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WO2016088620A1 - Composé contenant un groupe perfluoropolyéther halogéné et son procédé de production - Google Patents

Composé contenant un groupe perfluoropolyéther halogéné et son procédé de production Download PDF

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WO2016088620A1
WO2016088620A1 PCT/JP2015/083061 JP2015083061W WO2016088620A1 WO 2016088620 A1 WO2016088620 A1 WO 2016088620A1 JP 2015083061 W JP2015083061 W JP 2015083061W WO 2016088620 A1 WO2016088620 A1 WO 2016088620A1
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ocf
atom
group
independently
integer
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Japanese (ja)
Inventor
尚志 三橋
敬 並川
真由子 高野
健太郎 平賀
杉山　明平
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Daikin Industries Ltd
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Daikin Industries Ltd
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Priority claimed from JP2014261744A external-priority patent/JP6020546B2/ja
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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
    • C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
    • 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
    • C07C43/12—Saturated ethers containing halogen
    • 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
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements

Definitions

  • the present invention relates to a halogenated perfluoropolyether group-containing compound and a method for producing the same.
  • fluorine-containing silane compounds can provide excellent water repellency, oil repellency, antifouling properties and the like when used for surface treatment of a substrate.
  • a layer obtained from a surface treatment agent containing a fluorine-containing silane compound (hereinafter also referred to as “surface treatment layer”) is applied as a so-called functional thin film to various substrates such as glass, plastic, fiber, and building materials. ing.
  • Patent Document 1 discloses the following general formula: [Wherein Rf is a perfluoroalkyl group, Z is a fluorine or trifluoromethyl group, and a, b, c, d and e are each independently 0 or an integer of 1 or more.
  • Y is hydrogen or an alkyl group having 1 to 4 carbon atoms
  • X is hydrogen, bromine or iodine
  • R 1 is a hydroxyl group or a hydrolyzable substituent
  • R 2 is hydrogen or 1 Is a valent hydrocarbon group
  • 1 is 0, 1 or 2
  • m is 1, 2 or 3
  • n is an integer of 2 or more.
  • the above compounds can be synthesized by an iodine transfer polymerization method (see Patent Document 2). Specifically, in Patent Document 1, iodine is introduced at the end of the fluoropolymer chain, and a silane compound having an ethylenic double bond is added to the compound having iodine at the end of the obtained fluoropolymer chain. It is synthesized by living polymerization (iodine transfer polymerization).
  • iodination as described in Patent Documents 1 and 3 can be suitably used when the fluorine-containing polymer chain has a repeating unit represented by — (OCF 2 CF 2 CF 2 ) —.
  • the fluoropolymer chain has a repeating unit represented by — (OCF 2 CF 2 ) — and — (OCF 2 ) —, the fluorine-containing polymer chain is decomposed and a by-product is generated. It was difficult.
  • An object of the present invention is to provide a method for suitably producing a perfluoropolyether group-containing compound having a halogen atom at the terminal regardless of the structure of the fluorine-containing polymer (that is, perfluoropolyether group).
  • Another object of the present invention is to provide a synthetic intermediate having a novel structure for synthesizing a perfluoropolyether group-containing silane compound.
  • the present inventors have made a perfluoropolyether by reacting an alcohol having a perfluoropolyether group with a compound having a halogen atom at one end and a double bond at the other end. Even when the group has any structure, it has been found that a perfluoropolyether group-containing compound having a halogen atom at the terminal can be preferably produced, and the present invention has been completed.
