Composition for gas permeable membranes, cured product for gas permeable membranes, and gas permeable membrane

Abstract

To provide: a composition for gas permeable membranes that is capable of forming a gas permeable membrane excellent in both of the CO2 gas permeability coefficient and the separation factor (CO2 / N2); a cured product for gas permeable membranes; and a gas permeable membrane.SOLUTION: A composition for gas permeable membranes comprises: a compound (A), which has a structure represented by the formula (1) defined by -(CH2-CH2-O)n- (where n is an integer equal to or greater than 2) and has three or more (meth)acryloyl groups as terminal groups; and a compound (B) represented by the formula (2) in the figure (where m is an integer equal to or greater than 1).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a composition for a gas-permeable membrane, a cured product for a gas-permeable membrane, and a gas-permeable membrane. [Background technology]

[0002] CO 2 As a technology that aims to reduce CO emissions into the atmosphere to zero, 2 A method known as CCUS (Carbon dioxide Capture, Utilization and Storage) is known, in which carbon dioxide is separated, captured, and stored underground or converted into chemical products or fuel for use.

[0003] CO 2 There are many technologies to capture CO 2 The problem is that the cost can be high depending on the concentration. 2 The recovery is driven by pressure difference and requires small equipment size, making it a technology that can be operated at low cost. Membrane CO 2 In the capture, the CO 2 Gas permeability coefficient and separation factor (CO 2 / N 2 ) are in a trade-off relationship. 2 There are only a limited number of materials that can be used for the gas permeable membrane to selectively recover CO 2 It has excellent affinity for CO 2 / N 2 Polyethylene oxide (PEO) is known as a material with high molecular weight. However, PEO crystallizes and is easily degraded by CO 2 This method cannot be applied to gas-permeable membranes because the gas permeability coefficient becomes significantly low.

[0004] CO by crystallization 2Materials capable of suppressing the decrease in gas permeability coefficient include cured products using ethylene oxide (EO)-modified bifunctional acrylate monomers. Non-Patent Document 1 discloses a cured product using a bifunctional acrylate monomer with an EO modification number (EO addition mole number) of 14, and a membrane composed of the cured product. Non-Patent Document 2 discloses a cured product using a bifunctional acrylate monomer with an EO modification number (EO addition mole number) of 15, and a membrane composed of the cured product. However, the membranes described in Non-Patent Documents 1 and 2 are 2 Although the gas permeability coefficient is sufficiently high, the separation factor (CO 2 / N 2 ) is low. [Prior art documents] [Non-patent literature]

[0005] [Non-Patent Document 1] Kusuma et al., Journal of Membrane Science, 327, 2009, 195-207. [Non-Patent Document 2] Ricards et al., Chemical Engineering Science, 64, 2009, 4707-4718. Summary of the Invention [Problem to be solved by the invention]

[0006] The present invention provides an excellent 2 Gas permeability coefficient and separation factor (CO 2 / N 2 The present invention aims to provide a composition for a gas-permeable film, a cured product for a gas-permeable film, and a gas-permeable film, which can provide a gas-permeable film that satisfies both of the above requirements. [Means for solving the problem]

[0007] The present invention includes the following configurations. [1] A compound (A) having a structure represented by the following formula (1) and having three or more (meth)acryloyl groups as terminal groups, A composition for a gas-permeable film, comprising: a compound (B) represented by the following formula (2): -(CH 2 -CH 2 -O) n - (1) (In the above formula (1), n ​​is an integer of 2 or more.)

