WO2016032179A1 - 내열성 및 내화학성이 우수한 폴리술폰 공중합체 및 그 제조방법 - Google Patents
내열성 및 내화학성이 우수한 폴리술폰 공중합체 및 그 제조방법 Download PDFInfo
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- WO2016032179A1 WO2016032179A1 PCT/KR2015/008808 KR2015008808W WO2016032179A1 WO 2016032179 A1 WO2016032179 A1 WO 2016032179A1 KR 2015008808 W KR2015008808 W KR 2015008808W WO 2016032179 A1 WO2016032179 A1 WO 2016032179A1
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- polysulfone copolymer
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- polysulfone
- diol
- anhydrosugar
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
- C08G75/23—Polyethersulfones
Definitions
- the present invention relates to a polysulfone copolymer having excellent heat resistance and chemical resistance, and a method of manufacturing the same. More specifically, the problem of exhaustion of petroleum resources as a finite resource by including a sulfone-based compound and an anhydrosugar alcohol as a biological origin as a repeating unit.
- the present invention relates to a polysulfone copolymer and a method of manufacturing the same, which are environmentally friendly and do not emit carbon dioxide even after disposal after use, and have significantly improved heat resistance and chemical resistance compared to conventional polysulfone copolymers.
- Hydrogenated sugar means a compound obtained by adding hydrogen to a reducing end group of a saccharide, and generally HOCH 2 (CHOH) n CH 2 OH (where n is an integer of 2 to 5). ) And are classified according to carbon number to trititol, pentitol, hexitol and heptitol (4, 5, 6 and 7 carbon atoms, respectively). Among them, hexitol having 6 carbon atoms includes sorbitol, mannitol, iditol, galactitol and the like, and sorbitol and mannitol are particularly useful substances.
- Anhydrosugar alcohols have a diol form having two hydroxyl groups in the molecule, and may be prepared using hexitol derived from starch (eg, Korean Patent No. 10-1079518, Korean Patent Publication No. 10). -2012-0066904). Since anhydrosugar alcohols are environmentally friendly materials derived from renewable natural resources, many studies have been conducted for a long time with a great deal of interest. Among these anhydrosugar alcohols, isosorbide made from sorbitol has the widest range of industrial applications at present.
- anhydrosugar alcohols is very diverse, such as treatment of heart and vascular diseases, adhesives of patches, mouthwashes and the like, solvents of the composition in the cosmetic industry, emulsifiers in the food industry.
- it can also be used as an environmentally friendly solvent of adhesives, environmentally friendly plasticizers, biodegradable polymers, water-soluble lacquer.
- anhydrosugar alcohols are receiving a lot of attention due to their various applicability, and their use in actual industries is also gradually increasing.
- Polysulfone is one of the compounds that is usefully used as an electrically insulating material requiring heat resistance, various molding materials or membrane materials requiring dimensional stability and chemical resistance.
- the polysulfones are generally manufactured using raw materials derived from petroleum resources, and there is a need to provide polysulfones using raw materials obtained from biomass resources such as plants due to the depletion of finite petroleum resources.
- biomass resources such as plants due to the depletion of finite petroleum resources.
- carbon-neutral monomers derived from carbon-neutral plants may not be released even after disposal. Development of polysulfone as a raw material is required.
- the prior patent document discloses a fine filtration membrane comprising a polysulfone-based polymer and a method for manufacturing the same, and more specifically, when the polysulfone-based polymer is used for the production of a microfiltration membrane or an ultrafiltration membrane, the shape and size of the filtration membrane It is disclosed that the pore can be properly adjusted (for example, Korean Patent Publication No. 2014-0054765).
- Korean Patent Publication No. 2014-0054765 Korean Patent Publication No. 2014-0054765
- the problem of resource depletion can be solved by including an alternative material, and a polysulfone copolymer that is environmentally friendly and does not emit carbon dioxide even after disposal after use is excellent in heat resistance and chemical resistance.
