JP2015184331A5

JP2015184331A5 -

Info

Publication number: JP2015184331A5
Application number: JP2014058188A
Authority: JP
Filing date: 2014-03-20
Publication date: 2016-12-15
Anticipated expiration: 2034-03-20

Description

本発明の実施形態は、少なくとも、炭素数９〜２４のアルキル基を有するエチレン性不飽和単量体（ｃ−１）（ただし、下記（ｃ−２）である場合を除く）と、下記一般式（１）で表されるエチレン性不飽和単量体（ｃ−２）と，下記一般式（２）で表されるエチレン性不飽和単量体（ｃ−３）、もしくは下記一般式（３）で表されるエチレン性不飽和単量体（ｃ−４）とを共重合してなる、液体現像剤用の高分子分散剤に関する。
一般式（１）

ＣＨ₂＝Ｃ（Ｒ１）ＣＯＯ（ＡＯ）ｎＲ２

（式中、Ｒ１は水素原子又はＣＨ ₃ 基を表し、
Ｒ２は水素原子又は炭素数が１〜２２の炭化水素基を表し、
ｎは１〜２００の整数を表し、
Ａは炭素数が２〜４のアルキレン基を表す。）
一般式（２）

ＣＨ（Ｒ３）＝Ｃ（Ｒ４）ＣＯＮＲ５Ｒ６

（式中、Ｒ３は水素原子、又は、アルコキシル基、水酸基、および、カルボキシル基のいずれかを有しても良い炭素数が１〜８の炭化水素基を表し、
Ｒ４は水素原子又はＣＨ ₃ 基を表し、
Ｒ５、Ｒ６は水素原子又はアルコキシル基、水酸基、カルボキシル基を有しても良い炭素数が１〜８の炭化水素基を表し、
Ｒ５とＲ６は、環を形成しても良く、
Ｒ３とＲ５が、カルボニル基を含む環を形成しても良い。）
一般式（３）

ＣＨ₂＝ＣＨＮ（Ｒ７）（ＣＯ）Ｒ８

（式中、Ｒ７、Ｒ８は水素原子又はアルコキシル基、水酸基、カルボキシル基を有しても良い炭素数が１〜８の炭化水素基を表し、
Ｒ７とＲ８が、カルボニル基を含む環を形成しても良い。） Embodiments of the present invention include at least an ethylenically unsaturated monomer (c-1) having an alkyl group having 9 to 24 carbon atoms (except for the case of (c-2) below) and the following general The ethylenically unsaturated monomer (c-2) represented by the formula (1), the ethylenically unsaturated monomer (c-3) represented by the following general formula (2), or the following general formula ( The present invention relates to a polymer dispersant for a liquid developer obtained by copolymerizing the ethylenically unsaturated monomer (c-4) represented by 3).
General formula (1)

_{CH 2 = C (R1) COO} (AO) nR2

(Wherein, R1 represents a hydrogen atom or a CH ₃ group,
R2 represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms ,
n represents an integer of 1 to 200,
A represents an alkylene group having 2 to 4 carbon atoms. )
General formula (2)

CH (R3) = C (R4) CONR5R6

(In the formula, R3 represents a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms which may have any of an alkoxyl group, a hydroxyl group and a carboxyl group ;
R4 represents a hydrogen atom or a CH ₃ group,
R5 and R6 represent a hydrogen atom or an alkoxyl group, a hydroxyl group, a hydrocarbon group having 1 to 8 carbon atoms which may have a carboxyl group ,
R5 and R6 may form a ring,
R3 and R5 may form a ring containing a carbonyl group. )
General formula (3)

CH ₂ = CHN (R7) (CO) R8

(Wherein R7 and R8 represent a hydrogen atom or an alkoxyl group, a hydroxyl group, a hydrocarbon group having 1 to 8 carbon atoms which may have a carboxyl group,
R7 and R8 may form a ring containing a carbonyl group. )

一般式（１）
ＣＨ₂＝Ｃ（Ｒ１）ＣＯＯ（ＡＯ）ｎＲ２
（式中、Ｒ１は水素原子又はＣＨ ₃ 基を表し、Ｒ２は水素原子又は炭素数が１〜２２の炭化水素基を表し、ｎは１〜２００の整数を表し、Ａは炭素数が２〜４のアルキレン基を表す。） General formula (1)
_{CH 2 = C (R1) COO} (AO) nR2
(In the formula, R 1 represents a hydrogen atom or a CH ₃ group , R 2 represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms , n represents an integer of 1 to 200, and A represents 2 to 2 carbon atoms. 4 represents an alkylene group.)

