IP Library Granted Patent US 10,967,358
Granted Patent B2
US 10,967,358 · App. 16/081,479 · Granted Apr 6, 2021

Composite granules including polymeric sorbent for aldehydes

Inventors: Michael W. Kobe (Lake Elmo, MN); Michael S. Wendland (North St. Paul, MN)
Assignee: 3M Innovative Properties Company
B01J20/261B01D53/1456B01D53/72B01J20/265B01J20/267B01J20/2803B01J20/28057B01J20/3042B01D2253/202B01D2253/25B01D2257/708B01J2220/49C08F212/08C08F212/36C08F222/06C08L1/02
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Quick Facts
Patent No.
US 10,967,358
App. No.
16/081,479
Granted
Apr 6, 2021
Kind
B2
Abstract

Composite granules that contain a binder and a polymeric sorbent material for capturing aldehydes such as formaldehyde are provided. Additionally, methods of making the composite granules, methods of using the composite granules to capture aldehydes, and compositions formed by reacting the composite granules with aldehydes are provided. The polymeric sorbent material included in the composite granules is a reaction product of a divinylbenzene/maleic anhydride precursor polymeric material with a nitrogen-containing compound. This reaction results in the formation of nitrogen-containing groups that are covalently attached to the polymeric sorbent. Aldehydes can react with the nitrogen-containing groups.

Claims (41)

1. Composite granules comprising:

a polymeric sorbent comprising a reaction product of

(a) a precursor polymeric material comprising a free radical polymerization product of a polymerizable composition comprising

(1) 20 to 65 weight percent maleic anhydride based on the total weight of monomers in the polymerizable composition;

(2) 30 to 85 weight percent divinylbenzene based on the total weight of monomers in the polymerizable composition; and

(3) 0 to 40 weight percent of a styrene-type monomer based on the total weight of monomers in the polymerizable composition, wherein the styrene-type monomer is styrene, an alkyl-substituted styrene, or a combination thereof; and

(4) a free radical initiator; and

(b) a nitrogen-containing compound that is selected from ammonia, a compound having a single primary amino group (—NH 2 ), or a compound having at least two amino groups of formula —NHR where R is hydrogen or alkyl; and

a binder, wherein the binder is blended with particles of the polymeric sorbent and wherein multiple particles of the polymeric sorbent are held together by the binder in the composite granules.

2. The composite granules of claim 1 , wherein the amount of the binder is in a range of 1 to 30 weight percent based on the weight of the composite granules.

3. The composite of claim 1 , wherein the binder comprises a salt or a polymeric material.

4. The composite granules of claim 3 , wherein the binder comprises a silicate salt.

5. The composite granules of claim 3 , wherein the binder comprises a carboxylate salt, wherein the carboxylate salt has 10 to 20 carbon atoms.

6. The composite granules of claim 3 , wherein the binder comprises a naturally occurring polymer.

7. The composite granules of claim 3 , wherein the binder comprises a cellulosic resin.

8. The composite granules of claim 1 , wherein the nitrogen-containing compound is of Formula (V)

R 4 NHR 1   (V)

wherein

R 1 is hydrogen or an alkyl;

R 4 is hydrogen, an alkyl, a group of formula —R 5 —NHR 6 , or —(C═NH)—NH 2 ;

R 5 is a covalent bond, an alkylene, an arylene, an aralkylene, a heteroalkylene having one or more oxy (—O—) groups, or a heteroalkylene having one or more —NH— groups; and

R 6 is hydrogen, an alkyl, or —(C═NH)—NH 2 .

9. The composite granules of claim 1 , wherein the nitrogen-containing compound is of Formula (VI)

R 7 —(NHR 1 ) z   (VI)

wherein

R 1 is hydrogen or an alkyl;

R 7 is a z-valent radical of an alkane or a z-valent radical of a heteroalkane; and

z is an integer in a range of 3 to 10.

10. The composite granules of claim 1 , wherein the polymeric sorbent further comprises an acid-base colorimetric indicator.

11. The composite granules of claim 1 , wherein the polymeric sorbent has a BET surface area equal to at least 25 m 2 /gram.

12. A method of sorbing an aldehyde, the method comprising:

providing composite granules comprising a binder and a polymeric sorbent according to claim 1 ; and

exposing the composite granules to the aldehyde; and

sorbing the aldehyde on the polymeric sorbent, the aldehyde being of Formula (I)

R 2 —(CO)—H  (I)

wherein

R 2 is hydrogen, alkyl, vinyl, or aryl; and

the molecular weight of the aldehyde of Formula (I) is no greater than 200 grams/mole.

13. The method of claim 12 , wherein R 2 is hydrogen or methyl.

14. The method of claim 12 , wherein the polymeric sorbent sorbs an amount of aldehyde in a range of 0.35 to 10 millimoles per gram based on the weight of the composite granules.

15. The method of claim 12 , wherein the polymeric sorbent comprises an acid-base indicator and wherein the acid-base indicator changes color when the aldehyde sorption capacity of the polymeric sorbent is reached or is close to being reached.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 31, 2018
From: KOBE, MICHAEL W.; WENDLAND, MICHAEL S.
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 046764/0914 →
Continuity (5)
Provisional Application 62465221 · Mar 1, 2017
Provisional Application 62465214 · Mar 1, 2017
Provisional Application 62465209 · Mar 1, 2017
Provisional Application 62307831 · Mar 14, 2016
Related Publication 20190060870A1 · Feb 28, 2019