Polymer and epoxy resin compositions
View Patent ↗The present invention provides a vinyl polymer with an epoxy group terminally introduced therein and an epoxy resin composition comprising (A) an epoxy resin and (B) a vinyl polymer which has a main chain produced by living radical polymerization and has a reactive functional group at a main chain terminus. A flexible epoxy resin composition can be obtained using these compounds. The invention further provides an epoxy resin composition having an epoxy group at a main chain terminus thereof.
1. An epoxy resin composition
which comprises a vinyl polymer having a group represented by the following general formula (1) at a main chain terminus thereof:
wherein, R 1 , R 2 and R 3 are the same or different and each represents a hydrogen atom, a monovalent hydrocarbon group containing 1 to 10 carbon atoms or a monovalent group containing 1 to 10 carbon atoms as derived from two hydrocarbon groups by being bound together via an ether bond or ester bond, and R 1 and R 2 or R 2 and R 3 may be combined together at respective other termini to form a cyclic structure;
wherein the vinyl polymer having a group represented by the general formula (1) at a main chain terminus thereof is obtained by reacting a reactive functional group of a vinyl polymer having the reactive functional group at a main chain terminus thereof with a compound represented by the following general formula (2):
wherein R 1 , R 2 and R 3 are defined as above, R 4 and R 5 are the same or different and each represents a hydrogen atom, a monovalent hydrocarbon group containing 1 to 10 carbon atoms or a monovalent group containing 1 to 10 carbon atoms as derived from two hydrocarbon groups by being bound together via an ether bond or ester bond and X represents a chlorine, bromine or iodine atom; and
wherein the reactive functional group is a phenolic hydroxyl group.
2. The epoxy resin composition according to claim 1 , wherein a main chain of the vinyl polymer is obtained polymerization of a (meth)acrylic monomer.
3. The epoxy resin composition according to claim 2 , wherein the (meth)acrylic monomer is a (meth)acrylic acid ester monomer.
4. The epoxy resin composition according to claim 3 , wherein the (math)acrylic acid ester monomer is an acrylic acid ester monomer.
5. The epoxy resin composition according to claim 1 , wherein a main chain of the vinyl polymer is obtained by polymerization of a styrenic monomer.
6. The epoxy resin composition according to claim 1 , wherein the vinyl polymer has a ratio (Mw/Mn) between weight average molecular weight (Mw) and number average molecular weight (Mn) of less than 1.8 as determined by gel permeation chromatography.
7. The epoxy resin composition according to claim 1 , wherein the vinyl polymer has a number average molecular weight within the range of 1,000 to 100,000.
8. The epoxy resin composition according to claim 1 , wherein the vinyl polymer having a reactive functional group at a main chain terminus thereof is obtained by (1) carrying out polymerization of a vinyl monomer by the living radical polymerization technique and (2) reacting, at the end point of the polymerization, the resulting polymer with a compound having both a reactive functional group and an ethylenically unsaturated group.
9. The epoxy resin composition according to claim 8 , wherein the living radical polymerization is carried out in the manner of atom transfer radical polymerization.
10. The epoxy resin composition according to claim 1 , wherein the vinyl polymer having a reactive functional group at a main chain terminus thereof is obtained by (1) producing a vinyl polymer having a halogen atom at a main chain terminus thereof by atom transfer radical polymerization and (2) converting said halogen atom to a substituent having a reactive functional group.
11. The epoxy resin composition according to claim 1 , wherein the vinyl polymer having a reactive functional group at a main chain terminus thereof is obtained by radical polymerization of a vinyl monomer using a chain transfer agent.
12. A vinyl polymer having a group represented by the following general formula (1) at a main chain terminus thereof:
wherein, R 1 , R 2 and R 3 are the same or different and each represents a hydrogen atom, a monovalent hydrocarbon group containing 1 to 10 carbon atoms or a monovalent group containing 1 to 10 carbon atoms as derived from two hydrocarbon groups by being bound together via an ether bond or ester bond, and R 1 and R 2 or R 2 and R 3 may be combined together at respective other termini to form a cyclic structure;
which polymer is obtained by reacting a reactive functional group of a vinyl polymer having the reactive functional group at a main chain terminus thereof with a compound represented by the following general formula (2):
wherein R 1 , R 2 and R 3 are defined as above, R 4 and R 5 are the same or different and each represents a hydrogen atom, a monovalent hydrocarbon group containing 1 to 10 carbon atoms or a monovalent group containing 1 to 10 carbon atoms as derived from two hydrocarbon groups by being bound together via an ether bond or ester bond and X represents a chlorine, bromine or iodine atom,
wherein the reactive functional group is selected from a phenolic hydroxyl group.
13. The vinyl polymer according to claim 12 , wherein the main chain thereof is obtained by polymerization of a (meth)acrylic monomer.
14. The vinyl polymer according to claim 13 , wherein the (meth)acrylic monomer is a (meth) acrylic acid ester monomer.
15. The vinylpolymer according to claim 14 , wherein the (meth)acrylic acid ester monomer is an acrylic acid ester monomer.
16. The vinyl polymer according to claim 12 , wherein the main chain thereof is obtained by polymerization of a styrenic monomer.
17. The vinyl polymer according to claim 12 which has a ratio (Mw/Mn) between weight average molecular weight (Mw) and number average molecular weight (Mn) of less than 1.8 as determined by gel permeation chromatography.
18. The vinyl polymer according to claim 12 which has a number average molecular weight within the range of 1,000 to 100,000.
19. The vinyl polymer according to claim 12 , wherein the vinyl polymer having a reactive functional group at a main chain terminus thereof is obtained by (1) carrying out polymerization of a vinyl monomer by the living radical polymerization technique and (2) reacting, at the end point of the polymerization, the resulting polymer with a compound having both a reactive functional group and an ethylenically unsaturated group.
20. The epoxy resin composition according to claim 19 , wherein the living radical polymerization is carried out in the manner of atom transfer radical polymerization.
21. The vinyl polymer according to claim 12 , wherein the vinyl polymer having a reactive functional group at a main chain terminus thereof is obtained by (1) producing a vinyl polymer having a halogen atom at a main chain terminus thereof by atom transfer radical polymerization and (2) converting said halogen atom to a substituent having a reactive functional group.
22. The vinyl polymer according to claim 12 , wherein the vinyl polymer having a reactive functional group at a main chain terminus thereof is obtained by radical polymerization of a vinyl monomer using a chain transfer agent.