SU811750A1 - Bis-bicarbonates of aliphatic diols as monomers for preparing polyurethanes and process for producing the same - Google Patents

Bis-bicarbonates of aliphatic diols as monomers for preparing polyurethanes and process for producing the same

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SU811750A1
SU811750A1 SU792810010A SU2810010A SU811750A1 SU 811750 A1 SU811750 A1 SU 811750A1 SU 792810010 A SU792810010 A SU 792810010A SU 2810010 A SU2810010 A SU 2810010A SU 811750 A1 SU811750 A1 SU 811750A1
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monomers
bicarbonates
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SU792810010A
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М.М. Заалишвили
Р.Д. Кацарава
Т.М. Картвелишвили
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Институт Физиологии Им.С.И.Бериташвили
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Изобретение относитс к синтезу новых химических Лединений - бискарбонатов общей формулы: х-о-с-о-к-о-с-сж. The invention relates to the synthesis of new chemical Ledineny - biskarbonatov general formula: X-O-C-O-to-O-C-cm. где В сНг-сН2 сн -СНг сН2-сн-, X-4O W2;- p --N02-, ci .ei Cl Gl и choco6 их получени . wherein in the CIS-CH2-CH2 CH -SNg CH-, X-4O W2; - p --N02-, ci .ei Cl Gl choco6 and their preparation. Активированные бис карбонаты алифатических диолов вл ютс высокореакционными бифункциональными соединени ми и могут быть использованы дл получени высокомолекул рных поли уретанов и поликарбонатов. Bis-activated carbonates of aliphatic diols are highly reactive difunctional compounds and can be used to prepare high molecular weight poly urethanes and polycarbonates. Указанные соединени , их свойства и способ получени в .литературе не описаны. These compounds, their properties and method of preparation is not described in .literature. . . Известны Cl 3 бифункциональные соJeдйнeни на основе алифатических дио1лов - бис-хлорформиаты диолов, используемые в качестве мономеров в услови х поликонденсации дл синтеза поли уретанов и поликарбонатов. Known difunctional soJedyneni Cl 3 based on aliphatic dio1lov - bis-chloroformates diols used as monomers in polycondensation conditions for the synthesis of poly urethanes and polycarbonates. Использование бис-хлорформиатов в i качестве мономеров в поликонденсации pЯJ недостатков 2 3 « -бис-хлорформиаты токсичные веществ вызывание коррозию; Use of a bis-chloroformates i as monomers in the polycondensation pYaJ drawbacks 2 3 «bis-chloroformates toxic substances induction of corrosion; -они легко гидролизуютс и их хранение затруднено , при гидролизе выдел ютс 2 моль двуокиси углерода и 2 «ОЛЬ .хлористого водорода и необходимо учитывать опасность повышени давани ; -they are readily hydrolyzed and storage is difficult, during the hydrolysis are recovered 2 moles of carbon dioxide and 2 "ROLE .hloristogo hydrogen and should be considered dangerous increase Davani; -бис-хлорформиаты практически не пригодны дл синтеза полиуретанов поликонденсацией в растворе, они реагируют со многими органическими растворител ми, что затрудн ет подбор растворителей дл проведени поликонденсации; bis-chloroformates practically not suitable for synthesis of polyurethanes polycondensation in solution, they react with many organic solvents, making it difficult to carry out the selection of solvents for polycondensation; 8П7 5 «О 15 20 25 02 -бис-хлорфррмиаты бурно реагируют также с третичными аминами, используемыми в качестве акцептора хлористого водорода, что приводит к гибели функциональных групп и образованию низкомолекул рных полимеров - при синтезе бис-хлорформиатов различных диолов необходимо многократное использование фосгена, что осложн ет технологию процесса; 5 8P7 "On February 25 15 20 bisphosphonic hlorfrrmiaty also react violently with tertiary amines are used as hydrogen chloride acceptor, leading to the death of the functional groups and the formation of low molecular weight polymers - the synthesis of various bis-chloroformates diols must reuse phosgene, that complicates the process technology; -большинство бис-хлорформиатов алифатических диолов, - жидкости, что создает неудобства при работе с ними, они имеют высокие температуры кипеии и очищаютс лишь перегонкой в вакууме; -Most bis-chloroformates of aliphatic diols, - the liquid that creates inconvenience when working with them, they have a high temperature and a bale cleaned only by distillation in vacuo; -при синтезе р д бис-хлорформиатов, с короткой углеводородной цепью в качестве побочных продуктов образуютс циклические карбонаты, что приводит к нарушению эквимолекул рности при проведении реакции поликонденсации. -with the synthesis of a number of bis-chloroformates, with a short hydrocarbon chain as byproducts formed cyclic carbonates, which leads to disruption ekvimolekul polarity during the polycondensation reaction. Целью изобретени вл етс синтез активированных бис-карбонатов алифатических диолов, которые могут быть использованы дл получени высокомолекул рных полиуретанов и поликарбонатов ., Поставленна цель достигаетс ноо структурой химических соединений бщей формулы: x-0-coKoc-oXi гЗе R -cHrCH2-cH2-v -сНз СН2-СН2-СНСГ С1 Указанные соединени получают заимодействием бис-хлорформиата алиатического диола с соединением, вы ранным ,из групп: нитрофенол, динитофенол , трихлорфенол, пентахлорфенрл, ли алифатический диол с хлорформиа3 том соединений из той же группы , в The aim of the invention is the synthesis of bis-activated carbonates of aliphatic diols which may be used to form high molecular weight polyurethanes and polycarbonates This aim is achieved by the structure DOE bschey chemical compounds of formula:. X-0-coKoc-oXi gZe R -cHrCH2-cH2-v -sNz CH2-CH2-C1 SNSG These compounds interacting ones obtained bis-chloroformate aliaticheskogo diol compound, you rannym from groups nitrophenol dinitofenol, trichlorophenol, pentahlorfenrl whether aliphatic diol hlorformia3 that compounds from this group среде Органического растворител в присутствии третичного амина в каО /-Л и ОглО/ ° Among the organic solvent in the presence of a tertiary amine Kao / -A and OglO / °

