IP Library Granted Patent US 8,258,215
Granted Patent B2
US 8,258,215 · App. 12/701,121 · Granted Sep 4, 2012

Mixed alkyl-alkylaryl-phenyl phosphite polymer additive

Assignee: Dover Chemical Corporation
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Quick Facts
Patent No.
US 8,258,215
App. No.
12/701,121
Granted
Sep 4, 2012
Kind
B2
Abstract

A process to stabilize a polymer is described utilizing the step of adding a phosphite reaction product of a triphenyl phosphite or lower molecular weight trialkyl phosphite (e.g., trimethyl phosphite) or triaryl phosphite, with from approximately 1 to 2 moles of preferably a paracumyl phenol, and with from approximately 1 to 2 moles of at least C 12-20 carbon alkyl or C 12-20 alkenyl alcohol. In one embodiment of the invention, the phosphite reaction product is formula (I) wherein R 1 is independently selected from the group consisting of H and C 1-2 alkyls; R 2 is independently selected from the group defined previously for R 1 ; x is an integral value ranging from 0 to 4 inclusive; y is an integral value ranging from 0 to 4 inclusive; n is an integral value ranging from 1 to 2; R 3 is independently selected from the group consisting of C 12-20 alkyl or C 12-20 alkenyl; R 4 is independently selected from the group consisting of C 1-10 , alkyl and C 9-15 arylalkyl; R 5 is independently selected from the group defined previously for R 4 .

Claims (53)

1. A process to stabilize a polymer comprising the step of adding a phosphite of formula (I), said phosphite having less estrogenic activity when compared to polymer blends which use tris(nonylphenyl) phosphite:

wherein

R 1 is independently selected from the group consisting of H and C 1-2 alkyls;

R 2 is independently selected from the group defined previously for R 1 ;

x is an integral value ranging from 0 to 4 inclusive;

y is an integral value ranging from 0 to 4 inclusive;

n is an integral value ranging from 1 to 2;

R 3 is independently selected from the group consisting of C 12-20 alkyl or C 12-20 alkenyl;

R 4 is independently selected from the group consisting of C 1-10 ; alkyl and C 9-15 arylalkyl;

R 5 is independently selected from the group defined previously for R 4 .

2. The process of claim 1 wherein

formula (I) is as illustrated in formula (II) and comprises a combination of monophosphites and diphosphites illustrated below,

wherein

R 6 is selected from the group consisting of C 12-18 alkyl and C 12-18 alkenyl; and

n is 1 or 2.

3. The process of claim 1 wherein formula (I) comprises a combination of monophosphites and diphosphites of C 12-14 alkyl, p-cumylphenyl phosphites illustrated below

wherein

a is 1 or 2.

4. The process of claim 1 wherein formula (I) comprises a combination of monophosphites and diphosphites of C 18 alkenyl, p-cumylphenyl phosphates illustrated below

wherein

a is 1 or 2.

5. The process of claim 1 wherein formula (I) comprises a combination of monophosphites and diphosphites of C 12-14 alkyl, p-cumylphenyl phosphites illustrated below

wherein

a is 1 or 2.

6. The process of claim 1 wherein formula (I) comprises a combination of monophosphites and diphosphites of C 16-18 alkyl, p-cumylphenyl phosphites illustrated below

wherein

a is 1 or 2.

7. The process of claim 1 wherein formula (I) comprises a combination of monophosphites and diphosphites of C 12-18 alkyl, p-cumylphenyl phosphites illustrated below

wherein

a is 1 or 2.

8. The process of claim 1 wherein formula (I) comprises a combination of monophosphites and diphosphites of C 18 alkenyl, p-cumylphenyl phosphites illustrated below

wherein

a is 1 or 2.

9. The process of claim 1 wherein formula (I) comprises a combination of monophosphites and diphosphites of C 14-15 alkyl, p-cumylphenyl phosphites illustrated below

wherein

a is 1 or 2.

10. The process of claim 1 wherein formula (I) comprises a combination of monophosphites and diphosphites of C 12-14 alkyl, p-cumylphenyl phosphites illustrated below

wherein

a is 1 or 2.

11. The process of claim 1 wherein formula (I) comprises a combination of monophosphites and diphosphites of C 16-18 alkyl, tripropylene glycol, p-cumylphenyl phosphites illustrated below

wherein

b is 1 or 2;

c is 0.5 or 1;

d is 0.5 or 1;

and further wherein b+c+d=3.

12. The process of claim 1 wherein

said polymer is selected from the group consisting of polyolefins, polyvinyl chloride and SBR rubbers.

13. The process of claim 12 wherein

said polyolefin is selected from the group consisting of high density polyethylene, medium density polyethylene, low density polyethylene, linear low density polyethylene and polypropylene.

14. The process of claim 1 wherein

said phosphites are added at a level of between 0.01 to 2% by weight of said polymer.

15. The process of claim 14 wherein

said phosphites perform in a manner which is similar to tris(nonylphenyl) phosphite in said polymers, yet provide less estrogenic activity when compared to polymers which use tris(nonylphenyl) phosphite.

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 Jun 25, 2010
From: JAKUPCA, MICHAEL; LANCE, JACOB M.; BERSAGLINI, NINA; STEVENSON, DONALD
To: DOVER CHEMICAL CORPORATION
Reel/Frame 024593/0085 →
Continuity (1)
Related Publication 20110196079A1 · Aug 11, 2011