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

An epoxy polymer having an alkoxysilyl group which is at least one selected from the group consisting of the following Chemical Formulae AP to KP:

• in Chemical Formulae AP to KP, at least one of a plurality of Q is Chemical Formula S1, each of the remainder of Q is independently selected from the group consisting of the following Chemical Formula S3, hydrogen and —CRbRc—CRa═CH2 (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, the alkyl group may have a linear chain or a branched chain),
• m is an integer of 1 to 100, and
• in Chemical Formula DP above, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• —CRbRc—CHRa—CH2—SiR1R2R3 [Chemical Formula S1]
• in Chemical Formula S1, each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, at least one of R1 to R3 is an alkoxy group having 1 to 6 carbon atoms, and a remainder of R1 to R3 is an alkyl group having 1 to 10 carbon atoms, and
• the alkyl group and the alkoxy group may be a linear chain or a branched chain,
• in Chemical Formula S3, each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be a linear chain or a branched chain.

A method of preparing an epoxy compound having an alkoxysilyl group of Chemical Formulae A(14) to K(14), comprising:

• a 1st step of preparing one intermediate product (11) from the following Chemical Formulae (A11) to (K11) by reacting one starting material from the following Chemical Formulae (AS) to (KS) with an allyl compound of the following Chemical Formula B1 in a presence of a base and an optional solvent;
• a 2nd step of preparing one intermediate product (12) from the following Chemical Formulae (A12) to (K12) by heating one of the intermediate product (11) in a presence of an optional solvent;
• a 3rd step of preparing one intermediate product (13) from the following Chemical Formulae (A13) to (K13) by reacting one of the intermediate product (12) with epichlorohydrin in a presence of a base and an optional solvent;
• an optional 3-1-th step of preparing one intermediate product (13′) from the following Chemical Formulae (A13′) to (K13′) by reacting one of intermediate product (13) with a peroxide compound in a presence of an optional base and an optional solvent;
• and
• a 4th step of reacting one of the intermediate product (13) or one of the intermediate product (13′) with an alkoxysilane of the following Chemical Formula B2 in a presence of a metal catalyst and an optional solvent,
• in Chemical Formula DS, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• in Chemical Formulae A11 to K11, at least one of K is —O—CH2—CRa═CRbRc (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, the alkyl group may have a linear chain or a branched chain), and the remainder of K is a hydroxyl group, and
• in Chemical Formula D11 above, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• in Chemical Formulae A12 to K12, at least one of L is —CRbRc—CRa═CH2 (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, the alkyl group may have a linear chain or a branched chain), and the remainder of L is hydrogen, and
• in Chemical Formula D12 above, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• in Chemical Formulae A13 to K13, at least one of M is —CRbRc—CRa═CH2 (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, the alkyl group may have a linear chain or a branched chain), and the remainder of M is hydrogen, and
• in Chemical Formula D13 above, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• in Chemical Formulae A13′ to K13′, one of N is —CRbRc—CRa═CH2 (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, the alkyl group may have a linear chain or a branched chain), and the remainder of N follows Chemical Formula S3, and
• in Chemical Formula D13′ above, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• in Chemical Formula S3, each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be a linear chain or a branched chain,
• in Chemical Formulae A14 to K14, at least one of P is Chemical Formula S1, each of the remainder of P is independently selected from the group consisting of the following Chemical Formula S3, hydrogen and —CRbRc—CRa═CH2 (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, the alkyl group may have a linear chain or a branched chain), and
• in Chemical Formula D14 above, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• —CRbRc—CHRa—CH2—SiR1R2R3 [Chemical Formula S1]
• in Chemical Formula S1, each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, at least one of R1 to R3 is an alkoxy group having 1 to 6 carbon atoms, and the remainder of R1 to R3 is an alkyl group having 1 to 10 carbon atoms, and the alkyl group and the alkoxy group may be a linear chain or a branched chain
• the epoxy compound of Chemical Formula F14 having one of S1, in which all of Ra, Rb and Rc are hydrogen, and all of R1 to R3 are the alkoxy group having 1 to 6 carbon atoms is excluded,
• in Chemical Formula S3, each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be a linear chain or a branched chain,
• in Chemical Formula B1, X is Cl, Br, I, —O—SO2—CH3, —O—SO2—CF3, or —O—SO2—C6H4—CH3, each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may have a linear chain or a branched chain
• HSiR1R2R3 [Chemical Formula B2]
• in Chemical Formula B2, at least one of R1 to R3 is an alkoxy group having 1 to 6 carbon atoms, the remainder of R1 to R3 is an alkyl group having 1 to 10 carbon atoms, and the alkyl group may have a linear chain or a branched chain.

