IP Library Granted Patent US 8,987,494
Granted Patent B2
US 8,987,494 · App. 13/777,704 · Granted Mar 24, 2015

Low molecular weight carbosilanes, precursors thereof, and methods of preparation

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Quick Facts
Patent No.
US 8,987,494
App. No.
13/777,704
Granted
Mar 24, 2015
Kind
B2
Abstract

A series of silicon compounds are provided, which are excellent precursors to small carbosilanes, such as 1,3,5-trisilapentane, 2,4,6-trisilaheptane, tris(silylmethyl)silane and tetrakis(silylmethyl)silane. A method of preparing a carbosilane involves forming a Grignard, lithium, or metallic reagent from a halomethyltrialkoxysilane, reacting the Grignard, lithium, or metallic reagent with a dihalodihydridosilane, a trihalohydridosilane, a tetrahalosilane, a dialkoxydihydridosilane, a trialkoxyhydridosilane, or a tetraalkoxysilane to yield a carbosilane precursor, and reducing the precursor to form the carbosilane.

Claims (14)

1. A carbosilane having formula (IX):

wherein X 1 and X 2 are each independently selected from the group consisting of hydrogen, methyl, and CH 2 SiR, wherein R is H 3 or H 2 CH 3 , and wherein X 3 is CH 2 SiH 3 .

2. The carbosilane according to claim 1 , wherein X 1 =X 2 =CH 2 SiH 3 and the carbosilane has formula (XII):

3. The carbosilane according to claim 1 , wherein X 1 =X 2 =H and the carbosilane has formula (VI):

4. The carbosilane according to claim 1 , wherein X 1 =H, X 2 =CH 2 SiH 3 and the carbosilane has formula (VII):

5. The carbosilane according to claim 1 , wherein X 1 =H, X 2 =CH 3 and the carbosilane has formula (VIII):

6. A carbosilane having formula (XI):

7. A silicon compound having formula (II):

wherein R 1 , R 4 and R 11 are linear or branched alkoxy groups having one to about eight carbon atoms, R 2 , R 3 , R 5 , R 6 , R 9 , and R 12 are each independently selected from the group consisting of isopropyl, isobutyl, and tert-butyl groups, and R 10 is selected from the group consisting of hydrogen, chlorine, bromine, methoxy, and ethoxy groups.

8. The silicon compound according to claim 7 , wherein R 1 , R 4 and R 11 are isopropoxy groups, R 2 , R 3 , R 5 , R 6 , R 9 , and R 12 are each independently selected from the group consisting of isopropyl, isobutyl, and tert-butyl groups, and R 10 is selected from the group consisting of hydrogen, chlorine, bromine, methoxy, and ethoxy groups.

9. The silicon compound according to claim 8 , wherein R 2 , R 3 , R 5 , R 6 , R 9 , and R 12 are isopropyl groups.

10. The silicon compound according to claim 7 , wherein R 1 , R 4 and R 11 are isobutoxy groups, R 2 , R 3 , R 5 , R 6 , R 9 , and R 12 are each independently selected from the group consisting of isopropyl, isobutyl, and tert-butyl groups, and R 10 is selected from the group consisting of hydrogen, chlorine, bromine, methoxy, and ethoxy groups.

11. The silicon compound according to claim 7 , wherein R 1 , R 4 and R 11 are methoxy groups, R 2 , R 3 , R 5 , R 6 , R 9 , and R 12 are each independently selected from the group consisting of isopropyl, isobutyl, and tert-butyl groups, and R 10 is selected from the group consisting of hydrogen, chlorine, bromine, methoxy, and ethoxy groups.

12. The silicon compound according to claim 7 , wherein R 1 , R 4 and R 11 are ethoxy groups, R 2 , R 3 , R 5 , R 6 , R 9 , and R 12 are each independently selected from the group consisting of isopropyl, isobutyl, and tert-butyl groups, and R 10 is selected from the group consisting of hydrogen, chlorine, bromine, methoxy, and ethoxy groups.

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 Feb 27, 2013
From: LARSON, GERALD L.; PAN, YOULIN; ARKLES, BARRY C.
To: GELEST TECHNOLOGIES, INC.
Reel/Frame 029887/0371 →