MATERIALS FOR OBTURATION
A curable mixture and method of using the mixture are disclosed. In some embodiments, the mixture comprises a water soluble acrylate-based monomer, a water-soluble acrylamide-based monomer, or a mixture thereof, and has properties suitable for use as a tooth filling after curing.
1 . A curable mixture of ingredients, comprising:
(a) a water-soluble acrylate-based monomer, a water-soluble acrylamide-based monomer, a water-soluble chelating monomer, or a mixture thereof;
(b) a free-radical polymerization initiator;
(c) a radiopaque material, wherein the radiopaque material is selected from the group consisting of 2,4,6-Triiodo-5-[(1-oxo-2-propen-1-yl)amino]-1,3-benzenedicarboxylic acid, 5-acryloylamino-N,N′-bis-[(2-hydroxy-1,1-bis-hydroxymethyl-ethylcarbamoyl)-methyl]-2,4,6-triiodoisophthalamide, 5-acryloylamino-N-(2,3-dihydroxypropyl)-N′-(2-hydroxy-1,1-bis-hydroxymethylethyl)-2,4,6-triiodoisophthalamide, and combinations thereof; and
(d) an aqueous carrier;
wherein the ingredients (a), (b), (c), and (d) are selected to provide the curable mixture with properties suitable for use as a tooth filling after curing the mixture to form a cured mixture by polymerization of ingredient (a) that is initiated by ingredient (b).
2 . The curable mixture of claim 1 , wherein the free radical initiator comprises a light initiator, thermal initiator, chemical initiator or a combination thereof.
3 . The curable mixture of claim 1 or 2 , wherein the water-soluble acrylamide-based monomer comprises 3-acrylamidopropyl trimethylammonium chloride, 3-methacrylamidopropyl trimethylammonium chloride, 3-acrylamidopropyl trimethylammonium methyl sulfate, 3-methacrylamidopropyl trimethylammonium methyl sulfate, Jeffamine (ED-900) diacrylate, Jeffamine (ED-2003) diacrylate, poly(ethylene glycol) diacrylamide, 3-Arm poly(ethylene glycol) triacrylamide, or a combination thereof.
4 . The curable mixture of any of claims 1 to 3 , wherein the water-soluble acrylate-based monomer comprises [2-(methacryloyloxy)ethyl] trimethylammonium chloride, [2-(acryloyloxy)ethyl] trimethylammonium chloride, [2-(acryloyloxy)ethyl] trimethylammonium methyl sulfate, [2-(methacryloyloxy)ethyl] trimethylammonium methyl sulfate, (hydroxyethyl)methacrylate (HEMA), or a combination thereof.
5 . The curable mixture of any of claims 1 to 4 , wherein the water-soluble acrylate-based monomer comprises poly(ethylene glycol) diacrylate, ethoxylated trimethylolpropane triacrylate, or a combination thereof.
6 . The curable mixture of any one of claims 1 to 5 , wherein the chelating monomer comprises 4-methacryloxyethyl trimellitic acid (4-MET) or glycerol phosphate dimethacrylate (GPDM).
7 . The curable mixture of any one of claims 1 to 6 , wherein the radiopaque material comprises 2,4,6-Triiodo-5-[(1-oxo-2-propen-1-yl)amino]-1,3-benzenedicarboxylic acid.
8 . The curable mixture of claim 7 , wherein the radiopaque material comprises 5-acryloylamino-N,N′-bis-[(2-hydroxy-1,1-bis-hydroxymethyl-ethylcarbamoyl)-methyl]-2,4,6-triiodoisophthalamide.
9 . The curable mixture of any one of claims 1 to 6 , wherein the radiopaque material comprises 5-acryloylamino-N-(2,3-dihydroxypropyl)-N′-(2-hydroxy-1,1-bis-hydroxymethylethyl)-2,4,6-triiodoisophthalamide.
10 . The curable mixture of claim 9 , wherein the radiopaque material comprises 5-acryloylamino-N,N′-bis-[(2-hydroxy-1,1-bis-hydroxymethyl-ethylcarbamoyl)-methyl]-2,4,6-triiodoisophthalamide, 2,4,6-Triiodo-5-[(1-oxo-2-propen-1-yl)amino]-1,3-benzenedicarboxylic acid, or a combination thereof.
