JPH09503295A - キラール界面活性剤及びそれらのキラール分離における使用方法 - Google Patents
キラール界面活性剤及びそれらのキラール分離における使用方法Info
- Publication number
- JPH09503295A JPH09503295A JP7509896A JP50989695A JPH09503295A JP H09503295 A JPH09503295 A JP H09503295A JP 7509896 A JP7509896 A JP 7509896A JP 50989695 A JP50989695 A JP 50989695A JP H09503295 A JPH09503295 A JP H09503295A
- Authority
- JP
- Japan
- Prior art keywords
- chiral
- surfactant
- separation
- compound
- linker
- 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
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- 230000003247 decreasing effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000021483 diet soft drink Nutrition 0.000 description 1
- 150000002009 diols Chemical group 0.000 description 1
- 229950010030 dl-alanine Drugs 0.000 description 1
- PBULHKIPTBIZHO-UHFFFAOYSA-N dodecane-1-sulfonyl chloride Chemical compound CCCCCCCCCCCCS(Cl)(=O)=O PBULHKIPTBIZHO-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IFNMTQARFPYRSV-QGZVFWFLSA-N dodecyl n-[(2s)-1-hydroxy-3-methylbutan-2-yl]carbamate Chemical compound CCCCCCCCCCCCOC(=O)N[C@H](CO)C(C)C IFNMTQARFPYRSV-QGZVFWFLSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004193 electrokinetic chromatography Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000003821 enantio-separation Methods 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NWYYWIJOWOLJNR-RXMQYKEDSA-N l-valinol Chemical compound CC(C)[C@H](N)CO NWYYWIJOWOLJNR-RXMQYKEDSA-N 0.000 description 1
- 150000002613 leucine derivatives Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- KUGLDBMQKZTXPW-JEDNCBNOSA-N methyl (2s)-2-amino-3-methylbutanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)C(C)C KUGLDBMQKZTXPW-JEDNCBNOSA-N 0.000 description 1
- DEZPANARNACQPX-YFKPBYRVSA-N methyl (2s)-3-methyl-2-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoylamino)butanoate Chemical compound COC(=O)[C@H](C(C)C)NC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F DEZPANARNACQPX-YFKPBYRVSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000004244 micellar electrokinetic capillary chromatography Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- NPDBDJFLKKQMCM-UHFFFAOYSA-N tert-butylglycine Chemical compound CC(C)(C)C(N)C(O)=O NPDBDJFLKKQMCM-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 150000003679 valine derivatives Chemical class 0.000 description 1
