Orthodontic articles prepared using a polycarbonate diol, and methods of making same

Patent metadata

Field	Value
Publication number	US-11104758-B2
Application number	US-201917042384-A
Country	US
Kind code	B2
Filing date	May 21, 2019
Priority date	Jun 29, 2018
Publication date	Aug 31, 2021
Grant date	Aug 31, 2021

Abstract

The present disclosure provides an orthodontic article including the reaction product of the photopolymerizable composition. The photopolymerizable composition includes i) a monofunctional (meth)acrylate monomer whose cured homopolymer has a glass transition temperature of 90 degrees Celsius or greater; ii) a photoinitiator; and iii) a polymerization reaction product of components. The components include 1) an isocyanate; 2) a (meth)acrylate mono-ol; 3) a polycarbonate diol; and 4) a catalyst. Further, the present disclosure provides a method of making an orthodontic article. The method includes obtaining a photopolymerizable composition and selectively curing the photopolymerizable 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) a polymerized reaction product of a photopolymerizable composition comprising:
i) a monofunctional (meth)acrylate monomer whose cured homopolymer has a T g of 90° C. or greater;
ii) a photoinitiator; and
iii) a polymerization reaction product of components, the components comprising:
1) an isocyanate;
2) a (meth)acrylate mono-ol;
3) a polycarbonate diol 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; and

4) a catalyst;

wherein the polymerized reaction product of the photopolymerizable composition has a shape of the orthodontic article.

2. The orthodontic article of claim 1 , wherein the (meth)acrylate mono-ol is of Formula (II):
HO-Q-(A) p   (II)

wherein Q is a polyvalent organic linking group, A is a (meth)acryl functional group of the formula —XC(═O)C(R 3 )═CH 2 , wherein X is O, S, or NR 4 , R 4 is H or an alkyl of 1 to 4 carbon atoms, R 3 is a lower alkyl of 1 to 4 carbon atoms or H, and wherein p is 1 or 2.

3. The orthodontic article of claim 1 , wherein the photopolymerizable composition further comprises a compound of Formula (III):
(H 2 C═C(R 3 )C(═O)—X) p -Q-OC(═O)NH—R di —NHC(═O)O-Q-(X—C(═O)(R 3 )C═CH 2 ) p   (III),

wherein X, Q, p, and R 3 are as defined for Formula (II), and R di is the residue of a diisocyanate.

4. The orthodontic article of claim 3 , wherein the compound of Formula (III) is added to the photopolymerizable composition.

5. The orthodontic article of claim 3 , wherein the compound of Formula (III) is present in an amount of 5 to 20 wt. %, based on the weight of the polymerizable composition.

6. The orthodontic article of claim 3 , wherein the compound of Formula (III) is of Formula (IV):
(IV).

7. The orthodontic article of claim 1 , wherein the monofunctional (meth)acrylate monomer is selected from the group consisting of dicyclopentadienyl acrylate, isobornyl acrylate, dicyclopentanyl acrylate, dimethyl-1-adamantyl acrylate, cyclohexyl methacrylate, tert-butyl methacrylate, 3,3,5-trimethylcyclohexyl methacrylate, cis-4-tert-butyl-cyclohexylmethacrylate, 2-decahydronapthyl methacrylate, 1-adamantyl acrylate, 73/27 trans/cis-4-tert-butylcyclohexylmethacrylate, dicyclopentadienyl methacrylate, dicyclopentanyl methacrylate, trans-4-tert-butylcyclohexyl methacrylate, d,l-isobornyl methacrylate, dimethyl-1-adamantyl methacrylate, d,l-bornyl methacrylate, 3-tetracyclo[4.4.0.1.1]dodecyl methacrylate, 1-adamantyl methacrylate, or combinations thereof.

8. The orthodontic article of claim 1 , wherein the polycarbonate diol has a molecular weight of 800 g/mol to 2,200 g/mol, or 1,800 g/mol to 2,200 g/mol.