  • Rf independently represents each alkyl group having 1 to 16 carbon atoms which may be substituted with one or more fluorine atoms at each occurrence;
  • PFPE has the general formula: -(OC 4 F 8 ) a- (OC 3 F 6 ) b- (OC 2 F 4 ) c- (OCF 2 ) d- Wherein a, b, c and d are each independently an integer of 0 to 200, and the sum of a, b, c and d is at least 1, and the subscripts a, b, c or d
  • a group represented by: Q is a divalent organic group containing at least one hydrogen atom and at least one fluorine atom bonded to a carbon atom; R 1 is a hydrogen atom or a fluorine atom; Y is a chlorine
  • PFPE has the general formula: -(OC 4 F 8 ) a- (OC 3 F 6 ) b- (OC 2 F 4 ) c- (OCF 2 ) d- Wherein a, b, c and d are each independently an integer of 0 to 200, and the sum of a, b, c and d is at least 1, and the subscripts a, b, c or d
  • a group represented by: Q ′′ is a divalent organic group containing at least one fluorine atom bonded to a carbon atom; R 1 is a hydrogen atom or a fluorine atom; Y is a chlorine atom, a bromine
  • a novel halogenated perfluoropolyether group-containing compound can be synthesized.
  • this halogenated perfluoropolyether group-containing compound can be used as an intermediate for the production of perfluoropolyether group-containing silane compounds, enabling the synthesis of perfluoropolyether group-containing silane compounds having various structures. To do.
  • the present invention relates to the following general formula (I): [Where: Rf independently represents each alkyl group having 1 to 16 carbon atoms which may be substituted with one or more fluorine atoms at each occurrence; PFPE has the general formula: -(OC 4 F 8 ) a- (OC 3 F 6 ) b- (OC 2 F 4 ) c- (OCF 2 ) d- Wherein a, b, c and d are each independently an integer of 0 to 200, and the sum of a, b, c and d is at least 1, and the subscripts a, b, c or d The order of existence of each repeating unit with parentheses attached with is arbitrary in the formula.) A group represented by: Q is a divalent organic group containing at least one hydrogen atom and at least one fluorine atom bonded to a carbon atom; R 1 is a hydrogen atom or a fluorine atom; Y is a chlorine atom, a bromine
  • Rf represents an alkyl group having 1 to 16 carbon atoms which may be substituted with one or more fluorine atoms.
  • alkyl group having 1 to 16 carbon atoms in the alkyl group having 1 to 16 carbon atoms which may be substituted with one or more fluorine atoms may be linear or branched. Preferably, it is a linear or branched alkyl group having 1 to 6 carbon atoms, particularly 1 to 3 carbon atoms, and more preferably a linear alkyl group having 1 to 3 carbon atoms.
  • Rf is preferably an alkyl group having 1 to 16 carbon atoms, which is substituted with one or more fluorine atoms, more preferably a CF 2 H—C 1-15 fluoroalkylene group, still more preferably Is a perfluoroalkyl group having 1 to 16 carbon atoms.
  • the perfluoroalkyl group having 1 to 16 carbon atoms may be linear or branched, and preferably has 1 to 6 carbon atoms, particularly 1 to 6 carbon atoms. 3 perfluoroalkyl group, more preferably a linear perfluoroalkyl group having 1 to 3 carbon atoms, specifically —CF 3 , —CF 2 CF 3 , or —CF 2 CF 2 CF 3 . .
  • PFPE has the general formula: -(OC 4 F 8 ) a- (OC 3 F 6 ) b- (OC 2 F 4 ) c- (OCF 2 ) d- Represents a perfluoro (poly) ether group.
  • a, b, c and d are each independently an integer of 0 or 1 and are not particularly limited as long as the sum of a, b, c and d is at least 1.
  • a, b, c and d are each independently an integer of 0 to 200, for example, an integer of 1 to 200, more preferably an integer of 0 to 100, for example, 1 An integer of 100 or less.
  • the sum of a, b, c and d is 10 or more, preferably 20 or more, and 200 or less, preferably 100 or less. Further, the order of presence of each repeating unit with a, b, c or d in parentheses is arbitrary in the formula.