11 . The curable mixture of any one of claims 1 to 10 , provided in two parts, each of which comprises a liquid.
12 . The curable mixture of claim 11 , wherein each of the two liquid part is degassed.
13 . The curable mixture of any one of claims 1 to 12 , further comprising a polymerization cross-linker.
14 . The curable mixture of claim 13 , wherein the polymerization cross-linker comprises N, N′-methylenebis(acrylamide) (MBAA), triethylene glycol dimethacrylate (TEGDMA), or a combination thereof.
15 . The curable mixture of ingredients of claim 1 , wherein the free radical initiator comprises a light initiator.
16 . The curable mixture of ingredients of claim 15 , comprising camphorquinone (CQ), 7,7-dimethyl-2,3-dioxobicyclo[2.2.1] heptane-1-carboxylic acid (CC Q), 1-phenyl-1,2-propanedione (PPD), 2,2′-azobis[2-methyl-N-(2-hydroxyethyl)propionamide (VA-086).
17 . The curable mixture of ingredients of claim 15 , comprising a co-initiator selected from N-phenylglycine, 2-pyrrolidinone, dimethylaminoethyl acrylate (DMAEA), triethanolamine (TEOA), 1-vinyl-2-pyrrolidone and L-arginine.
18 . The curable mixture of ingredients of any one of claims 1 to 14 , wherein the free radical initiator comprises a heat initiator.
19 . The curable mixture of ingredients of claim 18 , wherein the heat initiator comprises 2,2′-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride.
20 . The curable mixture of ingredients of any one of claims 1 to 14 , wherein the initiator comprises potassium persulfate.
21 . The curable mixture of ingredients of claim 20 , further comprising a co-initiator selected from N-phenylglycine, 2-pyrrolidinone, dimethylaminoethyl acrylate (DMAEA), triethanolamine (TEOA), 1-vinyl-2-pyrrolidone and L-arginine.
22 . The curable mixture of ingredients of any one of claims 1 to 21 , further comprising methacrylic acid.
23 . The curable mixture of ingredients of any one of claims 1 to 22 , comprising from wt % to 60 wt % of the aqueous carrier, based on the weight of the curable mixture.
24 . The curable mixture of ingredients of any one of claims 1 to 23 , wherein the aqueous carrier has a pH in the range of about 7.0 to about 8.4.
25 . An obturation material for use as a radiopaque tooth filling after curing, the obturation material, provided as two or more liquid parts, comprising:
(a) a water-soluble acrylate-based monomer, a water-soluble acrylamide-based monomer, a water-soluble chelating monomer, or a mixture thereof, selected from the group consisting of a multi-arm poly(ethylene glycol) acrylate, a multi-arm poly(ethylene glycol) acrylamide, an acrylate functionalized polyether, an acrylamide functionalized polyether, a methacrylamide functionalized polyether, and combinations thereof;
(b) a free-radical polymerization initiator;
(c) a radiopaque material; and
(d) an aqueous carrier;
wherein at least one liquid part has a viscosity less than 100 cP (at 25° C.), wherein (a), (b), (c), and (d) are selected to form a curable mixture, and wherein the obturation material is curable in a tooth by polymerization of ingredient (a) that is initiated by ingredient (b).
26 . The obturation material of claim 25 , wherein at least one liquid part has a viscosity less than 20 cP (25° C.).
27 . The obturation material of claim 25 or 26 , wherein at least one of the two or more liquid parts is a degassed liquid.
28 . The obturation material of claim 27 , wherein each of the degas sed liquid parts has a percent oxygen content reduction of at least 10%.
29 . The obturation material of any one of claims 25 to 28 , wherein the free radical initiator comprises a light initiator, chemical initiator, thermal initiator, or a combination thereof.
30 . The obturation material of any one of claims 25 to 28 , wherein the free radical initiator comprises a light initiator and a thermal initiator.
