WO2007080949A1 - 含フッ素エーテルアルコールおよびその製造法 - Google Patents

含フッ素エーテルアルコールおよびその製造法 Download PDF

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Publication number
WO2007080949A1
WO2007080949A1 PCT/JP2007/050292 JP2007050292W WO2007080949A1 WO 2007080949 A1 WO2007080949 A1 WO 2007080949A1 JP 2007050292 W JP2007050292 W JP 2007050292W WO 2007080949 A1 WO2007080949 A1 WO 2007080949A1
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WO
WIPO (PCT)
Prior art keywords
ether alcohol
fluorinated ether
terminal
group
fluorine
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.)
Ceased
Application number
PCT/JP2007/050292
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English (en)
French (fr)
Japanese (ja)
Inventor
Seiichiro Murata
Keisuke Kokin
Takehiro Sonoi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unimatec Co Ltd
Original Assignee
Unimatec Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Unimatec Co Ltd filed Critical Unimatec Co Ltd
Priority to US12/087,884 priority Critical patent/US20090171127A1/en
Priority to EP07713599A priority patent/EP1972610A4/en
Publication of WO2007080949A1 publication Critical patent/WO2007080949A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/13—Saturated ethers containing hydroxy or O-metal groups
    • C07C43/137—Saturated ethers containing hydroxy or O-metal groups containing halogen

Definitions

  • the present invention relates to a fluorine-containing ether alcohol and a method for producing the same. More specifically, the present invention relates to a fluorinated ether alcohol having a perfluoromethoxy group at the molecular end and a method for producing the same.
  • Fluorine-containing ether alcohols are considered to be widely used as surfactants and the like.
  • the terminal group of the fluorine-containing ether alcohol is a perfluoroethoxy group or a perfluoropropoxy group, and a fluorine-containing ether alcohol having a terminal perfluoromethoxy group is known. ,,,.
  • Patent Document 1 Japanese Patent Laid-Open No. 58-90524
  • Patent Document 2 Japanese Patent Laid-Open No. 2003-12606
  • a fluorine-containing ether alcohol having a terminal perfluoromethoxy group is independent from the specificity of the reaction at the terminal site, and is a terminal perfluoroethoxy group or a terminal perfluoropropoxy group.
  • An object of the present invention is to provide a novel fluorine-containing ether alcohol having a terminal perfluoromethoxy group and a method for producing the same.
  • a novel fluorine-containing ether alcohol having a terminal perfluoromethoxy group is provided, and the fluorine-containing ether alcohol is obtained by reacting cyclohexyl fluoride with hexafluoropropylene oxide.
  • the corresponding fluorine-containing ether carboxylate alkyl ester obtained by reacting the carboxylic acid fluoride with alcohol can be easily produced.
  • it is expected to exhibit unique interfacial activity characteristics as a mixture of it and a fluorine-containing ether alcohol having a terminal perfluoroethoxy group or a terminal perfluoropropoxy group. Is planned.
  • a fluorine-containing ether carboxylic acid alkyl ester which is a raw material for the synthesis of a fluorine-containing ether alcohol, is produced in accordance with a conventional method in the presence of a catalyst such as KF on carbon fluoride COF.
  • the alcohol used in this reaction is not particularly limited, but from the viewpoints of handleability, price, etc., those having 1 to 12 carbon atoms and 1 to 4 carbon atoms are particularly preferred. Methanol or ethanol is used. Since hydrogen fluoride is generated during this reaction, it is possible to have a metal fluoride equivalent to the raw material acid fluoride and an amine equivalent in the reaction system as a hydrogen fluoride scavenger. Is preferred.
  • Reduction of the fluorine-containing ether carboxylic acid alkyl ester thus obtained is generally used for lithium aluminum hydride, lithium diisobutylaluminum hydride, sodium borohydride, cyanobium borohydride, diborane and the like.
  • the reducing agent Although it is used, it is particularly preferable to use sodium borohydride from the viewpoint of safety, reducing ability, and price.
  • Sodium borohydride which is generally used in an amount of about 0.5 to 1 mol% with respect to the fluorine-containing ether carboxylic acid alkyl ester, may be used as a solid or may be used in the form of a basic aqueous solution. There is no difference in their reduction ability.
  • a solvent can be appropriately used for the reduction reaction.
  • alcohols such as methanol, ethanol and isopropanol
  • ethers such as tetrahydrofuran, dioxane and jetyl ether are used, and ethanol and isopropanol are particularly preferable.
  • the reaction temperature is in the range of about 20 to 30 ° C from the viewpoint of ease of force control, which can take a wide range in consideration of the number of n of the raw fluorine-containing ether carboxylic acid alkyl ester and the boiling point of the alcohol solvent. I prefer to be! /.
  • the fluorine-containing ether alcohol which is a product of the reduction reaction, can take an integer of 0 to 12, but is preferably 1 to 5 for ease of production.
  • This colorless and transparent liquid was subjected to simple distillation under the conditions of an internal pressure of 3 to 4 mmHg (400 to 533 Pa), an internal temperature of 52 to 53 ° C, and an overhead temperature of 50 to 52 ° C, and the target product 153 g (99.8 GC%, A distillation yield of 98.2%) was obtained.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/JP2007/050292 2006-01-13 2007-01-12 含フッ素エーテルアルコールおよびその製造法 Ceased WO2007080949A1 (ja)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US12/087,884 US20090171127A1 (en) 2006-01-13 2007-01-12 Fluorine-Containing Ether Alcohol and Process For Producing The Same
EP07713599A EP1972610A4 (en) 2006-01-13 2007-01-12 FLUORINATED ETHERE ALCOHOL AND PROCESS FOR PRODUCING THE SAME

