Organosilicon compound, method for producing thereof, and curable silicone composition containing the same

1. An organosilicon compound represented by the following general formula (I):

wherein

R 1 represents a substituted or non-substituted, saturated divalent hydrocarbon group having 3 to 12 carbon atoms, or a substituted or non-substituted divalent hydrocarbon group having 3 to 12 carbon atoms and having an unsaturated carbon-carbon double bond or triple bond, with the provisos that when R 1 is a branched chain, no aliphatic unsaturated carbon-carbon bond is contained at the terminal of the molecular chain of the branched chain, and that when R 1 has a substituent, no aliphatic unsaturated carbon-carbon bond is contained at the terminal of the molecular chain of the substituent;

R 2 is a monovalent hydrocarbon group having 1 to 10 carbon atoms and having no aliphatic unsaturated bond at the terminal of the molecular chain;

R 3 is a monovalent hydrocarbon group having 1 to 18 carbon atoms and having no aliphatic unsaturated bond at the terminal of the molecular chain, or an alkoxyalkyl group having 2 to 18 carbon atoms;

R 4 is a substituted or non-substituted divalent hydrocarbon group having 1 to 12 carbon atoms, with the provisos that when R 4 is a branched chain, no aliphatic unsaturated carbon-carbon bond is contained at the terminal of the molecular chain of the branched chain, and that when R 4 has a substituent, no aliphatic unsaturated carbon-carbon bond is contained at the terminal of the molecular chain of the substituent;

each R 5 is independently a monovalent hydrocarbon group having 1 to 10 carbon atoms and having no aliphatic unsaturated bond at the terminal of the molecular chain;

m is an integer ranging from 1 to 20; and

n is 0, 1 or 2.

2. A method for producing the organosilicon compound according to claim 1 , the method comprising reacting an alkenyl-functional succinic anhydride represented by the following general formula (II):

wherein

R 6 is a substituted or non-substituted divalent hydrocarbon group having 1 to 10 carbon atoms; and

an organosilicon compound represented by the following general formula (III):

wherein

R 2 , R 3 , R 4 , R 5 , m and n are the same as defined above in the general formula (I), in the presence of a hydrosilylation reaction-catalyst.

3. A curable silicone composition comprising the organosilicon compound according to claim 1 as an adhesion promoter.

4. A method for producing a succinic anhydride-functional organosilicon compound, the method comprising reacting an alkenyl-functional organosilicon compound and maleic anhydride, wherein the alkenyl-functional organosilicon compound has a silicon-bonded group that contains a structure: H 2 C═CH—CH 2 — at the terminal of the molecular chain, or a silicon-bonded 2-propenyl group.

5. A method for producing a succinic anhydride-functional organosilicon compound represented by the following general formula (IV):

wherein

R 2 is a monovalent hydrocarbon group having 1 to 10 carbon atoms and having no aliphatic unsaturated bond at the terminal of the molecular chain;

R 3 is a monovalent hydrocarbon group having 1 to 18 carbon atoms and having no aliphatic unsaturated bond at the terminal of the molecular chain, or an alkoxyalkyl group having 2 to 18 carbon atoms;

R 7 represents a single bond directly bonding between —CH 2 — at the left of R 7 and Si atom at the right of R 7 ;

a saturated divalent hydrocarbon group having 1 to 21 carbon atoms, or a substituted or non-substituted divalent hydrocarbon group having 2 to 21 carbon atoms and having an unsaturated carbon-carbon double bond or triple bond, with the provisos that when R 7 is a branched chain, no aliphatic unsaturated carbon-carbon bond is contained at the terminal of the molecular chain of the branched chain, and that when R 7 has a substituent, no aliphatic unsaturated carbon-carbon bond is contained at the terminal of the molecular chain of the substituent; or

a group represented by the following formula:

