JPH06124002A - Toner for electrostatic image development - Google Patents

Toner for electrostatic image development

Info

Publication number
JPH06124002A
JPH06124002A JP4237031A JP23703192A JPH06124002A JP H06124002 A JPH06124002 A JP H06124002A JP 4237031 A JP4237031 A JP 4237031A JP 23703192 A JP23703192 A JP 23703192A JP H06124002 A JPH06124002 A JP H06124002A
Authority
JP
Japan
Prior art keywords
toner
parts
group
exemplified compound
developing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP4237031A
Other languages
Japanese (ja)
Other versions
JP3136792B2 (en
Inventor
Hitoshi Ono
均 小野
Osamu Ando
修 安藤
Masako Takeuchi
昌子 竹内
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Chemical Corp
Original Assignee
Mitsubishi Kasei Corp
Mitsubishi Chemical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mitsubishi Kasei Corp, Mitsubishi Chemical Industries Ltd filed Critical Mitsubishi Kasei Corp
Priority to JP04237031A priority Critical patent/JP3136792B2/en
Publication of JPH06124002A publication Critical patent/JPH06124002A/en
Application granted granted Critical
Publication of JP3136792B2 publication Critical patent/JP3136792B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Abstract

(57)【要約】 (修正有) 【目的】 時間を経てもコピー汚れの発生しにくい高品
質の静電荷像現像用トナーを提供する。 【構成】 少なくとも樹脂及び着色剤を含有してなる静
電荷像現像用トナーにおいて、下記一般式(I),(I
I)で表わされるサイクロオリゴ糖又はその誘導体を1
種以上含有する。 〔式中、R〜Rは、それぞれ、水素原子、アルキル
基、アシル基、等を表わし、m,nは6〜8のいずれか
の数を表わす。またR〜Rはすべて同一であっても
異っていてもよい。〕
(57) [Summary] (Correction) [Purpose] To provide a high-quality toner for developing an electrostatic charge image in which stains on a copy are less likely to occur over time. A toner for developing an electrostatic charge image containing at least a resin and a colorant, comprising the following general formulas (I) and (I
Cyclooligosaccharide represented by I) or its derivative 1
Contains more than one species. [In the formula, R 1 to R 6 each represent a hydrogen atom, an alkyl group, an acyl group, or the like, and m and n represent any number from 6 to 8. R 1 to R 6 may be the same or different. ]

Description

【発明の詳細な説明】Detailed Description of the Invention

【0001】[0001]

【産業上の利用分野】本発明は、電子複写機等で使用さ
れる静電荷像現像用トナーに関するものである。
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrostatic charge image developing toner used in electronic copying machines and the like.

【0002】[0002]

【従来の技術】電子複写機等で使用される現像剤は、そ
の現像工程において、例えば静電荷像が形成されている
感光体等の像担持体に一旦付着せしめられ、次に転写工
程において感光体から転写紙に転写された後、定着工程
においてコピー紙面に定着される。その際、潜像保持面
上に形成される静電荷像を現像するための現像剤とし
て、キャリアとトナーとから成る二成分系現像剤、およ
びキャリアを必要としない一成分系現像剤(磁性トナ
ー)が知られている。
2. Description of the Related Art A developer used in an electronic copying machine or the like is temporarily adhered to an image bearing member such as a photoconductor on which an electrostatic charge image is formed in the developing process and then exposed in a transfer process. After being transferred from the body to the transfer paper, it is fixed on the copy paper surface in the fixing step. At that time, as a developer for developing the electrostatic charge image formed on the latent image holding surface, a two-component developer composed of a carrier and a toner, and a one-component developer not requiring a carrier (magnetic toner). )It has been known.

