WO2020190240A2 - A method for obtaining a biodegradable gel - Google Patents
A method for obtaining a biodegradable gel Download PDFInfo
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- WO2020190240A2 WO2020190240A2 PCT/TR2020/050212 TR2020050212W WO2020190240A2 WO 2020190240 A2 WO2020190240 A2 WO 2020190240A2 TR 2020050212 W TR2020050212 W TR 2020050212W WO 2020190240 A2 WO2020190240 A2 WO 2020190240A2
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- 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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
- C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
-
- 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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/87—Non-metals or inter-compounds thereof
Definitions
- the present invention relates to a method for obtaining a transparent biodegradable gel (elastomer) which is self-healing (autonomously) without needing any external effect at room temperature, has high strength and stretching features simultaneously and can provide linear capacitance response at small strain values in nano-micro Farad levels.
- Biodegradable materials are the ones that can participate in the cycle in nature upon being degraded by efficiency of biological agents. Some natural gases such as CO 2 , N 2 , water and inorganic salts occur in consequence of this degradation. Biodegradable materials have become an issue due to environmental damages caused by plastics today and many studies have been done in order to improve them, and they are continued to be done as well. Products produced with this technology are environmentally friendly. Biodegradable materials have area of use in the healthcare industry as well as in the plastics industry. These materials are grouped as the ones obtained by starch based, cellulose based, chemical synthesis and the ones produced by bacteria. Biodegradable gels, a type of biodegradable materials, can be produced in elastomer structure.
- the hydrogel is obtained by intermixing and cross-linking N-carboxyethyl chitosan solution and PEGDA polymer solution.
- the hydrogel obtained by these solutions has a self-healing property and it does not need environmental stimulation for this property.
- the hydrogel obtained is used for producing biodegradable biomedical materials.
- the hydrogel displays a self-healing performance after externally applied strain changes.
- the Chinese patent document no. CN106009003 discloses an injectable self-repairing hydrogel, a preparation method and application thereof to biological tissue engineering.
- Gel is obtained by mixing a solution derivative of natural polymer chitosan with increased water solubility and sodium hyaluronate.
- the gel obtained has high strength, well biocompatibility and degradability and it is used in commercial biomedical products. It can be shaped as desired according to the wound area to be used. When the gel is mechanically damaged in the middle thereof, the intermediate gap shrinks gradually over time and eventually disappears completely.
- An objective of the present invention is to realize a method for obtaining a biodegradable gel which has high stretching feature and strength simultaneously and is used for preparing tissue scaffolds that will help regeneration of flexible soft tissue such as artificial skin, muscle, tendon, etc.
- Another objective of the present invention is to realize a method for obtaining a biodegradable gel which eliminates the need for a second surgical procedure by degrading in time after being placed in the body, leaving its place to the newly formed (incipient) tissue.
- An objective of the present invention is to realize a method for obtaining a biodegradable gel which heals itself autonomously by contacting broken parts with each other, and which has completely original features.
- An objective of the present invention is to realize a method for obtaining a biodegradable gel which provides feature of giving capacitive response at very small strain values in nano-micro Farad levels.
- Figure l is a view of the flow chart of the inventive method for obtaining a biodegradable gel.
- the inventive method for obtaining a biodegradable gel (100) which is self-healing (autonomously) without needing any external effect at room temperature, has high strength and stretching features simultaneously and can provide linear capacitance response at small strain values in nano-micro Farad levels comprises the steps of: carrying out prepolymer reaction of a bifunctional polyethyleneglycol molecule with a diacid in the presence of a catalyst in a reactor (101); and - carrying out -OH condensation by cross-linking the polymers obtained in the prepolymer reaction (102).
- the bifunctional poly ethyleneglycol molecule at the step of carrying out prepolymer reaction (101) is a polyethyleneglycoldiglycidyl ether.
- the diacid used is a sebasic acid (C10H18O4).
- Caffeine is used as a catalyst in order that reaction between polyethyleneglycoldiglycidyl ether and sebasic acid is carried out.
- the said prepolymer reaction is preferably carried out in a microwave reactor.
- the prepolymer reaction carried out is completed in a period of 3-10 minutes.
- the prepolymer reaction (101) carried out in the inventive method (100) is in the form of:
- Polyethyleneglycolsebacate prepolymer is obtained at the end of the reaction.
