JP5443682B2 - ヒドロキシ基又は第1級アミノ基を有する多孔質樹脂粒子とその製造方法 - Google Patents
ヒドロキシ基又は第1級アミノ基を有する多孔質樹脂粒子とその製造方法 Download PDFInfo
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- JP5443682B2 JP5443682B2 JP2007286836A JP2007286836A JP5443682B2 JP 5443682 B2 JP5443682 B2 JP 5443682B2 JP 2007286836 A JP2007286836 A JP 2007286836A JP 2007286836 A JP2007286836 A JP 2007286836A JP 5443682 B2 JP5443682 B2 JP 5443682B2
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- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- XNTUJOTWIMFEQS-UHFFFAOYSA-N octadecanoyl octadecaneperoxoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCCCCCCCC XNTUJOTWIMFEQS-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000002515 oligonucleotide synthesis Methods 0.000 description 1
- MMSLOZQEMPDGPI-UHFFFAOYSA-N p-Mentha-1,3,5,8-tetraene Chemical compound CC(=C)C1=CC=C(C)C=C1 MMSLOZQEMPDGPI-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
- C07K1/042—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers characterised by the nature of the carrier
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
- C08K5/3725—Sulfides, e.g. R-(S)x-R' containing nitrogen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
- Y10T428/2985—Solid-walled microcapsule from synthetic polymer
- Y10T428/2987—Addition polymer from unsaturated monomers only
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Saccharide Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
HS−R−X … (I)
(式中、Rは炭素原子数2〜12のアルキレン基を示し、官能基Xはヒドロキシ基又は第1級アミノ基から選ばれる官能基を示す。)
で表されるメルカプト化合物を懸濁重合反応系に加えて懸濁共重合を行うことからなる官能基Xを有する多孔質樹脂粒子の製造方法が提供される。
HS−R−X … (I)
(式中、Rは炭素原子数2〜12のアルキレン基を示し、官能基Xはヒドロキシ基又は第1級アミノ基から選ばれる官能基を示す。)
で表されるメルカプト化合物を懸濁重合反応系に加えて懸濁共重合を行うことからなる。
冷却機、攪拌機及び窒素導入管を備えた500mL容量のセパラブルフラスコにポリビニルアルコール1.97gと蒸留水197gを入れ、200rpmにて攪拌してポリビニルアルコールを水に溶解させた。別に、スチレン22.4g、ジビニルベンゼン(純度55%、残余の殆どはエチルベンゼン)22.4g、2−エチルヘキサノール41.9g、イソオクタン17.5g及び過酸化ベンゾイル(25%含水物)0.84gを混合し、溶解させて単量体溶液とした。この単量体溶液を上記セパラブルフラスコに投入し、窒素気流下、室温にて攪拌速度480rpmで攪拌した後、80℃に昇温して、重合を開始した。重合を開始して、2時間経過したとき、メルカプトエタノール2.50gを懸濁重合反応系(即ち、懸濁重合反応液)に加えて、更に、8時間、重合を続けた。重合後、得られた重合生成物を濾取し、蒸留水、アセトン及びメタノールを用いて洗浄した後、真空乾燥して、ヒドロキシ基を有する多孔質樹脂粒子Aを粉末として得た。
重合を開始して、4時間経過したときにメルカプトエタノール2.50gを
加えた以外は、実施例1と同様にして、ヒドロキシ基を有する多孔質樹脂粒子Bを粉末として得た。
スチレン13.5g、ジビニルベンゼン31.4g及びメルカプトエタノール1.73gを用いた以外は、実施例1と同様にして、ヒドロキシ基を有する多孔質樹脂粒子Cを粉末として得た。
スチレン13.5gとジビニルベンゼン31.4gを用いて重合を開始して4時間が経過したときに、メルカプトエタノールに代えて、メルカプトヘキサノール4.50gを懸濁重合反応系に加えた以外は、実施例1と同様にして、ヒドロキシ基を有する多孔質樹脂粒子Dを粉末として得た。
メルカプトエタノールに代えて、2−メルカプトエチルアミン1.73gを用いた以外は、実施例1と同様にして、第1級アミノ基を有する多孔質樹脂粒子Eを粉末として得た。
(懸濁重合)
冷却機、攪拌機及び窒素導入管を備えた500mL容量のセパラブルフラスコにポリビニルアルコール2.5gと蒸留水250gを投入し、200rpmにて攪拌して、ポリビニルアルコールを水に溶解させた。別に、スチレン49g、p−アセトキシスチレン4g、ジビニルベンゼン(純度55%、残余の殆どはエチルベンゼン)7g、2−エチルヘキサノール55g、イソオクタン23g及び過酸化ベンゾイル(25%含水物)1gを混合、溶解して単量体溶液とした。この単量体溶液を上記セパラブルフラスコに入れ、窒素気流下、室温にて攪拌速度400rpmで攪拌した後、80℃に昇温し、その後、10時間、重合を続けた。重合後、重合生成物を濾取し、蒸留水、アセトン及びメタノールを用いて洗浄した後、真空乾燥して、スチレン−アセトキシスチレン−ジビニルベンゼン共重合体からなる多孔質樹脂粒子40gを粉末として得た。
