Epoxy compound, curable composition containing the same, and cured product obtained by curing curable composition

Patent metadata

Field	Value
Publication number	US-10464943-B2
Application number	US-201716308110-A
Country	US
Kind code	B2
Filing date	Jun 8, 2017
Priority date	Jun 10, 2016
Publication date	Nov 5, 2019
Grant date	Nov 5, 2019

Abstract

The present invention discloses a composition comprising at least one or more stereoisomers of a compound represented by the following Formula (1), wherein, in a gas chromatogram obtained by analyzing the composition by gas chromatography, the ratio of the area of the maximum peak with respect to the total area of peaks derived from the stereoisomers is 60% or more; and wherein the maximum peak is present within the range of retention time of from 27.6 to 28.0 minutes. The present invention also discloses: a curable composition comprising the above described composition, and one selected from the group consisting of a thermal cationic polymerization initiator, an acid anhydride-based curing agent and a curing accelerator, and a photo-cationic polymerization initiator; as well as a cured product therefrom. The above described curable composition is useful in that it allows for the production of a cured product having a high heat resistance.

(In the Formula (1), R 1 to R 18 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 composition comprising at least one or more stereoisomers of a compound represented by the following Formula (1):

(wherein R 1 to R 18 are each independently selected from the group consisting of a hydrogen atom, an alkyl group and an alkoxy group)
wherein, in a gas chromatogram obtained by analyzing the composition by gas chromatography under the following analysis conditions, the ratio of the area of the maximum peak with respect to the total area of peaks derived from the stereoisomers is 60% or more,
wherein the maximum peak is present within the range of retention time of from 27.6 to 28.0 minutes, and
wherein the analysis conditions are as follows:

column: HP-1 (manufactured by Agilent Technologies Inc.), length: 60.0 m, inner diameter: 250 μm, film thickness: 0.25 μm;
liquid phase: 100% dimethylpolysiloxane;
carrier gas: N 2 ;
flow velocity: 1.3 mL/min;
sample inlet temperature: 140° C.;
detector temperature: 250° C.;
sample injection volume: 0.2 μL; and
temperature increase conditions: 80° C. (3 min), 80 to 150° C. (10° C./min), 150 to 250° C. (5° C./min), 250° C. (20 min).

2. A composition comprising at least one or more stereoisomers of a compound represented by the following Formula (1):

(wherein R 1 to R 18 are each independently selected from the group consisting of a hydrogen atom, an alkyl group and an alkoxy group)
wherein, in a gas chromatogram obtained by analyzing the composition by gas chromatography under the following analysis conditions, the ratio of the area of the maximum peak within the range of retention time of from 27.6 to 28.0 minutes with respect to the total area of peaks within the range of retention time of from 27.5 to 29.0 minutes is 60% or more, and
wherein the analysis conditions are as follows:

column: HP-1 (manufactured by Agilent Technologies Inc.), length: 60.0 m, inner diameter: 250 μm, film thickness: 0.25 μm;
liquid phase: 100% dimethylpolysiloxane;
carrier gas: N 2 ;
flow velocity: 1.3 mL/min;
sample inlet temperature: 140° C.;
detector temperature: 250° C.;
sample injection volume: 0.2 μL; and
temperature increase conditions: 80° C. (3 min), 80 to 150° C. (10° C./min), 150 to 250° C. (5° C./min), 250° C. (20 min).

3. The composition according to claim 1 , wherein the compound represented by the Formula (1) is a reaction product of a compound represented by the following Formula (2):

(wherein R 1 to R 18 are each independently selected from the group consisting of a hydrogen atom, an alkyl group and an alkoxy group)
with a peracid.

4. The composition according to claim 1 , wherein the maximum peak is the first peak among the peaks derived from the stereoisomers.

5. The composition according to claim 1 , wherein the maximum peak is the first peak appearing after a retention time of 27.5 minutes, among the peaks within the range of retention time of from 27.5 to 29.0 minutes.

