DE2112487A1 - Process for the production of objects which are intended for repeated and long-term contact with living tissues and mucous membranes - Google Patents
Process for the production of objects which are intended for repeated and long-term contact with living tissues and mucous membranesInfo
- Publication number
- DE2112487A1 DE2112487A1 DE19712112487 DE2112487A DE2112487A1 DE 2112487 A1 DE2112487 A1 DE 2112487A1 DE 19712112487 DE19712112487 DE 19712112487 DE 2112487 A DE2112487 A DE 2112487A DE 2112487 A1 DE2112487 A1 DE 2112487A1
- Authority
- DE
- Germany
- Prior art keywords
- long
- intended
- repeated
- objects
- mucous membranes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/16—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transplantation (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
PATENTANWALTPATENT ADVOCATE
15. März 1971 Anwl-Akte: 75/312March 15, 1971 Anwl file: 75/312
PATENTANMELDUNGPATENT APPLICATION
Ceskoslovenskä akademie ved, PraliaCeskoslovenskä academy ved, Pralia
"Verfahren zur Herstellung von Gegenständen, die zum sich wiederholenden und langfristigen Kontakt mit lebenden Geweben und Schleimhäuten bestimmt sind.""Process for the manufacture of objects that are intended for repeated and long-term contact with living tissues and mucous membranes are intended. "
Es sind Hydrogele bekannt, die als hydrophile Komponente Einheiten mit N-Monoalkylmethakrylamid-Gruppen enthalten und die sich zur Herstellung von Gegenständen, die zum sich wiederholenden und langfristigen Kontakt mit lebenden Geweben und Schleimhäuten bestimmt sind, d.ho zur herstellung von Implantaten, Prothesen oder deren !teilen und ähnlichem geeignet sind.There are known hydrogels which contain, as hydrophilic component units with N-Monoalkylmethakrylamid groups and which are suitable for the production of articles that are to repetitive and long-term contact determined with living tissues and mucous membranes, ie o for the manufacture of implants, prostheses or their ! share and the like are suitable.
Die bekannten analogen N-Monoalkylakrylamide bilden demgegenüber keine genügend stabilen Polymere, diesich für ähmliche Zwecke bewähren könnten. Es überrascht daher, daß Ν,Ν-Dialkylakrylamide bezüglich ihrer chemischen Stabilität und ihrer biologischen Verträglichkeit völlig entsprechen, und Hydrogele mit guten mechanisch-physikali-In contrast, the known analogous N-monoalkylakrylamides form no sufficiently stable polymers that are suitable for ugly purposes could prove useful. It is therefore surprising that Ν, Ν-dialkyl acrylamides with regard to their chemical stability and their biological compatibility fully correspond, and hydrogels with good mechanical-physical
109842/1811 -2109842/1811 -2
seilen Eigenschaften liefern»deliver ropes properties »
Gemäß der Erfindung werden Gegenstände, die zum sich wiederholenden und langfristigen Kontakt mit lebenden Geweben und Schleimhäuten bestimmt sind, durch Polymerisation vo-n hydrophilen Monomeren oder von Gemischen hydrophiler oder hydrophoben Monomeren ait einer kleinen Menge (mit Yorteil Von 2f>) eines Hetzbildners derart hergestellt, daß als Hauptmonomer, das mindestens 50 '-/Ό des Monomeransatzes bildet, ein I\T,2r-Dialkylakrylamid verwendet· wird, dessen Alkyle gegebenenfalls auch noch mit einer Hydroxyl-, Polyhydroxyalkyl- oder Aminogruppe, bzw. mit zwei Typen dieser Gruppe gleichzeitig substituiert sein können» Es ist von Vorteil, die Polymerisation in der an sich bekannten Weise in Anwesenheit von Wasser oder einer mit Wasser mischbarenflüssigkeit vorzunehmen. -According to the invention, objects which are intended for repeated and long-term contact with living tissues and mucous membranes are produced in this way by polymerizing hydrophilic monomers or mixtures of hydrophilic or hydrophobic monomers with a small amount (with part of 2f>) of a hardening agent that as the main monomer, which forms at least 50 '- / Ό of the monomer batch, an I \ T, 2r-dialkyl acrylamide is used, the alkyls of which may also have a hydroxyl, polyhydroxyalkyl or amino group, or with two types of this group can be substituted at the same time »It is advantageous to carry out the polymerization in the manner known per se in the presence of water or a water-miscible liquid. -
