Phosphorus-containing organosilicon compound, a method for producing the same, and a resin composition or a coating composition containing the same
View Patent ↗The present invention provides a novel phosphorus-containing organosilicon compound furnished with performance of an oxaphosphorin compound, a method for producing therefore and a resin composition containing the same, particularly a polyester or polycarbonate resin composition and a coating composition containing the same, characterized by that said phosphorus-containing organosilicon compound has in the molecule a phosphorus-containing group (an X group) bonded to a silicon atom and represented by the following chemical formula (1)
1. A phosphorus-containing organosilicon compound, characterized by having in the molecule a phosphorus-containing group (an X group) bonded to a silicon atom and represented by the following chemical formula (6′):
wherein R 3 and R 4 each independently represents a substituted or unsubstituted bivalent hydrocarbon group; and R 10 and R 11 may be the same or different each other and each represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
2. A phosphorus-containing organosilicon compound, characterized by being represented by the following chemical formula (2):
X a R 5 b SiO (4−a−b)/2 (2)
[wherein X is a phosphorus-containing group represented by the chemical formula (6′):
wherein R 3 and R 4 each independently represents a substituted or unsubstituted bivalent hydrocarbon group; and R 10 and R 11 may be the same or different each other and each represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.); R 5 represents the same or different an organic groups selected from an alkyl group, an aryl group, an aralkyl group, and a fluorine-substituted alkyl or alkoxy group each having 1 to 30 carbon atoms; a and b are numbers in the range of 0.001≦a≦1.5 and 0≦b≦3.0, respectively].
3. The phosphorus-containing organosilicon compound according to claim 2 , wherein the chemical formula (2) is represented by the following chemical formula (3).
R 5 3 SiO—(R 5 2 SiO)x(R 5 XSiO)y-SiR 5 3 (3)
(wherein, R 5 and X are each the same as the above; x is an integer of 0 or not less than 1; and y is an integer of not less than 1).
4. A phosphorus-containing organosilicon compound or a condensate thereof, characterized by being represented by the following chemical formula (4):
XSiR 6 c (OR 7 ) (3−c) (4)
[wherein X is a phosphorus-containing group represented by the chemical formula (6′):
wherein R 3 and R 4 each independently represents a substituted or unsubstituted bivalent hydrocarbon group; and R 10 and R 11 may be the same or different each other and each represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.); R 6 is the same or different organic groups selected from an alkyl group, an aryl group, an aralkyl group, or a fluorine-substituted alkyl group each having 1 to 30 carbon atoms; R 7 represents the same or different organic groups selected from an alkyl group, an aryl group, an aralkyl group, or a fluorine-substituted alkyl group each having 1 to 30 carbon atoms; and c is 0 or 1].
5. A phosphorus-containing organosilicon compound, characterized by being represented by the following chemical formula (5):
XSiR 5 c (OSiR 8 3 ) (3−c) (5)
[wherein X is a phosphorus-containing group represented by the chemical formula (6′):
wherein R 3 and R 4 each independently represents a substituted or unsubstituted bivalent hydrocarbon group; and R 10 and R 11 may be the same or different each other and each represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.); R 5 is the same or different organic groups selected from an alkyl group, an aryl group, an aralkyl group, and a fluorine-substituted alkyl or alkoxy group each having 1 to 30 carbon atoms; R 8 represents the same or different organic groups selected from an alkyl group, an aryl group, an aralkyl group, and a fluorine-substituted alkyl or alkoxy group each having 1 to 30 carbon atoms; and c is 0 or 1].
6. A method for producing the phosphorus-containing organosilicon compound or the condensate thereof according to claim 1 , characterized by that they are obtained by reaction of a compound represented by the following chemical formula (7):
(wherein R 1 and R 2 may be the same or different, and each represents a linear or branched alkyl group having 1 to 8 carbon atoms, an alicyclic group having 5 to 6 carbon atoms in the ring, an unsubstituted or substituted aryl group having 6 to 10 carbon atoms, or a group forming a 5 to 8-membered ring with a phosphorus atom; and m is 0 or 1) and a silicon compound having in the molecule an unsaturated ester group bonded to a silicon atom, represented by the following chemical formula (8):
(wherein R 4 represents a substituted or unsubstituted bivalent hydrocarbon group; and R 9 represents a substituted or unsubstituted unsaturated hydrocarbon group).
7. A method for producing the phosphorus-containing organosilicon compound, or the condensate thereof according to claim 4 , characterized by that they are obtained by reaction of a compound represented by the following chemical formula (7):
(wherein R 1 and R 2 may be the same or different, and each represents a linear or branched alkyl group having 1 to 8 carbon atoms, an alicyclic group having 5 to 6 carbon atoms in the ring, an unsubstituted or substituted aryl group having 6 to 10 carbon atoms, or a group forming a 5 to 8-membered ring with a phosphorus atom; and m is 0 or 1) and a silicon compound represented by the following chemical formula (9):
YSiR 6 c (OR 7 ) (3−c) (9)
[wherein Y is an unsaturated ester group represented by the chemical formula (8):
(wherein R 4 represents a substituted or unsubstituted bivalent hydrocarbon group; R 9 represents a substituted or unsubstituted unsaturated hydrocarbon group); R 6 represents the same or different organic groups selected from an alkyl group, an aryl group, an aralkyl group or a fluorine-substituted alkyl group each having 1 to 30 carbon atoms; R 7 represents the same or different organic groups selected from an alkyl group, an aryl group, an aralkyl group or a fluorine-substituted alkyl group each having 1 to 30 carbon atoms; and c is 0 or 1].
