Preparation method for epoxy compound having alkoxysilyl group

Patent metadata

Field	Value
Publication number	US-11512100-B2
Application number	US-202016918311-A
Country	US
Kind code	B2
Filing date	Jul 1, 2020
Priority date	May 8, 2018
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

Provided is a method for preparing an epoxy compound having an alkoxysilyl group effectively by using a mild catalyst as well as an aromatic alcohol ring-opening agent. The preparation method for an epoxy compound having an alkoxysilyl group includes: performing a ring opening step by reacting an epoxy compound having an epoxide group, which is a starting material, with an aromatic alcohol ring-opening agent in the presence of a phosphine-based catalyst and an optional solvent so as to obtain an intermediate having a partially ring-opened epoxide group; and performing an alkoxysilylation step by reacting the intermediate having a partially ring-opened epoxide with isocyanate alkoxysilane.

First claim

What is claimed is:

1. A method for preparing an epoxy resin having an alkoxysilyl group, the method comprising:
performing a ring opening step by reacting at least one epoxy resin selected from a group consisting of Formulae BS, CS, FS, and IS having three or more epoxide groups with an aromatic alcohol having one hydroxyl group as a ring-opening agent in the presence of a phosphine-based catalyst and an optional solvent to provide an intermediate having a ring-opened epoxide group; and
performing an alkoxysilylation step by reacting the intermediate having a ring-opened epoxide group with isocyanate alkoxysilane represented by Formula B below,
wherein the phosphine-based catalyst is represented by Formula A:
PRxRyRz  Formula A

in Formula A, Rx, Ry, and Rz are each independently a C1-C10 alkyl group, a C6 or C10 aryl group, or a C6-C10 cycloalkyl group,
wherein the epoxy compound having the alkoxysilyl group following the alkoxysilylation step is represented by at least one selected from a group consisting of Formulae BF, CF, FF, and IF:

wherein in Formula BF:
S is

wherein in Formulae BF, CF, FF, and IF:
at least one of the M's is of Formula C;
at least two of the M's is an epoxy group of Formula E1; and remainder of M's are hydrogen,

and,
in Formula C, at least one of R 1 to R 3 is a C1-C5 alkoxy group, and the others are C1-C10 alkyl groups, and Y is represented by Formula 3 or 4,

wherein in Formula 3 or Formula 4,
each X is independently selected from the group consisting of H, a C1 to C10 alkyl group, an allyl group, and a C6 or C10 aryl group, wherein the C6 or C10 aryl group is substitutable with a C1-C3 alkyl group, and n′ is an integer from 1 to 5; and
n in Formulae BF and CF is an integer from 1 to 30,
wherein the Formulae BF, CF, FF, and IF are prepared from epoxy resins BS, CS, FS, and IS, respectively,

wherein in Formulae BS, CS, FS, and IS, at least three of the K's is an epoxy group of Formula E1, and the remaining are hydrogen,
S in Formula BS is the same as in Formula BF except M in Formula BF is K as defined in Formula BS, and
n in Formulae BF and CF is the same as in Formula BS and CS, respectively,
OCN(CH 2 ) 3 SiR 1 R 2 R 3   [Formula B]

where at least one of R 1 to R 3 is a C1-05 alkoxy group, and the others are C1-C10 alkyl groups.

2. The method of claim 1 , wherein in situ the alkoxysilylation step is carried out continuously following the ring opening.

3. The method of claim 1 , wherein the ring opening step does not require the subsequent purification process for the intermediate product having a ring-opened epoxide group.

4. The method of claim 1 , wherein the aromatic alcohol is represented by Formulae 1 or 2 below:

wherein in Formulae 1 and 2, each X is independently H, a C1 to C10 alkyl group, an allyl group, or a C6 or C10 aryl group, wherein the C6 or C10 aryl group is substitutable with a C1-C3 alkyl group, and n′ is an integer ranging from 1 to 5.

5. The method of claim 1 , wherein 0.1 to 2 parts by weight of the phosphine-based catalyst are used per 100 parts by weight of the epoxy resin having three or more epoxide groups.

6. The method of claim 1 , wherein the ring opening step is performed for 10 minutes to 48 hours.

7. The method of claim 1 , wherein a degree of ring opening does not need to be controlled by reaction time in the ring opening step.

8. An article comprising the epoxy resin having an alkoxysilyl group of claim 1 , the article selected from an electronic material, semiconductor substrate, IC substrate, laminate in which a metal layer is provided on a base layer, prepreg, encapsulant, printed circuit board, electronic component, adhesive, painting, or composite material.

9. The method of claim 1 , wherein 0.05 to 0.9 equivalents of the aromatic alcohol ring-opening agent is used per one equivalent of epoxy group of the epoxy resins selected from a group consisting of Formulae BS, CS, FS, and IS.

10. The method of claim 1 , wherein the ring-opening step is performed at a temperature of 60° C. to 200° C.

Assignees

• Korea Inst Ind Tech

Inventors

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

Classifications

• B01J2531/002

  Materials · CPC title

• C07F7/0801 Primary

  General processes · CPC title

• B01J31/0267

  Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen · CPC title

• C07D303/04

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

• B01J2231/44

  Allylic alkylation, amination, alkoxylation or analogues · CPC title