HU199695B - Process for producing lactic adid - glycolic acid kopolymeres - Google Patents

Process for producing lactic adid - glycolic acid kopolymeres Download PDF

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HU199695B
HU199695B HU85213A HU21382A HU199695B HU 199695 B HU199695 B HU 199695B HU 85213 A HU85213 A HU 85213A HU 21382 A HU21382 A HU 21382A HU 199695 B HU199695 B HU 199695B
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glycolic acid
lactic acid
copolymers
acid
copolymer
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Francis G Hutchinson
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Ici Plc
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
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    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
    • A61K9/1647—Polyesters, e.g. poly(lactide-co-glycolide)
    • A—HUMAN NECESSITIES
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    • A61K9/204—Polyesters, e.g. poly(lactide-co-glycolide)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7007—Drug-containing films, membranes or sheets
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • C08G63/08—Lactones or lactides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S930/00—Peptide or protein sequence
    • Y10S930/01—Peptide or protein sequence
    • Y10S930/28—Bound to a nonpeptide drug, nonpeptide label, nonpeptide carrier, or a nonpeptide resin

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Description

A találmány tárgya eljárás tejsav-egységeket és glikolsav-egységeket tartalmazó, új tejsav-glikolsav kopolimerek előállítására. A találmány szerinti eljárással előállítható kopolimerek mátrix-anyagokként használhatók fel olyan gyógyászati készítmények előállításához, amelyek hatóanyagokként savakkal szemben stabilis polipeptideket tartalmaznak, és amelyekből a hatóanyag vizes, fiziológiás környezetben hosszabb idő alatt, folyamatosan szabadul fel.
Már régóta felismerték, hogy a klinika: gyakorlatban komoly előnyök származnának olyan gyógyászati készítmények felhasználásából, amelyekből — egyszeri beadás után — a hatóanyag időben elnyújtva, folyamatosan szabadul fel. A klinikai gyakorlatban alkalmazható, nyújtott hatású gyógyászati készítmények előállítását többek között a következő közlemények ismertetik: Remington’s Pharmaceutical Sciences (kiadó: Mack Publishing Co., Easton, Pennsylvania, USA; 15. kiadás, 1975, 1618—1631. oldal (orálisan adagolható kompozíciók) és 1631 —1643. oldal (parenterálisan adagolható kompozíciók) ), 1 351 409 sz. nagy-britanniai szabadalmi leírás (helyileg adagolható kompozíciók). A parenterálisan adagolható kompozíciók például szubdermális injekciók vagy a hatóanyagot tartalmazó, a testbe beágyazható szilárd készítmények (így tabletták vagy filmek) lehetnek. A szakirodalomban eddig már igen sokféle gyógyhatású anyagot tartalmazó beágyazható készítményt ismertettek. Ezeknél a beágyazható készítményeknél a nyújtott hatást úgy érik el, hogy a gyógyhatású anyagot biológiailag lebontható polimer kapszulába töltik, vagy a gyógyhatású anyagot biológiailag lebontható polimer mátrixban diszpergálják; ekkor a gyógyhatású anyag a polimer mátrix lebomlásával párhuzamosan szabadul fel.
A nyújtott hatású gyógyszerkészítmények előállításában felhasználható, biológiailag lebontható polimerek számos képviselője ismert. Ilyen anyagok például a vizes, fiziológiás környezetben hidrolízis révén fokozatosan lebomló poliészterek. E poliészterek közül a szakirodalomban elsősorban a hidroxi-karbonsav-alapú vegyületeket, köztük az a-hidroxi-karbonsavakból (így racém vagy optikailag aktív tejsavból vagy glikolsavból) levezethető észter-homopolimereket és -kopolimereket ismertették [3 773 919 és 3 887 699 sz. amerikai egyesült államokbeli szabadalmi leírás; Jackanicz és munkatársai: Contraception 8, 227—234 (1973); Anderson és munkatársai: Contraception 11, 375—384 (1976); Wise és munkatársai: Life Sciences 19, 867— 874 (1976); Woodland és munkatársai: J. Med Chem. 16, 897—901 (1973); Yolles és munkatársai: Bulletin of the Parenteral Drug Association 30, 306—312 (1976); Wise és munkatársai: J. Pharm. and Pharmacol. 30, 686— 689 (1978) és 31,201-204 (1979)].
