JP2009513348A - 不飽和フッ素化炭化水素類を含む溶媒組成物 - Google Patents
不飽和フッ素化炭化水素類を含む溶媒組成物 Download PDFInfo
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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Abstract
Description
本願は、2005年11月1日出願の米国特許公報(特許文献1)の優先権の利益を主張する。
(a)フッ素系潤滑剤と溶媒を組み合わせて、潤滑剤−溶媒の組合せを形成するステップであって、前記溶媒が、式E−またはZ−R1CH=CHR2(式中、R1およびR2は独立に、C1〜C6パーフルオロアルキル基、またはC1〜C6ヒドロフルオロアルキル基である)を有する不飽和フッ素化炭化水素類からなる群から選択される不飽和フッ素化炭化水素を含むステップと、
(b)潤滑剤−溶媒の組合せを表面と接触させるステップと、
(c)溶媒を表面から蒸発させて、フッ素系潤滑剤コーティングを表面に形成するステップとを含む方法である。
(a)界面活性剤をさらに含む本発明の組成物と基板を接触させるステップと、次いで
(b)基板を前記組成物との接触から取り外すステップとを含む方法である。
a)基板を、界面活性剤を含有する本発明の組成物と接触させ、それによって前記基板を脱水するステップと、
b)脱水された基板を組成物から回収するステップとを含む方法に関する。
(1,1,1,4,4,5,5,6,6,7,7,7−ドデカフルオロヘプタ−2−エン(F14E)の合成)
(C4F9CH2CHICF3の合成)
パーフルオロ−n−ブチルヨージド(180.1gm、0.52モル)および2,2,2−トリフルオロプロペン(25.0gm、0.26モル)を、400mlのハステロイ(Hastelloy)(商標)シェーカーチューブに添加し、自己圧力下で200℃に8時間加熱し、圧力は最大428psig(3.05Mpa)に上昇した。生成物を室温で回収した。上記の反応を、これらの条件で再度実施し、生成物を合わせた。次いで、同じ400mlの反応器で、パーフルオロ−n−ブチルヨージドおよび2,2,2−トリフルオロプロペンの量を2倍にして繰り返した。この場合、圧力は573psig(3.85Mpa)に上昇した。3回の反応の生成物を合わせ、蒸留して、322.4gmのC4F9CH2CHICF3(52.2°/35mm)を収率70%で得た。
撹拌棒を装備し、充填した蒸留塔および蒸留ヘッドに連結させた2Lの丸底フラスコに、C4F9CH2CHICF3(322.4gm、0.73モル)を滴下漏斗で滴下した。フラスコには、イソプロピルアルコール(95ml)、KOH(303.7gm、0.54モル)、および水(303ml)が入っていた。生成物を回収し、メタ重亜硫酸ナトリウム、水で洗浄し、MgSO4で乾燥し、ガラスヘリックスを充填した6インチの塔/カラムを用いて蒸留した。生成物F14E(173.4gm、76%)は78.2℃で沸騰する。19F NMR(δ −66.7(CF3, m, 3F), −81.7(CF3, m 3F), −124.8 (CF2, m, 2F), −126.4 (CF2, m, 2F)、および−114.9ppm(CF2, m, 2F))、1H NMR(δ 6.45)で特徴付けた(クロロホルム−d溶液)。
(1,1,1,2,2,5,5,6,6,7,7,8,8,8−テトラデカフルオロオクタ−3−エン(F24E)の合成)
(C4F9CHICH2C2F5の合成)
パーフルオロエチルヨージド(220gm、0.895モル)および3,3,4,4,5,5,6,6,6−ノナフルオロヘキサ−1−エン(123gm、0.50モル)を、400mlのハステロイ(Hastelloy)シェーカーチューブに添加し、自己圧力下で200℃に10時間加熱した。これからの生成物と、同様な条件下で実施された2つの他の生成物を組み合わせ、10重量%の重亜硫酸ナトリウム水溶液200mLで2回洗浄した。有機相を塩化カルシウムで乾燥し、次いで蒸留して、277.4gmのC4F9CH2CHICF3(79〜81℃/67〜68mmHg)を収率37%で得た。
