JP5218813B2 - (Meth) acryloyl group-containing rosin derivative and method for producing the same - Google Patents

Description

The present invention relates to a novel rosin derivative having a (meth) acryloyl group and a method for producing the same.

Since a rosin derivative containing a (meth) acryloyl group has a three-dimensional cyclic skeleton derived from a resin acid and a polymerizable functional group in the molecule, it is highly useful as an industrial material. As the rosin derivative, for example, a (meth) acryloyl group-containing rosin derivative obtained by further reacting (meth) acrylic acid with a glycidyl ester compound obtained by reacting a stabilized rosin and epihalohydrin in the presence of a basic catalyst. It is known and can be used as a photosensitive conductive paste or the like (see, for example, Patent Document 1).

JP 2003-248307 A

An object of the present invention is to provide a novel rosin derivative having a (meth) acryloyl group.

The present inventor has found that a (meth) acryloyl group-containing rosin derivative represented by the following general formula (1) (hereinafter sometimes simply referred to as a rosin derivative) is novel and can be easily produced industrially. That is, the present invention provides:

1. General formula (1): Ro [—COO—CH (CH ₃ ) —O—R—A] _X (In the formula (1), Ro is tetrahydroabietic acid, dehydroabietic acid, dihydroabietic acid, acrylopimaric acid, and acrylopimaric acid. A cyclic hydrocarbon residue of one kind of resin acid selected from the group consisting of hydrides of the following: R is an alkylene group having 2 to 20 carbon atoms, an oxyalkylene group having 2 to 20 carbon atoms and 6 to 11 carbon atoms A (meth) acryloyl group-containing rosin derivative represented by one selected from the group consisting of the following aromatic groups, A represents a (meth) acryloyl group, and X represents an integer of 1 to 3.

2 . The general formula _{(1), Ro [-COO-} CH (CH 3) -O- (C 2 H 4 O) -A] is _X, the 1. (Meth) acryloyl group-containing rosin derivatives.

3 . Hydrogenated rosin or α, β unsaturated carboxylic acid modified rosin and general formula (2): CH ₂ ═CH—O—R—A (wherein R is an alkylene group having 2 to 20 carbon atoms, carbon A (meth) acryloyl group-containing monomolecule represented by the following: one selected from the group consisting of oxyalkylene groups having 2 to 20 carbon atoms and aromatic groups having 6 to 11 carbon atoms, and A represents a (meth) acryloyl group) A (meth) acryloyl group-containing rosin derivative obtained by subjecting a vinyl ether compound to a hemiacetal esterification reaction.

5. 3. The rosin is a hydrogenated rosin or an α, β unsaturated carboxylic acid-modified rosin. (Meth) acryloyl group-containing rosin derivatives.

6). Represented by the above general formula (2) (meth) acryloyl group-containing vinyl ether compound is a (meth) acrylic acid 2- (vinyloxy) ethyl, the three. (Meth) acryloyl group-containing rosin derivatives.

5 . Hydrogenated rosin or α, β-unsaturated carboxylic acid-modified rosin and general formula (2): CH ₂ ═CH—O—R—A (wherein R is an alkylene group having 2 to 20 carbon atoms, carbon number A (meth) acryloyl group-containing monovinyl ether compound represented by 2 to 20 oxyalkylene groups and one kind selected from aromatic groups having 6 to 11 carbon atoms, and A represents a (meth) acryloyl group) A method for producing a (meth) acryloyl group-containing rosin derivative, wherein a hemiacetal esterification reaction is performed.

6 . Represented by the above general formula (2) (meth) acryloyl group-containing vinyl ether compound is a (meth) acrylic acid 2- (vinyloxy) ethyl, the 5. The manufacturing method.

Since the rosin derivative of the present invention has a (meth) acryloyl group in the molecule, it can be used as a raw material for various (co) polymers, for example, together with other polymerizable monomers or alone. Further, the rosin derivative is a conventionally known application using rosins as a raw material, such as sizing agents, tackifiers, printing inks, road marking agents, synthetic rubber emulsifiers, soldering fluxes, and photosensitive conductive pastes. Can be used in applications.

The rosin derivative of the present invention is represented by the general formula (1): Ro [—COO—CH (CH ₃ ) —O—R—A] _X.