Die Menge des Hetzbildners richtet sich nach dem angestrebten Yernetzungsgrad und somit nicht nur nach der i&enge des mehr als zwe if unkt ioneilen Monomers, sonders, auch nach seiner Art und seiner IPfeähigkeit unter den gegebenen Umständen mit den in Frage kommenden Monomeren ein vernetztes Polymer zu bilden» Weniger aktive STetzbilder müssen somit in größeren Mengen zugegeben werden als wirksamere üietzbildner, bei welchen der optimale Bereich bei 0,1 - 2 f> liegt j der Gehalt des lietzbildnersThe amount of Hetzbildners depends on the desired Yernetzungsgrad and thus not only to the i & narrowness of more than zwe if oint ioneilen monomer, Sonders, also according to its kind and its IPfeähigkeit under the circumstances to form with the candidate monomers a crosslinked polymer “Less active bonding agents must therefore be added in larger quantities than more effective bonding agents, in which the optimal range is 0.1 - 2 f> j the content of bonding agents
10 9 8 4 2/161110 9 8 4 2/1611
BAD ORIGINALBATH ORIGINAL
kann sowohl holier als auch niedriger seino £eeigenere Netzbildner sind z.B. N,i\!-i£ethylen-bis-akrylamid, Methyl en-bis-methakrylamid, ü-lykoldimethakrylat oder dergleichen. can be both holier and lower. O £ own network formers are, for example, N, i \! - i £ ethylene-bis-acrylamide, methylene-bis-methacrylamide, glycol dimethacrylate or the like.
Verschiedene Dialkylakrylamide können sowohl untereinander, als auch mit anderEn Monomeren kopolymerisiert werden, wie Zc-bo mit Methakrylonitril, Akrylonitril, Akrylamid, JU-substiuierten oder disubstituierten Methakrylamiden und N-monosubstituierten Akrylamiden. Palls als Ko-?.:onomer ein Ιί,ΙΤ-Dialkylmethakrylamid verwendet wird, muß der Gehalt an Ιί,Ιί-Dialkylakrylamid dessen Menge wesentlich übersteigen, da Dialkylmethakrylamide an sich keiner radikal Polymerisation unterliegen.Different dialkyl acrylamides can be used with each other, as well as with other monomers are copolymerized, like Zc-bo with methacrylonitrile, acrylonitrile, acrylamide, JU-substituted or disubstituted methacrylamides and N-monosubstituted acrylic amides. Palls as Ko -?.: Onomer a Ιί, ΙΤ-dialkyl methacrylamide is used, the amount of Ιί, Ιί-dialkyl acrylamide must be essential since dialkyl methacrylamides are not subject to radical polymerization.
Die Polymerisation kann d uroh Zugabe üblicher Initiatoren für Radikalpolymerisationen, z.B. durch Anwendung verschiedener Peroxyde, Peroxosulfate, substituierter Azoverbindungen usw., initiiert werden.The polymerization can be carried out by adding customary initiators for radical polymerizations, e.g. by using various peroxides, peroxosulfates, substituted azo compounds etc., can be initiated.
Eine 70 τέ-ige wässrige U,N-M/hydroxyäthyl/-akrylamid-Lösung mit 1 Gew.-5ö Iriäthylenglykoldimethakrylat und 0,1 Gew.-$ Wasserstoffperoxyd wird 10 Stunden lang auf 7O0C erwärmt. Man gewinnt ein durchsichtiges, elastisches G-el .A 70-τέ aqueous U, NM / hydroxyethyl / -akrylamid solution with 1 part by weight 5 NC Iriäthylenglykoldimethakrylat and 0.1 wt .- $ of hydrogen peroxide is heated to 7O 0 C for 10 hours. A transparent, elastic gel is obtained.
