JP2017116810A5 - - Google Patents
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- JP2017116810A5 JP2017116810A5 JP2015253946A JP2015253946A JP2017116810A5 JP 2017116810 A5 JP2017116810 A5 JP 2017116810A5 JP 2015253946 A JP2015253946 A JP 2015253946A JP 2015253946 A JP2015253946 A JP 2015253946A JP 2017116810 A5 JP2017116810 A5 JP 2017116810A5
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- styrene acrylic
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- acrylic resin
- resin
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- 239000000203 mixture Substances 0.000 claims description 44
- 229920005792 styrene-acrylic resin Polymers 0.000 claims description 42
- 229920005989 resin Polymers 0.000 claims description 25
- 239000011347 resin Substances 0.000 claims description 25
- 229920001225 Polyester resin Polymers 0.000 claims description 18
- 239000004645 polyester resin Substances 0.000 claims description 18
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 16
- 239000002245 particle Substances 0.000 claims description 11
- 239000011230 binding agent Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- -1 polyethylene Polymers 0.000 claims description 6
- 229920002456 HOTAIR Polymers 0.000 claims description 3
- 238000004898 kneading Methods 0.000 claims description 3
- 239000004698 Polyethylene (PE) Substances 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 2
- 239000004743 Polypropylene Substances 0.000 claims 1
- 238000006068 polycondensation reaction Methods 0.000 claims 1
- 229920001155 polypropylene Polymers 0.000 claims 1
- 238000004381 surface treatment Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 description 25
- 239000006185 dispersion Substances 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N Heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
本発明は、結着樹脂、結晶性ポリエステル樹脂、ワックス、及びスチレンアクリル系樹脂組成物を含有するトナー粒子であって、
該結着樹脂は、非晶性ポリエステル樹脂を含有し、
該スチレンアクリル系樹脂組成物は、脂肪族系炭化水素樹脂でグラフト変性させているスチレンアクリル系樹脂を含有し、該脂肪族系炭化水素樹脂でグラフト変性させているスチレンアクリル系樹脂組成物は、下記式（１）で表わされる化合物に由来するユニットを含有し、該脂肪族系炭化水素樹脂でグラフト変性させているスチレンアクリル系樹脂組成物の含有量が、該トナー粒子１００質量部に対して１．０質量部以上１０質量部以下であることを特徴とするトナーに関する。
The binder resin contains an amorphous polyester resin,
The styrene acrylic resin composition contains a styrene acrylic resin that is graft-modified with an aliphatic hydrocarbon resin, and the styrene acrylic resin composition that is graft-modified with the aliphatic hydrocarbon resin. The content of the styrene acrylic resin composition containing units derived from the compound represented by the following formula (1) and graft-modified with the aliphatic hydrocarbon resin is 100 parts by mass of the toner particles. The present invention relates to a toner that is 1.0 part by mass or more and 10 parts by mass or less.
本発明のトナーは、結着樹脂としての非晶性ポリエステル樹脂、軟化剤としての結晶性ポリエステル樹脂、ワックス、及びワックス分散剤としてのスチレンアクリル系樹脂組成物を含有するトナー粒子であって、該スチレンアクリル系樹脂組成物は、脂肪族系炭化水素樹脂でグラフト変性させているスチレンアクリル系樹脂を含有し、該脂肪族系炭化水素樹脂でグラフト変性させているスチレンアクリル系樹脂組成物は、下記式（１）で表わされる化合物に由来するユニットを含有し、該脂肪族系炭化水素樹脂でグラフト変性させているスチレンアクリル系樹脂組成物の含有量が、該トナー粒子１００質量部に対して１．０質量部以上１０質量部以下であることを特徴とする。
＜スチレンアクリル系樹脂組成物Ａ１の製造例＞
温度計および撹拌機の付いたオートクレーブ反応槽中に、キシレン３００質量部、ポリエチレン１０質量部を入れ充分溶解し、窒素置換後、スチレン６８質量部、ステアリルメタクリレート２質量部、アクリロニトリル３０質量部およびキシレン２５０質量部の混合溶液を１８０℃で３時間滴下し重合し、さらにこの温度で３０分間保持した。次いで脱溶剤を行い、ワックス分散剤としてのスチレンアクリル系樹脂組成物Ａ１を得た。
<Production Example of Styrene Acrylic Resin Composition A1>
In an autoclave reaction vessel equipped with a thermometer and a stirrer, 300 parts by mass of xylene and 10 parts by mass of polyethylene were sufficiently dissolved, and after substitution with nitrogen, 68 parts by mass of styrene, 2 parts by mass of stearyl methacrylate, 30 parts by mass of acrylonitrile and xylene 250 parts by mass of the mixed solution was added dropwise at 180 ° C. for 3 hours for polymerization, and further maintained at this temperature for 30 minutes. Next, the solvent was removed to obtain a styrene acrylic resin composition A1 as a wax dispersant.