一般式（２）において、Ｒ３は水素原子、又は、アルコキシル基、水酸基、および、カルボキシル基のいずれかを有しても良い炭素数が１〜８の炭化水素基を表し、Ｒ４は水素原子又はＣＨ ₃ 基を表し、Ｒ５、Ｒ６は水素原子又はアルコキシル基、水酸基、カルボキシル基を有しても良い炭素数が１〜８の炭化水素基を表し、Ｒ５とＲ６は、環を形成しても良く、Ｒ３とＲ５が、カルボニル基を含む環を形成しても良い。 In the general formula (2), R3 represents a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms which may have any of an alkoxyl group, a hydroxyl group and a carboxyl group, and R4 represents a hydrogen atom or represents CH ₃ group, R5, R6 is hydrogen atom or an alkoxyl group, a hydroxyl group, carbon atoms, which may have a carboxyl group represents a 1-8 hydrocarbon group, R5 and R6, may form a ring R3 and R5 may form a ring containing a carbonyl group.

一般式（２）で表されるエチレン性不飽和単量体（ｃ−３）としては、Ｎ−ヒドロキシエチル（メタ）アクリルアミド〔Ｎ−ヒドロキシエチルアクリルアミドとＮ−ヒドロキシエチルメタクリルアミドとを併せて「Ｎ−ヒドロキシエチル（メタ）アクリルアミド」と表記する。以下同様。〕、Ｎ−ヒドロキシプロピル（メタ）アクリルアミド、Ｎ−ヒドロキシブチル（メタ）アクリルアミド、Ｎ−ヒドロキシヘキシル（メタ）アクリルアミド、Ｎ−ヒドロキシオクチル（メタ）アクリルアミド等の水酸基含有の（メタ）アクリルアミド類；Ｎ−（２−オキソブタノイルエチル）（メタ）アクリルアミド、Ｎ−（２−オキソブタノイルプロピル）（メタ）アクリルアミド、Ｎ−（２−オキソブタノイルブチル）（メタ）アクリルアミド、ダイアセトン（メタ）アクリルアミド等のカルボニル基を有する（メタ）アクリルアミド類；
（メタ）アクリルアミド、Ｎ−メチル（メタ）アクリルアミド、Ｎ−エチル（メタ）アクリルアミド、Ｎ−プロピル（メタ）アクリルアミド、Ｎ−イソプロピル（メタ）アクリルアミド、Ｎ−ブチル（メタ）アクリルアミド、Ｎ−プロピル（メタ）アクリルアミド、Ｎ−ｔｅｒｔ−ブチル（メタ）アクリルアミド、Ｎ−ヘキシル（メタ）アクリルアミド、Ｎ−オクチル（メタ）アクリルアミド、Ｎ−（４−カルバモイルフェニル）（メタ）アクリルアミド、β−（２−フリル）（メタ）アクリルアミド、２，３−ビス（２−フリル）アクリルアミド、Ｎ−（９Ｈ−フルオレン−２−イル）（メタ）アクリルアミド、Ｎ−（５，５−ジメチルヘキシル）（メタ）アクリルアミド、Ｎ，Ｎ−ジエチル−（メタ）アクリルアミド、Ｎ−（ジブチルアミノメチル）（メタ）アクリルアミド、Ｎ，Ｎ−ジメチル（メタ）アクリルアミド、Ｎ，Ｎ−ジエチル−（メタ）アクリルアミド、クロトンアミド、マレインアミド、フマルアミド、メサコンアミド、シトラコンアミド、イタコンアミド、３−フェニル−２−プロペンアミドなどの脂肪族系、あるいは芳香族系の（メタ）アクリルアミド類；
Ｎ−メトキシメチル（メタ）アクリルアミド、Ｎ−メトキシエチル（メタ）アクリルアミド、Ｎ−メトキシプロピル（メタ）アクリルアミド、Ｎ−メトキシブチル（メタ）アクリルアミド、Ｎ−メトキシヘキシル（メタ）アクリルアミド、Ｎ−メトキシオクチル（メタ）アクリルアミド、Ｎ−メトキシデシル（メタ）アクリルアミド、Ｎ−メトキシドデシル（メタ）アクリルアミド、Ｎ−メトキシオクタデシル（メタ）アクリルアミド、Ｎ−エトキシメチル（メタ）アクリルアミド、Ｎ−エトキシエチル（メタ）アクリルアミド、Ｎ−エトキシプロピル（メタ）アクリルアミド、Ｎ−エトキシブチル（メタ）アクリルアミド、Ｎ−エトキシヘキシル（メタ）アクリルアミド、Ｎ−エトキシオクチル（メタ）アクリルアミド、Ｎ−イソプロポキシメチル（メタ）アクリルアミド、Ｎ−イソプロポキシエチル（メタ）アクリルアミド、Ｎ−イソプロポキシプロピル（メタ）アクリルアミド、Ｎ−イソプロポキシブチル（メタ）アクリルアミド、Ｎ−イソプロポキシヘキシル（メタ）アクリルアミド、Ｎ−イソプロポキシオクチル（メタ）アクリルアミド、Ｎ−ブトキシメチル（メタ）アクリルアミド、Ｎ−ブトキシエチル（メタ）アクリルアミド、Ｎ−ブトキシプロピル（メタ）アクリルアミド、Ｎ−ブトキシブチル（メタ）アクリルアミド、Ｎ−ブトキシヘキシル（メタ）アクリルアミド、Ｎ−ブトキシオクチル（メタ）アクリルアミド、Ｎ−イソブトキシメチル（メタ）アクリルアミド、Ｎ−イソブトキシエチル（メタ）アクリルアミド、Ｎ−イソブトキシプロピル（メタ）アクリルアミド、Ｎ−イソブトキシブチル（メタ）アクリルアミド、Ｎ−イソブトキシヘキシル（メタ）アクリルアミド、Ｎ−イソブトキシオクチル（メタ）アクリルアミド、Ｎ，Ｎ−ジ（メトキシメチル）メタ）アクリルアミド、Ｎ，Ｎ−ジ（エトキシメチル）（メタ）アクリルアミド、等のＮ−アルコキシ基含有の（メタ）アクリルアミド類；
４−アクリロイルモルホリンなどの複素環アミン基含有（メタ）アクリルアミド類；マレイミド、メチルマレイミド、エチルマレイミド、プロピルマレイミド、ブチルマレイミド、オクチルマレイミド、フェニルマレイミドなどのマレイミド誘導体類などが挙げられる。
