IP Library Granted Patent US 8,563,637
Granted Patent B2
US 8,563,637 · App. 12/907,343 · Granted Oct 22, 2013

Alkylphenol free-liquid polymeric phosphite polymer stabilizers

Inventors: Michael Jakupca (Canton, OH); Jacob M. Lance (Dover, OH); Donald Stevenson (Dover, OH)
Assignee: Dover Chemical Corporation
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Quick Facts
Patent No.
US 8,563,637
App. No.
12/907,343
Granted
Oct 22, 2013
Kind
B2
Abstract

An alkylphenol-free liquid polymeric phosphite 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 3-22 alkenyl, C 6-40 cycloalkyl, C 7-40 cycloalkylene, C 1-20 methoxy alkyl glycol ethers, C 1-20 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. The alkylphenol-free liquid polymeric phosphite is useful in reducing phosphite migration within polymers.

Claims (98)

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 12-20 alkyl, C 12-22 alkenyl, C 12-40 cycloalkyl, C 12-40 cycloalkylene, C 12-20 methoxy 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 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; and

x is an integral value ranging from 1 to 1,000, and

further wherein said polymeric polyphosphite is a reaction product of:

at least one monohydroxy-terminated reactant selected from the group consisting of R 1 —OH, R 2 —OH, R 3 —OH and R 4 —OH; and

at least one dihydroxy-terminated reactant selected from the group HO—Y—OH, and

a trifunctional reactant comprising at least one phosphorus moiety,

said polymeric polyphosphite having less terminal hydroxy groups than said reaction product formed using dihydroxy-terminated reactants.

2. The polymeric polyphosphite of claim 1 wherein

said polymeric polyphosphite is not based on either an aromatic phenol or an alkylphenol.

3. The polymeric polyphosphite of claim 1 wherein

said polymeric polyphosphite is comprised of a polyalkylene glycol.

4. The polymeric polyphosphite of claim 3 wherein

said polyalkylene glycol is selected from the group consisting of polyethylene glycol and polypropylene glycol.

5. The polymeric polyphosphite of claim 1 wherein

each R 1 , R 2 , R 3 and R 4 are aliphatic, and wherein said polymeric polyphosphite further comprises

an alkanolamine.

6. 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 which does not include the addition of a tris(nonylphenyl) phosphite or the liquid polymeric polyphosphite of formula (IV), 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 12-20 alkyl, C 12-22 alkenyl, C 12-40 cycloalkyl, C 12-40 cycloalkylene, C 12-20 methoxy 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 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 cycloalkenyl and 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 wherein said polymeric polyphosphite is a reaction product of:

at least one monohydroxy-terminated reactantselected from the group consisting of R 1 —OH, R 2 —OH, R 3 —OH and R 4 —OH; and

at least one dihydroxy-terminated reactantselected from the group HO—Y—OH, and

a trifunctional reactant comprising at least one phosphorus moiety,

said polymeric polyphosphite having less terminal hydroxy groups than said reaction product formed using dihydroxy-terminated reactants.

7. The process of claim 6 wherein

said polymeric polyphosphite is not based on either an aromatic phenol or an alkylphenol.

8. The process of claim 6 wherein

said polymeric polyphosphite is comprised of a polyalkylene glycol.

9. The process of claim 8 wherein

said polyalkylene glycol is selected from the group consisting of polyethylene glycol and polypropylene glycol.

10. The process of claim 6 wherein

each R 1 , R 2 , R 3 and R 4 are aliphatic; and wherein said polymeric polyphosphite further comprises

an alkanolamine.

11. The process of claim 6 which comprises:

adding between 0.01-2 weight percent of said polymeric polyphosphite to at least one polymer.

12. The process of claim 11 wherein

said polymer is a carbon-based polymer.

13. The process of claim 11 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.

14. 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 12-20 alkyl, C 12-22 alkenyl, C 12-40 cycloalkyl, C 12-40 cycloalkylene, C 12-20 methoxy 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 2-40 alkylene, C 3-20 alkyl glycol ethers, 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; and

x is an integral value ranging from 1 to 1,000, and

further wherein said polymeric polyphosphite is a reaction product of:

at least one monohydroxy-terminated reactantselected from the group consisting of R 1 —OH, R 2 —OH, R 3 —OH and R 4 —OH; and

at least one dihydroxy-terminated reactantselected from the group HO—Y—OH; and

a trifunctional reactant comprising at least one phosphorus moiety,

said polymeric polyphosphite having less terminal hydroxy groups than said reaction product formed using dihydroxy-terminated reactants.

15. The polymeric polyphosphite of claim 14 wherein

said polymeric polyphosphite is not based on either an aromatic phenol or an alkylphenol.

16. The polymeric polyphosphite of claim 14 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 14 wherein

each R 1 , R 2 , R 3 and R 4 are aliphatic and wherein said polymeric polyphosphite further comprises

an alkanolamine.

19. The polymeric polyphosphite of claim 1 wherein

said polymeric polyphosphite has a weight % P ranging from approximately 3.7% to 8.9%.

20. The polymeric polyphosphite of claim 19 wherein

said trifunctional reactant comprising at least one phosphorus moiety is aromatic.

21. The polymeric polyphosphite of claim 6 wherein

said polymeric polyphosphite has a weight % P ranging from approximately 3.7% to 8.9%.

22. The polymeric polyphosphite of claim 21 wherein

said trifunctional reactant comprising at least one phosphorus moiety is aromatic.

23. The polymeric polyphosphite of claim 14 wherein

said polymeric polyphosphite has a weight % P ranging from approximately 3.7% to 8.9%.

24. The polymeric polyphosphite of claim 23 wherein

said trifunctional reactant comprising at least one phosphorus moiety is aromatic.

25. A process for making 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 12-20 alkyl, C 12-22 alkenyl, C 12-40 cycloalkyl, C 12-40 cycloalkylene, C 12-20 methoxy 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 2-40 alkylene, C 3-20 alkyl glycol ethers, 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; and

x is an integral value ranging from 1 to 1,000, and

further wherein said steps comprise:

adding at least one monohydroxy-terminated reactant selected from the group consisting of R 1 —OH, R 2 —OH, R 3 —OH and R 4 —OH; and

adding at least one dihydroxy-terminated reactantselected from the group HO—Y—OH; and

adding a trifunctional reactant comprising at least one aromatic phosphorus moiety.

26. The process of claim 25 which further comprises the step of:

adding an alkanolamine.

27. The process of claim 25 which further comprises the step of:

adding a carbon-based polymer.

28. The process of claim 27 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, an alkanolamine, a metal stearate and a hydrotalcite.

Assignments (3)
SECURITY INTEREST Recorded Jan 19, 2017
From: DOVER CHEMICAL CORPORATION
To: WELLS FARGO BANK, NATIONAL ASSOCIATION
Reel/Frame 041021/0849 →
SECURITY AGREEMENT Recorded Mar 10, 2011
From: DOVER CHEMICAL CORPORATION; KEIL CHEMICAL CORPORATION
To: THE HUNTINGTON NATIONAL BANK
Reel/Frame 025921/0382 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 3, 2011
From: JAKUPCA, MICHAEL; LANCE, JACOB M.; STEVENSON, DONALD
To: DOVER CHEMICAL CORPORATION
Reel/Frame 025738/0490 →
Continuity (2)
Provisional Application 61306014 · Feb 19, 2010
Related Publication 20110263760A1 · Oct 27, 2011