【0003】そして、従来より現像剤に帯電性を付与す
るものとしてニグロシン系染料、4級アンモニウム塩、
含金属錯塩染料等の帯電制御剤やキャリアのコーティン
グ剤等が知られていた。しかしながら、これら従来の帯
電性付与剤は、帯電性付与効果が必ずしも十分ではなく
特に該効果が経時変化する為に連続複写によるコピー汚
れが発生し、コピー品質が低下するという問題点を有し
ていた。
Conventionally, nigrosine dyes, quaternary ammonium salts, and
Charge control agents such as metal-containing complex salt dyes and carrier coating agents have been known. However, these conventional chargeability-imparting agents have a problem that the chargeability-imparting effect is not always sufficient, and in particular, the effect is changed over time, copy smear occurs due to continuous copying, and copy quality deteriorates. It was

【0004】[0004]

【発明が解決しようとする課題】本発明の目的は、時間
を経てもコピー汚れ等の発生しにくい高品質の静電荷像
現像用トナーを提供することにある。
SUMMARY OF THE INVENTION An object of the present invention is to provide a high-quality toner for developing an electrostatic charge image, which is unlikely to cause copy stains over time.

【0005】[0005]

【問題点を解決するための手段】本発明者等は上記課題
を解決する為、鋭意検討を行なった結果、特定の構造を
有する化合物をトナー中に含有させることにより、これ
らの問題点が解決されることを見い出し、本発明に到達
した。すなわち、本発明は、少なくとも樹脂及び着色剤
を含有してなる静電荷像現像用トナーにおいて、サイク
ロオリゴ糖又はその誘導体を一種以上含有することを特
徴とする静電荷像現像用トナーである。
The inventors of the present invention have made extensive studies in order to solve the above-mentioned problems, and as a result, these problems were solved by incorporating a compound having a specific structure into the toner. As a result, they have reached the present invention. That is, the present invention is an electrostatic charge image developing toner comprising at least a resin and a colorant, which contains one or more cyclooligosaccharides or derivatives thereof.

【0006】以下、本発明を詳細に説明する。本発明の
静電荷像現像用トナーは、サイクロオリゴ糖又はその誘
導体を1種以上含有することを特徴とする。サイクロオ
リゴ糖とは、一般に単糖類が水分子を失なって6個ない
し8個環状に縮重合したものをさす。サイクロオリゴ糖
を構成する単糖類としては、グルコース、フルクトー
ス、キシロース、ガラクトース、マンノース、アラビノ
ースなどが挙げられる。
The present invention will be described in detail below. The toner for developing an electrostatic charge image of the present invention is characterized by containing at least one cyclooligosaccharide or a derivative thereof. The cyclooligosaccharide generally refers to a monosaccharide in which 6 to 8 cyclic polycondensations have been lost due to the loss of water molecules. Examples of monosaccharides constituting the cyclooligosaccharide include glucose, fructose, xylose, galactose, mannose, arabinose and the like.

【0007】本発明に用いられるサイクロオリゴ糖とし
ては、フルクトースから成るサイクロイヌロオリゴ糖、
若しくはグルコースから成るサイクロデキストリン又は
その誘導体が特に好適であり、下記一般式(I)又は
(II) で表わされる化合物である。
Cyclooligosaccharides used in the present invention include cycloinulooligosaccharides composed of fructose,
Alternatively, cyclodextrin composed of glucose or a derivative thereof is particularly preferable, and is a compound represented by the following general formula (I) or (II).

【0008】[0008]

【化1】 [Chemical 1]

【0009】〔式中、R1 ,R2 及びR3 は、それぞ
れ、水素原子、アルキル基、アシル基、等を表わし、n
は6〜8のいずれかの数を表わす。またR1 ,R2 ,R
3 はすべて同一であっても異っていてもよい。〕
[In the formula, R 1 , R 2 and R 3 each represent a hydrogen atom, an alkyl group, an acyl group or the like, and n
Represents any number from 6 to 8. In addition, R 1 , R 2 , R
All three may be the same or different. ]

【0010】[0010]

【化2】 [Chemical 2]

