CN102643544A - Fluorine-containing polyimide infrared low-emissivity thin film material and preparation method thereof - Google Patents
Fluorine-containing polyimide infrared low-emissivity thin film material and preparation method thereof Download PDFInfo
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- CN102643544A CN102643544A CN2012100603052A CN201210060305A CN102643544A CN 102643544 A CN102643544 A CN 102643544A CN 2012100603052 A CN2012100603052 A CN 2012100603052A CN 201210060305 A CN201210060305 A CN 201210060305A CN 102643544 A CN102643544 A CN 102643544A
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- 0 CC(*)(*)c(cc1)ccc1-c(cc1)ccc1N(C(c(c1c2)ccc2C(Oc(ccc2c3cccc2)c3-c(c(cccc2)c2cc2)c2OC(c(cc2C(N3C(C)(*)*)=O)ccc2C3=O)=O)=O)=O)C1=O Chemical compound CC(*)(*)c(cc1)ccc1-c(cc1)ccc1N(C(c(c1c2)ccc2C(Oc(ccc2c3cccc2)c3-c(c(cccc2)c2cc2)c2OC(c(cc2C(N3C(C)(*)*)=O)ccc2C3=O)=O)=O)=O)C1=O 0.000 description 1
- BEKFRNOZJSYWKZ-UHFFFAOYSA-N Nc1ccc(C(C(F)(F)F)(C(F)(F)F)c(cc2)ccc2N)cc1 Chemical compound Nc1ccc(C(C(F)(F)F)(C(F)(F)F)c(cc2)ccc2N)cc1 BEKFRNOZJSYWKZ-UHFFFAOYSA-N 0.000 description 1
- SGRLLEGISGXGEQ-UHFFFAOYSA-N O=C(c(cc1C(O2)=O)ccc1C2=O)Oc1ccc(cccc2)c2c1-c1c(cccc2)c2ccc1OC(c(cc1C(O2)=O)ccc1C2=O)=O Chemical compound O=C(c(cc1C(O2)=O)ccc1C2=O)Oc1ccc(cccc2)c2c1-c1c(cccc2)c2ccc1OC(c(cc1C(O2)=O)ccc1C2=O)=O SGRLLEGISGXGEQ-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention discloses a fluorine-containing polyimide infrared low-emissivity thin film material and a preparation method thereof. The thin film material is prepared through polymerization by using diamine and dianhydride which is synthesized by R-shaped or S-shaped 1, 1'-binaphthyl-2, 2'-diphenol monomers. A binaphthyl group is introduced into fluorine-containing polyimide formed in a polyimide chain. The thermal stability is good, the chain structure is adjustable, the crystallization performance is good, the solvent resistance is good and the average infrared emissivity at an 8-14mum band is 0.30-0.70. Therefore, the fluorine-containing polyimide infrared low-emissivity thin film material can be used as a high-performance novel infrared stealth material and the application prospect in the technical field of military use and civil use is better.
Description
Technical field
The invention belongs to the macromolecule membrane technical field, be specifically related to a kind of fluorinated polyimide infrared low-emissivity thin-film material and preparation method thereof, can be used as the infrared stealth material and be applied to military or civil area.
Background technology
Stealth material is the key of stealthy technique, is the indispensable basic substance of stealthy weapon, and primary study and exploitation are all given by each developed country of the world.Wherein, infrared stealth require to reduce the target infrared yield of radiation, generally all is through cooling, infraredly blocks, uses the low infrared emissivity coating to realize.The material that is used for infrared stealth generally should have low infrared emittance or stronger temperature control ability, has rational surface tissue and lower solar absorptance, can be compatible with other wave band.The many new infrared stealth materials of research mainly contain conductive polymers, inorganic nano film, ultramicron, strong magnetic material, semiconductor material etc. at present.Because the temperature difference between target and the background is difficult to be reduced to the limit of requirement, so the infrared emittance of regulating stealthy target surface is an effective means.The core that reduces infrared emittance be exactly search out have excellent processing characteristics, the low infrared emissivity material of Adjustable structure.