- 4 -109842/1611- 4 -109842/1611
. - >4 - 1112487. -> 4 - 1112487
Ein ähmliches entsteht■, wenn eine 80 fö-ige 1T,JN-Dipropylakrylamid-Losung in n-Butanol mit 0,7 Gew.*-yo Glykoldimethakrylat und 0,05 ü-ew,—fi Azo-bis-isobutyronitril 8 ο tunden lang auf 600O erwärmt wird*A ähmliches ■ arises when a 80-fö strength 1T, JN-Dipropylakrylamid-solution in n-butanol with 0.7 wt. * - yo Glykoldimethakrylat and 0.05 u-ew, - fi azo-bis-isobutyronitrile 8 ο HOURS is heated to 60 0 O for a long time *
Sine 80 ji-ige wässrige JJ-äthyl-ii-iiydroxäthylakrylaiaid-Losung mit 1>2 Gew*-/ Methyl en-bis— akrylaraid und 0,05 iiew»^/o m Azö--T3is-methyliso'butyrät wird 7 Stunden laiig auf 6Q0C erwärmt. Man gewinnt ein Hydrogel ähnlicher Beschaffenheit wie in Beispiel 1 "beschrieben.Its 80% aqueous 1/2-ethyl-2-hydroxyethylakrylaide solution with 1> 2% by weight methylene-bis-acrylaride and 0.05% m azo-T3is-methyliso'butyrät is 7 hours laiig warmed to 0 C 6Q. A hydrogel similar in nature to that described in Example 1 is obtained.
Eine 80 ^ige Lösung von Η,ΐί-Dipropylakrylamid und liethakrylamid (Molverhältnis 5 i 2) in ii-Butanol mit 0*4 ■Gew.-^ -Methylen-bis-methakrylamid und 0,05 Gew.-y'o Diisopropyiperkarbönat wird mehrere Stunden auf 6O0O erwärmt* Man * gewinnt ein Hydrogel mit guten physikalischen Eigenschaften, ähnliche G-elle fallen auch in den nachfolgenden Beispielen aa,An 80 ^ ige solution of Η, ΐί-dipropylakrylamid and liethakrylamid (molar ratio 5 i 2) in ii-butanol with 0 * 4 ■ wt .- ^ -Methylene-bis-methacrylamide and 0.05 wt-y'o diisopropyl percarbonate is heated to 6O 0 O for several hours * A hydrogel with good physical properties is obtained, similar gels are also found in the following examples aa,
- wässrige
Eine 80 -/fc-igeyiösung eines Gemisches aus !^,i
xyäthyl/-akrylamid und lijii-BimethyaiEthakrylamid
hältnis 4 : l) mit 0,5 Gew.-fo Trlniethylolpropantrlmethakrylat
und 0,1 Gew.-/» Äzo-bis-isobutyronitril wird mehrere
Stunden auf 700C erwärmt.- watery
An 80% strength solution of a mixture of 1, 1 xyethyl / acrylamide and 1/2-bimethyl / ethacrylamide ratio 4: 1) with 0.5% by weight of triethylolpropane methacrylate and 0.1% by weight of azo-bis-isobutyronitrile is heated to 70 0 C for several hours.
1096.42/ 161 1 ;h - BADORiOtNAL1096.42 / 161 1 ; h - BADORiOtNAL
Eine 60 /ί-ige wässrige Lösung eines Gemisches aus JT,U-Dimethyl-akrylamid und Diglykolmonomethakrylat (3 ! 2) mit 0,2 gew./o Diglykoldimethakrylat und 0,05 Gew.-^ Diisopropylperkarbonat wird 10 Stunden lang auf 600G erwärmt.A 60 / ί strength aqueous solution of a mixture of JT, U-dimethyl acrylamide and diglycol monomethacrylate (3! 2) with 0.2 wt. / o Diglycol dimethacrylate and 0.05 wt .- ^ diisopropyl percarbonate is heated to 60 0 G for 10 hours.
'Eine 80-/o-ige Äthanollösung eines Gemisches aus Ή,N-Di/-hydroxyäthyl/-akrylamid und Kethylmethakrylat (4: l) mit 0,1 Gew.-jo Glykoldimethakrylat und 0,05 Gew„-/o Azo-Tois- -isobutyronitril wird mehrere Stunden auf 600C erwärmt.'An 80% ethanol solution of a mixture of Ή, N-di / hydroxyethyl / acrylamide and methyl methacrylate (4: 1) with 0.1% by weight of glycol dimethacrylate and 0.05% by weight of azo Tois- -isobutyronitrile several hours is heated to 60 0 C.