【0011】〔式中、R4 ,R5 及びR6 は、それぞ
れ、水素原子、アルキル基、又はアシル基等を表わし、
mは6〜8のいずれかの数を表わす。またR4 ,R5
6 はすべて同一であっても異っていてもよい。〕置換
基R1 ,R2 ,R3 の具体例をあげれば、水素原子;メ
チル基,エチル基,プロピル基,ブチル基等のアルキル
基;アセチル基,プロピオニル基,ブチリル基,イソブ
チリル基等のアシル基が挙げられ、中でもR1 が水素原
子,R2 ,R3 がメチル基が好ましい。またnについて
は6が好ましい。
[In the formula, R 4 , R 5 and R 6 each represent a hydrogen atom, an alkyl group, an acyl group or the like,
m represents any number from 6 to 8. In addition, R 4 , R 5 ,
R 6 s may all be the same or different. Specific examples of the substituents R 1 , R 2 and R 3 include hydrogen atom; alkyl group such as methyl group, ethyl group, propyl group and butyl group; acetyl group, propionyl group, butyryl group, isobutyryl group and the like. An acyl group is mentioned, and among them, R 1 is preferably a hydrogen atom, and R 2 and R 3 are preferably methyl groups. Further, n is preferably 6.

【0012】置換基R4 ,R5 ,R6 の具体例をあげれ
ば、水素原子;メチル基,エチル基,プロピル基,ブチ
ル基等のアルキル基;アセチル基,プロピオニル基,ブ
チリル基,イソブチリル基等のアシル基が挙げられ、中
でもR4 が水素原子,R5 ,R6 がメチル基が好まし
い。またmについては6が好ましい。また、R1
2 ,R3 が全て水素原子の場合には、水溶性が高くな
り電気特性に若干問題が生じる可能性がある。
Specific examples of the substituents R 4 , R 5 and R 6 include hydrogen atom; alkyl groups such as methyl group, ethyl group, propyl group and butyl group; acetyl group, propionyl group, butyryl group and isobutyryl group. And the like, and among them, R 4 is preferably a hydrogen atom, and R 5 and R 6 are preferably methyl groups. Further, m is preferably 6. Also, R 1 ,
When R 2 and R 3 are all hydrogen atoms, the solubility in water becomes high, which may cause some problems in electrical characteristics.

【0013】一般式(I)あるいは(II)で表わされる
サイクロオリゴ糖又はその誘導体の中で本発明の静電荷
像用トナーに含有せしめるのに好適なものの具体例とし
ては下記の構造式で表わされる化合物を挙げることがで
きるが、これらに限定されるものではない。
Among the cyclooligosaccharides represented by the general formula (I) or (II) or their derivatives, those suitable for being contained in the toner for electrostatic charge image of the present invention are shown by the following structural formulas. Examples of such compounds include, but are not limited to:

【0014】[0014]

【表1】 [Table 1]

【0015】このようなサイクロオリゴ糖又はその誘導
体は、その製造法によらず本発明に用いることができる
が、具体的製造方法の一例としては特開平2−2527
01号公報記載の方法が挙げられる。本発明に、使用し
得る樹脂成分としては、静電荷像現像用トナーに適した
公知の種々のものが使用できる。例えば、スチレン系樹
脂、スチレンアクリル系共重合樹脂、ポリエステル系樹
脂、エポキシ系樹脂及びこれらの混合樹脂、また、これ
らのアルキル側鎖にアミノ基を有するもの等がある。
Such a cyclooligosaccharide or a derivative thereof can be used in the present invention regardless of its production method, but as an example of a concrete production method, JP-A-2-2527 is used.
The method described in the No. 01 publication can be mentioned. As the resin component that can be used in the present invention, various known components suitable for toners for developing electrostatic image can be used. For example, there are styrene resins, styrene acrylic copolymer resins, polyester resins, epoxy resins and mixed resins thereof, and those having an amino group in their alkyl side chains.

