Photopolymerizable compositions including a polypropylene oxide component, articles, and methods

Patent metadata

Field	Value
Publication number	US-12104000-B2
Application number	US-201916960566-A
Country	US
Kind code	B2
Filing date	Mar 6, 2019
Priority date	Mar 15, 2018
Publication date	Oct 1, 2024
Grant date	Oct 1, 2024

Abstract

The present disclosure provides a photopolymerizable composition. The photopolymerizable composition includes at least one polypropylene oxide component and an initiator, plus optionally a urethane component, a multifunctional reactive diluent, and/or an inhibitor. The present disclosure also provides an article including the reaction product of the photopolymerizable composition. Typically, the article exhibits an elongation at break of 30% or greater. Further, the present disclosure provides a method of making an article. The method includes (i) providing a photopolymerizable composition and (ii) selectively curing the photopolymerizable composition to form an article. The method optionally also includes (iii) curing unpolymerized polypropylene oxide component, urethane component and/or multifunctional reactive diluent remaining after step (ii). Further, methods are provided, including receiving, by a manufacturing device having one or more processors, a digital object comprising data specifying an article; and generating, with the manufacturing device by an additive manufacturing process, the article based on the digital object. A system is also provided, including a display that displays a 3D model of an 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 article.

First claim

The invention claimed is:

1. A photopolymerizable composition comprising a blend of:
a. 1 to 80 wt. %, inclusive, of at least one polypropylene oxide component based on the total weight of the photopolymerizable composition, wherein the at least one polypropylene oxide component is of any of Formula VII, Formula VIII, Formula IX, Formula X, Formula XI, or Formula XII:

wherein n is 5 to 70;

wherein n is 5 to 70 or 5 to 40;

wherein n is 5 to 70 or 15 to 20;

wherein n is 5 to 70 or 15 to 20;

wherein n is 5 to 70 or 15 to 20; or

n is 5 to 70 or 15 to 20;

b. optionally 30 wt. % or greater of at least one urethane component, if present, based on the total weight of the photopolymerizable composition;
with the proviso that when the at least one urethane component is not present then the at least one polypropylene oxide component is of Formulae IX, X, or XI, and
with the proviso that when the at least one polypropylene oxide component is of Formula VII, then the at least one urethane component is present;
c. optionally at least one multifunctional reactive diluent in an amount of 1 to 30 wt. %, inclusive, if present, based on the total weight of the photopolymerizable composition;
d. 0.1 to 5 wt. %, inclusive, of at least one initiator; and
e. an optional inhibitor in an amount of 0.001 to 1 wt. %, inclusive, if present, based on the total weight of the photopolymerizable composition.

2. The photopolymerizable composition of claim 1 , wherein the at least one polypropylene oxide component is of Formula VII:

wherein n is 5 to 60.

3. The photopolymerizable composition of claim 1 , wherein the at least one polypropylene oxide component is of Formula VIII:

wherein n is 5 to 70 or 5 to 40.

4. The photopolymerizable composition of claim 1 , wherein the at least one polypropylene oxide component is of Formula IX:

wherein n is 5 to 70 or 15 to 20.

5. The photopolymerizable composition of claim 1 , wherein the at least one polypropylene oxide component is of Formula X:

wherein n is 5 to 70 or 15 to 20.

6. The photopolymerizable composition of claim 1 , wherein the at least one polypropylene oxide component is of Formula XI:

wherein n is 5 to 70 or 15 to 20.

7. The photopolymerizable composition of claim 1 , wherein the at least one polypropylene oxide component is of Formula XII:

wherein n is 5 to 70 or 15 to 20.

8. The photopolymerizable composition of claim 1 , wherein the at least one multifunctional reactive diluent is present and comprises a polyester methacrylate.

9. The photopolymerizable composition of claim 1 , wherein the polypropylene oxide segment has a molecular weight of 400 to 2,000 grams per mole (g/mol).

10. An article comprising a reaction product of a photopolymerizable composition of claim 1 ,
wherein the article comprises an orthodontic article.

11. The article of claim 10 , wherein the article comprises a plurality of layers.

12. The article of claim 10 , exhibiting an elongation at break of 30% or greater.

13. A method of making an article, the method comprising:
a. providing a photopolymerizable composition of claim 1 ;
b. selectively curing the photopolymerizable composition to form an article; and
c. optionally curing unpolymerized polypropylene oxide component, urethane component, and/or reactive diluent remaining after step (b).

14. The method of claim 13 , 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).

15. A non-transitory machine readable medium comprising data representing a three-dimensional model of an article, when accessed by one or more processors interfacing with a 3D printer, causes the 3D printer to create an article comprising a reaction product of the photopolymerizable composition of claim 1 .

16. A method comprising:
a. receiving, by a manufacturing device having one or more processors, a digital object comprising data specifying a plurality of layers of an article; and
b. generating, with the manufacturing device by an additive manufacturing process, the article based on the digital object, the article comprising a reaction product of the photopolymerizable composition of claim 1 .

17. A system comprising:
a. a display that displays a 3D model of an article; and
b. 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 article, the article comprising a reaction product of the photopolymerizable composition of claim 1 .

18. The photopolymerizable composition of claim 1 , wherein the urethane component is a urethane (meth)acrylate or a urethane (meth)acrylate oligomer.

19. The photopolymerizable composition of claim 1 , wherein the at least one polypropylene oxide component is present in an amount of at least 10 wt %.

20. The photopolymerizable composition of claim 1 , comprising:
a polypropylene oxide component of Formula VIII present in an amount of 10 wt % to 20 wt %; and
at least one urethane (meth)acrylate or urethane (meth)acrylate oligomer.

Assignees

• 3M Innovative Properties Company
• Solventum Intellectual Properties Company

Inventors

• Abuelyaman Ahmed S
• Parkar Zeba
• Riedesel John M

Classifications

• C07C271/22

  to carbon atoms of hydrocarbon radicals substituted by carboxyl groups · CPC title

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title

• B29K2071/02

  Polyalkylene oxides, e.g. PEO, i.e. polyethylene oxide, or derivatives thereof · CPC title

• B29C64/135

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

• B29C64/393

  for controlling or regulating additive manufacturing processes · CPC title