Amine composition useful for making polyurethane foam

Patent metadata

Field	Value
Publication number	US-11021561-B2
Application number	US-201715647009-A
Country	US
Kind code	B2
Filing date	Jul 11, 2017
Priority date	Jul 11, 2016
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

Abstract

A catalyst composition for making polyurethane foam, the catalyst composition including a compound having a general formula R 1 R 2 R 3 N, wherein each of R 1 , R 2 and R 3 are independently selected from the group consisting of:
a compound according to formula (I):

wherein n=1 to 5; and R4, R5 and R6 are each independently hydrogen, methyl, ethyl and propyl groups; hydrogen, a C1-C6 alkyl group compound, a C1-C6 cycloalkyl group compound, a C1-C6 alkenyl group compound, a C1-C6 alkynyl group compound, a C1-C6 aryl group compound, and a C1-C6 aralkyl group compound, each group being substituted or unsubstituted; wherein at least one of R 1 , R 2 and R 3 is a compound according to formula (I). A polyurethane composition and method for forming a polyurethane foam are also disclosed.

First claim

The invention claimed is:

1. A composition comprising a contact product of at least one active hydrogen-containing compound, at least one polyisocyanate, at least one blowing agent, at least one additive, and a catalyst composition, wherein the catalyst composition comprises a combination of a first compound and a second compound, wherein the first compound is selected from the group consisting of:
(a). a compound with a general formula R 1 R 2 R 3 N wherein each of R 1 , R 2 and R 3 is a moiety according to formula (I):

wherein n=1 to 5; and R 4 , R 5 and R 6 are each hydrogen; and

(b). a compound with a general formula R 1 R 2 R 3 N wherein each of R 1 and R 2 is a moiety according to formula (I):

wherein n=1 to 5; R 4 , R 5 and R 6 are each hydrogen; and R 3 is hydrogen, C 1 -C 6 alkyl group, cycloalkyl, alkenyl, alkynyl, aryl, or aralkyl, any of which are substituted or unsubstituted;

wherein the second compound is selected from the group consisting of (a), (b), and
(c). a compound with a general formula R 1 R 2 R 3 N wherein R 1 is a moiety according to formula (I):

wherein n=1 to 5; R 4 , R 5 and R 6 are each hydrogen; and R 2 and R 3 are each independently hydrogen, C 1 -C 6 alkyl group, cycloalkyl, alkenyl, alkynyl, aryl, or aralkyl, any of which are substituted or unsubstituted;

and wherein the first compound and the second compound are optionally blocked with a carboxylic or sulfonic acid.

2. The composition of claim 1 , wherein the contact product further comprises a tertiary amine.

3. The composition of claim 1 , wherein the at least one additive is selected from the group consisting of cell stabilizer, flame retardant, chain extender, epoxy resin, acrylic resin, filler, and pigment.

4. The composition of claim 1 , wherein the catalyst composition is present in amounts from about 0.05 to about 20 parts by weight per hundred weight parts of the at least one active hydrogen-containing compound.

5. A polyurethane flexible foam product formed from the composition of claim 1 .

6. A polyurethane rigid foam product formed from the composition of claim 1 .

7. A method for preparing a polyurethane foam by reacting an organic polyisocyanate and a polyol in the presence of a blowing agent, a cell stabilizer and a catalyst composition, wherein the catalyst composition comprises a combination of a first compound and a second compound, wherein the first compound is selected from the group consisting of:
(a). a compound with a general formula R 1 R 2 R 3 N wherein each of R 1 , R 2 and R 3 is a moiety according to formula (I):

wherein n=1 to 5; and R 4 , R 5 and R 6 are each hydrogen; and

(b). a compound with a general formula R 1 R 2 R 3 N wherein each of R 1 and R 2 is a moiety according to formula (I):

wherein n=1 to 5; R 4 , R 5 and R 6 are each hydrogen; and R 3 is hydrogen, C 1 -C 6 alkyl group, cycloalkyl, alkenyl, alkynyl, aryl, or aralkyl, any of which are substituted or unsubstituted;

wherein the second compound is selected from the group consisting of (a), (b), and
(c). a compound with a general formula R 1 R 2 R 3 N wherein R 1 is a moiety according to formula (I):

wherein n=1 to 5; R 4 , R 5 and R 6 are each hydrogen; and R 2 and R 3 are each independently hydrogen, C 1 -C 6 alkyl group, cycloalkyl, alkenyl, alkynyl, aryl, or aralkyl, any of which are substituted or unsubstituted;

and wherein the first compound and the second compound are optionally blocked with a carboxylic or sulfonic acid.

