KR20170030931A - Composition for interfacial polymerizing polyamide, method for preparing reverse osmosis membrane using the same, and reverse osmosis membrane and water treatment module comprising the compound - Google Patents
Composition for interfacial polymerizing polyamide, method for preparing reverse osmosis membrane using the same, and reverse osmosis membrane and water treatment module comprising the compound Download PDFInfo
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- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
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- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
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Abstract
Description
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a composition for interfacial polymerization of polyamide and a process for producing a reverse osmosis membrane using the same. The present invention also relates to a reverse osmosis membrane manufactured using the composition for interfacial polymerization of polyamide and a water treatment module including the reverse osmosis membrane.
The phenomenon that the solvent moves between the two solutions separated by the semi-permeable membrane through the membrane from the solution with a low solute concentration to the solution with a high solute concentration is called osmotic phenomenon. The pressure acting on the solution side Is called osmotic pressure. However, when an external pressure higher than osmotic pressure is applied, the solvent moves toward the solution having a low solute concentration. This phenomenon is called reverse osmosis. By using the reverse osmosis principle, it is possible to separate various salts or organic substances through the semipermeable membrane using the pressure gradient as a driving force. Water treatment membranes using this reverse osmosis phenomenon have been used to supply water for domestic, architectural and industrial purposes by separating substances at a molecular level and removing salts from brine or seawater.
Typical examples of such a water treatment separation membrane include a polyamide-based water treatment separation membrane, and a polyamide-based water treatment separation membrane is produced by a method of forming a polyamide active layer on a microporous layer support. More specifically, Forming a microporous support by immersing the microporous support in an aqueous solution of m-Phenylene Diamine (mPD) to form an mPD layer, and then adding tri- mesoyl chloride, TMC) in an organic solvent so that the mPD layer is brought into contact with the TMC to perform interfacial polymerization, thereby forming a polyamide layer.
The present invention provides an alkylene oxide-based compound, a composition for interfacial polymerization comprising the same, a process for preparing a reverse osmosis membrane using the same, and a reverse osmosis membrane and a water treatment module comprising the compound.
One embodiment of the present disclosure relates to a composition comprising at least one of an amine compound and an acyl halide compound; And a compound represented by the following formula (1): < EMI ID =
[Chemical Formula 1]
In Formula 1,
m, n and p are each an integer of 1 to 50, o is an integer of 0 to 5, q is an integer of 0 to 2,
X 1 to X 14 are the same or different from each other and are each independently hydrogen or a halogen atom,
Y is selected from the following formulas,
* Is a moiety bonded to Formula 1,
M and M 'are the same or different and each independently hydrogen or monovalent cation.
Another embodiment of the present disclosure provides a method of preparing a porous support, comprising: preparing a porous support; And forming a polyamide active layer on the porous support using the composition for interfacial polymerization of polyamide described above.
According to one example, the composition for polyamide interfacial polymerization includes an amine compound and the compound of Formula 1, and the polyamide active layer is formed by interfacial polymerization by contacting the polyamide interfacial polymerization composition with an acyl halide compound .
According to another example, the composition for interfacial polymerization of polyamide includes an acyl halide compound and a compound of formula (1), and the interfacial polymerization is carried out by contacting the composition for interfacial polymerization of polyamide with an amine compound to form a polyamide active layer .
Another embodiment of the present disclosure relates to a porous support; And a polyamide active layer provided on the porous support, wherein the polyamide active layer comprises the compound of the above-mentioned formula (1) or the following formula (2): < EMI ID =
(2)
In Formula 2,
m, n, p, q, X 1 to X 14 are as defined in formula (1)
Y 'is selected from the following formulas,
* Is a moiety bonded to Formula 2,
M is hydrogen or a monovalent cation.
Another embodiment of the present disclosure provides a water treatment module comprising a reverse osmosis membrane as described above.
