JP2012522112A - 疎水性モノマー、疎水的に誘導体化された支持体、並びにその製造及び使用方法 - Google Patents
疎水性モノマー、疎水的に誘導体化された支持体、並びにその製造及び使用方法 Download PDFInfo
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- JP2012522112A JP2012522112A JP2012503481A JP2012503481A JP2012522112A JP 2012522112 A JP2012522112 A JP 2012522112A JP 2012503481 A JP2012503481 A JP 2012503481A JP 2012503481 A JP2012503481 A JP 2012503481A JP 2012522112 A JP2012522112 A JP 2012522112A
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- Prior art keywords
- monomer
- hydrophobic
- aryl
- alkylaryl
- alkyl
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- 230000002209 hydrophobic effect Effects 0.000 title claims abstract description 105
- 238000000034 method Methods 0.000 title claims description 55
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 61
- 239000000203 mixture Substances 0.000 claims abstract description 57
- 125000003118 aryl group Chemical group 0.000 claims abstract description 56
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 50
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 48
- 238000004132 cross linking Methods 0.000 claims abstract description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000001165 hydrophobic group Chemical group 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- 239000002245 particle Substances 0.000 claims description 102
- -1 phenoxyethyl Chemical group 0.000 claims description 25
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 16
- 102000004169 proteins and genes Human genes 0.000 claims description 16
- 108090000623 proteins and genes Proteins 0.000 claims description 16
- 229920001223 polyethylene glycol Polymers 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
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- 238000004519 manufacturing process Methods 0.000 claims description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 2
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 20
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- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical group O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
- 230000003993 interaction Effects 0.000 description 18
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 150000003141 primary amines Chemical class 0.000 description 14
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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Abstract
CH2=CR4C(O)NHC(R1R1)(C(R1R1))nC(O)XR3
