WO2007081008A1 - Nouvel agent tensioactif fluore et nouveau compose fluore - Google Patents

Nouvel agent tensioactif fluore et nouveau compose fluore Download PDF

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Publication number
WO2007081008A1
WO2007081008A1 PCT/JP2007/050423 JP2007050423W WO2007081008A1 WO 2007081008 A1 WO2007081008 A1 WO 2007081008A1 JP 2007050423 W JP2007050423 W JP 2007050423W WO 2007081008 A1 WO2007081008 A1 WO 2007081008A1
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group
fluorine
ring
carbon atoms
compound
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PCT/JP2007/050423
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English (en)
Japanese (ja)
Inventor
Takashi Okazoe
Yuriko Akiyama
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Asahi Glass Company, Limited
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Priority to JP2007553971A priority Critical patent/JPWO2007081008A1/ja
Publication of WO2007081008A1 publication Critical patent/WO2007081008A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/42—Halogen atoms or nitro radicals

Definitions

  • the present invention relates to a novel fluorine-based surfactant and a novel fluorine-containing compound.
  • a fluorine-containing compound having a hydrophilic group and a fluorine-containing hydrophobic group is excellent in chemical stability and surface activity, and is used as a surfactant.
  • the hydrophilic group in the fluorine-containing compound include an ionic group, a cationic group, an amphoteric group, and a nonionic group.
  • examples of the fluorine-containing hydrophobic group in the fluorine-containing compound include an etheric oxygen atom and may include a polyfluoroalkyl group.
  • an acyclic fluorine-containing compound having one hydrophilic group and two fluorine-containing hydrophobic groups for example, a compound represented by the following formula (si)
  • Patent Document 2 a compound represented by the following formula (s2)
  • Patent Document 3 discloses a fluorine-containing surfactant having a ring structure represented by the following formula as a fluorine-based surfactant used in suspension polymerization or emulsion polymerization of fluorine-containing olefins in water. Compounds are described.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 64-536
  • Patent Document 2 JP-A-4-248543
  • Patent Document 3 Japanese Patent Laid-Open No. 7-292008
  • the present invention has the following gist.
  • the two chain-like fluorine-containing hydrophobic groups are bonded to one carbon atom selected from the ring carbon atoms or two adjacent carbon atoms, and the hydrophilic group is bonded.
  • a fluorine-containing surfactant comprising a fluorine-containing compound having a structure in which a ring carbon atom and a ring carbon atom to which a chain-like fluorine-containing hydrophobic group is bonded are not adjacent to each other.
  • Ring force is a saturated ring composed of only 4 or more carbon atoms, or a saturated ring composed of 3 or more carbon atoms and 1 or 2 oxygen atoms. Fluorosurfactant listed.
  • ⁇ 3> The above ⁇ 1> or ⁇ 1>, wherein the ring is a saturated ring composed of 3, 4 or 5 carbon atoms and 1 or 2 oxygen atoms and is a 5-membered or 6-membered ring Fluorine-based surfactant according to 2>.
  • hydrophilic group is directly bonded to the ring according to any one of the above ⁇ 1> to ⁇ 4> Fluorosurfactant.
  • the hydrophilic group is a group selected from the group consisting of a carboxyl group, a carboxyl group-derived group, a sulfonic acid group, and a sulfonic acid group-derived group, according to any one of the above ⁇ 1> to ⁇ 5> Fluorosurfactant.
  • the chain fluorine-containing hydrophobic group has an etheric oxygen atom having 1 to 20 carbon atoms and may be V, or may be a polyfluoroalkyl group in the above 1> to ⁇ 7> !,
  • the fluorine-based surfactant according to any one of the above.
  • X 1 and X 2 each independently —O— or —CF—.
  • Y group represented by the formula — CY 1 Y 2 — or group represented by the formula — CFY FY 4 — (where Y 1 , ⁇ 2 , ⁇ 3 , and ⁇ 4 are each independently a carboxyl group, Derived group of carboxylic group, sulfonic acid group, and group strength of derivatized group of sulfonic acid group Selected group, or a polyfluoroalkyl group having a C 1-10 etheric oxygen atom having the group ) 0
  • ⁇ a group represented by the formula — CZZ 2 — or a group represented by the formula — CFZ 3 CFZ 4 — (wherein Z and Z 4 each independently have an etheric oxygen atom having 1 to 20 carbon atoms) And a polyfluoroalkyl group that may be present).