メカニカルスターラ、滴下漏斗、冷却器、および熱電対を装備した1Lの丸底フラスコに、C4F9CHICH2C2F5(277.4gm、0.56モル)およびイソプロパノール(217.8g)を加えた。滴下漏斗に、83.8gの水に溶解させた水酸化カリウム(74.5g、1.13モル)溶液を入れた。フラスコに、KOH溶液を、急速に撹拌しながら約1時間かけて滴下したとき、温度は徐々に21℃から42℃に上昇した。反応塊を水で希釈し、生成物を相分離によって回収した。生成物を50mLの10重量%の重亜硫酸ナトリウム水溶液および50mLの水で洗浄し、塩化カルシウムで乾燥し、次いで大気圧で蒸留した。生成物F24E(128.7gm、63%)は95.5℃で沸騰する。19F NMR (δ −81.6 (CF3, m, 3F), −85.4(CF3, m 3F), −114.7 (CF2, m, 2F), −118.1 (CF2, m, 2F), −124.8 ppm (CF2, m, 2F), −126.3 ppm (CF2, m, 2F))、および1H NMR(δ6.48)で特徴付けた(クロロホルム−d溶液)。
(CF3CH=CHCF(CF3)2(F13iE)の合成)
(CF3CHICH2CF(CF3)2の合成)
(CF3)2CFI(265gm、0.9モル)および2,2,2−トリフルオロプロペン(44.0gm、0.45モル)を、400mlのハステロイ(Hastelloy)シェーカーチューブに添加し、自己圧力下で200℃に8時間加熱した(最大585psig(4.14MPa))。生成物を室温で回収して、110gmの(CF3)2CFCH2CHICF3(76−77℃/200mm)を収率62%で得た。
500mlの丸底フラスコに撹拌棒および滴下漏斗を装備し、短いパスの蒸留塔およびドライアイスのトラップに連結させた。フラスコに、イソプロピルアルコール(50ml)、水酸化カリウム(109gm、1.96モル)、および水(109ml)を加えた。(CF3)2CFCH2CHICF3(109gm、0.28モル)を、42℃において、滴下漏斗で徐々に滴下した。滴下中、温度は42から55℃に上昇し、生成物をフラスコから留出させた。30分間還流した後、フラスコ内の温度は62℃に上昇した。生成物を回収し、水で洗浄し、MgSO4で乾燥し、蒸留した。生成物F13iE(41gm、55%)は48〜50℃で沸騰し、19F NMR(δ −187.6 (CF, m 1F), −77.1 (CF3, m 6F), − 66.3 (CF3, m 3F)で特徴付けた(クロロホルム−d溶液)。
(C4F9CHICH2C2F5の合成)
3,3,4,4,5,5,6,6,6−ノナフルオロヘキサ−1−エン(20.5gm、0.0833モル)、ビス(トリフェニルホスフィン)ニッケル(0)ジカルボニル(0.53g、0.0008モル)、およびパーフルオロエチルヨージド(153.6gm、0.625モル)を、210mlのハステロイ(Hastelloy)シェーカーチューブに添加し、自己圧力下で100℃において8時間加熱した。生成物のGC−MS分析によって、C4F9CHICH2C2F5(64.3 GC面積%)およびジ付加物(3.3 GC面積%)の存在が示唆された。3,3,4,4,5,5,6,6,6−ノナフルオロヘキサ−1−エンの変換は80.1%であった。
不飽和フルオロオレフィン化合物に、所与の量の油を混合物が濁りまたは2相に分離するまで添加することによって、不飽和フルオロオレフィン化合物のフッ素化油を溶解する能力を決定した。表1の結果から、不飽和フルオロオレフィン化合物のフッ素化油を溶解する能力が高いことがわかる。さらに、不飽和フルオロオレフィン化合物中0.5重量%の油の溶液を調製した。この実施例では、不飽和フルオロオレフィンは1,1,1,2,2,5,5,6,6,7,7,8,8,8−テトラデカフルオロオクタ−3−エン(F24E)であった。予め計量した金属試片を溶液中に部分的に浸漬し、溶媒を蒸発させ、試片を再計量した。表5に、この部分的コーティング方法で得られた平均的コーティングを示す。したがって、不飽和フルオロオレフィン化合物を、フッ素化油を基板に被着させるための担体流体として使用することができる。
クライトックス(Krytox)GPL 106油を、スワブで重量既知の清浄な金属試片に塗りつけた。試片を再度計量し、次いで室温で1,1,1,2,2,5,5,6,6,7,7,8,8,8−テトラデカフルオロオクタ−3−エン(F24E)に浸漬することによって清浄した。試片を1分間浸漬し、次いで風乾した。次いで、試片を再計量し、除去された油のパーセントを決定した。表6のこれらの結果から、溶媒は、フッ素化油を清浄する際に優れた効率を示すことがわかる。
Claims (30)
- 残渣を表面から除去する方法であって、
a)表面を、式E−またはZ−R1CH=CHR2(式中、R1およびR2は独立に、C1〜C6パーフルオロアルキル基、またはC1〜C6ヒドロフルオロアルキル基である)を有する化合物からなる群から選択される少なくとも1つの不飽和フッ素化炭化水素を含む組成物と接触させるステップと:
