Hydrolyzed divinylbenzene/maleic anhydride polymeric material

Patent metadata

Field	Value
Publication number	US-10000596-B2
Application number	US-201415101201-A
Country	US
Kind code	B2
Filing date	Dec 16, 2014
Priority date	Dec 19, 2013
Publication date	Jun 19, 2018
Grant date	Jun 19, 2018

Abstract

Hydrolyzed divinylbenzene/maleic anhydride polymeric materials and methods of making these polymeric materials are provided. These polymers have a high BET specific surface area that results from the presence of micropores and/or mesopores. The polymers are useful for the adsorption of low molecular weight (e.g., no greater than 150 gram/mole), basic nitrogen-containing compounds.

First claim

We claim:

1. A hydrolyzed polymeric material comprising a reaction product of
a) a non-hydrolyzed precursor polymer comprising a polymerized product of a polymerizable composition comprising
i) a monomer mixture comprising
1) 10 to 40 weight percent maleic anhydride based on a total weight of monomers in the monomer mixture; and
2) 50 to 75 weight percent divinylbenzene based on the total weight of monomers in the monomer mixture; and
3) 1 to 20 weight percent of a third monomer based on the total weight of monomers in the monomer mixture, wherein the third monomer is styrene, an alkyl substituted styrene, or a combination thereof; and

ii) an organic solvent comprising a ketone, an ester, acetonitrile, or a mixture thereof, wherein the polymerizable composition is a single phase prior to polymerization; and

b) a hydrolyzing agent
wherein the hydrolyzed polymeric material has a plurality of carboxylic acid groups and a BET specific surface area equal to at least 100 m 2 /gram.

2. The hydrolyzed polymeric material of claim 1 , wherein the BET specific surface area is equal to at least 150 m 2 /gram.

3. The hydrolyzed polymeric material of claim 1 , wherein, the monomer mixture comprises 15 to 35 weight percent maleic anhydride, 55 to 75 weight percent divinylbenzene, and 1 to 20 weight percent third monomer.

4. The hydrolyzed polymeric material of claim 1 , wherein the monomer mixture comprises 20 to 30 weight percent maleic anhydride, 55 to 75 weight percent divinylbenzene, and 1 to 20 weight percent third monomer.

5. The hydrolyzed polymeric material of claim 1 , wherein at least 50 percent of the BET specific surface area is attributable to micropores, mesopores, or a combination thereof.

6. The hydrolyzed polymeric material of claim 1 , wherein the organic solvent comprises a ketone comprising methyl ethyl ketone, methyl isobutyl ketone, or a mixture thereof.

7. The hydrolyzed polymeric material of claim 1 , wherein the organic solvent comprises an ester comprising an acetate ester comprising ethyl acetate, amyl acetate, tert-butyl acetate, or a combination thereof.

8. The hydrolyzed polymeric material of claim 1 , wherein the organic solvent comprises acetonitrile.

9. The hydrolyzed polymeric material of claim 1 , wherein the polymerizable composition has percent solids equal to at least 5 weight percent.

10. The hydrolyzed polymeric material of claim 1 , wherein the BET specific surface area is in a range of 150 to 600 m 2 /gram and the concentration of carboxylic acid groups is in a range of 2 to 10 mmoles/gram.

11. The hydrolyzed polymeric material of claim 1 , wherein at least 99 weight percent of the monomers in the monomer mixture are divinylbenzene, maleic anhydride, and the third monomer.

12. The hydrolyzed polymeric material of claim 1 , wherein the hydrolyzed polymeric material adsorbs at least 0.25 mmoles per gram of a basic nitrogen-containing compound having a molecular weight no greater than 150 grams per mole.

13. A method of making a hydrolyzed polymeric material, the method comprising:
preparing a polymerizable composition comprising
i) a monomer mixture comprising
1) 10 to 40 weight percent maleic anhydride based on a total weight of monomers in the monomer mixture; and
2) 50 to 75 weight percent divinylbenzene based on the total weight of monomers in the monomer mixture; and
3) 1 to 20 weight percent of a third monomer based on the total weight of monomers in the monomer mixture, wherein the third monomer is styrene, an alkyl substituted styrene, or a combination thereof; and

ii) an organic solvent comprising a ketone, an ester, acetonitrile, or a mixture thereof, wherein the polymerizable composition is a single phase prior to polymerization;

forming a non-hydrolyzed precursor polymer by polymerizing the polymerizable composition; and
reacting the non-hydrolyzed precursor polymer with a hydrolyzing agent to form the hydrolyzed polymeric material, wherein the hydrolyzed polymeric material has a plurality of carboxylic acid groups and a BET specific surface area equal to at least 100 m 2 /gram.

Assignees

• 3M Innovative Properties Co

Inventors

• Wendland Michael S
• Kobe Michael W

Classifications

• C08F212/08

  Styrene · CPC title

• C08F8/12

  Hydrolysis · CPC title

• C08F222/08

  with vinyl aromatic monomers · CPC title

• C08F2800/20

  as weight or mass percentages · CPC title

• B01J39/20

  obtained by reactions only involving unsaturated carbon-to-carbon bonds · CPC title