CN107793568B - Biphenyl polyether sulfone resin containing methoxy biphenyl ether group and synthesis method and application thereof - Google Patents
Biphenyl polyether sulfone resin containing methoxy biphenyl ether group and synthesis method and application thereof Download PDFInfo
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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
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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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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K2201/002—Physical properties
- C08K2201/003—Additives being defined by their diameter
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K2201/002—Physical properties
- C08K2201/004—Additives being defined by their length
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
The invention discloses biphenyl polyether sulfone resin containing methoxy biphenyl ether group, a synthesis method and application thereof, wherein the structural formula of the resin is as follows:
wherein R is1，R2，R3Each independently represents H and-OCH3And R is1，R2，R3Two of them are simultaneously H, and the other one is-OCH3(ii) a n = 2-2000. The synthesis method comprises the following steps: 4, 4' -dihydroxybiphenyl, component B: 4, 4' -dichlorodiphenyl sulfone, component C: the method is characterized in that methoxy biphenyl metal phenolate is used as a reaction monomer, sulfolane is used as a solvent, alkali metal carbonate is used as a salt forming agent, and solution polymerization technology is adopted for polymerization. According to the invention, a methoxyl biphenyl metal phenolate monomer is introduced into a PPSU polymer as an end capping agent, so that the prepared biphenyl polyether sulfone resin containing methoxyl biphenyl ether groups has the chlorine content of less than 900ppm, the light transmittance of more than 83%, the haze of less than 3% and the yellowness index of less than 15, and has the characteristics of remarkably improved transparency and color level, long-term high temperature resistance and no discoloration.
Description
Technical Field
The invention belongs to the technical field of high polymer materials, and particularly relates to biphenyl polyether sulfone resin containing methoxy biphenyl ether groups, and a synthesis method and application thereof.
Background
One of the production monomers used in the commercially available biphenyl polyethersulfone (PPSU) is dichlorodiphenylsulfone, and the terminal groups of the polymer chains contain bonded chlorine, typically over 3000ppm, for thermal stability and molecular weight considerations. The content of polymer-bound halogen, especially chlorine, is too high for many applications because of the potential for corrosion of metals and generally does not meet the flame retardant requirements. Applications in the electronics field, such as switches, circuit breakers, fuses, IC holders, housings, foils, generally require very low chlorine contents, for example less than 900 ppm. In addition, the known biphenyl polyethersulfone polymers also have relatively high residual solvent content.
The patent CN102365312B discloses a method for preparing PPSU with low chlorine content, which is to add monochlorodiphenylsulfone to reduce the chlorine end group content to below 800ppm, and at the same time, to improve the elongation at break and to improve the fluidity under low shear, but researches have found that monochlorodiphenylsulfone has low activity, will generate more unreacted monomer residues, and is not easily removed in the post-treatment purification process, resulting in obvious changes in the heat resistance and color of the resin, and will generate bubbles due to the gasification of small molecules, thereby bringing hidden troubles to normal use. The method for preparing PPSU disclosed in patent CN 102498158A is to prepare resin with lower chlorine end group content than 400ppm and lighter color by adding aqueous solution of metal hydroxide at the later stage of polymerization, but the preparation process is difficult to control stably and has potential safety hazard because the material system is at high temperature higher than 190 ℃ in the polymerization stage, and if the aqueous solution is added, a large amount of water vapor and high-temperature material splash can be generated and even ejected out of the polymerization equipment.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide the biphenyl polyether sulfone resin containing the methoxy biphenyl ether group, which has low chlorine content, light color, high transparency and no color change at high temperature for a long time.
The invention also aims to provide a synthesis method of the biphenyl polyether sulfone resin containing the methoxyl biphenyl ether group.
