JP2016011971A5 - - Google Patents

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JP2016011971A5
JP2016011971A5 JP2014132076A JP2014132076A JP2016011971A5 JP 2016011971 A5 JP2016011971 A5 JP 2016011971A5 JP 2014132076 A JP2014132076 A JP 2014132076A JP 2014132076 A JP2014132076 A JP 2014132076A JP 2016011971 A5 JP2016011971 A5 JP 2016011971A5
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group
carbon atoms
toner
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polymer
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Claims (9)

有機ケイ素重合体を含有する表層と荷電制御剤を有するトナー粒子を有するトナーであり、
該有機ケイ素重合体は、下記式(T3R)
Figure 2016011971
(式中のRは炭素数が1以上6以下の炭化水素基である。)
で表わされるユニットを有し、
前記トナー粒子の表面のESCA(Electron Spectroscopy for Chemical Analysis)を用いた測定において、トナー粒子表面の炭素元素濃度dC、酸素元素濃度dO、ケイ素元素濃度dSiの合計濃度(dC+dO+dSi)に対するケイ素元素濃度dSiが0.50atomic%以上であり、
前記荷電制御剤が式(a1)で示される構造aを有する重合体Aであることを特徴とするトナー。
Figure 2016011971
(式中、R1は、ヒドロキシル基、カルボキシル基、炭素数1以上18以下のアルキル基、または、炭素数1以上18以下のアルコキシル基を表し、R2は、水素原子、ヒドロキシル基、炭素数1以上18以下のアルキル基、または、炭素数1以上18以下のアルコキシル基を表し、gは1以上3以下の整数を表し、hは0以上3以下の整数を表し、hが2または3の場合、R1はそれぞれ独立して選択でき、※※は重合体Aにおける結合部位である。)
A toner having toner particles having a surface layer containing an organosilicon polymer and a charge control agent;
The organosilicon polymer has the following formula (T3R)
Figure 2016011971
(R in the formula is a hydrocarbon group having 1 to 6 carbon atoms.)
Having a unit represented by
In measurement using ESCA (Electron Spectroscopy for Chemical Analysis) of the surface of the toner particles, the carbon element concentration dC surface of the toner particles, an oxygen element concentration dO, silicon element concentration dSi for the total concentration of the silicon element concentration dSi (dC + dO + dSi) 0.50 atomic% or more,
A toner, wherein the charge control agent is a polymer A having a structure a represented by the formula (a1).
Figure 2016011971
(Wherein R 1 represents a hydroxyl group, a carboxyl group, an alkyl group having 1 to 18 carbon atoms, or an alkoxyl group having 1 to 18 carbon atoms, and R 2 represents a hydrogen atom, a hydroxyl group, or a carbon number. Represents an alkyl group having 1 to 18 carbon atoms, or an alkoxyl group having 1 to 18 carbon atoms, g represents an integer of 1 to 3, h represents an integer of 0 to 3, and h is 2 or 3. In this case, R 1 can be independently selected, and ** is a binding site in the polymer A.)
該トナー粒子のTHF不溶分の29Si−NMRの測定において、該有機ケイ素重合体の全ピーク面積に対する前記式(T3R)の構造のピーク面積の割合RS(T3R)が、
RS(T3R)≧0.20 (1)
を満たすことを特徴とする請求項1に記載のトナー。
In the measurement of 29 Si-NMR of the THF-insoluble matter of the toner particles, the ratio RS (T3R) of the peak area of the structure of the formula (T3R) to the total peak area of the organosilicon polymer is
RS (T3R) ≧ 0.20 (1)
The toner according to claim 1, wherein:
前記トナー粒子のTHF不溶分の29Si−NMRの測定において、該有機ケイ素重合体の全ピーク面積に対し、ケイ素に結合するシロキシ基の数が3.0である(SX3)の構造のピーク面積の割合S(SX3)とケイ素に結合するO1/2の数が2.0である(SX2)構造のピーク面積S(SX2)の割合の関係が
S(SX3)/S(SX2)≧1.00 (2)
を満たすことを特徴とする請求項1又は2に記載のトナー。
In the 29 Si-NMR measurement of the THF-insoluble matter of the toner particles, the peak area of the structure (SX3) in which the number of siloxy groups bonded to silicon is 3.0 with respect to the total peak area of the organosilicon polymer. The relationship between the ratio S (SX3) and the ratio of the peak area S (SX2) of the (SX2) structure in which the number of O 1/2 bonded to silicon is 2.0 is S (SX3) / S (SX2) ≧ 1 .00 (2)
The toner according to claim 1, wherein the toner satisfies the following condition.
透過型電子顕微鏡(TEM)を用いた前記トナー粒子の断面の観察によって測定される、有機ケイ素重合体を含有する表層の平均厚みDが2.5nm以上150.0nm以下であることを特徴とする請求項1〜3のいずれか1項に記載のトナー。   The average thickness D of the surface layer containing the organosilicon polymer, measured by observing the cross section of the toner particles using a transmission electron microscope (TEM), is 2.5 nm or more and 150.0 nm or less. The toner according to claim 1. 該有機ケイ素重合体は、下記式(Z)
Figure 2016011971
(式中のR1は炭素数1〜6の炭化水素基であり、R2、R3及びR4は、それぞれ独立してハロゲン原子、水酸基またはアルコキシ基である。)
で表わされる構造を有する化合物重合体であることを特徴とする請求項1〜4のいずれか1項に記載のトナー。
The organosilicon polymer has the following formula (Z)
Figure 2016011971
(R1 in the formula is a hydrocarbon group having 1 to 6 carbon atoms, and R2, R3 and R4 are each independently a halogen atom, a hydroxyl group or an alkoxy group.)
The toner according to claim 1, wherein the toner is a polymer of a compound having a structure represented by:
前記式(Z)中のR1はメチル基、エチル基、プロピル基またはアリール基であることを特徴とする請求項5に記載のトナー。   The toner according to claim 5, wherein R 1 in the formula (Z) is a methyl group, an ethyl group, a propyl group, or an aryl group. 前記式(Z)中のR2、R3及びR4は、それぞれ独立してアルコキシ基であることを特徴とする請求項5又は6に記載のトナー。   7. The toner according to claim 5, wherein R 2, R 3, and R 4 in the formula (Z) are each independently an alkoxy group. 前記構造aが式(a2)で表される部分構造で、前記重合体A中に含まれることを特徴とする請求項1〜7のいずれか1項に記載のトナー。
Figure 2016011971
(式中、R3は、ヒドロキシル基、カルボキシル基、炭素数1以上18以下のアルキル基、または、炭素数1以上18以下のアルコキシル基を表し、
4は、水素原子、ヒドロキシル基、炭素数1以上18以下のアルキル基、または、炭素数1以上18以下のアルコキシル基を表し、
5は水素原子またはメチル基を表し、
iは1以上3以下の整数を表し、jは0以上3以下の整数を表し、jが2または3の場合、R 3 はそれぞれ独立して選択できる。)
The toner according to claim 1, wherein the structure a is a partial structure represented by the formula (a2) and is contained in the polymer A.
Figure 2016011971
(In the formula, R 3 represents a hydroxyl group, a carboxyl group, an alkyl group having 1 to 18 carbon atoms, or an alkoxyl group having 1 to 18 carbon atoms,
R 4 represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 18 carbon atoms, or an alkoxyl group having 1 to 18 carbon atoms,
R 5 represents a hydrogen atom or a methyl group,
i represents an integer of 1 to 3, j represents an integer of 0 to 3, and when j is 2 or 3, R 3 can be independently selected. )
前記重合体A中の構造aの含有量が10μmol/g以上1500μmol/g以下であることを特徴とする請求項1〜8のいずれか1項に記載のトナー。   The toner according to claim 1, wherein the content of the structure a in the polymer A is 10 μmol / g or more and 1500 μmol / g or less.
JP2014132076A 2014-06-27 2014-06-27 toner Active JP6316117B2 (en)

