Highly heat-resistant and highly transparent polycarbonate ester, and preparation method therefor

Patent metadata

Field	Value
Publication number	US-9975991-B2
Application number	US-201715445080-A
Country	US
Kind code	B2
Filing date	Feb 28, 2017
Priority date	Jul 24, 2013
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

Disclosed is a bio-based polycarbonate ester comprising: (i) repeat unit 1 obtained from a condensation reaction of 1,4:3,6-dianhydrohexitol and carbonate; and (ii) repeat unit 2 obtained from a condensation reaction of 1,4:3,6-dianhydrohexitol and 1,4-cyclohexanedicarboxylate; and a preparation method for the bio-based polycarbonate ester, comprising the steps of: (1) preparing a compound 1,4-diphenyl-cyclohexanedicarboxylate through a trans-esterification or esterification reaction of a compound represented by

and phenol; and (2) preparing a compound comprising a repeat unit represented by

through a polycarbonate melt polycondensation reaction of the 1,4-diphenyl-cyclohexanedicarboxylate prepared in step (1), a compound represented by

First claim

What is claimed is:

1. A method for manufacturing a bio-based polycarbonate ester comprising:
(1) subjecting a compound of Formula 2 and phenol to a transesterification or esterification reaction to obtain a compound of Formula 3; and
(2) subjecting the compound of Formula 3 obtained in (1), a compound of Formula 4, and 1,4:3,6-dianhydrohexitol to a polycarbonate melt polycondensation reaction to prepare a polycarbonate ester consisting of a repeating unit of Formula 1:

wherein, in Formula 1, x satisfies 0<x<1,
in Formula 2, R is methyl or hydrogen, and
in Formula 4, R 1 and R 2 are each independently an aliphatic group having 1 to 18 carbon atoms or an aromatic group having 6 to 20 carbon atoms which may have an optional substituent, and
wherein the ratio of cis/trans cyclohexanedicarboxylate unit is 20/80% to 80/20% in the repeating unit of Formula 1.

2. The method of claim 1 , wherein the ratio of cis/trans cyclohexanedicarboxylate unit is 40/60% in the repeating unit of Formula 1.

3. The method of claim 1 , wherein the reaction in (1) is conducted at 150 to 250° C. under a normal pressure, or at 150 to 300° C. under a pressure of 0.1 to 10 bar, for 5 minutes to 48 hours.

4. The method of claim 1 , wherein phenol is used in (1) in an amount of 2 to 50 times of the total mole number of the compound of Formula 2.

5. The method of claim 1 , wherein the compound of Formula 4 is dimethyl carbonate, diethyl carbonate, di-t-butyl carbonate, diphenyl carbonate, or ditolyl carbonate.

6. The method of claim 1 , wherein the melt polycondensation of (2) includes a first part of the reaction and a second part of the reaction,
the first part of the reaction is carried out under a reduced pressure of 5 to 700 Torr at a temperature of 130 to 250° C. for 0.1 to 10 hours, and
the second part of the reaction is carried out under a reduced pressure of 20 Torr or less at a temperature of 210 to 290° C. for 0.1 to 10 hours.

7. The method of claim 1 , wherein the compound of Formula 3 is obtained by a reaction of 1,4-dimethyl-cyclohexane dicarboxylate or 1,4-cyclohexanedicarboxylic acid with phenol.

Assignees

• Sk Chemicals Co Ltd

Inventors

• Oh Kwang Sei
• Cha Il-Hoon
• Kim Ji-Hoon

Classifications

• C08G63/78

  Preparation processes · CPC title

• C08G63/64 Primary

  Polyesters containing both carboxylic ester groups and carbonate groups · CPC title

• C08G64/20 Primary

  General preparatory processes · CPC title

• C08L69/00

  Compositions of polycarbonates; Compositions of derivatives of polycarbonates · CPC title

• C08L67/00

  Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain (of polyester-amides C08L77/12; of polyester-imides C08L79/08); Compositions of derivatives of such polymers · CPC title