CN100595184C - Application of fluorine monomer containing anthracene benzophenone substituent - Google Patents
Application of fluorine monomer containing anthracene benzophenone substituent Download PDFInfo
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- CN100595184C CN100595184C CN200810050318A CN200810050318A CN100595184C CN 100595184 C CN100595184 C CN 100595184C CN 200810050318 A CN200810050318 A CN 200810050318A CN 200810050318 A CN200810050318 A CN 200810050318A CN 100595184 C CN100595184 C CN 100595184C
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Abstract
The invention relates to a fluorine monomer with anthracene benzene ketone substituting group, the preparation method and the application, belonging to the technical field of macromolecular material.The fluorine monomer with anthracene benzene ketone substituting group is a new compound by the name of 9- (4- monofluoro-benzene acyl group) anthracene; the preparation is achieved through a step byFriedel-crafts alkylation. The fragrant ether alkone resin obtained from the fluorine monomer with anthracene benzene ketone substituting group and the hydroxyl sealed end polymer polymerization designed and synthesized by the fluorine monomer with anthracene benzene ketone substituting group has high thermostability, good solubility and mechanical strength; and the preparation method embodies theauto-crosslinking and good optical quality, thus has very broad application prospect in the fields of high temperature, high exposure and optics.
Description
Technical field
The invention belongs to the technical field of macromolecular material and preparation method thereof; Being particularly related to contain the substituent 4-fluoro-of anthracene benzophenone 9-anthracene benzophenone compound is the synthetic method that contains anthracene benzophenone polyaryletherketone resinous materials of raw material.
Background technology
The fire-resistant high-performance macromolecular material is the focus and the forward position research topic of field of polymer technology in recent years.A lot of thermoplastic resins such as polymeric amide, polyethersulfone, polyarylether, polyaryletherketone all have high thermostability, good excellent performances such as mechanical property, in a lot of fields important application prospects are being arranged.The polyaryletherketone base polymer contains rigidity, stable on heating phenylene and flexibility, stable on heating ehter bond in molecular structure, show high thermotolerance and high physical and mechanical properties.Wherein, with the PES of ICI company, PEEK, PEK and the polyphenylene thioether PPS S that developed afterwards, polyketone thioether PKS is representative, has showed important use value.
The prior art close with the present invention can be with reference to MATERIALS LETTERS 2006,60 (11): 1369-1373.Along with the introducing of crosslinkable groups in the molecular structure,, make polymkeric substance have controlled crosslinked character as introducing phenylacetylene base.But they also exist deficiency, it is exactly the synthetic method relative complex, the introducing of phenylacetylene group has destroyed the aromaticity of polymkeric substance, by its prepared high-performance line polymer, there is not sufficiently high chemoresistance ability, there is not good solvent resistivity, the easy optical property of dissolving, swelling or the excellence breaking, do not possess etc. in solvent.
Summary of the invention
The technical problem to be solved in the present invention is to overcome the deficiencies in the prior art, in polymkeric substance, introduce crosslinkable anthracene benzophenone group with the polyaryletherketone structural similitude, when not destroying the polyaryletherketone aromaticity, that can utilize anthracene nucleus is beneficial to thermostability that bridging property comes impact polymer, heat cross-linking, cross-linking radiation etc.; Simultaneously, embody the optical property of the not available excellence of prior art 4-phenylacetylene base phenol.
The structure that contains the substituent fluorine monomer of anthracene benzophenone of the present invention is:
Called after 9-(4-fluorobenzene acyl group) anthracene.
This compound is introduced in fluorine monomer and is contained anthracene benzophenone structure, can be when not changing the polyaryletherketone aromaticity, and introducing has anthracene benzophenone structure, and this structure has controlled self-crosslinking and excellent optical property.This structure is introduced polymkeric substance, make polymkeric substance have self heat cross-linking and excellent optical.
The preparation method who contains the substituent fluorine monomer of anthracene benzophenone of the present invention makes by Fu Shi acylations single step reaction.Reactions steps is as follows:
With anthracene, fluorobenzoyl chloride, methylene chloride are joined reaction system, add Zinc Chloride Anhydrous under the stirring at room, system refluxed 8～12 hours, steaming vibrating dichloromethane, discharging is used alkali liquid washing in acidic aqueous solution, vacuum-drying.Ethyl alcohol recrystallization gets light yellow solid, called after 9-(4-fluorobenzene acyl group) anthracene.Productive rate: 80～85%.Wherein anthracene, be 1: 1～1.2: 4～6 to the mol ratio of fluorobenzoyl chloride, Zinc Chloride Anhydrous, the amount ratio of anthracene and solvent is 1mol: 2000～6000ml.
