JPH05117283A - Fluorine-containing silane coupling agent - Google Patents
Fluorine-containing silane coupling agentInfo
- Publication number
- JPH05117283A JPH05117283A JP3301182A JP30118291A JPH05117283A JP H05117283 A JPH05117283 A JP H05117283A JP 3301182 A JP3301182 A JP 3301182A JP 30118291 A JP30118291 A JP 30118291A JP H05117283 A JPH05117283 A JP H05117283A
- Authority
- JP
- Japan
- Prior art keywords
- coupling agent
- silane coupling
- fluorine
- acid
- glass
- 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.)
- Pending
Links
- 239000006087 Silane Coupling Agent Substances 0.000 title claims description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims description 11
- 229910052731 fluorine Inorganic materials 0.000 title claims description 10
- 239000011737 fluorine Substances 0.000 title claims description 10
- 239000002253 acid Substances 0.000 abstract description 13
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract description 5
- 239000007822 coupling agent Substances 0.000 abstract description 5
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 abstract description 4
- 150000004702 methyl esters Chemical class 0.000 abstract description 4
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002862 amidating effect Effects 0.000 abstract 1
- 239000011521 glass Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- -1 perfluoro groups Chemical group 0.000 description 7
- YSYRISKCBOPJRG-UHFFFAOYSA-N 4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC1=C(F)OC(C(F)(F)F)(C(F)(F)F)O1 YSYRISKCBOPJRG-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 4
- 229920002313 fluoropolymer Polymers 0.000 description 4
- 239000004811 fluoropolymer Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011162 core material Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- GBOMEIMCQWMHGB-UHFFFAOYSA-N 2-butyltetrahydrofuran Chemical compound CCCCC1CCCO1 GBOMEIMCQWMHGB-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000013307 optical fiber Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- FYJQJMIEZVMYSD-UHFFFAOYSA-N perfluoro-2-butyltetrahydrofuran Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C1(F)F FYJQJMIEZVMYSD-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Surface Treatment Of Glass (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は新規なシランカップリン
グ剤に関するものであり、含フッ素化合物の他基材への
接着性、密着性の向上を可能にするものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel silane coupling agent, which is capable of improving the adhesiveness and adhesiveness of a fluorine-containing compound to other substrates.
【０００２】[0002]
【従来の技術および発明が解決しようとする課題】ガラ
スや金属とエポキシ樹脂、アクリル樹脂との接着性、密
着性の向上を図るためのシランカップリング剤の開発は
なされているが、フッ素樹脂と他の物質間との接着性、
密着性をもたらす改質材は開発されていない。また、含
フッ素シランカップリング剤も知られているが、これは
ガラス表面の耐水性、耐油性、耐擦傷性の向上や、金属
の耐腐食防止を可能とはするものの、やはり、フッ素樹
脂と他の物質との接着性、密着性の向上を図るための改
質材としての効力はほとんどない。PRIOR ART AND PROBLEMS TO BE SOLVED BY THE INVENTION Although a silane coupling agent has been developed for improving the adhesiveness and adhesion between glass and metal and epoxy resin and acrylic resin, fluororesin has been developed. Adhesion between other substances,
No modifier has been developed to provide adhesion. Further, a fluorine-containing silane coupling agent is also known, but it is possible to improve the water resistance, oil resistance, and scratch resistance of the glass surface and prevent corrosion of metal, but it is still a fluororesin. It has almost no effect as a modifier for improving the adhesion and adhesion with other substances.
【０００３】また、これまでにいくつかのパーフルオロ
基を含むフッ素樹脂の開発がなされ、その優れた特性を
生かして様々な分野で利用されている。中でも、パーフ
ルオロ（-2,2−ジメチル-1,3−ジオキソール）を主要モ
ノマ成分とする重合体は、透明性、低屈折率性、低誘電
性、耐熱性といった優れた特徴を有しており、光学材料
や電子材料として有望視されているが、他素材との接着
性、密着性に乏しいことから、その用途範囲が限定され
たものとなっている。Fluorine resins containing several perfluoro groups have been developed so far and are utilized in various fields by taking advantage of their excellent properties. Among them, a polymer containing perfluoro (-2,2-dimethyl-1,3-dioxole) as a main monomer component has excellent characteristics such as transparency, low refractive index, low dielectric property and heat resistance. However, it is considered to be promising as an optical material and an electronic material, but its application range is limited due to its poor adhesiveness and adhesion to other materials.
