Fluorine-containing ether compound and production method therefor, compound and production method therefor, fluorine-containing ether composition, coating liquid, and article and production method therefor

A compound represented by formula (B1) or formula (B2) below:

• RfO—(Rf1O)m—R1-L1-R2-Q11(-CH—CH2) formula (B1)
• (CH2═CH—)Q11-R2-L1-R1—O—(RfO)m—R1-L1-R2-Q1(-CH═CH2)n formula (B2)
• wherein
• Rf is a fluoroalkyl group having 1 to 20 carbon atoms;
• Rf1 is a fluoroalkylene group having 1 to 6 carbon atoms, and a plurality of Rf1, when present, may be the same as or different from each other;
• R1 is an alkylene group optionally having a fluorine atom, and a plurality of R1, when present, may be the same as or different from each other;
• R2 is a single bond or an alkylene group optionally having a fluorine atom, and a plurality of R2, when present, may be the same as or different from each other;
• L1 is —CH(OH)—, —C(═O)—, or —CH═CH—, and a plurality of L1, when present, may be the same as or different from each other;
• Q11 is a (1+n)-valent linking group, and a plurality of Q11, when present, may be the same as or different from each other;
• m is an integer of 0 to 210;
• and
• n is an integer of 2 to 20, and a plurality of n, when present, may be the same as or different from each other.

A method for producing a compound represented by formula (B11) or formula (B12) below, the method comprising reacting a compound represented by formula (C1) or formula (C2) below with a compound represented by formula (D1) below:

• RfO—(Rf1O)m—R1—C(═O)—OR11 formula (C1)
• R11O—C(═O)—R1—O—(Rf1O)m—R1—C(═O)—OR11 formula (C2)
• (CH2—CH—)nQ11-R2—MgX formula (D1)
• RfO—(Rf1O))m—R1-L11-R2-Q11(—CH═CH2)n formula(B11)
• (CH2═CH—)nQ11-R2-L11-R1—O—(Rf1O)m—R1-L1-R2-Q11(—CH═CH)n formula (B12)
• wherein
• Rf is a fluoroalkyl group having 1 to 20 carbon atoms;
• Rf1 is a fluoroalkylene group having 1 to 6 carbon atoms, and a plurality of Rf1, when present, may be the same as or different from each other;
• R1 is an alkylene group optionally having a fluorine atom, and a plurality of R1, when present, may be the same as or different from each other;
• R2 is a single bond or an alkylene group optionally having a fluorine atom, and a plurality of R2, when present, may be the same as or different from each other;
• R11 is an alkyl group, and a plurality of R11, when present, may be the same as or different from each other;
• L11 is —CH(OH)—, —C(═O)—, —CH═CH—, or —CH2—, and a plurality of L11, when present, may be the same as or different from each other;
• Q11 is a (1+n)-valent linking group, and a plurality of Q11, when present, may be the same as or different from each other;
• X is a halogen atom;
• m is an integer of 0 to 210;
• and
• n is an integer of 2 to 20, and a plurality of n, when present, may be the same as or different from each other.

A method for producing a fluorine-containing ether compound represented by formula (A11) or formula (A12) below, the method comprising introducing an adhesion group T into a compound represented by formula (B11) or formula (B12) below:

• RfO—(Rf1O)m—R1-L11-R2-Q11(—CH═CH2)n formula (B11)
• (CH2═CH—)nQ11-R2-L1-R1—O—(RfO)m—R1-L11-R2-Q1(—CH═CH2) formula(B12)
• RfO—(RfO)m—R1-L11-R2-Q1(-T)n formula(A11)
• (T-)nQ1-R2-L1-R1—O—(RfO)m—R1-L11-R2-Q1(-T)n formula (A12)
• wherein
• Rf is a fluoroalkyl group having 1 to 20 carbon atoms;
• Rf1 is a fluoroalkylene group having 1 to 6 carbon atoms, and a plurality of Rf1, when present, may be the same as or different from each other;
• R1 is an alkylene group optionally having a fluorine atom, and a plurality of R1, when present, may be the same as or different from each other;
• R2 is a single bond or an alkylene group optionally having a fluorine atom, and a plurality of R2, when present, may be the same as or different from each other;
• L11 is —CH(OH)—, —C(═O)—, —CH═CH—, or —CH2—, and a plurality of L11, when present, may be the same as or different from each other;
• Q1 is a (1+n)-valent linking group, and a plurality of Q1, when present, may be the same as or different from each other;
• Q11 is a (1+n)-valent linking group, and a plurality of Q11, when present, may be the same as or different from each other;
• m is an integer of 0 to 210;
• n is an integer of 2 to 20, and a plurality of n, when present, may be the same as or different from each other;
• and
• T is an adhesion group and a plurality of T may be the same as or different from each other.

A fluorine-containing ether composition comprising a fluorine-containing ether compound represented by formula (A1) below and a fluorine-containing ether compound represented by formula (A2) below:

• RfO—(Rf1O)m—R1-L1-R2-Q1(-T)n formula (A1)
• (T-)nQ1-R2-L1-R1—O—(Rf1O))m—R1-L1-R2-Q1(-T)n formula (A2)
• wherein
• Rf is a fluoroalkyl group having 1 to 20 carbon atoms;
• Rf1 is a fluoroalkylene group having 1 to 6 carbon atoms, and a plurality of Rf1, when present, may be the same as or different from each other;
• R1 is an alkylene group optionally having a fluorine atom, and a plurality of R1, when present, may be the same as or different from each other;
• R2 is a single bond or an alkylene group optionally having a fluorine atom, and a plurality of R2, when present, may be the same as or different from each other;
• L1 is —CH(OH)—, —C(═O)—, or —CH═CH—, and a plurality of L1, when present, may be the same as or different from each other;
• Q1 is a (1+n)-valent linking group, and a plurality of Q1, when present, may be the same as or different from each other;
• T is an adhesion group, and a plurality of T may be the same as or different from each other;
• m is an integer of 0 to 210;
• and
• n is an integer of 2 to 20, and a plurality of n, when present, may be the same as or different from each other.