Cyclic amine compound and process for producing polyurethane resin by using it

Patent metadata

Field	Value
Publication number	US-9657129-B2
Application number	US-201113996642-A
Country	US
Kind code	B2
Filing date	Dec 22, 2011
Priority date	Dec 22, 2010
Publication date	May 23, 2017
Grant date	May 23, 2017

Abstract

To provide a novel cyclic amine compound and a process for producing a polyurethane resin by using it. A 3-hydroxy-1,5-diazabicyclo[3.2.2]nonane represented by the following formula (1), and a process for producing a polyurethane resin by using a catalyst for producing a polyurethane resin, which contains the 3-hydroxy-1,5-diazabicyclo[3.2.2]nonane. When the compound represented by the formula (1) has optical isomers, diastereomers or geometric isomers, the compound includes both a mixture of any of them and an isolated isomer of any of them.

[in the above formula (1), each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 which are independent of one another, is a hydrogen atom, a C 1-4 alkyl group, a hydroxy group, a hydroxymethyl group or a C 1-4 alkoxy group.]

First claim

The invention claimed is:

1. A 3-hydroxy-1,5-diazabicyclo[3.2.2]nonane represented by the following formula (1), provided that when the compound represented by the formula (1) has optical isomers, diastereomers or geometric isomers, the compound includes both a mixture of any of them and an isolated isomer of any of them:

in the formula (1), each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 which are independent of one another, is a hydrogen atom, a C 1-4 alkyl group, a hydroxy group, a hydroxymethyl group or a C 1-4 alkoxy group.

2. The 3-hydroxy-1,5-diazabicyclo[3.2.2]nonane according to claim 1 , wherein in the formula (1), at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 or R 8 is a methyl group or a hydroxymethyl group.

3. The 3-hydroxy-1,5-diazabicyclo[3.2.2]nonane according to claim 1 , wherein in the formula (1), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are all hydrogen atoms.

4. A catalyst for producing a polyurethane resin, which contains the 3-hydroxy-1,5-diazabicyclo[3.2.2]nonane as defined in claim 1 .

5. A catalyst for producing a polyurethane resin, which contains a 3-hydroxy-1,5-diazabicyclo[3.2.2]nonane represented by the following formula (1), provided that when the compound represented by the formula (1) has optical isomers, diastereomers or geometric isomers, the compound includes both a mixture of any of them and an isolated isomer of any of them:

in the formula (1), each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 which are independent of one another, is a hydrogen atom, a C 1-4 alkyl group, a hydroxy group, a hydroxymethyl group or a C 1-4 alkoxy group, and
a hydroxyalkyl-substituted-1,4-diazabicyclo[2.2.2]octane represented by the following formula (2), provided that when the compound represented by the formula (2) has optical isomers, diastereomers or geometric isomers, the compound includes both a mixture of any of them and an isolated isomer of any of them:

in the formula (2), each of R 1 and R 2 which are independent of each other, is a hydrogen atom, a C 1-4 alkyl group, a hydroxy group, a hydroxymethyl group or a C 1-4 alkoxy group, and m is 1 or 2.

6. The catalyst for producing a polyurethane resin according to claim 5 , wherein in the formula (2), each of R 1 and R 2 is a hydrogen atom, a methyl group, an ethyl group or a hydroxymethyl group (provided that R 1 and R 2 are not all the same substituents).

7. The catalyst for producing a polyurethane resin according to claim 5 , wherein in the formula (2), R 1 and R 2 are all hydrogen atoms.

8. The catalyst for producing a polyurethane resin according to claim 5 , wherein a weight ratio of the 3-hydroxy-1,5-diazabicyclo[3.2.2]nonane to the hydroxyalkyl-substituted-1,4-diazabicyclo[2.2.2]octane is 0.01:1 to 0.3:1.

9. A catalyst for producing a polyurethane resin, which contains a 3-hydroxy-1,5-diazabicyclo[3.2.2]nonane represented by the following formula (1), provided that when the compound represented by the formula (1) has optical isomers, diastereomers or geometric isomers, the compound includes both a mixture of any of them and an isolated isomer of any of them:

in the formula (1), each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 which are independent of one another, is a hydrogen atom, a C 1-4 alkyl group, a hydroxy group, a hydroxymethyl group or a C 1-4 alkoxy group;
a hydroxyalkyl-substituted-1,4-diazabicyclo[2.2.2]octane represented by the following formula (2), provided that when the compound represented by the formula (2) has optical isomers, diastereomers or geometric isomers, the compound includes both a mixture of any of them and an isolated isomer of any of them:

in the formula (2), each of R 1 and R 2 which are independent of each other, is a hydrogen atom, a C 1-4 alkyl group, a hydroxy group, a hydroxymethyl group or a C 1-4 alkoxy group, and m is 1 or 2; and
an aminourea derivative.

10. The catalyst for producing a polyurethane resin according to claim 9 , wherein the hydroxyalkyl-substituted-1,4-diazabicyclo[2.2.2]octane is an amine compound represented by the following formula (2a):

in the formula (2a), X is a hydroxymethyl group or a hydroxyethyl group.

11. The catalyst for producing a polyurethane resin according to claim 9 , wherein the aminourea derivative is at least one member selected from the group consisting of a mono(tertiary aminoalkyl)urea, a bis(tertiary aminoalkyl)urea and a mixture thereof.

12. The catalyst for producing a polyurethane resin according to claim 9 , wherein the aminourea derivative is one or more compounds selected from the group consisting of 2-dimethylaminoethylurea, N,N′-bis(2-dimethylaminoethyl)urea, N,N-bis(2-dimethylaminoethyl)urea, 3-dimethylaminopropylurea, N,N′-bis(3-dimethylaminopropyl)urea, N,N-bis(3-dimethylaminopropyl)urea, 1-(N-methyl-3-pyrrolidino)methylurea, 1,3-bis(N-methyl-3-pyrrolidino)methylurea, 3-piperidinopropylurea, N,N′-bis(3-piperidinopropyl)urea, 3-morpholinopropylurea, N,N′-bis(3-morpholinopropyl)urea, 2-piperidinoethylurea, N,N′-bis(2-piperidinoethyl)urea, 2-morpholinoethylurea and N,N′-bis(2-morpholinoethyl)urea.

13. The catalyst for producing a polyurethane resin according to claim 4 , which does not contain lead, tin, mercury or any compound thereof.

14. A process for producing a polyurethane resin, which comprises reacting a polyol and a polyisocyanate in the presence of the catalyst for producing a polyurethane resin as defined in claim 4 .

15. The process for producing a polyurethane resin according to claim 14 , wherein the amount of the catalyst for producing the polyurethane resin is within a range of from 0.01 to 30 parts by weight per 100 parts by weight of the polyol.

Assignees

• Kiso Hiroyuki
• Suzuki Takao
• Takahashi Yoshihiro
• Tosoh Corp

Inventors

• Kiso Hiroyuki
• Suzuki Takao
• Takahashi Yoshihiro

Classifications

• C08G18/4009

  Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64 · CPC title

• C08G18/3275

  containing two hydroxy groups · CPC title

• C08G18/4804

  Two or more polyethers of different physical or chemical nature · CPC title

• C07D487/08

  Bridged systems · CPC title

• C08G18/2815

  Monohydroxy compounds · CPC title