- 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001796 valino group Chemical group 0.000 description 1
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.一般式 を有するキラール界面活性剤。 式中、R1=C4〜C18の直鎖アルキル、C4〜C18の分岐鎖アルキル、C4〜C18 のハロゲン置換直鎖アルキル、C4〜C18のポリエーテル炭化水素、C4〜C18 のキラール中心をもつアルキル、上記のすべてのアルキルは不飽和結合を有して いてもよく、及びコレステロール炭化水素(cholesterolic hydrocarbons)であ り、Y=O、NH又はCH2であり、A=NH、CO、SO又はSO2であり、X =CO、O又はNHであり、C=炭素であり、aとbは同一でなく、nは1から 5までであればよく、Z=COO-、SO4 -、SO3 -、PO3 -、PO4 -、NR’3 + 、PR’3 +、−OH、ポリエーテル、両性イオン、ポリアルコールであり、R ’=H又はC1〜C4の直鎖又は分岐の炭化水素であり、ハロゲン化されていても よく、不飽和結合を有していてもよい、そしてR1が直鎖の炭化水素であり、Y =CH2であり、A=COであり、X=NHであり、Z=COO-であり、a又は b=Hであるがaとbは同一でないときは、a又はbはメチル又はイソプロピル でない。 2.請求項1記載の一般式を有するキラール界面活性剤。 式中、Y=O、A=CO、X=NH、a=アミノ酸側鎖かつb=H、又はその逆 、そしてZ=OH、SO4 -又はCOO-である。 3.請求項1記載の一般式を有するキラール界面活性剤。 式中、Y=NH、A=CO、X=NH、a=アミノ酸側鎖かつb=H、又はその 逆、そしてZ=OH、SO4 -、又はCOO-である。 4.請求項1記載の一般式を有するキラール界面活性剤。 式中、Y=CH2、A=SO2、X=NH、a=アミノ酸側鎖かつb=H、又はそ の逆、そしてZ=OH、SO4 -、又はCOO-である。 5.請求項4記載の一般式を有するキラール界面活性剤。 式中、Y=CH2、A=CO、X=NH、a=アミノ酸側鎖かつb=H、又はそ の逆、そしてZ=OH、SO4 -、又はCOO-である。 6.請求項1記載の一般式を有するキラール界面活性剤。 式中、Y=CH2、A=NH、X=CO、a=アミノ酸側鎖かつb=H、又はそ の逆、そしてZ=NR’3 +、ここで、R’=H又はC1〜C8の直鎖又は分岐の炭 化水素であり、 ハロゲン化されていてもよく不飽和であってもよい。 7.下記一般式を有するキラール界面活性剤。 式中、R1=C4〜C18の直鎖アルキル、C4〜C18の分岐鎖アルキル、C4〜C18 のハロゲン置換直鎖アルキル、C4〜C18のポリエーテル炭化水素、C4〜C18 のキラール中心をもつアルキル、上記のすべてのアルキルは不飽和結合を有して いてもよく、及びコレステロール炭化水素であり、R2,R3=H又はC1〜C8の 直鎖又は分岐のアルキル又はアルケニル炭化水素であり、Y=CH2、A=NH 、X=CO、C=炭素、Z=COO-、SO4 -、SO3 -、PO3 -、PO4 -、NR ’3 +、PR’3 +、−OH、ポリエーテル、両性イオン、ポリアルコールであり、 R’=H又はC1〜C4の直鎖又は分岐の炭化水素であり、ハロゲン化されていて もよく、不飽和結合を有していてもよい。 8.下記一般式を有するキラール界面活性剤。 式中、R1=C4〜C18の直鎖アルキル、C4〜C18の分岐鎖アルキル、C4〜C18 のハロゲン置換直鎖アルキル、C4 〜C18のポリエーテル炭化水素、C4〜C18の1個から5個までのキラール中心 をもつアルキル、上記のすべてのアルキルは不飽和結合を有していてもよく、及 びコレステロール炭化水素であり、Y=O、NH又はCH2であり、A=NH、 CO、SO又はSO2であり、X=O又はNHであり、C=炭素原子であり、a とbは同一でなく、nは1から5までであればよく、Z=COO-、SO4 -、S O3 -、PO3 -、PO4 -、NR’3 +、PR’3 +、−OH、ポリエーテル、両性イオ ン、又はポリアルコールであり、R’=H又はC1〜C4の直鎖又は分岐の炭化水 素であり、ハロゲン化されていてもよく、不飽和結合を有していてもよい。 9.下記のものを有してなるキラール界面活性剤。 (a)キラール選択部、該キラール選択部は少なくとも1個のキラール中心 を有するもの、 (b)該キラール選択部に結合している親水性の頭部であって、該キラール 選択部との組合せによりキラール化合物の実質的分離を行うのに充分な程に該キ ラール界面活性剤のキラール選択性を強化するもの、 (c)該キラール選択部に結合しているリンカーであって、該キラール選択 部との組合せによりキラール化合物の実質的分離を行うのに充分な程に該キラー ル界面活性剤のキラール選択性を強化するもの、及び (d)該リンカーに結合している疎水性の尾部であって、該キラール選択部 との組合せによりキラール化合物の実質 的分離を行うのに充分な程に該キラール界面活性剤のキラール選択性を強化する もの。 