[0008] [ka]

[0009] (In the above formula (2), m is an integer of 1 or more.) [2] The composition for a gas-permeable film according to [1], wherein the compound (A) has a group represented by the following formula (3):

[0010] [ka]

[0011] (However, R in the above formula (3) 1 is a hydrogen atom or a methyl group. n is an integer of 2 or more. -* represents a bond. [3] The composition for a gas-permeable membrane according to [1] or [2], wherein the content of the compound (B) is 10% by mass or more and 90% by mass or less based on the total mass of the compound (A) and the compound (B). [4] A cured product for a gas-permeable membrane obtained by curing the composition for a gas-permeable membrane according to any one of [1] to [3]. [5] A gas-permeable membrane comprising the cured material for gas-permeable membrane according to [4]. [6] CO 2 The gas permeability coefficient is 50 Barrer or more, and the separation factor (CO 2 / N 2 ) is 60 or more. Effect of the Invention

[0012] According to the present invention, excellent CO 2 Gas permeability coefficient and separation factor (CO 2 / N 2 The present invention provides a gas-permeable membrane composition which can provide a gas-permeable membrane that satisfies both of the above requirements, a cured product for the gas-permeable membrane, and the gas-permeable membrane. [Brief description of the drawings]

[0013] [Figure 1] FIG. 1 is a double logarithmic graph plotting the separation factor (CO2 / N2) versus the CO2 gas permeability coefficient for the gas permeable membranes prepared in the examples and comparative examples. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] [Gas-permeable membrane composition] The composition for a gas-permeable film according to the embodiment is a curable composition used for a gas-permeable film, and contains a compound (A) and a compound (B) described below.

[0015] (Compound (A)) Compound (A) is a compound having a structure represented by the following formula (1) (hereinafter also referred to as "structure (1)") and having three or more (meth)acryloyl groups as terminal groups. That is, compound (A) is a polyfunctional (meth)acrylic monomer having an EO modification number (EO addition mole number) of 2 or more and a functionality of 3 or more. -(CH 2 -CH 2 -O) n - (1) In the above formula (1), n ​​is an integer of 2 or more.

[0016] The n in formula (1), i.e., the EO modification number (the number of moles of EO added), is 2 or more, preferably 5 or more, and more preferably 8 or more. When n is equal to or more than the lower limit, the separation factor (CO 2 / N 2 ) is likely to be obtained. n is preferably 20 or less, and more preferably 15 or less. The preferable lower limit and upper limit of n can be arbitrarily combined, and for example, 2 to 20 are preferable. Furthermore, when compound (A) contains a plurality of structures (1), the upper limit of the total number of n is preferably not more than 100, more preferably not more than 90, further preferably not more than 80, and particularly preferably not more than 65. When the total number of n is not more than the upper limit, the crosslink density falls within an appropriate value, and the film is easily self-supporting.

[0017] The number of (meth)acryloyl groups that the compound (A) has as terminal groups is 3 or more, preferably 4 or more, more preferably 5 or more, and even more preferably 6 or more. When the number of (meth)acryloyl groups is equal to or more than the lower limit, the crosslink density increases and the strength of the gas permeable membrane increases. In addition, the separation factor (CO 2 / N 2 ) is easily obtained. The number of (meth)acryloyl groups that the compound (A) has as an end group is preferably 10 or less, more preferably 9 or less, even more preferably 8 or less, and particularly preferably 6 or less. When the number of (meth)acryloyl groups is equal to or less than the upper limit, the crosslinking density becomes appropriate and the film can be easily molded. The preferable lower limit and upper limit of the number of (meth)acryloyl groups can be arbitrarily combined, and for example, 3 to 6 are preferable.

[0018] CO 2 Gas permeability coefficient and separation factor (CO 2 / N 2 As compound (A), a compound having a group represented by the following formula (3) (hereinafter also referred to as "group (3)") is preferred, since such a compound easily gives a gas-permeable membrane having a high molecular weight.

[0019] [ka]

[0020] However, R in the above formula (3) 1 is a hydrogen atom or a methyl group. -* indicates a bond.

[0021] The group (3) is a group containing a (meth)acryloyl group as a terminal group and the structure (1). 2 Gas permeability coefficient and separation factor (CO 2 / N2 It is preferred that the compound (A) has all of its terminal (meth)acryloyl groups as part of the group (3), since this makes it easier to obtain a gas-permeable membrane with high molecular weight.

