Sol-gel based matrix

Patent metadata

Field	Value
Publication number	US-11236233-B2
Application number	US-201916294153-A
Country	US
Kind code	B2
Filing date	Mar 6, 2019
Priority date	Oct 24, 2013
Publication date	Feb 1, 2022
Grant date	Feb 1, 2022

Abstract

A method for the production of a sol-gel based matrix resulting in a sol-gel based matrix with high stability and high porosity. The sol-gel based material may be used for the production of a composite or sensor suitable for monitoring analytes.

First claim

What is claimed is:

1. A sol-gel matrix comprising:
a first polymer component prepared from polymerization of a first alkoxysilane of the general formula R 1 —Si(OR 2 ) 3 and an additional alkoxysilane of the formula R 5 —Si(OR 2 ) 3 ,
a second sol-gel component comprising a Lewis acid and a second polymer component prepared from Lewis acid catalyzed polymerization of a second alkoxysilane of the general formula

wherein
R 1 is selected from the group consisting of a straight and branched C 1 -C 6 alkyl, a C 2 -C 6 alkenyl, a C 3 -C 6 cycloalkyl, a C 1 -C 6 aminoalkyl, a C 1 -C 6 hydroxyalkyl, a C 1 -C 6 cyanoalkyl, a phenyl, and a group of the formula —Y—(X—Y) n H, with Y being independently selected from the group consisting of straight and branched C 1 -C 6 alkylene, X being a hetero atom or group selected from the group consisting of O, S, and NH, and n being an integer of 1-5, or R 1 represents a C 1 -C 6 alkyl substituted with a group Z, with Z being independently selected form the group consisting of hydrogen, cyano, halogen, hydroxy, nitro, amide C 1 -C 24 -alkyl, C 1 -C 24 -haloalkyl, C 2 -C 24 -alkenyl, C 2 -C 24 -alkynyl, aryl, C 1 -C 24 -alkoxy, C 1 -C 24 -alkylsulfonyl, amino, aminocarbonyl, aminothiocarbonyl, aminocarbonylamino, aminothiocarbonylamino, aminocarbonyloxy, aminosulfonyl, aminosulfonyloxy, aminosulfonylamino, amidino, carboxyl, carboxyl ester comprising a C 1 -C 6 alkyl alcohol moiety, (carboxyl ester)amino comprising a C 1 -C 6 alkyl alcohol moiety, (carboxyl ester)oxy comprising a C 1 -C 6 alkyl alcohol moiety, sulfonyl, sulfonyloxy, thiol, thiocarbonyl, C 1 -C 24 -alkylthio, 5 or 6 membered heteroaryl, and a C 3 -C 7 cycloalkyl;
R 2 independently represents a straight or branched C 1 -C 6 alkyl;
R 3 represents a linker selected from a group of the formula —R 4 —(X—R 4 ) 0-12 —, wherein R 4 is independently selected from straight or branched C 2 -C 6 alkylene, C 2 -C 24 -haloalkylene, and X is a hetero atom or group selected from the group consisting of 0, S and NH; and
R 5 represents a group of the general formula
—R 3 —NH—C(═O)—X—R 3 -Q

wherein R 3 and X are as defined above and independently selected, and Q represents an indicator and/or a reference dye derived from triangulenium compounds, acridinium compounds, ruthenium doped sol-gel particles, ruthenium-based compounds with α-diimine ligands, porphorin with Pt or Pd as the central metal atom, Ru(bpy) 2 (dpp)Cl 2 , Ru(bpy) 3 Cl 2 a lanthanide containing complex, or polymeric metal containing structure.

2. The sol-gel matrix according to claim 1 ,
wherein the second polymer component is prepared from polymerization of the second alkoxysilane and the additional alkoxysilane.

3. The sol-gel matrix according to claim 1 , wherein Q is an indicator dye derived from 8-hydroxypyrene-1,3,6-trisulfonic acid (HPTS), fluorescein, or rhodamine B.

4. The sol-gel matrix according to claim 1 , wherein the Lewis acid is a triagonal planar species.

5. The sol-gel matrix according to claim 4 , wherein the Lewis acid is selected from the group consisting of TiCl 3 , AlCl 3 , and BF 3 , or solvates or etherates thereof.

6. The sol-gel matrix according to claim 1 , wherein the first alkoxysilane is selected from the group consisting of ethyltriethoxysilane (ETEOS), methyltriethoxysilane (MTEOS), propyltriethoxysilane (PrTEOS), n-octyltriethoxysilane (n-octyl TEOS), methyltrimethoxysilane (MTMOS), aminopropyltrimethoxysilane (APTMOS), phenyltriethoxysilane (PhTEOS), and phenyl trimethoxysilane (PhTMOS).

7. The sol-gel matrix according to claim 1 , wherein second alkoxysilane is 3-glycidoxypropyltrimethoxysilane (GPTMS).

8. A composite comprising a layer of sol-gel matrix according to claim 1 and a platform comprising a microstructure area, wherein the sol-gel matrix is attached to the microstructure area.

9. The composite according to claim 8 , wherein the microstructure area comprises a plurality of pillars having a height in the range of 0.1 μm to 500 μm and a distance between each pillar in the range of 0.1 μm to 500 μm.

10. The composite according to claim 8 , wherein the distance between each pillar is in the range of 5 to 40 μm, the height of the pillars is in the range of 11 to 40 μm and the width of each pillar is in the range of 5 to 40 μm.

11. The composite according to claim 8 , wherein the layer of the sol-gel matrix has a thickness smaller than the height of the microstructure.

12. The composite according to claim 8 , comprising an array of sol-gel matrices attached to different areas on the microstructure area.

13. The composite according to claim 8 , wherein sol-gel matrix comprises an indicator or reference dye.

14. The composite according to claim 13 , wherein the sol-gel matrix includes at least two different indicator or reference dyes.

15. The composite according to claim 8 , wherein the platform is an inner surface of a container or conduit for transporting a fluid.

16. The composite according to claim 15 , wherein the container comprises an opening and cylindrical or tapered sides, and is closed opposite to the opening.

17. The composite according to claim 8 , wherein the platform is an inner surface of a disposable container for transporting a fluid.

18. The composite according to claim 8 , wherein the microstructure area has been prepared by a process selected from the group consisting of injection molding, hot embossing, laser microstructuring, micromachining, chemical etching, and photoresist layer structuring.

19. A method of monitoring of a bioculture, the method comprising the steps of:
providing a composite according to claim 13 ,
applying the bioculture to the platform,
exposing the sol-gel matrix to light, and
detecting light emitted from the sol-gel matrix.

Assignees

• Univ Copenhagen

Inventors

• Sorensen Thomas Just
• Rosenberg Martin
• Laursen Bo W

Classifications

• G01N21/80

  Indicating pH value · CPC title

• C09B69/008

  Dyes containing a substituent, which contains a silicium atom · CPC title

• C09B69/109

  containing other specific dyes · CPC title

• C08G77/14

  containing silicon bound to oxygen-containing groups · CPC title

• C08G77/398

  containing boron or metal atoms · CPC title