10.該キラール選択部がアミノ酸類、アミノアルコール類、タートレーツ(tar trates)、及びそれらの各塩からなる群より選ばれるものである、請求項9記載 のキラール界面活性剤。 11.該リンカーがカルバメート類、スルフォンアミド類、及びウレア類からな る群より選ばれるものである、請求項9記載のキラール界面活性剤。 12.該親水性頭部が第4級アンモニウム類、アンモニウム塩類、カルボキシレ ート類、アルコール類、スルフェート類、スルフォン酸類、ポリアルコール類、 両性イオン類、及びそれらの各塩からなる群より選ばれるものである、請求項9 記載のキラール界面活性剤。 13.該疎水性尾部が直鎖アルキル類、置換直鎖アルキル類、直鎖アルケニル類 、ハロゲン置換直鎖アルケニル類、コレステロール炭化水素類、及びポリエーテ ル炭化水素類からなる群より選ばれるものである請求項9記載のキラール界面活 性剤。 14.該キラール選択部がアミノ酸である請求項9記載のキ ラール界面活性剤。 15.該キラール選択部がアミノアルコールである請求項9記載のキラール界面 活性剤。 16.該キラール選択部が酒石酸又はその誘導体である請求項9記載のキラール 界面活性剤。 17.電解質中に少なくとも1個の請求項1に記載のキラール界面活性剤を単独 で又は混合物として含有してなる物質の組成物。 18.該界面活性剤が図3aに示すものである請求項1記載のキラール界面活性 剤。 19.該界面活性剤が図3bに示すものである請求項1記載のキラール界面活性 剤。 20.該界面活性剤が図3akに示すものである請求項1記載のキラール界面活 性剤。 21.該界面活性剤が図3aeに示すものである請求項1記載のキラール界面活 性剤。 22.該界面活性剤が図3aoに示すものである請求項1記 載のキラール界面活性剤。 23.該界面活性剤が図3gに示すものである請求項1記載のキラール界面活性 剤。 24.該界面活性剤が図3hに示すものである請求項1記載のキラール界面活性 剤。 25.該界面活性剤が図31に示すものである請求項1記載のキラール界面活性 剤。 26.該界面活性剤が図3mに示すものである請求項1記載のキラール界面活性 剤。 27.該界面活性剤が図3nに示すものである請求項1記載のキラール界面活性 剤。 28.該界面活性剤が図3bdに示すものである請求項1記載のキラール界面活 性剤。 29.該界面活性剤が図3bgに示すものである請求項1記載のキラール界面活 性剤。 30.該界面活性剤が図3bhに示すものである請求項1記載のキラール界面活 性剤。 31.該界面活性剤が図3blに示すものである請求項1記載のキラール界面活 性剤。 32.請求項18〜31のいずれか1項に記載のキラール界面活性剤の光学鏡像 体。 33.請求項1記載のキラール界面活性剤とを組合わせた、キラールな化合物を それらの構成成分である対掌体に分離するための装置であって、 (a)ミセル・キラール毛管電気泳動に有効な電解質、 (b)該電解質を含むことができるチャンネル(channel)、 (c)少なくとも約10V/cm〜約1kV/cmの電界強度を作りだすこ とができる電源、 (d)該チャンネルの該両端に電気的に連結された少なくとも1個の陽極と 陰極、そして (e)該分離された対掌体の存在を検知するための検出器、 を含んでなる装置。 34.キラールな化合物をそれらの構成成分である対掌体に分離するためのキッ トであって、狭い空間(close confinement)内に1以上の容 器が収容できるよう に仕切られており、請求項1記載のキラール界面活性剤を含む第1の容器を組合 せ中に含んでなるキット。 35.組合せ中に請求項1記載の異なるキラール界面活性剤を含む第2の容器を 少なくとも含んでなる請求項34記載のキットであって、該異なるキラール界面 活性剤が混合キラール界面活性剤処方となるように混ぜあわされるものであるキ ット。 36.キラールでない界面活性剤を含む付加的容器を少なくとも1個含む請求項 34記載のキット。 37.キラールな化合物をそれらの構成成分である対掌体に分離するための方法 であって、電気泳動的毛管クロマトグラフィーの条件下にミセル状のキラール界 面活性剤の有効量と該キラール化合物を接触させる工程を含み、該キラール界面 活性剤が下記のものを含んでなる方法。 (a)キラール選択部、該キラール選択部は少なくとも1個のキラール中心 を有するもの、 (b)該キラール選択部に結合している親水性の頭部であって、該キラール 選択部との組合せによりキラール化合物の実質的分離を行うのに充分な程に該キ ラール界面活性剤のキラール選択性を強化するもの、 (c)該キラール選択部に結合しているリンカーであって、該キラール選択 部との組合せによりキラール化合物の実 質的分離を行うのに充分な程に該キラール界面活性剤のキラール選択性を強化す るもの、及び (d)該リンカーに結合している疎水性の尾部であって、該キラール選択部 との組合せによりキラール化合物の実質的分離を行うのに充分な程に該キラール 界面活性剤のキラール選択性を強化するもの。 38.