JPH0368734B2 - - Google Patents
Info
- Publication number
- JPH0368734B2 JPH0368734B2 JP61187712A JP18771286A JPH0368734B2 JP H0368734 B2 JPH0368734 B2 JP H0368734B2 JP 61187712 A JP61187712 A JP 61187712A JP 18771286 A JP18771286 A JP 18771286A JP H0368734 B2 JPH0368734 B2 JP H0368734B2
- Authority
- JP
- Japan
- Prior art keywords
- membrane
- separation
- liquid
- separation membrane
- coupling agent
- 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.)
- Expired
Links
- 239000012528 membrane Substances 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 238000000926 separation method Methods 0.000 claims description 23
- 239000007788 liquid Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 17
- 229920002379 silicone rubber Polymers 0.000 claims description 15
- 239000004945 silicone rubber Substances 0.000 claims description 15
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000005373 pervaporation Methods 0.000 claims description 7
- 239000010409 thin film Substances 0.000 claims description 7
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- APXIUGUTGQHDAX-UHFFFAOYSA-N diethoxymethyl(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[SiH2]C(OCC)OCC APXIUGUTGQHDAX-UHFFFAOYSA-N 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010408 film Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 5
- 239000012466 permeate Substances 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 230000035699 permeability Effects 0.000 description 3
- -1 polydimethylsiloxane skeleton Polymers 0.000 description 3
- 239000002344 surface layer Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- YTEISYFNYGDBRV-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)oxy-dimethylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)C YTEISYFNYGDBRV-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0081—After-treatment of organic or inorganic membranes
- B01D67/0093—Chemical modification
- B01D67/00931—Chemical modification by introduction of specific groups after membrane formation, e.g. by grafting
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/36—Pervaporation; Membrane distillation; Liquid permeation
- B01D61/365—Osmotic distillation or osmotic evaporation
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Transplantation (AREA)
- Inorganic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Description
（産業上の利用分野）
本発明は、液体混合物の分離膜、詳しくは有機
液体と水との混合物（以後有機液体／水の混合物
と略記）から有機液体を優先的に透過させる分離
膜に関するものである。
（従来技術）
従来揮発性有機液体／水の混合物から揮発性有
機液体を膜により分離濃縮する方法として浸透気
化法（pervaporation）が提案されている。
これは分離膜を介して片側に分離される対象で
ある揮発性有機液体／水の混合物を流し、もう一
方側をポンプにより真空に引くもしくは不活性ガ
スをキヤリアとして流すことにより膜透過物を蒸
気として得、透過物を冷却することにより捕集す
る方法である。
（発明が解決しようとする問題点）
しかしながら難分離性揮発性有機液体／水の混
合物の代表例であるエタノール／水系については
エタノール（EtOH）を優先的に透過させる膜は
数少なく、既知のものではシリコーンゴム膜（特
開昭52−68078号、膜7353（1982）参照）が有名で
あり、その他では最近ポリトリメチルシリルプロ
ピン膜（特開昭60−75306号参照）やポリフルオ
ロアルキルアクリレートグラフトポリスチレンを
コートしたシリコーンゴム膜（Poly−mer
Preprints Japan 34（７）1841（1985）参照）が
報告されているが、いずれも透過性能が充分でな
いか、もしくは膜の作成に高度の技術を要するか
で高い透過性能の膜は一般的には得られにくいの
が現状である。
上記に鑑み本発明はこのような問題点を解消す
るため開発されたものである。
（問題点を解決するための手段）
即ち、本発明の液体混合物の分離膜は、揮発性
有機液体／水の混合物を浸透気化分離する膜にお
いて、シリコーンゴムの薄膜、または有機シリコ
ーン化合物をモノマーとしてプラズマ重合させた
薄膜を長鎖アルキル基を有するシランカツプリン
グ剤により表面処理したことを特徴とするもので
ある。
以下、本発明を発明の経緯と共に詳細に説明す
る。
前記のとおり揮発性有機液体／水の混合物の代
表例であるエタノール／水系からエタノールを優
先的に透過させる膜は数少なく、その性能を再現
性良く、一端的に発揮し得る膜は現在のところシ
リコーンゴム膜のみである。シリコーンゴム膜は
ポリジメチルシロキサン骨格からなり、素材とし
てきわめて疎水性が高く、エタノールとの親和性
が大きいためエタノール優先透過膜となつている
と考えられる。
一方浸透気化法における透過は一般的に溶解−
拡散機構が認められており、浸透気化分離膜にお
いてエタノール優先透過性を向上させるためには
分離膜へのエタノールの溶解性を高めること、分
離膜中でのエタノールの拡散性を増大することが
重要と考えられる。
拡散性を増大することは分離膜の厚みを薄くす
ることで解決できると考えられる。溶解性を高め
ることは、ポリジメチルシロキサンよりもさらに
疎水性の高い薄層を分離膜表面に形成することに
よりなし得ると推定し検討を続けた結果、シリコ
ーンゴム膜の表面層を長鎖アルキル基を持つシラ
ンカツプリング剤で処理することにより、より疎
水性の高い表面層を形成させ得る可能性があるこ
とに想到し、本発明を完成するに至つた。
即ち本発明はエタノール／水の混合物を主な分
離対象とする浸透気化膜に関するもので、長鎖ア
ルキル基を有するシランカツプリング剤によりシ
リコーンゴム膜表面を処理することにより得られ
る膜である。
（作用）
使用するシランカツプリング剤は疎水性の強い
官能基を持つほど性能が高くなると予想され、ア
ルキル基ではC8以上のものが望ましい。もちろ
んＣ鎖の長さは長いほどよいが、分離膜を処理す
るうえでシランカツプリング剤が液状であること
