Endoluminal device and polymer
Various embodiments relate to compositions for use in endoluminal devices and to methods of using compositions in endoluminal devices. The compositions include two parts, a first part including a first solution and a second part including a second solution, wherein the first solution comprises one or more pre-polymers, a non-aqueous solvent, a polymerization co-initiator or initiator and optionally one or more chain extenders and additives, and the second solution comprises a polymerization initiator or co-initiator, a non-aqueous solvent and optionally one or more chain extenders and additives.
1. An organogel composition comprising two parts, a first part comprising a first solution and a second part comprising a second solution, wherein
the first solution comprises one or more pre-polymers, a non-aqueous solvent, a polymerization co-initiator or initiator, and optionally one or more chain extenders and additives; and
the second solution comprises a polymerization initiator or co-initiator, a non-aqueous solvent, and optionally one or more chain extenders and additives,
wherein the first part and the second part are separate from each other,
wherein the non-aqueous solvent of the first solution does not react with the one or more pre-polymers in the first solution,
wherein the one or more pre-polymers comprises compounds having at least two functional groups selected from acrylate, methacrylate, and vinyl functional groups, the one or more pre-polymers selected from the group consisting of ethoxylated (3) bisphenol A diacrylate, ethoxylated (30) bisphenol A diacrylate (EBPADA), ethoxylated (9) trimethylolpropane triacrylate, ethoxylated (15) trimethylolpropane triacrylate, ethoxylated (20) trimethylolpropane triacrylate (PEG-T), propoxylated (3) trimethylolpropane triacrylate (PTMPTA), pentaerythritol triacrylate, ethoxylated (4) pentaerythritol tetraacrylate, pentaerythritol tetraacrylate, the methacrylic variants of the aforesaid acrylates, divinyl adipate, 1,4-dibutane diol divinyl ether, di and tri-ethylene glycol divinyl ether, allyl ether, diallyl maleate, trimethyl propane diallyl ether, and combinations thereof, and
wherein a combination of the first part and second part
exhibits a viscosity of from about 5 cP to about 100 cP, at 25° C., 30% solution, and
forms an organogel exhibiting a static compressive modulus of from about 0.1 MPa to about 50 MPa, measured in accordance with ASTM D575-91, within a gel time of about 30 seconds to about 30 minutes.
2. The organogel composition of claim 1 , wherein the non-aqueous solvent comprises aliphatic and/or aromatic solvents selected from the group consisting of alcohols, aldehydes, amides, carbonates, ethers, esters, glycols, glycol ethers, glycol esters, hydrocarbons, ketones, sulfoxides, and vegetable oils.
3. The organogel composition of claim 2 , wherein the non-aqueous solvent is selected from the group consisting of methanol, glycerin, ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol, diethylene glycol, tripropylene glycol, polyethylene glycol, ethyl ether, tripropylene glycol methyl ether, di(propylene glycol) butyl ether, propylene carbonate, butylene carbonate, benzene, toluene, xylene, methyl ethyl ketone, castor oil, linseed oil, sesame oil, soybean oil, olive oil, and combinations thereof.
4. The organogel composition of claim 1 , wherein the chain extender comprises mono-- or di-functional compounds having acrylate, methacrylate or vinyl functional groups.
5. The organogel composition of claim 4 , wherein the chain extender is selected from the group consisting of polyethylene glycol monoacrylate (PEGMA), polypropylene glycol monoacrylate (PPGMA), polyethylene glycol diacrylate (PEGDA), polypropylene glycol diacrylate (PPGDA), dipropylene glycol diacrylate (DPGDA), tetraethylene glycol diacrylate (TEGDA), tripropylene glycol diacrylate (TPGDA), polyethylene glycol mono methacrylate (PEGMMA), polypropylene glycol mono methacrylate (PPGMMA), polyethylene glycol methyl ether methacrylate (PEGMEMA), polyethylene glycol dimethacrylate (PEGDMA), polypropylene glycol dimethacrylate (PPGDMA), and combinations thereof.
6. The organogel composition of claim 1 , wherein the polymerization initiator comprises peroxides and hydroperoxides.
7. The organogel composition of claim 6 , wherein the polymerization initiator is selected from the group consisting of benzoyl peroxide (BPO), cumene hydroperoxide (CHP), Di-cumyl peroxide (CPO), lauryl peroxide, tert-amyl hydroperoxide (t-AHP), tert-butyl hydroperoxide (t-BHP), di-tert-butyl peroxide (DTBP), tributyl hydroperoxide (TBPH), tetra-methyl butyl hydroperoxide (MBHP), and combinations thereof.
8. The organogel composition of claim 1 , wherein the polymerization co-initiator is selected from the group consisting of tri-ethanol amine (TEA), 1-(2-pyridyl)-2-thiourea (PTU), 1-acetyl-2-thiourea (ATU), N, N-dihydroxyethyl-p-toluidine (DHEPT), 4-(di-methyl amino) phenethyl alcohol (DMAPE), ethyl 4-(dimethylamino)benzoate (EDMAB), 2-[4-(dimethylamino)phenyl]ethanol, N,N-dimethyl-p-toluidine (DMPT), bis(hydroxyethyl)-p-toluidine, and combinations thereof.
9. The organogel composition of claim 1 , wherein either or both of the first and second solutions further comprise a co-solvent.
