WO2020130686A1 - 여과막을 이용한 유기 아연 촉매의 분리 방법 - Google Patents
여과막을 이용한 유기 아연 촉매의 분리 방법 Download PDFInfo
- Publication number
- WO2020130686A1 WO2020130686A1 PCT/KR2019/018131 KR2019018131W WO2020130686A1 WO 2020130686 A1 WO2020130686 A1 WO 2020130686A1 KR 2019018131 W KR2019018131 W KR 2019018131W WO 2020130686 A1 WO2020130686 A1 WO 2020130686A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- organic zinc
- zinc catalyst
- polyalkylene carbonate
- carbonate resin
- carbon atoms
- Prior art date
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- 239000011701 zinc Substances 0.000 title claims abstract description 112
- 239000003054 catalyst Substances 0.000 title claims abstract description 107
- 229910052725 zinc Inorganic materials 0.000 title claims abstract description 107
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title claims abstract description 101
- 238000001914 filtration Methods 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 title claims abstract description 30
- 239000012528 membrane Substances 0.000 title claims description 67
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 61
- 229920001281 polyalkylene Polymers 0.000 claims abstract description 61
- 229920005989 resin Polymers 0.000 claims abstract description 54
- 239000011347 resin Substances 0.000 claims abstract description 54
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- 239000000463 material Substances 0.000 claims description 44
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 24
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- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 12
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- 239000000377 silicon dioxide Substances 0.000 claims description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
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- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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- 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
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- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
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- Y02W30/62—Plastics recycling; Rubber recycling
Definitions
- the present invention relates to a method for separating an organic zinc catalyst dispersed in a solution by filtering the polyalkylene carbonate resin solution.
- Plastic is used as a material for various products due to its ease of manufacture and ease of use, and is used in various fields such as packaging materials, disposable cups and disposable plates, as well as construction materials and automobile interior materials.
- plastic waste increases, and most of it is not decomposed in the natural environment, so waste is mainly treated through incineration, but there is a problem that environmental pollution occurs due to the release of toxic gas during incineration.
- biodegradable plastics that naturally decompose even in the natural environment have been developed.
- Biodegradable plastic is a plastic that gradually decomposes in moisture due to its chemical structure, and begins to decompose in a few weeks in a wet environment such as soil or seawater, and disappears within 1 to several years.
- the decomposition products of biodegradable plastics are decomposed into components that are harmless to the human body, such as water or carbon dioxide, environmental damage is less.
- Polyalkylene carbonate resins by polymerization of carbon dioxide and epoxides have been spotlighted as a kind of biodegradable resin.
- Polyalkylene carbonate is an amorphous transparent resin, unlike an aromatic polycarbonate, which is a similar engineering plastic, has only an aliphatic structure, and is synthesized by a copolymerization reaction under a catalyst using carbon dioxide and epoxide as direct monomers (main raw materials).
- Polyalkylene carbonate has excellent transparency, elongation, and oxygen barrier performance, exhibits biodegradability, and has the advantage of not leaving carbon residues because it is completely decomposed into carbon dioxide and water during combustion.
- the organic zinc catalyst is formed by reacting a dicarboxylic acid such as a zinc precursor and glutaric acid, and has a fine crystalline particle shape. These organic zinc catalysts are evenly dispersed in the polymerization solution after the polymerization reaction of the polyalkylene carbonate resin in the solution phase is completed due to the form of fine crystalline particles, and the particle size is small, so it is easily separated using a conventional filter or centrifugation. There were difficult limits.
- Patent Document 1 KR 10-2018-0043681 A
- the object of the present invention is to use an organic zinc catalyst dispersed in a polyalkylene carbonate resin solution by using a composite filtration membrane in the form of a hydroxy group-containing material and a polyolefin composite material and a polyolefin coated with a hydroxy group-containing material. It provides an efficient and economical method of separation.
- the present invention comprises the steps of injecting a polyalkylene carbonate resin solution containing a polyalkylene carbonate resin and an organic zinc catalyst into a composite filtration membrane, wherein the composite filtration membrane contains a hydroxy group-containing material.
- a method for separating an organic zinc catalyst which is a form in which a hydroxy group-containing material is coated on one or both surfaces of the polyolefin.
- the organic zinc catalyst particles can be efficiently removed from the polyalkylene carbonate resin solution to obtain a transparent high purity polyalkylene carbonate solution.