が好ましくそれにより自ずから限界は生じてく
る。一般的に入手できるものではオクタデシル基
（C18H37−）を持つものが最も適当である。疎水
性の官能基はアルキル基である必要はなく、不飽
和結合を含むものや、フルオロカーボン鎖などで
あつても良いが、本発明の用途に供し得るほど長
鎖のセグメントを持つシランカツプリング剤は一
般的には入手が困難である。
シランカツプリング剤により処理を受けるシリ
コーンゴム膜はポリジメチルシロキサン骨格、ポ
リハイドロメチルシロキサン骨格を有するものな
ら何でも良いが、本用途に供し得るほどの薄膜と
し得るためには溶剤可能で、加熱架橋型のものが
望ましい、しかしこれに限定されるものではな
い。
また、シリコーンゴム膜は薄膜化した際には分
離膜に用い得るほどの強度はないため、適当な支
持膜上に作成する。これにより20μｍ以下の薄膜
であつても分離膜として使用できる強度を得るこ
とができる。しかし数μｍ以下の薄膜を得るため
には上記の方法は用いらず、この際にはプラズマ
重合法が利用できる。有機シリコーン化合物をモ
ノマーとして適当な支持膜上にプラズマの重合物
を堆積させることにより、1μｍ以下のシリコー
ンゴム類似の薄膜を得ることができ、本用途に好
適な膜が得られる。
シランカツプリング剤による処理は一般的には
シランカツプリング剤をシリコーンゴム膜表面に
適当な時間接触させ、そののち、シリコーンゴム
膜を熱処理することによつてなされる。しかしこ
れらの処理条件はシランカツプリング剤及びシリ
コーンゴム膜の種類などにより適宜適当な条件を
決定する必要がある。
（実施例）
以下に本発明の理解を助けるため実施例を述べ
る。
実施例 １
住友電工製フロロポア（商品名）FP022上にト
ーレシリコーン製SE6720をフレオン113に約10wt
％に溶解したものを塗布し、120℃で1hr熱処理す
ることにより約2μｍ厚のシリコーンゴム膜を得
た。この膜をホルダーに固定し、膜の表面にオク
タデシルジエトキシメチルシランを1hr接触させ
た後120℃1hrの熱処理を行ない、目的の膜を得
た。この膜の分離性能をエタノール／水の混合液
の浸透気化実験で試したところ透過速度1.6×
10-2Kg／m2hr、分離係数αETOH＝16.3が得られた。
（第１表No.１参照）
(Industrial Application Field) The present invention relates to a separation membrane for liquid mixtures, and more particularly, to a separation membrane that preferentially permeates organic liquids from mixtures of organic liquids and water (hereinafter abbreviated as organic liquid/water mixtures). It is. (Prior Art) Pervaporation has been proposed as a method for separating and concentrating a volatile organic liquid from a volatile organic liquid/water mixture using a membrane. This is done by passing the volatile organic liquid/water mixture to be separated on one side of the separation membrane, and evacuating the other side with a pump or flowing an inert gas as a carrier to vaporize the membrane permeate. This method collects the permeate by cooling it. (Problem to be solved by the invention) However, for the ethanol/water system, which is a typical example of a difficult-to-separate volatile organic liquid/water mixture, there are only a few membranes that allow ethanol (EtOH) to permeate preferentially, and there are no known membranes. Silicone rubber membranes (see JP-A-52-68078, Membrane 7353 (1982)) are famous, and other recently developed films include polytrimethylsilylpropyne membranes (see JP-A-60-75306) and polyfluoroalkyl acrylate grafted polystyrene. Coated silicone rubber film (Polymer
Preprints Japan 34 (7) 1841 (1985)), but membranes with high permeability are generally not available, either because their permeability is not sufficient or because they require advanced technology to create. The current situation is that it is difficult to obtain. In view of the above, the present invention has been developed to solve these problems. (Means for Solving the Problems) That is, the liquid mixture separation membrane of the present invention is a membrane for pervaporation separation of a volatile organic liquid/water mixture, and a thin film of silicone rubber or an organic silicone compound as a monomer. This method is characterized in that a plasma-polymerized thin film is surface-treated with a silane coupling agent having a long-chain alkyl group. Hereinafter, the present invention will be explained in detail along with the history of the invention. As mentioned above, there are only a few membranes that preferentially permeate ethanol from the ethanol/water system, which is a typical example of a volatile organic liquid/water mixture.Currently, the only membranes that can demonstrate this performance with good reproducibility are silicone membranes. It is only a rubber membrane. The silicone rubber membrane consists of a polydimethylsiloxane skeleton, and is considered to be an ethanol-permeable membrane because it is extremely hydrophobic as a material and has a high affinity for ethanol. On the other hand, permeation in pervaporation is generally dissolved
