JP2016161592A5 - Toner and toner production method - Google Patents
Toner and toner production method Download PDFInfo
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- JP2016161592A5 JP2016161592A5 JP2015037236A JP2015037236A JP2016161592A5 JP 2016161592 A5 JP2016161592 A5 JP 2016161592A5 JP 2015037236 A JP2015037236 A JP 2015037236A JP 2015037236 A JP2015037236 A JP 2015037236A JP 2016161592 A5 JP2016161592 A5 JP 2016161592A5
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- toner
- pigment
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- 238000004519 manufacturing process Methods 0.000 title claims 3
- 239000000049 pigment Substances 0.000 claims 10
- 239000002270 dispersing agent Substances 0.000 claims 7
- 150000002148 esters Chemical class 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 239000000178 monomer Substances 0.000 claims 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 4
- 229920000642 polymer Polymers 0.000 claims 4
- 125000005647 linker group Chemical group 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 2
- 239000011230 binding agent Substances 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 230000002209 hydrophobic Effects 0.000 claims 2
- 239000002245 particle Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 238000001556 precipitation Methods 0.000 claims 2
- 239000011347 resin Substances 0.000 claims 2
- 229920005989 resin Polymers 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 1
- 230000000379 polymerizing Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atoms Chemical group 0.000 claims 1
Claims (3)
該エステルワックスは、２価以上のアルコールと１価カルボン酸とのエステル、又は２価以上のカルボン酸と１価アルコールとのエステルであり、
該顔料分散剤は、下記式（１）で表される顔料吸着部位とポリマー部位とを有し、
該顔料分散剤の疎水性パラメータをＨＰ１、該多官能エステルワックスの疎水性パラメータをＨＰ２とした時、ＨＰ１とＨＰ２の差の絶対値が０．００以上０．１９以下であることを特徴とするトナー。
（ＨＰ１は、該顔料分散剤のクロロホルム溶液にヘプタンを添加した際の該顔料分散剤の析出点におけるヘプタンの体積分率である。ＨＰ２は、該多官能エステルワックスのクロロホルム溶液にヘプタンを添加した際の該多官能エステルワックスの析出点におけるヘプタンの体積分率である。）
［式（１）中、Ｒ１は、置換若しくは無置換のアルキル基又は置換若しくは無置換のフェニル基を表し、Ａｒは置換若しくは無置換のアリール基を表し、Ａｒ及びＲ２〜Ｒ６は、下記（ｉ）及び（ｉｉ）の少なくとも一方の条件を満たす。
（ｉ）Ａｒが、アリール基の炭素原子に結合してなる、該ポリマー部位との結合部を構成する連結基を有する。
（ｉｉ）Ｒ２〜Ｒ６のうちの少なくとも一つは、該ポリマー部位との結合部を構成する連結基を有する。
Ｒ２〜Ｒ６が該連結基を有さない場合、Ｒ２〜Ｒ６は、それぞれ独立して、水素原子、ハロゲン原子、アルキル基、アルコキシ基、ヒドロキシ基、アミノ基、シアノ基、トリフ
ルオロメチル基、カルボキシ基、又は、下記式（２）で表される基を表す。
但し、Ａｒ及びＲ２〜Ｒ６は、下記（ｉｉｉ）及び（ｉｖ）の少なくとも一方の条件を満たす。
（ｉｉｉ）Ａｒは、置換基として、下記式（２）で表される基を有する。
（ｉｖ）Ｒ２〜Ｒ６のうちの少なくとも一つは、下記式（２）で表される基である。］
［式（２）中、＊は、式（１）中のＡｒ、又はＲ２〜Ｒ６を有する芳香環との結合位置を表す。Ｒ７は、水素原子、置換若しくは無置換のアルキル基、アラルキル基、置換若しくは無置換のアルキルオキシカルボニル基、若しくは、置換若しくは無置換のアラルキルオキシカルボニル基、又は、式（２）で表される基がＡｒ若しくはＲ２〜Ｒ６を有する芳香環と結合することによって５員複素環を形成するための、Ａｒ、又はＲ２〜Ｒ６を有する芳香環との結合位置を表す。Ａは、酸素原子、硫黄原子、又はＮＲ８基を表し、Ｒ８は、水素原子、置換若しくは無置換のアルキル基、置換若しくは無置換のアルキルオキシカルボニル基、又は置換若しくは無置換のアラルキルオキシカルボニル基を表す。］ A binder resin, a pigment, a toner having a pigment dispersing agent, and the toner particles containing an ester wax,
The ester wax is an ester of a dihydric or higher alcohol and a monovalent carboxylic acid, or an ester of a divalent or higher carboxylic acid and a monohydric alcohol,
The pigment dispersant has a pigment adsorption site and a polymer site represented by the following formula (1):
When the hydrophobic parameter of the pigment dispersant is HP1 and the hydrophobic parameter of the polyfunctional ester wax is HP2, the absolute value of the difference between HP1 and HP2 is 0.00 or more and 0.19 or less. toner.
(HP1 is the volume fraction of heptane at the precipitation point of the pigment dispersant when heptane is added to the chloroform solution of the pigment dispersant. HP2 is heptane added to the chloroform solution of the polyfunctional ester wax. This is the volume fraction of heptane at the precipitation point of the polyfunctional ester wax.
[In Formula (1), R 1 represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted phenyl group, Ar represents a substituted or unsubstituted aryl group, and Ar and R 2 to R 6 are Satisfy at least one of the following conditions (i) and (ii).
