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

Patent metadata

Field	Value
Publication number	US-11106131-B2
Application number	US-201615253640-A
Country	US
Kind code	B2
Filing date	Aug 31, 2016
Priority date	Aug 31, 2016
Publication date	Aug 31, 2021
Grant date	Aug 31, 2021

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. An additive manufacturing resin, comprising:
a photo polymerizable compound;
a click-chemistry compatible compound comprising a terminal azide group having a protecting group functionalized thereto, 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; and
a pore-forming compound.

2. The additive manufacturing resin as recited in claim 1 , wherein the photo polymerizable compound comprises ethylene glycol dimethacrylate (EGDMA).

3. The additive manufacturing resin as recited in claim 1 , wherein the photo polymerizable compound comprises hexanediol functionalized with at least one epoxide functional group.

4. The additive manufacturing resin as recited in claim 1 , wherein the photo polymerizable compound is characterized by a partial structure selected from the group consisting of:

wherein X and A are each independently selected from the group consisting of: —H, and —C n H 2n+1 ;
wherein Y is selected from the group consisting of: —NH—, —CH 2 , and —N(C n H 2n+1 )-;
wherein Z is an organic azide;
wherein A is selected from the group consisting of: —H, - and C n H 2n+1 ;
wherein D is an olefin; and
wherein R is a linker comprising at least one functional group selected from the group consisting of: an aromatic group, dimethylsiloxane, an ester, an amide, an amine, a urea, a carbamate, a carbonate, and a sulfone.

5. The additive manufacturing resin as recited in claim 1 , further comprising: a photoinitiator; a photoactivator; a stabilizer; and a photoabsorber.

6. An additive manufacturing resin suitable for fabricating a click-chemistry compatible composition of matter, the additive manufacturing resin comprising:
a photo polymerizable compound comprising a polyethylene-glycol backbone functionalized with at least one epoxide functional group; and
a click-chemistry compatible compound;
wherein the photo polymerizable compound is characterized by a partial structure selected from the group consisting of:

wherein X and A are each independently selected from the group consisting of: —H, and —C n H 2n+1 ;
wherein Y is selected from the group consisting of: —NH—, —CH 2 , and —N(C n H 2n+1 )-;
wherein Z is an organic azide;
wherein A is selected from the group consisting of: —H, - and C n H 2n+1 ;
wherein D is an olefin; and
wherein R is a linker comprising at least one functional group selected from the group consisting of: an aromatic group, dimethylsiloxane, an ester, an amide, an amine, a urea, a carbamate, a carbonate, and a sulfone.

7. The additive manufacturing resin as recited in claim 6 , wherein the photo polymerizable compound is characterized by the partial structure

8. The additive manufacturing resin as recited in claim 6 , wherein the photo polymerizable compound is characterized by the partial structure

9. The additive manufacturing resin as recited in claim 6 , wherein the photo polymerizable compound is characterized by the partial structure

10. The additive manufacturing resin as recited in claim 6 , wherein the photo polymerizable compound is characterized by the partial structure

11. The additive manufacturing resin as recited in claim 10 , wherein D is characterized by a partial structure selected from the group consisting of:

Assignees

• L Livermore Nat Security Llc

Inventors

• Campbell Patrick
• Duoss Eric
• Oakdale James

Classifications

• B33Y70/00

  Materials specially adapted for additive manufacturing · CPC title

• G03F7/008

  Azides (G03F7/075 takes precedence) · CPC title

• G03F7/038

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• G03F7/0037 Primary

  Production of three-dimensional images · CPC title

• G03F7/0755

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