JP7175886B2 - 制御された粒径分布 - Google Patents
制御された粒径分布 Download PDFInfo
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- 238000009826 distribution Methods 0.000 title claims description 65
- 239000002245 particle Substances 0.000 title claims description 51
- 239000000178 monomer Substances 0.000 claims description 192
- 239000011324 bead Substances 0.000 claims description 85
- 229920000642 polymer Polymers 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 29
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 25
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 24
- 229920002554 vinyl polymer Polymers 0.000 claims description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 description 26
- 238000006116 polymerization reaction Methods 0.000 description 22
- 239000012736 aqueous medium Substances 0.000 description 20
- 239000003999 initiator Substances 0.000 description 20
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 16
- 230000000712 assembly Effects 0.000 description 13
- 238000000429 assembly Methods 0.000 description 13
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- 239000002609 medium Substances 0.000 description 12
- 238000010557 suspension polymerization reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000012530 fluid Substances 0.000 description 8
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- 229910052739 hydrogen Inorganic materials 0.000 description 6
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- 238000006243 chemical reaction Methods 0.000 description 5
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- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
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- 125000003118 aryl group Chemical group 0.000 description 3
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
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- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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- 229920002125 Sokalan® Polymers 0.000 description 2
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- 125000003636 chemical group Chemical group 0.000 description 2
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- 235000019322 gelatine Nutrition 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
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- 125000000962 organic group Chemical group 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 238000012935 Averaging Methods 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
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- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- -1 etc.) Chemical group 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
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- 230000000379 polymerizing effect Effects 0.000 description 1
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- 230000005855 radiation Effects 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
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- 239000012508 resin bead Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
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- 239000008107 starch Substances 0.000 description 1
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- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- 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
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/06—Hydrocarbons
- C08F12/08—Styrene
-
- 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
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/18—Suspension polymerisation
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
- C08F20/68—Esters
-
- 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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- 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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/34—Monomers containing two or more unsaturated aliphatic radicals
- C08F212/36—Divinylbenzene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N15/00—Investigating characteristics of particles; Investigating permeability, pore-volume or surface-area of porous materials