31 . The obturation material of any one of claims 25 to 30 , wherein the obturation material is curable upon exposure to human body temperature, and the obturation material has a Shore A hardness of at least 15 when cured.
32 . The obturation material of any one of claims 25 to 31 , wherein the multi-arm poly(ethylene glycol) acrylate and the multi-arm poly(ethylene glycol) acrylamide are selected from the group consisting of 3-arm PEG acrylate, 3-arm PEG methacrylate, 3-arm poly(ethylene glycol) acrylamide, 3-arm poly(ethylene glycol) triacrylamide, and 4-arm poly(ethylene glycol) acrylamide, or a combination thereof.
33 . The obturation material of any one of claims 25 to 31 , wherein the acrylate functionalized polyether, the acrylamide functionalized polyether and the methacrylamide functionalized polyether are selected from the group consisting of a Jeffamine® ED-900 acrylate, a Jeffamine® ED-900 acrylamide, a Jeffamine® ED-900 methacrylamide, a Jeffamine® ED 2003 acrylate, a Jeffamine® ED 2003 acrylamide, and a Jeffamine® ED 2003 methacrylamide, or a combination thereof.
34 . The obturation material of claim 33 , wherein the acrylate functionalized polyether and the acrylamide functionalized polyether are selected from the group consisting of Jeffamine® ED-900 diacrylate, Jeffamine® ED-900 triacrylamide, Jeffamine® ED 2003 diacrylate, and Jeffamine® ED 2003 triacrylamide, or a combination thereof.
35 . The obturation material of any one of claims 25 to 34 , wherein the radiopaque material comprises sodium diatrizoate hydrate or 5-acrylamido-2,4,6 triiodo isophthalic acid.
36 . The obturation material of any one of claims 25 to 35 , comprising a cross-linker comprises N,N′-methylenebis(acrylamide) (MB AA), triethylene glycol dimethacrylate (TEGDMA), or a combination thereof.
37 . The obturation material of any one of claims 25 to 36 , where the obturation material has a hardness value of at least 40 Shore A within 40 seconds of exposure to light energy.
38 . A method of preparing a hydrogel comprising forming a reaction mixture comprising the curable mixture or obturation material of any one of claims 1 to 37 , wherein the reaction mixture forms the hydrogel upon exposure to human body temperature for a period of time effective to cure the curable mixture.
39 . The method of claim 38 , further comprising degassing the reaction mixture prior to delivering the reaction mixture to a tooth inside the human body.
40 . A method of filling a tooth, comprising:
identifying a tooth having a cavity in need of filling;
positioning the curable mixture or obturation material of any one of claims 1 to 37 within the cavity; and curing the curable mixture or obturation material within the cavity.
41 . A method of filling a root canal, comprising:
identifying a tooth having a root canal in need of filling;
positioning the curable mixture or obturation material of any one of claims 1 to 37 within the root canal; and
curing the curable mixture or obturation material within the root canal.
42 . A method of filling a root canal with a hydrogel polymer, comprising:
(a) identifying a tooth having a root canal in need of filling;
(b) positioning an aqueous curable mixture or obturation material of any of claims 1 to 37 within a handpiece, comprising delivering the curable mixture or obturation material to the handpiece in two liquid parts;
(c) forming a liquid jet within the handpiece and using the liquid jet to deliver the two parts;
(d) partially curing the curable mixture or obturation material within the root canal with light energy; and
(e) exposing the partially cured mixture or obturation material within the root canal to heat to form a cured hydrogel polymer within the root canal.
43 . A curable mixture of ingredients, comprising:
(a) 14 wt. % to 65 wt. % poly(ethylene glycol) diacrylate;
(b) 15 wt. % to 45 wt. % of 5-acrylamido-2,4,6-triiodo isophthalic acid;
(c) 0.2 wt. % to 6 wt. % a free-radical polymerization initiator; and
(d) 20 wt. % to 60 wt. % of an aqueous carrier,
wherein the ingredients are selected to provide the curable mixture with properties suitable for use as a tooth filling material after curing.
44 . The curable mixture of claim 43 , where the free-radical polymerization initiator is a chemical initiator.