The present invention is to be that starting raw material begins to synthesize with anthracene, is prepared into needed fluorine monomer through the Guo Fushi acylation reaction.In the acylations process, use ZnCl
2Replace the AlCl that uses always as catalyzer
3Better effects if, reaction can be more abundant, and reaction process is gentle more steadily, condition is easily controlled.
The purposes that contains the substituent fluorine monomer of anthracene benzophenone of the present invention is, is the polymkeric substance that the feedstock production end group contains anthracene benzophenone group with 9-(4-fluorobenzene acyl group) anthracene.
With 9-(4-fluorobenzene acyl group) anthracene is that the detailed process of polymkeric substance such as the synthetic end group of the raw material polyaryletherketone that contains anthracene benzophenone group, polyarylether is as described below.
Synthetic method 1:(end-blocking homopolymer)
Two fluorine monomers or two chlorine monomer, biphenol monomer, catalyzer Anhydrous potassium carbonate, solvent N-Methyl pyrrolidone (NMP) or tetramethylene sulfone, band aqua toluene or dimethylbenzene are joined in the container that nitrogen port, mechanical stirring, thermometer, water-taker and reflux condensing tube are housed; Under nitrogen protection, reflux and be with water 1.5～2 hours; After getting rid of toluene, be warmed up to 160～190 ℃, continue reaction 4～8 hours; Then 9-(4-fluorobenzene acyl group) anthracene is put in the reaction system, 140～170 ℃ of reactions 4～8 hours; Last discharging through pulverizing, washing, drying, obtains the homopolymer of purified anthracene benzophenone group end capping in acidic aqueous solution.
Wherein, biphenol monomer and two fluorine monomers or the monomeric mol ratio 1+1/n of two chlorine: 1 (1＜n＜10000); Biphenol monomer is 1: 1.03～1.05 with the amount of substance ratio of catalyzer; The two fluorine monomers of every 0.01mol or two chlorine monomer add solvent 20～30mL, band aqua 15～20mL.The mol ratio of 9-(4-fluorobenzene acyl group) anthracene and biphenol monomer is 2/n～2.1/n: 1+1/n.Described pair of fluorine monomer or two chlorine monomer comprise 4,4 '-difluorodiphenyl base ketone, 4,4 '-dichloro diphenyl sulfone, 1,4-two (4-fluorobenzene carbonyl) benzene, decafluorobiphenyl, 2,6-difluorobenzonilyile or other two fluorine monomers; Described biphenol monomer comprises 2,2-two (4-hydroxyphenyl) propane, 4,4 '-dihydroxy diphenylsulphone, Resorcinol, Resorcinol, 2,2-two (4-hydroxyphenyl) HFC-236fa, m-trifluoromethylphenyl Resorcinol or 3,5-two trifluoromethyl Resorcinol.
Synthetic method 2:(end-blocking random copolymers)
Two fluorine monomers or two chlorine monomer, biphenol monomer 1, biphenol monomer 2, catalyzer Anhydrous potassium carbonate, solvent N-Methyl pyrrolidone (NMP) or tetramethylene sulfone, band aqua toluene or dimethylbenzene are joined in the container that nitrogen port, mechanical stirring, thermometer, water-taker and reflux condensing tube are housed; Under nitrogen protection, reflux and be with water 1.5～2 hours; After getting rid of toluene, be warmed up to 160～190 ℃, continue reaction 4～8 hours; Then 9-(4-fluorobenzene acyl group) anthracene is put in the reaction system, 140～170 ℃ of reactions 4～8 hours; Last discharging through pulverizing, washing, drying, obtains the random copolymers of purified anthracene benzophenone group end capping in acidic aqueous solution.
Wherein, biphenol monomer summation and two fluorine monomer mol ratio 1+1/n: 1 (1＜n＜10000), the mol ratio of catalyzer and biphenol monomer summation is 1.03～1.05: 1; The two fluorine monomers of every 0.01mol, solubilizing agent 20～30mL, band aqua 10～15mL; 9-(4-fluorobenzene acyl group) anthracene is (2～2.1)/n: 1+1/n by the mol ratio with the biphenol monomer summation.Described pair of fluorine monomer or two chlorine monomer comprise 4,4 '-difluorodiphenyl base ketone, 4,4 '-dichloro diphenyl sulfone, 1,4-two (4-fluorobenzene carbonyl) benzene, decafluorobiphenyl, 2,6-difluorobenzonilyile or other two fluorine monomers; Described biphenol monomer 1, biphenol monomer 2 are 2,2-two (4-hydroxyphenyl) propane, 4,4 '-dihydroxy diphenylsulphone, Resorcinol, Resorcinol, 2,2-two (4-hydroxyphenyl) HFC-236fa, m-trifluoromethylphenyl Resorcinol or 3, in the 5-two trifluoromethyl Resorcinol different two kinds.
