JPH01305045A - Fluorine-containing diol and production thereof - Google Patents
Fluorine-containing diol and production thereofInfo
- Publication number
- JPH01305045A JPH01305045A JP63134569A JP13456988A JPH01305045A JP H01305045 A JPH01305045 A JP H01305045A JP 63134569 A JP63134569 A JP 63134569A JP 13456988 A JP13456988 A JP 13456988A JP H01305045 A JPH01305045 A JP H01305045A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- water
- fluorine
- compound
- containing diol
- 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.)
- Granted
Links
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 150000002009 diols Chemical class 0.000 title claims abstract description 14
- 239000011737 fluorine Substances 0.000 title claims abstract description 14
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000007524 organic acids Chemical class 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- 150000002576 ketones Chemical class 0.000 claims abstract description 3
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 3
- 150000002170 ethers Chemical class 0.000 claims abstract 2
- 239000003960 organic solvent Substances 0.000 claims abstract 2
- 150000003457 sulfones Chemical class 0.000 claims abstract 2
- 150000003462 sulfoxides Chemical class 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 239000011347 resin Substances 0.000 abstract description 8
- 229920005989 resin Polymers 0.000 abstract description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 7
- 239000004593 Epoxy Substances 0.000 abstract description 4
- 238000010521 absorption reaction Methods 0.000 abstract description 4
- 239000003607 modifier Substances 0.000 abstract description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 abstract description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は樹脂改質剤として有用な新規の含フツ素ジオー
ルおよびその製造法に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a novel fluorine-containing diol useful as a resin modifier and a method for producing the same.
（従来技術とその問題点）
既知の含フツ素ジオールは、一般式
Ｃ式中Ｒｆは炭素数１〜２０のペルフルオロアルキル基
であり、ＸはＣＨｔ 、Ｓ Ｏｓ 、またはＳＯ基）で
表わされる化合物で、樹脂に撥水・撥油性、低屈折率等
を付与するための改質剤として使用されている（特公昭
６２−２２９８２号公報。(Prior art and its problems) Known fluorine-containing diols are compounds represented by the general formula C (where Rf is a perfluoroalkyl group having 1 to 20 carbon atoms and X is a CHt, SOs, or SO group). It is used as a modifier to impart water and oil repellency, low refractive index, etc. to resins (Japanese Patent Publication No. 62-22982).
特公昭６２−２２９８３号公報１％開昭５３−８４９０
９号公報、特開昭６２−２２７３５号公報、ドイツ特許
１５６８３７８号明細書）。Special Publication No. Sho 62-22983 1% Kai Sho 53-8490
9, Japanese Patent Application Laid-Open No. 62-22735, German Patent No. 1568378).
近年、樹脂の撥水・撥油性、低屈折率の特性の向上が要
求されてきており、そのような用途に前記の既知含フツ
素ジオールを中間体として使用した場合、撥水・撥油性
、低屈折率の向上は見られるものの、（Ｉ）式中のＸが
ＳＯｌおよびＳＯ基である化合物は吸水性が高く、耐候
性に乏しいという欠点があった。また、Ｃ１式のＸがＣ
ＨＩである化金物は、上記の欠点が改良されているもの
の、これを用いて合成された樹脂は弾性に乏しいという
欠点があった。In recent years, there has been a demand for improved water and oil repellency and low refractive index properties of resins, and when the above-mentioned known fluorine-containing diols are used as intermediates for such applications, water and oil repellency, Although an improvement in low refractive index can be seen, compounds in which X in formula (I) is an SOI or SO group have the drawbacks of high water absorption and poor weather resistance. Also, X in formula C1 is C
Although the above-mentioned drawbacks of the metal compound, which is HI, have been improved, the resin synthesized using it has the drawback of poor elasticity.
（発明の目的）
本発明者らは上記の問題点を解決し、撥水・撥油性、低
屈折率の向上の確保とともに、吸水性。(Objective of the Invention) The present inventors have solved the above problems, and have improved water repellency, oil repellency, and low refractive index, as well as water absorption.
