IP Library Granted Patent US 8,921,579
Granted Patent B2
US 8,921,579 · App. 14/200,147 · Granted Dec 30, 2014

Pendant dipodal silanes having a disilapropyl terminus

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Quick Facts
Patent No.
US 8,921,579
App. No.
14/200,147
Granted
Dec 30, 2014
Kind
B2
Abstract

Pendant dipodal silanes having formula (I) and methods for their synthesis are provided. In formula (I), R is an organic radical other than methyl and X may be a halogen, an alkoxy group, an acetoxy group, or a dialkylamino group. Films, adhesives, and composites formed from the inventive dipodal silanes generally demonstrate significantly greater hydrolytic resistance and film-forming ability than conventional silanes. RSiX 2 CH 2 SiX 3   (I)

Claims (33)

1. A pendant dipodal silane having formula (I), wherein R is a linear or branched, saturated, substituted or unsubstituted hydrocarbon having about four to about thirty carbon atoms and X is selected from the group consisting of a halogen and an alkoxy group:

RSiX 2 CH 2 SiX 3   (I);

and wherein the silane having formula (I) is selected from the group consisting of:

a silane having formula (I), wherein X is chloro and R is 3-chloro-2-methylpropyl;

a silane having formula (I), wherein X is methoxy and R is 3-chloro-2-methylpropyl;

a silane having formula (I), wherein X is ethoxy and R is 3-chloro-2-methylpropyl;

a silane having formula (I), wherein X is chloro and R is 3-cyanopropyl;

a silane having formula (I), wherein X is ethoxy and R is 3-amino-2-methylpropyl;

a silane having formula (I), wherein X is ethoxy and R is 2-aminoethyl-3-amino-2-methylpropyl;

a silane having formula (I), wherein X is ethoxy and R is 3-glycidoxypropyl;

a silane having formula (I), wherein X is methoxy and R is 3-methacryloxypropyl;

a silane having formula (I), wherein X is ethoxy and R is 3-mercapto-2-methylpropyl;

a silane having formula (I), wherein X is ethoxy and R is 3-(N-methylamino)propyl;

a silane having formula (I), wherein X is ethoxy and R is methoxypolyethyleneoxypropyl;

1,1,1,3,3-pentachloro-1,3-disilatridecane; and

1,1,1,3,3-pentamethoxy-1,3-disilatridecane.

2. A pendant dipodal silane having formula (I), wherein R is a linear or branched, saturated or unsaturated substituted hydrocarbon having about four to about thirty carbon atoms, and wherein R is substituted with a functional group selected from the group consisting of an aromatic group, an ether group, an ester group, an epoxy group, a halogen, an amino group, a cyano group, a mercapto group, a sulfide group, an isothiocyanate group, and an isocyanate group; and X is selected from the group consisting of a halogen, an alkoxy group, a dialkylamino group, and an acetoxy group:

RSiX 2 CH 2 SiX 3   (I).

3. A pendant dipodal silane having formula (I), wherein R is a linear or branched, saturated or unsaturated, substituted or unsubstituted hydrocarbon having about four to about thirty carbon atoms and X is selected from the group consisting of chloro, bromo, fluoro, a methoxy group, an ethoxy group, an acetoxy group, and a dialkylamino group:

RSiX 2 CH 2 SiX 3   (I).

4. A pendant dipodal silane having formula (I), wherein R is a linear or branched substituted or unsubstituted alkyl group having about ten to about thirty carbon atoms and X is selected from the group consisting of a halogen, an alkoxy group, a dialkylamino group, and an acetoxy group:

RSiX 2 CH 2 SiX 3 —  (I).

5. The silane according to claim 4 , wherein the alkyl group has an aromatic terminus.

6. The silane according to claim 4 , wherein the alkyl group has a halogen terminus selected from the group consisting of fluorine, chlorine, and bromine.

7. The silane according to claim 4 , wherein all hydrogens other than hydrogens in alpha or beta positions with respect to silicon are replaced with fluorine.

8. A surface modified with a silane compound according to claim 1 .

9. The surface according to claim 8 , wherein the surface is glass.

10. A surface modified with a silane compound according to claim 2 .

11. The surface according to claim 9 , wherein the surface is glass.

12. A surface modified with a silane compound according to claim 3 .

13. The surface according to claim 12 , wherein the surface is glass.

14. A surface modified with a silane compound according to claim 4 .

15. The surface according to claim 11 , wherein the surface is glass.

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 22, 2024
From: GELEST TECHNOLOGIES, INC.
To: GELEST, INC.
Reel/Frame 068467/0243 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2022
From: GELEST TECHNOLOGIES, INC.
To: GELEST, INC.
Reel/Frame 058668/0350 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 28, 2021
From: GELEST TECHNOLOGIES, INC.
To: GELEST, INC.
Reel/Frame 058595/0701 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 7, 2021
From: GELEST TECHNOLOGIES, INC.
To: GELEST, INC.
Reel/Frame 056272/0183 →
RELEASE OF SECURITY INTEREST Recorded Oct 1, 2020
From: ANTARES CAPITAL LP
To: GELEST BIOSYSTEMS, LLC; GELEST, INC.; GELEST TECHNOLOGIES, INC.
Reel/Frame 053946/0556 →
RELEASE OF SECURITY INTEREST Recorded Jun 24, 2019
From: WELLS FARGO BANK, NATIONAL ASSOCIATION
To: GELEST TECHNOLOGIES, INC.; GELEST, INC.; GELEST BIOSYSTEMS, LLC
Reel/Frame 049567/0194 →
PATENT SECURITY AGREEMENT Recorded Jun 21, 2019
From: GELEST, INC.; GELEST TECHNOLOGIES, INC.; GELEST BIOSYSTEMS, LLC
To: ANTARES CAPITAL LP
Reel/Frame 049557/0526 →
SECURITY INTEREST Recorded Aug 14, 2017
From: GELEST, INC.; GELEST TECHNOLOGIES, INC.; GELEST BIOSYSTEMS, LLC
To: WELLS FARGO BANK, NATIONAL ASSOCIATION
Reel/Frame 043540/0963 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 7, 2014
From: ARKLES, BARRY C; PAN, YOULIN; LARSON, GERALD L
To: GELEST TECHNOLOGIES, INC.
Reel/Frame 032374/0530 →