Polymerizable sulfonate ionic liquids and liquid polymers therefrom
AssigneeThe United States of America as represented by the Secretary of the Navy
InventorsHolly L. Ricks-Laskoski, Arthur W. Snow
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Abstract
Disclosed is a new ionic liquid monomer salt and methods of is synthesis and polymerization. The ionic liquid monomer salt is prepared by mixing equimolar amounts of an amine, such as tris[2-(2-methoxyethoxy)-ethyl]amine and an acid functionalized polymerizable monomer, such as 2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS), which is stirred at ambient temperature until salt formation is complete. Also disclosed is a new ionic liquid polymer salts and method for making the same. The synthesis of AMPS-ammonium salt polymer is accomplished by adding 2,2′-azobisisobutyronitrile (AIBN) to the ionic liquid monomer salt and heating the homogeneous melt at 70° C. for 18 hr.
Claims4
An ionic liquid monomer salt having the general formula:
- wherein A=H or CH3;
- X═—COY—, -p-C6H4—, -o-C6H4—, -m-C6H4—, —O—, or —CH2—;
- Y═—O(CH2)n— where n=1 to 4, or
- —(OCH2CH2)n where n=1 to 6, or
- —NHCH(CH3)—, —NHC(CH3)2—, —N(C12H25)CH2CH2—,
- —NHC(CH3)CH2—, or —NHCH(C6H5)CH2—,
- wherein R, R′, and/or R″ are each independently selected from H or
- —(CH2)nCH3 where n=1 to 12, or
- —(CH2CH2O)nCH3 where n=1 to 4, or
- —(CH)3(Si(CH3)2O)nCH3 where n=1 to 6, or
- —(CF2)nCF3, —CH2(CF2)nCF3 where n=1 to 8.
An ionic liquid polymer salt having the general formula:
- wherein m>1;
- A=H or CH3;
- X═—COY—, -p-C6H4—, -o-C6H4—, -m-C6H4—, —O—, or —CH2—;
- Y═—O(CH2)n— where n=1 to 4, or
- —(OCH2CH2)n— where n=1 to 6, or
- —NHCH(CH3)—, —NHC(CH3)2—, —N(C12H25)CH2CH2—,
- —NHC(CH3)CH2—, or —NHCH(C6H5)CH2—;
- wherein R, R′, and/or R″ are each independently selected from H or
- —(CH2)nCH3 where n=1 to 12, or
- —(CH2CH2O)nCH3 where n=1 to 4, or
- —(CH)3(Si(CH3)2O)nCH3 where n=1 to 6, or
- —(CF2)nCF3, —CH2(CF2)nCF3 where n=1 to 8.
A method for making an ionic liquid monomer salt comprising:
- mixing an equimolar amount of a sulfonic acid functionalized monomer having the general formula:
- wherein A=H or CH3;
- X═—COY—, -p-C6H4—, -o-C6H4—, -m-C6H4—, —O—, or —CH2—;
- Y═—O(CH2)n— where n=1 to 4, or
- —(OCH2CH2)n where n=1 to 6, or
- —NHCH(CH3)—, —NHC(CH3)2—, —N(C12H25)CH2CH2—,
- —NHC(CH3)CH2—, or —NHCH(C6H5)CH2—;
- with an organic amine base having the general formula:
- wherein R, R′, and/or R″ are each independently selected from H or
- —(CH2)nCH3 where n=1 to 12, or
- —(CH2CH2O)nCH3 where n=1 to 4, or
- —(CH)3(Si(CH3)2O)nCH3 where n=1 to 6, or
- —(CF2)nCF3, —CH2(CF2)nCF3 where n=1 to 8;
- and
- stirring said mixture under an inert atmosphere until said sulfonic acid functionalized monomer is dissolved, wherein the dissolution completes formation of the ionic liquid monomer salt.
Dependencies are inferred from the claim text.