Polysiloxane compound and method of producing the same
A polysiloxane represented by the formula (1) or (2): where R, R 1 , R 2 , m and n are defined in the specification.
1. A polysiloxane represented by the formula (1):
where in the formula (1):
R independently represents
alkyl having 1 to 45 carbon atoms whereby optional hydrogen may be replaced by fluorine and optional —CH 2 — may be replaced by —O—, —CH═CH—, or cycloalkylene;
cycloalkyl having 4 to 8 carbon atoms;
substituted or unsubstituted aryl whereby optional hydrogen on aryl may be replaced by halogen or alkyl having 1 to 10 carbon atoms in which optional hydrogen may be replaced by fluorine and optional —CH 2 — may be replaced by —O—, —CH═CH—, or phenylene; or
substituted or unsubstituted arylalkyl whereby optional hydrogen on aryl may be replaced by halogen or alkyl having 1 to 10 carbon atoms in which optional hydrogen may be replaced by fluorine, and optional —CH 2 — may be replaced by —O—, —CH═CH—, or phenylene, and alkylene of the arylalkyl has 1 to 10 carbon atoms whereby optional hydrogen may be replaced by fluorine and optional —CH 2 — may be replaced by —O—, —CH═CH—, or phenylene;
m and n independently represent an integer of 1 to 1,000;
wherein when m=1, R 1 is independently selected from the group consisting of alkoxy, acetoxy, and —OSi(A) 3 , and when 2≦m≦1,000, R1 is independently selected from the group consisting of hydrogen, hydroxyl, halogen, alkoxy, acetoxy, —OSi(A) 3 , and a group defined in the same manner as R;
in —OSi(A) 3 , A independently represents
hydrogen;
alkyl having 1 to 10 carbon atoms whereby optional hydrogen may be replaced by hydroxyl, halogen, carboxyl, ester, 2,4-dioxo-3-oxacyclopentyl, acetoxy, amino group, isocyanate, oxiranyl, 3,4-epoxycyclohexyl, oxetanyl, cyano, vinyl, (meth)acryloyl, 4-vinylphenyl, alkyleneoxy, or mercapto, and optional —CH 2 — may be replaced by —O—, —CH═CH— or phenylene; or phenyl.
2. A polysiloxane represented by the formula (1-0):
where in the formula (1-0):
m represents an integer of 1 to 1,000;
when m=1, R 1 is independently selected from the group consisting of alkoxy, acetoxy, and —OSi(A) 3 , and when 2≦m≦1,000, R 1 is independently selected from the group consisting of hydrogen, hydroxyl, halogen, alkoxy, acetoxy, —OSi(A) 3 , alkyl having 1 to 10 carbon atoms, and phenyl;
in —OSi(A) 3 , A independently represents
hydrogen;
alkyl having 1 to 10 carbon atoms whereby optional hydrogen may be replaced by hydroxyl, halogen, carboxyl, ester, 2,4-dioxo-3-oxacyclopentyl, acetoxy, amino group, isocyanate, oxiranyl, 3,4-epoxycyclohexyl, oxetanyl, cyano, vinyl, (meth)acryloyl, 4-vinylphenyl, alkyleneoxy, or mercapto, and optional —CH 2 — may be replaced by —O—, —CH═CH— or phenylene; or phenyl.
3. A polysiloxane represented by the formula (1-1):
where in the formula (1-1), m represents an integer of 1 to 1,000.
4. A polysiloxane represented by the formula (1-2):
where in the formula (1-2), m represents an integer of 2 to 1,000.
5. A polysiloxane represented by the formula (1-3):
where in the formula (1-3), A independently represents
hydrogen;
alkyl having 1 to 10 carbon atoms whereby optional hydrogen may be replaced by hydroxyl, halogen, carboxyl, ester, 2,4-dioxo-3-oxacyclopentyl, acetoxy, amino group, isocyanate, oxiranyl, 3,4-epoxycyclohexyl, an oxetanyl, cyano, vinyl, (meth)acryloyl , 4-vinylphenyl, alkyleneoxy, or mercapto, and optional —CH 2 — may be replaced by —O—, —CH═CH— or phenylene; or
phenyl; and
m represents an integer of 1 to 1,000.
6. A polysiloxane represented by the formula (1-4):
where in the formula (1-4), m represents an integer of 1 to 1,000.
7. A polysiloxane represented by the formula (1-5):
where in the formula (1-5), m represents an integer of 2 to 1,000.
8. A polysiloxane represented by the formula (1-6):
where in the formula (1-6), m represents an integer of 1 to 1,000.
