JP2017082097A5 - - Google Patents

Claims (7)

A method for producing a polyester resin comprising a repeating unit represented by the following formula (1) and a repeating unit represented by the following formula (2), wherein the divalent phenol represented by the following formula (4-1) and the following A step of reacting the dicarboxylic acid chloride represented by the formula (5) to obtain an ester oligomer, and a reaction of the ester oligomer with a dihydric phenol represented by the following formula (4-2) to obtain a polyester resin. A method for producing a polyester resin, comprising a step, wherein a residual amount of a dicarboxylic acid chloride monomer represented by the following formula (5) in the ester oligomer satisfies the following formula (6):

(In formula (1), X ¹ is a divalent group represented by the following formula (3), and Y ¹ and Y ² are each independently a divalent group. In formula (2), X ² is a group containing a divalent aromatic group, provided that Y
¹ may be the same as Y ² and X ² is not the same as X ¹ . )

(In the formula ^{(3), R 1, R} 2 are each independently a hydrogen atom, an alkyl group which may have a substituent having 1 to 20 carbon atoms, an optionally substituted group having 1 to 20 carbon atoms Represents an alkoxyl group which may be substituted, or an aromatic group which may have a substituent having 1 to 20 carbon atoms, and n ¹ and n ² each represent an integer of 0 to ^4. R ³ and R ⁴ represent Each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aromatic group optionally having a substituent having 1 to 20 carbon atoms, provided that R ³ and R ⁴ are bonded to each other; A ring may be formed.)

In the step of obtaining the ester oligomer, the charged molar ratio of the dihydric phenol represented by the formula (4-1) and the dicarboxylic acid chloride represented by the formula (5) is

The method for producing a polyester resin according to claim 1, wherein: In the formula (2), X ^2, characterized in that at least one divalent group containing an aromatic selected from the following formulas (7) to (10), according to claim 1 or 2 Of manufacturing polyester resin.

(In the formula (7), R ⁵ is a hydrogen atom, an alkyl group which may have a substituent having 1 to 20 carbon atoms, an alkoxyl group which may have a substituent having 1 to 20 carbon atoms, carbon. 1-20 substituents aromatic group which may have a, or a halogen group, n ³ is an integer of 0-4.)

(In the formula (8), R ⁶ is a hydrogen atom, an alkyl group which may have a substituent having 1 to 20 carbon atoms, optionally alkoxyl group which may have a substituent having 1 to 20 carbon atoms, carbon 1-20 substituents aromatic group which may have a, or a halogen group, n ⁴ represents an integer of 0-6.)

(In Formula (9), R <^7> , R < ⁸ > has a hydrogen atom, the alkyl group which may have a C1-C20 substituent, and a C1-C20 substituent each independently. An alkoxyl group,
An aromatic group which may have a substituent having 1 to 20 carbon atoms or a halogen group, and n ⁵ , n
⁶ represents an integer of 0 to 4. W ¹ represents any ^one of a single bond, an oxygen atom, a sulfur atom, and a methylene group. )

(In Formula (10), Ar ¹ and Ar ² each independently represent an arylene group which may have a substituent having 6 to 16 carbon atoms. Z represents an arylene which may have a substituent. Represents an alkylene group having 2 to 20 carbon atoms which may have a group or a substituent, and s represents an integer of 0 or 1.) The content of the repeating unit represented by the formula (2) in the polyester resin is the formula (1).
) 0.45 ≧ (2) / ((1) + (2)) ≧ 0.0 in terms of molar ratio with the repeating unit represented by
5. The method for producing a polyester resin according to claim 1, wherein: 5 is satisfied. In said Formula (1) and Formula (2), Y < ¹ >, Y < ² > is a bivalent group represented by following formula (11), The any one of Claims 1-4 characterized by the above-mentioned. The manufacturing method of the polyester resin as described in 2.

(In formula (11), Ar ³ and Ar ⁴ each independently represent an arylene group optionally having a substituent. Z represents a single bond, an oxygen atom, a sulfur atom, or formula (12). Structure or formula (
13) represents a divalent group having the structure represented by R ⁹ and R ^{10 in} Formula (12) each independently represent a hydrogen atom, an alkyl group, an aryl group, or a cycloalkylidene group formed by combining R ⁹ and R ¹⁰ . Furthermore, in formula (13), R ¹¹ represents an alkylene group, an arylene group, or a group represented by formula (14). In formula (14), R ¹² and R ¹³ each independently represent an alkylene group, and Ar ⁵ represents an arylene group. k represents an integer of 0 to 5. )

The method for producing the polyester resin is a solution polymerization method.
The manufacturing method of the polyester resin of any one of these. In an electrophotographic photosensitive member having at least a photosensitive layer on a conductive support, the photosensitive layer comprises:
A polyester resin containing a repeating unit represented by the following formula (1) and a repeating unit represented by the following formula (2) is contained, and the polyester resin is a residual dicarboxylic acid chloride monomer represented by the following formula (5): An ester oligomer satisfying the following formula (6) and the following formula (4-2)
The ester oligomer is a reaction product with a dihydric phenol represented by the following formula (4-1):
) Reaction of a dihydric phenol represented by the formula (5) with a dicarboxylic acid chloride represented by the following formula (5)
An electrophotographic photoreceptor, which is a product.

(In formula (1), X ¹ is a divalent group represented by the following formula (3), and Y ¹ and Y ² are each independently a divalent group. In formula (2), X ² is a group containing a divalent aromatic group, provided that X
² is not the same as ^{X 1.} )

(In the formula ^{(3), R 1, R} 2 are each independently a hydrogen atom, an alkyl group which may have a substituent having 1 to 20 carbon atoms, an optionally substituted group having 1 to 20 carbon atoms Represents an alkoxyl group which may be substituted, or an aromatic group which may have a substituent having 1 to 20 carbon atoms, and n ¹ and n ² each represent an integer of 0 to ^4. R ³ and R ⁴ represent Each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aromatic group optionally having a substituent having 1 to 20 carbon atoms, provided that R ³ and R ⁴ are bonded to each other; A ring may be formed.)