Publication number is that the one Chinese patent application of CN101863152A discloses a kind of nano periodic structure infrared low-emissivity thin-film material, and this kind thin-film material is composited by the composite Nano germanium and the zinc sulfide film in five cycles each other.Publication number is silit infrared stealth material and the preparation technology thereof that the one Chinese patent application of CN1657585A discloses a kind of coated with barium ferrite film.Publication number is that the one Chinese patent application of CN1552660A discloses a kind of indium tin oxide films and preparation method who has low-launch-rate at infrared band.What the low infrared emissivity material that these patented claims relate to used all is inorganics, seldom relates to and utilizes the organic polymer thin film material to prepare infrared low-emissivity material.
Organic polymer thin film is widely used because having advantage such as Adjustable structure, variation, in light weight, density is low, physical and chemical performance uniqueness, and wherein fluoro-containing copolymer film is the novel high polymer mould material that development in recent years is got up.See from structure, fluorine element is introduced in the polymkeric substance, can effectively improve its optical transparence and solubility, reduce specific inductivity, and do not sacrifice its good thermal property.
Summary of the invention
Technical purpose of the present invention is the state of the art to existing infrared low-emissivity material, and a kind of fluorinated polyimide infrared low-emissivity thin-film material and preparation method thereof is provided.This thin-film material has good thermostability, adjustable chain structure, good crystal property and good solvent resistance, can have the material of low-launch-rate as infrared band, is used for the technical fields such as polymeric substrates of infrared stealth material.
The present invention realizes that the technical scheme that above-mentioned technical purpose adopts is: a kind of fluorinated polyimide infrared low-emissivity thin-film material, and its general structure is:
Wherein, polymerization degree n is 1～1000; R
1And/or R
2In comprise fluorine atom, and R
1Be selected from a kind of in the following structure:
R
2Be selected from a kind of in the following structure:
In the technique scheme:
As preferably, described fluorinated polyimide infrared low-emissivity thin-film material is 0.30～0.70 in the average infrared emittance of 8～14 mu m wavebands, further is preferably 0.40～0.60.
As preferably, the glass transition temp of described fluorinated polyimide infrared low-emissivity thin-film material further is preferably 220～240 ℃ greater than 200 ℃.
As preferably, the heat decomposition temperature of described fluorinated polyimide infrared low-emissivity thin-film material further is preferably 270～300 ℃ greater than 250 ℃.
The preparation method of a kind of fluorinated polyimide infrared low-emissivity of the present invention thin-film material is: the fluorinated polyimide film adopts three-step approach to synthesize,
Step 1: adopt following route A or route B to synthesize and contain 1,1 '-dinaphthalene-2, the monomeric dianhydride monomer of 2 '-diphenol;
Route A:
(1) at N
2Protection down; Will an amount of (R)-or (S)-and after binaphthol, 4-nitro phthalic nitrile and salt of wormwood mix, add the anhydrous DMF of capacity, stirred under the room temperature 15～30 hours; The mixture that obtains is poured suction filtration in the Hydrogen chloride of capacity into; Extremely neutral with the deionized water washing then, the mixed solvent recrystallization with methyl alcohol and acetonitrile obtains intermediate compound one;
(2) get an amount of intermediate compound one, sodium hydroxide, H
2O
2After mixing with water, 40～80 ℃ were stirred 10～30 hours down, refluxed afterwards 30～60 hours, obtained white solid, suction filtration, used the concentrated hydrochloric acid acidifying with deionized water dilution back, obtained intermediate compound two;
(3) get an amount of intermediate compound two and be dissolved in the YLENE, 100～250 ℃ were refluxed 1～10 hour, and the solid cooled that obtains, suction filtration, vacuum-drying obtain containing 1,1 '-dinaphthalene-2, the monomeric dianhydride monomer of 2 '-diphenol;
Route B:
(1) an amount of trimellitic anhydride chloride and pyridine are dissolved in the capacity toluene, obtain solution one; Will an amount of (R)-or (S)-binaphthol is dissolved in the toluene, obtains solution two; Solution two is slowly obtained mixing solutions in the adding solution one, mixing solutions slowly is warming up to temperature of reaction, lasting stirring obtains reaction soln;
(2) reaction soln is poured in the normal hexane of capacity separated out solid, washing, suction filtration, vacuum-drying, the mixed solvent recrystallization with acetic anhydride and acetic acid obtains containing 1,1 '-dinaphthalene-2, the monomeric dianhydride monomer of 2 '-diphenol;
Step 2: contain 1 with what step 1 obtained; 1 '-dinaphthalene-2; The monomeric dianhydride monomer of 2 '-diphenol and diamine monomer reacting by heating in organic solvent are filtered the film on the sheet glass upper berth of cleaning afterwards with gained solution, place the baking oven imidization then; Then in zero(ppm) water, soak demoulding, obtain the fluorinated polyimide film after drying.
