KR101704490B1 - Polysulfone copolymer having excellent tensile property and method for preparing the same - Google Patents
Polysulfone copolymer having excellent tensile property and method for preparing the same Download PDFInfo
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- KR101704490B1 KR101704490B1 KR1020150080211A KR20150080211A KR101704490B1 KR 101704490 B1 KR101704490 B1 KR 101704490B1 KR 1020150080211 A KR1020150080211 A KR 1020150080211A KR 20150080211 A KR20150080211 A KR 20150080211A KR 101704490 B1 KR101704490 B1 KR 101704490B1
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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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/06—Polysulfones; Polyethersulfones
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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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/61—Permeability
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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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/71—Purification
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
The present invention relates to a polysulfone-based copolymer having excellent tensile properties and a method for producing the same. More specifically, the present invention can solve the problem of depletion of petroleum resources by using anhydrosugar alcohol as a raw material as a raw material, Based copolymer and a method for producing the same.
Description
The present invention relates to a polysulfone-based copolymer having excellent tensile properties and a method for producing the same. More specifically, the present invention can solve the problem of depletion of petroleum resources by using anhydrosugar alcohol as a raw material as a raw material, Based copolymer and a method for producing the same.
Hydrogenated sugar (also referred to as " sugar alcohol ") refers to a compound obtained by adding hydrogen to a reducing end group of a saccharide, generally HOCH 2 (CHOH) n CH 2 OH (where n is an integer of 2 to 5 ), And classified into tetritol, pentitol, hexitol and heptitol (C 4, 5, 6 and 7, respectively), depending on the number of carbon atoms. Among them, hexitol having 6 carbon atoms includes sorbitol, mannitol, iditol, galactitol and the like, and sorbitol and mannitol are particularly useful substances.
Anhydrosugar alcohol has a diol form with two hydroxyl groups in the molecule and can be prepared by utilizing hexitol derived from starch (for example, Korean Patent No. 10-1079518, Korean Patent Laid- -2012-0066904). Since alcohol-free alcohol is an eco-friendly substance derived from renewable natural resources, there has been much interest for a long time and studies on the manufacturing method have been carried out. Among these alcohol-free alcohols, isosorbide prepared from sorbitol has the widest industrial application currently.
The use of anhydrous alcohol is widely used in the treatment of cardiovascular diseases, patches, adhesives, oral cleansers and the like, solvents for compositions in the cosmetics industry, and emulsifiers in the food industry. Because alcohol-free alcohol is an eco-friendly material derived from natural materials, it is very useful in the plastics industry such as bioplastics. It is also known to be used as an environmentally friendly solvent for adhesives, environmentally friendly plasticizers, biodegradable polymers, and water-soluble lacquers.
As such, alcohol-free alcohol has attracted a great deal of attention due to its versatility and its use in real industry is increasing.
One of the compounds useful for the material of the membrane is a sulfonic polymer. However, the polysulfone is generally manufactured using a raw material derived from petroleum resources. Due to the exhaustion of finite resources, it is required to provide polysulfone using raw materials obtained from biomass resources such as plants. In addition, there is concern that an increase in carbon dioxide emissions, global warming due to accumulation may cause climate change, and even in the case of disposal after use, carbon-neutral, polysulfone derived from plant- Has been demanded. In addition, conventional sulfonic membranes have a strong mechanical property but are insufficient in tensile properties, and thus can only be used in the form of a plate membrane, and the membrane has a limited durability during long-term operation.
Accordingly, there is a demand for the development of a novel sulfonic polymer capable of having enhanced tensile properties and having excellent durability and excellent stretchability when applied to a membrane, and which can also be used as a fiber.
Disclosure of Invention Technical Problem [8] Accordingly, the present invention has been made to solve the above problems of the prior art, and it is an object of the present invention to solve the problem of depletion of petroleum resources by using anhydrosugar alcohol as a raw material as a raw material, And an object of the present invention is to provide an improved polysulfone-based copolymer and a method for producing the same.
In order to solve the above-mentioned technical problems, the present invention provides a process for producing a diol compound, which comprises repeating units derived from a diol compound component comprising an anhydrosugar alcohol having at least one end added with an adduct selected from ethylene oxide and aliphatic diol; And a repeating unit derived from a sulfone compound component.