9. A method of producing a polysiloxane represented by the formula (1-a), comprising reacting a compound represented by the formula (1-0-1) with a compound represented by the formula (1-0-2):
where in the formula (1-0-1),
R independently represents
alkyl having 1 to 45 carbon atoms whereby optional hydrogen may be replaced by fluorine, and optional —CH 2 — may be replaced by —O— or —CH═CH—;
cycloalkyl having 4 to 8 carbon atoms;
substituted or unsubstituted aryl whereby optional hydrogen on aryl may be replaced by halogen or alkyl having 1 to 10 carbon atoms in which optional hydrogen may be replaced by fluorine, and optional —CH 2 — may be replaced by —O— or —CH═CH—; or
substituted or unsubstituted arylalkyl whereby optional hydrogen on aryl may be replaced by halogen or alkyl having 1 to 10 carbon atoms in which optional hydrogen may be replaced by fluorine, and optional —CH 2 — may be replaced by —O— or —CH═CH—, and alkylene of the arylalkyl has 1 to 10 carbon atoms, and optional —CH 2 — in the alkylene may be replaced by —O—; and
in the formula (1-0-2),
X represents a group capable of reacting with silanol;
where in the formula (1-a),
R represents a group defined in the same manner as R in the formula (1-0-1);
X represent a group defined in the same manner as X in the formula (1-0-2); and
m and n represent an integer of 1 to 1,000.
10. A method of producing a polysiloxane represented by the formula (1-a′), comprising reacting a compound represented by the formula (1-0-1′) with a compound represented by the formula (1-0-2′):
where in the formula (1-0-1′) and (1-0-2′)
M is alkali metal, and R independently represents
alkyl having 1 to 45 carbon atoms whereby optional hydrogen may be replaced by fluorine, and optional —CH 2 — may be replaced by —O— or —CH═CH—;
cycloalkyl having 4 to 8 carbon atoms;
substituted or unsubstituted aryl whereby optional hydrogen on aryl may be replaced by halogen or alkyl having 1 to 10 carbon atoms in which optional hydrogen may be replaced by fluorine, and optional —CH 2 — may be replaced by —O— or —CH═CH—; or
substituted or unsubstituted arylalkyl whereby optional hydrogen on aryl may be replaced by halogen or alkyl having 1 to 10 carbon atoms in which optional hydrogen may be replaced by fluorine, and optional —CH 2 — may be replaced by —O— or —CH═CH—, and alkylene of the arylalkyl has 1 to 10 carbon atoms, and optional —CH 2 —in the alkylene may be replaced by —O—; and
X 1 represents halogen;
where in the formula (1-a′),
R represents a group defined in the same manner as R in the formula (1-0-1′);
X 1 represents a group defined in the same manner as X 1 in the formula (1-0-2′); and
m and n represent an integer of 1 to 1,000.
11. A method of producing a compound represented by the formula (1-b), comprising producing a compound represented by the formula (1-a) by the method according to claim 9 , and hydrolyzing the resultant compound represented by the formula (1-a):
where in the formula (1-b),
R represents a group defined in the same manner as in the formula (1-a); and
m represents an integer of 2 to 1,000.
12. A method of producing a compound represented by the formula (1-b), comprising producing a compound represented by the formula (1-a′) by the method according to claim 10 , and hydrolyzing the compound represented by the formula (1-a′):
where in the formula (1-b),
R represents a group defined in the same manner as R in the formula (1-a′); and
m represents an integer of 2 to 1,000.
13. A method of producing a compound represented by the formula (1-c), comprising producing a compound represented by the formula (1-b) by the method according to claim 11 or 12 , and reacting the compound represented by the formula (1-b) with a compound represented by the formula (1-0-3):
where in the formula (1-0-3) and (1-c),
R represents a group defined in the same manner as R in the formula (1-b);
m represents an integer of 1 to 1,000;
X represents a group capable of reacting with silanol;
A independently represents
hydrogen;
alkyl having 1 to 10 carbon atoms whereby optional hydrogen may be replaced by hydroxyl, halogen, carboxyl, ester, 2,4-dioxo-3-oxa-cyclopentyl, acetoxy, amino group, isocyanate, oxiranyl, 3,4-epoxycyclohexyl, oxetanyl, cyano, vinyl, (meth)acryloyl, 4-vinylphenyl, alkyleneoxy, or mercapto, and optional —CH 2 — may be replaced by —O—, —CH═CH— or phenylene; or
phenyl.
14. A method of producing a compound represented by the formula (1-c), comprising producing a compound represented by the formula (1-a) by the method according to claim 9 , and reacting the compound represented by the formula (1-a) with a compound represented by the formula (1-0-4):
where in the formula (1-0-4) and (1-c),
R represents a group defined in the same manner as R in the formula (1-a);
m represents an integer of 1 to 1,000;
A independently represents
hydrogen;
alkyl having 1 to 10 carbon atoms whereby optional hydrogen may be replaced by hydroxyl, halogen, carboxyl, ester, 2,4-dioxo-3-oxa-cyclopentyl, acetoxy , amino group, isocyanate, oxiranyl, 3,4-epoxycyclohexyl, oxetanyl, cyano, vinyl, (meth)acryloyl, 4-vinylphenyl, alkyleneoxy, or mercapto, and optional —CH 2 — may be replaced by —O—, —CH═CH— or phenylene; or
phenyl.