Eine 80 /έ-ige Äthanollösung eines Gemisches aus N,H-Dimethylolakrylamid und Methykrylonitril (3 : l) mit 0,9 Gew.~^ Methylen-"bis-methakrylamid und 0,1 iiewo-^ Benzoyl~ peroxyd wird Io Stunden lang auf 600O erwärmt.A 80 / έ-ethanol solution of a mixture of N, H-Dimethylolakrylamid and Methykrylonitril. (3: l) with 0.9 wt ~ ^ methylene "bis-methacrylamide and 0.1 iiew o - ^ ~ benzoyl peroxide is Io hours warmed to 60 0 O for a long time.
Eine 80 /-ige Lösung eines Gemisches aus ϊΓ,Ν-Dimethylakrylamid und II-Hydroxyäthylmethakrylamid (3 > 2) in n-Butanol mit 0,3 G®w.-% Glykoldimethakrylat und 0,05 Gew.-;o A^o-bis-isobutyroriitril wird 7 Stunden lang auf 700G erwärmteAn 80% solution of a mixture of ϊΓ, Ν-dimethylakrylamide and II-hydroxyethyl methacrylamide (3 > 2) in n-butanol with 0.3% by weight of glycol dimethacrylate and 0.05% by weight; o A ^ o -bis-isobutyroriitril 7 hours, heated to 70 0 G
2/16112/1611
BAD ORIGINALBATH ORIGINAL
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CS202070 | 1970-03-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2112487A1 true DE2112487A1 (en) | 1971-10-14 |
Family
ID=5356071
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19712112487 Pending DE2112487A1 (en) | 1970-03-26 | 1971-03-16 | Process for the production of objects which are intended for repeated and long-term contact with living tissues and mucous membranes |
Country Status (5)
Country | Link |
---|---|
AU (1) | AU2694871A (en) |
CA (1) | CA1002677A (en) |
DE (1) | DE2112487A1 (en) |
FR (1) | FR2085122A5 (en) |
GB (1) | GB1319751A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4023578A1 (en) * | 1990-07-25 | 1992-01-30 | Chemie Linz Deutschland | Copolymer from hydroxy:ethyl acrylate] and N-substd. acrylamide] - or methacrylic] analogues, forming strong hydrogels useful e.g. for controlled release of pharmaceuticals |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CS154386B1 (en) * | 1970-07-10 | 1974-04-30 | ||
GB2114578B (en) * | 1979-11-06 | 1984-06-27 | Ki Med I | Polyacrylamide gel for medical and biological application and method of its preparation |
FR2477033A1 (en) * | 1980-02-28 | 1981-09-04 | Ki Med I | Polyacrylamide gels for medical and biological use - comprising acrylamide copolymer and physiological soln. |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CS154386B1 (en) * | 1970-07-10 | 1974-04-30 |
-
1971
- 1971-03-16 DE DE19712112487 patent/DE2112487A1/en active Pending
- 1971-03-24 AU AU26948/71A patent/AU2694871A/en not_active Expired
- 1971-03-25 CA CA108,749A patent/CA1002677A/en not_active Expired
- 1971-03-25 FR FR7110523A patent/FR2085122A5/fr not_active Expired
- 1971-04-19 GB GB2519371A patent/GB1319751A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4023578A1 (en) * | 1990-07-25 | 1992-01-30 | Chemie Linz Deutschland | Copolymer from hydroxy:ethyl acrylate] and N-substd. acrylamide] - or methacrylic] analogues, forming strong hydrogels useful e.g. for controlled release of pharmaceuticals |
Also Published As
Publication number | Publication date |
---|---|
AU2694871A (en) | 1972-09-28 |
FR2085122A5 (en) | 1971-12-17 |
CA1002677A (en) | 1976-12-28 |
GB1319751A (en) | 1973-06-06 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
OHJ | Non-payment of the annual fee |