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JP2016011971A JP2016011971A (en) 2016-01-21
JP2016011971A5 true JP2016011971A5 (en) 2017-08-10
JP6316117B2 JP6316117B2 (en) 2018-04-25

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9733584B2 (en) * 2015-04-08 2017-08-15 Canon Kabushiki Kaisha Toner
JP6489909B2 (en) * 2015-04-08 2019-03-27 キヤノン株式会社 TONER AND METHOD FOR MANUFACTURING TONER
JP6643121B2 (en) * 2016-02-03 2020-02-12 キヤノン株式会社 toner
JP6849379B2 (en) * 2016-10-13 2021-03-24 キヤノン株式会社 Manufacturing method of toner particles
JP7204413B2 (en) * 2018-10-19 2023-01-16 キヤノン株式会社 toner
JP7479879B2 (en) 2019-04-25 2024-05-09 キヤノン株式会社 toner

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* Cited by examiner, † Cited by third party
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JP2001330996A (en) * 2000-05-19 2001-11-30 Canon Inc Method for image formation
JP2004325756A (en) * 2003-04-24 2004-11-18 Canon Inc Toner and method for manufacturing the same
JP4966058B2 (en) * 2006-03-16 2012-07-04 株式会社リコー Non-magnetic toner, image forming apparatus and process cartridge
WO2012157781A1 (en) * 2011-05-18 2012-11-22 Canon Kabushiki Kaisha Toner
US9029056B2 (en) * 2011-05-18 2015-05-12 Canon Kabushiki Kaisha Toner
EP2860584B1 (en) * 2013-10-09 2017-04-05 Canon Kabushiki Kaisha Toner

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