15. A method of producing a compound represented by the formula (1-c), comprising producing a compound represented by the formula (1-a′) by the method according to claim 10 , and reacting the compound represented by the formula (1-a′) with a compound represented by the formula (1-0-4):
where in the formula (1-0-4) and (1-c),
R represents a group defined in the same manner as R in the formula (1-a′);
m represents an integer of 1 to 1,000;
A independently represents
hydrogen;
alkyl having 1 to 10 carbon atoms whereby optional hydrogen may be replaced by hydroxyl, halogen, carboxyl, ester, 2,4-dioxo-3-oxa-cyclopentyl, acetoxy, amino group, isocyanate, oxiranyl, 3,4-epoxycyclohexyl, oxetanyl, cyano, vinyl, (meth)acryloyl, 4-vinylphenyl, alkyleneoxy, or mercapto, and optional —CH 2 — may be replaced by —O—, —CH═CH— or phenylene; or
phenyl.
16. A method of producing a compound represented by the formula (1-d), comprising producing a compound represented by the formula (1-c) in which at least one of A's represents hydrogen, and remaining of A's represent alkyl having 1 to 10 carbon atoms, phenyl, or phenylalkyl by the method according to claim 13 , and reacting the resultant compound with a compound represented by the formula (1-0-5):
where in the formula (1-0-5) and (1-d),
A 1 represents alkyl having 1 to 8 carbon atoms whereby optional hydrogen may be replaced by hydroxyl, halogen, carboxyl, ester, 2,4-dioxo-3-oxa-cyclopentyl, acetoxy, amino group, isocyanate, oxiranyl, 3,4-epoxycyclohexyl, oxetanyl, cyano, vinyl, (meth)acryloyl, 4-vinylphenyl, alkyleneoxy, or mercapto, and optional —CH 2 — may be replaced by —O—, —CH═CH— or phenylene;
R represents a group defined in the same manner as R in the formula (1-c); and
at least one of A 2 's represents —CH 2 CH 2 A 1 , and remaining of A 2 's are independently selected from the group consisting of alkyl having 1 to 10 carbon atoms, phenyl, and phenylalkyl.
17. A method of producing a compound represented by the formula (1-d), comprising producing a compound represented by the formula (1-c) in which at least one of A's represents hydrogen, and remaining of A's represent alkyl having 1 to 10 carbon atoms, phenyl, or phenylalkyl by the method according to claim 14 , and reacting the resultant compound with a compound represented by the formula (1-0-5):
where in the formula (1-0-5) and (1-d),
A 1 represents alkyl having 1 to 8 carbon atoms whereby optional hydrogen may be replaced by hydroxyl, halogen, carboxyl, ester, 2,4-dioxo-3-oxa-cyclopentyl, acetoxy, amino group, isocyanate, oxiranyl, 3,4-epoxycyclohexyl, oxetanyl, cyano, vinyl, (meth)acryloyl, 4-vinylphenyl, alkyleneoxy, or mercapto, and optional —CH 2 — may be replaced by —O—, —CH═CH— or phenylene;
R represents a group defined in the same manner as R in the formula (1-c); and
at least one of A 2 's represents —CH 2 CH 2 A 1 , and remaining of A 2 's are independently selected from the group consisting of alkyl having 1 to 10 carbon atoms, phenyl, and phenylalkyl.
18. A method of producing a compound represented by the formula (1-d), comprising producing a compound represented by the formula (1-c) in which at least one of A's represents hydrogen, and remaining of A's represent alkyl having 1 to 10 carbon atoms, phenyl, or phenylalkyl by the method according to claim 15 , and reacting the resultant compound with a compound represented by the formula (1-0-5):
where in the formula (1-0-5) and (1-d),
A 1 represents alkyl having 1 to 8 carbon atoms whereby optional hydrogen may be replaced by hydroxyl, halogen, carboxyl, ester, 2,4-dioxo-3-oxa-cyclopentyl, acetoxy, amino group, isocyanate, oxiranyl, 3,4-epoxycyclohexyl, oxetanyl, cyano, vinyl, (meth)acryloyl, 4-vinylphenyl, alkyleneoxy, or mercapto, and optional —CH 2 — may be replaced by —O—, —CH═CH—, or phenylene;
R represents a group defined in the same manner as R in the formula (1-c); and
at least one of A 2 's represents —CH 2 CH 2 A 1 , and remaining of A 2 's are independently selected from the group consisting of alkyl having 1 to 10 carbon atoms, phenyl, and phenylalkyl.