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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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 technology of the present invention relates to a kind of bisphenol type poly arylate and its production and use, and it is applicable to the polymeric coating layer of anti-silver-plated erosion variable color.Belong to protection against corrosion and use the polymeric coating layer field.
Background technology
As everyone knows, silver has excellent decoration, good electroconductibility, thermal conductivity and weldability.Therefore silver plate is widely used in instrument, instrument and various electronic product.But silver very easily corrodes variable color in atmospheric environment, has reduced not only that it is ornamental, has influenced the weldability of electrical element, and the silver plate surface resistivity is increased, and electric energy loss strengthens, and makes the stability of electronics, reliability decrease, even major accident takes place.
Usually adopt following three kinds of methods in order to prevent silver plate corrosion variable color: surperficial method of purification; Organism class protection embrane method; Polymkeric substance protection embrane method.
The surface passivation method adopts chemical purification usually, electrolysis purifying and electrophoretic deposition etc.This method is to make silver surface shape one deck oxide compound and chromate protective film.This method has severe contamination to ecotope, and surperficial purification layer compactness is relatively poor, and non-refractory, non-UV resistant, anti-corrosion capability are not strong, handles the surface luster of back malleable silver.(Liu Yongnian. improve the research of silver plate discoloration-resisting, " radar and antagonism " 1995 (4): 66-69; Liu Zhong. the chemical passivation of silvered film, " material protection " 1986, (1) 39-41; )
Organism class protection embrane method: using more organism class protective membrane mainly is mercaptan or nitrogen azole compounds, as hexadecyl or Stearyl mercaptan, and benzotriazole, 1 phenyl-5-mercapto tetrazole, mercaptobenzimidazole, mercaptobenzoxazole etc.These organism all are because of being combined into ligand with silver, forming compact protective film.But sulfur-bearing, nitrogen-atoms organism class protective membrane are oxidized easily under atmospheric environment, and film is destroyed with the coordination structure of silver; Influence the anti-color changeable effect of protective membrane; Organism class protective membrane is often selected water or high boiling solvent in addition, needs dip-coating under heating, and high temperature is the oven dry film forming down, and coating processes is miscellaneous.(Li Ruimin. anti-variable color protection " material protection " 1990,23 (11): the 35-38 of silvered film; Fang J.L.Tarnish protection of plated silver " plating and surfaceFinishing " 1988,75 (2): 56-61).
Polymkeric substance protection embrane method: receive publicity with the anti-silver corrosion of polymkeric substance color changing method in recent years.Apply one deck polymeric membrane silver surface and hazardous medium isolation on every side at silver layer surface, thereby play anti-silver corrosion color changeable effect.These superpolymer have urethane, epoxy resin, silicone resin etc.But these superpolymer insulativity generally more by force after silver layer surface applies, increase surface contacted resistance greatly and reduce weldability, are not suitable as the protective membrane of silver-plated electrical element very much.(Lin Yichao. the variable color of silverwork and protection " material protection " 1993,26 (3) 28-31).
Summary of the invention
The objective of the invention is provides a kind of bisphenol type poly arylate and its production and use at the deficiencies in the prior art.Be characterized in that this polyarylester is little and become the polymeric coating layer that silver-plated protection against corrosion variable color is used to the influence of silver plate electroconductibility and welding property.
The present invention finds that with phthalyl chloride and bisphenol cpd be basic raw material, and organic quaternary amine is a catalyzer, adopts interface fasculation method to synthesize bisphenol type poly arylate.This polymkeric substance can form o-hydroxy ketone structure under illumination, form very thin one deck UV protection layer at silver surface, thereby prevent that the ultraviolet damage silvered film from improving anticorrosion metachrosis.Exist the P-of phenyl ring and carbonyl pi-conjugated in institute's synthetic polymer chain, form conjugated electrons cloud system, help transfer transport, reduce the influence of polymer coating film contact resistance.By the molecular weight of telomerized polymer, molecular weight distribution, and the end group kind is to reach the weldability of improving polymer coating film.
Purpose of the present invention is realized that by following technical measures wherein said raw material umber is parts by weight except that specified otherwise.
The chemical structural formula of bisphenol type poly arylate is:
Wherein, X=-S-,
R＝O，-CH
2-CH＝CH
2
n＝50～180
The recipe ingredient of bisphenol type poly arylate starting raw material is:
25～57 parts of phthalyl chlorides
36～50 parts of bisphenol cpds
0.2～0.8 part of organic quaternary amine
232～336 parts of hydrochloric ethers
18～23 parts in sodium hydroxide
890～990 parts of distilled water
1～3 part of end-capping reagent
Phthalyl chloride is p-phthaloyl chloride and m-phthaloyl chloride, p-phthaloyl chloride and m-phthaloyl chloride by weight proportion 10～90: 90～10.