【0016】トナー中のサイクロオリゴ糖又はその誘導
体の含有率は、樹脂100重量部に対して0.1〜20
重量部が好ましく、より好ましくは1〜15重量部であ
る。サイクロオリゴ糖又はその誘導体の含有率が少なす
ぎると帯電性の向上効果が期待できず、また過剰である
とトナーの品質が低下するので好ましくない。本発明で
用いる着色剤としては、従来から用いられているもので
あれば特に制限されるものではなく、黒色トナーを得る
には、カーボンブラック等を使用する。また、サイクロ
オリゴ糖又はその誘導体は、通常白色なので、青、赤、
黄等のカラートナーに含有せしめてもよく、この場合は
相当する色の染顔料等からなる着色剤を用いる。
The content of cyclo-oligosaccharide or its derivative in the toner is 0.1 to 20 with respect to 100 parts by weight of the resin.
It is preferably part by weight, more preferably 1 to 15 parts by weight. If the content of the cyclooligosaccharide or its derivative is too low, the effect of improving the charging property cannot be expected, and if it is excessive, the quality of the toner is deteriorated, which is not preferable. The colorant used in the present invention is not particularly limited as long as it is conventionally used, and carbon black or the like is used to obtain a black toner. In addition, cyclooligosaccharide or its derivative is usually white, so blue, red,
It may be contained in a color toner such as yellow. In this case, a colorant composed of a dye or pigment of a corresponding color is used.

【0017】着色剤の含有率は、樹脂100重量部に対
して3〜20重量部とするのが好ましい。更に、本発明
のトナーには、サイクロオリゴ糖又はその誘導体とは別
に、公知のものを含めて他の帯電制御剤、例えば、ニグ
ロシン系染料、4級アンモニウム塩、含金錯素塩染料等
を含有せしめてもよい。
The content of the colorant is preferably 3 to 20 parts by weight with respect to 100 parts by weight of the resin. Further, in addition to cyclo-oligosaccharide or its derivative, the toner of the present invention contains other charge control agents including known ones such as nigrosine dye, quaternary ammonium salt, and metal complex complex dye. You may make it contain.

【0018】その他、本発明のトナー構成成分として、
定着性や流動性を向上させるため、低分子量オレフィン
重合体や微粉末シリカ等の添加剤を含有せしめてもよ
い。トナーの製造法としては、上記の各成分をニーダー
等で混練し冷却後、粉砕し分級すればよい。又、本発明
のトナーは二成分系現像剤の他に、カプセル化トナーや
重合トナー及びマグネタイト含有トナー等のいわゆる一
成分系現像剤(磁性トナー)にも適用することができ
る。
In addition, as a toner constituent component of the present invention,
In order to improve fixability and fluidity, an additive such as a low molecular weight olefin polymer or fine powder silica may be contained. As a method for producing a toner, each of the above components may be kneaded with a kneader or the like, cooled, pulverized and classified. In addition to the two-component developer, the toner of the present invention can be applied to so-called one-component developer (magnetic toner) such as encapsulated toner, polymerized toner and magnetite-containing toner.

【0019】トナーの平均粒径は5〜20μmが好適で
ある。本発明のトナーと混合して現像剤を形成するキャ
リアとしては、特に制限はないが10〜200μmの平
均粒径を有する鉄粉が好ましい。なお、鉄粉の粒径には
特に制限はない。この場合、連続使用時の耐久性向上の
目的でフッ素系樹脂等をコーティングしたいわゆるコー
ティングキャリアも使用することができる。又、フェラ
イト系、マグネタイト系等を初めとする公知の他のキャ
リアも使用することができる。これらキャリアは、トナ
ー1重量部に対して、5〜100重量部使用することが
好ましい。
The average particle size of the toner is preferably 5 to 20 μm. The carrier for forming the developer by mixing with the toner of the present invention is not particularly limited, but iron powder having an average particle diameter of 10 to 200 μm is preferable. The particle size of the iron powder is not particularly limited. In this case, a so-called coating carrier coated with a fluororesin or the like can be used for the purpose of improving durability during continuous use. Further, other known carriers such as ferrite type and magnetite type may be used. It is preferable to use 5 to 100 parts by weight of these carriers with respect to 1 part by weight of the toner.

【0020】[0020]

【実施例】以下、実施例により本発明を更に詳細に説明
するが、本発明はその要旨を超えない限り、以下の実施
例によりなんら制限されるものではない。なお、下記実
施例中単に「部」とあるのはいずれも「重量部」を意味
するものとする。
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to the following examples as long as the gist thereof is not exceeded. In the following examples, "parts" simply means "parts by weight".

