IP Library Granted Patent US 10,881,598
Granted Patent B2
US 10,881,598 · App. 16/110,837 · Granted Jan 5, 2021

Method of using personal and home care compositions containing a sol-gel derived material

Inventors: Paul L. Edmiston (Wooster, OH); Stacey L. Dean (Broadview Heights, OH)
Assignee: ABS MATERIALS, INC.
A61K8/585A61K8/042A61Q5/02A61Q19/008A61Q19/10
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Quick Facts
Patent No.
US 10,881,598
App. No.
16/110,837
Granted
Jan 5, 2021
Kind
B2
Abstract

Disclosed is a method for removing fatty oil from a surface containing the fatty oil comprising the steps of applying to the surface containing the fatty oil a composition comprising a sol-gel derived material, the sol-gel derived material including a plurality of alkylsiloxy substituents and the sol-gel derived material obtained from (a) at least one first alkoxysilane precursor having the formula: (R′O) 3 —Si—(CH 2 ) n —Ar—(CH 2 ) m —Si—(OR′) 3   (1) where n and m are individually an integer from 1 to 8, Ar is a single-, fused-, or poly-aromatic ring, and each R′ is independently a C 1 to C 5 alkyl group and (b) optionally, at least one second precursor having the formula: where x is 1, 2, 3 or 4; y is 0, 1, 2, 3; z is 0, 1; the total of x+y+z is 4; each R is independently an organic functional group; each an R′ is independently a C 1 to C 5 alkyl group and R″ is an organic bridging group and then moving the composition from the surface to remove the fatty oil.

Claims (43)

1. A method of making a sol-gel derived material, the method comprising:

combining

(a) at least one first alkoxysilane precursor having a formula:

(R′O) 3 —Si—(CH 2 ) n —Ar—(CH 2 ) m —Si—(OR′) 3

where n and m are individually an integer from 1 to 8, Ar is a single-, fused-, or poly-aromatic ring, and each R′ is independently a C 1 to C 5 alkyl group; and

(b) at least one second alkoxysilane precursor having a formula:

where x is 1; y is 2 or 3; z is 0 or 1; the total of x+y+z is 4; each R is independently an organic functional group, each an R′ is independently a C 1 to C 5 alkyl group and R″ is an organic bridging group; and

(c) a solvent, to form an alkoxysilane precursor reaction medium; and

catalyzing hydrolysis and condensation of the alkoxysilane precursors by adding to the reaction medium a catalytic solution comprising a catalyst and water,

thereby obtaining the sol-gel derived material.

2. The method of claim 1 , wherein the catalyst is a base catalyst.

3. The method of claim 2 , wherein the base catalyst is selected from tetrabutylammonium fluoride (TBAF), potassium fluoride, 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), and propylamines.

4. The method of claim 3 , wherein the base catalyst is TBAF.

5. The method of claim 4 , wherein the TBAF is present in the catalytic solution at a concentration of about 0.00001 to about 0.002 M.

6. The method of claim 4 , wherein the TBAF is present in the catalytic solution at a concentration of about 0.001 to about 0.01 M.

7. The method of claim 1 , further comprising, after formation of the sol-gel derived material, aging the reaction product.

8. The method of claim 7 , further comprising rinsing during or after the aging process, to provide a sol-gel derived material characterized by residual silanol groups.

9. The method of claim 8 , further comprising reacting the residual silanol groups with a derivatization reagent, resulting in end-capped silanol groups.

10. The method of claim 9 , wherein the derivatization reagent is selected from halosilanes, silazanes, and disilazanes.

11. The method of claim 1 , wherein y is 2 and z is 1, and R′ is a methyl, ethyl, or propyl group.

12. The method of claim 1 , wherein R comprises an unsubstituted or substituted straight-chain hydrocarbon group, branched-chain hydrocarbon group, cyclic hydrocarbon group, or aromatic hydrocarbon group.

13. The method of claim 1 , wherein the plurality of alkylsiloxy groups have the formula:

—(O) w —Si—(R 1 ) 4-w

where each R 1 is independently an organic group as described above and w is an integer from 1 to 3.

14. The method of claim 1 wherein the at least one first alkoxysilane precursor comprises a bis(trialkoxysilylalkyl)benzene.

15. The method of claim 14 where the at least one first alkoxysilane precursor comprises 1,4-bis(trimethoxysilylmethyl)benzene (BTMB), bis(triethoxysilylethyl)benzene (BTEB), or mixtures thereof.

16. A method of making a sol-gel derived material, the method comprising:

combining

(a) at least one first alkoxysilane precursor having a formula:

(R′O) 3 —Si—(CH 2 ) n —Ar—(CH 2 ) m —Si—(OR′) 3

where

n and m are individually an integer from 1 to 8, Ar is a single-, fused-, or poly-aromatic ring, and each R′ is independently a C 1 to C 5 alkyl group; and

(b) at least one second alkoxysilane precursor having a formula:

where x is 1; y is 2 or 3; z is 0 or 1; the total of x+y+z is 4; each R is independently an organic functional group, each an R′ is independently a C 1 to C 5 alkyl group and R″ is an organic bridging group; and

(c) a solvent, to form an alkoxysilane precursor reaction medium; and

catalyzing hydrolysis and condensation of the alkoxysilane precursors by adding to the reaction medium a catalytic solution comprising a base catalyst and water, thereby obtaining a reaction product;

aging the reaction product

thereby obtaining a sol-gel derived material having residual silanol groups; and

reacting the residual silanol groups with a derivatization reagent, thereby obtaining a sol-gel derived material having end-capped silanol groups.

17. The method of claim 16 , wherein the base catalyst is tetrabutylammonium fluoride (TBAF).

18. The method of claim 16 , wherein y is 2 and z is 1, and R′ is a methyl, ethyl, or propyl group.

19. The method of claim 16 , wherein R comprises an unsubstituted or substituted straight-chain hydrocarbon group, branched-chain hydrocarbon group, cyclic hydrocarbon group, or aromatic hydrocarbon group.

20. The method of claim 16 , further comprising rinsing the reaction product during or after the aging process and before reacting the residual silanol groups with the derivatization reagent.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2021
From: ABS MATERIALS, INC.
To: ABM (ABC), LLC
Reel/Frame 057045/0429 →
SECURITY INTEREST Recorded Jul 31, 2021
From: ABSM (ABC), LLC
To: AQUANEX TECHNOLOGIES, LLC
Reel/Frame 057045/0455 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 28, 2018
From: EDMISTON, PAUL L.; DEAN, STACEY L.
To: ABS MATERIALS, INC.
Reel/Frame 046728/0621 →