Epoxy compound having alkoxysilyl group, method of preparing the same, composition and cured product comprising the same, and uses thereof

Patent metadata

Field	Value
Publication number	US-9896535-B2
Application number	US-201514805339-A
Country	US
Kind code	B2
Filing date	Jul 21, 2015
Priority date	Aug 25, 2011
Publication date	Feb 20, 2018
Grant date	Feb 20, 2018

Abstract

Disclosed are an epoxy compound having an alkoxysilyl group, a composite of which exhibits good heat resistant properties and/or a cured product of which exhibits good flame retardant properties, a method of preparing the same, a composition comprising the same, and a cured product and a use of the composition. An alkoxysilylated epoxy compound comprising at least one of Chemical Formula S1 substituent and at least two epoxy groups in a core, a method of preparing the epoxy compound by an allylation, a claisen rearrangement, an epoxidation and an alkoxysilylation, an epoxy composition comprising the epoxy compound, and a cured product and a use of the composition are provided. The composite of the disclosed exhibits improved chemical bonding, good heat resistant properties, a low CTE, a high glass transition temperature or Tg-less. The cured product of the composition exhibits good flame retardant properties.

First claim

The invention claimed is:

1. An epoxy compound having an alkoxysilyl group comprising at least one substituent of Chemical Formula S1 and two epoxy groups at a core selected from the group consisting of the following Chemical Formulae A′ to C′, E′ and G′ to K′:
—CR b R c —CHR a —CH 2 —SiR 1 R 2 R 3   [Chemical Formula S1]

in Chemical Formula S1, each of R a , R b and R c is independently H or an alkyl group having 1 to 6 carbon atoms, at least one of R 1 to R 3 is an alkoxy group having 1 to 6 carbon atoms, and a remainder of R 1 to R 3 is an alkyl group having 1 to 10 carbon atoms.

2. The epoxy compound having an alkoxysilyl group of claim 1 , wherein the two epoxy groups are of the following Chemical Formula S2:

3. The epoxy compound having an alkoxysilyl group of claim 1 , further comprising a substituent of the following Chemical Formula S3:

in Chemical Formula S3, each of R a , R b and R c is independently H or an alkyl group having 1 to 6 carbon atoms.

4. The epoxy compound having an alkoxysilyl group of claim 1 , wherein the epoxy compound having the alkoxysilyl group is at least one selected from the group consisting of the following Chemical Formulae (AI) to (CI), (EI) and (GI) to (KI):

in Chemical Formulae (AI) to (CI), (EI) and (GI) to (KI), at least one Q is Chemical Formula S1, and each remaining Q is Chemical Formula S3, hydrogen or —CR b R c —CHR a ═CH 2 , in which each of R a , R b and R c is independently H or an alkyl group having 1 to 6 carbon atoms,

in Chemical Formula S3, each of R a , R b and R c is independently H or an alkyl group having 1 to 6 carbon atoms.

5. The epoxy compound having an alkoxysilyl group of claim 4 , wherein at least one Q is Chemical Formula S3.

6. A method of preparing an epoxy compound having an alkoxysilyl group selected from Chemical Formulae (A14) to (C14), (E14) and (G14) to (K14), the method comprising:
preparing a first intermediate product selected from the following Chemical Formulae (A11) to (C11), (E11) and (G11) to (K11) by reacting at least one OH group of a starting material selected from the following Chemical Formulae (AS) to (CS), (ES) and (GS) to (KS) with an allyl compound of Chemical Formula B1 in the presence of a base:

in Chemical Formulae A11 to C11, E11 and G11 to K11, one K is —O—CH 2 —CR a ═CR b R c , in which each of R a , R b and R c is independently H or an alkyl group having 1 to 6 carbon atoms, and the other K is a hydroxyl group or —O—CH 2 —CR a ═CR b R c ,

