US 9,725,590 B2Granted

Epoxy compound having alkoxysilyl group, method for preparing the same, composition including the same, cured product made from the composition, and use of the composition

AssigneeKorea Institute of Industrial Technology

InventorsHyun-Aee Chun, Yun-Ju Kim, Su-Jin Park, Sang-Yong Tak, Sung-Hwan Park, Kyung-Nam Kang, Sook-Yeon Park

Life of this patent

Estimating the term…

Loading patent…

Abstract

Provided are an alkoxysilylated epoxy compound, a composite of which exhibits good heat resistance properties, particularly low CTE and increased glass transition temperature, and a cured product thereof exhibits good flame retardancy and composition of which does not require additional silane coupling agent, a method for preparing the same and a composition and a cured product including the same. An alkoxysilylated epoxy compound including at least one alkoxysilyl group and at least two epoxy groups, a method for preparing the same by epoxide 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. Thus, the composite exhibits good heat resistance properties and the cured product exhibits good flame retardancy.

Claims16

Dependent claims

An epoxy compound having an alkoxysilyl group, comprising:

at least one alkoxysilyl group (1) independently selected from the group consisting of Formulae S11 to S16, (2) independently selected from the group consisting of Formulae S21 to S26, (3) independently selected from the group consisting of Formulae S11 to S16 and Formulae S31 to S38 or (4) independently selected from the group consisting of Formulae S21 to S26 and Formulae S31 to S38;
and
at least two epoxy groups independently selected from the group consisting of Formulae S51 to S58 attached to a core,
wherein the core is one selected from the group consisting of Formulae A′ to N′:
in Formula A′, -q- is —CH2— or a direct linkage,
in Formula D′, -r- is —C(CH3)2—, —CH2—, —C(CF3)2—, —SO2—, —S—,
in Formula K′, s is
in Formula N′, t is
and
in Formulae K′ to N′, n is an integer equal to or greater than 1,
for each Si atom
in each formula of Formulae S11 to S16, at least one of R1 to R3 is an alkoxy group having 1 to 5 carbon atoms, the remainder thereof are alkyl groups having 1 to 10 carbon atoms, and the alkoxy group and the alkyl group are linear or branched;
for each Si atom
in each formula of Formulae S21 to S26, at least one of R1 to R3 is an alkoxy group having 1 to 5 carbon atoms, the remainder thereof are alkyl groups having 1 to 10 carbon atoms, and the alkoxy group and the alkyl group are linear or branched;
for each Si atom
in each formula of Formulae S31 to S38, at least one of R1 to R3 is an alkoxy group having 1 to 5 carbon atoms, the remainder thereof are alkyl groups having 1 to 10 carbon atoms, and the alkoxy group and the alkyl group are linear or branched;
for each Si atom
in each formula of Formulae S56 to S58, at least one of R1 to R3 is an alkoxy group having 1 to 5 carbon atoms, the remainder thereof are alkyl groups having 1 to 10 carbon atoms, and the alkoxy group and the alkyl group are linear or branched.

15 more elements

A method for preparing an epoxy compound having an alkoxysilyl group, comprising:

a first step of preparing an intermediate by reacting a starting material of an epoxy compound having at least three epoxy groups and allyl alcohol in the presence of a base and an optional solvent, wherein the starting material of the epoxy compound having at least three epoxy groups includes a core selected from the group consisting of Formulae (A′) to (N′) and at least three epoxy groups selected from the group consisting of Formulae S51 to S54;
and
a second step of reacting the intermediate and a compound of the following Formula B1 in the presence of a base and an optional solvent to prepare an epoxy compound including at least one alkoxysilyl group independently selected from the group consisting of Formulae S11 to S16 and at least two epoxy groups selected from the group consisting of Formulae S51 to S55 and S57 attached to the core,
wherein the core is selected from the group consisting of Formulae (A′) to (N′):
in Formula A′, -q- is —CH2— or a direct linkage,
in Formula D′, -r- is —C(CH3)2—, —CH2—, —C(CF3)2—, —SO2—, —S—,
in Formula K′, s is
in Formula N′, t is, and
in Formulae K′ to N′, n is an integer equal to or greater than 1,
OCN(CH2)3SiR1R2R3 [Formula B1]
in Formula B1, at least one of R1 to R3 is an alkoxy group having 1 to 5 carbon atoms, the remainder thereof are alkyl groups having 1 to 10 carbon atoms, and the alkoxy group and the alkyl group are linear or branched,
in each formula of Formulae S11 to S16, at least one of R1 to R3 is an alkoxy group having 1 to 5 carbon atoms, the remainder thereof are alkyl groups having 1 to 10 carbon atoms, and the alkoxy group and the alkyl group are linear or branched,
in Formula S57, at least one of R1 to R3 is an alkoxy group having 1 to 5 carbon atoms, the remainder thereof are alkyl groups having 1 to 10 carbon atoms, and the alkoxy group and the alkyl group are linear or branched.

10 more elements

A method for preparing an epoxy compound having an alkoxysilyl group, comprising:

a first step of preparing an intermediate by reacting a starting material of an epoxy compound having at least three epoxy groups and allyl alcohol in the presence of a base and an optional solvent, wherein the starting material of the epoxy compound having at least three epoxy groups includes a core selected from the group consisting of Formulae (A′) to (N′) and at least three epoxy groups selected from the group consisting of Formulae S51 to S54;
and
a second step of reacting the intermediate and a compound of the following Formula B2 in the presence of a metal catalyst and an optional solvent to prepare an epoxy compound including at least one alkoxysilyl group independently selected from the group consisting of Formulae S21 to S26 and at least two epoxy groups selected from the group consisting of Formulae S51 to S56 attached to the core,
wherein the core is selected from the group consisting of Formulae (A′) to (N′):
in Formula A′, -q- is —CH2— or a direct linkage,
in Formula D′, -r- is —C(CH3)2—, —CH2—, —C(CF3)2—, —SO2—, —S—,
in Formula K′, s is
in Formula N′, t is
and
in Formulae K′ to N′, n is an integer equal to or greater than 1,
HSiR1R2R3 [Formula B2]
in Formula B2, at least one of R1 to R3 is an alkoxy group having 1 to 5 carbon atoms, the remainder thereof are alkyl groups having 1 to 10 carbon atoms, and the alkoxy group and the alkyl group are linear or branched,
for each Si atom
in each formula of Formulae S21 to S26, at least one of R1 to R3 is an alkoxy group having 1 to 5 carbon atoms, the remainder thereof are alkyl groups having 1 to 10 carbon atoms, and the alkoxy group and the alkyl group are linear or branched,
in Formula S56, at least one of R1 to R3 is an alkoxy group having 1 to 5 carbon atoms, the remainder thereof are alkyl groups having 1 to 10 carbon atoms, and the alkoxy group and the alkyl group are linear or branched.

12 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/427,990Filed 17 Sep 2013
Priority: KR 10-2012-010293217 Sep 2012
Published: US 2015/0247033 A13 Sep 2015
Granted: 8 Aug 2017
Term ends: Not estimatedThe source records don’t support an estimate.

Classification10 codes

C08L 63/00
Compositions of epoxy resins
C07F 7/1804
Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages: compounds having Si-O-C linkages
C08G 59/306
Containing atoms other than carbon, hydrogen, oxygen and nitrogen: containing silicon
C08G 59/3281
Containing atoms other than carbon, hydrogen, oxygen or nitrogen: containing silicon