According to the embodiments described herein, the compound of Chemical Formula 1 is added during the production of the polyamide active layer of the reverse osmosis membrane, and the compound of Chemical Formula 1 may serve as an anionic surfactant. The compound of Chemical Formula 1 can effectively prevent turbidity and sedimentation by additives such as a flux enhancer and a rejection improver used in the production of the polyamide active layer, thereby preventing contamination of the membrane production facility. Thus, the reverse osmosis membrane having high water permeability and high salt removal efficiency can be efficiently produced. In addition, the dispersion stability of the composition for preparing the polyamide active layer of the reverse osmosis membrane can be improved, and the physical properties and quality of the reverse osmosis membrane can be improved.
1 is a photograph showing the degree of turbidity of the compositions prepared in Comparative Examples 1 (a) and 1 (b), respectively.
When a member is referred to herein as being "on " another member, it includes not only a member in contact with another member but also another member between the two members.
Whenever a component is referred to as "comprising ", it is to be understood that the component may include other components as well, without departing from the specification unless specifically stated otherwise.
The composition for polyamide interfacial polymerization according to one embodiment of the present invention comprises at least one of an amine compound and an acyl halide compound; Which comprises the compound of the above-mentioned formula (1). The composition may contain only one kind of the compound represented by the above-mentioned formula (1), or may include two or more kinds.
According to another embodiment of the present invention, M and M 'in the above formula (1) are the same or different from each other, and each independently represents hydrogen, Na + , K + , NH 4 + , or alkylammonium ion.
In the present specification, the halogen atom is fluorine, chlorine, bromine or iodine.
In the present specification, alkyl is straight chain or branched chain alkyl having 1 to 20 carbon atoms.
According to another embodiment of the present invention, m in Formula 1 is an integer of 1 to 20.
According to another embodiment of the present invention, m in Formula 1 is an integer of 1 to 10.
According to another embodiment of the present invention, m in Formula 1 is an integer of 1 to 5.
According to another embodiment of the present invention, m in the formula (1) is 1 or 2.
According to another embodiment of the present invention, n in Formula 1 is an integer of 1 to 20.
According to another embodiment of the present invention, n in the general formula (1) is an integer of 1 to 10.
According to another embodiment of the present invention, o in Formula 1 is an integer of 0 to 3.
According to another embodiment of the present invention, o in formula (1) is 0 or 1.
According to another embodiment of the present invention, q in the formula (1) is 0, 1 or 2.
According to another embodiment of the present invention, q in the formula (1) is 0 or 1.
According to another embodiment of the present invention, Y in the formula (1) is represented by the following formula and q is 1.
According to another embodiment of the present invention, Y in the formula (1) is the following structural formula and q is 0.
According to another embodiment of the present disclosure, X 1 to X 12 are hydrogen.
According to another embodiment of the present invention, M and M 'in Formula 1 are the same or different and independently selected from the following formulas.
According to another embodiment of the present invention, the formula (1) may be represented by the following structural formula, but is not limited thereto.
The compounds of Formula 1 are available from commercial sources, such as Sigma Aldrich.
According to one embodiment, the compound of the formula (1) is contained in the polyamide interfacial polymerization composition in an amount of 0.001 to 1% by weight, preferably 0.01 to 0.5% by weight, more preferably 0.05 to 0.3% by weight, % ≪ / RTI > by weight. When the compound of Formula 1 is added in an amount of 0.001% by weight or more, the dispersing effect of the components in the composition is excellent and it is advantageous in terms of the processability on the porous support for producing the membrane. The inclusion of 1 wt% of the compound of formula (1) is advantageous in forming a film of uniform thickness, thereby increasing the permeation flow rate and preventing the salt removal rate from being reduced, which is advantageous for use as a water treatment separator.
The composition for interfacial polymerization of polyamide may further contain a solvent as required. As the solvent, those known to be used for polyamide polymerization may be used. For example, water or an organic solvent may be used.
For example, when the composition for interfacial polymerization of polyamide includes an amine compound, the composition may contain at least one compound selected from the group consisting of water, acetone, dimethylsulfoxide (DMSO), 1-methyl-2-pyrrolidinone (NMP) Hexamethylphosphoramide (HMPA), and the like.
