IP Library Granted Patent US 8,906,961
Granted Patent B2
US 8,906,961 · App. 13/941,687 · Granted Dec 9, 2014

Glycerol levulinate ketals and their use in the manufacture of polyurethanes, and polyurethanes formed therefrom

Inventor: Sergey Selifonov (Plymouth, MN)
Assignee: Segetis, Inc.
C08G18/4283C07D493/08C07D317/30C07D493/18
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Quick Facts
Patent No.
US 8,906,961
App. No.
13/941,687
Granted
Dec 9, 2014
Kind
B2
Abstract

The present disclosure relates to the preparation of ketal compounds from glycerol and levulinic acid and esters, and uses thereof, in particular the manufacture of polyurethanes.

Claims (46)

1. A plasticizer composition comprising:

i) a first plasticizer having the formula:

wherein R 3 is a linear, branched, or cyclic alkyl or alkenyl, aryl, aralkyl, or alkyloxyalkyl, and R 6 is hydrogen, or is a linear, branched, or cyclic alkyl or alkenyl, aryl, aralkyl, alkyloxyalkyl, or oxoalkyl; and

ii) a second plasticizer selected from aromatic dicarboxylic esters, aliphatic dicarboxylic esters, epoxidized triglycerides, or a combination thereof.

2. The plasticizer composition of claim 1 , wherein R 3 and R 6 are each independently selected from linear or branched alkyls having between 1 and 23 carbons.

3. The plasticizer composition of claim 1 , wherein R 3 and R 6 are each independently selected from linear or branched alkyls having between 1 and 12 carbons.

4. A polymer composition comprising:

i) a base polymer; and

ii) a plasticizer composition comprising:

1) a first plasticizer having the formula:

wherein R 3 is a linear, branched, or cyclic alkyl or alkenyl, aryl, aralkyl, or alkyloxyalkyl, and R 6 is hydrogen, or is a linear, branched, or cyclic alkyl or alkenyl, aryl, aralkyl, alkyloxyalkyl, or oxoalkyl; and

2) a second plasticizer selected from aromatic dicarboxylic esters, aliphatic dicarboxylic esters, epoxidized triglycerides, or a combination thereof.

5. The polymer composition of claim 4 , wherein the base polymer is selected from vinyl chloride polymer, poly(3-hydroxyalkanoate) polymer, poly(lactate) polymer, or polysaccharide polymer.

6. The polymer composition of claim 4 , wherein R 3 and R 6 are each independently selected from linear or branched alkyls having between 1 and 23 carbons.

7. The polymer composition of claim 4 , wherein R 3 and R 6 are each independently selected from linear or branched alkyls having between 1 and 12 carbons.

8. The polymer composition of claim 4 , wherein the base polymer is a vinyl chloride polymer.

9. The polymer composition of claim 4 , wherein the first plasticizer having the formula:

comprises between 5 and 80% by weight of the polymer composition.

10. The polymer composition of claim 9 , wherein the plasticizer having the formula:

comprises between 5 and 25% by weight of the polymer composition.

11. The polymer composition of claim 4 , wherein the base polymer comprises poly(vinyl chloride) homopolymer or copolymer, a poly(3-hydroxyalkanoate) homopolymer or copolymer, poly(3-hydroxybutyrate), poly(lactate), or polysaccharide homopolymer or copolymer.

12. The polymer composition of claim 4 , further comprising one or more additives comprising a stabilizer, an inorganic or organic filler, reinforcing fibers, pigments, and dyes.

13. The polymer composition of claim 4 , wherein the composition is cast, molded, or extruded into a shape.

14. The polymer composition of claim 13 , wherein the shape comprises film, fiber, tubing, or pipe.

15. A fragrance formulation comprising:

i) a fragrance; and

ii) a compound having the formula:

wherein R 3 is a linear, branched, or cyclic alkyl or alkenyl, aryl, aralkyl, or alkyloxyalkyl, and R 6 is hydrogen, or is a linear, branched, or cyclic alkyl or alkenyl, aryl, aralkyl, alkyloxyalkyl, or oxoalkyl.

16. The fragrance formulation of claim 15 , wherein R 3 and R 6 are each independently selected from linear or branched alkyls having between 1 and 23 carbons.

17. The fragrance formulation of claim 15 , wherein R 3 and R 6 are each independently selected from linear or branched alkyls having between 1 and 12 carbons.

18. A biologically active formulation comprising:

i) a biologically active agent; and

ii) a compound having the formula:

wherein R 3 is a linear, branched, or cyclic alkyl or alkenyl, aryl, aralkyl, or alkyloxyalkyl, and R 6 is hydrogen, or is a linear, branched, or cyclic alkyl or alkenyl, aryl, aralkyl, alkyloxyalkyl, or oxoalkyl.

19. The biologically active formulation of claim 18 , wherein R 3 and R 6 are each independently selected from linear or branched alkyls having between 1 and 23carbons.

20. The biologically active formulation of claim 18 , wherein R 3 and R 6 are each independently selected from linear or branched alkyls having between 1 and 12carbons.

21. A plasticizer composition comprising:

i) a first plasticizer having the formula:

wherein R 3 is a linear, branched, or cyclic alkyl or alkenyl, aryl, aralkyl, or alkyloxyalkyl, and R 6 is hydrogen, or is a linear, branched, or cyclic alkyl or alkenyl, aryl, aralkyl, alkyloxyalkyl, or oxoalkyl; and

ii) a second plasticizer different from the first plasticizer.

22. A polymer composition comprising:

i) a base polymer; and

ii) a plasticizer composition comprising:

1) a first plasticizer having the formula:

wherein R 3 is a linear, branched, or cyclic alkyl or alkenyl, aryl, aralkyl, or alkyloxyalkyl, and R 6 is hydrogen, or is a linear, branched, or cyclic alkyl or alkenyl, aryl, aralkyl, alkyloxyalkyl, or oxoalkyl; and

2) a second plasticizer different from the first plasticizer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 7, 2016
From: SEGETIS, INC.
To: GFBIOCHEMICALS LIMITED
Reel/Frame 038373/0362 →
Continuity (5)
Continuation 13445297 · Apr 12, 2012
Continuation 13184064 · Jul 15, 2011
Division 11915549
Provisional Application 60738988 · Nov 22, 2005
Related Publication 20130303648A1 · Nov 14, 2013