- the organic zinc catalyst can be removed without additional additives such as silica and diatomaceous earth, the organic zinc catalyst can be easily and easily separated without contaminating the polyalkylene carbonate resin solution.
- the main object of the present invention is to form a polyalkylene carbonate resin by polymerization reaction of carbon dioxide and epoxide under an organic zinc catalyst, and to effectively separate the organic zinc catalyst dispersed finely and dispersed in the polyalkylene carbonate resin solution to obtain high purity. It is for finally obtaining a polyalkylene carbonate.
- the organic zinc catalyst Since the organic zinc catalyst has a sponge-like shape with a soft texture rather than a rigid ceramic structure, deformation easily occurs in a polyalkylene carbonate resin solution, and is simply performed using a filtration membrane having pores smaller than the particle size. There were limitations in the method of physical separation. On the other hand, the organic zinc catalyst is hydrophilic, while the solvent contained in the polyalkylene carbonate resin solution, the polyalkylene carbonate polymer, and other by-products are hydrophobic.
- the organic zinc catalyst is not physically collected by simply adjusting the pore size of the filtration membrane, but the material of the filtration membrane is selected as a hydroxy group-containing material, thereby causing an interaction between the organic zinc catalyst and the filtration membrane, resulting in polyalkyl. It is characterized in that the organic zinc catalyst is more efficiently separated from the rene carbonate resin solution.
- the hydroxy group-containing material has an advantage of having strong interaction with an organic zinc catalyst, but it has good hygroscopicity, and is vulnerable to deformation, so that the physical properties of the filter membrane are deteriorated.
- the separation efficiency of the organic zinc catalyst and the stability of the composite filtration membrane were secured by using the composite filtration membrane in a coated form.
- the present invention comprises the steps of introducing a polyalkylene carbonate resin solution containing a polyalkylene carbonate resin and an organic zinc catalyst into a composite filtration membrane, wherein the composite filtration membrane is a composite material comprising a hydroxy group-containing material and a polyolefin,
- a method for separating organic zinc catalysts in which a hydroxy group-containing material is coated on one or both sides of a polyolefin.
- the organic zinc catalyst may be dispersed in a particle state in the polyalkylene carbonate resin solution.
- the organic zinc catalyst Due to the interaction between the polyalkylene carbonate contained in the polyalkylene carbonate resin solution and the organic zinc catalyst, the organic zinc catalyst is evenly dispersed in the particle state on the polyalkylene carbonate resin solution. For this reason, it has been difficult to separate the organic zinc catalyst dispersed in a fine particle state according to the conventional method for separating the organic zinc catalyst, especially when using a filtration membrane made of a single material such as metal or polyolefin, polyalkylene carbonate. Due to the interaction of the organo-zinc catalyst with the organo-zinc catalyst, the opaque polyalkylene carbonate resin solution still remains, even though the organo-zinc catalyst is not efficiently collected on the filtration membrane and has undergone a filtration process.
- the organic zinc catalyst dispersed in the form of particles in a polyalkylene carbonate polymerization solution simply uses pore size Instead of physically filtering, the organic zinc catalyst is strongly captured in the filter membrane by using the interaction between the hydroxy group of the composite filter membrane and the zinc ion of the organic zinc catalyst, and the organic zinc catalyst finely dispersed in the solution is collected. It can be separated more effectively.
- the material of the composite filter membrane is a composite material containing a hydroxy group-containing material and a polyolefin.
- a hydroxy group-containing material when used as the sole component of the filtration membrane, it is susceptible to deformation by water due to its excellent hygroscopic properties, and problems such as mechanical properties such as strength of the composite filtration membrane may be deteriorated.
- the composite filtration membrane is made of a composite material comprising a hydroxy group-containing material and a polyolefin.
- the strength of the composite filter membrane can be improved, and the surface area of the hydroxy group-containing material can be maximized, thereby increasing the likelihood of contact with the organic zinc catalyst, thereby increasing the hydroxy group-containing material and the organic zinc catalyst. Inducing the interaction more actively, it is possible to further improve the separation efficiency of the organic zinc catalyst.
- the organic zinc catalyst is effectively confined in the composite filtration membrane by mixing a hydroxy group-containing material with polyalkylene and using it as a material for the composite filtration membrane in order to ensure both interaction with the organic zinc catalyst and excellent mechanical properties. While preventing structural deformation of the composite filtration membrane, it is possible to increase the stability of the filtration process.