500mL容量のセパラブルフラスコに上記スチレン−アセトキシスチレン−ジビニルベンゼン共重合体の粉末40gとエタノール250gを入れ、500rpmにて攪拌して、上記共重合体をエタノール中に分散させた。この分散液に水酸化ナトリウム2gを蒸留水100gに溶解させた水溶液を加えた後、80℃に昇温して、24時間、加水分解反応を行った。これを塩酸で中和した後、蒸留水とアセトンを用いて、濾過洗浄を行った。この分散液を濾過し、減圧乾燥して、ヒドロキシ基を有する多孔質樹脂粒子Fを粉末として得た。
上記実施例1〜5及び比較例1で得られた多孔質樹脂粒子A〜Fについて、以下の物性値を求めた。結果を表1に示す。
JIS K 0070に準拠した滴定法よって定量した。
微量全窒素分析装置(三菱化学(株)製TN−110)を用いて窒素を定量した。
水銀圧入法によって求めた。即ち、約0.2gの測定試料を水銀ポロシメータ(Quantachrome Co.製PoreMater 60GT)に投入し、水銀接触角140°、水銀表面張力480dyn/cmの条件における水銀注入圧から、測定試料の平均細孔径と比表面積を求めた。
レーザー回折(光散乱式)によってメジアン径を求めた。
多孔質樹脂粒子1gを20mL容量メスシリンダーに入れて見掛けの体積(即ち、乾燥体積Vd)を測定した。次に、上記メスシリンダーに大過剰量の有機溶媒を加え、室温にて24時間静置して、膨潤させた。このようにして、多孔質樹脂粒子が膨潤した後の見掛けの体積(即ち、膨潤体積Vs)を求め、Vs/Vdを膨潤度とした。結果を表2に示す。
Claims (7)
- ラジカル重合可能な芳香族モノビニル単量体と芳香族ジビニル単量体を重合開始剤と共に有機溶媒に溶解させて単量体溶液とし、この単量体溶液を分散安定剤の存在下に水中に分散させ、懸濁重合反応系として、懸濁共重合を行う際に、上記芳香族モノビニル単量体と上記芳香族ジビニル単量体の合計量に基づいて、芳香族ジビニル単量体の割合が6〜80重量%の範囲にあると共に、全重合時間の10〜50%が経過したときに、上記芳香族モノビニル単量体と芳香族ジビニル単量体の合計量において、3〜12重量%の範囲にて、一般式(I)
HS−R−X … (I)
(式中、Rは炭素原子数2〜12のアルキレン基を示し、官能基Xはヒドロキシ基又は第1級アミノ基から選ばれる官能基を示す。)
で表されるメルカプト化合物を懸濁重合反応系に加えて懸濁共重合を行うことからなる官能基Xを有する多孔質樹脂粒子の製造方法。 - 芳香族モノビニル単量体がスチレンである請求項1に記載の官能基Xを有する多孔質樹脂粒子の製造方法。
- ラジカル重合可能な芳香族モノビニル単量体と芳香族ジビニル単量体を重合開始剤と共に有機溶媒に溶解させて単量体溶液とし、この単量体溶液を分散安定剤の存在下に水中に分散させ、懸濁重合反応系として、懸濁共重合を行う際に、上記芳香族モノビニル単量体と上記芳香族ジビニル単量体の合計量に基づいて、芳香族ジビニル単量体の割合が6〜80重量%の範囲にあると共に、全重合時間の10〜50%が経過したときに、上記芳香族モノビニル単量体と芳香族ジビニル単量体の合計量において、3〜12重量%の範囲にて、一般式(I)
HS−R−X … (I)
(式中、Rは炭素原子数2〜12のアルキレン基を示し、官能基Xはヒドロキシ基又は第1級アミノ基から選ばれる官能基を示す。)
で表されるメルカプト化合物を懸濁重合反応系に加えて懸濁共重合を行うことによって得られる官能基Xを有する多孔質樹脂粒子。 - 芳香族モノビニル単量体がスチレンである請求項3に記載の官能基Xを有する多孔質樹脂粒子。
- ヒドロキシ基又は第1級アミノ基を10〜1500μmol/gの範囲で有する請求項3又は4に記載の官能基Xを有する多孔質樹脂粒子。
- 請求項3から5のいずれかに記載の官能基Xを有する多孔質樹脂粒子からなる固相合成用担体。
- オリゴヌクレオチド又はその誘導体の合成用である請求項6に記載の固相合成用担体。
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JP2007286836A JP5443682B2 (ja) | 2007-11-05 | 2007-11-05 | ヒドロキシ基又は第1級アミノ基を有する多孔質樹脂粒子とその製造方法 |
DE200860000612 DE602008000612D1 (de) | 2007-11-05 | 2008-11-04 | Poröse Harzpartikel mit Hydroxygruppe oder primärer Aminogruppe und Herstellungsverfahren dafür |
AT08019289T ATE456585T1 (de) | 2007-11-05 | 2008-11-04 | Poröse harzpartikel mit hydroxygruppe oder primärer aminogruppe und herstellungsverfahren dafür |
EP20080019289 EP2055723B1 (en) | 2007-11-05 | 2008-11-04 | Porous resin particle having hydroxy group or primary amino group and production method thereof |
US12/265,270 US8076383B2 (en) | 2007-11-05 | 2008-11-05 | Porous resin particle having hydroxy group or primary amino group and production method thereof |
CN2008101744297A CN101429262B (zh) | 2007-11-05 | 2008-11-05 | 具有羟基或伯氨基的多孔树脂粒子以及其制备方法 |
