Epoxy-containing dental composition curable by multiple polymerization mechanisms
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
A61K-006/08
A61K-006/00
C08G-059/17
C08G-059/42
C08L-063/00
C08F-222/10
출원번호
US-0377441
(2010-06-11)
등록번호
US-9345647
(2016-05-24)
국제출원번호
PCT/US2010/038293
(2010-06-11)
§371/§102 date
20120227
(20120227)
국제공개번호
WO2010/144787
(2010-12-16)
발명자
/ 주소
Jin, Shuhua
Jia, Weitao
출원인 / 주소
Pentron Clinical Technologies, LLC
대리인 / 주소
Wood, Herron & Evans, LLP
인용정보
피인용 횟수 :
0인용 특허 :
14
초록▼
Polymerizable compositions are provided that contain an epoxy compound and a polymerizable, ethylenically-unsaturated resin having an acid functional group where the epoxy compound is polymerized by cationic polymerization initiated by the acid functional group and the polymerizable, ethylenically-u
Polymerizable compositions are provided that contain an epoxy compound and a polymerizable, ethylenically-unsaturated resin having an acid functional group where the epoxy compound is polymerized by cationic polymerization initiated by the acid functional group and the polymerizable, ethylenically-unsaturated resin is polymerized by free-radical polymerization. To that end, a two-part polymerizable composition is provided that has a first part containing the epoxy compound; and a second part containing the polymerizable, ethylenically-unsaturated resin having an acid functional group. The first part and/or the second part further contain a radical initiator effective to initiate either self-curing or light-curing by free-radical polymerization.
대표청구항▼
1. A two-part polymerizable dental root canal sealer composition comprising: a first part comprising a cycloaliphatic epoxy compound, a free radical initiator system including a photo-initiator and a tertiary amine polymerization accelerator, and an acid-reactive filler; anda second part comprising
1. A two-part polymerizable dental root canal sealer composition comprising: a first part comprising a cycloaliphatic epoxy compound, a free radical initiator system including a photo-initiator and a tertiary amine polymerization accelerator, and an acid-reactive filler; anda second part comprising a polymerizable, ethylenically-unsaturated resin having an acid functional group selected from 4-methacryloxyethyl trimellitic anhydride, 4-methacryloxyethyl trimellitic acid, adduct reaction product of pyromellitic di-anhydride with 2-hydroxyethylmethacrylate, adduct reaction product of pyromellitic di-anhydride with glycerol dimethacrylate, or adduct reaction product of benzenetetracarboxylic acid di-anhydride with 2-(6-hydroxy-1-oxo-hexyloxy)ethyl methacrylate, a polymerizable ethylenically-unsaturated resin without an acid functional group, and a self-cure free radical initiator system,wherein free-radical polymerization of the polymerizable ethylenically-unsaturated resin and epoxy-ring opening polymerization of the cycloaliphatic epoxy compound are initiated upon mixing of the first and second parts to form a dental root canal sealer; and wherein contact between the acid-reactive filler and the acidic functional group upon mixing of the first and the second parts effects an ionic reaction of the acidic functional group and a surface of the acid-reactive filler. 2. The dental root canal sealer composition of claim 1, wherein the self-cure free radical initiator system comprises a peroxide compound. 3. The dental root canal sealer composition of claim 1, wherein the second part further comprises a non-epoxy-containing polymerizable compound having no acid functional group. 4. The dental root canal sealer composition of claim 1, wherein the polymerizable, ethylenically-unsaturated resin having the acid functional group is 4-methacryloxyethyl trimellitic anhydride, 4-methacryloxyethyl trimellitic acid, or a combination thereof. 5. The dental root canal sealer composition of claim 1, wherein the second part further comprises an ethylenically unsaturated phosphoric acid ester having the general formula: (CH2═C(CH3)CO2—R—O)mP(O)(OH)3-n wherein R is a substituted or unsubstituted alkyl or aryl group having about 1 to about 36 carbon atoms and n equals 1 or 2. 6. The dental root canal sealer composition of claim 1, wherein the cycloaliphatic epoxy compound includes 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, 3,4-epoxy-2-methylcyclohexylmethyl-3,4-epoxy-2-methylcyclohexane carboxylate, or bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate. 7. A kit comprising: the polymerizable composition of claim 1, wherein the first part and the second part are provided in packaging that physically separates the first part from the second part; andinstructions for mixing to effect a self-cure. 8. The kit of claim 7, wherein the instructions further include a light cure step. 9. The polymerizable dental root canal sealer composition of claim 1, wherein the polymerizable, ethylenically-unsaturated resin having the acid functional group is 4-methacryloxyethyl trimellitic anhydride, 4-methacryloxyethyl trimellitic acid, or a combination thereof; and wherein the cycloaliphatic epoxy compound includes 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, 3,4-epoxy-2-methylcyclohexylmethyl-3,4-epoxy-2-methylcyclohexane carboxylate, or bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate. 10. The polymerizable dental root canal sealer composition of claim 1, wherein the cycloaliphatic epoxy compound comprises 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, the photo-initiator comprises camphorquinone, the tertiary amine polymerization accelerator comprises ethyl-4-dimethyl benzoate, the polymerizable, ethylenically-unsaturated resin having the acid functional group comprises 4-methacryloxyethyl trimellitic anhydride, and the self-cure free radical initiator system comprises benzoyl peroxide. 