- the hydroxy group-containing material may be at least one selected from the group consisting of cellulose, glass fiber, hydroxypropyl cellulose, polyvinyl alcohol, silica and alumina.
- the silica and alumina are metal oxides and contain a hydroxy group-containing material on the surface. Specifically, silanol (SiOH) is present on the silica surface, and aluminol (AlOH) is present on the surface of the alumina.
- the cellulose (cellulose) is a molecular formula (C 6 H 10 O 5 ) n
- cellulose is a hydrophilic polysaccharide compound containing a high proportion of hydroxy groups (-OH).
- Cellulose can be effectively used as a component of the composite filtration membrane because it can effectively hold the organic zinc catalyst by causing a strong interaction with the organic zinc catalyst, such as hydrogen bonding.
- the glass fiber is a material in which glass is thinly drawn like a fiber and contains a high proportion of hydroxy groups, so it has the characteristic of effectively separating an organic zinc catalyst by interaction with an organic zinc catalyst like cellulose.
- the polyolefin is high density polyethylene, low density polyethylene, linear low density polyethylene, ultra high molecular weight polyethylene, polypropylene, polybutylene, polypentene, polypropylene polyethylene terephthalate, polybutylene terephthalate, polyester , Polyacetal, polyamide, polycarbonate, polyimide, polyetheretherketone, polyethersulfone, polyphenyleneoxide, polyphenyl It may be a film or a nonwoven fabric formed of one or more selected from the group consisting of polyphenylenesulfidro and polyethylenenaphthalene, but is not limited thereto.
- the polyolefin may be a nonwoven fabric made of polypropylene.
- the composite material constituting the composite filtration membrane of the present invention may be a composite material using cellulose as a hydroxy group-containing material or polypropylene as a polyolefin, and the combination of the two materials may be preferably used as a composite filtration membrane.
- the composite filtration membrane is a type in which a hydroxy group-containing material is coated on one or both sides of a polyolefin.
- the composite filtration membrane of the present invention used a composite material containing a hydroxy group-containing material and a polyolefin, and the two materials are not simply mixed, but have a form in which a hydroxy group-containing material is coated on the polyolefin.
- the polyolefin and the hydroxy group-containing material are uniformly mixed, there may be a problem that it cannot be used as a filtration membrane because it cannot exhibit filtration characteristics.
- the composite filter membrane may be a substrate made of spunlace, spunbond, meltblown, coform, airlaid, or a combination thereof, but is not limited thereto.
- the hydroxy group-containing material may be coated with a thickness of 10 ⁇ m to 10 mm, and specifically, may be coated with a thickness of 10 ⁇ m to 1000 ⁇ m.
- the thickness may mean a thickness coated on one of them.
- a coating of a hydroxy group-containing material may exist such that the weight per unit area of the entire composite filter membrane is 50 to 1000 g/m 2 , but is not limited thereto.
- the weight ratio of the hydroxy group-containing material and the polyolefin may be 1:0.1 to 1:10, preferably 1:0.1 to 1:5, or 1:0.15 To 1:2.
- the content of the polyolefin outside the weight ratio is small, the physical properties and strength of the filter membrane are lowered, which may cause a problem that the filter membrane is easily deformed even with a small impact or external stimulus, and when the content of the polyolefin outside the weight ratio is excessive, the filter membrane Since the hydrophilicity of is not sufficient, the organic zinc catalyst may not be effectively separated.
- the organic zinc catalyst may include a zinc dicarboxylate-based compound.
- the zinc dicarboxylate-based compound may include a zinc salt of an aliphatic dicarboxylate having 3 to 20 carbon atoms or a zinc salt of an aromatic dicarboxylate having 8 to 40 carbon atoms.
- the aliphatic dicarboxylate having 3 to 20 carbon atoms includes glutarate, malonate, succinate, or adipate, and the aromatic dicarboxylate having 8 to 40 carbon atoms is terephthalate, isophthalate, homo Phthalate or phenylglutarate, and the like, and preferably zinc glutarate may be used in terms of activity of the organic zinc catalyst, but is not limited thereto.
- the dicarboxylate is a corresponding dicarboxylic acid, for example, an aliphatic dicarboxylic acid having 3 to 20 carbon atoms such as glutaric acid, malonic acid, succinic acid or adipic acid, but terephthalic acid, isophthalic acid, homo It is derived from aromatic dicarboxylic acids having 8 to 40 carbon atoms such as phthalic acid or phenyl glutaric acid, and can be formed by reaction of these dicarboxylic acids with zinc.
