JP2007133216A5 - - Google Patents

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JP2007133216A5
JP2007133216A5 JP2005327287A JP2005327287A JP2007133216A5 JP 2007133216 A5 JP2007133216 A5 JP 2007133216A5 JP 2005327287 A JP2005327287 A JP 2005327287A JP 2005327287 A JP2005327287 A JP 2005327287A JP 2007133216 A5 JP2007133216 A5 JP 2007133216A5
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Japan
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group
bond
toner
carbon atoms
copolymer
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JP2005327287A
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JP2007133216A (en
JP4732137B2 (en
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Priority claimed from JP2005327287A external-priority patent/JP4732137B2/en
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Claims (11)

少なくとも
1)下記一般式(1)又は(2)又は(3)で表される構造を有するユニットA、
2)カルボキシル基を有するユニットB、および
3)芳香族ビニルモノマー由来のユニットC
を含む共重合体であって、
該共重合体におけるユニットAのユニット数基準の含有割合が、
ユニットA:その他のユニット=1:99〜15:85
であって、
該共重合体におけるユニットBのユニット数基準の含有割合が、
ユニットB:その他のユニット=0.05:99.95〜8.00:92.00
であることを特徴とするトナー用樹脂。
Figure 2007133216
(式中、R1〜4は独立に水素原子、水酸基、炭素数1〜12のアルキル基、アリール基、アルコキシ基を表し、R5は炭素数1〜12のアルキル基、アリール基を表し、A1はアミド結合、ウレタン結合、ウレア結合、エステル結合、エーテル結合を表す。)
Figure 2007133216
(式中、R6〜9は独立に水素原子、水酸基、炭素数1〜12のアルキル基、アリール基、アルコキシ基を表し、また、隣接する同士が5員環又は6員環の芳香族環を形成していてもよく、R10は炭素数1〜12のアルキル基、アリール基を表し、A2はアミド結合、ウレタン結合、ウレア結合、エステル結合、エーテル結合を表す。)
Figure 2007133216
(式中、R11〜16は独立に水素原子、水酸基、炭素数1〜12のアルキル基、アリール基、アルコキシ基を表し、また、隣接する同士が5員環又は6員環の芳香族環を形成していてもよく、R10は炭素数1〜12のアルキル基、アリール基を表し、A3はアミド結合、ウレタン結合、ウレア結合、エステル結合、エーテル結合を表す。)
At least 1) a unit A having a structure represented by the following general formula (1) or (2) or (3);
2) Unit B having a carboxyl group, and 3) Unit C derived from an aromatic vinyl monomer.
A copolymer comprising
The content ratio based on the number of units of unit A in the copolymer is:
Unit A: Other units = 1: 99 to 15:85
Because
The content ratio based on the number of units of unit B in the copolymer is:
Unit B: Other units = 0.05: 99.95 to 8.00: 92.00
Resin for toner characterized by the above-mentioned.
Figure 2007133216
(Wherein R1 to 4 independently represent a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an aryl group or an alkoxy group, R5 represents an alkyl group having 1 to 12 carbon atoms or an aryl group, and A1 represents (Represents an amide bond, urethane bond, urea bond, ester bond, or ether bond.)
Figure 2007133216
(Wherein R6 to 9 independently represent a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an aryl group, or an alkoxy group, and adjacent to each other represent a 5-membered or 6-membered aromatic ring. R10 represents an alkyl group having 1 to 12 carbon atoms or an aryl group, and A2 represents an amide bond, a urethane bond, a urea bond, an ester bond, or an ether bond.
Figure 2007133216
(Wherein R11 to 16 independently represent a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an aryl group, or an alkoxy group, and adjacent to each other are 5-membered or 6-membered aromatic rings. R10 represents an alkyl group having 1 to 12 carbon atoms or an aryl group, and A3 represents an amide bond, a urethane bond, a urea bond, an ester bond or an ether bond.
前記共重合体が、少なくとも下記式(4)で表されるモノマーと(メタ)アクリル酸とスチレンとを共重合して得られた共重合体であることを特徴とする請求項1に記載のトナー用樹脂。
Figure 2007133216
(式中、R18は水素原子又はメチル基を表し、Bは下記式(5)又は(6)又は(7)で表される。)
Figure 2007133216
(式中、R19〜22は独立に水素原子、水酸基、炭素数1〜12のアルキル基、アリール基、アルコキシ基を表し、R23は炭素数1〜12のアルキル基、アリール基を表し、A4はアミド結合、ウレタン結合、ウレア結合、エステル結合、エーテル結合を表す。)
Figure 2007133216
(式中、R24〜27は独立に水素原子、水酸基、炭素数1〜12のアルキル基、アリール基、アルコキシ基を表し、また、隣接する同士が5員環又は6員環の芳香族環を形成していてもよく、R28は炭素数1〜12のアルキル基、アリール基を表し、A5はアミド結合、ウレタン結合、ウレア結合、エステル結合、エーテル結合を表す。)
Figure 2007133216
(式中、R29〜34は独立に水素原子、水酸基、炭素数1〜12のアルキル基、アリール基、アルコキシ基を表し、また、隣接する同士が5員環又は6員環の芳香族環を形成していてもよく、R35は炭素数1〜12のアルキル基、アリール基を表し、A6はアミド結合、ウレタン結合、ウレア結合、エステル結合、エーテル結合を表す。)
2. The copolymer according to claim 1, wherein the copolymer is a copolymer obtained by copolymerizing at least a monomer represented by the following formula (4), (meth) acrylic acid, and styrene. Resin for toner.
Figure 2007133216
(In the formula, R18 represents a hydrogen atom or a methyl group, and B is represented by the following formula (5) or (6) or (7).)
