JP2009001738A5

JP2009001738A5 -

Info

Publication number: JP2009001738A5
Application number: JP2007166143A
Authority: JP
Filing date: 2007-06-25
Publication date: 2010-10-07
Anticipated expiration: 2027-06-25

Description

本発明者は先に、下記一般式で表わされる含フッ素ポリエーテル化合物を主成分とする硬化性組成物を提案している(WO 2008/126436)。

(X：ヨウ素原子または臭素原子) The present inventor has previously proposed a curable composition containing as a main component a fluorine-containing polyether compound represented by the following general formula ( WO 2008/126436 ).

(X: iodine atom or bromine atom)

また、下記一般式で表わされる含フッ素ポリエーテル化合物を主成分とする硬化性組成物も提案されている(特開2009-1709号公報)。

X：ヨウ素原子または臭素原子 In addition, a curable composition mainly composed of a fluorine-containing polyether compound represented by the following general formula has been proposed ( Japanese Patent Laid-Open No. 2009-1709 ).

X: iodine atom or bromine atom

本発明によって、一般式

(ここで、R¹は水素原子、炭素数1〜3のアルキル基またはフェニル基であり、Xはヨウ素原子または臭素原子であり、Xのフェニル基上の置換位置はNR¹結合置換基に対してm-またはp-位であり、Rfは下記一般式で表わされる2価のパーフルオロポリエーテル基であり、
-CF₂O(CF₂CF₂O)_p(CF₂O)_qCF₂-
ただし(CF₂CF₂O)基および(CF₂O)基は、パーフルオロポリエーテル高分子主鎖に沿ってランダム分布しているパーフルオロオキシアルキレン基であって、p/qは0.2〜5であり、その数平均分子量Mnは500〜20000であり、Zは

であり、ただしR²は水素原子、炭素数1〜3のアルキル基またはフェニル基であり、R³は炭素数2〜10の2価の脂肪族炭化水素基、炭素数6〜20の2価の芳香族炭化水素基あるいは窒素原子、酸素原子または硫黄原子を含む炭素数2〜10の2価のヘテロ環化合物基であり、R⁴は炭素数2〜6の2価の脂肪族炭化水素基であり、nは1以上の整数である)で表わされ、25℃における粘度が10〜3000Pa・sである含フッ素ポリエーテル化合物が提供される。 According to the invention, the general formula

(Wherein R ¹ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a phenyl group, X is an iodine atom or a bromine atom, and the substitution position on the phenyl group of X is relative to the NR ¹ bond substituent. M- or p-position, and Rf is a divalent perfluoropolyether group represented by the following general formula:
-CF ₂ O (CF ₂ CF ₂ O) _p (CF ₂ O) _q CF _2-
However, the (CF ₂ CF ₂ O) group and the (CF ₂ O) group are perfluorooxyalkylene groups randomly distributed along the perfluoropolyether polymer main chain, and p / q is 0.2 to 5 Its number average molecular weight Mn is 500-20000, Z is

Wherein R ² is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a phenyl group, R ³ is a divalent aliphatic hydrocarbon group having 2 to 10 carbon atoms , and a divalent atom having 6 to 20 carbon atoms. An aromatic hydrocarbon group or a divalent heterocyclic compound group having 2 to 10 carbon atoms containing a nitrogen atom, oxygen atom or sulfur atom, and R ⁴ is a divalent aliphatic hydrocarbon group having 2 to 6 carbon atoms And n is an integer of 1 or more), and a fluorine-containing polyether compound having a viscosity at 25 ° C. of 10 to 3000 Pa · s is provided.

かかる含フッ素ポリエーテル化合物は、一般式

(ここで、Rfは下記一般式で表わされる2価のパーフルオロポリエーテル基であり、
-CF₂O(CF₂CF₂O)_p(CF₂O)_qCF₂-
ただし(CF₂CF₂O)基および(CF₂O)基は、パーフルオロポリエーテル高分子主鎖に沿ってランダム分布しているパーフルオロオキシアルキレン基であって、p/qは0.2〜5であり、その数平均分子量Mnは500〜20000であり、Zは