  • Q A1 and Q A2 each independently a single bond, carbon number 1 to: perfluoroalkylene group of L0, or carbon atom number 2 to 10 containing an etheric oxygen atom between one carbon atom Oalkylene group.
  • T A — C (0) OH or C (0) ONH.
  • R A1 and R A2 each independently a C 1 to C: perfluoroalkyl group having L 0 or a C 2 to C 10 perfluoroalkyl group containing an etheric oxygen atom between one carbon atom.
  • a fluorosurfactant having excellent surface activity is provided.
  • the present invention also provides a novel fluorine-containing compound that is useful as a surfactant.
  • the compound represented by the formula (1) is also referred to as a compound (1).
  • the fluorosurfactant of the present invention comprises two hydrophilic groups, two chain-like fluorine-containing hydrophobic groups, and a force, each of which contains a structure bonded to a ring directly or via a linking group.
  • the ring is a carbon atom or a ring of four or more members composed of a carbon atom and a heteroatom, and the two hydrophilic groups are carbon atoms of the ring.
  • a fluorine-containing compound having a structure in which a ring carbon atom to which a hydrophilic group is bonded and a ring carbon atom to which a chain-like fluorine-containing hydrophobic group is bonded are not adjacent to each other.
  • the ring in the fluorine-containing compound is a saturated ring composed of only 4 or more carbon atoms. It is preferably a saturated ring composed of 3 or more carbon atoms and 1 or 2 oxygen atoms. It is composed of 3 or more carbon atoms and 1 or 2 oxygen atoms. Particularly preferred is a saturated ring. Further, the upper limit of carbon atoms in the saturated ring is not particularly limited, and preferably 10 or less, particularly preferably 5 or less.
  • a preferred embodiment of the ring in the fluorine-containing compound is a saturated ring composed of 3, 4 or 5 carbon atoms and 1 or 2 oxygen atoms, and is a 5-membered or 6-membered ring. A ring is mentioned.
  • Groups other than the two hydrophilic groups and the two chain-like fluorine-containing hydrophobic groups bonded to the ring carbon atom in the fluorine-containing compound are a hydrogen atom, a fluorine atom, an alkyl group, and an alkoxy group.
  • Group Force One or more groups selected are preferably a hydrogen atom, a fluorine atom, an alkyl group having 1 to 6 carbon atoms, and an alkoxy group force having 1 to 6 carbon atoms.
  • a hydrogen atom or a fluorine atom with a particularly preferred hydrogen atom or a fluorine atom being particularly preferred is most preferred.
  • the two hydrophilic groups in the fluorine-containing compound are preferably directly bonded to the ring, which may be directly bonded to the ring via a linking group which may be directly bonded to the ring.
  • the linking group is a difluoromethylene group, which is preferably a perfluoroalkylene group having 1 to 5 carbon atoms, which is preferably a polyfluoroalkylene group which may have an etheric oxygen atom having 1 to 10 carbon atoms. Is particularly preferred.
  • the two hydrophilic groups are preferably the same hydrophilic group, which may be the same hydrophilic group or different hydrophilic groups.
  • the kind of the hydrophilic group is not particularly limited, and a carboxyl group, a derivative group thereof, a sulfonic acid group, or a derivative group thereof is particularly preferable.
  • the derivative group of the carboxyl group is a group represented by the formula —C (0) OW R1 or a formula —C (0) N (
  • w R1 Lithium, potassium, sodium, or ammonium.
  • W R2 A hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms.
  • w Quaternary ammonium halide salt, betaine, amine oxide, and carboxylate group power of force selected 1 compound with 1 or more hydrogen atoms bonded to carbon atoms, 1 hydrogen atom removed, 1 Valent group.
  • W R2 and W R3 may be bonded to each other to form a divalent group.
  • the divalent group is a quaternary ammonium halide salt, betaine, amine oxide, and a group force that also has an amino acid salt power, and a compound power that requires two or more hydrogen atoms bonded to carbon atoms. Except that it is preferably a divalent group.
  • C (0) OW R1 Specific examples of the group represented by the formula C (0) OW R1 include C (0) OLi, 1C (0) ONa, 1C (0) OK, -C (0) ONH .