＜スチレンアクリル系樹脂組成物Ａ２及びＡ３の製造例＞
スチレンアクリル系樹脂組成物Ａ１の製造例において、脂肪族系炭化水素樹脂が表１となるように適宜条件を変更した以外は、スチレンアクリル系樹脂組成物Ａ１の製造例と同様の操作を行い、スチレンアクリル系樹脂組成物Ａ２及びＡ３を得た。得られたワックス分散剤の組成、ＳＰ値を表１に示す。
<Production Example of Styrene Acrylic Resin Compositions A2 and A3>
In the production example of the styrene acrylic resin composition A1, the same operation as in the production example of the styrene acrylic resin composition A 1 was carried out except that the conditions were appropriately changed so that the aliphatic hydrocarbon resin was as shown in Table 1. The styrene acrylic resin compositions A2 and A3 were obtained. The composition and SP value of the obtained wax dispersant are shown in Table 1.
＜スチレンアクリル系樹脂組成物Ａ４の製造例＞
スチレンアクリル系樹脂組成物Ａ１の製造例において、脂肪族系炭化水素樹脂及びＳＰ値が表１となるように適宜条件とモノマー比率を変更した以外は、スチレンアクリル系樹脂組成物Ａ１の製造例と同様の操作を行い、スチレンアクリル系樹脂組成物Ａ４を得た。得られたワックス分散剤の組成、ＳＰ値を表１に示す。
<Production Example of Styrene Acrylic Resin Composition A4>
In the production example of the styrene acrylic resin composition A1, the production example of the styrene acrylic resin composition A 1 was changed except that the aliphatic hydrocarbon resin and the SP value were appropriately changed so that the SP value was as shown in Table 1. The same operation was performed to obtain a styrene acrylic resin composition A4. The composition and SP value of the obtained wax dispersant are shown in Table 1.
＜スチレンアクリル系樹脂組成物Ａ５及びＡ６の製造例＞
スチレンアクリル系樹脂組成物Ａ１の製造例において、脂肪族系炭化水素樹脂及び式（１）の化合物が表１となるように適宜条件を変更した以外は、スチレンアクリル系樹脂組成物Ａ１の製造例と同様の操作を行い、スチレンアクリル系樹脂組成物Ａ５及びＡ６を得た。得られたワックス分散剤の組成、ＳＰ値を表１に示す。
<Production Example of Styrene Acrylic Resin Compositions A5 and A6>
In the production examples of the styrene acrylic resin composition A1, except that the compound of the aliphatic hydrocarbon resin and (1) changes the appropriate conditions such that the Table 1, the production of styrene acrylic resin composition A 1 Styrene acrylic resin compositions A5 and A6 were obtained in the same manner as in the examples. The composition and SP value of the obtained wax dispersant are shown in Table 1.