The invention is realized by the following technical scheme:
a biphenyl polyether sulfone resin containing methoxyl biphenyl ether group has a structural formula as follows:
wherein R is1，R2，R3Each independently represents H and-OCH3And R is1，R2，R3Two of them are simultaneously H, and the other one is-OCH3；
n=2-2000。
Preferably, R2，R3At the same time being H, R1is-OCH3。
A synthetic method of the biphenyl polyether sulfone resin containing the methoxyl biphenyl ether group comprises the following steps: 4, 4' -dihydroxybiphenyl, component B: 4, 4' -dichlorodiphenyl sulfone, component C: the method is characterized in that methoxy biphenyl metal phenolate is used as a reaction monomer, sulfolane is used as a solvent, alkali metal carbonate is used as a salt forming agent, and a solution polymerization technology is adopted for polymerization, and the method comprises the following steps:
a. sequentially adding 4,4 '-dihydroxybiphenyl, 4, 4' -dichlorodiphenyl sulfone and sulfolane into a polymerization kettle provided with a thermometer, a nitrogen introducing pipe, a condensation water separator and a stirrer, adding sulfolane, stirring, heating to 100 ℃, dissolving monomers until the solution is transparent, adding a salt forming agent, then adding xylene, continuously stirring, heating until a salt forming reaction starts, blowing an azeotrope generated by water and xylene in a system into a condensing pipe by protective gas, condensing and dripping into the water separator for layering, and refluxing the xylene on the upper layer into the system;
b. maintaining the temperature within the range of 200-210 ℃, when the collected water amount reaches a theoretical value, continuously refluxing for 20-30min, observing that no water drops fall off, proving that the salt formation is complete, distilling and releasing dimethylbenzene, gradually heating to the temperature of 220-240 ℃ to start the polymerization reaction, and keeping the temperature for 1-3 hours to basically finish the polymerization reaction;
c. adding methoxyl biphenyl metal phenolate to continue reacting for 20-30min, stopping stirring and heating, adding sulfolane to dilute, then placing the solution into a filter to filter out solid components, slowly placing the filtrate into deionized water to cool the solution into white strip-shaped solid, crushing the solid into powder by a crusher, boiling the powder for 1-2 h by the deionized water, filtering the solution to remove water, repeating the steps until the filtrate is detected by silver nitrate to be not turbid, and drying the polymer to constant weight by a vacuum oven after filtering to obtain the product.
The metal phenolate of the methoxyl biphenyl is one or a mixture of a plurality of sodium p-methoxyl diphenol, potassium p-methoxyl diphenol, sodium m-methoxyl diphenol, potassium m-methoxyl diphenol, sodium o-methoxyl diphenol or potassium o-methoxyl diphenol, and preferably one or a mixture of two of sodium p-methoxyl diphenol or potassium p-methoxyl diphenol.
The molar ratio of the 4,4 '-dihydroxybiphenyl to the 4, 4' -dichlorodiphenyl sulfone is 1: 1.001-1: 1.05.
the mole number of the component C and the mole number of the component A and the component B satisfy the relation: c =2 (B-a).
The alkali metal carbonate is Na2CO3、K2CO3Or mixtures thereof in different proportions.
The invention also provides a modified biphenyl polyether sulfone resin composition which comprises the biphenyl polyether sulfone resin containing the methoxyl biphenyl ether group.
The modified biphenyl polyethersulfone resin composition further comprises at least one of reinforcing filler, other polymer resin, pigment or dye.
The modified biphenyl polyethersulfone resin composition can be prepared by blending and modifying the biphenyl polyethersulfone resin containing methoxyl biphenyl ether groups with a reinforcing filler by adopting a general method and a general technology, wherein the reinforcing filler comprises a fibrous reinforcing filler, the average fiber length of the fibrous reinforcing filler is 0.01-20 mm, preferably 0.1-6 mm, the length-diameter ratio of the fibrous reinforcing filler is 5:1-2000:1, preferably 30:1-600:1, and the content of the fibrous reinforcing filler is 10-50 wt%, preferably 10-30 wt% based on the total weight of the modified biphenyl polyethersulfone resin composition; one or more selected from glass fiber, carbon fiber, potassium titanate fiber, metal-clad glass fiber, ceramic fiber, wollastonite fiber, metal carbide fiber, metal solidified fiber, asbestos fiber, alumina fiber, silicon carbide fiber, gypsum fiber or boron fiber, preferably glass fiber and carbon fiber; also included are non-fibrous reinforcing fillers having an average particle size of from 0.001 μm to 100 μm, preferably from 0.01 μm to 50 μm, selected from one or more of potassium titanate whiskers, zinc oxide whiskers, aluminum borate whiskers, wollastonite, zeolite, sericite, kaolin, mica, talc, clay, pyrophyllite, bentonite, montmorillonite, hectorite, synthetic mica, asbestos, aluminosilicate, alumina, silica, magnesia, zirconia, titania, iron oxide, calcium carbonate, magnesium carbonate, dolomite, calcium sulfate, barium sulfate, magnesium hydroxide, calcium hydroxide, aluminum hydroxide, glass beads, ceramic beads, boron nitride, silicon carbide or silica.
