IP Library Granted Patent US 8,158,731
Granted Patent B2
US 8,158,731 · App. 12/694,426 · Granted Apr 17, 2012

Biopolymer compositions having improved flexibility

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Quick Facts
Patent No.
US 8,158,731
App. No.
12/694,426
Granted
Apr 17, 2012
Kind
B2
Abstract

The present disclosure is directed to polymer blends comprising a biopolymer and a substituted or unsubstituted aliphatic polyester. The aliphatic polyester comprises repeating units derivable from a substituted or unsubstituted aliphatic diacid, repeating units derivable from a substituted or unsubstituted aliphatic diol, and one or two terminator units derivable from a substituted or unsubstituted aliphatic alcohol. The polymer blends disclosed herein provide improved flexibility, and are useful, for example, in the production of packaging materials, industrial products, durable goods, and the like.

Claims (35)

1. A method for increasing the flexibility of a biopolymer comprising mixing a biopolymer and a compatible polyester to form a polymer blend, wherein the polyester comprises repeating units derivable from succinic acid, repeating units derivable from a substituted or unsubstituted C 2 to C 20 aliphatic diol, and one or two terminator units derivable from a substituted or unsubstituted C 1 to C 20 aliphatic alcohol;

wherein the polyester is present in an amount of about 5 to about 30 parts by weight per hundred parts by weight of the biopolymer; and wherein the polymer blend has at least a 10-fold increase in elongation percentage at break compared to the elongation percentage at break of the biopolymer.

2. A polymer blend comprising

(i) a biopolymer, and

(ii) a compatible aliphatic polyester comprising repeating units derivable from succinic acid; repeating units derivable from a substituted or unsubstituted C 2 to C 20 aliphatic diol; and one or two terminator units derivable from a substituted or unsubstituted C 1 to C 20 aliphatic alcohol; wherein the polyester is present in an amount of about 5 to about 30 parts by weight per hundred parts by weight of the biopolymer; and wherein the polymer blend has at least a 10-fold increase in elongation percentage at break compared to the elongation percentage at break of the biopolymer.

3. The polymer blend of claim 2 , wherein the polyester has an acid value of about 8 to about 20 and a hydroxyl value of about 40 to about 110.

4. The polymer blend of claim 2 , wherein the polyester has a number average molecular weight of about 400 to about 10,000 g/mol.

5. The polymer blend of claim 2 , wherein the polyester has an acid value of zero to about 20.

6. The polymer blend of claim 2 , wherein the polyester has an acid value of about 8 to about 20.

7. The polymer blend of claim 2 , wherein the polyester has a hydroxyl value of about zero to about 110.

8. The polymer blend of claim 2 , wherein the polyester has a hydroxyl value of about 40 to about 110.

9. The polymer blend of claim 2 , wherein the biopolymer is selected from the group consisting of polylactic acid, polyhydroxybutyrate, polyvinyl alcohol, polybutylene succinate, polyhydroxyalkanoates, polycaprolactones, aliphatic-aromatic copolyesters, starches, celluloses, and mixtures thereof.

10. The polymer blend of claim 2 , wherein the biopolymer is polylactic acid.

11. The polymer blend of claim 2 , wherein the aliphatic diol is a substituted or unsubstituted C 2 to C 10 aliphatic diol.

12. The polymer blend of claim 2 , wherein the aliphatic diol is a substituted or unsubstituted C 2 to C 4 aliphatic diol.

13. The polymer blend of claim 2 , wherein the aliphatic diol is selected from the group consisting of aliphatic diols having 3 carbon atoms and aliphatic diols having 4 carbon atoms.

14. The polymer blend of claim 2 , wherein the substituted or unsubstituted C 1 to C 20 aliphatic alcohol is selected from the group consisting of methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, eicosanol, cis-9-dodecenol, cis-9-tetradecenol, cis-9-hexadecenol, cis-9-octadecenol, cis-cis-9,12-octadecadienol, cis-cis-cis-9,12,15-octadecatrienol, cis-trans-trans-9,11,13-octadecatrienol, octadecatetraenol, cis-11-eicosenol, eicosadienol, eicosatrienol, 5,8,11,14-eicosatetraenol, eicosapentaenol, cis-13-docosenol, docosatetraenol, 4,8,12,15,19-docosapentaenol, docosahexaenol, tetracosenol, 4,8,12,15,18,21-tetracosahexaenol, and mixtures thereof.

15. The polymer blend of claim 2 , wherein the polymer blend has at least a 5% reduction in tensile strength compared to the tensile strength of the biopolymer and at least a 5% reduction in tensile at break compared to the tensile at break of the biopolymer.

16. The polymer blend of claim 2 , wherein the aliphatic polyester has a formula I:

wherein

n is 1 to 1000;

R 1 is —(CH 2 ) 2 —;

R 2 is a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms;

X 1 is selected from the group consisting of —OH,—O 2 C—R 1 —CO 2 H, and —O 2 C—R 1 —CO 2 R 3 ;

X 2 is selected from the group consisting of —H, —R 2 —OH, and R 3 ; and

R 3 is a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms;

with the proviso that if X 1 is —OH or —O 2 C—R 1 —CO 2 H, then X 2 is R 3 .

17. The polymer blend of claim 16 , wherein n is 2 to 40, R 2 is C 1 to C 10 alkyl and R 3 is C 1 to C 20 alkyl.

18. The polymer blend of claim 16 , wherein n is 2 to 20, R 2 is C 3 alkyl and R 3 is C 8 to C 10 alkyl.

19. The polymer blend of claim 16 , wherein R 2 is an alkyl group having from 2 to 4 carbon atoms.

20. The polymer blend of claim 16 , wherein R 2 is selected from the group consisting of —(CH 2 ) 3 —, —CH 2 CH(CH 3 )—, and —CH(CH 3 )CH 2 —.

21. The polymer blend of claim 16 , wherein R 3 is a mixture comprising —(CH 2 ) 7 CH 3 and —(CH 2 ) 9 CH 3 —.

22. The method of claim 1 , wherein the polymer blend has at least a 5% reduction in tensile strength compared to the tensile strength of the biopolymer and at least a 5% reduction in tensile at break compared to the tensile at break of the biopolymer.

23. The method of claim 1 , wherein the polymer blend comprises polymers, the polymers consisting of (i) the biopolymer and (ii) the polyester.

24. The polymer blend of claim 2 , wherein the polymer blend comprises polymers, the polymers consisting of (i) the biopolymer and (ii) the polyester.

Assignments (5)
THIRD AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Dec 20, 2024
From: THE HALLSTAR COMPANY; HALLSTAR INNOVATIONS CORP.; HALLSTAR BEAUTY AND PERSONAL CARE INNOVATIONS COMPANY; UNIPLEX COMPANY
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 069747/0045 →
THIRD AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Nov 3, 2023
From: THE HALLSTAR COMPANY; HALLSTAR INNOVATIONS CORP.; HALLSTAR BEAUTY AND PERSONAL CARE INNOVATIONS COMPANY; UNIPLEX COMPANY
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 065448/0262 →
SECOND AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Nov 25, 2014
From: HALLSTAR INNOVATIONS CORP.
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 034468/0854 →
AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Feb 21, 2012
From: HALLSTAR INNOVATIONS CORP.
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 027742/0917 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 24, 2010
From: STEFANISIN, KIMBERLY L.; SHAH, URVIL B.; O'ROURKE, STEPHEN; WENTWORTH, GARY
To: HALLSTAR INNOVATIONS CORP.
Reel/Frame 024878/0286 →