＜スチレンアクリル系樹脂組成物Ａ７の製造例＞
スチレンアクリル系樹脂組成物Ａ１の製造例において、脂肪族系炭化水素樹脂、式（１）の化合物、及びＳＰ値が表１となるように適宜条件とモノマー比率を変更した以外は、スチレンアクリル系樹脂組成物Ａ１の製造例と同様の操作を行い、スチレンアクリル系樹脂組成物Ａ７を得た。得られたワックス分散剤の組成、ＳＰ値を表１に示す。
<Production Example of Styrene Acrylic Resin Composition A7>
In the production examples of the styrene acrylic resin composition A1, aliphatic hydrocarbon resins, compounds of formula (1), and except that the SP value is changed as appropriate conditions and monomer ratios such that the Table 1, styrene-acrylic Operation similar to the manufacture example of resin composition A1 was performed, and styrene acrylic resin composition A7 was obtained. The composition and SP value of the obtained wax dispersant are shown in Table 1.
＜スチレンアクリル系樹脂組成物Ａ８乃至Ａ１０の製造例＞
スチレンアクリル系樹脂組成物Ａ１の製造例において、脂肪族系炭化水素樹脂、式（１）の化合物及びその他の化合物が表１となるように適宜条件とモノマー比率を変更した以外は、スチレンアクリル系樹脂組成物Ａ１の製造例と同様の操作を行い、スチレンアクリル系樹脂組成物Ａ８乃至Ａ１０を得た。得られたワックス分散剤の組成、ＳＰ値を表１に示す。
<Production Example of Styrene Acrylic Resin Compositions A8 to A10>
In the production examples of the styrene acrylic resin composition A1, aliphatic hydrocarbon resins, except that compound and other compounds of formula (1) changes the appropriate conditions and monomer ratios such that the Table 1, styrene-acrylic Operation similar to the manufacture example of resin composition A1 was performed, and styrene acrylic resin composition A8 thru | or A10 was obtained. The composition and SP value of the obtained wax dispersant are shown in Table 1.
＜トナー１の製造例：熱風処理工程を含む溶融混練製法＞
・結着樹脂Ｃ ３５質量部
・結着樹脂Ｄ ６５質量部
・結晶性ポリエステル樹脂Ｂ１ ７．５質量部
・フィッシャートロプシュワックス（炭化水素ワックス、最大吸熱ピークのピーク温度９０℃） ５質量部
・スチレンアクリル系樹脂組成物Ａ１ ５質量部
・Ｃ．Ｉ．ピグメントブルー１５：３ ７質量部
・３，５−ジ−ｔ−ブチルサリチル酸アルミニウム化合物（ボントロンＥ８８ オリエント化学工業社製） ０．３質量部
上記材料をヘンシェルミキサー（ＦＭ−７５型、三井鉱山（株）製）を用いて、回転数２０ｓ-1、回転時間５ｍｉｎで混合した後、温度１３０℃に設定した二軸混練機（ＰＣＭ−３０型、株式会社池貝製）にて混練した。得られた混練物を冷却し、ハンマーミルにて１ｍｍ以下に粗粉砕し、粗砕物を得た。得られた粗砕物を、機械式粉砕機（Ｔ−２５０、ターボ工業（株）製）にて微粉砕した。さらにファカルティＦ−３００（ホソカワミクロン社製）を用い、分級を行い、トナー粒子１を得た。運転条件は、分級ローター回転数を１３０ｓ-1、分散ローター回転数を１２０ｓ-1とした。
<Production Example of Toner 1: Melt-kneading production method including hot air treatment step>
-Binder resin C 35 parts by mass-Binder resin D 65 parts by mass-Crystalline polyester resin B1 7.5 parts by mass-Fischer-Tropsch wax (hydrocarbon wax, peak temperature of maximum endothermic peak 90 ° C) 5 parts by mass- Styrene Acrylic resin composition A1 5 parts by mass / C.I. I. Pigment Blue 15: 3 7 parts by mass, 3,5-di-t-butylsalicylic acid aluminum compound (Bontron E88 manufactured by Orient Chemical Industry Co., Ltd.) 0.3 parts by mass Henschel mixer (FM-75 type, Mitsui Mine Co., Ltd.) The product was mixed at a rotation speed of 20 s −1 and a rotation time of 5 minutes, and then kneaded in a biaxial kneader (PCM-30 type, manufactured by Ikegai Co., Ltd.) set at a temperature of 130 ° C. The obtained kneaded material was cooled and coarsely pulverized to 1 mm or less with a hammer mill to obtain a coarsely pulverized material. The obtained coarsely crushed material was finely pulverized with a mechanical pulverizer (T-250, manufactured by Turbo Kogyo Co., Ltd.). Furthermore, classification was performed using Faculty F-300 (manufactured by Hosokawa Micron Corporation) to obtain toner particles 1. The operating conditions were a classification rotor rotational speed of 130 s −1 and a distributed rotor rotational speed of 120 s −1 .
