ALKYLPHENOL FREE - LIQUID POLYMERIC POLYPHOSPHITE POLYMER STABILIZERS
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.
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.