According to another aspect of the present invention, there is provided a process for producing a diol compound and a sulfone compound, comprising the steps of: (1) polymerizing a diol compound component and a sulfone compound component containing an anhydropolydoic alcohol having at least two adducts selected from ethylene oxide and aliphatic diol at both ends in the presence of an alkali metal salt catalyst ; (2) diluting the polymerization reaction product, and then removing the alkali metal halide therefrom; And (3) precipitating the result of the diluted polymerization reaction, followed by washing the resultant, and a process for producing the polysulfone-based copolymer.
According to still another aspect of the present invention, there is provided a molded article produced by extrusion or injection molding the polysulfone-based copolymer.
The polysulfone-based copolymer according to the present invention can solve the problem of depletion of petroleum resources by using anhydrosugar alcohol as a raw material as a raw material, and exhibits significantly improved tensile properties as compared with conventional sulfonic copolymers, It can be expected to increase the durability due to the improvement in stretchability when it is applied to a membrane, and it can be suitably used for textile applications.
Hereinafter, the present invention will be described in more detail.
The sulfone-based copolymer of the present invention is a copolymer comprising repeating units derived from a diol compound component comprising an anhydrosugar alcohol having at both ends thereof at least one adduct selected from ethylene oxide and aliphatic diol; And a repeating unit derived from a sulfone compound component.
The alcohol-free alcohol in which at least one adduct selected from ethylene oxide and aliphatic diol is added is a compound obtained by adding hydrogen to the reducing end group of a saccharide, which is generally called hydrogenated sugar or sugar alcohol. Refers to a compound obtained by adding one or more adducts selected from ethylene oxide and aliphatic diol to both ends of an anhydropoly alcohol, which is a substance obtained by removing one or more water molecules from the reaction product. Although not limited thereto, the number of adducts added at both ends of anhydrosugar alcohol can be independently within the range of 1 to 15.
As the adduct, aliphatic diols include aliphatic dihydroxy compounds such as ethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, 1,3- Butanediol, 1,5-heptanediol, 1,6-hexanediol, and combinations thereof, but are not limited thereto.
As the anhydrosugar alcohol, dianhydrohexitol, which is a dehydrate of hexitol, can be preferably used. More preferably, the anhydrosugar alcohol is isosorbide (1,6-dianhydroisorbitol), isomannide (1, Dianhydroiodide), isodide (1,6-dianhydroiditol), and mixtures thereof.
In the present invention, the diol compound component may further include a diol compound other than the anhydrous alcohol to which the adduct is added, and may further include an aromatic diol, an aliphatic diol, an alicyclic diol, or a combination thereof .
Examples of the aromatic diol include bisphenol A, hydroquinone, 4,4'-dihydroxydiphenyl sulfone (DHDPS), 4,4'-biphenol, 3- (4-hydroxyphenoxy) phenol, And the aliphatic diol may be selected from the group consisting of ethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, 1,3-butanediol, 1,5-heptanediol, 1,6-hexanediol, and combinations thereof. The alicyclic diol may be selected from the group consisting of 1,4-cyclohexanedimethanol, 1,3-cyclohexanedimethanol , 1,2-cyclohexanedimethanol, tricyclodecane dimethanol, adamantanediol, pentacyclopentadecane dimethanol, and combinations thereof, but is not limited thereto.
The diol compound component is preferably used in an amount of 0.1 to 25 mol%, more preferably 0.5 to 20 mol%, further preferably 1 to 20 mol%, based on 100 mol% of the total diol compound, To 20 mol% of the diol compound (s) and contains the remainder of the diol compound (such as an aromatic diol or an aliphatic diol, preferably an aromatic diol) other than the anhydropoly alcohol to which the adduct is added. If the content of anhydrosugar alcohol to which the adduct is added in the diol compound component is less than 0.1 mol%, the effect of improving the tensile properties of the resultant copolymer may not be sufficient. If it exceeds 25 mol%, the production cost increases and the glass transition temperature And mechanical properties may deteriorate.
The sulfone compound component may preferably be a dihalogenated sulfone compound, more specifically, a dihalogenated diaryl sulfone, and more specifically, 4,4'-dichlorodiphenyl sulfone, 4,4'-di Fluorodiphenyl sulfone, and combinations thereof.