Biológiailag lebontható tejsav-glikolsav kopolimerek előállításáról számol be a Polymer 20, 1459—1464 (1979) közlemény, amely szerint a monomereket katalizátor jelenlétében 200°C-on 3—5 percig reagáltatják, és a kopolimert 10—15%-os hozammal kapják. Biológiailag lebontható polilaktidok és tejsav-glikolsav· kopolimerek előállításával foglalkozik továbbá a J. Bíomed. Mater. Rés. 11, 711—719 (1977), a Life Sciences 17, 18771886 (1975), a J. Pharm. Sci. 68, 1534—1538 és a Midland Macromol. Monogr. 1978, 121— 128 közlemény. Az idézett közleményekben leírt eljárások közös jellemzője, hogy a szabad karbonsav-monomerekből, tehát racém vagy optikailag aktív tejsavból és glikolsavból indulnak ki, és homogén összetételű termékeket kapnak.
Polipeptideket tartalmazó, nyújtott vagy késleltetett hatású gyógyszerkészítményeket korábban csak az 1 325 209 sz. nagy-britanniai szabadalmi leírásban (és az annak megfelelő 3 773 919 sz. amerikai egyesült államokbeli szabadalmi leírásban), valamint a 3 887 669 sz. amerikai egyesült államokbeli szabadalmi leírásban említettek. Az utóbbi közlemény a polipeptidek közül csak az inzulint említi meg. Polipeptideket tartalmazó, nyújtott vagy késleltetett hatású gyógyszerkészítmények konkrét összetételéről vagy előállításmódjáról az idézett közlemények semmiféle információt nem tartalmaznak. A közlemények a polipeptideket csak a készítménybe bevihető hatóanyagok felsorolásánál említik meg; a megadott felsorolások pedig a lehető legkülönfélébb hatóanyag-típusokat tartalmazzák. Az idézett szabadalmi leírásokban említett, polipeptidektöl eltérő hatóanyagok csaknem mindegyike viszonylag kis molekulatömegű, többé-kevésbé hidrofób jellegű vegyület, és a szabadalmi leírások nem számolnak be azokról a problémákról és megoldási módjukról, amelyek a viszonylag nagy molekulatömegű, hidrofil jellegűnek tekinthető polipeptidek feldolgozásakor fellépnek.
Rá kell mutatnunk arra, hogy a hatóanyag „nyújtott vagy „késleltetett felszabadulása folyamatosan és szakaszosan egyaránt végbemehet. Kísérleteink során azt tapasztaltuk, hogy ha a szakirodalomban — elsősorban az 1 325 209 sz. nagy-britanniai szabadalmi leírásban — ismertetett gyógyszertechnológiai eljárásokat savakkal szemben stabilis polipeptideket tartalmazó készítmények előállítására alkalmazzuk, a kapott készítményekből ugyan késleltetetten szabadul fel a hatóanyag, a felszabadulás azonban rendszerint szakaszos. így például az 1 325 209 sz. nagy-britanniai szabadalmi leírásban ismertetett polilaktid polimerből a polipeptid hatóanyag gyakran csak egy meglehetősen hosszú indukciós periódus után kezd felszabadulni, vagy a polipeptid lépcsősen szabadul fel, azaz a kezdeti időszakban bizonyos mennyiségű polipeptid eltávozik a készítményből, az ezt követő időszak alatt polipeptid egyáltalán
-2HU 199695 Β nem vagy csak elenyészően kis mennyiségben szabadul fel, és a maradék polipeptid felszabadulása csak a harmadik időszakban következik be.
Azt tapasztaltuk, hogy ha a tejsav-glikdlsav kopolimereket nem a megfelelő karbonsav-monomerekből, hanem a tejsav és glikolsav gyűrűs dimerjeiből képezzük 170°C-ot meg nem haladó hőmérsékleten, polimerizációs katalizátor és láncletörőszer jelenlétében, olyan heterogén tejsav-glikolsav kopolimereket kapunk, amelyekből a beágyazott, savakkal szemben stabilis polipeptid hatóanyag — egy esetleges igen rövid, kezdeti indukciós periódustól eltekintve — folyamatosan szabadul fel, azaz nincs olyan időszak, amikor csak csekély mértékű hatóanyag-felszabadulást észlelnénk, illetve hatóanyag-felszabadulást egyáltalán nem észlelnénk. A hordozóanyagokként a találmány szerint előállított tejsav-glikolsav kopolimereket tartalmazó gyógyászati készítményekből tehát a polipeptid hatóanyag megszakítás nélkül szabadul fel; grafikusan ábrázolva a hatóanyag-felszabadulást, a görbének inflexiós pontja lehet ugyan, telítési szakasza (platója) azonban nincs.