【０００４】特に芯材をガラス、鞘材をパーフルオロ
（-2,2−ジメチル-1,3−ジオキソール）を主要モノマと
した重合体にて構成された光ファイバは、鞘材が優れた
透明性、低屈折率性、耐熱性を備えていることから、高
性能な光ファイバとなっているが、芯材と鞘材との密着
性に乏しく、鞘材が芯材から剥離を起こしやすいという
難点を有している。In particular, an optical fiber composed of a polymer having a core material of glass and a sheath material of perfluoro (-2,2-dimethyl-1,3-dioxole) as a main monomer has an excellent transparent sheath material. Although it is a high-performance optical fiber because of its high properties, low refractive index, and heat resistance, it has poor adhesion between the core material and the sheath material, and the sheath material easily peels from the core material. There are difficulties.
【０００５】[0005]
【課題を解決するための手段】そこで本発明者等は上記
課題を解決すべく鋭意検討し、パーフルオロ（-2,2−ジ
メチル-1,3−ジオキソール）を主要モノマとする重合体
をはじめとするフッ素樹脂とガラスや金属との密着性を
付与し得る改質材を見出すべく検討した結果、パーフル
オロアルキルエーテル構造を有するシランカップリング
剤が、上記課題を解決しうるものとして使用しうること
を見出し本発明を完成した。[Means for Solving the Problems] Therefore, the present inventors diligently studied to solve the above-mentioned problems, and started to study a polymer containing perfluoro (-2,2-dimethyl-1,3-dioxole) as a main monomer. As a result of studying to find a modifier capable of imparting adhesion between a fluororesin and glass or a metal, a silane coupling agent having a perfluoroalkyl ether structure can be used as a material capable of solving the above problems. It was found that the present invention has been completed.
【０００６】本発明のシランカップリング剤にて接合す
るフッ素樹脂として、特にパーフルオロ（-2,2−ジメチ
ル-1,3−ジオキソール）を主要モノマとするものであ
り、共重合可能な他の単量体としては、特に制限されな
いが、α−オレフィン、シクロオレフィン、ビニルエー
テル、CF3CF=CF2,CF3CH=CFCF3,CF2=CFCF2CHF2,CF3CF2CF
=CH2,CF3CH2CH=CH2,CF3CH=CHCH3,CF2=CHCH2CH3,CH2=CFC
H2CH3,CF3(CF2)2CF=CF2, CF3(CF2)3CF=CF2等のフルオロ
オレフィンを挙げることができる。As the fluororesin to be bonded with the silane coupling agent of the present invention, particularly perfluoro (-2,2-dimethyl-1,3-dioxole) is a main monomer, and other copolymerizable resins are used. The monomer is not particularly limited, α-olefin, cycloolefin, vinyl ether, CF 3 CF = CF 2 , CF 3 CH = CFCF 3 , CF 2 = CFCF 2 CHF 2 , CF 3 CF 2 CF
= CH 2 , CF 3 CH 2 CH = CH 2 , CF 3 CH = CHCH 3 , CF 2 = CHCH 2 CH 3 , CH 2 = CFC
Fluoroolefins such as H 2 CH 3 , CF 3 (CF 2 ) 2 CF = CF 2 , CF 3 (CF 2 ) 3 CF = CF 2 can be mentioned.
【０００７】パーフルオロ（-2,2−ジメチル-1,3−ジオ
キソール）を主要モノマ成分とする重合体を、他の基材
と接合するにはフッ素化合物よりなる溶剤を用いて行う
のがよく、その具体例としては、F-[CF(CF3)CF2O]n-CF2
CF3 （デュポン社製：商品名；Krytox）、CF3O-[CF(C
F3)CFCF20]m-(CF2O)n-CF3 （モンテフルオロ社製：商品
名；Fomblin Y ）、CF3O-(CF2CF2O)m-(CF2O)n-CF3 （モ
ンテフルオロ社製：商品名；Fomblin Z ）、F-(CF2CF2C
F2O)n-CF2CF3（ダイキン工業社製：商品名；デムナム）
等を挙げることができる。To bond a polymer containing perfluoro (-2,2-dimethyl-1,3-dioxole) as a main monomer component to another substrate, it is often preferable to use a solvent composed of a fluorine compound. , As a specific example, F- [CF (CF 3 ) CF 2 O] n -CF 2
CF 3 (manufactured by DuPont: trade name; Krytox), CF 3 O- [CF (C
F 3 ) CFCF 2 0] m- (CF 2 O) n -CF 3 (manufactured by Montefluoro Corporation: trade name; Fomblin Y), CF 3 O- (CF 2 CF 2 O) m- (CF 2 O) n -CF 3 (manufactured by Monte Fluor: product name; Fomblin Z), F- (CF 2 CF 2 C
F 2 O) n -CF 2 CF 3 (manufactured by Daikin Industries, Ltd .: trade name; Dem Nam)
Etc. can be mentioned.
