IP Library Granted Patent US 10,391,470
Granted Patent B2
US 10,391,470 · App. 15/264,536 · Granted Aug 27, 2019

Sol-gel derived compositions

Inventors: Paul L. Edmiston (Wooster, OH); Stephen R. Spoonamore (Wooster, OH); Tatiana Eliseeva (Houston, TX)
Assignee: ABS Materials, Inc.
B01J20/262B01D15/02B01D15/08B01J20/265B01J20/2803B01J20/28047B01J20/28064B01J20/28066B01J20/28073B01J20/28076B09C1/08C02F1/705C08G77/48C08G77/52B01D53/02B01D2253/202B01D2257/2066B01J2220/56C02F1/281C02F1/681C02F2101/32C02F2101/36C02F2305/08C08G77/70C08G2220/00Y02P20/154
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Quick Facts
Patent No.
US 10,391,470
App. No.
15/264,536
Granted
Aug 27, 2019
Kind
B2
Abstract

Disclosed are sol gel derived materials obtained from at least one first precursor and at least one second precursor, as well as sol gel derived compositions containing a plurality of alkylsiloxy substituents obtained from such sol-gel derived materials.

Claims (26)

1. A sol-gel composition obtained from at least a first alkoxysilane precursor and a second alkoxysilane precursor, where at least the second alkoxysilane precursor is a bis(trialkoxysilylalkyl)benzene that is 1,4-bis(trimethoxysilylmethyl)benzene (BTB), bis(triethoxysilylethyl)benzene (BTEB), or a mixture thereof, and where the sol-gel composition is swellable to at least 1.5 times its dry volume, when placed in excess acetone.

2. The sol-gel composition of claim 1 wherein

the first alkoxysilane precursor has the formula:

(RO) x (R 2 ) y Si((R 1 )Si(R 2 ) y (OR) x ) z   (1)

where x is 2, 3 or 4, y is 0, 1 or 2 and z is 0 or 1, where the sum of x+y+z is 4, and where each R is independently a C 1 to C 6 alkyl, R 1 is an alkyl or aromatic bridging group and each R 2 is individually an organic group and

the second alkoxysilane precursor has the formula:

(RO) 3 Si—(CH 2 ) n —Ar—(CH 2 ) m —Si—(OR) 3   (2)

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 an alkyl group as defined above; and

wherein the second alkoxysilane precursor is 1,4-bis(trimethoxysilylmethyl) benzene (BTB), bis(triethoxysilylethyl)benzene (BTEB), or a mixture thereof.

3. The sol-gel composition of claim 2 , wherein the amount of first alkoxysilane precursor to second alkoxysilane precursor is from about 5:95 mol:mol to about 60:40 mol:mol.

4. The sol-gel composition of claim 2 , wherein the amount of first alkoxysilane precursor to second alkoxysilane precursor is from about 20:80 mol:mol to about 50:50 mol:mol.

5. The sol-gel composition of claim 2 , wherein R is methyl or ethyl.

6. The sol-gel composition of claim 2 , wherein each R 2 is independently an aliphatic or non-aliphatic hydrocarbon containing up to about 30 carbons.

7. The sol-gel composition of claim 6 , wherein the hydrocarbon is a straight-chain hydrocarbon, a branched-chain hydrocarbon, a cyclic hydrocarbon or an aromatic hydrocarbon.

8. The sol-gel composition of claim 1 , wherein the sol-gel composition contains a plurality of alkylsiloxy substituents.

9. The sol-gel composition of claim 8 , wherein each of the alkylsiloxy substituents correspond to the formula:

—(O) w —Si—(R 3 ) 4-w   (3)

where R 3 is independently a hydrocarbon containing up to about 2 carbons, and w is an integer from 1 to 3.

10. The sol-gel composition of claim 9 , wherein each of the alklysiloxy substituents include at least one heteroatom selected from sulfur, oxygen, nitrogen, phosphorous, a halogen, or a combination thereof.

11. The sol-gel composition of claim 1 , wherein the first precursor is tetramethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysiliane, aminopropyl-trimethoxysilane, 1,4-bis(triethoxysilyl)benzene, 2-(trimethoxysilylethyl)pyridine, bis(triethoxysilylpropyl)amine, para-trifluoromethylterafluorophenyltrimethoxysilane, (tridecafluoro-1,1,2,2-tetrahydro-octyl)trimethoxysilane, 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-cyanopropyltrimethoxysilane, 3-sulfoxypropyltrimethoxysilane, isocyanatopropyltrimethoxysilane 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and trimethoxypropylbenzylcarbamate.

12. The sol-gel composition of claim 1 , wherein the bis(trialkoxysilylalkyl)benzene is BTEB.

13. The sol-gel composition of claim 1 , wherein the sol-gel composition is swellable to at least five times its dry volume, when placed in excess acetone.

14. The sol-gel composition of claim 1 , wherein the sol-gel composition absorbs from about 5 to about 15 times its dry weight, of acetone, when placed in excess acetone.

15. The sol-gel composition of claim 14 , wherein the sol-gel composition absorbs from about 8 to about 12 its dry weight, of acetone, when placed in excess acetone.

16. The sol-gel composition of claim 1 , wherein the sol-gel composition has a pore volume of from about 0.9 mL/g to about 1.1 mL/g.

17. The sol-gel composition of claim 1 , wherein the sol-gel composition has a surface area from about 600 m 2 /g to about 1200 m 2 /g.

Assignments (6)
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 →
[AMENDED AND RESTATED] CONVERTIBLE PROMISSORY NOTE Recorded Apr 12, 2021
From: ABS MATERIALS, INC.
To: BRIGGS, ADAM
Reel/Frame 056798/0194 →
CONVERTIBLE PROMISSORY NOTE Recorded Apr 8, 2021
From: ABS MATERIALS, INC.
To: BRIGGS, ADAM
Reel/Frame 055874/0702 →
AMENDED AND RESTATED CONVERTIBLE PROMISSORY NOTE Recorded Apr 8, 2021
From: ABS MATERIALS, INC
To: BRIGGS, ADAM
Reel/Frame 057133/0814 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2016
From: EDMISTON, PAUL L.; SPOONAMORE, STEPHEN R.; ELISEEVA, TATIANA V.
To: ABS MATERIALS, INC.
Reel/Frame 039770/0843 →
Continuity (6)
Continuation 13565718 · Aug 2, 2012
Continuation In Part 13025445 · Feb 11, 2011
Continuation In Part 12560002 · Sep 15, 2009
Continuation In Part 11537944 · Oct 2, 2006
Provisional Application 60722619 · Sep 30, 2005
Related Publication 20170028380A1 · Feb 2, 2017