A diffusion mechanism has been recognized, and in order to improve the preferential permeability of ethanol in pervaporation separation membranes, it is important to increase the solubility of ethanol in the separation membrane and increase the diffusivity of ethanol in the separation membrane. it is conceivable that. It is thought that increasing the diffusivity can be solved by reducing the thickness of the separation membrane. We presumed that increasing solubility could be achieved by forming a thin layer on the surface of the separation membrane that was even more hydrophobic than polydimethylsiloxane, and as a result of continued investigation, we found that the surface layer of the silicone rubber membrane could be formed with long-chain alkyl groups. The inventors came up with the idea that it is possible to form a surface layer with higher hydrophobicity by treating the surface layer with a silane coupling agent having a silane coupling agent, and thus completed the present invention. That is, the present invention relates to a pervaporation membrane that primarily separates ethanol/water mixtures, and is a membrane obtained by treating the surface of a silicone rubber membrane with a silane coupling agent having a long-chain alkyl group. (Function) It is expected that the performance of the silane coupling agent used will be higher as it has a more hydrophobic functional group, and an alkyl group with C8 or higher is preferable. Of course, the longer the length of the C chain, the better; however, when treating separation membranes, it is preferable that the silane coupling agent be in liquid form, which naturally imposes a limit. Among the commonly available ones, those having an octadecyl group (C 18 H 37 −) are most suitable. The hydrophobic functional group does not need to be an alkyl group, and may be one containing an unsaturated bond or a fluorocarbon chain, but the silane coupling agent has a segment long enough to be used in the present invention. are generally difficult to obtain. The silicone rubber film to be treated with the silane coupling agent may be of any type as long as it has a polydimethylsiloxane skeleton or a polyhydromethylsiloxane skeleton; Preferably, but not limited to. Furthermore, since silicone rubber membranes do not have enough strength to be used as separation membranes when made thin, they are prepared on a suitable support membrane. As a result, even a thin film of 20 μm or less can have the strength to be used as a separation membrane. However, in order to obtain a thin film of several μm or less, the above method is not used, and in this case, a plasma polymerization method can be used. By depositing a plasma polymer on a suitable support film using an organic silicone compound as a monomer, a thin film similar to silicone rubber of 1 μm or less can be obtained, and a film suitable for this purpose can be obtained. Treatment with a silane coupling agent is generally carried out by bringing the silane coupling agent into contact with the surface of the silicone rubber film for an appropriate period of time, and then heat-treating the silicone rubber film. However, these processing conditions must be appropriately determined depending on the type of silane coupling agent and silicone rubber film. (Examples) Examples will be described below to help understand the present invention. Example 1 Approximately 10wt of Toray Silicone SE6720 and Freon 113 on Sumitomo Electric Fluoropore (product name) FP022
A silicone rubber film having a thickness of about 2 μm was obtained by applying a solution dissolved in 100% and heat-treating it at 120° C. for 1 hour. This membrane was fixed on a holder, and the surface of the membrane was brought into contact with octadecyldiethoxymethylsilane for 1 hour, and then heat treated at 120°C for 1 hour to obtain the desired membrane. The separation performance of this membrane was tested in a pervaporation experiment of an ethanol/water mixture, and the permeation rate was 1.6×.
10 −2 Kg/m 2 hr and a separation factor α ETOH =16.3 were obtained.
