Process to produce polyesters which incorporate isosorbide

• US 20030204029A1
• Filed: 04/26/2002
• Published: 10/30/2003
• Est. Priority Date: 04/26/2002
• Status: Active Grant

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Brandenburg, Charles J., Hayes, Richard Allen
• Granted Patent: US 6,818,730 B2
• Time in Patent Office: Days
• US Class Current: 525/444
• CPC Class Codes: C08G 63/668 derived from polycarboxylic acids and polyhydroxy compounds

Abstract

The present invention provides a process to produce isosorbide-containing polyesters. The process allows for higher isosorbide incorporation than previously found while maintaining high polymeric molecular weights.

Claims

1. A process to produce polyesters comprising:

melt mixing a first polyester which incorporates isosorbide comprised essentially of;

45.0 to 50.0 mole percent of a dicarboxylic acid component;

5.0 to 50.0 mole percent of isosorbide;

0 to 45.0 mole percent of a diol component other than ethylene glycol or di(ethylene glycol); and

0 to 5.0 mole percent of a polyfunctional branching agent component;

with a second polyester comprised essentially of;

45.0 to 50.0 mole percent of a dicarboxylic acid component, 45.0-50.0 mole percent of a diol component other than isosorbide; and

0 to 5.0 mole percent of a polyfunctional branching agent component;

at a temperature and for a time sufficient to effect transesterification, optionally followed by a finishing process.

3. The process of claim 1 or the polyester of claim 2 wherein the dicarboxylic acid component has 2 carbons to 36 carbons.

4. The process of claim 3 wherein the dicarboxylic acid component is selected from the group consisting of unsubstituted and substituted aromatic, aliphatic, unsaturated, and alicyclic dicarboxylic acids and the lower alkyl esters of dicarboxylic acids.

5. The process of claim 1 or the polyester of claim 2 wherein the dicarboxylic acid component is selected from the group consisting of terephthalic acid, dimethyl terephthalate, isophthalic acid, dimethyl isophthalate, 2,6-napthalene dicarboxylic acid, dimethyl-2,6-naphthalate, 2,7-naphthalenedicarboxylic acid, dimethyl-2,7-naphthalate, 3,4′

-diphenyl ether dicarboxylic acid, dimethyl-3,4′

diphenyl ether dicarboxylate, 4,4′

-diphenyl ether dicarboxylic acid, dimethyl-4,4′

-diphenyl ether dicarboxylate, 3,4′

-diphenyl sulfide dicarboxylic acid, dimethyl-3,4′

-diphenyl sulfide dicarboxylate, 4,4′

-diphenyl sulfide dicarboxylic acid, dimethyl-4,4′

-diphenyl sulfide dicarboxylate, 3,4′

-diphenyl sulfone dicarboxylic acid, dimethyl-3,4′

-diphenyl sulfone dicarboxylate, 4,4′

-diphenyl sulfone dicarboxylic acid, dimethyl-4,4′

-diphenyl sulfone dicarboxylate, 3,4′

-benzophenonedicarboxylic acid, dimethyl-3,4′

-benzophenonedicarboxylate, 4,4′

-benzophenonedicarboxylic acid, dimethyl-4,4′

-benzophenonedicarboxylate, 1,4-naphthalene dicarboxylic acid, dimethyl-1,4-naphthalate, 4,4′

-methylene bis(benzoic acid), dimethyl-4,4′

-methylenebis(benzoate), oxalic acid, dimethyl oxalate, malonic acid, dimethyl malonate, succinic acid, dimethyl succinate, methylsuccinic acid, glutaric acid, dimethyl glutarate, 2-methylglutaric acid, 3-methylglutaric acid, adipic acid, dimethyl adipate, 3-methyladipic acid, 2,2,5,5-tetramethylhexanedioic acid, pimelic acid, suberic acid, azelaic acid, dimethyl azelate, sebacic acid, 1,11-undecanedicarboxylic acid, 1,10-decanedicarboxylic acid, undecanedioic acid, 1,12-dodecanedicarboxylic acid, hexadecanedioic acid, docosanedioic acid, tetracosanedioic acid, dimer acid, 1,4-cyclohexanedicarboxylic acid, dimethyl-1,4-cyclohexanedicarboxylate, 1,3-cyclohexanedicarboxylic acid, dimethyl-1,3-cyclohexanedicarboxylate, 1,1-cyclohexanediacetic acid, metal salts of 5-sulfo-dimethylisophalate, fumaric acid, maleic anhydride, maleic acid, hexahydrophthalic acid phthalic acid and mixtures derived therefrom.

6. The process of claim 1 or the polyester of claim 2 wherein the diol component is selected from the group consisting of unsubstituted, substituted, straight chain, branched, cyclic aliphatic, aliphatic-aromatic and aromatic diols having from 2 carbon atoms to 36 carbon atoms and poly(alkylene ether) glycols with molecular weights between about 250 to 4,000, excluding ethylene glycol and di(ethylene glycol).

7. The process of claim 1 or the polyester of claim 2 wherein the branching agent is selected from the group consisting of any material with three or more carboxylic acid functions, hydroxy functions and a mixture thereof.

8. The process of claim 1 or the polyester of claim 2 wherein the branching agent is selected from the group consisting of 1,2,4-benzenetricarboxylic acid, (trimellitic acid), trimethyl-1,2,4-benzenetricarboxylate, 1,2,4-benzenetricarboxylic an hydride, (trimellitic anhydride), 1,3,5-benzenetricarboxylic acid, 1,2,4,5-benzenetetracarboxylic acid, (pyromellitic acid), 1,2,4,5-benzenetetracarboxylic dianhydride, (pyromellitic anhydride), 3,3′

,4,4′

-benzophenonetetracarboxylic dianhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride, citric acid, tetrahydrofuran-2,3,4,5-tetracarboxylic acid, 1,3,5-cyclohexanetricarboxylic acid, pentaerythritol, 2-(hydroxymethyl)-1,3-propanediol, 2,2-bis(hydroxymethyl)propionic acid, trimer acid, and mixtures therefrom.

2. A polyester comprised essentially of 45 to 50 mole percent of a dicarboxylic acid component, 0.1 to 40 mole percent isosorbide, 10 to 49.9 mole percent of an other diol component, and 0 to 5.0 mole percent of a polyfunctional branching agent component.

9. The polyester of claim 2 wherein the polyester is a block copolymer.