また、これらは２種類以上を併用しても良い。 Examples of the ethylenically unsaturated monomer (c-3) represented by the general formula (2) include N-hydroxyethyl (meth) acrylamide [N-hydroxyethylacrylamide and N-hydroxyethylmethacrylamide together. It describes with "N-hydroxyethyl (meth) acrylamide". The same applies below. ], Hydroxyl-containing (meth) acrylamides such as N-hydroxypropyl (meth) acrylamide, N-hydroxybutyl (meth) acrylamide, N-hydroxyhexyl (meth) acrylamide, N-hydroxyoctyl (meth) acrylamide; N- (2-oxobutanoylethyl) (meth) acrylamide, N- (2-oxobutanoylpropyl) (meth) acrylamide, N- (2-oxobutanoylbutyl) (meth) acrylamide, diacetone (meth) acrylamide, etc. (Meth) acrylamides having a carbonyl group of
(Meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-butyl (meth) acrylamide, N-propyl (meth) ) Acrylamide, N-tert-butyl (meth) acrylamide, N-hexyl (meth) acrylamide, N-octyl (meth) acrylamide, N- (4-carbamoylphenyl) (meth) acrylamide, β- (2-furyl) ( (Meth) acrylamide, 2,3-bis (2-furyl) acrylamide, N- (9H-fluoren-2-yl) (meth) acrylamide, N- (5,5-dimethylhexyl) (meth) acrylamide, N, N -Diethyl- (meth) acrylamide, N- (dibutyla Nomethyl) (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl- (meth) acrylamide, crotonamide, maleinamide, fumaramide, mesaconamide, citraconic amide, itaconic amide, 3-phenyl-2- Aliphatic or aromatic (meth) acrylamides such as propenamide;
N-methoxymethyl (meth) acrylamide, N-methoxyethyl (meth) acrylamide, N-methoxypropyl (meth) acrylamide, N-methoxybutyl (meth) acrylamide, N-methoxyhexyl (meth) acrylamide, N-methoxyoctyl ( (Meth) acrylamide, N-methoxydecyl (meth) acrylamide, N-methoxydodecyl (meth) acrylamide, N-methoxyoctadecyl (meth) acrylamide, N-ethoxymethyl (meth) acrylamide, N-ethoxyethyl (meth) acrylamide, N -Ethoxypropyl (meth) acrylamide, N-ethoxybutyl (meth) acrylamide, N-ethoxyhexyl (meth) acrylamide, N-ethoxyoctyl (meth) acrylamide, N-isopropoxy Methyl (meth) acrylamide, N-isopropoxyethyl (meth) acrylamide, N-isopropoxypropyl (meth) acrylamide, N-isopropoxybutyl (meth) acrylamide, N-isopropoxyhexyl (meth) acrylamide, N-isopropoxy Octyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide, N-butoxyethyl (meth) acrylamide, N-butoxypropyl (meth) acrylamide, N-butoxybutyl (meth) acrylamide, N-butoxyhexyl (meth) acrylamide N-butoxyoctyl (meth) acrylamide, N-isobutoxymethyl (meth) acrylamide, N-isobutoxyethyl (meth) acrylamide, N-isobutoxypropyl (meth) acryl Amide, N-isobutoxybutyl (meth) acrylamide, N-isobutoxyhexyl (meth) acrylamide, N-isobutoxyoctyl (meth) acrylamide, N, N-di (methoxymethyl) meth) acrylamide, N, N-di N-alkoxy group-containing (meth) acrylamides such as (ethoxymethyl) (meth) acrylamide;
Examples include heterocyclic amine group- containing (meth) acrylamides such as 4-acryloylmorpholine; maleimide derivatives such as maleimide, methylmaleimide, ethylmaleimide, propylmaleimide, butylmaleimide, octylmaleimide, and phenylmaleimide.
Two or more of these may be used in combination.