8. A method for producing the phosphorus-containing organosilicon compound, according to claim 1 , characterized by that they are obtained using the phosphorus-containing organosilicon compound, or the condensate thereof as an intermediate, the phosphorus-containing organosilicon compound or a condensate thereof, being represented by the following chemical formula (4):
XSiR 6 c (OR 7 ) (3−c) (4)
[wherein X is a phosphorus-containing group represented by the chemical formula (6′):
(wherein R 3 and R 4 each independently represents a substituted or unsubstituted bivalent hydrocarbon group; and R 10 and R 11 may be the same or different each other and each represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.); R 6 is the same or different organic groups selected from an alkyl group, an aryl group, an aralkyl group, or a fluorine-substituted alkyl group each having 1 to 30 carbon atoms; R 7 represents the same or different organic groups selected from an alkyl group, an aryl group, an aralkyl group, or a fluorine-substituted alkyl group each having 1 to 30 carbon atoms; and c is 0 or 1].
9. A resin composition, characterized by containing the phosphorus-containing organosilicon compound, or the condensate thereof according to claim 1 .
10. The resin composition according to claim 9 , characterized by being a polyester or polycarbonate resin composition.
11. A coating composition, characterized by containing the phosphorus-containing organosilicon compound, or the condensate thereof according to claim 1 .
12. A method for producing the phosphorus-containing organosilicon compound or the condensate thereof according to claim 2 , characterized by that they are obtained by reaction of a compound represented by the following chemical formula (7):
(wherein R 1 and R 2 may be the same or different, and each represents a linear or branched alkyl group having 1 to 8 carbon atoms, an alicyclic group having 5 to 6 carbon atoms in the ring, an unsubstituted or substituted aryl group having 6 to 10 carbon atoms, or a group forming a 5 to 8-membered ring with a phosphorus atom; and m is 0 or 1) and a silicon compound having in the molecule an unsaturated ester group bonded to a silicon atom, represented by the following chemical formula (8):
(wherein R 4 represents a substituted or unsubstituted bivalent hydrocarbon group; and R 9 represents a substituted or unsubstituted unsaturated hydrocarbon group).
13. A method for producing the phosphorus-containing organosilicon compound or the condensate thereof according to claim 4 , characterized by that they are obtained by reaction of a compound represented by the following chemical formula (7):
(wherein R 1 and R 2 may be the same or different, and each represents a linear or branched alkyl group having 1 to 8 carbon atoms, an alicyclic group having 5 to 6 carbon atoms in the ring, an unsubstituted or substituted aryl group having 6 to 10 carbon atoms, or a group forming a 5 to 8-membered ring with a phosphorus atom; and m is 0 or 1) and a silicon compound having in the molecule an unsaturated ester group bonded to a silicon atom, represented by the following chemical formula (8):
(wherein R 4 represents a substituted or unsubstituted bivalent hydrocarbon group; and R 9 represents a substituted or unsubstituted unsaturated hydrocarbon group).
14. A method for producing the phosphorus-containing organosilicon compound or the condensate thereof according to claim 5 , characterized by that they are obtained by reaction of a compound represented by the following chemical formula (7):
(wherein R 1 and R 2 may be the same or different, and each represents a linear or branched alkyl group having 1 to 8 carbon atoms, an alicyclic group having 5 to 6 carbon atoms in the ring, an unsubstituted or substituted aryl group having 6 to 10 carbon atoms, or a group forming a 5 to 8-membered ring with a phosphorus atom; and m is 0 or 1) and a silicon compound having in the molecule an unsaturated ester group bonded to a silicon atom, represented by the following chemical formula (8):
(wherein R 4 represents a substituted or unsubstituted bivalent hydrocarbon group; and R 9 represents a substituted or unsubstituted unsaturated hydrocarbon group).
15. A method for producing the phosphorus-containing organosilicon compound, according to claim 2 , characterized by that they are obtained using the phosphorus-containing organosilicon compound, or the condensate thereof as an intermediate, the phosphorus-containing organosilicon compound or a condensate thereof, being represented by the following chemical formula (4):
XSiR 6 c (OR 7 ) (3−c) (4)
[wherein X is a phosphorus-containing group represented by the chemical formula (6′):
(wherein R 3 and R 4 each independently represents a substituted or unsubstituted bivalent hydrocarbon group; and R 10 and R 11 may be the same or different each other and each represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.); R 6 is the same or different organic groups selected from an alkyl group, an aryl group, an aralkyl group, or a fluorine-substituted alkyl group each having 1 to 30 carbon atoms; R 7 represents the same or different organic groups selected from an alkyl group, an aryl group, an aralkyl group, or a fluorine-substituted alkyl group each having 1 to 30 carbon atoms; and c is 0 or 1].
16. A method for producing the phosphorus-containing organosilicon compound, according to claim 5 , characterized by that they are obtained using the phosphorus-containing organosilicon compound, or the condensate thereof as an intermediate, being represented by the following chemical formula (4):
XSiR 6 c (OR 7 ) (3−c) (4)
[wherein X is a phosphorus-containing group represented by the chemical formula (6′):
(wherein R 3 and R 4 each independently represents a substituted or unsubstituted bivalent hydrocarbon group; and R 10 and R 11 may be the same or different each other and each represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.); R 6 is the same or different organic groups selected from an alkyl group, an aryl group, an aralkyl group, or a fluorine-substituted alkyl group each having 1 to 30 carbon atoms; R 7 represents the same or different organic groups selected from an alkyl group, an aryl group, an aralkyl group, or a fluorine-substituted alkyl group each having 1 to 30 carbon atoms; and c is 0 or 1].