US 12,240,978 B2
Methods for producing polycarbonate copolymer and polysiloxane compound, polycarbonate copolymer, polysiloxane compound, composition, and molded body
Kazuyoshi Uera, Tokyo (JP); Kohei Kamatani, Tokyo (JP); Keisuke Tomita, Tokyo (JP); and Hisato Akimoto, Tokyo (JP)
Assigned to MITSUBISHI GAS CHEMICAL COMPANY, INC., Tokyo (JP)
Filed by MITSUBISHI GAS CHEMICAL COMPANY, INC., Tokyo (JP)
Filed on Oct. 4, 2021, as Appl. No. 17/492,937.
Application 17/492,937 is a continuation of application No. 17/439,490, previously published as PCT/JP2020/012523, filed on Mar. 19, 2020.
Claims priority of application No. 2019-055563 (JP), filed on Mar. 22, 2019; and application No. 2019-055569 (JP), filed on Mar. 22, 2019.
Prior Publication US 2022/0033655 A1, Feb. 3, 2022
Int. Cl. C08L 83/16 (2006.01); C08G 64/08 (2006.01); C08G 64/16 (2006.01); C08G 64/38 (2006.01); C08G 77/448 (2006.01); C08G 77/60 (2006.01); C08L 69/00 (2006.01); G02B 1/04 (2006.01); C08G 77/00 (2006.01); C08G 77/08 (2006.01)
CPC C08L 83/16 (2013.01) [C08G 64/085 (2013.01); C08G 64/1666 (2013.01); C08G 64/38 (2013.01); C08G 77/448 (2013.01); C08G 77/60 (2013.01); C08L 69/00 (2013.01); G02B 1/041 (2013.01); C08G 77/08 (2013.01); C08G 77/80 (2013.01)] 12 Claims
 
1. A method for producing a polysiloxane compound, which includes polymerization of monomers comprising:
an oxy silane compound comprising at least any one of a diaryloxy silane compound that is any one of dialkyldiaryloxy silane, diaryldiaryloxy silane and monoalkylmonoaryldiaryloxy silane, and a dialkoxy silane compound that is any one of dialkyldialkoxy silane, diaryldialkoxy silane and monoalkylmonoaryldialkoxy silane; and
a diol compound selected from

OG Complex Work Unit Chemistry
wherein
in the polymerization, the oxy silane compound and the diol compound are polymerized using a transesterification catalyst, while removing the generated aryl alcohol and/or alkyl alcohol, in a molten state and under reduced pressure,
the monomers for polymerization do not comprise a carbonate compound, and
the amount of the transesterification catalyst to the diol compound is 0.01 μmol/mol to 16,000 μmol/mol at a molar ratio, so that
a poly(arylene/alkylene) siloxane compound with a weight average molecular weight of 10,000 to 300,000, comprising a constituent unit represented by any one of the following formulae (1-1′) to (1-4′), is produced:

OG Complex Work Unit Chemistry
wherein, in the above formulae (1-1) to (1-4) and (1-1′) to (1-4′), R1 and R2 each independently represent an alkyl group containing 1 to 20 carbon atoms and optionally having a substituent, or an aryl group containing 6 to 30 carbon atoms and optionally having a substituent,
R3 to R10 and R30 to R33 each independently represent hydrogen, halogen, alkoxy, an alkyl group containing 1 to 20 carbon atoms and optionally having a substituent, an alkenyl group containing 2 to 20 carbon atoms and optionally having a substituent, or an aryl group containing 6 to 30 carbon atoms and optionally having a substituent,
Z1 and Z2 each independently represent an alkylene group containing 1 to 5 carbon atoms and optionally having a substituent,
J1 each independently represent an integer of 0 or more and 5 or less,
K1 each independently represents an integer of 0 or more and 5 or less,
A1 and A2 each independently represent either —O—or —CH—,
L1 and L2 each independently represent an integer of 0 or more and 3 or less,
m1 to m4 each represent the total number of constituent units in each formula, which is a natural number of 10 or more and 1000 or less, and
X represents a single bond or any one of structural formulae represented by the following formula (2):

OG Complex Work Unit Chemistry
wherein R11 and R12 each independently represent hydrogen, halogen, an alkyl group containing 1 to 20 carbon atoms and optionally having a substituent, or an aryl group containing 6 to 30 carbon atoms and optionally having a substituent, or R11 and R12 bind to each other to form a carbocyclic or heterocyclic ring containing 1 to 20 carbon atoms and optionally having a substituent,
a and b each independently represent an integer of 0 or 1 or more and 5000 or less;
wherein the transesterification catalyst comprises an alkali metal compound and/or an alkaline-earth metal compound comprising any one or more of a carbonate, a hydroxide and an oxide;
wherein the polymerization is initially carried out at atmospheric pressure followed by a step-wise reduction in pressure to a final pressure of 400 Pa or less; and
in the polymerization, the polysiloxane compound is produced, while removing alcohol generated as a by-product.