(式中、nは0又は1の整数であり;R1は、水素原子、アルキル、アリール、及びアルキルアリールの少なくとも1つから独立して選択され、該アルキル、アリール、及びアルキルアリールは全体で10個以下の炭素原子を有し;R3は、アルキル、アリール、アルキルアリール及びエーテルの少なくとも1つから選択される疎水性基であり、該アルキル、アリール、アルキルアリール及びエーテルは全体で4〜30個の範囲の炭素原子を有し;R4は、H又はCH3であり;XはO又はNHである。)を有する疎水性モノマーを含む組成物を開示する。特定の実施形態では、疎水性モノマーは、疎水性指数が25以下であるアミン又はアルコール(HXR3)から誘導される。前記疎水性モノマーを含み、場合により架橋モノマー及び/又は非架橋モノマーを含みうる重合性組成物も開示する。この重合性混合物を使用して、疎水的に誘導体化された支持体を形成することが可能であり、このような疎水的に誘導体化された支持体を疎水性相互作用クロマトグラフィーのような用途において使用することができる。
Description
CH2=CR4C(O)NHC(R1R1)(C(R1R1))nC(O)XR3
[式中、nは0又は1の整数であり;R1は、水素原子、アルキル、アリール、及びアルキルアリールの少なくとも1つから独立して選択され、前記アルキル、アリール、及びアルキルアリールは全体で10個以下の炭素原子を有し;R3は、アルキル、アリール、アルキルアリール及びエーテルの少なくとも1つから選択される疎水性基であり、前記アルキル、アリール、アルキルアリール及びエーテルは全体で4〜30個の範囲の炭素原子を有し;R4は、H又はCH3であり;XはO又はNHである。]を有する疎水性モノマーを含む組成物であって、該疎水性モノマーが、親水性指数が25以下であるアミン又はアルコール(HXR3)から誘導される組成物を提供する。
CH2=CR4C(O)NHC(R1R1)(C(R1R1))nC(O)XR3
[式中、nは0又は1の整数であり;R1は、水素原子、アルキル、アリール、及びアルキルアリールの少なくとも1つから独立して選択され、前記アルキル、アリール、及びアルキルアリールは全体で10個以下の炭素原子を有し;R3は、アルキル、アリール、アルキルアリール及びエーテルの少なくとも1つから選択される疎水性基であり、前記アルキル、アリール、アルキルアリール及びエーテルは全体で4〜30個の範囲の炭素原子を有し;R4は、H又はCH3であり;XはO又はNHである。]を有する疎水性モノマーを含む重合性混合物を提供する。
(a)混合物を提供する工程であって、該混合物が、
(ii)下記構造:
CH2=CR4C(O)NHC(R1R1)(C(R1R1))nC(O)XR3
[式中、nは0又は1の整数であり;R1は、水素原子、アルキル、アリール、及びアルキルアリールの少なくとも1つから独立して選択され、前記アルキル、アリール、及びアルキルアリールは全体で10個以下の炭素原子を有し;R3は、アルキル、アリール、アルキルアリール及びエーテルの少なくとも1つから選択される疎水性基であり、前記アルキル、アリール、アルキルアリール及びエーテルは全体で4〜30個の範囲の炭素原子を有し;R4は、H又はCH3であり;XはO又はNHである。]を有する疎水性モノマーと、
(ii)架橋モノマーと、
(iii)場合により、非架橋モノマーと、を含む工程と、
(b)前記混合物を重合する工程と、を含む方法が提供される。
(a)下記構造:
CH2=CR4C(O)NHC(R1R1)(C(R1R1))nC(O)XR3
[式中、nは0又は1の整数であり;R1は、水素原子、アルキル、アリール、及びアルキルアリールの少なくとも1つから独立して選択され、前記アルキル、アリール、及びアルキルアリールは全体で10個以下の炭素原子を有し;R3は、アルキル、アリール、アルキルアリール及びエーテルの少なくとも1つから選択される疎水性基であり、前記アルキル、アリール、アルキルアリール及びエーテルは全体で4〜30個の範囲の炭素原子を有し;R4は、H又はCH3であり;XはO又はNHである。]を有する疎水性モノマーと、
(b)基材を与える工程と、
(c)前記疎水性モノマーを前記基材と接触させる工程と、
(d)前記疎水性モノマーを重合する工程と、を含む方法が提供される。
式中、nは0又は1の整数であり;R1は、水素原子、アルキル、アリール、及びアルキルアリールの少なくとも1つから独立して選択され;R3は、アルキル、アリール、アルキルアリール及びエーテルの少なくとも1つから選択される疎水性基であり;R4は、H又はCH3であり、XはO又はNHである。
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)4C6H5;
CH2=CHC(O)NHC(CH3)(CH3)C(O)O(CH2)4C6H5;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NHCH2C6H5;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)2C6H5;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)2OC6H5;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)3C6H5;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)3CH3;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)5CH3;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)7CH3;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)11CH3;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)17CH3;又はこれらの組み合わせが挙げられる。
