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US-20260125496-A1 - MONOMERS AND CURABLE COMPOSITIONS FOR CRYSTALLINITY CONTROL IN POLYMERIC MATERIALS FOR 3D-PRINTED DENTAL DEVICES

US20260125496A1US 20260125496 A1US20260125496 A1US 20260125496A1US-20260125496-A1

Abstract

The present disclosure provides monomers and curable compositions comprising such monomers for preparing polymeric materials with controlled crystallinity. Orthodontic appliances made from these polymeric materials are also provided.

Inventors

  • Michael Christopher Cole
  • Jenny Shao
  • Umesh Upendra Choudhary

Assignees

  • ALIGN TECHNOLOGY, INC.

Dates

Publication Date
20260507
Application Date
20251104

Claims (20)

  1. 1 . A curable composition comprising a monomer having the following structure (I): wherein: Ar 1 and Ar 2 are independently an arylene or heteroarylene group; L 1 and L 2 are independently an ether or ester linkage; L 3 and L 4 are independently an ether or ester linkage; R 1 is an alkylene, cycloalkylene, heteroalklyene or heteroatomic linker, wherein the alkylene or heteroalkylene is optionally interrupted by —OC(O)O—, —C(O)—, —C(O)O—, arylene or heteroarylene; R 2 and R 3 are independently an optional alkylene or heteroalkylene linker; and G 1 and G 2 are independently a reactive functional group comprising an ethylenically unsaturated moiety or a thiol moiety.
  2. 2 . The curable composition of claim 1 , wherein: (A) Ar 1 and Ar 2 are independently phenylene, naphthalene, thienylene or furanylene; (B) L 1 and L 2 are each an ester linkage, L 1 is an ether linkage and L 2 is an ester linkage, or L 1 is an ester linkage and L 2 is an ether linkage; and (C) L 3 and L 4 are each an ester linkage, L 3 is an ether linkage and L 4 is an ester linkage, or L 3 is an ester linkage and L 4 is an ether linkage.
  3. 3 .- 10 . (canceled)
  4. 11 . The curable composition of claim 2 , wherein Ar 1 and Ar 2 are each phenylene and L 1 , L 2 , L 3 , and L 4 are each an ester linkage, the monomer having the following structure (IA):
  5. 12 . The curable composition of claim 2 , wherein Ar 1 and Ar 2 are each phenylene, L 1 and L 4 are each an ether linkage, and L 2 and L 3 are each an ester linkage, the monomer having the following structure (IB):
  6. 13 . The curable composition of claim 2 , wherein Ar 1 and Ar 2 are each phenylene, L 1 and L 4 are each an ester linkage, and L 2 and L 3 are each an ether linkage, the monomer having the following structure (IC):
  7. 14 . (canceled)
  8. 15 . The curable composition of claim 1 , wherein R 1 has one of the following structures: —(CH 2 ) x —; —(CH 2 ) y —O—(CH 2 ) z —; —(CH 2 ) y —S—(CH 2 ) z —; wherein x, y and z are independently an integer from 1 to 12.
  9. 16 . The curable composition of claim 1 , wherein R 2 and R 3 independently have one of the following structures: wherein x, y and z are independently an integer from 1 to 12.
  10. 17 .- 19 . (canceled)
  11. 20 . The curable composition of claim 1 , wherein G 1 and G 2 independently have one of the following structures: wherein: R e , at each occurrence, independently H, halogen or C 1 -C 3 alkyl; R f , at each occurrence, independently H, halogen, C 1 -C 3 alkyl, C 1 -C 6 alkoxy and aryl; and p, q and r are independently an integer from 1 to 6.
  12. 21 .- 23 . (canceled)
  13. 24 . The curable composition of claim 1 , wherein the monomer of structure (I) is a compound having one of the following structures: wherein G 1 and G 2 are G 1 and G 2 are —SH, or G 1 is and G 2 is —SH.
  14. 25 . The curable composition of claim 1 , further comprising a monomer having the following structure (II): wherein: Ar is an arylene or heteroarylene group; R 4 and R 5 are independently an optional alkylene linker; L 6 and L 7 are independently a carbonate, ether, or ester linkage; R 6 and R 7 are independently an optional alkylene or heteroalkylene linker, wherein the alkylene or heteroalkylene is optionally interrupted by —OC(O)O—, —C(O)— or —C(O)O—; and G 1 and G 2 are independently a reactive functional group comprising an ethylenically unsaturated moiety or a thiol moiety.
  15. 26 . The curable composition of claim 25 , wherein: (A) Ar is phenylene, naphthalene, thienylene or furanylene; (B) R 4 and R 5 are each a direct bond or R 4 and R 5 are each a linear or branched C 1-12 alkylene; and (C) R 6 and R 7 independently have one of the following structures: —(CH 2 ) x —; —(CH 2 ) y —O—(CH 2 ) z —; wherein x, y and z are independently an integer from 1 to 12.
  16. 27 .- 30 . (canceled)
  17. 31 . The curable composition of claim 26 , wherein Ar is phenylene, R 4 and R 5 are each a direct bond, and L 6 and L 7 are each an ester linkage, the monomer having the following structure (IIA):
  18. 32 . The curable composition of claim 26 , wherein Ar is phenylene, R 4 and R 5 are each a direct bond, and L 6 and L 7 are each an ether linkage, the monomer having the following structure (IIB):
  19. 33 . The curable composition of claim 26 , wherein Ar is phenylene, R 4 and R 5 are independently an optionally substituted linear or branched C 1-4 alkylene, and L 6 and L 7 are each a carbonate linkage, the monomer having the following structure (IIC):
  20. 34 .- 41 . (canceled)

