Multifunctional (meth)acrylate manufacturing method

Patent metadata

Field	Value
Publication number	US-2017204044-A1
Application number	US-201515302061-A
Country	US
Kind code	A1
Filing date	Mar 10, 2015
Priority date	Apr 16, 2014
Publication date	Jul 20, 2017
Grant date	—

Abstract

[Problem] The purpose of the present invention is to obtain a multifunctional (meth)acrylate with good yield by an ester exchange reaction of a polyhydric alcohol such as pentaerythritol or dipentaerythritol with a monofunctional (meth)acrylate.
[Solution] A multifunctional (meth)acrylate manufacturing method characterized in that when manufacturing a multifunctional (meth)acrylate by an ester exchange reaction of a polyhydric alcohol with a monofunctional (meth)acrylate, catalyst (A) and catalyst (B) are used together. Catalyst (A): One or more kinds of compounds selected from a group consisting of cyclic tertiary amines with an azabicyclo structure or salts or complexes thereof, amidines or salts or complexes thereof, and compounds with a pyridine ring or salts or complexes thereof. Catalyst (B): One or more kinds of compounds selected from a group consisting of zinc-containing compounds.

First claim

1 . A multifunctional (meth)acrylate manufacturing method, wherein the following catalyst A and catalyst B are used in combination for manufacturing a multifunctional (meth)acrylate by a transesterification of a polyhydric alcohol and a monofunctional (meth)acrylate:
Catalyst A: one or more kinds of compounds selected from the group consisting of cyclic tertiary amines with an azabicyclo structure or salts or complexes thereof, amidines or salts or complexes thereof, and compounds with a pyridine ring or salts or complexes thereof, Catalyst B: one or more kinds of compounds selected from the group consisting of zinc-containing compounds.

2 . The multifunctional (meth)acrylate manufacturing method according to claim 1 , wherein the polyhydric alcohol is a polyhydric alcohol having 3 or more alcoholic hydroxyl groups.

3 . The multifunctional (meth)acrylate manufacturing method according to claim 1 , wherein the polyhydric alcohol is any one of trimethylolethane, trimethylolpropane, glycerin, an alkylene oxide adduct of glycerin, tris(2-hydroxyethyl)isocyanurate, triethanolamine, ditrimethylolethane, ditrimethylolpropane, diglycerin, an alkylene oxide adduct of diglycerin, pentaerythritol, an alkylene oxide adduct of pentaerythritol, xylitol, dipentaerythritol, an alkylene oxide adduct of dipentaerythritol, and D-sorbitol.

4 . The multifunctional (meth)acrylate manufacturing method according to claim 1 , wherein the polyhydric alcohol is pentaerythritol or dipentaerythritol.

5 . The multifunctional (meth)acrylate manufacturing method according claim 1 , wherein the monofunctional (meth)acrylate is any one of methyl acrylate, ethyl acrylate, n-butyl acrylate, i-butyl acrylate, and 2-methoxyethyl acrylate

6 . The multifunctional (meth)acrylate manufacturing method according to claim 1 , wherein the monofunctional (meth)acrylate is 2-methoxyethyl acrylate.

7 . The multifunctional (meth)acrylate manufacturing method according to claim 1 , wherein the catalyst A is any one of quinuclidine, 3-hydroxy quinuclidine, triethylenediamine, N-methylimidazole, 1,8-diazabicyclo[5,4,0]undec-7-ene, and N,N-dimethyl-4-aminopyridine.

8 . The multifunctional (meth)acrylate manufacturing method according to claim 1 , wherein the catalyst B is a zinc-containing compound represented by the following General Formula (2) and/or General Formula (3):

wherein R3 and R4 are the same or different from each other and are a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched alkenyl group having 1 to 20 carbon atoms, an aryl group having 6 to 24 carbon atoms, or a cycloalkyl group having 5 to 20 carbon atoms,

wherein R5, R6, R7, R8, R9, and R10 are the same or different from each other and are a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched alkenyl group having 1 to 20 carbon atoms, an aryl group having 6 to 24 carbon atoms, or a cycloalkyl group having 5 to 20 carbon atoms.

9 . The multifunctional (meth)acrylate manufacturing method according to claim 1 , wherein the catalyst B is any one of zinc acetate, zinc propionate, zinc acrylate, zinc methacrylate, and zinc acetylacetonate.

10 . The multifunctional (meth)acrylate manufacturing method according to claim 1 , wherein the catalyst A is triethylenediamine and the catalyst B is zinc acetate.

Assignees

• Toagosei Co Ltd

Inventors

• Hashimoto Naoki
• Yamaguchi Shuuhei
• Ootsuka Motoo

Classifications

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title

• B01J31/04

  containing carboxylic acids or their salts {(B01J31/0277 - B01J31/0298 take precedence; multi-metal carboxylate complexes like Pd (II) acetate, i.e. Pd3 (OAc) 6 or Cr(II)acetate, i.e. Cr2(OAc)4 B01J31/2226)} · CPC title

• B01J31/0244

  with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine · CPC title

• C07C67/03 Primary

  by reacting an ester group with a hydroxy group · CPC title

• C07D251/30

  Only oxygen atoms · CPC title