  • the derivative group of the sulfonic acid group is a group represented by the formula SO (OW sl ) or a formula SO N (—
  • a group represented by 2 2 w S2 ) (-w S3 ) is preferred.
  • w sl Lithium, potassium, sodium, or ammonium.
  • W S2 and W S3 each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms.
  • the two chain-like fluorine-containing hydrophobic groups in the fluorine-containing compound are directly bonded to the ring, which may be directly bonded to the ring via a linking group or may be bonded to the ring. I like it.
  • the two chain fluorine-containing hydrophobic groups may be the same chain fluorine-containing hydrophobic group or different chain fluorine-containing hydrophobic groups.
  • the type of the chain fluorine-containing hydrophobic group is not particularly limited, and has an etheric oxygen atom having 1 to 20 carbon atoms! /, May! /, A carbon preferred for a polyfluoroalkyl group.
  • a perfluoroalkyl group having 1 to 10 carbon atoms is more preferable, and a perfluoroalkyl group having 4 to 10 carbon atoms is particularly preferable!
  • the molecular weight of the fluorine-containing compound is 300-3000 force ⁇ , 600-1500 force
  • the fluorine atom content of the fluorine-containing compound is preferably from 30 to 70 mass%, particularly preferably from 45 to 70 mass%.
  • the fluorine-containing compound in the present invention is preferably the following compound (S).
  • X 1 and X 2 are each —O 2, are each —CF—, or
  • one is O and the other is CF-
  • Y is a group represented by the formula —CY or a group represented by the formula —CFY 3 CFY 4 —.
  • ⁇ ⁇ ⁇ 2, ⁇ 3 , and Upsilon 4 are each independently a carboxyl group, derivative groups, sulfonic acid groups, and groups selected from the group consisting of induction of sulfonic groups a carboxyl group or a base, 1 to C: a polyfluoroalkyl group optionally having an etheric oxygen atom of L0.
  • ⁇ ⁇ ⁇ 2 , ⁇ 3 , and ⁇ 4 are each independently preferably C (0) OLi, C (0) ONa, carboxy group-derived group or sulfonate group-derived group.
  • C (0) OK or C (0) ONH is more preferred, C (0) ONH
  • Y 1 and Y 2 are preferably the same group.
  • Y 3 and Y 4 are preferably the same group.
  • Z is a group represented by the group or the formula CFZ 3 CFZ 4 Formula CZ Z 2.
  • Z 3 and Z 4 each independently represent a polyfluoroalkyl group optionally having an etheric oxygen atom having 1 to 20 carbon atoms.
  • zzz and And z 4 are each independently a perfluoroalkyl group having 4 to 10 carbon atoms, preferably a perfluoroalkyl group having 1 to 10 carbon atoms.
  • Z 1 and Z 2 may be the same group or different groups.
  • Z 3 and Z 4 may be the same group or different groups.
  • Preferred embodiments of the compound (S) include the following compound (A) and the following compound (B).
  • Q A1 and Q A2 in the compound (A) are each particularly preferably a single bond or a single bond, preferably a perfluoroalkylene group having 1 to 10 carbon atoms.
  • Q A1 and Q A2 may be the same or different.
  • C (0) ONH is preferable.
  • R A1 and R A2 are each independently preferably a perfluoroalkyl group having 4 to 10 carbon atoms, which is preferably a C 1 to C perfluoroalkyl group! / ⁇ .
  • R A1 and R A2 may be the same group or different groups.
  • Q B1 and Q B2 are each independently a single bond, carbon number 1 to: perfluoroalkylene group of LO, or carbon atom Perfluoro having 2 to 10 carbon atoms including an etheric oxygen atom between carbon atoms Loalkylene group.
  • T B -C (O) OH or C (O) ONH.
  • R B1 and R B2 each independently, a C 1 to C: perfluoroalkyl group having L 0, or a C 2 to C 10 perfluorinated alkyl group containing an etheric oxygen atom between carbon atoms.
  • Q m and in the compound) are particularly preferably a single bond or a single bond, preferably a perfluoroalkylene group having 1 to 10 carbon atoms.
  • Q B1 and Q B2 may be the same group or different groups.
  • T B in the compound (B) is preferably —C (0) ONH.
  • R 1 and R 2 in the compound are each independently preferably a perfluoroalkyl group having 1 to 10 carbon atoms, preferably a perfluoroalkyl group having 4 to 10 carbon atoms, preferably a LO perfluoroalkyl group! / ⁇ .