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006005696A JP2007186454A (ja) 2006-01-13 2006-01-13 含フッ素エーテルアルコールおよびその製造法
JP2006-005696 2006-01-13

Publications (1)

Publication Number Publication Date
WO2007080949A1 true WO2007080949A1 (ja) 2007-07-19

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2007/050292 Ceased WO2007080949A1 (ja) 2006-01-13 2007-01-12 含フッ素エーテルアルコールおよびその製造法

Country Status (4)

Country Link
US (1) US20090171127A1 (enExample)
EP (1) EP1972610A4 (enExample)
JP (1) JP2007186454A (enExample)
WO (1) WO2007080949A1 (enExample)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014136894A1 (ja) 2013-03-06 2014-09-12 ユニマテック株式会社 含フッ素ナノコンポジット粒子およびその製造法
WO2014136896A1 (ja) 2013-03-06 2014-09-12 ユニマテック株式会社 含フッ素カルシウムコンポジット粒子、その製造法およびそれを有効成分とする表面処理剤
WO2014136893A1 (ja) 2013-03-06 2014-09-12 ユニマテック株式会社 含フッ素ナノシリカコンポジット粒子およびその製造法
KR20160134697A (ko) 2014-03-11 2016-11-23 유니마테크 가부시키가이샤 함불소 산화 타이타늄-나노 실리카 복합 입자 및 그 제조법
KR20160134696A (ko) 2014-03-11 2016-11-23 유니마테크 가부시키가이샤 수지-함불소 붕산 복합 입자의 복합체
KR20160134695A (ko) 2014-03-11 2016-11-23 유니마테크 가부시키가이샤 함불소 붕산 복합 입자
KR20170126957A (ko) 2015-03-10 2017-11-20 유니마테크 가부시키가이샤 함불소 붕산 pvb 컴퍼지트
US10088396B2 (en) 2014-03-11 2018-10-02 Unimatec Co., Ltd. Fluorine-containing boric acid composite capsule particles
WO2019239927A1 (ja) 2018-06-14 2019-12-19 ユニマテック株式会社 パーフルオロポリエーテルリン酸エステル、その製造法およびそれを有効成分とする表面処理剤
WO2025057528A1 (ja) * 2023-09-11 2025-03-20 ユニマテック株式会社 パーフルオロポリエーテルリン酸エステル又はその塩、表面処理剤、コーティング剤、離型剤並びにパーフルオロポリエーテルリン酸エステル又はその塩の製造方法

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JP5609646B2 (ja) * 2008-09-09 2014-10-22 旭硝子株式会社 水酸基を有するペルフルオロ化合物の製造方法
US10488753B2 (en) 2015-09-08 2019-11-26 Canon Kabushiki Kaisha Substrate pretreatment and etch uniformity in nanoimprint lithography
US20170066208A1 (en) 2015-09-08 2017-03-09 Canon Kabushiki Kaisha Substrate pretreatment for reducing fill time in nanoimprint lithography
US10620539B2 (en) 2016-03-31 2020-04-14 Canon Kabushiki Kaisha Curing substrate pretreatment compositions in nanoimprint lithography
US10134588B2 (en) * 2016-03-31 2018-11-20 Canon Kabushiki Kaisha Imprint resist and substrate pretreatment for reducing fill time in nanoimprint lithography
US10095106B2 (en) 2016-03-31 2018-10-09 Canon Kabushiki Kaisha Removing substrate pretreatment compositions in nanoimprint lithography
US10509313B2 (en) 2016-06-28 2019-12-17 Canon Kabushiki Kaisha Imprint resist with fluorinated photoinitiator and substrate pretreatment for reducing fill time in nanoimprint lithography
US10317793B2 (en) 2017-03-03 2019-06-11 Canon Kabushiki Kaisha Substrate pretreatment compositions for nanoimprint lithography
CN110857263B (zh) * 2018-08-23 2023-02-03 乳源东阳光氟有限公司 一种全氟聚醚醇的制备方法

