Epoxy compound, curable composition, cured product, method of producing epoxy compound, and reactive diluent

Patent metadata

Field	Value
Publication number	US-10995079-B2
Application number	US-201716084375-A
Country	US
Kind code	B2
Filing date	Mar 13, 2017
Priority date	Mar 14, 2016
Publication date	May 4, 2021
Grant date	May 4, 2021

Abstract

The present invention discloses a monoepoxy compound represented by the following Formula (1), a curable composition containing the same, a cured product therefrom, a method of producing the monoepoxy compound, and a reactive diluent containing the monoepoxy compound. The monoepoxy compound represented by the Formula (1) is useful in that it is capable of reducing the viscosity of a curable composition containing the monoepoxy compound, while preventing a reduction in the heat resistance of the curable composition as well as a reduction in the weight of the curable composition upon curing.

(In the Formula (1), R 1 to R 6 are each independently selected from the group consisting of a hydrogen atom, an alkyl group, and an alkoxy group.)

First claim

The invention claimed is:

1. A monoepoxy compound represented by the following Formula (1):

wherein R 1 to R 6 are each independently selected from the group consisting of a hydrogen atom, an alkyl group having from 1 to 10 carbon atoms, and an alkoxy group having from 1 to 10 carbon atoms.

2. The monoepoxy compound according to claim 1 , comprising a stereoisomer(s) of the compound represented by the Formula (1), wherein the ratio, as measured by 13 C-NMR analysis, of a peak area(s) derived from a stereoisomer(s) in which the bridgehead of the norbornane skeleton and the vinyl group in the Formula (1) are in a trans relationship, to the total peak area within the chemical shift range of from 140 to 145 ppm, is 66% or more.

3. The monoepoxy compound according to claim 2 , wherein R 1 to R 6 are all hydrogen atoms, and the stereoisomer(s) in which the bridgehead of the norbornane skeleton and the vinyl group are in a trans relationship is/are represented by any of the following Formulae:

4. The monoepoxy compound according to claim 1 , wherein, in the 13 C-NMR analysis of the compound represented by the Formula (1), the ratio of the total peak area within the chemical shift range of from 140 to 142 ppm to the total peak area within the chemical shift range of from 140 to 145 ppm is 66% or more.

5. The monoepoxy compound according to claim 2 , wherein, in the 13 C-NMR analysis of the compound represented by the Formula (1), the ratio of the area of the first peak from the low magnetic field side, among peaks within the chemical shift range of from 140 to 142 ppm, to the total peak area within the chemical shift range of from 140 to 145 ppm is 35% or more.

6. A curable composition comprising:
the monoepoxy compound according to claim 1 ; and
one kind selected from the group consisting of a curing agent, a thermal cationic polymerization initiator, and a photo-cationic polymerization initiator.

7. The curable composition according to claim 6 , wherein the curing agent is one or more curing agents selected from the group consisting of phenol compounds, amine compounds, acid anhydride-based compounds, and an amide compounds.

8. The curable composition according to claim 6 , wherein the thermal cationic polymerization initiator is selected from the group consisting of aromatic sulfonium salt-based thermal cationic polymerization initiators, aromatic iodonium salt-based thermal cationic polymerization initiators, and aluminum complex-based thermal cationic polymerization initiators.

9. The curable composition according to claim 6 , wherein the photo-cationic polymerization initiator is an aromatic sulfonium salt-based photo-cationic polymerization initiator.

10. The curable composition according to claim 6 , further comprising another epoxy compound different from the monoepoxy compound represented by the Formula (1).

11. The curable composition according to claim 10 , wherein the other epoxy compound different from the monoepoxy compound represented by the Formula (1) is selected from the group consisting of glycidyl ether-type epoxides, glycidyl ester-type epoxides, alicyclic epoxides, and epoxy resins.

12. The curable composition according to claim 10 , wherein the content ratio of the monoepoxy compound to the other epoxy compound different from the monoepoxy compound represented by the Formula (1), in the curable composition, is from 1:99 to 75:25 on a mass basis.

13. A method of producing a cured product, the method comprising the step of curing the curable composition according to claim 6 .

14. A cured product from the curable composition according to claim 6 .

15. A method of producing the monoepoxy compound according to claim 1 , the method comprising the step of allowing a compound represented by the following Formula (2):

wherein R 1 to R 6 are each independently selected from the group consisting of a hydrogen atom, an alkyl group having from 1 to 10 carbon atoms, and an alkoxy group having from 1 to 10 carbon atoms to react with a peracid,
wherein the peracid is used in an amount of from 0.10 to 1.80 mol, with respect to 1.00 mol of the compound represented by the Formula (2).

16. The method according to claim 15 , wherein the peracid is hydrogen peroxide or an organic peracid.

17. A reactive diluent comprising at least the monoepoxy compound according to claim 1 .

Assignees

• Eneos Corp

Inventors

• Kameyama Atsushi
• Ueno Ryuichi
• Sone Hisashi
• Suzuki Hiroaki
• TAKATA Shohei
• Seki Takashi

Classifications

• C07D303/04

  containing only hydrogen and carbon atoms in addition to the ring oxygen atoms · CPC title

• C08G65/14

  Unsaturated oxiranes · CPC title

• C08G65/105

  Onium compounds · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C07D301/12

  with hydrogen peroxide or inorganic peroxides or peracids · CPC title