【０００８】本発明のパーフルオロアルキルエーテル構
造を含むシランカップリング剤は、例えば、ポリ（ヘキ
サフルオロプロピレンオキシド）酸およびその酸誘導
体、例えば、メチルエステル酸フロリドなどとγ−アミ
ノプロピルトリエトキシシランとをアミド化反応させる
ことにより得られる。The silane coupling agent containing a perfluoroalkyl ether structure of the present invention includes, for example, poly (hexafluoropropylene oxide) acid and acid derivatives thereof such as methyl ester acid fluoride and γ-aminopropyltriethoxysilane. Is obtained by amidation reaction of.
【０００９】原料となるパーフルオロアルキルエーテル
の酸メチルエステルはヘキサフルオロプロピレンオキシ
ドをフッ素イオン触媒で開環重合すると［式Ｉ］に従っ
て反応が起り、対応する酸フロライドが得られる。The acid methyl ester of perfluoroalkyl ether as a raw material undergoes ring-opening polymerization of hexafluoropropylene oxide with a fluorine ion catalyst to cause a reaction according to [Formula I] to obtain a corresponding acid fluoride.
【００１０】[0010]
得られた酸フロライドをエーテル、ジオキサンなどの溶
媒中で過剰のメタノールの存在下、10〜20℃で反応させ
ることにより対応する［式II］で示されるメチルエステ
ルが得られる。 By reacting the obtained acid fluoride in a solvent such as ether or dioxane in the presence of excess methanol at 10 to 20 ° C., the corresponding methyl ester represented by the formula [II] can be obtained.
【００１１】[0011]
さらにこのエステル化物を求核性官能基であるアミノ基
およびカップリング剤としての反応性基であるトリアル
コキシシリル基を有するγ−アミノプロピルトリエトキ
シシランとを［式III]に従って反応させることにより、
本発明のパーフルオロアルキルエーテル構造を有する含
フッ素シランカップリング剤を合成することができる。 Furthermore, by reacting this esterified product with γ-aminopropyltriethoxysilane having an amino group which is a nucleophilic functional group and a trialkoxysilyl group which is a reactive group as a coupling agent according to [Formula III],
The fluorine-containing silane coupling agent having the perfluoroalkyl ether structure of the present invention can be synthesized.
【００１２】[0012]
【００１３】本発明の含フッ素シランカップリング剤を
用いてフッ素重合体をガラスに接合する場合を示すと次
のごとくなる。その１は、ガラスを含フッ素シランカッ
プリング剤で処理した後、フッ素重合体の溶液をコーテ
ィングし、乾燥する方法、その２は、含フッ素シランカ
ップリング剤をフッ素重合体の溶液に混合し、この溶液
をガラスにコーティングし、乾燥する方法、その３は、
ガラスをまず求核性官能基（アミノ基など）をもつトリ
アルコキシシラン（またはトリハロゲン化シラン）で処
理し、続いてパーフルオロアルキルエーテル酸あるいは
その酸誘導体で処理してカップリング剤をガラス面上に
生成した後、フッ素重合体の溶液をコーティングし、乾
燥する方法、その４は、ガラスをまずその３と同様の求
核性官能基を有するシランで処理した後、パーフルオロ
アルキルエーテル酸あるいはその酸誘導体を含フッ素重
合体溶液に混合したものをコーティングする方法、など
の方法をとることができるが、これらの方法に限られな
い。The case where a fluoropolymer is bonded to glass using the fluorine-containing silane coupling agent of the present invention will be described as follows. The first is a method of treating glass with a fluorine-containing silane coupling agent, followed by coating with a solution of a fluoropolymer and drying, and the second is mixing the fluorine-containing silane coupling agent with a solution of the fluorine polymer, The method of coating this solution on glass and drying it, 3 is
The glass is first treated with a trialkoxysilane (or trihalogenated silane) having a nucleophilic functional group (such as an amino group), and then with a perfluoroalkyl ether acid or its acid derivative to treat the coupling agent on the glass surface. A method of coating with a solution of a fluoropolymer after being formed on the above, and drying, 4 is a method in which glass is first treated with a silane having a nucleophilic functional group similar to that in 3 and then perfluoroalkyl ether acid or A method such as coating a mixture of the acid derivative with a fluoropolymer solution can be used, but the method is not limited to these methods.