であり、ただしR²は水素原子、炭素数1〜3のアルキル基またはフェニル基であり、R³は炭素数2〜10の2価の脂肪族炭化水素基、炭素数6〜20の2価の芳香族炭化水素基あるいは窒素原子、酸素原子または硫黄原子を含む炭素数2〜10の2価のヘテロ環化合物基であり、R⁴は炭素数2〜6の2価の脂肪族炭化水素基であり、nは1以上の整数である)で表わされる含フッ素ジカルボン酸フルオリド化合物を、一般式

(ここで、R¹は水素原子、炭素数1〜3のアルキル基またはフェニル基であり、Xはヨウ素原子または臭素原子であり、Xのフェニル基上の置換位置はNR¹結合置換基に対してm-またはp-位である)で表わされる芳香族1級または2級アミン化合物と、好ましくはピリジン等の活性水素を有しない塩基性含窒素複素環化合物またはトリエチルアミン等の3級アミン化合物の存在下で反応させることにより製造される。 Such fluorine-containing polyether compounds have the general formula

(Where Rf is a divalent perfluoropolyether group represented by the following general formula:
-CF ₂ O (CF ₂ CF ₂ O) _p (CF ₂ O) _q CF _2-
However, the (CF ₂ CF ₂ O) group and the (CF ₂ O) group are perfluorooxyalkylene groups randomly distributed along the perfluoropolyether polymer main chain, and p / q is 0.2 to 5 Its number average molecular weight Mn is 500-20000, Z is

Wherein R ² is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a phenyl group, R ³ is a divalent aliphatic hydrocarbon group having 2 to 10 carbon atoms , and a divalent atom having 6 to 20 carbon atoms. An aromatic hydrocarbon group or a divalent heterocyclic compound group having 2 to 10 carbon atoms containing a nitrogen atom, oxygen atom or sulfur atom, and R ⁴ is a divalent aliphatic hydrocarbon group having 2 to 6 carbon atoms Wherein n is an integer of 1 or more), a fluorine-containing dicarboxylic acid fluoride compound represented by the general formula

(Wherein R ¹ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a phenyl group, X is an iodine atom or a bromine atom, and the substitution position on the phenyl group of X is relative to the NR ¹ bond substituent. An aromatic primary or secondary amine compound, preferably a basic nitrogen-containing heterocyclic compound having no active hydrogen such as pyridine, or a tertiary amine compound such as triethylamine. It is produced by reacting in the presence.

Rfは、下記一般式で表わされる2価のパーフルオロポリエーテル基であり、
-CF₂O(CF₂CF₂O)_p(CF₂O)_qCF₂-
(CF₂CF₂O)基および(CF₂O)基は、パーフルオロポリエーテル高分子主鎖に沿ってランダム分布しているパーフルオロオキシアルキレン基であって、p/qは0.2〜5であり、その数平均分子量Mnは500〜20000である。 Rf is a divalent perfluoropolyether group represented by the following general formula:
-CF ₂ O (CF ₂ CF ₂ O) _p (CF ₂ O) _q CF _2-
(CF ₂ CF ₂ O) group and (CF ₂ O) group are perfluorooxyalkylene groups randomly distributed along the main chain of the perfluoropolyether polymer, and p / q is 0.2-5. The number average molecular weight Mn is 500-20000.

また、Zは、

であり、R²は水素原子、炭素数1〜3のアルキル基またはフェニル基であり、R³は炭素数2〜10の2価の脂肪族炭化水素基、炭素数6〜20の2価の芳香族炭化水素基または窒素原子、酸素原子、硫黄原子等のヘテロ原子を含む炭素数2〜10の2価の複素環化合物基であり、R⁴は炭素数2〜6の2価の脂肪族炭化水素基である。 Z is

R ² is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a phenyl group, R ³ is a divalent aliphatic hydrocarbon group having 2 to 10 carbon atoms , and a divalent aliphatic hydrocarbon group having 6 to 20 carbon atoms . An aromatic hydrocarbon group or a divalent heterocyclic compound group having 2 to 10 carbon atoms containing a hetero atom such as a nitrogen atom, oxygen atom or sulfur atom, and R ⁴ is a divalent aliphatic having 2 to 6 carbon atoms It is a hydrocarbon group.