For example, when the composition for polyamide interfacial polymerization includes an acyl halide compound, the composition may further include an organic solvent. Examples of the organic solvent include aliphatic hydrocarbon solvents such as Freon and hydrophobic liquids such as hexane, cyclohexane, heptane and alkane having 5 to 12 carbon atoms which are immiscible with water, for example, alkanes having 5 to 12 carbon atoms And mixtures thereof, such as IsoPar (Exxon), ISOL-C (SK Chem), and ISOL-G (Exxon).
In addition, the composition for interfacial polymerization of polyamide may further include a permeation flux enhancer or a rejection enhancer as necessary. As a flux enhancing agent and a salt removal enhancer, those known in the art can be used. The content of the flux enhancing agent or the salt elimination enhancer may be determined depending on the kind and the necessity, for example, 0.01 wt% to 10 wt% based on 100 wt% of the composition.
The permeation flow rate improver may be a metal chelate compound including a metal atom or a metal ion and a metal atom or a metal ion and a bidentate ligand. Wherein the metal may be a Group 2 to Group 15 metal on the IUPAC Periodic Table. According to one example, the metal may be a Group 2 or Group 13 metal on the IUPAC Periodic Table. According to one example, the metal may be selected from the group consisting of alkaline earth metals such as beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr) and barium (Ba). The bidentate ligand may be selected, for example, from the following structural formulas.
Wherein each of R 1 , R 2 , R 3 , R 4 and R 5 is independently C 1 -C 10 alkyl, halogenated C 1 -C 10 alkyl, a 5-membered or 6-membered aromatic ring, a condensed 6- An aromatic heterocyclic ring system containing two ring atoms and an aromatic ring system containing a five-membered ring condensed with a six-membered aromatic ring. Each of R 1 , R 2 , R 3 , R 4 and R 5 may be independently selected from C 1 -C 6 alkyl and halogenated C 1 -C 6 alkyl. Wherein one of R 1 , R 2 , R 3 , R 4 and R 5 is phenyl, benzyl, a C 1 -C 5 aromatic ring containing 1 to 4 heteroatoms selected from N, O and S, C 5 -C, which contains 1 to 4 hetero atoms selected from S and can be selected from 9 bicyclic aromatic ring system. Any one of R 1 , R 2 , R 3 , R 4 or R 5 is selected from furanyl, pyrrolyl, thiopheny, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, phenyl, pyridinyl, Benzothiophenylyl, indazolyl, benzo [c] thiophenylyl, isoquinolyl, isoquinolyl, isoquinolyl, isoquinolyl, Indolyl, isobenzofuranyl, naphthaleneyl, quinolinyl, quinoxalinyl, quinazolidinyl, and isoquinolinyl.
The bidentate ligand may be acetylacetonate (aca) or fluorinated acetylacetonate. The bidentate ligand may be a beta-diketonate or a fluorinated beta-diketonate. For example, the bidentate ligand may be pentane-2,4-dionate; 1,5-difluoropentane-2,4-dionate; 1,1,5,5-tetrafluoropentane-2,4-dionate; 1,1,1,5,5,5-hexafluoropentane-2,4-dionate; Propane-1,3-dionate; Butane-1,3-dionate; 4-fluorobutane-1,3-dionate; 4,4-difluoro-butane-1,3-dionate; 4,4,4-Trifluorobutane-1,3-dionate; Heptane-3,5-dionate; 1-fluoro-hexane-2,4-dionate; 1,5-difluoropentane-2,4-dionate; 1,1,5-trifluoropentane-2,4-dionate; 1,1,5,5-tetrafluoropentane-2,4-dionate; 1,1,1,5,5-pentafluoropentane-2,4-dionate; 1,1,1,5,5,5-hexafluoropentane-2,4-dionate; And octane-3,5-dionate, and combinations thereof.