耐候性の改良及び弾性の増進を可能ならしめる含フツ素
ジオールな提供すべく、鋭意研究した結果、分子中にエ
ーテル結合な有する含フツ素ジオールが上記目的を達成
することを見出し、本発明に到達した。In order to provide a fluorine-containing diol that can improve weather resistance and increase elasticity, as a result of intensive research, it was discovered that a fluorine-containing diol having an ether bond in the molecule achieves the above objectives, and the present invention Reached.
（発明の構成）
すなわち、本発明によれば、
Ｒｆ（ＣＨＩ ） ｎ０ｃＨｔ ＣＨＣＨ＊ Ｏｆ（・
・・’ ・（１）Ｈ
Ｃ式中Ｒ７は炭素原子数４〜２０のペルフルオロアルキ
ル基、ｎは１または２の整数）で表わされることを特徴
とする含フツ素ジオールが得られる。(Structure of the Invention) That is, according to the present invention, Rf(CHI) n0cHt CHCH* Of(・
...' (1) A fluorine-containing diol is obtained, characterized in that R7 in the H C formula is represented by a perfluoroalkyl group having 4 to 20 carbon atoms, and n is an integer of 1 or 2.
本発明の含フツ素ジオールは、分子中に存在する２個の
水酸基が反応することによって縮合型のモノマーとして
作用することが可能となり、かつペルフルオロアルキル
基が撥水・撥油性、低屈折率といったフッ素化合物特有
の性質な付与し、また、ＳＯｌ、Ｓｏ基を含まないので
吸水性を解消して耐候性を向上し、さらに、分子中に存
在するエーテル結合が分子に柔軟性を付与し、これによ
って樹脂の弾性を高めるものである。The fluorine-containing diol of the present invention can act as a condensed monomer by the reaction of two hydroxyl groups present in the molecule, and the perfluoroalkyl group has properties such as water repellency, oil repellency, and low refractive index. It imparts properties unique to fluorine compounds, and since it does not contain SOI or So groups, it eliminates water absorption and improves weather resistance.Furthermore, the ether bond present in the molecule imparts flexibility to the molecule. This increases the elasticity of the resin.
本発明の含フツ素ジオールはこのように、樹脂改質剤と
して従来のものより一層有用な化合物である。The fluorine-containing diol of the present invention is thus a more useful compound as a resin modifier than conventional ones.
本発明の一般式（１）式で表わされる含フツ素ジオール
において、Ｒｆは炭素原子数４〜２Ｇに限定されたペル
フルオロアルキル基であり、直鎖型、分枝鎖な有するも
ののいずれであってもよい。また、ｎは１または２の整
数である。In the fluorine-containing diol represented by the general formula (1) of the present invention, Rf is a perfluoroalkyl group having a limited number of carbon atoms of 4 to 2G, and may be either a linear type or a branched type. Good too. Further, n is an integer of 1 or 2.
本発明はまた、一般式
（式中Ｒｆは炭素原子数４〜２０のペルフルオロアルキ
ル基、ｎは１または２の整数）で表わされるエポキシ化
合物と水とを、無機または有機酸を触媒として、ケトン
類、エーテル類、スルホキシド数スルホン類より成る群
から選ばれた非反応性有機溶媒中で反応させることｆｔ
特徴とする前記一般弐ｍで表わされる含フツ素ジオール
の製造法を提供するものである。本発明の製造法におい
て、一般式（１）で表わされるエポキシ化合物は一般式
％式％］
Ｃ式中Ｒｆ、ｎは一般式ｆｉｌに同じ）で表わされる化
合物とエビクロロヒドリンとをアルカリ金属水酸化物の
存在下反応させることにより容易に得られる（米国特許
第３．３６１．６８５号明細蓄、同第３，４１７，０３
５号明細書参照）。The present invention also provides an epoxy compound represented by the general formula (in the formula, Rf is a perfluoroalkyl group having 4 to 20 carbon atoms, n is an integer of 1 or 2) and water, using an inorganic or organic acid as a catalyst, to produce a ketone. ft.
The present invention provides a method for producing a fluorine-containing diol characterized by the above-mentioned general formula 2m. In the production method of the present invention, the epoxy compound represented by the general formula (1) is prepared by combining a compound represented by the general formula (% formula %] C (in which Rf and n are the same as the general formula fil) and shrimp chlorohydrin with an alkali metal compound. It can be easily obtained by reaction in the presence of hydroxide (U.S. Pat. No. 3,361,685, U.S. Pat. No. 3,417,03).