【0021】[0021]

【表2】実施例−1 スチレン系樹脂 100部 (三洋化成社製、商品名SBM−600) カーボンブラック 10部 (三菱化成(株)製#44) 例示化合物(1) 2部[Table 2] Example-1 Styrene-based resin 100 parts (manufactured by Sanyo Chemical Co., Ltd., trade name SBM-600) Carbon black 10 parts (Mitsubishi Chemical Co., Ltd. # 44) Exemplified Compound (1) 2 parts

【0022】上記の材料を配合混練し、粉砕分級して平
均粒子径11μmの黒色正帯電トナーを得た。このトナ
ー5部と平均粒径約100μmのフッ素系樹脂コーティ
ングキャリア100部とを混合攪拌して現像剤を作製し
た。次いでこの現像剤を有機光導電体を感光体とする複
写機で実写したところ白地部の地汚れ、いわゆるカブリ
の少ない鮮明なコピーが得られた。
The above materials were blended, kneaded, pulverized and classified to obtain a black positively charged toner having an average particle diameter of 11 μm. 5 parts of this toner and 100 parts of a fluororesin coating carrier having an average particle size of about 100 μm were mixed and stirred to prepare a developer. Next, when this developer was actually copied by a copying machine using an organic photoconductor as a photoreceptor, a clear copy with less background stains on the white background and so-called fog was obtained.

【0023】実施例−2 帯電制御剤として、例示化合物(1)2部のかわりに例
示化合物(2)を1部使用する以外は、実施例−1と全
く同様にしたところ、実施例−1と同様に良好なコピー
が得られた。
Example-2 Except that 1 part of Exemplified Compound (2) was used as the charge control agent instead of 2 parts of Exemplified Compound (1), the same procedure as in Example-1 was carried out. Good copies were obtained as well.

【0024】実施例−3 帯電制御剤として、例示化合物(1)2部のかわりに例
示化合物(4)を3部使用する以外は、実施例−1と全
く同様にしたところ、実施例−1と同様に良好なコピー
が得られた。
Example-3 The procedure of Example-1 was repeated except that 3 parts of Exemplified Compound (4) was used as the charge control agent instead of 2 parts of Exemplified Compound (1). Good copies were obtained as well.

【0025】実施例−4 帯電制御剤として、例示化合物(1)2部のかわりに例
示化合物(7)を5部使用する以外は、実施例−1と全
く同様にしたところ、実施例−1と同様に良好なコピー
が得られた。
Example-4 Except that 5 parts of Exemplified Compound (7) was used as a charge control agent instead of 2 parts of Exemplified Compound (1), the same procedure as in Example-1 was carried out. Good copies were obtained as well.

【0026】実施例−5 帯電制御剤として、例示化合物(1)2部のかわりに例
示化合物(10)を3部使用する以外は、実施例−1と
全く同様にしたところ、実施例−1と同様に良好なコピ
ーが得られた。
Example-5 Except that 3 parts of Exemplified Compound (10) was used as the charge control agent instead of 2 parts of Exemplified Compound (1), the same procedure as in Example-1 was carried out. Good copies were obtained as well.

【0027】実施例−6 帯電制御剤として、例示化合物(1)2部のかわりに例
示化合物(11)を2部使用する以外は、実施例−1と
全く同様にしたところ、実施例−1と同様に良好なコピ
ーが得られた。
Example-6 Except that 2 parts of Exemplified Compound (11) was used as the charge control agent instead of 2 parts of Exemplified Compound (1), the same procedure as in Example-1 was carried out. Good copies were obtained as well.

【0028】実施例−7 帯電制御剤として、例示化合物(1)2部のかわりに例
示化合物(13)を3部使用する以外は、実施例−1と
全く同様にしたところ、実施例−1と同様に良好なコピ
ーが得られた。
Example-7 The procedure of Example-1 was repeated except that 3 parts of Exemplified Compound (13) was used as the charge control agent instead of 2 parts of Exemplified Compound (1). Good copies were obtained as well.

