Organosilica materials, methods of making, and uses thereof

• US 10,435,514 B2
• Filed: 06/10/2016
• Issued: 10/08/2019
• Est. Priority Date: 06/10/2016
• Status: Active Grant

• Current Assignee: ExxonMobil Research & Engineering Company (Exxon Mobil Corporation)
• Original Assignee: ExxonMobil Research & Engineering Company (Exxon Mobil Corporation)
• Inventors: Calabro, David C., Johnson, Ivy D., Li, Quanchang, Podsiadlo, Paul, Weston, Simon C., Afeworki, Mobae
• Primary Examiner(s): Moore, Margaret G
• Application Number:
  US15/178,961
• Publication Number:
  US 20170355822A1
• Time in Patent Office: 1,215 Days
• CPC Class Codes: C01B 33/113 Silicon oxides; Hydrates thereof preparing monoxide by reduction of siliceous material C01B33/182
• CPC Class Codes: C01B 37/00 Compounds having molecular sieve properties but not having base-exchange properties
• CPC Class Codes: C08G 77/04 Polysiloxanes
• CPC Class Codes: C08G 77/06 Preparatory processes C08G77/045 takes precedence
• CPC Class Codes: C08G 77/26 nitrogen-containing groups

Abstract

Organosilica materials made from monomers including at least a source of silica that is reactive to polymerize, optionally in combination with at least one additional cyclic monomer. Methods for making such organosilica materials are also described herein.

Claims

1. A method of producing an organosilica material comprising:

(a) providing an aqueous mixture that contains no added structure directing agent, no added porogen, and no organic solvent;

(b) adding into the aqueous mixture to form a solution at least one compound of;

(i) Formula (I), wherein Formula (I) is 1,1,3,3,5,5-hexaethoxy-1,3,5-trisilacyclohexane;

(ii) a cyclic polyurea monomer of formula (IV),

2. The method of claim 1, wherein at least one compound of Formula (IV) is added to the aqueous mixture, and wherein:

each X⁵ represents a C₁-C₂ alkyl group;

X⁶ and X⁷ each independently represent a C₁-C₂ alkyl group or a C₁-C₂ alkoxy group; and

each X⁸ represents a C₁-C₄ alkylene group bonded to a nitrogen atom of the cyclic polyurea monomer.

3. The method of claim 1, wherein at least one compound of Formula (IV) is added to the aqueous mixture, and the at least one compound of Formula (IV) is tris(3-trimethoxysilylpropyl)isocyanurate.

4. The method of claim 1, wherein the source of silica comprises a particulate silica having an average particle size up to about 150 nm and/or having a particle size distributions such that a d95 is up to about 250 nm.

5. The method of claim 4, wherein the source of silica comprises a particulate silica having an average particle size from about 3 nm to about 50 nm and/or having a particle size distributions such that a d95 is from about 5 nm to about 60 nm.

6. The method of claim 4, wherein the source of silica comprises a colloidal silica.

7. The method of claim 1, further comprising adding to the aqueous mixture at least one compound selected from the group consisting of:

(i) a further compound of Formula (I);

(ii) a further compound of Formula (IV);

(iii) a compound of Formula (II) Z⁵OZ⁶Z⁷Z⁸Si, wherein each Z⁵ can be a hydrogen atom, a C₁-C₄ alkyl group or a bond to a silicon atom of another monomer; and

Z⁶, Z⁷ and Z⁸ each independently can be selected from the group consisting of a hydroxyl group, a C₁-C₄ alkyl group, a C₁-C₄ alkoxy group, a nitrogen-containing C₁-C₁₀ alkyl group, a nitrogen-containing heteroaralkyl group, and a nitrogen-containing optionally substituted heterocycloalkyl group, and an oxygen atom bonded to a silicon atom of another monomer;

(iv) a compound of of Formula (III), Z⁹Z¹⁰Z¹¹Si—

R—

SiZ⁹Z¹⁰Z¹¹wherein each Z⁹ independently can be a hydroxyl group, a C₁-C₄ alkoxy group, or an oxygen atom bonded to a silicon atom of another monomer;

Z¹⁰ and Z¹¹ each independently can a hydroxyl group, a C₁-C₄ alkoxy group, a C₁-C₄ alkyl group, or an oxygen atom bonded to a silicon atom of another monomer, and each R can be selected from the group consisting a C₁-C₈ alkylene group, a C₂-C₈ alkenylene group, a C₂-C₈ alkynylene group, a nitrogen-containing C₁-C₁₀ alkylene group, an optionally substituted C₆-C₂₀ aralkyl, and an optionally substituted C₄-C₂₀ heterocycloalkyl group;

(v) a compound of Formula (V), M¹(OZ¹²)_3, wherein M¹ represents a Group 13 metal and each Z¹² independently represents a hydrogen atom, a C₁-C₆ alkyl, or a bond to a silicon atom of another monomer;

(vi) a compound of Formula (VI), (Z¹³O)₂M²-O—

Si(OZ¹⁴)_3, wherein M² represents a Group 13 metal and Z¹³ and Z¹⁴ each independently represent a hydrogen atom, a C₁-C₆ alkyl group or a bond to a silicon atom of another monomer; and

(vii) a combination thereof.

8. The method of claim 1, wherein the aqueous mixture comprises a base and has a pH from about 8 to about 14.

9. The method of claim 8, wherein the base is ammonium hydroxide, a metal hydroxide, or a metal hydrogen carbonate.

10. The method of claim 1, wherein the aqueous mixture comprises an acid and has a pH from about 0.01 to about 6.0.

11. The method of claim 10, wherein the acid is an inorganic acid.

12. An organosilica material made according to the method of claim 1.