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CN107793567B - Polyether sulfone resin containing methoxyl diphenyl sulfone ether group and synthetic method and application thereof - Google Patents

Polyether sulfone resin containing methoxyl diphenyl sulfone ether group and synthetic method and application thereof Download PDF

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CN107793567B
CN107793567B CN201611182979.4A CN201611182979A CN107793567B CN 107793567 B CN107793567 B CN 107793567B CN 201611182979 A CN201611182979 A CN 201611182979A CN 107793567 B CN107793567 B CN 107793567B
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sulfone
diphenyl sulfone
ether group
resin containing
polyether sulfone
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CN107793567A (en
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代惊奇
高红军
陈锐斌
孙学科
曹民
姜苏俊
曾祥斌
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Kingfa Science and Technology Co Ltd
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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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/08—Stabilised against heat, light or radiation or oxydation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/10—Transparent films; Clear coatings; Transparent materials

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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyethers (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
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Abstract

The invention discloses polyether sulfone resin containing methoxyl diphenyl sulfone ether group, a synthesis method and application thereof, wherein the structural formula is as follows:
Figure DEST_PATH_IMAGE002
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' -dihydroxydiphenyl sulfone, component B: 4,4 ¢ -dichlorodiphenyl sulfone, component C: the method is characterized in that methoxy diphenyl sulfone 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 methoxy diphenyl sulfone metal phenolate monomer is introduced into a PES polymer as a capping agent, so that the prepared polyether sulfone resin containing the methoxy diphenyl sulfone ether group 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

