Biodegradable polyester

Patent metadata

Field	Value
Publication number	US-11746174-B2
Application number	US-202016952748-A
Country	US
Kind code	B2
Filing date	Nov 19, 2020
Priority date	Nov 19, 2019
Publication date	Sep 5, 2023
Grant date	Sep 5, 2023

Abstract

A biodegradable polyester is provided. The biodegradable polyester is a transesterification or esterification reaction product of a reactant (a) and a reactant (b). The reactant (a) is a modified linear saccharide oligomer. The reactant (b) is a polyester, or the reactant (b) includes a dicarboxylic acid and a diol. The modified saccharide oligomer is a reaction product of a saccharide oligomer and a modifier.

First claim

What is claimed is:

1. A biodegradable polyester, which is a transesterification reaction product or esterification reaction product of a reactant (A) and a reactant (B), wherein the reactant (A) is a modified saccharide oligomer, and the reactant (B) is a polyester, or the reactant (B) consists of a dicarboxylic acid and a dihydric alcohol, wherein the modified saccharide oligomer is a reaction product of a saccharide oligomer and a modifier, and wherein the saccharide oligomer is dextrin, chitosan, or a combination thereof.

2. The biodegradable polyester as claimed in claim 1 , wherein the modifier is a carboxylic acid, anhydride, siloxane having at least one reactive functional group, or a combination thereof, wherein the reactive functional group is acrylate group, methacrylate group, glycidyl group, oxiranyl group, oxetanyl group, or 3,4-epoxycyclohexyl group.

3. The biodegradable polyester as claimed in claim 1 , wherein the modifier is formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, heptanoic acid, caprylic acid, benzoic acid, acetic anhydride, succinic anhydride, maleic anhydride, methylpropanoic anhydride, 3-dodecyloxolane-2,5-dione, tetradecylsuccinicanhydride, benzoic anhydride, 3-glycidyloxypropyl)trimethoxysilane, 3-glycidyloxypropyltriethoxysilane, 3-(trimethoxysilyl)propyl methacrylate, 3-(triethoxysilyl)propyl methacrylate, 3-(trimethoxysilyl)propyl acrylate, 3-(triethoxysilyl)propyl acrylate, [2-(3,4-epoxycyclohexyl)ethyl]trimethoxysilane, [2-(3,4-epoxycyclohexyl)ethyl]triethoxysilane, or a combination thereof.

4. The biodegradable polyester as claimed in claim 1 , wherein the weight ratio of the reactant (A) to the reactant (B) is 1:100 to 30:100.

5. The biodegradable polyester as claimed in claim 1 , wherein the modified saccharide oligomer has a weight average molecular weight of 500 to 15,000.

6. The biodegradable polyester as claimed in claim 1 , wherein each anhydroglucose unit (AGU) of the modified saccharide oligomer has an average degree of substitution from 0.5 to 2.5.

7. The biodegradable polyester as claimed in claim 1 , wherein the modified saccharide oligomer comprises a saccharide oligomer having at least one repeating unit of Formula (I), a saccharide oligomer having at least one repeating unit of Formula (II) or a combination thereof

wherein R 3 and R 4 are —NH 2 , and R 1 , R 2 , R 5 , R 6 , R 7 , R 8 and R 9 are independently —OH, —NH 2 ,

at least one of R 1 , R 2 , R 5 , and R 6 is

at least one of R 7 , R 8 and R 9 is

R is hydrogen, C 1-8 alkyl group, aryl group or C 2-18 carboxyl group; R 10 , R 11 and R 12 are independently C 1-8 alkyl group, C 1-8 alkoxy group or Z—R 13 ); is single bond, unsubstituted C 1-8 alkylene group or substituted C 2-8 alkylene group; when Z is substituted C 2-8 alkylene group, wherein at least one —CH 2 — of C 2-8 alkylene group is replaced with —O—, —CO—, —OCO—, —COO—, —CONH—, or —NHCO—; R 13 is acrylate group, methacrylate group, glycidyl group, oxiranyl group, oxetanyl group, 3,4-epoxycyclohexyl group, or glycidyloxypropyl group; and at least one of R 10 , R 11 , and R 12 is Z—R 13 ).

8. The biodegradable polyester as claimed in claim 1 , wherein the dicarboxylic acid is a compound having a structure represented by Formula (III), and the dihydric alcohol is a compound having a structure represented by Formula (IV)

wherein R a and R b are independently unsubstituted C 1-8 alkylene group or phenylene group.

9. The biodegradable polyester as claimed in claim 1 , wherein the molar ratio of the dicarboxylic acid to the dihydric alcohol is 1.2:1 to 1:1.2.

10. The biodegradable polyester as claimed in claim 1 , wherein the polyester has at least one repeating unit of Formula (V)

wherein R a and R b are independently unsubstituted C 1-8 alkylene group or phenylene group.

11. The biodegradable polyester as claimed in claim 1 , wherein the polyester has a weight average molecular weight of 500 to 100,000.

12. The biodegradable polyester as claimed in claim 1 , wherein the polyester is polybutylene succinate (PBS), polybutylene succinate adipate (PBSA), polyethylene succinate (PES), polybutylene adipate/terephthalate (PBAT), or a combination thereof.

Assignees

• Ind Tech Res Inst

Inventors

• Huang Shu-Jiuan
• Kuo Shin-Liang
• Chang Hung Ming
• Chang Sheng-Lung
• Wu Jin-An

Classifications

• C08F283/02 Primary

  on to polycarbonates or saturated polyesters {(C08F283/004 takes precedence)} · CPC title

• C08B3/04

  Cellulose formate · CPC title

• C08B3/06

  Cellulose acetate {, e.g. mono-acetate, di-acetate or tri-acetate} · CPC title

• C08B31/00

  Preparation of derivatives of starch (derivatives of amylose C08B33/00; derivatives of amylopectin C08B35/00) · CPC title

• C08G63/668 Primary

  derived from polycarboxylic acids and polyhydroxy compounds · CPC title