In the general formula (1), Ro represents a cyclic hydrocarbon residue of one kind of resin acid selected from the group consisting of tetrahydroabietic acid, dehydroabietic acid, dihydroabietic acid, acrylopimaric acid, and hydride of acrylopimaric acid. Represent. Here, the “ cyclic hydrocarbon residue ” refers to the remaining cyclic hydrocarbon group in the cyclic hydrocarbon skeleton of various resin acids , excluding one or more of the carboxyl groups present on the skeleton. Specifically, for example, when the resin acid is acrylopimaric acid described later, as the Ro in the general formula (1), the general formula (i):

A hydrocarbon group (the remaining structure excluding primary COOH and secondary COOH), and general formula (ii);

Examples of such hydrocarbon groups in which carboxyl groups remain (remaining structures excluding secondary COOH) can be exemplified. (In general formula (i) and general formula (ii), the broken line part in each cyclic hydrocarbon residue represents that a carbon-carbon double bond may exist there.)

These general formulas do not limit the shape of the cyclic hydrocarbon residue.

R in the general formula (1) is an alkylene group having 2 to 20 (preferably 2 to 6) carbon atoms (which may be linear, branched or cyclic), and 2 carbon atoms. 1 type chosen from -20 (preferably 4-10) oxyalkylene group and a C6-C11 aromatic group. The general formula (1) is preferably Ro [—COO—CH (CH ₃ ) —O— (C ₂ H ₄ O) —A] _X.

A in the general formula (1) represents an acryloyl group (—OC—HC═CH ₂ ) or a methacryloyl group (—OC— (CH ₃ ) C═CH ₂ ).

Moreover, X in the said General formula (1) represents the integer of 1-3. Note that the number of the (meth) acryloyl groups bonded to the Ro is determined according to the value of X.

  The specific structure of the rosin derivative according to the present invention is shown below. In addition, these are only illustrations and do not limit the structure shown by the said General formula (1) at all.

[When X = 1]

[When X = 2]

[When X = 3]

(In the general formulas (iii) to (vii), a broken line part in each cyclic hydrocarbon residue indicates that a carbon-carbon double bond may exist there.)

The rosin derivative of the present invention includes a hydrogenated rosin or an α, β-unsaturated carboxylic acid-modified rosin and a general formula (2): CH ₂ ═CH—O—R—A (wherein R is a carbon number of 2 1 type selected from the group consisting of an alkylene group of -20, an oxyalkylene group of 2-20 carbon atoms and an aromatic group of 6-11 carbon atoms, and A represents a (meth) acryloyl group). It is obtained by subjecting a (meth) acryloyl group-containing monovinyl ether compound to a hemiacetal esterification reaction. In the present invention, when the rosins contain a plurality of types of resin acids, a plurality of types of rosin derivatives can be obtained simultaneously as a composition.

The hydrogenated rosin or alpha, as the rosin as a raw material for β-unsaturated carboxylic acid-modified rosin such as natural rosin [gum rosin, tall oil rosin, wood rosin, etc.] and the like. The hydrogenated rosin is a rosin obtained by stabilizing the natural rosin by various known methods , and preferably has a color number of 3 or less by the Gardner colorimetric method (JISK0071-2). The rosin constituting the α, β unsaturated carboxylic acid modified rosin is the natural rosin, and the α, β unsaturated carboxylic acid is acrylic acid, methacrylic acid, itaconic acid, (anhydrous) maleic acid, fumaric acid. An α, β unsaturated carboxylic acid-modified rosin is obtained by subjecting the natural rosin and the α, β unsaturated carboxylic acid to a Diels-Alder reaction .

The hydrogenated rosin or the α, β-unsaturated carboxylic acid-modified rosin may contain resin acids described below in various composition ratios, and may contain impurities, impurities, and the like. In the present invention, when it is desired to produce the (meth) acryloyl group-containing rosin derivative represented by the general formula (1) in a high yield, the hydrogenated rosin or the α, β unsaturated carboxylic acid-modified rosin is: Those previously purified by various known methods (for example, recrystallization method) or those adjusted to a specific resin acid ratio can be used.

Specific examples of the resin acids contained in the natural rosin, hydrogenated rosin and α, β unsaturated carboxylic acid-modified rosin include monobasic resin acids [abietic acid, neoabietic acid, parastrinic acid, levopimaric acid, Dehydroabietic acid, dihydroabietic acid, tetrahydroabietic acid, pimaric acid, isopimaric acid, sandaracopimalic acid, etc.]; dibasic resin acid [dimer of the monobasic resin acid, acrylopimaric acid, etc.]; tribasic resin acid [fumaropimar Acid etc.]; monobasic resin acids having an anhydrous ring [maleopimaric acid, etc.] , resin acids obtained by hydrogenating these, and the like.

