Sulfoalkylation of polybenzimidazole

Claim 2

A process for preparing a substituted polybenzimidazole polymer comprising the steps of: a. preparing a polybenzimidazole polymer solvent solution; and b. reacting the polybenzimidazole polymer with a beta sultone having the general formula: ##STR11## wherein R 2 and R 3 are the same as or different from each other and are selected from the group consisting of hydrogen, halides, or a C 1 to C 3 unsubstituted alkyl group and R 4 and R 5 are the same as or different from each other and are selected from the group consisting of hydrogen, a halide or a C 1 to C 6 substituted or unsubstituted alkyl substituent to produce an N-substituted sulfopropyl derivative of the polybenzimidazole polymer.

Claim 3

A process for preparing a substituted polybenzimidazole polymer comprising the steps of: a. preparing a polybenzimidazole polymer solvent solution; b. mixing with the polybenzimidazole polymer an alkali hydride to produce a polybenzimidazole polyanion; and c. reacting the polybenzimidazole polyanion with a sultone having the general formula: ##STR12## wherein R 7 is a divalent substituted or unsubstituted C 3 or C 4 alkyl member wherein the substituents are the same as or different from each other and are selected from the group consisting of hydrogen, halides and C 1 to C 3 substituted or unsubstituted alkyl groups to produce a sulfoalkyl derivative of the polybenzimidazole polymer.

Claim 4

A process for preparing a substituted polybenzimidazole polymer comprising the steps of: a. preparing a polybenzimidazole polymer solvent solution; b. mixing with the polybenzimidazole polymer an alkali hydride to produce a polybenzimidazole polyanion; and c. reacting the polybenzimidazole polyanion with a sultone having the general formula: ##STR12## wherein R 7 is a divalent substituted or unsubstituted C 3 or C 4 alkyl member wherein the substituents are the same as or different from each other and are selected from the group consisting of hydrogen, halides and C 1 to C 3 substituted or unsubstituted alkyl groups to produce a sulfoalkyl derivative of the polybenzimidazole polymer.

Claim 5

The process of claim 1 wherein the sultone is 2-hydroxy-1-propane sulfonic acid sultone.

Claim 6

The process as in any of claim 2 wherein the sultone is 3-hydroxy-1-propane sulfonic acid sultone.

Claim 7

The process as in any of claims 1 or 2 wherein the polybenzimidazole polymer starting material is comprised of recurring monomeric units of: ##STR13## wherein Z is an aromatic nucleus having the nitrogen atoms forming the benzimidazole ring paired upon adjacent carbon atoms of the aromatic nucleus.

Claim 8

The process as in any of claims 1 or 2 wherein the polybenzimidazole polymer is poly-2,2'-(m-phenylene)-5,5'-bibenzimidazole.

Claim 9

The process as in any of claims 1 or 2 wherein at least about 40 percent of the reactive imidazole nitrogen-hydrogen sites are substituted with a sulfoalkyl substituent.

Claim 10

The process as in any of claims 1 or 2 wherein the concentration of the polybenzimidazole in the solvent solution is from about 5 to about 20 percent by weight based on the total solution weight.

Claim 11

The process as in any of claims 1 or 2 wherein the sultone is present in at least a stoichiometric quantity with respect to the imidazole nitrogen-hydrogen sites.

Claim 12

The process as in any of claims 1 or 2 wherein the ratio of the sultone to each imidazole nitrogen-hydrogen site on the polybenzimidazole polymer is from about 1:1 to about 4:1.

Claim 13

The process as in any of claims 1 or 2 wherein the sultone reaction is conducted at a temperature from about 40° C. to about 150° C. for a period from about 12 to about 72 hours.

Claim 14

The process of claim 2 wherein the alkali hydride is selected from the group consisting of sodium hydride, lithium hydride and potassium hydride.

Claim 15

The process of claim 2 wherein the alkali hydride is lithium hydride.

Claim 16

The process of claim 2 wherein the alkali hydride is mixed with the polybenzimidazole solvent solution for a period from about 4 to about 12 hours, heated to a temperature from about 40° C. to about 120° C. and maintained at that temperature.

Claim 17

The process of claim 2 wherein at least about 0.75 alkali hydride units are present for each imidazole nitrogen-hydrogen site on the polybenzimidazole polymer.

Claim 18

The process of claim 2 wherein the ratio of the alkali hydride units to the polybenzimidazole imidazole nitrogen-hydrogen sites ranges from about 1:1 to about 3:1.