Zは、

である。ここで、R²は水素原子、炭素数1〜3のアルキル基またはフェニル基であるが、分子内または分子間水素結合および硬化における副反応を避けるために、炭素数1〜3のアルキル基またはフェニル基が好ましい。特に原料の入手のし易さから、メチル基が選ばれる。R³は炭素数2〜10の2価の脂肪族炭化水素基、炭素数6〜20の2価の芳香族炭化水素基、または窒素原子、酸素原子、硫黄原子等ヘテロ原子を含む素炭数2〜10の2価の複素環化合物基であり、R⁴は炭素数2〜6の2価の脂肪族炭化水素基である。Zの具体例としては、前記したものが挙げられる。 Z is

It is. Here, R ² is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a phenyl group, but in order to avoid side reactions in intramolecular or intermolecular hydrogen bonding and curing, an alkyl group having 1 to 3 carbon atoms or A phenyl group is preferred. In particular, a methyl group is selected because of easy availability of raw materials. R ³ is the number Motosumi containing divalent aliphatic hydrocarbon group having 2 to 10 carbon atoms, divalent aromatic hydrocarbon group having 6 to 20 carbon atoms or a nitrogen atom, an oxygen atom, a sulfur atom or the like heteroatom a divalent heterocyclic compound group of 2 to 10, R ⁴ is a divalent aliphatic hydrocarbon group having 2 to 6 carbon atoms. Specific examples of Z include those described above.

その他、分子内に2個のリン原子を有する、一般式

で表わされる二座配位子有機リン化合物も用いることができる。ここで、R⁹は置換基を有し得るフェニル基または炭素数1〜6の脂肪族炭化水素基であり、Yは炭素数1〜10の2価の脂肪族炭化水素基、炭素数6〜20の2価の芳香族炭化水素基またはメタロセン基である。 Other general formulas with two phosphorus atoms in the molecule

A bidentate organophosphorus compound represented by the formula can also be used. Here, R ⁹ is a phenyl group which may have a substituent or an aliphatic hydrocarbon group having 1 to 6 carbon atoms, Y is a divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, 6 to 6 carbon atoms 20 divalent aromatic hydrocarbon group or metallocene group.

(2) 上記(1)で得られた含フッ素ジカルボン酸フルオリド、フッ化セシウムおよびテトラグライムからなる混合物120g(約6.9ミリモル)を、含フッ素系溶媒(住友3M製品HFE-7100)100mlに溶解し、そこにトリエチルアミン2.7g(27ミリモル)およびジエチルエーテル40mlを加えた。これに、p-ヨード-N-メチルアニリン3.9g(17ミリモル)を加え、室温で1時間反応を行った。得られた反応混合物を飽和食塩水に加え、分離した有機層を無水硫酸マグネシウムで乾燥し、ロ過した。減圧下でロ液から含フッ素系溶媒およびジエチルエーテルを留去した後、得られた粘稠な液体をジエチルエーテルで数回洗浄し、次いで減圧下でジエチルエーテルを完全に留去した。このようにして、含フッ素ポリエーテル化合物

を、僅かに黄色味を帯びた透明な液体として104g得た。E型粘度計(東機産業製TEV-22)により粘度を測定したところ、15Pa・s(25℃)であった。
¹⁹F-NMR(ケミカルシフトはCFCl₃基準)： -123ppm(F^b)
-146ppm(F^c)
¹H-NMR(ケミカルシフトはTMS基準)： 7.5ppm(H^a)
6.7ppm(H^b)
3.0ppm(H^c)
IR(neat)： 1702cm^-1(C=O)
1488cm^-1(Ar) (2) 120 g (about 6.9 mmol) of a mixture comprising the fluorine-containing dicarboxylic acid fluoride, cesium fluoride and tetraglyme obtained in (1) above was dissolved in 100 ml of a fluorine-containing solvent (Sumitomo 3M product HFE-7100). Thereto were added 2.7 g (27 mmol) of triethylamine and 40 ml of diethyl ether. To this, 3.9 g (17 mmol) of p-iodo-N-methylaniline was added and reacted at room temperature for 1 hour. The obtained reaction mixture was added to saturated brine, and the separated organic layer was dried over anhydrous magnesium sulfate and filtered. After distilling off the fluorine-containing solvent and diethyl ether from the filtrate under reduced pressure, the resulting viscous liquid was washed several times with diethyl ether, and then diethyl ether was completely distilled off under reduced pressure. Thus, a fluorine-containing polyether compound

