WO2009145132A1 - Effaceur - Google Patents

Effaceur Download PDF

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Publication number
WO2009145132A1
WO2009145132A1 PCT/JP2009/059505 JP2009059505W WO2009145132A1 WO 2009145132 A1 WO2009145132 A1 WO 2009145132A1 JP 2009059505 W JP2009059505 W JP 2009059505W WO 2009145132 A1 WO2009145132 A1 WO 2009145132A1
Authority
WO
WIPO (PCT)
Prior art keywords
eraser
polyisocyanate
weight
diisocyanate
ester
Prior art date
Application number
PCT/JP2009/059505
Other languages
English (en)
Japanese (ja)
Inventor
正充 高橋
英敏 福尾
Original Assignee
株式会社サクラクレパス
広谷 誠
辻尾 伸二
北口 貴之
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 株式会社サクラクレパス, 広谷 誠, 辻尾 伸二, 北口 貴之 filed Critical 株式会社サクラクレパス
Priority to JP2010514459A priority Critical patent/JPWO2009145132A1/ja
Publication of WO2009145132A1 publication Critical patent/WO2009145132A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B43—WRITING OR DRAWING IMPLEMENTS; BUREAU ACCESSORIES
    • B43L—ARTICLES FOR WRITING OR DRAWING UPON; WRITING OR DRAWING AIDS; ACCESSORIES FOR WRITING OR DRAWING
    • B43L19/00—Erasers, rubbers, or erasing devices; Holders therefor
    • B43L19/0025—Eraser or rubber material, e.g. comprising hard particles

