JP6625643B2 - 感温変色性色彩記憶性組成物及びそれを内包した感温変色性色彩記憶性マイクロカプセル顔料 - Google Patents
感温変色性色彩記憶性組成物及びそれを内包した感温変色性色彩記憶性マイクロカプセル顔料 Download PDFInfo
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- JP6625643B2 JP6625643B2 JP2017532473A JP2017532473A JP6625643B2 JP 6625643 B2 JP6625643 B2 JP 6625643B2 JP 2017532473 A JP2017532473 A JP 2017532473A JP 2017532473 A JP2017532473 A JP 2017532473A JP 6625643 B2 JP6625643 B2 JP 6625643B2
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- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- DSOWAKKSGYUMTF-GZOLSCHFSA-M sodium;(1e)-1-(6-methyl-2,4-dioxopyran-3-ylidene)ethanolate Chemical compound [Na+].C\C([O-])=C1/C(=O)OC(C)=CC1=O DSOWAKKSGYUMTF-GZOLSCHFSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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- B43—WRITING OR DRAWING IMPLEMENTS; BUREAU ACCESSORIES
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- B43—WRITING OR DRAWING IMPLEMENTS; BUREAU ACCESSORIES
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- B43K8/04—Arrangements for feeding ink to writing-points
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- B43—WRITING OR DRAWING IMPLEMENTS; BUREAU ACCESSORIES
- B43L—ARTICLES FOR WRITING OR DRAWING UPON; WRITING OR DRAWING AIDS; ACCESSORIES FOR WRITING OR DRAWING
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Description
本発明は、(a)電子供与性呈色性有機化合物と、(b)電子受容性化合物と、(c)前記(a)成分および前記(b)成分の呈色反応をコントロールする反応媒体として、下記式(1)で示されるエステル化合物と、を含んでなる感温変色性色彩記憶性組成物に関するものである。
さらに本発明は、前記のマイクロカプセル顔料と、ビヒクルとを含んでなるインキ組成物にも関するものである。
図1において、縦軸に色濃度、横軸に温度が表されている。温度変化による色濃度は矢印に沿って変化する。ここで、Aは完全消色状態に達する温度T4(以下、完全消色温度と称す)における濃度を示す点であり、Bは完全発色状態を保持できる温度T3(以下、消色開始温度と称す)における濃度を示す点であり、Cは完全消色状態を保持できる温度T2(以下、発色開始温度と称す)における濃度を示す点であり、Dは完全発色状態に達する温度T1(以下、完全発色温度と称す)における濃度を示す点である。
本発明の(a)成分、即ち電子供与性呈色性有機化合物は、色を決める成分であって、顕色剤である(b)成分に電子を供与し、発色する化合物である。
3,3−ビス(p−ジメチルアミノフェニル)−6−ジメチルアミノフタリド、