  • R m and R B2 may be the same or different.
  • Specific examples of the compound (B) include the following compounds.
  • the method for producing the compound (A) is not particularly limited, and it is preferably produced by chemical conversion of the —COF group of the following compound (A1).
  • the chemical conversion is not particularly limited, and a known method can be applied.
  • the compound ( ⁇ ) wherein -C ( ⁇ ) ⁇ is produced by reacting the compound (A1) with methanol and then subjecting it to a hydrolysis reaction.
  • T Alpha is - C (0) compound which is ONH (A) is
  • T A is prepared by reacting one C (0) compound is OH (A) and ammonia
  • Specific examples of the compound (A1) include the following compounds.
  • the compound (Al) is obtained by subjecting the following compound (A5) and the following compound (A4) to an acetal reaction to obtain the following compound (A3), and then fluorinating the compound (A3) to produce the following compound (A2 It is preferable that the compound (A2) is produced by an ester decomposition reaction.
  • R al fluorinated in the same group as radicals or R A1 to be R A1.
  • R a2 fluorinated in the same group as radicals or R A2 as the R A2.
  • Q al single bond, fluorinated in the Q A1 group or the same group as Q A1,.
  • Q a2 a single bond, fluorinated in Q A2 become group or Q A2 same group as.
  • V al and V a2 each independently an alkyl group which may contain a tellurium oxygen atom between carbon atoms having 120 carbon atoms and carbon atoms, or ether between carbon atoms having 120 carbon atoms and carbon atoms A perfluoroalkyl group containing a reactive oxygen atom.
  • V A1 and V A2 each independently a perfluoroalkyl group containing a tellurium oxygen atom between a carbon atom having 120 carbon atoms and a carbon atom.
  • R A1 R A2 Q A1 and Q A2 have the same meaning as described above.
  • R al is preferably a group that is fluorinated and becomes R A1
  • R a2 is preferably a group that is fluorinated and becomes R A2
  • an alkyl group having 1 to 10 carbon atoms, or a carbon atom Particularly preferred is an alkyl group having 2 10 carbon atoms containing an etheric oxygen atom.
  • Q al prefers a single bond or fluorinated group to form Q A1
  • Q a2 prefers a single bond or fluorinated group to form Q A2 independently of each other, a single bond, carbon
  • An alkylene group having 1 10 carbon atoms, or an alkylene group having 2 10 carbon atoms containing an etheric oxygen atom between carbon atoms is more preferable, and a single bond is particularly preferable! /.
  • the acetal reaction, the fluorination reaction, and the ester decomposition reaction are preferably carried out according to known methods.
  • the fluorination reaction is particularly preferably carried out by a liquid phase fluorination method, preferably a liquid phase fluorination method, an electrolytic fluorination method or a cobalt fluorination method.
  • a liquid phase fluorination method preferably a liquid phase fluorination method, an electrolytic fluorination method or a cobalt fluorination method.
  • the liquid phase fluorination method the liquid phase fluorination method described in International Publication No. 00Z56694 pamphlet is preferable.
  • Specific examples of the compound (A5) include the following compounds.
  • Specific examples of the compound (A3) include the following compounds.
  • the compound (B) is also a novel compound whose literature is unknown.
  • the production method of the compound (B) is not particularly limited, and it is preferably produced by chemical conversion of the COF group of the following compound (B1).
  • the chemical conversion is not particularly limited, and a known method can be applied.
  • ⁇ ⁇ gar C The compound (B) which is (O) OH is preferably produced by reacting the compound (Bl) with methanol and then performing a hydrolysis reaction.
  • T B is —C (0) ONH
  • B) is preferably produced by reacting ammonia with a compound (B) in which T B is —C (0) OH.
  • Specific examples of the compound (B1) include the following compounds.
  • Compound (Bl) is obtained by subjecting the following compound (B5) and the following compound (B4) to an acetalization reaction to obtain the following compound (B3), and then fluorinating the compound (B3) to obtain the following compound (B2). It is preferable that the compound (B2) is produced by an ester decomposition reaction.
  • R bl fluorinated in the same group as radicals or R B1 as the R B1.
  • R b2 fluorinated in the same group as radicals or R B2 serving as R B2.
  • Q bl a single bond, a group that is fluorinated to form Q B1 , or the same group as Q B1 .
