• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    A method for producing polyetherimide of general formula I: ;-( cis), - where Rj is O or CH, j, p 5-30 by reacting the alkali metal salt of 2,2-di- (p-oxyphenyl) propane with a common bisphthalimide halide Formulas I: -Kg where R - has the indicated values, X is a halogen, in an aprotic solvent medium at 25-150 ° C, characterized in that, in order to intensify the process and increase the degree of polymerization, the compound halogenated bisphthalimide of general formula 1J is used formulas P, where X - 3 - or 4-fluorine,
    公开号:SU1151201A3
    申请号:SU742062706
    申请日:1974-09-27
    公开日:1985-04-15
    发明作者:Джервис Вильямс Фрэнк
    申请人:Дженерал Электрик Компани (Фирма)；
    IPC主号:
    专利说明:

    1 The invention relates to the preparation of polyethernmides of the general formula about 1t. where Rj is -O- or, p 5-30. Polyetherprimes can be used as components for injection molding and composition for wire coating. A known method of producing polyether imides by reacting salts of a diatomic phenol, for example 2,2-di- (p-hydroxyphenyl) propane with bis-chlorophthalimide in an aprotic solvent medium at 25-150 seconds. The disadvantage of this method is considerable time ( sometimes for several days at temperatures of 100 ° C), and the polymers thus obtained are characterized by low intrinsic viscosity generally less than 0.2. The purpose of the invention is to intensify the process and increase the degree of polymerization. The goal is achieved by the fact that according to the method polyetherimides are obtained by reacting alkali metal salt of 2,2-di- (p-hydroxyphenyl) propane with halide with aqueous bisphthalimide of the general formula de R -O- or -CHj-, p 5-30 is halogen, the medium of an aprotic solvent at 5–150 ° C, as a halide bisphthalimide of the general formula 11, a compound of the formula II is used, where X is 3- and 6-fluoro. Suitable dipolar aprotic organic solvents include, for example, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, hexamethylphosphorous triamide, tetramethylene sulfone, etc. The reaction between bis- (fluorimide) and the alkali salt of a dihydric phenol promotes the stirring of the reaction mixture to facilitate the interaction between the reactants. In addition to these dipolar aprotic solvents, additional solvents such as toluene, benzene, xylene, etc. can be used. The reaction time varies from 10 to 2 hours or less depending on such factors as the reagents used, the degree of mixing, the temperature at which the reaction is conducted, etc. An acid such as acetic acid can be added to the end of the reaction in order to neutralize the residual alkali metal ions. If necessary, an additional solvent can be added to the mixture. The resulting mixture can then be added to a precipitating solvent such as methanol to effect the separation and separation of the polymer. The polymer can be recovered by standard methods such as filtration. The extracted polymer is then rinsed with additional solvent, namely chlorophoma), and planted out again. Examples of the method (all parts are by weight). . 3 Example 1. The sodium salt of bis-phenol A is prepared by stirring a mixture of 1.659 parts of a 50% aqueous solution of sodium hydroxide and 2.363 parts of bis-phenol A with 15 parts of dimethyl sulfoxide and 25 parts of toluene under a nitrogen atmosphere. The mixture is heated with reverse cooling with a nickname and water forms an azeotr with it. After removing water, toluene is distilled off until the temperature in the boiler reaches. The mixture is cooled to 65 ° C. Bis-4- (3-fluorophaptamide) phenyl methane is obtained by mixing with si 10.04 parts of 3-fluorophthalic anhydride and 5.99 parts of methylenedianiline in 100 parts of glacial acetic acid in nitrogen atmosphere. After the mixture was boiled under reflux for 3 h, it was cooled to room temperature. In this way, a crude product is obtained, which is collected and washed three times with diethyl ether. The initial product is then dried in a vacuum oven at 65 ° C, which gives a 92% yield of that crystalline material with a melting point of 233.5-234 ,. Based on the method of production and analysis of elements. Calculated,%: C, 70.4; H 3.3; N 5.7.