The modified biphenyl polyethersulfone resin composition can be prepared by blending and modifying the biphenyl polyethersulfone resin containing methoxyl biphenyl ether group with other polymer resins by adopting a common method and technique, wherein the other polymer resins comprise polyamide resin (PA), polycarbonate resin (PC), polysulfone resin (PSU), polyethersulfone resin (PES), Liquid Crystal Polymer (LCP), polyether ether ketone resin (PEEK), polyetherimide resin (PEI), polyimide resin (PI) and the like.
The modified biphenyl polyethersulfone resin composition can also be used for coloring the biphenyl polyethersulfone resin containing methoxyl biphenyl ether group by adopting a general method and a general technology, and can be used for preparing various colors in nature by adopting inorganic and organic pigments and dyes.
The invention also provides application of the biphenyl polyether sulfone resin containing the methoxy biphenyl ether group in electronic appliances, such as switches, circuit breakers, fuses, IC supports, shells and foils.
Compared with the prior art, the invention has the following beneficial effects:
according to the invention, the methoxyl biphenyl metal phenolate monomer is introduced into the PPSU polymer as the end capping agent, so that the reaction degree can be improved, the content of chlorine in a molecular chain is reduced, the molecular chain end group contains a methoxyl biphenyl ether end group structure, the thermal stability is higher, no residue exists, even a small amount of residual monomer exists in the polymerization stage, the residual monomer can be dissolved and easily washed away in the post-treatment water washing purification stage, the color change or bubble generation caused by micromolecule residue under the high-temperature condition of the resin material is avoided, the chlorine content of the prepared methoxyl biphenyl ether group-containing biphenyl polyether sulfone resin is less than 900ppm, the light transmittance is more than 83%, the haze is less than 3%, the yellowness index is less than 15, the transparency and the color level are obviously improved, and the resin has the characteristics of long-term high-temperature resistance and no color.
Detailed Description
The present invention is further illustrated by the following specific embodiments, which are not intended to limit the scope of the invention.
The raw materials used in the examples and comparative examples of the present invention were all commercially available.
Example 1:
5.586kg (30 mol) of 4,4 '-dihydroxybiphenyl, 8.787kg (30.6 mol) of 4, 4' -dichlorodiphenyl sulfone and 32.62kg of sulfolane are sequentially added into a 50L polymerization kettle provided with a thermometer, a nitrogen pipe, a condensation water separator and a stirrer, stirred and heated to 100 ℃ to dissolve the monomers until the solution is transparent, and 3.505kg (33 mol) of a salt forming agent Na is added2CO3Then adding 2L of dimethylbenzene, continuously stirring and heating until a salt forming reaction starts, blowing out an azeotrope generated by water and the dimethylbenzene in the system into a condenser pipe by protective gas, condensing and dripping into a water separator for layering, and refluxing the upper layer of dimethylbenzene into the system; the temperature was maintained in the range of 200 ℃ to 210 ℃ and when the amount of collected water reached the theoretical value (540 g), the reflux was continued for another 20 minutes without any observationWater drops fall to prove that the salt formation is complete, then xylene is distilled and discharged, the temperature is gradually increased to 230 ℃ to start the polymerization reaction, and the polymerization reaction is basically finished after the constant temperature is kept for 2.5 hours; adding 0.267kg (1.2 mol) of p-methoxy sodium diphenol, continuing to react for 30min, and finishing the reaction; stopping stirring and heating, adding 7kg of sulfolane for dilution, then placing the mixture into a filter to filter out solid components, slowly placing the filtrate into deionized water to be cooled into white strip-shaped solid, crushing the white strip-shaped solid into powder by using a crusher, boiling the powder for 1 hour by using the deionized water, filtering out water, repeating the operation for 10 times until the filtrate is detected by silver nitrate to be not turbid, washing out the byproduct salt in the powder, filtering, and drying the polymer by using a vacuum oven at 120 ℃ to constant weight to obtain the biphenyl polyether sulfone resin containing the methoxyl biphenyl ether group; the performance index test results are shown in table 1.
Example 2:
the preparation process conditions were the same as in example 1 except that 0.267kg (1.2 mol) of sodium p-methoxydiphenol added at the late stage of the polymerization was changed to 0.267kg (1.2 mol) of sodium m-methoxydiphenol.
