Organosilicon compound, method for producing thereof, and use thereof

Patent metadata

Field	Value
Publication number	US-12024535-B2
Application number	US-201917281661-A
Country	US
Kind code	B2
Filing date	Sep 26, 2019
Priority date	Oct 1, 2018
Publication date	Jul 2, 2024
Grant date	Jul 2, 2024

Abstract

An organosilicon compound having not more than 200 silicon atoms per molecule is provided. The organosilicon compound is represented by the following average compositional formula (I): YaR1bSiO(4-a-b)/2 wherein R1 is an alkyl group having 1 to 12 carbon atoms, alkenyl group having 2 to 12 carbon atoms, aryl group having 6 to 20 carbon atoms, alkoxy group having 1 to 6 carbon atoms, or a hydroxyl group; Y is a specific acylphosphinate residue; and subscripts a and b are numbers satisfying the following conditions: 0<a≤2, 0<b≤3, and a≤b. The organosilicon compound is compatible with organopolysiloxanes and is useful as a photo-initiator for various types of photo-curable compositions.

First claim

What is claimed is:

1. A method for producing an organosilicon compound having not more than 200 silicon atoms per molecule, and represented by the following average compositional formula (I):
Y a R 1 b SiO (4-a-b)/2   (I)

wherein R 1 is an alkyl group having 1 to 12 carbon atoms, alkenyl group having 2 to 12 carbon atoms, aryl group having 6 to 20 carbon atoms, alkoxy group having 1 to 6 carbon atoms, or a hydroxyl group; Y is an acylphosphinate residue represented by the following general formula (II):

wherein R 2 is a non-substituted or halogen-substituted alkyl group having 1 to 12 carbon atoms, a non-substituted or halogen-substituted aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms; R 3 is a linear or branched alkylene group having 1 to 12 carbon atoms; R 4 is an alkylene group having 2 to 6 carbon atoms; Ar is a non-substituted, an alkoxy-substituted, or a halogen-substituted aryl group having 6 to 20 carbon atoms; and subscript m is an integer of from 0 to 100; and
subscripts a and b are numbers satisfying the following conditions: 0<a≤2, 0<b≤3, and a≤b; the method comprising the following steps:
i) reacting an organosilicon compound represented by the following average compositional formula (IV):
Z a R 1 b SiO (4-a-b)/2   (IV)

wherein R 1 and subscripts a and b are each as described above; and Z is a group represented by the following general formula (V):

wherein R 3 , R 4 and subscript m are each as described above;
with an organophosphine compound represented by the following general formula (VI):

wherein R 2 is as described above; and X are the same or different halogen atoms, to obtain a reaction product; and then
ii) reacting the reaction product of step i) with a carboxylic halide represented by the following general formula (VII):

 wherein X and Ar are each as described above.

2. The method according to claim 1 , wherein R 2 is an aryl group having 6 to 20 carbon atoms.

3. The method according to claim 1 , wherein subscript m is 0.

4. The method according to claim 1 , wherein subscripts a and b are numbers satisfying the following condition: a+b≤3.

5. The method according to claim 1 , wherein subscripts a and b are numbers satisfying the following condition: 1.5≤a+b≤2.3.

6. The method according to claim 1 , wherein the organosilicon compound is an organosiloxane represented by the following general formula (III):
R 5 3 SiO(R 5 2 SiO) n SiR 5 3   (III)

wherein each R 5 is independently R 1 or Y as described above, provided at least one R 5 per molecule is Y; and subscript n is an integer of from 0 to 198.

7. The method according to claim 1 , wherein the organosilicon compound is liquid at 25° C.

Assignees

• Dow Toray Co Ltd
• Dow Global Technologies Llc

Inventors

• Jang Eun Sil
• Ogawa Takuya
• Okawa Tadashi

Classifications

• C07F7/0838 Primary

  Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21) · CPC title

• C08G77/14

  containing silicon bound to oxygen-containing groups · CPC title

• C08G77/395

  containing phosphorus · CPC title

• C08L83/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen · CPC title

• C08L83/04

  Polysiloxanes · CPC title