FIELD OF THE INVENTION:

The present invention generally relates to condoms. More particularly, the invention relates to poly(gIycerol sebacate) (PGS) based condoms with increased sensitivity and protection against STIs & unplanned pregnancy.

BACKGROUND OF THE INVENTION:

Condoms are barrier devices used for both contraception and protection against sexually transmitted disease during intercourse. In recent years, incidence of sexually transmitted disease is increased which warrants the widespread use of condoms. Condoms are generally made of natural rubber, synthetic rubber, polyurethane, polyester, etc. Nowadays, polymer composites have also been used for producing condoms as the polymer composites exhibit enhanced physico-chemical properties than host polymer. Also, biodegradable polymers and personal care products including condoms formed from eco-friendly biodegradable polymers are becoming increasingly important.

Poly(gIycerol sebacate) (PGS) is a biodegradable polymer prepared by polycondensation of glycerol and sebacic acid. PGS elastomers have shown good flexibility (similar to vulcanized rubber), biocompatibility and biodegradability. PGS forms a covalently crossiinked, three-dimensional network of random coils with hydroxy! groups attached to its backbone. Both crosslinking and the hydrogen bonding interactions between the hydroxyl groups likely contribute to the unique properties of this elastomer. As a result, a number of patents have already been filed to biomedical applications, ranging from hard to soft tissue engineering, controlled drug delivery and tissue adhesives.

United States Patent Application No. 20130071930 to Chu; Hunghao et a!., entitled "Polyesters, methods of making polyesters and uses therefor" describes a lot of personal care items including condoms comprising po!y(sebacoyI diglyceride) by ring opening polymerization instead of Poly(glyceroI sebacate), which is produced by polycondensation reactions. Here, the inventors mainly used epoxide as starting material followed by functional ization with quaternary amine or ammonium group for antimicrobial activities.

United States Patent Application No. 20100215708 to Zumbuehl; Andreas et aiy entitled "Coating of devices with effector compounds" describes a method and composition for coating substrates, materials or devices including condoms comprising a polymer and effector compounds for preventing and treating various diseases. The materials of this invention may comprise metallic, ceramic, or polymeric materials, or a combination thereof in which the polymer may comprise poIy(gJycero! sebacate) (PGSA).

United States Patent Application No. 20130195841 to Gabbay; Jeffrey S. entitled "Biofilm resistant materials" describes a biofiJm resistant material comprising an active agent essentially made of an insoluble copper oxide and a polymeric resin. The materials of this invention may comprise metallic, ceramic, or polymeric materials, or a combination thereof in which the polymer may comprise poly(glycerol sebacate). Here, the substrate may be a part of, or in the form of a condom.

However, the above prior art does not disclose the use of poly(glycerol sebacate) exclusively to produce condoms.

The present invention aims to produce green and cheaper condoms using poly(glycerol sebacate) as a main constituent.

SUMMARY OF THE INVENTION:

An object of the present invention is to produce a library of poly (glycerol sebacate) materials with nanocomposites/aromatic/amide/aliphatic soft segments monomers/different cross linking agents and studying the physico-chemical-mechanical-degradation properties.

Another object of the present invention is to choose the best performing material from above made library and formulating either for dipping process i.e. pre-polymer dissolved in an organic solvent (THF/DCM/CHCb), followed by dipping and curing produces the condoms or film extrusion followed by high frequency welding to produce condoms.

According to the present invention, better-green-cheaper condoms are produced using PGS as a main constituent. The other additives such as graphene oxide/reduced graphene oxide/ clay/silica, 3-diamino-2-hydroxy propane/bis hydroxy ethylene te re phtha late/poly tetramethylene glycol/furan di carboxylic acids and acrylates are also included. The produced condoms are observed to have better physico-chemical-mechanical properties compare to latex made condoms. In addition, the produced condoms are bio-degradable and produced at cheaper cost.

These and other objective of the present invention will be more clearly understood from the following detailed description taken in conjunction with the accompanying drawings and claims.