(See specification No. 5).
また、一般式ａ）で表わされる化合物は、フッ素化学工
業の原料として一般的な化合物で容易に入手できる。具
体的には次の如きものである。Further, the compound represented by the general formula a) is a common compound and can be easily obtained as a raw material for the fluorochemical industry. Specifically, it is as follows.
ＣｓＦ＋５ＣＨｔＣＨｔＯＨ，ＣｔＦｔａＣＨｔＯＨＣ
ｍ Ｆｔｙ ＣＨｔ ＣＨｚ ＯＨ
使用する水は、一般式ｆｆｆｌで表わされる化合物に対
し１モル以上、好ましくは５モル当量以上用いられ、ま
た酸触媒の使用量は、通常一般式＋ｆｆｌで示される化
合物に対して０．０１ないし５重−１１％であり、使用
する酸としては硫酸、塩酸、硝酸等の鉱酸、あるいは酢
酸、ｐ−トルエンスルホノ酸等の有機酸のいずれであっ
てもよい。反応は３０ないし１００℃、好ましくは６０
ないし９０℃の温度範囲で加熱攪拌することによって行
なわれる。CsF+5CHtCHtOH, CtFtaCHtOHC
m Fty CHt CHz OH The water used is used in an amount of 1 mol or more, preferably 5 mol equivalent or more, based on the compound represented by the general formula fffl, and the amount of the acid catalyst used is usually 1 mol or more, preferably 5 mol equivalent or more, based on the compound represented by the general formula + ffl. The acid used may be mineral acids such as sulfuric acid, hydrochloric acid or nitric acid, or organic acids such as acetic acid or p-toluenesulfonate. The reaction is carried out at 30 to 100°C, preferably 60°C.
This is carried out by heating and stirring at a temperature range of 90°C to 90°C.
次に、本発明を実施例によって具体的に説明するが、以
下の実施例は本発明の範囲を限定するものではない。EXAMPLES Next, the present invention will be specifically explained with reference to Examples, but the following Examples do not limit the scope of the present invention.
実施例１
温度計、攪拌装置、還流冷却器を備えたＳＯＯす
１０２、７ｇ（０−２２５ｍ−） ｙ水５ｏｒｎｌ、溶
媒としテ１．４−ジオ＊＋ ７３００ ｒｒｔｌ、 ｆ
ｌＪ硫酸０６５ｄを入れ油浴を用いて系内な８０℃に力
口熱し、１２時間攪拌を行った。ガスクロマトグラフ分
析の結果、上記エポキシドの消失と反応生成物の存在を
確認した。Example 1 SOO with thermometer, stirrer, reflux condenser 102, 7 g (0-225 m-) y 5 ornl water, 1,4-dio** as solvent 7300 rrtl, f
1J sulfuric acid 065d was added, and the system was vigorously heated to 80° C. using an oil bath, and stirred for 12 hours. As a result of gas chromatography analysis, the disappearance of the epoxide and the presence of reaction products were confirmed.
反応混合液Ｔｉｃ Ｃａ （ＯＨ） ｔを入れて中和し
た後、生成した沈殿をろ別し、減圧蒸溜して８３，２Ｉ
の生成物（ゼリー状）を得た。そのときの収率は７７．
９ ％。得られた生成物の沸点は１０６℃１０、１ ｔ
ｍ Ｈｉであった。赤外分光分析によＩＪ ３１００〜
３６００３ ．２９００ｃｍ 、１２６０〜−１
＋
１１２０ぼ にヒータが存在した。After neutralizing the reaction mixture by adding Tic Ca (OH) t, the generated precipitate was filtered and distilled under reduced pressure to obtain 83,2I.
A product (jelly-like) was obtained. The yield at that time was 77.
9%. The boiling point of the product obtained is 106℃10, 1t
It was m Hi. IJ 3100~ by infrared spectroscopy
36003. 2900cm, 1260~-1
There was a heater at +1120.
ガスマス分析にて以下の７ラグメントを得た。The following 7 fragments were obtained by gas mass analysis.
