Polycarbonate copolymer, and coating liquid and electrophotographic photosensitive body using same

Patent metadata

Field	Value
Publication number	US-9529285-B2
Application number	US-201214369570-A
Country	US
Kind code	B2
Filing date	Dec 26, 2012
Priority date	Dec 27, 2011
Publication date	Dec 27, 2016
Grant date	Dec 27, 2016

Abstract

A polycarbonate copolymer, a coating liquid and an electrophotographic photosensitive body are provided. The polycarbonate copolymer has good abrasion resistance and stable solubility in an organic solvent. The copolymer comprises a repeating unit A of formula (1); a repeating unit B of formula (2); and a repeating unit C of formula (3), in which: the polycarbonate copolymer has a presence ratio represented by
Ar 1 /(Ar 1 +Ar 2 +Ar 3 ) of from 50 to 65 mol %, a presence ratio represented by
Ar 2 /(Ar 1 +Ar 2 +Ar 3 ) of from 25 to 45 mol %, and a presence ratio represented by
Ar 3 /(Ar 1 +Ar 2 +Ar 3 ) of from 3 to 25 mol %:

Ar 1 , Ar 2 , and Ar 3 are each independently a divalent aromatic group, and X 1 and X 2 are each independently a single bond or —NH—, provided that Ar 1 and Ar 2 are not identical to each other. In the copolymer the repeating units B are not directly bonded to each other.

First claim

The invention claimed is:

1. A polycarbonate copolymer, comprising:
a repeating unit A of formula (1);
a repeating unit B of formula (2); and
a repeating unit C of formula (3),
wherein:
the polycarbonate copolymer has
a presence ratio represented by Ar 1 /(Ar 1 +Ar 2 +Ar 3 ) of from 50 to 65 mol %,
a presence ratio represented by Ar 2 /(Ar 1 +Ar 2 +Ar 3 ) of from 25 to 45 mol %, and
a presence ratio represented by Ar 3 /(Ar 1 +Ar 2 +Ar 3 ) of from 3 to 25 mol %; and
the repeating units B are not directly bonded to each other:

wherein,
Ar 1 , Ar 2 , and Ar 3 are each independently a divalent aromatic group, and X 1 and X 2 are each independently a single bond or —NH—, with the proviso that Ar 1 and Ar 2 are not identical to each other.

2. The polycarbonate copolymer according to claim 1 , wherein Ar 1 is of formula (4):

wherein
R 1 and R 2 are each independently a halogen atom, an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an optionally substituted aryl group having 6 to 12 ring-forming carbon atoms, an optionally substituted alkoxy group having 1 to 12 carbon atoms, an optionally substituted aryloxy group having 6 to 12 ring-forming carbon atoms, or an optionally substituted arylalkyl group having 7 to 20 carbon atoms;
p1 and p2 are each independently an integer of from 0 to 4,
wherein when p1 is an integer of 2 or more, a plurality of R 1 may be identical to or different from each other, and when p2 is an integer of 2 or more, a plurality of R 2 may be identical to or different from each other;
X 3 is a single bond, —O—, —CO—, —S—, —SO—, —SO 2 —, —CR 3 R 4 —, an optionally substituted cycloalkylidene group having 5 to 20 carbon atoms, an optionally substituted bicyclo- or tricyclo-hydrocarbon-diyl group having 5 to 20 carbon atoms, an optionally substituted α,ω-alkylene group having 2 to 12 carbon atoms, an optionally substituted 9,9-fluorenylidene group, an optionally substituted 1,8-menthanediyl group, an optionally substituted 2,8-menthanediyl group, an optionally substituted arylene group having 6 to 12 ring-forming carbon atoms, any one of divalent groups of formulae (5), or an alkylidene-arylene-alkylidene group having 8 to 16 carbon atoms of formula (6); and
R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, or an optionally substituted aryl group having 6 to 12 ring-forming carbon atoms:

wherein,
R 5 to R 7 are each independently a halogen atom, an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an optionally substituted aryl group having 6 to 12 ring-forming carbon atoms, an optionally substituted alkoxy group having 1 to 12 carbon atoms, an optionally substituted aryloxy group having 6 to 12 ring-forming carbon atoms, or an optionally substituted arylalkyl group having 7 to 20 carbon atoms;

wherein,
R 8 to R 11 are each independently a halogen atom, an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an optionally substituted aryl group having 6 to 12 ring-forming carbon atoms, an optionally substituted alkoxy group having 1 to 12 carbon atoms, an optionally substituted aryloxy group having 6 to 12 ring-forming carbon atoms, or an optionally substituted arylalkyl group having 7 to 20 carbon atoms.