In some embodiments, the metal chelating additive containing a bidentate ligand with the metal atom or metal ion is Al (acac) 3, Al ( F 6 acac) 3, Be (acac) 2, Be (F 6 acac) 2, Ca (acac) 2, Ca ( F 6 acac) 2, Cd (acac) 2, Cd (F 6 acac) 2, Ce (acac) 3, Ce (F 6 acac) 3, Cr (acac) 3, Co ( acac) 3, Cu (acac) 2, Cu (F 6 acac) 2, Dy (acac) 3, Er (acac) 3, Fe (acac) 2, Fe (acac) 3, Ga (acac) 3, Hf ( acac) 4, In (acac) 3, K (acac), Li (acac), Mg (acac) 2, Mg (F 6 acac) 2, Mn (acac) 2, Mn (acac) 3, MoO 2 (acac ) 2, MoO 2 (F 6 acac) 2, Na (acac), Nd (acac) 3, Nd (F 6 acac) 3, Ni (acac) 2, Ni (F 6 acac) 2, Pd (acac) 2 , Pr (acac) 3, Pr (F 6 acac) 3, Ru (acac) 3, Ru (F 6 acac) 3, Sc (acac) 2, Sc (F 6 acac) 2, Sm (acac) 3, Sn (acac) 2, Sn (acac ) 2 Cl 2, t-butyl-Sn (acac) 2, t-butyl-Sn (acac) 2 Cl 2, Sn (F 6 acac) 2, Sr (acac) 2, Sr (F 6 acac) 2, Tb (acac) 3, V (acac) 3, Y (acac) 3, Y (F 6 acac) 3, Zn (acac) 2, Zn (F 6 acac) 2, and Zr ( acac) 4 , and F 6 acac refers to 1,1,1,5,5,5-hexafluoroacetyl-acetonate.
As the salt elimination enhancing agent, a compound containing a hetero atom such as N, O or S may be used. According to one example, as the salt removal enhancer, biguanide, dicarbonate, pentathionate, or a polymer including at least one of the structures may be used. The polymer may include at least one structure selected from the following structural formulas, for example.
In the above structural formulas, X is a direct bond or alkylene having 1 to 60 carbon atoms, specifically 1 to 30 carbon atoms, and n is an integer of 1 to 60. The terminal of the polymer is determined according to the polymerization material and method, and may be, for example, hydrogen or alkyl of 1 to 30 carbon atoms. The composition for interfacial polymerization of polyamide may include only one of an amine compound and an acyl halide compound, and may include both an amine compound and an acyl halide compound. The amine compound and the acyl halide compound may be those known to be usable for interfacial polymerization of polyamide.
The amine compound is not limited as long as it can be used in the polymerization of polyamide. Specific examples thereof include m-phenylenediamine (mPD), p-phenylenediamine (PPD), 1,3,6-benzenetriamine ), 4-chloro-1,3-phenylenediamine, 6-chloro-1,3-phenylenediamine, 3-chloro-1,4-phenylenediamine or a mixture thereof can be preferably used. The content of the amine compound may be 0.1 wt% or more and 20 wt% or less based on 100 wt% of the composition.
The acyl halide compound is not limited as long as it can be used in the polymerization of polyamides. Specific examples of the acyl halide compound include aromatic compounds having 2 to 3 carboxylic acid halides such as trimethoyl chloride, isophthaloyl chloride and terephthaloyl And a mixture of two or more selected from the group consisting of chlorides. The content of the acyl halide compound may be 0.05 wt% or more and 1 wt% or less based on 100 wt% of the composition.
Another embodiment of the present disclosure relates to a method of preparing a reverse osmosis membrane, comprising: preparing a porous support; And forming a polyamide active layer on the porous support using the composition for interfacial polymerization of polyamide described above.
According to one example, the composition for polyamide interfacial polymerization includes an amine compound and the compound of Formula 1, and the polyamide active layer is formed by interfacial polymerization by contacting the polyamide interfacial polymerization composition with an acyl halide compound . For example, after forming a composition layer containing an amine compound and the compound of Formula 1 on the porous support, an acyl halide compound may be brought into contact with the composition layer to interfacially polymerize the polyamide, Can be formed. The acyl halide compound may be contacted on the composition layer in a state contained in an organic solvent.
According to another example, the composition for interfacial polymerization of polyamide includes an acyl halide compound and a compound of formula (1), and the interfacial polymerization is carried out by contacting the composition for interfacial polymerization of polyamide with an amine compound to form a polyamide active layer . For example, after an amine compound layer is formed on a porous support, a polyamide may be interfacially polymerized by contacting the amine compound layer with an acyl halide compound and a composition containing the compound of Formula 1 to form a polyamide active layer . The amine compound layer may be formed by an aqueous solution containing an amine compound.
