JPH03284642A - Fluorine-containing allyl ether and production thereof - Google Patents
Fluorine-containing allyl ether and production thereofInfo
- Publication number
- JPH03284642A JPH03284642A JP8383890A JP8383890A JPH03284642A JP H03284642 A JPH03284642 A JP H03284642A JP 8383890 A JP8383890 A JP 8383890A JP 8383890 A JP8383890 A JP 8383890A JP H03284642 A JPH03284642 A JP H03284642A
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- fluoride
- formula
- allyl ether
- allyl
- 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
- 229910052731 fluorine Inorganic materials 0.000 title abstract description 14
- 239000011737 fluorine Substances 0.000 title abstract description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title abstract description 13
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 title abstract description 9
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 perfluoro Chemical group 0.000 claims abstract description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 6
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 229920001774 Perfluoroether Polymers 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 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
- 239000007788 liquid Substances 0.000 description 8
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001793 charged compounds Chemical class 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 235000003270 potassium fluoride Nutrition 0.000 description 3
- 239000011698 potassium fluoride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- GAKSVIQMUADMSK-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-(trifluoromethoxy)propanoyl fluoride Chemical compound FC(=O)C(F)(C(F)(F)F)OC(F)(F)F GAKSVIQMUADMSK-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- AHLATJUETSFVIM-UHFFFAOYSA-M rubidium fluoride Chemical compound [F-].[Rb+] AHLATJUETSFVIM-UHFFFAOYSA-M 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UVHZTXUBKSUXED-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-(1,1,2,2,2-pentafluoroethoxy)propanoyl fluoride Chemical compound FC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)F UVHZTXUBKSUXED-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 description 1
- OEERIBPGRSLGEK-UHFFFAOYSA-N carbon dioxide;methanol Chemical compound OC.O=C=O OEERIBPGRSLGEK-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、新規な含フツ素アリルエーテルおよびその製
造法に関する。更に詳しくは、各種の含フツ素化合物の
合成中間体や共単量体成分として有用な含フツ素アリル
エーテルおよびその製造法に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel fluorine-containing allyl ether and a method for producing the same. More specifically, the present invention relates to a fluorine-containing allyl ether useful as a synthetic intermediate or comonomer component for various fluorine-containing compounds, and a method for producing the same.
特開昭６３−２５３，０４４号公報には、次のような含
フツ素アリルエーテルが記載されている。JP-A-63-253,044 describes the following fluorine-containing allyl ethers.
ＣＦ３ ＣＦ３
しかしながら、この含フツ素アリルエーテルは、炭素数
３のへキサフルオロプロペンオキサイドから導かれる化
合物とアリルハライドとから合成されるため、パーフル
オロアルコキシ末端基の炭素数は３に限定されている。CF3 CF3 However, since this fluorine-containing allyl ether is synthesized from a compound derived from hexafluoropropene oxide having 3 carbon atoms and allyl halide, the number of carbon atoms in the perfluoroalkoxy end group is limited to 3. .
本発明の目的は、炭素数１または２のパーフルオロアル
コキシ末端基を有する含フツ素アリルエーテルを提供す
ることにある。An object of the present invention is to provide a fluorine-containing allyl ether having a perfluoroalkoxy terminal group having 1 or 2 carbon atoms.
本発明により、一般式
％式％［
（ここで、Ｒは水素原子またはメチル基であり、ｎは０
またはｌであり、園は１以上の整数である）で表わされ
る含フツ素アリルエーテルが提供され、がかる含フツ素
アリルエーテルは、一般式（ここで、ｎは０または１で
あり、Ｑは０または１以上の整数である）で表わされる
パーフルオロ（２−アルコキシプロピオン酸）フロライ
ド、アルカリ金属フロライドおよび（メタ）アリルハラ
イドを反応させることにより製造される。According to the present invention, the general formula % formula % [ (where R is a hydrogen atom or a methyl group and n is 0
or l, where n is an integer of 1 or more), and the fluorine-containing allyl ether is represented by the general formula It is produced by reacting perfluoro(2-alkoxypropionic acid) fluoride (which is an integer of 0 or 1 or more), an alkali metal fluoride, and (meth)allyl halide.
［■コ＋ＭＦ 十ＸＣＨ２ＣＲ＝ ＣＨ，→［Ｉコアル
カリ金属フロライドとしては、例えばフッ化ナトリウム
、フッ化カリウム、フッ化セシウム。[■Co+MF 1XCH2CR= CH, → [I Coalkali metal fluoride includes, for example, sodium fluoride, potassium fluoride, and cesium fluoride.
