CN1944488A - Bisphenol type poly arylate and its preparing method and use - Google Patents
Bisphenol type poly arylate and its preparing method and use Download PDFInfo
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- CN1944488A CN1944488A CN 200610022133 CN200610022133A CN1944488A CN 1944488 A CN1944488 A CN 1944488A CN 200610022133 CN200610022133 CN 200610022133 CN 200610022133 A CN200610022133 A CN 200610022133A CN 1944488 A CN1944488 A CN 1944488A
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- bisphenol
- polyarylate
- weight
- chloride
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 229920001230 polyarylate Polymers 0.000 title claims abstract description 36
- 229930185605 Bisphenol Natural products 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000012071 phase Substances 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 239000012153 distilled water Substances 0.000 claims abstract description 18
- 238000003756 stirring Methods 0.000 claims abstract description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 9
- -1 bisphenol compound Chemical class 0.000 claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 8
- 239000012074 organic phase Substances 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 8
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 18
- 239000004332 silver Substances 0.000 claims description 18
- 229910052709 silver Inorganic materials 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims description 9
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical group ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 9
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- 238000001556 precipitation Methods 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 8
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 claims description 7
- 239000012295 chemical reaction liquid Substances 0.000 claims description 7
- 230000009477 glass transition Effects 0.000 claims description 7
- 239000012264 purified product Substances 0.000 claims description 7
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims description 6
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 5
- 238000002845 discoloration Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
- 229960001701 chloroform Drugs 0.000 claims description 3
- 235000010292 orthophenyl phenol Nutrition 0.000 claims description 3
- 239000001294 propane Substances 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 2
- 238000012696 Interfacial polycondensation Methods 0.000 claims description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 claims description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 claims description 2
- 238000007747 plating Methods 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 2
- 239000011247 coating layer Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical group O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 238000000638 solvent extraction Methods 0.000 abstract 1
- 238000000576 coating method Methods 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 15
- 230000001681 protective effect Effects 0.000 description 11
- 230000007797 corrosion Effects 0.000 description 7
- 238000005260 corrosion Methods 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 230000004224 protection Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000008859 change Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 238000005536 corrosion prevention Methods 0.000 description 3
- 238000004649 discoloration prevention Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 238000003466 welding Methods 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical group OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- GGZHVNZHFYCSEV-UHFFFAOYSA-N 1-Phenyl-5-mercaptotetrazole Chemical compound SC1=NN=NN1C1=CC=CC=C1 GGZHVNZHFYCSEV-UHFFFAOYSA-N 0.000 description 1
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006388 chemical passivation reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001652 electrophoretic deposition Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002103 nanocoating Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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- Polyesters Or Polycarbonates (AREA)
Abstract
The present invention discloses one kind of bisphenol type polyarylate and its preparation process and use. The preparation process of bisphenol type polyarylate includes the following steps: mixing distilled water 890-990 weight portions, sodium hydroxide 18-23 weight portions, bisphenol compound 36-50 weight portions and organic quaternary ammonium salt 0.2-0.8 weight portions via stirring to dissolve and form water phase; dropping chlorohydrocarbon 232-336 weight portions as solvent and phenyl diformyl chloride 25-57 weight portions to form oil phase; stirring to react at 10-35 deg.c; adding end capping agent 1-3 weight portions before further reaction for 1-3 hr; neutralizing the reacted liquid, stilling to separate two phase, dropping the organic phase to settling agent via violent stirring to settle; washing the settled product with distilled water until reaching no chlorine ion; stoving; solvent extraction to purify and final stoving.
Description
Technical Field
The invention relates to bisphenol type polyarylester and a preparation method and application thereof, which are suitable for a high polymer coating for preventing silver-plated film from corrosion and discoloration. Belongs to the field of polymer coating for corrosion prevention.
Background
Silver is known to have excellent decorative properties, excellent electrical conductivity, thermal conductivity and solderability. Therefore, the silver-plated member is widely applied to instruments, meters and various electronic products. However, silver is extremely easy to corrode and discolor in atmospheric environment, which not only reduces the decoration performance and influences the weldability of electrical elements, but also increases the surface resistance of silver-plated parts, increases the electric energy loss, and reduces the stability and reliability of electronic equipment, even causes serious accidents.