Claim 19

The process as in any of claims 1 or 2 wherein the polybenzimidazole polymer consists essentially of recurring units of the formula: ##STR14## where R is a tetravalent aromatic nucleus with the nitrogen atoms forming the bibenzimidazole rings being paired upon adjacent carbon atoms of the aromatic nucleus, and R' is a divalent substituent selected from aliphatic, alicyclic or aromatic radicals.

Claim 20

An N-sulfopropyl substituted polybenzimidazole polymer produced by the process of claim 1.

Claim 21

An N-sulfoalkyl derivative of polybenzimidazole produced by the process of claim 2.

Claim 22

A process for preparing a substituted polybenzimidazole polymer comprising the steps of: a. preparing a solvent solution containing about a 5 to about a 20 percent by weight based on the total solution weight of poly-2,2'-(m-phenylene)5,5' bibenzimidazole; and b. reacting the polymer with 2-hydroxy-1-propane sulfonic acid sultone to produce sulfopropyl polybenzimidazole polymer.

Claim 23

A process for preparing a substituted polybenzimidazole polymer comprising the steps of: a. preparing a solvent solution containing about a 5 to about a 20 percent by weight based on the total solution weight of poly-2,2'-(m-phenylene)5,5' bibenzimidazole; and b. reacting the polymer with 2-hydroxy-1-propane sulfonic acid sultone to produce sulfopropyl polybenzimidazole polymer.

Claim 24

An N-sulfopropyl derivative of polybenzimidazole produced by the process of claim 20.

Claim 25

A process for preparing a substituted polybenzimidazole polymer comprising the steps of: a. preparing a poly-2,2'-(m-phenylene)5,5'-bibenzimidazole polymer solution wherein the concentration of the polymer in the solvent solution is from about 5 to about 20 percent by weight based on the total solution weight; b. mixing lithium hydride with the polymer solution wherein the ratio of the lithium hydride to the polybenzimidazole imidazole nitrogen-hydrogen sites ranges from about 1:1 to about 3:1, to produce a polybenzimidazole polyanion; and c. reacting the polybenzimidazole polyanion with 3-hydroxy-1-propane sulfonic acid sultone wherein at least a stoichiometric quantity of the sultone is present in relation to the available polybenzimidazole polyanion sites to produce a sulfopropyl derivative of the polybenzimidazole polymer.

Claim 26

A process for preparing a substituted polybenzimidazole polymer comprising the steps of: a. preparing a poly-2,2'-(m-phenylene)5,5'-bibenzimidazole polymer solution wherein the concentration of the polymer in the solvent solution is from about 5 to about 20 percent by weight based on the total solution weight; b. mixing lithium hydride with the polymer solution wherein the ratio of the lithium hydride to the polybenzimidazole imidazole nitrogen-hydrogen sites ranges from about 1:1 to about 3:1, to produce a polybenzimidazole polyanion; and c. reacting the polybenzimidazole polyanion with 3-hydroxy-1-propane sulfonic acid sultone wherein at least a stoichiometric quantity of the sultone is present in relation to the available polybenzimidazole polyanion sites to produce a sulfopropyl derivative of the polybenzimidazole polymer.

Claim 27

An N-sulfopropyl derivative of polybenzimidazole produced by the process of claim 22.

Claim 28

An N-substituted sulfonated polybenzimidazole polymer having units of the general formula: ##STR15## where R is a tetravalent aromatic nucleus with the nitrogen atoms forming the bibenzimidazole rings being paired upon adjacent carbon atoms of the aromatic nucleus; R' is a divalent substituent selected from aliphatic, alicyclic or aromatic radicals; and R 8 is a C 2 to C 4 substituted or unsubstituted alkyl member, wherein the substituents are the same as or different from each other and are selected from the group consisting of hydrogen, halides and C 1 to C 6 unsubstituted alkyl members.

Claim 29

An N-substituted sulfonated polybenzimidazole polymer having units of the general formula: ##STR15## where R is a tetravalent aromatic nucleus with the nitrogen atoms forming the bibenzimidazole rings being paired upon adjacent carbon atoms of the aromatic nucleus; R' is a divalent substituent selected from aliphatic, alicyclic or aromatic radicals; and R 8 is a C 2 to C 4 substituted or unsubstituted alkyl member, wherein the substituents are the same as or different from each other and are selected from the group consisting of hydrogen, halides and C 1 to C 6 unsubstituted alkyl members.