- the present invention is to solve the problems of the prior art as described above, by including a sulfone-based compound and an anhydrosugar alcohol which is a bio-based material as a repeating unit can solve the problem of depletion of petroleum resources, finite resources, disposal after use Even if it does not emit carbon dioxide, it is environmentally friendly, and a technical problem to provide a polysulfone copolymer and a method of manufacturing the same significantly improved heat resistance and chemical resistance compared to the conventional polysulfone copolymer.
- the present invention to solve the above technical problem, a repeating unit derived from a diol component containing anhydrosugar alcohol; And repeating units derived from a dihalogenated sulfone compound.
- the step of polymerizing a diol component comprising an anhydrosugar alcohol, and a dihalogenated sulfone compound (2) diluting the polymerization reaction product and then removing alkali metal halide therefrom; And (3) precipitating the diluted polymerization reaction product, and then washing the diluted polymerization reaction product.
- a molded article produced using the polysulfone copolymer.
- the polysulfone copolymer according to the present invention can solve the problem of depletion of petroleum resources as a finite resource by including a sulfone compound and anhydrosugar alcohol which is a bio-based material as a repeating unit, and does not emit carbon dioxide even when disposed of after use.
- a sulfone compound and anhydrosugar alcohol which is a bio-based material as a repeating unit
- it since it exhibits significantly improved heat resistance and chemical resistance compared to the existing polysulfone copolymer, it can be used very suitably for the use of resin processed products such as membranes.
- the polysulfone copolymer of the present invention includes a repeating unit derived from a diol component containing anhydrosugar alcohol; And repeating units derived from a dihalogenated sulfone compound.
- the anhydrosugar alcohol refers to any substance obtained by removing one or more water molecules from a compound obtained by adding hydrogen to a reducing end group of a saccharide, commonly called hydrogenated sugar or sugar alcohol. do.
- the anhydrosugar alcohol dianhydrohexitol, which is a dehydration product of hexitol, may be preferably used. More preferably, the anhydrosugar alcohol is isosorbide (1,6-dianhydrosorbitol), iso Mannide (1,6- dianhydromannitol), isoidide (1,6- dianhydroiditol), and mixtures thereof.
- the diol component used in the preparation of the polysulfone copolymer may further include a diol compound other than the anhydrosugar alcohol, such as an aromatic diol, an alicyclic diol, an aliphatic diol, or a combination thereof, and is preferable. It may further comprise an aromatic diol.
- aromatic diol examples include bisphenol A, 4,4'-dihydroxy-diphenyl sulfone, 4,4'-biphenol, hydroquinone, 4,4'-dihydroxy-diphenyl ether, and 3- (4 -Hydroxyphenoxy) phenol, bis (4-hydroxyphenyl) sulfide and combinations thereof can be preferably used.
- Examples of the alicyclic diols include 1,4-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,2-cyclohexanedimethanol, tricyclodecanedimethanol, adamantanediol, and pentacyclopentadedecane
- 1,4-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,2-cyclohexanedimethanol, tricyclodecanedimethanol, adamantanediol, and pentacyclopentadedecane One selected from the group consisting of methanol and combinations thereof can be preferably used.
- aliphatic diols examples include ethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, 1,3-butanediol, 1,2-butanediol, 1,5-heptanediol, 1, It is preferable to use those selected from the group consisting of 6-hexanediol, 1,4-cyclohexanedimethanol and combinations thereof.
- R 1 and R 2 each independently represent a cycloalkyl group having 4 to 20 carbon atoms or a cycloalkoxy group having 6 to 20 carbon atoms.
- the diol component used in the production of the polysulfone copolymer is preferably a diol compound other than 0.1 to 99 mol% of anhydrosugar alcohol and anhydrosugar alcohol (for example, aromatic) based on 100 mol% of all diol components.
- anhydrosugar alcohol is less than 0.1 mol% (that is, when the diol compound other than anhydrosugar alcohol is more than 99.9 mol%) of the total diol components, the effect of increasing the heat resistance and chemical resistance properties of the sulfone resin is insignificant, If it exceeds 99 mol% it may be difficult to obtain the desired molecular weight.
