SU1016314A1 - Process for producing polyester urethanes - Google Patents

Process for producing polyester urethanes

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SU1016314A1
SU1016314A1 SU792854648A SU2854648A SU1016314A1 SU 1016314 A1 SU1016314 A1 SU 1016314A1 SU 792854648 A SU792854648 A SU 792854648A SU 2854648 A SU2854648 A SU 2854648A SU 1016314 A1 SU1016314 A1 SU 1016314A1
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example
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process
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SU792854648A
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Russian (ru)
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Малхаз Михайлович Заалишвили
Рамаз Давидович Кацарава
Тамара Михайловна Картвелишвили
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Институт Физиологии Им.И.С.Бериташвили
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Abstract

СПОСОБ ПОЛУЧЕНИЯ ПОЛИЭФИРУРЕТАНрВ путем взаимодействи в . METHOD FOR PRODUCING POLIEFIRURETANrV by reacting a. (расплаве сложного гидроксилсодержащего блигоэфира с гексаметилендиизоцианатом в присутствии диола, от- i личающийс тем, что, с целью придани конечному продукту биодеградируемых свойств, в качестве сложного гидроксилсодержащего олигоэфира используют соединение общей формулы pf-f 0-сн-со ) со-сн-О ti н, где с 0-20; (Melt complex hydroxyl bligoefira with hexamethylene diisocyanate in the presence of a diol, i The relative lichayuschiys in that, in order to impart biodegradable properties to the final product, as oligoester hydroxyl compound used is a compound of general formula pf-f 0-CH-w) Co-O-CH ti n, where 0-20; Е 0-20 (причемЛ 0, t О, , 1. 0); E 0-20 (prichemL 0, t G, 1. 0); R-Mi CHjилиК р-Н, или R R-CH5V. R-Mi CHjiliK p-H or R R-CH5V. CHv § -№)2r{ l«2i3 , СИ, Ч ca2)(CH2-oi CHv § -№) 2r {l «2i3, SI, B ca2) (CH2-oi

Description

Изобретение относитс к синтезу полйэфируретанов, которые могут быть использованы в медицине, например, ; The invention relates to polyefiruretanov synthesis, which can be used in medicine, for example; в качестве саморассасьшанмдихс хирур гических материалов. as samorassasshanmdihs hirur cal materials. Известен способ получени полиэфи уретанов путем взаимодействи гидроксцлсодержащих олигомеров сложноэфирного- , типа с диизоцианатом в присутствии диола l3. Known process for the preparation of urethanes by reacting Polief gidrokstslsoderzhaschih slozhnoefirnogo- oligomers, such as a diisocyanate with a diol in the presence l3. Недостатком известного рпособа получени полйэфируретанов йвл етс их непригодность дл использовани в медицине в качестве биодеградируемых материалов Наиболее близкий по технической сущности к предлагаемому вл етс способ получеин полйэфируретанов путем взаимодействи в расплаве слож ного гидроксилсодержащего олигоэФира с гексаметилендиизоцианатом в при- , сутствии диола. The disadvantage of this preparation rposoba polyefiruretanov yvl is their unsuitability for use in medicine as biodegradable materials The closest in technical essence to the proposed method is poluchein polyefiruretanov by reacting in the melt complexity Nogo hydroxyl oligoesters with hexamethylene diisocyanate in the Examples, presence of a diol. В качестве сложного гидроксилсоЬёржащего олигоэФира используют продукт конденсации дикарбоновой кислот и диола, например адипиновой кислоты и этиленгликол в расплаве С2. As complex gidroksilsoorzhaschego oligoesters using the condensation product of a dicarboxylic acid and a diol, for example adipic acid and ethylene glycol in the melt C2. Недостатком, полученных известным способом,.полйэфируретанов вл етс отсутствие в нх макромолекулах св зей , способных подвергатьс ферментативной биодеградации. The disadvantage derived in known manner, is .polyefiruretanov absence Hx macromolecules bonds capable to undergo enzymatic biodegradation. Целью изобретени вл етс придание биодеградируемых свойств конечному продукту. The aim of the invention is biodegradable imparting properties to the final product. Указанна цель достигаетс тем, что согласно способу при получении полйэфируретанов путем взаимодействи в расплаве сложного гидроксилсодер ащего олигоэФира используют соедиени формулы RК II Jlf (Jfl СО-(Н- О -)- Н, де Ч 0-20 0-20 (причем 1с О, С О, ) е О, 1 О R--H R--CHj или RRH , или Р Р--СНэ, , .СНз R- - 1 5Н21г rl iHjts , (jHj iCH2)2-iH-,-(SH2)f-0-( и процесс провод т ступенчато: при 90-120с в течение 0,5-1 ч, при 160190°С в течение 4-5 ч. Блоксополимерную структуру полученных полимеров подтверждают изучением их растворимости в органических растворител х и сравнением с растворимостью соответствующ Said object is achieved in that according to the preparation method polyefiruretanov by reacting in the melt complex gidroksilsoder aschego oligoesters used soedieni formula Rc II Jlf (Jfl CO- (H-O -) - H H 0-20 0-20 de (1c O wherein , C O) e O O 1 R - H R - CHj or RRH, or P P - ROE, .SNz R- - 1 5N21g rl iHjts, (jHj iCH2) 2-iH -, - ( SH2) f-0- (and the process is carried out in stages:. 90-120s at during 0.5-1 hours at 160 190 ° C for 4-5 hours, the block copolymer structure of the polymers obtained confirmed the study of their solubility in organic solvents and comparing with suitable solubility х гомополимеров , а также изучением их ИК- и ЯМР-спектров. синтезированные полиэФируретаны облгщают пленко- и волокнообразующими свойствами- Они раствор ютс во многих органических раст ворител х, образу высококонцентрированные растворы, из этих раствором методом полива на стекл нные подложки были получены эластичные пленки, имеющие прочность на разрыв 300400 кг/см2 и разрывное удлинение 100200% . x homopolymers, as well as the study of their infrared and NMR spectra. polyetherurethane synthesized oblgschayut film- and fiber-forming svoystvami- They are soluble in many organic stretch voritel x to form highly concentrated solutions of these solution irrigation method on glass substrates elastic films were obtained having a tensile strength of 300 400 kg / cm2 and a breaking elongation of 100200%. Строение и характеристики испольгюванных полиэфирных смол привод тс . The structure and characteristics ispolgyuvannyh polyester resin are shown. в табл.1. in Table 1. Т а б л и ц а 1 Table 1

