IP Library Granted Patent US 9,884,838
Granted Patent B2
US 9,884,838 · App. 15/223,925 · Granted Feb 6, 2018

Stabilized levulinic ester ketals

Inventors: Brian D. Mullen (Delano, MN); Vivek Badarinarayana (St. Louis Park, MN); Eric S. Hall (Plymouth, MN); Matthew J. Tjosaas (Minneapolis, MN); Cora M. Leibig (Maple Grove, MN)
Assignee: GFBIOCHEMICALS LIMITED
C07D317/30C09D7/125
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Quick Facts
Patent No.
US 9,884,838
App. No.
15/223,925
Granted
Feb 6, 2018
Kind
B2
Abstract

The invention describes methods of preparation and compositions of plasticizers. The plasticizers include at least 2 alkyl ketal ester moieties and have a molecular weight of greater than 300. In one aspect, the alkyl ketal ester moieties are levulinic ester ketals. Certain compositions contain at least one of an antioxidant, a UV stabilizer, a thermal stabilizer or mixtures thereof, present in the composition from about 0.01 to about 5.0 percent by weight of the total composition.

Claims (35)

1. A process to prepare a plasticizer, wherein the plasticizer has a molecular weight of greater than 300 with at least 2 alkyl ketal ester moieties, comprising the step:

contacting under reaction conditions, an alkyl ketal ester, a multihydric hydrocarbyl moiety, or a monohydric alkyl ketal ester; a catalyst; an antioxidant; and optionally a thermal stabilizer or mixtures thereof.

2. The process of claim 1 , wherein the plasticizer has a formula comprising:

or

combinations thereof, wherein

each a, independently, is selected from 0 or an integer of 1 to 12;

each b, independently, is 0 or 1;

c is from 0 to 12;

d is 0 or 1;

each e, independently, is from 0 to 12;

each f, independently, is from 0 to 12;

each i is 0 or 1;

each j, independently, is 0 to 100;

each R 1 , independently, is a hydrogen, a hydrocarbyl group, or a substituted hydrocarbyl group;

each R 2 , R 3 and R 4 are independently methylene, alkylmethylene, or dialkylmethylene;

R 5 is a hydrogen or

R 6 is a hydrocarbyl group or a substituted hydrocarbyl group;

each R 7 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 8 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 10 , independently, is a hydrocarbyl or a substituted hydrocarbyl group;

R 11 is a hydrocarbyl group, or a substituted hydrocarbyl group;

R 12 , is a covalent bond, a hydrocarbyl group or a substituted hydrocarbyl group;

each R 14 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 15 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 19 , independently, is a hydrocarbyl group, a substituted hydrocarbyl group, or a hydrocarbyl group substituted with up to 5 hydroxyl groups;

each R 23 is a hydrocarbyl group or substituted hydrocarbyl group having between 1 and 12 carbon atoms

each Z, independently, is —O—, —NH— or —NR— where R is a hydrocarbyl or a substituted hydrocarbyl group;

n is from 1 to 100;

s is at least one;

v is from 0 to 100;

w is from 1 to 100;

x is at least 1;

y is 0 or a positive number.

3. The process of claim 2 , wherein the plasticizer is the compound of formula (IV) wherein R 11 is a C4 alkyl.

4. The process of claim 3 , wherein each a=2 and each b=0.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 30, 2017
From: MULLEN, BRIAN D.; BADARINARAYANA, VIVEK; HALL, ERIC S.; TJOSAAS, MATTHEW J.; LEIBIG, CORA M.
To: SEGETIS, INC.
Reel/Frame 042878/0516 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 30, 2017
From: SEGETIS, INC.
To: GFBIOCHEMICALS LIMITED
Reel/Frame 042878/0605 →
Continuity (3)
Division 13648252 · Oct 9, 2012
Provisional Application 61545849 · Oct 11, 2011
Related Publication 20160332983A1 · Nov 17, 2016