- an aliphatic dicarboxylic acid having 3 to 20 carbon atoms such as glutaric acid, malonic acid, succinic acid or adipic acid, but terephthalic acid, isophthalic acid, homo
- aromatic dicarboxylic acids having 8 to 40 carbon atoms such as phthalic acid or phenyl glutaric acid, and can be formed by reaction of these dicarboxylic acids with zinc.
- the viscosity of the polyalkylene carbonate resin solution may be 10 to 10000 cP, preferably 10 to 5000 cP, more preferably 50 to 300 cP.
- the viscosity refers to the amount of fluid that is difficult to flow, that is, the degree of stickiness. Due to the viscosity of the polyalkylene carbonate resin solution, it is more difficult to separate the organic zinc catalyst from the solution, which is a polyalkylene carbonate resin. The higher the viscosity of the solution, the more so.
- the organic zinc catalyst can be effectively separated from the solution due to the strong interaction between the filtration membrane and the organic zinc catalyst.
- the average pore size of the composite filtration membrane may be 0.1 to 10 ⁇ m, preferably 1 to 10 ⁇ m, and more preferably 1 to 5 ⁇ m.
- the organic zinc catalyst has a nanometer-scale particle size, but exists in agglomerated form of the catalyst particles in a medium to form agglomerates with a large particle size and a small surface area.
- the average particle diameter of the aggregate may be 1 to 100 ⁇ m, 10 to 90 ⁇ m, 50 to 80 ⁇ m, but is not limited thereto.
- the average pore size of the filtration membrane of the present invention is not simply to collect it using pores smaller than the particles of the organic zinc catalyst, but increases the inter-membrane by increasing the interaction between the organic zinc catalyst and the filtration membrane, the size of other by-products, and the pore size. It was decided considering all of the differential pressures. If the pore size of the filtration membrane is not excessively larger than the average particle diameter of the aggregate, the organic zinc catalyst may be trapped on the filtration membrane due to the interaction of the above-described organo zinc catalyst and the filtration membrane, while other by-products can be effectively permeated through the pores of the filtration membrane.
- the average pore size of the filtration membrane as described above, it not only prevents an excessive increase in the differential pressure, but also allows other by-products to pass smoothly, and at the same time, it is organic due to the interaction between the organic zinc catalyst and the filtration membrane.
- the zinc catalyst can be effectively captured.
- the average pore size of the filtration membrane is less than 0.1 ⁇ m, the possibility of separating a small sized organic zinc catalyst increases, but the inter-membrane differential pressure ( ⁇ P) increases, and when the average pore size of the filter membrane exceeds 10 ⁇ m, the small size Organic zinc catalyst and other by-products of the may pass through the filter membrane.
- the composite filtration membrane in the present invention in the step of injecting the polyalkylene carbonate resin solution into the composite filtration membrane, to be filtered while applying a pressure of 1 to 10 bar, or 2 to 8 bar, or 2 to 4 bar Can.
- the present invention in the presence of an organic zinc catalyst, polymerizing a monomer containing carbon dioxide and an epoxide compound; And by removing the organic zinc catalyst by the separation method of the organic zinc catalyst of the present invention to obtain a polyalkylene carbonate resin; including, provides a method for producing a polyalkylene carbonate resin.
- the organic zinc catalyst may be used in the form of a heterogeneous catalyst, and the step of polymerizing may proceed to liquid phase polymerization in a solvent.
- the solvent used in the liquid phase polymerization is methylene chloride, ethylene dichloride, trichloroethane, tetrachloroethane, chloroform, acetonitrile, propionitrile, dimethylformamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide , Nitromethane, 1,3-dioxolane, 1,4-dioxane, hexane, toluene, tetrahydrofuran, methylethylketone, methylamineketone, methyl isobutyl ketone, acetone, cyclohexanone, trichloroethylene, methyl Acetate, vinyl acetate, ethyl acetate, propyl acetate, butyrolactone, caprolactone, nitropropane, benzene, styrene, xylene and methyl propasol or mixtures of two or more thereof can be used, preferably
- the epoxide compound may include halogen or an alkylene oxide having 2 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 5 carbon atoms; A cycloalkylene having 4 to 20 carbon atoms unsubstituted or substituted with halogen or an alkyl group having 1 to 5 carbon atoms; And it may be one or more selected from the group consisting of; or styrene oxide having 8 to 20 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms, but is not limited thereto.
