# US 10,766,994 B2 · Reduction of aldehydes in amine catalysts

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- Number: US 10,766,994 B2
- Document ID: US10766994B2
- Status: Granted
- Kind: B2
- Application number: 15/534,814
- Filed: 2015-01-13
- Published: 2018-12-13
- Granted: 2020-09-08
- Earliest claimed: 2014-12-31
- Assignees: Huntsman Petrochemical Corporation
- Applicants: Huntsman Petrochemical LLC
- Inventors: Ernest L. Rister, Jr.; Haibo Zhao; Robert A. Grigsby, Jr.; Robert B. Moore
- Web page: https://patentgrep.com/patent/US10766994B2

## CPC

- C08G 18/1833: {having ether, acetal, or orthoester groups}
- C07C 209/84: Purification
- C08G 18/18: containing secondary or tertiary amines or salts thereof
- C08G 18/1825: {having hydroxy or primary amino groups}
- C08G 18/3218: {containing cyclic groups having at least one oxygen atom in the ring}
- C08G 18/3228: {acyclic}
- C08G 18/4816: {mixtures of two or more polyetherpolyols having at least three hydroxy groups}
- C08G 18/4841: {containing oxyethylene end groups}
- C08G 18/5024: {containing primary and/or secondary amino groups}
- C08G 18/7664: {containing alkylene polyphenyl groups}
- C08G 2110/005: < 50kg/m3
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present disclosure provides a method for reducing the aldehyde content in an amine catalyst by treating the amine catalyst with a treating agent selected from a non-cyclic amide substituted with an isocyanate reactive group, a guanidine substituted with an isocyanate reactive group, a polyether amine adducted with a urea compound or a guanidine compound, a free radical scavenger and a mixture thereof. The treated amine catalyst may then be used in the production of polyurethane materials which exhibit reduced aldehyde emissions.

## Claims

### Claim 1

A method for reducing the aldehyde content in an amine catalyst comprising (i) mixing an amine catalyst containing one or more aldehyde impurities and a treating agent selected from a polyether amine adducted with a urea compound or a guanidine compound to form a catalyst mixture and (ii) subjecting the catalyst mixture to conditions such that the level of aldehyde impurities in the catalyst mixture are reduced, wherein the polyether amine adducted with a urea compound or a guanidine compound is represented by the general formula (III):
R4—NH-A-NH2 (III)
where R4 is a linear or branched alkoxylated polyether polyamine, and
A is C═O or C═NH.

### Claim 2 (depends on 1)

The method of claim 1 wherein the conditions include maintaining the catalyst mixture at approximately room temperature for at least about 3 hours.

### Claim 3 (depends on 1)

The method of claim 1 wherein R4 is an alkoxylated polyether polyamine represented by the general formula (IV):
where w is an integer ranging from about 1.5 to about 150.

### Claim 4 (depends on 1)

The method of claim 1 wherein the treating agent further comprises a free radical scavenger comprising a sterically hindered phenol having the formula (VIII):
where R5, R6 and R7 are independently selected from H or a C1-C10 alkyl group and R8 is H or a C1-C12 alkyl group.

### Claim 5 (depends on 4)

The method of claim 4 wherein R5, R6 and R7 are independently selected from H or a CH3 group and R8 is H or a C1-C4 alkyl group.

### Claim 6 (depends on 4)

The method of claim 4 wherein R5, R6 and R7 are each a CH3 group and R8 is H, a methyl group, an ethyl group, a propyl group or an isopropyl group.

### Claim 7

A method, for reducing the aldehyde content in an amine catalyst comprising (i) mixing an amine catalyst containing one or more aldehyde impurities and a treating agent selected from a polyether amine adducted with a urea compound or a guanidine compound to form a catalyst mixture and (ii) subjecting the catalyst mixture to conditions such that the level of aldehyde impurities in the catalyst mixture are reduced, wherein the polyether amine adducted with a urea compound or a guanidine compound is represented by the general formula (III):
R4—NH-A-NH2 (III)
where R4 is a linear or branched alkoxylated polyether polyamine, and
A is C═O or C═NH and wherein the conditions include maintaining the catalyst mixture at a temperature of between about 60°−150° C. for at least about 3 hours.