Alkylphenol free - liquid polymeric polyphosphite polymer stabilizers

Abstract

An alkylphenol-free liquid polymeric polyphosphite is described of general Structure IV illustrated below wherein each R 1 , R 2 , R 3 and R 4 can be the same or different and independently selected from the group consisting of C 1-20 alkyl, C 2-22 alkenyl, C 6-40 cycloalkyl, C 7-40 cycloalkylene, C 3-20 methoxy alkyl glycol ethers, C 3-20 alkyl glycol ethers, and or Y—OH; Y is selected from the group consisting of C 2-40 alkylene, C 2-40 alkyl lactone, —R 7 —N(R 8 )—R 9 —, wherein R 7 , R 8 and R 9 are independently selected from the group previously defined for R 1 , R 2 , R 3 and R 4 , now further including H; m is an integral value ranging from 2 to 100 inclusive; and x is an integral value ranging from 1 to 1,000 and further in which by controlling a molar ratio of reactants, the number of terminal hydroxyl groups is minimized. The alkylphenol-free liquid polymeric phosphite is useful in reducing phosphite migration within polymers.

What is claimed is: 
     
         1 . An alkylphenol-free liquid polymeric polyphosphite which comprises: 
       
         
           
           
               
               
           
         
         wherein
 each R 1 , R 2 , R 3  and R 4  can be the same or different and independently selected from the group consisting of C 1-20  alkyl, C 2-22  alkenyl, C 3-40  cycloalkyl, C 3-40  cycloalkylene, C 3-20  methoxy alkyl glycol ethers, C 3-20  alkyl glycol ethers and Y—OH as an end-capping group; 
 each Y is independently selected from the group consisting of C 1-20  alkyl, C 6-40  cycloalkyl, C 7-40  cycloalkylene, C 3-20  methoxy alkyl glycol ethers, C 3-20  alkyl glycol ethers, C 2-40  alkylene, C 3-40  alkyl lactone, and —R 7 —N(R 8 )—R 9 —; 
 R 7 , R 8  and R 9  are independently selected from the group consisting of C 1-20  alkyl, C 2-22  alkenyl, C 6-40  cycloalkyl, C 7-40  cycloalkylene and H; 
 m is an integral value ranging from 2 to 100 inclusive; 
 x is an integral value ranging from 1 to 1,000; and further wherein 
 no more than two of R 1 , R 2 , R 3  and R 4  are terminated with an hydroxyl group. 
 
       
     
     
         2 . The polymeric polyphosphite of  claim 1  wherein
 no more than one of R 1 , R 2 , R 3  and R 4  are terminated with an hydroxyl group. 
 
     
     
         3 . The polymeric polyphosphite of  claim 1  wherein
 essentially all of R 1 , R 2 , R 3  and R 4  are terminated by an alkyl group. 
 
     
     
         4 . The polymeric polyphosphite of  claim 1  wherein
 said polymeric polyphosphite is comprised of a polyalkylene glycol. 
 
     
     
         5 . The polymeric polyphosphite of  claim 4  wherein
 said polyalkylene glycol is selected from the group consisting of polyethylene glycol and polypropylene glycol. 
 
     
     
         6 . The polymeric polyphosphite of  claim 1  wherein
 each R 1 , R 2 , R 3  and R 4  are aliphatic and which further comprises an alkanolamine. 
 
     
     
         7 . An alkylphenol-free liquid polymeric polyphosphite which comprises: 
       
         
           
           
               
               
           
         
         wherein
 each R 1 , R 2 , R 3  and R 4  can be the same or different and independently selected from the group consisting of C 1-20  alkyl, C 2-22  alkenyl, C 6-40  cycloalkyl, C 7-40  cycloalkylene, C 3-20  methoxy alkyl glycol ethers, C 3-20  alkyl glycol ethers, and Y—OH as an end-capping group; 
 each Y is independently selected from the group consisting of C 1-20  alkyl, C 6-40  cycloalkyl, C 7-40  cycloalkylene, C 3-20  methoxy alkyl glycol ethers, C 3-20  alkyl glycol ethers, C 2-40  alkylene, C 2-40  C 3-40  alkyl lactone, and —R 7 —N(R 8 )—R 9 —; 
 R 7 , R 8  and R 9  are independently selected from the group consisting of C 1-20  alkyl, C 2-22  alkenyl, C 6-40  cycloalkyl, C 7-40  cycloalkylene and H previously defined for R 1 , R 2 , R 3  and R 4 , now further including H; 
 m is an integral value ranging from 2 to 100 inclusive; 
 x is an integral value ranging from 1 to 1,000; and further wherein 
 no more than two of R 1 , R 2 , R 3  and R 4  are difunctional having two reactive terminal groups and a remainder are monofunctional with one reactive terminal group. 
 
       
     
     
         8 . The polymeric polyphosphite of  claim 7  wherein
 no more than one of R 1 , R 2 , R 3  and R 4  is difunctional having two reactive terminal groups and a remainder are monofunctional with one reactive terminal group. 
 