9. The orthodontic article of claim 1 , wherein the photopolymerizable composition further comprises a UV absorber comprising an optical brightener in an amount of 0.001 to 5% by weight, based on the total weight of the photopolymerizable composition.

10. The orthodontic article of claim 9 , wherein the optical brightener comprises a compound of Formula (V):
(V).

11. The orthodontic article of claim 1 , wherein the polyurethane (meth)acrylate polymer has a molecular weight of 6,000 g/mol to 35,000 g/mol.

12. The orthodontic article of claim 1 , wherein a cured homopolymer of the monofunctional (meth)acrylate monomer has a T g of 100° C. or greater, 170° C. or greater, or 180° C. or greater.

13. The orthodontic article of claim 1 , exhibiting at least two properties selected from the group consisting of an initial relaxation modulus of 100 megapascals (MPa) or greater measured at 2% strain at 37° C., a percent loss of relaxation modulus of 70% or less, a 30 minute relaxation modulus of 100 MPa or greater, an elongation at break of a printed article of 20% or greater, and a tensile strength at yield of 14 MPa or greater.

14. The orthodontic article of claim 1 , exhibiting a peak in loss modulus of 20° C. or less and a tan delta peak of 80° C. or greater.

15. The orthodontic article of claim 1 , further comprising an inhibitor in an amount of 0.001 to 1 wt. %, based on the total weight of the photopolymerizable composition.

16. The orthodontic article of claim 1 , wherein the photoinitiator is present in an amount of 0.2 wt. % to 5 wt. %.

17. The orthodontic article of claim 1 , wherein the monofunctional (meth)acrylate monomer has a log of octanol/water partition coefficient (log P) value of greater than 3, greater than 2, or greater than 1.

18. A method of making an orthodontic article, the method comprising:
a) obtaining a photopolymerizable composition comprising:
i) a monofunctional (meth)acrylate monomer whose cured homopolymer has a T g of 90° C. or greater;
ii) a photoinitiator; and
iii) a polymerization reaction product of components, the components comprising:
1) an isocyanate;
2) a (meth)acrylate mono-ol;
3) a polycarbonate diol 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; and
4) a catalyst;

b) selectively curing the photopolymerizable composition; and
c) repeating steps a) and b) to form multiple layers and create the orthodontic article.

19. The method of claim 18 , wherein the photopolymerizable composition is cured using actinic radiation comprising UV radiation, e-beam radiation, visible radiation, or a combination thereof.

20. The method of claim 18 , further comprising subjecting the orthodontic article to a heat treatment.

21. A non-transitory machine readable medium comprising data representing a three-dimensional model of an orthodontic article, when accessed by one or more processors interfacing with a 3D printer, causes the 3D printer to create an orthodontic article comprising a reaction product of a photopolymerizable composition comprising a blend of:
a) a monofunctional (meth)acrylate monomer whose cured homopolymer has a T g of 90° C. or greater;
b) a photoinitiator; and
c) a polymerization reaction product of components, the components comprising:
i) an isocyanate;
ii) a (meth)acrylate mono-ol;
iii) a polycarbonate diol 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; and
iv) a catalyst.

22. A method comprising:
a) retrieving, from a non-transitory machine readable medium, data representing a 3D model of an article;
b) executing, by one or more processors, a 3D printing application interfacing with a manufacturing device using the data; and
c) generating, by the manufacturing device, a physical object of the orthodontic article, the orthodontic article comprising a reaction product of a photopolymerizable composition, the photopolymerizable composition comprising a blend of:
i) a monofunctional (meth)acrylate monomer whose cured homopolymer

Assignees

• 3M Innovative Properties Co

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
• Dailey Ian
• Olson David B

Classifications

• A61K6/887

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

• A61K6/62

  Photochemical radical initiators · CPC title

• C08G18/765

  alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring · CPC title

• C08G18/44 Primary

  Polycarbonates · CPC title

• B33Y80/00

  Products made by additive manufacturing · CPC title