WO2010057691A2 - Hydrofluoroalcools ayant une stabilité thermique et chimique améliorée - Google Patents

Hydrofluoroalcools ayant une stabilité thermique et chimique améliorée Download PDF

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Publication number
WO2010057691A2
WO2010057691A2 PCT/EP2009/060302 EP2009060302W WO2010057691A2 WO 2010057691 A2 WO2010057691 A2 WO 2010057691A2 EP 2009060302 W EP2009060302 W EP 2009060302W WO 2010057691 A2 WO2010057691 A2 WO 2010057691A2
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WO
WIPO (PCT)
Prior art keywords
formula
alcohols
hydrofluoro
group
chain
Prior art date
Application number
PCT/EP2009/060302
Other languages
English (en)
Other versions
WO2010057691A3 (fr
Inventor
Giuseppe Marchionni
Ugo De Patto
Marco Avataneo
Original Assignee
Solvay Solexis S.P.A.
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 Solvay Solexis S.P.A. filed Critical Solvay Solexis S.P.A.
Priority to CN200980140098.8A priority Critical patent/CN102177123B/zh
Priority to JP2011522491A priority patent/JP5743217B2/ja
Priority to EP09781636.7A priority patent/EP2331491B1/fr
Priority to US13/058,297 priority patent/US8946136B2/en
Publication of WO2010057691A2 publication Critical patent/WO2010057691A2/fr
Publication of WO2010057691A3 publication Critical patent/WO2010057691A3/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C07C319/08—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by replacement of hydroxy groups or etherified or esterified hydroxy groups
    • 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
    • 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
    • C07C41/34—Separation; Purification; Stabilisation; Use of additives
    • C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
    • C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/313—Compounds having groups containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/65—Halogen-containing esters of unsaturated acids
    • C07C69/653—Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
    • C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
    • C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M147/00—Lubricating compositions characterised by the additive being a macromolecular compound containing halogen
    • C10M147/04—Monomer containing carbon, hydrogen, halogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
    • C10M2213/0606—Perfluoro polymers used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/185—Magnetic fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • the present invention relates to hydro fluoro alcohols with improved chemical stability, in particular to acids and bases, in combination with better thermal stability, and to the process for preparing them.
  • hydrofluoro alcohols are compounds characterized by a low vapour pressure and low surface tension values.
  • hydro fluoropolyether alcohols for example the products known as Fomblin ® Z-DOL and Fomblin ® Z-DOL TX, sold by Solvay Solexis, also show low glass transition (Tg) values.
  • Tg glass transition
  • the ester derivatives obtained therefrom show improved hydrolytic stability.
  • R h is chosen from :
  • an aromatic ring in which, optionally, one or more carbon atoms of the said aromatic ring are substituted with a heteroatom, or a C6-C 2 0 alkyl chain comprising one or more of the said aromatic rings,
  • R h may contain one or more unsaturations ; the cyclic and/or aromatic rings may have one or more hydrogen atoms replaced with C 1 -C 1 0 (fluoro)alkyl chains, which are linear or branched where possible.
  • R h is preferably an alkyl chain, which is linear or branched where possible, more preferably of C 2 -C 1 0 and even more preferably of C 2 -C6, optionally containing one or more unsaturations.
  • R h may optionally contain one or more heteroatoms, for instance non-ether oxygen, N, etc.
  • R f is a PFPE chain having a number-average molecular weight from about 100 to about 10 000 ; when it is a (per)fluoroalkyl chain, it is preferably a C 1 -C30 (per)fluoroalkyl chain, which is a linear or branched, where possible.
  • the chain R f may contain one or more C3-C 1 0 (per)fluorinated cyclic rings, optionally substituted with fluorine atoms or with one or more Ci-Cio (per)fluoroalkyl chains, which are linear or branched where possible.
  • Example 6 12 meq. of the product obtained in Example 6 are placed in a glass 25 ml round-bottomed flask. 1O g of aqueous HI at 20% by weight (16 mmol) are added with stirring, and the solution is gradually heated to a temperature Of IOOoC. Every three hours, samples are taken for 19 F NMR analysis - 2-3 drops of sample diluted with about 1.5 ml of deuterated acetone.
  • Example 12 is repeated, but using the hydro fluoro alcohol CF 3 CF 2 CF 2 CF 2 CH 2 CH 2 OH from Aldrich.
  • the 19 F NMR spectrum of the product obtained indicates and approximately 7 mol% degradation of the hydrofluoro alcohol.
  • the NMR analysis does not reveal any degradation of the hydrofluoro alcohol.
  • the NMR spectrum indicates approximately 10 mol% degradation of the hydrofluoro alcohol.
  • the main degradation product is :

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
  • Lubricants (AREA)
  • Polyethers (AREA)

Abstract

La présente invention concerne des hydrofluoroalcools de formule : A-(Rf)a-CFX-O-RhO-(CFX-(Rf)a*-CFX-O-RhO-)nH (I) dans laquelle : Rh est une chaîne à base hydrocarbonée; X est F ou un (per)fluoroalkyle en C1-C6; a ou a* est 0 ou 1; Rf est une chaîne (per)fluoro(poly)oxyalkylène ou une chaîne (per)fluoroalkyle; A est choisi parmi -F, -Cl et -H (possible uniquement lorsque a = 1) ou est HO-Rh-O-CFX-; n est un entier de 0 à 200, à condition que n = 0 lorsque A est choisi parmi -F, -Cl et -H.
PCT/EP2009/060302 2008-08-11 2009-08-07 Hydrofluoroalcools ayant une stabilité thermique et chimique améliorée WO2010057691A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN200980140098.8A CN102177123B (zh) 2008-08-11 2009-08-07 具有改进的热以及化学稳定性的氢氟醇
JP2011522491A JP5743217B2 (ja) 2008-08-11 2009-08-07 熱安定性及び化学的安定性が改善されたハイドロフルオロアルコール
EP09781636.7A EP2331491B1 (fr) 2008-08-11 2009-08-07 Procede de preparation d'hydrofluoroalcools ayant une stabilité thermique et chimique améliorée
US13/058,297 US8946136B2 (en) 2008-08-11 2009-08-07 Hydrofluoroalcohols with improved thermal and chemical stability

