# US 11,299,585 B2 · Oligocarbonate polyols obtained from dianhydrohexitol dialkylcarbonate or a dimer of dianhydrohexitol carbonate, method for the production thereof and uses thereof

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- Number: US 11,299,585 B2
- Document ID: US11299585B2
- Status: Granted
- Kind: B2
- Application number: 16/756,346
- Filed: 2018-10-15
- Published: 2020-10-15
- Granted: 2022-04-12
- Earliest claimed: 2017-10-16
- Assignees: Roquette Freres
- Applicants: Roquette Freres
- Inventors: Jean-Marc Corpart; René Saint-Loup
- Web page: https://patentgrep.com/patent/US11299585B2

## CPC

- C08G 64/02: Aliphatic polycarbonates
- C08G 64/305: {and alcohols}
- C08G 18/44: Polycarbonates
- C08G 64/0208: {saturated}
- C08G 64/403: {Recovery of the polymer}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Provided is a method for producing an oligocarbonate polyol devoid of aromatic groups and phenolic functions, comprising a step of polycondensation by transesterification of monomers (A1) and/or dimers (A2) and of diol monomers (B1) and/or of triol monomers (B2), in a particular molar ratio, in order to obtain an oligocarbonate polyol having a molar mass of less than 5000 g/mol and at least two hydroxyl-type chain ends, the monomer (A1) corresponding to the following formula: (A1) and the dimer (A2) corresponding to the following formula: (A2) as well as the oligocarbonate polyol that can be obtained by this method and the polycarbonate that can be obtained by reacting this oligocarbonate with a polyisocyanate.

## Claims

### Claim 1

A process for the preparation of a polycarbonate-urethane, wherein an oligocarbonate polyol is reacted with a polyisocyanate, wherein the oligocarbonate polyol is obtained by a second process comprising the steps of:
a stage (1) of introduction, into a reactor:
of a monomer of formula (A1):
in which R1 and R2 are identical or different alkyl groups, or of a dimer of formula (A2):
in which R3 and R4 are identical or different alkyl groups, or of a mixture of (A1) and (A2);
a stage (2) of introduction, into the reactor, of a diol monomer (B1) or of a triol monomer (B2) or of a mixture of (B1) and (B2), (B1) and (B2) both being different from (A1) and (A2);
the molar ratio in the reactor of (A1) and (A2) with respect to (B1) and (B2) corresponding to the following formula:
[
(
A
⁢
1
)
2
+
(
A
⁢
2
)
2
]
[
(
B
⁢
1
)
2
+
(
B
⁢
2
)
3
]
<
1
,
a subsequent stage (3) of polycondensation by transesterification of the monomers and dimers (A1), (A2), (B1) and (B2) in order to obtain an oligocarbonate polyol having a molar mass of less than 5000 g/mol and two or more hydroxyl chain end groups, and
a stage (4) of recovery of the oligocarbonate polyol;
wherein the diol monomer (B1) is chosen from ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol or 1,10-decanediol, 1,2-propanediol, 1,3-butanediol, 2,3-butanediol, 1,3-pentanediol, 1,4-hexanediol, 2,2-dimethyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 2,2-dimethyl-1,3-propanediol or 2-methyl-1,3-propanediol or from the following cyclic diols:
cyclohexanedimethanols;
tricyclodecanedimethanols;
pentacyclopentanedimethanols;
decalindimethanols;
norbornanedimethanols;
adamantanedimethanols,
cyclohexanediols,
tricyclodecanediols,
pentacyclopentadecanediols,
decalindiols,
norbornanediols,
adamantanediols,
spiroglycol,
2,2,4,4-tetramethyl-1,3-cyclobutanediol;
di-O-methylene-D-glucitol and dimethyl di-O-methylene-D-glucarate.

### Claim 2 (depends on 1)

The process as claimed in claim 1, wherein the monomer (A1) is introduced into the reactor in stage (1) alone or as a mixture with the dimer (A2).

### Claim 3 (depends on 1)

The process as claimed in claim 1, wherein the molar ratio in the reactor of (A1) and (A2) with respect to (B1) and (B2), corresponding to the following formula:
[
(
A
⁢
1
)
2
+
(
A
⁢
2
)
2
]
[
(
B
⁢
1
)
2
+
(
B
⁢
2
)
3
]
is strictly less than 1 and greater than 0.5.

### Claim 4 (depends on 1)

The process as claimed in claim 1, wherein R1, R2, R3 and R4 are independently chosen from alkyl groups comprising from 1 to 10 carbon atoms.

### Claim 5 (depends on 2)

The process as claimed in claim 2, wherein the monomer (A1) is an isosorbide bis(alkyl carbonate).

### Claim 6 (depends on 1)

The process as claimed in claim 1, wherein the triol monomer (B2) is chosen from aliphatic diols and triols, branched aliphatic diols and triols and cyclic aliphatic diols and triols.

### Claim 7 (depends on 1)

The process as claimed in claim 1, wherein stage (3) takes place in the presence of a catalyst of polycondensation by transesterification.

### Claim 8 (depends on 7)

The process as claimed in claim 7, wherein the molar amount of catalyst with respect to the amount of the monomer (A1) and of the dimer (A2) advantageously ranges from 10−7% to 1% by weight.

### Claim 9 (depends on 1)

The process as claimed in claim 1, wherein stage (3) is carried out under an inert atmosphere.

### Claim 10 (depends on 1)

The process as claimed in claim 1, wherein a part of stage (3) is carried out at a temperature ranging from 100° C. to 250° C.

### Claim 11 (depends on 1)

The process as claimed in claim 1, wherein the oligocarbonate polyol comprises a phenol content of less than 50 ppb.

### Claim 12 (depends on 1)

The process as claimed in claim 1, wherein the polyisocyanate is a diisocyanate.

### Claim 13 (depends on 12)

The process as claimed in claim 12, wherein the diisocyanate is a linear or cyclic aliphatic diisocyanate.

### Claim 14 (depends on 1)

A polycarbonate-urethane obtained by the process as claimed in claim 1, having a molar mass greater than 5000 g/mol.

### Claim 15 (depends on 14)

The polycarbonate-urethane as claimed in claim 14, exhibiting a maximum flexural stress of greater than 1800 MPa, as measured according to Standard ISO 178:2010.

### Claim 16 (depends on 14)

The polycarbonate-urethane as claimed in claim 14, exhibiting a notched impact strength of greater than 20 kJ/m2, as measured according to the Charpy method DIN EN ISO 179:2010.

### Claim 17 (depends on 14)

The polycarbonate-urethane as claimed in claim 14, that wherein the polycarbonate does not break during an unnotched Charpy test according to Standard DIN EN ISO 179:2010.

### Claim 18 (depends on 14)

The polycarbonate-urethane as claimed in claim 14, exhibiting an elongation at break in tension of greater than 50%, as measured according to Standard ISO 527-1:2012.