SU876663A1 - Method of producing polyarylates - Google Patents

Method of producing polyarylates

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SU876663A1
SU876663A1 SU792854671A SU2854671A SU876663A1 SU 876663 A1 SU876663 A1 SU 876663A1 SU 792854671 A SU792854671 A SU 792854671A SU 2854671 A SU2854671 A SU 2854671A SU 876663 A1 SU876663 A1 SU 876663A1
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aliphatic
method
acids
example
dl
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SU792854671A
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Russian (ru)
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Малхаз Михайлович Заалишвили
Рамаз Давидович Кацарава
Дареджан Петровна Харадзе
Ламара Мартыновна Авалишвили
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Институт Физиологии Им. Академика И.С.Бериташвили Ан Гсср
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С54)- СПОСОБ ПОЛУЧЕНИЯ ПОЛИАРИЛАТОВ C54) - METHOD FOR PRODUCING polyarylates

1 one

Изобре -гзние относитс к синтезу высокомолекул рных полиарилатов на основе алифатических дикарбоновых кислот и бис-фенолов,которые могут j найти применение в различных област х народного хоз йства, как пленко-и волокнообразующие полимеры. IMAGE -gznie relates to the synthesis of high molecular weight polyarylates based on aliphatic dicarboxylic acids, bis-phenols, j which can find application in various fields of the national host-keeping, film-like and fiber-forming polymers.

Известен способ получени полиарилатов на основе бис-фенолов и ди- |Q хлорангидридов алифатических дикарбоновых кислот в услови х межфаз ой поликонденсации CllПолиарилаты , полученные этим.способом , имеют низкие в зкостные характеристики из-за высокой скорости гйдро- 15 лиза хлорангидридных групп алифатических дикарбоновых кислот водно-щелочным раствором, что приводит к остановке роста цепи макромолекул. Known is a method for preparing polyarylates based on the bis-phenols and di- | Q chlorides of aliphatic dicarboxylic acids in conditions interphase second polycondensation CllPoliarilaty obtained etim.sposobom have low viscosity characteristics of the high speed gydro- 15 Lisa acid chloride groups of aliphatic dicarboxylic acids an aqueous alkaline solution, resulting in stopping the growth of the macromolecules chain.

Наиболее близким к предлагаемому по технической сущности и достигаемому эффекту вл етс способ получени полиарилатов путем взаимодействи производных дикарбоновых кислот в . The closest to the proposed technical essence and attainable effect is a process for producing polyarylates by the reaction of derivatives of dicarboxylic acids. среде органического растворител в присутствии третичного амина 2. an organic solvent in the presence of a tertiary amine 2.

Этим способом (метод растворной поликонденсаций) полиарилаты на основе ди хлора и гидридов ароматической кислоты и бис-фенола имеют высокие в з- 30 In this manner (by solution polycondensation) based polyarylates di chlorine and hydrides of aromatic acid and bis-phenol have high in z- 30

костные характеристики н обладают хорошими пленко-и волокнообразующими свойствами. n bone characteristics have good film-and fiber-forming properties.

На основе, дихлорангйдридов алифатических кислот методом растворной поликонденсации получают полиарилаты с низкими в зкостными характеристиками , что обусловлено протеканием побочных процессов образовани кетена при взаимодействии кислот с третичными аминами, и имеющие неоднородное , разнозвенное строение полимерных цепей. On the basis dihlorangydridov aliphatic acids is prepared by solution polycondensation of polyarylates with low viscosity characteristics, due to the occurrence of side reactions forming by reacting ketene acids with tertiary amines, and having a non-uniform, heterounit structure of the polymer chains. . .

Цель изобретени - упрощение технолог-ии процесса. The purpose of the invention - simplified technology-ii process.

Поставленна цель достигаетс тем, что в способе получени полиарилатов путем взаимодействи производных дикарбоновых кислот в среде органического растворител в присутстВИИ третичного амина, в качестве производных дикарбоновых кислот используют дизфиры алифатических дикарбоновых кислот общей формулыV This aim is achieved in that in the method for producing polyarylates by the reaction of dicarboxylic acid derivatives in an organic solvent in the presence of a tertiary amine as derivatives of dicarboxylic acids are used dizfiry aliphatic dicarboxylic acids of the general formulyV

X - ОСО -R- ОСО - Х гдек -(СПо) (п 1-8) , X - CCA CCA -R- - X SppK = SpaK - (PPS) (n 1-8)

Х - X -

а but

, / со-с. , / Co-s. -н( I -n (I

-CO-CHt -CO-CHt

а а as well as

и процесс провод т при 25-65 С. and the process is carried out at 25-65 C.