（ｍ／ｅ、相対強度、帰属）４７４（１，２％。(m/e, relative intensity, attribution) 474 (1,2%.
＋
Ｍ ）、４５７（２，１％ｒ Ｍ−ＯＨ）、４４３（
１５％、Ｍ−ＣＨ，ＯＨ）、４１３ （６，３ｓ。+ M), 457 (2,1% r M-OH), 443 (
15%, M-CH,OH), 413 (6,3s.
ＯＨ
６１（１００％、ＣＨ（、’ｔ（，０Ｉ（）実施例２
実施例１で用いた装置に、
ｍ−）、水２０ゴ、溶媒としてアセトｙ １５０ ｍ／
。OH 61 (100%, CH(,'t(,0I()) Example 2 Into the apparatus used in Example 1, m-), 20 m of water, and 150 m/m of acetate as a solvent were added.
.
濃塩酸１ｄＩｋ入れ、油浴を用いて系内を６０℃に加熱
し、１８時間攪拌を行った。実施例１と同じ条件でガス
クロマトグラフ分析を行った結果、上記エポキシドの消
失と反応生成物の存在な確認した。減圧蒸溜により、５
３．１．９の生成物を得た（収率５２チ）。1 dIk of concentrated hydrochloric acid was added, and the inside of the system was heated to 60° C. using an oil bath, and stirred for 18 hours. As a result of gas chromatography analysis conducted under the same conditions as in Example 1, the disappearance of the epoxide and the presence of reaction products were confirmed. By vacuum distillation, 5
A product of 3.1.9 was obtained (yield 52 cm).
実施例３
１．４−ジオキサンの代りに、ジメチルスルホキシド（
３００ｍ）を用い、反応温度を９０℃とした以外は実施
例１と同一の条件で反応を行った。Example 3 1. Dimethyl sulfoxide (
The reaction was carried out under the same conditions as in Example 1, except that the reaction temperature was 90°C.
実施例１と同様の操作により６７．４ ｆｌの生成物を
得た。そのときの収率は６１１％であった。The same operation as in Example 1 was performed to obtain 67.4 fl of a product. The yield at that time was 611%.
実施例４
温度計、攪拌装置、還流冷却器を備えた３００４２、０
９ （ｏ、 １ｍｃＪ ） ＊水２０ゴ、溶媒として１
．４−ジオキサｙ１５０ｍｊ、濃硫酸０．２Ｍを入ね１
油浴を用いて系内な８０℃に加熱し、２０時間攪拌を行
った。ガスクロマトグラフ分析の結果、上記エポキシド
の消失と反応生成物の存在を確認した。Example 4 30042,0 equipped with thermometer, stirrer and reflux condenser
9 (o, 1 mcJ) *20 g of water, 1 g as solvent
．． Add 150 mj of 4-dioxa and 0.2 M of concentrated sulfuric acid 1
The system was heated to 80° C. using an oil bath and stirred for 20 hours. As a result of gas chromatography analysis, the disappearance of the epoxide and the presence of reaction products were confirmed.
反応混合液にＣａ （ＯＨ） ２を入れて中和した後、
生成した沈殿をろ別し、減圧蒸溜して３７．２ｙの生成
物（ゼリー状）を得た。そのときの収率は８５．０％。After neutralizing the reaction mixture with Ca(OH)2,
The generated precipitate was filtered and distilled under reduced pressure to obtain a 37.2y product (jelly-like). The yield at that time was 85.0%.
得られた生成物の沸点は１２５℃７０、２ ｍｘ ［（
９であった。The boiling point of the product obtained was 125°C 70, 2 mx [(
It was 9.
赤外分光分析により３１００〜３ａｏｏｃｒｎ 。3100-3aoocrn by infrared spectroscopy.
２９００ｃｒｒＬ 、１２６０〜１１２０ｃＩｆｔ に
ヒータが存在した。A heater was present at 2900 crrL and 1260 to 1120 cIft.
