Polyester carbonate and method for producing polyester carbonate

Patent metadata

Field	Value
Publication number	US-11505698-B2
Application number	US-201816957470-A
Country	US
Kind code	B2
Filing date	Dec 27, 2018
Priority date	Dec 28, 2017
Publication date	Nov 22, 2022
Grant date	Nov 22, 2022

Abstract

The present invention relates to a production method of a poly(ester)carbonate, including subjecting a diol and a carbonate ester to a transesterification reaction in the presence of a catalyst, wherein the catalyst comprises aluminum or a compound thereof, and a phosphorus compound.

First claim

The invention claimed is:

1. A polyester carbonate comprising 50 mol % or more of a stereostructural component unit based on all units, wherein
the stereostructural component unit contains a unit derived from a monomer represented by the following formula (A),

wherein
each ring Z is the same or different and represents an aromatic group or a fused polycyclic aromatic group,
R a and R b independently represent a hydrogen atom, a halogen atom or a hydrocarbon group having a carbon number of 1 to 12 or a carbon number of 1 to 20, which may contain an aromatic group,
Ar 1 and Ar 2 represent a hydrogen atom or an aromatic group having a carbon number of 6 to 10, which may contain a substituent,
L 1 and L 2 independently represent a divalent linking group, and
m and n independently represent 0 or 1, and/or

a unit derived from a monomer represented by the following formula (B),

wherein
R 11 and R 12 independently represent a hydrocarbon group having a carbon number of 1 to 10, which may contain an aromatic group,
o and p independently represent an integer of 0 or more,
R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a hydrocarbon group having a carbon number of 1 to 20, which may contain an aromatic group,
the refractive index nD is 1.672 or more,
the specific viscosity measured for a solution prepared by dissolving the polyester carbonate at 0.52 mass % in methylene chloride (a solution prepared by dissolving 0.7 g of the polyester carbonate in 100 ml of methylene chloride) is from 0.12 to 0.40, and
the b* value of CIE1976 (L*a*b*) color system measured for a solution prepared by dissolving the polyester carbonate at 13 mass % in methylene chloride (a solution prepared by dissolving 1.0 g of the polyester carbonate in 5 ml of methylene chloride) is 4.0 or less.

2. The polyester carbonate according to claim 1 , wherein the stereostructural component unit has a fluorene-based component unit and/or a binaphthyl-based component unit.

3. The polyester carbonate according to claim 1 , which contains 70 mol % or more of the stereostructural component unit based on all units.

4. The polyester carbonate according to claim 1 , which is substantially free of titanium, germanium, antimony and tin.

5. An optical member comprising the polyester carbonate according to claim 1 .

6. The optical member according to claim 5 , which is an optical lens.

7. A method of producing the polyester carbonate according to claim 1 , comprising:
subjecting a carbonate ester, a carboxylic acid or an ester-forming derivative thereof and
(i) a diol represented by the following formula (A),

wherein
each ring Z is the same or different and represents an aromatic group or a fused polycyclic aromatic group,
R a and R b independently represent a hydrogen atom, a halogen atom or a hydrocarbon group having a carbon number of 1 to 12 or a carbon number of 1 to 20, which may contain an aromatic group,
Ar 1 and Ar 2 represent a hydrogen atom or an aromatic group having a carbon number of 6 to 10, which may contain a substituent,
L 1 and L 2 independently represent a divalent linking group, and
m and n independently represent 0 or 1, and/or
(ii) a diol represented by the following formula (B),

wherein
R 11 and R 12 independently represent a hydrocarbon group having a carbon number of 1 to 10, which may contain an aromatic group,
and p independently represent an integer of 0 or more,
R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a hydrocarbon group having a carbon number of 1 to 20, which may contain an aromatic group,
to a transesterification reaction in the presence of a catalyst, wherein the catalyst comprises aluminum or a compound thereof, and a phosphorus compound,
to produce the polyester carbonate having a refractive index nD of 1.672 or more, and wherein
the specific viscosity measured for a solution prepared by dissolving the polyester carbonate at 0.52 mass % in methylene chloride (a solution prepared by dissolving 0.7 g of the polyester carbonate in 100 ml of methylene chloride) is from 0.12 to 0.40, and
the b* value of CIE1976 (L*a*b*) color system measured for a solution prepared by dissolving the polyester carbonate at 13 mass % in methylene chloride (a solution prepared by dissolving 1.0 g of the polyester carbonate in 5 ml of methylene chloride) is 4.0 or less.

8. The method according to claim 7 , wherein the phosphorus compound is at least one compound selected from the group consisting of a phosphonic acid-based compound, a phosphinic acid-based compound, a phosphine oxide-based compound, a phosphonous acid-based compound, a phosphinous acid-based compound, and a phosphine-based compound.

9. The method according to claim 7 , wherein the aluminum or a compound thereof is an aluminum salt, an aluminum alkoxide, or an aluminum chelate compound.

10. The method according to claim 7 , wherein the carbonate ester is diphenyl carbonate.

11. The method according to claim 7 , wherein the catalyst is used in an amount of 8×10 −5 mol or more and 1×10 −3 mol or less per mol of the total of all monomer units used.

12. The method according to claim 7 , wherein the stereostructural component unit has a fluorene-based component unit and/or a binaphthyl-based component unit.

Assignees

• Teijin Ltd

Inventors

• Nunome Kazunori
• Matsui Manabu
• Yanagida Takatsune
• Ogasawara Kazuyoshi
• Sato Keisuke
• Yamada Kyosuke
• Oyama Tatsuya

Classifications

• C08G64/305 Primary

  and alcohols · CPC title

• C08G64/307

  and phenols · CPC title

• C08G63/87

  Non-metals or inter-compounds thereof (boron C08G63/84) · CPC title

• C08G63/64 Primary

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

• C08G64/06

  not containing aliphatic unsaturation · CPC title