В зкостные характеристики полученных полиэфиров составл ют 0,22 0 ,94 дл/г в зависимости от природы активирующей группы и условий синтез полиэфира. The viscometric characteristics of the obtained polyester was dissolved 0.22 0, 94 dl / g depending on the nature of the activating group and the conditions of polyester synthesis.

Полученные полиэфиры растворимы в 1,2-дихлорэтане, NN-димётилацетамиде , гексаметилфосфорамиде, М-метил-2-пирролидоне , диметилсульфоксиде , образу высококонцентрированные растворы. The resulting polyesters are soluble in 1,2-dichloroethane, NN-dimotilatsetamide, hexamethylphosphoramide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, forming highly concentrated solutions.

Их 10%-ных растворов полиэфиров в 1,2-дихлорэтане методом полива на стекл нные подложки получают пленки, имеющие прочность на разрыв 8001200 кг/см и удлинение 5-10%. They are 10% solutions of the polyesters in 1,2-dichloroethane irrigation method on a glass substrate obtained film having a tensile strength of 8001200 Kg / cm and an elongation of 5-10%.

Пример 1.К2,39г (0,005 моль} бис- 2,4-динитрофениладипината добавл ют 1,59 г (0,005 моль) фенолфталеина, 5,5 мл 1,2-дИхлорэтана и 2,8 мл триэтиламина (концентраци 0,6 моль/л. Реакционную смесь перемешивают при в течение 3 ч. В зкий реакционный раствор выливают в спирт, выпавший полимер отфильтровывают и экстрагируют этилацетатом в аппарате Сокслетта, затем сушат. Выход 97%, tnP 0,94 дл/г в 1,2-дихлорэтане при 25с, С 0,5 г/дл. EXAMPLE 1.K2,39g (0.005 mol 2,4-bis} dinitrofeniladipinata was added 1.59 g (0.005 mol) of phenolphthalein, 5.5 ml of 1,2-dichloroethane and 2.8 ml of triethylamine (0.6 mol concentration / liter. The reaction mixture was stirred at for 3 hours. The viscous reaction solution was poured into ethanol, the precipitated polymer is filtered and extracted with ethyl acetate apparatus Soksletta, then dried. Yield 97%, tnP 0,94 dl / g in 1,2-dichloroethane at 25c, c = 0.5 g / dl.

Пример 2. Синтез полимера осуществл ют в соответствии с методикой , приведенной в примере 1, но в качестве диэфира используют бис-2, динитрофениловый,эфир нтарной кислоты . Example 2. Synthesis of a polymer was carried out according to the procedure described in Example 1, but using the diester as bis-2 dinitrophenyl ester, succinic acid. Реакционную смесь перемешивают при в течение 1 ч, а затем при 25с в течение 2ч. The reaction mixture was stirred at for 1 hour and then at 25C for 2h. Выход полимера 97%, tnp / дл/г в 1,2-дихлорэтане при 25°С С 0,5 г/дл. Polymer yield 97%, tnp / dl / g in 1,2-dichloroethane at 25 ° C C of 0.5 g / dl.

Пример 3. Синтез полимера провод т в соответствии с методикой, приведенной в примере 1, но в качестве растворител используют метилэтилкетон . Example 3. Synthesis of a polymer was carried out according to the procedure described in Example 1, but the solvent is methyl ethyl ketone. Реакционную смесь перемешивают при 50°С в течение 0,5 ч, а затем при в течение 2,5 ч. Выход полимера 98%,tnp 0,82 дл/г в 1,2дихлорэтане при 25°С, С 0,5 г/дл. The reaction mixture was stirred at 50 ° C for 0.5 h and then at for 2.5 h. The polymer yield 98%, tnp 0,82 dl / g 1,2dihloretane at 25 ° C, 0.5 g of C / dl.

Пример 4. Синтез полимера осуществл ют в соответствии с методикой , приведенной в примере 1, но в качестве растворител используют бензол. Example 4. Synthesis of a polymer was carried out according to the procedure described in Example 1, except that benzene is used as solvent. Реакционную смесь перемешивают при в течение 1ч, а затем при 25С в течение 2 ч. Выход полимера ,пр 0,58 дл/г в 1,2дихлорэтане при 25е, С 0,5 г/дл. The reaction mixture was stirred at for 1 h and then at 25C for 2 hours. The polymer yield, etc. 0.58 dl / g at 1,2dihloretane 25e, C 0.5 g / dl. П р и м е р 5. Синтез полимера осуществл ют в соответствии с методикой , приведенной в примере 1, но в качестве диэфира используют бИс-п-нитрофениладипинат . EXAMPLE Example 5 Synthesis of polymer carried out according to the procedure described in Example 1, but as the diester, bis-p-nitrofeniladipinat. Реакционную смес the reaction mixture

перемешивают при 65°С в течение 1 ч, а затем при 25°С в течение 2 ч. Выход полимера 92%, .р 0,38 дл/г. stirred at 65 ° C for 1 hour and then at 25 ° C for 2 hours. The polymer yield 92%, born in 0.38 dl / g. в 1,2-дихлорэтане при 25с, С 0,5 г/дл. in 1,2-dichloroethane at 25c C 0.5 g / dl. , .

