JPH0578558B2 - - Google Patents

Description

[Detailed description of the invention]

A. Industrial Application Field The present invention relates to a novel acrylate compound represented by the formula () and a method for producing the same.

[C] The acrylate compound represented by the formula () is
It can be easily homopolymerized or copolymerized with other unsaturated group-containing compounds in the presence of heat, ultraviolet rays, ionizing radiation, or a radical polymerization initiator. B. Prior Art Various acrylic esters have been known so far. For example, monofunctional monomers such as methyl methacrylate, ethyl acrylate, and 2-ethylhexyl acrylate, and polyfunctional monomers such as trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, and pentaerythritol triacrylate are generally known.
Among monofunctional monomers, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, and the like are known as 2-hydroxyalkyl acrylates. As for the production method of the above-mentioned 2-hydroxypropyl acrylates, there are
-1465, 1977-15988, 40069, 40069, 28081, 28082, 28082, 48-
28599, a method in which an epoxy compound and acrylic acid are reacted in the presence of a catalyst is known, but a method in which a spiro ring is introduced into β-hydroxyalkyl acrylate as in the present invention and a method for producing the same are still unknown. It hasn't been done yet. On the other hand, as a method for producing diacrylate using a diepoxide compound as a raw material, U.S. Patent No.
3770602 is known. This is a method in which an acid anhydride of acrylic acid and acrylic acid or other carboxylic acid is reacted with a diepoxy compound in the presence of a catalyst to obtain a tetraester compound containing two or more acryloyl groups in one molecule. It is. However, the anhydride of acrylic acid and carboxylic acid used here is expensive, and from an economic standpoint, its practical use as a crosslinking agent or resin modifier is poor. C. Means, action, and effect for solving the problem In contrast, in the present invention, diacrylate is produced using acrylic acid or acrylic ester as a raw material, all of which are easily and inexpensively available as industrial raw materials. It's something you get. Furthermore, the compound obtained here has excellent solubility because it has a hydroxyl group, and provides a cured resin product that has excellent flexibility due to its spiro structure. Therefore, the acrylate compound of the present invention, the ink,
In addition to being useful as a raw material or modifier for paints, adhesives, coatings, and molding resins, it can also be used as a reaction intermediate for organic synthesis by using the hydroxyl group as a reaction site. What the present invention encompasses is a novel 3,9-bis[1,1-dimethyl-2-
(2(or 3)-acryloyloxy-3(or 2)-hydroxypropoxy)ethyl]-2,4,
This invention relates to 8,10-tetraoxaspiro[5,5]undecane and its production method. The new compound represented by the chemical formula () uses spiroglycol diglycidyl ether represented by the formula () as a starting material.

[Chemical formula] For the compound represented by the formula (), catalysts known as hydroxyesterification catalysts for epoxy compounds, such as imidazoles such as 2-methylimidazole, quaternary ammonium salts such as tetramethylammonium chloride, benzyl dimethyl A compound represented by the formula () is synthesized by reacting with acrylic acid in the presence of an amine, tertiary amines such as tributylamine, or lauric acid ester such as dibetyltin dilaurate. The reaction temperature is advantageously carried out at 75 to 120°C from the viewpoint of shortening the reaction time and preventing polymerization. A polymerization inhibitor is added to prevent thermal polymerization of acrylic acid. Such polymerization inhibitors include hydroquinone, p-methoxyphenol,
2,4-dimethyl-6-t-butylphenol,
3-Hydroxythiophenol, α-nitroso-
Examples include β-naphthol, p-benzoquinone, 2,5-dihydroxy-p-quinone, copper salts, and the like. D Examples The present invention will be explained below with reference to Examples. Spiroglycol diglycidyl ether 104g,
Acrylic acid 36g, p-methoxyphenol 0.5g,
Triethylbenzylammonium chloride 0.2
A solution of g in 200 ml of benzene was refluxed with stirring, reacted for 6 hours, and then cooled. After neutralizing the reaction mixture with saturated aqueous sodium carbonate solution,
It was washed with saturated saline until it no longer showed alkalinity. When benzene was distilled off under reduced pressure, 124 g of a pale yellow liquid compound () was obtained. The liquid compound () obtained in the example has low odor and has the following properties. ●Infrared absorption spectrum (liquid film, cm ^-1 ) 3460 (stretching vibration of OH group) 2980-2880 (CH stretching vibration) 1730 (C=O stretching vibration of acrylic ester) 1630, 1620 (CH stretching vibration of acrylic ester) ₂ = CH−
Stretching vibration) 1405 (CH ₂ = CH- in-plane bending vibration of acrylic ester) 1180 (C-O- stretching vibration of acrylic ester) 1095 (C-O- stretching vibration of spiro ring) Nuclear magnetic resonance spectrum ( ^13C -NMR, 22.5MHz, _CDCl3 ), δ (ppm)

[ka] a: 131.0 g: 69.7 b: 127.8 h: 19.4 c: 165.8 i: 39.0 d: 79.1 j: 104.7 e: 71.6 k: 70.2 f:71.2 l:32.2

Claims (1)

[Claims] 1. An acrylate compound represented by the following chemical formula (). [Chemical Formula] 2. A method for producing an acrylate compound represented by the following chemical formula (), which comprises reacting spiroglycol diglycidyl ether with acrylic acid or an acrylic ester. [ka]