Ternary photoinitiator system for addition polymerization
AssigneeMinnesota Mining and Manufacturing Company
InventorsMichael C. Palazzotto, F. Andrew Ubel, III, Joel D. Oxman, M. Zaki Ali
Life of this patent
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Abstract
Photocurable addition-polymerizable compositions containing a free-radically-polymerizable monomer and a photoinitiator system containing i) an arylidonium salt, ii) a sensitizing compound, and iii) an electron donor having an oxidation potential that is greater than zero and less than or equal to that of p-dimethyoxybenzene (1.32 volts vs. S.C.E.). The compositions cure rapidly and deeply under ultraviolet or visible light.
Claims35
An addition-polymerizable composition comprising:
- a) free-radically-polymerizable monomer, and
- b) photoinitiator system, soluble in said monomer, comprising photochemically effective amounts of
- i) aryliodonium salt,
- ii) sensitizing compound capable of absorbing light within the range of wavelengths between about 300 and about 1000 nanometers and capable of sensitizing 2-methyl-4,6-bis(trichloromethyl)-s-triazine, and
- iii) electron donor compound, said donor being different from said sensitizing compound wherein the oxidation potential of said donor is greater than zero and less than or equal to p-dimethoxybenzene vs. a saturated calomel electrode.
An addition-polymerizable composition comprising:
- a) free-radically-polymerizable monomer, and
- b) photoinitiator system, soluble in said monomer, comprising 0.1 to 4 parts each of
- i) diphenyliodonium metal complex salt,
- ii) ketone, ketocoumarin, aminoarylketone or p-substituted aminostyryl ketone sensitizing compound capable of absorbing light somewhere within the range of wavelengths between about 400 and about 600 nanometers and capable of sensitizing 2-methyl-4,6-bis(trichloromethyl)-s-triazine, and
- iii) electron donor compound containing a nitrogen donor atom and having an abstractable hydrogen atom bonded to a carbon or silicon atom alpha to said nitrogen atom,
- wherein said donor compound is different from said sensitizing compound and wherein the oxidation potential of said donor is greater than about 0.5 and less than or equal to about 1 volt vs. a saturated calomel electrode.
A method for addition photopolymerization comprising the step of irradiating a composition with light having a wavelength between about 300 and about 1000 nanometers until said composition gels or hardens, said composition comprising:
- a) free-radically-polymerizable monomer, and
- b) photoinitiator system, soluble in said monomer, comprising photochemically effective amounts of
- i) aryliodonium salt,
- ii) sensitizing compound capable of absorbing light somewhere within the range of wavelengths between about 300 and about 1000 nanometers and capable of sensitizing 2-methyl-4,6-bis(trichloromethyl)-s-triazine, and
- iii) electron donor compound, said donor being different from said sensitizing compound and ..Wherein the oxidation potential of said donor is greater than zero vs. a saturated Calomel electrode.
An addition-polymerizable dental adhesive composition comprising:
- a) free-radically-polymerizable monomer, and
- b) photoinitiator system, soluble in said monomer, comprising photochemically effective amounts of
- i) aryliodonium salt,
- ii) sensitizing compound capable of absorbing light within the range of wavelengths between about 300 and about 1000 nanometers and capable of sensitizing 2-methyl-4,6-bis(trichloromethyl)-s-triazine, and
- iii) electron donor compound, said donor being different from said sensitizing compound and wherein the oxidation potential of said donor is greater than and less than or equal to vs. a saturated calomel electrode.
An addition-polymerizable dental composite composition comprising:
- a) free-radically-polymerizable monomer, and
- b) photoinitiator system, soluble in said monomer, comprising photochemically effective amounts of
- i) aryliodonium salt,
- ii) sensitizing compound capable of absorbing light within the range of wavelengths between about 300 and about 1000 nanometers and capable of sensitizing 2-methyl-4,6-bis(trichloromethyl)-s-triazine, and
- iii) electron donor compound, said donor being different from said sensitizing compound and wherein the oxidation potential of said donor is greater than and less than or equal to vs. a saturated calomel electrode.
An addition-polymerizable orthodontic adhesive composition comprising:
- a) free-radically-polymerizable monomer, and
- b) photoinitiator system, soluble in said monomer, comprising photochemically effective amounts of
- i) aryliodonium salt,
- ii) sensitizing compound capable of absorbing light within the range of wavelengths between about 300 and about 1000 nanometers and capable of sensitizing 2-methyl-4,6-bis(trichloromethyl)-s-triazine, and
- iii) electron donor compound, said donor being different from said sensitizing compound and wherein the oxidation potential of said donor is greater than and less than or equal to vs. a saturated calomel electrode.
A photoinitiator system for initiating polymerization of an addition polymerizable composition comprising:
- i) atyliodonium salts,
- ii) sensitizing compound capable of absorbing light within the range of wavelengths between about 300 and about 1000 nanometers and capable of sensitizing 2-methyl-4,6-bis(trichloromethyl)s-triazine, and
- iii) an electron donor compound, said donor being different from said sensitizing compound wherein the oxidation potential of said donor is greater than zero and less than or equal to p-dimethoxybenzene vs. a saturated calomel electrode.
Dependencies are inferred from the claim text.