45 . The curable mixture of claim 43 or 44 , comprising 0.3 wt. % to 1.0 wt. % of a second free-radical polymerization initiator that is a light initiator.
46 . A curable mixture of ingredients, comprising:
(a) 14 wt. % to 65 wt. % poly(ethylene glycol) diacrylate;
(b) 0.2 wt. % to 6 wt. % potassium persulfate;
(c) 0.3 wt. % to 1.0 wt. % 1-phenyl-1,2-propanedione (PPD);
(d) 15 wt. % to 50 wt. % of 5-acrylamido-2,4,6-triiodo isophthalic acid; and
(e) 20 wt. % to 60 wt. % of an aqueous carrier,
wherein the ingredients are selected to provide properties suitable for use as a tooth filling material after curing.
47 . The curable mixture of any of claims 43 through 46 , comprising
(a) 15 wt. % to 55 wt. % poly(ethylene glycol) diacrylate; and
(b) 20 wt. % to 40 wt. % of 5-acrylamido-2,4,6-triiodo isophthalic acid.
48 . The curable mixture of any of claims 43 through 47 , comprising from 30 wt % to wt % aqueous carrier.
49 . The curable mixture of any of claims 43 through 47 , comprising from 40 wt % to wt % aqueous carrier.
50 . The curable mixture of any of claims 43 through 49 , further comprising a quaternary ammonium salt.
51 . The curable mixture of any of claims 43 through 49 , further comprising from 0.2 wt % to 5 wt % [2-(acryloyloxy)ethyl]trimethyl-ammonium chloride (EGAA).
52 . The curable mixture of any of claims 43 through 51 , comprising a co-initiator selected from N-phenylglycine, 2-pyrrolidinone, dimethylaminoethyl acrylate (DMAEA), triethanolamine (TEOA), 1-vinyl-2-pyrrolidone and L-arginine.
53 . The curable mixture of any of claims 43 through 52 , further comprising from 0.2 wt % to 5 wt % of an acrylamide-based monomer.
54 . The curable mixture of any of claims 43 through 52 , further comprising an 8-arm poly(ethylene glycol) acrylate crosslinker.
55 . The curable mixture of any of claims 43 through 54 , further comprising triethanolamine (TEOA).
56 . An obturation material for use as a radiopaque tooth filling after curing, the obturation material, provided as two or more liquid parts, comprising:
(a) 15 wt. % to 65 wt. % poly(ethylene glycol) diacrylate;
(b) 15 wt. % to 45 wt. % of 5-acrylamido-2,4,6-triiodo isophthalic acid;
(c) 0.2 wt. % to 6 wt. % a first free-radical polymerization initiator;
(d) 0.3 wt. % to 1.0 wt. % a second free-radical polymerization initiator that is a light initiator; and
(e) 20 wt. % to 60 wt. % of an aqueous carrier,
wherein at least one liquid part comprising (a) through (d) has a viscosity less than 60 cP (at 25° C.); wherein(a), (b), (c), and (d) are selected to form a curable mixture;
and wherein the obturation material is curable in a tooth by a polymerization of ingredient (a) that is initiated by ingredients (c) and (d).
57 . The obturation material of claim 56 , comprising
(a) 15 wt. % to 60 wt. % poly(ethylene glycol) diacrylate;
(b) 15 wt. % to 45 wt. % of 5-acrylamido-2,4,6-triiodo isophthalic acid
(c) 0.2 wt. % to 6 wt. % potassium persulfate;
(d) 0.3 wt. % to 1.0 wt. % 1-phenyl-1,2-propanedione (PPD); and
(e) 30 wt. % to 60 wt. % of an aqueous carrier.
58 . The obturation material of claim 56 or 57 , wherein at least one liquid part has a viscosity less than 20 cP (25° C.).
59 . The obturation material of any one of claims 56 through 58 , curable to a Shore A hardness of at least 15 upon light curing with an exposure of 10 seconds.
