Dental compositions and methods with arylsulfinate salts
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C08F-002/50
C08F-002/46
A61K-006/00
A61K-006/10
A61K-006/083
A61K-006/02
출원번호
US-0778381
(2007-07-16)
등록번호
US-7465758
(2008-12-16)
발명자
/ 주소
Falsafi,Afshin
Kalgutkar,Rajdeep S.
Oxman,Joel D.
출원인 / 주소
3M Innovative Properties Company
대리인 / 주소
Edman,Sean J.
인용정보
피인용 횟수 :
1인용 특허 :
65
초록
Polymerizable compositions and methods are provided that include an ethylenically unsaturated compound and an arylsulfinate salt. The polymerizable compositions are useful as hardenable dental compositions.
대표청구항▼
What is claimed: 1. A method of hardening a composition comprising irradiating a polymerizable dental composition suitable for use in the oral environment and comprising: an ethylenically unsaturated compound; a dental additive; a sensitizer capable of absorbing a wavelength of actinic radiation in
What is claimed: 1. A method of hardening a composition comprising irradiating a polymerizable dental composition suitable for use in the oral environment and comprising: an ethylenically unsaturated compound; a dental additive; a sensitizer capable of absorbing a wavelength of actinic radiation in the range of 250 to 1000 nanometers; and an initiator system comprising an arylsulfinate salt having an anion of Formula I description="In-line Formulae" end="lead"Ar1--SO2- Idescription="In-line Formulae" end="tail" and a cation selected from: 1) a phosphorus-containing cation of Formula III: where each R2 is independently an unsubstituted alkyl, an alkyl substituted with a hydroxy, an unsubstituted aryl, an aryl substituted with an alkyl, hydroxy, or combinations thereof; or 2) a nitrogen-containing cation having a ring structure comprising a 4 to 12 member heterocyclic group having a positively charged nitrogen atom, said heterocyclic being saturated or unsaturated and having up to 3 heteroatoms selected from oxygen, sulfur, nitrogen, or combinations thereof, wherein said ring structure is unsubstituted or substituted with a substituent selected from an alkyl, aryl, acyl, alkoxy, aryloxy, halo, mercapto, amino, hydroxy, azo, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, halocarbonyl, or combinations thereof, wherein the arylsulfinate salt has an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, and wherein Ar1 is a C6-30 aryl or a C3-30 heteroaryl that is unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group. 2. The method of claim 1 wherein the sensitizer is selected from the group consisting of camphorquinone, benzil, furil, 3,3,6,6-tetramethylcyclohexanedione, phenanthraquinone, 1-phenyl-1,2-propanedione, and combinations thereof. 3. The method of claim 1 wherein the polymerizable dental composition further comprises an electron acceptor having a reduction potential in N,N-dimethylformamide of +0.4 to-1.0 volts versus a silver/silver nitrate reference electrode. 4. A method of hardening a polymerizable dental composition suitable for use in the oral environment comprising: combining components to form a hardenable dental composition; and allowing the dental composition to harden, wherein the components comprise: an ethylenically unsaturated compound; a dental additive; an electron acceptor having a reduction potential in N,N-dimethylformamide of '+0.4 to-1.0 volts versus a silver/silver nitrate reference electrode; and an initiator system comprising an arylsulfinate salt having an anion of Formula I description="In-line Formulae" end="lead"Ar1--SO2- Idescription="In-line Formulae" end="tail" and a cation selected from: 1) a phosphorus-containing cation of Formula III: where each R2 is independently an unsubstituted alkyl, an alkyl substituted with a hydroxy, an unsubstituted aryl, an aryl substituted with an alkyl, hydroxy, or combinations thereof; or 2) a nitrogen-containing cation having a ring structure comprising a 4 to 12 member heterocyclic group having a positively charged nitrogen atom, said heterocyclic being saturated or unsaturated and having up to 3 heteroatoms selected from oxygen, sulfur, nitrogen, or combinations thereof, wherein said ring structure is unsubstituted or substituted with a substituent selected from an alkyl, aryl, acyl, alkoxy, aryloxy, halo, mercapto, amino, hydroxy, azo, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, halocarbonyl, or combinations thereof, wherein the arylsulfinate salt has an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, and wherein Ar1 is a C6-30 aryl or a C3-30 heteroaryl that is unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group. 5. The method of claim 4 wherein the electron acceptor is an iodonium salt, a hexaarylbisimidizole, a persulfate, a peroxide, a metal ion in an oxidized state, or combinations thereof. 6. The method of claim 4 wherein the components further comprise a sensitizer capable of absorbing a wavelength of actinic radiation in the range of 250 to 1000 nanometers. 7. The method of claim 6 wherein the method further comprises irradiating the hardenable dental composition. 