(b)前記表面を前記組成物から回収するステップと
を含むことを特徴とする方法。 - R1およびR2が独立に、CF3、C2F5、CF2CF2CF3、CF(CF3)2、CF2CF2CF2CF3、CF(CF3)CF2CF3、CF2CF(CF3)2、C(CF3)3、CF2CF2CF2CF2CF3、CF2CF2CF(CF3)2、C(CF3)2C2F5、CF2CF2CF2CF2CF2CF3、CF(CF3)CF2CF2C2F5、C(CF3)2CF2C2F5、CHF2、CH2F、C2HF4、C2H2F3、C2H3F2、C3HF6、i−C3HF6、C3H2F5、C3H3F4、C4HF8、C4H3F6、C5HF10、C5H3F8、またはC6HF12であることを特徴とする請求項1に記載の方法。
- 前記少なくとも1つの不飽和フッ素化炭化水素が、CF3CH=CHCF3、CF3CH=CHC2F5、CF3CH=CHCF2C2F5、CF3CH=CHCF(CF3)2、C2F5CH=CHC2F5、CF3CH=CH(CF2)3CF3、CF3CH=CHCF2CF(CF3)2、CF3CH=CHCF(CF3)C2F5、CF3CH=CHC(CF3)3、C2F5CH=CHCF2C2F5、C2F5CH=CHCF(CF3)2、CF3CH=CH(CF2)4CF3、CF3CH=CHCF2CF2CF(CF3)2、CF3CH=CHC(CF3)2C2F5、C2F5CH=CH(CF2)3CF3、C2F5CH=CHCF2CF(CF3)2、C2F5CH=CHCF(CF3)C2F5、C2F5CH=CHC(CF3)3、C2F5CF2CH=CHCF2C2F5、(CF3)2CFCH=CHCF(CF3)2、C2F5CF2CH=CHCF(CF3)2、CF3CH=CH(CF2)5CF3、CF3CH=CHCF(CF3)(CF2)2C2F5、CF3CH=CHC(CF3)2CF2C2F5、C2F5CH=CH(CF2)4CF3、C2F5CH=CHCF2CF2CF(CF3)2、C2F5CH=CHC(CF3)2C2F5、C2F5CF2CH=CH(CF2)3CF3、C2F5CF2CH=CHCF2CF(CF3)2、C2F5CF2CH=CHCF(CF3)C2F5、C2F5CF2CH=CHC(CF3)3、(CF3)2CFCH=CH(CF2)3CF3、(CF3)2CFCH=CHCF2CF(CF3)2、(CF3)2CFCH=CHCF(CF3)C2F5、(CF3)2CFCH=CHC(CF3)3、C2F5CH=CH(CF2)5CF3、C2F5CH=CHCF(CF3)(CF2)2C2F5、C2F5CH=CHC(CF3)2CF2C2F5、C2F5CF2CH=CH(CF2)4CF3、C2F5CF2CH=CHCF2CF2CF(CF3)2、C2F5CF2CH=CHC(CF3)2C2F5、(CF3)2CFCH=CH(CF2)4CF3、(CF3)2CFCH=CHCF2CF2CF(CF3)2、(CF3)2CFCH=CHC(CF3)2C2F5、CF3(CF2)3CH=CH(CF2)3CF3、CF3(CF2)3CH=CHCF2CF(CF3)2、CF3(CF2)3CH=CHCF(CF3)C2F5、CF3(CF2)3CH=CHC(CF3)3、(CF3)2CFCF2CH=CHCF2CF(CF3)2、(CF3)2CFCF2CH=CHCF(CF3)C2F5、(CF3)2CFCF2CH=CHC(CF3)3、C2F5CF(CF3)CH=CHCF(CF3)C2F5、C2F5CF(CF3)CH=CHC(CF3)3、または(CF3)3CCH=CHC(CF3)3の少なくとも1つであることを特徴とする請求項1に記載の方法。
- 前記不飽和フッ素化炭化水素が、(CF3)2CFCH=CH2、CF3CF2CF2CH=CH2、CH2=CFCF2CF2CHF2、CF2=CHCF2CH2CF3、CF3CF=C(CF3)(CH3)、CH2=CFCH(CF3)2、CHF=CHCH(CF3)2、CH2FCH=C(CF3)2、CH3CF=C(CF3)2、(CF3)2C=CHCH3、CHF2CF2CF=CFCH3、C2F5CF=CHCH3、CF3C(CH3)=CHCF3、CH2=CHCF2CHFCF3、CH2=C(CF3)CH2CF3、CF3CH=CFCH2CH3、CF3CH=C(CH3)2、CF3(CF2)3CF=CF2、CF3CF2CF=CFCF2CF3、(CF3)2C=C(CF3)2、(CF3)2CFCF=CFCF3、(CF3)2C=CHC2F5、(CF3)2CFCF=