Amine catalyst for curing polyisocyanate compound and polyisocyanate adhesive composition containing amine catalyst for curing polyisocyanate compound

Patent metadata

Field	Value
Publication number	US-9777199-B2
Application number	US-201314416914-A
Country	US
Kind code	B2
Filing date	Jul 26, 2013
Priority date	Jul 26, 2012
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

To provide an amine catalyst for curing a polyisocyanate which can satisfy both initial moldability before a thermal compression step and high reactivity at the time of thermal compression molding, and an adhesive composition containing it.
A catalyst comprising an amine compound (1) represented by the formula (1) and an amine compound (2) represented by the formula (2) is used as an amine catalyst for curing a polyisocyanate compound.

wherein each of R 1 and R 2 which are independent of each other, is a C 1-4 hydrocarbon group, and R 3 is a C 1-4 hydrocarbon group having a hydroxy group or an amino group;

wherein each of R 4 and R 5 which are independent of each other, is a C 1-4 hydrocarbon group, R 6 is a C 1-4 hydrocarbon group or a C 1-4 hydrocarbon group having a hydroxy group or an amino group, R 7 is a C 1-4 hydrocarbon group having a hydroxy group or an amino group, and m is an integer of from 2 to 6.

First claim

The invention claimed is:

1. An amine catalyst for curing a polyisocyanate compound, which consists of
an amine compound (1) represented by the following formula (1):

wherein each of R 1 and R 2 which are independent of each other, is a C 1-4 hydrocarbon group, and R 3 is a C1-4 hydrocarbon group having an amino group; and
an amine compound (2) represented by the following formula (2):

wherein each of R 4 and R 5 which are independent of each other, is a C1-4 hydrocarbon group, R 6 is a C 1-4 hydrocarbon group or a C 1-4 hydrocarbon group having a hydroxy group, R 7 is a C 1-4 hydrocarbon group having a hydroxy group, and m is an integer within a range of from 2 to 6, and
wherein the content ratio of the amine compound (1) to the amine compound (2) is within a range of from 40/60 to 90/10 by the weight ratio.

2. The amine catalyst for curing a polyisocyanate compound according to claim 1 , wherein in the amine compound (1), each of R 1 and R 2 which are independent of each other, is a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group or a tert-butyl group, and R 3 is an aminomethyl group, a 2-aminoethyl group, a 3-aminopropyl group, a 2-aminopropyl group, a 4-aminobutyl group, a 3-aminobutyl group, a 2-aminobutyl group, a 2-methyl-3-aminopropyl group, a 2-methyl-2-aminopropyl group or a 1,1-dimethyl-2-aminoethyl group.

3. The amine catalyst for curing a polyisocyanate compound according to claim 1 , wherein in the amine compound (2), each of R 4 and R 5 which are independent of each other, is a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group or a tert-butyl group, R 6 is a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a hydroxymethyl group, a 2-hydroxyethyl group, a 3-hydroxypropyl group, a 2-hydroxypropyl group, a 4-hydroxybutyl group, a 3-hydroxybutyl group, a 2-hydroxybutyl group, a 2-methyl-3-hydroxypropyl group, a 2-methyl-2-hydroxypropyl group, a 1,1-dimethyl-2-hydroxyethyl group, and R 7 is a hydroxymethyl group, a 2-hydroxyethyl group, a 3-hydroxypropyl group, a 2-hydroxypropyl group, a 4-hydroxybutyl group, a 3-hydroxybutyl group, a 2-hydroxybutyl group, a 2-methyl-3-hydroxypropyl group, a 2-methyl-2-hydroxypropyl group, or a 1,1-dimethyl-2-hydroxyethyl group.

4. The amine catalyst for curing a polyisocyanate compound according to claim 1 , wherein the amine compound (1) is at least one compound selected from the group consisting of dimethyl-2-aminoethylamine, diethyl-2-aminoethylamine, dimethyl-3-aminopropylamine, diethyl-3-aminopropylamine, dimethyl-2-aminopropylamine, diethyl-2-aminopropylamine and dimethyl-4-aminobutylamine.

5. The amine catalyst for curing a polyisocyanate compound according to claim 1 , wherein the amine compound (2) is at least one compound selected from the group consisting of N,N,N′-trimethyl-2-hydroxyethylethylenediamine, N,N,N′-triethyl-2-hydroxyethylethylenediamine, N,N,N′-trimethyl-3-hydroxypropylethylenediamine, N,N,N′-trimethyl-2-hydroxypropylethylenediamine, N,N-diethyl-N′-methyl-2-hydroxyethylethylenediamine, N,N,N′-trimethyl-2-hydroxyethylpropylenediamine, N,N,N′-trimethyl-2-hydroxyethylbutylenediamine, N,N-dimethyl-N′,N′-bis(2-hydroxyethyl)ethylenediamine, N,N-diethyl-N′,N′-bis(2-hydroxyethyl)ethylenediamine, N,N-dimethyl-N′,N′-bis(3-hydroxypropyl)ethylenediamine, N,N-dimethyl-N′,N′-bis(2-hydroxypropyl)ethylenediamine, N,N-dimethyl-N′,N′-bis(3-hydroxypropyl)propylenediamine, N,N-dimethyl-N′,N′-bis(2-hydroxypropyl)propylenediamine, N,N-diethyl-N′,N′-bis(2-hydroxypropyl)ethylenediamine, and N,N-diethyl-N′,N′-bis(2- hydroxypropyl)propylenediamine.

