US5545676A — Ternary photoinitiator system for addition polyme…

Claim 1

Independent Claim 83 words

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.

Claim 2

Dependent Claim 83 words

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.

Claim 3

Dependent Claim 20 words

A composition according to claim 1, wherein said aryliodonium salt comprises a diphenyliodonium simple salt or diphenyliodonium metal complex salt.

Claim 4

Dependent Claim 18 words

A composition according to claim 1, wherein said range of wavelengths is about 400 to about 700 nanometers.

Claim 5

Dependent Claim 18 words

A composition according to claim 1, wherein said range of wavelengths is about 400 to about 600 nanometers.

Claim 6

Dependent Claim 50 words

A composition according to claim 1, wherein said sensitizing compound is selected from the group consisting of ketones, coumarin dyes, xanthene dyes, acridine dyes, thiazole dyes, thiazine dyes, oxazine dyes, azine dyes, aminoketone dyes, porphyrins, aromatic polycyclic hydrocarbons, p-substituted aminostyryl ketone compounds, aminotriaryl methanes, merocyanines squarylium dyes and pyridinium dyes.

Claim 7

Dependent Claim 20 words

A composition according to claim 1, wherein said sensitizing compound comprises a ketone, ketocoumarin, aminoarylketone or p-substituted aminostyryl ketone compound.

Claim 8

Dependent Claim 16 words

A composition according to claim 1, wherein said sensitizing compound contains at least one julolidinyl moiety.

Claim 9

Dependent Claim 31 words

A composition according to claim 1, wherein said sensitizing compound comprises an α-diketone having an extinction coefficient below about 1000 at the wavelength at which said composition is irradiated when photopolymerized.

Claim 10

Dependent Claim 12 words

A composition according to claim 1, wherein said sensitizing compound comprises camphorquinone.

Claim 11

Dependent Claim 90 words

A composition according to claim 1, wherein said sensitizing compound has the formula: ACO(X).sub.b B where X is CO or CR 1 R 2 , where R 1 and R 2 are the same or different, and are hydrogen, alkyl, alkaryl or aralkyl, b is zero or 1, and A and B are the same or different and are substituted or unsubstituted aryl, alkyl, alkaryl or aralkyl groups, or together A and B form a cyclic structure which is a substituted or unsubstituted cycloaliphatic, aromatic, heteroaromatic or fused aromatic ring.

Claim 12

Dependent Claim 25 words

A composition according to claim 1, wherein the oxidation potential of the donor is between about 0.5 and 1 volts vs. a saturated calomel electrode.

Claim 13

Dependent Claim 52 words

A composition according claim 1 wherein said donor is selected from the group consisting of amines, amides, ethers, ureas, ferrocene, sulfinic acids and their salts, salts of ferrocyanide, ascorbic acid and its salts, dithiocarbamic acid and its salts, salts of xanthates, salts of ethylene diamine tetraacetic acid and salts of tetraphenylboronic acid.

Claim 14

Dependent Claim 35 words

A composition according to claim 1, wherein said donor contains a nitrogen, oxygen, phosphorus or sulfur donor atom and an abstractable hydrogen atom bonded to a carbon or silicon atom alpha to said donor atom.

Claim 15

Dependent Claim 17 words

A composition according to claim 1, wherein said donor comprises a tertiary amine containing an aromatic ring.

Claim 16

Dependent Claim 18 words

A composition according to claim 14, wherein there is at least one electron-withdrawing group on said aromatic ring.

Claim 17

Dependent Claim 15 words

A composition according to claim 1, wherein said donor contains one or more julolidinyl moieties.

Claim 18

Dependent Claim 12 words

A composition according to claim 16, wherein said donor comprises 9-julolidine carboxyaldehyde.

Claim 19

Dependent Claim 38 words

A composition according to claim 1, wherein said composition contains, for every 100 parts by weight of said monomer, about 0.005 to about 10 parts by weight each of said aryliodonium salt, said sensitizing compound and said donor.

Claim 20

Dependent Claim 38 words

A composition according to claim 18, wherein said composition contains, for every 100 parts by weight of said monomer, about 0.1 to about 4 parts by weight each of said aryliodonium salt, said sensitizing compound and said donor.

Claim 21

Dependent Claim 27 words

A composition according to claim 18, wherein said composition further comprises about 10% to 90% reinforcing and/or extending fillers, based on the total weight of said composition.

Claim 22

Dependent Claim 18 words

A composition according to claim 20, in the form of a photocurable adhesive applied to an orthodontic bracket.

Claim 23

Dependent Claim 17 words

A composition according to claim 21, wherein said sensitizing compound comprises camphorquinone and said donor comprises triethanolamine.

Claim 24

Dependent Claim 20 words

A composition according to claim 20, in the form of a photocurable composite suitable for use as a dental restorative.

Claim 25

Dependent Claim 19 words

A composition according to claim 1, in the form of a photocurable or photocured image-bearing coating atop a support.

Claim 26

Dependent Claim 32 words

A composition according to claim 24, wherein said coating and said support comprise a printing plate-in which, before photopolymerization, said sensitizing compound comprises a ketene, ketocoumarin, aminoarylketone or p-substituted aminostyryl ketone compound.

Claim 27

Dependent Claim 12 words

A composition according to claim 25, wherein said donor comprises 9-julolidine carboxaldehyde.

Claim 28

Dependent Claim 124 words

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.

Claim 29

Dependent Claim 124 words

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.

Claim 30

Independent Claim 107 words

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.

Claim 31

Independent Claim 107 words

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.

Claim 32

Dependent Claim 84 words

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.

Claim 33

Dependent Claim 84 words

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.

Claim 34

Dependent Claim 55 words

The composition of claim 29, wherein i) the aryliodonium salt is the salt of diphenyl iodonium; ii) the sensitizing compound is an a-diketone having an extinction coefficient below about 1000 at the wavelength at which said composition is irradiated when photopolymerized; and iii) the electron donor compound is a tertiary amine containing an aromatic ring.

Claim 35

Dependent Claim 84 words

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.

Claim 36

Dependent Claim 84 words

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.

Claim 37

Dependent Claim 55 words

The composition of claim 31, wherein i) the aryliodonium salt is the salt of diphenyl iodonium; ii) the sensitizing compound is an a-diketone having an extinction coefficient below about 1000 at the wavelength at which said composition is irradiated when photopolymerized; and iii) the electron donor compound is a tertiary amine containing an aromatic ring.

Claim 38

Dependent Claim 84 words

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.

Claim 39

Dependent Claim 84 words

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.

Claim 40

Dependent Claim 55 words

The composition of claim 33, wherein i) the aryliodonium salt is the salt of diphenyl iodonium; ii) the sensitizing compound is an a-diketone having an extinction coefficient below about 1000 at the wavelength at which said composition is irradiated when photopolymerized; and iii) the electron donor compound is a tertiary amine containing an aromatic ring.

Claim 41

Dependent Claim 76 words

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.

Claim 42

Dependent Claim 76 words

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.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1999-08-13	2000-02-12	2000-08-13	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	2003-08-13	2004-02-12	2004-08-13	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2007-08-13	2008-02-12	2008-08-13	$7700.00	Window Closed / Lapsed

Ternary photoinitiator system for addition polymerization

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