Click-chemistry compatible structures, click-chemistry functionalized structures, and materials and methods for making the same

Patent metadata

Field	Value
Publication number	US-2018059540-A1
Application number	US-201615253640-A
Country	US
Kind code	A1
Filing date	Aug 31, 2016
Priority date	Aug 31, 2016
Publication date	Mar 1, 2018
Grant date	—

Abstract

According to several embodiments, a composition of matter includes: a three-dimensional structure comprising photo polymerized molecules. At least some of the photo polymerized molecules further comprise one or more protected click-chemistry compatible functional groups; and at least portions of one or more surfaces of the three-dimensional structure are functionalized with one or more of the protected click-chemistry compatible functional groups. An additive manufacturing resin suitable for fabricating a click-chemistry compatible composition of matter includes: a photo polymerizable compound; and a click-chemistry compatible compound. A method of forming an additive manufacturing resin suitable for fabricating a click-chemistry compatible composition of matter includes: reacting a compound comprising a terminal alkyne group or a terminal azide group with a protecting reagent to form a protected reactive diluent precursor, reacting the precursor with a compound to form a protected reactive diluent; and mixing the protected reactive diluent with a photo polymerizable compound.

First claim

What is claimed is:

1 . A composition of matter, comprising:
a three-dimensional structure comprising photo polymerized molecules; wherein at least some of the photo polymerized molecules further comprise one or more protected click-chemistry compatible functional groups; and wherein at least portions of one or more surfaces of the three-dimensional structure are functionalized with one or more of the protected click-chemistry compatible functional groups.

2 . The composition of matter as recited in claim 1 , wherein the one or more protected click-chemistry compatible functional groups are selected from a group consisting of: an alkyne coupled to a protecting group and an azide coupled to the protecting group; and
wherein the protecting group is selected from a group consisting of: a trimethylsilyl, a triethylsilyl, a t-butyl dimethylsilyl, a triisopropylsilyl, and a 2-(2-hydroxypropyl)alkyne.

3 . The composition of matter as recited in claim 1 , wherein the one or more click-chemistry compatible functional groups are deprotected.

4 . The composition of matter as recited in claim 1 , wherein the three-dimensional structure is structurally characterized by features having a feature size on a scale of several hundred nanometers to several millimeters.

5 . An additive manufacturing resin suitable for fabricating a click-chemistry compatible composition of matter, the resin comprising:
a photo polymerizable compound; and a click-chemistry compatible compound.

6 . The additive manufacturing resin as recited in claim 5 , the photo polymerizable compound comprising a functional group selected from a group consisting of: acrylates, epoxides, and thiol-enes.

7 . The additive manufacturing resin as recited in claim 5 , the click-chemistry compatible compound comprising a functional group selected from a group consisting of: acrylates, epoxides, and thiol-enes.

8 . The additive manufacturing resin as recited in claim 5 , the click-chemistry compatible compound comprising a terminal alkyne group or a terminal azide group.

9 . The additive manufacturing resin as recited in claim 8 , wherein the click-chemistry compatible compound comprises a protecting group functionalized to the terminal alkyne group or the terminal azide group; and
wherein the protecting group is selected from a group consisting of: a trimethylsilyl, a triethylsilyl, a t-butyl dimethylsilyl, a triisopropylsilyl, and a 2-(2-hydroxypropyl)alkyne.

10 . The additive manufacturing resin as recited in claim 5 , wherein the click-chemistry compatible compound is a monomer.

11 . A method of forming an additive manufacturing resin suitable for fabricating a click-chemistry compatible composition of matter, the method comprising:
reacting a compound comprising a terminal alkyne group or a terminal azide group with a protecting reagent to form a protected reactive diluent precursor, the precursor comprising the terminal alkyne group or the terminal azide group; reacting the precursor with a compound comprising a photo polymerizable group to form a protected reactive diluent; and mixing the protected reactive diluent with a photo polymerizable compound to form the additive manufacturing resin.

12 . The method as recited in claim 11 , wherein the photo polymerizable compound comprises a polyethylene-glycol backbone functionalized with at least one photo polymerizable moiety selected from a group consisting of: acrylates, epoxides, and thiol-enes.

13 . The method as recited in claim 11 , wherein the photo polymerizable compound comprises a hexanediol backbone functionalized with at least one photo polymerizable moiety selected from a group consisting of: acrylates, epoxides, and thiol-enes.

14 . The method as recited in claim 11 , wherein the protecting reagent comprises a protecting group selected from a group consisting of: a trimethylsilyl, a triethylsilyl, a t-butyl dimethylsilyl, a triisopropylsilyl, and a 2-(2-hydroxypropyl)alkyne.

15 . The method as recited in claim 11 , wherein reacting the compound comprising the terminal alkyne group or a terminal azide group with the protecting reagent attaches a protecting group to the terminal alkyne group or the terminal azide group.

16 . The method as recited in claim 11 , wherein reacting the compound comprising the terminal alkyne group or the terminal azide group with the protecting reagent comprises:
reacting the compound comprising the terminal alkyne group or the terminal azide group with an organolithium reagent; and treating, with an acid, a product of reacting the compound comprising the terminal alkyne group or the terminal azide group with the organolithium reagent.

17 . The method as recited in claim 16 , wherein the organolithium reagent comprises n-butyllithium; and
wherein the acid comprises hydrochloric acid.

18 . The method as recited in claim 11 , wherein the compound comprising the photo polymerizable group is an acryloyl halide reagent.

19 . The method as recited in claim 11 , wherein the compound comprising the photo polymerizable group is selected from a group consisting of acryloyl chloride and 2-methyl-2-propenoyl chloride.

20 . The method as recited in claim 11 , wherein reacting the precursor with the compound comprising the photo polymerizable group is performed in the presence of a base.

Assignees

• L Livermore Nat Security Llc

Inventors

• Campbell Patrick
• Duoss Eric
• Oakdale James

Classifications

• G03F7/20

  Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00) · CPC title

• G03F7/027

  Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) · CPC title

• G03F7/008

  Azides (G03F7/075 takes precedence) · CPC title

• G03F7/025

  Non-macromolecular photopolymerisable compounds having carbon-to-carbon triple bonds, e.g. acetylenic compounds (G03F7/075 takes precedence) · CPC title

• G03F7/0755

  Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence) · CPC title