＜トナー２乃至トナー１２、トナー１４乃至トナー２６及びトナー２８の製造例＞
トナー１の製造例において、スチレンアクリル系樹脂組成物Ａの種類と含有量、結晶性ポリエステル樹脂Ｂの種類と含有量を表３に示したように変更したほかは同様の操作を行い、トナー２乃至トナー１２、トナー１４乃至トナー２６及び、トナー２８を得た。
<Production Examples of Toner 2 to Toner 12, Toner 14 to Toner 26, and Toner 28>
In the production example of the toner 1, the same operation was performed except that the type and content of the styrene acrylic resin composition A and the type and content of the crystalline polyester resin B were changed as shown in Table 3, and the toner 2 Through toner 12, toner 14 through toner 26, and toner 28 were obtained.
（ワックス分散液）
・フィッシャートロプシュワックス（炭化水素ワックス、最大吸熱ピークのピーク温度９０℃） ４５質量部
・スチレンアクリル系樹脂組成物Ａ１ ４５質量部
・アニオン性界面活性剤 ５質量部
・イオン交換水 １５０質量部
以上を９５℃に加熱して、ホモジナイザーを用いて分散した後、圧力吐出型ゴーリンホモジナイザーで分散処理し、体積平均粒径が２１０ｎｍである離型剤を分散させてなる離型剤分散液（ワックス濃度：２０％）を調製した。
・非晶性ポリエステル樹脂分散液 ５００質量部
・結晶性ポリエステル樹脂Ｂ１分散液 ７５質量部
以上を丸型ステンレス製フラスコ中においてホモジナイザーで混合・分散した。これにポリ塩化アルミニウム０．１５部を加え、ウルトラタラックスで分散操作を継続した。その後、
・着色剤分散液 ３０．５質量部
・離型剤分散液 ２５質量部
以上を追加し、さらにポリ塩化アルミニウム０．０５質量部を加え、ウルトラタラックスで分散操作を継続した。
(Wax dispersion)
-45 parts by mass of Fischer-Tropsch wax (hydrocarbon wax, maximum endothermic peak peak temperature 90 ° C)-45 parts by mass of styrene acrylic resin composition A1-5 parts by mass of anionic surfactant-150 parts by mass of ion-exchanged water After being heated to 95 ° C. and dispersed using a homogenizer, a release agent dispersion (wax concentration: dispersed by a pressure discharge type gorin homogenizer and dispersed with a release agent having a volume average particle size of 210 nm) 20%) was prepared.
-Amorphous polyester resin dispersion 500 parts by mass-Crystalline polyester resin B1 dispersion 75 parts by mass The above was mixed and dispersed with a homogenizer in a round stainless steel flask. To this, 0.15 part of polyaluminum chloride was added, and the dispersion operation was continued with an ultra turrax. after that,
-Colorant dispersion 30.5 parts by mass-Release agent dispersion 25 parts by mass The above was added, 0.05 parts by mass of polyaluminum chloride was further added, and the dispersion operation was continued with an ultra turrax.
