IP Library Granted Patent US 6,858,654
Granted Patent B1
US 6,858,654 · App. 10/695,515 · Granted Feb 22, 2005

Catalyst blends for producing low thermal desorption polyurethane foams

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Quick Facts
Patent No.
US 6,858,654
App. No.
10/695,515
Granted
Feb 22, 2005
Kind
B1
Abstract

A catalyst composition for catalyzing a polyurethane forming reaction includes a gelling catalyst and a blowing catalyst selected such that the resulting polyurethane foam has a low level of volatile and/or malodorous material in it. The gelling catalysts are selected from tertiary aminoalkyl substituted primary or secondary amines; and the blowing catalysts are selected from bis(aminoalkyl) ethers comprising alkanol moieties, primary amine moieties, or ureido moieties derived from such primary amine moieties.

Claims (67)

1. A formulation for producing a polyurethane foam, the formulation comprising a polyol, a polyisocyanate, water, and a catalyst composition comprising:

1) a gelling catalyst represented by the general formula:

in which:

A represents CH or N,

R 1 represents hydrogen or the group

n represents an integer between 1 and 3, inclusive,

R 2 and R 3 each represent hydrogen or a C1-C6 alkyl group, and

R 6 represents H or 3-aminopropyl, provided that:

when A is N, R 4 and R 5 each represents a C1-C6 alkyl group or together represent a C2-C5 alkylene group which may contain a ring amine moiety —NR—, where R is hydrogen, a C1-C4 alkyl group,

 and

when A is CH, R 4 and R 5 together represent a C2-C5 alkylene group containing a ring amine moiety —NR—, where R is a C1-C4 alkyl group or the group

 and

2) a blowing catalyst according to the general formula:

wherein:

R 7 , R 8 , and R 9 each independently represents a C1-C4 alkyl group;

R 10 represents H, a C1-C4 alkyl group, a C6-C20 aryl group, or a C6-C20 aralkyl group;

m, p, and q each independently represents an integer between 1 and 4, inclusive; and Z represents —OH, —NH 2 , —NH—CO—NH 2 , or

2. The formulation of claim 1 , wherein R 4 and R 5 are each a methyl group, A is nitrogen, and R 2 and R 3 are each hydrogen.

3. The formulation of claim 1 , wherein R 7 , R 8 , and R 9 are each a methyl group, m and p are each equal to 2, and q is either 2 or 3.

4. The formulation of claim 1 , wherein A is CH, n is an integer between 1 and 3, inclusive, and R 4 and R 5 together constitute —CH 2 CH 2 N(CH 3 )CH 2 —.

5. The formulation of claim 1 , wherein the gelling catalyst comprises N,N,N″,N″-tetramethyldipropylenetriamine.

6. The formulation of claim 1 , wherein the gelling catalyst comprises 3-dimethylaminopropylamine.

7. The formulation of claim 1 , wherein the gelling catalyst comprises N,N-bis(3-dimethylaminopropyl)-1,3-propanediamine.

8. The formulation of claim 1 , wherein the blowing catalyst comprises N,N,N′-trimethyl-N′-2-hydroxyethylbis(aminoethyl) ether.

9. The formulation of claim 8 , wherein the gelling catalyst comprises N,N,N″,N″-tetramethyldipropylenetriamine.

10. The formulation of claim 8 , wherein the gelling catalyst comprises 3-dimethylaminopropylamine.

11. The formulation of claim 8 , wherein the gelling catalyst comprises N,N-bis(3-dimethylaminopropyl)-1,3-propanediamine.

12. The formulation of claim 1 , wherein the blowing catalyst comprises N,N,N′-trimethyl-N′-3-aminopropylbis(aminoethyl) ether.

13. The formulation of claim 1 , wherein the blowing catalyst comprises N,N,N′-trimethyl-N′-3-ureidopropylbis(aminoethyl) ether.

14. The formulation of claim 1 , further comprising a carboxylic acid that forms a salt with one or both of the gelling catalyst and the blowing catalyst.

15. A polyurethane foam comprising a product of a reaction between a polyol and a polyisocyanate, the reaction taking place in the presence of water and a catalyst composition comprising:

1) a gelling catalyst represented by the general formula:

in which:

A represents CH or N,

R 1 represents hydrogen or the group

n represents an integer between 1 and 3, inclusive,

R 2 and R 3 each represent hydrogen or a C1-C6 alkyl group, and

R 6 represents H or 3-aminopropyl, provided that:

when A is N, R 4 and R 5 each represents a C1-C6 alkyl group or together represent a C2-C5 alkylene group which may contain a ring amine moiety —NR—, where R is hydrogen, a C1-C4 alkyl group, or the group

 and

when A is CH, R 4 and R 5 together represent a C2-C5 alkylene group containing a ring amine moiety —NR—, where R is a C1-C4 alkyl group or the group

 and PS 2) a blowing catalyst according to the general formula:

wherein:

R 7 , R 8 , and R 9 each independently represents a C1-C4 alkyl group;

R 10 represents H, a C1-C4 alkyl group, a C6-C20 aryl group, or a C6-C20 aralkyl group;

m, p, and q each independently represents an integer between 1 and 4, inclusive; and Z represents —OH, —NH 2 , —NH—CO—NH 2 , or

16. A method of making a polyurethane foam, the method comprising mixing together a polyol, a polyisocyanate, water, and a catalyst composition comprising:

1) a gelling catalyst represented by the general formula:

in which:

A represents CH or N,

R 1 represents hydrogen or the group

n represents an integer between 1 and 3, inclusive,

R 2 and R 3 each represent hydrogen or a C1-C6 alkyl group, and

R 6 represents H or 3-aminopropyl, provided that

when A is N, R 4 and R 5 each represents a C1-C6 alkyl group or together represent a C2-C5 alkylene group which may chain a ring amine moiety —NR—, where R is hydrogen, a C1-C4 alkyl group, or the group

 and

when A is CH, R 4 and R 5 together represent a C2-C5 alkylene group containing a ring amine moiety —NR—, where R is a C1-C4 alkyl group or the group

2) a blowing catalyst according to the general formula:

wherein:

R 7 , R 8 , and R 9 each independently represents a C1-C4 alkyl group;

R 10 represents H, a C1-C4 alkyl group, a C6-C20 aryl group, or a C6-C20 aralkyl group;

m, p, and q each independently represents an integer between 1 and 4, inclusive; and Z represents —OH, —NH 2 , —NH—CO—NH 2 , or

.

17. The method of claim 16 , wherein the blowing catalyst comprises N,N,N′-trimethyl-N′-2-hydroxyethylbis(aminoethyl) ether.

18. The method of claim 16 , wherein the blowing catalyst comprises N,N,N′-trimethyl-N′-3-aminopropylbis(aminoethyl) ether.

19. The method of claim 16 , wherein the blowing catalyst comprises N,N,N′-trimethyl-N′-3-ureidopropylbis(aminoethyl) ether.

20. The method of claim 16 , wherein the catalyst composition further comprises a carboxylic acid that forms a salt with one or both of the gelling catalyst and the blowing catalyst.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2017
From: AIR PRODUCTS AND CHEMICALS, INC.
To: EVONIK DEGUSSA GMBH
Reel/Frame 042378/0791 →