  • — (OC 4 F 8 ) — represents — (OCF 2 CF 2 CF 2 CF 2 ) —, — (OCF (CF 3 ) CF 2 CF 2 ) —, — (OCF 2 CF (CF 3 ) CF 2 )-,-(OCF 2 CF 2 CF (CF 3 ))-,-(OC (CF 3 ) 2 CF 2 )-,-(OCF 2 C (CF 3 ) 2 )-,-(OCF (CF 3 ) CF (CF 3 ))-,-(OCF (C 2 F 5 ) CF 2 )-and-(OCF 2 CF (C 2 F 5 ))-may be used, but preferably — (OCF 2 CF 2 CF 2 CF 2 ) —.
  • -(OC 3 F 6 )- is any of-(OCF 2 CF 2 CF 2 )-,-(OCF (CF 3 ) CF 2 )-and-(OCF 2 CF (CF 3 ))- Preferably, it is — (OCF 2 CF 2 CF 2 ) —.
  • — (OC 2 F 4 ) — may be any of — (OCF 2 CF 2 ) — and — (OCF (CF 3 )) —, preferably — (OCF 2 CF 2 ) —. is there.
  • PFPE is — (OC 3 F 6 ) b — (wherein b is an integer of 1 to 200, preferably 10 to 100), preferably — (OCF 2 CF 2 CF 2 ) b — (wherein b is as defined above).
  • the PFPE is -(OC 4 F 8 ) a- (OC 3 F 6 ) b- (OC 2 F 4 ) c- (OCF 2 ) d-
  • a and b are each independently an integer of 0 or more or 1 or more and 30 or less, preferably 0 or more and 10 or less
  • c and d are each independently 1 or more and 200 or less, preferably 10 or more. It is an integer of 100 or less, and the sum of a, b, c and d is 10 or more, preferably 20 or more, and 200 or less, preferably 100 or less.
  • each repeating unit in parentheses is arbitrary in the formula), preferably — (OCF 2 CF 2 CF 2 ) a — (OCF 2 CF 2 CF 2 ) b — (OCF 2 CF 2 ) c — (OCF 2 ) d — (wherein a, b, c and d are as defined above).
  • PFPE may be — (OCF 2 CF 2 ) c — (OCF 2 ) d — (wherein c and d are as defined above).
  • PFPE is a group represented by — (OC 2 F 4 —R 8 ) e —.
  • R 8 is a group selected from OC 2 F 4 , OC 3 F 6 and OC 4 F 8 , or a combination of 2 or 3 groups independently selected from these groups is there.
  • the combination of 2 or 3 groups independently selected from OC 2 F 4 , OC 3 F 6 and OC 4 F 8 is not particularly limited.
  • the e is an integer of 2 to 100, preferably an integer of 2 to 50.
  • OC 2 F 4 , OC 3 F 6 and OC 4 F 8 may be either linear or branched, preferably linear.
  • the PFPE is preferably — (OC 2 F 4 —OC 3 F 6 ) e — or — (OC 2 F 4 —OC 4 F 8 ) e —.
  • Q is a divalent organic group containing at least one hydrogen atom bonded to a carbon atom and at least one fluorine atom.
  • divalent organic group means a divalent group containing carbon. Such a divalent organic group means a group in which two hydrogen atoms are eliminated from a hydrocarbon. Such a divalent organic group is not particularly limited, but is a divalent hydrocarbon group having 1 to 20 carbon atoms which may be substituted with one or more substituents, for example, an aliphatic group. A hydrocarbon group, an aromatic hydrocarbon group, etc. are mentioned.
  • the “aliphatic hydrocarbon group” may be linear, branched or cyclic, and may be either saturated or unsaturated.
  • the hydrocarbon group may also contain one or more ring structures. Such a hydrocarbon group may have one or more N, O, S, Si, amide, sulfonyl, siloxane, carbonyl, carbonyloxy and the like at its terminal or molecular chain.
  • the substituent of the hydrocarbon group is not particularly limited.
