Stable alkenyl or alkynyl-containing organosilicon precursor compositions

Patent metadata

Field	Value
Publication number	US-11713328-B2
Application number	US-201916547468-A
Country	US
Kind code	B2
Filing date	Aug 21, 2019
Priority date	Aug 23, 2018
Publication date	Aug 1, 2023
Grant date	Aug 1, 2023

Abstract

A method for producing an alkenyl or alkynyl-containing organosilicon precursor composition, the method comprising the steps of distilling at least once a composition comprising an alkenyl or alkynyl-containing organosilicon compound having the formula RnSiR14−n wherein R is selected a linear or branched C2 to C6 alkenyl group, a linear or branched C2 to C6 alkynyl group; R1 is selected from hydrogen, a linear or branched C1 to C10 alkyl group, and a C3 to C10 cyclic alkyl group; and n is a number selected from 1 to 4, wherein a distilled alkenyl or alkynyl-containing organosilicon precursor composition is produced after distilling; and packaging the distilled alkenyl or alkynyl-containing organosilicon precursor composition in a container, wherein the container permits transmission into the container of no more than 10% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.

First claim

The invention claimed is:

1. A method for producing an alkenyl or alkynyl-containing organosilicon precursor composition for use as precursors to dielectric materials, the method comprising the steps of:
distilling at least once a composition comprising at least one alkenyl or alkynyl-containing organosilicon compound having a formula RnSiR14-n wherein R is selected from the group consisting of a linear or branched C2 to C6 alkenyl group, and a linear or branched C2 to C6 alkynyl group; R1 is selected from the group consisting of hydrogen, a linear or branched C1 to C10 alkyl group, and a C3 to C10 aryl group; and n is 1 to 4, wherein a distilled alkenyl or alkynyl-containing organosilicon precursor composition is produced after distilling, wherein the at least one alkenyl or alkynyl-containing organosilicon compound comprises tetravinylsilane, and wherein the distilled alkenyl or alkynyl-containing organosilicon precursor composition includes less than 100 ppm (0.01 wt. %) of >1000 amu impurities as determined by Gel Permeation Chromatography (GPC); and
packaging the distilled alkenyl or alkynyl-containing organosilicon precursor composition in a container, wherein the container is made of stainless steel and permits transmission into the container of no more than 10% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm; and
wherein the distilled alkenyl or alkynyl-containing organosilicon precursor composition includes less than 50 ppm water impurity and less than 10 ppm halide impurity.

2. The method of claim 1 further comprising adding a stabilizer compound to the distilled alkenyl or alkynyl-containing organosilicon precursor composition prior to said packing step.

3. The method of claim 2 wherein the stabilizer compound is selected from the group consisting of 2,6-di-tert-butyl-4-methyl phenol, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO), 2-tert-butyl-4-hydroxyanisole, 3-tert-butyl-4-hydroxyanisole, propyl ester 3,4,5-trihydroxy-benzoic acid, 2-(1,1-dimethylethyl)-1,4-benzenediol, diphenylpicrylhydrazyl, 4-tert-butylcatechol, N-methylaniline, p-methoxydiphenylamine, diphenylamine, N,N′-diphenyl-p-phenylenediamine, p-hydroxydiphenylamine, phenol, octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, tetrakis (methylene (3,5-di-tert-butyl)-4-hydroxy-hydrocinnamate) methane, phenothiazines, alkylamidonoisoureas, thiodiethylene bis (3,5-di-tert-butyl-4-hydroxy-hydrocinnamate, 1,2-bis (3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl) hydrazine, tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, cyclic neopentanetetrayl bis (octadecyl phosphite), 4,4′-thiobis (6-tert-butyl-m-cresol), 2,2′-methylenebis (6-tert-butyl-p-cresol), oxalyl bis (benzylidenehydrazide), raw seed oils, wheat germ oil, tocopherols and gums.

4. The method of claim 1 wherein the container permits transmission into the container of no more than 7% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.

5. The method of claim 4 wherein the container permits transmission into the container of no more than 1% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.

6. The method of claim 5 wherein the container permits 0% transmission into the container of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.

7. The method of claim 1 , wherein the distilled alkenyl or alkynyl-containing organosilicon precursor composition comprises at least about 98.73 wt. % tetravinylsilane.

8. The method of claim 7 , wherein the distilled alkenyl or alkynyl-containing organosilicon precursor composition comprises at least about 99.15 wt. % tetravinylsilane.

Assignees

• Versum Mat Us Llc

Inventors

• Ridgeway Robert G
• Vrtis Raymond N
• Lei Xinjian
• Rao Madhukar B
• Mayorga Steven Gerard
• Osterwalder Neil
• Xiao Manchao
• Wang Meiliang

Classifications

• C07F7/0896

  Compounds with a Si-H linkage · CPC title

• B65D65/16

  with provision for excluding or admitting light · CPC title

• C07F7/0825 Primary

  Preparations of compounds not comprising Si-Si or Si-cyano linkages · CPC title

• B65D25/14

  Linings or internal coatings (of containers made by folding or erecting blanks made of paper B65D5/56 {; linings for domestic water storage heaters F24H1/183}) · CPC title

• C07F7/20 Primary

  Purification, separation · CPC title