6. The composition according to claim 1 , wherein the R 1 to R 18 are all hydrogen atoms.

7. The composition according to claim 1 , wherein the stereoisomer corresponding to the maximum peak is represented by the following Formula (3):

(wherein R 1 to R 18 are each independently selected from the group consisting of a hydrogen atom, an alkyl group and an alkoxy group).

8. An epoxy compound represented by the following Formula (3):

(wherein R 1 to R 18 are each independently selected from the group consisting of a hydrogen atom, an alkyl group and an alkoxy group),
wherein, in a gas chromatogram obtained by analyzing the composition by gas chromatography under the following analysis conditions, the ratio of the area of the maximum peak with respect to the total area of peaks derived from the stereoisomers is 60% or more,
wherein the maximum peak is present within the range of retention time of from 27.6 to 28.0 minutes, and
wherein the analysis conditions are as follows:

column: HP-1 (manufactured by Agilent Technologies Inc.), length: 60.0 m, inner diameter: 250 μm, film thickness: 0.25 μm;
liquid phase: 100% dimethylpolysiloxane;
carrier gas: N 2 ;
flow velocity: 1.3 mL/min;
sample inlet temperature: 140° C.;
detector temperature: 250° C.;
sample injection volume: 0.2 μL; and
temperature increase conditions: 80° C. (3 min), 80 to 150° C. (10° C./min), 150 to 250° C. (5° C./min), 250° C. (20 min).

9. A curable composition comprising:
the epoxy composition according to claim 1 or an epoxy compound represented by the following Formula (3):

(wherein R 1 to R 18 are each independently selected from the group consisting of a hydrogen atom, an alkyl group and an alkoxy group),
wherein, in a gas chromatogram obtained by analyzing the composition by gas chromatography under the following analysis conditions, the ratio of the area of the maximum peak with respect to the total area of peaks derived from the stereoisomers is 60% or more,
wherein the maximum peak is present within the range of retention time of from 27.6 to 28.0 minutes, and
wherein the analysis conditions are as follows:

column: HP-1 (manufactured by Agilent Technologies Inc.), length: 60.0 m, inner diameter: 250 μm, film thickness: 0.25 μm;
liquid phase: 100% dimethylpolysiloxane;
carrier gas: N 2 ;
flow velocity: 1.3 mL/min;
sample inlet temperature: 140° C.;
detector temperature: 250° C.;
sample injection volume: 0.2 μL; and
temperature increase conditions: 80° C. (3 min), 80 to 150° C. (10° C./min), 150 to 250° C. (5° C./min), 250° C. (20 min); and
one selected from the group consisting of: a thermal cationic polymerization initiator, an acid anhydride-based curing agent and a curing accelerator, and a photo-cationic polymerization initiator.

10. The curable composition according to claim 9 , further comprising one kind, or two or more kinds selected from the group consisting of an epoxy compound other than the compound represented by the Formula (1), an oxetane compound and a vinyl ether.

11. The curable composition according to claim 9 , 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.

12. The curable composition according to claim 11 , wherein the thermal cationic polymerization initiator is an aromatic sulfonium salt-based thermal cationic polymerization initiator.

13. The curable composition according to claim 10 , wherein, in cases where the curable composition does not comprise any of the epoxy compound other than the compound represented by the Formula (1), the oxetane compound and the vinyl ether, the content of the thermal cationic polymerization initia

Assignees

• Jxtg Nippon Oil & Energy Corp

Inventors

• TAKATA Shohei
• Ueno Ryuichi
• Sone Hisashi
• Kameyama Atsushi

Classifications

• C08G59/24

  carbocyclic · CPC title

• C08K5/3445

  Five-membered rings · CPC title

• C07B2200/07

  Optical isomers · CPC title

• C08K5/0091

  Complexes with metal-heteroatom-bonds · CPC title

• C07D493/04 Primary

  Ortho-condensed systems · CPC title