A találmány tárgya eljárás legalább 25 mól% tejsav-egységet és legföljebb 75 mól% glikolsav-egységet tartalmazó, heterogén tejsav-glikolsav kopolimerek előállítására, amelyek benzolban oldhatatlanok és 1 tömeg/térfogat%-os kloroformos vagy dioxános oldatban mért határviszkozitásuk 1,36-nál kisebb, tejsav- és glikolsav-egységek polimerizációs katalizátor jelenlétében végrehajtott kopolimerizációja útján. A találmány értelmében tejsav és glikolsav gyűrűs dimer jeinek elegyéből indulunk ki, és a gyűrűs dimereket 170°C-ot meg nem haladó hőmérsékleten, láncletörőszer jelenlétében, a gyűrű felnyitása közben kopolimerizáljuk.
A leírásban és az igénypontsorozatban a „tejsav-glikolsav kopolimerek megjelölést a legszélesebb értelemben alkalmazzuk, azaz ezen a megjelölésen a racém vagy optikailag aktív tejsav glikolsavval képezett kopolimerjeit, valamint e kopolimerek egymással képezett elegyeit egyaránt értjük. A „heterogén tejsav-glikolsav kopolimer megjelölésen a glikolidban dús és laktidban dús molekulák szempontjából nagymértékben heterogén öszszetételű tejsav-glikolsav kopolimereket vagy nagymértékben polidiszperz tejsav-glikolsav kopolimereket, továbbá két vagy több, egymástól a laktid/glikolid összetétel és/vagy az Μω-érték tekintetében eltérő tejsav-glikolsav kopolimer keverékeit értjük.
Azt a tényt, hogy egy adott tejsav-glikolsav kopolimer a fenti értelemben heterogénnel tekinthető-e vagy sem, a kopolimer 25 MHz-en felvett ,3C-NMR spektrumának vizsgálata alapján dönthetjük el. A spektrumot például hexadeutero-dimetil-szulfoxidos közegben vehetjük fel. Homogén kopolimerek esetén (ilyenek például a korábban idézett közle4 ményekben ismertetett eljárásokkal, tejsavés glikolsav-monomerekből kialakított kopol.imerek) a glikolsav-egységek karbonil-szénatomjának 0=166,0—166,2 ppm-nél megjelenő vonala két dublettet képez, ami megfelel annak, hogy ez a szénatom négy különböző molekuláris környezetben létezhet lényegében egyforma valószínűséggel. Ez a négy különböző molekuláris környezet a GGG, LÖG,
GGL és LGL szerkezet (itt G a glikolsav-egységet, L a tejsav-egységet jelenti, a csillag pedig az éppen vizsgált glikolsav-egységet jelöli). Heterogén kopolimerekben — így a találmány szerint előállított kopolimerekben — azonban az LGL szerkezet előfordulásának valószínűsége csekély; ezért az NMR spektrum említett tartományában egy dublett és egy szingulett jelenik meg. Sok esetben azt tapasztaltuk, hogy a heterogén kopolimerekben a glikolsav-egységek karbonil-szénatomjának 0=166,0—166,2 ppmnél megjelenő vonala csak két szingulett. A „heterogén kopolimer megjelölésen tehát spektroszkópiai szempontból olyan kopolimereket értünk, amelyekben a glikolsav-egységek karbonil-szénatomjának vonala a l3C-NMR spektrumban dublett-pártól eltérő.