Among the above-mentioned preparation method; Described diamines is O-Phenylene Diamine, mphenylenediamine, Ursol D, 4; 4 '-(hexafluoro sec.-propyl) pentanoic, 4,4 '-(4,4 '-hexafluoro isopropyl diphenyl base-1; 1 '-dioxy) pentanoic, 4, the mixture of one or more diamines in 4 '-diaminobenzene anilide, quadrol, tn, tetramethylenediamine, pentamethylene diamine, hexanediamine, heptamethylene diamine, octamethylenediamine, the nonamethylene diamine.
As preferably, the organic solvent described in second step is one or more the combination in DMF, DMAc, DMSO, the acetonitrile.
As preferably, in the described route B mixing solutions slowly is warming up to temperature of reaction, continue to stir 1～8 hour.
As preferably, the temperature of reaction in the described route B is 50～100 ℃, further is preferably 70～90 ℃
Compared with prior art, fluorinated polyimide infrared low-emissivity thin-film material of the present invention has following characteristics:
(1) the dinaphthalene group is introduced in the polyimide chain, formed stable fluorinated polyimide.This type of polymer thermostable property and conformational stability are excellent, can be applicable to the infrared stealth material very high to stability requirement.
(2) the selection diamines is allocated and is optimized.Through structure design, can adjust polymer architecture, and then reach the purpose of adjusting and controlling polymers chain structure and polymkeric substance infrared emittance.
(3) this fluorinated polyimide thin-film material has advantages such as film forming properties excellence, processing characteristics is superior, density is low, cost is few.
Therefore; Fluorinated polyimide thin-film material processing characteristics of the present invention is superior, cost is low; Have good solvent resistance, good thermostability and conformational stability, higher optical property; The substrate that not only can be used as infrared low-emissivity material is used, and can directly use as the infrared stealth material, is a kind of rising infrared stealth novel material; Its research and application have potential economic benefit and social benefit, in military and civilian technology field application promise in clinical practice are arranged all.
Embodiment
Below in conjunction with embodiment the present invention is described in further detail, it is pointed out that the following stated embodiment is intended to be convenient to understanding of the present invention, and it is not played any qualification effect.
Embodiment 1:
In the present embodiment, the structural formula of fluorinated polyimide infrared low-emissivity thin-film material is:
The preparation method of above-mentioned fluorinated polyimide infrared low-emissivity thin-film material is following:
Step 1: adopt following reaction scheme one Synthetic 2,2 '-two-(3,4 '-di carboxyl phenyloxy)-1,1 '-naphthyl naphthalene-dicarboxylic anhydride-bis ether acid anhydride (3), specific as follows:
At N
2Protection down, with 2.86g (R)-or (S)-binaphthol, the 4-nitro phthalic nitrile of 3.82g and the K of 4.74g
2CO
3After the mixing, add the anhydrous DMF of 30mL, stirred 20 hours under the room temperature; The mixture that obtains is poured in the Hydrogen chloride of 50mL2mol/L, and suction filtration is extremely neutral with the deionized water washing; With the mixed solvent recrystallization of methyl alcohol and acetonitrile, make 2,2 '-two-(3; 4 '-dicyano phenoxy)-1,1 '-naphthyl naphthalene (1).
With 2,2 ' of 5.39g-two-(3,4 '-dicyano phenoxy)-1, the sodium hydroxide of 1 '-naphthyl naphthalene (1), 8.0g, 10mL mass percent concentration are 30% H
2O
2After the mixing of 50mL water, 80 ℃ were stirred 12 hours down.Refluxed afterwards 48 hours, and obtained white solid, suction filtration after the deionized water dilution, is used the concentrated hydrochloric acid acidifying, makes 2,2 '-two-(3,4 '-di carboxyl phenyloxy)-1,1 '-naphthyl naphthalene (2).
