IP Library Granted Patent US 12,024,535
Granted Patent B2
US 12,024,535 · App. 17/281,661 · Granted Jul 2, 2024

Organosilicon compound, method for producing thereof, and use thereof

Inventors: Eun Sil Jang (Midland, MI); Takuya Ogawa (Tokyo, JP); Tadashi Okawa (Tokyo, JP)
Assignees: DOW TORAY CO., LTD.; DOW GLOBAL TECHNOLOGIES LLC
C07F9/3264
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Quick Facts
Patent No.
US 12,024,535
App. No.
17/281,661
Granted
Jul 2, 2024
Kind
B2
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): Y a R 1 b SiO (4-a-b)/2 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 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.

Claims (21)

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.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2024
From: JANG, EUN SIL
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 067322/0747 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2024
From: OKAWA, TADASHI; OGAWA, TAKUYA
To: DOW TORAY CO., LTD.
Reel/Frame 067322/0906 →
Continuity (1)
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