К 2,783 г (0,02 моль) п-нитрофенола при комнатной температуре прили- ю веют 30 мл сухого хлорбензола и 2,8мл {0,02 моль) триэтиламина. To 2,783 g (0.02 mol) of p-nitrophenol at room temperature prili- w veyut 30 ml of dry chlorobenzene and 2,8ml {0.02 mol) of triethylamine. После пол1 эго растворени п-нитрофенола раствор охлаж;с ают до -15 и медленно , аокапл м (риливакп раствор js 7,0t г (о,01 моль )бисхлорформиата li,3 пропандиола в 5 мл хлорбензола. После доьавлени всего количества бисх Т-урформиата реакционную смесь перемешивают 15 мин,после чего охлаждение 2о After pol1 ego dissolve p-nitrophenol solution COOLING c ayut to -15 and slowly aokapl m (js 7,0t solution rilivakp g (about 01 moles) biskhlorformiata li, 3 propanediol in 5 ml of chlorobenzene after doavleni total amount biskh T. -urformiata reaction mixture was stirred for 15 minutes, after which cooling 2o

Оо oo

51 « / 51 "/

;О о-с-о-(сн21з-о-с-о- р. тч Щ Синтез осуществл ют в соответствии - методикой, приведенной в примере 1, с той разницей, что вместо п-нитроФенола берут 2,-динитрофенол.Продукт получаетс в осадке в смеси с сол нокислым триэтиламином, его от фильтровывают, промывают спиртом и Синтез осуществл ют в соответствии с. методикой, приведенной в примере 1, с той разницей, что вместо п-нитрофенола берут 2,4,6-трихлорфенол. Продукт реакции - в растворе, поэтому реакционную смесь отфильтровывают от .выгнавшего сол нокислого триэтиламина, осадок промывают дважды небо ; O o-c-o- (sn21z-o-c-o- p mv w Synthesis was carried out in accordance - procedure described in Example 1, with the difference that instead of p-nitrophenol takes 2 -dinitrofenol.Produkt. is obtained in the precipitate in a mixture with triethylamine hydrochloride, from its filtered off, washed with ethanol and synthesis is carried out according to. the procedure described in example 1, with the difference that instead of p-nitrophenol, 2,4,6-trichlorophenol taken. The product reaction - in the solution, so the reaction mixture was filtered from triethylamine hydrochloride .vygnavshego, washed twice sky льшими О - oy-Q- -(() Cl Cl Синтез осуществл ют в соответствии с методикой, приведенной в примере 1, с той разницей, что вместо п-нитро- , фенола берут пентахлорФенол. Продукт выпадает из реакционного раствора вместе с сол нокислым триэтиламином, осадок отфильтровывают, промывают этиснимают и перемешивание продолжают при комнатной температуре в течение |1 ч. Продукт вместе с сол нокислым триэтиламином выпадает в осадок, который отфильтровывают и дл удалени сол нокислого триэтиламина промывают этиловым спиртом и, сушат. lshimi O - oy-Q- - (() Cl Cl synthesis was carried out according to the procedure described in Example 1, with the difference that instead of p-nitro phenol take pentachlorophenol product precipitated from the reaction solution with hydrochloride. triethylamine, filtered off, washed etisnimayut and stirring was continued at room temperature for |. Product 1 hour with triethylamine hydrochloride precipitates, which is filtered off and to remove the triethylamine hydrochloride was washed with ethanol and dried. Получают . Receive. практически чистое белое кристаллическое вещество с т.пл. almost pure white crystalline solid, m.p. 131132°С. 131132 ° C. Выход после перекристаллизации мз толуола т.