Get 2,2 ' of 6.14g-two-(3,4 '-di carboxyl phenyloxy)-1; 1 '-naphthyl naphthalene (2) is dissolved in the 10mL YLENE, and 170 ℃ were refluxed the solid cooled that obtains 3 hours; Suction filtration, vacuum-drying makes 2; 2 '-two-(3,4 '-di carboxyl phenyloxy)-1,1 '-naphthyl naphthalene-dicarboxylic anhydride-bis ether acid anhydride (3).
Reaction scheme one:
Step 2: adopt following reaction scheme two preparation fluorinated polyimide films, be specially:
At N
2Protection is dissolved in 4,4 ' of 0.274g-(hexafluoro sec.-propyl) pentanoic among the DMAc of anhydrous 4mL down; Join slowly then that 0.5785g step 1 makes 2; 2 '-two-(3,4 '-di carboxyl phenyloxy)-1 are in 1 '-naphthyl naphthalene-dicarboxylic anhydride-bis ether acid anhydride (3); Heated and stirred 12 hours obtains heavy-gravity liquid.Liquid through strainer filtering, is vacuumized except that bubble, and the film on the sheet glass upper berth of cleaning places the baking oven imidization then.From baking oven, take out sheet glass, in zero(ppm) water, soak half a hour after, carry out demoulding, dry and obtain the fluorinated polyimide film.
Through measuring, the second-order transition temperature of the above-mentioned fluorinated polyimide film for preparing is 250 ℃, 280 ℃ of heat decomposition temperatures, and the average infrared emittance of 8～14 mu m wavebands is 0.483.
Reaction scheme two:
Embodiment 2:
In the present embodiment, the structural formula of fluorinated polyimide infrared low-emissivity thin-film material is:
The preparation method of above-mentioned fluorinated polyimide infrared low-emissivity thin-film material is following:
Step 1: adopt following reaction scheme one Synthetic 2,2 '-two-(3,4 '-di carboxyl phenyloxy)-1,1 '-naphthyl naphthalene-dicarboxylic anhydride-dibasic acid esters acid anhydride (5), specific as follows:
16.18g trimellitic anhydride chloride and 6.2mL pyridine are dissolved in the 50mL toluene, obtain solution one; 10.00g (R)-or (S)-binaphthol is dissolved in the 50mL toluene, obtains solution two; Solution two is slowly added in the solution one, mixing solutions slowly is warming up to 80 ℃, continue to stir 4 hours.After the reaction mixing solutions is poured in the normal hexane of q.s, separates out solid, wash suction filtration 2 times; Vacuum-drying with the mixed solvent recrystallization of acetic anhydride and acetic acid 2 times, obtains 2; 2 '-two-(3,4 '-di carboxyl phenyloxy)-1,1 '-naphthyl naphthalene-dicarboxylic anhydride-dibasic acid esters acid anhydride (5).
Reaction scheme one:
Step 2: adopt following reaction scheme two preparation fluorinated polyimide films, be specially:
At N
2Under the protection, with 0.274g 4,4 '-(hexafluoro sec.-propyl) pentanoic is dissolved among the anhydrous 4mL DMAc; Join slowly then that 0.6345g step 1 makes 2; 2 '-two-(3,4 '-di carboxyl phenyloxy)-1 are in 1 '-naphthyl naphthalene-dicarboxylic anhydride-dibasic acid esters acid anhydride (5); Heated and stirred 12 hours obtains heavy-gravity liquid.Liquid through strainer filtering, is vacuumized except that bubble, and the film on the sheet glass upper berth of cleaning places the baking oven imidization then.From baking oven, take out sheet glass, in zero(ppm) water, soak half a hour after, carry out demoulding, dry and obtain the fluorinated polyimide film.
Through mensuration, 260 ℃ of the above-mentioned fluorinated polyimide film glass transition temperatures for preparing, 290 ℃ of heat decomposition temperatures, the average infrared emittance of 8～14 mu m wavebands is 0.575.
Reaction scheme two:
Embodiment 3:
In the present embodiment, the structural formula of fluorinated polyimide infrared low-emissivity thin-film material is:
The preparation method of above-mentioned fluorinated polyimide infrared low-emissivity thin-film material is following:
Step 1: adopt and embodiment 1 identical reaction scheme one Synthetic 2,2 '-two-(3,4 '-di carboxyl phenyloxy)-1,1 '-naphthyl naphthalene-dicarboxylic anhydride-bis ether acid anhydride (3) specifically sees also the step of implementing in 11.