BRIEF DESCRIPTION OF THE DRAWINGS:

The objective of the present invention will now be described in more detail with reference to the accompanying drawing, in which:

FIG. 1 is a schematic diagram showing the production of nanomaterial/1, 3-diamino propanol/bis hydroxy ethylene terephthalate/poly tetramethylene glycol/furan dicarboxylic acids incorporated poly(glycerol sebacate), which is used to produce the condoms.

DETAILED DESCRIPTION OF THE INVENTION:

Aspects of the present invention described herein, discloses a green and inexpensive poly (glycerol sebacate) (PGS) based condoms that have equivalent mechanical properties with the currently existing condom making polymers. In addition, the produced materials degrade completely within few weeks in the environment.

In the present invention, PGS condoms are produced from glycerol/glycerol derivatives such as 2,3-dihydroxypropyl 2-naphthoate or l,3-dihydroxypropan-2-yl 2-naphthoate/poly tetramethylene glycol (PTMEG), sebacic acid and nanomaterials such as graphene oxide/reduced graphene oxide/clay/silica, 3-diamino-2-hydroxy propane/bis hydroxy ethylene terephthalate/poly tetramethylene glycol/furan dicarboxylic acids and acrylates. Referring to FIG. 1 illustrates the production of nanomaterial/1, 3-diamino propanol incorporated poly (glycerol sebacate) using the three ingredients i.e. glycerol/glycerol derivatives, sebacic acid, and X where X is nanomaterial/1, 3-diamino propanol/ bis hydroxy ethylene terephthalate/poly tetramethylene glycol/furan dicarboxylic acids, which is used to produce condoms.

In one embodiment, the present invention provides a green and inexpensive condom with poly (glycerol sebacate) (PGS) nanocomposites. First, the PGS pre polymers are synthesised by taking 1 mole of sebacic acid, 0,1 to 0.95 mole of PTMEG and 0.1 to 0.5 w/w % of total reaction mixture of catalyst such as FASCAT 9100/FASCAT 4100/Titanium isopropoxide/Titanium butoxide into a round bottom flask at 100-200 °C under vacuum (1000 mbar to 0.1 mbar) for 8-24 hours. In the second step, the anhydrous glycerol (remaining amount of PTMEG to keep 1:1 mole diol/di acid ratios) are dissolved in dry DMF and reacted with napthoyl chloride (dissolved in dry DMF) to produce 2,3-dihydroxypropyl 2-naphthoate or l,3-dihydroxypropan-2-yl 2-naphthoate, which is then purified using column chromatography/solvent extraction methods. The above monomer mixture from step 1 and step 2 are mixed in appropriate ratio and stirred at 130 - 150 °C under vacuum (500 mbar to 0.1 mbar) for 4-24 hrs. Afterwards, 0.1 to 25 wt% of nanomaterials such as graphene/graphene oxide/reduced graphene oxide/silica/clay are mixed with the pre-polymers of PGS. Mixing is done using solvent mixing by THF/ CHCb/ CH2CI2 or melt mixing.

Further, the above prepared PGS nanocomposites are used to form films with varying thickness of 0.1 to 1mm by film extrusion/solvent casting. The films are characterized using different spectrometric techniques such as Transmission electron microscope (TEM) / Scanning electron microscopy (SEM)/ Atomic force microscopy and X-ray diffraction analysis. The thermal stability and the glass transition temperature are analysed using thermo gravimetric analysis (TGA) and differential scanning calorimetry (DSC). The tensile strength (5-25 MPa), elongation at break (250-900 %) and modulus (0.5-5 Mpa) are observed for the produced PGS-nanocomposites films. The optimized film from the above characterization methods are used for condom making by high frequency film welding/dipping technique.