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WO2012059510A1 (en) * | 2010-11-02 | 2012-05-10 | Girindus America, Inc. | Back pressure control during solid-phase synthesis on polymeric supports |
EP3546486A1 (en) * | 2018-03-26 | 2019-10-02 | Institute of Chemical Process Fundamentals of the CAS, v. v. i. | Method of solid-state peptide synthesis using a polymeric support |
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NL154220B (nl) | 1968-04-16 | 1977-08-15 | Octrooien Mij Activit Nv | Werkwijze voor het bereiden van ionenuitwisselaars. |
US4098727A (en) | 1970-07-23 | 1978-07-04 | Mobil Oil Corporation | Insoluble polymers having functional groups containing chemically bonded Group VIII metal |
DE3500180A1 (de) | 1985-01-04 | 1986-07-10 | Ernst Prof. Dr. 7400 Tübingen Bayer | Pfropfcopolymerisate aus vernetzten polymeren und polyoxyethylen, verfahren zu ihrer herstellung und ihre verwendung |
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US5248435A (en) * | 1991-12-17 | 1993-09-28 | Mitsubishi Kasei Corporation | Ion exchange resin, process for producing the same, and method for removing impurities from condensate |
US5227463A (en) | 1992-06-12 | 1993-07-13 | Polysar Rubber Corporation | Process for the manufacture of functionalized resins from styrene, divinyl benzene and alkane dithiol |
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US6147159A (en) * | 1998-09-30 | 2000-11-14 | Argonaut Technologies | Compositions for organic synthesis on solid phase and methods of using the same |
US6656653B2 (en) * | 1999-12-15 | 2003-12-02 | Mitsubishi Chemical Corporation | Toner for the development of electrostatic image and method for producing the same |
US6984702B2 (en) * | 2000-03-22 | 2006-01-10 | Dynal Biotech Asa | Process for the preparation of functionalized polymer particles |
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JP2004300248A (ja) * | 2003-03-31 | 2004-10-28 | National Institute Of Advanced Industrial & Technology | 感熱性高分子化合物の分子量制御方法 |
JP4392491B2 (ja) * | 2003-05-14 | 2010-01-06 | 独立行政法人産業技術総合研究所 | 複数種の官能基を持つ異方性高分子微粒子とその製造方法 |
JP4602011B2 (ja) * | 2003-08-29 | 2010-12-22 | 日東電工株式会社 | 多孔質樹脂ビーズおよびその製造方法 |
JP4799831B2 (ja) | 2004-05-14 | 2011-10-26 | 日東電工株式会社 | 多孔質樹脂の製造方法 |
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JP4970881B2 (ja) * | 2006-09-21 | 2012-07-11 | 日東電工株式会社 | 固相合成用担体 |
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Also Published As
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US8076383B2 (en) | 2011-12-13 |
ATE456585T1 (de) | 2010-02-15 |
CN101429262A (zh) | 2009-05-13 |
CN101429262B (zh) | 2013-11-20 |
DE602008000612D1 (de) | 2010-03-18 |
EP2055723B1 (en) | 2010-01-27 |
EP2055723A1 (en) | 2009-05-06 |
US20090124714A1 (en) | 2009-05-14 |
JP2009114271A (ja) | 2009-05-28 |
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