キラールな化合物をそれらの構成成分である対掌体に分離するための方法 であって、電気泳動的毛管クロマトグラフィーの条件下にミセル状のキラール界 面活性剤の有効量と該キラール化合物を接触させる工程を含み、該キラール界面 活性剤が下記のものを含んでなる方法。 (a)アミノ酸類、アミノアルコール類、タートレーツ(tartrates)、及び それらの塩類からなる群より選ばれるキラール選択部であって、該キラール選択 部が少なくとも1個のキラール中心を有するもの、 (b)第4級アンモニウム類、アンモニウム塩類、カルボキシレート類、ア ルコール類、スルフェート類、スルホン酸類、ポリアルコール類、両性イオン類 、及びそれらの各塩類からなる群より選ばれる親水性頭部であって、該頭部が該 キラール選択部に結合しており、該キラール選択部との組合せによりキラール化 合物の実質的分離を行うのに充分な程に該キラール界面活性剤のキラール選択性 を強化するもの、 (c)カルバメート類、スルホンアミド類、及びウレア類からなる群より選 ばれるリンカーであって、該リンカーが 該キラール選択部に結合しており、該キラール選択部との組合せによりキラール 化合物の実質的分離を行うのに充分な程に該キラール界面活性剤のキラール選択 性を強化するもの、 (d)直鎖アルキル類、置換直鎖アルキル類、直鎖アルケニル類、ハロゲン 置換直鎖アルケニル類、コレステロール炭化水素類、及びポリエーテル炭化水素 類からなる群より選ばれる疎水性尾部であって、該尾部が該リンカーに結合して おり、該キラール選択部との組合せによりキラール化合物の実質的分離を行うの に充分な程に該キラール界面活性剤のキラール選択性を強化するもの。 39.該キラール界面活性剤が実質的水溶液中において臨界ミセル濃度で又はそ れ以上の濃度で存在する、請求項37又は38記載の方法。 40.該電気泳動条件が実質的な電気浸透流を含むものである請求項37又は3 8記載の方法。 41.該キラール化合物が生体液(biological fluid)中で混合されるものである 、請求項37又は38記載の方法。 42.該生体液が尿である請求項41記載の方法。 43.アスパルテームを分析する方法であって、アスパルテ ームの試料を、請求項1記載のキラール界面活性剤を含む電解質を有するミセル 電気動力学毛管電気泳動装置中に注入する工程、アスパルテームの対掌体を分離 する工程、及び次いで分離された対掌体を検出する工程を含んでなる方法。
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CA1335686C (fr) * | 1986-01-13 | 1995-05-23 | Rao K. S. P. Bhushana | Vinblastine et composition pharmaceutique les contenant |
US5084150A (en) * | 1987-03-24 | 1992-01-28 | Northeastern University | Selective high performance electrokinetic separations employing the surface of moving charged colloidal particles |
JPH07116064B2 (ja) * | 1987-07-21 | 1995-12-13 | 三菱化学株式会社 | 分離剤 |
DK255889D0 (da) * | 1989-05-25 | 1989-05-25 | Novo Nordisk As | Fremgangsmaade til fremstilling af organiske forbindelser |
FR2649697A1 (fr) * | 1989-07-11 | 1991-01-18 | Oreal | Nouveaux derives d'urethanne, leur preparation et leur application notamment comme agents hydratants dans des compositions cosmetiques ou pharmaceutiques destinees au traitement des peaux seches |
JP2568129B2 (ja) * | 1990-03-20 | 1996-12-25 | ジーエルサイエンス株式会社 | 動電クロマトグラフィー用界面活性剤及びこれをキャリヤーとして使用する光学分割方法及び動電クロマトグラフィー |
JP2558537B2 (ja) * | 1990-03-20 | 1996-11-27 | ジーエルサイエンス株式会社 | 動電クロマトグラフィー用界面活性剤、及びこれをキャリヤーとして使用する光学分割方法及び動電クロマトグラフィー |
-
1994
- 1994-09-20 JP JP50989695A patent/JP3699115B2/ja not_active Expired - Lifetime
- 1994-09-20 CA CA2172282A patent/CA2172282C/en not_active Expired - Lifetime
- 1994-09-20 WO PCT/US1994/010655 patent/WO1995008529A1/en active IP Right Grant