  • a halogen atom a C 1-6 alkyl group which may be substituted with one or more halogen atoms C 2-6 alkenyl group, C 2-6 alkynyl group, C 3-10 cycloalkyl group, C 3-10 unsaturated cycloalkyl group, 5-10 membered heterocyclyl group, 5-10 membered unsaturated heterocyclyl group , One or more groups selected from C 6-10 aryl groups and 5- to 10-membered heteroaryl groups.
  • Q is represented by the following formula: — (CH 2 ) n —O—CR 2 2 —CR 3 2 —Q′-CFR 4 —
  • Q ′ is a divalent organic group;
  • Each R 2 is independently a hydrogen atom or a fluorine atom;
  • Each R 3 is independently a hydrogen atom or a fluorine atom;
  • R 4 is a hydrogen atom or a fluorine atom;
  • n is an integer of 1 to 6.
  • Q ′ is a divalent organic group.
  • Q ′ is represented by the following formula: -(R 11 ) p- (R 12 ) q- It is group represented by these.
  • the order of presence of each repeating unit in parentheses with the suffix p or q is arbitrary in the formula.
  • R 11 is independently at each occurrence an oxygen atom, —NR 13 — (wherein R 13 may be substituted with a hydrogen atom, or one or more fluorine atoms. Represents a good lower alkyl group) or a divalent polar group.
  • the lower alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, and a propyl group. May be substituted by one or more fluorine atoms.
  • R 11 is an oxygen atom.
  • the “divalent polar group” in Q ′ is not particularly limited, but —C (O) —, —C ( ⁇ NR 13 ) —, and —C (O) NR 13 — (in these formulas, R 13 has the same meaning as described above, and represents a hydrogen atom or a lower alkyl group which may be substituted with one or more fluorine atoms.
  • the lower alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, and a propyl group. May be substituted by one or more fluorine atoms.
  • R 12 is independently at each occurrence, —CR 14 2 — (wherein R 14 is independently a hydrogen atom, a fluorine atom, or one or more fluorine atoms.
  • R 14 is independently a hydrogen atom, a fluorine atom, or one or more fluorine atoms.
  • the lower alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, and a propyl group. May be substituted by one or more fluorine atoms.
  • R 12 is —CF 2 — or —CF (CF 3 ) —.
  • Q ′ is such that R 11 is an oxygen atom, and R 12 is independently —CF 2 — or —CF (CF 3 ) —.
  • p is an integer of 1 to 6, preferably an integer of 1 to 3.
  • Q is an integer of 0 to 20, preferably an integer of 0 to 10, and more preferably an integer of 0 to 6.
  • Q ′ are not particularly limited, but include the following groups: -O-, -OCF 2- , -OCF 2 CF 2- , -OCFCF 2 CF 2- —OCF 2 CF (CF 3 ) O— —OCF 2 CF (CF 3 ) OCF 2 — —OCF 2 CF (CF 3 ) OCF 2 CF 2 — -CF 2 O-, -CF 2 OCF 2- , -CF 2 OCF 2 CF 2- , -CF 2 OCF (CF 3 ) CF 2 O-, —CF 2 OCF (CF 3 ) CF 2 OCF 2 —, or —CF 2 OCF (CF 3 ) CF 2 OCF 2 CF 2 —, Is mentioned.
  • Q ′ is -O- -OCF 2- , —OCF 2 CF 2 — or —OCF 2 CF 2 CF 2 — It is.
  • R 2 is independently a hydrogen atom or a fluorine atom
  • R 3 is independently a hydrogen atom or a fluorine atom. In one embodiment, at least one of R 3 is a hydrogen atom.
  • R 4 is a hydrogen atom or a fluorine atom, preferably a fluorine atom.
  • n is an integer of 1 to 6, preferably an integer of 1 to 3.