- the -OH (hydroxyl) groups occurring in the prepolymer obtained at the step of carrying out prepolymer reaction (101) are cross-linked at a temperature range of 110-160 ° C. In a preferred embodiment, 120°C is chosen as the optimum temperature value.
- Cross-linking is carried out at vacuum values less than 100 mBar. The time required for cross-linking is between 24-48 hours. In a preferred embodiment, the desired gel properties are achieved after cross-linking carried out in 24 hours. A suitable material is obtained between a time period of 32- 48 hours however as the time extends, decrease occurs in the flexibility feature.
- - OH groups are consumed as a result of cross-linking and polyethyleneglycolsebacate, i.e. biodegradable gel (elastomer), is obtained.
- the biodegradable gel obtained by the inventive method (100) has area of use as drug delivery system platform, muscle-tendon repair material including surgical threads in fiber form or woven-nonwoven medical textile products, wound bum cover materials (dressings), membranes, medical patches, tissue scaffold for soft and hard tissue repair/regeneration, guided tissue repair material, nails, plates and screws for orthopaedic applications, particle forms as well. Besides these areas, biodegradability has potential for use in the development of wearable sensor platforms, in sensor units at different soft robotics applications in biomedical field, and also in food, environment and other non-medical issues in terms of its flexing and capacitive feature.
- the biodegradable gel obtained by the inventive method (100) is enhanced due to the cross-links contained by thereof and its flexibility feature is simultaneously enhanced by means of the raw materials used and the obtaining conditions as well. Besides, it displays high transparency when it is stretched.
- the said gel which can have high strength and stretching features simultaneously is used for preparing tissue scaffolds that may help regeneration of many flexible soft tissues such as artificial skin, muscle, tendon, etc.
- the regeneration materials used in this way eliminate the need for a second surgical procedure leaves its place to the newly formed (incipient) tissue upon degrading in time.
- the products formed as a result of degradation like the gel itself are also non-toxic products.
- the biodegradable gel obtained by the inventive method (100) has a self-healing feature autonomously without temperature, UV and other factors.
- the biodegradable gel heals itself in a short time by contacting two broken parts with each other and regains its original strength and stretching property features completely. It is can be applied in industry as a meniscus repair material due to this feature and returned to its original condition by reuniting after contact upon it is degraded under loads. It can solve an existing problem by transferring the strength required during regeneration, to the related tissue by means of this feature in muscle, tendon and other similar applications.
- the biodegradable gel obtained by the inventive method (100) has the feature of giving capacitive response at very small strain values in nano-micro Farad levels.
- a gel having this feature offers the potential to meet the already existing need for preparing platforms in flexible and wearable optoelectronic applications.
- the capacitive sensor prepared with the said gel helps to monitor tissue regeneration (for example heart muscle) or a physiological data (arterial pressure) in vivo by means of a biodegradable sensor.
- the gel can be utilized in different platforms due to this feature in many wearable, flexible and biodegradable electronic or biomedical applications. In the event that it is configured as a sensor, a linear response is received from the sensor element as sensitive to very small strain (for example a muscle movement) or pressure to fall on the sensor.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Biological Depolymerization Polymers (AREA)
- Materials For Medical Uses (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
The present invention relates to a method (100) for obtaining a transparent biodegradable gel (elastomer) which is self-healing (autonomously) without needing any external effect at room temperature, has high strength and stretching features simultaneously and can provide linear capacitance response at small strain values in nano-micro Farad levels.
Description
A METHOD FOR OBTAINING A BIODEGRADABLE GEL
Technical Field
The present invention relates to a method for obtaining a transparent biodegradable gel (elastomer) which is self-healing (autonomously) without needing any external effect at room temperature, has high strength and stretching features simultaneously and can provide linear capacitance response at small strain values in nano-micro Farad levels.