- alkylene oxide having 2 to 20 carbon atoms unsubstituted or substituted with the halogen or an alkyl group having 1 to 5 carbon atoms include ethylene oxide, propylene oxide, butene oxide, pentene oxide, hexene oxide, octene oxide, decene oxide, and dodecene Oxide, tetradecene oxide, hexadecene oxide, octadecene oxide, butadiene monooxide, 1,2-epoxy-7-octene, epifluorohydrin, epichlorohydrin, epibromohydrin, isopropyl glycidyl Ether, butyl glycidyl ether, t-butyl glycidyl ether, 2-ethylhexyl glycidyl ether, allyl glycidyl ether, and the like.
- alkylene oxide having 4 to 20 carbon atoms unsubstituted or substituted with the halogen or alkyl group having 1 to 5 carbon atoms examples include cyclopentene oxide, cyclohexene oxide, cyclooctene oxide, cyclododecene oxide, alpha-pinene oxide, 2,3-epoxynorbornene, limonene oxide, dieldrin, and the like.
- Examples of the styrene oxide having 8 to 20 carbon atoms substituted or provided with the halogen or alkyl group having 1 to 5 carbon atoms include 2,3-epoxypropylbenzene, styrene oxide, phenylpropylene oxide, stilbene oxide, chlorostilbene oxide and dichloro Stilben oxide, 1,2-epoxy-3-phenoxypropane, benzyloxymethyl oxirane, glycidyl-methylphenyl ether, chlorophenyl-2,3-epoxypropyl ether, epoxypropyl methoxyphenyl ether, biphenyl glycine Cydyl ether, glycidyl naphthyl ether, and the like.
- the method and process conditions for polymerizing a monomer containing carbon dioxide and an epoxide compound can be used without limitation, typical polymerization conditions for the production of polyalkylene carbonate resins.
- a polyalkylene carbonate resin solution was synthesized using an organic zinc catalyst.
- a polyalkylene carbonate resin solution containing a solvent, a polyalkylene carbonate resin, an organic zinc catalyst, and the like was used in the following experiment.
- Example 2 in which the organic zinc catalyst was removed using the cellulose (80%)-polypropylene (20%) composite filter according to the present invention, the organic zinc catalyst was effectively separated and transparent It was confirmed that it was in a state.
- Comparative Example 1 using a metal filter it was found that the organic zinc catalyst that was finely distributed was not effectively separated, and as a result, it was found that the transparency was not significantly increased compared to the polyalkylene carbonate resin solution before separation. there was.
- Example 1 the residual Zn content after filtration was very low, and thus the organic zinc catalyst was effectively separated, but the polyolefin content was low, and the stability of the composite filtration membrane was poor. It was confirmed that it was measured, and in Example 3 in which the pressure was increased to 4 bar or more during filtration, it was found that all other reaction conditions slightly decreased the filtration power compared to Example 2.
- Example 6 since the pore size of the composite filtration membrane was small as 0.04 ⁇ m, the organic zinc catalyst was well separated. It was judged to be low. Also in Examples 8 and 9 using glass fibers as the hydroxy group-containing material and Examples 10 and 11 using polyethylene as the polyolefin, the results of the efficient separation of the organic zinc catalyst were confirmed.
- Comparative Example 1 using a metal as a filtration membrane Comparative Examples 2 and 3 using a filtration membrane not coated with a hydroxy group-containing substance, and Comparative Example 4 used as a filtration membrane by uniformly mixing with polypropylene without coating cellulose It was found that separation of the zinc catalyst was not effectively performed.