Step 2: adopt following reaction scheme two preparation fluorinated polyimide films, be specially:
At N
2Under the protection, with 0.428g 4,4 '-(4; 4 '-hexafluoro isopropyl diphenyl base-1,1 '-dioxy) pentanoic is dissolved among the anhydrous 4mLDMAc, join slowly then that 0.5785g step 1 makes 2; 2 '-two-(3,4 '-di carboxyl phenyloxy)-1 are in 1 '-naphthyl naphthalene-dicarboxylic anhydride-bis ether acid anhydride (3); Heated and stirred 12 hours obtains heavy-gravity liquid.This liquid through strainer filtering, is vacuumized except that bubble, and the film on the sheet glass upper berth of cleaning places the baking oven imidization then.From baking oven, take out sheet glass, in zero(ppm) water, soak half a hour after, carry out demoulding, dry and obtain the fluorinated polyimide film.
Through mensuration, 250 ℃ of the second-order transition temperatures of this fluorinated polyimide film, 280 ℃ of heat decomposition temperatures, the average infrared emittance of 8～14 mu m wavebands is 0.584.
Reaction scheme two:
Embodiment 4:
In the present embodiment, the structural formula of fluorinated polyimide infrared low-emissivity thin-film material is:
The preparation method of above-mentioned fluorinated polyimide infrared low-emissivity thin-film material is following:
Step 1: adopt and embodiment 2 identical reaction scheme one Synthetic 2s, 2 '-two-(3,4 '-di carboxyl phenyloxy)-1,1 '-naphthyl naphthalene-dicarboxylic anhydride-dibasic acid esters acid anhydride (5) specifically sees also the step of implementing in 21.
Step 2: adopt following reaction scheme two preparation fluorinated polyimide films, be specially:
At N
2Under the protection, with 0.428g 4,4 '-(4; 4 '-hexafluoro isopropyl diphenyl base-1,1 '-dioxy) pentanoic is dissolved among the anhydrous 4mLDMAc, join slowly then that 0.6345g step 1 makes 2; 2 '-two-(3,4 '-di carboxyl phenyloxy)-1 are in 1 '-naphthyl naphthalene-dicarboxylic anhydride-dibasic acid esters acid anhydride (5); Heated and stirred 12 hours obtains heavy-gravity liquid.This liquid through strainer filtering, is vacuumized except that bubble, and the film on the sheet glass upper berth of cleaning places the baking oven imidization then.From baking oven, take out sheet glass, in zero(ppm) water, soak half a hour after, carry out demoulding, dry and obtain the fluorinated polyimide film.
Through mensuration, 260 ℃ of the second-order transition temperatures of the above-mentioned fluorinated polyimide film for preparing, 290 ℃ of heat decomposition temperatures, the average infrared emittance of 8～14 mu m wavebands is 0.697.
Reaction scheme two:
Above-described embodiment specifies technical scheme of the present invention; Be understood that the above is merely specific embodiment of the present invention; Be not limited to the present invention; All any modifications of in principle scope of the present invention, being made, replenish or similar fashion substitutes etc., all should be included within protection scope of the present invention.
Claims (10)
1. fluorinated polyimide infrared low-emissivity thin-film material, it is characterized in that: its general structure is:
Wherein, polymerization degree n is 1～1000; R
1And/or R
2In comprise fluorine atom, and R
1Be selected from a kind of in the following structure:
R
2Be selected from a kind of in the following structure:
2. fluorinated polyimide infrared low-emissivity thin-film material as claimed in claim 1 is characterized in that: the average infrared emittance of 8～14 mu m wavebands is 0.30～0.70.
3. fluorinated polyimide infrared low-emissivity thin-film material as claimed in claim 1 is characterized in that: the average infrared emittance of 8～14 mu m wavebands is 0.45～0.60.
4. fluorinated polyimide infrared low-emissivity thin-film material as claimed in claim 1, it is characterized in that: glass transition temp is greater than 200 ℃.
5. fluorinated polyimide infrared low-emissivity thin-film material as claimed in claim 1, it is characterized in that: heat decomposition temperature is greater than 250 ℃.
6. fluorinated polyimide infrared low-emissivity thin-film material as claimed in claim 1 is characterized in that: described glass transition temp is 220～240 ℃, and heat decomposition temperature is 270～300 ℃.
