Silica-based organogels via hexahydrotriazine-based reactions

Patent metadata

Field	Value
Publication number	US-10189969-B2
Application number	US-201715482369-A
Country	US
Kind code	B2
Filing date	Apr 7, 2017
Priority date	Apr 7, 2017
Publication date	Jan 29, 2019
Grant date	Jan 29, 2019

Abstract

Silica-based organogels, including aerogels, incorporating hexahydrotriazine and/or hemiaminal species are described. These organo-silica gel materials can have applications as insulating materials. In a particular example, an aerogel includes silica groups and a hexahydrotriazine moiety with at least one nitrogen atom that is covalently linked to a silica group. Methods of making such silica-based organogels are also described.

First claim

What is claimed is:

1. An aerogel, comprising:
a plurality of silica groups; and
a hexahydrotriazine group having at least one nitrogen atom that is covalently linked to at least one silica group in the plurality of silica groups by a linking group.

2. The aerogel of claim 1 , wherein the linking group includes an aromatic group.

3. The aerogel of claim 2 , wherein the aromatic group is a benzene ring.

4. The aerogel of claim 3 , wherein the benzene ring is covalently linked to the at least one silica group via an alkyl group.

5. The aerogel of claim 4 , wherein the benzene ring is covalently bonded to a nitrogen atom of the hexahydrotriazing group, and the alkyl group is at a para position of the benzene ring with respect to the covalent bond of the benzene ring to the nitrogen atom of the hexahydrotriazine group.

6. The aerogel of claim 5 , wherein the alkyl group is an ethanediyl group.

7. The aerogel of claim 4 , wherein the alkyl group is an ethanediyl group.

8. The aerogel of claim 1 , wherein each nitrogen atom of the hexahydrotriazine group is covalently linked to at least one silica group in the plurality of silica groups.

9. The aerogel of claim 1 , wherein the silica groups are nanoparticles of silica.

10. The aerogel of claim 1 , wherein the linking group has the structure:

wherein a nitrogen atom of the hexahydrotriazine group is covalently linked at one starred bond of the linking group, L′ is a divalent group selected from the group consisting of O, S, N(R′), N(H), and R″, wherein R′ and R″ each comprise at least 1 carbon, and the other starred bond of the linking group is bonded to a nitrogen atom of another hexahydrotriazine group.

11. An insulating material, comprising:
an organo-silica gel including:
a plurality of silica groups; and
a hexahydrotriazine group having at least one nitrogen atom of the hexahydrotriazine group covalently linked to at least one silica group in the plurality of silica groups.

12. The insulating material of claim 11 , wherein the organo-silica gel is an aerogel.

13. The insulating material of claim 11 , wherein the at least one nitrogen atom of the hexahydrotriazine group is covalently linked to the at least one silica group via an aromatic group and an alkyl group.

14. The insulating material of claim 11 , wherein the hexahydrotriazine group has the following structure:

wherein each R group independently represents an alkanediyl group covalently linked to at least one silica group in the plurality of silica groups.

15. The insulating material of claim 11 , wherein a nitrogen atom of the hexahydrotriazine group is covalently linked, at one starred bond, to a linking group having the structure:

wherein L′ is a divalent group selected from the group consisting of O, S, N(R′), N(H), and R″, wherein R′ and R″ each comprise at least 1 carbon, and the other starred bond of the linking group is bonded to a nitrogen atom of another hexahydrotriazine group.

Assignees

• IBM

Inventors

• Boday Dylan J
• Garcia Jeannette M
• Hedrick James L
• Wertz Jason T
• Wojtecki Rudy J

Classifications

• C08J9/28 Primary

  by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum · CPC title

• C08G2101/0091

  Chemistry & Metallurgy · mapped topic

• C08J2383/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• C08J2205/026

  Aerogel, i.e. a supercritically dried gel · CPC title

• C08G2110/0091

  Aerogels; Xerogels · CPC title