IP Library Granted Patent US 9,308,520
Granted Patent B2
US 9,308,520 · App. 11/638,167 · Granted Apr 12, 2016

Silica based material

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Quick Facts
Patent No.
US 9,308,520
App. No.
11/638,167
Granted
Apr 12, 2016
Kind
B2
Abstract

An organo-modified silica based material to be used for making a stationary phase for liquid chromatography comprising a part which is unmodified silica, and a part which is silica comprising organic groups bonded to the silica. A method for preparing an organo-modified silica based material comprising mixing in an aqueous medium a silica based material and an organosilane compound, and reacting the mixture. A stationary phase separation material prepared by functionalizing the organo-modified silica based material is also disclosed.

Claims (20)

1. Stationary phase separation material comprising an organo-modified silica based material comprising an inner part which is unmodified silica, and a part which is silica comprising organic groups bonded to the silica, wherein said organic groups are distributed from the surface of the silica based material, including pore surfaces, into the silica based material in a gradually decreasing concentration, which further comprises a surface-functionalisation of the organo-modified silica based material in the form of one or more functional groups groups selected from the group consisting of diol-substituted alkyl, amino-substituted alkyl, cyanoalkyl, fluoralkyl, phenyl, fluorophenyl, phenylalkyl, C 1 -C 30 alkyl, and combinations thereof;

wherein the ratio of the amount of silicon atoms having a T2 structure to the amount of silicon atoms having a T3 structure is less than about 1, as determined by solid state NMR spectroscopy.

2. Stationary phase separation material according to claim 1 , wherein the ratio of the amount of T3 to the amount of all of (T1+T2+T3) in the stationary phase separation material is more than, or equal to, about 0.70, as determined by solid state NMR spectroscopy.

3. Stationary phase separation material according to claim 1 , having an alkaline stability, determined as ppm silicon per specific surface area (BET method) [ppm Si/m 2 /g] in the eluate from the procedure of pumping 41.5 mL of 100 mM NaOH mixed with ethanol in a 1:1 volume relation, at 1 mL/min, at a temperature of 25° C., through a column of 215 mm length and 4.6 mm inner diameter packed with about 2.5 g of the organo-modified silica based material, of less than about 0.2 [ppm Si/m 2 /g].

4. Stationary phase separation material according to claim 1 , wherein the surface-functionalisation in the form of one or more functional groups is selected from the group consisting of C 4 -alkyl, C 8 -alkyl, C 18 -alkyl, and mixtures thereof.

5. Stationary phase separation material according to claim 1 , wherein said organic groups are selected from the group consisting of alkyl groups, alkenyl groups, alkynyl groups, alkylene groups, alkenylene groups, alkynylene groups and mixtures thereof.

6. Stationary phase separation material according to claim 1 , wherein the ratio of the amount of silicon atoms having a T2 structure to the amount of all of (T1+T2+T3) is less than about 0.40, as determined by solid state NMR spectroscopy.

7. Stationary phase separation material according to claim 1 , wherein the ratio of the amount of silicon atoms having a T1 structure to the amount of all of (T1+T2+T3) in the stationary phase separation material, as determined by solid state NMR spectroscopy, is from about 0 to about 0.05.

8. The stationary phase separation material according to claim 1 , wherein the ratio of the amount of T3 to the amount of all of (T1+T2+T3) in the stationary phase separation material is more than, or equal to, about 0.70, as determined by solid state NMR spectroscopy; and

wherein the stationary phase separation material has an alkaline stability, determined as ppm silicon per specific surface area (BET method) [ppm Si/m2/g] in the eluate from the procedure of pumping 41.5 mL of 100 mM NaOH mixed with ethanol in a 1:1 volume relation, at 1 mL/min, at a temperature of 25° C., through a column of 215 mm length and 4.6 mm inner diameter packed with about 2.5 g of the organo-modified silica based material, of less than about 0.2 [ppm Si/m2/g].