60 . A curable mixture of ingredients, comprising:
(a) 20 wt. % to 65 wt % 3-arm poly(ethylene glycol) acrylate;
(b) 15 wt % to 30 wt. % of 5-acrylamido-2,4,6-triiodo isophthalic acid;
(c) at least one free-radical polymerization initiator in an amount of 0.2 wt. % to 1.5 wt %; and
(d) 20 wt % to 60 wt % of an aqueous carrier.
61 . The curable mixture of claim 60 , comprising 0.3 wt % to 1.0 wt % of a second free-radical polymerization initiator, wherein at least one is a light initiator.
62 . The curable mixture of claim 60 , comprising 0.2 wt % to 6% of a co-initiator.
63 . The curable mixture of claim 60 , comprising 0.2 wt. % to 1.5 wt % potassium persulfate.
64 . The curable mixture of claim 60 or 63 , comprising 0.3 wt % to 1.0 wt % 1-phenyl-1,2-propanedione (PPD).
65 . The curable mixture of any one of claims 60 through 64 , comprising 0.1 wt % to 3 wt % triethanolamine (TEOA).
66 . An obturation material for use as a radiopaque tooth filling after curing, the obturation material, provided as two or more liquid parts, comprising:
(a) 20 wt. % to 65 wt % 3-arm poly(ethylene glycol) acrylate;
(b) 15 wt % to 30 wt. % of 5-acrylamido-2,4,6-triiodo isophthalic acid;
(c) 0.2 wt. % to 1.5 wt % of a first free-radical polymerization initiator;
(d) optionally, 0.3 wt % to 1.0 wt % of a second free-radical polymerization initiator that is a light initiator;
(e) optionally, 0.2 wt % to 6% of a co-initiator; and
(f) 20 wt % to 60 wt % of an aqueous carrier,
wherein at least one liquid part has a viscosity less than 60 cP (at 25° C.), wherein
(a), (b), (c), (d) and (e) are selected to form a curable mixture, and wherein the obturation material is curable in a tooth by a polymerization of ingredient (a) that is initiated by ingredient (c) and/or (d).
67 . The obturation material of claim 66 , wherein at least one liquid part has a viscosity less than 20 cP (25° C.).
68 . The obturation material of claim 66 or 67 , curable to a Shore A hardness of at least 15 upon light curing with an exposure of 10 seconds.
69 . A method of filling a root canal with the hydrogel polymer of claim, comprising:
(a) identifying a tooth having a root canal in need of filling;
(b) positioning an aqueous curable mixture or obturation material of any of claims 43 through 68 , within a handpiece, comprising delivering the curable mixture or obturation material to the handpiece in two liquid parts;
(c) forming a liquid jet within the handpiece and using the liquid jet to deliver the two parts;
(d) partially curing the curable mixture or obturation material within the root canal with light energy; and
(e) exposing the partially cured mixture or obturation material within the root canal to heat to form a cured hydrogel polymer within the root canal.
70 . A curable mixture of ingredients, comprising:
(a) 15 wt. % to 65 wt. % water soluble acrylamide-based monomer;
(b) 15 wt. % to 45 wt. % water soluble ionic or non-ionic iodinated X-ray contrast acrylate monomer;
(c) 0.2 wt. % to 6 wt. % a free-radical polymerization initiator; and
(d) 15 wt. % to 60 wt. % of an aqueous carrier,
wherein the ingredients are selected to provide the curable mixture with properties suitable for use as a tooth filling after curing of the curable mixture to form a cured mixture.
71 . The curable mixture of claim 70 , comprising:
(a) 15 wt. % to 60 wt. % water soluble acrylamide-based monomer;
(b) 15 wt. % to 45 wt. % 5-acrylamido-2,4,6-triiodo isophthalic acid;
(c) 0.2 wt. % to 6 wt. % of a free-radical polymerization initiator;
(d) 0.1 wt % to 0.3 wt % of a quaternary ammonium salt; and
(d) 15 wt. % to 60 wt. % of an aqueous carrier.
72 . The curable mixture of claim 71 , wherein the acrylamide-based monomer comprises acrylamide, diacrylamide, triacrylamide, methacrylamide, or a combination thereof.
