Tertiary alkanolamines containing surface active alkyl groups
View Patent ↗The present invention relates to novel tertiary alkanolamines useful as catalysts for preparing polyurethane foams and as additives to reduce the dynamic surface tension of aqueous solutions. The tertiary alkanolamines may be represented by formula (I): wherein A, R 1 –R 6 , and n are defined herein.
1. A compound represented by formula (I):
wherein A represents CH or N;
R 1 represents
and R 6 represents —CH 2 C(R 7 )(OH)CH 2 OR 8 ; or R 1 represents —CH 2 C(R 7 )(OH)CH 2 OR 8 and R 6 represents an alkyl or alkenyl group having C 4 –C 36 carbon atoms; or
R 1 represents
and R 6 represents —CH 2 C(R 7 )(OH)R 8 ; or R 1 represents —CH 2 C(R 7 )(OH)R 8 and R 6 represents an alkyl or alkenyl group having C 4 –C 36 carbon atoms;
R 2 and R 3 each represent hydrogen or an alkyl or alkenyl group having C 1 –C 6 carbon atoms;
R 4 and R 5 each represent an alkyl group having C 1 –C 6 carbon atoms when A represents N; or R 4 and R 5 together represent a C 2 –C 5 alkylene group when A represents N; or
R 4 and R 5 together represent a C 2 –C 5 alkylene group containing NR 10 or NR 11 when A is CH or N, where R 10 is hydrogen or an alkyl group having C 1 –C 4 carbon atoms and R 11 is an alkyl group having C 1 –C 4 carbon atoms or
R 7 represents hydrogen or an alkyl or alkenyl group having C 1 –C 5 carbon atoms;
R 8 represents an alkyl or alkenyl group having C 4 –C 36 carbon atoms or —COR 9 , where R 9 represents an alkyl or alkenyl group having C 3 –C 35 carbon atoms; and
n is an integer from 1 to 3.
2. The compound of claim 1 , wherein R 1 is
3. The compound of claim 1 , wherein R 2 and R 3 are hydrogen.
4. The compound of claim 1 , wherein R 4 and R 5 are alkyl groups having C 1 –C 6 carbon atoms when A represents N.
5. The compound of claim 1 , wherein R 4 and R 5 together represent —CH 2 CH 2 N(CH 3 )CH 2 —.
6. The compound of claim 1 , wherein R 7 is hydrogen.
7. The compound of claim 1 , wherein R 8 is an alkyl or alkenyl group having C 4 –C 22 carbon atoms or —COR 9 .
8. The compound of claim 1 , wherein R 9 is an alkyl or alkenyl group having C 3 –C 22 carbon atoms.
9. The compound of claim 1 , wherein n is 2 or 3.
10. The compound of claim 1 , wherein the compound is selected from the group consisting of N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octadecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexadecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-decyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hexanol) amine, N-(3-dimethylaminopropyl)-N-(2-hexanol) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-octanol) amine, N-(3-dimethylaminopropyl)-N-(2-octanol) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-decanol) amine, N-(3-dimethylaminopropyl)-N-(2-decanol) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-dodecanol) amine, N-(3-dimethylaminopropyl)-N-(2-dodecanol) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-tetradecanol) amine, N-(3-dimethylaminopropyl)-N-(2-tetradecanol) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hexadecanol) amine, N-(3-dimethylaminopropyl)-N-(2-hexadecanol) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-octadecanol) amine, N-(3-dimethylaminopropyl)-N-(2-octadecanol) amine; N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl butyl ether) amine; and N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-neodecanoic ester) amine.
11. The compound of claim 10 , wherein the compound is selected from the group consisting of N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octadecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexadecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-decyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl butyl ether) amine; and N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-neodecanoic ester) amine.
12. The compound of claim 11 , wherein the compound is N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl butyl ether) amine.
13. The compound of claim 11 , wherein the compound is N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether) amine.
14. The compound of claim 11 , wherein the compound is N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether) amine.
15. The compound of claim 11 , wherein the compound is N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether) amine.
16. The compound of claim 11 , wherein the compound is N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-neodecanoic ester) amine.
17. The compound of claim 11 , wherein the compound is a mixture of N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether) amine and N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether) amine.