Polyether sulfone resin containing methoxyl diphenyl sulfone ether group and synthetic method and application thereof
Technical Field
The invention belongs to the technical field of high polymer materials, and particularly relates to polyether sulfone resin containing methoxyl diphenyl sulfone ether, a synthetic method and application thereof.
Background
The commercial Polyethersulfone (PES) uses dichlorodiphenyl sulfone as the production monomer, and the terminal groups of the polymer chain contain bonded chlorine, generally over 3000ppm, for thermal stability and molecular weight. 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 easy to be 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, which brings 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 provides the polyether sulfone resin containing the methoxyl diphenyl sulfone ether group, which has low chlorine content, light color and high transparency and does not discolor at high temperature for a long time.
The invention also aims to provide a synthesis method of the polyether sulfone resin containing the methoxyl diphenyl sulfone ether group.
The invention is realized by the following technical scheme:
the polyether sulfone resin containing the methoxyl diphenyl sulfone ether group has a structural formula as follows:
Figure 426968DEST_PATH_IMAGE001
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。
The method for synthesizing the polyether sulfone resin containing the methoxyl diphenyl sulfone ether group comprises the following steps: 4, 4' -dihydroxydiphenyl sulfone, component B: 4,4 ¢ -dichlorodiphenyl sulfone, component C: the method is characterized in that methoxy diphenyl sulfone 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 '-dihydroxydiphenyl sulfone and 4, 4' -dichlorodiphenyl sulfone 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 diphenyl sulfone metal phenolate to continue reacting for 20-30min, stopping stirring and heating, adding sulfolane for dilution, then putting the diluted sulfolane into a filter to filter out solid components, slowly putting the filtrate into deionized water to cool the filtrate into white strip-shaped solid, crushing the solid into powder by a crusher, boiling the powder by the deionized water for 1-2 h, 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 methoxyl diphenyl sulfone metal phenate is one or a mixture of a plurality of P-methoxyl diphenyl sulfone phenol sodium, P-methoxyl diphenyl sulfone phenol potassium, M-methoxyl diphenyl sulfone phenol sodium, M-methoxyl diphenyl sulfone phenol potassium, O-methoxyl diphenyl sulfone phenol sodium or O-methoxyl diphenyl sulfone phenol potassium, preferably one or a mixture of P-methoxyl diphenyl sulfone phenol sodium or P-methoxyl diphenyl sulfone phenol potassium.
The molar ratio of the 4,4 '-dihydroxydiphenyl sulfone 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 polyether sulfone resin composition which comprises the polyether sulfone resin containing the methoxyl diphenyl sulfone ether group.
The modified polyether sulfone resin composition also comprises at least one of a reinforcing filler, other polymer resin, a pigment or a dye.
The modified polyether sulfone resin composition can be prepared by blending and modifying the polyether sulfone tree containing the methoxyl diphenyl sulfone ether group 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 material is 0.01-20 mm, preferably 0.1-6 mm, the length-diameter ratio of the fibrous reinforcing material 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 polyether sulfone 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 filler reinforcements having an average filler 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 polyether sulfone resin composition can be prepared by blending and modifying the polyether sulfone tree containing the methoxyl diphenyl sulfone ether group with other polymer resins by adopting a common method and technology, wherein the other polymer resins comprise polyamide resin (PA), polycarbonate resin (PC), polysulfone resin (PSU), polyether sulfone resin (PES), Liquid Crystal Polymer (LCP), polyether ether ketone resin (PEEK), polyether imide resin (PEI), polyimide resin (PI) and the like.
The modified polyether sulfone resin composition can be used for coloring the polyether sulfone tree containing the methoxyl diphenyl sulfone ether group by adopting a general method and a general technology, comprises inorganic and organic pigments and dyes, and can be used for preparing various colors in nature.
The invention also provides application of the polyether sulfone resin containing the methoxyl diphenyl sulfone 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 methoxy diphenyl sulfone metal phenolate monomer is introduced into the PES polymer as a 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 methoxy diphenyl sulfone ether end group structure, the thermal stability is higher, no residue exists, even a small amount of residual monomer exists in a polymerization stage, the residual monomer can be dissolved and easily washed away in a post-treatment water washing purification stage, the color change or bubble generation caused by small molecule residue cannot be influenced under the high-temperature condition of a resin material, the chlorine content of the prepared polyether sulfone resin containing the methoxy diphenyl sulfone ether group is less than 900ppm, the light transmittance is greater 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 polyether sulfone resin has the characteristics of long-term high-temperature resistance and.
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:
7.508kg (30 mol) of 4,4 '-dihydroxydiphenyl sulfone, 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 Na2CO3Then 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; maintaining the temperature within the range of 200-210 ℃, when the collected water amount is close to a theoretical value (540 g), continuously refluxing for 20 minutes, observing that water drops fall, proving that the salt formation is complete, distilling and discharging dimethylbenzene, gradually heating to 230 ℃ to start a polymerization reaction, and keeping the temperature for 2.5 hours to basically finish the polymerization reaction; adding 0.344kg (1.2 mol) of p-methoxy diphenylsulfone phenol sodium, continuing to react for 30min, and finishing the reaction; stopping stirring and heating, adding sulfolane 7kg for dilution, filtering to remove solid component in filter, slowly cooling the filtrate in deionized water to obtain white strip solid, and pulverizing into powderBoiling with deionized water for 1 hour, filtering to remove water, repeating the process for 10 times until the filtrate is detected with silver nitrate and is not turbid, which indicates that the by-product salt in the powder is washed out completely, and drying the polymer in a vacuum oven at 120 ℃ to constant weight after filtering to obtain biphenyl polyether sulfone resin containing methoxyl diphenyl sulfone 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 0.344kg (1.2 mol) of sodium p-methoxydiphenylsulfone phenolate added at the end of the polymerization was changed to 0.344kg (1.2 mol) of sodium m-methoxydiphenylsulfone phenolate.
Example 3:
the preparation process conditions were the same as in example 1 except that 0.344kg (1.2 mol) of sodium p-methoxydiphenylsulfone phenolate added at the end of the polymerization was changed to 0.344kg (1.2 mol) of sodium o-methoxydiphenylsulfone phenolate.
Example 4:
the preparation process conditions were the same as in example 1 except that 0.344kg (1.2 mol) of sodium p-methoxydiphenylsulfone phenolate added at the end of the polymerization was changed to 0.363kg (1.2 mol) of potassium p-methoxydiphenylsulfone phenolate.
Example 5:
the same procedures as in example 1 were repeated except that the amount of 4, 4' -dichlorodiphenyl sulfone added as a raw material monomer was changed to 8.623kg (30.03 mol), and the amount of sodium p-methoxydiphenyl sulfone phenolate added at the latter stage of the polymerization was changed to 17.2g (0.06 mol).
Example 6:
the same procedures as in example 1 were repeated except that the amount of 4, 4' -dichlorodiphenyl sulfone added as a raw material monomer was changed to 8.701kg (30.3 mol), and the amount of sodium p-methoxydiphenyl sulfone phenolate added at the latter stage of the polymerization was changed to 0.172kg (0.6 mol).
Example 7:
the same procedure as in example 1 was repeated except that the amount of 4, 4' -dichlorodiphenyl sulfone used as the starting monomer was changed to 9.045kg (30.9 mol), and the amount of sodium p-methoxydiphenyl sulfone phenolate added at the latter stage of the polymerization was changed to 0.516kg (1.8 mol).
Example 8:
the same procedure as in example 1 was repeated except that the amount of 4, 4' -dichlorodiphenyl sulfone added as a raw material monomer was changed to 9.045kg (31.5 mol), and the amount of sodium p-methoxydiphenyl sulfone phenolate added at the latter stage of the polymerization was changed to 0.86kg (3 mol).
Comparative example 1:
no sodium p-methoxydiphenylsulfone phenolate was added at the end of the polymerization, and the other preparation process conditions were the same as in example 1.
Comparative example 2:
no sodium p-methoxydiphenylsulfone phenolate was added at the end of the polymerization, and the other preparation process conditions were the same as in example 5.
Comparative example 3:
no sodium p-methoxydiphenylsulfone phenolate was added at the end 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 device from IKA, 100 mg of polyether sulfone resin samples containing methoxydiphenylsulfone ether groups were weighed into an acetobutyrate capsule equipped with an ignition wire and connected to the two electrodes of the decomposition device, 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
Figure 609687DEST_PATH_IMAGE002
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 methoxy diphenyl sulfone metal phenolate monomer as a capping agent into the PES polymer, meets the low halogen requirement of electronic appliances, and has light color, high transparency and no discoloration for a long time at high temperature.

