Organosilicon compound, method for producing thereof, and use thereof
View Patent ↗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.
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.