＜トナー２７の製造例：溶融混練製法＞
トナー１の製造例で、スチレンアクリル系樹脂組成物Ａの種類、結晶性ポリエステル樹脂Ｂの種類と含有量を表２に示したように変更し、トナー粒子１を熱風処理しなかったほかは、トナー１と同様の製造方法でトナー２７を得た。得られたトナー２７を５５℃／４１％ＲＨに４８時間放置し、ＤＳＣ測定を行ったところ、結晶性樹脂に由来する吸熱ピークとワックスに由来する吸熱ピークがそれぞれ観察された。
<Manufacturing example of toner 27: melt-kneading method>
In the production example of the toner 1, except that the type of the styrene acrylic resin composition A and the type and content of the crystalline polyester resin B were changed as shown in Table 2, and the toner particles 1 were not treated with hot air, Toner 27 was obtained by the same production method as Toner 1. The obtained toner 27 was allowed to stand at 55 ° C./41% RH for 48 hours and subjected to DSC measurement. As a result, an endothermic peak derived from the crystalline resin and an endothermic peak derived from the wax were observed.
＜トナー２９及びトナー３０の製造例＞
トナー１の製造例において、結晶性ポリエステル樹脂を用いず、スチレンアクリル系樹脂組成物Ａの種類と含有量を表２に示したように変更したほかは同様の操作を行い、トナー２９及びトナー３０を得た。得られたトナー２９及びトナー３０を５５℃／４１％ＲＨに４８時間放置し、ＤＳＣ測定を行ったところ、ワックスに由来する吸熱ピークが観察された。
<Production Example of Toner 29 and Toner 30>
In the production example of the toner 1, the same operation was performed except that the crystalline polyester resin was not used and the type and content of the styrene acrylic resin composition A were changed as shown in Table 2. Got. The obtained toner 29 and toner 30 were allowed to stand at 55 ° C./41% RH for 48 hours and subjected to DSC measurement. As a result, an endothermic peak derived from wax was observed.
Claims (7)
該結着樹脂は、非晶性ポリエステル樹脂を含有し、
該スチレンアクリル系樹脂組成物は、脂肪族系炭化水素樹脂でグラフト変性させているスチレンアクリル系樹脂を含有し、該脂肪族系炭化水素樹脂でグラフト変性させているスチレンアクリル系樹脂組成物は、下記式（１）で表わされる化合物に由来するユニットを含有し、該脂肪族系炭化水素樹脂でグラフト変性させているスチレンアクリル系樹脂組成物の含有量が、該トナー粒子１００質量部に対して１．０質量部以上１０質量部以下であることを特徴とするトナー。
The binder resin contains an amorphous polyester resin,
The styrene acrylic resin composition contains a styrene acrylic resin that is graft-modified with an aliphatic hydrocarbon resin, and the styrene acrylic resin composition that is graft-modified with the aliphatic hydrocarbon resin. The content of the styrene acrylic resin composition containing units derived from the compound represented by the following formula (1) and graft-modified with the aliphatic hydrocarbon resin is 100 parts by mass of the toner particles. 1.0 to 10 parts by mass of toner.
該結晶性ポリエステル樹脂の含有量が、該非晶性ポリエステル樹脂１００質量部に対し１．０質量部以上１５質量部以下である請求項１乃至５のいずれか１項に記載のトナー。 The crystalline polyester resin is a crystalline polyester resin obtained by polycondensation of an aliphatic diol having 6 to 12 carbon atoms and an aliphatic dicarboxylic acid having 6 to 12 carbon atoms,
6. The toner according to claim 1, wherein the content of the crystalline polyester resin is 1.0 part by mass or more and 15 parts by mass or less with respect to 100 parts by mass of the amorphous polyester resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015253946A JP6700779B2 (en) | 2015-12-25 | 2015-12-25 | toner |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015253946A JP6700779B2 (en) | 2015-12-25 | 2015-12-25 | toner |
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| Publication Number | Publication Date |
|---|---|
| JP2017116810A JP2017116810A (en) | 2017-06-29 |
| JP2017116810A5 true JP2017116810A5 (en) | 2019-02-14 |
| JP6700779B2 JP6700779B2 (en) | 2020-05-27 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015253946A Active JP6700779B2 (en) | 2015-12-25 | 2015-12-25 | toner |
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| JP6331502B2 (en) * | 2014-03-10 | 2018-05-30 | 株式会社リコー | Toner, developer, and image forming apparatus |
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