10. The organogel composition of claim 9 , wherein the co-solvent is selected from the group consisting of nonanol, dimethyl sulfoxide, butylene carbonate, di-ethylene glycol ethyl ether, di-propylene glycol methyl ether, di-propylene glycol butyl ether, tri-propylene glycol methyl ether and tri-propylene glycol butyl ether, and combinations thereof.
11. The organogel composition of claim 1 , further comprising one or more additives.
12. The organogel composition of claim 11 , wherein the one or more additives are selected from the group consisting of fillers, contrast agents, processing aids, plasticizers, and viscosity-reducing agents.
13. An organogel comprising the composition of claim 1 , wherein the organogel is formed from the combination of the first part and the second part.
14. The organogel of claim 13 , wherein the organogel exhibits a static compressive modulus of from about 1 MPa to about 18 MPa, measured in accordance with ASTM D575-91.
15. The organogel of claim 13 , wherein the organogel exhibits a gel time of about 1 min to about 20 min.
16. The organogel composition of claim 1 , further comprising a total composition weight, wherein the non-aqueous solvent in the first part is present in an amount greater than 50% by weight of the total composition weight.
17. A system for treating an aneurysm, the system comprising a filling structure filled with the organogel composition according to claim 1 .
18. An organogel composition comprising two parts, a first part comprising a first solution and a second part comprising a second solution, wherein
the first solution comprises one or more pre-polymers, a non-aqueous solvent, a polymerization co-initiator or initiator, and optionally one or more chain extenders and additives; and
the second solution comprises a polymerization initiator or co-initiator, a non-aqueous solvent, and optionally one or more chain extenders and additives,
wherein the first part and the second part are separate from each other,
wherein the non-aqueous solvent of the first solution does not react with the one or more pre-polymers in the first solution,
wherein the one or more pre-polymers comprises compounds having at least two functional groups selected from acrylate, methacrylate, and vinyl functional groups, the one or more pre-polymers selected from the group consisting of ethoxylated (3) bisphenol A diacrylate, ethoxylated (30) bisphenol A diacrylate (EBPADA), ethoxylated (9) trimethylolpropane triacrylate, ethoxylated (15) trimethylolpropane triacrylate, ethoxylated (20) trimethylolpropane triacrylate (PEG-T), propoxylated (3) trimethylolpropane triacrylate (PTMPTA), pentaerythritol triacrylate, ethoxylated (4) pentaerythritol tetraacrylate, pentaerythritol tetraacrylate, the methacrylic variants of the aforesaid acrylates, divinyl adipate, 1,4-dibutane diol divinyl ether, di and tri-ethylene glycol divinyl ether, allyl ether, diallyl maleate, trimethyl propane diallyl ether, and combinations thereof,
wherein the non-aqueous solvent includes aliphatic and/or aromatic solvents, the non-aqueous solvent selected from the group consisting of alcohols, aldehydes, amides, carbonates, ethers, esters, glycols, glycol ethers, glycol esters, hydrocarbons, ketones, sulfoxides, and vegetable oils, and
wherein a combination of the first part and second part forms an organogel exhibiting a static compressive modulus of from about 0.1 MPa to about 50 MPa, measured in accordance with ASTM D575-91, within a gel time of about 30 seconds to about 30 minutes.
19. A system for treating an aneurysm, the system comprising a filling structure filled with the organogel composition according to claim 18 .
20. A method of forming an organogel comprising:
contacting a first part of a composition and a second part of the composition, wherein
the first part of the composition comprises a first solution comprising one or more pre-polymers, a non-aqueous solvent, a polymerization co-initiator or initiator, and optionally one or more chain extenders and additives; and
the second part of the composition comprises a second solution comprising a polymerization initiator or co-initiator, a non-aqueous solvent, and optionally one or more chain extenders and additives,
wherein the first part and second part are separate from each other prior to contacting,
wherein the non-aqueous solvent of the first solution does not react with the one or more prepolymers in the first solution,
wherein the one or more pre-polymers comprises compounds having at least two functional groups selected from acrylate, methacrylate, and vinyl functional groups, the one or more pre-polymers selected from the group consisting of ethoxylated (3) bisphenol A diacrylate, ethoxylated (30) bisphenol A diacrylate (EBPADA), ethoxylated (9) trimethylolpropane triacrylate, ethoxylated (15) trimethylolpropane triacrylate, ethoxylated (20) trimethylolpropane triacrylate (PEG-T), propoxylated (3) trimethylolpropane triacrylate (PTMPTA), pentaerythritol triacrylate, ethoxylated (4) pentaerythritol tetraacrylate, pentaerythritol tetraacrylate, the methacrylic variants of the aforesaid acrylates, divinyl adipate, 1,4-dibutane diol divinyl ether, di and tri-ethylene glycol divinyl ether, allyl ether, diallyl maleate, trimethyl propane diallyl ether, and combinations thereof; and
initiating polymerization of the one or more pre-polymers to form the composition exhibiting a viscosity of from about 5 cP to about 100 cP, at 25° C., 30% solution, wherein the composition forms an organogel exhibiting a static compressive modulus of from about 0.1 MPa to about 50 MPa, measured in accordance with ASTM D575-91, within a gel time of about 30 seconds to about 30 minutes.
21. The method of claim 20 , wherein the one or more additives are selected from the group consisting of fillers, contrast agents, processing aids, plasticizers, and viscosity-reducing agents.