JP5007812B2 - パーフルオロポリエーテル変性アミノシランを含む表面処理剤並びに該アミノシランの硬化被膜を有する物品 - Google Patents
パーフルオロポリエーテル変性アミノシランを含む表面処理剤並びに該アミノシランの硬化被膜を有する物品 Download PDFInfo
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- JP5007812B2 JP5007812B2 JP2007146910A JP2007146910A JP5007812B2 JP 5007812 B2 JP5007812 B2 JP 5007812B2 JP 2007146910 A JP2007146910 A JP 2007146910A JP 2007146910 A JP2007146910 A JP 2007146910A JP 5007812 B2 JP5007812 B2 JP 5007812B2
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- aminosilane
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- perfluoropolyether
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- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 title claims description 23
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- 238000000576 coating method Methods 0.000 claims description 21
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
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- 239000010702 perfluoropolyether Substances 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
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- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 2
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- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- SJBBXFLOLUTGCW-UHFFFAOYSA-N 1,3-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(F)(F)F)=C1 SJBBXFLOLUTGCW-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
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- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
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- 239000006116 anti-fingerprint coating Substances 0.000 description 1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000001680 brushing 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
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- ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
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- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
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- 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
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- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
- C09D5/1675—Polyorganosiloxane-containing compositions
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- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
- C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- 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
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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
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- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
- C08G65/33306—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group acyclic
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- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
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- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/10—Block or graft copolymers containing polysiloxane sequences
- C09D183/12—Block or graft copolymers containing polysiloxane sequences containing polyether sequences
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- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/46—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing halogen
- C08G2650/48—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing halogen containing fluorine, e.g. perfluropolyethers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T428/31609—Particulate metal or metal compound-containing
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- Polymers & Plastics (AREA)
- Geochemistry & Mineralogy (AREA)
- Paints Or Removers (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
で示されるようなフルオロアミノシラン化合物が開示されている。このフルオロアミノシラン化合物は、一般溶剤での希釈が可能なものの、1分子中の加水分解性基の割合(質量%)が少ないため、硬化までに時間を要するなど、処理被膜を形成する上で十分な性能を有しているとは言えなかった。