73 . The curable mixture of claim 71 , wherein the acrylamide-based monomer comprises poly(ethylene glycol) acrylamide, poly(ethylene glycol) diacrylamide, poly(ethylene glycol) triacrylamide, or a combination thereof.
74 . The curable mixture of claim 71 , wherein the acrylamide-based monomer comprises a multi-arm poly(ethylene glycol) acrylamide-based monomer.
75 . The curable mixture of claim 71 , wherein the acrylamide-based monomer comprises a 3-arm poly(ethylene glycol) acrylamide-based monomer, 4-arm poly(ethylene glycol) acrylamide-based monomer, 8-arm poly(ethylene glycol) acrylamide-based monomer, or a combination thereof.
76 . The curable mixture of claim 71 , wherein the acrylamide-based monomer comprises N,N′-(dimethyl)-ethylenebisacrylamide, bis[2-(2-methyl-acrylamino)-ethoxycarbonyl]-hexamethylenediamine, or N,N′-diethyl-1,3-propylene-bis-acrylamide, or a combination thereof.
77 . An obturation material for use as a radiopaque tooth filling after curing, the obturation material, provided as two or more liquid parts, comprising:
(a) 15 wt. % to 65 wt. % water soluble acrylamide-based monomer;
(b) 15 wt % to 30 wt. % of 5-acrylamido-2,4,6-triiodo isophthalic acid;
(c) 0.2 wt. % to 1.5 wt % of a free-radical polymerization initiator;
(d) optionally, 0.3 wt % to 1.0 wt % of a second free-radical polymerization initiator that is a light initiator;
(e) optionally, 0.2 wt % to 6% of a co-initiator; and
(f) 20 wt % to 60 wt % of an aqueous carrier,
wherein at least one liquid part has a viscosity less than 60 cP (at 25° C.), wherein (a), (b), (c), (d) and (e) are selected to form a curable mixture, and wherein the obturation material is curable in a tooth by a polymerization of ingredient (a) that is initiated by ingredient (c) and/or (d).
78 . A method of filling a root canal with the hydrogel polymer of claim, comprising:
(a) identifying a tooth having a root canal in need of filling;
(b) positioning an aqueous curable mixture or obturation material of any of claims 71 through 77 , within a handpiece, comprising delivering the curable mixture or obturation material to the handpiece in two liquid parts;
(c) forming a liquid collimated jet within the handpiece and using the liquid jet to deliver the two parts;
(d) at least partially curing the curable mixture or obturation material within the root canal with light energy; and
(e) allowing the partially cured mixture or obturation material within the root canal to further chemically cure to form a cured hydrogel polymer within the root canal;
wherein at least one liquid part has a viscosity less than 60 cP (at 25° C.).
79 . A curable mixture of ingredients, comprising:
(a) 15 wt. % to 65 wt. % water soluble acrylate-based monomer, acrylamide-based monomer, or a combination thereof;
(b) 15 wt. % to 45 wt. % water soluble iodinated X-ray contrast acrylate monomer;
(c) 0.2 wt. % to 6 wt. % a free-radical polymerization initiator; and
(d) 15 wt. % to 60 wt. % of an aqueous carrier,
wherein the ingredients are selected to provide properties suitable for use as a tooth filling material after curing.
80 . The curable mixture of claim 79 , wherein the iodinated X-ray contrast acrylate monomer is ionic.
81 . The curable mixture of claim 79 , wherein the iodinated X-ray contrast acrylate monomer is non-ionic.
82 . The curable mixture of claim 79 , wherein the X-ray contrast acrylate monomer comprises 5-acrylamido-2,4,6-triiodo isophthalic acid, 2,4,6-Triiodo-5-[(1-oxo-2-propen-1-yl)amino]-1,3-benzenedicarboxylic acid, 5-acryloylamino-N,N′-bis-[(2-hydroxy-1,1-bis-hydroxymethyl-ethylcarbamoyl)-methyl]-2,4,6-triiodoisophthalamide, 5-acryloylamino-N-(2,3-dihydroxypropyl)-N′-(2-hydroxy-1,1-bis-hydroxymethylethyl)-2,4,6-triiodoisophthalamide, or a combination thereof.