Пример 1.В трехгорлую , снабженную мешалкой, вводом и выводом дл аргона помещают 0,005 моль олигомера СЭ-1-0 (табл.1) и колбу нагревают до 120-125°С. Example 1. In a three-necked equipped with a stirrer, input and output for the argon was placed 0.005 mole of oligomer SE-1-0 (Table 1) and the flask was heated to 120-125 ° C. К образовавшемус расплаву добавл ют половину (0,05 моль) гексаметилендиизоцианата (суммарное количество гексаметилендиизоцианата 0,1 моль). To the resulting melt were added one half (0.05 mole) of hexamethylene diisocyanate (the total amount of hexamethylene diisocyanate 0.1 mol). Расплав перемешивают в течение 30 мин, после .чеГО температуру снижают до 90-10Ь°С и ввод т Qf095 моль удлинител (диола )S 1,3-пропандиола. The melt is stirred for 30 minutes, after .cheGO temperature was lowered to 90-10 ° C and introduced Qf095 mol extender (diol) S 1,3-propanediol. Смесь вновь .нагребают до и перемешивают еще 30 мий к затем осторожно, по пор ) ди м ввод т оставше ес количество (0,05 моль дииэоцианата). The mixture was again .nagrebayut up and stirred for another 30 to my then cautiously pore) m di administered ec remaining amount (0.05 mol diieotsianata). Реакционна масра быстро загустевает и не переме шиваетс . The reaction Masra quickly thickens and Move shivaets. Температуру медленно повышают до так, чтобы реакционна смесь легко пе ремешивалась и выдержи Ьают при данной температуре в течени 4 ч Расплав выливают на чашку Петри и охлаждают. The temperature was slowly raised to, so that the reaction mixture was easily and ne remeshivalas ayut soak at this temperature for 4 h melt is poured onto a petri dish and cooled. Приведенна в зкость 0,64 д-л/г в м-крезоле, t 2УС, С в 0,5 г/дл. The normalized viscosity of 0.64 dl / g in m-cresol, t 2US C in 0.5 g / dl. . . Пример 2. В трехгорлую Колбу , снабженную мешалкой, вводоми выводом дл аргона помещают 0,0в5 мо олигомёра СЭ-06-04, колбу нагревают до 9Q°C и к образоваввюмус расплаву добавл ют половину 0,05 моль гексаметилендиизоцианата . Example 2. In a three-necked flask equipped with a stirrer, an argon vvodomi terminal placed 0,0v5 mo oligomora SE-06-04, the flask was heated to 9Q ° C and to melt obrazovavvyumus half added 0.05 mol of hexamethylene diisocyanate. Реакционную смеЪь нагревают до в течение 30 мин затем охлаждают до 90°С и ввод т 0, моль пропандиола, вновь нагревают ДО 120°С в течение 30 миН охлаждают до 90°е и осторожно ввод т оставшеес количество диизоцианата. The reaction was heated to sme for 30 minutes then cooled to 90 ° C and administered 0 mol propanediol, again heated to 120 ° C for 30 min, cooled to 90 ° e and carefully administered remaining amount of diisocyanate. Смесь медленно нагревают до 1бО°С, причем теютературу повышают так, чтобы в колбе был хорошо перемешиваеквдй расплав. The mixture was slowly warmed to 1bO ° C, wherein teyuteraturu increased so that in the flask was well peremeshivaekvdy melt. Реакционную смесь: вы держивают при в течение 5 ч,, после чеговыливают на чашку Петри н охлаждают. The reaction mixture was: if you refrain for 5 hours after chegovylivayut ,, n per petri dish was cooled. Чпр 0,58 дл/г в смеси тетрахлорзтан: фенол (3:1), t° 25с, С 0,5 г/дл. Chpr 0.58 dl / g in tetrahlorztan mixture of phenol (3: 1), t ° 25c C 0.5 g / dl. Пример 3. Синтез полимера осуществл ют в соответствии с методикой , приведенной в. Example 3. Synthesis of a polymer was carried out according to the procedure described in. примере 2, с той лишь разницей, что вместо олиго-, мера СЭ-Об-04 (табл.) используют олигомер СЭ-05-05 (табл.1), а вкачестве удлинител цепи вместо.1,3пропандиола используют зтиленгликольц 0,52 дл/г в смеси тетрахлорт зтан: енол (3:1), t 25«с, С 0,5 г/дл. Example 2, with the only difference that instead of oligo- measure SE Ob-04 (tab.) using oligomer SE-05-05 (Table 1) and vmesto.1,3propandiola vkachestve chain extender used ztilenglikolts 0.52 dl / g in a mixture tetrahlort ztan: enol (3: 1), t 25 "s, c = 0.5 g / dl. Пример 4. Синтез полимера осуществл ют в соответствии с методикой приведенной в примере 2, с той разницей, что вместо оп гомера СЭ-06-04; Example 4. Synthesis of a polymer was carried out according to the procedure described in Example 2, with the difference that instead of the op-Homer SE 06-04; берут олигомер СЭ-05-05, . take oligomer SE-05-05,. 0,5d дл/г в смеси тетрёиелорэтана с фенолом 3:l,t° 25°С, С 0,5 г/дл,, П р и м е р 5. Синтез полимера осуществл ют в соответствии с методикой , приведенной впримере 2 с -той разницей, что вместо олигомёра СЭ-06-04 берут олигомер СЭ-04-05, «Injp 0,4 дл/г в смеси тетрахлорэтана С фенолом 3:1, t , С 0,5 г/дл. 0,5d dl / g in a mixture with phenol tetroieloretana 3: l, t ° C 25 ° C 0.5 g / dL ,, EXAMPLE EXAMPLE 5 Synthesis of polymer carried out according to the procedure described vprimere 2 with -th difference that instead oligomora SE-06-04 take oligomer SE-04-05, «Injp 0,4 dl / g in a mixture of phenol tetrachloroethane C 3 1, t, c = 0.5 g / dl. Пример 6. СийЧгез полимера осуществл ют в соответствии с методикой , приведенной в примере 2, с той разницей, что вместо олигомёра СЭ-06-04 берут олигомер СЭ-0-1 , - 0,48 дл/г в смеси твтргослорэтана с фенолом (3:1), t® 25°С, С 0,5 г/дл. Example 6 SiyChgez polymer carried out according to the procedure described in Example 2, with the difference that instead oligomora SE-06-04 take oligomer SE-0-1 - 0.48 dl / g in a mixture with phenol tvtrgosloretana ( 3: 1), t® 25 ° C, c = 0.5 g / dl. Пример 7. Синтез пЬлимера осу1цествл 1от в соответствии с методикой , приведенной в примере 1, с той разницей, что вместо олигомёра СЭ-1-0 беруt олигомер СП-1-0 (табл.1) H«p 0,60 дл/г в м-крезоле, , С 0,5 г/дл. Example 7. Synthesis plimera osu1tsestvl 1ot according to the procedure described in Example 1, with the difference that instead oligomora SE-1-0 berut oligomer SP-1-0 (Table 1) H «p 0,60 dl / g in m-cresol, C 0.5 g / dl. Услови синтеза и основные характеристики полученнш полиэфируретанов приведены в табл.2. The synthesis conditions and the main characteristics poluchennsh urethanes are shown in Table 2.