  In addition, as the (meth) acryloyl group-containing monovinyl ether compound (hereinafter referred to as monovinyl ether compound) represented by the general formula (2), various known compounds can be used without particular limitation. Specifically, for example, an alkylene group-containing monovinyl ether compound [(meth) acrylate 2-vinyloxyethyl, (meth) acrylate 3-vinyloxypropyl, (meth) acrylate 1-methyl-2-vinyloxyethyl, (meth) 2-vinyloxypropyl acrylate, 4-vinyloxybutyl (meth) acrylate, 1-methyl-3-vinyloxypropyl (meth) acrylate, 1-vinyloxymethylpropyl (meth) acrylate, (meth) acrylic acid 2 -Methyl-3-vinyloxypropyl, 1,1-dimethyl-2-vinyloxyethyl (meth) acrylate, 3-vinyloxybutyl (meth) acrylate, 1-methyl-2-vinyloxypropyl (meth) acrylate, (meth ) 2-vinyloxybutyl acrylate, 4-vinyloxycyclohexane (meth) acrylate Sil, 6-vinyloxyhexyl (meth) acrylate, 4-vinyloxymethylcyclohexylmethyl (meth) acrylate, 3-vinyloxymethylcyclohexylmethyl (meth) acrylate, 2-vinyloxymethylcyclohexyl (meth) acrylate Methyl, etc.]; oxyalkylene group-containing monovinyl ether compounds [2- (vinyloxyethoxy) ethyl (meth) acrylate, 2- (vinyloxyisopropoxy) ethyl (meth) acrylate, 2- (vinyl) (meth) acrylate (Roxyethoxy) propyl, 2- (vinyloxyethoxy) isopropyl (meth) acrylate, 2- (vinyloxyisopropoxy) propyl (meth) acrylate, 2- (vinyloxyisopropoxy) isopropyl (meth) acrylate, ( META) ACRYLIC ACID 2- (VINYLOXIETO) Ciethoxy) ethyl, 2- (vinyloxyethoxyisopropoxy) ethyl (meth) acrylate, 2- (vinyloxyisopropoxyethoxy) ethyl (meth) acrylate, 2- (vinyloxyisopropoxyisopropoxy) (meth) acrylate ) Ethyl, 2- (vinyloxyethoxyethoxy) propyl (meth) acrylate, 2- (vinyloxyethoxyisopropoxy) propyl (meth) acrylate, 2- (vinyloxyisopropoxyethoxy) propyl (meth) acrylate, 2- (vinyloxyisopropoxyisopropoxy) propyl (meth) acrylate, 2- (vinyloxyethoxyethoxy) isopropyl (meth) acrylate, 2- (vinyloxyethoxyisopropoxy) isopropyl (meth) acrylate, (meta ) Acrylic acid 2- (vinyloxy) Cyisopropoxyethoxy) isopropyl, 2- (vinyloxyisopropoxyisopropoxy) isopropyl (meth) acrylate, 2- (vinyloxyethoxyethoxyethoxy) ethyl (meth) acrylate, 2- (vinyloxy) (meth) acrylate Ethoxyethoxyethoxyethoxy) ethyl, (meth) acrylic acid polyethylene glycol monovinyl ether, (meth) acrylic acid polypropylene glycol monovinyl ether, etc.]; aromatic group-containing monovinyl ether compound [(meth) acrylic acid p-vinyloxymethylphenylmethyl, (Meth) acrylic acid m-vinyloxymethylphenylmethyl, (meth) acrylic acid o-vinyloxymethylphenylmethyl, etc.]. The monovinyl ether compound is preferably the oxyalkylene group-containing monovinyl ether compound, particularly 2- (vinyloxyethoxy) ethyl (meth) acrylate.

The hemiacetal esterification reaction is not particularly limited, and various known methods can be employed. Specifically, for example, the hydrogenated rosin or α, β unsaturated carboxylic acid-modified rosin and the monovinyl ether compound are usually about 30 to 150 ° C. (preferably in the presence or absence of a catalyst or an organic solvent). Is 50 to 120 ° C.), usually about 10 minutes to 6 hours (preferably 20 minutes to 5 hours).