3−(4−ジエチルアミノフェニル)−3−(1−エチル−2−メチルインドール−3−イル)フタリド、
3,3−ビス(1−n−ブチル−2−メチルインドール−3−イル)フタリド、
3,3−ビス(2−エトキシ−4−ジエチルアミノフェニル)−4−アザフタリド、
3−(2−エトキシ−4−ジエチルアミノフェニル)−3−(1−エチル−2−メチルインドール−3−イル)−4−アザフタリド、
3−(2−ヘキシルオキシ−4−ジエチルアミノフェニル)−3−(1−エチル−2−メチルインドール−3−イル)−4−アザフタリド、
3−〔2−エトキシ−4−(N−エチルアニリノ)フェニル〕−3−(1−エチル−2−メチルインドール−3−イル)−4−アザフタリド、
3−(2−アセトアミド−4−ジエチルアミノフェニル)−3−(1−プロピルインドール−3−イル)−4−アザフタリド、
3,6−ビス(ジフェニルアミノ)フルオラン、
3,6−ジメトキシフルオラン、
3,6−ジ−n−ブトキシフルオラン、
2−メチル−6−(N−エチル−N−p−トリルアミノ)フルオラン、
3−クロロ−6−シクロヘキシルアミノフルオラン、
2−メチル−6−シクロヘキシルアミノフルオラン、
2−(2−クロロアミノ)−6−ジブチルアミノフルオラン、
2−(2−クロロアニリノ)−6−ジ−n−ブチルアミノフルオラン、
2−(3−トリフルオロメチルアニリノ)−6−ジエチルアミノフルオラン、
2−(3−トリフルオロメチルアニリノ)−6−ジペンチルアミノフルオラン、
2−(ジベンジルアミノ)−6−ジエチルアミノフルオラン、
2−(N−メチルアニリノ)−6−(N−エチル−N−p−トリルアミノ)フルオラン、
1,3−ジメチル−6−ジエチルアミノフルオラン、
2−クロロ−3−メチル−6−ジエチルアミノフルオラン、
2−アニリノ−3−メチル−6−ジエチルアミノフルオラン、
2−アニリノ−3−メトキシ−6−ジエチルアミノフルオラン、
2−アニリノ−3−メチル−6−ジ−n−ブチルアミノフルオラン、
2−アニリノ−3−メトキシ−6−ジ−n−ブチルアミノフルオラン、
2−キシリジノ−3−メチル−6−ジエチルアミノフルオラン、
2−アニリノ−3−メチル−6−(N−エチル−N−p−トリルアミノ)フルオラン、
1,2−ベンツ−6−ジエチルアミノフルオラン、
1,2−ベンツ−6−(N−エチル−N−イソブチルアミノ)フルオラン、
1,2−ベンツ−6−(N−エチル−N−イソアミルアミノ)フルオラン、
2−(3−メトキシ−4−ドデコキシスチリル)キノリン、
スピロ〔5H−(1)ベンゾピラノ(2,3−d)ピリミジン−5,1′(3′H)イソベンゾフラン〕−3′−オン,2−(ジエチルアミノ)−8−(ジエチルアミノ)−4−メチル、
スピロ〔5H−(1)ベンゾピラノ(2,3−d)ピリミジン−5,1′(3′H)イソベンゾフラン〕−3′−オン,2−(ジ−n−ブチルアミノ)−8−(ジ−n−ブチルアミノ)−4−メチル、
スピロ〔5H−(1)ベンゾピラノ(2,3−d)ピリミジン−5,1′(3′H)イソベンゾフラン〕−3′−オン,2−(ジ−n−ブチルアミノ)−8−(ジエチルアミノ)−4−メチル、
スピロ〔5H−(1)ベンゾピラノ(2,3−d)ピリミジン−5,1′(3′H)イソベンゾフラン〕−3′−オン,2−(ジ−n−ブチルアミノ)−8−(N−エチル−N−i−アミルアミノ)−4−メチル、
スピロ〔5H−(1)ベンゾピラノ(2,3−d)ピリミジン−5,1′(3′H)イソベンゾフラン〕−3′−オン,2−(ジブチルアミノ)−8−(ジペンチルアミノ)−4−メチル、
4,5,6,7−テトラクロロ−3−〔4−(ジメチルアミノ)−2−メトキシフェニル〕−3−(1−ブチル−2−メチル−1H−インドール−3−イル)−1(3H)−イソベンゾフラノン、
4,5,6,7−テトラクロロ−3−〔4−(ジエチルアミノ)−2−エトキシフェニル〕−3−(1−エチル−2−メチル−1H−インドール−3−イル)−1(3H)−イソベンゾフラノン、
4,5,6,7−テトラクロロ−3−〔4−(ジエチルアミノ)−2−エトキシフェニル〕−3−(1−ペンチル−2−メチル−1H−インドール−3−イル)−1(3H)−イソベンゾフラノン、
4,5,6,7−テトラクロロ−3−[4−(ジエチルアミノ)−2−メチルフェニル]−3−(1−エチル−2−メチル−1H−インドール−3−イル)−1(3H)−イソベンゾフラノン、