Azt a tényt, hogy egy adott tejsav-glikolsav kopolimer homogén vagy heterogén-e, a polimer bomlásának vizsgálatával is eldönthetjük. A vizsgálat során a kopolimer mintáját 7,4-es pH-értékű, 37°C-os pufferoldatba helyezzük, a mintát időről időre kiemeljük a pufferoldatból, megszárítjuk, és NMR spektrum alapján meghatározzuk a tejsav- és glikolsav-egységek részarányát. Ha a kopolimer heterogén, az L/G arány az idő előrehaladtával nő, mert a glikolsav-egységek a tejsav-egységeknél könnyebben hidrolizálnak. Homogén kopolimerek esetén ezzel szemben az L/G arány időben gyakorlatilag változatlan, állandó érték marad.
A kopolimerek tejsav-komponensként előnyösen racém (D,L) tejsavat vagy L-tejsavat tartalmazhatnak.
Egy különösen előnyös módszer szerint a találmány értelmében kis-közepes (60 000-ig terjedő) Mu-értékü, nagymértékben polidiszperz (nagy Mu/M„ értékű) tejsav-glikolsav kopolimereket állítunk el. A technika állásához tartozó közlemények a tejsav- és glikolsav-egységeket tartalmazó kopolimereket általánosságban ismertetik, és sem a speciálisan kis molekulatömegű kopolimerek, sem a nagymértékben polidiszperz kopolimerek előállításánál alkalmazandó konkrét körülményekről nem adnak tájékoztatást. A korábbi közleményekben ismertetett tejsav-glikolsav kopolimerek Mu-értéke általában 30 000— 60 000-nél nagyobb (a kopolimerek határviszkozitása meghaladja a 0,5-öt), és a kopolimerek polidiszperzitása csekély. Ez annak tulajdonítható, hogy a technika állásához tartozó közlemények szerint a tejsav-glikolsav kopolimereket vízmentes körülmények 3
-3HU 199695 Β között, láncletörőszer beadagolása nélkül állítják elő. Kísérleteink során megállapítottuk, hogy a tejsav és a glikolsav gyűrűs dimerjeinek reakciókészsége azonos polimerizációs körülmények között eltérő; így a polimer-összetétel szempontjából nagymértékben heterogén végtermékeket állíthatunk elő akkor, ha a két gyűrűs dimer elegyét láncletörőszer jelenlétében vetjük alá gyűrűnyításos polimerizációnak. Ezzel az eljárással 0,5-nél kisebb határviszkozitású tejsav-glikolsav kopolimereket is előállíthatunk. Adott polimerizációs körülmények, között a glikolsav gyűrűs dimerje a reakcióképesebb komponens, így a polimerizáció kezdeti szakaszában képződő kopolimer molekulák glikolsav-egységekben dús anyagok. A polimerizáció későbbi szakaszában szükségszerűen csak tejsav-egységekben dús kopolimer molekulák képződhetnek; így a kialakuló végtermék az összetétel szempontjából mindig nagymértékben heterogén.
A találmány szerinti eljárásban láncletörőszerként például vizet, víztartalmú tejsavat vagy glikolsavat, egyéb hidroxisavakat, alkoholokat vagy karbonsavakat használhatunk fel.
A polimerizációhoz katalizátorként például cink-oxidot. cink-karbonátot, bázikus cink-karbonátot, dietil-cinket, szerves ónvegyületeket (így ón(II)-oktanoátot), tributil-alumíniumot, titán-, magnézium- vagy bárium-vegyületeket vagy ólom-oxidot használhatunk fel. Különösen előnyös katalizátornak bizonyult az ón(II)-oktanoát.
A gyűrűs dimerek gyűrűfelnyításos kopolimerizációját 170°C-ot meg nem haladó hőmérsékleten végezzük. A reakció rendszerint körülbelül 6 órát igényel.
A találmány szerinti eljárást az oltalmi kör korlátozása nélkül az alábbi példákban részletesen ismertetjük.
A. példa
Keverővei, hőmérővel és vízhűtőhöz csatlakozó desztilláló feltéttel felszerelt, 2 liter űrtartalmú, háromnyakú gömblombikba 800 g D,L-tejsavat és 16 g cink-oxidot mérünk be. Az elegyet keverés közben körülbelül 135°C-ra melegítjük; ekkor megindul a víz eltávozása. A melegítést 8 órán át folytatjuk, ezalatt az elegy hőmérsékletét körülbelül 190°C-ra növeljük. Amikor az elegyből több víz már nem desztillál ki, csökkentjük a nyomást, és a desz6 tillációt addig folytatjuk, amíg a hűtőben szilárd anyag nem kezd kondenzálódni. Ekkor a vízhűtőt léghűtőre cseréljük, a maradékot lehűtjük, majd csökkentett nyomáson (2—8 Hgmm) desztilláljuk. A 130—160°C-on desztilláló, körülbelül 300. g tömegű frakciót összegyűjtjük. Ez a termék a D,L-tejSav gyűrűs dimerje (D,L-laktid, azaz 3,6-dimetil-l,4-dioxán-2,5-dion).