The hydrogenated rosin or alpha, beta-unsaturated carboxylic acid-modified rosin, and the amount of the monovinyl ether compound is not particularly limited, from the stoichiometric point of view, the hydrogenated rosin or alpha, beta-unsaturated carboxylic acid-modified It is preferable that the vinyl ether group of the monovinyl ether compound is usually in the range of about 0.5 to 3.0 mol (preferably 1.0 to 2.0 mol) with respect to 1 mol of the carboxyl group in the rosin . If it is less than 0.5, the yield of the target product will be small, while if it is 3.0 or more, the residual ratio of unreacted products tends to be large. In the present invention, the molar ratio of hydrogenated rosin or α, β unsaturated carboxylic acid-modified rosin to monovinyl ether compound (number of moles of carboxyalkyl group / number of moles of vinyl ether group), hydrogenated rosin or α, β By changing the type of unsaturated carboxylic acid-modified rosin , the shape of Ro in the general formula (1) (remaining carboxyl group, etc.) and the value of X (change in the number of (meth) acryloyl groups) Etc. becomes possible.

As the catalyst, various known catalysts can be used without particular limitation. Specific examples include phosphate ester acid catalysts [di-n-butyl phosphate, 2-ethylhexyl phosphate, monooctyl phosphate, etc.]. The amount of the catalyst used is usually about 0.01 to 3 parts by weight (preferably 0.1 to 3 parts by weight based on 100 parts by weight of the total of the hydrogenated rosin or α, β unsaturated carboxylic acid modified rosin and the vinyl ether compound. ~ 1.5 parts by weight).

The organic solvent is preferably used for controlling the reaction, and various known solvents can be used without particular limitation. Specifically, for example, aromatic hydrocarbons [benzene, toluene, xylene, ethylbenzene, aromatic petroleum naphtha, tetralin, turpentine oil, Solvesso # 100 (registered trademark of Exxon Chemical Co., Ltd.), Solvesso # 150 (Exxon Chemical ( (Registered trademark) etc.]; ethers (dioxane, tetrahydrofuran, etc.); esters (methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, sec-butyl acetate, amyl acetate, etc.) ] Ether esters [diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol diethyl ether, triethylene glycol diethyl ether, diethylene glycol dibutyl ether, triethylene glycol dibutyl ether Propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, methoxybutyl acetate, etc.]; glycol ether acetates [ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, etc.]; ketones [acetone, methyl ethyl ketone, Methyl isobutyl ketone, methyl amyl ketone, cyclohexanone, isophorone, mesityl oxide, methyl isoamyl ketone, ethyl butyl ketone, ethyl amyl ketone, diisobutyl ketone, diethyl ketone, methyl propyl ketone, diisopropyl ketone, etc.]; Phosphate esters [trimethyl phosphate , Triethyl phosphate, tributyl phosphate, etc.). It can be used singly or in combination of two or more species. The amount of the organic solvent used is preferably such that the solid content concentration of the reaction system is usually in the range of about 20 to 95% by weight (preferably 30 to 90% by weight) so that the reaction proceeds smoothly.

In the reaction, various known radical polymerization inhibitors can be used without particular limitation for the purpose of suppressing radical polymerization of the raw material and the product itself from the viewpoint of improving the yield. Specifically, for example, quinone polymerization inhibitors [methoquinone, hydroquinone, methoxyhydroquinone, benzoquinone, p-tert-butylcatechol, etc.]; alkylphenol polymerization inhibitors [2,6-di-tert-butylphenol, 2,4 -Di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-methylphenol, 2,4,6-tri-tert-butylphenol, etc.]; amine Polymerization inhibitors [alkylated diphenylamine, N, N′-diphenyl-p-phenylenediamine, phenothiazine, 4-hydroxy-2,2,6,6-tetramethylpiperidine, 4-benzoyloxy-2,2,6, 6-tetramethylpiperidine, 1,4-dihydroxy-2,2,6,6 Tetramethylpiperidine, 1-hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine etc.]; copper dithiocarbamate polymerization inhibitors [copper dimethyldithiocarbamate, copper diethyldithiocarbamate, copper dibutyldithiocarbamate, etc. N-oxyl polymerization inhibitor [2,2,6,6-tetramethylpiperidine-N-oxyl, 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl, 4-benzoyloxy -2,2,6,6-tetramethylpiperidine-N-oxyl, esters of 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl, etc.]; It can be used alone or in combination of two or more. The addition amount of the radical polymerization inhibitor is usually 0.0005 to 0.5 mass with respect to the total weight of the rosins and the vinyl ether compound, from the viewpoint of yield, suppression of polymerization, and economical reasons. % (Preferably 0.001 to 0.1% by mass). Moreover, at the time of the said reaction, superposition | polymerization inhibition means, such as air bubbling, can be taken.

