An alkoxyvinyl ether is disclosed having the chemical structure R.sub.fC(OR)═CHR.sub.f′, wherein R.sub.f is an at least partially fluorinated functional group having at least one carbon atom, R.sub.f′ is an at least partially fluorinated functional group having at least two carbon atoms, and R is a functional group. A method for preparing an alkoxyvinyl ether is disclosed, comprising R.sub.fCFHCFHR.sub.f′+KOH/ROH.fwdarw.R.sub.fC(OR)═CHR.sub.f′, wherein R.sub.f is a perfluoro functional group, R.sub.f′ is a perfluoro functional group, and R is an alkyl functional group. Another method for preparing an alkoxyvinyl ether is disclosed, comprising R.sub.fCF═CHR.sub.f′+KOH/ROH.fwdarw.R.sub.fC(OR)═CHR.sub.f′, wherein R.sub.f is a perfluoro functional group, R.sub.f′ is a perfluoro functional group, and R is an alkyl functional group.

The present invention relates to a process of preparing polyfluoroether compounds with unsaturated end groups and to compounds prepared by said process.

The present invention relates to a process of preparing polyfluoroether compounds with unsaturated end groups and to compounds prepared by said process.

##STR00001##

##STR00002##

Described herein is a method to synthesize a perfluorinated allyl ether compound of formula (I) or a perfluorinated allyl amine compound of formula (II) Where R.sub.f.sup.1 and R.sub.f.sup.2 are (i) independently selected from a perfluorinated alkyl group comprising 1-7 carbon atoms, a perfluorinated aryl group comprising a 5- or 6-membered ring, or combinations thereof, and optionally comprising one or more catenated heteroatoms selected from N or O; or (ii) bonded together to form a perfluorinated ring structure having 4-8 ring carbon atoms, optionally comprising at least one catenated O or N atom; and R.sub.f.sup.3 is a perfluorinated alkyl group comprising 1-3 carbon atoms. The resulting perfluorinated allyl ether compounds disclosed herein may be used in polymer synthesis.

##STR00001##

##STR00002##

Described herein is a method to synthesize a perfluorinated allyl ether compound of formula (I) or a perfluorinated allyl amine compound of formula (II) Where R.sub.f.sup.1 and R.sub.f.sup.2 are (i) independently selected from a perfluorinated alkyl group comprising 1-7 carbon atoms, a perfluorinated aryl group comprising a 5- or 6-membered ring, or combinations thereof, and optionally comprising one or more catenated heteroatoms selected from N or O; or (ii) bonded together to form a perfluorinated ring structure having 4-8 ring carbon atoms, optionally comprising at least one catenated O or N atom; and R.sub.f.sup.3 is a perfluorinated alkyl group comprising 1-3 carbon atoms. The resulting perfluorinated allyl ether compounds disclosed herein may be used in polymer synthesis.

Provided are a fluorine-containing ether compound, fluorine-containing ether composition and coating liquid that can form a surface layer having excellent durability, an article having a surface layer that has excellent durability, and a compound that is useful as a raw material of a fluorine-containing ether compound. The fluorine-containing ether compound is represented by the following formula (A1) or formula (A2):

R.sup.f—O—(R.sup.f1O).sub.m—R.sup.f2[—R.sup.1—C(—R.sup.2-T).sub.a(—R.sup.3).sub.3-a].sub.b  Formula (A1)

[(T-R.sup.2—).sub.a(R.sup.3—).sub.3-aC—R.sup.1—].sub.bR.sup.f2—O—(R.sup.f1O).sub.m—R.sup.f2[—R.sup.1—C(—R.sup.2-T).sub.a(-R.sup.3).sub.3-a].sub.b   Formula (A2) wherein each of the reference signs in the formulas are as described in the specification.

A method includes combining first components including at least one of CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl or CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, a polyfluorinated compound having at least one ketone or carboxylic acid halide, and fluoride ion to provide a compound comprising at least one perfluorinated allyl ether group. A method includes combining second components including B(OSO.sub.2Cl).sub.3 and hexafluoropropylene to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl. Another method includes combining second components including M(OSO.sub.2CF.sub.3).sub.3 and hexafluoropropylene at a temperature above 0° C. to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, wherein M is Al or B. The compound CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl is also provided.

A method includes combining first components including at least one of CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl or CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, a polyfluorinated compound having at least one ketone or carboxylic acid halide, and fluoride ion to provide a compound comprising at least one perfluorinated allyl ether group. A method includes combining second components including B(OSO.sub.2Cl).sub.3 and hexafluoropropylene to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl. Another method includes combining second components including M(OSO.sub.2CF.sub.3).sub.3 and hexafluoropropylene at a temperature above 0° C. to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, wherein M is Al or B. The compound CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl is also provided.

An aim of the present disclosure is to provide a method for producing a fluoroalkoxide, said method being more useful than conventional methods, and the like. The aim can be achieved by a method for producing a compound represented by the following formula (1):

##STR00001## (wherein R.sup.1 is a fluoroalkyl group optionally containing an oxygen atom between carbon atoms, or a fluoroalkoxy group optionally containing an oxygen atom between carbon atoms, and each R.sup.2 is identical to or different from each other and is a hydrocarbon group), the method comprising the step of reacting a compound represented by the following formula (2):

##STR00002## with a compound represented by the following formula (3):

.sup.⊖F.sup.⊕NR.sup.2).sub.4  (3).

An aim of the present disclosure is to provide a method for producing a fluoroalkoxide, said method being more useful than conventional methods, and the like. The aim can be achieved by a method for producing a compound represented by the following formula (1):

##STR00001## (wherein R.sup.1 is a fluoroalkyl group optionally containing an oxygen atom between carbon atoms, or a fluoroalkoxy group optionally containing an oxygen atom between carbon atoms, and each R.sup.2 is identical to or different from each other and is a hydrocarbon group), the method comprising the step of reacting a compound represented by the following formula (2):

##STR00002## with a compound represented by the following formula (3):

.sup.⊖F.sup.⊕NR.sup.2).sub.4  (3).