The following three methods are generally adopted in order to prevent the silver-plated article from being discolored by corrosion: a surface purification method; an organic protective film method; polymer protective film method.
The surface passivation method generally employs chemical purification, electrolytic purification, electrophoretic deposition, and the like. This method forms a protective film of oxide and chromate on the silver surface. The method has serious pollution to ecological environment, the compactness of a surface purification layer is poor, the surface purification layer is not high-temperature resistant, ultraviolet resistant and not strong in corrosion resistance, and the surface gloss of the silver is easy to change after the surface purification layer is treated. (Liu Yong year. research on improving discoloration resistance of silver-plated part, radar and countermeasure 1995 (4): 66-69; Liu Zhong. chemical passivation of silver-plated layer, Material protection 1986, (1) 39-41;)
Organic substance protective film method: the organic protective film mainly comprises mercaptan or azole compounds, such as hexadecyl or octadecyl mercaptan, benzotriazole, 1-phenyl-5-mercaptotetrazole, mercaptobenzimidazole, mercaptobenzoxazole, etc. These organic materials are capable of binding with silver as a ligand to form a dense protective film. But the sulfur and nitrogen atom-containing organic matter protective film is easily oxidized in the atmospheric environment, and the coordination structure of the film and the silver is damaged; the discoloration prevention effect of the protective film is influenced; in addition, the organic protective film is usually selected from water or high boiling point solvent, needs to be dip-coated under heating and dried at high temperature to form a film, and the coating process is complicated. (Lerunmin. discoloration prevention protection of silver coating Material protection 1990, 23 (11): 35-38; Fang J.L. tarnish protection of plated silver 1988, 75 (2): 56-61).
Polymer protective film method: in recent years, attention has been paid to a method for preventing silver-corrosion discoloration by using a polymer. The surface of the silver layer is coated with a layer of polymer film to isolate the silver surface from the surrounding harmful media, thereby playing the role of silver corrosion and discoloration prevention. The high polymer includes polyurethane, epoxy resin, silicone resin, etc. However, these high polymers have generally strong insulating property, and after the silver layer is coated on the surface, the high polymers greatly increase the surface contact resistance and reduce the solderability, and are not suitable for being used as protective films of silver-plated electrical elements. (Lin Yi Chao super. color change and protection of silver artware material protection 1993, 26(3) 28-31).
Disclosure of Invention
The invention aims to provide a bisphenol type polyarylate and a preparation method and application thereof aiming at the defects of the prior art. The polyarylester is characterized in that the polyarylester has small influence on the conductivity and the welding performance of a silver-plated piece and is a high-molecular coating for silver plating corrosion prevention and color change.
The invention discovers that bisphenol type polyarylate is synthesized by using phthaloyl chloride and bisphenol compounds as basic raw materials and organic quaternary ammonium salt as a catalyst and adopting an interfacial polycondensation method. The polymer can form an o-hydroxybenzophenone structure under illumination, and a very thin ultraviolet protective layer is formed on the surface of silver, so that ultraviolet rays are prevented from damaging a silver coating, and the corrosion and color change resistance is improved. The synthesized polymer chain has P-pi conjugation of benzene ring and carbonyl group to form a conjugated electron cloud system, which is favorable for electron transfer and reduces the influence of the polymer coating on contact resistance. The molecular weight, molecular weight distribution and terminal group species of the polymer are adjusted to improve the weldability of the polymer coating film.
The aim of the invention is realized by the following technical measures, wherein the parts of the raw materials are parts by weight except for special instructions.
The chemical structural formula of the bisphenol type polyarylate is as follows:
wherein, X is-S-,
R＝O，-CH2-CH＝CH2
n＝50～180
the formula of the bisphenol type polyarylate starting material comprises the following components:
25-57 parts of phthaloyl chloride
36-50 parts of bisphenol compound
0.2 to 0.8 portion of organic quaternary ammonium salt
232 to 336 parts of chlorinated hydrocarbon
18-23 parts of sodium hydroxide
890-990 parts of distilled water
1-3 parts of end-capping agent
The phthaloyl chloride is terephthaloyl chloride and isophthaloyl chloride, and the weight ratio of the terephthaloyl chloride to the isophthaloyl chloride is 10-90: 90-10.