Background of the Invention
Biodegradable materials are the ones that can participate in the cycle in nature upon being degraded by efficiency of biological agents. Some natural gases such as CO2, N2, water and inorganic salts occur in consequence of this degradation. Biodegradable materials have become an issue due to environmental damages caused by plastics today and many studies have been done in order to improve them, and they are continued to be done as well. Products produced with this technology are environmentally friendly. Biodegradable materials have area of use in the healthcare industry as well as in the plastics industry. These materials are grouped as the ones obtained by starch based, cellulose based, chemical synthesis and the ones produced by bacteria. Biodegradable gels, a type of biodegradable materials, can be produced in elastomer structure. As the amount of cross-links formed during the synthesis increases, the final strength of the material increases however its stretching features reduce. Therefore, there is need for a gel which has high strength and stretching features simultaneously, in order to be used in wearable electronic device applications, biomaterial and tissue engineering fields and which is also degradable in time and is self-healing without needing any external stimulus in case of damage.
The Chinese patent document no. CN106750416, an application in the state of the art, discloses an injectable hydrogel with self-healing and pH response properties. It is not required to add chemical reagents in the process of obtaining hydrogel and no post-purification is needed. The resulting hydrogel is non-toxic and ready for use. The hydrogel is obtained by intermixing and cross-linking N-carboxyethyl chitosan solution and PEGDA polymer solution. The hydrogel obtained by these solutions has a self-healing property and it does not need environmental stimulation for this property. The hydrogel obtained is used for producing biodegradable biomedical materials. The hydrogel displays a self-healing performance after externally applied strain changes.
The Chinese patent document no. CN106009003, another application in the state of the art, discloses an injectable self-repairing hydrogel, a preparation method and application thereof to biological tissue engineering. Gel is obtained by mixing a solution derivative of natural polymer chitosan with increased water solubility and sodium hyaluronate. The gel obtained has high strength, well biocompatibility and degradability and it is used in commercial biomedical products. It can be shaped as desired according to the wound area to be used. When the gel is mechanically damaged in the middle thereof, the intermediate gap shrinks gradually over time and eventually disappears completely.
As can also be seen in the patent documents mentioned above, although there are self-healing gels in the state of the art, none of these have self-healing feature without temperature, UV and other factors.
Summary of the Invention
An objective of the present invention is to realize a method for obtaining a biodegradable gel which has high stretching feature and strength simultaneously
and is used for preparing tissue scaffolds that will help regeneration of flexible soft tissue such as artificial skin, muscle, tendon, etc.
Another objective of the present invention is to realize a method for obtaining a biodegradable gel which eliminates the need for a second surgical procedure by degrading in time after being placed in the body, leaving its place to the newly formed (incipient) tissue.
An objective of the present invention is to realize a method for obtaining a biodegradable gel which heals itself autonomously by contacting broken parts with each other, and which has completely original features.
An objective of the present invention is to realize a method for obtaining a biodegradable gel which provides feature of giving capacitive response at very small strain values in nano-micro Farad levels.
Detailed Description of the Invention
“A Method for Obtaining a Biodegradable Gel” realized to fulfil the objectives of the present invention is shown in the figure attached, in which:
Figure l is a view of the flow chart of the inventive method for obtaining a biodegradable gel.
The components illustrated in the figure are individually numbered, where the numbers refer to the following:
100. Method
The inventive method for obtaining a biodegradable gel (100) which is self-healing (autonomously) without needing any external effect at room temperature, has high
strength and stretching features simultaneously and can provide linear capacitance response at small strain values in nano-micro Farad levels comprises the steps of: carrying out prepolymer reaction of a bifunctional polyethyleneglycol molecule with a diacid in the presence of a catalyst in a reactor (101); and - carrying out -OH condensation by cross-linking the polymers obtained in the prepolymer reaction (102).
In the inventive method (100), the bifunctional poly ethyleneglycol molecule at the step of carrying out prepolymer reaction (101) is a polyethyleneglycoldiglycidyl ether. The diacid used is a sebasic acid (C10H18O4). Caffeine is used as a catalyst in order that reaction between polyethyleneglycoldiglycidyl ether and sebasic acid is carried out. The said prepolymer reaction is preferably carried out in a microwave reactor. The prepolymer reaction carried out is completed in a period of 3-10 minutes.
The prepolymer reaction (101) carried out in the inventive method (100) is in the form of:
Polyethyleneglycolsebacate prepolymer is obtained at the end of the reaction.
