IP Library Granted Patent US 8,618,014
Granted Patent B2
US 8,618,014 · App. 13/547,756 · Granted Dec 31, 2013

Fast demold/extended cream time polyurethane formulations

Inventors: Gary Dale Andrew (Walnutport, PA); Mark Leo Listemann (Kutztown, PA); Patrick Gordon Stehley (Allentown, PA); James Douglas Tobias (Center Valley, PA); John William Miller (Allentown, PA)
Assignee: Air Products and Chemicals, Inc.
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,618,014
App. No.
13/547,756
Granted
Dec 31, 2013
Kind
B2
Abstract

Catalyst compositions for use in forming polyurethane products include a gelling catalyst, a trimerization catalyst, and a cure accelerator. The gelling catalyst is a tertiary amine, mono(tertiary amino) urea, bis(tertiary amino) urea, or a combination of any of these. Any known trimerization catalyst may be used. The cure accelerator may be a diol having at least one primary hydroxyl group, and having from five to 17 chain backbone atoms chosen from carbon, oxygen, or both between the hydroxyl groups, provided that at least five of the backbone atoms are carbon. Alternatively or in addition, the cure accelerator may be a polyol having three or more hydroxyl groups, at least two of which are primary, and having molecular weights between 90 g/mole and 400 g/mole. Delayed initiation of the polyurethane-forming reaction and/or reduced demold time for producing the polyurethane part can be obtained by using these catalyst compositions.

Claims (49)

1. A composition for use in making a polyurethane foam, the composition comprising:

(a) a catalyst combination comprising

(i) a gelling catalyst comprising at least one of a tertiary amine or a mono(tertiary amino) or bis(tertiary amino) urea derivative thereof; and

(ii) a trimerization catalyst comprising a compound selected from the group consisting of TEDA propylene oxide 2-ethylhexanoic acid quat; 1,8-diazabicyclo[5.4.0]undec-7-ene, either alone or blocked with a phenol or a carboxylic acid; N-hydroxyalkyl quaternary ammonium carboxylate salts; N,N′,N″-tris(dimethylaminopropyl)hexahydrotriazine; alkali metal carboxylates and a combinations of any of these;

(b) one or more cure accelerators selected from the group consisting of glycerol, trim ethylol propane, diglycerol, pentaerythritol, dipentaerythritol, and a combination of these; and

(c) a blowing catalyst comprising a compound selected from the group consisting of pentamethyldiethylenetriamine, permethylated polyamine, branched polyamine, alkoxylated polyamine, permethylated triethylenetetramine, 2-[N-(dimethylaminoethoxyethyl)-N-methylamino)ethanol, aminopropyl-bis(aminoethyl)ether, bis(dimethylaminoethyl)ether, and a combination of these; and wherein the gelling catalyst, the trimerization catalyst, the blowing catalyst and the cure accelerator are present in the amounts as shown in wt %:

Catalyst composition

wt %

Gelling catalyst

 14-35

Trimerization catalyst

1.4-6

Blowing catalyst

0.8-4

Cure accelerator

 55-83.8.

2. The composition of claim 1 , wherein the cure accelerator comprises glycerol.

3. The composition of claim 1 , wherein the cure accelerator comprises trimethylol propane.

4. The composition of claim 1 , wherein the composition further comprises a phenol or a carboxylic acid that forms a salt with at least a portion of at least one of the gelling catalyst and the blowing catalyst.

5. The composition of claim 4 , wherein the phenol or carboxylic acid comprises the compound phenol.

6. The composition of claim 4 , wherein the phenol or carboxylic acid comprises 2-ethylhexanoic acid.

7. The composition of claim 1 , wherein the gelling catalyst comprises triethylenediamine.

8. The composition of claim 1 , wherein the trimerization catalyst comprises 1,8-diazabicyclo[5.4.0]undec-7-ene phenol salt.