8. A method of treating a dental structure surface comprising: applying a hardenable dental composition to the dental structure surface; and irradiating the dental composition, wherein the hardenable dental composition comprises: an ethylenically unsaturated compound; a sensitizer capable of absorbing a wavelength of actinic radiation in the range of 250 to 1000 nanometers; and an initiator system comprising an arylsulfinate salt having an anion of Formula I description="In-line Formulae" end="lead"Ar1--SO2- Idescription="In-line Formulae" end="tail" and a cation selected from: 1) a phosphorus-containing cation of Formula III: where each R2 is independently an unsubstituted alkyl, an alkyl substituted with a hydroxy, an unsubstituted aryl, an aryl substituted with an alkyl, hydroxy, or combinations thereof; or 2) a nitrogen-containing cation having a ring structure comprising a 4 to 12 member heterocyclic group having a positively charged nitrogen atom, said heterocyclic being saturated or unsaturated and having up to 3 heteroatoms selected from oxygen, sulfur, nitrogen, or combinations thereof, wherein said ring structure is unsubstituted or substituted with a substituent selected from an alkyl, aryl, acyl, alkoxy, aryloxy, halo, mercapto, amino, hydroxy, azo, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, halocarbonyl, or combinations thereof, wherein the arylsulfinate salt has an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, and wherein Ar1 is a C6-30 aryl or a C3-30 heteroaryl that is unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group, and wherein the hardenable dental composition is a polymerizable dental material suitable for use in the oral environment. 9. The method of claim 8 wherein the hardenable dental composition further comprises a dental additive. 10. The method of claim 8 wherein the sensitizer is selected from the group consisting of camphorquinone, benzil, furil, 3,3,6,6-tetramethylcyclohexanedione, phenanthraquinone, 1-phenyl-1,2-propanedione, and combinations thereof. 11. The method of claim 8 wherein the hardenable dental composition further comprises an electron acceptor having a reduction potential in N,N-dimethylformamide of +0.4 to-1.0 volts versus a silver/silver nitrate reference electrode. 12. A method of treating a dental structure surface comprising: applying a hardenable dental composition to the dental structure surface; and allowing the hardenable dental composition to harden, wherein the dental composition comprises: an ethylenically unsaturated compound; an electron acceptor having a reduction potential in N,N-dimethylformamide of +0.4 to-1.0 volts versus a silver/silver nitrate reference electrode; and an initiator system comprising an arylsulfinate salt having an anion of Formula I description="In-line Formulae" end="lead"Ar1--SO2- Idescription="In-line Formulae" end="tail" and a cation selected from: 1) a phosphorus-containing cation of Formula III: where each R2 is independently an unsubstituted alkyl, an alkyl substituted with a hydroxy, an unsubstituted aryl, an aryl substituted with an alkyl, hydroxy, or combinations thereof; or 2) a nitrogen-containing cation having a ring structure comprising a 4 to 12 member heterocyclic group having a positively charged nitrogen atom, said heterocyclic being saturated or unsaturated and having up to 3 heteroatoms selected from oxygen, sulfur, nitrogen, or combinations thereof, wherein said ring structure is unsubstituted or substituted with a substituent selected from an alkyl, aryl, acyl, alkoxy, aryloxy, halo, mercapto, amino, hydroxy, azo, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, halocarbonyl, or combinations thereof, wherein the arylsulfinate salt has an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, and wherein Ar1 is a C6-30 aryl or a C3-30 heteroaryl that is unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group, and wherein the hardenable dental composition is a polymerizable dental material suitable for use in the oral environment. 13. The method of claim 12 wherein the hardenable dental composition further comprises a dental additive. 14. The method of claim 12 wherein the electron acceptor is an iodonium salt, a hexaarylbisimidizole, a persulfate, a peroxide, a metal ion in an oxidized state, or combinations thereof. 15. The method of claim 12 wherein the hardenable dental composition further comprises a sensitizer capable of absorbing a wavelength of actinic radiation in the range of 250 to 1000 nanometers. 16. The method of claim 15 wherein the method further comprises irradiating the hardenable dental composition. 