  • Q include, but are not limited to, the following groups: -CH 2 OCF 2 CHFOCF 2- , -CH 2 OCF 2 CHFOCF 2 CF 2- , -CH 2 OCF 2 CHFOCF 2 CF 2 CF 2- , —CH 2 OCF 2 CHFOCF 2 CF (CF 3 ) OCF 2 —, —CH 2 OCF 2 CHFOCF 2 CF (CF 3 ) OCF 2 CF 2 —, -CH 2 OCF 2 CHFOCF 2 CF ( CF 3) OCF 2 CF 2 CF 2 -, -CH 2 OCH 2 CHFCF 2 OCF 2- , -CH 2 OCH 2 CHFCF 2 OCF 2 CF 2- , -CH 2 OCH 2 CHFCF 2 OCF 2 CF 2 CF 2- , —CH 2 OCH 2 CHFCF 2 OCF 2 CF 2 CF 2- , —CH 2 OCH 2 CHFCF 2 OCF 2 CF 2 CF 2- , —CH 2 OCH 2 CHFCF 2
  • R 1 is a hydrogen atom or a fluorine atom. In one embodiment, R 1 is a fluorine atom. In the above formula (I), when l is 0, that is, when Q is not present, R 1 is a hydrogen atom.
  • Y is a chlorine atom, a bromine atom or an iodine atom, preferably an iodine atom.
  • m is an integer of 0 to 3, preferably an integer of 0 to 2, for example 0 or 1.
  • the compound represented by the formula (I) is represented by the following general formula (Ia): [Where: Rf independently represents each alkyl group having 1 to 16 carbon atoms which may be substituted with one or more fluorine atoms at each occurrence; PFPE has the general formula: -(OC 4 F 8 ) a- (OC 3 F 6 ) b- (OC 2 F 4 ) c- (OCF 2 ) d- Wherein a, b, c and d are each independently an integer of 0 to 200, and the sum of a, b, c and d is at least 1, and the subscripts a, b, c or d The order of existence of each repeating unit with parentheses attached with is arbitrary in the formula.) A group represented by: Q ′ is a divalent organic group; Each R 1 is independently a hydrogen atom or a fluorine atom; Each R 2 is independently a hydrogen atom or a fluorine atom; R 3 is a
  • the compound represented by the formula (I) and the formula (Ia) is a compound other than CF 3 (OCF 2 CF 2 ) 20 (OCF 2 ) 16 OCF 2 CH 2 OCF 2 CHFOCF 2 CF 2 I It is. That is, the compounds represented by the above formulas (I) and (Ia) do not include CF 3 (OCF 2 CF 2 ) 20 (OCF 2 ) 16 OCF 2 CH 2 OCF 2 CHFOCF 2 CF 2 I.
  • the present invention provides a CF 3 (OCF 2 CF 2) 20 (OCF 2) 16 OCF 2 CH 2 OCF 2 CHFOCF 2 CF 2 I.
  • the compound of the present invention is used as a synthetic intermediate for a perfluoropolyether group-containing silane compound useful as a water / oil repellent.
  • the compound represented by the formula (I) is represented by the following formula: [Where: R 21 represents, independently at each occurrence, a hydroxyl group or a hydrolyzable group; R 22 independently represents a hydrogen atom or an alkyl group at each occurrence; s is an arbitrary integer, for example, an integer of 1 to 20; t is an integer of 1 to 3. ] Is reacted with a compound represented by the following formula: [Wherein, Rf, PFPE, R 1 , Q, Y, m, l, R 21 , R 22 , s and t are as defined above, and u is an integer of 1 to 10. ] Can be obtained.