Designed and synthetic contains the fluorine monomer and the biphenol monomer of anthracene benzophenone structure or contains the fluorine monomer of anthracene benzophenone structure and polyaryletherketone resin that biphenol monomer and two fluorine monomer polymerization obtain with the present invention, have high glass transition and thermostability, solvability and mechanical strength preferably, its heat cross-linking temperature is at 260～340 ℃, the feature uv-absorbing has embodied good heat cross-linking behavior and optical property at 300～400nm.Thereby very wide application prospect is arranged at high temperature, high irradiation field, optical field.
Description of drawings
Fig. 1 is the nucleus magnetic hydrogen spectrum figure that the embodiment of the invention 1 makes sample.
Fig. 2 is the uv atlas that the embodiment of the invention 1 makes sample.
Fig. 3 is the infrared spectrum of the polymkeric substance that makes of the embodiment of the invention 3.
Embodiment
Synthetic (one) of embodiment 1:9-(4-fluorobenzene acyl group) anthracene
With anthracene (17.8g, 0.1mol), to fluorobenzoyl chloride (15.8g, 0.1mol), methylene chloride joins container (three-necked flask) reaction system, slowly add under the stirring at room Zinc Chloride Anhydrous (54.4g, 0.4mol); Anthracene, be 1: 1: 4 to the mol ratio of fluorobenzoyl chloride, Zinc Chloride Anhydrous, the amount ratio of anthracene and methylene chloride is 1mol: 2000ml; System refluxed 8 hours, steaming vibrating dichloromethane, and discharging is used the alkali lye repetitive scrubbing, vacuum-drying in water.Ethyl alcohol recrystallization gets light yellow solid, called after 9-(4-fluorobenzene acyl group) anthracene.
The nucleus magnetic hydrogen spectrum figure and the uv atlas of 9-(4-fluorobenzene acyl group) anthracene are seen Fig. 1 and Fig. 2 respectively.
Synthetic (two) of embodiment 2:9-(4-fluorobenzene acyl group) anthracene
With anthracene (17.8g, 0.1mol), to fluorobenzoyl chloride (18.96g, 0.12mol), methylene chloride joins container (three-necked flask) reaction system, slowly add under the stirring at room Zinc Chloride Anhydrous (81.6g, 0.6mol); Anthracene, be 1: 1.2: 6 to the mol ratio of fluorobenzoyl chloride, Zinc Chloride Anhydrous, the amount ratio of anthracene and methylene chloride is 1mol: 6000ml; System refluxed 12 hours, steaming vibrating dichloromethane, and discharging is used the alkali lye repetitive scrubbing, vacuum-drying in water.Ethyl alcohol recrystallization gets light yellow solid, called after 9-(4-fluorobenzene acyl group) anthracene.
Embodiment 3: synthetic () of containing the homopolymer of anthracene benzophenone end group
With 4,4 '-difluorodiphenyl base ketone 4.36g (20mmol), Resorcinol 2.42g (22mmol), Anhydrous potassium carbonate 3.188g (23.1mmol), N-Methyl pyrrolidone 60ml, toluene 40ml join in the 100ml there-necked flask that nitrogen port, mechanical stirring, thermometer, water-taker and reflux condensing tube are housed.Under the nitrogen protection, refluxing toluene band water 2 hours.After getting rid of toluene, be warmed up to 160 ℃, continue reaction 4 hours, add 9-(4-fluorobenzene acyl group) anthracene 1.2g (4mmol).Be warming up to 140 ℃ then, reacted 4 hours, in product impouring sour water,, obtain the refining homopolymer that contains anthracene benzophenone end group through pulverizing, washing, drying.
The infrared spectrum that contains the homopolymer of anthracene benzophenone end group is seen Fig. 3.
Embodiment 4: synthetic (two) of containing the homopolymer of anthracene benzophenone end group
With 4,4 '-difluorodiphenyl base ketone 4.36g (20mmol), Resorcinol 2.42g (22mmol), Anhydrous potassium carbonate 3.127g (22.66mmol), N-Methyl pyrrolidone 40ml, toluene 30ml join in the 100ml there-necked flask that nitrogen port, mechanical stirring, thermometer, water-taker and reflux condensing tube are housed.Under the nitrogen protection, refluxing toluene band water 1.5 hours.After getting rid of toluene, be warmed up to 190 ℃, continue reaction 8 hours, add 9-(4-fluorobenzene acyl group) anthracene 1.2g (4mmol).Be warming up to 170 ℃ then, reacted 8 hours, in product impouring sour water,, obtain the refining homopolymer that contains anthracene benzophenone end group through pulverizing, washing, drying.