104 g were obtained as a slightly yellowish transparent liquid. When the viscosity was measured with an E-type viscometer (TEV-22 manufactured by Toki Sangyo), it was 15 Pa · s (25 ° C.).
¹⁹ F-NMR (chemical shift based on CFCl ₃ ): -123 ppm (F ^b )
-146ppm (F ^c )
¹ H-NMR (chemical shift is based on TMS): 7.5 ppm (H ^a )
6.7ppm (H ^b )
3.0ppm (H ^c)
IR (neat): 1702cm ^-1 (C = O)
1488cm ^-1 (Ar)

参考例２
含フッ素ジカルボン酸フルオリド

50g(約6.1ミリモル)を、含フッ素系溶媒(HFE-7100)50mlに溶解し、そこにトリエチルアミン2.4g(24ミリモル)およびジエチルエーテル20mlを加えた。これに、p-ヨード-N-メチルアニリン3.5g(15ミリモル)を室温で加えて、1時間反応を行った。得られた反応混合物を飽和食塩水中に加え、分離した有機層を無水硫酸マグネシウムで乾燥し、ロ過した。減圧下でロ液から含フッ素系溶媒およびジエチルエーテルを留去した後、得られた粘稠な液体をジエチルエーテルで数回洗浄し、次いで減圧下でジエチルエーテルを完全に留去した。このようにして、含フッ素ポリエーテル化合物(n=0)

を黄色味を帯びた液体として35g得た。E型粘度計(東機産業製TEV-22)により粘度を測定したところ、6.0Pa・s(25℃)であった。

¹⁹F-NMR(ケミカルシフトはCFCl₃基準)： -52ppm -OCF₂CF₂OCF ₂OCF₂CF₂O-
-53ppm -OCF₂OCF ₂OCF₂CF₂O-
-55ppm -OCF₂OCF ₂OCF₂O-
-89ppm -OCF₂CF₂OCF ₂CF ₂OCF₂CF₂O-
-OCF₂OCF₂CF ₂OCF₂CF₂O-
-90ppm -OCF₂OCF ₂CF₂OCF₂CF₂O-
-OCF₂OCF ₂CF ₂OCF₂O-
-68ppm -OCF₂OCF ₂CON(CH₃)-
-70ppm -OCF₂CF₂OCF ₂CON(CH₃)-
¹H-NMR(ケミカルシフトはTMS基準)： 7.5ppm(H^a)
6.7ppm(H^b)
3.0ppm(H^c)
IR(neat)： 1710cm^-1(C=O)
1490cm^-1(Ar) Reference example 2
Fluorine-containing dicarboxylic acid fluoride

50 g (about 6.1 mmol) was dissolved in 50 ml of a fluorine-containing solvent (HFE-7100), and 2.4 g (24 mmol) of triethylamine and 20 ml of diethyl ether were added thereto. To this, 3.5 g (15 mmol) of p-iodo-N-methylaniline was added at room temperature and reacted for 1 hour. The obtained reaction mixture was added to saturated brine, and the separated organic layer was dried over anhydrous magnesium sulfate and filtered. After distilling off the fluorine-containing solvent and diethyl ether from the filtrate under reduced pressure, the resulting viscous liquid was washed several times with diethyl ether, and then diethyl ether was completely distilled off under reduced pressure. In this way, fluorine-containing polyether compound (n = 0)

Was obtained as a yellowish liquid. The viscosity was measured with an E-type viscometer (TEV-22 manufactured by Toki Sangyo Co., Ltd.) and found to be 6.0 Pa · s (25 ° C.).

