Polycarbonate copolymer and preparation method therefor

Patent metadata

Field	Value
Publication number	US-10081708-B2
Application number	US-201515537562-A
Country	US
Kind code	B2
Filing date	Dec 18, 2015
Priority date	Dec 19, 2014
Publication date	Sep 25, 2018
Grant date	Sep 25, 2018

Abstract

The present invention relates to a polycarbonate copolymer and a preparation method therefor and, more specifically, to a polycarbonate copolymer comprising a fluorene ester oligomer and a polycarbonate as polymerization units, and a preparation method therefor.

First claim

What is claimed is:

1. A polycarbonate copolymer comprising, as polymerization units,
a fluorene ester oligomer prepared from: a compound having a fluorene backbone selected from dicarboxylic compounds, dihalide compounds, dicyanide compounds and combinations thereof; and a dihydroxy compound; and
a polycarbonate.

2. The polycarbonate copolymer according to claim 1 , wherein the compound having a fluorene backbone is represented by the following formula 1:

wherein,
each of R 1 and R 2 is independently hydrogen, an alkyl group having 1 to 30 carbons, a cycloalkyl group having 3 to 30 carbons, or an aryl group having 6 to 30 carbons;
each of X 1 and X 2 is independently an alkylene group having 1 to 30 carbons, a cycloalkylene group having 3 to 30 carbons, an arylene group having 6 to 30 carbons, or

where Z is O, N, S or (C═O), and each of m and n is an integer of 0 to 30;
k is an integer of 0 to 5; and
Y is carboxylic group, acyl group, halogen group, carbonyl halide or isocyano group.

3. The polycarbonate copolymer according to claim 1 , wherein the dihydroxy compound is selected from the group consisting of bis(4-hydroxyphenyl)methane, bis(4-hydroxyphenyl)phenylmethane, bis(4-hydroxyphenyl)naphthylmethane, bis(4-hydroxyphenyl)-(4-isobutylphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 1-ethyl-1,1-bis(4-hydroxyphenyl)propane, 1-phenyl-1,1-bis(4-hydroxyphenyl)ethane, 1-naphthyl-1,1-bis(4-hydroxypheny)pethane, 1,2-bis(4-hydroxyphenyl)ethane, 1,10-bis(4-hydroxyphenyl)decane, 2-methyl-1,1-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)pentane, 2,2-bis(4-hydroxyphenyl)hexane, 2,2-bis(4-hydroxyphenyl)nonane, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 2,2-bis(3-fluoro-4-hydroxyphenyl)propane, 4-methyl-2,2-bis(4-hydroxyphenyl)pentane, 4,4-bis(4-hydroxyphenyl)heptane, diphenyl-bis(4-hydroxyphenyl)methane, resorcinol, hydroquinone, 4,4′-dihydroxyphenyl ether [bis(4-hydroxyphenyl)ether], 4,4′-dihydroxy-2,5-dihydroxydiphenyl ether, 4,4′-dihydroxy-3,3′-dichlorodiphenyl ether, bis(3,5-dimethyl-4-hydroxyphenyl)ether, bis(3,5-dichloro-4-hydroxyphenyl)ether, 1,4-dihydroxy-2,5-dichlorobenzene, 1,4-dihydroxy-3-methylbenzene, 4,4′-dihydroxydiphenol [p,p′-dihydroxyphenyl], 3,3′-dichloro-4,4′-dihydroxyphenyl, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(3,5-dimethyl-4-hydroxyphenyl)cyclohexane, 1,1-bis(3,5-dichloro-4-hydroxyphenyl)cyclohexane, 1,1-bis(3,5-dimethyl-4-hydroxyphenyl)cyclododecane, 1,1-bis(4-hydroxyphenyl)cyclododecane, 1,1-bis(4-hydroxyphenyl)butane, 1,1-bis(4-hydroxyphenyl)decane, 1,4-bis(4-hydroxyphenyl)propane, 1,4-bis(4-hydroxyphenyl)butane, 1,4-bis(4-hydroxyphenyl)isobutane, 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(3-chloro-4-hydroxyphenyl)propane, bis(3,5-dimethyl-4-hydroxyphenyl)methane, bis(3,5-dichloro-4-hydroxyphenyl)methane, 2,2-bis(3,5-dimethyl-4-hydroxyphenyl)propane, 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane, 2,2-bis(3,5-dichloro-4-hydroxyphenyl)propane, 2,4-bis(4-hydroxyphenyl)-2-methyl-butane, 4,4′-thiodiphenol [bis(4-hydroxyphenyl)sulfone], bis(3,5-dimethyl-4-hydroxyphenyl)sulfone, bis(3-chloro-4-hydroxyphenyl)sulfone, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxyphenyl)sulfoxide, bis(3-methyl-4-hydroxyphenyl)sulfide, bis(3,5-dimethyl-4-hydroxyphenyl)sulfide, bis(3,5-dibromo-4-hydroxyphenyl)sulfoxide, 4,4′-dihydroxybenzophenone, 3, 3′, 5, 5′-tetramethyl-4,4′-dihydroxybenzophenone, 4,4′-dihydroxy diphenyl, methylhydroquinone, 1,5-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, isosorbide, isomannide, isoidide and combinations thereof.

4. The polycarbonate copolymer according to claim 1 , wherein the fluorene ester oligomer has a viscosity average molecular weight of 1,000 to 8,000.

5. The polycarbonate copolymer according to claim 1 , wherein the copolymer has a viscosity average molecular weight of 10,000 to 80,000.

6. A method for preparing a polycarbonate copolymer, comprising the steps of:
(1) polymerizing a fluorene ester oligomer by reacting a compound having a fluorene backbone selected from dicarboxylic compounds, dihalide compounds, dicyanide compounds and combinations thereof; and a dihydroxy compound; and
(2) copolymerizing the fluorene ester oligomer obtained in said step (1) and a polycarbonate in the presence of a first polymerization catalyst.

7. The method for preparing a polycarbonate copolymer according to claim 6 , wherein the compound having a fluorene backbone is represented by the following formula 1:

wherein,
each of R 1 and R 2 is independently hydrogen, an alkyl group having 1 to 30 carbons, a cycloalkyl group having 3 to 30 carbons, or an aryl group having 6 to 30 carbons;
each of X 1 and X 2 is independently an alkylene group having 1 to 30 carbons, a cycloalkylene group having 3 to 30 carbons, an arylene group having 6 to 30 carbons, or

where Z is O, N, S or (C═O), and each of m and n is an integer of 0 to 30;
k is an integer of 0 to 5; and
Y is carboxylic group, acyl group, halogen group, carbonyl halide or isocyano group.

8. The method for preparing a polycarbonate copolymer according to claim 6 , wherein in step (2), the fluorene ester oligomer is used in an amount of 10 to 50% by weight based on the total weight of reactants.

9. A molded product comprising the polycarbonate copolymer of claim 1 .

10. The molded product according to claim 9 , which is an optical material or an automotive part.

Assignees

• Samyang Corp

Inventors

• Shin Kyung Moo
• Son So Ri
• Kim Mi Ran
• Kim Ji Eun

Classifications

• C08G64/42

  Chemical after-treatment · CPC title

• C08L69/00

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

• C08G18/3215

  containing aromatic groups or benzoquinone groups · CPC title

• C08G63/64

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

• C08G64/06 Primary

  not containing aliphatic unsaturation · CPC title