フッ化ルビジウム、酸性フッ化ナトリウム、酸性フッ化
カリウムなどが用いられる。また、（メタ）アリルハラ
イドとしては、塩化アリル、臭化アリル、ヨウ化アリル
またはそれらの２−メチル置換体が用いられる。酸フロ
ライドに対して、アルカリ金属フロライドおよび（メタ
）アリルハライドは、いずれもわずかに過剰となるモル
比で用いられる。Rubidium fluoride, acidic sodium fluoride, acidic potassium fluoride, etc. are used. Further, as the (meth)allyl halide, allyl chloride, allyl bromide, allyl iodide, or 2-methyl substituted products thereof are used. Both the alkali metal fluoride and the (meth)allyl halide are used in a slightly excess molar ratio with respect to the acid fluoride.
反応は、好ましくは非プロトン性極性溶媒、例えばテト
ラエチレングリコールジメチルエーテル。The reaction is preferably carried out in an aprotic polar solvent, such as tetraethylene glycol dimethyl ether.
トリエチレングリコールジメチルエーテル、ジエチレン
グリコールジメチルエーテル、エチレングリコールジメ
チルエーテルなどのグライム類、ジオキサン、テトラヒ
ドロフランなどの環状エーテル類、アセトニトリルなど
の溶媒の存在下で行われる。具体的には、アルカリ金属
フロライドをけん濁させたこれらの溶媒中に酸フロライ
ドを仕込み、約１〜１２時間程度撹拌してから（メタ）
アリルハライドを仕込み、約０〜１００℃の温度で約２
４時間程度反応させることにより行わわる。なお、反応
に用いられる各反応原料および溶媒は、十分に脱水して
用いられなければならない。It is carried out in the presence of glymes such as triethylene glycol dimethyl ether, diethylene glycol dimethyl ether, and ethylene glycol dimethyl ether, cyclic ethers such as dioxane and tetrahydrofuran, and solvents such as acetonitrile. Specifically, acid fluoride is added to these solvents in which alkali metal fluoride is suspended, and after stirring for about 1 to 12 hours, (meth)
Prepare allyl halide and heat it at a temperature of about 0 to 100℃ for about 2 hours.
This is done by reacting for about 4 hours. Note that each reaction raw material and solvent used in the reaction must be sufficiently dehydrated before use.
（発明の効果〕
パーフルオロ（２−アルコキシプロピオン酸）フロライ
ドを、アルカリ金属フロライドおよび（メタ）アリルハ
ライドを反応させることにより、炭素数１または２のパ
ーフルオロアルコキシ末端基を有する新規の含フツ素ア
リルエーテルが製造される。(Effect of the invention) By reacting perfluoro(2-alkoxypropionic acid) fluoride with an alkali metal fluoride and (meth)allyl halide, a new fluorine-containing product having a perfluoroalkoxy terminal group having 1 or 2 carbon atoms is produced. Allyl ether is produced.
これらの含フツ素アリルエーテルは、各種の含フツ素化
合物の合成中間体や共単量体成分として有効に使用する
ことができる。These fluorine-containing allyl ethers can be effectively used as synthetic intermediates and comonomer components for various fluorine-containing compounds.
次に、実施例について本発明を説明する。 Next, the present invention will be explained with reference to examples.
実施例１
撹拌機、温度計および冷却管を備えた容量５００ｍｎの
四ロフラスコに、共に十分に乾燥させたフッ化カリウム
３２ｇとジエチレングリコールジメチルエーテル２００
ｇとを仕込み、そこに形成されたけん濁液中にパーフル
オロ（２−メトキシプロピオン酸）フロライド１１６ｇ
を、ドライアイス−メタノール冷却管を通して仕込んだ
。２時間後に、そこに臭化アリル６６．６ｇを滴下し、
５０℃で２４時間反応させた。Example 1 32 g of potassium fluoride and 200 g of diethylene glycol dimethyl ether, both thoroughly dried, were placed in a 500 mm capacity four-hole flask equipped with a stirrer, a thermometer, and a condenser.
and 116 g of perfluoro(2-methoxypropionic acid) fluoride in the suspension formed therein.
was charged through a dry ice-methanol cooling tube. After 2 hours, 66.6 g of allyl bromide was added dropwise.