Embodiment 5: synthetic () of containing the random copolymers of anthracene benzophenone end group
With 4,4 '-difluorodiphenyl base ketone 4.36g (20mmol), 2,2-two (4-hydroxyphenyl) propane 4.56g (20mmol), Resorcinol (0.22g, 2mmol), Anhydrous potassium carbonate 3.188g (23.1mmol), N-Methyl pyrrolidone 60ml, toluene 40ml join in the 100ml there-necked flask that nitrogen port, mechanical stirring, thermometer, water-taker and reflux condensing tube are housed.Under the nitrogen protection, refluxing toluene band water 1.5 hours.After getting rid of toluene, be warmed up to 160 ℃, continue reaction 4 hours, add 9-(4-fluorobenzene acyl group) anthracene 1.2g (4mmol) then.Be warming up to 140 ℃ of reactions 4 hours then, in product impouring sour water,, obtain the refining random copolymers that contains anthracene benzophenone end group through pulverizing, washing, drying.
Embodiment 6: synthetic (two) of containing the random copolymers of anthracene benzophenone end group
With 4,4 '-difluorodiphenyl base ketone 4.36g (20mmol), 2,2-two (4-hydroxyphenyl) propane 4.56g (20mmol), Resorcinol (0.22g, 2mmol), Anhydrous potassium carbonate 3.127g (22.66mmol), N-Methyl pyrrolidone 40ml, toluene 30ml join in the 100ml there-necked flask that nitrogen port, mechanical stirring, thermometer, water-taker and reflux condensing tube are housed.Under the nitrogen protection, refluxing toluene band water 2 hours.After getting rid of toluene, be warmed up to 190 ℃, continue reaction 8 hours, add 9-(4-fluorobenzene acyl group) anthracene 1.2g (4mmol) then.Be warming up to 170 ℃ of reactions 8 hours then, in product impouring sour water,, obtain the refining random copolymers that contains anthracene benzophenone end group through pulverizing, washing, drying.
Embodiment 7: other contain synthetic (one) of the polymkeric substance of anthracene benzophenone end group
Just change among the embodiment 3 to 64,4 '-difluoro benzophenone is 4,4 '-dichloro diphenyl sulfone or 4,4 '-difluoro diketone or decafluorobiphenyl, remainder is entirely with method among the embodiment 3 to 7, also can access polymkeric substance such as polyethersulfone that desired end group is the anthracene benzophenone, polyether-ether-ketone, polyarylether.
Change perhaps that biphenol monomer is 2 among the embodiment 3 to 6,2-two (4-hydroxyphenyl) propane, 4,4 '-dihydroxy diphenylsulphone, Resorcinol, Resorcinol, 2,2-two (4-hydroxyphenyl) HFC-236fa, m-trifluoromethylphenyl Resorcinol or 3, in the 5-two trifluoromethyl Resorcinol a kind of or different two kinds, remainder is entirely with method among the embodiment 3 to 7, also can access polymkeric substance such as polyethersulfone that desired end group is the anthracene benzophenone, polyether-ether-ketone, polyarylether.
Embodiment 8: other contain synthetic (two) of the polymkeric substance of anthracene benzophenone end group
The N-N-N,N-DIMETHYLACETAMIDE or the N-Methyl pyrrolidone that just change among the embodiment 3 to 7 are tetramethylene sulfone, and remaining method together, also can be waited until polymkeric substance such as desired polyether-ether-ketone, polyethersulfone, polyarylether entirely.
The toluene that just changes among the embodiment 3 to 7 is dimethylbenzene, and remaining method together, also can be waited until polymkeric substance such as desired polyether-ether-ketone, polyethersulfone, polyarylether entirely.
Embodiment 9: other contain synthetic (three) of the polymkeric substance of anthracene benzophenone end group
Just change biphenol monomer summation and the two fluorine monomers among the embodiment 3 to 8 and contain anthracene benzophenone fluorine monomer mol ratio at 1+1/n: 1: (2～2.1)/n (1＜n＜10000), remainder method entirely with, also can access polymkeric substance such as the different polyether-ether-ketone of a series of molecular weight differences, anthracene benzophenone content, polyethersulfone, polyarylether.