一般式（３）で表されるエチレン性不飽和単量体（ｃ−４）としては、Ｎ−ビニル−２−ピロリドン、Ｎ−ビニル−ε−カプロラクタムなどのビニル環状アミド類；
Ｎ-ビニルコハク酸イミド、Ｎ−ビニルアセトアミドなどが挙げられる。
また、これらは２種類以上を併用しても良い。

Examples of the ethylenically unsaturated monomer (c-4) represented by the general formula (3) include vinyl cyclic amides such as N-vinyl-2-pyrrolidone and N-vinyl-ε-caprolactam;
N-vinyl succinimide, N-vinyl acetamide, etc. are mentioned.
Two or more of these may be used in combination.

Claims

At least the ethylenically unsaturated monomer (c-1) having an alkyl group having 9 to 24 carbon atoms (excluding the case where it is the following (c-2)) and the following general formula (1) Ethylenically unsaturated monomer (c-2), ethylenically unsaturated monomer (c-3) represented by the following general formula (2), or ethylene represented by the following general formula (3) A polymer dispersant for a liquid developer, which is obtained by copolymerizing a polymerizable unsaturated monomer (c-4).
General formula (1)

_{CH 2 = C (R1) COO} (AO) nR2

(Wherein, R1 represents a hydrogen atom or a CH ₃ group,
R2 represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms ,
n represents an integer of 1 to 200,
A represents an alkylene group having 2 to 4 carbon atoms. )
General formula (2)

CH (R3) = C (R4) CONR5R6

(In the formula, R3 represents a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms which may have any of an alkoxyl group, a hydroxyl group and a carboxyl group ;
R4 represents a hydrogen atom or a CH ₃ group,
R5 and R6 represent a hydrogen atom or an alkoxyl group, a hydroxyl group, a hydrocarbon group having 1 to 8 carbon atoms which may have a carboxyl group ,
R5 and R6 may form a ring,
R3 and R5 may form a ring containing a carbonyl group. )

General formula (3)

CH ₂ = CHN (R7) (CO) R8

(Wherein R7 and R8 represent a hydrogen atom or an alkoxyl group, a hydroxyl group, a hydrocarbon group having 1 to 8 carbon atoms which may have a carboxyl group ,
R7 and R8 may form a ring containing a carbonyl group. )

The polymer dispersant according to claim 1, wherein the weight average molecular weight Mw is 500 ≦ Mw ≦ 40,000.

A liquid developer containing at least a binder resin (A), a colorant (B), a polymer dispersant (C), and a carrier liquid (D), wherein the polymer dispersant (C) is claimed. A liquid developer which is the polymer dispersant according to 1 or 2.

The liquid developer according to claim 3, wherein the binder resin (A) contains at least a polyester resin and has a softening temperature of 80 to 140 ° C. 5.

5. The liquid developer according to claim 3, wherein the binder resin (A) has a weight average molecular weight Mw of 2,000 ≦ Mw ≦ 100,000.

The binder resin (A) includes a polyester resin (a-1) and at least one resin (a-2) selected from the group consisting of a styrene resin, an acrylic resin, and a styrene-acrylic copolymer resin. The liquid developer according to claim 3.

Mass ratio of polyester resin (a-1) and at least one resin (a-2) selected from the group consisting of styrene resin, acrylic resin, and styrene-acrylic copolymer resin [(a-2) / The liquid developer according to claim 6, wherein (a-1)] is 1 or less.

The liquid developer according to claim 3, wherein the carrier liquid (D) is an aliphatic hydrocarbon.

A printed matter obtained using the liquid developer according to claim 3.