JP5757947B2 - 2,5−フランジカルボン酸と異性体デカノールとのエステルおよびその使用 - Google Patents
2,5−フランジカルボン酸と異性体デカノールとのエステルおよびその使用 Download PDFInfo
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- JP5757947B2 JP5757947B2 JP2012525962A JP2012525962A JP5757947B2 JP 5757947 B2 JP5757947 B2 JP 5757947B2 JP 2012525962 A JP2012525962 A JP 2012525962A JP 2012525962 A JP2012525962 A JP 2012525962A JP 5757947 B2 JP5757947 B2 JP 5757947B2
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- Prior art keywords
- mixture
- furan
- dicarboxylic acid
- esters
- isomeric
- 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.)
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- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 title claims description 109
- 150000002148 esters Chemical class 0.000 title claims description 67
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 title description 33
- 239000000203 mixture Substances 0.000 claims description 135
- 239000003054 catalyst Substances 0.000 claims description 48
- -1 decyl ester Chemical class 0.000 claims description 48
- 239000004014 plasticizer Substances 0.000 claims description 35
- 229920001944 Plastisol Polymers 0.000 claims description 28
- 239000004999 plastisol Substances 0.000 claims description 28
- 239000004800 polyvinyl chloride Substances 0.000 claims description 25
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 19
- 150000001298 alcohols Chemical class 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 229920003023 plastic Polymers 0.000 claims description 14
- 239000004033 plastic Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 239000000853 adhesive Substances 0.000 claims description 11
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- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 9
- PDSULNVJASBMLP-UHFFFAOYSA-N furan-2,5-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)O1 PDSULNVJASBMLP-UHFFFAOYSA-N 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
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- 239000000976 ink Substances 0.000 claims description 6
- 239000003973 paint Substances 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 6
- 239000004626 polylactic acid Substances 0.000 claims description 6
- 238000007789 sealing Methods 0.000 claims description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
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- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
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- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims description 3
