Biodegradable aliphatic-aromatic polyesters

• US 8,193,298 B2
• Filed: 03/17/2006
• Issued: 06/05/2012
• Est. Priority Date: 03/18/2005
• Status: Active Grant

• Current Assignee: Novamont S.p.a.
• Original Assignee: Novamont S.p.a.
• Inventors: Bastioli, Catia, Milizia, Tiziana, Floridi, Giovanni, Lallaro, Andrea Scaffidi, Cella, Giandomenico, Tosin, Maurizio
• Primary Examiner(s): Seidleck, James J
• Assistant Examiner(s): Tischler, Frances
• Application Number:
  US11/909,012
• Publication Number:
  US 20080214702A1
• Time in Patent Office: 2,272 Days
• Field of Search: 528/271, 528/272, 528/437, 528/302, 528/300, 528/303, 528/304, 528/305, 528/306, 528/308, 528/308.1, 528/308.3, 428/35.1, 428/480, 428/35.2, 428/35.7, 428/36.4, 428/77, 428/221, 428/357, 428/409, 428/411.1, 524/35, 524/47, 524/27, 525/418, 525/419, 525/437
• US Class Current: 528/302
• CPC Class Codes: C08G 63/16 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C08L 1/00 Compositions of cellulose, modified cellulose or cellulose derivatives
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 3/02 Starch; Degradation products thereof, e.g. dextrin
• CPC Class Codes: C08L 67/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C08L67/06 takes precedence
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence
• CPC Class Codes: Y10T 428/1331 Single layer [continuous layer]
• CPC Class Codes: Y10T 428/1334 Nonself-supporting tubular film or bag [e.g., pouch, envelope, packet, etc.]
• CPC Class Codes: Y10T 428/1352 Polymer or resin containing [i.e., natural or synthetic]
• CPC Class Codes: Y10T 428/249921 Web or sheet containing structurally defined element or component
• CPC Class Codes: Y10T 428/29 Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
• CPC Class Codes: Y10T 428/31504 Composite [nonstructural laminate]
• CPC Class Codes: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]

Abstract

Biodegradable aliphatic/aromatic copolyester comprising 50 to 60 mol % of an aromatic dicarboxylic acid and 40 to 50 mol % of an aliphatic acid, at least 90% of which is a long-chain dicarboxylic acid (LCDA) of natural origin selected from azelaic acid, sebacic acid, brassylic acid or mixtures thereof; and a diol component.

Claims

1. Biodegradable aliphatic/aromatic copolyester (AAPE) comprising:

A) an acid component comprising repeating units of;

1) 50 to 60 mol % of an aromatic polyfunctional acid;

2) 40 to 50 mol % of an aliphatic acid, at least 90% of which is a long-chain dicarboxylic acid (LCDA) of natural origin selected from azelaic acid, sebacic acid, brassylic acid or mixtures thereof;

B) at least one diol component;

said aliphatic long-chain dicarboxylic acid (LCDA) and said diol component (B) having a number of carbon atoms according to the following formula;

(C_LCDA·

Y_LCDA)/2+C_B Y_B>

7.5 where;

C_LCDA is the number of carbon atoms of the LCDA and can be 9, 10 or 13;

Y_LCDA is the molar fraction of each LCDA on the total number of moles of LCDA;

C_B is the number of carbon atoms of each diol component;

Y_B is the molar fraction of each diol on the total number of moles of the diol component (B) said AAPE having;

a biodegradability after 90 days higher than 70%, with respect to pure cellulose according to the Standard ISO 14855Amendment 1,

a density of equal to or less than 1.2 g/cc;

a number average molecular weight of 40,000-140,000;

an inherent viscosity of 0.8-1.5.

2. Biodegradable polyester according to claim 1, wherein said aromatic dicarboxylic acid is selected from the group consisting of the phthalic acids.

3. Biodegradable polyester according to claim 2, wherein said aromatic dicarboxylic acid is terephthalic acid.

4. Biodegradable polyester according to claim 1, wherein the polydispersity index M_w/M_n, is between 1.7 and 2.6.

5. Biodegradable polyester according to claim 4, wherein said polydispersity index M_w/M_n is between 1.8 and 2.5.

6. Biodegradable polyester according to claim 1, wherein said diol is selected from the group consisting of:

1,2-ethanediol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-dodecanediol, 1,13-tridecanediol, 1,4-cyclohexanedimethanol, propylene glycol, neo-pentyl glycol, 2-methyl-1,3-propanediol, dianhydrosorbitol, dianhydromannitol, dianhydroiditol, cyclohexanediol, and cyclohexanemethanediol.

7. Biodegradable polyester according to claim 1, wherein said diol has from 2 to 10 carbon atoms.

8. Biodegradable polyester according to claim 7, wherein said diol has from 2 to 4 carbon atoms.

9. Biodegradable polyester according to claim 1, characterized in that said aliphatic long-chain dicarboxylic acid (LCDA) and said diol component (B) have a number of carbon atoms according to the following formula:

(C_LCDA·

Y_LCDA)/2+C_B·

Y_B>

8.

10. Biodegradable polyester according to claim 1, wherein said biodegradability after 90 days is higher than 80%.

11. Biodegradable polyester according to claim 1, having a crystallization temperature T_c higher than 25°

C.

12. Biodegradable polyester according to claim 11, having a crystallization temperature T_c higher than 30°

C.

13. Biodegradable polyester according to claim 12, having a crystallization temperature T_c higher than 40°

C.

14. Biodegradable polyester according to claim 1, wherein said aliphatic acid comprises at least one hydroxy acid in an amount of up to 10 mol % with respect to the total molar content of the aliphatic acid.

15. A film comprising the polyesters according to claim 1.