Tertiary amine composition and method for making the composition

Patent metadata

Field	Value
Publication number	US-9708436-B2
Application number	US-201615055744-A
Country	US
Kind code	B2
Filing date	Feb 29, 2016
Priority date	Oct 3, 2011
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

A composition and method for producing a tertiary amine is disclosed. The tertiary amine is contacted with an inert gas. The inert gas is nitrogen or more preferably argon. The amine composition is useful in producing polyurethane foam with lower levels of chemical emissions particularly lower emissions of toxic chemicals.

First claim

The invention claimed is:

1. A method of making a polyurethane comprising contacting at least one polyisocyanate with at least one polyol in the presence of a catalytically effective amount of a composition obtained by contacting at least one tertiary amine with at least one inert gas wherein the tertiary amine and gas are in equilibrium, wherein the partial pressure of oxygen in the composition is less than under ambient conditions, wherein the amine contains at least one isocyanate reactive group comprising at least one member selected from the group consisting of secondary amine, hydroxyl, amide, and urea, wherein a concentration of DMF in the composition is less than about 10 parts per million, wherein a concentration of formaldehyde in the composition is less than about 10 parts per million, and wherein a concentration of antioxidants in the composition is less than about 5 parts per million.

2. The method of claim 1 , wherein the contacting of the at least one polyisocyanate and the polyol occurs in the presence of at least one blowing agent under conditions sufficient to produce a polyurethane foam.

3. The method of claim 1 wherein the inert gas comprises at least one of nitrogen and argon.

4. The method of claim 3 wherein the inert gas comprises argon.

5. The method of claim 1 wherein the concentration of antioxidants in the composition is less than about 1 parts per million, wherein the concentration of DMF in the composition is less than about 1 parts per million, and wherein the concentration of formaldehyde in the composition is less than about 1 parts per million.

6. The method of claim 1 wherein the contacting of the at least one polyisocyanate and the polyol occurs in the presence of water, at least one crosslinker, and at least one silicone surfactant.

7. The method of claim 1 wherein at least one tertiary amine comprises N,N,N′-trimethyl-N′-3-aminopropyl-bis(aminoethyl) ether.

8. The method of claim 1 wherein the at least one tertiary amine comprises a blowing catalyst.

9. The method of claim 8 further comprising at least one member selected from the group consisting of triethylenediamine, bis(dimethylaminopropyl) amine, dimethylaminoethoxyethanol, dimethylaminopropylureas, N,N-bis(dimethylamino propyl)-N-(2-hydroypropyl)amine, N-dimethylaminopropyl-N-(2-hydroxyethyl)-N-methylamine, and N-dimethylaminoethyl-N-(2-hydroxyethyl)-N-methyl amine.

10. The method of claim 1 wherein the composition comprises at least one liquid tertiary amine catalyst that has been bubbled with at least one inert gas wherein the amine catalyst and gas are in equilibrium and wherein the partial pressure of oxygen in the amine catalyst is less than under ambient conditions and wherein the composition is substantially free of anti-oxidants, DMF and formaldehyde.

11. The method of claim 1 wherein the composition is obtained by contacting at least one liquid tertiary amine catalyst with at least one inert gas wherein the amine catalyst and gas are in equilibrium; wherein the composition is substantially free of anti-oxidants and wherein the partial pressure of inert gas is higher than about 600 mmHg (0.79 atm) and the partial pressure of oxygen is lower than about 160 mm Hg (0.21 atm).

12. The method of claim 1 wherein the tertiary amine catalyst contains at least one isocyanate-reactive group comprising at least one member consisting of primary amine, secondary amine, hydroxyl group, amide and urea.

13. The method of claim 1 wherein the tertiary amine catalyst comprises at least one member selected from the group consisting of N,N-bis(3-dimethylaminopropyl)-N-isopropanolamine; N,N-dimethylaminoethyl-N′-methyl ethanolamine; N,N,N′-trimethylaminopropyl ethanolamine, N,N-dimethylethanolamine; N,N-dimethyl-N′,N′-2-hydroxy(propyI)-1,3-propylenediamine; dimethylaminopropylamine; (N,N-dimethylaminoethoxy)ethanol, methyl-hydroxy-ethyl-piperazine, bis(N,N-dimethyl-3-aminopropyl)amine, N,N-dimethylaminopropyl urea, N,N′-bis(3-dimethylaminopropyl) urea, bis(dimethylamino)-2-propanol, N-(3-aminopropyl)imidazole, N-(2-hydroxypropyl)imidazole, and N-(2-hydroxyethyl) imidazole.

14. The method of claim 1 wherein the tertiary amine catalyst comprises at least one member selected from the group consisting of 2-[N-(dimethylaminoethoxyethyl)-N-methylamino]ethanol, N, N-dimethylaminoethyl-N′-methyl-N-ethanol, dimethylaminoethoxyethanol and N,N,N′-trimethyl-N′-3-aminopropyl-bis(aminoethyl) ether.

15. The method of claim 1 wherein the tertiary amine catalyst comprises at least one member selected from the group consisting of diazabicyclooctane, tris(dimethyalminopropyl)amine, dimethylaminocyclohexylamine, bis(dimethylaminopropyl)-N-methylamine, N,N-dimethylcyclohexyl amine, and N-Methyldicyclohexylamine.

16. The method of claim 1 wherein the tertiary amine catalyst comprises at least one member selected from the group consisting of bis-dimethylaminoethyl ether, pentamethyldiethylenetriamine, hexamethyltriethylenetetramine, heptamethyltetraethylenepentamine, 24N-(dimethylaminoethoxyethyl)-N-methylamino]ethanol, alkoxylated polyamines; imidazole-boron compositions; and amino propyl-bis(amino-ethyl)ether compositions.

17. The method of claim 1 wherein the method further comprising molding a contact product of polyol and polyisocyanate.

18. An article of manufacture comprising the polyurethane foam prepared by the method of claim 17 .

Assignees

• Evonik Degussa Gmbh

Inventors

• Burdeniuc Juan Jesus
• Al-Rashid Jennifer Elizabeth Antoline
• Wang Andrew Wilson
• Dunn Diana Sue
• Jeon You-Moon
• Kniss Jane Garrett
• Wendel Stephan Hermann

Classifications

• C08G18/14

  Manufacture of cellular products · CPC title

• C08G18/632

  onto polyethers · CPC title

• C08G18/1825

  having hydroxy or primary amino groups · CPC title

• C08J2203/06

  CO2, N2 or noble gases · CPC title

• C08G18/4072

  Mixtures of compounds of group C08G18/63 with other macromolecular compounds · CPC title