Preparation method of epoxy compound having alkoxysilyl group, epoxy compound having alkoxysilyl group, composition comprising the same, and use thereof

Patent metadata

Field	Value
Publication number	US-10968308-B2
Application number	US-201816181351-A
Country	US
Kind code	B2
Filing date	Nov 6, 2018
Priority date	Nov 7, 2017
Publication date	Apr 6, 2021
Grant date	Apr 6, 2021

Abstract

Provided are a preparation method of an epoxy compound having an alkoxysilyl group in which an increase in the epoxy equivalent weight (EEW) of the epoxy compound is minimized because alkoxysilylation occurs through a simple one-step reaction using a hydroxyl group formed during the synthesis of the epoxy compound, an epoxy compound having an alkoxysilyl group prepared by the method, a composition comprising the same, and a use thereof. The method includes the reaction of an epoxy compound having a hydroxyl group with an isocyanate alkoxysilane in the presence of amine-based base catalyst, wherein the epoxy compound having an alkoxysilyl group has a mole ratio of [epoxide group]:[alkoxysilyl group] of n:1 ranging from 2:1 to 10:1, and an EEW increase of the epoxy compound having an alkoxysilyl group is less than 260/n. The epoxy compound has good physical properties when being cured.

First claim

What is claimed is:

1. A method of preparing an epoxy compound having an alkoxysilyl group, the method comprising reacting an epoxy compound having a hydroxyl group as a starting material with an isocyanate alkoxysilane of Formula 1 in the presence of at least one amine-based base catalyst selected from the group consisting of triethylamine, diisopropylethylamine, pyridine, and imidazole,
wherein the hydroxyl group of the epoxy compound having a hydroxyl group as a starting material is formed by a side reaction during a synthesis of the epoxy compound,
wherein 0.5 to 1 equivalent of the amine-based catalyst is used per 1 equivalent of the hydroxyl group of the epoxy compound having a hydroxyl group as a starting, material,
wherein the epoxy compound having an alkoxysilyl group has a mole ratio of [epoxide group]:[alkoxysilyl group] of n:1 ranging from 2:1 to 10:1, and
an increase in an epoxy equivalent weight (EEW) of the epoxy compound having an alkoxysilyl group is less than 260/n (where n is mole ratio of an epoxide group to 1 mol of the alkoxysilyl group in the epoxy compound having an alkoxysilyl group, and n ranges from 2 to 10) compared to an EEW of the epoxy compound having a hydroxyl group as a starting material,
OCN(CH 2 ) 3 SiR 1 R 2 R 3   Formula 1

where at least one of R 1 to R 3 is an alkoxy group having 1 to 5 carbon atoms, and the remainder are alkyl groups having 1 to 10 carbon atoms.

2. The method of claim 1 , wherein the epoxy compound having a hydroxyl group as a starting material is selected from the group consisting of Formulae AS to IS below:

in Formula BS, S is

in Formula DS, t is

in Formulae AS to DS, n is an integer equal to or greater than 1,
in Formula ES, -q- is —CH 2 — or a direct linkage,
in Formula GS, R is hydrogen, a hydroxyl group, a C1-C10 alkyl group, or a C6 or C10 aromatic group,
in Formulae AS to IS, at least one of Ks is a structure having a hydroxyl group selected from the group consisting of —CH 2 CHOHCH 2 OH (Formula S11), —CH 2 CHOHCH 2 Cl (Formula S12), and —CH(CH 2 OH)(CH 2 Cl) (Formula S13), and the remainder are structures having an epoxide group of Formula E1 below:

wherein the structures of Formulae AS to IS may be connected through a linker having a hydroxyl group of Formula LG1 below at one position of Ks:

3. The method of claim 1 , wherein 1 equivalent of the hydroxyl group of the epoxy compound having a hydroxyl as a starting material group reacts with 1 equivalent of the isocyanate alkoxysilane of Formula 1.

4. The method of claim 1 , wherein the reacting is performed at a temperature range of 90° C. to 150° C.

5. The method of claim 1 , wherein the reacting is performed for 72 hours to 120 hours.

6. The method of claim 1 , wherein the epoxy compound having an alkoxysilyl group is one-selected from the group consisting of Formulae AF to IF below:

in Formula BF, S is

in Formula DF, t is

in Formulae AF to DF, n is an integer equal to or greater than 1,
in Formula EF, -q- is —CH 2 — or a direct linkage,
in Formula GF, R is hydrogen, a hydroxyl group, a C1-C10 alkyl group, or a C6 or C10 aromatic group,
in Formulae AF to IF, at least one of Ms is a structure having an alkoxysilyl group selected from the group consisting of —CH 2 CHOXCH 2 OX (Formula S21), —CH 2 CHOXCH 2 Cl (Formula S22), and —CH(CH 2 OX)(CH 2 Cl) (Formula S23), and the remainder are structures having an epoxide group of Formula E1 below:

in Formulae S21 to S23, X is CONH(CH 2 ) 3 SiR 1 R 2 R 3 , wherein at least one of R 1 to R 3 is an alkoxy group having 1 to 5 carbon atoms and the remainder are alkyl groups having 1 to 10 carbon atoms,

wherein the structures of Formulae AF to IF may be connected to each other at one of Ms through a linker having an alkoxysilyl group of Formula LG2 below:

in Formula LG2, at least one of R 1 to R 3 is an alkoxy group having 1 to 5 carbon atoms, and the remainder are alkyl groups having 1 to 10 carbon atoms.

Assignees

• Korea Inst Ind Tech

Inventors

• Chun Hyun Aee
• Kim Yun Ju
• Park Sook Yeon
• Park Su Jin

Classifications

• C08G18/718

  containing silicon · CPC title

• C08G18/2027

  having two nitrogen atoms in the ring · CPC title

• C08G18/18

  containing secondary or tertiary amines or salts thereof · CPC title

• C08G59/3281

  containing silicon · CPC title

• C08G59/1477

  containing nitrogen · CPC title