     
     
         9 . The polymeric polyphosphite of  claim 8  wherein
 essentially all of R 1 , R 2 , R 3  and R 4  are terminated by an alkyl group. 
 
     
     
         10 . The polymeric polyphosphite of  claim 1  wherein
 said polymeric polyphosphite is comprised of a polyalkylene glycol. 
 
     
     
         11 . The polymeric polyphosphite of  claim 10  wherein
 said polyalkylene glycol is selected from the group consisting of polyethylene glycol and polypropylene glycol. 
 
     
     
         12 . The polymeric polyphosphite of  claim 1  wherein
 each R 1 , R 2 , R 3  and R 4  are aliphatic and which further comprises an alkanolamine. 
 
     
     
         13 . A process for stabilizing a polymer, as indicated by essentially matching or lowering the Yellowness Index of a polymer when compared to a polymeric composition using a tris(nonylphenyl) phosphite, comprising the step of adding an alkylphenol-free liquid polymeric polyphosphite which comprises: 
       
         
           
           
               
               
           
         
         wherein
 each R 1 , R 2 , R 3  and R 4  can be the same or different and independently selected from the group consisting of C 1-20  alkyl, C 2-22  alkenyl, C 3-40  cycloalkyl, C 3-40  cycloalkylene, C 3-20  methoxy alkyl glycol ethers, C 3-20  alkyl glycol ethers and Y—OH as an end-capping group; 
 each Y is independently selected from the group consisting of C 1-20  alkyl, C 6-40  cycloalkyl, C 7-40  cycloalkylene, C 3-20  methoxy alkyl glycol ethers, C 3-20  alkyl glycol ethers, C 2-40  alkylene, C 3-40  alkyl lactone, and —R 7 —N(R 8 )—R 9 —; 
 R 7 , R 8  and R 9  are independently selected from the group consisting of C 1-20  alkyl, C 2-22  alkenyl, C 6-40  cycloalkyl, C 7-40  cycloalkylene and H; 
 m is an integral value ranging from 2 to 100 inclusive; 
 x is an integral value ranging from 1 to 1,000; and 
 further wherein no more than two of R 1 , R 2 , R 3  and R 4  are terminated with an hydroxyl group. 
 
       
     
     
         14 . The polymeric polyphosphite of  claim 13  wherein
 no more than one of R 1 , R 2 , R 3  and R 4  are terminated with an hydroxyl group. 
 
     
     
         15 . The polymeric polyphosphite of  claim 13  wherein
 essentially all of R 1 , R 2 , R 3  and R 4  are terminated by an alkyl group. 
 
     
     
         16 . The polymeric polyphosphite of  claim 13  wherein
 said polymeric polyphosphite is comprised of a polyalkylene glycol. 
 
     
     
         17 . The polymeric polyphosphite of  claim 16  wherein
 said polyalkylene glycol is selected from the group consisting of polyethylene glycol and polypropylene glycol. 
 
     
     
         18 . The polymeric polyphosphite of  claim 13  wherein
 each R 1 , R 2 , R 3  and R 4  are aliphatic and which further comprises an alkanolamine. 
 
     
     
         19 . The process of  claim 13  which comprises:
 adding between 0.01-2 weight percent of said polymeric polyphosphite to at least one polymer. 
 
     
     
         20 . The process of  claim 16  wherein
 said polymer is a carbon-based polymer. 
 
     
     
         21 . The process of  claim 16  which further comprises the step of adding at least one other additive selected from the group consisting of
 a hindered phenol, a hindered amine light stabilizer, a benzotriazole, a thioester, a second phosphite, a metal stearate and a hydrotalcite. 
 
     
     
         22 . An alkylphenol-free liquid polymeric polyphosphite which comprises: 
       
         
           
           
               
               
           
         
         wherein
 each R 1 , R 2 , R 3 , R 4  and R 5  can be the same or different and independently selected from the group consisting of C 1-20  alkyl, C 2-22  alkenyl, C 3-40  cycloalkyl, C 3-40  cycloalkylene, C 3-20  methoxy alkyl glycol ethers, C 3-20  alkyl glycol ethers and A-OH and B—OH as an end-capping group; 
 each A and B is independently selected from the group consisting of C 2-40  alkylene, C 1-20  alkyl, C 6-40  cycloalkyl, C 7-40  cycloalkylene, C 3-20  methoxy alkyl glycol ethers, C 3-20  alkyl glycol ethers, C 3-40  alkyl lactone, and —R 7 —N(R 9 )—R 9 — wherein R 7 , R 9  and R 9  are independently selected from the group previously defined for R 1 , R 2 , R 3 , R 4  and R 5 ; 
 m and n are integral values ranging from 2 to 100 inclusive; 
 x is an integral value ranging from 1 to 1,000; and further wherein 
 no more than two of R 1 , R 2 , R 3 , R 4  and R 5  are terminated with an hydroxyl group. 
 