The content ratio of the repeating unit derived from the diol compound component and the repeating unit derived from the sulfone compound component contained in the polysulfone-based copolymer of the present invention is not particularly limited, but the ratio of the repeating unit derived from the sulfone compound The content is preferably 0.5 to 3 moles, and more preferably 0.8 to 1.5 moles. If the amount of the repeating unit of the sulfone compound is excessively small or excessively larger than the total repeating unit of the diol component contained in the polysulfone copolymer, the reaction between the diol component and the sulfone compound may not be properly performed, and thus it may be difficult to obtain the desired molecular weight.
According to some embodiments of the present invention, the polysulfone-based copolymer of the present invention may include a structure represented by any one of the following general formulas (1) to (5) in a copolymer, wherein parentheses [ ] Represents a repeating unit, n is an integer of 1 to 15, and m is an integer of 1 to 10).
[Chemical Formula 1]
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
According to another aspect of the present invention, there is provided a process for producing a diol compound and a sulfone compound, comprising the steps of: (1) polymerizing a diol compound component and a sulfone compound component containing an anhydropolydoic alcohol having at least two adducts selected from ethylene oxide and aliphatic diol at both ends in the presence of an alkali metal salt catalyst ; (2) diluting the polymerization reaction product, and then removing the alkali metal halide therefrom; And (3) precipitating the result of the diluted polymerization reaction, followed by washing the resultant, and a process for producing the polysulfone-based copolymer.
As the sulfone compound used in the production of the polysulfone-based copolymer of the present invention, a dihalogenated sulfone compound, more specifically a dihalogenated diaryl sulfone, may be used, and more specifically, 4,4'-dichloro Diphenyl sulfone, 4,4'-difluorodiphenyl sulfone, and combinations thereof.
In addition to the dihalogenated sulfone compound, other dihalogenated compounds may be further used. Preferably, 1 to 50 parts by weight of the dihalogenated compound may be further added to 100 parts by weight of the dihalogenated sulfone compound.
The alkali metal salt catalyst is preferably selected from the group consisting of potassium carbonate, sodium carbonate, sodium hydroxide, potassium hydroxide, and mixtures thereof. There is no particular limitation on the amount of the catalyst to be used, but if the amount of the catalyst is too small, the reaction rate will be slow. On the other hand, if the amount is too large, the residual catalyst may discolor or deteriorate the physical properties of the product. According to one embodiment of the present invention, for example, 0.8 to 3 moles, more preferably 1 to 1.5 moles of catalyst, based on 1 mole of the total diol component can be used.
The polymerization reaction may be carried out in a reaction solvent (e.g., N-methyl-2-pyrrolidone (NMP), dimethylsulfoxide (DMSO), dimethylacetamide (For example, dichloromethane, dimethylformamide, dimethylformamide, sulfolane, diphenylsulfone (DPS), dimethylsulfone (DMS) and the like or a mixed solvent thereof) (THF) or the like, or a mixed solvent thereof), but the present invention is not limited thereto. After completion of the polymerization, the polymerization reaction product is diluted (the same solvent as the polymerization reaction solvent can be used as the diluting solvent, for example, NMP can be used), and the alkali metal halide A salt of a halogen derived from an alkali metal salt catalyst and a halogen salt derived from a dihalogenated sulfone compound, for example, KCl) is removed by, for example, a celite filter or a decanter centrifuge using a difference in specific gravity. Thereafter, the resulting diluted and filtered reaction product is precipitated in a solvent (for example, an alcohol such as methanol or ultrapure water) and then washed with distilled water or the like to prepare the polysulfone copolymer of the present invention.
As described above, the polysulfone-based copolymer of the present invention can solve the problem of depletion of petroleum resources because it uses anhydrous alcohol which is a biogenic material as a raw material and has remarkably excellent mechanical properties as compared with conventional sulfonic polymers, And can be suitably used for various molding materials and resin processed products such as membranes. In addition, since it exhibits significantly improved tensile properties as compared with conventional sulfonic copolymers, it can be expected to increase the durability due to the improvement in stretchability when applied to a membrane of conventional use, and can be suitably used for fiber applications.