- dihalogenated diaryl sulfone can be preferably used, and more specifically, 4,4'-dichlorodiphenyl sulfone, 4,4 Those selected from the group consisting of '-difluorodiphenylsulfone and combinations thereof can be preferably used.
- the amount of the diol component and the dihalogenated sulfone compound used in the preparation of the polysulfone copolymer is not particularly limited, but the amount of the dihalogenated sulfone compound is preferably 50 mol to 100 mol based on 100 mol of the total diol component. It may be 300 mol, more preferably 80 to 150 mol.
- the amount of dihalogenated sulfone is too small or too large compared to the total diol component used in the preparation of the polysulfone copolymer, the diol component and the dihalogen sulfone reaction may not be properly performed, which may cause difficulty in obtaining a desired molecular weight.
- dihalogen compounds may be used in addition to the dihalogenated sulfone compound.
- 1-50 weight part of other dihalogen compounds other than a dihalogenation sulfone compound can be used with respect to 100 weight part of dihalogenated sulfone compounds.
- 1,4-chlorobenzene, 1,4-diflurobenzene, bis (4-chlorophenyl) sulfide, di, (4-fluorophenyl) sulfide or combinations thereof may be used. Can be.
- the polysulfone copolymer of the present invention may include a structure represented by any one of the following Chemical Formulas 3 to 6 in the copolymer (in parentheses []) The part indicated is a repeating unit).
- the step of polymerizing a diol component comprising an anhydrosugar alcohol, and a dihalogenated sulfone compound (2) diluting the polymerization reaction product and then removing alkali metal halide therefrom; And (3) precipitating the diluted polymerization reaction product, and then washing the diluted polymerization reaction product.
- the alkali metal salt catalyst one selected from the group consisting of potassium carbonate, sodium carbonate, sodium hydroxide, potassium hydroxide and mixtures thereof can be preferably used.
- the amount of catalyst used there is no particular limitation on the amount of catalyst used, but when the amount of the catalyst is too small, the reaction rate is slow. On the contrary, when the amount of the catalyst is too high, the residual catalyst may discolor the product or degrade the physical properties. According to one embodiment of the invention, for example, based on 100 moles of the diol component, 80 to 300 moles of catalyst, more preferably 100 to 130 moles may be used.
- the polymerization reaction is, for example, the reaction solvent N-methyl-2-pyrrolidone (NMP), dimethyl sulfoxide (DMSO), dimethylacetamide (for 5 to 10 hours at a temperature of 160 to 200 °C and atmospheric pressure) DMAc), dimethylformamide (DMF), sulfolane, diphenyl sulfone (DPS), dimethylsulfone (DMS) and the like, solvents such as chlorobenzene, tetrahydrofuran (THF), or mixed solvents thereof It may be performed, but is not limited thereto.
- NMP N-methyl-2-pyrrolidone
- DMSO dimethyl sulfoxide
- DMAc dimethylacetamide
- DMF dimethylformamide
- sulfolane sulfolane
- DPS diphenyl sulfone
- DMS dimethylsulfone
- solvents such as chlorobenzene, tetrahydrofuran (THF),
- the polymerization reaction product is diluted (the same solvent as the polymerization solvent can be used), and from the diluted reaction product, the alkali metal halide (alkali metal salt obtained from the alkali metal salt catalyst) Salts of halogens from the dihalogenated sulfone compounds, such as KCl, are removed by means of decanter centrifuge centrifuges, for example using a celite filter pass or a specific gravity difference.
- the diluted and filtered reaction product can then be precipitated in a solvent (eg alcohol or water such as methanol) and then washed with water or the like to produce the polysulfone copolymer of the present invention.
- a solvent eg alcohol or water such as methanol
- the polysulfone copolymer of the present invention includes a sulfone-based compound and an anhydrosugar alcohol, which is a bio-based material, as a repeating unit, thereby solving the problem of depletion of petroleum resources, which are finite resources, and carbon dioxide even if disposed of after use. It is environmentally friendly because it does not emit, and since it is remarkably superior in heat resistance and chemical resistance compared to the conventional polysulfone copolymer, it can be used very suitably for various molding materials and resin processed products such as membranes.
