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

Patent metadata

Field	Value
Publication number	US-11945900-B2
Application number	US-201917052221-A
Country	US
Kind code	B2
Filing date	Jun 27, 2019
Priority date	Jun 29, 2018
Publication date	Apr 2, 2024
Grant date	Apr 2, 2024

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 the reaction product of a polymerizable composition comprising:
30-65 parts by weight of monofunctional (meth)acrylate monomer(s) per 100 parts of the total polymerizable composition, wherein a cured homopolymer of 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, wherein the at least one urethane (meth)acrylate comprises a reaction product of at least one of the following:
i) an aliphatic polycarbonate diol, a diisocyanate, a diol (meth)acrylate, and a hydroxy functional (meth)acrylate;
ii) an aliphatic polycarbonate diol and an isocyanate functional (meth)acrylate;
iii) an aliphatic polycarbonate diol, a diisocyanate, and an isocyanate functional (meth)acrylate; or
iv) an aliphatic polycarbonate diol, a diisocyanate, a diol (meth)acrylate, and an isocyanate functional (meth)acrylate.

2. The orthodontic article of claim 1 , wherein the monofunctional (meth)acrylate monomer(s) having a T g of at least 30° C. 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 the reaction product of an aliphatic polycarbonate diol, a diisocyanate, and a hydroxy functional (meth)acrylate.

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

wherein Q is a polyvalent organic linking group and A is a (meth)acryl functional group of the 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):
(A) p -Q-OC(O)NH—R di —NH—C(O)—[O—R dOH —OC(O)NH—R di —NH—C(O)] r —O-Q-(A) p   (VI),

wherein A has the 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 the residue of a diisocyanate, R dOH is the 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 the reaction product of an aliphatic polycarbonate diol, a diisocyanate, a diol (meth)acrylate, and a hydroxy functional (meth)acrylate.

7. The orthodontic article of claim 6 , wherein the at least one urethane (meth)acrylate is of Formula (V):
(A) p -Q-OC(O)NH—R di —NH—C(O)—[O—R dOH —OC(O)NH—R di —NH—C(O)] s —[O—R AD —OC(O)NH—R di —NH—C(O)] t —O-Q-(A) p   (V),

wherein A has the 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 the residue of a diisocyanate, R dOH is the 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 the residue of a (meth)acrylated diol.

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

9. The orthodontic article of claim 8 , wherein the at least one urethane (meth)acrylate is of Formula (VIII):
(H 2 C═C(R 3 )C(═O)—O) p -Q-NH—C(═O)—(O—R 1 —O—C(═O)) m —O—R 2 —O—C(═O)NH-Q-(O—C(═O)C(R 3 )═CH 2 ) p   (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 the reaction product of an aliphatic polycarbonate diol, a diisocyanate, and an isocyanate functional (meth)acrylate.

11. The orthodontic article of claim 10 , wherein the at least one urethane (meth)acrylate is of Formula (XI):
(A) p -Q-NHC(O)[O—R dOH —OC(O)NH—R di —NH—C(O)] u —O—R dOH —O—C(O)NH-Q-(A) p    (XI),

wherein u is 0 to 15, A has the 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 the residue of a diisocyanate, and R dOH is the residue of a polycarbonate polyol.

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

13. The orthodontic article of claim 12 , wherein the at least one urethane (meth)acrylate is of Formula (XII):
(A) p -Q-NHC(O)—[—R dOH —OC(O)NH—R di —NH—C(O)] v —[O—R AD —OC(O)NH—R di —NH—C(O)] w —O—R dOH1 —O—C(O)NH-Q-(A) p   (XII),

wherein, R di is the residue of a diisocyanate, R AD is the residue of a (meth)acrylated diol, Q is a polyvalent organic linking group, A has the 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 the provisos that if v is 0 then R dOH1 is R dOH , and if w is 0 then R dOH1 is R AD .

14. The orthodontic article of claim 1 , wherein the urethane (meth)acrylate further comprises polymerized units of a polyester diol, wherein the 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):
(A) p -Q-OC(O)NH—R di —NH—C(O)—[O—R dOH2 —OC(O)NH—R di —NH—C(O)] x —O-Q-(A) p   (XIII),

wherein Q is a polyvalent organic linking group, A is a (meth)acryl functional group of the 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 the residue of a diisocyanate, and each R dOH2 is independently selected from the residue of a polyester polyol or the residue of a polycarbonate polyol, with the proviso that x is greater than 2.

16. The orthodontic article of claim 1 , wherein the aliphatic polycarbonate diol is of Formula (I):
H(O—R 1 —O—C(═O)) m —O—R 2 —OH  (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 the total weight of the polymerizable composition, and 20 wt. % or less, 15 wt. %, 12 wt. %, 10 wt. %, 8 wt. %, or 5 wt. % or less, based

Assignees

• Solventum Intellectual Properties Company
• 3M Innovative 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

• C08G18/44 Primary

  Polycarbonates · CPC title

• A61C7/002

  Orthodontic computer assisted systems · CPC title

• A61C7/08

  Mouthpiece-type retainers {or positioners, e.g. for both the lower and upper arch (arch-shaped medicament applicators for teeth or gums A61C19/063; mouthguards for protecting the teeth of sportsmen A63B71/085)} · CPC title

• A61C13/0019

  using three dimensional printing · CPC title

• B29C71/0009

  using liquids, e.g. solvents, swelling agents (spectacle cases, e.g. for cleaning contact lenses A45C11/04; disinfecting or sterilising contact lenses A61L12/00, using liquid substances A61L2/20; cleaning involving the use of liquid in general B08B3/00; for hydrating contact lenses B29D11/00067) · CPC title