Figure 2007133216
(In the formula, R19 to 22 independently represent a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an aryl group or an alkoxy group, R23 represents an alkyl group having 1 to 12 carbon atoms or an aryl group, and A4 represents (Represents an amide bond, urethane bond, urea bond, ester bond, or ether bond.)
Figure 2007133216
(In the formula, R24 to 27 independently represent a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an aryl group, or an alkoxy group, and adjacent to each other are 5-membered or 6-membered aromatic rings. R28 represents an alkyl group having 1 to 12 carbon atoms or an aryl group, and A5 represents an amide bond, a urethane bond, a urea bond, an ester bond or an ether bond.
Figure 2007133216
(In the formula, R29 to 34 each independently represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an aryl group, or an alkoxy group, and adjacent to each other are 5-membered or 6-membered aromatic rings. R35 may represent an alkyl group having 1 to 12 carbon atoms or an aryl group, and A6 represents an amide bond, urethane bond, urea bond, ester bond or ether bond.)
前記共重合体のゲルパーミエーションクロマトグラフィーにより算出した重量平均分子量が2000〜200000の範囲にあることを特徴とする請求項1又は2に記載のトナー用樹脂。   3. The resin for toner according to claim 1, wherein the copolymer has a weight average molecular weight calculated by gel permeation chromatography in the range of 2000 to 200000. 4. 前記共重合体のゲルパーミエーションクロマトグラフィーにより算出した重量平均分子量(Mw)と数平均分子量(Mn)において、Mw/Mnが1.0〜6.0の範囲にあることを特徴とする請求項1乃至3のいずれかに記載のトナー用樹脂。   The weight average molecular weight (Mw) and number average molecular weight (Mn) calculated by gel permeation chromatography of the copolymer are such that Mw / Mn is in the range of 1.0 to 6.0. The toner resin according to any one of 1 to 3. 前記共重合体が、示差走査熱量計により測定されるDSC曲線において、45〜90℃の範囲にガラス転移点を有することを特徴とする請求項1乃至4のいずれかに記載のトナー用樹脂。 5. The resin for toner according to claim 1, wherein the copolymer has a glass transition point in a range of 45 ° C. to 90 ° C. in a DSC curve measured by a differential scanning calorimeter. . 前記共重合体の酸価が、3.0〜40.0mgKOHgであることを特徴とする請求項1乃至5のいずれかに記載のトナー用樹脂。 6. The toner resin according to claim 1, wherein the copolymer has an acid value of 3.0 to 40.0 mg KOH / g. 前記共重合体が、少なくとも前記式(3)で表されるモノマーと(メタ)アクリル酸とスチレンと下記式(8)で表されるモノマーとを共重合して得られた共重合体であることを特徴とする請求項1乃至6のいずれかに記載のトナー用樹脂。
Figure 2007133216
(式中、R36は水素原子又はメチル基を表し、R37は置換基を有していても良い炭素数1〜20のアルキル基を表し、置換基としては水酸基、メトキシ基、エトキシ基、アセチル基、アミノ基である。)
The copolymer is a copolymer obtained by copolymerizing at least a monomer represented by the formula (3), (meth) acrylic acid, styrene, and a monomer represented by the following formula (8). The toner resin according to claim 1, wherein the toner resin is a toner resin.
Figure 2007133216
(In the formula, R36 represents a hydrogen atom or a methyl group, R37 represents an alkyl group having 1 to 20 carbon atoms which may have a substituent, and the substituent includes a hydroxyl group, a methoxy group, an ethoxy group, and an acetyl group. An amino group.)
少なくとも結着樹脂、着色剤、及び、請求項1乃至のいずれかに記載のトナー用樹脂を含有するトナー粒子を有することを特徴とするトナー。 At least a binder resin, a colorant, and the toner which is characterized by having toner particles containing a toner resin according to any one of claims 1 to 7. 前記トナー用樹脂の含有量が、前記結着樹脂100質量部に対して0.1〜20質量部であることを特徴とする請求項に記載のトナー。 The toner according to claim 8, wherein the content of the toner resin, characterized in that said 0.1 to 2 0 mass part of the binder resin 10 0 mass part. 前記トナーは、前記トナー用樹脂を有する組成物を水系媒体中で分散する工程を有する製造方法により形成させたトナー粒子を有することを特徴とする請求項8または9に記載のトナー。 The toner according to claim 8 or 9, characterized in that having toner particles were formed by a manufacturing method having a step of dispersing a composition comprising the toner resin in an aqueous medium. 少なくともトナーとキャリアとを有する二成分現像剤であって、該トナーが請求項8乃至10のいずれかに記載のトナーであることを特徴とする二成分現像剤。 A two-component developer comprising at least a toner and a carrier, wherein the toner is the toner according to any one of claims 8 to 10 .
JP2005327287A 2005-11-11 2005-11-11 Charge control resin for toner, toner and method for producing toner particle Expired - Fee Related JP4732137B2 (en)

