Orthodontic articles comprising cured free-radically polymerizable composition with improved strength in aqueous environment

Patent metadata

Field	Value
Publication number	US-2023159680-A1
Application number	US-202318094019-A
Country	US
Kind code	A1
Filing date	Jan 6, 2023
Priority date	Jun 29, 2018
Publication date	May 25, 2023
Grant date	—

Abstract

Orthodontic articles and polymerizable resin compositions are described. The orthodontic article comprises a cured composition comprising the reaction product of free-radically polymerizable resin comprising 30 to 70 wt. %, inclusive, of at least one urethane component, and 25 to 70 wt. %, inclusive, of reactive diluent(s) comprising at least one monofunctional (meth)acrylate monomer. The polymerizable resin comprises no greater than 35 wt. % of reactive diluent(s) having a high affinity for water. Reactive diluent(s) such as monofunctional (meth)acrylate monomers having a high affinity for water have low log P values. In one embodiment, the polymerizable resin comprises at least one acidic monomer.

First claim

1 . A method of making an orthodontic article, the method comprising:
a) providing a photopolymerizable composition, the photopolymerizable composition comprising:
30 to 70 wt. %, inclusive, of at least one urethane component,
25 to 70 wt. %, inclusive, of reactive diluent(s) comprising at least one monofunctional (meth)acrylate monomer, and
at least one ethylenically unsaturated component with acid functionality;
wherein the free-radically polymerizable resin comprises no greater than 35 wt. % of reactive diluent(s) having a high affinity for water;
b) selectively curing the photopolymerizable composition to form an article; and c) optionally curing unpolymerized urethane component and/or reactive diluent remaining after step (b).

2 . The method of claim 1 , further comprising (d) repeating steps (a) and (b) to form multiple layers and create the article having a three-dimensional structure prior to step (c).

3 . The method of claim 1 , further comprising subjecting the article to heating in an oven.

4 . The method of claim 3 , wherein the oven is set at a temperature of 60° C. or higher.

5 . The method of claim 3 , wherein the article is subjected to stepwise heating to 60, 80 and then 100° C.

6 . The method of claim 1 , wherein curing utilizes actinic radiation having a wavelength range of 375-400 nm.

7 . The method of claim 1 , further including postcuring the article using actinic radiation or heat.

8 . The method of claim 7 , wherein the postcuring the article using actinic radiation utilizes a wavelength range of 365 up to but not including 375 nm.

9 . The method of claim 1 , wherein the article comprises less than 0.1 wt-% extractables in a solution of 5% ethanol in water.

10 . The method of claim 1 , wherein the cured photopolymerizable composition exhibits an elongation at break of 150% or greater and a tensile strength at yield of at least 10 MPa as determined according to ASTM D638-14 after conditioning in phosphate-buffered saline having a pH of 7.4 for 24 hours at a temperature of 37° C.

11 . The method of claim 1 , wherein the cured photopolymerizable composition exhibits a 3-point bend modulus of at least 100 MPa as determined according to dynamic mechanical analysis at 2% strain after conditioning in deionized water at a temperature of 25° C. for 48 hours.

12 . A method comprising:
retrieving, from a non-transitory machine readable medium, data representing a 3D model of an orthodontic article; executing, by one or more processors, a 3D printing application interfacing with a manufacturing device using the data; and generating, by the manufacturing device, a physical object of the article, the article comprising a reaction product of a photopolymerizable composition, the photopolymerizable composition comprising:
30 to 70 wt. %, inclusive, of at least one urethane component,
25 to 70 wt. %, inclusive, of reactive diluent(s) comprising at least one monofunctional (meth)acrylate monomer, and
at least one ethylenically unsaturated component with acid functionality;
wherein the free-radically polymerizable resin comprises no greater than 35 wt. % of reactive diluent(s) having a high affinity for water.

13 . A method comprising:
receiving, by a manufacturing device having one or more processors, a digital object comprising data specifying a plurality of layers of an orthodontic article; and generating, with the manufacturing device by an additive manufacturing process, the article based on the digital object, the article comprising a reaction product of a photopolymerizable composition, the photopolymerizable composition comprising:
30 to 70 wt. %, inclusive, of at least one urethane component,
25 to 70 wt. %, inclusive, of reactive diluent(s) comprising at least one monofunctional (meth)acrylate monomer, and
at least one ethylenically unsaturated component with acid functionality;
wherein the free-radically polymerizable resin comprises no greater than 35 wt. % of reactive diluent(s) having a high affinity for water.

Assignees

• 3M Innovative Properties Company

Inventors

• Wu Tianyu
• Chakraborty Saswata
• Macmurray Benjamin C
• Pokorny Richard J
• Klun Thomas P
• Mahoney Wayne S
• Amb Chad M
• Abuelyaman Ahmed
• Clough Robert S
• Riedesel John M
• Hansen James D
• Dailey Ian
• Skamser Daniel J
• Nelson Eric W
• Griesgraber George W
• Reed Dana R

Classifications

• B29L2031/7536

  Artificial teeth · CPC title

• B29C64/135

  the energy source being concentrated, e.g. scanning lasers or focused light sources · CPC title

• A61K6/887 Primary

  Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• A61K6/893

  Polyurethanes · CPC title

• B33Y10/00

  Processes of additive manufacturing · CPC title