пл.132-133°С. Yield after recrystallisation toluene Moh t.pl.132-133 ° C. Приме-р 2. 8П750 чес1йр катализатора и акцептора хлоригтого водорода при -15 - . Prima-r 2. 8P750 ches1yr catalyst and hydrogen acceptor at -15 hlorigtogo -. . . Пример 1. о 1 , сушат. EXAMPLE 1 1 of dried. Получают практически чистое, белое кристаллическоевещество с Т.пл. Obtained practically pure, white kristallicheskoeveschestvo m.p. 87-88 е, выход 65%, после перекристаллизации из смеси толуола с :гексаном т.пл. 87-88 e, 65% yield, after recrystallisation from toluene: hexane m.p. . . П р и м е р 3. ) з-о-с-о ( по 5 мл ) порци ми хлорбензола. EXAMPLE EXAMPLE 3) s-O-C-O (5 ml) portionwise chlorobenzene. Объединенный фильтр упаривают в вакууме. The combined filter is evaporated in vacuo. Получают белое кристаллическое вещество с т.пл. A white crystalline solid with m.p. 107-110°С, выход 50, после перекристаллизации из гексана т.пл. 107-110 ° C, yield 50, after recrystallization from hexane m.p. 110-112 С. Пример t. 110-112 C. Example t. С1 С1 -Q. C1 C1 -Q. СГ С1 ловым спиртом и сушат. SG C1 sexually-alcohol and dried. Получают белое кристаллическое, практически чистое вещество с т.пл. A white crystalline, practically pure substance, m.p. , выход 75. После перекристаллизации из смеси толуола с гексаном т.пл. Exit 75. After recrystallization from a mixture of toluene and hexane m.p. 17б-178 с. 17b-178. Примерз. Froze.

ОСКз О About OSKz

Ю)-о-с-о- Шг сНг са-о-с-о Yu) -O-C-O- Hfr CIS sa-of-a-o

Синтез осуществл ют в cooTBetciBHM с методикой, приведенной в 1римере t, с той разницей, мто вместо бис-хлорформиата 1,3-прбпандиола используют бис-хлорфррмиат t,З-бутандиола. The synthesis is carried out in cooTBetciBHM to the procedure described in 1rimere t, with the difference MTO bis-chloroformate instead of 1,3-bis-prbpandiola use hlorfrrmiat t, H-butanediol. Продукт выпадает из реакционного раствора в виде осадка вместе с сол нокисг The product precipitated from the reaction solution as precipitate with hydrochloric nokisg

ЧО)-о-с-о-снгсН2--си-о-с о CHO) -o-with-a-sngsN2 - si-o-with a

Синтез осуществл ют в соответствии 20 с методикой приведенной в примере 1, . Synthesis was carried out according 20 to the procedure described in Example 1. с той разницей, что BMeicto бисхлорформиата 1 13-пропандиола используют бис-хлорформиат 1,3-бутандиола, а with the difference that 13 January BMeicto biskhlorformiata-propanediol using bis-chloroformate of 1,3-butanediol, and

вместо п-нитрофенола - пеНтахлорфенол 5 Продукт реакции в растворе, поэтому реакционную смесь отфильтровывают от выпавшего сол нокислого триэтиламина. instead of p-nitrophenol - 5 Pentachlorophenol reaction product in solution, however, the reaction mixture was filtered from precipitated triethylamine hydrochloride.

лым триэтиламииом, осадок отфильтровывают , промывают этиловым спиртом и сушат. lym trietilamiiom, the precipitate was filtered off, washed with ethanol and dried. Получают белое, кристаллическое вещество с т.пл. A white, crystalline solid with m.p. , выход 6k%t после перекристаллизации из толуЬ а т.пл. Yield 6k% t after recrystallisation from a toluyl m.p. l47-lA8 t, Синтез 6. l47-lA8 t, Synthesis 6.