The bisphenol compound is at least one of 2.2-bis (4-hydroxyphenyl) propane, 4.4' -dihydroxyphenyl sulfide, and 2.2-bis (6-allyl, 4-hydroxyphenyl) propane.
The organic quaternary ammonium salt is at least one of sodium dodecyl sulfate, cetyl trimethyl ammonium bromide, triethyl benzyl ammonium chloride and tetrabutyl ammonium bromide.
The chlorinated hydrocarbon is at least one of dichloromethane, tetrachloroethane, trichloromethane, 1, 2-dichloroethane and 1, 1-trichloroethane.
The end capping agent is at least one of p-tert-butylphenol, o-phenylphenol, p-cumylphenol and phenol.
The preparation method of the bisphenol type polyarylate comprises the following steps:
adding 890-990 parts of distilled water, 18-23 parts of sodium hydroxide, 36-48 parts of bisphenol complex and 0.2-0.8 part of organic quaternary ammonium salt into a three-necked bottle with a stirrer and a thermometer, and stirring and dissolving to form a water phase; and dripping oil phase which is composed of 232-336 parts of chlorinated hydrocarbon as a solvent and 25-57 parts of phthaloyl chloride into the reactor. The reaction is carried out at a stirring speed of 600-1200 r/min and a temperature of 10-35 ℃. And then adding 1-3 parts of end-capping reagent, and stopping the reaction after keeping the reaction for 1-5 hours. Neutralizing the reaction liquid with acid to neutrality, standing to separate two phases, dropping the organic phase into settling agent via stirring to settle, washing the settling product with distilled water until no chlorine ion exists, and stoving in a vacuum oven at 40-60 deg.c to constant weight. And (3) putting the prepared product into a soxhlet extractor, extracting and purifying by using a solvent, and putting the purified product into a vacuum oven to be dried at the temperature of 40-60 ℃ for constant weight to obtain the bisphenol type polyarylester.
The solvent for precipitation and extraction purification is any one of methanol, ethanol, n-hexane, acetone, ethyl acetate and water.
The performance test of the bisphenol type polyarylate shows that: the intrinsic viscosity [ eta ] is 0.5 to 1.1dl/g, the glass transition temperature Tg is 150 to 220 ℃, and the thermal decomposition temperature Td is 400 to 550 ℃.
The bisphenol type polyarylate is used for the high polymer coating which can prevent the silver coating from corroding and discoloring. For example, 3 to 5 parts of bisphenol type polyarylate is weighed and prepared into a polyarylate solution with a concentration of 1 to 5% using a chlorinated hydrocarbon solvent. And respectively soaking the silver-plated test pieces of different substrates into the polyarylate solution, taking out after uniform dip-coating, and naturally drying in air or drying in an oven at the temperature of 60-90 ℃ for 1-5 minutes.
The invention has the following advantages:
1. the coating has good light transmission, ultraviolet resistance and ethanol scrubbing resistance.
2. The mechanical property of the coating is good, and the coating film with the impact strength of more than 30kg. The flexibility was such that the coating film did not crack by bending with a radius of curvature of 1. The adhesion belongs to grade 0.
3. The coating film has little influence on contact resistance and welding performance.
4. After the high-low temperature and damp-heat performance test, the coating film does not crack, yellow or fall off.
5. The mould resistance is between 0 and 2 grades.
6. The process is simple and easy to operate, the coating and the film forming can be carried out at room temperature, heating is not needed, and energy is saved.
Detailed Description
The present invention is described in detail below by way of examples, it should be noted that the examples are only for illustrating the present invention and should not be construed as limiting the scope of the present invention, and those skilled in the art can make modifications and adjustments in the above-mentioned contents.
