IP Library Granted Patent US 8,865,802
Granted Patent B2
US 8,865,802 · App. 13/892,227 · Granted Oct 21, 2014

Chemical modification of lignin and lignin derivatives

Inventors: Nhiem Cao (Fort Smith, AR); Kevin Oden (Fayetteville, AR); Wolfgang G. Glasser (Richmond, VA)
Assignee: Cyclewood Solutions, Inc.
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Quick Facts
Patent No.
US 8,865,802
App. No.
13/892,227
Granted
Oct 21, 2014
Kind
B2
Abstract

In one example implementation, a trans-esterified APL can include an APL and a polyester including polyester chains. The polyester may be an aliphatic polyester, a semi-aromatic polyester, or an aromatic polyester. In other examples, an acetate ester of the APL can be used to swap carboxylic acid groups with the alcohol oligomer units in the polyester chains.

Claims (40)

1. A trans-esterified acetyoxypropyl lignin (APL) comprising:

an APL; and

a polyester including polyester chains.

2. The trans-esterified APL of claim 1 , wherein the polyester is an aliphatic polyester, a semi-aromatic polyester, or an aromatic polyester.

3. The trans-esterified APL of claim 1 , wherein an acetate ester of the APL is used to swap carboxylic acid groups with alcohol oligomer units in the polyester chains.

4. The trans-esterified APL of claim 1 , wherein polyester oligomer units are covalently-bonded to the APL while one or more of the polyester chains are shortened and terminated with acetate esters.

5. The trans-esterified APL of claim 1 , wherein the trans-esterified APL is represented by the formula R′COOR, wherein R′ represents the APL and R represents the polyester.

6. The trans-esterified APL of claim 1 , wherein transesterification occurs with the replacement of one alcohol group in the ester by another different alcohol group.

7. A trans-esterified acetyoxypropyl lignin (APL) blend comprising:

a APL; and

a polyester including polyester chains; and

one or more additives.

8. The trans-esterified APL blend of claim 7 , wherein the one or more additives are selected from the group consisting of catalysts, compatibilizers, odor neutralizers, fragrances, and process aids.

9. The trans-esterified APL blend of claim 7 , further comprising:

a plasticizer.

10. The trans-esterified APL blend of claim 9 , wherein the plasticizer reduces a glass transition temperature of the trans-esterified APL.

11. The trans-esterified APL blend of claim 7 , wherein the trans-esterified APL blend comprises by weight:

1% to 99% of the APL;

1% to 99% of the polyester; and

less than 50% of the one or more additives.

12. The trans-esterified APL blend of claim 9 , wherein the trans-esterified APL is represented by the formula R′COOR, wherein R′ represents the APL and R represents the polyester.

13. The trans-esterified APL blend of claim 9 , wherein an alkyl ester of the APL is used to swap carboxylic acid groups with an alcohol terminated segment in the polyester chains.

14. A non-trans-esterified acetyoxypropyl lignin (APL) blend comprising:

an APL; and

a non-trans-esterified polymer.

15. The non-trans-esterified APL blend of claim 14 , further comprising:

one or more additives, wherein the one or more additives are selected from the group consisting of catalysts, compatibilizers, odor neutralizers, fragrances, and process aids.

16. The non-trans-esterified APL blend of claim 14 , further comprising:

a plasticizer.

17. The non-trans-esterified APL blend of claim 16 , wherein the plasticizer reduces a glass transition temperature of the non-trans-esterified APL.

18. The non-trans-esterified APL blend of claim 14 , wherein the non-trans-esterified APL blend comprises by weight:

the APL in the range of 1% to 99%;

the non-trans-esterified polymer in the range of 1% to 99%; and

one or more additives in the range of 0% to 50%.

19. The non-trans-esterified APL blend of claim 14 , wherein the non-trans-esterified APL blend comprises by weight:

the APL in the range of about 1% to about 99%;

the non-trans-esterified polymer in the range of about 1% to about 99%;

one or more additives in the range of about 0% to about 50%; and

a plasticizer in the range of about 0% to about 50%.

20. The non-trans-esterified APL blend of claim 14 , wherein the non-trans-esterified polymer is selected from the group consisting of polyolefins, polyesters, amides, urethanes, acrylics and polysaccharides.

Assignments (3)
ASSIGNMENT OF SELLER'S INTEREST IN ASSIGNED ASSETS Recorded Jun 24, 2016
From: COMERICA BANK
To: WEISS, ROBERT
Reel/Frame 039153/0236 →
SECURITY INTEREST Recorded Jun 17, 2014
From: CYCLEWOOD SOLUTIONS, INC.
To: COMERICA BANK, A TEXAS BANKING ASSOCIATION
Reel/Frame 033186/0943 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 30, 2013
From: CAO, NHIEM; ODEN, KEVIN; GLASSER, WOLFGANG G.; MCKELLAR, BERNARD ROBERT
To: CYCLEWOOD SOLUTIONS, INC.
Reel/Frame 030518/0010 →
Continuity (2)
Provisional Application 61646149 · May 11, 2012
Related Publication 20130303667A1 · Nov 14, 2013