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP08425563 2008-08-11
EP08425563.7 2008-08-11

Publications (2)

Publication Number Publication Date
WO2010057691A2 true WO2010057691A2 (fr) 2010-05-27
WO2010057691A3 WO2010057691A3 (fr) 2010-10-14

Family

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PCT/EP2009/060302 WO2010057691A2 (fr) 2008-08-11 2009-08-07 Hydrofluoroalcools ayant une stabilité thermique et chimique améliorée

Country Status (6)

Country Link
US (1) US8946136B2 (fr)
EP (1) EP2331491B1 (fr)
JP (1) JP5743217B2 (fr)
KR (1) KR101632762B1 (fr)
CN (1) CN102177123B (fr)
WO (1) WO2010057691A2 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016083280A1 (fr) 2014-11-27 2016-06-02 Solvay Specialty Polymers Italy S.P.A. Mélanges de polymères fluorés non, mono- et bifonctionnels comprenant une pluralité de segments polyéther (per)fluoré
WO2016083279A1 (fr) 2014-11-27 2016-06-02 Solvay Specialty Polymers Italy S.P.A. Polymères fluorés bifonctionnels comprenant une pluralité de segments (per)fluoropolyéther
WO2017144413A1 (fr) 2016-02-23 2017-08-31 Solvay Specialty Polymers Italy S.P.A. Procédé de fabrication de polymères fluorés et polymères pouvant être obtenus à partir de ces derniers
WO2017202772A1 (fr) * 2016-05-26 2017-11-30 Solvay Specialty Polymers Italy S.P.A. Polymères fluorés comprenant des groupes terminaux aromatiques
WO2018108864A1 (fr) 2016-12-14 2018-06-21 Solvay Specialty Polymers Italy S.P.A. Polymères de (per)fluoropolyéther
WO2019202079A1 (fr) 2018-04-20 2019-10-24 Solvay Specialty Polymers Italy S.P.A. Procédé de production d'un mélange de polymères
WO2019243404A1 (fr) 2018-06-20 2019-12-26 Solvay Specialty Polymers Italy S.P.A. Procédé de production d'un mélange de polymères
WO2019243403A1 (fr) * 2018-06-20 2019-12-26 Solvay Specialty Polymers Italy S.P.A. Polymères de (per)fluoropolyéther

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US20140234666A1 (en) * 2013-02-19 2014-08-21 Wd Media, Inc. Lubricants comprising pfpe terminated with benzene or functional benzene end groups for magnetic recording media structure
WO2018019804A1 (fr) * 2016-07-25 2018-02-01 Solvay Specialty Polymers Italy S.P.A. Électrolytes liquides pour batteries au lithium
TWI823842B (zh) * 2016-12-14 2023-12-01 義大利商首威專業聚合物義大利公司 全氟聚醚聚合物
WO2022138509A1 (fr) * 2020-12-25 2022-06-30 Ａｇｃ株式会社 Procédé de fabrication de composition de polyéther, procédé de fabrication de composition de polyéther fluoré, et composition de polyéther

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WO2016083279A1 (fr) 2014-11-27 2016-06-02 Solvay Specialty Polymers Italy S.P.A. Polymères fluorés bifonctionnels comprenant une pluralité de segments (per)fluoropolyéther
CN107001610A (zh) * 2014-11-27 2017-08-01 索尔维特殊聚合物意大利有限公司 包含多个（全）氟聚醚链段的双官能氟化聚合物
WO2016083280A1 (fr) 2014-11-27 2016-06-02 Solvay Specialty Polymers Italy S.P.A. Mélanges de polymères fluorés non, mono- et bifonctionnels comprenant une pluralité de segments polyéther (per)fluoré
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US10533071B2 (en) 2014-11-27 2020-01-14 Solvay Specialty Polymers Italy S.P.A. Mixtures of mono-, bi- and non-functional fluorinated polymers comprising a plurality of (per)fluoropolyether segments
WO2017144413A1 (fr) 2016-02-23 2017-08-31 Solvay Specialty Polymers Italy S.P.A. Procédé de fabrication de polymères fluorés et polymères pouvant être obtenus à partir de ces derniers
WO2017202772A1 (fr) * 2016-05-26 2017-11-30 Solvay Specialty Polymers Italy S.P.A. Polymères fluorés comprenant des groupes terminaux aromatiques
WO2018108864A1 (fr) 2016-12-14 2018-06-21 Solvay Specialty Polymers Italy S.P.A. Polymères de (per)fluoropolyéther
US10899883B2 (en) 2016-12-14 2021-01-26 Solvay Specialty Polymers Italy S.P.A. (Per)fluoropolyether polymers
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WO2019243403A1 (fr) * 2018-06-20 2019-12-26 Solvay Specialty Polymers Italy S.P.A. Polymères de (per)fluoropolyéther
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EP2331491B1 (fr) 2016-03-30
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CN102177123B (zh) 2016-05-04
US8946136B2 (en) 2015-02-03
JP2011530565A (ja) 2011-12-22
US20110136713A1 (en) 2011-06-09
KR20110068996A (ko) 2011-06-22
WO2010057691A3 (fr) 2010-10-14
JP5743217B2 (ja) 2015-07-01
CN102177123A (zh) 2011-09-07

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