# US 9,040,654 B2 · Process for manufacturing polycarbonate from dianhydrohexitol Dialkylcarbonate

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- Number: US 9,040,654 B2
- Document ID: US9040654B2
- Status: Granted
- Kind: B2
- Application number: 14/110,292
- Filed: 2012-04-05
- Published: 2014-01-30
- Granted: 2015-05-26
- Earliest claimed: 2011-04-05
- Assignees: Roquette Freres
- Applicants: Mathias Ibert; Emilie Josien; Herve Wyart
- Inventors: Mathias Ibert; Emilie Josien; Herve Wyart
- Web page: https://patentgrep.com/patent/US9040654B2

## CPC

- C08G 64/0208: {saturated}
- C08G 64/305: {and alcohols}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

A process for manufacturing a polycarbonate, having a glass transition temperature greater than or equal to 50° C., includes: a step (1) of introducing into a reactor a monomer of formula (I) and R1 and R2 being identical or different alkyl groups; a step (2) of introducing into the reactor at least one cyclic diol or a mixture of diols (B) including at least 20 mol % of cyclic diols; a subsequent step (3) of polycondensation via transesterification of the mixture of monomers including the monomers (A) and (B); a step (4) of recovering the polycarbonate formed during step (3).

## Claims

### Claim 1

A process for manufacturing a polycarbonate with a glass transition temperature of greater than or equal to 50° C., comprising:
a step (1) of introducing, into a reactor, a monomer (A) of formula:
R1 and R2 being identical or different alkyl groups;
a step (2) of introducing, into the reactor, at least one cyclic diol or a mixture of diols (B) comprising at least 20 mol % of cyclic diols;
a step (3) of polycondensation by transesterification of the mixture comprising monomers (A) and (B); and
a step (4) of recovering the polycarbonate formed in step (3).

### Claim 2 (depends on 1)

The process of claim 1, wherein the alkyl groups R1 and R2 comprise from 1 to 10 carbon atoms.

### Claim 3 (depends on 1)

The process of claim 1, wherein (B) is a mixture of diols comprising, relative to the total number of diols, at least 50 mol % of a cyclic diol or of a mixture of cyclic diols.

### Claim 4 (depends on 1)

The process of claim 1, wherein the at least one cyclic diol(s) are selected from the group consisting of:
bisphenols such as 2,2-bis(4-hydroxyphenyl)propane (bisphenol A), 2,2-bis(3,5-dimethyl-4-hydroxyphenyl)propane, bis(4-hydroxyphenyl)methane (bisphenol F), 1,1-bis(4-hydroxyphenyl)cyclohexane (bisphenol C), and 1,1-bis(4-hydroxyphenyl)ethane (bisphenol AD);
dianhydrohexitols such as isosorbide, isomannide and isoidide;
cyclohexanedimethanols such as 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol and 1,4-cyclohexanedimethanol;
tricyclodecanedimethanols;
pentacyclopentanedimethanols;
decalindimethanols such as 2,6-decalindimethanol, 1,5-decalindimethanol and 2,3-decalindimethanol;
norbornanedimethanols such as 2,3-norbornanedimethanol and 2,5-norbornanedimethanol;
adamantanedimethanols such as 1,3-adamantanedimethanol;
cyclohexanediols such as 1,2-cyclohexanediol, 1,3-cyclohexanediol and 1,4-cyclohexanediol;
tricyclodecanediols;
pentacyclopentadecanediols;
decalindiols;
norbornanediols; and
adamantanediols.

### Claim 5 (depends on 1)

The process of claim 1, wherein the at least one cyclic diol is isosorbide, isomannide, isoidide, 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, or 1,4-cyclohexanedimethanol.

### Claim 6 (depends on 1)

The process of claim 1, further comprising a step (1′) of introducing, into the reactor, a monomer (C) of formula:
R3 and R4 being identical or different alkyl groups comprising from 1 to 10 carbon atoms.

### Claim 7 (depends on 1)

The process of claim 1, wherein the monomer (A) is an isosorbide dialkyl carbonate.

### Claim 8 (depends on 6)

The process of claim 6, wherein the molar amounts of monomers (A), (B) and (C) introduced are, relative to their total number:
from 1% to 60% of (A);
from 40% to 60% of (B); and
from 0% to 39% of (C),
the sum of (A), (B) and (C) being 100%.

### Claim 9 (depends on 6)

The process of claim 6, wherein the monomers (A), (B) and (C) constitute more than 90 mol % of the total amount of monomers introduced into the reactor.

### Claim 10 (depends on 1)

The process of claim 1, wherein step (3) takes place in the presence of a transesterification catalyst.

### Claim 11 (depends on 10)

The process of claim 10, wherein the catalyst comprises at least one of an alkali metal ion, an alkaline earth metal ion, a cyclic nitrogen compound, a quaternary ammonium ion, a quaternary phosphonium ion, a basic boron-based compound, or a basic phosphorous-based compound.

### Claim 12 (depends on 10)

The process of claim 10, wherein the molar amount of the catalyst is in a range of from 10−7% to 1%, relative to the amount of (A) and (C).

### Claim 13 (depends on 1)

The process of claim 1, wherein at least part of step (3) is performed at a temperature in a range of from 100° C. to 250° C.

### Claim 14 (depends on 1)

The process as claimcd in of claim 1, wherein at least part of step (3) is performed at a pressure in a range of from 30 kPa to 110 kPa.

### Claim 15 (depends on 1)

The process of claim 1, wherein the polycarbonate recovered in step (4) has a glass transition temperature in a range of from 90° C. to 180° C. and preferably from 110° C. to 170° C.

### Claim 16 (depends on 1)

The process of claim 1, wherein the alkyl groups R1 and R2 independently are methyl or ethyl groups.

### Claim 17 (depends on 1)

The process of claim 1, wherein the at least one cyclic diol is isosorbide.

### Claim 18 (depends on 6)

The process of claim 6, wherein the alkyl groups R3 and R4 independently are methyl or ethyl groups.

### Claim 19 (depends on 6)

The process of claim 6, wherein the molar amounts of monomers (A), (B) and (C) introduced are, relative to their total number:
from 39% to 59% of (A);
from 40% to 60% of (B); and
from 1% to 10% of (C),
the sum of (A), (B) and (C) being 100%.

### Claim 20 (depends on 10)

The process of claim 10, wherein the catalyst comprises cesium carbonate.