Abstract
Description
하이드록시기 함유 물질 | 폴리올레핀 | 형태 | 중량비 | 평균 기공 크기(㎛) | 압력 | |
실시예 1 | 셀룰로오스 | 폴리프로필렌 | 코팅 | 1:0.05 | 3 | 2~4 bar |
실시예 2 | 셀룰로오스 | 폴리프로필렌 | 코팅 | 1:0.25 | 3 | 2~4 bar |
실시예 3 | 셀룰로오스 | 폴리프로필렌 | 코팅 | 1:0.25 | 3 | 4 bar 이상 |
실시예 4 | 셀룰로오스 | 폴리프로필렌 | 코팅 | 1:1 | 3 | 2~4 bar |
실시예 5 | 셀룰로오스 | 폴리프로필렌 | 코팅 | 1:15 | 3 | 2~4 bar |
실시예 6 | 셀룰로오스 | 폴리프로필렌 | 코팅 | 1:0.25 | 0.04 | 2~4 bar |
실시예 7 | 셀룰로오스 | 폴리프로필렌 | 코팅 | 1:0.25 | 25 | 2~4 bar |
실시예 8 | 유리 섬유 | 폴리프로필렌 | 코팅 | 1:0.25 | 3 | 2~4 bar |
실시예 9 | 유리 섬유 | 폴리프로필렌 | 코팅 | 1:1 | 3 | 2~4 bar |
실시예 10 | 셀룰로오스 | 폴리에틸렌 등 | 코팅 | 1:0.25 | 8 | 2~4 bar |
실시예 11 | 유리 섬유 | 폴리에틸렌 등 | 코팅 | 1:0.25 | 8 | 2~4 bar |
비교예 1 | - (금속 사용) | - | - | 3 ㎛ | 2~4 bar | |
비교예 2 | - | 폴리프로필렌 | - | - | - | 2~4 bar |
비교예 3 | - | 폴리에틸렌+폴리프로필렌 | 코팅 | 1:1 | - | 2~4 bar |
비교예 4 | 셀룰로오스 | 폴리프로필렌 | 단순 혼합 | 1:0.25 | 3 ㎛ | 2~4 bar |
폴리알킬렌 카보네이트 수지 용액의 Zn 함량(ppm) | ||
여과 전 | 여과 후 | |
실시예 1 | 9375 | 70 -> 6220 |
실시예 2 | 55 | |
실시예 3 | 175 | |
실시예 4 | 110 | |
실시예 5 | 3370 | |
실시예 6 | 50 | |
실시예 7 | 2300 | |
실시예 8 | 60 | |
실시예 9 | 135 | |
실시예 10 | 240 | |
실시예 11 | 310 | |
비교예 1 | 8455 | |
비교예 2 | 8790 | |
비교예 3 | 8560 | |
비교예 4 | 7180 |
Claims (13)
- 폴리알킬렌 카보네이트 수지 및 유기 아연 촉매를 포함하는 폴리알킬렌 카보네이트 수지 용액을 복합 여과막에 투입하는 단계;를 포함하고,상기 복합 여과막은 하이드록시기 함유 물질 및 폴리올레핀을 포함하는 복합재로서, 폴리올레핀의 일면 또는 양면에 하이드록시기 함유 물질이 코팅되어 있는 형태인, 유기 아연 촉매의 분리 방법.
- 청구항 1에 있어서,상기 하이드록시기 함유 물질은 셀룰로오스, 유리 섬유, 하이드록시프로필셀룰로오스, 폴리비닐알코올, 실리카 및 알루미나로 이루어진 군으로부터 선택된 1종 이상인 것인, 유기 아연 촉매의 분리 방법.
- 청구항 1에 있어서,상기 폴리올레핀은 고밀도 폴리에틸렌, 저밀도 폴리에틸렌, 선형저밀도 폴리에틸렌, 초고분자량 폴리에틸렌, 폴리프로필렌, 폴리부틸렌, 폴리펜텐, 폴리프로필렌폴리에틸렌테레프탈레이트, 폴리부틸렌테레프탈레이트, 폴리에스테르, 폴리아세탈, 폴리아미드, 폴리카보네이트, 폴리이미드, 폴리에테르에테르케톤, 폴리에테르설폰, 폴리페닐렌옥사이드, 폴리페닐렌설파이드로 및 폴리에틸렌나프탈렌으로 이루어진 군으로부터 선택된 1종 이상으로 형성된 필름 혹은 부직포인 것인, 유기 아연 촉매의 분리 방법.
- 청구항 1에 있어서,상기 유기 아연 촉매는 아연 디카르복실레이트계 화합물을 포함하는 것인, 유기 아연 촉매의 분리 방법.
- 청구항 4에 있어서,상기 아연 디카르복실레이트계 화합물은 탄소수 3 내지 20의 지방족 디카르복실레이트의 아연염 또는 탄소수 8 내지 40의 방향족 디카르복실레이트의 아연염을 포함하는 것인, 유기 아연 촉매의 분리 방법.
- 청구항 1에 있어서,상기 하이드록시기 함유 물질은 10 ㎛ 내지 10 mm 두께로 코팅되어 있는 것인, 유기 아연 촉매의 분리 방법.
