IP Library Granted Patent US 9,440,869
Granted Patent B2
US 9,440,869 · App. 13/565,718 · Granted Sep 13, 2016

Sol-gel derived compositions

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Quick Facts
Patent No.
US 9,440,869
App. No.
13/565,718
Granted
Sep 13, 2016
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 (22)

1. A sol-gel composition comprising:

a sol-gel composition containing a plurality of alkylsiloxy substituents, the sol-gel composition obtained by gelling a reaction medium consisting essentially of:

at least one first alkoxysilane precursor having 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

at least one second alkoxysilane precursor having 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.

2. The sol-gel material of claim 1 , wherein the amount of first alkoxysilane precursor to second alkoxysilane precursor is from about 5:95 mol:mol to about 60:40 mol:mol.

3. The sol-gel material of claim 1 , wherein the amount of first alkoxysilane precursor to second alkoxysilane precursor is from about 20:80 mol:mol to about 50:50 mol:mol.

4. The sol-gel composition of claim 1 , wherein 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 30 carbons, w is an integer from 1 to 3.

5. The sol-gel composition of claim 4 , wherein the alklysiloxy substituents include at least one heteroatom selected from sulfur, oxygen, nitrogen, phosphorous or halogen atom or combinations thereof.

6. The sol-gel composition of claim 1 , wherein R is methyl or ethyl.

7. The sol-gel composition of claim 1 , wherein each R 2 is independently an aliphatic or non-aliphatic hydrocarbon containing up to about 30 carbons.

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

9. The sol-gel composition of claim 7 , wherein the hydrocarbon is substituted with a primary amine, a secondary amine, a tertiary amine, a thiol, an isocyanate, a carbamate, an alcohol, an alkene, a pyridine, a halogen, a halogenated hydrocarbon or combinations thereof.

10. 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.

11. The sol-gel derived composition of claim 10 , wherein the second precursor is a bis(trialkoxysilylalkyl)benzene.

12. The sol-gel composition of claim 11 , wherein the bis(trialkoxysilylalkyl)benzene is 1,4-bis(trimethoxysilylmethyl)benzene (BTB), bis(triethoxysilylethyl)benzene (BTEB) or mixtures thereof.

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

Assignments (9)
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 →
CONVERTIBLE PROMISSORY NOTE Recorded Apr 8, 2021
From: ABS MATERIALS, INC.
To: BRIGGS, ADAM
Reel/Frame 055874/0929 →
AMENDED AND RESTATED CONVERTIBLE PROMISSORY NOTE Recorded Apr 8, 2021
From: ABS MATERIALS, INC
To: BRIGGS, ADAM
Reel/Frame 057133/0814 →
SECOND AMENDED AND RESTATED CONVERTIBLE PROMISSORY NOTE Recorded Apr 5, 2021
From: ABS MATERIALS, INC.
To: BRIGGS, ADAM
Reel/Frame 055818/0766 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 11, 2016
From: ELISEEVA, TATIANA V.
To: ABS MATERIALS, INC.
Reel/Frame 039126/0370 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 16, 2012
From: EDMISTON, PAUL L.; SPOONAMORE, STEPHEN R.
To: ABS MATERIALS, INC.
Reel/Frame 029140/0040 →