       
     
     
         23 . The polymeric polyphosphite of  claim 22  wherein
 no more than one of R 1 , R 2 , R 3 , R 4  and R 5  are terminated with an hydroxyl group. 
 
     
     
         24 . The polymeric polyphosphite of  claim 23  wherein
 essentially all of R 1 , R 2 , R 3 , R 4  and R 5  are terminated by an alkyl group. 
 
     
     
         25 . The polymeric polyphosphite of  claim 22  wherein
 said polymeric polyphosphite is comprised of a polyalkylene glycol. 
 
     
     
         26 . The polymeric polyphosphite of  claim 25  wherein
 said polyalkylene glycol is selected from the group consisting of polyethylene glycol and polypropylene glycol. 
 
     
     
         27 . The polymeric polyphosphite of  claim 22  wherein
 each R 1 , R 2 , R 3 , R 4  and R 5  are aliphatic and which further comprises an alkanolamine. 
 
     
     
         28 . A process to control the molecular weight and hydroxyl termination of an alkylphenol-free liquid polymeric polyphosphite of formula (IV) 
       
         
           
           
               
               
           
         
       
       wherein
 each R 1 , R 2 , R 3  and R 4  can be the same or different and independently selected from the group consisting of C 1-20  alkyl, C 2-22  alkenyl, C 3-40  cycloalkyl, C 3-40  cycloalkylene, C 3-20  methoxy alkyl glycol ethers, C 3-20  alkyl glycol ethers and Y—OH as an end-capping group; 
 each Y is independently selected from the group consisting of C 1-20  alkyl, C 6-40  cycloalkyl, C 7-40  cycloalkylene, C 3-20  methoxy alkyl glycol ethers, C 3-20  alkyl glycol ethers, C 2-40  alkylene, C 3-40  alkyl lactone, and —R 7 —N(R 8 )—R 9 —; 
 R 7 , R 8  and R 9  are independently selected from the group consisting of C 1-20  alkyl, C 2-22  alkenyl, C 6-40  cycloalkyl, C 7-40  cycloalkylene and H; 
 m is an integral value ranging from 2 to 100 inclusive; 
 x is an integral value ranging from 1 to 1,000; and 
 further wherein no more than two of R 1 , R 2 , R 3  and R 4  are terminated with an hydroxyl group 
 comprising the steps of:
 reacting a triphosphite with a limiting molar amount of a dihydroxy-terminated reactant with a molar excess of a monofunctional chain stopper; 
 adding a base; 
 heating said triphosphite, dihydroxy-terminated reactant and monofunctional chain stopper and base; and 
 isolating said alkylphenol-free liquid polymeric polyphosphite. 
 
 
     
     
         29 . The alkylphenol-free liquid polymeric polyphosphite of  claim 28  wherein
 said triphosphite comprises a triphenylphosphite; 
 said dihydroxy-terminated reactant comprises at least one polyalkylene glycol; and 
 said monofunctional chain stopper comprises at least one alcohol group. 
 
     
     
         30 . A process to control the molecular weight and hydroxyl termination of an alkylphenol-free liquid polymeric polyphosphite of formula 
       
         
           
           
               
               
           
         
         wherein
 each R 1 , R 2 , R 3 , R 4  and R 5  can be the same or different and independently selected from the group consisting of C 1-20  alkyl, C 2-22  alkenyl, C 3-40  cycloalkyl, C 3-40  cycloalkylene, C 3-20  methoxy alkyl glycol ethers, C 3-20  alkyl glycol ethers and A-OH and B—OH as an end-capping group; 
 each A and B is independently selected from the group consisting of C 2-40  alkylene, C 1-20  alkyl, C 6-40  cycloalkyl, C 7-40  cycloalkylene, C 3-20  methoxy alkyl glycol ethers, C 3-20  alkyl glycol ethers, C 3-40  alkyl lactone, and —R 7 —N(R 9 )—R 9 — wherein R 7 , R 9  and R 9  are independently selected from the group previously defined for R 1 , R 2 , R 3 , R 4  and R 5 ; 
 m and n are integral values ranging from 2 to 100 inclusive; 
 x is an integral value ranging from 1 to 1,000; and further wherein 
 no more than two of R 1 , R 2 , R 3 , R 4  and R 5  are terminated with an hydroxyl group. 
 
         comprising the steps of:
 reacting a triphosphite with a limiting molar amount of at least two dihydroxy-terminated reactants with a molar excess of a monofunctional chain stopper; 
 adding a base; 
 heating said triphosphite, at least two dihydroxy-terminated reactants and monofunctional chain stopper and base; and 
 isolating said alkylphenol-free liquid polymeric polyphosphite. 
 
       
     
     
         31 . The alkylphenol-free liquid polymeric polyphosphite of  claim 30  wherein
 said triphosphite comprises a triphenylphosphite; 
 said dihydroxy-terminated reactant comprises at least two polyalkylene glycols; and 
 said monofunctional chain stopper comprises at least one alcohol group.