Description

PRIORITY CLAIM AND CROSS-REFERENCE This application claims the benefit of U.S. Provisional Patent Application No. 63/716,609, filed Nov. 5, 2024, which is incorporated by reference herein in its entirety. BACKGROUND Orthodontic procedures involve repositioning a patient's teeth to correct malocclusions and enhance aesthetics. This is typically accomplished using orthodontic appliances such as braces, retainers, and shell aligners, which guide the tooth through controlled movements. Periodic adjustments, often requiring modification or replacement of these appliances, are necessary to achieve optimal results. Polymeric materials play a crucial role in the fabrication of orthodontic appliances due to their ability to support controlled tooth repositioning. Polymeric materials that exhibit both stiffness and elasticity are particularly desirable, as are 3D printable resins suitable for producing such polymeric materials. BRIEF SUMMARY Provided herein are monomers and curable compositions comprising such monomers, which enable control over the degree of crystallinity in the resulting polymeric materials. Also provided herein are methods for making orthodontic appliances using these compositions, as well as orthodontic appliances comprising polymeric materials with controlled crystallinity. In one aspect, provided is a monomer having the following structure (I): wherein Ar1 and Ar2 are independently an arylene or heteroarylene group; L1 and L2 are independently an ether or ester linkage; L3 and L4 are independently an ether or ester linkage; R1 is an alkylene, cycloalkylene, heteroalklyene or heteroatomic linker, wherein the alkylene or heteroalkylene is optionally interrupted by —OC(O)O—, —C(O)—, —C(O)O—, arylene or heteroarylene; R2 and R3 are independently an optional alkylene or heteroalklyene linker; and G1 and G2 are independently a reactive functional group comprising an ethylenically unsaturated moiety or a thiol moiety. In some embodiments, Ar1 and Ar2 are independently phenylene, naphthalene, thienylene or furanylene. In some embodiments, L1 and L2 are the same or different. In some embodiments, L1 and L2 are each an ester linkage. In some embodiments, L1 is an ether linkage, and L2 is an ester linkage. In some embodiments, L1 is an ester linkage, and L2 is an ether linkage. In some embodiments, L3 and L4 are the same or different. In some embodiments, L3 and L4 are each an ester linkage. In some embodiments, L3 is an ether linkage, and L4 is an ester linkage. In some embodiments, L3 is an ester linkage, and L4 is an ether linkage. In some embodiments, Ar1 and Ar2 are each phenylene, and L1, L2, L3, and L4 are each an ester linkage, the monomer having the following structure (IA): In some embodiments, Ar1 and Ar2 are each phenylene, L1 and L4 are each an ether linkage, and L2 and L3 are each an ester linkage, the monomer having the following structure (IB): In some embodiments, Ar1 and Ar2 are each phenylene, L1 and L4 are each an ester linkage, and L2 and L3 are each an ether linkage, the monomer having the following structure (IC): In some embodiments, R1 is C1-12 alkylene, wherein the C2-12 alkylene is optionally interrupted by —OC(O)O—, —C(O)—, —C(O)O—, arylene or heteroarylene. In some embodiments, R1 has one of the following structures: —(CH2)x—; —(CH2)y—O—(CH2)z—; —(CH2)y—S—(CH2)z—; wherein x, y and z are independently an integer from 1 to 12. In some embodiments, R2 and R3 independently have one of the following structures: wherein x, y and z are independently an integer from 1 to 12. In another aspect, provided is a monomer having the following structure (II): wherein Ar is an arylene or heteroarylene group; R4 and R5 are independently an optional alkylene linker; L6 and L7 are independently a carbonate, ether, or ester linkage; R6 and R7 are independently an optional alkylene or heteroalklyene linker, wherein the alkylene or heteroalkylene is optionally interrupted by —OC(O)O—, —C(O)— or —C(O)O—; and G1 and G2 are independently a reactive functional group comprising an ethylenically unsaturated moiety or a thiol moiety. In some embodiments, Ar is phenylene, naphthalene, thienylene or furanylene. In some embodiments, R4 and R5 are each a direct bond. In some embodiments, R4 and R5 are each a linear or branched C1-12 alkylene. In some embodiments, R4 and R5 are each methylene or (dimethyl)methylene. In some embodiments, L6 and L7 are the same. In some embodiments, Ar is phenylene, R4 and R5 are each a direct bond, and L6 and L7 are each an ester linkage, the monomer having the following structure IIA): In some embodiments, Ar is phenylene, R4 and R5 are each a direct bond, and L6 and L7 are each an ether linkage, the monomer having the following structure (IIB): In some embodiments, Ar is phenylene, R4 and R5 are independently an optionally substituted linear or branched C1-4 alkylene, and L6 and L7 are each a carbonate linkage, the monomer having the following structure (IIC): In some embodime