    The above procedure is repeated except that an equivalent amount of bis- (chlorofthalimide) is used instead of bis- (fluorophthalimide). After a 6-hour reaction at 70 ° C, the characteristic viscosity of the product in dimethylformamide is 0.099.
    Then the reaction was conducted for 16 h at. A product was obtained having an intrinsic viscosity of 0.154 () in a dimeshmoform.
    The reaction with mezvdu bis- (Atorphthalimide) is much faster with the sodium salt of bis-Lenol
    with comparable bis- (chlorophthalimide). In addition, molecular weight
    polyetherimide, obtained by reaction with bis- (fluorophthalimide), is significantly higher than the molecular weight of the polyetherimide from chemically bound units of bis- (chlorine (talimide).
    Example 2 The sodium salt of bisphenol A is prepared in the same manner as in Example 1 by reaction of 1.554 hours, a 50% aqueous solution of sodium hydroxide and 2.215 parts of bisfeiol A in a mixture of toluene-dimethylsulfoxide. This mixture 014 C29H ,, 04N2Pi Found,%: C 70.2; H 3.4; N 5.5 The product was bis- (4- (3-fluorophthalimide) phenylJ methane. To the sodium bisphenol A salt obtained above, add 5 h of the above mentioned bis- (fluorophthalimide) and 15 h of anhydrous toluene. The resulting mixture is stirred for 6 h. at 70. Then the mixture is allowed to cool to room temperature and approximately 0.1 parts of acetic acid is added dropwise. The mixture is then diluted with 30 parts of a mixture of dimethyl sulfoxide and toluene 1: 1. The resulting mixture is added dropwise to 600 hours of methanol. The product is precipitated and separated by filtration, dried and again dissolved. in chloroform and precipitated in methanol. After drying at 65 ° C in a vacuum oven, a product with a characteristic viscosity in dimethylformamide of 0.277 (n 15) is obtained. A longer reaction time does not increase the characteristic viscosity of the product. Based on the preparation method, the product is polyether: mid, composed, per week, of the following chemical bonded units: I cooled before and 4.815 parts (3-fluorophthalimide) fer NIL oxide followed by washing with toluene are added. Above C (3-torphthalimide) Lenil J oxide is produced by Ivanov mixture of 10.71 hours. 3-ftorftalezogo anhydride and oxydianiline 6.46 h at 107 h. of glacial acetic acid under a nitrogen atmosphere. After the mixture is refluxed for 3 hours, it is cooled to room temperature. A product is obtained which is separated and washed twice with diethyl ether. After that, the crude product is dried in a vacuum oven at 65 ° C. which gives a 98% yield of yellow crystalline material with a melting point of 298.5-229.5 ° C. Based on the method of obtaining and analyzing the elements of OB-1, this product was bis-C4- (3-fluorophthalimide) phenyl 3 seed.
    Example 3. The sodium salt of bis-phenol A is prepared according to the method of Example 1 by the reaction of 3.5691 parts of a 50% aqueous solution of sodium hydroxide and 5.0909 parts of bis-phenol A in a mixture of dimethyl sulphoxide and toluene. The mixture is cooled before and 6.8779 parts of 1,6-bis- (3-fluorophthalimido) hexane is added, followed by washing with toluene.
    The indicated 1,6-bic- (3-fluorophthalide) hexane is prepared by stirring a mixture of 16 parts of 3-fluorophthalic anhydride and 5.60 parts of hexamethylenediamine (HMDA) in 135 ml of glacial acetic acid in a nitrogen atmosphere. After the mixture is refluxed for 3 hours, it is cooled to room temperature. In this way, a product is obtained which is separated and washed with dithyl ether. The crude product is then dried in a vacuum oven at, which gives
    5 90% yield of material with melting point t69-170 ° C. Based on the method of obtaining and analyzing elements.
    Calculated: C 64.1; H 4.4; 0 N 6.8.
     C zHi40 N.F ,,
    Found:% C 64.2, - H 4.5, N 6.7.
