JP6234202B2 - ポリエステルポリマートナー樹脂中のチモール誘導体 - Google Patents
ポリエステルポリマートナー樹脂中のチモール誘導体 Download PDFInfo
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- JP6234202B2 JP6234202B2 JP2013255625A JP2013255625A JP6234202B2 JP 6234202 B2 JP6234202 B2 JP 6234202B2 JP 2013255625 A JP2013255625 A JP 2013255625A JP 2013255625 A JP2013255625 A JP 2013255625A JP 6234202 B2 JP6234202 B2 JP 6234202B2
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- 229920000642 polymer Polymers 0.000 title claims description 40
- 229920000728 polyester Polymers 0.000 title claims description 27
- 125000003639 thymyl group Chemical class C1(=CC(C)=CC=C1C(C)C)* 0.000 title claims description 4
- 229920005989 resin Polymers 0.000 title description 42
- 239000011347 resin Substances 0.000 title description 42
- 239000002245 particle Substances 0.000 claims description 71
- DBEFONQGRSUFQO-UHFFFAOYSA-N 3-(2-Methylpropanoyloxy)-8-(2-methylbutanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene Polymers C=1C=C(C)C=C(OC(=O)C(C)C)C=1C1(COC(=O)C(C)CC)CO1 DBEFONQGRSUFQO-UHFFFAOYSA-N 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 11
- 229920005862 polyol Polymers 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 9
- 229920006038 crystalline resin Polymers 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 229920006127 amorphous resin Polymers 0.000 claims description 4
- 239000003086 colorant Substances 0.000 claims description 3
- XIHHEYPANRXLFS-UHFFFAOYSA-N 3-(5-methyl-2-propan-2-ylphenoxy)propane-1,2-diol Chemical group CC(C)C1=CC=C(C)C=C1OCC(O)CO XIHHEYPANRXLFS-UHFFFAOYSA-N 0.000 claims description 2
- 150000003601 thymols Polymers 0.000 claims description 2
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- 239000000203 mixture Substances 0.000 description 41
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 30
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- 238000000034 method Methods 0.000 description 19
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- 239000000049 pigment Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
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- 150000003839 salts Chemical class 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- MJXSSIDXOOAJHN-UHFFFAOYSA-N 1,2-dihydroxyethanesulfonic acid Chemical compound OCC(O)S(O)(=O)=O MJXSSIDXOOAJHN-UHFFFAOYSA-N 0.000 description 3
- JFMGYULNQJPJCY-UHFFFAOYSA-N 4-(hydroxymethyl)-1,3-dioxolan-2-one Chemical compound OCC1COC(=O)O1 JFMGYULNQJPJCY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- PKYXMVZTROVMSE-UHFFFAOYSA-N 1,3-dihydroxypropane-2-sulfonic acid Chemical compound OCC(CO)S(O)(=O)=O PKYXMVZTROVMSE-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 2
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 2
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- VZUAUHWZIKOMFC-ARJAWSKDSA-N [(z)-4-acetyloxybut-2-enyl] acetate Chemical compound CC(=O)OC\C=C/COC(C)=O VZUAUHWZIKOMFC-ARJAWSKDSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
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- 239000003513 alkali Substances 0.000 description 2
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- 229920005603 alternating copolymer Polymers 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
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- 229920001400 block copolymer Polymers 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- TUZBYYLVVXPEMA-UHFFFAOYSA-N butyl prop-2-enoate;styrene Chemical compound C=CC1=CC=CC=C1.CCCCOC(=O)C=C TUZBYYLVVXPEMA-UHFFFAOYSA-N 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
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- SAQPWCPHSKYPCK-UHFFFAOYSA-N carbonic acid;propane-1,2,3-triol Chemical compound OC(O)=O.OCC(O)CO SAQPWCPHSKYPCK-UHFFFAOYSA-N 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