In another embodiment, the present invention provides a green and inexpensive poly (glycerol sebacate) (PGS) condoms incorporated with other functional monomers such as terephthalic /furan di carboxylic acids/ bis hydroxy ethylene terephthalate/sebacic acid as a hard segment and aliphatic (poly(tetramethylene glycol)/ 3-diamino-2-hydroxy propane) as a soft segment. The prepolymers are made by 0 to 1 mole of sebacic acid / 0 to 0.5 mole of terephthalic acid / 0 to 0.5 mole of furan di carboxylic acids and 0.1 to 1 mole of glycerol / 0.1 to 0.9 mole of PTMEG in a round bottom flask at 100-200 °C in presence of 0.1 to 0.5 w/w % of total reaction mixture of catalysts such as FASCAT 9100/ FASCAT 4100/ Titanium isopropoxide/ Titanium butoxide under controlled vacuum (1000 to 0.1 mbar) for 8-24 hrs. 1 to 20 wt% of nanomaterials such as graphene/graphene oxide/reduced graphene oxide/silica/clay was mixed with the pre-polymers of PGS with different functional monomers. Mixing is done using solvent mixing by THF/DCM/CHCI3 or melt mixing.

Then, PGS nanocomposites film prepared with varying thickness of 0.1 to 1mm by film extrusion/solvent casting technique. These films are characterized using different spectrometric techniques such as Transmission electron microscope (TEM) / Scanning electron microscopy (SEM)/ Atomic force microscopy and X-ray diffraction analysis. The thermal stability and the glass transition temperature are analysed using thermo gravimetric analysis (TGA) and differential scanning calorimetry (DSC). The tensile strength (5-30 MPa), elongation at break (250- 1200 %) and modulus (0.5 -10 Mpa) are observed for the produced PGS-nanocomposites films. The optimized film from the above characterization methods are used for condom making by high frequency film welding / dipping technique.

In yet another embodiment, the present invention provides a green and inexpensive poly (glycerol sebacate) (PGS) condoms with crosslinking agents. The prepolymers are made by sebacic acid, glycerol and the above mentioned functional monomers at 100-200 °C in presence of 0.1 to 0.5 wt/wt % of total reaction mixture of catalysts such as FASCAT 9100/ FASCAT 4100/Titanium isopropoxide/Titanium butoxide under controlled vacuum (1000 to 0.1 mbar) for 8-24 hrs. This hydroxy functionalized PGS prepolymers are acrylated with varying amounts of (0.1 to 0.5 moI% acryloyl chloride/acrylic anhydride) using the following procedure.

A round-bottom flask is charged with the above prepared prepolymer and dissolved in 50-100 ml of anhydrous dichloromethane, and 4-(dimethylamino) pyridine (DMAP). The reaction flask is cooled to 0 °C under a positive pressure of N2. Acryloyl chloride (0.25-0.80 mol/mol of hydroxyl groups on the PGS prepolymer) is slowly added parallel to an equimolar amount of triethylamine. The reaction is allowed to reach room temperature and is stirred for an additional 24 hours. Polymer networks are formed by mixing linear polymer with 0.1% (w/w % of acrylate group attached) photoinitiator (2, 2-dimethoxy-2-phenylacetophenone), and the polymerization reaction is initiated by exposure to ultraviolet (365 nm) light for 10-20 min. The tensile strength (5-35 MPa), elongation at break (250- 600 %) and modulus (0.5 -12 Mpa) are found for the PGS-nanocomposites. The optimized film from the above characterization methods are used for condom making by high frequency film welding / dipping technique.

While this invention has been particularly shown and described with references to preferred embodiments thereof, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the scope of the invention encompassed by the appended claims.

We claim:

1. A composition for producing PGS condoms with increased sensitivity and protection against STIs and unplanned pregnancy comprising:

(a) a compound selected from the group consisting of glycerol, glycerol derivatives and poly tetramethylene glycol (PTMEG);

(b) sebacic acid; and

(c) one or more additional ingredients selected from the group consisting of nanomaterials, functional monomers and crosslinking agents.

2. The composition according to claim 01, wherein said glycerol derivative is selected from a group consisting of 2,3-dihydroxypropyl 2-naphthoate and l,3-dihydroxypropan-2-yl 2-naphthoate.

3. The composition according to claim 01, wherein said nanomaterial is selected from a group consisting of graphene oxide, reduced graphene oxide, clay, and functionalised silica.

4. The composition according to claim 01, wherein said functional monomer is selected from a group consisting of 3-diamino-2-hydroxy propane, 1,3-diamino propanol, terephthalic, bis hydroxy ethylene terephthalate, poly tetramethylene glycol, and furan di carboxylic acids.