    The product is 1,6-bis - (3-fluorophthalimido) hexane.
    The mixture of sodium bis-phenol. A and bis- (fluorophthalimide) are stirred for approximately 6 hours at 70 s. The mixture is then cooled to room temperature and approximately 0.1 parts of acetic acid are added dropwise. The resulting solution is added dropwise to 600 parts of methanol. The precipitated product is separated by filtration, dried and redissolved in chloroform and precipitated in methanol. After drying in a vacuum oven at 65 ° C 1 Calculated,%: C 67.6, and 2.8; 5.6. fj Found,%: C 67.3; H 2.9.5, 3. N This mixture of sodium bisphenol A and bis- (fluorophthalimide) is stirred for 6 hours at. The mixture is then cooled to room temperature and approximately 0.1 parts of acetic acid are added. Thereafter, the resulting solution is added dropwise to 600 parts of methanol. The precipitated product is separated by filtration, dried and redissolved in chloroform and precipitated in methanol. After drying in a vacuum oven at 65 ° C, a product is obtained having a characteristic viscosity in dimethylformamide of 0.270 (p 13). Based on the production process, the product is a polyether compound consisting essentially of the following chemically linked units:
    a product is obtained having a characteristic viscosity in dimethylformamide in 0.176 (p 7). Exodus from
    11512018
    The method of obtaining the product was polyetherimide, consisting essentially of the following chemically bound units:
    Example 5: The effect of speed on the polyetrimimide preparation was carried out using bis- (fluorophthalimide) and bis- (chlorophthalimide), by measuring changes in the intrinsic viscosity of the polyetrimimide after 3; 6 and 16 hours, respectively, in accordance with the procedure of Example 1. The following results are obtained in which Fluoride indicates a polymer made from sodium bisphenol Au bis- 4- (3-fluorophthalimide) phenyl Zmetane, Chlorine to a polymer in which used (3-chlorophthalimide) phenyl} methane,. Time — The time taken to sample a mixture to measure intrinsic viscosity (X.V.)
    Time, h.V.
    30.20
    60,207
    160,209
    3 0.079
    60,099
    160,154
    Example 6 The sodium salt of bis-phenol A is prepared by stirring a mixture of 1.659 parts of a 50% aqueous solution of sodium hydroxide and 2.303 parts of bis-phenol Ac 15 parts of dimethyl sulfoxide and 25 parts of toluene under a nitrogen atmosphere. The mixture is heated under reflux, and the water is removed by distillation in the azeotropic mixture. After the total amount of water has been extracted, toluene is distilled off until the temperature of the mixture undergoing distillation reaches 160 ° C. Mixture allowed to cool to.
    (3-fluorophthalimide) phenyl-mangan is obtained by stirring a mixture of 10.04 parts of 3-fluorophthalic anhydride p 5.99 parts of methylene dianiline in 100 parts of glacial acetic acid in a nitrogen atmosphere. After heating the mixture under reflux, it is cooled to room temperature for 3 hours. A crude product is obtained, which is collected and washed 3 times with diethyl ether. Then the product, which is wet in frequency, is dried in a vacuum-basic cabinet at 65 ° C, which gives a yellow crystalline material having a melting point of 233.5-234, with a 92% yield. The product was (3-fluoro-phthalimide) fensch-13 methane on the basis of the method of obtaining the product and the following elemental analysis data: Calculated,%: 0-70.4; H-3.3; “75.7. Found,%: C70.2, H-3.4; 5.5. To the sodium bisphenol A salt prepared as indicated above, 5 parts of the bis (fluorine phthalimide) described above are added. The resulting mixture is stirred for about 3 hours at 150 ° C. The mixture is then allowed to cool to room temperature and about 0.1 h of acetic acid is added dropwise. The mixture is then diluted with 30 parts of a mixture of dimethyl sulfoxide and toluene 1: 1. Next, the resulting solution is added dropwise to 600 parts of methanol. The precipitated product is collected by