Claims (9)

1. The polyether sulfone resin containing the methoxyl diphenyl sulfone ether group has a structural formula as follows:
Figure 508740DEST_PATH_IMAGE001
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 polyether sulfone resin containing methoxy diphenyl sulfone ether group as defined in claim 1,
the method comprises the following steps: 4, 4' -dihydroxydiphenyl sulfone, component B: 4, 4' -dichlorodiphenyl sulfone, component C: the method is characterized in that methoxy diphenyl sulfone 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 '-dihydroxydiphenyl sulfone and 4, 4' -dichlorodiphenyl sulfone 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 diphenyl sulfone metal phenolate to continue reacting for 20-30min, stopping stirring and heating, adding sulfolane for dilution, then putting the diluted sulfolane into a filter to filter out solid components, slowly putting the filtrate into deionized water to cool the filtrate into white strip-shaped solid, crushing the solid into powder by a crusher, boiling the powder by the deionized water for 1-2 h, 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 polyether sulfone resin containing methoxy diphenyl sulfone ether group as claimed in claim 2, wherein the methoxy diphenyl sulfone metal phenolate is one or a mixture of p-methoxy diphenyl sulfone phenol sodium or p-methoxy diphenyl sulfone phenol potassium.
4. The method for synthesizing polyether sulfone resin containing methoxy diphenyl sulfone ether group according to claim 2, wherein the molar ratio of 4,4 '-dihydroxy diphenyl sulfone to 4, 4' -dichloro diphenyl sulfone is 1: 1.001-1: 1.05.
5. the method for synthesizing polyether sulfone resin containing methoxy diphenyl sulfone ether group as claimed in claim 2, wherein the mole numbers of the component C and the components A and B satisfy the relation: c =2 (B-a).
6. The method for synthesizing polyether sulfone resin containing methoxy diphenyl sulfone ether group as claimed in claim 2, wherein the alkali metal carbonate is Na2CO3、K2CO3Or mixtures thereof in different proportions.
7. A modified polyethersulfone resin composition comprising the polyethersulfone resin containing methoxydiphenylsulfone ether group of claim 1.
8. The modified polyethersulfone resin composition of claim 7, further comprising at least one of reinforcing fillers, other polymeric resins, pigments or dyes.
9. The use of the polyether sulfone resin containing methoxydiphenyl sulfone ether group according to claim 1 in electronic appliances.
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