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JP2007133216A JP2007133216A (en) 2007-05-31
JP2007133216A5 true JP2007133216A5 (en) 2008-12-25
JP4732137B2 JP4732137B2 (en) 2011-07-27

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5252885B2 (en) * 2007-11-09 2013-07-31 キヤノン株式会社 Resin production method
JP5219484B2 (en) * 2007-12-11 2013-06-26 キヤノン株式会社 Two-component developer and image forming method using the two-component developer
JP5078643B2 (en) * 2008-02-06 2012-11-21 キヤノン株式会社 toner
JP5344552B2 (en) * 2008-09-03 2013-11-20 キヤノン株式会社 Toner and toner production method
JP2010091704A (en) * 2008-10-07 2010-04-22 Canon Inc Toner
WO2011062289A1 (en) * 2009-11-19 2011-05-26 Canon Kabushiki Kaisha Resin for toners, and toner
JP6012422B2 (en) * 2012-11-15 2016-10-25 キヤノン株式会社 toner
CN105745581B (en) * 2013-11-28 2019-10-08 日本瑞翁株式会社 Negatively charged toner and its manufacturing method

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* Cited by examiner, † Cited by third party
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JP2623684B2 (en) * 1988-05-12 1997-06-25 ミノルタ株式会社 toner
JPH0830017A (en) * 1994-07-11 1996-02-02 Canon Inc Electrostatic charge image developing one-component toner
JP4416488B2 (en) * 2002-12-27 2010-02-17 キヤノン株式会社 A novel polyhydroxyalkanoate having an amide group, a sulfonic acid group, and a sulfonic acid ester group, a method for producing the same, a charge control agent, a toner, an image forming method, and an image forming apparatus.
JP4378185B2 (en) * 2004-02-06 2009-12-02 キヤノン株式会社 Method for producing magnetic toner

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