Definitions

  • the present invention typically relates to an eraser for rubbing a handwriting formed with a pencil on paper and erasing it.
  • Japanese Patent Laid-Open No. 10-193880 JP 2004-188850 A JP 05-147392 A Japanese Patent Laid-Open No. 2000-025391
  • an object of the present invention is to provide an eraser based on polyurethane which is more excellent in erasing performance as well as slipping during erasing.
  • polyurethane obtained by reacting 20 to 50% by weight of at least one polyol selected from castor oil and hardened castor oil and 5 to 17% by weight of polyisocyanate, 3 to 30% by weight of plasticizer, and abrasive 10
  • an eraser comprising ⁇ 40% by weight and 5-20% by weight filler.
  • at least one polyol selected from castor oil and hardened castor oil, together with 3 to 30% by weight of a plasticizer, 10 to 40% by weight of an abrasive, and 5 to 20% by weight of a filler is 20 to 50% by weight.
  • polyisocyanate 5 to 17% by weight of polyisocyanate is dissolved at room temperature or under heating if necessary, and the resulting mixture is poured into a mold to react the polyisocyanate with the polyol under heating. Is completed, and the molded product obtained is taken out from the mold and cut into a required shape.
  • a polyurethane having a high crosslinking density obtained by reacting at least one polyol selected from castor oil and hydrogenated castor oil and polyisocyanate is used as a base material, and a plasticizer, an abrasive and a filler are combined.
  • a uniform composition it is possible to obtain an eraser that can be erased well by lightly rubbing the handwriting on the paper surface, that is, with good sliding and light touch.
  • the eraser according to the present invention comprises a polyurethane obtained by reacting 20 to 50% by weight of at least one polyol selected from castor oil and hardened castor oil and 5 to 17% by weight of polyisocyanate, 3 to 30% by weight of a plasticizer, and abrasive 10 It contains about 40% by weight and 5-20% by weight filler.
  • the proportion of each component used in the production of the eraser is defined as a percentage based on the weight of the resulting eraser (ie, wt%), and thus the eraser obtained using each of the above components. Constitutes 100% by weight.
  • At least one selected from castor oil and hardened castor oil is used as a polyol for obtaining polyurethane as a base material.
  • the main component (about 90%) of castor oil is ricinoleic acid triglyceride, which is an unsaturated oxyacid having a hydroxy group and a double bond in the molecule. Therefore, castor oil is mainly composed of a trifunctional polyol, and the hydroxyl value of castor oil is usually in the range of 150 to 170 mgKOH / g.
  • Hardened castor oil is a wax-like one having a melting point of about 85 ° C.
  • a polyurethane having a high crosslinking density obtained by reacting such a polyol with a polyisocyanate described later is used as a base material, and a plasticizer, an abrasive, and a filler are contained in the base material on the paper surface.
  • An eraser that can be erased well by sliding lightly, that is, with a smooth and light touch can be obtained.
  • the polyol is usually used in the range of 20 to 50% by weight based on the weight of the eraser.
  • the amount of the polyol used is out of the above range, a solidified product cannot be obtained even if the polyisocyanate is used in the proportion specified in the present invention together with the plasticizer, abrasive and filler described later.
  • the polyisocyanate may be aliphatic, alicyclic, aromatic and aromatic fat as long as it can be dissolved in a mixture of a polyol to be used and a plasticizer described below at room temperature or under heating as necessary.
  • Any of the group polyisocyanates can be used.
  • Specific examples of such polyisocyanates include tetramethylene diisocyanate, dodecamethylene diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, lysine diisocyanate, 2-methyl.
  • Aliphatic polyisocyanates such as pentane-1,5-diisocyanate, 3-methylpentane-1,5-diisocyanate, isophorone diisocyanate, hydrogenated xylylene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 1,4-cyclohexane diisocyanate, Alicyclic polyisocyanates such as methylcyclohexylene diisocyanate and 1,3-bis (isocyanatomethyl) cyclohexane, Aromatics such as polydiisocyanate, diphenylmethane diisocyanate, polymethylene polyphenyl polyisocyanate, tolidine diisocyanate, 4,4'-dibenzyl diisocyanate, 1,5-naphthylene diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate Examples thereof include araliphatic polyis
  • examples of the polyisocyanate preferably used in the present invention include tolylene diisocyanate, diphenylmethane diisocyanate, polymethylene polyphenyl polyisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethylxylylene diisocyanate, hydrogenated xylylene diisocyanate, and the like. be able to.
  • tolylene diisocyanate, polymethylene polyphenyl polyisocyanate, hexamethylene diisocyanate or isophorone diisocyanate is preferably used. These may be used alone or in combination of two or more.
  • these polyisocyanates may be reacted with the above-described polyol in advance and used as a prepolymer.
  • the adduct or isocyanurate of the above polyisocyanate can be used together with the polyisocyanate in the present invention, as long as it can be dissolved in a mixture of a polyol to be used and a plasticizer described later under heating at an ordinary temperature or if necessary. Alone, it is used as a polyisocyanate.