Example 3:
the preparation process conditions were the same as in example 1 except that 0.267kg (1.2 mol) of sodium p-methoxydiphenol added at the late stage of the polymerization was changed to 0.267kg (1.2 mol) of sodium o-methoxydiphenol.
Example 4:
the preparation process conditions were the same as in example 1 except that 0.267kg (1.2 mol) of sodium p-methoxybenzophenone added at the end of the polymerization was changed to 0.286kg (1.2 mol) of potassium p-methoxybenzophenone.
Example 5:
the same procedures as in example 1 were repeated except that the amount of 4, 4' -dichlorodiphenyl sulfone used as a starting monomer was changed to 8.623kg (30.03 mol), and the amount of sodium p-methoxydiphenol added at the latter stage of the polymerization was changed to 13.35g (0.06 mol).
Example 6:
the same procedures as in example 1 were repeated except that the amount of 4, 4' -dichlorodiphenyl sulfone used as a starting monomer was changed to 8.701kg (30.3 mol), and sodium p-methoxydiphenol added at the latter stage of the polymerization was changed to 0.134kg (0.6 mol).
Example 7:
the same procedures as in example 1 were repeated except that the amount of 4, 4' -dichlorodiphenyl sulfone used as a starting monomer was changed to 9.045kg (30.9 mol), and sodium p-methoxydiphenol added at the latter stage of the polymerization was changed to 0.401kg (1.8 mol).
Example 8:
the same procedures as in example 1 were repeated except that the amount of 4, 4' -dichlorodiphenyl sulfone used as a starting monomer was changed to 9.045kg (31.5 mol), and the amount of sodium p-methoxydiphenol added at the latter stage of the polymerization was changed to 0.667kg (3 mol).
Comparative example 1:
no sodium p-methoxydiphenol was added in the late stage of the polymerization, and the other preparation process conditions were the same as in example 1.
Comparative example 2:
no sodium p-methoxydiphenol was added in the late stage of the polymerization, and the other preparation process conditions were the same as in example 5.
Comparative example 3:
no sodium p-methoxydiphenol was added in the late stage of the polymerization, and the other preparation process conditions were the same as in example 8.
The performance test method comprises the following steps:
the determination method of the chlorine content comprises the following steps:
the chlorine content was determined by means of ion chromatography. First, samples were prepared as follows:
for the determination of the chlorine content, the decomposition of the samples was carried out using an oxygen decomposition apparatus from IKA, 100 mg of biphenyl polyether sulfone resin samples containing methoxy biphenyl ether groups were weighed into an acetobutyrate capsule equipped with an ignition wire and connected to the two electrodes of the decomposition apparatus, as absorption solution, ignition was carried out using 10 ml of 30% hydrogen peroxide under 30 bar oxygen, the decomposition solution was filtered, filled into vials, and finally the chloride was analyzed by ion chromatography, the chlorine content being obtained by calculation.
Ion chromatography was performed with the following parameters:
device ICS-90 (Dionex corporation)
Column IonPac AS12A Analytical Column (4X 200 mm)
Eluent 2.7 mM sodium carbonate
0.3 mM sodium bicarbonate
Detection-conductivity detector
The flow rate was 1 ml/min.
Evaluation was performed by external standard method. For this purpose, calibration curves were determined from 3 different chloride solutions of known concentration.
Light transmittance: measured using ASTM D-1003 on 2mm thick samples;
haze: measured using ASTM D-1003 on 2mm thick samples;
yellowness index: the measurements were carried out using ASTM D-1925 on 2mm thick specimens.
Table 1 results of performance testing
As can be seen from the results of the examples and comparative examples in Table 1, the invention reduces the chlorine content by introducing the methoxybiphenyl metal phenolate monomer as an end-capping agent into the PPSU polymer, meets the low halogen requirement of electronic and electric appliances, and has light color, high transparency and no discoloration for a long time at high temperature.