6. A method for curing a polyisocyanate compound, the method comprising contacting an amine catalyst with the polyisocyante compound,
wherein the amine catalyst comprises:
an amine compound (1) represented by the following formula (1):

wherein each of R 1 and R 2 which are independent of each other, is a C 1-4 hydrocarbon group, and R 3 is a C 1-4 hydrocarbon group having an amino group; and
an amine compound (2) represented by the following formula (2):

wherein each of R 4 and R 5 which are independent of each other, is a C 1-4 hydrocarbon group, R 6 is a C 1-4 hydrocarbon group or a C 1-4 hydrocarbon group having a hydroxy group, R 7 is a C 1-4 hydrocarbon group having a hydroxy group, and m is an integer within a range of from 2 to 6, and
wherein the content ratio of the amine compound (1) to the amine compound (2) is within a range of from 40/60 to 90/10 by the weight ratio.

7. The method according to claim 6 , wherein in the amine compound (1), each of R 1 and R 2 which are independent of each other, is a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group or a tert-butyl group, and R 3 is an aminomethyl group, a 2-aminoethyl group, a 3-aminopropyl group, a 2-aminopropyl group, a 4-aminobutyl group, a 3-aminobutyl group, a 2-aminobutyl group, a 2-methyl-3-aminopropyl group, a 2-methyl-2-aminopropyl group or a 1,1-dimethyl-2-aminoethyl group.

8. The method according to claim 6 , wherein in the amine compound (2), each of R 4 and R 5 which are independent of each other, is a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group or a tert-butyl group, R 6 is a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a hydroxymethyl group, a 2-hydroxyethyl group, a 3-hydroxypropyl group, a 2-hydroxypropyl group, a 4-hydroxybutyl group, a 3-hydroxybutyl group, a 2-hydroxybutyl group, a 2-methyl-3-hydroxypropyl group, a 2-methyl-2-hydroxypropyl group, a 1,1-dimethyl-2-hydroxyethyl group, and R 7 is a hydroxymethyl group, a 2-hydroxyethyl group, a 3-hydroxypropyl group, a 2-hydroxypropyl group, a 4-hydroxybutyl group, a 3-hydroxybutyl group, a 2-hydroxybutyl group, a 2-methyl-3-hydroxypropyl group, a 2-methyl-2-hydroxypropyl group, or a 1,1-dimethyl-2-hydroxyethyl group.

9. The method according to claim 6 , wherein the amine compound (1) is at least one compound selected from the group consisting of dimethyl-2-aminoethylamine, diethyl-2-aminoethylamine, dimethyl-3-aminopropylamine, diethyl-3-aminopropylamine, dimethyl-2-aminopropylamine, diethyl-2-aminopropylamine and dimethyl-4-aminobutylamine.

10. The method according to claim 6 , wherein the amine compound (2) is at least one compound selected from the group consisting of N,N,N′-trimethyl-2-hydroxyethylethylenediamine, N,N,N′-triethyl-2-hydroxyethylethylenediamine, N,N,N′-trimethyl-3-hydroxypropylethylenediamine, N,N,N′-trimethyl-2-hydroxypropylethylenediamine, N,N-diethyl-N′-methyl-2-hydroxyethylethylenediamine, N,N,N′-trimethyl-2-hydroxyethylpropylenediamine, N,N,N′-trimethyl-2-hydroxyethylbutylenediamine, N,N-dimethyl-N′,N′-bis(2-hydroxyethyl)ethylenediamine, N,N-diethyl-N′,N′-bis(2-hydroxyethyl)ethylenediamine, N,N-dimethyl-N′,N′-bis(3-hydroxypropyl)ethylenediamine, N,N-dimethyl-N′,N′-bis(2-hydroxypropyl)ethylenediamine, N,N-dimethyl-N′,N′-bis(3-hydroxypropyl

Assignees

• Tosoh Corp

Inventors

• Miyagawa Yasumichi
• Kiso Hiroyuki

Classifications

• C09J175/04

  Polyurethanes · CPC title

• C09J175/00

  Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers · CPC title

• C08G18/1825

  having hydroxy or primary amino groups · CPC title

• C08G18/1808

  having alkylene polyamine groups · CPC title

• C08G18/18 Primary

  containing secondary or tertiary amines or salts thereof · CPC title