- a molded article preferably a membrane, made using the polysulfone copolymer of the present invention may be provided.
- the molding process include solution spinning, casting (coating), extrusion, injection, and the like, but are not limited thereto.
- Applications of the membrane provided according to the present invention include water treatment R / O membranes, fuel cell electrolyte membranes, Medical hemodialysis membranes, electrical and electronic connectors, automotive parts, etc., but is not limited thereto.
- the method for producing a molded article such as a membrane using the polysulfone copolymer of the present invention is not particularly limited, and a method generally used for producing a resin molded article can be used as it is or as appropriately modified.
- Isosorbide (ISB) (0.05 mole), 4,4'-dichlorodiphenyl sulfone (DCDPS) (1.0 mole), bisphenol A (bisphenol A, BPA) (0.95 mole), potassium carbonate (1.1 mole), N-Methyl-2-pyrrolidone (NMP) (10.1 mole) and chlorobenzene (1.11 mole) was supplied.
- the reaction mixture was rapidly heated to a reaction temperature (160 ° C.) under nitrogen purging, and it was confirmed that chlorobenzene, which was added as a co-solvent, was azeotropically reacted with H 2 O as a reaction by-product over time. . After 9 hours of reaction time at a temperature of 192 ° C., the final reaction mixture turned dark brown, and the viscosity of the reaction mixture was visually confirmed.
- the final reaction mixture was cooled down to room temperature and then diluted in a pre-prepared solvent NMP.
- the diluted reaction mixture was filtered through celite and then precipitated in methanol.
- the precipitated product was washed with distilled water and filtered, and then dried to obtain an isosorbide (ISB) -containing polysulfone copolymer.
- ISB isosorbide
- Isosorbate 1 L three-necked flask with stirrer, thermometer and condenser isosorbide (ISB) (0.1 mole), 4,4'-dichlorodiphenyl sulfone (DCDPS) (1.0 mole), bisphenol A (BPA) (0.9 mole) Isosorbate was carried out in the same manner as in Example 1, except that potassium carbonate (1.1 mole), N-methyl-2-pyrrolidone (NMP) (10.1 mole) and chlorobenzene (1.11 mole) were supplied. Polysulfone copolymers containing beads (ISB) (10 mole%) were obtained.
- Isosorbate 1 L three-necked flask with stirrer, thermometer and condenser isosorbide (ISB) (0.2 mole), 4,4'-dichlorodiphenyl sulfone (DCDPS) (1.0 mole), bisphenol A (BPA) (0.8 mole) Isosorbate was carried out in the same manner as in Example 1, except that potassium carbonate (1.1 mole), N-methyl-2-pyrrolidone (NMP) (10.1 mole) and chlorobenzene (1.11 mole) were supplied. A polysulfone copolymer containing beads (ISB) (20 mole%) could be obtained.
- Isosorbate 1 L three-necked flask with stirrer, thermometer and condenser isosorbide (ISB) (0.4 mole), 4,4'-dichlorodiphenyl sulfone (DCDPS) (1.0 mole), bisphenol A (BPA) (0.6 mole) Isosorbate was carried out in the same manner as in Example 1, except that potassium carbonate (1.1 mole), N-methyl-2-pyrrolidone (NMP) (10.1 mole) and chlorobenzene (1.11 mole) were supplied. A polysulfone copolymer containing beads (ISB) (40 mole%) could be obtained.
- Isosorbate 1 L three-necked flask with stirrer, thermometer and condenser isosorbide (ISB) (0.5 mole), 4,4'-dichlorodiphenyl sulfone (DCDPS) (1.0 mole), bisphenol A (BPA) (0.5 mole) Isosorbate was carried out in the same manner as in Example 1, except that potassium carbonate (1.1 mole), N-methyl-2-pyrrolidone (NMP) (10.1 mole) and chlorobenzene (1.11 mole) were supplied. A polysulfone copolymer containing beads (ISB) (50 mole%) could be obtained.
