Polyether polyols, polyester polyols and polyurethanes of low residual aldehyde content

Abstract

The present invention describes a process for preventing the formation of aldehydic contaminants in polyether polyols, polyester polyols or polyurethanes which comprises incorporating into said polyether polyols, polyester polyols or polyurethanes an effective amount of a) a phenolic antioxidant and b) one or more compounds selected from (i) aminic antioxidants, (ii) benzofuran-2-ones, (iii) phosphites or phosphonites and (iv) mixtures thereof.

What is claimed is: 
     
         1 . A process for preventing the formation of aldehydic, contaminants in polyether polyols, polyester polyols or polyurethanes which comprises incorporating into said polyether polyols, polyester polyols or polyurethanes an effective amount of
 (a) a phenolic antioxidant and   (b) one or more compounds selected from
 (i) aminic antioxidants, 
 (ii) benzofuran-2-ones, 
 (iii) phosphites or phosphonites and 
 (iv) mixtures thereof. 
   
     
     
         2 . A process according to  claim 1 , wherein the phenolic antioxidant as component (a) is a compound of the formula 1 
       
         
           
           
               
               
           
         
         in which 
         R 1  is hydrogen or C 1 -C 4 alkyl, 
         n is 1, 2, 3 or 4, 
         X is methylene, 
       
       
         
           
           
               
               
           
         
         Y is hydrogen or —NH—; and, 
         if n is 1, 
         X is 
       
       
         
           
           
               
               
           
         
       
       where Y is attached to R 2 , and
 R 2  is C 1 -C 25 alkyl; and, 
 if n is 2, 
 X is 
 
       
         
           
           
               
               
           
         
       
       where Y is attached to R 2 , and
 R 2  is C 2 -C 12 alkylene, C 4 -C 12 alkylene interrupted by oxygen or sulfur; or, if Y is —NH—, R 2  is additionally a direct bond; and, 
 if n is 3, 
 X is methylene or 
 
       
         
           
           
               
               
           
         
       
       where the ethylene group is attached to
 R 2 , and 
 R 2  is 
 
       
         
           
           
               
               
           
         
         if n is 4, 
         X is 
       
       
         
           
           
               
               
           
         
       
       where Y is attached to R 2 , and
 R 2  is C 4 -C 10 alkanetetrayl. 
 
     
     
         3 . A process according to  claim 1 , comprising incorporating one or more (i) aminic antioxidants of formula II 
       
         
           
           
               
               
           
         
         wherein 
         R 25  is C 1 -C 16 alkyl, phenyl-C 1 -C 4 alkyl, C 5 -C 12 cycloalkyl, phenyl, naphthyl; phenyl or naphthyl each of which is substituted by C 1 -C 12 alkyl or C 1 -C 12 alkoxy or benzyl or α,α-dimethylbenzyl, R 26  is phenyl, naphthyl; phenyl or naphthyl, each of which is substituted by C 1 -C 12 alkyl or C 1 -C 12 alkoxy or benzyl or α,α-dimethylbenzyl, or 
         R 25  and R 26  form a radical of formula III 
       
       
         
           
           
               
               
           
         
         wherein 
         R 27  and R 25  are hydrogen or C 1 -C 18 alkyl, 
         R 29  is hydrogen, and 
         R 27  and R 29 , taken together, form a group of formula 
       
       
         
           
           
               
               
           
         
       
     
     
         4 . A process according to  claim 1 , comprising incorporating one or more (ii) benzofuran-2-ones of formula IV 
       
         
           
           
               
               
           
         
         wherein 
         R9 is hydrogen or C 1 -C 8 alkyl, 
         R 10  is C 1 -C 12 alkyl, 
         R 11  is hydrogen, C 1 -C 4 alkyl or C 2 -C 8 alkanoyl, 
         R 12  is hydrogen or C 1 -C 8 alkyl, 
         R 13  is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy, and 
         R 14  is hydrogen or C 1 -C 12 alkyl. 
       
     
     
         5 . A process according to  claim 1 , comprising incorporating one or more (iii) phosphites or phosphonites of formula V, VI, VII or VIII 
       
         
           
           
               
               
           
         
         in which 
         n′ is the number 2 and y′ is the number 1, 2 or 3; 
         A′ is C 2 -C 18 alkylene, p-phenylene or p-biphenylene, 
         E′, if y′ is 1, is C 1 -C 18 alkyl, —OR′ 1  or fluorine; 
         E′, if y′ is 2, is p-biphenylene, 
         E, if y′ is 3, is N(CH 2 CH 2 O—) 3 , 
         R′ 1 , R 2  and R′ 3  independently of one another are C 1 -C 18 alkyl, C 7 -C 9 phenylalkyl, cyclohexyl, phenyl, or phenyl substituted by 1 to 3 alkyl radicals having in total 1 to 18 carbon atoms; 
         R′ 14  is hydrogen or C 1 -C 9 alkyl, 
         R′ 15  is hydrogen or methyl; 
         X′ is a direct bond, 
         Y′ is oxygen, 
         Z′ is a direct bond or —CH(R′ 16 )—, and 
         R′ 16  is C 1 -C 4 alkyl. 
       
     
     
         6 . A process according to  claim 1 , wherein component (a) is present in an amount of 0,01 to 10% based on the weight of the polyether polyols, polyester polyols or polyurethanes. 
     
     
         7 . A process according to  claim 1 , wherein component (b) is present in an amount of 0.01 to 10% based on the weight of the polyether polyols, polyester polyols or polyurethanes. 
     
     
         8 . A process according to  claim 1 , comprising incorporating further additives. 
     
     
         9 . A process according to  claim 8 , wherein the further additives are light-stabilizers.