П .р и м е р 6. Синтез полимера Осуществл ют в.соответствии с методикой , приведенной в.примере 1, но в качестве диэфира используют -бис-пентахлорфениладипинат . N born in EXAMPLE 6. Synthesis of polymer v.sootvetstvii carried out with the technique presented B. Example 1 was used as the diester bisphosphonic pentahlorfeniladipinat. Реакционную смесь перемешивают при 65°С в течение 2 ч, а затем при в течение 1.4. The reaction mixture was stirred at 65 ° C for 2 h and then at over 1.4. Выход полимера 93%, tnp -0,29 дл/г в 1,2-дихлорэтане при 25с, С 0,.5 г/дл. Polymer yield 93%, tnp -0,29 dl / g in 1,2-dichloroethane at 25c C 0 .5 g / dL.

Пример 7. Синтез полимера осуществл ют аналогично методике, приведенной в примере 1, но в качестве диэфира используют бис-N-оксисукцинимидадипинат . EXAMPLE 7 Synthesis of the polymer is carried out analogously to the procedure described in Example 1, but using the diester as bis-N-oksisuktsinimidadipinat. Выход полимера 94%, tnP 0,28 дл/г в 1,2-дихлорэтане при 250с, С 0,5 г/дл. Polymer yield 94%, tnP 0,28 dl / g in 1,2-dichloroethane at 250c, c = 0.5 g / dl.

Пример 8. Синтез полимера .осуществл ют аналогично методике, Приведенной в примере 1, но в качестве растворител используют диметилсульфоксид . Example 8. Synthesis of polymer dissolved .osuschestvl the same manner as in Example 1, except that dimethyl sulfoxide is used as solvent. Выход полимера 93%, ЛпР 0,26 дл/г в 1,2-дихлорэтане при 25С, С 0,5 г/дл. Polymer yield: 93% DMP 0.26 dl / g in 1,2-dichloroethane at 25 ° C, c = 0.5 g / dl.

Пример 9. Синтез полимера осуществл ют в соответствии с методикой , приведенной в примере 1, но в качестве растворител используют N,Ы-диметилацетамид. Example 9. Synthesis of a polymer was carried out according to the procedure described in Example 1, but the solvent is N, N-dimethylacetamide. Выход полимера 91%, tnp 0,22 дл/г в 1,2-дихлорэтане при 25 С, ,5 г/дл. Polymer yield 91%, tnp 0,22 dl / g in 1,2-dichloroethane at 25 C, 5 g / dl.

.Пример 10. Синтез полимера осуществл ют в соответствии с методикой , приведенной в примере 1, но в качестве бис-фенола используют диан. Example 10. The polymer synthesis was carried out according to the procedure described in Example 1, but as the bis-phenol is used Dian. Выход полимера 96%,1пр 0,82 дл/г в 1, 2-дихлорэтане при 25°С, ,5 г/д Polymer yield 96% 1pr 0.82 dl / g in 1, 2-dichloroethane at 25 ° C, 5 g / d

П р и м е ры 11-16. EXAMPLE 11-16 e ra. Синтез полиэфиров осуществл ют в соответствии с примером 1, но в качестве диэфира используют бис-2,4- динитрофениловые эфиры малоновой, глутаровой, пимелиновой , пробковой, азелаиновой, себациноЬой кислот. The synthesis of polyesters is carried out in accordance with Example 1, but using as the diester of bis-2,4-dinitrophenyl ester of malonic, glutaric, pimelic, suberic, azelaic, sebatsinooy acids.