17. A self-etching, polymerizable dental composition comprising: an ethylenically unsaturated compound with acid functionality; an ethylenically unsaturated compound without acid functionality; and an initiator system comprising an arylsulfinate salt having an anion of Formula I description="In-line Formulae" end="lead"Ar1--SO2- Idescription="In-line Formulae" end="tail" and a cation selected from: 1) a phosphorus-containing cation of Formula III: where each R2 is independently an unsubstituted alkyl, an alkyl substituted with a hydroxy, an unsubstituted aryl, an aryl substituted with an alkyl, hydroxy, or combinations thereof; or 2) a nitrogen-containing cation having a ring structure comprising a 4 to 12 member heterocyclic group having a positively charged nitrogen atom, said heterocyclic being saturated or unsaturated and having up to 3 heteroatoms selected from oxygen, sulfur, nitrogen, or combinations thereof, wherein said ring structure is unsubstituted or substituted with a substituent selected from an alkyl, aryl, acyl, alkoxy, aryloxy, halo, mercapto, amino, hydroxy, azo, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, halocarbonyl, or combinations thereof, wherein the arylsulfinate salt has an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, and wherein Ar1 is a C6-30 aryl or a C3-30 heteroaryl that is unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group, and wherein the polymerizable composition is a dental material suitable for use in the oral environment. 18. The self-etching, polymerizable dental composition of claim 17 wherein the composition is a primer, a dental adhesive, an orthodontic adhesive, a coating, a sealant, a cement, a restorative, or combinations thereof. 19. The self-etching, polymerizable dental composition of claim 17 wherein the composition is non-aqueous. 20. The self-etching, polymerizable dental composition of claim 17 wherein the initiator system further comprises a sensitizer capable of absorbing a wavelength of actinic radiation in the range of 250 to 1000 nanometers. 21. The self-etching, polymerizable dental composition of claim 17 wherein the initiator system further comprises an electron acceptor having a reduction potential in N,N-dimethylformamide of +0.4 to-1.0 volts versus a silver/silver nitrate reference electrode. 22. The self-etching, polymerizable dental composition of claim 21 wherein the initiator system further comprises a sensitizer capable of absorbing a wavelength of actinic radiation in the range of 250 to 1000 nanometers. 23. The self-etching, polymerizable dental composition of claim 17 wherein the composition further comprises a filler. 24. The self-etching, polymerizable dental composition of claim 23 wherein the filler is a nanofiller. 25. The self-etching, polymerizable dental composition of claim 17 wherein the acid functionality comprises carboxylic acid functionality, phosphoric acid functionality, sulfonic acid functionality, or combinations thereof. 26. The self-etching, polymerizable dental composition of claim 17 further comprising a photobleachable dye. 27. A self-etching, polymerizable dental composition comprising: an ethylenically unsaturated compound with acid functionality; an ethylenically unsaturated compound without acid functionality a surfactant; water; and an initiator system comprising an arylsulfinate salt having an anion of Formula I description="In-line Formulae" end="lead"Ar1--SO2- Idescription="In-line Formulae" end="tail" and a cation having selected from: 1) a phosphorus-containing cation of Formula III: where each R2 is independently an unsubstituted alkyl, an alkyl substituted with a hydroxy, an unsubstituted aryl, an aryl substituted with an alkyl, hydroxy, or combinations thereof; or 2) a nitrogen-containing cation having a ring structure comprising a 4 to 12 member heterocyclic group having a positively charged nitrogen atom, said heterocyclic being saturated or unsaturated and having up to 3 heteroatoms selected from oxygen, sulfur, nitrogen, or combinations thereof, wherein said ring structure is unsubstituted or substituted with a substituent selected from an alkyl, aryl, acyl, alkoxy, aryloxy, halo, mercapto, amino, hydroxy, azo, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, halocarbonyl, or combinations thereof, wherein the arylsulfinate salt has an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, and wherein Ar1 is a C6-30 aryl or a C3-30 heteroaryl that is unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group, and wherein the self-etching, polymerizable dental composition is an emulsion suitable for use in the oral environment. 28. The self-etching, polymerizable dental composition of claim 27 wherein the emulsion is a water-in-oil emulsion. 29. The self-etching, polymerizable dental composition of claim 27 wherein the emulsion is physically stable. 30. The self-etching, polymerizable dental composition of claim 27 wherein the composition comprises less than 30% by weight water. 31. The self-etching, polymerizable dental composition of claim 27 wherein the composition is a water-in-oil micro-emulsion. 32. The self-etching, polymerizable dental composition of claim 27 wherein the composition further comprises a filler. 33. The self-etching, polymerizable dental composition of claim 32 wherein the filler is a nanofiller. 