- Isosorbate 1 L three-necked flask with stirrer, thermometer and condenser isosorbide (ISB) (0.7 mole), 4,4'-dichlorodiphenyl sulfone (DCDPS) (1.0 mole), bisphenol A (BPA) (0.3 mole) Isosorbate was carried out in the same manner as in Example 1, except that potassium carbonate (1.1 mole), N-methyl-2-pyrrolidone (NMP) (10.1 mole) and chlorobenzene (1.11 mole) were supplied. A polysulfone copolymer containing beads (ISB) (70 mole%) could be obtained.
- the polysulfone copolymer is completely dissolved in DMAc at a concentration of 25%.
- Each polymer solution was cast on a support made of polypropylene (PP) film using a sparger at a thickness of 200 ⁇ m and 0.2 m / min, followed by a temperature of 20 to 30 ° C. and a humidity of 30 to 80
- the upper layer was exposed for about 2 minutes in% air, followed by primary desolvation for 3 minutes in a MeOH coagulation bath.
- the polysulfone (PSU) film is peeled off from the PP support.
- the exfoliated PSU film is immersed in a H 2 O coagulation bath, and then completely desolventized for about 3 hours, and then dried at 80 ° C. for 3 hours to obtain a dried PSU film.
- Weight average molecular weight (Mw) and molecular weight distribution (MWD) are Weight average molecular weight (Mw) and molecular weight distribution (MWD)
- Mn number average molecular weight
- the polysulfone copolymer of the present invention has a glass transition temperature (Tg) value as the ISB content increases This increased and has excellent heat resistance, it was found to have excellent chemical resistance in the solvent experiment of DMAc, toluene, THF. Therefore, the polysulfone copolymer of the present invention is excellent in heat resistance and chemical resistance compared to the comparative example of the conventional polysulfone copolymer, which is suitable for the production of resin molded articles such as membranes, and includes finite resources by containing anhydrosugar alcohol, which is a biological material. It can solve the problem of depletion of petroleum resources, and it is environmentally friendly because it does not emit carbon dioxide even after disposal.
- Tg glass transition temperature
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Abstract
Description
Claims (11)
- 무수당 알코올을 포함하는 디올 성분으로부터 유래된 반복 단위; 및 디할로겐화 술폰 화합물로부터 유래된 반복 단위;를 포함하는 폴리술폰 공중합체.
- 제1항에 있어서, 무수당 알코올이 이소소르비드, 이소만니드, 이소이디드 및 이들의 혼합물로 이루어진 그룹으로부터 선택되는 것을 특징으로 하는 폴리술폰 공중합체.
- 제1항에 있어서, 디올 성분이, 무수당 알코올 이외의 디올 화합물을 더 포함하는 것을 특징으로 하는 폴리술폰 공중합체.
- 제3항에 있어서, 무수당 알코올 이외의 디올 화합물이 방향족 디올, 지환식 디올, 지방족 디올 또는 이들의 조합인 것을 특징으로 하는 폴리술폰 공중합체.
- 제4항에 있어서,방향족 디올이 비스페놀 A, 4,4’-디하이드록시-디페닐 술폰, 4,4’-비페놀, 하이드로퀴논, 4,4’-디하이드록시-디페닐에테르, 3-(4-하이드록시페녹시)페놀, 비스(4-하이드록시페닐)술파이드 및 이들의 조합으로 이루어진 그룹으로부터 선택되고,지환식 디올이 1,4-사이클로헥산디메탄올, 1,3-사이클로헥산디메탄올, 1,2-사이클로헥산디메탄올, 트리시클로데칸디메탄올, 아다만탄디올, 펜타시클로펜타데칸디메탄올 및 이들의 조합으로 이루어진 그룹으로부터 선택되고,지방족 디올이 에틸렌글리콜, 1,3-프로판디올, 1,2-프로판디올, 1,4-부탄디올, 1,3-부탄디올, 1,2-부탄디올, 1,5-헵탄디올, 1,6-헥산디올, 1,4-사이클로헥산디메탄올 및 이들의 조합으로 이루어진 그룹으로부터 선택되는 것을 특징으로 하는 폴리술폰 공중합체.