Example 1: 946 parts of distilled water, 20 parts of sodium hydroxide, 45.8 parts of 2, 2-bis (4-hydroxyphenyl) propane (bisphenol A) and 0.32 part of triethyl benzyl ammonium chloride are added into a three-necked bottle provided with a stirrer and a thermometer, and a water phase is formed after stirring and dissolving; an oil phase consisting of 315 parts of methylene chloride, 12.24 parts of terephthaloyl chloride and 28.56 parts of isophthaloyl chloride is added dropwise to the reactor. After the reaction was carried out at 10 ℃ for half an hour, 1.7 parts of t-butylphenol was added, and the reaction was stopped after the reaction was continued for 1 hour. Neutralizing the reaction liquid with acetic acid to neutrality, standing to separate two phases, dripping the next organic phase into methanol under strong stirring for precipitation, filtering the precipitate, washing the precipitate with distilled water until no chloride ion exists, finally placing the product in a vacuum oven, and drying at 50 ℃ to constant weight to obtain the bisphenol A polyarylate.
The prepared bisphenol A polyarylate product is put in a Soxhlet extractor and extracted and purified by absolute ethyl alcohol, and the purified product is put in a vacuum oven and dried at the temperature of 50 ℃ to have constant weight. Determining intrinsic viscosity [ eta ] of the product to be 0.7 dl/g; the glass transition temperature Tg is 163 ℃; the thermal decomposition temperature Td is 497 ℃.
Example 2: adding 890 parts of distilled water, 18 parts of sodium hydroxide, 36 parts of 2, 2-bis (4-hydroxyphenyl) propane (bisphenol A) and 0.2 part of triethyl benzyl ammonium chloride into a three-necked bottle provided with a stirrer and a thermometer, and stirring and dissolving to form a water phase; an oil phase consisting of 232 parts of methylene chloride, 28.56 parts of terephthaloyl chloride and 12.24 parts of isophthaloyl chloride is added dropwise to the reactor. After the reaction was carried out at 20 ℃ for half an hour, 1 part of phenol was added, and the reaction was stopped after 1.5 hours. Neutralizing the reaction liquid with acetic acid to neutrality, standing to separate two phases, dripping the next organic phase into strongly stirred n-hexane for precipitation, filtering the precipitate, washing the precipitate with distilled water until no chloride ion exists, finally placing the product in a vacuum oven, and drying at the temperature of 40 ℃ until the weight is constant to obtain the bisphenol polyarylate.
The prepared bisphenol A polyarylate product is put in a Soxhlet extractor and extracted and purified by absolute ethyl alcohol, and the purified product is put in a vacuum oven to be dried at the temperature of 40 ℃ and the constant weight. Determining the intrinsic viscosity [ eta ] of the product to be 0.53 dl/g; the glass transition temperature Tg is 192 ℃; the thermal decomposition temperature Td was 547 ℃.
Example 3: 990 parts of distilled water, 23 parts of sodium hydroxide, 48 parts of 2, 2-bis (4-hydroxyphenyl) propane (bisphenol A) and 0.5 part of hexadecyltrimethylammonium bromide are added into a three-necked bottle provided with a stirrer and a thermometer, and a water phase is formed after stirring and dissolving; an oil phase consisting of 336 parts of trichloromethane, 34.2 parts of terephthaloyl chloride and 22.8 parts of isophthaloyl chloride is added dropwise into the reactor. Reacting for half an hour at the temperature of 30 ℃, adding 2 parts of tert-butyl phenol, and stopping the reaction after continuing the reaction for 2 hours. Neutralizing the reaction liquid with acetic acid to neutrality, standing to separate two phases, dripping the next organic phase into hot water under strong stirring for precipitation, filtering the precipitate, washing with distilled water until no chloride ion exists, and finally drying the product in a vacuum oven at the temperature of 60 ℃ to constant weight to obtain the bisphenol polyarylate.
The prepared bisphenol A polyarylate product is put in a Soxhlet extractor and extracted and purified by absolute ethyl alcohol, and the purified product is put in a vacuum oven to be dried at the temperature of 60 ℃ and the constant weight. Determining the intrinsic viscosity [ eta ] of the product to be 1.1 dl/g; the glass transition temperature Tg is 172 ℃; the thermal decomposition temperature Td is 507 ℃.