Ίθ A kapott nyers D,L-laktidot körülbelül 600 ml etil-acetátból háromszor átkristályosítjuk, majd a tisztított terméket 24—48 órán át 45°C-on, 2 Hgmm nyomáson szárítjuk. A tisztított termék 124—125°C-on olvad.
B. példa
W.R. Sorenson és T.W. Campbell módszerével [Preparative Methods in Polymer Chemistry, 2. kiadás, 363. oldal (kiadó: Inter20 Science; 1968)] glikolidot (l,4-dioxán-2,5-diont) állítunk elő. Ez a vegyület a glikolsav gyűrűs dimerje. A kapott nyers glikolidot tisztítás céljából vízmentes etil-acetátból háromszor átkristályosítjuk, majd 24—48 órán át 45°C-on, 2—8 Hgmm nyomáson szárítjuk. A tisztított vegyület 82—84°C-on olvad.
1—3. példa
A következőképpen állítunk elő D,L-laktid/glikolid kopolimereket:
Előzetesen kiszárított üvegcsőbe az A. példa szerint előállított, tiszta, száraz D,L-laktidot és a B. példa szerint előállított, tiszta, száraz glikolidot töltünk. A két gyűrűs dimert minden esetben 42 g összmennyiség35 ben használjuk fel. A gyűrűs dimer-keverékhez az I. táblázatban megadott mennyiségű, körülbelül 12 tömeg% víztartalmú kereskedelmi D,L-tejsavat és 1 ml 8 tómeg%-os hexános ón (II) -oktanoát oldatot adunk. A hexánt csökkentett nyomáson elpárologtatjuk, majd a reaktorcsövet 160°C-ra fűtjük fel, és az elegyet 6 órán át ezen a hőmérsékleten tartjuk. Ezalatt az elegyet lehetőség szerint folyamatosan keverjük. A reaktorcsövet porított, szi4g lárd szén-dioxiddal lehűtjük, a képződött kopolimert eltávolítjuk a reaktoTcsőből, apró darabokra zúzzuk, majd 400 ml kloroformban oldjuk. A kloroformos oldatot szűrjük, és a szűrletet 2 liter metanolba öntjük. A ki50 vált szilárd kopolimert leszűrjük, és 24 ólán át 40°C-on, majd 24 órán át 80°C-on, csökkentett nyomáson szárítjuk. A reagens-arányokat és a kapott termékek jellemzőit az I. táblázatban közöljük.
I, táblázat
A példa , száma D,L-lak.tid (L) g Glikolid (G) g L/G mól- arány D,L-tej- sav /ul Határvisz- kozitás (közelitó)
1. 23,0 18,5 50/50 400 0,25 15 200
2. 23,0 18,5 50/50 920 0,126* csekély
3« 23,0 18,5 50/50 1380 0,108* csekély
-4HU 199695 Β
Az Mu értékeket polisztirol standardra vonatkoztatva adtuk meg.
*A termék 1 tömeg/térfogat%-os kloroformos oldatának redukált fajlagos viszkozitása.
A kapott termékek benzolban oldhatatlanok.
Eljárhatunk úgy is, hogy a laktid, a glikolid és a vizes tejsav elegyét először 160°C-ra melegítjük, és ezután indítjuk be a polimerizációt 0.08 g ón (Il)-oktanoát hozzáadásával.
4. példa
Az 1—3, példákban közöltek szerint járunk el, azonban a kopolimert kloroform helyett dioxánban oldjuk. Az 1—3. példákban megadottakhoz hasonló minőségű termékeket kapunk.