CHCF3、CF3CF2CF2CF2CH=CH2、CH2=CHC(CF3)3、(CF3)2C=C(CH3)(CF3)、CH2=CFCF2CH(CF3)2、CF3CF=C(CH3)CF2CF3、CF3CH=CHCH(CF3)2、(CF3)2CFCF=CHCH3、CF3CF2CF2CF=CHCH3、CH2=CHCF2CF2CF2CHF2、(CF3)2C=CHCF2CH3、CH2=C(CF3)CH2C2F5、CF3CF2CF2C(CH3)=CH2、CF3CF2CF2CH=CHCH3、CH2=CHCH2CF2C2F5、CF3CF2CF=CFC2H5、CH2=CHCH2CF(CF3)2、CF3CF=CHCH(CF3)(CH3)、(CF3)2C=CFC2H5、(CH3)2C=CFCF2CF3、(CF3)2C=C(CH3)2、CF3CF=CFCF2CF2C2F5、CF3CF2CF=CFCF2C2F5、CF3CH=CFCF2CF2C2F5、CF3CF=CHCF2CF2C2F5、CF3CF2CH=CFCF2C2F5、CF3CF2CF=CHCF2C2F5、CF3CF2CF2CF2CF=CHCH3、CF3CF2CF2CF=CHCH2CH3、(CH3)2C=CFCF2CF2CF3、シクロ−CF2CH=CHCF2CF2CF2−、シクロ−CF2CF=CFCF2CF2CF2−、CF2=CHCF2Br、CF2=CFCBrH2、CHF=CBrCF3、CHF=CHCBrF2、CHF=CBrCHF2、CHBr=CFCF3、CHBr=CHCF3、CH2=CBrCF3、CH2CFCBrF2、CFBr=CHCF3、CFBr=CFCF3、CH2=CBrCF2CF3、CHBr=CHCF2CF3、CH2=CHCF2CF2Br、CH2=CHCBrFCF3、CF3CBr=CFCF3、CH3CBr=CHCF3、CF3CBr=CHCH3、(CF3)2C=CHBr、CF3CF=CBrCF2CF3、CHF2CBr=CFC2F5、CF2=CBrCHFC2F5、CHBr=CF(CF2)2CHF2、CH2=CBrCF2C2F5、CF2=CHCF2CH2CBrF2、(CF3)2CFCBr=CH2、CF2=C(CH2Br)CF3、CH2=C(CBrF2)CF3、(CF3)2CHCH=CHBr、(CF3)2C=CHCH2Br、CH2=CHCF(CF3)CBrF2、CF3CF2CF2CBr=CH2、CF3(CF2)3CBr=CH2、CHCl=CFCClF2、CHCl=CClCF3、CHCl=CHCH2F、CHCl=CFCH3、CH2=CClCH2F、CHF=CClCH3、CH2=CClCClF2、CH2=CFCCl2F、CHCl=CClCHF2、CHCl=CHCClF2、CHF=CClCHClF、CCl2=CFCH3、CH2=CClCHClF、CH2=C(CHF2)CClF2、CH2=CHCF2CHClF、CHCl=C(CH3)CF3、CH2=CHCHClCF3、CH3CF=CHCClF2、CH2=CClCF2CF3、CHCl=CHCF2CF3、CH2=CHCF2CF2Cl、CH2=CHCClFCF3、CH3CCl=CHCF3、CF3CCl=CHCH3、CH2=CHCClFCHCl2、CH2=CClCClFCClF2、CH2=CClCH2CClF2、CH2=CHCF2CHCl2、CH2=CHCClFCClF2、CCl2=C(CH3)CF3、CCl2=CHCH2CF3、CH2=CFCClFCClF2、CClF=CHC2H5、CHCl=CHCF2CH3、CH2=CClCF2CH3、CH3CH=CHCClF2、(CF3)2C=CHCl、CF3CH=C(CClF2)CF3、CHCl=CHCF2CClFCF3、CHCl=CHCF(CClF2)CF3、CF3CF=CClCF2CF3、CHCl=CF(CF2)2CHF2、CH2=CClCF2C2F5、CF2=CHCF2CH2CClF2、(CF3)2CFCCl=CH2、(CF3)2CHCH=CHCl、(CF3)2C=CHCH2Cl、CH2=CHCF(CF3)CClF2、CH2=CClCF2CF2C2F5、およびCHCl=CHCF2CF2C2F5からなる群から選択される少なくとも1つの不飽和フッ素化炭化水素をさらに含むことを特徴とする請求項1に記載の方法。
- 前記組成物がエアロゾル噴射剤をさらに含むことを特徴とする請求項1に記載の方法。
- 前記組成物が界面活性剤をさらに含むことを特徴とする請求項1に記載の方法。
- 前記組成物が共溶媒をさらに含むことを特徴とする請求項1に記載の方法。
- 前記接触が蒸気脱脂によって行われることを特徴とする請求項1に記載の方法。
