Method for Preparing Crosslinker Compound

Patent metadata

Field	Value
Publication number	US-2021024451-A1
Application number	US-201916968999-A
Country	US
Kind code	A1
Filing date	Oct 7, 2019
Priority date	Nov 28, 2018
Publication date	Jan 28, 2021
Grant date	—

Abstract

The present disclosure relates to a method for preparing a crosslinker compound in which a crosslinker compound capable of using for the production of a super absorbent polymer can be obtained in a higher yield by a simple manner. The crosslinker compound obtained by the above method can be used as a thermally decomposable crosslinker in the process of producing a super absorbent polymer.

First claim

1 . A method for preparing a crosslinker compound which is used as an internal crosslinking agent or a thermally decomposable crosslinker for production of a super absorbent polymer, the method comprising the steps of:
hydrogenating a compound of the following Chemical Formula 1 under a noble metal catalyst to form a compound of the following Chemical Formula 2; and subjecting the compound of the following Chemical Formula 2 and a compound of the following Chemical Formula 3 to an esterification reaction to form a compound of the following Chemical Formula 4,

wherein, R 1 ′ has a triple bond and is a divalent organic group having 1 to 10 carbon atoms, R 1 is a divalent organic group comprising an alkyl group having 1 to 10 carbon atoms, R 2 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms, R 4 is hydrogen or a methyl group, and X is halogen.

2 . The method for preparing a crosslinker compound according to claim 1 , wherein the compound of Chemical Formula 1 is formed by reacting a compound of the following Chemical Formula 1a with ketone in the presence of a base:

wherein, R 1 ″ has a triple bond at the terminal and is a monovalent organic group having 1 to 9 carbon atoms, and R 2 ′ and R 3 ′ are each independently hydrogen or an alkyl group having 1 to 5 carbon atoms.

3 . The method for preparing a crosslinker compound according to claim 2 , wherein the base comprises one or more selected from the group consisting of potassium hydroxide, sodium hydroxide, sodium hydride and potassium hydride.

4 . The method for preparing a crosslinker compound according to claim 1 , wherein in the hydrogenation step, the noble metal catalyst comprises at least one selected from the group consisting of Pd, Pt, Ni and Rh.

5 . The method for preparing a crosslinker compound according to claim 1 , wherein the hydrogenation step is performed in the presence of one or more solvents selected from the group consisting of ethyl acetate, methanol, isopropanol, and tetrahydrofuran.

6 . The method for preparing a crosslinker compound according to claim 1 , wherein the esterification step is performed in the presence of an amine-based base selected from the group consisting of triethylamine, dimethylaminopyridine, diisopropylethylamine, and 1,8-diazabicyclo[5,4,0]undec-7-ene.

7 . The method for preparing a crosslinker compound according to claim 1 , wherein in Chemical Formula 4, R 1 is methane-1,1-diyl, propane-1,3-diyl, propane-1,2-diyl, propane-1,1-diyl, n-butane-1,4-diyl, n-butane-1,3-diyl, n-butane-1,2-diyl, n-butane-1,1-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, 2-methylpropane-1,1-diyl, 2-methylbutane-1,4-diyl, 2-methylbutane-2,4-diyl, 2-methylbutane-3,4-diyl, 2-methylbutane-4,4-diyl, 2-methylbutane-1,3-diyl, 2-methylbutane-1,2-diyl, 2-methylbutane-1,1-diyl or 2-methylbutane-2,3-diyl.

8 . A method for producing a super absorbent polymer comprising the steps of:
forming a crosslinker compound by the method of claim 1 ; performing crosslinking polymerization of a water-soluble ethylenically unsaturated monomer having an acidic group of which at least a part is neutralized, in the presence of an internal crosslinking agent including the crosslinker compound to form a hydrogel polymer; drying, pulverizing and classifying the hydrogel polymer to form a base resin powder; and further cross-linking the surface of the base polymer powder in the presence of a surface crosslinking agent to form a surface cross-linked layer.

9 . A super absorbent polymer produced by the method of claim 8 .

10 . The method for preparing a crosslinker compound according to claim 2 , wherein the ketone is used in an amount of 1 to 4 molar equivalents with respect to the compound of Chemical Formula 1a.

11 . The method for preparing a crosslinker compound according to claim 2 , wherein the step of reacting the compound of Chemical Formula 1a with ketone is performed at a temperature of 20 to 50° C. for 1 to 24 hours.

12 . The method for preparing a crosslinker compound according to claim 1 , wherein in the hydrogenation step, the noble metal catalyst comprises Pd/C.

13 . The method for preparing a crosslinker compound according to claim 1 , wherein in the hydrogenation step, the noble metal catalyst is used in an amount of 0.1 to 5 mol % with respect to the compound of Chemical Formula 1.

14 . The method for preparing a crosslinker compound according to claim 1 , wherein the hydrogenation step is performed at a temperature of 10 to 50° C.

Assignees

• Lg Chemical Ltd

Inventors

• Kim Ji Eun
• Lim Won Taeck
• Kim Yongjin
• Kim Gicheul
• Choi Wonmun
• Kim Ki Hyun

Classifications

• C08K5/0025

  Crosslinking or vulcanising agents; including accelerators · CPC title

• C07C29/172

  with the obtention of a fully saturated alcohol · CPC title

• C07C33/046

  Butynediols · CPC title

• C08J3/24

  Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K) · CPC title

• C07C31/20

  Dihydroxylic alcohols · CPC title