実施例1:以下の手順を用いて4−フェニルブチルアミン/VDM付加物を調製した。メチル−tert−ブチルエーテル(MTBE、100mL)を、凝縮器、400回転/分(rpm)のオーバーヘッド混合パドル、及び窒素取り入れ口を備えた3つ口フラスコに氷浴中で加えた。ビニルジメチルアズラクトン(VDM、10.44g)をフラスコに加えた。4−フェニルブチルアミン(10g)を添加漏斗に加えた。4−フェニルブチルアミンが保管されたボトルを、添加漏斗に加える前に少量ずつのMTBE(全体で10mL)ですすいだ。ボトルをすすぐのに用いたMTBEを添加漏斗に加えた。4−フェニルブチルアミンをVDMが入ったフラスコに10分間かけて滴下した。VDMへの4−フェニルブチルアミンの添加の完了後、添加漏斗を10mLのMTBEですすいだ。白色の沈殿物(生成物)がほぼすぐに形成された。この後、窒素下で混合しながら0℃で60分間、反応を進行させた。
実施例12:ヘプタン(174mL)及び1.4mLのポリマー安定剤溶液(トルエン1mL当たり(イソオクチルアクリレート:VDM(アンモニアによって開環したもの)の比=92.5:7.5からなるポリマー0.1g)を含むもの)を、オーバーヘッドスターラー、熱電対、環流凝縮器、及び窒素ガス取り入れ口を備えた1Lのモートン型丸底フラスコに加えた。オーバーヘッドスターラーを約300rpmの攪拌速度に調節し、反応フラスコを徐々に窒素ガスでパージしながら35℃に加熱した。メチレンビスアクリルアミド(MBA、11.31g)、2.09gのアクリルアミド(AAm)、及び0.60gの4−フェニルブチルアミン/VDM付加物(PhBVDM、上記実施例1に従って調製したもの)を、スターラーバーを備えた250mLの三角フラスコに加えた。イソプロピルアルコール(62.5mL)及び42mLの水を加えて固体を溶解した。次いでPEG 2,000の50%水溶液を10g加えた。固体がすべて溶解した時点で、過硫酸ナトリウムを攪拌した溶液に加えた(6mLの水に0.56gを加えたもの)。水相を有機相に加え、反応混合物が35℃に達するまで混合した。テトラメチルエチレンジアミン(0.55mL)を加えて重合を開始させた。粒子が形成されつつある間に重合反応液を2時間攪拌した。
クロマトグラフィーカラムの調製:クロマトグラフィーカラムは、例示的な粒子をオミフィット社(Omifit)(英国、ケンブリッジ、CB1 3HD)によって供給される3.0mm×150mmのガラスチューブにスラリー充填することによって調製した。多孔質テフロン(登録商標)フリット(25μmの平均孔径、スモールパーツ社(Small Parts, Inc.)(フロリダ州マイアミレイクス))をチューブの両端に入れて、クロマトグラフィーカラムを形成した。
実施例17:上記で述べた方法を用いて実施例12で調製した粒子をチューブに充填してクロマトグラフィーカラムを形成し、上記に述べたようなタンパク質分析法を用いて分析を行った。図1にクロマトグラムを示す。
Claims (26)
- 疎水性モノマーを含む組成物であって、
下記構造:
CH2=CR4C(O)NHC(R1R1)(C(R1R1))nC(O)XR3
(式中、nは0又は1の整数であり;R1は、水素原子、アルキル、アリール、及びアルキルアリールの少なくとも1つから独立して選択され、該アルキル、アリール、及びアルキルアリールは全体で10個以下の炭素原子を有し;R3は、アルキル、アリール、アルキルアリール及びエーテルの少なくとも1つから選択される疎水性基であり、該アルキル、アリール、アルキルアリール及びエーテルは全体で4〜30個の範囲の炭素原子を有し;R4は、H又はCH3であり;XはO又はNHである。)
を有し、
前記疎水性モノマーは、親水性指数が25以下であるアミン又はアルコール(HXR3)から誘導される組成物。 - R1が、メチル、エチル、フェニル、又はこれらの組み合わせの少なくとも1つから独立して選択される、請求項1に記載の組成物。
- R3が、ベンジル、フェネチル、フェノキシエチル、フェニルプロピル、ブチル、ペンチル、ヘキシル、オクチル、ドデシル、オクタデシル、フェニルブチル、又はこれらの組み合わせの少なくとも1つから選択される、請求項1又は2に記載の組成物。
- 前記疎水性モノマーが、
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)4C6H5;
CH2=CHC(O)NHC(CH3)(CH3)C(O)O(CH2)4C6H5;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NHCH2C6H5;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)2C6H5;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)2OC6H5;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)3C6H5;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)3CH3;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)5CH3;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)7CH3;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)11CH3;
CH2=CHC(O)NHC(CH3)(CH3)C(O)NH(CH2)17CH3;又はこれらの組み合わせの少なくとも1つから選択される構造を有する、請求項1〜3のいずれか一項に記載の組成物。 - 請求項1〜4のいずれか一項に記載の疎水性モノマーを含む重合性混合物。
- 架橋モノマーを更に含む、請求項5に記載の重合性混合物。
- 前記架橋モノマーが、N,N’−アルキレンビス(メタ)アクリルアミド、アルキレンビス(メタ)アクリレート、ジビニル芳香族化合物、ポリアリルエステル、又はこれらの組み合わせの少なくとも1つから選択される、請求項6に記載の重合性混合物。