5. The composition according to claim 01, wherein said crosslinking agent is an acrylating agent selected from acryloyl chloride and acrylic anhydride.

6. A method of producing PGS condoms with nanomaterials comprising the steps of:

(a) synthesizing PGS pre-polymer comprising the steps of:
1. preparing monomer mixture by taking sebacic acid and PTMEG into a round bottom flask at 100-200 °C in presence of a catalyst selected from FASCAT 9100, FASCAT 4100, Titanium isopropoxide and Titanium butoxide under vacuum for 8-24 hours;

2. producing 2,3-dihydroxypropyl 2-naphthoate or l,3-dihydroxypropan-2-yl 2-naphthoate by dissolving anhydrous glycerol in dry DMF and reacting with napthoyl chloride; and

3. mixing the monomer mixture from steps (1) and (2) in appropriate ratio and stirring at 130 - 150 °C under vacuum for 4-24 hrs.

(b)mixing said PGS pre-polymer with nanomaterials selected from graphene, graphene oxide, reduced graphene oxide, silica and clay; wherein said mixing is done using solvent mixing by an organic solvent selected from THF, CHCl3and CH2CI2 or melt mixing;

(c) preparing PGS nanocomposite films using film extrusion or solvent casting; and

(d)making condoms using said films by high frequency film welding or dipping process.

7. The method according to claim 06, wherein said amount of nanomaterials used ranges from 0.1 to25wt%.

8. A method of producing PGS condoms with functional monomers comprising the steps of:

(a) synthesizing PGS pre-polymer by glycerol or its derivatives, sebacic acid and one or more functional monomers selected from 3-diamino-2-hydroxy propane, 1,3-diamino propanol, terephthalic, bis hydroxy ethylene terephthalate, poly tetramethylene glycol, and furan di carboxylic acids in a round bottom flask at 100-200 °C in presence of a catalyst selected from FASCAT 9100, FASCAT 4100, Titanium isopropoxide and Titanium butoxide under controlled vacuum for 8-24 hours;

(b)mixing said PGS pre-polymer with nanomaterials selected from graphene, graphene oxide, reduced graphene oxide, silica and clay; wherein said mixing is done using solvent mixing by an organic solvent selected from THF, CHCI3 and CH2CI2 or melt mixing;

(c) preparing PGS nanocomposite films using film extrusion or solvent casting; and (d)making condoms using said films by high frequency film welding or dipping process.

9. The method according to claim 08, wherein said amount of nanomaterials used ranges from 1 to 20 wt%.

10. A method of producing PGS condoms with crosslinking agents comprising the steps of:

(a) synthesizing PGS pre-polymer by glycerol or its derivatives, sebacic acid and one or more functional monomers selected from 3-diamino-2-hydroxy propane, 1,3-diamino propanol, terephthalic, bis hydroxy ethylene terephthalate, poly tetramethylene glycol, and furan di carboxylic acids in a round bottom flask at 100-200 °C in presence of a catalyst selected from FASCAT 9100, FASCAT 4100, Titanium isopropoxide and Titanium butoxide under controlled vacuum for 8-24 hours;

(b)dissolving said pre-polymer in anhydrous dichloromethane with 4-(dimethylamino) pyridine (DMAP) and cooling the reaction flask to 0 °C under a positive pressure of nitrogen;

(c) adding 0.1 to 0.5 mol% of an acrylating agent such as acryloyl chloride or acrylic anhydride to glycerol, parallel to an equimolar amount of triethylamine;

(d)allowing the reaction to reach room temperature and stirring for an additional 24 hours;

(e) forming PGS nanocomposites via polymerization reaction by mixing linear polymer obtained from step (e) with a photoinitiator in presence of UV light for 10-20 min;

(f) preparing PGS nanocomposite films; and

(g)making condoms using said films by high frequency film welding or dipping process.

11. The method according to any of the preceding claims, wherein said PGS nanocomposite films has thickness ranges from 0.1 to 1mm.

12. The condom according to claim 01, has better physico-chemical-mechanical properties compared to latex made condoms.

13. The condom according to claim 01, is bio-degradable and inexpensive.