The reaction was carried out at 50°C for 24 hours.
反応終了後、反応混合物を数回水洗し１４２ｇの液体を
得、これを蒸留して沸点９３〜９５℃の透明な液体８８
．０ｇ（収率６０．３％）を得た。この液体は、下記の
分析結果から１．ＣＦ３０ＣＦ （ＣＦ、 ）ＣＦ、
０ＣＨ２ＣＨ＝ ＣＨ２の構造を有する化合物であると
同定された。After the reaction was completed, the reaction mixture was washed with water several times to obtain 142 g of liquid, which was distilled to obtain 88 g of a transparent liquid with a boiling point of 93-95°C.
．． 0 g (yield 60.3%) was obtained. Based on the analysis results below, this liquid is 1. CF30CF (CF, )CF,
It was identified as a compound having the structure 0CH2CH=CH2.
ＧＣ−ＭＳスペクトル：
Ｍ／ｅ ２９２（分子イオン）
Ｍ／ｅ ６９ ＣＦ３’
Ｈ７ｅ ４］ ＣＭ、ＣＨ＝ＣＨ２”Ｈ−ＮＭＲ
：
■ ■
■ ４ 、６３ｐｐ＋ａ
■ ５．９２ｐｐＨ
■ ５．２４ｐｐｍ
■ ５．３（ｌｐｐｍ
１３Ｃ−ＮＭＲ（完全デカップリング）：Ｌ；ｔ’３
■ ６７．８ｐｐｍ
［Ｆ］ １３２．ｌＰＰｌ１
■ １１９．７ＰＰ！１
”Ｆ−ＮＭＲ（ＣＦ３ＣＯＯＨ基準）：Ｏ■Ｏ
ＣＦ、 ０ＣＦＣＦ２０ＣＨ，ＣＨ＝ ＣＨ。GC-MS spectrum: M/e 292 (molecular ion) M/e 69 CF3' H7e 4] CM, CH=CH2''H-NMR
: ■ ■ ■ 4, 63pp+a ■ 5.92ppH ■ 5.24ppm ■ 5.3(lppm 13C-NMR (complete decoupling): L; t'3 ■ 67.8ppm [F] 132.lPPl1 ■ 119.7PP! 1"F-NMR (CF3COOH standard): O■O CF, 0CFCF20CH, CH=CH.
■ ＋２０ｐρｍ
■ −７ｐｐｍ
Ｏ−１１ｐｐｍ
■ −７０ｐｐｍ
実施例２
実施例１において、パーフルオロ（２−メトキシプロピ
オン酸）フロライドの代わりに、パーフルオロ（２−エ
トキシプロピオン酸）フロライド１４１ｇを用い、沸点
１０７〜１０８℃の液体１１６ｇ（収率６７．８％）を
得た。この液体は、下記の分析結果などから。■ +20 ppm ■ -7 ppm O-11 ppm ■ -70 ppm Example 2 In Example 1, 141 g of perfluoro(2-ethoxypropionic acid) fluoride was used instead of perfluoro(2-methoxypropionic acid) fluoride, and the boiling point was 107~ 116 g (yield 67.8%) of a liquid at 108° C. was obtained. This liquid is based on the analysis results below.
ＣＦ、 ＣＦ２０ＣＦ （ＣＦ３）ＣＦ、 ０ＣＨ２Ｃ
Ｈ＝ ＣＨ２の構造を有する化合物であると同定された
。CF, CF20CF (CF3)CF, 0CH2C
It was identified as a compound having the structure H=CH2.
ＧＣ−ＭＳスペクトル：
Ｎ／ｅ ３４２（分子イオン）
実施例３
実施例１において、臭化アリルの代わりに塩化メタアリ
ル４９゜８ｇを滴下し、７０℃で２４時間反応させた。GC-MS spectrum: N/e 342 (molecular ion) Example 3 In Example 1, 49.8 g of metaallyl chloride was added dropwise instead of allyl bromide, and the mixture was reacted at 70°C for 24 hours.
反応混合物を数回水洗して得られた１２８ｇの液体を蒸
留し、沸点１０９℃の透明な液体７４ｇ（収率４８．４
％）を得た。この液体は、下記の分析結果から、ＣＦ
ｓ ＯＣＦ （ＣＦ ３ ） ＣＦ ２０ Ｃ）（ｚ
Ｃ（ＣＦ１３ ） ＝ＣＨ２の構造を有する化合物であ
ると同定された。The reaction mixture was washed with water several times and 128 g of the obtained liquid was distilled to give 74 g of a transparent liquid with a boiling point of 109°C (yield 48.4
%) was obtained. From the analysis results below, this liquid is CF
s OCF (CF 3 ) CF 20 C) (z
It was identified as a compound having the structure C(CF13)=CH2.