Пример 17. Синтез полиэфира осуществл ют в присутствии алифатического 1,3-пропандиОла. Example 17. Synthesis of polyester is carried out in the presence of an aliphatic 1,3-propanediol. К смеси 2,39 г (0,005 моль) бис-2,4-дини7 трофениладипината, 1,59 г (0,005моль фенолфталеина 2,8 мл: триэтиламина в 5,5 мл 1,2-дихлорэтана добавл ют 0,76 г (0,01 моль) 1,3-пропандиола и реакционную смесь перемешивают при 25С в течение 3 ч. Получают полимер с выходом 96%,1пр 0,88 дл/г в 1,2-дихлорэтане при 25°С, ,5 г/дл. To a mixture of 2.39 g (0.005 mol) of bis-2,4-dini7 trofeniladipinata, 1.59 g (0,005mol phenolphthalein 2.8 ml: 5.5 ml of triethylamine in 1,2-dichloroethane was added 0.76 g of ( 0.01 moles) of 1,3-propanediol and the reaction mixture was stirred at 25C for 3 hours. The polymer was obtained in a yield of 96%, 1pr 0.88 dl / g in 1,2-dichloroethane at 25 ° C, 5 g / dl.

Образование высокомолекул рного полиэфира при соотношении диол: активированный эфир 3:1 свидетельствует об отсутствии взаимодействи .между активированным диэфиром и алифатическими гидроксильными группами. The formation of high molecular weight polyester at a ratio of diol: activated ester 3: 1 indicates the absence of reacting an activated diester .mezhdu and aliphatic hydroxyl groups. В противном случае в результате нарушени эквимол рности должны были бы Otherwise, as a result of disturbances equimolar polarity should have

S876663 S876663

образоватьс лишь ниэкомолекул рныесобности активированных диэфиров по be formed only niekomolekul rnyesobnosti activated diesters of

продукты.сравиеиию с дихлорангидридё1ми. produkty.sravieiiyu with dihlorangidrido1mi.

Данный пример свидетельствует ополиарилатов, полученных по примерам This example demonstrates opoliarilatov obtained in Examples

высокой селективной ацилируквдей спо-1-17, приведены в таблице. high selective atsilirukvdey spo-1-17 are listed in the table.

Услови синтеза и характеристики The synthesis conditions and the characteristics

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Claims (2)

  1. в -е Предлагаемый способ позвол ет синтезировать высокомолекул рные по лиэфиры на основе алифатических дикарбоновых кислот, высока селектив ность способа (ацилйруютс ароматические гидроксильные группы и не затрагиваютс алифатические) дает возможность синтезировать регул рны Полиэфиры/ облсщающие пленко- и во локнообразуюадими свойствами (из-за отсутстви протекани - побочных процессов взаимодействи диэфиров с тр тичными аминами и реакций гидролиза функциональных групп). in -e proposed method allows to synthesize high molecular weight liefiry based on aliphatic dicarboxylic acids, high selectivity NOSTA method (atsilyruyuts aromatic hydroxyl groups are not affected and aliphatic) makes it possible to synthesize regulator rny Polyethers / oblsschayuschie film- and in loknoobrazuyuadimi properties (due absence of flow - secondary processes reacting diesters with mp cal amine functional groups and hydrolysis reactions). Таким образом, использование в качестве производных дикарбоновых кислот диэфиров алифатических дикар боновых кислот общей формулы I в способе получени полиарилатов позвол ет упростить технологию процесс Формула изобретени Способ получени полиарилатов путем взаимодействи производных ди карбоновых кислот в среде органического растворител в присутствии третичного амина, отличаюийс тем, что, с целью упроени технологии процесса, в качестве роизводных дикарбоновых кислот исользуютс диэфиры алифатических диарбоновых кислот общей формул Thus, the use of derivatives of dicarboxylic acids, diesters of aliphatic Qar slick acids of general formula I in a method for preparing polyarylates allows to simplify the technology process CLAIMS A method for producing polyarylates by the reaction of derivatives of di carboxylic acids in an organic solvent in the presence of a tertiary amine otlichayuiys in that in order uproeni process technology as roizvodnyh isolzuyuts dicarboxylic acid diesters of aliphatic acids of general formulas diarbonovyh X - ОСО - R;- ОСО - X, де R -(СН2)г, (п-1-8), Х- - СО-СНг г , и процесс провод т при 25-65 С. Источники информации, прин тые во внимание при экспертизе 1. мЬрган П.У. X - OCO - R; - OCO - X, de R - (CH2) r, (n-1-8), X - CO-CIS g, and the process is carried out at 25-65 C. Sources of information received into account in the examination 1. mrgan PU Поликонденсационные процессы синтеза полимеров. Polycondensation polymer synthesis processes. М., Хими , 1970, с, 312. M., Chemistry, 1970, p. 312.
  2. 2. Коршак В.В. 2. VV Korshak и др. Неравновесна поликонденсаци , М., Наука, 1972 с. et al. nonequilibrium polycondensation, Nauka, Moscow 1972 s. 164 (прототип) , 164 (prototype)
SU792854671A 1979-11-11 1979-11-11 Method of producing polyarylates SU876663A1 (en)

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