Anion-conducting polymer, composition, and membrane

A membrane comprising a polymeric reaction product of the reaction of a monomer of the formula

• with one at least one second monomer of the formula
• wherein D is halide selected from F, Cl, Br, and I;
• wherein E is selected from —SO2—, —C(═O)—, and —P(═O)(aryl)-;
• wherein Z is a direct bond or —C(CX3)2— where X is hydrogen or fluorine;
• wherein R1 and R2 independently of one another denote H, an alkyl, cycloalkyl, alkenyl, aryl, or aralkyl group having 1 to 10 carbon atoms or a heterocyclic group having 4 to 20 carbon atoms;
• wherein R1 and R2 may together form a —(CH2)2—, —(CH2)3—, —(CH2)4—, —(CH2)5—, —CH═CH—, or —CH═CH—CH═CH—;
• wherein A1, A2, A3, and A4 are independently selected from hydrogen, alkyl, cycloalkyl, alkenyl, aryl, aralkyl having 1 to 10 carbon atoms, a heterocyclic group having 4 to 20 carbon atoms, and a residue of the formula
• wherein R3 is a direct bond or a group selected from —(CH2CH2)—, —(C6H4)—, —(CF2CF2)—, —(CH2CH2CH2)—;
• wherein R4 and R5 independently of one another denote an alkyl, cycloalkyl, alkenyl, aryl, or aralkyl group having 1 to 10 carbon atoms or a heterocyclic group having 4 to 20 carbon atoms;
• wherein R4 and R5 may together form a —(CH2)2—, —(CH2)3—, —(CH2)4—, —(CH2)5—, —CH═CH—,
• or —CH═CH—CH═CH—;
• wherein R6 is selected from H, alkyl, cycloalkyl;
• wherein Q is any anion;
• and with the caveat that the polymeric reaction product is prepared from first monomer and/or second monomer having at least 5 mole percent of the residue.

A composition comprising a support and a salt embedded in the support, the salt being selected from the group consisting of salts of the formula

• wherein R4 and R5 independently of one another denote an alkyl, cycloalkyl, alkenyl, aryl, or aralkyl group having 1 to 10 carbon atoms or a heterocyclic group having 4 to 20 carbon atoms;
• wherein R4 and R5 may together form a —(CH2)2—, —(CH2)3—, —(CH2)4—, —(CH2)5—, —CH═CH—, or —CH═CH—CH═CH—;
• wherein R6 is selected from H, alkyl, cycloalkyl;
• and wherein Q is any anion.

A polymer of the formula

• wherein n is an integer of 3 or greater;
• wherein Z is a direct bond or a chemical group independently selected from —O—, —S—, —SO2—, —C(CH3)2—, —C(CF3)2—, —C(═O)—, —P(═O)(aryl)-, phenyl;
• wherein R1 and R2 independently of one another denote H, an alkyl, cycloalkyl, alkenyl, aryl, or aralkyl group having 1 to 10 carbon atoms or a heterocyclic group having 4 to 20 carbon atoms;
• wherein R1 and R2 together may form a —(CH2)2—, —(CH2)3—, —(CH2)4—, —(CH2)5—, —CH═CH—, or —CH═CH—CH═CH—;
• and wherein A1 and A2 are selected from hydrogen, alkyl, cycloalkyl, alkenyl, aryl, aralkyl group having 1 to 10 carbon atoms, a heterocyclic group having 4 to 20 carbon atoms, and a residue selected from those of the formula
• wherein R3 is a direct bond or a group selected from —(CH2CH2)—, —(C6H4)—, —(CF2CF2)—, —(CH2CH2CH2)—;
• wherein R4 and R5 independently of one another denote an alkyl, cycloalkyl, alkenyl, aryl, or aralkyl group having 1 to 10 carbon atoms or a heterocyclic group having 4 to 20 carbon atoms;
• wherein R4 and R5 may together form a —(CH2)2—, —(CH2)3—, —(CH2)4—, —(CH2)5—, —CH═CH—,
• or —CH═CH—CH═CH—;
• wherein R6 is selected from H, alkyl or cycloalkyl;
• wherein Q is any anion;
• and with the caveat that the polymer comprises at least 1 weight percent of the residue.

An anion-conducting membrane comprising a polymer of the formula

• wherein n is an integer of 3 or greater;
• wherein Z is a direct bond or a chemical group independently selected from —O—, —S—, —SO2—, —C(CH3)2—, —C(CF3)2—, —C(═O)—, —P(═O)(aryl)-, phenyl;
• wherein R1 and R2 independently of one another denote H, an alkyl, cycloalkyl, alkenyl, aryl, or aralkyl group having 1 to 10 carbon atoms or a heterocyclic group having 4 to 20 carbon atoms;
• wherein R1 and R2 together may form a —(CH2)2—, —(CH2)3—, —(CH2)4—, —(CH2)5—, —CH═CH—, or —CH═CH—CH═CH—;
• and wherein A1 and A2 are selected from hydrogen, alkyl, cycloalkyl, alkenyl, aryl, aralkyl group having 1 to 10 carbon atoms, a heterocyclic group having 4 to 20 carbon atoms, and a residue selected from those of the formula
• wherein R3 is a direct bond or a group selected from —(CH2CH2)—, —(C6H4)—, —(CF2CF2)—, —(CH2CH2CH2)—;
• wherein R4 and R5 independently of one another denote an alkyl, cycloalkyl, alkenyl, aryl, or aralkyl group having 1 to 10 carbon atoms or a heterocyclic group having 4 to 20 carbon atoms;
• wherein R4 and R5 may together form a —(CH2)2—, —(CH2)3—, —(CH2)4—, —(CH2)5—, —CH═CH—,
• or —CH═CH—CH═CH—;
• wherein R6 is selected from H, alkyl or cycloalkyl;
• wherein Q is any anion;
• and with the caveat that the polymer comprises at least 1 weight percent of the residue.

A polymer of the formula

• wherein n is any integer greater than 1;
• wherein Z is NR1R2 or N(═PZ3);
• and wherein R1 and R2 are independently selected from C1 to C10 alkyl, C1 to C10 partially fluorinated alkyl, or C1 to C10 fluorinated alkyl, and also wherein R1 and R2 may together form a —(CH2)2—, —(CH2)3—, —(CH2)4—, —(CH2)5—, —CH═CH—,
• or —CH═CH—CH═CH—.

The polymeric reaction product of water and a polymer of the formula

• wherein n is any integer greater than 1;
• wherein Z is NR1R2 or N(═PZ3);
• and
• wherein R1 and R2 are independently selected from C1 to C10 alkyl, C1 to C10 partially fluorinated alkyl, or C1 to C10 fluorinated alkyl, and also wherein R1 and R2 may together form a —(CH2)2—, —(CH2)3—, —(CH2)4—, —(CH2)5—, —CH═CH—,
• or —CH═CH—CH═CH—.