- XFDQLDNQZFOAFK-UHFFFAOYSA-N 2-benzoyloxyethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOC(=O)C1=CC=CC=C1 XFDQLDNQZFOAFK-UHFFFAOYSA-N 0.000 claims description 3
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 3
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
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- 238000005984 hydrogenation reaction Methods 0.000 description 17
- 150000005690 diesters Chemical class 0.000 description 15
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- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 230000009471 action Effects 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
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- 238000005809 transesterification reaction Methods 0.000 description 6
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 5
- YKGYQYOQRGPFTO-UHFFFAOYSA-N bis(8-methylnonyl) hexanedioate Chemical compound CC(C)CCCCCCCOC(=O)CCCCC(=O)OCCCCCCCC(C)C YKGYQYOQRGPFTO-UHFFFAOYSA-N 0.000 description 5
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/68—Esters
- C10M129/72—Esters of polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
- C10M2207/2825—Esters of (cyclo)aliphatic oolycarboxylic acids used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/285—Esters of aromatic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/285—Esters of aromatic polycarboxylic acids
- C10M2207/2855—Esters of aromatic polycarboxylic acids used as base material
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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Description
同時にここ数年来、C10オキソアルコール、殊に2−プロピルヘプタノールの生産高がとりわけ有利な原料ベースのために著しく上昇し、さらになお生産能力の向上を追求することに期待できる。可塑剤のための出発物質としての前記アルコールの使用は、実際に殆ど専ら相応するDIDPまたはDPHPに制限されている。前記使用は、実際にいわゆる標準可塑剤に含まれるが、その使用技術的性質のために、DEHP、DINPおよびDOTPに比べて比較的重要なプラスチゾルマーケットにおいて、僅かなゲル化および劣悪な可塑的性質のために著しく制限されてのみ使用されることができる。従って、このような性質を有する、イソデカノールのエステル、有利に高い2−プロピルヘプタノール含量を有するイソデカノールの前記エスエルは、古典的な熱可塑的使用、例えばシート、ケーブル外被および部分的に屋根材用メンブレンと共にますますプラスチゾルの用途に使用されてもよいことが望まれている。
原理的に、デカノールの全ての工業用混合物、特に一般的な総和式C10H21OHを有する第1アルコールまたはアルコール混合物が使用されてよい。特に、2−プロピルヘプタノールまたはn−デカノールの割合、ならびに第四級C原子を有する、ポリ置換されたC10アルコールの含量に関連して上記の範囲内にあるような式C9H19CH2OHを有する異性体デカノールの混合物が使用される。2−プロピルヘプタノールの高い割合を有するデカノールは、特に好ましい。
a)C4オレフィンまたはC4オレフィン混合物は、相応するC5アルデヒドにヒドロホルミル化される。
b)a)で生じたアルデヒドは、デセナールにアルドール縮合される。
c)工程b)で生じたデセナールは、デカノールに水素化される。
2−プロピルヘプタノール、4−メチル−2−プロピル−ヘキサノール、5−メチル−2−プロピル−ヘキサノール、2−イソプロピル−4−メチル−ヘキサノール、2−イソプロピル−5−メチル−ヘキサノール。挙げられたデカノールは、それぞれ少なくとも2つの立体異性体からなる。
フラン−2,5−ジカルボン酸(FDCA、CAS−No.3238−40−2)は、これまで大工業的には使用不可能であったが、しかし、刊行物の記載により製造されることができるか、または商業的に入手することができる。場合によっては望ましいかまたは好ましい、ジクロリドへの移行は、実施例中に詳細に記載されている。
