012-11-05 | 2015-08-12 | ダイキン工業株式会社 | パーフルオロ（ポリ）エーテル基含有シラン化合物 |
| JP2015221888A (ja) | 2014-04-30 | 2015-12-10 | ダイキン工業株式会社 | パーフルオロ（ポリ）エーテル基含有シラン化合物 |
| JP2016017176A (ja) * | 2014-07-11 | 2016-02-01 | ダイキン工業株式会社 | 表面処理剤 |
| CN109890896B (zh) | 2016-10-31 | 2021-09-17 | Ａｇｃ株式会社 | 含氟醚组合物、涂布液以及物品 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW202419570A (zh) | 2024-05-16 |
| JP2020029565A (ja) | 2020-02-27 |
| CN110402271A (zh) | 2019-11-01 |
| JP7243783B2 (ja) | 2023-03-22 |
| JP6617853B2 (ja) | 2019-12-11 |
| CN110402271B (zh) | 2023-04-14 |
| TWI875427B (zh) | 2025-03-01 |
| JP6969599B2 (ja) | 2021-11-24 |
| JP2022001653A (ja) | 2022-01-06 |
| TW201839051A (zh) | 2018-11-01 |
| JPWO2018168497A1 (ja) | 2020-01-16 |
| TWI831741B (zh) | 2024-02-11 |
| WO2018168497A1 (ja) | 2018-09-20 |
| KR20190125297A (ko) | 2019-11-06 |
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