Thus, according to another aspect of the present invention, a molded article, preferably a membrane, made using the polysulfone copolymer of the present invention may be provided. The forming process includes, but is not limited to, solution spinning, casting (coating), extrusion, injection, and the like. The application fields of the membrane provided according to the present invention include water treatment R / O membranes, fuel cell electrolyte membranes, Medical blood dialysis membranes, electrical and electronic connectors, automotive parts, and the like, but are not limited thereto. The method for producing a molded product such as a membrane by using the polysulfone copolymer of the present invention is not particularly limited, and a method generally used for producing a molded resin product can be used as it is or modified appropriately.
Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples. However, the scope of the present invention is not limited thereto.
[ Example ]
Example 1-3
Bisphenol A (BPA) (0.95 mole), isosorbide (EO-ISB) added with ethylene oxide at both terminals, and ethylene oxide added at each end were added to a 1 L three-necked flask equipped with a stirrer, a thermometer and a condenser (0.05 mole), 4,4'-dichlorodiphenyl sulfone (DCDPS) (1.0 mole), N-methyl-2-pyrrolidone -pyrrolidone, NMP) (10.1 mole), potassium carbonate (1.1 mole) and chlorobenzene (1.11 mole). The reaction mixture was rapidly heated to a reaction temperature (160 ° C) under nitrogen purge, and then the reaction was allowed to proceed. It was confirmed that the chlorobenzene added as the co-solvent was azeotropically distilled out of the reaction by-product, H 2 O, over the reaction time. After a reaction time of 9 hours 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 at room temperature and then diluted with a solvent NMP previously prepared. The diluted reaction mixture was filtered through celite and then precipitated in methanol. The precipitated product was washed with distilled water, filtered and dried to prepare a polysulfone-based copolymer of Example 1 containing isosorbide (ISB) with ethylene oxide added thereto.
Polysulfone-based copolymers of Examples 2 and 3 were prepared in the same manner as in Example 1 using raw materials having the molar ratios shown in Table 1 below.
Example 4 to 6
4,4'-dihydroxydiphenyl sulfone (DHDPS) (0.95 mole) and the same ethylene oxide-adducted isosorbide (EO-ISB) (0.05 mole , 1.0 mole of 4,4'-dichlorodiphenyl sulfone (DCDPS), 10.1 mole of N-methyl-2-pyrrolidone (NMP), 1.1 mole of potassium carbonate and 1.11 mole of chlorobenzene The polysulfone-based copolymer of Example 4 was prepared in the same manner as in Example 1, except that it was used.
The polysulfone-based copolymers of Examples 5 and 6 were prepared in the same manner as in Example 4, using the raw materials having the molar ratios shown in Table 2 below.
Example 7 ~ 9
(4,4'-dihydroxybiphenyl, DHBP) (0.95 mole), the same ethylene oxide-adduct isosorbate as in Example 1 1.0 mole of 4,4'-dichlorodiphenylsulfone (DCDPS), 10.1 mole of N-methyl-2-pyrrolidone (NMP) and 1.1 mole of potassium carbonate (EO-ISB) ) And chlorobenzene (1.11 moles) were used in place of the polyisobutylene-based copolymer (1).
Polysulfone-based copolymers of Examples 8 and 9 were prepared in the same manner as in Example 7 by using raw materials having the molar ratios shown in Table 3 below.
Example 10-12
Bisphenol A (BPA) (0.45 mole), 1,4-cyclohexanedimethanol (CHDM) (0.5 mole), and the same ethylene oxide-adducted isosorbide (EO- ISB) (0.05 mole), 4,4'-dichlorodiphenyl sulfone (DCDPS) (1.0 mole), N-methyl-2-pyrrolidone (NMP) (10.1 mole), potassium carbonate (1.11 moles) was used in place of the polyisocyanate compound (1).
Polysulfone-based copolymers of Examples 11 and 12 were prepared in the same manner as in Example 10, using the raw materials having the molar ratios shown in Table 4 below.
Comparative Example One
1.0 mole of bisphenol A (BPA), 1.0 mole of 4,4'-dichlorodiphenylsulfone (DCDPS), 10.1 mole of N-methyl-2-pyrrolidone (NMP) 1.1 mole) and chlorobenzene (1.11 moles) were used in place of the polyisobutylene-based copolymer.
Comparative Example 2
As Comparative Example 2, a PSU product (SOLVAY P-3500) for a membrane manufactured by Solvay was used.