本発明によるエステルを製造するために、2,5−フランジカルボン酸かまたは反応性誘導体、例えば相応するジクロリド(実施例参照)は、異性体デカノールの混合物と反応される。好ましくは、エステル化は、フランジカルボン酸およびイソデカノールから出発して触媒を用いて行なわれる。
他の選択可能な方法によれば、本発明によるジイソデシルエステルは、フラン−2,5−ジカルボン酸ジエステルをイソデカノール混合物とエステル交換することによって取得されることができる。反応体として、エステル基のO原子上に結合したアルキル基が1〜9個のC原子を有するフラン−2,5−ジカルボン酸ジエステルが使用される。前記基は、脂肪族、直鎖状または分枝鎖状、脂環式または芳香族であってよい。前記のアルキル基の1個または複数のメチレン基は、酸素によって置換されていてよい。反応体エステルに基づくアルコールが使用されたイソデカノール混合物よりも低温で沸騰することは、好ましい。好ましい原料は、フラン−2,5−ジカルボン酸ジメチルエステルである。
2,5−フランジカルボン酸の異性体デシルエステルの本発明による混合物は、可塑剤として、殊にプラスチック組成物、接着剤、封止用コンパウンド、塗料、染料、プラスチゾル、人工皮革、繊維床仕上げ材、アンダーシーラント、被覆された織物、壁紙またはインキ中に使用されてよい。特に、本発明による可塑剤は、異形成形材、シール材、食品包装材、シート、玩具、医薬用製品、屋根材用メンブレン、人工皮革、繊維床仕上げ材、アンダーシーラント、被覆された織物、壁紙、ケーブルおよび線材外被中、特に有利に食品包装材、玩具、医薬用製品中、例えば注入、透析およびドレナージのための袋およびチューブ、壁紙、繊維床仕上げ材および被覆された織物中に使用されてよい。
本発明によるエステルは、最初に2段階の合成においてフラン−2,5−ジカルボン酸から出発してジクロリドを経て製造された。
還流冷却器および滴下漏斗を装備した、250mlの三口フラスコ中にアルゴン雰囲気下にフラン−2,5−ジカルボン酸72.1g(462mmol)を予め装入した。10分間に亘って、N,N−ジメチルホルムアミド2,3滴を添加した塩化チオニル165g(1.39mol)を添加した。この懸濁液を還流温度に加熱し、生じるガスをKOH水溶液を有する洗浄瓶に通して導出した。更に、4時間、ガス発生が終結しかつ固体が完全に溶解するまで還流下に加熱した。
還流冷却器および滴下漏斗を装備した三口フラスコ中でアルゴン雰囲気下でジクロリドを予め装入し、および加熱することによって溶融した。液体に2,4当量のアルコールを徐々に滴加し、その際にガスの発生を伴って発熱反応が生じた。生じるガスを、KOH水溶液を有する洗浄瓶に導通した。転化が完了した後に、80〜100℃の温度で16時間攪拌した。
2−プロピルヘプタノール85.3質量%;2−プロピル−4−メチルヘキサノール13.4質量%;残分0.3質量%。
本発明によるエステルで達成可能な好ましい性質は、以下、プラスチゾルおよびこれから得られた半製品につき示される。
種々のプラスチゾルについての成分の使用した秤量した量は、以下の第2表から確認することができる。
プラスチゾルのゲル化挙動の試験をPhysica MCR 101中で振動モードで、剪断応力を制御して運転される、プレート−プレート測定システム(Platte−Platte Messsystem)(PP25)を用いて行なった。付加的な温調ボンネット(Temperrierhaube)を、最適な熱分布を達成させるために、機器に接続した。
モード:温度勾配
開始温度:25℃
最終温度:180℃
加熱/冷却速度:5℃/分
測定後の温度:25℃
振動周波数:4〜0.1Hz 勾配、対数列
角振動数Ω:10 1/s
測定点の数:63
測定点の時間:0.5分
自動ギャップ補償F:0 N
一定の測定点時間
ギャップ幅:0.5mm。
測定システムの下方のプレート上に、へらを用いて、測定すべきプラスチゾル処方の液滴を気泡不含であるように施与した。その際、測定システムを閉じた後に、幾らかのプラスチゾルが一様に測定システムから滲出しうることに注目した(周囲約6mm以下)。引続き、温調ボンネットを試料上に位置決めし、測定を開始した。
ショアー硬度Aは、試験体の軟度についての1つの基準である。一定の測定時間において、規定のニードルが試験体中に進入することができればできるほど、測定値はますます低下する。最も高い効率を有する可塑剤は、同じ可塑剤量で、ショアー硬度について最も低い値をもたらす。反対に、極めて効率の高い可塑剤の場合、処方中で或る程度の割合を節約することができ、このことは、多くの場合、加工業者にとってコストの低下を意味する。
試験体を製造するために、最初に第3表からのそれぞれの処方について厚さ1mmのシートを製造した。このために、最初に、高光沢剥離紙(Sappi社、イタリア国)を30×44cmの寸法に切断し、Mathis炉用の塗布装置LTSVの張り枠に設置した。その後、張り枠をガイド枠上に載置し、Mathis炉(LTF型)を200℃に調節し、この温度に達した後に枠を15秒間予熱した。その後、コーターを張設装置に設置し、ゲル化終了後のシートの厚さが、1mm(±0.05mm)となるように、前試験によりコーターのギャップを調節した。紙の前側の縁部に接着ストリップを施与して過剰のペーストを捕集した。その後、該ペーストをコーターの前方に施与し、コーターと共にガイド枠を引っ張ることによって張設された剥離紙上にペーストを塗り広げた(速度約6m/分)。その後、コーターを取り出し、過剰のペーストと共に接着ストリップを除去した。引続き、溶融ロールを降下させ、張り枠を炉中へ移動させた。ゲル化(200℃で2分間)後に、枠を再び炉から取り出し、冷却後にシートを紙から剥離した。