Example 4: adding 920 parts of distilled water, 19 parts of sodium hydroxide, 34.28 parts of 2, 2-bis (4-hydroxyphenyl) propane (bisphenol A), 15.35 parts of 2, 2-bis (6-allyl, 4-hydroxyphenyl) propane and 0.8 part of tetrabutyl sodium bromide into a three-necked flask provided with a stirrer and a thermometer, and stirring and dissolving to form a water phase; an oil phase consisting of 1.1.2.2-tetrachloroethane 315.8 parts, terephthaloyl chloride 18.1 parts and isophthaloyl chloride 39.9 parts was added dropwise to the reactor. After the reaction was carried out at 35 ℃ for half an hour, 1.5 parts of o-phenylphenol was added, and the reaction was stopped after the reaction was continued for 1 hour. Neutralizing the reaction liquid with acetic acid to neutrality, standing to separate two phases, dropping the next organic phase into acetone under strong stirring to precipitate, filtering the precipitate, washing with distilled water until no chloride ion exists, and stoving the product in a vacuum oven at 50 deg.c to constant weight to obtain bisphenol polyarylate.
The prepared product is put into a Soxhlet extractor to be extracted and purified by absolute ethyl alcohol, and the purified product is put into a vacuum oven to be dried at the temperature of 50 ℃ and constant weight. Determining intrinsic viscosity [ eta ] of the product to be 0.52 dl/g; the glass transition temperature Tg of 210 ℃; the thermal decomposition temperature Td is 450 ℃.
Example 5: 946.8 parts of distilled water, 22 parts of sodium hydroxide, 34.28 parts of 2, 2-bis (4-hydroxyphenyl) propane (bisphenol A), 10.14 parts of 4, 4' -dihydroxy phenyl sulfide, 0.32 part of triethyl benzyl ammonium chloride and 0.32 part of lauryl sodium sulfate are added into a three-necked flask provided with a stirrer and a thermometer, and a water phase is formed after stirring and dissolving; an oil phase consisting of 232 parts of methylene chloride, 1.1.2.2 parts of tetrachloroethane, 104 parts of terephthaloyl chloride and 28.56 parts of isophthaloyl chloride is added dropwise to the reactor. After the reaction was carried out at 30 ℃ for half an hour, 1.7 parts of t-butylphenol was added, and the reaction was stopped after the reaction was continued for 1 hour. Neutralizing the reaction liquid with acetic acid to neutrality, standing to separate two phases, dripping the next organic phase into methanol under strong stirring for precipitation, filtering the precipitate, washing with distilled water until no chloride ion exists, and finally drying the product in a vacuum oven at 50 ℃ to constant weight to obtain the bisphenol type polyarylate.
The prepared product is put into a soxhlet extractor to be extracted and purified by absolute methanol, and the purified product is put into a vacuum oven to be dried at the temperature of 50 ℃ and the constant weight. Determining the intrinsic viscosity [ eta ] of the product to be 0.458 dl/g; the glass transition temperature Tg is 158 ℃; the thermal decomposition temperature Td was 400 ℃.
Application example:
1 part of the bisphenol A polyarylate obtained in example 1 was weighed and mixed with a solvent mixture of methylene chloride and tetrachloroethane (1: 1 weight ratio) to prepare a 3% polymer solution. The silver-plated test pieces of various base materials are respectively immersed in the polyarylate solution, taken out after being evenly dipped and dried naturally in the air or dried in a drying oven at the temperature of 80 ℃ for 2 minutes. The silver-plated test piece after being dip-coated with the polymer was subjected to a test of corrosion properties of hydrogen sulfide and sodium sulfide, and the results are shown in table 1.
And (4) supplementary notes: (1) measured according to GJB 1300-91; (2) about 0.5 ml of a 1% strength sodium sulfide solution was added dropwise to the test piece, and the discoloration time was observed.
TABLE 1 Corrosion resistance of bisphenol A polyarylate coatings
Claims (9)
1. A bisphenol type polyarylate characterized in that the chemical structural formula of the bisphenol type polyarylate is:
wherein,
R＝O，-CH2-CH＝CH2
n＝50-180
the formula of the polyarylate starting material comprises the following components in parts by weight:
25-57 parts of phthaloyl chloride
36-50 parts of bisphenol compound
0.2 to 0.8 portion of organic quaternary ammonium salt
232 to 336 parts of chlorinated hydrocarbon
18-23 parts of sodium hydroxide
890-990 parts of distilled water
1-3 parts of end-capping agent
Intrinsic viscosity [ eta ] of bisphenol polyarylate prepared by interfacial polycondensation]0.5 to 1.1dL/g, glass transition temperature Tg155-220 ℃ and thermal decomposition temperature Td＝400～550℃。
2. The bisphenol-type polyarylate according to claim 1, wherein the phthaloyl chloride is terephthaloyl chloride and isophthaloyl chloride, wherein the weight ratio of terephthaloyl chloride to isophthaloyl chloride is 10-90: 90-10.