3′,6′−ビス〔フェニル(2−メチルフェニル)アミノ〕−スピロ[イソベンゾフラン−1(3H),9′−〔9H〕キサンテン]−3−オン、
3′,6′−ビス〔フェニル(3−メチルフェニル)アミノ〕−スピロ[イソベンゾフラン−1(3H),9′−〔9H〕キサンテン]−3−オン、
3′,6′−ビス〔フェニル(3−エチルフェニル)アミノ〕−スピロ[イソベンゾフラン−1(3H),9′−〔9H〕キサンテン]−3−オン、
2,6−ビス(2′−エチルオキシフェニル)−4−(4′−ジメチルアミノフェニル)ピリジン、
2,6−ビス(2′,4′−ジエチルオキシフェニル)−4−(4′−ジメチルアミノフェニル)ピリジン、
2−(4′−ジメチルアミノフェニル)−4−メトキシ−キナゾリン、
4,4′−(エチレンジオキシ)−ビス〔2−(4−ジエチルアミノフェニル)キナゾリン〕。
本発明に用いられるエステル化合物は、式(1):
又、本発明における(a)、(b)、および(c)成分は各々2種以上の混合であってもよい。本発明における(c)成分は、式(1)を満たす化合物を二種以上含んでなるものであってもよい。また、前記(c)成分は、式(1)以外のエステル、アルコール、カルボン酸、ケトン及びアミド等、従来より公知の、(a)成分及び(b)成分による電子授受反応を特定温度域において可逆的に生起させる反応媒体と組み合わせて用いることもできる。
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(1)玩具類
人形又は動物形象玩具、人形又は動物形象玩具用毛髪、人形の家や家具、衣類、帽子、鞄、および靴等の人形用付属品、アクセサリー玩具、ぬいぐるみ、描画玩具、玩具用絵本、ジグソーパズル等のパズル玩具、積木玩具、ブロック玩具、粘土玩具、流動玩具、こま、凧、楽器玩具、料理玩具、鉄砲玩具、捕獲玩具、背景玩具および乗物、動物、植物、建築物、および食品等を模した玩具等、
(2)衣類
Tシャツ、トレーナー、ブラウス、ドレス、水着、レインコート、およびスキーウェア等の被服、靴や靴紐等の履物、ハンカチ、タオル、およびふろしき等の布製身の回り品、手袋、ネクタイ、帽子等、
(3)屋内装飾品
絨毯、カーテン、カーテン紐、テーブル掛け、敷物、クッション、額縁、造花、写真立て等、
(4)家具
布団、枕、マットレス等の寝具、照明器具および冷暖房器具等、
(5)装飾品
指輪、腕輪、ティアラ、イヤリング、髪止め、付け爪、リボン、およびスカーフ等時計、眼鏡等、
(6)文房具類
筆記具、スタンプ具、消しゴム、下敷き、定規、粘着テープ等、
(7)日用品
口紅、アイシャドー、マニキュア、染毛剤、付け爪、付け爪用塗料等の化粧品、歯ブラシ等、
(8)台所用品
コップ、皿、箸、スプーン、フォーク、鍋、フライパン等、
(9)その他
カレンダー、ラベル、カード、記録材、および偽造防止用の各種印刷物、絵本等の書籍、鞄、包装用容器、刺繍糸、運動用具、釣り具、コースター、楽器、カイロ、蓄冷剤、財布等の袋物、傘、乗物、建造物、温度検知用インジケーター、および教習具等。
各実施例における感温変色性色彩記憶性組成物及びそれを内包したマイクロカプセル顔料の製造方法と、感温変色性色彩記憶性組成物及びマイクロカプセル顔料の温度変化によるヒステリシス特性の測定方法について説明する。
なお、実施例中の部は質量部を表す。
感温変色性色彩記憶性組成物の調製方法
(a)成分として、2−(2−クロロアニリノ)−6−ジ−n−ブチルアミノフルオラン1部、(b)成分として、2,2−ビス(4−ヒドロキシフェニル)ヘキサフルオロプロパン2部、(c)成分として、p−ヒドロキシ安息香酸ノニルのフェノキシエチルエーテル(化合物4)50部からなる三成分を混合し、加温して均質に溶解して感温変色性色彩記憶性組成物を得た。
この感温変色性色彩記憶性組成物は黒色から無色に変色するものであった。
感温変色性色彩記憶性組成物を内径1mm、長さ78mmの透明ガラス製毛細管に、毛細管底部から約10mmの高さまで封入し、測定試料を得た。