[0022] The number of groups (3) in the compound (A) is preferably 3 or more, more preferably 4 or more, even more preferably 5 or more, and particularly preferably 6 or more. When the number of groups (3) is equal to or more than the lower limit, the separation factor (CO 2 / N 2 ) is easily obtained. The number of groups (3) in the compound (A) is preferably 10 or less, more preferably 9 or less, even more preferably 8 or less, and particularly preferably 6 or less. When the number of groups (3) is equal to or less than the upper limit, the crosslinking density becomes appropriate and the film can be easily molded. The preferable lower limit and upper limit of the number of groups (3) can be arbitrarily combined, and for example, 3 to 6 are preferable. It is to be noted that the number of (meth)acryloyl groups, which are the terminal groups of the compound (A), and the number of EO modifications (the number of moles of EO added) should be considered together rather than being selected independently. The above-mentioned preferred lower and upper limits of the number of (meth)acryloyl groups and the number of EO modifications (the number of moles of EO added) can be arbitrarily combined. For example, it is preferable that the number of (meth)acryloyl groups is 3 or more and the number of EO modifications (the number of moles of EO added) is 2 or more, more preferably that the number of (meth)acryloyl groups is 4 or more and the number of EO modifications (the number of moles of EO added) is 5 or more, and even more preferably that the number of (meth)acryloyl groups is 5 or more and the number of EO modifications (the number of moles of EO added) is 8 or more.

[0023] The compound (A) is preferably a compound in which three or more hydrogen atoms of a hydrocarbon which may have an etheric oxygen atom are substituted with a group (3). The hydrocarbon which may have an etheric oxygen atom may be linear, branched, or cyclic. The number of carbon atoms in the hydrocarbon which may have an etheric oxygen atom is preferably 1 or more, more preferably 2 or more, and even more preferably 3 or more, and is preferably 15 or less, more preferably 14 or less, and even more preferably 12 or less.

[0024] Examples of the compound (A) include glycerin polyethoxy tri(meth)acrylate, dipentaerythritol polyethoxy hexa(meth)acrylate, a compound represented by the following formula (4), and a compound represented by the following formula (5). The composition for a gas-permeable film according to the embodiment preferably contains, as compound (A), either or both of a compound represented by formula (4) and a compound represented by formula (5).More preferably, as compound (A), either or both of a compound represented by formula (4) and a compound represented by formula (5).

[0025] [ka]

[0026] In the formula (4), n1 to n3 each independently represents an integer of 2 or more. The preferred range for each of n1 to n3 is the same as the preferred range for n. The preferred upper limit for the total number of n1 to n3 is the same as the preferred upper limit for the total number of n.

[0027] [ka]

[0028] In the formula (5), n4 to n9 each independently represents an integer of 2 or more. The preferred range for each of n4 to n9 is the same as the preferred range for n. The preferred upper limit for the total number of n4 to n9 is the same as the preferred upper limit for the total number of n.

[0029] The method for producing compound (A) is not particularly limited. For example, compound (A) can be produced by reacting a polyhydric alcohol having three or more functional groups with ethylene oxide (EO) to obtain a reaction product, and then reacting the reaction product with (meth)acrylic acid. Examples of the polyhydric alcohol having three or more functional groups include polyglycerols such as triglycerin and tetraglycerin, trimethylolpropane, and sorbitol. As the polyhydric alcohol having three or more functional groups, one type may be used alone, or two or more types may be used in combination.

[0030] (Compound (B)) The compound (B) is a compound represented by the following formula (2). Examples of the compound (B) include 2-methoxyethyl acrylate and methoxypolyethylene glycol acrylate.