СНз О About CH

IU IU

осадок промывают дважды небольшими порци ми по 5 мл хлорбензола. the precipitate was washed twice with small portions of 5 ml of chlorobenzene. Объединенный фильтрат упаривают в вакууме. The combined filtrate was evaporated in vacuo. Получают белое, кристаллическое вещество с т.пл. A white, crystalline solid with m.p. 137-139 0, выход 72%, после перекристаллизации из Н-бутанола т.пл. 137-139 0, 72% yield, after recrystallisation from n-butanol, m.p. UO-Ua С. UO-Ua S.

П р и м е р 7. EXAMPLE EXAMPLE 7.

|0 | 0

II II

0-с- о-( о- с-0 0-c- o- (o-s-0

к раствору 0,76 г {П,01 моль) 1,3-пропандиола и 1,б2 мл (0,02 моль) безводного пиридина в 30 мл сухого тетрагидрофурана при охлаждении до добавл ют г (0,02 моль) хлорформиата Г)-нитрофенола. to a solution of 0.76 g of {P, 01 mol) of 1,3-propanediol and 1, b2 ml (0.02 mol) of anhydrous pyridine in 30 ml of dry tetrahydrofuran under cooling is added to g (0.02 mol) of the chloroformate G) -nitrofenola. После добавлени всего количества хлорформиата охлаждение снимаюг и перемешиО After total addition of the chloroformate and cooling snimayug Shuffle

2лО/-о с-о(сН2)г сн-о-с-о- О) 2lO / -o c-o (CH2) r CH-o-c-o- O)

Синтез осуществл ют в соответствии с методикой, приведенной в примере 7, с той разницей , что вместо 1,3-пропандиола Synthesis was carried out according to the procedure described in Example 7, with the difference that instead of 1,3-propanediol

вание продолжают при комнатной температуре в течение 2 ч. Выпавший осадок отфил ьтровывают, промывают этиловым спиртом и сушат. vanie continued at room temperature for 2 hours. The precipitate otfil trovyvayut, washed with ethanol and dried. Т.пл. Mp полученного вещества 130-132 С, выход 85, после перекристаллизации из толуола, т.пл. substances obtained 130-132 C, yield: 85, after recrystallization from toluene, m.p. 132-133°С. 132-133 ° C. Пример 8. Example 8.

СНч о ELF on

используют 1,3-бутандиол, т. пл. use 1,3-butanediol, m. pl. продукта , выход 82. После перекристаллизации из толуола product, yield 82. Recrystallization from toluene

т.пл. mp , Основные А 71 132-133 1770 Толуол (перекристалА 65 88-90 1755 Толуол+гексан А 50 110-112 1765 Гексаи (перекристалА 75 176-178 1765 Толуол+гексаи А6. И7-1 8 1760- Толуол (перекристал1750 лизацией) . . (пЬемо) А72 1770 Н-бутанол (перё1780 криста лйзацией) (плв«ю) лизацией) (перекристаллизацией лизацией) (перекристаллизацией 7-в 750g характеристики активировэнмых бис-карбонатов общей формулы 50,16 3,23 6,61 (50.2«|)(3,)(6,9) «0,96 2,21 11,26 (1ц,13) (2,2) (11,29) 38,92 1,76 -Ю.Н ( 39,0) (1,,73) 3.78 ,0,76 -53,18 . (30,86) (0,91)-(53,7) 51,2« 3,68 6,58 (51 .««З) (3,81) (6,67) 31,92 V,02 -52,03 ( 32,0) (1,tS)152,6) Main A 71 132-133 1770 Toluene (perekristalA 65 88-90 1755 Toluene Hexane + A 1765 50 110-112 hexane (perekristalA 75 176-178 1765 Toluene Hexane + A6. I7-1 8 1760 Toluene (tion of perekristal1750). . (drink) A72 1770 N-butanol (crista pero1780 lyzatsiey) (plv "w) tion of) (recrystallization tion of) (recrystallized 7-750g characteristics aktivirovenmyh bis-carbonates of the general formula 50.16 3.23 6.61 (50.2" |) (3) (6.9) "0.96 2.21 11.26 (1C, 13) (2.2) (11.29) 38.92 1.76 -YU.N (39.0 ) (1, 73) 3.78, 0.76 -53.18 (30.86) (0.91) -.. (53.7) 51.2 "3.68 6.58 (51" 'B) (3,81) (6,67) 31,92 V, 02 -52.03 (32.0) (1, tS) 152,6)

SU792810010A 1979-08-07 1979-08-07 Bis-bicarbonates of aliphatic diols as monomers for preparing polyurethanes and process for producing the same SU811750A1 (en)

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