IP Library Granted Patent US 7,265,188
Granted Patent B2
US 7,265,188 · App. 10/407,301 · Granted Sep 4, 2007

Biodegradable polyester blend compositions and methods of making the same

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Quick Facts
Patent No.
US 7,265,188
App. No.
10/407,301
Granted
Sep 4, 2007
Kind
B2
Abstract

The present invention relates to tough and ductile biodegradable, aliphatic polyester blend compositions and methods for preparing such compositions. It relates to products made out of such blend compositions, including, but not limited to, films, fibers, nonwovens, sheets, coatings, binders, foams and molded products for packaging. The products exhibit a desirable combination of high strength, ductility and toughness, while maintaining flexibility, biodegradability and compostability. The products are useful for a variety of biodegradable articles, such as diaper topsheets, diaper backsheets, disposable wipes, shopping and lawn/leaf bags, agricultural films, disposable garments, medical disposables, paper coatings, biodegradable packaging, binders for cellulose fibers or synthetics, and the like.

Claims (32)

1. A polyester blend composition comprising:

(a) from about 70% to about 30% by weight of a polyhydroxyalkanoate copolymer comprising at least two randomly repeating monomer units wherein the first randomly repeating monomer unit has the structure (I):

wherein R 1 is H, or a C1-C2 alkyl, and n is 1 or 2; the second randomly repeating monomer unit comprises at least one monomer selected from the group consisting of the structures (II) and (III):

wherein R 2 is a C3-C19 alkyl or C3-C19 alkenyl, and

wherein m is from about 2 to about 16; and

(b) from 30% to about 70% by weight of an aliphatic ester polycondensate synthesized from an aliphatic polyhydric alcohol and an aliphatic polycarboxylic acid compound, wherein the weight average molecular weight of the ester polycondensate is from about 50,000 to about 500,000.

2. A polyester blend composition according to claim 1 , wherein the polyhydric alcohol is a dihydric alcohol, and further wherein the polycarboxylic acid compound is a dicarboxylic acid compound selected from the group consisting of dicarboxylic acids, dicarboxylic acid anhydrides and mixtures thereof.

3. A polyester blend composition according to claim 2 , wherein the aliphatic ester polycondensate is synthesized from a dicarboxylic acid compound selected from the group consisting of compounds having the formula:

wherein s is from about 1 to about 10; and a dihydric alcohol having the formula: HO——(CH 2 ) t ——OH wherein it is from about 2 to 10.

4. A polyester blend composition according to claim 2 , wherein the aliphatic ester polycondensate contains less than 50% by weight of aromatic diacids.

5. A polyester blend composition according to claim 1 , wherein the polyhydroxyalkanoate copolymer (a) further comprises a third randomly repeating monomer unit having the structure (IV):

wherein R 3 is H or a C 1-19 alkyl or alkenyl; and q is 1 or 2; and wherein the third randomly repeating monomer unit is not the same as the first randomly repeating monomer unit or the second randomly repeating monomer unit.

6. A polyester blend composition according to claim 5 , wherein the third randomly repeating monomer unit is selected from the group consisting of the monomer wherein R 3 is C 1 alkyl and q is 1, the monomer wherein R 3 is C 2 alkyl and q is 1, the monomer wherein R 3 is H and q is 2, the monomer wherein R 3 is H and q is 1, and mixtures thereof.

7. A polyester blend composition according to claim 1 , wherein the first randomly repeating monomer unit is selected from the group consisting of the monomer wherein R 1 is C 1 alkyl and n is 1, the monomer wherein R 1 is C 2 alkyl and n is 1, the monomer wherein R 1 is H and n is 2, the monomer wherein R 1 is H and n is 1, and mixtures thereof.

8. A polyester blend composition according to claim 1 , wherein at least 50% of the randomly repeating monomer units in copolymer (a) have the structure of the first monomer unit.

9. A polyester blend composition according to claim 1 , wherein the polyester blend is substantially free of compatibilizers.

10. A polyester blend composition according to claim 1 , wherein the polyester blend is substantially free of initiators.

11. A polyester blend composition according to claim 1 , wherein the polyester blend further comprises up to 20%, by weight, of a plasticizing agent.

12. A polyester blend composition according to claim 1 , wherein the polyester blend composition consists essentially of the polyhydroxyalkanoate copolymer and the aliphatic ester polycondensate.

13. A method of making a polyester blend composition, comprising the step of blending (a) a polyhydroxyalkanoate copolymer comprising at least two randomly repeating monomer units wherein the first randomly repeating monomer unit has the structure:

wherein R 1 is H, or a C1-C2 alkyl, and n is 1 or 2; the second randomly repeating monomer unit comprises at least one monomer selected from the group consisting of the structures (II) and (III):

wherein R 2 is a C3-C19 alkyl or C3-C19 alkenyl, and

wherein m is from about 2 to about 16; and

(b) an aliphatic ester polycondensate synthesized from an aliphatic polyhydric alcohol and an aliphatic polycarboxylic acid compound;

wherein the polyester blend composition is about 70% to about 30% by weight of the polyhydroxyalkanoate copolymer and from 30% to about 70% by weight of the aliphatic ester polycondensate and the weight average molecular weight of the ester polycondensate is from about 50,000 to about 500,000.

14. A method according to according to claim 13 , wherein the polyhydroxyalkanoate copolymer and aliphatic ester polycondensate are compatible and immiscible.

