Reduction of aldehydes in amine catalysts
AssigneeHuntsman Petrochemical Corporation
InventorsErnest L Rister, Jr., Srinivasa S Godavarthy, Henry Robertson, Robert A Grigsby, Jr., Robert B Moore, Geert Lodewijk Dries, Eugene P Wiltz, Jr.
Life of this patent
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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 cyclic urea substituted with at least one isocyanate reactive group, 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.
Claims17
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 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 treating agent comprises:
- 1) a substituted cyclic urea selected from at least one of 4-hydroxy-5-methyl propylene urea, 4-methoxy-5-methyl propylene urea, 4-hydroxy-5,5-dimethyl propylene urea, 4,5-dimethoxy-2-imidazolidinone, or a substituted cyclic urea having the formula (I):
- where R, R0, R1, R2, R3, and R4 are independently selected from H, OH, R11OH, or COOH, and R11 is a C1-C4 alkyl group, with the provisos that:
- (i) at least one of R or R0 is H,
- (ii) at least one of R0, R1, R2, R3, and R4 is OH, COOH, or R11OH, and
- (iii) if one of R1 and R2 is OH and the other is H, then one of R3 and R4 cannot be OH if the other is H;
- and
- 2) a free radical scavenger selected from the group consisting of:
- (a) a sterically hindered phenol having the formula (II):
- where R7, R8 and R9 are independently selected from H or a C1-C10 alkyl group and R10 is H or a C1-C12 alkyl group,
- (b) a phosphite, and
- (c) a combination thereof.
A method for reducing aldehyde emissions from a polyurethane material comprising (i) mixing an amine catalyst containing one or more aldehyde impurities, a treating agent, a polyol, and a polyisocyanate to form a reaction mixture, and (ii) subjecting the reaction mixture to conditions such that a polyurethane material is formed, wherein the treating agent comprises:
- 1) a substituted cyclic urea selected from at least one of 4-hydroxy-5-methyl propylene urea, 4-methoxy-5-methyl propylene urea, 4-hydroxy-5,5-dimethyl propylene urea, 4,5-dimethoxy-2-imidazolidinone, or a substituted cyclic urea having the formula (I):
- where R, R0, R1, R2, R3, and R4 are independently selected from H, OH, R11OH, or COOH, and R11 is a C1-C4 alkyl group, with the provisos that:
- (i) at least one of R or R0 is H,
- (ii) at least one of R0, R1, R2, R3, and R4 is OH, COOH, or R11OH, and
- (iii) if one of R1 and R2 is OH and the other is H, then one of R3 and R4 cannot be OH if the other is H;
- and
- 2) a free radical scavenger selected from the group consisting of:
- (a) a sterically hindered phenol having the formula (II):
- where R7, R8 and R9 are independently selected from H or a C1-C10 alkyl group and R10 is H or a C1-C12 alkyl group,
- (b) a phosphite, and
- (c) a combination thereof.
A packaged product comprising (i) a container having an outlet and (ii) a catalyst mixture within the container, the catalyst mixture comprising a treating agent and an amine catalyst containing one or more aldehyde impurities, wherein the catalyst mixture has been subjected to conditions such that the level of aldehyde impurities in the amine catalyst have been reduced, and wherein the treating agent comprises:
- 1) a substituted cyclic urea selected from at least one of 4-hydroxy-5-methyl propylene urea, 4-methoxy-5-methyl propylene urea, 4-hydroxy-5,5-dimethyl propylene urea, 4,5-dimethoxy-2-imidazolidinone, or a substituted cyclic urea having the formula (I):
- where R, R0, R1, R2, R3, and R4 are independently selected from H, OH, R11OH, or COOH, and R11 is a C1-C4 alkyl group, with the provisos that:
- (i) at least one of R or R0 is H,
- (ii) at least one of R0, R1, R2, R3, and R4 is OH, COOH, or R11OH, and
- (iii) if one of R1 and R2 is OH and the other is H, then one of R3 and R4 cannot be OH if the other is H;
- and
- 2) a free radical scavenger selected from the group consisting of:
- (a) a sterically hindered phenol having the formula (II):
- where R7, R8 and R9 are independently selected from H or a C1-C10 alkyl group and R10 is H or a C1-C12 alkyl group,
- (b) a phosphite, and
- (c) a combination thereof.
Dependencies are inferred from the claim text.