- 前記蒸気脱脂が
(i)前記組成物を沸騰させること、および
(ii)物品を、沸騰している該清浄剤組成物の蒸気に曝露すること
によって行われることを特徴とする請求項8に記載の方法。 - 前記接触が物品を前記組成物に浸漬することによって行われ、前記組成物が周囲温度または室温より高い温度であることを特徴とする請求項1に記載の方法。
- 前記組成物の温度が、前記組成物の沸点付近であることを特徴とする請求項10に記載の方法。
- 前記物品を前記組成物に浸漬した後、前記物品を前記組成物に浸漬するさらなるステップを含み、その際、前記組成物が第1の浸漬ステップの温度より低い温度であることを特徴とする請求項10に記載の方法。
- 第2の浸漬ステップの前記組成物が、周囲温度または室温であることを特徴とする請求項12に記載の方法。
- 第2の浸漬ステップの後、前記組成物を沸騰させるステップと、前記物品を該沸騰組成物の蒸気に曝露するステップとをさらに含むことを特徴とする請求項12に記載の方法。
- 前記組成物が周囲温度または室温であることを特徴とする請求項1に記載の方法。
- 前記組成物に浸した物体で物品を塗りつけることによって前記接触が行われることを特徴とする請求項1に記載の方法。
- フッ素系潤滑剤を表面に被着させる方法であって、
(a)フッ素系潤滑剤と溶媒を組み合わせて、潤滑剤−溶媒の組合せを形成するステップであって、前記溶媒が、式E−またはZ−R1CH=CHR2(式中、R1およびR2は独立に、C1〜C6パーフルオロアルキル基、またはC1〜C6ヒドロフルオロアルキル基である)を有する不飽和フッ素化炭化水素類からなる群から選択される不飽和フッ素化炭化水素を含むステップと、
(b)潤滑剤−溶媒の前記組合せを前記表面と接触させるステップと、
(c)前記溶媒を前記表面から蒸発させて、フッ素系潤滑剤コーティングを前記表面に形成するステップと
を含むことを特徴とする方法。 - 前記表面が、半導体材料、金属、金属酸化物、蒸着炭素、またはガラスの表面であることを特徴とする請求項17に記載の方法。
- 前記表面が磁気媒体の表面であることを特徴とする請求項18に記載の方法。
- 前記磁気媒体がコンピュータディスクであることを特徴とする請求項19に記載の方法。
- 前記接触ステップが、前記フッ素系潤滑剤を含む浴に前記表面を部分的または完全に浸漬する(dipping or immersing)ことによって行われることを特徴とする請求項17に記載の方法。
- 前記接触ステップが、前記表面に前記フッ素系潤滑剤を吹き付ける、またはスピンコーティングすることによって行われることを特徴とする請求項17に記載の方法。
- 前記潤滑剤−溶媒の組合せのフッ素系潤滑剤濃度が、約0.02重量パーセント〜0.5重量パーセントであることを特徴とする請求項17に記載の方法。
- 前記蒸発ステップが、約10℃〜約40℃の温度で行われることを特徴とする請求項17に記載の方法。
- 前記フッ素系潤滑剤がパーフルオロポリエーテルを含むことを特徴とする請求項17に記載の方法。
- 前記フッ素系潤滑剤が、パーフルオロポリエーテル類およびその混合物からなる群から選択されることを特徴とする請求項17に記載の方法。
- 濡れた基板の表面から、少なくとも水の一部分を除去する方法であって、
a)界面活性剤をさらに含む請求項1に記載の組成物と前記基板を接触させるステップと、次いで
b)前記基材を前記組成物との接触から外すステップと
を含むことを特徴とする方法。 - 式R1CH=CHR2を有する不飽和フッ素化炭化水素(式中、R1およびR2は独立に、C1〜C6パーフルオロアルキル基またはC1〜C6ヒドロフルオロアルキル基である)から本質的に構成されることを特徴とする溶媒組成物。
- R1およびR2が独立に、CF3、C2F5、CF2CF2CF3、CF(CF3)2、CF2CF2CF2CF3、CF(CF3)CF2CF3、CF2CF(CF3)2、C(CF3)3、CF2CF2CF2CF2CF3、CF2CF2CF(CF3)2、C(CF3)2C2F5、CF2CF2CF2CF2CF2CF3、CF(CF3)CF2CF2C2F5、C(CF3)2CF2C2F5、CHF2、CH2F、C2HF4、C2H2F3、C2H3F2、C3HF6、i−C3HF6、C3H2F5、C3H3F4、C4HF8、C4H3F6、C5HF10、C5H3F8、またはC6HF12であることを特徴とする請求項28に記載の溶媒組成物。