15. A method according to claim 14 , wherein the weight ratio of polyhydroxyalkanoate copolymer to aliphatic ester polycondensate is from between 70:30 to about 30:70 and wherein at least 50% of the randomly repeating monomer units in copolymer (a) have the structure of the first monomer unit.

16. A method according to claim 13 , wherein the step of blending comprises melt-blending.

17. A method according to claim 13 , wherein the step of blending comprises solution-blending a polyhydroxyalkanoate copolymer and an aliphatic ester polycondensate in a common solvent.

18. A method according to claim 13 , wherein the polyester blend composition is substantially free of initiators.

19. A method according to claim 13 , wherein the aliphatic ester polycondensate is synthesized from a dicarboxylic acid compound selected from the group consisting of compounds having the formula:

wherein s is from about 1 to about 10; and a dihydric alcohol having the formula: HO——(CH 2 ) t ——OH wherein t is from about 2 to about 10.

Assignments (13)
SECURITY INTEREST Recorded Dec 17, 2024
From: DANIMER SCIENTIFIC, INC.; MEREDIAN HOLDINGS GROUP, INC.; DANIMER SCIENTIFIC HOLDINGS, LLC; MEREDIAN, INC.; DANIMER SCIENTIFIC, L.L.C.; DANIMER BIOPLASTICS, INC.; DANIMER IPCO, LLC; DANIMER IPHOLDCO, LLC; NOVOMER, INC.
To: JEFFERIES CAPITAL SERVICES, LLC; RIVA RIDGE MASTER FUND, LTD.; BPI CREDIT 6, L.L.C.
Reel/Frame 069888/0715 →
SECURITY INTEREST Recorded Dec 4, 2024
From: DANIMER SCIENTIFIC, INC.; MEREDIAN HOLDINGS GROUP, INC.; DANIMER SCIENTIFIC HOLDINGS, LLC; DANIMER SCIENTIFIC MANUFACTURING, INC.; MEREDIAN, INC.; DANIMER SCIENTIFIC, L.L.C.; DANIMER SCIENTIFIC KENTUCKY, INC.; DANIMER BIOPLASTICS, INC.; DANIMER IPCO, LLC; NOVOMER, INC.; DANIMER IPHOLDCO, LLC
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 069483/0417 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 17, 2023
From: MEREDIAN BIOPLASTICS, INC.
To: DANIMER IPCO, LLC
Reel/Frame 063113/0294 →
RELEASE OF SECURITY INTEREST Recorded Mar 16, 2023
From: SOUTHEAST COMMUNITY DEVELOPMENT FUND X, L.L.C.
To: DANIMER BIOPLASTICS, INC.; MEREDIAN, INC.; MEREDIAN BIOPLASTICS, INC.; DANIMER SCIENTIFIC, L.L.C.
Reel/Frame 063006/0860 →
RELEASE OF SECURITY INTEREST Recorded Jan 20, 2023
From: WHITE OAK GLOBAL ADVISORS, LLC
To: DANIMER BIOPLASTICS, INC.; MEREDIAN, INC.; MEREDIAN BIOPLASTICS, INC.,; DANIMER SCIENTIFIC, L.L.C.
Reel/Frame 062440/0763 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 3, 2023
From: MEREDIAN BIOPLASTICS, INC.
To: MEREDIAN, INC.
Reel/Frame 062262/0001 →
RELEASE OF SECURITY INTEREST Recorded Aug 5, 2022
From: TRUIST BANK
To: DANIMER SCIENTIFIC, L.L.C.; DANIMER BIOPLASTICS, INC.; MEREDIAN, INC.; MEREDIAN BIOPLASTICS, INC.
Reel/Frame 061088/0018 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 29, 2022
From: MEREDIAN BIOPLASTICS, INC.
To: MEREDIAN, INC.
Reel/Frame 060674/0621 →
SECURITY INTEREST Recorded May 3, 2021
From: DANIMER SCIENTIFIC, L.L.C.; DANIMER BIOPLASTICS, INC.; MEREDIAN, INC.; MEREDIAN BIOPLASTICS, INC.
To: TRUIST BANK
Reel/Frame 056122/0473 →
RELEASE OF SECURITY INTEREST Recorded Feb 5, 2021
From: WHITE OAK GLOBAL ADVISORS, LLC
To: DANIMER BIOPLASTICS, INC.; MEREDIAN, INC.; MEREDIAN BIOPLASTICS, INC.; DANIMER SCIENTIFIC, L.L.C.
Reel/Frame 055225/0196 →
SECURITY INTEREST Recorded Mar 19, 2019
From: DANIMER BIOPLASTICS, INC.; MEREDIAN, INC.; MEREDIAN BIOPLASTICS, INC.; DANIMER SCIENTIFIC, L.L.C.
To: SOUTHEAST COMMUNITY DEVELOPMENT FUND X, L.L.C.
Reel/Frame 048639/0606 →
SECURITY INTEREST Recorded Mar 15, 2019
From: DANIMER BIOPLASTICS, INC.; MEREDIAN, INC.; MEREDIAN BIOPLASTICS, INC.; DANIMER SCIENTIFIC, L.L.C.
To: WHITE OAK GLOBAL ADVISORS, LLC
Reel/Frame 048612/0195 →
RELEASE OF SECURITY INTEREST Recorded Feb 4, 2019
From: UNITED NATIONAL BANK
To: MEREDIAN, INC.
Reel/Frame 048234/0522 →