3. The polycarbonate copolymer according to claim 1 , wherein Ar 2 and Ar 3 are each independently an optionally substituted naphthylene group or a divalent group of formula (7):

wherein
X 4 is a single bond, —O—, —CO—, —S—, —SO—, —SO 2 —, —CONH—, —CR 6 R 7 —, —O—R 8 —O—, an optionally substituted cycloalkylidene group having 5 to 20 carbon atoms, an optionally substituted bicyclo- or tricyclo-hydrocarbon-diyl group having 5 to 20 carbon atoms, an optionally substituted am-alkylene group having 2 to 12 carbon atoms, an optionally substituted 9,9-fluorenylidene group, an optionally substituted 1,8-menthanediyl group, an optionally substituted 2,8-menthanediyl group, an optionally substituted pyrazylidene group, an optionally substituted arylene group having 6 to 12 ring-forming carbon atoms, any one of divalent groups of formulae (5), or an alkylidene-arylene-alkylidene group having 8 to 16 carbon atoms of formula (6);
R 6 and R 7 are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, or an optionally substituted aryl group having 6 to 12 ring-forming carbon atoms;
R 8 is at least one of a carbonyl group, an alkylene group having 1 to 6 carbon atoms, a haloalkylene group having 1 to 6 carbon atoms and an arylene group having 6 to 12 ring-forming carbon atoms;
R 12 and R 13 are each independently a halogen atom, an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an optionally substituted aryl group having 6 to 12 ring-forming carbon atoms, an optionally substituted alkoxy group having 1 to 12 carbon atoms, an optionally substituted aryloxy group having 6 to 12 ring-forming carbon atoms, or an optionally substituted arylalkyl group having 7 to 20 carbon atoms;
p3 and p4 are each independently an integer of from 0 to 4,
wherein when p3 is an integer of 2 or more, a plurality of R 12 may be identical to or different from each other, and when p4 is an integer of 2 or more, a plurality of R 13 may be identical to or different from each other; and
n 0 is an integer of from 0 to 2, and when n 0 is 2, a plurality of R 12 may be identical to or different from each other, a plurality of p3 may be identical to or different from each other, and a plurality of X 4 may be identical to or different from each other:

wherein
R 5 to R 7 are each independently a halogen atom, an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an optionally substituted aryl group having 6 to 12 ring-forming carbon atoms, an optionally substituted alkoxy group having 1 to 12 carbon atoms, an optionally substituted aryloxy group having 6 to 12 ring-forming carbon atoms, or an optionally substituted arylalkyl group having 7 to 20 carbon atoms

wherein
R 8 to R 11 are each independently a halogen atom, an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an optionally substituted aryl group having 6 to 12 ring-forming carbon atoms, an optionally substituted alkoxy group having 1 to 12 carbon atoms, an optionally substituted aryloxy group having 6 to 12 ring-forming carbon atoms, or an optionally substituted arylalkyl group having 7 to 20 carbon atoms.

4. The polycarbonate copolymer according to claim 2 , wherein X 3 in the formula (4) is —CR 3 R 4 —, an optionally substituted cycloalkylidene group having 5 to 20 carbon atoms, or an optionally substituted bicyclo- or tricyclo-hydrocarbon-diyl group having 5

Assignees

• Idemitsu Kosan Co

Inventors

• Hirata Kengo

Classifications

• C08G69/44

  Polyester-amides · CPC title

• C09D169/005

  Polyester-carbonates · CPC title

• C08G64/24

  and phenols · CPC title

• C09D169/00

  Coating compositions based on polycarbonates; Coating compositions based on derivatives of polycarbonates · CPC title

• C09D177/12

  Polyester-amides · CPC title