(I) Ar has a linking group that forms a bond with the polymer moiety formed by bonding to a carbon atom of an aryl group.
(Ii) At least one of R 2 to R 6 has a linking group that constitutes a bond with the polymer moiety.
When R 2 to R 6 do not have the linking group, R 2 to R 6 are each independently a hydrogen atom, halogen atom, alkyl group, alkoxy group, hydroxy group, amino group, cyano group, trifluoro group. A methyl group, a carboxy group, or a group represented by the following formula (2) is represented.
However, Ar and R 2 to R 6 satisfy at least one of the following conditions (iii) and (iv).
(Iii) Ar has a group represented by the following formula (2) as a substituent.
(Iv) At least one of R 2 to R 6 is a group represented by the following formula (2). ]
[In Formula (2), * represents the bonding position with Ar in Formula (1) or an aromatic ring having R 2 to R 6 . R 7 is represented by a hydrogen atom, a substituted or unsubstituted alkyl group, an aralkyl group, a substituted or unsubstituted alkyloxycarbonyl group, a substituted or unsubstituted aralkyloxycarbonyl group, or the formula (2) group represents a bonding position to the aromatic ring having for forming a 5-membered heterocyclic ring by binding to the aromatic ring with Ar or R 2 ~R 6, Ar, or R 2 to R 6. A represents an oxygen atom, a sulfur atom, or an NR 8 group, and R 8 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyloxycarbonyl group, or a substituted or unsubstituted aralkyloxycarbonyl. Represents a group. ]
［式（３）中、Ｒ９は、水素原子又はアルキル基を表し、Ｒ１０は、置換若しくは無置換のフェニル基、カルボキシル基、置換若しくは無置換のカルボン酸エステル基、又は置換若しくは無置換のカルボン酸アミド基を表す。］ The toner according to claim 1, wherein the polymer part of the pigment dispersant has a monomer unit represented by the following formula (3).
[In Formula (3), R 9 represents a hydrogen atom or an alkyl group, and R 10 represents a substituted or unsubstituted phenyl group, a carboxyl group, a substituted or unsubstituted carboxylic acid ester group, or a substituted or unsubstituted group. Represents a carboxylic acid amide group. ]
前記顔料、前記顔料分散剤、前記エステルワックス、及び前記結着樹脂を形成する重合性単量体を含有する重合性単量体組成物を水系媒体中で造粒し、該重合性単量体組成物に含まれる前記重合性単量体を重合することによって前記トナー粒子を製造する工程を有するトナーの製造方法。 A toner production method according to claim 1 or 2,
Before SL pigment, the pigment dispersing agent, the an ester wax, and a polymerizable monomer composition containing a polymerizable monomer forming the binder resin and granulating in an aqueous medium, polymerizable Single A toner production method comprising a step of producing the toner particles by polymerizing the polymerizable monomer contained in a monomer composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015037236A JP6418978B2 (en) | 2015-02-26 | 2015-02-26 | Toner and toner production method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015037236A JP6418978B2 (en) | 2015-02-26 | 2015-02-26 | Toner and toner production method |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016161592A JP2016161592A (en) | 2016-09-05 |
| JP2016161592A5 true JP2016161592A5 (en) | 2018-03-29 |
| JP6418978B2 JP6418978B2 (en) | 2018-11-07 |
Family
ID=56846916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015037236A Active JP6418978B2 (en) | 2015-02-26 | 2015-02-26 | Toner and toner production method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP6418978B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10095144B2 (en) * | 2015-09-01 | 2018-10-09 | Canon Kabushiki Kaisha | Toner and method for manufacturing the same |
| JP6835409B2 (en) * | 2017-05-15 | 2021-02-24 | 花王株式会社 | Manufacturing method of toner for electrophotographic |
| JP7005873B2 (en) * | 2018-03-28 | 2022-01-24 | 花王株式会社 | Toner for static charge image development |
| JP7278751B2 (en) * | 2018-11-15 | 2023-05-22 | 花王株式会社 | Toner manufacturing method |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3210174B2 (en) * | 1993-05-20 | 2001-09-17 | キヤノン株式会社 | Electrostatic image developing toner and method of manufacturing the same |
| JP3577672B2 (en) * | 1994-01-31 | 2004-10-13 | コニカミノルタホールディングス株式会社 | Electrophotographic color toner and fixing method |
| JP2003195565A (en) * | 2001-12-28 | 2003-07-09 | Canon Inc | Toner and method of manufacturing the same, and image forming method using the toner |
| JP3984840B2 (en) * | 2002-03-01 | 2007-10-03 | キヤノン株式会社 | Toner production method |
| US20090280425A1 (en) * | 2008-05-09 | 2009-11-12 | Gary Allen Denton | Black Toner Formulations |
| JP2011059568A (en) * | 2009-09-14 | 2011-03-24 | Ricoh Co Ltd | Yellow toner for image formation |
| US20110091805A1 (en) * | 2009-10-21 | 2011-04-21 | Xerox Corporation | Toner compositions |
| JP4999997B2 (en) * | 2010-08-27 | 2012-08-15 | キヤノン株式会社 | Azo compound, pigment dispersant, pigment composition, pigment dispersion and toner containing the azo compound |
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- 2015-02-26 JP JP2015037236A patent/JP6418978B2/en active Active
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