In the inventive method (100), at the step of carrying out -OH condensation by cross-linking (102), the -OH (hydroxyl) groups occurring in the prepolymer obtained at the step of carrying out prepolymer reaction (101) are cross-linked at a temperature range of 110-160 ° C. In a preferred embodiment, 120°C is chosen as
the optimum temperature value. Cross-linking is carried out at vacuum values less than 100 mBar. The time required for cross-linking is between 24-48 hours. In a preferred embodiment, the desired gel properties are achieved after cross-linking carried out in 24 hours. A suitable material is obtained between a time period of 32- 48 hours however as the time extends, decrease occurs in the flexibility feature. - OH groups are consumed as a result of cross-linking and polyethyleneglycolsebacate, i.e. biodegradable gel (elastomer), is obtained.
The biodegradable gel obtained by the inventive method (100) has area of use as drug delivery system platform, muscle-tendon repair material including surgical threads in fiber form or woven-nonwoven medical textile products, wound bum cover materials (dressings), membranes, medical patches, tissue scaffold for soft and hard tissue repair/regeneration, guided tissue repair material, nails, plates and screws for orthopaedic applications, particle forms as well. Besides these areas, biodegradability has potential for use in the development of wearable sensor platforms, in sensor units at different soft robotics applications in biomedical field, and also in food, environment and other non-medical issues in terms of its flexing and capacitive feature.
Strength of the biodegradable gel obtained by the inventive method (100) is enhanced due to the cross-links contained by thereof and its flexibility feature is simultaneously enhanced by means of the raw materials used and the obtaining conditions as well. Besides, it displays high transparency when it is stretched. The said gel which can have high strength and stretching features simultaneously is used for preparing tissue scaffolds that may help regeneration of many flexible soft tissues such as artificial skin, muscle, tendon, etc. The regeneration materials used in this way eliminate the need for a second surgical procedure leaves its place to the newly formed (incipient) tissue upon degrading in time. The products formed as a result of degradation like the gel itself are also non-toxic products.
The biodegradable gel obtained by the inventive method (100) has a self-healing feature autonomously without temperature, UV and other factors. The biodegradable gel heals itself in a short time by contacting two broken parts with each other and regains its original strength and stretching property features completely. It is can be applied in industry as a meniscus repair material due to this feature and returned to its original condition by reuniting after contact upon it is degraded under loads. It can solve an existing problem by transferring the strength required during regeneration, to the related tissue by means of this feature in muscle, tendon and other similar applications.
The biodegradable gel obtained by the inventive method (100) has the feature of giving capacitive response at very small strain values in nano-micro Farad levels. A gel having this feature offers the potential to meet the already existing need for preparing platforms in flexible and wearable optoelectronic applications. The capacitive sensor prepared with the said gel helps to monitor tissue regeneration (for example heart muscle) or a physiological data (arterial pressure) in vivo by means of a biodegradable sensor. Similarly, the gel can be utilized in different platforms due to this feature in many wearable, flexible and biodegradable electronic or biomedical applications. In the event that it is configured as a sensor, a linear response is received from the sensor element as sensitive to very small strain (for example a muscle movement) or pressure to fall on the sensor.
Within these basic concepts; it is possible to develop various embodiments of the inventive method for obtaining a biodegradable gel (1); the invention cannot be limited to examples disclosed herein and it is essentially according to claims.
Claims
1. A method for obtaining a biodegradable gel (100) which is self-healing (autonomously) without needing any external effect at room temperature, has high strength and stretching features simultaneously and can provide linear capacitance response at small strain values in nano-micro Farad levels; characterized by the steps of:
carrying out prepolymer reaction of a bifunctional polyethyleneglycol molecule with a diacid in the presence of a catalyst in a reactor (101); and
carrying out -OH condensation by cross-linking the polymers obtained in the prepolymer reaction (102).
2. A method for obtaining a biodegradable gel (100) according to Claim 1;
characterized in that the bifunctional polyethyleneglycol molecule used is polyethyleneglycoldiglycidyl ether.
3. A method for obtaining a biodegradable gel (100) according to Claim 1;
characterized in that the diacid used is a sebasic acid (C10H18O4).
4. A method for obtaining a biodegradable gel (100) according to any of the preceding claims; characterized in that caffeine is used as a catalyst in order that reaction between polyethyleneglycoldiglycidyl ether and sebasic acid is carried out.
5. A method for obtaining a biodegradable gel (100) according to any of the preceding claims; characterized in that prepolymer reaction is carried out in a microwave reactor.