¹⁹ F-NMR (chemical shift based on CFCl ₃ ): -52 ppm -OCF ₂ CF ₂ OC F ₂ OCF ₂ CF ₂ O-
-53ppm -OCF ₂ OC F ₂ OCF ₂ CF ₂ O-
-55ppm -OCF ₂ OC F ₂ OCF ₂ O-
-89ppm -OCF ₂ CF ₂ OC F ₂ C F ₂ OCF ₂ CF ₂ O-
-OCF ₂ OCF ₂ C F ₂ OCF ₂ CF ₂ O-
-90ppm -OCF ₂ OC F ₂ CF ₂ OCF ₂ CF ₂ O-
-OCF ₂ OC F ₂ C F ₂ OCF ₂ O-
-68ppm -OCF ₂ OC F ₂ CON (CH ₃ )-
-70ppm -OCF ₂ CF ₂ OC F ₂ CON (CH ₃ )-
¹ H-NMR (chemical shift is based on TMS): 7.5 ppm (H ^a )
6.7ppm (H ^b )
3.0ppm (H ^c)
IR (neat): 1710cm ^-1 (C = O)
1490cm ^-1 (Ar)

実施例１
参考例2で用いられた含フッ素ジカルボン酸フルオリド60g(約7.4ミリモル)を、含フッ素系溶媒(HFE-7100)50mlに溶解し、そこにトリエチルアミン3.0g(30ミリモル)およびジエチルエーテル20mlを加えた。これにN,N′-ジメチル-p-フェニレンジアミン0.5g(3.7ミリモル)のジエチルエーテル溶液20mlを、室温で30分間かけて加え、さらに30分間反応を行った。次いで、p-ヨード-N-メチルアニリン2.6g(11ミリモル)を加えて、さらに1時間反応を行った。得られた反応混合物を飽和食塩水中に加え、分離した有機層を無水硫酸マグネシウムで乾燥し、ロ過した。減圧下でロ液から含フッ素系溶媒およびジエチルエーテルを留去した後、得られた粘稠な液体をジエチルエーテルで数回洗浄し、次いで減圧下でジエチルエーテルを完全に留去した。このようにして、含フッ素ポリエーテル化合物

Rf：-CF₂O(CF₂CF₂O)_p(CF₂O)_qCF₂-
を黄色味を帯びた液体として45g得た。E型粘度計(東機産業製TEV-22)により粘度を測定したところ、50Pa・s(25℃)であった。なお、¹⁹F-NMR、¹H-NMRおよびIRの特性値は、参考例２とほぼ同じ値であった。 Example 1
60 g (about 7.4 mmol) of the fluorine-containing dicarboxylic acid fluoride used in Reference Example 2 was dissolved in 50 ml of a fluorine-containing solvent (HFE-7100), and 3.0 g (30 mmol) of triethylamine and 20 ml of diethyl ether were added thereto. . To this, 20 ml of a diethyl ether solution of 0.5 g (3.7 mmol) of N, N′-dimethyl-p-phenylenediamine was added over 30 minutes at room temperature, and the reaction was further carried out for 30 minutes. Subsequently, 2.6 g (11 mmol) of p-iodo-N-methylaniline was added, and the reaction was further performed for 1 hour. The obtained reaction mixture was added to saturated brine, and the separated organic layer was dried over anhydrous magnesium sulfate and filtered. After distilling off the fluorine-containing solvent and diethyl ether from the filtrate under reduced pressure, the resulting viscous liquid was washed several times with diethyl ether, and then diethyl ether was completely distilled off under reduced pressure. Thus, a fluorine-containing polyether compound

Rf: -CF ₂ O (CF ₂ CF ₂ O) _p (CF ₂ O) _q CF _2-
Was obtained as a yellowish liquid. When the viscosity was measured with an E-type viscometer (TEV-22 manufactured by Toki Sangyo), it was 50 Pa · s (25 ° C.). The ¹⁹ F-NMR, ¹ H-NMR and IR characteristic values were almost the same as those in Reference Example 2.