34. The self-etching, polymerizable dental composition of claim 27 wherein the initiator system further comprises a sensitizer capable of absorbing a wavelength of actinic radiation in the range of 250 to 1000 nanometers. 35. The self-etching, polymerizable dental composition of claim 27 wherein the initiator system further comprises an electron acceptor having a reduction potential in N,N-dimethylformamide of +0.4 to-1.0 volts versus a silver/silver nitrate reference electrode. 36. The self-etching, polymerizable dental composition of claim 35 wherein the initiator system further comprises a sensitizer capable of absorbing a wavelength of actinic radiation in the range of 250 to 1000 nanometers. 37. The self-etching, polymerizable dental composition of claim 27 further comprising a photobleachable dye. 38. A self-adhesive, polymerizable dental composition comprising: an ethylenically unsaturated compound with acid functionality; an ethylenically unsaturated compound without acid functionality; at least 40% by weight filler; and an initiator system comprising an arylsulfinate salt having an anion of Formula I description="In-line Formulae" end="lead"Ar1--SO2- Idescription="In-line Formulae" end="tail" and cation selected from: 1) a phosphorus-containing cation of Formula III: where each R2 is independently an unsubstituted alkyl, an alkyl substituted with a hydroxy, an unsubstituted aryl, an aryl substituted with an alkyl, hydroxy, or combinations thereof; or 2) a nitrogen-containing cation having a ring structure comprising a 4 to 12 member heterocyclic group having a positively charged nitrogen atom, said heterocyclic being saturated or unsaturated and having up to 3 heteroatoms selected from oxygen, sulfur, nitrogen, or combinations thereof, wherein said ring structure is unsubstituted or substituted with a substituent selected from an alkyl, aryl, acyl, alkoxy, aryloxy, halo, mercapto, amino, hydroxy, azo, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, halocarbonyl, or combinations thereof, wherein the arylsulfinate salt has an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, and wherein Ar1 is a C6-30 aryl or a C3-30 heteroaryl that is unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group, and wherein the polymerizable composition is a dental material suitable for use in the oral environment. 39. The self-adhesive, polymerizable dental composition of claim 38 wherein the composition is non-aqueous. 40. The self-adhesive, polymerizable dental composition of claim 38 wherein the acid functionality comprises carboxylic acid functionality, phosphoric acid functionality, sulfonic acid functionality, or combinations thereof. 41. The self-adhesive, polymerizable dental composition of claim 38 wherein the filler is a nanofiller. 42. The self-adhesive, polymerizable dental composition of claim 38 further comprising a photobleachable dye. 43. The self-adhesive, polymerizable dental composition of claim 38 wherein the initiator system further comprises a sensitizer capable of absorbing a wavelength of actinic radiation in the range of 250 to 1000 nanometers. 44. The self-adhesive, polymerizable dental composition of claim 38 wherein the initiator system further comprises an electron acceptor having a reduction potential in N,N-dimethylformamide of +0.4 to-1.0 volts versus a silver/silver nitrate reference electrode. 45. The self-adhesive, polymerizable dental composition of claim 44 wherein the initiator system further comprises a sensitizer capable of absorbing a wavelength of actinic radiation in the range of 250 to 1000 nanometers. 46. A method of hardening a composition comprising irradiating a polymerizable dental composition suitable for use in the oral environment and comprising: an ethylenically unsaturated compound; a dental additive; a sensitizer capable of absorbing a wavelength of actinic radiation in the range of 250 to 1000 nanometers; and an initiator system comprising an arylsulfinate salt having an anion of Formula I description="In-line Formulae" end="lead"Ar1--SO2- Idescription="In-line Formulae" end="tail" and a cation of Formula II: where R1 and each R4 are independently alkyl groups having at least 3 carbon atoms, and wherein the arylsulfinate salt has an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, and wherein Ar1 is a C6-30 aryl or a C3-30 heteroaryl that is unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group. 47. A method of hardening a composition comprising: combining components to form a hardenable dental composition; and allowing the dental composition to harden, wherein the components comprise: an ethylenically unsaturated compound; a dental additive; an electron acceptor having a reduction potential in N,N-dimethylformamide of +0.4 to-1.0 volts versus a silver/silver nitrate reference electrode; and an initiator system comprising an arylsulfinate salt having an anion of Formula I description="In-line Formulae" end="lead"Ar1--SO2- Idescription="In-line Formulae" end="tail" and a cation of Formula II: where R1 and each R4 are independently alkyl groups having at least 3 carbon atoms, and wherein the arylsulfinate salt has an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, and wherein Ar1 is a C6-30 aryl or a C3-30 heteroaryl that is unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group, and wherein the hardenable dental composition is a polymerizable dental composition suitable for use in the oral environment. 