  • Q b2 single bond, fluorinated in the Q B2 group or Q B2 same group as.
  • V bl and V b2 each independently, a carbon atom number of 1 20 carbon atoms - an alkyl group which may contain a te Le oxygen atom between carbon atoms or carbon atoms of a carbon number of 1 20, - ether between carbon atoms A perfluoroalkyl group containing a reactive oxygen atom.
  • V B1 and V B2 each independently, a carbon atom number of 1 20 carbon atoms - contain ether oxygen atom between carbon atoms, even I, pel full O b alkyl group.
  • R m R B2 Q B1 and Q B2 have the same meaning as described above.
  • R bl is preferably a group fluorinated to become R B1
  • R b2 is preferably a group fluorinated to become R B2
  • an alkyl group having 1 to 10 carbon atoms, or a carbon atom Particularly preferred is an alkyl group having 2 10 carbon atoms containing an etheric oxygen atom.
  • Q bl is preferably a single bond or fluorinated group to form Q B1
  • Q b2 is preferably a single bond or fluorinated group to form Q B2 independently of each other, a single bond, carbon number 1 10 And an alkylene group having 2 to 10 carbon atoms containing an etheric oxygen atom between carbon atoms, more preferably a single bond!
  • the acetal reaction, the fluorination reaction, and the ester decomposition reaction are preferably carried out according to known methods.
  • the fluorination reaction is particularly preferably carried out by a liquid phase fluorination method, preferably a liquid phase fluorination method, an electrolytic fluorination method, or a cobalt fluorination method.
  • a liquid phase fluorination method preferably a liquid phase fluorination method, an electrolytic fluorination method, or a cobalt fluorination method.
  • the liquid phase fluorination method the liquid phase fluorination method described in International Publication No. 00Z56694 pamphlet is preferable.
  • Specific examples of the compound (B5) include the following compounds.
  • the compound (A) and the compound (B) of the present invention are useful as a monomer raw material, a fluorosurfactant and the like, and particularly useful as a fluorosurfactant.
  • CF-CICF CHC1F and CHCl CF CF are mixed with R-225 and CC1, respectively.
  • FCC1F is R-113
  • gas chromatography is GC
  • nuclear magnetic resonance method is NMR
  • Tetramethylsilane is referred to as TMS.
  • An autoclave (made of nickel, internal volume 3000 mL) was prepared, and a NaF pellet packed bed was installed at the gas outlet of the autoclave.
  • R-113 (1600 g) was placed in an autoclave and stirred while maintaining at 25 ° C. As it was, nitrogen gas was blown into the autoclave for 1 hour, and then fluorine gas diluted to 20% by volume with nitrogen gas (hereinafter referred to as 20% fluorine gas) was blown.
  • a solution obtained by dissolving the compound (A3-1) (25.0 g) obtained in Example 1-1 in R-113 was introduced into an autoclave, and 20% fluorine gas was blown in as it was.
  • the flask was charged with the compound (A2-1) (33. lg) obtained in Example 1-2 and KF powder (1. lg). The inside of the flask was heated to 40 ° C. and stirred for reaction for 8 hours. Thereafter, the obtained reaction crude liquid was distilled under reduced pressure to obtain a fraction (3.99 g) at 83 ° C./0.23 kPa (absolute pressure). As a result of analyzing the fraction by NMR, it was confirmed that the compound (A1-1) was produced.
  • An appropriate amount of compound (A-1) is added to water, an aqueous solution (A 1) containing 0.1% by mass of compound (A-1), and an aqueous solution containing 0.01% by mass of compound (A-1) (A2 )
  • the static surface tension of the aqueous solution (A1) was 18.3 mNZm, and the static surface tension of the aqueous solution (A2) was 35.3 mN / m.
  • a fluorosurfactant having excellent surface activity is provided.
  • a novel fluorine-containing compound useful as a fluorine-based surfactant or the like is provided.
  • the fluorosurfactant of the present invention includes an emulsifier, an ink, a paint, a resist, etc. used for emulsion polymerization of a fluorine-containing monomer (tetrafluoroethylene, hexafluoropropylene, etc.) in an aqueous medium.
  • a fluorine-containing monomer tetrafluoroethylene, hexafluoropropylene, etc.
