Organosilicon compound, method for producing thereof, and use thereof

Patent metadata

Field	Value
Publication number	US-2022017547-A1
Application number	US-201917281661-A
Country	US
Kind code	A1
Filing date	Sep 26, 2019
Priority date	Oct 1, 2018
Publication date	Jan 20, 2022
Grant date	—

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

1 . 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.

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

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

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

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

6 . The organosilicon compound 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 organosilicon compound according to claim 6 , wherein the organosilicon compound is liquid at 25° C.

8 . A method for producing the organosilicon compound according to claim 1 , 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.

9 . A photo-initiator comprising the organosilicon compound according to claim 1 .

10 . A photo-curable composition comprising the photo-initiator according to claim 9 .

11 . A photo-initiator comprising the organosilicon compound produced according to the method of claim 8 .

12 . A photo-curable composition comprising the photo-initiator according to claim 11 .

Assignees

• Dow Toray Co Ltd
• Dow Global Technologies Llc

Inventors

• Jang Eun Sil
• Ogawa Takuya
• Okawa Tadashi

Classifications

• C08G77/30

  phosphorus-containing groups · CPC title

• C08L83/08

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

• C08G77/395

  containing phosphorus · CPC title

• C08G77/14

  containing silicon bound to oxygen-containing groups · CPC title

• C08L83/04

  Polysiloxanes · CPC title