In the above production process, when an amine compound and an acyl halide compound are brought into contact with each other, an amine compound and an acyl halide compound react with each other to form a polyamide by interfacial polymerization, and a thin film is formed on the microporous support. The contact may be made by an immersion, spraying or coating method. As the interfacial polymerization conditions, those known in the art can be used.
The method of forming the composition layer containing the amine compound layer or the amine compound and the compound of the formula (1) on the porous support is not particularly limited. For example, spraying, coating, immersion, dropping, etc. may be used.
The preparation method may further include a step of removing an aqueous solution containing an excess amine compound as needed before the amine compound and the acyl halide compound are contacted. If the aqueous solution containing the amine compound formed on the porous support is too large, the composition in the aqueous solution may be uneven. If the composition in the aqueous solution is nonuniform, the non-uniform active layer may be formed by subsequent interfacial polymerization. Therefore, it is preferable to remove the excess aqueous solution after forming the amine aqueous solution layer on the porous support. The removal of the excess aqueous solution is not particularly limited, but can be performed using, for example, a sponge, an air knife, nitrogen gas blowing, natural drying, or a compression roll.
According to one embodiment of the present invention, the porous support may be formed with a coating layer of a polymer material on a nonwoven fabric. Examples of the polymeric material include polymeric materials such as polysulfone, polyethersulfone, polycarbonate, polyethylene oxide, polyimide, polyetherimide, polyetheretherketone, polypropylene, polymethylpentene, polymethyl chloride and polyvinylidene fluoride Rides, and the like may be used, but the present invention is not limited thereto. Specifically, polysulfone may be used as the polymer material.
According to one embodiment of the present disclosure, the thickness of the porous support may be 60 [mu] m to 100 [mu] m, but is not limited thereto and may be adjusted as necessary. The pore size of the porous support is preferably 1 nm to 500 nm, but is not limited thereto.
Another embodiment of the present disclosure relates to a porous support; And a polyamide active layer provided on the porous support, wherein the polyamide active layer provides a reverse osmosis membrane comprising a compound of the formula (1) or a compound of the formula (2)
(2)
In Formula 2,
m, n, p, q and X 1 to X 14 are as defined in formula (1)
Y 'is selected from the following formulas,
* Is a moiety bonded to Formula 2,
M is the same or different and is each independently hydrogen or monovalent cation.
The compound of formula (2) is a structure in which M and / or M 'are separated after the compound of formula (1) is incorporated into the polyamide active layer or the polyamide active layer. The compound of formula (1) or (2) may be dispersed in the reverse osmosis membrane, may be directly bonded to the material constituting the reverse osmosis membrane, or may be added to the material constituting the reverse osmosis membrane, Enhancers, and the like. Wherein the bond may be an ionic bond or a coordinative bond.
The compound of Formula 1 or 2 may be contained in an amount of 0.00001 wt% to 1 wt% based on the entire polyamide active layer of the reverse osmosis membrane.
The reverse osmosis membrane may further include an additional layer as required. For example, the reverse osmosis membrane may further include an anti-fouling layer provided on the polyamide active layer.
The water treatment separation membrane may be used as a microfiltration membrane, an ultrafiltration membrane, a nano filtration membrane or a reverse osmosis membrane, and may be specifically used as a reverse osmosis membrane.
One embodiment of the present invention provides a water treatment module including at least one of the above-mentioned water treatment separation membranes.
The specific type of the water treatment module is not particularly limited, and examples thereof include a plate & frame module, a tubular module, a hollow & fiber module, or a spiral wound module. In addition, as long as the water treatment module includes the water treatment separation membrane according to one embodiment of the present invention, other structures and manufacturing methods are not particularly limited and general means known in the art can be employed without limitation have.
On the other hand, the water treatment module according to one embodiment of the present invention has excellent salt removal rate and permeation flow rate, and is excellent in chemical stability, and thus can be used for water treatment devices such as household / industrial water purification devices, sewage treatment devices, have.
Hereinafter, the present invention will be described in detail by way of examples to illustrate the present invention. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the above-described embodiments. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.