6. A method for obtaining a biodegradable gel (100) according to any of the preceding claims; characterized in that the prepolymer reaction carried out is completed in a period of 3-10 minutes.
7. A method for obtaining a biodegradable gel (100) according to any of the preceding claims; characterized in that the prepolymer reaction is in the form of:
8. A method for obtaining a biodegradable gel (100) according to any of the preceding claims; characterized in that polyethyleneglycolsebacate prepolymer is obtained at the end of the prepolymer reaction.
9. A method for obtaining a biodegradable gel (100) according to any of the preceding claims; characterized in that at the step of carrying out -OH condensation by cross-linking (102), the -OH (hydroxyl) groups occurring in the prepolymer obtained at the step of carrying out prepolymer reaction (101) are cross-linked at a temperature range of 110-160 ° C.
10. A method for obtaining a biodegradable gel (100) according to any of the preceding claims; characterized in that the optimum temperature value for cross-linking is 120°C.
11. A method for obtaining a biodegradable gel (100) according to any of the preceding claims; characterized in that coss-linking is carried out at vacuum values less than 100 mBar.
12. A method for obtaining a biodegradable gel (100) according to any of the preceding claims; characterized in that the time required for cross-linking is between 24-48 hours.
13. A method for obtaining a biodegradable gel (100) according to any of Claim 1 to 11; characterized in that the desired gel properties can be achieved after cross-linking carried out in 24 hours.
14. A method for obtaining a biodegradable gel (100) according to any of Claim 1 to 11; characterized in that a suitable gel is obtained between a time period of 32-48 hours however as the time extends, decrease occurs in the flexibility feature.
15. A method for obtaining a biodegradable gel (100) according to any of the preceding claims; characterized in that -OH groups are consumed as a result of cross-linking and polyethyleneglycolsebacate, i.e. biodegradable gel (elastomer), is obtained.
16. A method for obtaining a biodegradable gel (100) according to any of the preceding claims; characterized in that the biodegradable gel obtained by following a method for obtaining a biodegradable gel (100) according to any of the preceding claims is used as at least one of drug delivery system platform, muscle-tendon repair material, wearable sensor and sensor unit at different soft robotics applications in biomedical field including surgical thread in fiber form or woven-nonwoven medical textile product, wound burn cover material, membran, medical patch, tissue scaffold for soft and
hard tissue repair/regeneration, guided tissue repair material, nail, plate and screw for orthopaedic applications, particle forms.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TR2019/04095A TR201904095A2 (en) | 2019-03-19 | 2019-03-19 | THE METHOD OF OBTAINING A BIO-DEGRADABLE GEL |
| TR2019/04095 | 2019-03-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2020190240A2 true WO2020190240A2 (en) | 2020-09-24 |
| WO2020190240A3 WO2020190240A3 (en) | 2020-10-22 |
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ID=72520454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/TR2020/050212 WO2020190240A2 (en) | 2019-03-19 | 2020-03-17 | A method for obtaining a biodegradable gel |
Country Status (2)
| Country | Link |
|---|---|
| TR (1) | TR201904095A2 (en) |
| WO (1) | WO2020190240A2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114853952A (en) * | 2022-06-10 | 2022-08-05 | 闽江学院 | Super-stretching self-repairing nano cellulose gel and preparation method thereof |
| CN115490841A (en) * | 2022-11-22 | 2022-12-20 | 颢箔医疗科技(上海)有限公司 | Polyether diol polyazelaic acid fatty triol ester and preparation method and application thereof |
-
2019
- 2019-03-19 TR TR2019/04095A patent/TR201904095A2/en unknown
-
2020
- 2020-03-17 WO PCT/TR2020/050212 patent/WO2020190240A2/en active Application Filing
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114853952A (en) * | 2022-06-10 | 2022-08-05 | 闽江学院 | Super-stretching self-repairing nano cellulose gel and preparation method thereof |
| CN114853952B (en) * | 2022-06-10 | 2024-03-08 | 闽江学院 | Super-stretching self-repairing nanocellulose gel and preparation method thereof |
| CN115490841A (en) * | 2022-11-22 | 2022-12-20 | 颢箔医疗科技(上海)有限公司 | Polyether diol polyazelaic acid fatty triol ester and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2020190240A3 (en) | 2020-10-22 |
| TR201904095A2 (en) | 2020-10-21 |
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