Claims (3)
1, a kind of purposes that contains the substituent fluorine monomer of anthracene benzophenone is to be the polymkeric substance that the feedstock production end group contains anthracene benzophenone group with 9-(4-fluorobenzene acyl group) anthracene; Described 9-(4-fluorobenzene acyl group) anthracene, structure is
According to the described purposes that contains the substituent fluorine monomer of anthracene benzophenone of claim 1, it is characterized in that 2, the polymkeric substance that said preparation end group contains anthracene benzophenone group is the end-blocking homopolymer; Preparation process is that two fluorine monomers or two chlorine monomer, biphenol monomer, catalyzer Anhydrous potassium carbonate, solvent N-Methyl pyrrolidone or tetramethylene sulfone, band aqua toluene or dimethylbenzene are joined in the container that nitrogen port, mechanical stirring, thermometer, water-taker and reflux condensing tube are housed; Under nitrogen protection, reflux and be with water 1.5～2 hours; After getting rid of toluene, be warmed up to 160～190 ℃, continue reaction 4～8 hours; Then 9-(4-fluorobenzene acyl group) anthracene is put in the reaction system, 140～170 ℃ of reactions 4～8 hours; Last discharging through pulverizing, washing, drying, obtains the homopolymer of purified anthracene benzophenone group end capping in acidic aqueous solution;
Wherein, biphenol monomer and two fluorine monomers or the monomeric mol ratio 1+1/n of two chlorine: 1,1＜n＜10000; Biphenol monomer is 1: 1.03～1.05 with the amount of substance ratio of catalyzer; The two fluorine monomers of every 0.01mol or two chlorine monomer add solvent 20～30mL, band aqua 15～20mL; The mol ratio of 9-(4-fluorobenzene acyl group) anthracene and biphenol monomer is 2/n～2.1/n: 1+1/n; Described pair of fluorine monomer or two chlorine monomer comprise 4,4 '-difluorodiphenyl base ketone, 4,4 '-dichloro diphenyl sulfone, 1,4-two (4-fluorobenzene carbonyl) benzene or 2,6-difluorobenzonilyile; Described biphenol monomer comprises 2,2-two (4-hydroxyphenyl) propane, 4,4 '-dihydroxy diphenylsulphone, Resorcinol, Resorcinol, 2,2-two (4-hydroxyphenyl) HFC-236fa, m-trifluoromethylphenyl Resorcinol or 3,5-two trifluoromethyl Resorcinol.
According to the described purposes that contains the substituent fluorine monomer of anthracene benzophenone of claim 1, it is characterized in that 3, the polymkeric substance that said preparation end group contains anthracene benzophenone group is the end-blocking random copolymers; Preparation process is that two fluorine monomers, biphenol monomer 1, biphenol monomer 2, catalyzer Anhydrous potassium carbonate, solvent N-Methyl pyrrolidone or tetramethylene sulfone, band aqua toluene or dimethylbenzene are joined in the container that nitrogen port, mechanical stirring, thermometer, water-taker and reflux condensing tube are housed; Under nitrogen protection, reflux and be with water 1.5～2 hours; After getting rid of toluene, be warmed up to 160～190 ℃, continue reaction 4～8 hours; Then 9-(4-fluorobenzene acyl group) anthracene is put in the reaction system, 140～170 ℃ of reactions 4～8 hours; Last discharging through pulverizing, washing, drying, obtains the random copolymers of purified anthracene benzophenone group end capping in acidic aqueous solution;
Wherein, biphenol monomer summation and two fluorine monomer mol ratio 1+1/n: 1,1＜n＜10000, the mol ratio of catalyzer and biphenol monomer summation is 1.03～1.05: 1; The two fluorine monomers of every 0.01mol, solubilizing agent 20～30mL, band aqua 10～15mL; The mol ratio of 9-(4-fluorobenzene acyl group) anthracene and biphenol monomer summation is 2/n～2.1/n: 1+1/n; Described pair of fluorine monomer comprises 4,4 '-difluorodiphenyl base ketone, 1,4-two (4-fluorobenzene carbonyl) benzene or 2,6-difluorobenzonilyile; Described biphenol monomer 1, biphenol monomer 2 are 2,2-two (4-hydroxyphenyl) propane, 4,4 '-dihydroxy diphenylsulphone, Resorcinol, Resorcinol, 2,2-two (4-hydroxyphenyl) HFC-236fa, m-trifluoromethylphenyl Resorcinol or 3, in the 5-two trifluoromethyl Resorcinol different two kinds.
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