【0029】実施例−8 帯電制御剤として、例示化合物(1)2部のかわりに例
示化合物(16)を4部使用する以外は、実施例−1と
全く同様にしたところ、実施例−1と同様に良好なコピ
ーが得られた。
Example-8 The procedure of Example-1 was repeated except that 4 parts of Exemplified Compound (16) was used as the charge control agent instead of 2 parts of Exemplified Compound (1). Good copies were obtained as well.

【0030】実施例−9 帯電制御剤として、例示化合物(1)2部のかわりに例
示化合物(18)を3部使用する以外は、実施例−1と
全く同様にしたところ、実施例−1と同様に良好なコピ
ーが得られた。
Example-9 Except that 3 parts of Exemplified Compound (18) was used as the charge control agent instead of 2 parts of Exemplified Compound (1), the same procedure as in Example-1 was carried out. Good copies were obtained as well.

【0031】実施例−10 帯電制御剤として、例示化合物(1)2部のかわりに例
示化合物(20)を4部使用する以外は、実施例−1と
全く同様にしたところ、実施例−1と同様に良好なコピ
ーが得られた。
Example-10 Except that 4 parts of Exemplified Compound (20) was used as the charge control agent instead of 2 parts of Exemplified Compound (1), the same procedure as in Example-1 was carried out. Good copies were obtained as well.

【0032】[0032]

【発明の効果】本発明の静電荷像現像用トナーは、連続
複写によるコピーの汚れ等の発生しない高品質の静電荷
像現像用トナーである。
The toner for developing an electrostatic charge image of the present invention is a toner for developing an electrostatic charge image of high quality which does not cause stains on copies due to continuous copying.

Claims (1)

【特許請求の範囲】[Claims] 【請求項1】 少なくとも樹脂及び着色剤を含有してな
る静電荷像現像用トナーにおいて、サイクロオリゴ糖又
はその誘導体を1種以上含有することを特徴とする静電
荷像現像用トナー。
1. An electrostatic charge image developing toner comprising at least a resin and a colorant, which contains at least one cyclooligosaccharide or a derivative thereof.
JP04237031A 1992-09-04 1992-09-04 Toner for developing electrostatic images Expired - Fee Related JP3136792B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP04237031A JP3136792B2 (en) 1992-09-04 1992-09-04 Toner for developing electrostatic images

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP04237031A JP3136792B2 (en) 1992-09-04 1992-09-04 Toner for developing electrostatic images

Publications (2)

Publication Number Publication Date
JPH06124002A true JPH06124002A (en) 1994-05-06
JP3136792B2 JP3136792B2 (en) 2001-02-19

Family

ID=17009373

Family Applications (1)

Application Number Title Priority Date Filing Date
JP04237031A Expired - Fee Related JP3136792B2 (en) 1992-09-04 1992-09-04 Toner for developing electrostatic images

Country Status (1)

Country Link
JP (1) JP3136792B2 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0687959A1 (en) * 1994-05-30 1995-12-20 Hoechst Aktiengesellschaft Use of cyclic oligosaccharides or polysaccharides as charge control agents
EP0822461A1 (en) * 1996-08-02 1998-02-04 Xerox Corporation Liquid developer compositions with cyclodextrins
JP2012530809A (en) * 2009-06-17 2012-12-06 ボード・オブ・リージエンツ,ザ・ユニバーシテイ・オブ・テキサス・システム Compositions and methods for cyclofructans as separating agents

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0687959A1 (en) * 1994-05-30 1995-12-20 Hoechst Aktiengesellschaft Use of cyclic oligosaccharides or polysaccharides as charge control agents
EP0822461A1 (en) * 1996-08-02 1998-02-04 Xerox Corporation Liquid developer compositions with cyclodextrins
JP2012530809A (en) * 2009-06-17 2012-12-06 ボード・オブ・リージエンツ,ザ・ユニバーシテイ・オブ・テキサス・システム Compositions and methods for cyclofructans as separating agents
US9175006B2 (en) 2009-06-17 2015-11-03 Board Of Regents, The University Of Texas System Compositions and methods for cyclofructans as separation agents

Also Published As

Publication number Publication date
JP3136792B2 (en) 2001-02-19

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