ＧＣ−ＭＳスペクトル： Ｍ／ｅ ３０６（分子イオン） Ｍ／ｅ ６９ ＣＦ、’ Ｍ／ｅ ５５ °ＣＨ，Ｃ＝ ＣＨ。GC-MS spectrum: M/e 306 (molecular ion) M/e 69 CF,' M/e 55 °CH, C=CH.
ＣＨ。CH.
１）１−ＮＭＲ： ■ ４．６３ｐｐｍ ■ ５．２４ｐｐｍ ■ ５．３０ｐｐｍ ■ ０■０ ＣＦ３０ＣＦＣＦ、０ＣＲ２Ｃ＝ＣＨ。1) 1-NMR: ■ 4.63ppm ■ 5.24ppm ■ 5.30ppm ■ 0■0 CF30CFCF, 0CR2C=CH.
ＣＦ、 ＣＨ３ ■ ■ ＋２０ｐｐｍ ［Ｆ］ −７ρｐｆｆｉ ■ −１１ｐｐｍ ■ −７０ｐｐｏ＋CF, CH3 ■ ■ +20ppm [F] −7ρpffi ■-11ppm ■-70ppo+
Claims (1)
または１であり、ｍは１以上の整数である）で表わされ
る含フッ素アリルエーテル。 ２、一般式 ▲数式、化学式、表等があります▼［II］ （ここで、ｎは０または１であり、ｌは０または１以上
の整数である）で表わされるパーフルオロ（２−アルコ
キシプロピオン酸）フロライド、アルカリ金属フロライ
ドおよび（メタ）アリルハライドを反応させることを特
徴とする一般式 ▲数式、化学式、表等があります▼［ I ］ （ここで、Ｒは水素原子またはメチル基であり、ｎは０
または１であり、ｍは１以上の整数である）で表わされ
る含フッ素アリルエーテルの製造法。[Claims] 1. General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [I] (Here, R is a hydrogen atom or a methyl group, and n is 0
or 1, and m is an integer of 1 or more). 2. General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [II] (where n is 0 or 1, and l is an integer of 0 or 1 or more) A general formula characterized by reacting acid) fluoride, alkali metal fluoride, and (meth)allyl halide ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [I] (Here, R is a hydrogen atom or a methyl group, n is 0
or 1, and m is an integer of 1 or more).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8383890A JP2813025B2 (en) | 1990-03-30 | 1990-03-30 | Fluorine-containing allyl ether and its production method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8383890A JP2813025B2 (en) | 1990-03-30 | 1990-03-30 | Fluorine-containing allyl ether and its production method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03284642A true JPH03284642A (en) | 1991-12-16 |
| JP2813025B2 JP2813025B2 (en) | 1998-10-22 |
Family
ID=13813849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8383890A Expired - Fee Related JP2813025B2 (en) | 1990-03-30 | 1990-03-30 | Fluorine-containing allyl ether and its production method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2813025B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015019809A1 (en) | 2013-08-09 | 2015-02-12 | ユニマテック株式会社 | Bis(perfluoroether alkyl carboxylic acid)amino ester and method for manufacturing same |
| US10000444B2 (en) | 2015-02-03 | 2018-06-19 | Unimatec Co., Ltd. | Fluorine-containing ether monocarboxylic acid aminoalkyl ester and a method for producing the same |
-
1990
- 1990-03-30 JP JP8383890A patent/JP2813025B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015019809A1 (en) | 2013-08-09 | 2015-02-12 | ユニマテック株式会社 | Bis(perfluoroether alkyl carboxylic acid)amino ester and method for manufacturing same |
| US9758470B2 (en) | 2013-08-09 | 2017-09-12 | Unimatec Co., Ltd. | Bis(perfluoroether carboxylic acid alkyl)amino ester and method for producing the same |
| US10000444B2 (en) | 2015-02-03 | 2018-06-19 | Unimatec Co., Ltd. | Fluorine-containing ether monocarboxylic acid aminoalkyl ester and a method for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2813025B2 (en) | 1998-10-22 |
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