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

Patent metadata

Field	Value
Publication number	US-9732182-B2
Application number	US-201514834387-A
Country	US
Kind code	B2
Filing date	Aug 24, 2015
Priority date	Feb 25, 2013
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

Provided are alkoxysilylated epoxy compounds, a composite of which exhibits good heat resistance properties, low CTE and increased glass transition temperature, and a cured product thereof exhibits good flame retardancy without requiring separate coupling agent, a method for preparing the same and a composition and a cured product including the same. An alkoxysilylated epoxy compound including an epoxy group and at least one alkoxysilyl group of an S1 substituent selected from Formulae S11 to S15 or an S2 substituent selected from Formulae S21 to S25; a method for preparing the same by epoxy ring-opening reaction of starting material and alkoxysilylation, an epoxy composition including the epoxy compound, and a cured product and a use of the composition, are provided. Since chemical bonds may be formed between alkoxysilyl group and filler and between alkoxysilyl groups, chemical bonding efficiency of the composite may be improved.

First claim

The invention claimed is:

1. An epoxy compound having an alkoxysilyl group, comprising:
at least two epoxy groups selected from the group consisting of Formulae S41 to S45 and at least one alkoxysilyl group of an S1 substituent independently selected from the group consisting of Formulae S11 to S15 or an S2 substituent independently selected from the group consisting of Formulae S21 to S25 coupled to a core selected from the group consisting of formulae A′ to C′ and E′ to N′:

in Formulae S11 to S15, X1 is OR 4 , OH, NR 4 R 5 , SR 4 or OCONH(CH 2 ) 3 SiR 1 R 2 R 3 , X1′ is CONH(CH 2 ) 3 SiR 1 R 2 R 3 , 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, and R 4 or R 5 may be an alkyl group, an alkenyl group, an aryl group or an aralkyl group having 1 to 20 carbon atoms and may include a hetero atom selected from a group consisting of N, O, P and S,

in Formulae S21 to S25, X2 is OR 4 , OH, NR 4 R 5 , SR 4 or O(CH 2 ) n CH 2 CH 2 SiR 1 R 2 R 3 , X2′ is (CH 2 ) n CH 2 CH 2 SiR 1 R 2 R 3 , 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, and R 4 or R 5 may be an alkyl group, an alkenyl group, an aryl group or an aralkyl group having 1 to 20 carbon atoms and may include a hetero atom selected from the group consisting of N, O, P and S,

in the formula S45, where X3 is OR 4 , OH, NR 4 R 5 , SR 4 , OCONH(CH 2 ) 3 SiR 1 R 2 R 3 or O(CH 2 ) n CH 2 CH 2 SiR 1 R 2 R 3 , X3′ is H, CONH(CH 2 ) 3 SiR 1 R 2 R 3 or (CH 2 ) n CH 2 CH 2 SiR 1 R 2 R 3 , 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, and R 4 or R 5 may be an alkyl group, an alkenyl group, an aryl group or an aralkyl group having 1 to 20 carbon atoms and may include a hetero atom selected from the group consisting of N, O, P and S,

in Formula E′, -q- is —CH 2 — or a direct linkage,
in Formula H′, R is hydrogen, a hydroxyl group, a C1-C10 alkyl group or aromatic group,
in Formula K′, S is

in Formula N′, t is

in Formulae K′ to N′, n is an integer equal to or greater than 1.

2. The epoxy compound having an alkoxysilyl group of claim 1 , wherein the cores selected from the group consisting of Formulae A′ to C′ and E′ to I′ are connected via a linking moiety of [Formula 5(2)] selected from the group consisting of Formulae LG1 to LG7, and the cores of Formula J′ are connected via Formula LG2,

3. The epoxy compound having an alkoxysilyl group of claim 1 , wherein the epoxy compound having an alkoxysilyl group further comprises a substituent selected from the group consisting of Formulae S31 to S35:

in Formulae S31 to S35, X is OR 4 , OH, NR 4 R 5 or SR 4 , and R 4 or R 5 may be an alkyl group, an alkenyl group, an aryl group or an aralkyl group having 1 to 20 carbon atoms and may include a hetero atom selected from a group consisting of N, O, P and S.

4. An epoxy composition comprising the epoxy compound having an alkoxysilyl group according to claim 1 , a curing agent and at least one filler selected from the group consisting of a fiber and inorganic particles.

5. The epoxy composition of claim 4 , further comprising at least one glycidyl-based epoxy compound.

6. A substrate comprising the epoxy composition according to claim 4 .

7. A film comprising the epoxy composition according to claim 4 .

8. A semiconductor packaging material comprising the epoxy composition of claim 4 .

9. A semiconductor device comprising the semiconductor packaging material of claim 8 .

10. An adhesive comprising the epoxy composition of claim 4 .

11. A paint comprising the epoxy composition of claim 4 .

12. A cured product of the epoxy composition of claim 4 .

Assignees

• Korea Ind Tech Inst

Inventors

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

Classifications

• C07D303/12 Primary

  with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms · CPC title

• C07F7/1804 Primary

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C08L63/00

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

• C08G59/306

  containing silicon · CPC title

• C08G59/06

  of polyhydric phenols · CPC title