Comparative Example One
0.1 wt% of mPD, 0.1 wt% of polyoxyethylene oleyl ether (Brij 98) represented by the following structural formula, 0.1 wt% of an N-containing compound as a salt removal rate improver, 0.07 wt% of a metal chelate compound as a permeation flow- An aqueous solution was applied to the polysulfone layer on the nonwoven fabric by a slot coating method. At this time, the aqueous solution became turbid white or yellow (Fig. 1 (a)). The excess aqueous solution film formed during coating was removed with an air knife, and then a solution composed of 95.81 wt% of Isopar G, 4 wt% of mesitylene and 0.19 wt% of TMC was applied. The resulting membrane was dried at 95 ° C. until all of the liquid components evaporated, and then washed under DIW bath. The obtained membranes were evaluated under a pressure of 800 psi in an aqueous solution containing 32,000 ppm NaCl and 5 ppm boron. The measured NaCl removal rate was 98.9%, flux 15 GFD, and the boron removal rate was 75%.
Example One
A film was prepared in the same manner as in Comparative Example 1, except that Oleth-10 carboxylic acid (OCA) represented by the following formula was used in place of polyoxyethylene oleyl ether (Brij98). The aqueous solution used in Example 1 was transparent without turbidity (Fig. 1 (b)). The film obtained in Example 1 was measured in the same manner as in Comparative Example 1, and found that the NaCl removal rate was 99.9%, the flux 23 GFD, and the boron removal rate was 90%.
Example 2
The procedure of Example 1 was repeated except that the amount of Oleth-10 carboxylic acid (OCA) was 0.05 wt%. Weak turbidity was found in the aqueous solution used in Example 2. The film obtained in Example 2 was measured in the same manner as in Comparative Example 1, and found that the NaCl removal rate was 99.7%, the flux 20 GFD, and the boron removal rate was 86%.
Example 3
The procedure of Example 1 was repeated except that the amount of Oleth-10 carboxylic acid (OCA) was used in an amount of 0.2 wt%. The aqueous solution used in Example 3 was transparent. The film obtained in Example 3 was measured in the same manner as in Comparative Example 1, showing that the NaCl removal rate was 99.4%, the flux 28 GFD, and the boron removal rate was 81%.
Example 4
The procedure of Example 1 was repeated except that LCA360 (= 2.2) shown in the following Table 1 was used as Laureth carboxylic acid (LCA) instead of Oleth-10 carboxylic acid (OCA). The aqueous solution used in Example 4 was transparent. The film obtained in Example 4 was measured in the same manner as in Comparative Example 1, and found that the NaCl removal rate was 99.8%, the flux 30 GFD, and the boron removal rate was 88%.
Example 5
The procedure of Example 1 was repeated except that LCA460 (= 4.5) shown in the following Table 1 was used as Laureth carboxylic acid (LCA) instead of Oleth-10 carboxylic acid (OCA). The aqueous solution used in Example 5 was transparent. The film obtained in Example 5 was measured in the same manner as in Comparative Example 1, and found that the NaCl removal rate was 99.8%, the flux 28 GFD, and the boron removal rate was 89%.
Example 6
The procedure of Example 1 was repeated except that LCA690 (= 9.4) described in the following Table 1 was used as Laureth carboxylic acid (LCA) instead of Oleth-10 carboxylic acid (OCA). The aqueous solution used in Example 6 was transparent. The film obtained in Example 6 was measured in the same manner as in Comparative Example 1, and found that the NaCl removal rate was 99.8%, the flux 24 GFD, and the boron removal rate was 88%.
The detected m
LCA structure:
Example 7
The procedure of Example 1 was repeated except that sodium lauryl sulfate (SLS) having the following structure was used instead of Oleth-10 carboxylic acid (OCA). The aqueous solution used in Example 7 was transparent. The film obtained in Example 7 was measured in the same manner as in Comparative Example 1. As a result, the NaCl removal rate was 99.7%, the flux 25 GFD, and the boron removal rate was 85%.