- 1994-09-20 US US08/617,916 patent/US6090250A/en not_active Expired - Lifetime
- 1994-09-20 AU AU79574/94A patent/AU7957494A/en not_active Abandoned
- 1994-09-20 EP EP94930460A patent/EP0721446B1/en not_active Expired - Lifetime
- 1994-09-20 DE DE69427765T patent/DE69427765T2/de not_active Expired - Lifetime
-
2004
- 2004-06-24 JP JP2004186516A patent/JP4061293B2/ja not_active Expired - Lifetime
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2005538151A (ja) * | 2002-09-05 | 2005-12-15 | ディービーエル・オーストラリア・プロプライアタリー・リミテッド | 尿素−、グリセラート−及びヒドロキシアミド−頭部形成した炭化水素鎖のリオトロピック相形成性界面活性剤 |
JP2007532880A (ja) * | 2004-04-07 | 2007-11-15 | ウオーターズ・インベストメンツ・リミテツド | エナンチオマーの分離用組成物及び方法 |
WO2006082978A1 (ja) * | 2005-02-07 | 2006-08-10 | Ajinomoto Co., Inc. | アディポネクチンの分泌促進または誘導作用を有するアシルアミド化合物 |
US7732637B2 (en) | 2005-02-07 | 2010-06-08 | Ajinomoto Co., Inc. | Acylamide compounds having secretagogue or inducer activity of adiponectin |
WO2018181906A1 (ja) * | 2017-03-31 | 2018-10-04 | ダイキン工業株式会社 | アルキル硫酸エステル又はその塩 |
WO2018181907A1 (ja) * | 2017-03-31 | 2018-10-04 | ダイキン工業株式会社 | スルホン酸、カルボン酸又はそれらの塩 |
JPWO2018181907A1 (ja) * | 2017-03-31 | 2019-07-11 | ダイキン工業株式会社 | スルホン酸、カルボン酸又はそれらの塩 |
JPWO2018181906A1 (ja) * | 2017-03-31 | 2019-07-25 | ダイキン工業株式会社 | アルキル硫酸エステル又はその塩 |
JP2021113235A (ja) * | 2017-03-31 | 2021-08-05 | ダイキン工業株式会社 | アルキル硫酸エステル又はその塩 |
US11279814B2 (en) | 2017-03-31 | 2022-03-22 | Daikin Industries, Ltd. | Production method for fluoropolymer, surfactant for polymerization, and use of surfactant |
US11440875B2 (en) | 2017-03-31 | 2022-09-13 | Daikin Industries, Ltd. | Sulfonic acid, carboxylic acid, and salts thereof |
US11999681B2 (en) | 2017-03-31 | 2024-06-04 | Daikin Industries, Ltd. | Alkyl sulfate ester or salt of same |
Also Published As
Publication number | Publication date |
---|---|
CA2172282C (en) | 2011-05-31 |
DE69427765T2 (de) | 2002-05-23 |
DE69427765D1 (de) | 2001-08-23 |
AU7957494A (en) | 1995-04-10 |
JP2005041863A (ja) | 2005-02-17 |
CA2172282A1 (en) | 1995-03-30 |
US6090250A (en) | 2000-07-18 |
JP3699115B2 (ja) | 2005-09-28 |
WO1995008529A1 (en) | 1995-03-30 |
EP0721446B1 (en) | 2001-07-18 |
EP0721446A1 (en) | 1996-07-17 |
JP4061293B2 (ja) | 2008-03-12 |
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