9. Stationary phase separation material comprising an organo-modified silica based material comprising an inner part which is unmodified silica, and a part which is silica comprising organic groups bonded to the silica, wherein said organic groups are distributed from the surface of the silica based material, including pore surfaces, into the silica based material in a gradually decreasing concentration, which further comprises a surface-functionalisation of the organo-modified silica based material in the form of one or more functional groups, and wherein the stationary phase separation material has an alkaline stability, determined as ppm silicon per specific surface area (BET method) [ppm Si/m 2 /g] in the eluate from the procedure of pumping 41.5 mL of 100 mM NaOH mixed with ethanol in a 1:1 volume relation, at 1 mL/min, at a temperature of 25° C., through a column of 215 mm length and 4.6 mm inner diameter packed with about 2.5 g of the organo-modified silica based material, of less than about 0.2 [ppm Si/m 2 /g] wherein the ratio of the amount of silicon atoms having a T2 structure to the amount of silicon atoms having a T3 structure is less than about 1, as determined by solid state NMR spectroscopy.

10. Stationary phase separation material according to claim 9 , wherein the surface-functionalisation in the form of one or more functional groups is selected from the group consisting of diol-substituted alkyl, amino-substituted alkyl, cyanoalkyl, fluoralkyl, phenyl, fluorophenyl, phenylalkyl, C 1 -C 30 alkyl, and mixtures thereof.

11. Stationary phase separation material according to claim 10 , wherein the surface-functionalisation in the form of one or more functional groups is selected from the group consisting of C 4 -alkyl, C 8 -alkyl, C 18 -alkyl, and mixtures thereof.

12. Stationary phase separation material according to claim 10 , wherein the surface-functionalisation in the form of one or more functional groups is selected from the group consisting of diol-substituted alkyl, amino-substituted alkyl, cyanoalkyl, fluoralkyl, phenyl, fluorophenyl, phenylalkyl, and mixtures thereof.

13. Stationary phase separation material comprising an organo-modified silica based material comprising an inner part which is unmodified silica, and a part which is silica comprising organic groups bonded to the silica, wherein said organic groups are distributed from the surface of the silica based material, including pore surfaces, into the silica based material in a gradually decreasing concentration, which further comprises that the organo-modified silica based material has been subjected to (i) surface-functionalisation and (ii) end-capping wherein the ratio of the amount of silicon atoms having a T2 structure to the amount of silicon atoms having a T3 structure is less than about 1, as determined by solid state NMR spectroscopy.

14. Stationary phase separation material according to claim 13 , wherein the surface-functionalisation is achieved by reaction of silanol groups of the organo-modified silica based material with one or more organosilanes comprising a functional group.

15. Stationary phase separation material according to claim 14 , wherein the functional group is selected from the group consisting of diol-substituted alkyl, amino-substituted alkyl, cyanoalkyl, fluoralkyl, phenyl, fluorophenyl, phenylalkyl, C 1 -C 30 alkyl, and mixtures thereof.

16. Stationary phase separation material according to claim 15 , wherein the functional group is selected from the group consisting of C 4 -alkyl, C 8 -alkyl, C 18 -alkyl, and mixtures thereof.

17. Stationary phase separation material according to claim 13 , wherein the end-capping is achieved by reaction of silanol groups of the organo-modified silica based material with an end-capping agent.

18. Stationary phase separation material according to claim 17 , wherein end-capping agent is selected from the group consisting of trimethyl chlorosilane, dimethyl dichlorosilane, and mixtures thereof.

Assignments (3)
CHANGE OF NAME Recorded Sep 18, 2019
From: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: NOURYON CHEMICALS INTERNATIONAL B.V.
Reel/Frame 050426/0671 →
SECURITY INTEREST Recorded Oct 1, 2018
From: STARFRUIT US MERGER SUB 1 LLC; STARFRUIT US MERGER SUB 2 LLC; AKZO NOBEL SURFACE CHEMISTRY LLC; AKZO NOBEL CHEMICALS B.V.; AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: WILMINGTON TRUST (LONDON) LIMITED, AS COLLATERAL AGENT
Reel/Frame 047231/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 13, 2017
From: AKZO NOBEL N.V.
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 044427/0759 →