Orthodontic articles prepared using a polycarbonate diol, polymerizable compositions, and methods of making the articles

Patent metadata

Field	Value
Publication number	US-12297316-B2
Application number	US-202418435149-A
Country	US
Kind code	B2
Filing date	Feb 7, 2024
Priority date	Jun 29, 2018
Publication date	May 13, 2025
Grant date	May 13, 2025

Abstract

The present disclosure provides an orthodontic article including the reaction product of the polymerizable composition. Further, the present disclosure provides polymerizable compositions and methods of making an orthodontic article. The method includes obtaining a polymerizable composition and selectively curing the polymerizable composition to form an orthodontic article. Further, methods are provided, including receiving, by a manufacturing device having one or more processors, a digital object comprising data specifying an orthodontic article; and generating, with the manufacturing device by an additive manufacturing process, the orthodontic article based on the digital object. A system is also provided, including a display that displays a 3D model of an orthodontic article; and one or more processors that, in response to the 3D model selected by a user, cause a 3D printer to create a physical object of an orthodontic article.

First claim

The invention claimed is:

1. An orthodontic article comprising a reaction product of a polymerizable composition comprising:
30-65 parts by weight of at least one monofunctional (meth)acrylate monomer per 100 parts of the polymerizable composition,
wherein the at least one monofunctional (meth)acrylate monomer is selected from a group comprising at least one of: a cycloaliphatic monofunctional (meth)acrylate, a tetrahydrofurfuryl methacrylate, a 2-phenoxyethyl methacrylate, a butyl methacrylate, a benzyl methacrylate, an n-propylmethacrylate, a tertiary butyl acrylate, or at least one combination thereof,
wherein the group excludes isobornyl (meth)acrylate, and
wherein a cured homopolymer of the at least one monofunctional (meth)acrylate monomer has a T g of 30 degrees Celsius (° C.) or greater, at least 40, 50, 60, 70, 80, or 90° C.; and

at least one urethane (meth)acrylate comprising polymerized units of an aliphatic polycarbonate diol.

2. The orthodontic article of claim 1 , wherein the at least one monofunctional (meth)acrylate monomer has a log P value of greater than 1, 1.5, 2, 2.5, or 3.

3. The orthodontic article of claim 1 , wherein the at least one urethane (meth)acrylate comprises a reaction product of at least two of: an aliphatic polycarbonate diol, a diisocyanate, or a hydroxy functional (meth)acrylate.

4. The orthodontic article of claim 3 , wherein the hydroxy functional (meth)acrylate is of Formula (II):

wherein Q is a polyvalent organic linking group and A is a (meth)acryl functional group of a formula —XC(═O)C(R 1 )═CH 2 , wherein X is O, S, or NR 4 , R 4 is H or alkyl of 1 to 4 carbon atoms, R 1 is a lower alkyl of 1 to 4 carbon atoms or H, and p is 1 or 2.

5. The orthodontic article of claim 3 , wherein the at least one urethane (meth)acrylate is of Formula (VI):

wherein A has a formula —XC(═O)C(R 1 )═CH 2 , wherein X is O, S, or NR 4 , R 4 is H or alkyl of 1 to 4 carbon atoms, and R 1 is a lower alkyl of 1 to 4 carbon atoms or H, p is 1 or 2, Q is a polyvalent organic linking group, R di is a residue of a diisocyanate, R dOH is a residue of a polycarbonate polyol, and r averages from 1 to 15.

6. The orthodontic article of claim 1 , wherein the at least one urethane (meth)acrylate comprises a reaction product of at least two of: an aliphatic polycarbonate diol, a diisocyanate, a diol (meth)acrylate, or a hydroxy functional (meth)acrylate.

7. The orthodontic article of claim 6 , wherein the at least one urethane (meth)acrylate is of Formula (V):

wherein A has a formula —XC(═O)C(R 1 )═CH 2 , wherein X is O, S, or NR 4 , R 4 is H or alkyl of 1 to 4 carbon atoms, and R 1 is a lower alkyl of 1 to 4 carbon atoms or H, p is 1 or 2, Q is a polyvalent organic linking group, R di is a residue of a diisocyanate, R dOH is a residue of a polycarbonate polyol, s and t are independently 1 or greater, and s+t averages from 2 to 15, wherein the s and t units may be connected to each other in any order, wherein R AD is a residue of a (meth)acrylated diol.

8. The orthodontic article of claim 1 , wherein the at least one urethane (meth)acrylate comprises a reaction product of at least two of: an aliphatic polycarbonate diol or an isocyanate functional (meth)acrylate.