filtration, dried, redissolved in chloroform and reprecipitated in methanol. After embroidering at 65 ° C in a vacuum drying oven, a product is obtained which has a characteristic viscosity in dimethylformamide 0.25. An increase in the duration of the reaction does not lead to an increase in the characteristic viscosity of the product. The product is a polyetherimide, trial by its method of preparation. Example. These operations are repeated to obtain (3-fluorophthalimide) phenyl methane and sodium salt of bisphenol A. The mixture is prepared by adding 15 parts of anhydrous toluene and 5 parts of the above-described bis-C4- (3-fluorophthalimide) phenyl methane to the aforementioned
    - About the sodium salt of bis-phenol A. The mixture is stirred for 24 hours at. To the sodium salt of bisphenol A, obtained as indicated above, is added 5 parts of the described bis- (fluorophthalimide). The resulting salt is stirred for approximately 3 hours at. The mixture is allowed to cool to room temperature and about 0.1 parts of acetic acid is added dropwise. The mixture is then diluted with 30 parts of a mixture of dimethyl sulfoxide and toluene 1: 1. The resulting solution is added dropwise to 600 parts of methanol. The product precipitated, which was collected by filtration, dried. And redissolved in chloroform, then reprecipitated in methanol. After drying at 65 ° C in a vacuum oven, a product is obtained having an intrinsic viscosity index in dimethylformamide of 0.25. An increase in the duration of the reaction does not lead to an increase in the characteristic viscosity of the product. Example 8. Following procedure 1, a nitride salt of bisphenol A was prepared in dimethyl sulfoxide / benzene, and an equal molar amount of 1,3-bis - (4-fluorophthalimido) benzene was added to this mixture with stirring. The whole mixture is kept in a nitrogen atmosphere at 80 ° C for 8 hours. From appropriate amounts of 4-fluorophthalic anhydride and m-phenylenediamine, a 1,3-bis (4-fluorophthalimido) benzol was prepared. The polymer is cooled to room temperature and added dropwise to methyl alcohol. The resulting precipitate is separated by filtration, dried and dissolved in chloroform and re-precipitated in methyl alcohol. After drying at 65 ° C in a vacuum oven, a product is obtained, the true viscosity of which in chloroform is 0.45. The product is a polyether1id consisting of the following chemically bound units:
    n115120112
    The results of the clear limit for the preparation of polyethernimide show that the proposed method is better than the method in which bis- (fluorofta-in which bis-Schlorphthalimide is used).
    权利要求:
    Claims (1)
    [1]
    METHOD FOR PRODUCING POLYESTER-
    IMIDA General Formula I:
    wherein wherein R 2 - or CH 2 0, η = 5-30 by reacting an alkali salt where R 1 - is as defined above, * • X - a halogen, in an aprotic solvent at 25-150 C e · I characterized in that , for the purpose of the intensification of 2,2-di- (p-hydroxyphenyl) propane with a halogen derivative of bisphthalimide of the general formula ft:
    process and increase the degree of polymerization, as the halide derivative of bisphthalimide of general formula 1J, a compound of formula I is used, where X is 3 or 4-fluoro.
    SU "1151201
    1 1512'01
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    同族专利:
    公开号 | 公开日
    FR2264807A1|1975-10-17|
    CA1053240A|1979-04-24|
    IT1022360B|1978-03-20|
    DE2437286A1|1975-04-03|
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    AU7156074A|1976-01-29|
    FR2272128A1|1975-12-19|
    JPS5911608B2|1984-03-16|
    BR7406782D0|1975-07-29|
    FR2264807B1|1979-01-05|
    NL175630B|1984-07-02|
    JPS5077499A|1975-06-24|
    DE2437286C2|1985-01-31|
    FR2272128B1|1978-04-28|
    US3847869A|1974-11-12|
    GB1482664A|1977-08-10|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US00401865A|US3847869A|1973-09-28|1973-09-28|Method for preparing polyetherimides|
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