- 청구항 1에 있어서,상기 폴리올레핀 및 하이드록시기 함유 물질의 중량비는 1:0.1 내지 1:10인, 유기 아연 촉매의 분리 방법.
- 청구항 1에 있어서,상기 복합 여과막의 평균 기공 크기는 0.1 내지 10 ㎛인, 유기 아연 촉매의 분리 방법.
- 청구항 1에 있어서,상기 투입하는 단계에서는 1 내지 10 bar의 압력을 가하는, 유기 아연 촉매의 분리 방법.
- 청구항 1에 있어서,상기 유기 아연 촉매는 상기 폴리알킬렌 카보네이트 수지 용액에 입자 상태로 분산되어 있는, 유기 아연 촉매의 분리 방법.
- 청구항 1에 있어서,상기 폴리알킬렌 카보네이트 수지 용액의 점도는 10 내지 10000 cP인, 유기 아연 촉매의 분리 방법.
- 유기 아연 촉매의 존재 하에 이산화탄소 및 에폭사이드 화합물을 포함하는 단량체 조성물을 중합하여, 폴리알킬렌 카보네이트 수지 및 유기 아연 촉매를 포함하는 폴리알킬렌 카보네이트 수지 용액을 제조하는 단계; 및청구항 1 내지 11 중 어느 한 항에 따른 방법으로 유기 아연 촉매를 분리하는 단계;를 포함하는, 폴리알킬렌 카보네이트 수지의 제조방법.
- 청구항 12에 있어서,상기 에폭사이드 화합물은 할로겐 또는 탄소수 1 내지 5의 알킬기로 치환 또는 비치환된 탄소수 2 내지 20의 알킬렌 옥사이드; 할로겐 또는 탄소수 1 내지 5의 알킬기로 치환 또는 비치환된 탄소수 4 내지 20의 사이클로 알킬렌 옥사이드; 및 할로겐 또는 탄소수 1 내지 5의 알킬기로 치환 또는 비치된 탄소수 8 내지 20의 스티렌 옥사이드;로 이루어진 군에서 선택된 1종 이상인, 폴리알킬렌 카보네이트 수지의 제조방법.
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US16/973,692 US20210253790A1 (en) | 2018-12-19 | 2019-12-19 | Method for separating organic zinc catalyst using filtering membrane |
EP19899341.2A EP3895791A4 (en) | 2018-12-19 | 2019-12-19 | PROCESS FOR THE SEPARATION OF AN ORGANIC ZINC CATALYST USING A FILTRATION MEMBRANE |
JP2020569791A JP7234263B2 (ja) | 2018-12-19 | 2019-12-19 | ろ過膜を用いた有機亜鉛触媒の分離方法 |
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20150050461A (ko) * | 2013-10-30 | 2015-05-08 | 주식회사 엘지화학 | 유기 아연 촉매의 제조 방법 및 폴리알킬렌 카보네이트 수지의 제조 방법 |
KR20170039674A (ko) * | 2014-08-12 | 2017-04-11 | 토소가부시키가이샤 | 알킬렌 옥사이드 중합 촉매 및 이것을 이용한 폴리알킬렌 옥사이드의 제조 방법 |
KR20170048222A (ko) * | 2015-10-26 | 2017-05-08 | 주식회사 엘지화학 | 유기 아연 촉매, 이의 제조 방법 및 상기 촉매를 이용한 폴리알킬렌 카보네이트 수지의 제조 방법 |
KR20170071519A (ko) * | 2014-10-22 | 2017-06-23 | 셰브런 유.에스.에이.인크. | 귀중한 금속 회수용 폐촉매를 제조하는 방법 |
KR20170128396A (ko) * | 2015-03-10 | 2017-11-22 | 도아고세이가부시키가이샤 | (메트)아크릴레이트의 제조 방법 |
KR20180043681A (ko) | 2016-10-20 | 2018-04-30 | 주식회사 엘지화학 | 유기 아연 촉매의 제조 방법 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4558640B2 (ja) * | 2005-12-22 | 2010-10-06 | トヨタ紡織株式会社 | フィルタ用ろ材、流体ろ過用フィルタ及びエンジン用オイルフィルタ |
US9010547B2 (en) | 2007-05-26 | 2015-04-21 | The Research Foundation Of State University Of New York | High flux fluid separation membranes comprising a cellulose or cellulose derivative layer |
EP2072532A1 (en) * | 2007-12-21 | 2009-06-24 | Lanxess Deutschland GmbH | A process for removing iron-residues, rhodium- and ruthenium-containing catalyst residues from optionally hydrogenated nitrile rubber |
KR100982641B1 (ko) * | 2008-12-09 | 2010-09-16 | 한국화학연구원 | 결정성 다공성 유무기혼성체를 함유하는 흡착제 |
