Organopolysiloxane compound, method for producing same, and antistatic agent and curable composition, each of which contains same

A method of preparing an organopolysiloxane represented by average structural formula (1)

• wherein Z is a single bond or a 2 to 20-valent group which includes an organopolysiloxane structure,
• each R1 is independently a single bond or a substituted or unsubstituted alkylene group of 1 to 20 carbon atoms,
• R2 and R3 are each independently a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms or aryl group of 6 to 10 carbon atoms,
• each Y is independently a polymerizable reactive group-containing monovalent hydrocarbon group, p1 is a number from 1 to 10, q is a number from 1 to 10, and p+q is a number from 2 to 20 corresponding to the valence of Z, with the proviso that when Z is a single bond, p and q are both 1,
• A- is a monovalent anion, and
• Q+is a monovalent cationic group represented by any one of formulas (2) (3) to (4) below:
• wherein R4 to R10 are each independently an alkyl group of 1 to 20 carbon atoms, an aryl group of 6 to 20 carbon atoms or an aralkyl group of 7 to 20 carbon atoms;
• R11 to R13 are each independently a hydrogen atom, an alkyl group of 1 to 20 carbon atoms or an aryl group of 6 to 20 carbon atoms;
• R4 and R5 may mutually bond to form, together with the nitrogen atom, a pyrrolidine ring which may have a substituent, a piperidine ring which may have a substituent or a pyridine ring which may have a substituent;
• R7 and R8 may mutually bond to form, together with the phosphorus atom, a phosphorane ring which may have a substituent, a phosphorinane ring which may have a substituent or a phosphorine ring which may have a substituent;
• and
• represents a site available for bonding;
• with the provisos that when R4 and R5 mutually bond to form a pyridine ring, R6 does not exist, and when R7 and R8 mutually bond to form a phosphorine ring, R9 does not exist;
• wherein the method comprises the step of reacting a polymerizable reactive group and silanolic hydroxyl group-containing organopolysiloxane compound of average structural formula (6)
• wherein wherein R1, R2, R3, Y, p, q and Z are as defined above, and OH is a silanolic hydroxyl group with a compound of formula (7)
• wherein wherein R1, R2, R3, A and Q+are as defined above, and X is a leaving group selected from alkoxy groups of 1 to 10 carbon atoms, halogen atoms and a hydroxyl group having a functional group capable of reacting with the silanolic hydroxyl group and having an ionic group.

A method of preparing an organopolysiloxane compound represented by average structural formula (5)

• wherein each R1 is independently a single bond or a substituted or unsubstituted alkylene group of 1 to 20 carbon atoms,
• R2 and R3 are each independently a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms or aryl group of 6 to 10 carbon atoms,
• Y is a polymerizable reactive group-containing monovalent hydrocarbon group,
• A- is a monovalent anion,
• Q+ is a monovalent cationic group represented by any one of formulas (2) (3) to (4) below:
• wherein R4 to R10 are each independently an alkyl group of 1 to 20 carbon atoms, an aryl group of 6 to 20 carbon atoms or an aralkyl group of 7 to 20 carbon atoms;
• R11 to R13 are each independently a hydrogen atom, an alkyl group of 1 to 20 carbon atoms or an aryl group of 6 to 20 carbon atoms;
• R4 and R5 may mutually bond to form, together with the nitrogen atom, a pyrrolidine ring which may have a substituent, a piperidine ring which may have a substituent or a pyridine ring which may have a substituent;
• R7 and R8 may mutually bond to form, together with the phosphorus atom, a phosphorane ring which may have a substituent, a phosphorinane ring which may have a substituent or a phosphorine ring which may have a substituent;
• and
• * represents a site available for bonding;
• with the provisos that when R4 and R5 mutually bond to form a pyridine ring, R6 does not exist, and when R7 and R8 mutually bond to form a phosphorine ring, R9 does not exist, R14 and R15 are each independently a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms or aryl group of 6 to 10 carbon atoms, and m is a number of 0 or more;
• wherein the method comprises the step of reacting a polymerizable reactive group and silanolic hydroxyl group-containing organopolysiloxane compound of average structural formula (8)
• wherein R1, R2, R3, R14, R15, Y and m are as defined above with a compound of formula (7)
• wherein R1, R2, R3, A1, and Q+and X are as defined above, and X is a leaving group selected from alkoxy groups of 1 to 10 carbon atoms, halogen atoms and a hydroxyl group having a functional group capable of reacting with the silanolic hydroxyl group and having an ionic group.