JP2020147714A - 重合体の製造方法 - Google Patents
重合体の製造方法 Download PDFInfo
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 239000002904 solvent Substances 0.000 claims abstract description 67
- 239000013557 residual solvent Substances 0.000 claims abstract description 65
- 239000000126 substance Substances 0.000 claims abstract description 28
- 239000007789 gas Substances 0.000 claims description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 14
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 9
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
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- 125000003158 alcohol group Chemical group 0.000 claims description 2
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- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 11
- 229940035429 isobutyl alcohol Drugs 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000005456 alcohol based solvent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
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- 229910052786 argon Inorganic materials 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
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- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
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Abstract
Description
フラスコにイソブチルアルコール(101kPaでの沸点:107℃)77重量部を添加し、105℃に加熱して窒素置換を行った。その後、攪拌しながら、窒素雰囲気下で、モノマーとしてメタクリル酸メチル3.0重量部、アクリル酸ブチル73.2重量部、メタクリル酸3−(トリメトキシシリル)プロピル1.9重量部、メタクリル酸3−(メチルジメトキシシリリル)プロピル1.9重量部、アクリル酸2−エチルヘキシル20重量部と、重合開始剤としてジメチル 2,2’−アゾビス(2−メチルプロピオネート)2.6重量部、イソブチルアルコール13重量部の溶液を5時間かけて滴下し、その後2時間重合を行った。以上により、重量平均分子量8,600の反応性ケイ素基を有する(メタ)アクリル酸エステル系重合体のイソブチルアルコール溶液を得た。
合成例で得られた反応性ケイ素基を有する(メタ)アクリル酸エステル系重合体のイソブチルアルコール溶液の温度を105℃に維持して、以下のとおりイソブチルアルコールの減圧脱揮を行った。
Claims (11)
- 重合体が溶媒に溶解している重合体溶液から、残存溶媒量が低減された重合体を製造する方法であって、
前記重合体溶液を含む系の気圧を1kPa以下にまで減圧して溶媒を留去する工程、
続いて、0℃での状態が気体である物質を前記系に導入して、前記系の気圧を10kPa以上にまで上昇させる工程、及び
その後、前記系の気圧を1kPa以下にまで減圧して重合体中の残存溶媒量を低減する工程を含み、
前記残存溶媒量が低減された重合体の23℃での粘度が0.1Pa・s〜300Pa・sである、重合体の製造方法。 - 前記残存溶媒量が低減された重合体中の残存溶媒量が、当該重合体全体に対して2000ppm以下である、請求項1に記載の製造方法。
- 前記残存溶媒量が低減された重合体中の残存溶媒量が、当該重合体全体に対して1000ppm以下である、請求項2に記載の製造方法。
- 前記0℃での状態が気体である物質が、不活性ガスである、請求項1〜3のいずれか1項に記載の製造方法。
- 前記溶媒を留去する工程時の系の温度が、前記溶媒の101kPaでの沸点±20℃である、請求項1〜4のいずれか1項に記載の製造方法。
- 前記溶媒を留去する工程時の系の温度が、前記溶媒の101kPaでの沸点よりも低い、請求項1〜5のいずれか1項に記載の製造方法。
- 前記溶媒が、アルコール系溶媒である、請求項1〜6のいずれか1項に記載の製造方法。
- 前記重合体が、(メタ)アクリル酸エステル系重合体を含む、請求項1〜7のいずれか1項に記載の製造方法。
- 前記重合体が、反応性シリル基を有する(メタ)アクリル酸エステル系重合体を含む、請求項8に記載の製造方法。
- 前記溶媒が、前記重合体を形成するための重合反応で使用された溶媒を含む、請求項1〜9のいずれか1項に記載の製造方法。
- 前記残存溶媒量を低減する工程の後、
再度、0℃での状態が気体である物質を前記系に導入して、前記系の気圧を10kPa以上にまで上昇させる工程、及び
その後、前記系の気圧を1kPa以下にまで減圧して重合体中の残存溶媒量をさらに低減する工程を実施する、請求項1〜10のいずれか1項に記載の製造方法。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5398383A (en) * | 1977-02-08 | 1978-08-28 | Nippon Zeon Co Ltd | Continuous production of cyclopentadiene resin and oil |
JP2000143721A (ja) * | 1998-11-06 | 2000-05-26 | Sanyo Chem Ind Ltd | 樹脂中の残存単量体の脱揮方法 |
JP2011074373A (ja) * | 2009-09-04 | 2011-04-14 | Idemitsu Kosan Co Ltd | 重合溶液の揮発成分除去装置、その方法、および、重合装置 |
JP2015054917A (ja) * | 2013-09-11 | 2015-03-23 | 旭硝子株式会社 | 末端不飽和基含有重合体の精製方法、末端不飽和基含有ポリエーテルの製造方法、および加水分解性シリル基含有ポリエーテルの製造方法 |
JP2015124247A (ja) * | 2013-12-25 | 2015-07-06 | 出光興産株式会社 | 重合溶液の揮発成分除去装置、および重合溶液の揮発成分除去方法 |
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- 2019-03-15 JP JP2019048342A patent/JP7285664B2/ja active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5398383A (en) * | 1977-02-08 | 1978-08-28 | Nippon Zeon Co Ltd | Continuous production of cyclopentadiene resin and oil |
JP2000143721A (ja) * | 1998-11-06 | 2000-05-26 | Sanyo Chem Ind Ltd | 樹脂中の残存単量体の脱揮方法 |
JP2011074373A (ja) * | 2009-09-04 | 2011-04-14 | Idemitsu Kosan Co Ltd | 重合溶液の揮発成分除去装置、その方法、および、重合装置 |
JP2015054917A (ja) * | 2013-09-11 | 2015-03-23 | 旭硝子株式会社 | 末端不飽和基含有重合体の精製方法、末端不飽和基含有ポリエーテルの製造方法、および加水分解性シリル基含有ポリエーテルの製造方法 |
JP2015124247A (ja) * | 2013-12-25 | 2015-07-06 | 出光興産株式会社 | 重合溶液の揮発成分除去装置、および重合溶液の揮発成分除去方法 |
Non-Patent Citations (1)
Title |
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"飽和水蒸気量", ウィキペディア, JPN6023000301, 5 December 2022 (2022-12-05), ISSN: 0004964720 * |
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