[0031] [ka]

[0032] In the above formula (2), m is an integer of 1 or more. In formula (2), m, i.e., the EO modification number (the number of moles of EO added), is preferably 2 or more, more preferably 4 or more, further preferably 6 or more, and particularly preferably 9 or more. 2 Gas permeability coefficient and separation factor (CO 2 / N 2 ) is easily obtained. m is preferably 30 or less, more preferably 20 or less, even more preferably 15 or less, and particularly preferably 13 or less. When m is equal to or less than the upper limit, the melting point is low and the compound (A) can be easily mixed. The preferable lower and upper limits of m can be arbitrarily combined, and for example, 9 to 13 are preferable.

[0033] The content of the compound (B) in the composition for a gas-permeable film according to the embodiment is preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more, based on the total mass of the compound (A) and the compound (B). 2 Gas permeability coefficient and separation factor (CO 2 / N 2The content of the compound (B) is preferably 90% by mass or less, more preferably 85% by mass or less, and even more preferably 80% by mass or less. When the content of the compound (B) is equal to or less than the upper limit, the composition for a gas-permeable film is easily cured. The preferable lower limit and upper limit of the content of the compound (B) can be arbitrarily combined, and for example, 10 to 90 mass % is preferable, 15 to 85 mass % is more preferable, and 20 to 80 mass % is even more preferable.

[0034] (Other Monomers) The composition for a gas-permeable film according to the embodiment may contain, in addition to the compound (A) and the compound (B), another (meth)acrylic monomer other than the compound (A) and the compound (B). Examples of (meth)acrylic monomers other than the compound (A) and the compound (B) include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenyloxypropyl (meth)acrylate, isoamyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, isooctyl (meth)acrylate, lauryl (meth)acrylate, isomyristyl (meth)acrylate, stearyl (meth)acrylate, isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methoxyethyl methacrylate, methoxyethylene glycol methacrylate, methoxydipropylene glycol (meth)acrylate, 2-ethoxyethyl (meth)acrylate, ethoxy-diethylene glycol (meth)acrylate, butoxyethyl (meth)acrylate, 2-ethylhexyl diethoxy (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, isobornyl (meth)acrylate, benzyl (meth)acrylate, carbitol (meth)acrylate, ethyl carbitol (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxy diethylene glycol (meth)acrylate, phenoxy polyethylene glycol (meth)acrylate, hydrogenated dicyclopentadiene (meth)acrylate, acryloylmorpholine, 1,4-butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 3-methyl-1,5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-Nonanediol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, 2-n-butyl-2-ethyl-3-propanediol di(meth)acrylate, tricyclodecane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolmethane tri(meth)acrylate, trimethylolpropane polypropoxy tri(meth)acrylate, tetramethylolmethane tri(meth)acrylate, tetramethylol Examples of the acrylates include arylmethane tetra(meth)acrylate, glycerin polypropoxy tri(meth)acrylate, bisphenol A polyethoxy di(meth)acrylate, bisphenol A polypropoxy di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and dipentaerythritol polypropoxy hexa(meth)acrylate. As the other (meth)acrylic monomer, one type may be used alone, or two or more types may be used in combination.

[0035] The total content of the compound (A) and the compound (B) in the composition for gas-permeable membrane according to the embodiment is preferably 90% by mass or more, more preferably 92.5% by mass or more, even more preferably 95% by mass or more, and particularly preferably 97.5% by mass or more, based on the total amount of the monomer components in the composition for gas-permeable membrane. 2 Gas permeability coefficient and separation factor (CO 2 / N 2 The upper limit of the total content of the compound (A) and the compound (B) is not particularly limited, and may be set to 100 mass %.

[0036] (Photoinitiator) The composition for a gas-permeable film according to the embodiment preferably contains a photoinitiator. The photoinitiator is not particularly limited, and examples thereof include ketones such as 1-hydroxycyclohexyl phenyl ketone (HCPK), benzophenone, etc. As the photoinitiator, one type may be used alone, or two or more types may be used in combination.