3. The bisphenol-type polyarylate as claimed in claim 1, wherein the bisphenol compound is at least one of 2.2-bis (4-hydroxyphenyl) propane, 4.4' -dihydroxyphenyl sulfide, and 2.2-bis (6-allyl, 4-hydroxyphenyl) propane.
4. The diaryl bisphenol of claim 1, wherein the quaternary organic amine salt is at least one of sodium dodecyl sulfate, cetyltrimethylammonium bromide, triethylbenzylammonium chloride, tetrabutylammonium bromide.
5. The bisphenol-type polyarylate as claimed in claim 1, wherein the chlorinated hydrocarbon is at least one of dichloromethane, tetrachloroethane, trichloromethane, 1.2-dichloroethane, 1.1.1-trichloroethane.
6. The diaryl bisphenol of claim 1, wherein the end-capping agent is at least one of p-tert-butylphenol, o-phenylphenol, p-cumylphenol.
7. The method for producing a bisphenol type polyarylate as claimed in any one of claims 1 to 6, characterized in that the method comprises the steps of:
adding 890-990 parts by weight of distilled water, 18-23 parts by weight of sodium hydroxide, 36-48 parts by weight of bisphenol compound and 0.2-0.8 part by weight of organic quaternary ammonium salt into a three-necked bottle with a stirrer and a thermometer, stirring and dissolving to form a water phase, dropwise adding 232-336 parts by weight of solvent chlorohydrocarbon and 25-57 parts by weight of phthaloyl chloride into the reactor to form an oil phase, reacting at the stirring speed of 600-1200 rpm and the temperature of 10-35 ℃, then adding 1-3 parts by weight of end-capping agent, stopping the reaction after keeping the reaction for 1-3 hours, neutralizing the reaction liquid to be neutral by using acid, standing to separate two phases, dropwise adding the organic phase into a strongly stirred precipitation agent for precipitation, washing the precipitated product to be free of chloride ions by using distilled water, then placing the product in a vacuum oven, drying at the temperature of 40-60 ℃ to constant weight, extracting and purifying the prepared product by using solvent in a Soxhlet extractor, and (3) placing the purified product in a vacuum oven to be dried at 40-60 ℃ for constant weight to obtain the bisphenol type polyarylate.
8. The process for producing a bisphenol polyarylate as claimed in claim 7, wherein the solvent for precipitation and extraction purification is any one of methanol, ethanol, n-hexane, acetone, ethyl acetate and water.
9. Use of the bisphenol polyarylate as claimed in claim 1, wherein the bisphenol polyarylate is used for a polymer coating layer which is resistant to the corrosive discoloration of a silver plating film.
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| CN102558518A (en) * | 2010-12-07 | 2012-07-11 | 上海杰事杰新材料(集团)股份有限公司 | Aromatic copolyester and preparation method thereof |
| CN102898630A (en) * | 2011-07-27 | 2013-01-30 | 上海杰事杰新材料(集团)股份有限公司 | Copolyarylate and its preparation method |
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| CN102898630A (en) * | 2011-07-27 | 2013-01-30 | 上海杰事杰新材料(集团)股份有限公司 | Copolyarylate and its preparation method |
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| CN112708114A (en) * | 2020-12-29 | 2021-04-27 | 四川大学 | Low-dielectric high-light-transmittance polyarylate, polyarylate film and preparation method thereof |
| CN113980561A (en) * | 2021-11-11 | 2022-01-28 | 合肥工业大学 | UV (ultraviolet) curing hard coating and preparation method thereof |
| CN114479029A (en) * | 2022-01-26 | 2022-05-13 | 安徽理工大学 | Preparation method of bisphenol-B type polyarylate material |
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