CN102311180B (zh) * | 2010-06-29 | 2013-02-06 | 中国石油化工股份有限公司 | 一种铜锌催化剂废水中铜锌的去除及回收方法 |
ES2758076T3 (es) * | 2013-08-02 | 2020-05-04 | Covestro Deutschland Ag | Procedimiento para la preparación de polietercarbonatopolioles |
WO2016093592A2 (ko) * | 2014-12-08 | 2016-06-16 | 주식회사 엘지화학 | 폴리알킬렌카보네이트 수지의 제조방법 |
KR101848797B1 (ko) * | 2015-02-17 | 2018-04-13 | 주식회사 엘지화학 | 선형 무기 배위 고분자, 금속 착화합물, 이를 포함하는 금속 나노 구조체 및 촉매 조성물 |
US10618037B2 (en) * | 2015-06-24 | 2020-04-14 | Zeon Corporation | Method for recovering catalyst |
KR102067687B1 (ko) * | 2016-03-11 | 2020-02-11 | 주식회사 엘지화학 | 열안정성 및 가공성이 향상된 폴리알킬렌 카보네이트를 포함하는 수지 조성물의 경제적 제조방법 |
EP3219741A1 (de) * | 2016-03-18 | 2017-09-20 | Covestro Deutschland AG | Verfahren zur herstellung von polyethercarbonatpolyolen |
JP7104807B2 (ja) * | 2018-12-20 | 2022-07-21 | エルジー・ケム・リミテッド | 有機亜鉛触媒の製造方法、及びこれから製造された有機亜鉛触媒を用いたポリアルキレンカーボネート樹脂の製造方法 |
-
2019
- 2019-12-19 KR KR1020190170675A patent/KR102379597B1/ko active IP Right Grant
- 2019-12-19 CN CN201980039877.2A patent/CN112312998A/zh active Pending
- 2019-12-19 WO PCT/KR2019/018131 patent/WO2020130686A1/ko unknown
- 2019-12-19 CA CA3105028A patent/CA3105028A1/en active Pending
- 2019-12-19 US US16/973,692 patent/US20210253790A1/en active Pending
- 2019-12-19 EP EP19899341.2A patent/EP3895791A4/en active Pending
- 2019-12-19 JP JP2020569791A patent/JP7234263B2/ja active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20150050461A (ko) * | 2013-10-30 | 2015-05-08 | 주식회사 엘지화학 | 유기 아연 촉매의 제조 방법 및 폴리알킬렌 카보네이트 수지의 제조 방법 |
KR20170039674A (ko) * | 2014-08-12 | 2017-04-11 | 토소가부시키가이샤 | 알킬렌 옥사이드 중합 촉매 및 이것을 이용한 폴리알킬렌 옥사이드의 제조 방법 |
KR20170071519A (ko) * | 2014-10-22 | 2017-06-23 | 셰브런 유.에스.에이.인크. | 귀중한 금속 회수용 폐촉매를 제조하는 방법 |
KR20170128396A (ko) * | 2015-03-10 | 2017-11-22 | 도아고세이가부시키가이샤 | (메트)아크릴레이트의 제조 방법 |
KR20170048222A (ko) * | 2015-10-26 | 2017-05-08 | 주식회사 엘지화학 | 유기 아연 촉매, 이의 제조 방법 및 상기 촉매를 이용한 폴리알킬렌 카보네이트 수지의 제조 방법 |
KR20180043681A (ko) | 2016-10-20 | 2018-04-30 | 주식회사 엘지화학 | 유기 아연 촉매의 제조 방법 |
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KR102379597B1 (ko) | 2022-03-29 |
JP2021526579A (ja) | 2021-10-07 |
EP3895791A1 (en) | 2021-10-20 |
KR20200076644A (ko) | 2020-06-29 |
US20210253790A1 (en) | 2021-08-19 |
JP7234263B2 (ja) | 2023-03-07 |
CA3105028A1 (en) | 2020-06-25 |
CN112312998A (zh) | 2021-02-02 |
EP3895791A4 (en) | 2022-03-23 |
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