Dialkyl 2, 5-furandicarboxylate plasticizers and plasticized polymeric compositions

Patent metadata

Field	Value
Publication number	US-9938423-B2
Application number	US-201414782211-A
Country	US
Kind code	B2
Filing date	May 12, 2014
Priority date	May 29, 2013
Publication date	Apr 10, 2018
Grant date	Apr 10, 2018

Abstract

Plasticizers comprising a dialkyl 2,5-furandicarboxylate and plasticized polymeric compositions comprising such plasticizers. Such plasticized polymeric compositions can be employed in forming various articles of manufacture, such as coated conductors.

First claim

The invention claimed is:

1. A phthalate-free plasticizer, comprising:
a first plasticizer component consisting of dialkyl 2,5-furandicarboxylate having the structure

wherein R 1 and R 2 are independently selected from 2-ethylhexyl groups, octyl groups, decyl groups, dodecyl groups, isotridecyl groups, and tridecyl groups; and
(ii) from 50 wt % to 90 wt % of a second plasticizer component selected from the group consisting of an epoxidized soybean oil, an epoxidized fatty acid methyl ester, and combinations thereof, based on the entire weight of the plasticizer,
wherein said plasticizer is a liquid at 22° C. and 1 atmosphere of pressure.

2. The plasticizer of claim 1 , wherein R 1 and R 2 each is a 2-ethylhexyl group.

3. The plasticizer of claim 1 , wherein said first plasticizer component and said second plasticizer component are present in a weight ratio of 1:1.

4. The plasticizer of claim 1 , wherein the second plasticizer component is the epoxidized soybean oil.

5. The plasticizer of claim 1 , wherein the second plasticizer component is the epoxidized fatty acid methyl ester.

6. A plasticized polymeric composition, comprising:
a polyvinyl chloride; and
a plasticizer according to claim 1 .

7. The composition of claim 6 , wherein said plasticizer is present in an amount ranging from 10 to 80 weight percent, based on the entire weight of said plasticized polymeric composition, wherein said polymer is present in an amount ranging from 20 to 90 weight percent, based on the entire weight of said plasticized polymeric composition.

8. A coated conductor comprising a conductive core and a polymeric layer surrounding at least a portion of said conductive core, wherein said plasticized polymeric composition of claim 6 constitutes said polymeric layer.

9. The plasticizer of claim 1 , wherein the plasticizer is devoid of trimellitates.

10. The plasticizer of claim 1 consisting of the first plasticizer component and the second plasticizer component.

11. The plasticizer of claim 1 , wherein R 1 and R 2 each is an isotridecyl group.

12. The plasticizer of claim 1 , wherein R 1 and R 2 are a mixture of 2-ethylhexyl groups, octyl groups, and decyl groups.

13. The plasticizer of claim 1 , wherein R 1 and R 2 are independently selected from 2-ethylhexyl groups, octyl groups, decyl groups, and isotridecyl groups; and
the second plasticizer component is the epoxidized soybean oil.

14. The composition of claim 6 , comprising:
from 50 wt % to 65 wt % of the polymer; and
from 25 wt % to 35 wt % of the plasticizer, based on the entire weight of the plasticized polymeric composition.

15. The composition of claim 14 wherein the first plasticizer is bis(2-ethylhexyl) 2,5-furancarboxylate, the second plasticizer component is epoxidized soybean oil; and
the composition has a tensile elongation retention from 54% to 79% after aging at 136° C. for 168 hours.

16. The composition of claim 14 wherein R 1 and R 2 of the first plasticizer component are a mixture of 2-ethylhexyl groups, octyl groups, and decyl groups;
the second plasticizer is epoxidized soybean oil; and
the composition has a tensile elongation retention from 73% to 87% after aging at 136° C. for 168 hours.

17. The composition of claim 14 wherein the first plasticizer is bis(diisotridecyl) 2,5 furancarboxylate and the second plasticizer is epoxidized soybean oil.

18. The composition of claim 14 wherein the first plasticizer is bis(diisotridecyl) 2,5 furancarboxylate and the second plasticizer is epoxidized fatty acid methyl ester.

Assignees

• Dow Global Technologies Llc

Inventors

• Chaudhary Bharat I

Classifications

• H01B3/443

  from vinylhalogenides or other halogenoethylenic compounds · CPC title

• C08K5/1535

  Five-membered rings · CPC title

• C07D303/48

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals · CPC title

• C08K5/1515

  Three-membered rings · CPC title

• C08L27/06

  Homopolymers or copolymers of vinyl chloride · CPC title