[0037] The content of the photoinitiator in the composition for gas permeable film is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, and even more preferably 0.1 parts by mass or more, based on 100 parts by mass of the monomer component. If the content of the photoinitiator is equal to or more than the lower limit, the composition for gas permeable film is easily cured. The content of the photoinitiator is preferably 1 part by mass or less, more preferably 0.5 parts by mass or less, and even more preferably 0.3 parts by mass or less. If the content of the photoinitiator is equal to or less than the upper limit, the gas permeability coefficient is not affected. The preferred lower and upper limits of the content of the photoinitiator can be arbitrarily combined, and for example, 0.1 to 0.3 parts by mass is preferable.

[0038] [Cured material for gas permeable membrane] The cured product for a gas-permeable film according to the embodiment is a cured product obtained by curing the composition for a gas-permeable film according to the embodiment described above.

[0039] The cured product for a gas-permeable film according to the embodiment can be obtained, for example, by curing the above-mentioned composition for a gas-permeable film with active energy rays. Examples of the active energy rays include electron beams, X-rays, ultraviolet rays, and visible light in the low wavelength region, with ultraviolet rays being preferred.

[0040] [Gas permeable membrane] The gas-permeable membrane according to the embodiment includes a cured material for a gas-permeable membrane according to the embodiment. The gas-permeable membrane according to the embodiment may be a membrane consisting of a single non-porous layer formed from the cured material for a gas-permeable membrane according to the embodiment, or may be a membrane including a porous support and a non-porous layer formed on the porous support from the cured material for a gas-permeable membrane according to the embodiment.

[0041] The form of the gas permeable membrane is not particularly limited, and may be a flat membrane or a hollow fiber membrane. For example, when the gas permeable membrane is a flat membrane, it may be a flat membrane of a two-layer structure having a porous support and a non-porous layer, or a flat membrane of a three-layer structure having a porous support on both sides of a non-porous layer. For example, when the gas permeable membrane is a hollow fiber membrane, it may be a two-layer hollow fiber membrane having a non-porous layer on the inside or outside of a hollow porous support, or it may be a three-layer hollow fiber membrane having a porous support on the inside and outside of a hollow non-porous layer.

[0042] The thickness of the non-porous layer is preferably 0.1 μm or more, and more preferably 0.5 μm or more. 2 The thickness of the non-porous layer is preferably 10 μm or less, more preferably 1 μm or less. If the thickness of the non-porous layer is equal to or less than the upper limit, the permeation resistance can be reduced, and therefore, the CO 2 can be efficiently recovered.

[0043] The porous support is not particularly limited as long as it has sufficient mechanical strength to reinforce the non-porous layer and can be integrated with the non-porous layer. Examples of materials constituting the porous support include polyolefin polymers such as polyethylene, polypropylene, poly-3-methylbutene-1, poly-4-methylpentene-1, etc., fluorine-based polymers such as polyvinylidene fluoride, polytetrafluoroethylene, etc., and hydrophobic polymers such as polystyrene, polyether ketone, etc. The materials constituting the porous support may be used alone or in combination of two or more.

[0044] The gas-permeable membrane according to the embodiment is 2 The gas permeability coefficient is 50 Barrer or more, and the separation factor (CO 2 / N 2 ) is preferably 60 or more.

[0045] Gas permeable membrane CO 2The higher the gas permeability coefficient, the better. In general, a gas permeability coefficient of 50 Barrer or more is preferable, a gas permeability coefficient of 70 Barrer or more is more preferable, and a gas permeability coefficient of 100 Barrer or more is even more preferable. 2 The upper limit of the gas permeability coefficient is not particularly limited, and is substantially 500 Barrer or less. In addition, the CO 2 The gas permeability coefficient is a value measured by the method described in the Examples section below.

[0046] Gas permeable membrane separation factor (CO 2 / N 2 The higher the separation factor (CO 2 / N 2 ) There is no particular upper limit, and it is practically 150 or less. The separation factor of the gas permeable membrane (CO 2 / N 2 ) is a value measured by the method described in the Examples below. The preferred lower and upper limits can be combined in any combination. 2 Gas permeability coefficient and separation factor (CO 2 / N 2 For example, the line k in Figure 1 is 2 / N 2 This is a straight line showing the Robson upper limit performance at Therefore, the CO 2 Gas permeability coefficient and separation factor of gas permeable membrane (CO 2 / N 2 ) are not considered independently of each other, and ideally both should be high.