7. the preparation method of fluorinated polyimide infrared low-emissivity thin-film material as claimed in claim 1 is characterized in that: comprise the steps:
Step 1: adopt following route A or route B to synthesize and contain 1,1 '-dinaphthalene-2, the monomeric dianhydride monomer of 2 '-diphenol;
Route A:
(1) at N
2Protection down; Will an amount of (R)-or (S)-and after binaphthol, 4-nitro phthalic nitrile and salt of wormwood mix, add the anhydrous DMF of capacity, stirred under the room temperature 15～30 hours; The mixture that obtains is poured suction filtration in the Hydrogen chloride of capacity into; Extremely neutral with the deionized water washing then, the mixed solvent recrystallization with methyl alcohol and acetonitrile obtains intermediate compound one;
(2) get an amount of intermediate compound one, sodium hydroxide, H
2O
2After mixing with water, 40～80 ℃ were stirred 10～30 hours down, refluxed afterwards 30～60 hours, obtained white solid, suction filtration, used the concentrated hydrochloric acid acidifying with deionized water dilution back, obtained intermediate compound two;
(3) get an amount of intermediate compound two and be dissolved in the YLENE, 100～250 ℃ were refluxed 1～10 hour, and the solid cooled that obtains, suction filtration, vacuum-drying obtain containing 1,1 '-dinaphthalene-2, the monomeric dianhydride monomer of 2 '-diphenol;
Route B:
(1) an amount of trimellitic anhydride chloride and pyridine are dissolved in the capacity toluene, obtain solution one; Will an amount of (R)-or (S)-binaphthol is dissolved in the toluene, obtains solution two; Solution two is slowly obtained mixing solutions in the adding solution one, mixing solutions slowly is warming up to temperature of reaction, lasting stirring obtains reaction soln;
(2) reaction soln is poured in the normal hexane of capacity separated out solid, washing, suction filtration, vacuum-drying, the mixed solvent recrystallization with acetic anhydride and acetic acid obtains containing 1,1 '-dinaphthalene-2, the monomeric dianhydride monomer of 2 '-diphenol;
Step 2: contain 1 with what step 1 obtained; 1 '-dinaphthalene-2; The monomeric dianhydride monomer of 2 '-diphenol and diamine monomer reacting by heating in organic solvent are filtered the film on the sheet glass upper berth of cleaning afterwards with gained solution, place the baking oven imidization then; Then in zero(ppm) water, soak demoulding, obtain the fluorinated polyimide film after drying.
8. the preparation method of fluorinated polyimide infrared low-emissivity thin-film material as claimed in claim 7; It is characterized in that: described diamines is O-Phenylene Diamine, mphenylenediamine, Ursol D, 4; 4 '-(hexafluoro sec.-propyl) pentanoic, 4; 4 '-(4; 4 '-hexafluoro isopropyl diphenyl base-1,1 '-dioxy) pentanoic, 4, the mixture of one or more diamines in 4 '-diaminobenzene anilide, quadrol, tn, tetramethylenediamine, pentamethylene diamine, hexanediamine, heptamethylene diamine, octamethylenediamine, the nonamethylene diamine.
9. the preparation method of fluorinated polyimide infrared low-emissivity thin-film material as claimed in claim 7 is characterized in that: the organic solvent in the described step 2 is one or more the combination in DMF, DMAc, DMSO, the acetonitrile.
10. the preparation method of fluorinated polyimide infrared low-emissivity thin-film material as claimed in claim 7 is characterized in that: temperature of reaction is 50～100 ℃ in the described route B.
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| CN104629362A (en) * | 2013-11-08 | 2015-05-20 | 中国科学院宁波材料技术与工程研究所 | Fluorine-containing polyimide composite film material with low infrared emissivity and preparation method thereof |
| CN110483771A (en) * | 2019-08-12 | 2019-11-22 | 天津理工大学 | A kind of purposes of polyimide resin and its synthetic method and the resin film based on binaphthalene ether skeleton structure |
| CN111363148A (en) * | 2020-03-26 | 2020-07-03 | 天津理工大学 | Preparation method of binaphthyl network type polyimide resin and film and application of binaphthyl network type polyimide resin and film in gas separation |
| WO2022270367A1 (en) * | 2021-06-22 | 2022-12-29 | 三菱瓦斯化学株式会社 | Thermoplastic resin and optical lens including same |
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| CN102643544B (en) | 2013-11-13 |
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