Reduction of aldehydes in amine catalysts

Patent metadata

Field	Value
Publication number	US-10131737-B2
Application number	US-201414767923-A
Country	US
Kind code	B2
Filing date	Sep 30, 2014
Priority date	Oct 1, 2013
Publication date	Nov 20, 2018
Grant date	Nov 20, 2018

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.

First claim

What is claimed is:

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 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, R 0 , R 1 , R 2 , R 3 , and R 4 are independently selected from H, OH, R 11 OH, or COOH, and R 11 is a C 1 -C 4 alkyl group, with the provisos that:
(i) at least one of R or R 0 is H,
(ii) at least one of R 0 , R 1 , R 2 , R 3 , and R 4 is OH, COOH, or R 11 OH, and
(iii) if one of R 1 and R 2 is OH and the other is H, then one of R 3 and R 4 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 R 7 , R 8 and R 9 are independently selected from H or a C 1 -C 10 alkyl group and R 10 is H or a C 1 -C 12 alkyl group,

(b) a phosphite, and
(c) a combination thereof.

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

3. The method of claim 1 wherein the substituted cyclic urea is 4-hydroxyethyl ethylene urea, 4-hydroxy-5-methyl propylene urea, 4-methoxy-5-methyl propylene urea, 4-hydroxy-5,5-dimethyl propylene urea, 1-(2-hydroxyethyl)-2-imidazolidinone, or a mixture thereof.

4. The method of claim 1 wherein R 7 , R 8 and R 9 are independently selected from H or a CH 3 group and R 19 is H or a C 1 -C 4 alkyl group.

5. The method of claim 4 wherein R 7 , R 8 and R 9 are each a CH 3 group and R 10 is H, a methyl group, an ethyl group, a propyl group or an isopropyl group.

6. The method of claim 1 , wherein the free radical scavenger is a phosphite selected from the group consisting of trioleyl phosphite, tris(dipropylene glycol) phosphite, trilauryl trithiophosphite, diethyl hydrogen phosphite, bis(2-ethylhexyl) hydrogen phosphite, dilauryl hydrogen phosphite, dioleyl hydrogen phosphite, diphenyl hydrogen phosphite, tetraphenyl dipropyleneglycol diphosphite, tetraphenyl tetra(dodecyl) pentaerythritol tetraphosphite/bis(2-ethylhexyl)phthalate, tetra(C 12 -C 15 alkyl)-4,4′-isopropylidene diphenyl diphosphite, bis(tridecyl)pentaerythritol diphosphite/bis(nonylphenyl)pentaerythritol diphosphite, bis(tridecyl) pentaerythritol diphosphite, hydrogenated bisphenol A pentaerythritol phosphite polymer, hydrogenated bisphenol A phosphite polymer, and mixtures thereof.

7. An amine catalyst produced according to the method of claim 1 .

8. 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, R 0 , R 1 , R 2 , R 3 , and R 4 are independently selected from H, OH, R 11 OH, or COOH, and R 11 is a C 1 -C 4 alkyl group, with the provisos that:
(i) at least one of R or R 0 is H,
(ii) at least one of R 0 , R 1 , R 2 , R 3 , and R 4 is OH, COOH, or R 11 OH, and
(iii) if one of R 1 and R 2 is OH and the other is H, then one of R 3 and R 4 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 R 7 , R 8 and R 9 are independently selected from H or a C 1 -C 10 alkyl group and R 10 is H or a C 1 -C 12 alkyl group,

(b) a phosphite, and
(c) a combination thereof.

9. The method of claim 8 , wherein the amine catalyst and treating agent in step (i) are first mixed to form a catalyst mixture and are subjected to conditions such that the level of aldehyde impurities in the catalyst mixture is reduced.

10. The method of claim 8 wherein the reaction mixture further comprises one or more additives.

11. The method of claim 10 wherein the one or more additives are selected from the group consisting of a blowing agent; a crosslinking agent, a flame retardant; a plasticizer; an internal mold release agent; a surfactant; an acid scavenger; a water scavenger; a cell regulator; a pigment; a dye; a UV stabilizer; a fungistatic or bacteriostatic substance; a filler; and a mixture thereof.

12. 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, R 0 , R 1 , R 2 , R 3 , and R 4 are independently selected from H, OH, R 11 OH, or COOH, and R 11 is a C 1 -C 4 alkyl group, with the provisos that:
(i) at least one of R or R 0 is H,
(ii) at least one of R 0 , R 1 , R 2 , R 3 , and R 4 is OH, COOH, or R 11 OH, and
(iii) if one of R 1 and R 2 is OH and the other is H, then one of R 3 and R 4 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 R 7 , R 8 and R 9 are independently selected from H or a C 1 -C 10 alkyl group and R 10 is H or a C 1 -C 12 alkyl group,

(b) a phosphite, and
(c) a combination thereof.

13. The packaged product of claim 12 wherein the conditions include maintaining the catalyst mixture at room temperature for at least about 3 hours.

Assignees

• Huntsman Petrochemical Llc

Inventors

• Rister Jr Ernest L
• Godavarthy Srinivasa S
• Robertson Henry
• Grigsby Jr Robert A
• Moore Robert B
• Dries Geert Lodewijk
• Wiltz Jr Eugene P

Classifications

• C08G2290/00

  Compositions for creating anti-fogging · CPC title

• C08G2101/0083

  Chemistry & Metallurgy · mapped topic

• C08G18/48

  Polyethers · CPC title

• C08G18/82

  Post-polymerisation treatment · CPC title

• C08G18/1825

  having hydroxy or primary amino groups · CPC title