48. A method of treating a dental structure surface comprising: applying a hardenable dental composition to the dental structure surface; and irradiating the dental composition, wherein the hardenable dental composition comprises: an ethylenically unsaturated compound; a sensitizer capable of absorbing a wavelength of actinic radiation in the range of 250 to 1000 nanometers; and an initiator system comprising an arylsulfinate salt having an anion of Formula I description="In-line Formulae" end="lead"Ar1--SO2- Idescription="In-line Formulae" end="tail" and a cation of Formula II: where R1 and each R4 are independently alkyl groups having at least 3 carbon atoms, and wherein the arylsulfinate salt has an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, and wherein Ar1 is a C6-30 aryl or a C3-30 heteroaryl that is unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group, and wherein the hardenable dental composition is a polymerizable dental material suitable for use in the oral environment. 49. A method of treating a dental structure surface comprising: applying a hardenable dental composition to the dental structure surface; and allowing the hardenable dental composition to harden, wherein the dental composition comprises: an ethylenically unsaturated compound; an electron acceptor having a reduction potential in N,N-dimethylformamide of +0.4 to-1.0 volts versus a silver/silver nitrate reference electrode; and an initiator system comprising an arylsulfinate salt having an anion of Formula I description="In-line Formulae" end="lead"Ar1--SO2- Idescription="In-line Formulae" end="tail" and a cation of Formula II: where R1 and each R4 are independently alkyl groups having at least 3 carbon atoms, and wherein the arylsulfinate salt has an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, and wherein Ar1 is a C6-30 aryl or a C3-30 heteroaryl that is unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group, and wherein the hardenable dental composition is a polymerizable dental material suitable for use in the oral environment. 50. A self-etching, polymerizable dental composition comprising: an ethylenically unsaturated compound with acid functionality; an ethylenically unsaturated compound without acid functionality; and an initiator system comprising an arylsulfinate salt having an anion of Formula I description="In-line Formulae" end="lead"Ar1--SO2- Idescription="In-line Formulae" end="tail" and a cation of Formula II: where R1 and each R4 are independently alkyl groups having at least 3 carbon atoms, and wherein the arylsulfinate salt has an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, and wherein Ar1 is a C6-30 aryl or a C3-30 heteroaryl that is unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group, and wherein the polymerizable composition is a dental material suitable for use in the oral environment. 51. A self-etching, polymerizable dental composition comprising: an ethylenically unsaturated compound with acid functionality; an ethylenically unsaturated compound without acid functionality a surfactant; water; and an initiator system comprising an arylsulfinate salt having an anion of Formula I description="In-line Formulae" end="lead"Ar1--SO2- Idescription="In-line Formulae" end="tail" and a cation of Formula II: where R1 and each R4 are independently alkyl groups having at least 3 carbon atoms, and wherein the arylsulfinate salt has an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, and wherein Ar1 is a C6-30 aryl or a C3-30 heteroaryl that is unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group, and wherein the self-etching, polymerizable dental composition is an emulsion suitable for use in the oral environment. 52. A self-adhesive, polymerizable dental composition comprising: an ethylenically unsaturated compound with acid functionality; an ethylenically unsaturated compound without acid functionality; at least 40% by weight filler; and an initiator system comprising an arylsulfinate salt having an anion of Formula I description="In-line Formulae" end="lead"Ar1--SO2- Idescription="In-line Formulae" end="tail" and a cation of Formula II: where R1 and each R4 are independently alkyl groups having at least 3 carbon atoms, and wherein the arylsulfinate salt has an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, and wherein Ar1 is a C6-30 aryl or a C3-30 heteroaryl that is unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group, and wherein the polymerizable composition is a dental material suitable for use in the oral environment.
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