【００１４】[0014]
【実施例】以下、実施例により本発明を詳細に説明す
る。The present invention will be described in detail below with reference to examples.
【００１５】[0015]
【実施例１】 （シランカップリング剤の合成）F-[CF(CF3)CF2O]2-CF
(CF3)COOCH3, 27.5ｇを無水エタノール100 mlに反応容
器内で溶解した。反応容器は空気中の水分の吸収を避け
るため塩化カルシウム管をとりつけ、容器温度を10〜15
℃に保った。γ−アミノプロピルトリエトキシシラン1
0.1ｇを無水エタノール50mlに溶解した溶液を１時間か
けて上記反応容器内に滴下し、さらに４時間反応させ
た。この間も反応容器を10〜15℃に保った。反応終了
後、エタノール、未反応エステルを反応容器内圧１mmH
g、温度50℃で蒸発させることにより、32ｇの反応生成
物を得た。得られた反応生成物を赤外線分析法およびＮ
ＭＲ法により分析した結果、下記構造のものであること
を確かめた。 F-[CF(CF3)CF2O]2-CF(CF3)CONHCH2CH2CH2Si(OEt)3 密着試験の評価法はJIS-K5400 の方法に従い、ガラス板
にフッ素樹脂フィルムをコーティング法にて形成し、こ
のフィルム面に巾１mm間隔の碁盤目を基板に達するよう
に入れ、この碁盤目面にセロハンテープを密着して剥離
し、ガラス基板上に残るフィルムの碁盤目の数を百分率
で示した。 （ガラス基板との密着試験）クロム酸混液にて洗浄した
ガラス板に実施例１で合成したシランカップリング剤の
１wt％エタノール溶液を塗布し、乾燥後、パーフルオロ
（-2,2−ジメチル−1,3-ジオキソール）／テトラフルオ
ロエチレン（65／35mol%）共重合体の20wt％パーフルオ
ロ（2-ブチルテトラヒドロフラン）溶液をコーティング
した。続いて200 ℃に加熱乾燥処理した後、密着性の評
価を剥離試験にて行ったところ、剥離率は０％であっ
た。Example 1 (Synthesis of Silane Coupling Agent) F- [CF (CF 3 ) CF 2 O] 2 -CF
(CF 3 ) COOCH 3 , 27.5 g was dissolved in 100 ml of absolute ethanol in the reaction vessel. The reaction vessel is equipped with a calcium chloride tube in order to avoid absorption of moisture in the air, and the vessel temperature is set to 10 to 15
It was kept at ℃. γ-aminopropyltriethoxysilane 1
A solution prepared by dissolving 0.1 g in 50 ml of absolute ethanol was dropped into the above reaction vessel over 1 hour, and further reacted for 4 hours. During this time, the reaction vessel was kept at 10 to 15 ° C. After the reaction is complete, add ethanol and unreacted ester to the reaction vessel with an internal pressure of 1 mmH.
g, evaporation at a temperature of 50 ° C. gave 32 g of reaction product. The obtained reaction product was analyzed by infrared analysis and N 2.
As a result of analysis by the MR method, it was confirmed to have the following structure. F- [CF (CF 3 ) CF 2 O] 2 -CF (CF 3 ) CONHCH 2 CH 2 CH 2 Si (OEt) 3 Adhesion test was evaluated according to JIS-K5400, and a fluororesin film was applied to the glass plate. The number of crosses of the film left on the glass substrate, which was formed by the coating method, was put on this film surface so that the cross-cuts with a width of 1 mm reached the substrate, and the cellophane tape was adhered to and peeled off from the cross-cut surface. Was expressed as a percentage. (Adhesion Test with Glass Substrate) A 1 wt% ethanol solution of the silane coupling agent synthesized in Example 1 was applied to a glass plate washed with a chromic acid mixed solution, dried, and then dried with perfluoro (-2,2-dimethyl-). A 20 wt% perfluoro (2-butyltetrahydrofuran) solution of a 1,3-dioxole) / tetrafluoroethylene (65/35 mol%) copolymer was coated. Then, after heat-drying at 200 ° C., the adhesion was evaluated by a peeling test, and the peeling rate was 0%.