測定試料の感温変色性色彩記憶性組成物を封入した部分全体を透明熱媒体の中に浸漬し、透明熱媒体の温度を変化させながら、感温変色性色彩記憶性組成物の変色状態を目視で観察して、T1(完全発色温度)、T2(発色開始温度)、T3(消色開始温度)、T4(完全消色温度)を測定し、TH〔T1とT2の中間の温度(T1+T2)/2〕、TG〔T3とT4の中間の温度(T3+T4)/2〕、ΔH(ヒステリシス幅TG−TH)を求めた。
実施例1の感温変色性色彩記憶性組成物はT1:15℃、T2:19℃、T3:42℃、T4:52℃、TH:17℃、TG:47℃、ΔH:30℃のヒステリシス特性を示した。
以下の表に記載した感温変色性色彩記憶性組成物の(a)成分、(c)成分を変更した以外は実施例1と同一方法で、実施例2〜4の感温変色性色彩記憶性組成物を調製し、実施例1と同様にして変色温度を測定した。
感温変色性色彩記憶性マイクロカプセル顔料の調製方法
(a)成分として3−(2−エトキシ−4−ジエチルアミノフェニル)−3−(1−エチル−2−メチルインドール−3−イル)−4−アザフタリド1部、(b)成分として2,2−ビス(4−ヒドロキシフェニル)ヘキサフルオロプロパン5部、(c)成分としてp−ヒドロキシ安息香酸ノニルのフェノキシエチルエーテル(化合物4)50部及びステアリン酸p−メチルベンジル3部からなる感温変色性色彩記憶性組成物を混合し、均一に加温溶解し、さらに壁膜材料として芳香族多価イソシアネートプレポリマー20部、酢酸エチル40部を混合した溶液を15%ゼラチン水溶液100部中に投入し、微小滴になるように乳化分散した。
感温変色性色彩記憶性マイクロカプセル顔料40部を、エチレン−酢酸ビニル樹脂エマルジョン50部、レベリング剤1部、消泡剤1部、粘度調整剤0.5部、水7.5部からなる水性インキビヒクルに均一に分散させて感温変色性色彩記憶性インキを調製した。このインキで上質紙にベタ柄をスクリーン印刷して測定試料を得た。
測定試料を色差計(TC−3600型色差計、東京電色株式会社製)の測定部分にセットし、試料部分を10℃/分の速度で昇温、降温させ、各温度における色濃度として明度値を測定し、色濃度−温度曲線を作成した。色濃度−温度曲線よりT1、T2、T3、T4、TH〔T1とT2の中間の温度(T1+T2)/2〕、TG〔T3とT4の中間の温度(T3+T4)/2〕、ΔH(ヒステリシス幅TG−TH)を求めた。
マイクロカプセルに内包させる感温変色性色彩記憶性組成物の(c)成分をp−ヒドロキシ安息香酸ノニルのフェノキシエチルエーテル(化合物4)50部及びステアリン酸p−メチルベンジル3部から、p−ヒドロキシ安息香酸ウンデシルのフェノキシエチルエーテル(化合物6)50部に変更した以外は実施例5と同様にして感温変色性マイクロカプセル顔料を調製し、青色から無色に変色する感温変色性色彩記憶性マイクロカプセル顔料を得た(平均粒子径1.8μm)。
実施例6で調製した感温変色性色彩記憶性マイクロカプセル顔料27部(予め−24℃以下に冷却して青色に発色させたもの)を、サクシノグリカン(剪断減粘性付与剤)0.3部、糖混合物〔三和澱粉工業株式会社製、商品名:サンデック70〕3.0部、リン酸エステル系界面活性剤0.5部、防黴剤0.1部、トリエタノールアミン1.0部、水68.1部ビヒクルに均一に分散させて感温変色性色彩記憶性液状組成物(筆記具用インキ)を調製した。
インキをポリプロピレン製パイプからなるインキ収容管に吸引充填し、樹脂製ホルダーを介して0.5mmステンレス鋼ボールを先端に抱持したボールペンチップと連結させた。
実施例5で調製した感温変色性色彩記憶性マイクロカプセル顔料27部(予め−19℃以下に冷却して青色に発色させたもの)を、キサンタンガム(剪断減粘性付与剤)0.33部、尿素10.0部、グリセリン10部、ノニオン系界面活性剤0.6部、変性シリコーン系消泡剤0.1部、防黴剤0.2部、水51.77部からなる水性インキビヒクルに均一に分散させて感温変色性色彩記憶性液状組成物(筆記具用インキ)を調製した。
インキをポリプロピレン製パイプに吸引充填し、樹脂製ホルダーを介して0.5mmステンレス鋼ボールを先端に抱持したボールペンチップと連結させた。