- 非架橋モノマーを更に含む、請求項5〜7のいずれか一項に記載の重合性混合物。
- 前記非架橋モノマーが、ジメチルアクリルアミド、アクリルアミド、メタクリルアミド、ヒドロキシエチル(メタ)アクリレート、又はこれらの組み合わせの少なくとも1つから選択される、請求項8に記載の重合性混合物。
- 前記架橋モノマーの量が前記非架橋モノマーの量よりも大きい、請求項8又は9に記載の重合性混合物。
- 前記非架橋モノマーの量が前記疎水性モノマーの量よりも大きい、請求項8〜10のいずれか一項に記載の重合性混合物。
- ポロゲンを更に含む、請求項5〜11のいずれか一項に記載の重合性混合物。
- 前記ポロゲンが、アルコール、エチレングリコール、ポリエチレングリコール、分散有機凝集体、プロピレングリコール、ポリプロピレングリコール、多糖類、又はこれらの組み合わせの少なくとも1つから選択される、請求項12に記載の重合性混合物。
- 請求項5〜13のいずれか一項に記載の重合性混合物の反応生成物を含む物品。
- 疎水的に誘導体化された支持体である、請求項14に記載の物品。
- 前記疎水性モノマーが前記物品の全体にわたって均一に分配されている、請求項14又は15に記載の物品。
- 前記物品が、タンパク質、抗体、融合タンパク質、ワクチン、ペプチド、酵素、DNA、RNA、又はこれらの組み合わせの少なくとも1つを精製するために使用される、請求項14〜16のいずれか一項に記載の物品の使用方法。
- 疎水的に誘導体化された支持体を製造するための方法であって、
(a)混合物であって、
(i)下記構造:
CH2=CR4C(O)NHC(R1R1)(C(R1R1))nC(O)XR3
(式中、nは0又は1の整数であり;R1は、水素原子、アルキル、アリール、及びアルキルアリールの少なくとも1つから独立して選択され、該アルキル、アリール、及びアルキルアリールは全体で10個以下の炭素原子を有し;R3は、アルキル、アリール、アルキルアリール及びエーテルの少なくとも1つから選択される疎水性基であり、該アルキル、アリール、アルキルアリール及びエーテルは全体で4〜30個の範囲の炭素原子を有し;R4は、H又はCH3であり;XはO又はNHである。)
を有する疎水性モノマーと、
(ii)架橋モノマーと、
(iii)場合により、非架橋モノマーと、
を含む混合物を提供する工程と、
(b)前記混合物を重合する工程と、
を含む方法。 - 前記架橋モノマーの量が前記非架橋モノマーの量よりも大きい、請求項18に記載の方法。
- 前記非架橋モノマーの量が前記疎水性モノマーの量よりも大きい、請求項18又は19に記載の方法。
- 前記重合性混合物が粒子である、請求項18〜20のいずれか一項に記載の方法。
- 前記重合性混合物が、織布、不織布、微多孔性繊維、微多孔性膜、フィルム、又はこれらの組み合わせの少なくとも1つにコーティング又はグラフトされる、請求項18〜21のいずれか一項に記載の方法。
- 疎水的に誘導体化された支持体を製造するための方法であって、
(a)疎水性モノマーであって、
下記構造:
CH2=CR4C(O)NHC(R1R1)(C(R1R1))nC(O)XR3
(式中、nは0又は1の整数であり;R1は、水素原子、アルキル、アリール、及びアルキルアリールの少なくとも1つから独立して選択され、該アルキル、アリール、及びアルキルアリールは全体で10個以下の炭素原子を有し;R3は、アルキル、アリール、アルキルアリール及びエーテルの少なくとも1つから選択される疎水性基であり、該アルキル、アリール、アルキルアリール及びエーテルは全体で4〜30個の範囲の炭素原子を有し;R4は、H又はCH3であり;XはO又はNHである。)
を有する疎水性モノマーを与える工程と、
(b)基材を与える工程と、
(c)前記疎水性モノマーを前記基材と接触させる工程と、
(d)前記疎水性モノマーを重合する工程と、
を含む方法。 - 前記重合する工程によって、前記基材上にコーティングが形成される、請求項23に記載の方法。
- 前記重合する工程によって、前記基材からのグラフトが形成される、請求項23に記載の方法。
- 前記基材が、多孔性膜、フィルム、不織布、又はこれらの組み合わせの少なくとも1つである、請求項23〜25のいずれか一項に記載の方法。
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- 2010-03-19 EP EP10762086.6A patent/EP2414321B1/en active Active
- 2010-03-19 CN CN201080014204.0A patent/CN102365262B/zh active Active
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US20160325268A1 (en) | 2016-11-10 |
JP5681166B2 (ja) | 2015-03-04 |
WO2010117598A2 (en) | 2010-10-14 |
US20120039920A1 (en) | 2012-02-16 |
WO2010117598A3 (en) | 2011-01-13 |
BRPI1006782A2 (pt) | 2016-03-15 |
EP2414321B1 (en) | 2020-02-12 |
EP2414321A4 (en) | 2012-10-24 |
US20200406231A1 (en) | 2020-12-31 |
US10807069B2 (en) | 2020-10-20 |
CN102365262B (zh) | 2014-09-17 |
EP2414321A2 (en) | 2012-02-08 |
CN102365262A (zh) | 2012-02-29 |
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