Bisphenol cpd is two (4-hydroxy phenyl) propane of 2.2-, 4.4 ' one dihydroxy phenyl thioethers, at least a in two (6-allyl group, the 4 hydroxy phenyls) propane of 2.2-.
Organic quaternary amine is a sodium lauryl sulphate, cetyl trimethylammonium bromide, triethyl benzyl ammonia chloride, at least a in the Tetrabutyl amonium bromide.
Hydrochloric ether is a methylene dichloride, at least a in tetrachloroethane, trichloromethane, 1.2-ethylene dichloride, 1.1.1 one trichloroethane.
End-capping reagent is a p-tert-butylphenol, orthoxenol, at least a in a cumylphenol, the phenol.
The preparation method of bisphenol type poly arylate:
With 890～990 parts of distilled water, 18～23 parts of sodium hydroxids, bis-phenol be than 36～48 parts of compounds, and 0.2～0.8 part of organic quaternary amine adds and has in the three-necked bottle of agitator and thermometer, forms water after the stirring and dissolving; And dropping is the oil phase of solvent and 25～57 parts of compositions of phthalyl chloride with 232～336 parts of chlorinated hydrocarbons in reactor.Low whipping speed 600～1200r/min, temperature is reacted for 10～35 ℃.Add 1～3 part of end-capping reagent then, keep reacting stopped reaction after 1-5 hour.Reaction solution is neutralized to neutrality with acid, leaves standstill to make two to be separated, and organism is added drop-wise to precipitating in the precipitating agent under the violent stirring mutually, and the precipitating product is washed with distilled water to no chlorion, places vacuum drying oven to dry to constant weight in temperature 40-60 ℃ again.Prepared product is placed in the cable-styled extractor with solvent extraction purifies, purified product places vacuum drying oven in 40～60 ℃ of oven dry of temperature constant weight, obtains bisphenol type poly arylate.
Precipitating and purification by liquid extraction solvent are methyl alcohol, ethanol, normal hexane, acetone, any in ethyl acetate and the water.
The performance test of bisphenol type poly arylate, the result shows: intrinsic viscosity [η]=0.5～1.1dl/g, second-order transition temperature Tg=150～220 ℃, heat decomposition temperature Td=400～550 ℃.
Bisphenol type poly arylate is used for the polymeric coating layer of anti-silver-plated erosion variable color.For example take by weighing 3～5 parts of bisphenol type poly arylates, be mixed with the polyarylester solution that concentration is 1-5% part with chlorinated hydrocarbon solvent.The silver-plated test piece of different substrate materials is immersed respectively in the polyarylester solution, and dip-coating evenly back is taken out, and dries up naturally in air or 60～90 ℃ of drying in oven of temperature 1～5 minute.
The present invention has following advantage:
1, the coating light transmission is good, UV resistant, and anti-ethanol is cleaned.
2, the mechanical property of coating is good, and shock strength＞30kg.cm films and do not chap.Snappiness is filmed by the bending of 1 radius-of-curvature and is not broken.Sticking power belongs to 0 grade.
3, film little to the influence of contact resistance and welding property.
4, film after high low temperature, damp and hot performance test, do not ftracture, non-yellowing, do not come off.
5, fungus resistance can be between the 0-2 level.
6, technology simple to operation, film and save energy all can at room temperature be carried out, be need not to heat to film forming.
Embodiment
Below by embodiment the present invention is carried out concrete description; be necessary to be pointed out that at this present embodiment only is used for the present invention is further specified; can not be interpreted as limiting the scope of the invention, the person skilled in the art in this field can do some nonessential improvement and adjustment according to the content of the invention described above.
Embodiment 1: with 946 parts of distilled water, and 20 parts of sodium hydroxids, 45.8 parts in two (4-hydroxy phenyl) propane (dihydroxyphenyl propane) of 2.2-, 0.32 part of triethyl benzyl ammonia chloride joins in the three-necked bottle that agitator and thermometer are housed, and forms water after the stirring and dissolving; Dropping in reactor is by 315 parts of methylene dichloride, 12.24 parts of p-phthaloyl chlorides, 28.56 parts of m-phthaloyl chlorides, the oil phase of composition.After 10 ℃ of temperature are reacted half an hour, add 1.7 parts of tert.-butyl phenols, continue to react stopped reaction after 1 hour.Extremely neutral with acetic acid neutralization reaction liquid, leave standstill and make two to be separated, following sublevel organism is added drop-wise to precipitating in the methyl alcohol under the violent stirring mutually, the filtration of precipitating thing is washed with distilled water to no chlorion, at last product is placed vacuum drying oven, dry to constant weight for 50 ℃ in temperature, obtain the polymer with bis phenol A aromatic ester.
The polymer with bis phenol A aromatic ester product that makes is placed on uses the dehydrated alcohol purification by liquid extraction in the cable-styled extractor, purified product places vacuum drying oven, in 50 ℃ of oven dry of temperature constant weight.Measure intrinsic viscosity [the η]=0.7dl/g of product; Second-order transition temperature Tg=163 ℃; Heat decomposition temperature Td=497 ℃.
Embodiment 2: with 890 parts of distilled water, and 18 parts of sodium hydroxids, 36 parts in two (4-hydroxy phenyl) propane (dihydroxyphenyl propane) of 2.2-, 0.2 part of triethyl benzyl ammonia chloride joins in the three-necked bottle that agitator and thermometer are housed, and forms water after the stirring and dissolving; Dropping in reactor is by 232 parts of methylene dichloride, 28.56 parts of p-phthaloyl chlorides, the oil phase of 12.24 parts of compositions of m-phthaloyl chloride.After 20 ℃ of temperature are reacted half an hour, add 1 part of phenol, continue to react stopped reaction after 1.5 hours.Extremely neutral with acetic acid neutralization reaction liquid, leave standstill and make two to be separated, to descend the sublevel organism to be added drop-wise to precipitating in the intensively stirred normal hexane mutually, the filtration of precipitating thing is washed with distilled water to no chlorion, at last product is placed vacuum drying oven, in 40 ℃ of temperature, dry, obtain the bis-phenol polyarylester to constant weight.
The polymer with bis phenol A aromatic ester product that makes is placed on and uses the dehydrated alcohol purification by liquid extraction in the cable-styled extractor, and purified product places vacuum drying oven in 40 ℃ of oven dry of temperature constant weight.Measure intrinsic viscosity [the η]=0.53dl/g of product; Second-order transition temperature Tg=192 ℃; Heat decomposition temperature Td=547 ℃.
Embodiment 3: with 990 parts of distilled water, and 23 parts of sodium hydroxids, 48 parts in two (4-hydroxy phenyl) propane (dihydroxyphenyl propane) of 2.2-, 0.5 part of hexadecyl front three brometo de amonio joins in the three-necked bottle that agitator and thermometer are housed, and forms water after the stirring and dissolving; Dropping in reactor is by 336 parts of trichloromethanes, 34.2 parts of p-phthaloyl chlorides, the oil phase of 22.8 parts of compositions of m-phthaloyl chloride.After 30 ℃ of temperature are reacted half an hour, add 2 parts of tert.-butyl phenols, continue to react stopped reaction after 2 hours.Extremely neutral with acetic acid neutralization reaction liquid, leave standstill and make two to be separated, sublevel organism down is added drop-wise to precipitating in the hot water under the violent stirring mutually, the precipitating thing is filtered be washed with distilled water to no chlorion, at last product is placed vacuum drying oven to dry to constant weight for 60 ℃, obtain the bis-phenol polyarylester in temperature.
The polymer with bis phenol A aromatic ester product that makes is placed on and uses the dehydrated alcohol purification by liquid extraction in the cable-styled extractor, and purified product places vacuum drying oven in 60 ℃ of oven dry of temperature constant weight.Measure intrinsic viscosity [the η]=1.1dl/g of product; Second-order transition temperature Tg=172 ℃; Heat decomposition temperature Td=507 ℃.
Embodiment 4: with 920 parts of distilled water, 19 parts of sodium hydroxids, 2.2-34.28 parts in two (4-hydroxy phenyl) propane (dihydroxyphenyl propane), 2.2-two (6-allyl groups, the 4-hydroxy phenyl) propane is 15.35 parts, 0.8 part in tetrabutyl phosphonium bromide sodium joins in the three-necked bottle that agitator and thermometer are housed, and forms water after the stirring and dissolving; Dropping in reactor is by 315.8 parts of 1.1.2.2-tetrachloroethane, 18.1 parts of p-phthaloyl chlorides, 39.9 parts of m-phthaloyl chlorides, the oil phase of composition.After 35 ℃ of temperature are reacted half an hour, add 1.5 parts of orthoxenols, continue to react stopped reaction after 1 hour.Extremely neutral with acetic acid neutralization reaction liquid, leave standstill and make two to be separated, following sublevel organism is added drop-wise to precipitating in the acetone under the violent stirring mutually, the filtration of precipitating thing is washed with distilled water to no chlorion, at last product is placed vacuum drying oven to dry to constant weight for 50 ℃, obtain the bis-phenol polyarylester in temperature.
The product that makes is placed on and uses the dehydrated alcohol purification by liquid extraction in the cable-styled extractor, and purified product places vacuum drying oven in 50 ℃ of oven dry of temperature constant weight.Measure intrinsic viscosity [the η]=0.52dl/g of product; Second-order transition temperature Tg=210 ℃; Heat decomposition temperature Td=450 ℃.
Embodiment 5: with 946.8 parts of distilled water, 22 parts of sodium hydroxids, 2.2-34.28 parts in two (4-hydroxy phenyl) propane (dihydroxyphenyl propane), 4.4 10.14 parts of ' one dihydroxy phenyl thioethers, 0.32 part of triethyl benzyl ammonia chloride, 0.32 part of sodium lauryl sulphate joins in the three-necked bottle that agitator and thermometer are housed, and forms water after the stirring and dissolving; Dropping in reactor is by 232 parts of methylene dichloride, 104 parts of 1.1.2.2.-tetrachloroethane, 12.24 parts of p-phthaloyl chlorides, the oil phase of 28.56 parts of compositions of m-phthaloyl chloride.After 30 ℃ of temperature are reacted half an hour, add 1.7 parts of tert.-butyl phenols, continue to react stopped reaction after 1 hour.Extremely neutral with acetic acid neutralization reaction liquid, leave standstill and make two to be separated, following sublevel organism is added drop-wise to precipitating in the methyl alcohol under the violent stirring mutually, the filtration of precipitating thing is washed with distilled water to no chlorion, at last product is placed vacuum drying oven to dry to constant weight for 50 ℃, obtain bisphenol type poly arylate in temperature.
Prepared product is placed on uses the anhydrous methanol purification by liquid extraction in the cable-styled extractor, purified product places vacuum drying oven in 50 ℃ of oven dry of temperature constant weight.Measure intrinsic viscosity [the η]=0.458dl/g of product; Second-order transition temperature Tg=158 ℃; Heat decomposition temperature Td=400 ℃.
Application example:
Take by weighing 1 part of polymer with bis phenol A aromatic ester that obtains by embodiment 1, be made into 3% polymers soln with methylene dichloride and tetrachloroethane (1: 1 weight ratio) mixed solvent.The silver-plated test piece of various different substrate materials is immersed respectively in the polyarylester solution, and dip-coating evenly back is taken out, and dries up naturally in air or 80 ℃ of drying in oven of temperature 2 minutes.Hydrogen sulfide is carried out in silver-plated test piece behind the dip-coating polymkeric substance, the test of sodium sulphite corrosive nature, the result is shown in table 1..
Note: (1) is pressed GJB1300-91 and is measured; (2) dripping about 0.5 ml concn on test piece is 1% sodium sulfide solution, observes its variable color time.
Table 1 polymer with bis phenol A aromatic ester corrosion resistance of coating
Claims (9)
1. bisphenol type poly arylate is characterized in that the chemical structural formula of this bisphenol type poly arylate is:
Wherein,
R＝O，-CH
2-CH＝CH
2
n＝50-180
The recipe ingredient of this polyarylester starting raw material is by weight:
25～57 parts of phthalyl chlorides
36～50 parts of bisphenol cpds
0.2～0.8 part of organic quaternary amine
232～336 parts of hydrochloric ethers
18～23 parts in sodium hydroxide
890～990 parts of distilled water
1～3 part of end-capping reagent
Intrinsic viscosity [η]=0.5～1.1dL/g of the bisphenol type poly arylate that the employing interface fasculation method makes, second-order transition temperature T
g=155～220 ℃, heat decomposition temperature T
d=400～550 ℃.
2. according to the described bisphenol type poly arylate of claim 1, it is characterized in that phthalyl chloride is p-phthaloyl chloride and m-phthaloyl chloride, p-phthaloyl chloride and m-phthaloyl chloride by weight proportion 10～90: 90～10.
3. according to the described bisphenol type poly arylate of claim 1, it is characterized in that bisphenol cpd is two (4-hydroxy phenyl) propane of 2.2-, 4.4 '-the dihydroxy phenyl thioether, at least a in two (6-allyl group, the 4 hydroxy phenyls) propane of 2.2-.
4. according to the described bisphenol type poly arylate of claim 1, it is characterized in that organic quaternary amine is a sodium lauryl sulphate, cetyl trimethylammonium bromide, triethyl benzyl ammonia chloride, at least a in the Tetrabutyl amonium bromide.
5. according to the described bisphenol type poly arylate of claim 1, it is characterized in that hydrochloric ether is a methylene dichloride, at least a in tetrachloroethane, trichloromethane, 1.2-ethylene dichloride, the 1.1.1-trichloroethane.
6. according to the described bisphenol type poly arylate of claim 1, it is characterized in that end-capping reagent is a p-tert-butylphenol, orthoxenol is to a cumylphenol. at least a in the phenol.
7. according to the preparation method of one of claim 1-6 described bisphenol type poly arylate, it is characterized in that this method may further comprise the steps:
With distilled water 890～990 weight parts, sodium hydroxid 18～23 weight parts, bisphenol cpd 36-48 weight part, organic quaternary amine 0.2～0.8 weight part, add and have in the three-necked bottle of agitator and thermometer, form water after the stirring and dissolving, and in reactor, be added dropwise to solvent hydrochloric ether 232～336 weight parts and phthalyl chloride 25～57 weight parts and form oil phase, low whipping speed 600～1200rpm, temperature is reacted for 10～35 ℃, add end-capping reagent 1～3 weight part then, keep reacting stopped reaction after 1～3 hour, reaction solution is neutralized to neutrality with acid, leaves standstill to make two to be separated, organism is added drop-wise to precipitating in the precipitating agent under the violent stirring mutually, the precipitating product is washed with distilled water to no chlorion, places vacuum drying oven to dry to constant weight for 40～60 ℃ in temperature again, and the product that makes is placed in the cable-styled extractor and purifies with solvent extraction, purified product places vacuum drying oven in 40-60 ℃ of oven dry constant weight, obtains bisphenol type poly arylate.
8. according to the preparation method of the described bisphenol type poly arylate of claim 7, it is characterized in that precipitating and purification by liquid extraction solvent are methyl alcohol, ethanol, normal hexane, acetone, any in ethyl acetate and the water.
9. according to the purposes of the described bisphenol type poly arylate of claim 1, it is characterized in that this bisphenol type poly arylate is used for the polymeric coating layer of anti-silver-plated erosion variable color.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN103965452A (en) * | 2014-05-09 | 2014-08-06 | 江阴市博生新材料科技有限公司 | Method for preparing, separating and purifying polyarylester (PAR) by adopting phase-transfer catalysis interface polycondensation process |
| CN112341608A (en) * | 2019-08-09 | 2021-02-09 | 四川斯派恩新材料有限公司 | High-temperature-resistant high-fluidity polyarylate and preparation method thereof |
| CN112708114A (en) * | 2020-12-29 | 2021-04-27 | 四川大学 | Low-dielectric high-light-transmittance polyarylate, polyarylate film and preparation method thereof |
| US20210202899A1 (en) * | 2019-05-13 | 2021-07-01 | Beijing Boe Display Technology Co., Ltd. | Oled display screen, display panel and manufacturing 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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2006
- 2006-10-27 CN CN 200610022133 patent/CN1944488A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN102558518B (en) * | 2010-12-07 | 2014-09-10 | 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 |
| CN103965452A (en) * | 2014-05-09 | 2014-08-06 | 江阴市博生新材料科技有限公司 | Method for preparing, separating and purifying polyarylester (PAR) by adopting phase-transfer catalysis interface polycondensation process |
| US20210202899A1 (en) * | 2019-05-13 | 2021-07-01 | Beijing Boe Display Technology Co., Ltd. | Oled display screen, display panel and manufacturing method thereof |
| CN112341608A (en) * | 2019-08-09 | 2021-02-09 | 四川斯派恩新材料有限公司 | High-temperature-resistant high-fluidity polyarylate and preparation method thereof |
| CN112341608B (en) * | 2019-08-09 | 2023-09-15 | 四川斯派恩新材料有限公司 | High-temperature-resistant high-fluidity polyarylester and preparation method thereof |
| 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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