Claim 30

A process for preparing a substituted polybenzimidazole polymer comprising the steps of: a. preparing a solvent solution containing about a 5 to about a 20 percent by weight based on the total solution weight of a polybenzimidazole polymer wherein the polybenzimidazole polymer consists essentially of recurring units of the formula: ##STR16## where R is a tetravalent aromatic nucleus with the nitrogen atoms forming the bibenzimidazole rings being paired upon adjacent carbon atoms of the aromatic nucleus, and R' is a divalent substituent selected from aliphatic, alicyclic or aromatic radicals b. reacting the polybenzimidazole polymer with a beta sultone having the general formula: ##STR17## wherein R 2 and R 3 are the same as or different from each other and are selected from the group consisting of hydrogen, halides, or C 1 to C 3 unsubstituted alkyl groups and R 4 and R 5 are the same as or different from each other and are selected from the group consisting of hydrogen, halides, and C 1 to C 6 substituted or unsubstituted alkyl substituents to produce a sulfoethyl derivative of the polybenzimidazole polymer.

Claim 31

A process for preparing a substituted polybenzimidazole polymer comprising the steps of: a. preparing a solvent solution containing about a 5 to about a 20 percent by weight based on the total solution weight of a polybenzimidazole polymer wherein the polybenzimidazole polymer consists essentially of recurring units of the formula: ##STR16## where R is a tetravalent aromatic nucleus with the nitrogen atoms forming the bibenzimidazole rings being paired upon adjacent carbon atoms of the aromatic nucleus, and R' is a divalent substituent selected from aliphatic, alicyclic or aromatic radicals b. reacting the polybenzimidazole polymer with a beta sultone having the general formula: ##STR17## wherein R 2 and R 3 are the same as or different from each other and are selected from the group consisting of hydrogen, halides, or C 1 to C 3 unsubstituted alkyl groups and R 4 and R 5 are the same as or different from each other and are selected from the group consisting of hydrogen, halides, and C 1 to C 6 substituted or unsubstituted alkyl substituents to produce a sulfoethyl derivative of the polybenzimidazole polymer.

Claim 32

A process for preparing a substituted polybenzimidazole polymer comprising the steps of: a. preparing a polybenzimidazole polymer solvent solution wherein the polybenzimidazole polymer consists essentially of recurring units of the formula: ##STR18## where R is a tetravalent aromatic nucleus with the nitrogen atoms forming the bibenzimidazole rings being paired upon adjacent carbon atoms of the aromatic nucleus, and R' is a divalent substituent selected from aliphatic, alicyclic or aromatic radicals; b. mixing with the polybenzimidazole polymer on alkali hydride selected from the group consisting of sodium hydride, lithium hydride and potassium hydride wherein at least about 0.75 alkali hydride units are present for each imidazole nitrogen-hydogen site on the polybenzimidazole polymer to produce a polybenzimidazole polyanion; and c. reacting the polybenzimidazole polyanion with a sultone having the general formula of: ##STR19## wherein R 7 is a divalent substituted or unsubstituted C 3 or C 4 alkyl member wherein the substituent may be the same as or different from each other and is selected from the group consisting of hydrogen, halides and C 1 to C 3 substituted or unsubstituted alkyl groups to produce a sulfoalkyl derivative of the polybenzimidazole polymer.

Claim 33

A process for preparing a substituted polybenzimidazole polymer comprising the steps of: a. preparing a polybenzimidazole polymer solvent solution wherein the polybenzimidazole polymer consists essentially of recurring units of the formula: ##STR18## where R is a tetravalent aromatic nucleus with the nitrogen atoms forming the bibenzimidazole rings being paired upon adjacent carbon atoms of the aromatic nucleus, and R' is a divalent substituent selected from aliphatic, alicyclic or aromatic radicals; b. mixing with the polybenzimidazole polymer on alkali hydride selected from the group consisting of sodium hydride, lithium hydride and potassium hydride wherein at least about 0.75 alkali hydride units are present for each imidazole nitrogen-hydogen site on the polybenzimidazole polymer to produce a polybenzimidazole polyanion; and c. reacting the polybenzimidazole polyanion with a sultone having the general formula of: ##STR19## wherein R 7 is a divalent substituted or unsubstituted C 3 or C 4 alkyl member wherein the substituent may be the same as or different from each other and is selected from the group consisting of hydrogen, halides and C 1 to C 3 substituted or unsubstituted alkyl groups to produce a sulfoalkyl derivative of the polybenzimidazole polymer.

Claim 34

An N-sulfoethyl derivative of polybenzimidazole produced by the process of claim 25.

Claim 35

An N-sulfoalkyl derivative of polybenzimidazole produced by the process of claim 26.