IP Library Granted Patent US 9,346,682
Granted Patent B2
US 9,346,682 · App. 14/362,115 · Granted May 24, 2016

Silica microcapsules, process of making the same and uses thereof

Inventors: Mathilde Gosselin (Granby, CA); Shaoyong Yu (Verdun, CA); Nabil Ghezal (Villeneuve-Saint-Georges, FR); Cé Guinto Gamys (Granby, CA)
Assignee: LES INNOVATIONS MATERIUM
C01B33/12A61K8/025A61K8/0241A61K8/11A61K8/25A61K8/97A61K9/501A61Q13/00A61Q19/00B01J13/185C09B67/009C09B67/0097F28D20/023H01B1/02H01B1/127H01B1/128A61K2800/412Y02E60/145Y10T428/2989
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Quick Facts
Patent No.
US 9,346,682
App. No.
14/362,115
Granted
May 24, 2016
Kind
B2
Abstract

The present document describes a microcapsule having silica shells, processes for making the same, processes for functionalizing said microcapsules and processes for encapsulating active agent in said microcapsules.

Claims (32)

1. A microcapsule comprising:

a silica shell having a thickness of from about 50 nm to about 500 μm, and a plurality of pores,

said shell forming a capsule having a diameter from about 0.2 μm to about 1500 μm, and having a density of about 0.001 g/cm 3 to about 1.0 g/cm 3 ,

wherein said shell comprises from about 0% to about 70% Q3 configuration, and from about 30% to about 100% Q4 configuration, or

wherein said shell comprises from about 0% to about 60% T2 configuration and from about 40% to about 100% T3 configuration, or

wherein said shell comprises a combination of T and Q configurations thereof, and

wherein an exterior surface of said microcapsule is covered by a functional group.

2. The microcapsule of claim 1 , wherein said shell comprises about 40% Q3 configuration and about 60% Q4 configuration, or about 100% Q4 configuration.

3. The microcapsule of claim 1 , wherein said pores have pore diameters from about 0.5 nm to about 100 nm.

4. The microcapsule of claim 1 , further comprising a surface layer.

5. The microcapsule of claim 4 , wherein said surface layer comprises a thickness from about 1 nm to about 10 nm.

6. The microcapsule of claim 4 , wherein said surface layer is functionalized with an organosilane.

7. The microcapsule of claim 6 , wherein said organosilane is chosen from a functional trimethoxysilane, a functional triethoxysilane, a functional tripropoxysilane, 3-aminopropyltriethoxysilane, vinyltriacetoxy silane, a vinyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-chloropropyltriethoxysilane, a bis-(triethoxysilylpropyl)tetrasulfane, a methyltriethoxysilane, a n-octyltriethoxysilane, and a phenyltrimethoxysilane and combinations thereof.

8. The microcapsule of claim 4 , wherein said surface layer is functionalized with a hydroxyl group, an amino group, a benzylamino group, a chloropropyl group, a disulfide group, an epoxy group, a mercapto group, a methacrylate group, a vinyl group, and combinations thereof.

9. The microcapsule of claim 1 , further comprising a conductive layer surrounding said exterior surface of said capsule.

10. The microcapsule of claim 9 , wherein said conductive layer is a metallic layer, or a conductive polymer layer.

11. The microcapsule of claim 10 , wherein said metallic layer is a layer of silver (Ag), gold (Au), copper (Cu), aluminum (Al), or combinations thereof.

12. The microcapsule of claim 10 , wherein said conductive polymer layer is a layer of polypyrrole, polythiophene, polyanilines or combinations thereof.

13. The microcapsule of claim 5 , further comprising an active agent.

14. The microcapsule of claim 13 , wherein said active agent is chosen from a catalyst for monomers polymerization, a polymer stabilizer chemical, a fire retardant chemical, a colorant, a pharmaceutically active drug, an enzyme, a cosmetic oil, a fragrance, a perfume, a food additives, an humidifier, an explosive, a phase change material (PCM), an insecticide, an herbicide, a fungicide and combinations thereof, and

wherein said polymer stabilizer chemical is chosen from butylated hydroxytoluene (BHT), α-tocopherol, tocopheryl acetate, an organophosphate, Tris(2,4-di-tert-butylphenyl) phosphite, trisnonylphenyl phosphite, dilauryl thiodipropionate, distearyl thiodipropionate, Bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, benzotriazoles, benzophenones and combinations thereof, and

wherein said fire retardant chemical is chosen from tetrabromobisphenol-A, decabromodiphenylethane, dibromoneopentylglycol, or combinations thereof, and

wherein said colorant is chosen from carbon black, molybdate orange, chrome oxide green, anthanthrone, anthraquinone, benzimidazole, and quinacridone.

15. The microcapsule of claim 13 , wherein said active agent is crosslinked to said surface layer, to said exterior surface, or both.

16. The microcapsule of claim 13 , wherein said active agent is encapsulated in said microcapsule.

17. The microcapsule of claim 1 , having the NMR spectrum as shown in FIG. 1 .

18. A process for the post-functionalization in solution of a microcapsule according to claim 1 comprising step a):

a) dispersion, under inert atmosphere, of the dried silica microcapsules in a dried organic solvent in the presence of one or more organo-reactive silanes and an organic acid or an organic base for a time sufficient and at a temperature sufficient obtain a functionalized microcapsule in a liquid dispersion.

19. The process of claim 18 , further comprising step b) after step a):

b) separating said functionalized microcapsule from said liquid dispersion.

20. The process of claim 19 , further comprising step c) after step b):

c) drying said functionalized microcapsule to obtain a dried functionalized microcapsule.

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE FIRST ASSIGNOR NAME PREVIOUSLY RECORDED AT REEL: 034418 FRAME: 0408. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Mar 4, 2015
From: GOSSELIN, MATHILDE; YU, SHAOYONG; GHEZAL, NABIL; GAMYS, CE GUINTO
To: LES INNOVATIONS MATERIUM
Reel/Frame 035131/0593 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 8, 2014
From: GOSSELEIN, MATHILDE; YU, SHAOYONG; GHEZAL, NABIL; GAMYS, CE GUINTO
To: LES INNOVATIONS MATERIUM
Reel/Frame 034418/0408 →
Continuity (5)
Provisional Application 61565576 · Dec 1, 2011
Provisional Application 61593509 · Feb 1, 2012
Provisional Application 61608121 · Mar 8, 2012
Provisional Application 61617057 · Mar 29, 2012
Related Publication 20140341958A1 · Nov 20, 2014