Content (wt%)
(%)
(GFD)
(%)
Example 8
Example 1 was carried out in the same manner as in Example 1, except that Oleth-10 carboxylic acid (OCA) was replaced with KONEMUL COP-140, a product of Hana Chemical Co., Ltd., in which Y in Chemical Formula 1 is phosphorus-containing compound. The aqueous solution used in Example 8 was transparent. The film obtained in Example 8 was measured in the same manner as in Comparative Example 1, and found that the NaCl removal rate was 99.5%, the flux 24 GFD, and the boron removal rate was 81%.
Example 9
Example 1 was carried out in the same manner as in Example 1, except that KOHEMUL TP-170 shown in Table 3 was used in place of Oleth-10 carboxylic acid (OCA) in which Y of formula (1) is a compound containing phosphorus (P). The aqueous solution used in Example 9 was transparent. The film obtained in Example 9 was measured in the same manner as in Comparative Example 1, and found that the NaCl removal rate was 99.3%, the flux 27 GFD, and the boron removal rate was 79%.
Example 10
The procedure of Example 1 was repeated with the exception that Oleth-10 carboxylic acid (OCA) was replaced with KOREMUL SEP-250, a concentrate of the following Table 3, in which Y of formula (1) was a compound containing phosphorus (P). The aqueous solution used in Example 10 was transparent. The film obtained in Example 10 was measured in the same manner as in Comparative Example 1, and found that the NaCl removal rate was 99.4%, the flux 25 GFD, and the boron removal rate was 81%.
Example 11
Example 3 was carried out in the same manner as in Example 1, except that Oleth-10 carboxylic acid (OCA) was replaced by KONEMUL LE-3P, a concentrating agent of the following Table 3, which is a compound containing Y (P) The aqueous solution used in Example 11 was transparent. The film obtained in Example 11 was measured in the same manner as in Comparative Example 1, and found that the NaCl removal rate was 99.4%, the flux 23 GFD, and the boron removal rate was 82%.
(n + 2o + p)
(m)
Content (wt%)
(%)
(GFD)
(%)
(KOREMUL COP-140)
(KOREMUL TP-170)
(KOREMUL SEP-250)
(KOREMUL LE-3P)
Claims (16)
A compound of the formula
: ≪ / RTI >
[Chemical Formula 1]
In Formula 1,
m, n and p are each an integer of 1 to 50, o is an integer of 0 to 5, q is an integer of 0 to 2,
X 1 to X 14 are the same or different from each other and are each independently hydrogen or a halogen atom,
Y is selected from the following formulas,
* Is a moiety bonded to Formula 1,
M and M 'are the same or different and each independently hydrogen or monovalent cation.
A process for producing a reverse osmosis membrane, comprising the step of forming a polyamide active layer on the porous support using the composition for interfacial polymerization of polyamide according to any one of claims 1 to 7.
And a polyamide active layer provided on the porous support,
Wherein the polyamide active layer comprises a compound represented by the following formula (1) or (2): < EMI ID =
[Chemical Formula 1]
(2)
In the above formulas (1) and (2)
m, n and p are each an integer of 1 to 50, o is an integer of 0 to 5, q is an integer of 0 to 2,
X 1 to X 14 are the same or different from each other and are each independently hydrogen or a halogen atom,
Y is selected from the following formulas,
Y 'is selected from the following formulas,
* Is a moiety bonded to Formula 1 or 2,
M and M 'are the same or different and each independently hydrogen or monovalent cation.
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| KR20190065655A (en) * | 2017-12-04 | 2019-06-12 | 주식회사 엘지화학 | Method for manufacturing water-treatment membrane and water-treatment membrane manufactured by thereby |
| KR20190130416A (en) * | 2018-05-14 | 2019-11-22 | 한국에너지기술연구원 | Defect-free membrane formed on mesh support layer, method for manufacturing the same and subtle energy harvesting device using the same |
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| KR20190065655A (en) * | 2017-12-04 | 2019-06-12 | 주식회사 엘지화학 | Method for manufacturing water-treatment membrane and water-treatment membrane manufactured by thereby |
| KR20190130416A (en) * | 2018-05-14 | 2019-11-22 | 한국에너지기술연구원 | Defect-free membrane formed on mesh support layer, method for manufacturing the same and subtle energy harvesting device using the same |
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