Antioxidant stabilizers for direct fabrication of orthodontic appliances
AssigneeAlign Technology, Inc.
InventorsMing Ren, Daniel Yilin Jiang, Jason Safko, Lance Robert Pickens
Life of this patent
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Abstract
This disclosure provides stable polymerizable resin compositions comprising one or more antioxidant stabilizers to prevent undesired polymerization and/or oxidation of polymerizable components as well as undesired depletion of photoinitiators in the polymerizable resin composition. Such polymerizable resin compositions can be used to produce polymeric materials with properties suitable for use in various mechanical appliances, such as orthodontic appliances.
Claims39
A polymerizable resin composition for forming an orthodontic appliance by additive manufacturing, the polymerizable resin composition comprising:
- an antioxidant stabilizer selected from the group consisting of vitamin E, octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-isocyanurate, bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl)-methane, 2,2′-methylenebis(4-methyl-6-tert-butylphenol), bis(2,4-di-tert-butylphenol) pentaerythritol diphosphite, tris(nonylphenyl)phosphite, tris(2,4-di-tert-butylphenyl)phosphite, ethylene bis[3,3-bis(3-tert-butyl-4-hydroxyphenyl)butyrate], tetrakis(2,4-di-tert-butylphenyl)[1,1′-biphenyl]-4,4′-diylbis(phosphonite), ethylene bis(oxyethylene)bis[β-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionate] and tetrakis[methylene-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]methane;
- a reactive diluent, wherein the reactive diluent is a polymerizable compound having a molecular weight of 0.1 to 1.0 kDa;
- and
- a telechelic compound comprising:
- an oligomeric or a polymeric chain of interconnected monomeric units having a first terminal end and a second terminal end;
- at least one first reactive functional group covalently bonded to the first terminal end;
- and
- at least one second reactive functional group covalently bonded to the second terminal.
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The composition of claim 341, further comprising a photoinitiator, wherein the photoinitiator comprises phenylbis(2,4,6-trimethylbenzoyl) phosphine oxide (BAPO), diphenyl-(2,4,6-trimethylbenzoyl) phosphine oxide (TPO), ethyl-(2,4,6-trimethylbenzoyl)phenylphosphinate (TPO-L), a polymeric TPO-L, alpha-hydroxyketone, benzil dimethyl ketal (BDK), or a combination thereof.
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A composition, comprising:
- a reactive diluent;
- and
- an antioxidant stabilizer for stabilizing the reactive diluent, wherein the antioxidant stabilizer selected from the group consisting of vitamin E, octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-isocyanurate, bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl)-methane, 2,2′-methylenebis(4-methyl-6-tert-butylphenol), bis(2,4-di-tert-butylphenol) pentaerythritol diphosphite, tris(nonylphenyl)phosphite, tris(2,4-di-tert-butylphenyl)phosphite, ethylene bis[3,3-bis(3-tert-butyl-4-hydroxyphenyl)butyrate], tetrakis(2,4-di-tert-butylphenyl)[1,1′-biphenyl]-4,4′-diylbis(phosphonite), ethylene bis(oxyethylene)bis[β-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionate] and tetrakis[methylene-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]methane.
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A composition, comprising:
- a photoinitiator;
- and
- an antioxidant stabilizer for stabilizing the photoinitiator, wherein the antioxidant stabilizer is selected from the group consisting of vitamin E, octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-isocyanurate, bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl)-methane, 2,2′-methylenebis(4-methyl-6-tert-butylphenol), bis(2,4-di-tert-butylphenol) pentaerythritol diphosphite, tris(nonylphenyl)phosphite, tris(2,4-di-tert-butylphenyl)phosphite, ethylene bis[3,3-bis(3-tert-butyl-4-hydroxyphenyl)butyrate], tetrakis(2,4-di-tert-butylphenyl)[1,1′-biphenyl]-4,4′-diylbis(phosphonite), ethylene bis(oxyethylene)bis[β-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionate] and tetrakis[methylene-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]methane.
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Dependencies are inferred from the claim text.