Claims (9)
1. A biphenyl polyether sulfone resin containing methoxyl biphenyl ether group has a structural formula as follows:
wherein R is1，R2，R3Each independently represents H and-OCH3And R is2，R3At the same time being H, R1is-OCH3；
n=2-2000。
2. A method for synthesizing biphenyl polyethersulfone resin containing methoxy biphenyl ether group as claimed in claim 1,
the method comprises the following steps: 4, 4' -dihydroxybiphenyl, component B: 4, 4' -dichlorodiphenyl sulfone, component C: the method is characterized in that methoxy biphenyl metal phenolate is used as a reaction monomer, sulfolane is used as a solvent, alkali metal carbonate is used as a salt forming agent, and a solution polymerization technology is adopted for polymerization, and the method comprises the following steps:
a. sequentially adding 4,4 '-dihydroxybiphenyl, 4, 4' -dichlorodiphenyl sulfone and sulfolane into a polymerization kettle provided with a thermometer, a nitrogen introducing pipe, a condensation water separator and a stirrer, adding sulfolane, stirring, heating to 100 ℃, dissolving monomers until the solution is transparent, adding a salt forming agent, then adding xylene, continuously stirring, heating until a salt forming reaction starts, blowing an azeotrope generated by water and xylene in a system into a condensing pipe by protective gas, condensing and dripping into the water separator for layering, and refluxing the xylene on the upper layer into the system;
b. maintaining the temperature within the range of 200-210 ℃, continuously refluxing for 20-30min when the collected water amount reaches a theoretical value, and when no water drop is observed, proving that the salt formation is complete, distilling and releasing dimethylbenzene, gradually heating to the temperature of 220-240 ℃ to start the polymerization reaction, and keeping the temperature for 1-3 hours to basically finish the polymerization reaction;
c. adding methoxyl biphenyl metal phenolate to continue reacting for 20-30min, stopping stirring and heating, adding sulfolane to dilute, then placing the solution into a filter to filter out solid components, slowly placing the filtrate into deionized water to cool the solution into white strip-shaped solid, crushing the solid into powder by a crusher, boiling the powder for 1-2 h by the deionized water, filtering the solution to remove water, repeating the steps until the filtrate is detected by silver nitrate to be not turbid, and drying the polymer to constant weight by a vacuum oven after filtering to obtain the product.
3. The method for synthesizing biphenyl polyether sulfone resin containing methoxy biphenyl ether group as claimed in claim 2, wherein the methoxy biphenyl metal phenolate is one or a mixture of p-methoxy diphenol sodium and p-methoxy diphenol potassium.
4. The method for synthesizing biphenyl polyether sulfone resin containing methoxy biphenyl ether group according to claim 2, wherein,
the molar ratio of the 4,4 '-dihydroxybiphenyl to the 4, 4' -dichlorodiphenyl sulfone is 1: 1.001-1: 1.05.
5. the method for synthesizing biphenyl polyether sulfone resin containing methoxy biphenyl ether group as claimed in claim 2, wherein the mole numbers of the component C, the component A and the component B satisfy the relation: c =2 (B-a).
6. The method for synthesizing biphenyl polyether sulfone resin containing methoxy biphenyl ether group as claimed in claim 2, wherein the alkali metal carbonate is Na2CO3、K2CO3Or mixtures thereof in different proportions.
7. A modified biphenyl polyethersulfone resin composition, comprising the biphenyl polyethersulfone resin containing methoxy biphenyl ether groups of claim 1.
8. The modified biphenyl polyethersulfone resin composition of claim 7, further comprising at least one of reinforcing fillers, other polymeric resins, pigments or dyes.
9. The biphenyl polyethersulfone resin containing methoxy biphenyl ether group as claimed in claim 1, wherein said biphenyl polyethersulfone resin is used in electronic appliances.
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| PCT/CN2017/113748 WO2018113494A1 (en) | 2016-12-20 | 2017-11-30 | Methoxydiphenyl ether-containing biphenyl polyethersulfone resin, synthesis method for same, and applications thereof |
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| CN110128656B (en) * | 2019-05-27 | 2021-07-02 | 江西金海新能源科技有限公司 | Low-chlorine-content end-capped sulfone polymer and preparation method and application thereof |
| CN110452383A (en) * | 2019-08-28 | 2019-11-15 | 江西金海新能源科技有限公司 | A kind of high thermal stability sealing end sulfone polymer, preparation method and its application on tableware |
| JPWO2021065770A1 (en) * | 2019-10-02 | 2021-04-08 | ||
| CN110951060A (en) * | 2019-12-20 | 2020-04-03 | 江门市德众泰工程塑胶科技有限公司 | High-fluidity wholly aromatic liquid crystal polyester and preparation method thereof |
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|---|---|
| CN107793568A (en) | 2018-03-13 |
| WO2018113494A1 (en) | 2018-06-28 |
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