  • An adduct is, for example, a trifunctional polyisocyanate obtained by addition reaction of 3 mole parts of diisocyanate to 1 mole part of a trihydric alcohol such as trimethylolpropane or glycerin.
  • a trihydric alcohol such as trimethylolpropane or glycerin.
  • the isocyanurate is a trifunctional polyisocyanate obtained by trimerizing diisocyanate, and can similarly include cyanurates such as tolylene diisocyanate, hexamethylene diisocyanate, and isophorone diisocyanate.
  • the polyisocyanate is usually used in the range of 5 to 17% by weight, preferably in the range of 5 to 10% by weight, based on the weight of the eraser.
  • the eraser is based on a polyurethane obtained by the reaction of 5 to 17% by weight of polyisocyanate, preferably 5 to 10% by weight and 20 to 50% by weight of polyol, based on its weight.
  • the plasticizer imparts appropriate elasticity to the resulting eraser to improve the touch during erasing, improve usability, and when rubbing the handwriting on the paper, adsorbs the handwriting made of graphite and erases it. It plays the role of improving the character performance. According to the present invention, various plasticizers are used.
  • plasticizer examples include aliphatic di-2-ethylhexyl adipate, diisononyl adipate, dibutyl sebacate, di-2-ethylhexyl sebacate, di-2-ethylhexyl azelate, and the like.
  • Dialkyl esters of basic acids such as acetyl citrate trialkyl esters such as acetyl triethyl acetyl citrate, tributyl acetyl citrate, acetyl ricinoleic acid alkyl esters such as methyl acetyl ricinolate and butyl acetyl ricinoleate, alkyl sulfonates such as phenyl alkyl sulfonate , Benzoic acid dialkylene glycol esters, trimellitic acid trialkyl esters such as trimellitic acid tris (2-ethylhexyl), 4,5-epoxy-1,2-cyclohexanedicarboxylic acid Bis (2-ethylhexyl) epoxidized cyclohexanedicarboxylic acid dialkyl esters such as tributyl phosphate, tri-2-ethylhexyl phosphate, triphen
  • Such a plasticizer is usually used in the range of 3 to 30% by weight, preferably in the range of 10 to 30% by weight, based on the eraser.
  • the proportion of the plasticizer in the eraser is less than 3% by weight, the obtained eraser is hard, the touch when erasing is poor, and the erasing performance is low.
  • the proportion of the plasticizer in the eraser is more than 30% by weight, the eraser obtained is too soft and unusable.
  • Abrasives when scrubbing the handwriting on the paper, shave the paper and handwriting to aid erasing and promote the action of causing the surface of the eraser to wear off and generating swarf, thus It plays the role of preventing adhesion of dirt such as graphite on the paper surface.
  • abrasives examples include calcium carbonate, talc, clay, mica, aluminum hydroxide, calcium hydroxide, magnesium hydroxide, calcium sulfate, zinc oxide, aluminum oxide, titanium oxide, anhydrous silicic acid, glass flakes and silica stone. Etc. are used.
  • the abrasive is usually used in the range of 10 to 40% by weight based on the eraser.
  • the proportion of the abrasive in the eraser is less than 10% by weight, the resulting eraser does not have sufficient erasing performance.
  • the proportion of the abrasive in the eraser is more than 40% by weight, not only the paper surface is damaged more than necessary but also the erasing performance is lowered. In addition, it is difficult for scraps to be collected.
  • spherical hollow fine particles are preferably used as the filler.
  • spherical hollow fine particles inorganic spherical hollow fine particles and organic spherical hollow fine particles are known, and these are used alone or in combination.
  • organic spherical hollow fine particles include a phenol balloon and a vinylidene chloride balloon.
  • These organic spherical hollow fine particles have, for example, a polyvinylidene chloride-acrylonitrile copolymer, an acrylonitrile-acrylic ester copolymer, an outer wall made of a resin such as polyethylene, polypropylene, styrene-acrylic copolymer, and an average particle diameter of about 50 ⁇ m.
  • a resin such as polyethylene, polypropylene, styrene-acrylic copolymer
  • inorganic spherical hollow fine particles glass balloons, shirasu balloons, silica balloons and the like are preferably used.
  • Such inorganic spherical hollow fine particles are usually hollow spheres of about several ⁇ m to several tens of ⁇ m.
  • the spherical hollow fine particles are used in the range of 5 to 20% by weight based on the eraser, thereby reducing the frictional resistance between the paper surface and the eraser during erasing, thereby reducing the light abrasion.
  • the characters can be erased with a light touch.
  • the proportion of the inorganic spherical hollow fine particles in the eraser is less than 5% by weight, the above effect cannot be obtained.
  • the proportion of the inorganic spherical hollow fine particles in the eraser is more than 20% by weight, there is a drawback that the eraser tends to break when the handwriting is rubbed during erasure.
  • inorganic spherical hollow fine particles are particularly preferably used from the viewpoint of excellent effect of reducing the frictional resistance between the paper surface and the eraser when erasing.
  • the eraser according to the present invention is not particularly limited in its production method, but usually, preferably in a reaction vessel, the mixture containing the predetermined amount of a plasticizer, an abrasive, a filler, and a polyol at room temperature.