Таким образом, п менение предлагаемого способа получени полиэфируретанов , содержащих в цеп х макромолекул олигоэфирные блоки на осиове ici-оксикислот Обеспечивает следук цие преимущества: использование в качестве исходных смол олигоэфиров на основе Ыгоксикислот позвол ет получать полиэфируретаны содержгицие в цеп х макро{молекул о6 дфнрные св зи способны под--, вергатьс ферментативной биодегргц1ации Thus, n Menenius proposed method for preparing urethanes containing chains of macromolecules oligoefirnye blocks on osiove ici-hydroxy acids Provides sleduk que advantages: the use as starting resin oligoesters based Ygoksikislot allows to obtain polyether soderzhgitsie in chains macro {molecules O6 dfnrnye communication communication capable pod--, vergats enzymatic biodegrgts1atsii

полученные полизфируретаны полезны дл 11спользованн в медицине в качестве саморассасывающихс материалов , поскольку содержат в цеп х макромолекул биодеградируемые cL-зфирные св зи; obtained polizfiruretany 11spolzovann are useful in medicine as samorassasyvayuschihs materials because they contain a biodegradable macromolecular chains cL-zfirnye bond;

растворимость полученных полиэфируретанов в органических растворител х , что облегчает их переработку в издели -пленки, пористые материалы и т.д. urethanes derived solubility in organic solvents, which facilitates their processing into the article -plenki, porous materials, etc.

SU792854648A 1979-12-17 1979-12-17 Process for producing polyester urethanes SU1016314A1 (en)

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