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JPS5890524A (ja) * 1981-11-24 1983-05-30 Daikin Ind Ltd フツ素含有アルコ−ルおよびその誘導体
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JP2003026795A (ja) * 2001-05-18 2003-01-29 Ausimont Spa 一方に末端基−ｃｈ２ｏｈおよび他方に塩素を含む末端基を有するフルオロポリオキシアルキレンの製造方法

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JP2003026795A (ja) * 2001-05-18 2003-01-29 Ausimont Spa 一方に末端基−ｃｈ２ｏｈおよび他方に塩素を含む末端基を有するフルオロポリオキシアルキレンの製造方法
JP2003012588A (ja) * 2001-07-02 2003-01-15 Asahi Glass Co Ltd 含フッ素化合物、その製造方法、含フッ素重合体および撥水撥油剤組成物

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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014136894A1 (ja) 2013-03-06 2014-09-12 ユニマテック株式会社 含フッ素ナノコンポジット粒子およびその製造法
WO2014136896A1 (ja) 2013-03-06 2014-09-12 ユニマテック株式会社 含フッ素カルシウムコンポジット粒子、その製造法およびそれを有効成分とする表面処理剤
WO2014136893A1 (ja) 2013-03-06 2014-09-12 ユニマテック株式会社 含フッ素ナノシリカコンポジット粒子およびその製造法
KR20150120527A (ko) 2013-03-06 2015-10-27 유니마테크 가부시키가이샤 함불소 칼슘 컴퍼지트 입자, 그 제조법 및 그것을 유효 성분으로 하는 표면 처리제
KR20150128776A (ko) 2013-03-06 2015-11-18 유니마테크 가부시키가이샤 함불소 나노 컴퍼지트 입자 및 그 제조법
US10093812B2 (en) 2014-03-11 2018-10-09 Unimatec Co., Ltd. Composite material of resin—fluorine-containing boric acid composite particles
KR20160134696A (ko) 2014-03-11 2016-11-23 유니마테크 가부시키가이샤 수지-함불소 붕산 복합 입자의 복합체
KR20160134695A (ko) 2014-03-11 2016-11-23 유니마테크 가부시키가이샤 함불소 붕산 복합 입자
EP3670580A1 (en) 2014-03-11 2020-06-24 Unimatec Co., Ltd. Fluorine-containing titanium oxide - nano-silica composite particles and method for producing the same
US10088396B2 (en) 2014-03-11 2018-10-02 Unimatec Co., Ltd. Fluorine-containing boric acid composite capsule particles
KR20160134697A (ko) 2014-03-11 2016-11-23 유니마테크 가부시키가이샤 함불소 산화 타이타늄-나노 실리카 복합 입자 및 그 제조법
US10562989B2 (en) 2015-03-10 2020-02-18 Unimatec Co., Ltd. Fluorine-containing boric acid PVB composite
KR20170126957A (ko) 2015-03-10 2017-11-20 유니마테크 가부시키가이샤 함불소 붕산 pvb 컴퍼지트
WO2019239927A1 (ja) 2018-06-14 2019-12-19 ユニマテック株式会社 パーフルオロポリエーテルリン酸エステル、その製造法およびそれを有効成分とする表面処理剤
KR20210013174A (ko) 2018-06-14 2021-02-03 유니마테크 가부시키가이샤 퍼플루오로폴리에테르인산에스테르, 그 제조법 및 그것을 유효성분으로 하는 표면처리제
JPWO2019239927A1 (ja) * 2018-06-14 2021-07-08 ユニマテック株式会社 パーフルオロポリエーテルリン酸エステルの製造法およびそれを有効成分とする離型剤
JP7045454B2 (ja) 2018-06-14 2022-03-31 ユニマテック株式会社 パーフルオロポリエーテルリン酸エステルの製造法
KR102610032B1 (ko) 2018-06-14 2023-12-06 유니마테크 가부시키가이샤 퍼플루오로폴리에테르인산에스테르, 그 제조법 및 그것을 유효성분으로 하는 표면처리제
US12157752B2 (en) 2018-06-14 2024-12-03 Unimatec Co., Ltd. Perfluoropolyether phosphate ester, method for producing the same, and surface treatment agent comprising the same as active ingredient
WO2025057528A1 (ja) * 2023-09-11 2025-03-20 ユニマテック株式会社 パーフルオロポリエーテルリン酸エステル又はその塩、表面処理剤、コーティング剤、離型剤並びにパーフルオロポリエーテルリン酸エステル又はその塩の製造方法

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Publication number Publication date
JP2007186454A (ja) 2007-07-26
EP1972610A4 (en) 2011-01-12
US20090171127A1 (en) 2009-07-02
EP1972610A1 (en) 2008-09-24

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