  • the predetermined amount of polyisocyanate is dissolved under heating, the resulting mixture is poured into a mold, and the reaction between the polyisocyanate and the polyol is completed under heating, and the resulting molding is obtained. It can be obtained by removing the object from the mold and cutting it into a required shape.
  • a polyol is charged together with the predetermined amount of the plasticizer, the abrasive and the filler in an appropriate reaction vessel, and stirred at room temperature or under heating at 50 to 100 ° C., if necessary. After making the mixture, it is heated to 50-100 ° C. After the temperature of the mixture is stabilized, the predetermined amount of polyisocyanate is added thereto and stirred for about 10 minutes to 1 hour. Thereafter, the mixture thus obtained is degassed, poured into a mold, and is not limited to an oven at 110 to 150 ° C., preferably 115 to 130 ° C. Heat for about 3 to 3 hours to complete the reaction between the polyisocyanate and the polyol. The molded product thus obtained is taken out from the mold and cut into a required shape to obtain the eraser according to the present invention.
  • a third compound such as triethylenediamine, N, N′-dimethylhexamethylenediamine, N, N′-dimethylbutanediamine, or the like is used.
  • Conventionally known urethanization catalysts such as class amines, organometallic compounds such as lead octylate and dibutyltin laurate may be used.
  • the eraser according to the present invention may contain additives such as a colorant and a flame retardant, if necessary, and a heat stabilizer for improving the durability and stability of the resulting eraser.
  • additives such as a colorant and a flame retardant, if necessary, and a heat stabilizer for improving the durability and stability of the resulting eraser.
  • an antioxidant, an ultraviolet absorber and the like may be appropriately contained.
  • each eraser was produced using the raw materials shown in Tables 1 to 3.
  • Tables 1 to 3 the amount of each raw material is parts by weight.
  • the raw materials shown in Tables 1 to 3 are as follows. Castor oil: No. 1 castor oil manufactured by Toyokuni Oil Co., Ltd. (hydroxyl value 161 mgKOH / g by neutralization titration method) Hardened castor oil: castor hardened oil manufactured by Ito Oil Co., Ltd.
  • Plasticizer 1 Daihachi Chemical Industry Co., Ltd. tricresyl phosphate plasticizer 2: Shin Nippon Rika Co., Ltd. sansosizer (diisononyl adipate) Plasticizer 3: Asahi Kasei Finechem Co., Ltd. acetyl tributyl citrate plasticizer 4: Lanxess Co., Ltd.
  • Plasticizer 5 Bis (2-ethylhexyl) 4,5-epoxy-1,2-cyclohexanecarboxylate manufactured by DIC Corporation “Monocizer W-150”
  • Plasticizer 6 Dialkylene glycol benzoate “Monocizer PB-3A” manufactured by DIC Corporation Plasticizer 7: Trimellitic acid tris (2-ethylhexyl) “Monocizer W-705” manufactured by DIC Corporation
  • Plasticizer 8 Methylacetylricinoleate “Rick Sizer C-101” manufactured by Ito Oil Co., Ltd.
  • Plasticizer 9 Butylacetylricinoleate “Rick Sizer C-401” manufactured by Ito Oil Co., Ltd.
  • Abrasive Snow pot silica grade No. 4 made by Marukagama Pottery Co., Ltd.
  • Filler Fuji Balloon S-35 (Glass Balloon) made by Fuji Silysia Chemical Co., Ltd.
  • Colorant Titanium oxide “R-25” manufactured by Sakai Chemical Industry Co., Ltd.
  • Polyisocyanate 1 Nippon Polyurethane Industry Co., Ltd.
  • Polyisocyanate 2 Polymethylene polyphenyl polyisocyanate “Millionate MR-100” manufactured by Nippon Polyurethane Industry Co., Ltd.
  • Polyisocyanate 3 Tolylene diisocyanate adduct “Sumijoule L-75” (Sumika Bayer Urethane Co., Ltd.) (ethyl acetate solution having a solid content of 75%)
  • Polyisocyanate 4 Hexamethylene diisocyanate trimer (isocyanurate) manufactured by Nippon Polyurethane Industry Co., Ltd.
  • the eraser according to the present invention not only has excellent erasing performance, but can be erased by rubbing the handwriting with a light touch.
  • Example 3 since the tolylene diisocyanate adduct was used as the polyisocyanate, it was somewhat harder than the eraser obtained in Example 1, and in Example 4, hexamethylene diisocyanate 3 was used as the polyisocyanate. Since the monomer (isocyanurate) was used, it was somewhat harder than the eraser obtained in Example 5, and therefore, it seems that the erasing performance was somewhat inferior to that extent.
  • the eraser of Comparative Example 1 has too little polyisocyanate used to obtain a solidified product.
  • Comparative Example 2 the amount of polyisocyanate used was too large to obtain a solidified product.
  • Comparative Example 3 the amount of polyol used was too large, and therefore the proportion of abrasive and filler was too small to obtain a solidified product, but it had almost no erasing performance.
  • the eraser according to Comparative Example 4 does not contain an abrasive and is inferior in erasing performance.
  • the eraser according to Comparative Example 5 does not contain a filler and cannot be erased unless it is rubbed relatively strongly during erasing.
  • the eraser according to Comparative Example 6 can be erased if the ratio of the filler is too high and rubs hard enough to bend the paper surface, but the touch is poor.
  • Comparative Example 7 has too much plasticizer, so it is too soft and difficult to use.
  • Comparative Example 8 does not contain a plasticizer and has a poor feel when erasing.
  • Comparative Example 9 both the amount of polyisocyanate and polyol used were too small, and a solidified product was barely obtained, but it was too soft and did not have a function as an eraser.