- 前記不飽和フッ素化炭化水素が、CF3CH=CHCF3、CF3CH=CHC2F5、CF3CH=CHCF2C2F5、CF3CH=CHCF(CF3)2、C2F5CH=CHC2F5、CF3CH=CH(CF2)3CF3、CF3CH=CHCF2CF(CF3)2、CF3CH=CHCF(CF3)C2F5、CF3CH=CHC(CF3)3、C2F5CH=CHCF2C2F5、C2F5CH=CHCF(CF3)2、CF3CH=CH(CF2)4CF3、CF3CH=CHCF2CF2CF(CF3)2、CF3CH=CHC(CF3)2C2F5、C2F5CH=CH(CF2)3CF3、C2F5CH=CHCF2CF(CF3)2、C2F5CH=CHCF(CF3)C2F5、C2F5CH=CHC(CF3)3、C2F5CF2CH=CHCF2C2F5、(CF3)2CFCH=CHCF(CF3)2、C2F5CF2CH=CHCF(CF3)2、CF3CH=CH(CF2)5CF3、CF3CH=CHCF(CF3)(CF2)2C2F5、CF3CH=CHC(CF3)2CF2C2F5、C2F5CH=CH(CF2)4CF3、C2F5CH=CHCF2CF2CF(CF3)2、C2F5CH=CHC(CF3)2C2F5、C2F5CF2CH=CH(CF2)3CF3、C2F5CF2CH=CHCF2CF(CF3)2、C2F5CF2CH=CHCF(CF3)C2F5、C2F5CF2CH=CHC(CF3)3、(CF3)2CFCH=CH(CF2)3CF3、(CF3)2CFCH=CHCF2CF(CF3)2、(CF3)2CFCH=CHCF(CF3)C2F5、(CF3)2CFCH=CHC(CF3)3、C2F5CH=CH(CF2)5CF3、C2F5CH=CHCF(CF3)(CF2)2C2F5、C2F5CH=CHC(CF3)2CF2C2F5、C2F5CF2CH=CH(CF2)4CF3、C2F5CF2CH=CHCF2CF2CF(CF3)2、C2F5CF2CH=CHC(CF3)2C2F5、(CF3)2CFCH=CH(CF2)4CF3、(CF3)2CFCH=CHCF2CF2CF(CF3)2、(CF3)2CFCH=CHC(CF3)2C2F5、CF3(CF2)3CH=CH(CF2)3CF3、CF3(CF2)3CH=CHCF2CF(CF3)2、CF3(CF2)3CH=CHCF(CF3)C2F5、CF3(CF2)3CH=CHC(CF3)3、(CF3)2CFCF2CH=CHCF2CF(CF3)2、(CF3)2CFCF2CH=CHCF(CF3)C2F5、(CF3)2CFCF2CH=CHC(CF3)3、C2F5CF(CF3)CH=CHCF(CF3)C2F5、C2F5CF(CF3)CH=CHC(CF3)3、または(CF3)3CCH=CHC(CF3)3の少なくとも1つであることを特徴とする請求項28に記載の溶媒組成物。
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2006
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- 2006-11-01 MY MYPI20113485 patent/MY151990A/en unknown
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2008
- 2008-05-30 KR KR1020087013071A patent/KR101343772B1/ko active IP Right Grant
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2010
- 2010-03-01 US US12/714,709 patent/US7959828B2/en active Active
- 2010-04-01 US US12/752,301 patent/US7846355B2/en not_active Expired - Fee Related
- 2010-10-26 US US12/912,144 patent/US20110041878A1/en not_active Abandoned
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2011
- 2011-06-06 US US13/153,599 patent/US8349213B2/en not_active Expired - Fee Related
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2013
- 2013-07-24 US US13/949,569 patent/US20140034867A1/en not_active Abandoned