以上の結果から、次のようなことがいえる。
(1)比較例1では、ヘキサフルオロプロペンオキシドくり返し単位を有する含フッ素ポリエーテル化合物を用いてはいるが、その硬化物のTgは-55℃である。
(2)比較例2では、(CF₂CF₂O)基と(CF₂O)基とのランダムくり返し単位からなる含フッ素ポリエーテル化合物が用いられており、その硬化物のTgは-105℃となるが、その硬化物強度は比較例1よりも低くなる傾向にある。
これは、その合成原料となるFOCCF₂(CF₂CF₂O)_p(CF₂O)_qCF₂COFでは分子量10000以上の高分子量物を得ることがその製法上困難であることおよび -OCF₂O- の回転障壁が -CF(CF₃)CF₂O- よりも低く、主鎖構造の剛性が低いことによる。
(3)このような点を考慮して、硬化物の機械的強度を増加させるために、本発明のような主鎖構造をオリゴマー化する方法がとられ、これにより主鎖構造を高分子量化することで低温特性を維持しながら、硬化物の機械的強度の向上を図ることができる。 From the above results, the following can be said.
(1) In Comparative Example 1, although a fluorinated polyether compound having hexafluoropropene oxide repeating units is used, the Tg of the cured product is -55 ° C.
(2) In Comparative Example 2, a fluorinated polyether compound composed of random repeating units of (CF ₂ CF ₂ O) group and (CF ₂ O) group is used, and the Tg of the cured product is −105 ° C. However, the strength of the cured product tends to be lower than that of Comparative Example 1.
This is because it is difficult to obtain a high molecular weight product having a molecular weight of 10,000 or more with FOCCF ₂ (CF ₂ CF ₂ O) _p (CF ₂ O) _q CF ₂ COF, which is a raw material for synthesis, and -OCF ₂ This is because the rotation barrier of O- is lower than that of -CF (CF ₃ ) CF ₂ O- and the rigidity of the main chain structure is low.
(3) Considering these points, in order to increase the mechanical strength of the cured product, a method of oligomerizing the main chain structure as in the present invention is taken, thereby increasing the molecular weight of the main chain structure. Thus, the mechanical strength of the cured product can be improved while maintaining the low temperature characteristics.

Claims

General formula

Wherein R ² is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a phenyl group, R ³ is a divalent aliphatic hydrocarbon group having 2 to 10 carbon atoms , and a divalent atom having 6 to 20 carbon atoms. An aromatic hydrocarbon group or a divalent heterocyclic compound group having 2 to 10 carbon atoms containing a nitrogen atom, oxygen atom or sulfur atom, and R ⁴ is a divalent aliphatic hydrocarbon group having 2 to 6 carbon atoms And n is an integer of 1 or more), and has a viscosity at 25 ° C. of 10 to 3000 Pa · s.

General formula

(Where Rf is a divalent perfluoropolyether group represented by the following general formula:
-CF ₂ O (CF ₂ CF ₂ O) _p (CF ₂ O) _q CF _2-
However, the (CF ₂ CF ₂ O) group and the (CF ₂ O) group are perfluorooxyalkylene groups randomly distributed along the main chain of the perfluoropolyether polymer, and p / q is 0.2 to 5, the number average molecular weight Mn is 500-20000, Z is

(Wherein R ¹ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a phenyl group, X is an iodine atom or a bromine atom, and the substitution position on the phenyl group of X is relative to the NR ¹ bond substituent. 2. The method for producing a fluorinated polyether compound according to claim 1, wherein the reaction is carried out with an aromatic primary or secondary amine compound represented by the formula (M- or p-position).

(A) 100 parts by weight of the fluorine-containing polyether compound according to claim 1
(B) General formula

(Where R ⁵ is a straight chain of 2 to 10 carbon atoms or
(This is a branched divalent aliphatic hydrocarbon group.)
Aromatic boronic acid ester compound represented by 0.1 to 10 parts by weight
(C) Zero or divalent organopalladium compound 0.0001 to 1 part by weight
(D) Basic inorganic compound or basic organic compound 0.1 to 10 parts by weight
(E) General formula

(Here, R ⁶ , R ⁷ and R ⁸ are each independently a chain aliphatic hydrocarbon group having 1 to 10 carbon atoms and a cyclic aliphatic hydrocarbon having 5 to 12 carbon atoms which may have a substituent. (A hydrocarbon group or an aromatic hydrocarbon group having 6 to 20 carbon atoms)
Or general formula

(Where R ⁹ is a phenyl group which may have a substituent or an aliphatic hydrocarbon group having 1 to 6 carbon atoms;
Y is a divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms ,
(It is a C6-C20 divalent aromatic hydrocarbon group or metallocene group.)
A curable fluorine-containing polyether composition comprising 0 to 5 parts by weight of an organic phosphorus compound represented by the formula: