CN1124745A - Polyaryl ether nitrile and producing process thereof - Google Patents

Polyaryl ether nitrile and producing process thereof Download PDF

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Publication number
CN1124745A
CN1124745A CN 94113026 CN94113026A CN1124745A CN 1124745 A CN1124745 A CN 1124745A CN 94113026 CN94113026 CN 94113026 CN 94113026 A CN94113026 A CN 94113026A CN 1124745 A CN1124745 A CN 1124745A
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Prior art keywords
arylene ether
ether nitrile
poly
raw material
sulfone
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CN1058729C (en
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张连来
顾宜
江璐霞
郭旭虹
蔡兴贤
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Sichuan Union University
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Abstract

The process for preparing polyaryl ethernitrile having arylether ketone and arylethersulfone structural units on its main chain features that such monomers as dihalophenyl cyanide, dihalodiphenylketone, dihalodiphenylsulfone, etc. and the reaction takes place under existance of non-protonic polar solvent, dewatering agent and alkali-metal carbonate. Obtained product has high refractory properties, belongs to special engineering plastics, and is used as refractory structural and insulating material with low cost.

Description

A kind of poly (arylene ether nitrile) and manufacture method thereof
The present invention relates to a kind of synthetic method of poly (arylene ether nitrile), this superpolymer contains structural units such as aryl oxide nitrile, aryl ether ketone and aryl ether sulfone in its molecular structure, combines the performance characteristics of each integral part, belongs to the special engineering plastics field.
The sixties Mo early seventies, the research of high-performance polymer is very active, polyphenylene oxide, polyphenylene sulfide, polyaryletherketone, polyether sulphone etc. are developed in succession, and realized industrialization, become the important project plastics variety so far, meanwhile, the research of poly (arylene ether nitrile) begins to see patent documentation.
The D.R.Heath of GE in 1973 etc. utilize the nitro substitution reaction to form ehter bond, prepared poly (arylene ether nitrile), and applied for United States Patent (USP) U.S.P3,730,946, it is more serious that this invents used nitro substitution reaction side reaction, and productive rate is low, the product poor heat resistance fails to obtain practical application always.
Nineteen eighty-two and nineteen eighty-three U.S. D.K.Mohanty etc. are monomer with the phenyl-dihalide formonitrile HCN, and it is higher to obtain molecular weight, the poly (arylene ether nitrile) that thermotolerance is high (ACS Polymer Preprints, 23 (1), 284 (1982); 24 (1), 147 (1983)) solvent for use is a N monomethyl pyrrolidone (NMP).
X represents Cl, F
The R table
The Japanese S.Matsuo of Idemitsu Kosen Co., Ltd. in 1986 etc. have applied for a kind of by the European patent EP O1921771987 of phenyl-dihalide formonitrile HCN with different dihydric phenol prepared in reaction poly (arylene ether nitrile)s, the said firm has applied for containing patent EP02430001992 the said firm of poly (arylene ether nitrile) of a bit architecture again with phenyl-dihalide formonitrile HCN and the dihydric phenol reaction that contains chromophore, preparation fluorescent poly (arylene ether nitrile), obtain United States Patent (USP) U.S.P.5,153,306,1993, the poly (arylene ether nitrile) application of the biphenyl contenting structure of the said firm Japanese Patent J.P.05,310,913.
In public publication, Japanese S.Matsuo in 1993 etc. have reported the different dihydric phenol prepared in reaction poly (arylene ether nitrile) with 12 kinds of phenyl-dihalide formonitrile HCN Journal of PolymerScience, PartA; Polymer Chemistry 31,3439 (1993).Reported the preparation Journal ofPolymer Science of the fluorescent poly (arylene ether nitrile) that contains chromophore recently again, Part A; Polymer Chemistry 32,1071 (1994).The molecular structure and the crystalline texture that contain the poly (arylene ether nitrile) of a bit architecture also have report Polymer 35,18 (1994) in recent years.
In sum, dinitrobenzene or phenyl-dihalide formonitrile HCN or with the reaction of single dihydric phenol or with two kinds of different dihydric phenols reactions, used dihydric phenol is confined to dihydroxyphenyl propane more, Resorcinol, Resorcinol, naphthalenediol etc., product structure is single, using value is little.
The objective of the invention is provides a kind of poly (arylene ether nitrile) and manufacture method thereof at the deficiencies in the prior art.Be characterized in that (one of them is 4 with phenyl-dihalide formonitrile HCN and two or more dihydric phenol, 4 ＇-dihydroxy benaophenonel or 4,4 ＇-dihydroxy diphenylsulphone) reaction, perhaps phenyl-dihalide formonitrile HCN and another kind of or multiple dihalo aromatic compound (containing ketone, sulfone structure) and dihydric phenol reaction, obtain poly (arylene ether nitrile), can adjust the product structure performance largely.
Poly (arylene ether nitrile) provided by the invention and manufacture method thereof, its starting raw material recipe ingredient (by weight) is:
10-170 parts of halogeno-benzene formonitrile HCNs (available 2,6-dichlorobenzonitrile, 2,6-difluorobenzonitrile, 4,4-dichlorobenzonitrile)
Contain 250-0 part of ketone, sulfone phenolic compound (available 4,4 ＇-dihydroxy benaophenonel, 4,4 ＇-dihydroxy diphenylsulphone)
0-250 parts of phenolic compounds (available Resorcinol, Resorcinol, dihydroxyphenyl propane, naphthalenediol and '-biphenyl diphenol)
Contain ketone, fragrant halides (available 4,4 ＇-difluoro benzophenone, 4,4 ＇-dichloro diphenyl sulfone, 4,4 ＇-difluorodiphenyl sulfone) 0-295 parts of sulfone
Solvent (available dimethyl sulfoxide (DMSO), N-Methyl pyrrolidone, tetramethylene sulfone)
1000-3500 parts
An alkali metal salt (available anhydrous sodium carbonate, anhydrous sodium bicarbonate, Anhydrous potassium carbonate)
100-165 parts
750-1200 parts of dewatering agents (available toluene, dimethylbenzene, chlorobenzene)
1. polycondensation
With the weighing respectively of above-mentioned recipe ingredient, add halogeno-benzene formonitrile HCN, aromatic halogenate, phenolic compound, solvent, an alkali metal salt and dewatering agent successively in the reactor that has water trap, agitator, thermometer and the nitrogen turnover mouth of pipe, logical nitrogen, start stirring, be warming up to 110-180 ℃ of dehydrations 1-8 hours, steam dewatering agent toluene, dimethylbenzene or chlorobenzene, elevated temperature obtains the poly (arylene ether nitrile) mixing solutions in 120-250 ℃ of reactions 1-20 hours.
2. aftertreatment
Above-mentioned reactor is stopped heating, be chilled to about 150 ℃, again with poly (arylene ether nitrile) mixing solutions impouring hot water/methanol solution first, constantly stir, regulating pH value with dilute hydrochloric acid is about 7, place natural subsidence, sucking-off supernatant liquid then, the thing that will settle out filters, obtained thick product down in dry 24 hours in 120-180 ℃, thick product is dissolved in refining solvent N,N-DIMETHYLACETAMIDE or N-Methyl pyrrolidone first, temperature is 150-200 ℃ again, constantly stirs precipitating in hot water/methyl alcohol down, remove supernatant liquid, settle out thing after filtering in 80-165 ℃ of vacuum-dryings 24 hours, obtain refining poly (arylene ether nitrile), its molecular structure is:
R 1For
R 2For
Figure A9411302600083
x x + y = 0.5 - 1 Perhaps
Ar 1＝R 1，R 2
Ar 2＝R 1 x x + y = 0.1 - 1
The poly (arylene ether nitrile) that the inventive method is made is a white, light grey to light brown powder or particulate thermoplastic resin, different according to the raw material variety that adopts with proportioning, can obtain crystallinity or unit's setting product respectively, its second-order transition temperature is 140-265 ℃, the fusing point of crystalline resin is 320-375 ℃, product has high thermostability, and weightless 5% temperature is between 380-485 ℃.
The present invention has following advantage:
1. introduce aryl ether ketone, aryl ether sulfone structural unit on the macromolecular chain, the resistance toheat of poly (arylene ether nitrile) is further improved.
2. by regulating the ratio of aromatic halogenate, phenolic compound, can control the structure and the performance of product.
3. monomer wide material sources, cost is low, and product price is significantly less than the Japanese Patent product, and higher performance is arranged, and is easy to apply, and remarkable economic efficiency and social benefit are arranged.
Embodiment
1. take into account in the four-necked bottle of the nitrogen turnover mouth of pipe having agitator, water trap, temperature, add 2,6-difluorobenzonitrile 351 grams, Resorcinol 138 grams, Resorcinol 138 grams, anhydrous sodium carbonate 292 grams add N-Methyl pyrrolidone 3000 grams then, toluene 1000 grams, logical nitrogen, start stirring, after 1-5 hours, steam toluene in 110-180 ℃ of backflows.Reacted 4-8 hours down at 150-200 ℃.Cooling, precipitates in water, filters to pH value 7 with hcl acidifying.Dried crude product is dissolved in the solvent of heat, precipitates in the water/methyl alcohol of heat, last vacuum-drying, and productive rate is 98%.
2. with 2,6-difluorobenzonitrile 70.2 restrains, Resorcinol 27.6 grams, 4,4 ＇-dihydroxy diphenylsulphone 62.1 grams, anhydrous sodium carbonate 58.3 grams, N-methyl-2-pyrrolidone 500 gram, toluene 150 restrain in the identical equipment of embodiment 1, logical nitrogen, start stirring, after 1-6 hours, steam toluene in 110-180 ℃ of backflows, 150-200 ℃ of down reactions 2-8 hours, product obtains productive rate 97% through the identical aftertreatment of embodiment 1, this product second-order transition temperature is 159.6 ℃, 335.2 ℃ of molten points.
3. with 2,6-dichlorobenzonitrile 43.1 restrains 4,4 ＇-dichloro diphenyl sulfone 71.8 grams, Resorcinol 55.1 grams, Anhydrous potassium carbonate 78.3 grams, N-Methyl pyrrolidone 500 gram, toluene 150 restrain the identical equipment first in embodiment 1, logical nitrogen, start stirring, in 110-150 ℃ of backflows 1～8 hour, steam toluene, reacted 4-8 hours down at 150-200 ℃, product obtains productive rate 97.8% through the identical method aftertreatment of embodiment 1.Product structure characterizes through FT-IR.Second-order transition temperature is 199.1 ℃, and weightless 5% temperature is 406.7 ℃.
4. with 2,6-dichlorobenzonitrile 21.5 restrains 4,4 ＇-dichloro diphenyl sulfone 35.9 grams, Resorcinol 27.6 grams, anhydrous sodium bicarbonate 22.8 grams, dimethyl sulfoxide (DMSO) 300 gram, chlorobenzene 100 restrain in the identical equipment of embodiment 1, logical nitrogen, start stirring, in 110-180 ℃ of backflows 2-6 hours, steam chlorobenzene, reacted 4-10 hours down at 150-200 ℃, product obtains productive rate 98% through the aftertreatment of embodiment 1 same procedure.
5. with 2,6-dichlorobenzonitrile, 43.1 grams, 4,4 ＇-difluoro benzophenone 54.5 grams, '-biphenyl diphenol 93.1 grams, anhydrous sodium carbonate 58.3 grams, tetramethylene sulfone 700 grams, dimethylbenzene 180 grams, logical nitrogen starts to stir in 110-180 ℃ and refluxed 1-5 hours, steam dimethylbenzene, reacted 4-5 hours down at 185～250 ℃, product obtains productive rate 97.3% through embodiment 1 same procedure aftertreatment.

Claims (9)

1. poly (arylene ether nitrile) is characterized in that this poly (arylene ether nitrile) starting raw material recipe ingredient (by weight) is:
10-170 parts of halogeno-benzene formonitrile HCNs
Contain 250-0 part of ketone, sulfone phenolic compound
0-250 parts of phenolic compounds
Contain 0-295 parts of ketone, sulfone aromatic halogenates
Solvent 1000-3500 part
An alkali metal salt 100-165 part
Dewatering agent 750-1200 part
2. according to the described poly (arylene ether nitrile) of claim 1, it is characterized in that this poly (arylene ether nitrile) starting raw material is 2 with the halogeno-benzene formonitrile HCN, 6-dichlorobenzonitrile, 2,6-difluorobenzonitrile, 2,4 dichloro benzene formonitrile HCN.
3. according to the described poly (arylene ether nitrile) of claim 1, it is characterized in that this poly (arylene ether nitrile) starting raw material with contain ketone, the sulfone phenolic compound is 4,4 ＇-dihydroxy benaophenonel, 4,4 ＇-dihydroxy diphenylsulphone.
4. according to the described poly (arylene ether nitrile) of claim 1, it is characterized in that this poly (arylene ether nitrile) starting raw material phenolic compound is a Resorcinol, Resorcinol, dihydroxyphenyl propane, naphthalenediol and '-biphenyl diphenol.
5. according to the described poly (arylene ether nitrile) of claim 1, it is characterized in that this poly (arylene ether nitrile) starting raw material with contain ketone, the sulfone aromatic halogenate is 4,4 ＇-difluoro benzophenone, 4,4 ＇-dichloro diphenyl sulfone, 4,4 ＇-difluorodiphenyl sulfone.
6. according to the described poly (arylene ether nitrile) of claim 1, it is characterized in that this poly (arylene ether nitrile) starting raw material solvent is a dimethyl sulfoxide (DMSO), N-Methyl pyrrolidone, tetramethylene sulfone.
7. according to the described poly (arylene ether nitrile) of claim 1, it is characterized in that this poly (arylene ether nitrile) starting raw material an alkali metal salt is an anhydrous sodium carbonate, anhydrous sodium bicarbonate, Anhydrous potassium carbonate.
8. according to the described poly (arylene ether nitrile) of claim 1, it is characterized in that this poly (arylene ether nitrile) starting raw material dewatering agent is a toluene, dimethylbenzene, chlorobenzene.
9. according to the manufacture method of the described poly (arylene ether nitrile) of claim 1, it is characterized in that:
(1) polycondensation
With the weighing respectively of above-mentioned recipe ingredient, add halogeno-benzene formonitrile HCN, aromatic halogenate, phenolic compound, solvent, an alkali metal salt and dewatering agent successively in the reactor that has water trap, agitator, thermometer and the nitrogen turnover mouth of pipe, logical nitrogen, start stirring, be warming up to 110-180 ℃ of dehydrations 1-8 hours, steam dewatering agent toluene, dimethylbenzene or chlorobenzene, 120-250 ℃ of reactions of elevated temperature 1-20 hours obtain the poly (arylene ether nitrile) mixing solutions.
(2) aftertreatment
Above-mentioned reactor is stopped heating, be chilled to about 150 ℃, again with in poly (arylene ether nitrile) mixing solutions impouring hot water/methanol solution, constantly stir, regulating pH value with dilute hydrochloric acid is about 7, place natural sedimentation, sucking-off supernatant liquid then, the thing that will settle out filters, obtained thick product down in dry 24 hours in 120-180 ℃, thick product is dissolved in refining solvent N,N-DIMETHYLACETAMIDE or the N-Methyl pyrrolidone, temperature is 150-200 ℃ again, constantly stirs precipitating in hot water/methyl alcohol down, remove supernatant liquid, settle out thing after filtering in 80-165 ℃ of vacuum-dryings 24 hours, obtain refining poly (arylene ether nitrile), its molecular structure is:
Figure A9411302600031
R 1For
R 2For
Figure A9411302600033
Figure A9411302600041
x x + y = 0.5 - 1 Perhaps
Ar 1＝R 1，R 2
Ar 2＝R 1 x x + y = 0.1 - 1
CN94113026A 1994-12-13 1994-12-13 Polyaryl ether nitrile and producing process thereof Expired - Fee Related CN1058729C (en)

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CN100343306C (en) * 2006-02-20 2007-10-17 扬州天辰精细化工有限公司 Polyarylether carbonitrile industrial production method
CN102121142A (en) * 2010-06-04 2011-07-13 中国工程物理研究院化工材料研究所 Preparation method of poly(arylene ether nitrile) fibers
CN102504242A (en) * 2011-11-29 2012-06-20 电子科技大学 Polyaryletherketone-nitrile copolymer and preparation method thereof
CN102516528A (en) * 2011-12-16 2012-06-27 四川飞亚新材料有限公司 Polyaryl ether nitrile resin, polyaryl ether nitrile fiber and preparation method thereof
CN102532516A (en) * 2011-12-16 2012-07-04 四川飞亚新材料有限公司 Poly aryl ether nitrile resin, poly aryl ether nitrile fiber and preparation methods thereof
CN102558558A (en) * 2011-12-20 2012-07-11 电子科技大学 Polyether sulphone-nitrile resin and industrialization synthetic method thereof
CN102585675A (en) * 2012-03-16 2012-07-18 中国科学院长春应用化学研究所 Insulation coating composition
CN102660016A (en) * 2012-03-16 2012-09-12 中国科学院长春应用化学研究所 2,6-dihalo benzonitrile-4,4'dihalobenzophenone-phenolphthalein terpolymer and preparation method thereof
CN102766256A (en) * 2012-07-31 2012-11-07 电子科技大学 Bisphenol A type polyarylene sulfide ether nitrile resin and preparation method thereof
WO2013135127A1 (en) * 2012-03-16 2013-09-19 中国科学院长春应用化学研究所 2,6-dihalobenzonitrile-4,4'-dihalobenzophenone-phenolphthalein terpolymer, preparation method thereof and insulating coating composition
CN103626999A (en) * 2013-11-27 2014-03-12 江门市优巨新材料有限公司 Industrial synthesis method of polyarylether sulfone resin
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WO2015135195A1 (en) * 2014-03-14 2015-09-17 绵阳鸿琪新材料科技有限公司 Self-foaming polyether sulfone resin and preparation method therefor
CN105754089A (en) * 2016-05-12 2016-07-13 绵阳鸿琪新材料科技有限公司 Synthesis method of high-temperature-resistant polyarylene ether nitrile resin
CN109535413A (en) * 2018-12-03 2019-03-29 电子科技大学 The synthesis of side chain poly (arylene ether nitrile) containing amino-functional group
CN110305312A (en) * 2019-07-05 2019-10-08 电子科技大学 A kind of synthetic method of high molecular weight polyarylether nitrile
CN113563579A (en) * 2021-08-17 2021-10-29 西南石油大学 Azobenzene-poly (arylene ether nitrile) composite material and preparation method thereof
CN114479063A (en) * 2020-10-26 2022-05-13 中国石油化工股份有限公司 Poly (arylene ether nitrile) containing naphthalene structure and preparation method and application thereof

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JPH01299823A (en) * 1988-05-27 1989-12-04 Idemitsu Kosan Co Ltd Polycyanoaryl ether and its production
JPH0245526A (en) * 1988-08-05 1990-02-15 Idemitsu Kosan Co Ltd Polycyanoaryl ether and production thereof
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CN100343306C (en) * 2006-02-20 2007-10-17 扬州天辰精细化工有限公司 Polyarylether carbonitrile industrial production method
CN102121142B (en) * 2010-06-04 2012-11-07 中国工程物理研究院化工材料研究所 Preparation method of poly(arylene ether nitrile) fibers
CN102121142A (en) * 2010-06-04 2011-07-13 中国工程物理研究院化工材料研究所 Preparation method of poly(arylene ether nitrile) fibers
CN102504242A (en) * 2011-11-29 2012-06-20 电子科技大学 Polyaryletherketone-nitrile copolymer and preparation method thereof
CN102516528A (en) * 2011-12-16 2012-06-27 四川飞亚新材料有限公司 Polyaryl ether nitrile resin, polyaryl ether nitrile fiber and preparation method thereof
CN102532516A (en) * 2011-12-16 2012-07-04 四川飞亚新材料有限公司 Poly aryl ether nitrile resin, poly aryl ether nitrile fiber and preparation methods thereof
CN102558558A (en) * 2011-12-20 2012-07-11 电子科技大学 Polyether sulphone-nitrile resin and industrialization synthetic method thereof
CN102585675A (en) * 2012-03-16 2012-07-18 中国科学院长春应用化学研究所 Insulation coating composition
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CN102585675B (en) * 2012-03-16 2014-02-19 中国科学院长春应用化学研究所 Insulation coating composition
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CN102766256A (en) * 2012-07-31 2012-11-07 电子科技大学 Bisphenol A type polyarylene sulfide ether nitrile resin and preparation method thereof
CN103626999A (en) * 2013-11-27 2014-03-12 江门市优巨新材料有限公司 Industrial synthesis method of polyarylether sulfone resin
WO2015135195A1 (en) * 2014-03-14 2015-09-17 绵阳鸿琪新材料科技有限公司 Self-foaming polyether sulfone resin and preparation method therefor
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CN114479063A (en) * 2020-10-26 2022-05-13 中国石油化工股份有限公司 Poly (arylene ether nitrile) containing naphthalene structure and preparation method and application thereof
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CN113563579B (en) * 2021-08-17 2023-09-15 西南石油大学 Azobenzene-polyarylether nitrile composite material and preparation method thereof

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