The tensile properties (elongation percentage,%) of the respective copolymers of the above Examples and Comparative Examples were measured according to the following method using a tensile strength tester (Tensile Tester H5K-T, manufactured by Hounsfield, UK) Respectively.
<Tensile Properties Measurement Method>
1. First, completely dissolve the copolymer to be tested at a concentration of 25% in DMAc.
2. Each polymer solution was cast on a support made of polypropylene (PP) film with a thickness of 200 μm and a speed of 0.2 m / min using an applicator, and the temperature was 20 to 30 ° C. and the humidity was 30 to 80 % Air for about 2 minutes, and then subjected to a primary desolvation in a MeOH coagulation bath for 3 minutes. Thereafter, the film of the copolymer to be tested is peeled from the PP support. Thereafter, the peeled film is immersed in a H 2 O coagulation bath, followed by complete desolvation for about 3 hours, followed by drying at 80 ° C. for 3 hours.
3. Measure the tensile properties of the prepared specimen using a tensile strength tester (H5K-T) after cutting the fully dried film to size of 6cm * 1cm using a specimen cutter.
Claims (14)
Wherein the diol compound component is selected from the group consisting of (i) an unmodified alcohol having at least one adduct selected from ethylene oxide and aliphatic diol at both ends; And (ii) an aromatic diol, an alicyclic diol, or combinations thereof,
Wherein the sulfone compound component is a dihalogenated sulfone compound,
Wherein the aromatic diol is selected from the group consisting of bisphenol A, hydroquinone, 4,4'-dihydroxydiphenyl sulfone, 4,4'-biphenol, 3- (4-hydroxy) phenol,
Wherein the alicyclic diol is selected from the group consisting of 1,4-cyclohexane dimethanol, 1,3-cyclohexane dimethanol, 1,2-cyclohexane dimethanol, tricyclodecane dimethanol, adamantanediol, pentacyclopentadecane dimethanol, ≪ / RTI > and combinations thereof.
Polysulfone-based copolymer.
(2) diluting the polymerization reaction product, and then removing the alkali metal halide therefrom; And
(3) precipitating the result of the diluted polymerization reaction and then washing it,
Wherein the diol compound component is selected from the group consisting of (i) an unmodified alcohol having at least one adduct selected from ethylene oxide and aliphatic diol at both ends; And (ii) an aromatic diol, an alicyclic diol, or combinations thereof,
Wherein the sulfone compound component is a dihalogenated sulfone compound,
Wherein the aromatic diol is selected from the group consisting of bisphenol A, hydroquinone, 4,4'-dihydroxydiphenyl sulfone, 4,4'-biphenol, 3- (4-hydroxy) phenol,
Wherein the alicyclic diol is selected from the group consisting of 1,4-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,2-cyclohexanedimethanol, tricyclodecanedimethanol, adamantanediol, pentacyclopentadecanedimethanol, ≪ / RTI > and combinations thereof.
A method for producing a polysulfone-based copolymer.
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| KR101898909B1 (en) * | 2017-07-12 | 2018-09-14 | 한국화학연구원 | Method for preparing poly(arylene ether) copolymers containing isohexide unit and poly(arylene ether) copolymers prepared therefrom |
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| KR101973671B1 (en) * | 2017-10-27 | 2019-04-29 | 주식회사 삼양사 | Method for preparing polysulfone copolymer and polysulfone copolymer for 3d printing prepared by the same |
| KR102052935B1 (en) | 2018-02-14 | 2019-12-06 | 한국화학연구원 | Poly(heteroarylene ether) copolymers and method for preparing the same |
| WO2024078975A1 (en) | 2022-10-11 | 2024-04-18 | Solvay Specialty Polymers Usa, Llc | Polyarylethersulfone copolymer having improved hydrophilicity |
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| US20030212244A1 (en) * | 2002-03-19 | 2003-11-13 | Richard Hayes | Polymers made from bis(2-hydroxyethyl)isosorbide and enduses thereof |
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| US20030212244A1 (en) * | 2002-03-19 | 2003-11-13 | Richard Hayes | Polymers made from bis(2-hydroxyethyl)isosorbide and enduses thereof |
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| KR101898909B1 (en) * | 2017-07-12 | 2018-09-14 | 한국화학연구원 | Method for preparing poly(arylene ether) copolymers containing isohexide unit and poly(arylene ether) copolymers prepared therefrom |
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