11. The polymerizable dental root canal sealer composition of claim 1, wherein a weight ratio between the cycloaliphatic epoxy compound and the polymerizable, ethylenically-unsaturated resin having the acid functional group is in a range from about 1:10 to about 10:1. 12. The polymerizable dental root canal sealer composition of claim 1, wherein the first part is free of polymerizable resins having an acid functional group and epoxy addition reaction polymerization initiators, and wherein the second part is free of epoxy resin. 13. A polymerizable dental root canal sealer composition comprising a first part and a second part that upon mixing has three distinct polymerization mechanisms, the composition comprising: a cycloaliphatic epoxy compound in the first part,a polymerizable, ethylenically-unsaturated resin having an acid functional group in the second part, the acid functional group selected from 4-methacryloxyethyl trimellitic anhydride, 4-methacryloxyethyl trimellitic acid, adduct reaction product of pyromellitic di-anhydride with 2-hydroxyethylmethacrylate, adduct reaction product of pyromellitic di-anhydride with glycerol dimethacrylate, or adduct reaction product of benzenetetracarboxylic acid di-anhydride with 2-(6-hydroxy-1-oxo-hexyloxy)ethyl methacrylate,a polymerizable ethylenically-unsaturated resin without an acid functional group in the second part, anda dual-cure free radical polymerization system including a photo-initiator for light-cure in the first part and a redox system for self-cure, the redox system including a reducing agent in the first part and a peroxide oxidizing agent in the second part, the dual-cure free radical polymerization system including a tertiary amine in the first part as a polymerization accelerator and/or as the reducing agent,wherein free-radical polymerization of the polymerizable ethylenically-unsaturated resins in the second part by self-cure using the redox system and epoxy-ring opening polymerization of the cycloaliphatic epoxy compound using the acid functional group are initiated upon mixing of the first and second parts to form a dental root canal sealer; and wherein free-radical polymerization of the polymerizable ethylenically-unsaturated resins in the second part by light-cure using the photo-initiator is initiated upon mixing of the first and second parts with an addition of visible light, andwherein the first part is free of polymerizable resins having an acid functional group and epoxy addition reaction polymerization initiators, and wherein the second part is free of epoxy resin. 14. The polymerizable dental root canal sealer composition of claim 13, further comprising an acid-reactive filler in the first part to provide a fourth polymerization mechanism wherein contact between the acid-reactive filler and the acidic functional group upon mixing of the first and the second parts effects an ionic reaction of the acidic functional group and a surface of the acid-reactive filler. 15. The polymerizable dental root canal sealer composition of claim 14, wherein the second part further comprises a non-epoxy-containing polymerizable compound having no acid functional group. 16. The polymerizable dental root canal sealer composition of claim 14, wherein the polymerizable, ethylenically-unsaturated resin having the acid functional group is 4-methacryloxyethyl trimellitic anhydride, 4-methacryloxyethyl trimellitic acid, or a combination thereof. 17. The polymerizable dental root canal sealer composition of claim 14, wherein the second part further comprises an ethylenically unsaturated phosphoric acid ester having the general formula: (CH2═C(CH3)CO2—R—O)nP(O)(OH)3-n wherein R is a substituted or unsubstituted alkyl or aryl group having about 1 to about 36 carbon atoms and n equals 1 or 2. 18. The polymerizable dental root canal sealer composition of claim 14, wherein the cycloaliphatic epoxy compound includes 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, 3,4-epoxy-2-methylcyclohexylmethyl-3,4-epoxy-2-methylcyclohexane carboxylate, or bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate. 19. The polymerizable dental root canal sealer composition of claim 14, wherein a weight ratio between the cycloaliphatic epoxy compound and the polymerizable, ethylenically-unsaturated resin having the acid functional group is in a range from about 1:10 to about 10:1. 20. A kit comprising: the polymerizable composition of claim 13, wherein the first part and the second part are provided in packaging that physically separates the first part from the second part;instructions for mixing to effect a self-cure; andinstructions to effect a light cure.
Bretscher Kathyrn R. ; Rusin Richard P. ; Craig Bradley D. ; Mitra Sumita B. ; Oxman Joel D. ; Gust Janis R. ; Hayne Cheryl A. ; Westberg James W. ; Trom Matthew C. ; Kolb Brant U. ; Jacobs Dwight W., Radiopaque cationically polymerizable compositions comprising a radiopacifying filler, and method for polymerizing same.
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