in Chemical Formula B1, X is Cl, Br, I, —O—SO 2 —CH 3 , —O—SO 2 —CF 3 , or —O—SO 2 —C 6 H 4 —CH 3 , and each of R a , R b and R c is independently H or an alkyl group having 1 to 6 carbon atoms;
preparing a second intermediate product from the following Chemical Formulae (A12) to (C12), (E12) and (G12) to (K12) by claisen rearrangement of each —O—CH 2 —CR a ═CR b R c group of the first intermediate product;

in Chemical Formulae A12 to C12, E12 and G12 to K12, one L is —CR b R c —CR a ═CH 2 , and the other L is hydrogen or —CR b R c —CR a ═CH 2 ;
preparing a third intermediate product from the following Chemical Formulae (A13) to (C13), (E13) and (G13) to (K13) by reacting the OH groups of the second intermediate product with epichlorohydrin in the presence of a base,

in Chemical Formulae A13 to C13, E13 and G13 to K13, one M is —CR b R c —CR a ═CH 2 , and the other M is —CR b R c —CR a ═CH 2 or hydrogen; and
reacting at least one —CR b R c —CR a ═CH 2 group of the third intermediate product with an alkoxysilane of Chemical Formula B2 in a presence of a metal catalyst resulting in the epoxy compound having an alkoxysilyl group selected from Chemical Formulae (A14) to (C14), (E14) and (G14) to (K14):
HSiR 1 R 2 R 3   [Chemical Formula B2]

in Chemical Formula B2, at least one of R 1 to R 3 is an alkoxy group having 1 to 6 carbon atoms, and the remainder of R 1 to R 3 is an alkyl group having 1 to 10 carbon atoms,

in Chemical Formulae A14 to C14, E14 and G14 to K14, one P is Chemical Formula S1, and the other P is Chemical Formula S1, Chemical Formula S3, hydrogen or —CR b R c —CR a ═CH 2 ,
—CR b R c —CHR a —CH 2 —SiR 1 R 2 R 3   [Chemical Formula S1]

in Chemical Formula S1, each of R a , R b and R c is independently H or an alkyl group having 1 to 6 carbon atoms, at least one of R 1 to R 3 is an alkoxy group having 1 to 6 carbon atoms, and the remainder of R 1 to R 3 is an alkyl group having 1 to 10 carbon atoms.

7. The method of claim 6 , further comprising:
after preparing the third intermediate product, preparing an intermediate product 13′ of the following Chemical Formulae (A13′) to (C13′), (E13′) and (G13′) to (K13′) by reacting an M group of the third intermediate product with a peroxide compound:

in Chemical Formulae (A13′) to (C13′), (E13′) and (G13′) to (K13′), one N is —CR b R c —CR a ═CH 2 , in which each of R a , R b and R c is independently H or an alkyl group having 1 to 6 carbon atoms, and the other N is Chemical Formula S3,

in Chemical Formula S3, each of R a , R b and R c is independently H or an alkyl group having 1 to 6 carbon atoms.

8. An epoxy composition comprising an epoxy compound having an alkoxysilyl group selected from the group consisting of Chemical Formulae AI to CI, EI and GI to KI:

in Chemical Formulae (AI) to (CI), (EI) and (GI) to (KI), one Q is Chemical Formula S1 and each remaining Q is Chemical Formula S1, Chemical Formula S3, hydrogen or —CR b R c —CR a ═CH 2 , in which each of R a , R b and R c is independently H or an alkyl group having 1 to 6 carbon atoms,
—CR b R c —CHR a —CH

Assignees

• Korea Inst Ind Tech

Inventors

• Chun Hyun Aee
• Tak Sang Yong
• Park Su Jin
• Kim Yun Ju
• Park Sung Hwan

Classifications

• C08J5/24

  Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs · CPC title

• C08L63/00

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

• C08K7/14

  Glass · CPC title

• C07F7/1876

  by reactions involving the formation of Si-C linkages · CPC title

• C08K3/36

  Silica · CPC title