9. The orthodontic article of claim 8 , wherein the at least one urethane (meth)acrylate is of Formula (VIII):

wherein Q is a polyvalent organic linking group, R 3 is a lower alkyl of 1 to 4 carbon atoms or H, p is 1 or 2, each R 1 and R 2 are independently an aliphatic, cycloaliphatic, or aliphatic/cycloaliphatic alkylene group and an average number of carbon atoms in a combination of all the R 1 and R 2 groups is 4 to 10, and m is 2 to 23.

10. The orthodontic article of claim 1 , wherein the at least one urethane (meth)acrylate comprises a reaction product of at least two of: an aliphatic polycarbonate diol, a diisocyanate, or an isocyanate functional (meth)acrylate.

11. The orthodontic article of claim 10 , wherein the at least one urethane (meth)acrylate is of Formula (XI):

wherein u is 0 to 15, A has a formula —XC(═O)C(R 1 )═CH 2 , wherein X is O, S, or NR 4 , R 4 is H or alkyl of 1 to 4 carbon atoms, and R 1 is a lower alkyl of 1 to 4 carbon atoms or H, p is 1 or 2, Q is a polyvalent organic linking group, R di is a residue of a diisocyanate, and R dOH is a residue of a polycarbonate polyol.

12. The orthodontic article of claim 1 , wherein the at least one urethane (meth)acrylate comprises a reaction product of at least two of: an aliphatic polycarbonate diol, a diisocyanate, a diol (meth)acrylate, or an isocyanate functional (meth)acrylate.

13. The orthodontic article of claim 12 , wherein the at least one urethane (meth)acrylate is of Formula (XII):

wherein, R di is a residue of a diisocyanate, R AD is a residue of a (meth)acrylated diol, Q is a polyvalent organic linking group, A has a formula —XC(═O)C(R 1 )═CH 2 , wherein X is O, S, or NR 4 , R 4 is H or alkyl of 1 to 4 carbon atoms, and R 1 is a lower alkyl of 1 to 4 carbon atoms or H, p is 1 or 2, v+w is 1 to 15, and R dOH1 is selected from R dOH or R AD , with a provisos that when v is 0 then R dOH1 is R dOH , and when w is 0 then R dOH1 is R AD .

14. The orthodontic article of claim 1 , wherein the at least one urethane (meth)acrylate further comprises polymerized units of a polyester diol, and wherein the at least one urethane (meth)acrylate contains the same or more polymerized units of the aliphatic polycarbonate diol than the polyester diol.

15. The orthodontic article of claim 14 , wherein the at least one urethane (meth)acrylate is of Formula (XIII):

wherein Q is a polyvalent organic linking group, A is a (meth)acryl functional group of a formula —XC(═O)C(R 1 )═CH 2 , wherein X is O, S, or NR 4 , R 4 is H or alkyl of 1 to 4 carbon atoms, R 1 is a lower alkyl of 1 to 4 carbon atoms or H, and wherein p is 1 or 2, R di is a residue of a diisocyanate, and each R dOH2 is independently selected from a residue of a polyester polyol or a residue of a polycarbonate polyol, with a proviso that x is greater than 2.

16. The orthodontic article of claim 1 , wherein the aliphatic polycarbonate diol is of Formula (I):

wherein each of R 1 in each (O—R 1 —O—C(═O)) repeat unit and each R 2 are independently an aliphatic, cycloaliphatic, or aliphatic/cycloaliphatic alkylene group and an average number of carbon atoms in a combination of all the R 1 and R 2 groups is 4 to 10, and m is 2 to 23.

17. The orthodontic article of claim 1 , wherein the polymerizable composition further comprises an antimicrobial lipid in an amount of 0.1 wt. % or greater, 0.5 wt. %, 1 wt. %, 1.5 wt. %, 2 wt. %, 3 wt. %, or 4 wt. % or greater, based on a total weight of the

Assignees

• Solventum Intellectual Properties Company

Inventors

• Klun Thomas P
• Parkar Zeba
• Riedesel John M
• Pokorny Richard J
• Amb Chad M
• Coonce Benjamin R
• Clough Robert S
• Wu Tianyu
• Chakraborty Saswata
• Lu Yongshang
• Macmurray Benjamin C
• Abuelyaman Ahmed S
• Geisler Karl J L
• Connell Jodi L
• Yu Ta-Hua

Classifications

• C08K5/3437

  condensed with carbocyclic rings · CPC title

• C08K5/0041

  Optical brightening agents, organic pigments · CPC title

• C08G2650/16

  Photopolymerisation · CPC title

• C08G64/305

  and alcohols · CPC title

• C08G18/3206

  aliphatic · CPC title