例6において製造した、厚さ約1mmを有するシートから、それぞれ50cm2の面積を有する2枚の円板を打ち抜いた。この試験体を少なくとも24時間、一定の空気湿度で乾燥ゲルを有するデシケーター中に貯蔵した。
Claims (15)
- エステルの混合物がC10側鎖中の2−プロピルヘプチル基の割合を50モル%から最大99モル%までの範囲内で有する、請求項1記載のフラン−2,5−ジカルボン酸の異性体デシルエステルの混合物。
- 請求項1記載の式Iのフラン−2,5−ジカルボン酸の異性体デシルエステルの混合物の製造法において、
a)フラン−2,5−ジカルボン酸を水の遊離下に異性体C10アルコールの混合物と接触させ;
b)その際、50%までモル過剰量の異性体C10アルコールの混合物が使用され;
c)ブレンステッド酸および/またはルイス酸の群から選択された、触媒を使用してa)に記載の反応を行なうことを特徴とする、
式Iのフラン−2,5−ジカルボン酸の異性体デシルエステルの混合物の製造法。 - 請求項1記載の式Iのフラン−2,5−ジカルボン酸の異性体デシルエステルの混合物の製造法において、
a)フラン−2,5−ジカルボン酸を相応するフラン−2,5−ジカルボン酸クロリドに変換し、このフラン−2,5−ジカルボン酸クロリドを、
b)引続き分離および精製の後に塩化水素の遊離下に異性体C10アルコールの混合物と接触させることを特徴とする、
式Iのフラン−2,5−ジカルボン酸の異性体デシルエステルの混合物の製造法。 - 請求項1記載の式Iのフラン−2,5−ジカルボン酸の異性体デシルエステルの混合物の製造法において、
a)フラン−2,5−ジカルボン酸ジメチルエステルをメタノールの遊離下に異性体C10アルコールの混合物と接触させ;
b)その際、ブレンステッド酸および/またはルイス酸の群から選択された、触媒を使用してa)に記載の反応を行なうことを特徴とする、
式Iのフラン−2,5−ジカルボン酸の異性体デシルエステルの混合物の製造法。 - 請求項1記載の式Iのフラン−2,5−ジカルボン酸の異性体デシルエステルの混合物ならびにアルキルベンゾエート、ジアルキルアジピエート、グリセリンエステル、クエン酸トリアルキルエステル、アシル化されたクエン酸トリアルキルエステル、トリアルキルトリメリテート、グリコールジベンゾエート、ジアルキルテレフタレート、ジアルキルフタレート、イソソルビドのジアルカノイルエステルおよび/または1,2−、1,3−または1,4−シクロヘキサンジカルボン酸のジアルキルエステルの群から選択された可塑剤を含有する組成物。
- 式Iのフラン−2,5−ジカルボン酸の異性体デシルエステル対可塑剤の比が1:15〜15:1の範囲内にある、請求項6記載の組成物。
- 前記組成物がポリ塩化ビニル、ポリビニルブチラール、ポリ乳酸、ポリヒドロキシブチラールおよび/またはポリアルキルメタクリレートから選択されたポリマーを有する、請求項6または7記載の組成物。
- 請求項1記載の式Iのフラン−2,5−ジカルボン酸の異性体デシルエステルの混合物、ならびにポリ塩化ビニル、ポリビニルブチラール、ポリ乳酸、ポリヒドロキシブチラールおよび/またはポリアルキルメタクリレートから選択されたポリマーを含有する組成物。
- ポリマー対式Iのフラン−2,5−ジカルボン酸の異性体デシルエステルの比が30:1〜1:2.5の範囲内にある、請求項9記載の組成物。
- 可塑剤としての請求項1または2に記載の式Iのフラン−2,5−ジカルボン酸の異性体デシルエステルの使用。
- 染料、インキ、接着剤若しくは接着剤成分、塗料、プラスチゾル、又は封止用コンパウンドの製造の際の、プラスチックまたはプラスチック成分における可塑剤としての、請求項6から10までのいずれか1項に記載の組成物の使用。
- 染料、インキ、接着剤若しくは接着剤成分、塗料、プラスチゾル、又は封止用コンパウンドの製造の際の溶剤としての、請求項6から10までのいずれか1項に記載の組成物の使用。
- 潤滑油成分としての請求項6から10までのいずれか1項に記載の組成物の使用。
- 金属加工の際の助剤としての請求項6から10までのいずれか1項に記載の組成物の使用。
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CN111876229A (zh) * | 2020-08-18 | 2020-11-03 | 上海金兆节能科技有限公司 | 抗磨润滑剂组合物及其制备方法及组合物制备的微量润滑剂 |
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BR112012004416A2 (pt) | 2020-08-18 |
CN102596928A (zh) | 2012-07-18 |
DK2470517T3 (da) | 2014-07-21 |
DE102009028976A1 (de) | 2011-03-03 |
CN102596928B (zh) | 2015-05-13 |
ES2481590T3 (es) | 2014-07-31 |
KR20120066644A (ko) | 2012-06-22 |
US20120202725A1 (en) | 2012-08-09 |
PL2470517T3 (pl) | 2014-09-30 |
JP2013503120A (ja) | 2013-01-31 |
WO2011023491A1 (de) | 2011-03-03 |
SI2470517T1 (sl) | 2014-08-29 |
US9169228B2 (en) | 2015-10-27 |
BR112012004416B1 (pt) | 2021-03-30 |
EP2470517B1 (de) | 2014-04-16 |
KR101718568B1 (ko) | 2017-03-21 |
EP2470517A1 (de) | 2012-07-04 |
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