  • Water and oil repellents used to improve the wettability or permeability of foams, foam stabilizers, foaming aids and leveling agents (wax etc.) used to improve foam generation or fire extinguishing performance.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

La présente invention concerne un nouvel agent tensioactif fluoré et un nouveau composé fluoré. La présente invention concerne plus spécifiquement un agent tensioactif fluoré composé d’un composé fluoré ayant essentiellement une structure dans laquelle deux groupes hydrophiles et deux groupes hydrophobes fluorés formant une chaîne sont respectivement liés à un cycle directement ou par l'intermédiaire d'un groupe de liaison. Le cycle est un cycle à quatre éléments ou plus qui est composé seulement d'atomes de carbone ou d’atomes de carbone et d’un autre atome. Les deux groupes hydrophiles sont liés à un atome de carbone ou à deux atomes de carbone adjacents choisis parmi les atomes de carbone de cycle, tandis que les deux groupes hydrophobes fluorés formant une chaîne sont liés à un atome de carbone ou à deux atomes de carbone adjacents choisis parmi les atomes de carbone du cycle. En outre, l'atome de carbone auquel le groupe hydrophile est lié et l'atome de carbone auquel le groupe hydrophobe fluoré formant une chaîne est lié ne sont pas adjacents. La présente invention concerne également plus spécifiquement un nouveau composé fluoré représenté par la formule (A-1). (A-1)
PCT/JP2007/050423 2006-01-16 2007-01-15 Nouvel agent tensioactif fluore et nouveau compose fluore WO2007081008A1 (fr)

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Cited By (5)

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KR20110041467A (ko) * 2008-07-08 2011-04-21 솔베이 솔렉시스 에스.피.에이. 플루오로중합체의 제조 방법
JP2013514415A (ja) * 2009-12-18 2013-04-25 ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア フルオロエラストマーの製造方法
JP2013514407A (ja) * 2009-12-18 2013-04-25 ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア フッ化ビニリデンポリマーの分散系の製造方法
JP2015520282A (ja) * 2012-06-20 2015-07-16 ソルベイ スペシャルティ ポリマーズ イタリー エス．ピー．エー． テトラフルオロエチレンコポリマー
JP2015131777A (ja) * 2014-01-10 2015-07-23 信越化学工業株式会社 オニウム塩、化学増幅型ポジ型レジスト組成物、及びパターン形成方法

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JP2003522094A (ja) * 1997-11-20 2003-07-22 シンセティック・ブラッド・インターナショナル・インコーポレイテッド 液体換気及び人工血液のための選択されたｃ１０パーフルオロ炭化水素
JP2003335773A (ja) * 2002-05-20 2003-11-28 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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JPS5498750A (en) * 1977-12-27 1979-08-03 Ciba Geigy Ag Perfluoroalkylliodeenorvolnane compound and surfactant comprising it
JP2003522094A (ja) * 1997-11-20 2003-07-22 シンセティック・ブラッド・インターナショナル・インコーポレイテッド 液体換気及び人工血液のための選択されたｃ１０パーフルオロ炭化水素
JP2003335773A (ja) * 2002-05-20 2003-11-28 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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JP2004131493A (ja) * 2002-09-20 2004-04-30 Dainippon Ink & Chem Inc フッ素系界面活性剤

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110041467A (ko) * 2008-07-08 2011-04-21 솔베이 솔렉시스 에스.피.에이. 플루오로중합체의 제조 방법
JP2011527362A (ja) * 2008-07-08 2011-10-27 ソルヴェイ・ソレクシス・エッセ・ピ・ア フルオロポリマーの製造方法
KR101707245B1 (ko) 2008-07-08 2017-02-15 솔베이 스페셜티 폴리머스 이태리 에스.피.에이. 플루오로중합체의 제조 방법
JP2013514415A (ja) * 2009-12-18 2013-04-25 ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア フルオロエラストマーの製造方法
JP2013514407A (ja) * 2009-12-18 2013-04-25 ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア フッ化ビニリデンポリマーの分散系の製造方法
JP2015520282A (ja) * 2012-06-20 2015-07-16 ソルベイ スペシャルティ ポリマーズ イタリー エス．ピー．エー． テトラフルオロエチレンコポリマー
JP2015131777A (ja) * 2014-01-10 2015-07-23 信越化学工業株式会社 オニウム塩、化学増幅型ポジ型レジスト組成物、及びパターン形成方法

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