  • the present invention provides the following general formula (I ′): [Where: Rf independently represents each alkyl group having 1 to 16 carbon atoms which may be substituted with one or more fluorine atoms at each occurrence; PFPE has the general formula: -(OC 4 F 8 ) a- (OC 3 F 6 ) b- (OC 2 F 4 ) c- (OCF 2 ) d- Wherein a, b, c and d are each independently an integer of 0 to 200, and the sum of a, b, c and d is at least 1, and the subscripts a, b, c or d The order of existence of each repeating unit with parentheses attached with is arbitrary in the formula.) A group represented by: Q ′′ is a divalent organic group containing at least one fluorine atom bonded to a carbon atom; R 1 is a hydrogen atom or a fluorine atom; Y is a chlorine atom, a bromine atom
  • the method of the present invention can be used for the synthesis of a synthesis intermediate of a perfluoropolyether group-containing silane compound useful as a water / oil repellent.
  • Rf, PFPE, R 1 , Y, m and l correspond to the same symbols in the above formula (I) and have the same meanings.
  • the embodiments of Rf, PFPE, R 1 , Y, m and l in the formula (I ′) are the same as the embodiments of these groups in the above formula (I).
  • Q ′′ is a divalent organic group containing at least one fluorine atom bonded to a carbon atom.
  • Q ′′ is a divalent organic group containing at least one hydrogen atom and at least one fluorine atom bonded to a carbon atom, and corresponds to Q in the above formula (I).
  • the aspect of Q ′′ in the formula (I ′) is the same as the aspect of Q in the above formula (I).
  • the compound represented by the above formula (I ′) may be a compound represented by the above formula (I).
  • the compound represented by the above formula (I ′) may be a compound represented by the above formula (Ia).
  • Q ′′ in formula (I ′) corresponds to — (CH 2 ) n —O—CR 2 2 —CR 3 2 —Q′—CFR 4 — in formula (Ia).
  • a suitable solvent such as 1,3-bis (trifluoromethyl) benzene
  • sodium hydroxide or potassium hydroxide for example, under alkaline conditions and heating at 50 to 100 ° C., it is easy.
  • the desired compound can be obtained.
  • Rf, PFPE, Q ′, R 1 , R 2 , R 3 , R 4 , Y, m and n are the same as those in the above formulas (I) and (Ia ) Is equivalent to the description.
  • Rf, PFPE, Q ′, R 1 , R 2 , R 3 , R 4 , Y, m, and n are represented by the above formula (I) or formula (Ia ) Are the same as those of these groups.
  • the compounds represented by the above formulas (A) and (B) are known compounds in the art and are commercially available or can be synthesized by those skilled in the art.
  • the compound represented by the formula (A) can be synthesized by a method of reducing a perfluoropolyether group-containing terminal acid fluoride or terminal carboxylic acid with a reducing agent such as NaBH 4.
  • a reducing agent such as NaBH 4.
  • the compound represented by the formula (Ia) obtained by the reaction of the compound represented by the above formula (A) and the compound represented by the formula (B) may have another formula (I It may be converted to a compound represented by -a).
  • the compound represented by the formula (Ia) obtained by reacting the compound represented by the formula (A) with the compound represented by the formula (B) is a fluorination reaction.
  • the compound can be converted to a compound represented by the formula (I) or the formula (I ′) by subjecting to a substitution reaction or the like.
  • fluorination such as a method in which a reactor internal temperature is 5 to 100 ° C. and an F 2 / N 2 mixed gas with an F 2 gas concentration adjusted to 1 to 20 vol% is circulated at 5 to 200 ml / min for 1 to 48 hours.
  • a part or all of hydrogen atoms bonded to carbon can be substituted with fluorine atoms.
  • the compound represented by formula (B) is represented by the following formula (C): [Wherein R 2 , R 3 , R 4 , Q ′ and Y are as defined in the formula (B); X is a halogen atom. ] It can obtain from the compound represented by these.
  • X is a halogen atom selected from a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably an iodine atom.
  • the compound represented by the formula (C) may be separately converted into a compound represented by the formula (B) or used together with the compound represented by the formula (A).
  • the conversion into the compound represented by the formula (B) and the reaction with the compound represented by the formula (A) may be carried out continuously.