8. The method of claim 7 , wherein the first compound is a compound with a general formula R 1 R 2 R 3 N wherein each of R 1 and R 2 is a moiety according to formula (I):

wherein n=1 to 5; R 4 , R 5 and R 6 are each hydrogen; and R 3 is hydrogen, C 1 -C 6 alkyl group, cycloalkyl, alkenyl, alkynyl, aryl, or aralkyl, any of which are substituted or unsubstituted.

9. The method of claim 7 , wherein the second compound is a compound with a general formula R 1 R 2 R 3 N wherein R 1 is a moiety according to formula (I):

wherein n=1 to 5; R 4 , R 5 and R 6 are each hydrogen; and R 2 and R 3 are each independently hydrogen, C 1 -C 6 alkyl group, cycloalkyl, alkenyl, alkynyl, aryl, or aralkyl, any of which are substituted or unsubstituted.

10. The method of claim 7 , wherein the first compound is selected from the group consisting of N,N-bis(3-imidazolylpropyl) amine, N,N-bis(3-imidazolylpropyI)-N-methyl-amine, N,N-bis(3-imidazolylpropyI)-N-ethyl-amine, N,N-bis(3-imidazolylpropyI)-N-propyl-amine, N,N-bis(3-imidazolylpropyI)-N-butyl-amine, N,N-bis(3-imidazolylpropyI)-N-pentyl-amine, N,N-bis(3-imidazolylpropyI)-N-hexyl-amine, N,N,N-tris(3-imidazolylpropyI)-amine, and combinations thereof.

11. The method of claim 10 , wherein the second compound is selected from the group consisting of N-(3-aminopropyl)-imidazole, N,N-dimethylaminopropylimidazole, and N-(3-imidazolylpropyl)-N-benzyl-N-methyl-amine.

12. The method of claim 7 , wherein the catalyst composition further comprises at least one tertiary amine having at least one isocyanate reactive group comprising a primary hydroxyl group, a secondary hydroxyl group, a primary amine group, a secondary amine group, a urea group or an amide group.

13. The method of claim 12 , wherein the tertiary amine is selected from the group consisting of N, N-bis(3-dimethylaminopropyl)-N-isopropanolamine, N, N-dimethylaminoethyl-N′-methyl ethanolamine, N, N, N′-trimethylaminopropylethanolamine, N, N-dimethylethanolamine, N, N-diethylethanolamine N, N-dimethyl-N′, N′-2-hydroxy(propyl)-1,3-propylenediamine,dimethylaminopropylamine, (N, N-dimethylaminoethoxy) ethanol, methyl-hydroxy-ethyl-piperazine, bis(N, N-dimethyl-3-aminopropyl) amine,N, N-dimethylaminopropyl urea, diethylaminopropyl urea, N, N′-bis(3-dimethylaminopropyl)urea, N, N′-bis(3-diethylaminopropyl)urea, bis(dimethylamino)-2-propanol, 6-dimethylamino-1-hexanol, N-(3-aminopropyl) imidazole), N-(2-hydroxypropyl) imidazole, N-(2-hydroxyethyl) imidazole, 2-[N-(dimethylaminoethoxyethyl)-N-methylamino] ethanol, N, N-dimethylaminoethyl-N′-methyl-N′-ethanol, dimethylaminoethoxyethanol, N, N, N′-trimethyl-N′-3-aminopropyl-bis(aminoethyl) ether, and combinations thereof.

14. The method of claim 7 , wherein the first compound and second compound are acid blocked with a carboxylic or sulfonic acid.

15. The method of claim 14 , wherein the first compound and second compound are acid blocked with an acid selected from the group consisting of formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, neopentanoic acid,

Assignees

• Evonik Operations Gmbh

Inventors

• Xi Kai
• Burdeniuc Juan Jesus
• Hsu Irene Joann
• Keller Renee Jo
• Miller Timothy Joseph
• Bender Jared Denis
• Kniss Jane

Classifications

• C08G18/1858

  having carbon-to-nitrogen double bonds · CPC title

• C08G18/225

  of alkali or alkaline earth metals · CPC title

• C08G18/1808 Primary

  having alkylene polyamine groups · CPC title

• C08G2110/0008

  flexible · CPC title

• C08G18/7671

  containing only one alkylene bisphenyl group · CPC title