[0047] As described above, in the present invention, by using the compound (A) and the compound (B) in combination, it is possible to obtain a particularly excellent CO 2 Gas permeability coefficient and separation factor (CO 2 / N 2 ) can be obtained.

[0048] The composition for a gas-permeable film, the cured product for a gas-permeable film, and the gas-permeable film of the present invention are not limited to the above-mentioned configurations. Within the scope of the present invention, the components in the above-mentioned embodiment may be appropriately replaced with well-known components, and the above-mentioned modified examples may be appropriately combined. EXAMPLES

[0049] The present invention will be specifically described below with reference to examples, but the present invention is not limited to the following description.

[0050] [Abbreviation] The abbreviations for the raw materials used in this example are as follows. (Compound (A)) A-1: MIRAMER M3150 (manufactured by Miwon, number of acryloyl groups: 3, compound represented by formula (4), n1 = n2 = n3 = 5) A-2: Syntech SA-TE60 (manufactured by Sakamoto Pharmaceutical Co., Ltd., number of acryloyl groups: 6, compound represented by formula (5), n4 = n5 = n6 = n7 = n8 = n9 = 10) (Compound (B)) B-1:CH 2 =CH-C(=O)-(O-CH 2 -CH 2 ) 9 -O-CH 3 (Compound represented by formula (2) above, where m=9) B-2:CH 2 =CH-C(=O)-(O-CH 2 -CH 2 ) 13 -O-CH 3 (Compound represented by formula (2) above, where m=13) (Photoinitiator) HCPK: 1-hydroxycyclohexyl phenyl ketone

[0051] [Measurement of gas permeability coefficient P (Barrer) and separation factor] (1) Preparation of gas-permeable membrane The composition for gas permeable membrane was applied onto a polyester film (hereinafter referred to as "PET film") (Cosmo Sunshine, manufactured by Toyobo Co., Ltd., thickness: 188 μm) with a spacer attached, and a PET film was further placed on top of it, and the film was spread so that the thickness of the film after curing between the two films would be about 200 μm. Next, a high-pressure mercury lamp (commercially available) was used to irradiate the film with ultraviolet light of 340 to 380 nm in wavelength in the air at an integrated light intensity of 500 mJ / cm. 2 The composition for a gas-permeable film was cured to form a gas-permeable film.

[0052] (2)Measurement method The resulting laminate including the gas-permeable membrane was cut into a circular shape with a diameter of 35 mm, and the PET film was peeled off to collect a measurement sample consisting of the gas-permeable membrane. Using a gas permeability measuring device (K-315N-01, manufactured by Tsukubarika Seiki Co., Ltd.), the obtained measurement samples were measured by the pressure method using nitrogen and carbon dioxide as the supply gases under the conditions of a temperature of 25.5°C and a measurement pressure of 102 kPa. 2 Gas permeability coefficient and N 2 The gas permeability coefficients of each were measured. The gas permeability coefficient P (Barrer) was calculated from the following formula (6). 2 Gas permeability coefficient N 2 Divide by the gas permeability coefficient to obtain the separation factor (CO 2 / N 2 ) was sought.

[0053]

number

[0054] The symbols in the formula (6) have the following meanings. V: Low pressure tank volume (cm 3 ) A: Permeable area (cm) of the measurement sample (gas permeable membrane) 2 ) T: Temperature in the cell (K) l: Thickness of the measurement sample (gas permeable membrane) (cm) P H : High pressure tank pressure (cmHg) P L : Low pressure tank pressure (cmHg)

[0055] [Example 1] A liquid composition for a gas-permeable membrane was prepared by mixing 80 parts by mass of compound (A-2) as compound (A), 20 parts by mass of compound (B-1) as compound (B), and 0.1 parts by mass of HCPK as a photoinitiator. A gas-permeable membrane is prepared using the composition for a gas-permeable membrane, and a CO 2 Gas permeability coefficient and separation factor (CO 2 / N 2 ) was measured.

