Polyurethane foams made with blowing catalyst compositions containing primary hydroxyl groups and high ethylenediamine backbones

Abstract

A method is provided for preparing polyurethane foams, which comprises contacting at least one organic isocyanate compound, at least one polyol, at least one blowing agent, and a tertiary amine catalyst composition. The catalyst composition has the general formula wherein R 1 , R 2 , and Y are, independently, an alkyl group having from one to three carbon atoms or —CH 2 CH 2 OH; Z is —CH 2 CH 2 OH; and n is an integer from 3 to 7, inclusive. Also provided is a method for catalyzing the reaction between at least one isocyanate compound and at least one active hydrogen-containing compound, such as a polyol and/or a blowing agent.

1 . A method to produce a foamed polyurethane comprising contacting 
 (a) at least one organic isocyanate compound;    (b) at least one polyol;    (c) at least one blowing agent; and    (d) at least one tertiary amine catalyst compound having the general formula                          wherein 
 R 1 , R 2 , and Y are, independently, an alkyl group having from one to three carbon atoms or —CH 2 CH 2 OH;  
 Z is —CH 2 CH 2 OH; and  
 n is an integer from 3 to 7, inclusive.  
   
   
   
       2 . A method according to  claim 1 , wherein R 1  and R 2  are methyl groups, Y is a methyl group or —CH 2 CH 2 OH, and n is an integer from 3 to 7, inclusive.  
   
   
       3 . A method according to  claim 1 , wherein the organic isocyanate compound is hexamethylene diisocyanate, phenylene diisocyanate, toluene diisocyanate, 4,4′-diphenylmethane diisocyanate, or any combination thereof.  
   
   
       4 . A method according to  claim 3 , wherein the organic isocyanate compound is 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, or any combination thereof.  
   
   
       5 . A method according to  claim 1 , wherein the polyol is selected from at least one polyalkylene ether polyol, at least one polyester polyol, at least one polymer polyol, or any combination thereof.  
   
   
       6 . A method according to  claim 5 , wherein the polyalkylene ether polyol is a poly(ethylene oxide) or poly(propylene oxide) polymer or copolymer with a terminal hydroxyl group.  
   
   
       7 . A method according to  claim 6 , wherein the polyalkylene ether polyol is ethylene glycol, propylene glycol, 1,3-butane diol, 1,4-butane diol, 1,6-hexane diol, neopentyl glycol, diethylene glycol, dipropylene glycol, pentaerythritol, glycerol, diglycerol, trimethylol propane, or any combination thereof.  
   
   
       8 . A method according to  claim 1 , wherein the ratio of the polyol to the catalyst composition ranges from about 10:1 to about 200:1.  
   
   
       9 . A method according to  claim 1 , wherein the ratio of the blowing agent to the catalyst composition ranges from about 1:1 to about 9:1.  
   
   
       10 . A method according to  claim 1 , wherein the blowing agent is water.  
   
   
       11 . A method according to  claim 1 , wherein the tertiary amine catalyst compound is 
 N-(2-hydroxyethyl)-N,N′,N″,N′″,N′″pentamethyltriethylenetetramine;    N′-(2-hydroxyethyl)-N,N,N″,N′″,N′″pentamethyltriethylenetetramine;    N,N′-bis-(2-hydroxyethyl)-N,N″,N′″,N′″tetramethyltriethylenetetramine;    N,N″-bis-(2-hydroxyethyl)-N,N′,N′″,N′″tetramethyltriethylenetetramine;    N,N′″-bis-(2-hydroxyethyl)-N,N′,N′″,N′″ tetramethyltriethylenetetramine;    N-(2-hydroxyethyl)-N,N′,N″,N′″,N″″,N″″hexamethyltetraethylenepentamine;    N′-(2-hydroxyethyl)-N,N,N″,N′″,N″″,N″″hexamethyltetraethylenepentamine;    N″-(2-hydroxyethyl)-N,N,N′,N′″,N″″,N″″hexamethyltetraethylenepentamine;    N′″-(2-hydroxyethyl)-N,N,N′,N″,N″″,N″″hexamethyltetraethylenepentamine;    or any combination thereof.    
   
   
       12 . A method according to  claim 1 , further comprising contacting (a), (b), (c), and (d) with at least one cell stabilizer, at least one crosslinking agent, at least one chain extender, at least one pigment, at least one filler, at least one flame retardant, at least one auxiliary gelling catalyst, at least one auxiliary blowing catalyst, at least one transition metal catalyst, or any combination thereof.  
   
   
       13 . A method according to  claim 12 , wherein the cell stabilizer is a silicon surfactant, an anionic surfactant, or any combination thereof.  
   
   
       14 . A method according to  claim 13 , wherein the silicon surfactant is polyalkylsiloxane, polyoxyalkylene polyol-modified dimethylpolysiloxane, alkylene glycol-modified dimethylpolysiloxane, or any combination thereof.  
   
   
       15 . A method according to  claim 13 , wherein the anionic surfactant is a salt of a fatty acid, a salt of a sulfuric acid ester, a salt of a phosphoric acid ester, a sulfonate, or any combination thereof.  
   
   
       16 . A method according to  claim 12 , wherein the crosslinking agent is a polyhydric alcohol, a polyamine, or any combination thereof.  
   
   
       17 . A method according to  claim 16 , wherein the polyhydric alcohol is ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, glycerol, trimethylolpropane, or any combination thereof.  
   
   
       18 . A method according to  claim 16 , wherein the polyamine is diethyltoluenediamine, chlorodiaminobenzene, diethanolamine, diisopropanolamine, triethanolamine, tripropanolamine, 1,6-hexanediamine, or any combination thereof.  
   
   
       19 . A method according to  claim 12 , wherein the chain extender is a glycol, an amine, a diol, water, or any combination thereof.  
   
   
       20 . A method according to  claim 19 , wherein the chain extender is ethylene glycol, propylene glycol, 1,4-butanediol, 1,3-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,10-decanediol, 1,12-dodecanediol, ethoxylated hydroquinone, 1,4-cyclohexanediol, N-methylethanolamine, N-methylisopropanolamine, 4-aminocyclo-hexanol, 1,2-diaminoethane, 2,4-toluenediamine, or any combination thereof.  
   
   
       21 . A method according to  claim 12 , wherein the auxiliary gelling catalyst is diazabicyclooctane (triethylenediamine), quinuclidine, a substituted quinuclidine, a substituted pyrrolidine, a substituted pyrrolizidine, an N,N-dimethylaminoalkyl urea, or any combination thereof.  
   
   
       22 . A method according to  claim 12 , wherein the auxiliary blowing catalyst is bis-dimethylaminoethyl ether, pentamethyl-diethylenetriamine, a higher permethylated polyamine, 2-[N-(dimethylaminoethoxyethyl)-N-methylamino]ethanol, an alkoxylated polyamine, an imidazole-boron composition, an amino propyl-bis(amino-ethyl)ether composition, or any combination thereof.  
   
   
       23 . A method to catalyze the reaction between an organic isocyanate compound and an active hydrogen-containing compound comprising contacting 
 (a) at least one organic isocyanate compound;    (b) at least one active hydrogen-containing compound; and    (c) at least one tertiary amine catalyst compound having the general formula                          wherein 
 R 1 , R 2 , and Y are, independently, an alkyl group having from one to three carbon atoms or —CH 2 CH 2 OH;  
 Z is —CH 2 CH 2 OH; and  
 n is an integer from 3 to 7, inclusive.  
   
   
   
       24 . A method according to  claim 23 , wherein the active hydrogen-containing compound is an alcohol, a polyol, an amine, or water.