実施例５
１．４−ジオキサンの代りに、テトラヒドロフラン（３
００１Ｍ）＋濃硫酸の代りにｐ−）ルエンスルホン酸（
ｏ、ｓ、ｌ、反応温度を７０℃とした以外は実施ｆＩＪ
４と同一の条件で反応を行い、実施例４と同様の操作に
より、２６．９ ｐの生成物な得た。Example 5 Tetrahydrofuran (3
001M) + p-) luenesulfonic acid (instead of concentrated sulfuric acid)
o, s, l, except that the reaction temperature was 70°C fIJ
The reaction was carried out under the same conditions as in Example 4, and a 26.9 p product was obtained by the same operation as in Example 4.
そのときの収率は６１．５％であった。The yield at that time was 61.5%.
特許出頭人 三菱金属株式会社Patent applicant: Mitsubishi Metals Corporation
Claims (2)
ルキル基、ｎは１または２の整数）で表わされることを
特徴とする含フッ素ジオール。(1) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・(I) (In the formula, R_f is a perfluoroalkyl group having 4 to 20 carbon atoms, and n is an integer of 1 or 2) A fluorine-containing diol characterized by:
I） （式中Ｒ＿ｆは炭素原子数４〜２０のペルフルオロアル
キル基、ｎは１または２の整数）で表わされるエポキシ
化合物と水とを（無機または有機酸を触媒として、ケト
ン類、エーテル類、スルホキシド類、スルホン類より成
る群から選ばれた非反応性有機溶媒中で反応させること
を特徴とする前記一般式（ I ）で表わされる含フッ素
ジオールの製造法。(2) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・(I
I) (wherein R_f is a perfluoroalkyl group having 4 to 20 carbon atoms, n is an integer of 1 or 2) and water (using an inorganic or organic acid as a catalyst, ketones, ethers, A method for producing a fluorine-containing diol represented by the general formula (I), characterized by carrying out the reaction in a non-reactive organic solvent selected from the group consisting of sulfoxides and sulfones.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63134569A JP2526993B2 (en) | 1988-05-31 | 1988-05-31 | Fluorine-containing diol manufacturing method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63134569A JP2526993B2 (en) | 1988-05-31 | 1988-05-31 | Fluorine-containing diol manufacturing method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01305045A true JPH01305045A (en) | 1989-12-08 |
| JP2526993B2 JP2526993B2 (en) | 1996-08-21 |
Family
ID=15131407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63134569A Expired - Lifetime JP2526993B2 (en) | 1988-05-31 | 1988-05-31 | Fluorine-containing diol manufacturing method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2526993B2 (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3385904A (en) * | 1962-10-30 | 1968-05-28 | Minnesota Mining & Mfg | Decyclization of fluorinated cyclic ethers to perfluorinated tertiary alcohols |
| JPS646046A (en) * | 1987-06-30 | 1989-01-10 | Toho Chem Ind Co Ltd | Agricultural film |
| JPS6443520A (en) * | 1987-08-10 | 1989-02-15 | Dainichiseika Color Chem | Polyurethane emulsion |
| JPH01180810A (en) * | 1988-01-08 | 1989-07-18 | Nippon Oil & Fats Co Ltd | Powder for make-up |
| JPH01224247A (en) * | 1988-03-04 | 1989-09-07 | Nippon Kayaku Co Ltd | (meth)acrylate and resin composition and coating agent for optical fiber using said (meth)acrylate |
-
1988
- 1988-05-31 JP JP63134569A patent/JP2526993B2/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3385904A (en) * | 1962-10-30 | 1968-05-28 | Minnesota Mining & Mfg | Decyclization of fluorinated cyclic ethers to perfluorinated tertiary alcohols |
| JPS646046A (en) * | 1987-06-30 | 1989-01-10 | Toho Chem Ind Co Ltd | Agricultural film |
| JPS6443520A (en) * | 1987-08-10 | 1989-02-15 | Dainichiseika Color Chem | Polyurethane emulsion |
| JPH01180810A (en) * | 1988-01-08 | 1989-07-18 | Nippon Oil & Fats Co Ltd | Powder for make-up |
| JPH01224247A (en) * | 1988-03-04 | 1989-09-07 | Nippon Kayaku Co Ltd | (meth)acrylate and resin composition and coating agent for optical fiber using said (meth)acrylate |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2526993B2 (en) | 1996-08-21 |
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