【００１６】[0016]
【比較例１】シランカップリング剤未処理のガラス板
に、パーフルオロ（-2,2−ジメチル−1,3-ジオキソー
ル）／テトラフルオロエチレン（65／35mol%）共重合体
の20wt％パーフルオロ（2-ブチルテトラヒドロフラン）
溶液を塗布、乾燥して製膜し、剥離試験を行ったとこ
ろ、剥離率は100%であった。[Comparative Example 1] 20 wt% perfluoro (-2,2-dimethyl-1,3-dioxole) / tetrafluoroethylene (65/35 mol%) copolymer of 20 wt% perfluoro was added to a glass plate not treated with a silane coupling agent. (2-butyltetrahydrofuran)
When the solution was applied, dried and formed into a film, and a peeling test was performed, the peeling rate was 100%.
【００１７】[0017]
【比較例２】洗浄処理したガラス板をC8F17CH2CH2Si(OC
H3)3の１wt％エタノール溶液にて処理した後、乾燥し、
この処理面に比較例１で用いたフッ素樹脂の溶液を塗
布、乾燥してガラス板上にフッ素樹脂塗膜を形成した。
この塗膜を実施例１と同様にして剥離試験したところ、
塗膜の残存率は０／100 であった。[Comparative Example 2] A glass plate that had been subjected to cleaning treatment was subjected to C 8 F 17 CH 2 CH 2 Si (OC
H 3 ) 3 in 1 wt% ethanol solution, then dried,
The solution of the fluororesin used in Comparative Example 1 was applied to this treated surface and dried to form a fluororesin coating film on the glass plate.
When this coating film was subjected to a peel test in the same manner as in Example 1,
The residual rate of the coating film was 0/100.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０９Ｊ 183/12 ＪＧＦ 8319−4Ｊ // Ｃ０８Ｇ 65/32 ＮＱＪ 9167−4Ｊ Ｃ０８Ｊ 5/12 ＣＥＷ 9267−4Ｆ (72)発明者 大西 宏明 広島県大竹市御幸町20番１号三菱レイヨン 株式会社大竹事業所内─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification number Internal reference number FI Technical indication C09J 183/12 JGF 8319-4J // C08G 65/32 NQJ 9167-4J C08J 5/12 CEW 9267- 4F (72) Inventor Hiroaki Onishi 20-1 Miyukicho, Otake City, Hiroshima Prefecture Mitsubishi Rayon Co., Ltd. Otake Office
Claims (1)
する含フッ素シランカップリング剤。1. A fluorine-containing silane coupling agent having a perfluoroalkyl ether structure.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3301182A JPH05117283A (en) | 1991-10-22 | 1991-10-22 | Fluorine-containing silane coupling agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3301182A JPH05117283A (en) | 1991-10-22 | 1991-10-22 | Fluorine-containing silane coupling agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05117283A true JPH05117283A (en) | 1993-05-14 |
Family
ID=17893771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3301182A Pending JPH05117283A (en) | 1991-10-22 | 1991-10-22 | Fluorine-containing silane coupling agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH05117283A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998049218A1 (en) * | 1997-04-30 | 1998-11-05 | Daikin Industries, Ltd. | Fluoropolymer, process for preparing the same, and use thereof |
| JP2014005353A (en) * | 2012-06-22 | 2014-01-16 | Nicca Chemical Co Ltd | Perfluoropolyether-modified silane compound, antifouling coating composition, antifouling coating and article having the coating |
| KR101384457B1 (en) * | 2011-08-04 | 2014-04-14 | 주식회사 엘지화학 | Silane-based compounds and photosensitive resin composition comprising the same |
| CN103788363A (en) * | 2013-12-25 | 2014-05-14 | 上海艾肯化工科技有限公司 | Method for preparing perfluoropolyether with high molecular weight |
-
1991
- 1991-10-22 JP JP3301182A patent/JPH05117283A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998049218A1 (en) * | 1997-04-30 | 1998-11-05 | Daikin Industries, Ltd. | Fluoropolymer, process for preparing the same, and use thereof |
| US6337135B1 (en) | 1997-04-30 | 2002-01-08 | Daikin Industries, Ltd. | Fluoropolymer, process for preparing the same, and use thereof |
| KR101384457B1 (en) * | 2011-08-04 | 2014-04-14 | 주식회사 엘지화학 | Silane-based compounds and photosensitive resin composition comprising the same |
| JP2014005353A (en) * | 2012-06-22 | 2014-01-16 | Nicca Chemical Co Ltd | Perfluoropolyether-modified silane compound, antifouling coating composition, antifouling coating and article having the coating |
| CN103788363A (en) * | 2013-12-25 | 2014-05-14 | 上海艾肯化工科技有限公司 | Method for preparing perfluoropolyether with high molecular weight |
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