- 제1항에 있어서, 디올 성분이, 전체 디올 성분 100몰%를 기준으로 무수당 알코올 0.1~99몰% 및 무수당 알코올 이외의 디올 화합물 1~99.9몰%를 포함하는 것을 특징으로 하는 폴리술폰 공중합체.
- 제1항에 있어서, 디할로겐화 술폰 화합물이 4,4’-디클로로디페닐술폰, 4,4’-디플루오로디페닐술폰 및 이들의 조합으로 이루어진 그룹으로부터 선택되는 것을 특징으로 하는 폴리술폰 공중합체.
- (1) 알칼리금속염 촉매의 존재하에, 무수당 알코올을 포함하는 디올 성분 및 디할로겐화 술폰 화합물을 중합하는 단계;(2) 중합 반응 결과물을 희석한 후, 그로부터 알칼리금속 할로겐화물을 제거하는 단계; 및(3) 희석된 중합 반응 결과물을 침전시킨 후, 이를 세정하는 단계;를 포함하는 폴리술폰 공중합체의 제조방법.
- 제8항에 있어서, 알칼리금속염 촉매가 탄산칼륨, 탄산나트륨, 수산화나트륨, 수산화칼륨 및 이들의 혼합물로 이루어진 그룹으로부터 선택되는 것을 특징으로 하는 폴리술폰 공중합체의 제조방법.
- 제1항 내지 제7항 중 어느 한 항의 폴리설폰 공중합체를 이용하여 제조된 성형제품.
- 제10항에 있어서, 멤브레인인 것을 특징으로 하는 성형제품.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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EP15835779.8A EP3170855B1 (en) | 2014-08-25 | 2015-08-24 | Polysulfone copolymer with excellent heat resistance and chemical resistance, and method for preparing same |
CN201580046011.6A CN106795286B (zh) | 2014-08-25 | 2015-08-24 | 耐热性及耐化学性优异的聚砜共聚物及其制备方法 |
JP2017511217A JP6662853B2 (ja) | 2014-08-25 | 2015-08-24 | 耐熱性及び耐化学性に優れたポリスルホン共重合体、及びその製造方法 |
US15/504,530 US20170240708A1 (en) | 2014-08-25 | 2015-08-24 | Polysulfone copolymer with excellent heat resistance and chemical resistance, and method for preparing same |
Applications Claiming Priority (4)
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KR20140110991 | 2014-08-25 | ||
KR10-2014-0110991 | 2014-08-25 | ||
KR10-2015-0078373 | 2015-06-03 | ||
KR1020150078373A KR101704475B1 (ko) | 2014-08-25 | 2015-06-03 | 내열성 및 내화학성이 우수한 폴리술폰 공중합체 및 그 제조방법 |
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WO2016032179A1 true WO2016032179A1 (ko) | 2016-03-03 |
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KR20180125509A (ko) * | 2016-03-15 | 2018-11-23 | 솔베이 스페셜티 폴리머스 이태리 에스.피.에이. | 설폰 중합체 멤브레인의 제조를 위한 조성물 및 방법 |
FR3085040A1 (fr) | 2018-08-20 | 2020-02-21 | Roquette Freres | Procede de preparation de polyethersulfones aromatiques a base d'isohexide |
WO2020053078A1 (en) * | 2018-09-11 | 2020-03-19 | Basf Se | Polyarylene ether copolymer |
WO2022128815A1 (en) * | 2020-12-18 | 2022-06-23 | Solvay Specialty Polymers Usa, Llc | Bio-based sulfone copolymers free of bpa and bps |
WO2023006830A1 (en) | 2021-07-30 | 2023-02-02 | Basf Se | Polyarylether copolymers based on diols sugar alcohols |
WO2023084062A1 (en) | 2021-11-15 | 2023-05-19 | Basf Se | Polyarylether copolymers based on diol sugar alcohols |
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WO2023006830A1 (en) | 2021-07-30 | 2023-02-02 | Basf Se | Polyarylether copolymers based on diols sugar alcohols |
WO2023084062A1 (en) | 2021-11-15 | 2023-05-19 | Basf Se | Polyarylether copolymers based on diol sugar alcohols |
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