9. The composition of claim 1 , wherein the trimerization catalyst comprises N,N′,N″-tris(dimethylaminopropyl)hexahydrotriazine.

10. The composition of claim 1 , wherein the blowing catalyst comprises a compound selected from the group consisting of pentamethyldiethylenetriamine, permethylated triethylenetetramine, bis(dimethylaminoethyl)ether, and mixtures of these.

11. The composition of claim 1 , further comprising a polymeric polyol.

12. The composition of claim 1 , wherein the composition further comprises a phenol or a carboxylic acid that forms a salt with at least a portion of at least one of the gelling catalyst and the blowing catalyst.

13. The composition of claim 1 , wherein the gelling catalyst comprises triethylenediamine, the trimerization catalyst comprises 1,8-diazabicyclo[5.4.0]undec-7-ene phenol salt, the blowing catalyst comprises pentamethyldiethylenetriamine, the cure accelerator comprises glycerol and the chain extender comprises ethylene glycol.

14. The composition of claim 1 wherein the blowing catalyst comprises pentamethyldiethylenetriamine.

15. The composition of claim 1 wherein the trimerization catalyst comprises 1,8-diazabicyclo[5.4.0]undec-7-ene or blocked with a phenol or a carboxylic acid.

16. The composition of claim 1 wherein the blowing catalyst comprises aminopropyl-bis(aminoethyl)ether.

17. The composition of claim 1 wherein the cure accelerator comprises glycerol.

18. The composition of claim 1 wherein the gelling catalyst comprises at least one member selected from the group consisting of TEDA; N,N,N″,N″-tetramethyldipropylenetriamine and dimethylaminopropylamine.

19. A composition for use in making a polyurethane foam, the composition comprising:

(a) a catalyst combination comprising

(i) a gelling catalyst comprising at least one of a tertiary amine or a mono(tertiary amino) or bis(tertiary amino) urea derivative thereof; and

(ii) a trimerization catalyst comprising a compound selected from the group consisting of TEDA propylene oxide 2-ethylhexanoic acid quat; 1,8-diazabicyclo[5.4.0]undec-7-ene, either alone or blocked with a phenol or a carboxylic acid; N-hydroxyalkyl quaternary ammonium carboxylate salts; N,N′,N″-tris(dimethylaminopropyl)hexahydrotriazine; alkali metal carboxylates and a combinations of any of these;

(b) one or more cure accelerators selected from the group consisting of glycerol, trimethylol propane, diglycerol, pentaerythritol, dipentaerythritol, and a combination of these; and

(c) a blowing catalyst comprising a compound selected from the group consisting of pentamethyldiethylenetriamine, permethylated polyamine, branched polyamine, alkoxylated polyamine, permethylated triethylenetetramine, 2-[N-(dimethylaminoethoxyethyl)-N-methylamino)ethanol, aminopropyl-bis(aminoethyl)ether, bis(dimethylaminoethyl)ether, and a combination of these; and wherein the gelling catalyst, the trimerization catalyst, the blowing catalyst and the cure accelerator are present in the amounts as shown in wt %:

Catalyst composition

wt %

Gelling catalyst

24-32

Trimerization catalyst

2-5

Blowing catalyst

1-3

Cure accelerator

60-73.

Assignments (3)
CHANGE OF NAME Recorded Apr 20, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 052445/0567 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2019
From: ANDREW, GARY DALE; LISTEMANN, MARK LEO; STEHLEY, PATRICK GORDON; TOBIAS, JAMES DOUGLAS; MILLER, JOHN WILLIAM
To: AIR PRODUCTS AND CHEMICALS, INC.
Reel/Frame 050842/0077 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2019
From: AIR PRODUCTS AND CHEMICALS, INC.
To: EVONIK DEGUSSA GMBH
Reel/Frame 050889/0121 →
Continuity (3)
Continuation 11131179 · May 18, 2005
Continuation In Part 10856042 · May 28, 2004
Related Publication 20120277093A1 · Nov 1, 2012