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- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/19—Hydroxy compounds containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08742—Binders for toner particles comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08755—Polyesters
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
- G03G9/08795—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by their chemical properties, e.g. acidity, molecular weight, sensitivity to reactants
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
- G03G9/08797—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by their physical properties, e.g. viscosity, solubility, melting temperature, softening temperature, glass transition temperature
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Developing Agents For Electrophotography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
250mLフラスコに75グラムのチモール、63.7グラムのグリセリンカーボネート(ヒドロキシメチルジオキソラン−2−オン)、および0.25グラムの炭酸カリウムを加えた。窒素雰囲気下、攪拌しつつ混合物を5時間かけて180℃まで加熱し、黄色粘性生成物を得た。構造を1H NMRおよび13C NMRによって確認した。
1リットルのParr反応器にメカニカルスターラー、底部ドレイン弁を取り付け、これに純度85%のアビエチン酸(1000mmol、1.20eq、302g)、グリセリンカーボネート(1120mmol、1.344eq、132g)、2−メチル−1H−イミダゾール触媒(3.33mmol、0.004eq、0.274g)を入れた。反応器内を窒素で覆い、攪拌しつつ、(固体が溶融したら)反応器の温度を175℃までゆっくりと上げた。5時間後、アビエチン酸とグリセリンカーボネートとを完全に反応させるため、酸価の分析のためにサンプルを採取した。窒素で覆いつつ、ゆっくりと機械攪拌しつつ、温度を一晩かけて110℃まで下げて生成物である(1R,4aR,4bR)−2,3−ジヒドロキシプロピル 7−イソプロピル−1,4a−ジメチル−1,2,3,4,4a,4b,5,6,10,10a−デカヒドロフェナントレン−1−カルボキシレートを得た。
約500グラムのジクロロメタンが入った2リットルのビーカー中、113グラムのチモール系樹脂を測定した。この混合物を室温、約300rpmで攪拌して樹脂を溶解させた。炭酸水素トリウム(1.05グラム)、4.83gのDOWFAX(46.75wt%)を、約700グラムの脱イオン水が入ったPyrex(登録商標)ガラスフラスコ反応器中で測定した。この水溶液をIKA Ultra Turrax T50ホモジナイザーを用いて4,000rpmで攪拌した。次いで、混合物を均質化しつつ、この樹脂溶液を上の水溶液にゆっくりと注ぎ、ホモジナイザーの速度を8,000rpmに上げ、混合物を約30分間均質化した。ガラスフラスコ反応器と内容物を加熱マントルに入れ、蒸留デバイスに接続した。この混合物を約200rpmで攪拌し、温度を約1℃/分の速度で50℃まで上げ、混合物からジクロロメタンを留去した。攪拌を50℃で約180分間続けた後、約2℃/分の速度で室温まで冷却した。生成物を25μmのふるいで分けた。得られた樹脂エマルションは、約35.0重量%の固形分が水中に含まれており、平均粒径は203nmであった。
Claims (16)
- ポリオールモノマーおよびポリ酸モノマーから構成されたポリエステルポリマーを含み、前記ポリオールモノマーがポリヒドロキシル化チモール誘導体を含み、
前記ポリヒドロキシル化チモール誘導体が、1−O−(2−イソプロピル−5−メチルフェニル)−グリセロールである、ポリエステルトナー樹脂組成物。 - 前記ポリエステルポリマーが、さらなるポリオールモノマーを含んで構成されたものである、請求項1に記載のトナー樹脂組成物。
- 前記ポリエステルポリマーの軟化点(Ts)が90℃〜150℃である、請求項1に記載のトナー樹脂組成物。
- 前記ポリエステルポリマーの数平均分子量(Mn)が1,000〜50,000である、請求項1に記載のトナー樹脂組成物。
- 前記ポリエステルポリマーの重量平均分子量(Mw)が2,000〜100,000である、請求項1に記載のトナー樹脂組成物。
- 前記ポリエステルポリマーの酸価が2〜30である、請求項1に記載のトナー樹脂組成物。
- 少なくとも30モル%の前記ポリヒドロキシル化チモール誘導体を含む、請求項1に記載のトナー樹脂組成物。
- アモルファス樹脂をさらに含む、請求項1に記載のトナー樹脂組成物。
- 結晶性樹脂をさらに含む、請求項1に記載のトナー樹脂組成物。
- 前記結晶性樹脂の融点が30℃〜120℃である、請求項9に記載のトナー樹脂組成物。
- 請求項1に記載のポリエステルトナー樹脂組成物を含むトナー粒子。
- 少なくとも1種類のアモルファス樹脂、任意要素の結晶性樹脂、任意要素のワックス、任意要素の着色剤をさらに含む、請求項11に記載のトナー粒子。
- 少なくとも2種類のアモルファス樹脂をさらに含む、請求項11に記載のトナー粒子。
- 少なくとも1つの着色剤をさらに含む、請求項11に記載のトナー粒子。
- シェルを有する、請求項11に記載のトナー粒子。
- 請求項11に記載のトナー粒子を含む現像剤。
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US13/718,471 | 2012-12-18 | ||
US13/718,471 US8795941B2 (en) | 2012-12-18 | 2012-12-18 | Thymol derivatives in polyester polymer toner resin |
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US9323167B2 (en) * | 2013-10-22 | 2016-04-26 | Xerox Corporation | Sustainable polyester resin of defined acid value |
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WO2008128193A1 (en) * | 2007-04-12 | 2008-10-23 | Rutgers, The State University Of New Jersey | Biodegradable polyanhydrides with natural bioactive molecules |
US8431303B2 (en) * | 2011-01-17 | 2013-04-30 | Xerox Corporation | Rosin-based resin and toner containing same |
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US8835589B2 (en) * | 2012-01-26 | 2014-09-16 | Xerox Corporation | Synthesis of abietic acid-based macromer for polyester resin process |
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