実施例6で調製した感温変色性色彩記憶性マイクロカプセル顔料25部(予め−24℃以下に冷却して青色に発色させたもの)、ヒドロキシエチルセルロース0.5部、櫛型高分子分散剤〔日本ルーブリゾール株式会社製、商品名:ソルスパース43000〕0.2部、有機窒素硫黄化合物〔北興化学工業株式会社製、商品名:ホクサイドR−150、2−メチル−4−イソチアゾリン−3−オンと5−クロロ−2−メチル−4−イソチアゾリン−3−オンの混合物〕1.0部、ポリビニルアルコール0.5部、グリセリン25.0部、消泡剤0.02部、水47.78部を混合して感温変色性色彩記憶性液状組成物(筆記具用インキ)を得た。
ポリエステルスライバーを合成樹脂フィルムで被覆したインキ吸蔵体内にインキ組成物を含浸させ、ポリプロピレン樹脂からなる軸筒内に収容し、ホルダーを介して軸筒先端部にポリエステル繊維の樹脂加工ペン体(砲弾型)と接続状態に組み立て、キャップを装着して筆記具(マーキングペン)を得た。
軸筒後端部には摩擦部材としてSEBS樹脂を装着してなる。
実施例6で調製した感温変色性色彩記憶性マイクロカプセル顔料2.5部及び非熱変色性蛍光ピンク色顔料1.5部を、塩化ビニル−酢酸ビニル共重合樹脂12.5部、キシレン38.3部、酢酸ブチル45部、粘度調整剤0.2部からなる油性インキビヒクルに均一に分散させて感温変色性色彩記憶性液状組成物(塗料)を調製した。
実施例5で調製した感温変色性色彩記憶性マイクロカプセル顔料(予め−19℃以下に冷却して青色に発色させたもの)30部をアクリル系樹脂エマルジョン(固形分45%)60部、粘度調整剤1部、消泡剤0.2部、水8.8部からなる水性インキビヒクルに均一に分散させて感温変色性色彩記憶性液状組成物(印刷インキ)を調製した。
実施例6で調製した感温変色性色彩記憶性マイクロカプセル顔料5部、分散剤1部、非熱変色性ピンク色顔料0.1部、ポリプロピレンホモポリマー93.9部をエクストルーダーにて180℃で溶融混合して感温変色性色彩記憶性成形用樹脂組成物(ペレット)を得た。
実施例5で調製した感温変色性色彩記憶性マイクロカプセル顔料20部(予め−19℃以下に冷却して青色に発色させたもの)を、アクリル系樹脂エマルジョン(固形分40%)78.0部、消泡剤2.0部からなる水性インキビヒクルに均一に分散させて感温変色性色彩記憶性液状組成物(印刷インキ)を調製した。
T2 発色開始温度
T3 消色開始温度
T4 完全消色温度
ΔH ヒステリシス幅
Claims (10)
- (a)電子供与性呈色性有機化合物と、(b)電子受容性化合物と、(c)前記(a)成分および(b)成分の呈色反応をコントロールする反応媒体として、下記式(1)で示されるエステル化合物と、を含んでなることを特徴とする感温変色性色彩記憶性組成物。
- 前記式(1)で表されるエステル化合物において、Rは炭素数6乃至16のアルキル基、炭素数6乃至8のシクロアルキルアルキル基、シクロヘキシル基のいずれかを示し、Xは水素原子、メチル基、エチル基、メトキシ基、またはエトキシ基のいずれかを示し、Yは水素原子、メチル基、エチル基、またはメトキシ基のいずれかである、請求項1に記載の組成物。
- Rは、炭素数6乃至14のアルキル基、シクロヘキシルメチル基のいずれかを示す、請求項1または2に記載の組成物。
- 前記(a)成分が、フタリド化合物、フルオラン化合物、スチリノキノリン化合物、ジアザローダミンラクトン化合物、ピリジン化合物、キナゾリン化合物、ビスキナゾリン化合物からなる群より選ばれる化合物である、請求項1〜3のいずれか1項に記載の組成物。
- 前記成分(b)および前記成分(c)の構成比が、質量基準で、前記成分(a)1部に対して、それぞれ、0.1〜50部、および1〜800部である、請求項1〜4のいずれか一項に記載の組成物。
- 請求項1〜5のいずれか1項に記載の感温変色性色彩記憶性組成物を内包してなることを特徴とする、感温変色性色彩記憶性マイクロカプセル顔料。
- 請求項6に記載のマイクロカプセル顔料と、ビヒクルと、を含んでなることを特徴とする、インキ組成物。
- 前記感温変色性色彩記憶性マイクロカプセル顔料の含有量が、前記インキ組成物の全質量に対し5〜40質量%である、請求項7に記載のインキ組成物。
- 請求項7または8に記載のインキ組成物を収容した軸筒及び前記軸筒内の前記インキ組成物を導出するペン体を備えてなることを特徴とする、筆記具。
- 摩擦部材をさらに備えてなる、請求項9に記載の筆記具。
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