[0056] [Examples 2 to 6] A composition for a gas-permeable membrane was prepared in the same manner as in Example 1, except that the monomer composition was changed as shown in Table 1. 2 Gas permeability coefficient and separation factor (CO 2 / N 2 ) was measured.

[0057] [Example 7] A composition for a gas-permeable membrane was prepared in the same manner as in Example 1, except that the compound (A-1) was used instead of the compound (A-2). 2 Gas permeability coefficient and separation factor (CO 2 / N 2 ) was measured.

[0058] [Example 8] A composition for a gas-permeable membrane was prepared in the same manner as in Example 7, except that the monomer composition was changed as shown in Table 1. 2 Gas permeability coefficient and separation factor (CO 2 / N 2 ) was measured.

[0059] [Comparative Example 1] A composition for a gas-permeable membrane was prepared in the same manner as in Example 1, except that 100 parts by mass of compound (A-2) was used instead of compound (B-1). 2 Gas permeability coefficient and separation factor (CO 2 / N 2 ) was measured.

[0060] [Comparative Example 2] A composition for a gas-permeable membrane was prepared in the same manner as in Example 7, except that 100 parts by mass of the compound (A-1) was used instead of the compound (B-1). 2 Gas permeability coefficient and separation factor (CO 2 / N 2 ) was measured.

[0061] CO of each gas permeable membrane 2 Gas permeability coefficient and separation factor (CO 2 / N 2 The results of the measurements are shown in Table 1. In Table 1, "EO modification number" means the total number of EO modifications in the compound. 2 Separation factor for gas permeability coefficient (CO 2 / N 2 ) is plotted on a double logarithmic graph in Figure 1. The line k in Figure 1 represents the 2 / N 2 This is a straight line showing the Robson upper limit performance at

[0062] [Table 1]

[0063] As shown in Table 1, Examples 1 to 6 in which the compound (A-2) was used in combination with the compound (B) had a higher CO 2 Gas permeability coefficient and separation factor (CO 2 / N 2 Similarly, in Examples 7 and 8 in which the compound (A-1) was used in combination with the compound (B), a higher CO 2Gas permeability coefficient and separation factor (CO 2 / N 2 ) was achieved. In addition, as shown in FIG. 1, by using compound (A) and compound (B) in combination, a gas permeable membrane with performance exceeding the line k indicating Robson's upper limit performance was obtained.

Claims

1. A compound (A) having a structure represented by the following formula (1) and having three or more (meth)acryloyl groups as terminal groups, A composition for a gas-permeable membrane comprising a compound (B) represented by the following formula (2): -(CH ２ -CH ２ -O) ｎ - ・・・(1) (In the above formula (1), n ​​is an integer of 2 or more.) 【Chemistry 1】 (In the above formula (2), m is an integer of 1 or more.)

2. The gas-permeable film composition according to claim 1 , wherein the compound (A) has a group represented by the following formula (3): 【Chemistry 2】 (However, R in the above formula (3) １ is a hydrogen atom or a methyl group. n is an integer of 2 or more. -* indicates a bond.

3. 2. The composition for a gas-permeable film according to claim 1, wherein the content of said compound (B) is 10% by mass or more and 90% by mass or less based on the total mass of said compound (A) and said compound (B).

4. A gas-permeable film cured product obtained by curing the gas-permeable film composition according to any one of claims 1 to 3.

5. A gas-permeable membrane comprising the cured product for gas-permeable membrane according to claim 4.

6. CO ２ The gas permeability coefficient is 50 Barrer or more, and the separation coefficient (CO ２ / N ２ 6. The gas-permeable membrane according to claim 5, wherein the molecular weight distribution (Mg) is 60 or more.

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