5—11. példa
Az 1—3. példákban közöltek szerint járunk el, azzal a különbséggel, hogy a kapott kopolimert jégecetben oldjuk, és a jégecetes oldatot a kopolimer kicsapása céljából metanolba csepegtetjük. A kivált kopolimert le10 szűrjük, majd csökkentett nyomáson 24 órán át 40°C-on, ezután 24 órán át 80°C-on szárítjuk.
A kiindulási anyagok mennyiségét és a kapott termékek minőségi jellemzőit a II. táb15 lázatban közöljük.
II. táblázat
„A példa száma D,L-Laktid (I>), g Glikolid (G), g L/G mólarány sav Katárv iszkozitás Molekulatömeg (közelitó) Ón(II)-oktánost
5· 33,3 26,7 50/50 36O /Ul 0,234 13 500 93 /ul
6. 11,1 8,9 50/50 120 /Ul 0,243 14 450 31 /ul
7. 11,1 3,9 50/50 120 /ul 0,265 16 800 31 /ul
3. 111,0 89,0 50/50 1,2 ml 0,257 15 850 0,31 ml
9. m-,0 89,0 50/50 1,2 ml 0,239 14 200 0,31 ml
10. 38,8 71,2 50/50 0,36 ml 0,262 16 600 0,25 ml
11. 22,2 17,3 50/50 1,38 ml 0,031 62 /Ul
U tömeg/térfogat %-os kloroformos oldat viszkozitása

Claims (1)

  1. SZABADALMI IGÉNYPONT
    Eljárás legalább 25 mól% tejsav-egységet és legföljebb 75 mól% glikolsav-egységet tartalmazó, heterogén tejsav-glikolsav kopolimerek előállítására, amelyek benzolban oldhatatlanok és 1 tömeg/térfogat%-os kloroformos vagy dioxános oldatban mért határviszkozitásuk 1,36-nál kisebb, tejsav35 és glikolsav-egységek polimerizációs katalizátor jelenlétében végrehajtott kopolimerizációja útján, azzal jellemezve, hogy tejsav és glikolsav gyűrűs dimerjeinek elegyéből indulunk ki, és a gyűrűs dimereket 170°C-ot
    40 meg nem haladó hőmérsékleten, láncletörőszer jelenlétében, a gyűrű felnyitása közben kopolimerizáljuk.
HU85213A 1981-02-16 1982-02-15 Process for producing lactic adid - glycolic acid kopolymeres HU199695B (en)

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JPH0157098B2 (hu) 1989-12-04
FI80594B (fi) 1990-03-30
JPH05221871A (ja) 1993-08-31
NO162103B (no) 1989-07-31
ATE22535T1 (de) 1986-10-15
ES509647A0 (es) 1983-08-01
JPH031330B2 (hu) 1991-01-10
EP0058481A1 (en) 1982-08-25
AU602623B2 (en) 1990-10-18
DK59182A (da) 1982-08-17
US4767628A (en) 1988-08-30
EP0058481B1 (en) 1986-10-01
AU560829B2 (en) 1987-04-16
AU6498886A (en) 1987-02-19
JPH0774143B2 (ja) 1995-08-09
DE3273501D1 (en) 1986-11-06
GR76791B (hu) 1984-09-04
US5004602A (en) 1991-04-02
YU44066B (en) 1990-02-28
PT74434A (en) 1982-03-01
US4767628B1 (hu) 1990-07-17
EP0058481B2 (en) 2003-05-21
ES8307845A1 (es) 1983-08-01
PT74434B (en) 1983-07-14
IE820165L (en) 1982-08-16
AU2840789A (en) 1989-05-04
CA1169090A (en) 1984-06-12
HU186904B (en) 1985-10-28
NO162103C (no) 1992-03-04
YU31582A (en) 1985-04-30
HK107890A (en) 1990-12-28
JPS57150609A (en) 1982-09-17
AU582920B2 (en) 1989-04-13
MY101545A (en) 1991-12-17
AU7998682A (en) 1982-08-26
JPH0686390B2 (ja) 1994-11-02
NO820433L (no) 1982-08-17
IE52535B1 (en) 1987-12-09
NZ199732A (en) 1985-08-30
DK164845B (da) 1992-08-31
ZA82565B (en) 1982-10-27
FI820467L (fi) 1982-08-17
JPS6264824A (ja) 1987-03-23
JPH05271051A (ja) 1993-10-19

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