—R 8 —(Si(R 10 ) 2 O) a —R 9 —

wherein each R 8 and R 9 is independently a substituted or non-substituted saturated divalent hydrocarbon group having 1 to 15 carbon atoms, or a substituted or non-substituted divalent hydrocarbon group having 2 to 15 carbon atoms and having an unsaturated carbon-carbon double bond or triple bond, with the provisos that when the divalent hydrocarbon group is a branched chain, no aliphatic unsaturated carbon-carbon bond is contained at the terminal of the molecular chain of the branched chain, and that when the divalent hydrocarbon group has a substituent, no aliphatic unsaturated carbon-carbon bond is contained at the terminal of the molecular chain of the substituent;

R 10 is a monovalent hydrocarbon group having 1 to 10 carbon atoms and having no aliphatic unsaturated bond at the terminal of the molecular chain; and

a is an integer ranging from 0 to 10; and

n′ is 0, 1 or 2;

the method comprising reacting

an alkenyl-functional organosilicon compound represented by the following general formula (V):

wherein

R 2 , R 3 , R 7 and n′ are the same as defined above in the formula (IV); and

a maleic anhydride represented by the following formula (VI):

6. The method according to claim 5 , wherein a temperature for the reaction between the alkenyl-functional organosilicon compound and maleic anhydride is in the range of 100° C. to 180° C.

7. The method according to claim 5 , wherein the alkenyl-functional organosilicon compound is used in amount ranging from 1 to 10 mol with respect to one mol of the maleic anhydride.

8. A curable silicone composition comprising:

(A) an organopolysiloxane having at least two alkenyl groups in a molecule, in an amount of 100 parts by mass;

(B) an organopolysiloxane having at least two silicon-bonded hydrogen atoms in a molecule, in an amount in which an amount of the silicon-bonded hydrogen atom in said component (B) ranges from 0.1 to 10 mol with respect to 1 mol of the alkenyl group of said component (A);

(C) a hydrosilylation-reaction catalyst, in a catalytic amount; and

(D) an acid anhydride represented by the following general formula (1):

wherein

R 1 represents a substituted or non-substituted, saturated divalent hydrocarbon group having 3 to 12 carbon atoms, or a substituted or non-substituted divalent hydrocarbon group having 3 to 12 carbon atoms and having an unsaturated carbon-carbon double bond or triple bond, with the provisos that when R 1 is a branched chain, no aliphatic unsaturated carbon-carbon bond is contained at the terminal of the molecular chain of the branched chain, and that when R 1 has a substituent, no aliphatic unsaturated carbon-carbon bond is contained at the terminal of the molecular chain of the substituent;

R 2 is a monovalent hydrocarbon group having 1 to 10 carbon atoms and having no aliphatic unsaturated bond at the terminal of the molecular chain;

R 3 is a monovalent hydrocarbon group having 1 to 18 carbon atoms and having no aliphatic unsaturated bond at the terminal of the molecular chain, or an alkoxyalkyl group having 2 to 18 carbon atoms;

R 4 is a substituted or non-substituted divalent hydrocarbon group having 1 to 12 carbon atoms, with the provisos that when R 4 is a branched chain, no aliphatic unsaturated carbon-carbon bond is contained at the terminal of the molecular chain of the branched chain, and that when R 4 has a substituent, no aliphatic unsaturated carbon-carbon bond is contained at the terminal of the molecular chain of the substituent;

each R 5 is independently a monovalent hydrocarbon group having 1 to 10 carbon atoms and having no aliphatic unsaturated bond at the terminal of the molecular chain;

m is an integer ranging from 1 to 20; and

n is 0, 1 or 2, in an amount ranging from 0.1 to 20 parts by mass.

9. The curable silicone composition according to claim 8 , wherein said component (A) is a mixture of (A1) a linear organopolysiloxane having at least two alkenyl groups in a molecule and (A2) a branched organopolysiloxane having at least two alkenyl groups in a molecule.

10. The curable silicone composition according to claim 8 , further comprising (E) an organotrialkoxysilane.

11. The method according to claim 6 , wherein the alkenyl-functional organosilicon compound is used in amount ranging from 1 to 10 mol with respect to one mol of the maleic anhydride.