Landscapes

  • Compositions Of Macromolecular Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention se rapporte à un effaceur comprenant un polyuréthane comme matériau de base. Grâce à l’effaceur, les marques de crayon sur le papier peuvent être bien effacées par le frottement léger des marques. L’effaceur comprend : un polyuréthane obtenu par la réaction de 20 à 50 % en poids d’au moins un polyol sélectionné parmi l’huile de ricin et l’huile de ricin durcie avec 5 à 17 % en poids de polyisocyanate ; 3 à 30 % en poids d’un agent plastifiant ; de 10 à 40 % en poids d’un agent abrasif ; et de 5 à 20 % en poids d’un agent de remplissage. L’effaceur est obtenu par les étapes consistant à : dissoudre, à température habituelle ou par chauffage si besoin, 5 à 17 % en poids de polyisocyanate dans un mélange comprenant 3 à 30 % en poids d’un agent plastifiant, 10 à 40 % en poids d’un agent abrasif, de 5 à 20 % en poids d’un agent de remplissage, et 20 à 50 % en poids d’au moins un polyol sélectionné parmi l’huile de ricin et l’huile de ricin durcie ; introduire le mélange obtenu dans un moule ; faire réagir complètement le  polyisocyanate avec le polyol par chauffage ; sortir du moule l’objet moulé obtenu ; et découper l’objet moulé selon une forme souhaitée.
PCT/JP2009/059505 2008-05-26 2009-05-25 Effaceur WO2009145132A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2010514459A JPWO2009145132A1 (ja) 2008-05-26 2009-05-25 消しゴム

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2008136835A JP5205123B2 (ja) 2008-05-26 2008-05-26 消しゴム
JP2008-136835 2008-05-26

Publications (1)

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WO2009145132A1 true WO2009145132A1 (fr) 2009-12-03

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JP (2) JP5205123B2 (fr)
TW (1) TWI500529B (fr)
WO (1) WO2009145132A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014094092A1 (fr) * 2012-12-17 2014-06-26 Centro De Tecnologia Mineral - Cetem Procédé d'obtention d'un matériau composite constitué par un polymère d'origine végétale, une charge minérale et un matériau abrasif, et utilisation de la composition obtenue pour le polissage de roches
US9079450B2 (en) 2011-03-24 2015-07-14 Sakura Color Products Corporation Plastic eraser, plastic eraser composite body, and method for producing thereof

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5596921B2 (ja) * 2008-12-26 2014-09-24 第一工業製薬株式会社 ポリウレタン樹脂組成物及びその硬化物
JP5938711B2 (ja) * 2012-05-09 2016-06-22 三菱鉛筆株式会社 消しゴム
JP6643051B2 (ja) * 2015-01-22 2020-02-12 三菱鉛筆株式会社 摩擦部材及び摩擦部材を備えた熱変色性筆記具

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10193880A (ja) * 1996-12-27 1998-07-28 Seed Gomme Kogyo Kk 消しゴム
JP2000025391A (ja) * 1998-07-13 2000-01-25 Porishisu:Kk プラスチック字消し

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW330208B (en) * 1996-11-13 1998-04-21 Horong-Bin Tsay A novel injection moldable composition for rubber erasers
TW200514705A (en) * 2003-10-24 2005-05-01 Flomo Plastics Ind Co Ltd Eraser composition

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10193880A (ja) * 1996-12-27 1998-07-28 Seed Gomme Kogyo Kk 消しゴム
JP2000025391A (ja) * 1998-07-13 2000-01-25 Porishisu:Kk プラスチック字消し

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9079450B2 (en) 2011-03-24 2015-07-14 Sakura Color Products Corporation Plastic eraser, plastic eraser composite body, and method for producing thereof
WO2014094092A1 (fr) * 2012-12-17 2014-06-26 Centro De Tecnologia Mineral - Cetem Procédé d'obtention d'un matériau composite constitué par un polymère d'origine végétale, une charge minérale et un matériau abrasif, et utilisation de la composition obtenue pour le polissage de roches

Also Published As

Publication number Publication date
JPWO2009145132A1 (ja) 2011-10-13
JP2011051093A (ja) 2011-03-17
TWI500529B (zh) 2015-09-21
JP5205123B2 (ja) 2013-06-05
TW201006690A (en) 2010-02-16

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