83 . An obturation material, for use as a tooth filling material after curing, comprising
a curable mixture provided as two or more liquid parts, comprising:
(a) a water-soluble acrylate-based monomer, a water-soluble acrylamide-based monomer, a water-soluble chelating monomer, or a mixture thereof;
(b) calcium silicate dispersed in a non-aqueous carrier;
(c) a free-radical polymerization initiator;
(d) a water-soluble radiopaque material; and
(e) a low viscosity liquid;
wherein components (a) and (b) are selected to provide properties suitable for use as a tooth filling material after curing to form a cured mixture by polymerization of ingredient (a) that is initiated by ingredient (c).
84 . The obturation material of claim 83 , wherein (a) comprises poly(ethylene glycol) diacrylate.
85 . The obturation material of claim 83 , wherein (d) comprises 5-acrylamido-2,4,6-triiodo isophthalic acid, 2,4,6-Triiodo-5-[(1-oxo-2-propen-1-yl)amino]-1,3-benzenedicarboxylic acid, 5-acryloylamino-N,N′-bis-[(2-hydroxy-1,1-bis-hydroxymethyl-ethylcarbamoyl)-methyl]-2,4,6-triiodoisophthalamide,5-acryloylamino-N-(2,3-dihydroxypropyl)-N′-(2-hydroxy-1,1-bis-hydroxymethylethyl)-2,4,6-triiodoisophthalamide, or a combination thereof.
86 . The obturation material of claim 83 further comprising a crosslinker.
87 . The obturation material of claim 83 further comprising an 8-arm poly(ethylene glycol) diacrylate.
88 . The obturation material of claim 83 further comprising MBAA.
89 . The obturation material of any of claims 83 through 88 wherein component (a) comprises between about 15 wt % to 40 wt % of at least one water-soluble acrylate-based monomer, water-soluble acrylamide-based monomer, or a combination thereof.
90 . The obturation material of any of claims 83 through 89 wherein (a) is provided as an aqueous solution.
91 . The obturation material of claim 90 , comprising an aqueous solution further comprising from about 0.1 wt % to about 5 wt % of a base selected from calcium hydroxide, lithium hydroxide or sodium hydroxide.
92 . The obturation material of any of claims 83 through 91 , wherein (b) comprises about 10 wt % to 60 wt % of calcium silicate, based on the total weight of the components of (b).
93 . The obturation material of any of claims 83 through 92 , wherein (b) comprises tricalcium silicate.
94 . The obturation material of any of claims 83 through 91 , wherein the calcium silicate consists essentially of tricalcium silicate.
95 . The obturation material of any of claims 83 through 94 , wherein (b) further comprises propylene glycol or poly(ethylene glycol) diacrylate as a non-aqueous carrier liquid.
96 . The obturation material of claim 94 , comprising less than 40 wt % tricalcium silicate based on the total weight of the curable material.
97 . The obturation material of claim 94 , comprising less than 30 wt % tricalcium silicate based on the total weight of the curable material.
98 . The obturation material of claim 94 , comprising less than 25 wt % tricalcium silicate based on the total weight of the curable material.
99 . The obturation material of claim 94 , comprising less than 20 wt % tricalcium silicate based on the total weight of the curable material.
100 . The obturation material of claim 94 , comprising less than 15 wt % tricalcium silicate based on the total weight of the curable material.
101 . The obturation material of any of claims 83 through 100 , wherein a first liquid part comprises from about 3 wt % to 20 wt % of a water-soluble radiopaque material and from about 80 wt % to 97 wt % of the water soluble monomer of (a), a second liquid part comprises water, and a third part comprises calcium silicate and a non-aqueous carrier liquid.
102 . The obturation material of any of claims 83 through 101 , further comprising potassium persulfate.
103 . The obturation material of claim 83 , wherein the low viscosity liquid has a viscosity less than 60 cP (at 25° C.).
104 . The obturation material of any one of claims 83 through 103 , wherein the curable mixture is provided as three parts.