  • Example 1 To a 1 L four-necked flask equipped with a reflux condenser, a thermometer and a stirrer, an average composition CF 3 (OCF 2 CF 2 ) 20 (OCF 2 ) 16 OCF 2 CH 2 OH (however, in the mixture (OCF 2 CF 2 CF 2 CF 2 ) and / or a compound containing a trace amount of a repeating unit of (OCF 2 CF 2 CF 2 ) (perfluoropolyether-modified alcohol) (150 g) 1,3-bis (Trifluoromethyl) benzene (100 ml) and sodium hydroxide (5.2 g) were charged, and the mixture was stirred at 70 ° C. for 2 hours.
  • CF 2 CFOCF 2 CF 2 it a (26.0 g) was added and stirred for 4 hours at 85 ° C.. Then, it cooled to room temperature, the perfluorohexane (220g) was added, the insoluble matter was filtered, and washing
  • Example 2 An average composition of CF 3 (OCF 2 CF 2 ) 19 (OCF 2 ) 14 OCF 2 CH 2 OH (however, (OCF in the mixture) was added to a 1 L four-necked flask equipped with a reflux condenser, thermometer and stirrer. 2 CF 2 CF 2 CF 2 ) and / or a compound containing a trace amount of a repeating unit (OCF 2 CF 2 CF 2 ) (perfluoropolyether-modified alcohol) (150 g) represented by 1,3- Bis (trifluoromethyl) benzene (100 ml) and sodium hydroxide (5.0 g) were charged and stirred at 70 ° C. for 2 hours.
  • OCF 2 CF 2 perfluoropolyether-modified alcohol
  • CF 2 CFOCF 2 CF 2 I a (25.2 g) was added and stirred for 4 hours at 85 ° C.. Then, it cooled to room temperature, the perfluorohexane (220g) was added, the insoluble matter was filtered, and washing
  • Example 3 To a 1 L four-necked flask equipped with a reflux condenser, a thermometer and a stirrer, an average composition CF 3 (OCF 2 CF 2 ) 18 (OCF 2 ) 30 OCF 2 CH 2 OH (however, in the mixture (OCF 2 CF 2 CF 2 CF 2 ) and / or a compound containing a trace amount of a repeating unit (OCF 2 CF 2 CF 2 ) (perfluoropolyether-modified alcohol) (150 g) represented by 1,3- Bis (trifluoromethyl) benzene (100 ml) and sodium hydroxide (6.2 g) were charged and stirred at 70 ° C. for 2 hours.
  • OCF 3 OCF 3
  • OCF 2 CF 2 ) 18 OCF 2 CH 2 OH
  • CF 2 CFOCF 2 CF 2 it a (31.2 g) was added and stirred for 4 hours at 85 ° C.. Then, it cooled to room temperature, the perfluorohexane (220g) was added, the insoluble matter was filtered, and washing
  • the present invention can be suitably used for producing a wide variety of perfluoropolyether group-containing silane compounds.

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Abstract

　L'invention concerne un procédé de production d'un composé représenté par la formule générale (I') [dans la formule, les symboles ont les mêmes significations que celles décrites dans la description]. Le procédé consiste à faire réagir un composé représenté par la formule générale (A) [dans la formule, les symboles ont les mêmes significations que celles décrites dans la description] et un composé représenté par la formule générale (B) [dans la formule, les symboles ont les mêmes significations que celles décrites dans la description].
PCT/JP2015/083061 2014-12-04 2015-11-25 Composé contenant un groupe perfluoropolyéther halogéné et son procédé de production Ceased WO2016088620A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2014245454 2014-12-04
JP2014-245454 2014-12-04
JP2014261744A JP6020546B2 (ja) 2014-12-04 2014-12-25 ハロゲン化パーフルオロポリエーテル基含有化合物およびその製造方法
JP2014-261744 2014-12-25

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