(See Table 1 No. 1)
【表】
実施例 ２
ポリプラスチツクス社製ジユラガード（商品
名）2400上にヘキサメチルトリシロキサンをプラ
ズマ重合することにより、厚さ約1μｍの膜を得
た。この膜を実施例１と同様の方法で処理を行な
い、分離性能を測定したところ、透過速度1.5×
10-2Kg／m2hr、分離係数αETOH＝18.0が得られた。
（第１表No.２参照）
（発明の効果）
以上の様に本発明の液体混合物の分離膜によれ
ば次の様な効果がある。
シリコーンゴム膜及びその類似の膜の性能をは
るかに越える分離性能の膜が得られる。[Table] Example 2 A film with a thickness of about 1 μm was obtained by plasma polymerizing hexamethyltrisiloxane on Jyuragard (trade name) 2400 manufactured by Polyplastics. This membrane was treated in the same manner as in Example 1, and the separation performance was measured; the permeation rate was 1.5×
10 −2 Kg/m 2 hr and a separation factor α ETOH =18.0 were obtained.
(See Table 1 No. 2) (Effects of the Invention) As described above, the liquid mixture separation membrane of the present invention has the following effects. A membrane with separation performance that far exceeds that of silicone rubber membranes and similar membranes is obtained.
Claims (1)
離する膜において、シリコーンゴムの薄膜、また
は有機シリコーンモノマーをプラズマ重合させて
作成した薄膜を長鎖アルキル基を有するシランカ
ツプリング剤で該薄膜を表面処理したことを特徴
とする液体混合物の分離膜。 ２ シランカツプリング剤として構造式RnPm−
Si−（OQ）ｊ、ここでSiはシリコン原子、Ｏは酸
素原子を示し、ＲはC8H17−以上の長鎖アルキル
基、Ｐ、ＱはCH3−、C2H5−、CH3CO−のいず
れかであり、ｎ＋ｍ＋ｊ＝４、３≧ｎ≧１、３≧
ｊ≧１、２≧ｍ≧０を満たす構造を有する化合物
を用いる特許請求の範囲第１項記載の液体混合物
の分離膜。 ３ シランカツプリング剤としてオクタデシルジ
エトキシメチルシランを用いる特許請求の範囲第
２項記載の液体混合物の分離膜。 ４ 揮発性有機液体がエタノールであるところの
特許請求の範囲第１項記載の液体混合物の分離
膜。[Scope of Claims] 1. In a membrane for pervaporative separation of a mixture of a volatile organic liquid and water, a thin film of silicone rubber or a thin film prepared by plasma polymerization of an organic silicone monomer is combined with a silane cup having a long-chain alkyl group. A separation membrane for a liquid mixture, characterized in that the thin membrane is surface-treated with a ring agent. 2 Structural formula RnPm- as a silane coupling agent
Si-(OQ)j, where Si is a silicon atom, O is an oxygen atom, R is a long-chain alkyl group of C8H17- or more, P, Q are CH3- , C2H5- , CH 3 CO-, n+m+j=4, 3≧n≧1, 3≧
The separation membrane for liquid mixtures according to claim 1, which uses a compound having a structure satisfying j≧1, 2≧m≧0. 3. A separation membrane for a liquid mixture according to claim 2, which uses octadecyldiethoxymethylsilane as a silane coupling agent. 4. A separation membrane for a liquid mixture according to claim 1, wherein the volatile organic liquid is ethanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61187712A JPS6344904A (en) | 1986-08-12 | 1986-08-12 | Separating membrane for liquid mixture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61187712A JPS6344904A (en) | 1986-08-12 | 1986-08-12 | Separating membrane for liquid mixture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6344904A JPS6344904A (en) | 1988-02-25 |
| JPH0368734B2 true JPH0368734B2 (en) | 1991-10-29 |
Family
ID=16210850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61187712A Granted JPS6344904A (en) | 1986-08-12 | 1986-08-12 | Separating membrane for liquid mixture |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6344904A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5215667A (en) * | 1991-08-20 | 1993-06-01 | Exxon Chemical Patents Inc. | Method for separating water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
| US5288818A (en) * | 1991-08-20 | 1994-02-22 | Exxon Chemical Patents Inc. | Method for separating a water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
| JPH07275677A (en) * | 1994-04-11 | 1995-10-24 | Nec Corp | Organic acid separation membrane and its production |
-
1986
- 1986-08-12 JP JP61187712A patent/JPS6344904A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6344904A (en) | 1988-02-25 |
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| Date | Code | Title | Description |
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| EXPY | Cancellation because of completion of term |