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2014
- 2014-11-25 US US14/552,949 patent/US20150080485A1/en not_active Abandoned
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JP2009514251A (ja) * | 2005-11-01 | 2009-04-02 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 不飽和フッ素化炭化水素類を含む溶媒組成物 |
JP2009513816A (ja) * | 2005-11-01 | 2009-04-02 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | トリデカフルオロ−3−ヘプテンとフッ化水素とを含む共沸組成物およびその使用 |
JP2011525209A (ja) * | 2008-06-20 | 2011-09-15 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | Z−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンの共沸および共沸混合物様組成物 |
JP2014224267A (ja) * | 2008-06-20 | 2014-12-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company | Z−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンの共沸および共沸混合物様組成物 |
JP2016186077A (ja) * | 2008-12-17 | 2016-10-27 | ハネウェル・インターナショナル・インコーポレーテッド | 洗浄組成物及び方法 |
JP2015110802A (ja) * | 2009-02-16 | 2015-06-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company | 新規なアルキルパーフルオロアルケンエーテルおよびその使用 |
JPWO2018159378A1 (ja) * | 2017-03-02 | 2020-01-16 | 昭和電工株式会社 | 磁気記録媒体用潤滑剤および磁気記録媒体の製造方法 |
WO2018159378A1 (ja) * | 2017-03-02 | 2018-09-07 | 昭和電工株式会社 | 磁気記録媒体用潤滑剤および磁気記録媒体の製造方法 |
JP7034135B2 (ja) | 2017-03-02 | 2022-03-11 | 昭和電工株式会社 | 磁気記録媒体用潤滑剤および磁気記録媒体の製造方法 |
US11514945B2 (en) | 2017-03-02 | 2022-11-29 | Showa Denko K.K. | Lubricant for magnetic recording medium, and method for producing magnetic recording medium |
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JPWO2019039521A1 (ja) * | 2017-08-25 | 2020-11-05 | Agc株式会社 | 溶剤組成物、洗浄方法、塗膜付き基材の製造方法及び熱移動媒体 |
US11254824B2 (en) | 2017-08-25 | 2022-02-22 | AGC Inc. | Solvent composition, cleaning method, method for producing substrate with coating film, and heat transfer fluid |
JP7205476B2 (ja) | 2017-08-25 | 2023-01-17 | Agc株式会社 | 溶剤組成物、洗浄方法、塗膜付き基材の製造方法及び熱移動媒体 |
JP2020139022A (ja) * | 2019-02-27 | 2020-09-03 | Agc株式会社 | 溶剤組成物、洗浄方法、塗膜付き物品の製造方法 |
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