IP Library Granted Patent US 9,670,067
Granted Patent B2
US 9,670,067 · App. 14/898,676 · Granted Jun 6, 2017

Particle of modified silica

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Quick Facts
Patent No.
US 9,670,067
App. No.
14/898,676
Granted
Jun 6, 2017
Kind
B2
Abstract

The present invention relates to a particle of modified silica which comprises a particle of silica which is covalently linked to at least one halohydrin moiety. Furthermore, the present invention relates to a method of preparing the particle of modified silica, a particle of modified silica obtained by such method, use of the particle of modified silica as a stationary phase for chromatography, as well as a separation column for chromatography comprising the particle of modified silica.

Claims (20)

1. A particle of modified silica, wherein the modified silica is of formula (I):

wherein A is a halogen, SiO 2 is silica, and R 1 is optionally substituted alkyl, alkenyl, alkynyl, aryl, alkylaryl, arylalkyl, heteroalkyl, heterocycle, alkylheterocycle, heterocyclealkyl, or a combination thereof, or R 1 is a steroid,

wherein the optionally substituted alkyl is an alkyl optionally substituted with a aldehylde; alkoxy; alkanoyloxy; alkoxycarbonyl; alkenyl; alkyl; alkynyl; alkylcarbonyloxy; -alkylNHC(O)alkyl; —C(NH)NH-alkyl; alkylamine; arylamino; arylalkylamino; when the alkyl is —CH 2 —, (a) R O —O—, wherein R O is a hydrocarbon of 1 to 30 carbons, (b) (R N1 ) 2 —N—, wherein each R N1 is independently a hydrocarbon of 1 to 30 carbons or (c) (R N2 ) 3 —N + —, wherein each R N2 is independent a hydrocarbon of 1 to 4 carbons; aroyl; aryl; aryloxy; azo; —OC(O)NH-alkyl; CONH 2 ; —CONH-alkyl, —CONH-aryl, —CONH-arylalkyl; carboxyl; cyano; methoxy; ethoxy; guanidine, halo, haloalkyl; heteroalkyl; nitrile; nitro; oxo; —SO 2 NH 2 ; alkylsulfonyl; arylsulfonyl; arylalkylsulfonyl; —NHCONH-alkyl.

2. The particle of modified silica according to claim 1 , wherein the silica is in the form of a porous particle or a monolithic material.

3. The particle of modified silica according claim 1 , wherein A is chlorine.

4. The particle of modified silica according claim 1 , wherein R 1 is an aryl moiety.

5. The particle of modified silica according claim 1 , wherein R 1 is a steroid moiety.

6. The particle of modified silica according claim 1 , wherein R 1 is R 2 —O—CH 2 —, and R 2 is a hydrocarbon having from 1 carbon atom up to 30 carbon atoms.

7. The particle of modified silica according claim 1 , wherein R 1 is

wherein each of R 3 and R 4 , independently of the other, is a hydrocarbon having from 1 carbon atom up to 30 carbon atoms.

8. The particle of modified silica according to claim 1 , wherein the surface density of the

moiety to particle of silica is from 0.1 to 4 μmoles/m 2 silica surface.

9. A method of preparing a particle of modified silica according to claim 1 , the method comprising reacting a particle of silica and at least one halohydrin compound to form a covalent bond between said particle of silica and said halohydrin compound, wherein the halohydrin compound is of formula (II):

wherein A is a halogen, SiO 2 is silica, and R 1 is optionally substituted alkyl, alkenyl, alkynyl, aryl, alkylaryl, arylalkyl, heteroalkyl, heterocycle, alkylheterocycle, heterocyclealkyl, or a combination thereof, or R 1 is a steroid, wherein the optionally substituted alkyl is an alkyl optionally substituted with an aldehylde; alkoxy; alkanoyloxy; alkoxycarbonyl; alkenyl; alkyl; alkynyl; alkylcarbonyloxy; -alkylNHC(O)alkyl; —C(NH)NH-alkyl; alkylamine; arylamino; arylalkylamino; when the alkyl is —CH 2 —, (a) R O —O—, wherein R O is a hydrocarbon of 1 to 30 carbons, (b) (R N1 ) 2 —N—, wherein each R N1 is independently a hydrocarbon of 1 to 30 carbons or (c) (R N2 ) 3 —N + , wherein each R N2 is independent a hydrocarbon of 1 to 4 carbons; aroyl; aryl; aryloxy; azo; —OC(O)NH-alkyl; CONH 2 ; —CONH-alkyl, —CONH-aryl, —CONH-arylalkyl; carboxyl; cyano; methoxy; ethoxy; guanidine, halo, haloalkyl; heteroalkyl; nitrile; nitro; oxo; —SO 2 NH 2 ; alkyl sulfonyl; aryl sulfonyl; arylalkylsulfonyl; —NHCONH-alkyl.

10. The method according to claim 9 , wherein the particle of silica is in the form of a porous particle or a monolithic material.

11. A particle of modified silica obtained by the method as claimed in claim 9 .

12. A stationary phase for chromatography comprising the particle of modified silica of claim 1 .

13. A separation column for chromatography comprising the particle of modified silica according to claim 1 .

14. The particle of modified silica according to claim 6 , wherein R 2 is a hydrocarbon having from 4 carbon atoms up to 18 carbon atoms.

15. The particle of modified silica according to claim 7 , wherein R 2 is a hydrocarbon having from 4 carbon atoms up to 18 carbon atoms.

Assignments (4)
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 →
CHANGE OF ADDRESS Recorded May 15, 2017
From: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 042745/0406 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 15, 2015
From: RESTORP, PER ANDERS; TORNCRONA, ANDERS; LIF, JOHAN; HOGBLOOM, JOAKIM ERIK PATRIK
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 037296/0578 →