- G01N15/02—Investigating particle size or size distribution
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- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
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- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Description
(a1)体積平均径DAV1を有し、且つ1.3未満の均質係数を有する第1のモノマー液滴の集合体を容器内の水性媒体中において形成すること;
(a2)体積平均径DAV2を有し、且つ1.3未満の均質係数を有する第2のモノマー液の滴集合体を容器内の水性媒体中において形成することであって、DAV1とDAV2とは、10μm以上だけ異なり、
工程(a1)及び工程(a2)は、同時に行われるか、又は工程(a2)は、第1のモノマー液滴の集合体が容器内に残っている間に工程(a1)後に行われるか、又はこれらの組み合わせのいずれかである、形成すること;及び
(b)工程(a1)及び(a2)後、懸濁重合によってモノマー液滴を重合させてポリマービーズを形成すること
を含む方法である。
(A1)直径PD1において最大のPM1を有し、且つ75μm以下の半値全幅を有する第1のピーク;
(A2)直径PD2において最大のPM2を有し、且つ75μm以下の半値全幅を有する第2のピーク;及び
(B1)PD1とPD2との間の直径においてVM1の最小値を有する谷
を含み、VM1は、0.25*PM1未満であり、及びVM1は、0.25*PM2未満でもあり、
ポリマービーズは、1種以上の一官能性ビニルモノマー及び1種以上の多官能性ビニルモノマーの重合された単位を含む、ポリマービーズの集合体である。
水性媒体中に懸濁されている液滴の懸濁液は、以降に記載の通りの粒径の集合体を用いて、米国特許第4,444,960号明細書に記載の通りの手順を使用して製造した。
充填密度は、以下の方法により測定した。重量Wの量の「受けとったままの状態」の樹脂を、乾燥した風袋測定したメスシリンダー中に入れた。一定体積Vまで樹脂試料を優しく軽くたたいた。充填密度は、以下の通りに計算した。
充填密度(kg/m3)=1000×W(g)/V(ml)
水性媒体中に懸濁されている液滴の懸濁液を、米国特許第4,444,960号明細書の記載と類似した手順を使用して製造した。
(態様)
(態様1)
ポリマービーズの集合体であって、ビーズ直径の関数として表される体積分布は、
(A1)直径PD1において最大のPM1を有し、且つ75μm以下の半値全幅を有する第1のピーク;
(A2)直径PD2において最大のPM2を有し、且つ75μm以下の半値全幅を有する第2のピーク;及び
(B1)PD1とPD2との間の直径においてVM1の最小値を有する谷
を含み、
VM1は、0.25*PM1未満であり、及びVM1は、0.25*PM2未満でもあり、
前記ポリマービーズは、1種以上の一官能性ビニルモノマー及び1種以上の多官能性ビニルモノマーの重合された単位を含む、ポリマービーズの集合体。
(態様2)
前記ポリマービーズは、スチレンモノマー、アクリルモノマー及びこれらの混合物から選択される1種以上のモノマーの重合された単位を含む、態様1に記載のポリマービーズの集合体。
(態様3)
スチレンモノマーの重合された単位の量と、アクリルモノマーの重合された単位の量との合計は、前記ポリマービーズの重量を基準として75重量%以上、より好ましくは85重量%以上、より好ましくは95重量%以上、より好ましくは99重量%以上である、態様1に記載のポリマービーズの集合体。
(態様4)
ビーズ直径の関数として表される前記体積分布は、
(A3)直径PD3において最大のPM3を有し、且つ75μm以下の半値全幅を有する第3のピーク;
(B2)PD1とPD3との間の直径においてVM2の最小値を有する谷であって、VM2は、0.25*PM1未満であり、及びVM2は、0.25*PM3未満でもある、谷;
(B3)PD3とPD2との間の直径においてVM3の最小値を有する谷であって、VM3は、0.25*PM3未満であり、及びVM1は、0.25*PM2未満でもある、谷
を追加的に含む、態様1に記載のポリマービーズの集合体。
Claims (4)
- ポリマービーズの集合体であって、ビーズ直径の関数として表される体積分布は、
(A1)直径PD1において最大のPM1を有し、且つ75μm以下の半値全幅を有する第1のピーク;
(A2)直径PD2において最大のPM2を有し、且つ75μm以下の半値全幅を有する第2のピーク;及び
(B1)PD1とPD2との間の直径においてVM1の最小値を有する谷
を含み、
VM1は、0.25*PM1未満であり、及びVM1は、0.25*PM2未満でもあり、
前記PD1とPD2とは25μm以上異なり、
前記ポリマービーズの集合体は0.9~1.0の体積平均真球度ψを有し、ここで真球度の指標(ψ)は式:
前記ポリマービーズは、全てのモノマーの重量を基準として、75重量%以上の1種以上の一官能性ビニルモノマー及び5~25重量%の1種以上の多官能性ビニルモノマーの重合された単位を含む、ポリマービーズの集合体。 - 前記ポリマービーズは、スチレンモノマー、アクリルモノマー及びこれらの混合物から選択される1種以上のモノマーの重合された単位を含む、請求項1に記載のポリマービーズの集合体。
- スチレンモノマーの重合された単位の量と、アクリルモノマーの重合された単位の量との合計は、前記ポリマービーズの重量を基準として75重量%以上である、請求項1に記載のポリマービーズの集合体。
- ビーズ直径の関数として表される前記体積分布は、
(A3)直径PD3において最大のPM3を有し、且つ75μm以下の半値全幅を有する第3のピーク;
(B2)PD1とPD3との間の直径においてVM2の最小値を有する谷であって、VM2は、0.25*PM1未満であり、及びVM2は、0.25*PM3未満でもある、谷;
(B3)PD3とPD2との間の直径においてVM3の最小値を有する谷であって、VM3は、0.25*PM3未満であり、及びVM1は、0.25*PM2未満でもある、谷
を追加的に含む、請求項1に記載のポリマービーズの集合体。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201662419135P | 2016-11-08 | 2016-11-08 | |
US62/419,135 | 2016-11-08 | ||
PCT/US2017/060129 WO2018089294A1 (en) | 2016-11-08 | 2017-11-06 | Controlled particle size distribution |
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JP2019533066A JP2019533066A (ja) | 2019-11-14 |
JP7175886B2 true JP7175886B2 (ja) | 2022-11-21 |
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US (1) | US11292855B2 (ja) |
EP (1) | EP3538563B1 (ja) |
JP (1) | JP7175886B2 (ja) |
CN (1) | CN109890849B (ja) |
RU (1) | RU2753011C2 (ja) |
WO (1) | WO2018089294A1 (ja) |
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US10988558B2 (en) * | 2016-11-08 | 2021-04-27 | DDP Specialty Electronic Materials US, Inc. | Controlled particle size distribution |
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EP3538563B1 (en) | 2021-07-07 |
WO2018089294A1 (en) | 2018-05-17 |
RU2019113645A (ru) | 2020-11-06 |
RU2753011C2 (ru) | 2021-08-11 |
US11292855B2 (en) | 2022-04-05 |
CN109890849A (zh) | 2019-06-14 |
US20190233554A1 (en) | 2019-08-01 |
CN109890849B (zh) | 2021-10-26 |
RU2019113645A3 (ja) | 2021-02-18 |
EP3538563A1 (en) | 2019-09-18 |
JP2019533066A (ja) | 2019-11-14 |
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