で表されるパーフルオロポリエーテル変性アミノシランを提案した(特許第3601580号公報:特許文献2)。このパーフルオロポリエーテル変性アミノシランは、撥水撥油性、防汚性、耐薬品性、潤滑性、離型性等に優れており、また、分子中に加水分解性シリル基を2個有しているため、従来のアミノシラン(上記式(2)で示されるフルオロアミノシラン化合物)よりも反応性が向上しており、各種基材表面にコーティングすることにより表面処理剤として利用することができる。しかし、このパーフルオロポリエーテル変性アミノシランは、分子中のフッ素含有率が高いため、基材に塗布する目的でこれを溶剤で希釈する場合、該溶剤としては溶解性の点からフッ素系溶剤に限定されてしまい、処理被膜を形成する上で十分な性能を有しているとは言えなかった。
で表される新規なパーフルオロポリエーテル変性アミノシランが、撥水撥油性、防汚性、耐薬品性、潤滑性、離型性等の各種特性を発現する上での必要最低限のフッ素を含有しており、各種基材表面にコーティングすることにより表面処理剤として利用することができ、また、アルコール等の一般溶剤での希釈が可能であるため、フッ素系溶剤での希釈の必要性がなく、更にその処理被膜は基材に強固に密着しているため、その効果を長期間持続させることができることを見出し、本発明をなすに至った。
Q1、Q2は2価の有機基であり、それぞれ同じでも異なっていてもよく、好ましくはCH2CH2CH2又はCH2CH2NHCH2CH2CH2のような炭素数1〜5の窒素原子を含んでもよいアルキレン基である。
nは2又は3のいずれかで、それぞれ同じでも異なっていてもよく、またn=2のものとn=3のものとを併用してもよい。
なお、上記処理条件は、使用するシラン化合物や他の添加剤によって異なるため、その都度最適化することが望ましい。
撥水撥油剤…紙、布、金属、ガラス、プラスチック、セラミックなど
離型剤…粘着テープ用、樹脂成形用金型、ロール用など
防汚加工剤…紙、布、金属、ガラス、プラスチック、セラミックなど
その他…塗料添加剤、樹脂改質剤、無機質充填剤の流動性、分散性を改質、テープ、フィルムなどの潤滑性の向上など
温度計、還流冷却器、撹拌機を取り付けた200mlの3つ口フラスコに、下記式(4)
−CH2CH 2Si≡ 0.5−0.6
−CH2CH 2CH2− 1.7−1.9
−CONCH 2CH2− 3.2−3.4
−Si(OCH 3)3 3.4−3.6
IR(KBr板、液膜法、cm-1、図2参照)
2950−2850(C−H)、1700(CON)、1315−1090(C−F)
合成例1で用いた化合物のうち、式(4)に示すパーフルオロポリエーテル変性ジアリルアミドの代わりに下記式(5)
合成例1で用いた化合物のうち、式(4)に示すパーフルオロポリエーテル変性ジアリルアミドの代わりに下記式(6)
合成例1で用いた化合物のうち、式(4)に示すパーフルオロポリエーテル変性ジアリルアミドの代わりに下記式(7)
合成例1、2で合成されたパーフルオロポリエーテル変性アミノシラン3.0gをイソプロピルアルコール97.0gに溶解させ、ガラス板(2.5×10×0.5cm)に刷毛塗りで塗布した。25℃、湿度70%の雰囲気下で1時間放置し、硬化被膜を形成させた。この試料片を用いて、下記(1)〜(4)の評価を行った。
接触角計(協和界面科学社製A3型)を用いて、硬化被膜の水及びn−ヘキサデカンに対する接触角を測定し、撥水撥油性の評価とした。
(2)離型性の評価
硬化被膜表面にセロハン粘着テープ(幅25mm)を貼り、その剥離力を測定して離型性の評価とした。測定は引張試験機を用いて180°の角度で剥離速度300mm/min.で行った。
(3)被膜の耐久性の評価
セルロース製不織布によって硬化被膜表面を一定の荷重で30往復拭いたのち、評価(1)で示した方法で水に対する接触角を測定して耐久性の評価とした。
(4)溶解性の評価
イソプロピルアルコールに対する溶解性を、固形分濃度3質量%で評価した。
上記(1)〜(4)の評価結果を表1に示す。
実施例1、2で用いたフルオロアミノシランの代わりに合成例3,4で合成されたフルオロアミノシランを用いた他は、実施例と同様の方法で評価した。評価結果を表1に示す。
実施例1、2で用いたフルオロアミノシランの代わりにKBM−7803(ヘプタデカトリフルオロデシルトリメトキシシラン、信越化学工業社製)を用いた他は、実施例と同様の方法で評価した。評価結果を表1に示す。
Claims (4)
- 極性溶媒がアルコール類、エステル系溶剤、又はエーテル系溶剤であることを特徴とする請求項1記載の表面処理剤。
- 請求項1又は2記載の表面処理剤を硬化させた硬化被膜を有する物品。
- 硬化被膜を有する物品が、サニタリー製品、輸送機用ガラス、一般産業用ガラス、ガラス製食器、建材又は電話ボックスであることを特徴とする請求項3記載の物品。
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EP20080009728 EP1997824B8 (en) | 2007-06-01 | 2008-05-28 | Perfluoropolyether-modified aminosilane, surface treating agent, and aminosilane-coated article |
US12/130,544 US20080299399A1 (en) | 2007-06-01 | 2008-05-30 | Perfluoropolyether-modified aminosilane, surface treating agent, and aminosilane-coated article |
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US10150889B2 (en) | 2013-09-16 | 2018-12-11 | Honeywell International Inc. | Poly fluorine-containing siloxane coatings |
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IT1402906B1 (it) * | 2010-11-30 | 2013-09-27 | Milano Politecnico | Rivestimento superficiale con composti perfluorurati come antifouling. |
JP2012219217A (ja) * | 2011-04-12 | 2012-11-12 | Shin-Etsu Chemical Co Ltd | 撥水処理剤及びその製造方法 |
CN102532550B (zh) * | 2011-12-29 | 2014-06-18 | 北京永泰和金属防腐技术有限公司 | 含氟烷基硅树脂制备方法及其应用 |
JP5731037B1 (ja) * | 2014-03-31 | 2015-06-10 | 三菱マテリアル株式会社 | 含フッ素シラン化合物 |
US9926339B2 (en) | 2014-03-31 | 2018-03-27 | Mitsubishi Materials Corporation | Fluorine-containing silane compound |
CN109072005A (zh) * | 2016-03-08 | 2018-12-21 | 科慕埃弗西有限公司 | 包含全氟(聚)醚基团的聚硅烷化合物 |
CN107814938B (zh) * | 2017-11-06 | 2021-01-22 | 九江学院 | 氟硅非离子表面活性剂的制备方法 |
JP7266438B2 (ja) * | 2019-03-27 | 2023-04-28 | 三菱マテリアル電子化成株式会社 | 防汚性膜形成用液組成物 |
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KR20210108673A (ko) | 2020-02-26 | 2021-09-03 | 삼성전자주식회사 | 불소 함유 (폴리)에테르기를 갖는 실란 화합물, 이를 포함하는 조성물, 이로부터 형성된 필름, 표시 장치 및 물품 |
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US10150889B2 (en) | 2013-09-16 | 2018-12-11 | Honeywell International Inc. | Poly fluorine-containing siloxane coatings |
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