A method of preparing an epoxy compound having an alkoxysilyl group of Chemical Formulae (A26) to (J26), comprising:

• a 1st step of preparing one intermediate product (11) from the following Chemical Formulae (A1) to (J1) by reacting one starting material from the following Chemical Formulae (AS) to (JS) with an allyl compound of the following Chemical Formula B1 in a presence of a base and an optional solvent;
• a 2nd step of preparing one intermediate product (12) from the following Chemical Formulae (A12) to (J12) by heating one of the intermediate product (11) in a presence of an optional solvent;
• a 2-1-th step of preparing one intermediate product (23) from the following Chemical Formulae (A23) to (J23) by reacting one of the intermediate product (12) with the allyl compound of the following Chemical Formula B1 in a presence of a base and an optional solvent;
• a 2-2-th step of preparing one intermediate product (24) from the following Chemical Formulae (A24) to (J24) by heating the intermediate product (23) in a presence of an optional solvent;
• a 3rd step of preparing one intermediate product (25) from the following Chemical Formulae (A25) to (J25) by reacting one of the intermediate product (24) with epichlorohydrin in a presence of a base and an optional solvent;
• an optional 3-1-th step of preparing one intermediate product (25′) from the following Chemical Formulae (A25′) to (J25′) by reacting one of intermediate product (25) with a peroxide compound in a presence of an optional base and an optional solvent;
• and
• a 4th step of reacting one of the intermediate product (25) or one of the intermediate product (25′) with an alkoxysilane of the following Chemical Formula B2 in a presence of a metal catalyst and an optional solvent,
• in Chemical Formula DS, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• in Chemical Formulae A11 to J11, at least one of K is —O—CH2—CRa═CRbRc (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may have a linear chain or a branched chain), and the remainder of K is a hydroxyl group, and
• in Chemical Formula D11 above, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• in Chemical Formulae A12 to J12, at least one of L is —CRbRc—CRa═CH2 (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, the alkyl group may have a linear chain or a branched chain), and the remainder of L is hydrogen, and
• in Chemical Formula D12 above, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• in Chemical Formulae A23 to J23, at least one of K′ is —O—CH2—CRa═CRbRc (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, the alkyl group may have a linear chain or a branched chain), and the remainder of K′ is hydroxyl group,
• at least one of L is —CRbRc—CRa═CH2 (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, the alkyl group may have a linear chain or a branched chain), and the remainder of L is hydrogen, and
• in Chemical Formula D23 above, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• in Chemical Formulae A24 to J24, at least two of a plurality of L′ are —CRbRc—CRa═CH2 (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, the alkyl group may have a linear chain or a branched chain), and the remainder of the plurality of the L′ is hydrogen, and
• in Chemical Formula D24 above, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• in Chemical Formulae A25 to J25, at least two of a plurality of M′ are —CRbRc—CRa═CH2 (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, the alkyl group may have a linear chain or a branched chain), and the remainder of the plurality of the M′ is hydrogen, and
• in Chemical Formula D25 above, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• in Chemical Formulae A25′ to J25′, one to three of a plurality of N′ are —CRbRc—CRa═CH2 (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, the alkyl group may have a linear chain or a branched chain), one to three of the plurality of the N′ are the following Chemical Formula S3, and the remainder of the plurality of the N′ is hydrogen, and
• in Chemical Formula D25′ above, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• in Chemical Formulae A26 to J26, at least one of P′ follows Chemical Formula S1, each of the remainder of P′ is independently selected from the group consisting of the following Chemical Formula S3, hydrogen and —CRbRc—CRa═CH2 (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may have a linear chain or a branched chain), and
• in Chemical Formula D26 above, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• —CRbRc—CHRa—CH2—SiR1R2R3 [Chemical Formula S1]
• in Chemical Formula S1, each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, at least one of R1 to R3 is an alkoxy group having 1 to 6 carbon atoms, and the remainder of R1 to R3 is an alkyl group having 1 to 10 carbon atoms, and the alkyl group and the alkoxy group may be a linear chain or a branched chain,
• the epoxy compound of Chemical Formula F26 having one of S1, in which all of Ra, Rb and Rc are hydrogen, and all of R1 to R3 are the alkoxy group having 1 to 6 carbon atoms is excluded,
• in Chemical Formula S3, each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be a linear chain or a branched chain,
• in Chemical Formula B1, X is Cl, Br, I, —O—SO2—CH3, —O—SO2—CF3, or —O—SO2—C6H4—CH3, each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may have a linear chain or a branched chain,
• HSiR1R2R3 [Chemical Formula B2]
• in Chemical Formula B2, at least one of R1 to R3 is an alkoxy group having 1 to 6 carbon atoms, the remainder of R1 to R3 is an alkyl group having 1 to 10 carbon atoms, and the alkyl group and the alkoxy group may have a linear chain or a branched chain.

An epoxy composition comprising at least one of an epoxy compound having an alkoxysilyl group selected from the group consisting of the following Chemical Formulae AI to KI:

• in Chemical Formulae (AI) to (KI), at least one of a plurality of Q is Chemical Formula S1, each of the remainder of the plurality of Q is independently selected from the group consisting of the following Chemical Formula S3, hydrogen and —CRbRc—CRa═CH2 (in which each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may have a linear chain or a branched chain), and
• in Chemical Formula DI above, Y is —CH2—, —C(CH3)2—, —C(CF3)2—, —S— or —SO2—,
• —CRbRc—CHRa—CH2—SiR1R2R3 [Chemical Formula S1]
• in Chemical Formula S1, each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, at least one of R1 to R3 is an alkoxy group having 1 to 6 carbon atoms, and the remainder of R1 to R3 is an alkyl group having 1 to 10 carbon atoms, and the alkyl group and the alkoxy group may be a linear chain or a branched chain,
• the epoxy compound of the Chemical Formula FI having one of S1, in which all of Ra, Rb and Rc are hydrogen, and all of R1 to R3 are the alkoxy group having 1 to 6 carbon atoms being excluded,
• in Chemical Formula S3, each of Ra, Rb and Rc is independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be a linear chain or a branched chain.