The (meth) acryloyl group-containing rosin derivative according to the present invention thus obtained can be used for various purposes as it is, but various purification treatments (filtration, distillation, solvent extraction, column separation, reprecipitation as necessary) Etc.).

EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated in detail, this invention is not limited to these.

Example 1
In a 300 ml flask equipped with a water pipe, 150 g of hydrogenated rosin (mainly containing dehydroabietic acid, dihydroabietic acid, and tetrahydroabietic acid as resin acids) manufactured by Arakawa Chemical Industries, Ltd., 0.23 g of methoquinone, phenothiazine 0.23 g was charged and the reaction system was heated to 120 ° C. with stirring to melt them. Next, 82.9 g of 2- (vinyloxyethoxy) ethyl acrylate was added dropwise to the reaction system taking 15 minutes from the dropping funnel, and then 2-ethylhexyl phosphate (trade name “AP-8” (Daihachi Chemical Industry Co., Ltd.). (Made by Co., Ltd.)) 0.15g was prepared, and it heat-retained at 100 degreeC for 1 hour, and obtained the acryloyl group containing rosin derivative.

Example 2
Acrylic acid-modified rosin hydride manufactured by Arakawa Chemical Industries (mainly acrylopimaric acid, acrylopimaric acid hydride, dehydroabietic acid, dihydroabietic acid, tetrahydroabieticin as a resin acid) (Containing acid) 130 g, methoquinone 0.23 g, and phenothiazine 0.23 g were charged, and the mixture was heated to 140 ° C. and melted while stirring under a reaction system. Subsequently, 102.4 g of ethyl (2-vinyloxyethoxy) acrylic acid was dropped into the reaction system taking 15 minutes from the dropping funnel, and then 2-ethylhexyl phosphate (trade name “AP-8” (Daihachi Chemical Industry Co., Ltd.). (Made by Co., Ltd.)) 0.15g was prepared, and it heat-retained at 100 degreeC for 1 hour, and obtained the acryloyl group containing rosin derivative.

Example 3
A 300 ml flask equipped with a diversion tube was charged with 120 g of polymerized rosin (mainly containing a dimer of a monobasic resin acid as a resin acid), 0.19 g of methoquinone, and 0.19 g of phenothiazine. While stirring, the reaction system was heated to 160 ° C. and melted. Subsequently, 55.8 g of ethyl (2-vinyloxyethoxy) acrylic acid was dropped into the reaction system taking 15 minutes from the dropping funnel, and then 2-ethylhexyl phosphate (trade name “AP-8” (Daihachi Chemical Industry Co., Ltd.). (Made by Co., Ltd.)) 0.12g was prepared, and it heat-retained at 100 degreeC for 1 hour, and obtained the acryloyl group containing rosin derivative.

Example 4
In a 300 ml flask equipped with a water pipe, 150 g of hydrogenated rosin (mainly containing dehydroabietic acid, dihydroabietic acid, and tetrahydroabietic acid as resin acids) manufactured by Arakawa Chemical Industries, Ltd., 0.23 g of methoquinone, phenothiazine 0.23 g was charged and the reaction system was heated to 120 ° C. with stirring to melt them. Next, 89.1 g of 2- (vinyloxyethoxy) ethyl methacrylate was added dropwise to the reaction system in 15 minutes from the dropping funnel, and then 2-ethylhexyl phosphate (trade name “AP-8” (Daihachi Chemical Industry Co., Ltd.). (Made by Co., Ltd.)) 0.15g was prepared, and it heat-retained at 100 degreeC for 1 hour, and obtained the methacryloyl group containing rosin derivative.

Each ¹ H NMR chart (measuring instrument: GEMINI-300 (manufactured by VARIAN)), 300 MHz, CDCl ₃ ), IR chart (measuring instrument: AVATAR-330) of the acryloyl group-containing rosin derivatives obtained in Examples 1 to 4 Thermo) and single reflection ATR) are shown in the figure.

The rosin derivative according to the present invention is a conventionally known application using rosins as a raw material, for example, sizing agent, tackifier, printing ink, road marking agent, synthetic rubber emulsifier, soldering flux, photosensitive conductive paste and the like. It can be used in the following applications.

1 is a ¹ H NMR chart of the rosin derivative obtained in Example 1. FIG. FIG. 2 is an IR chart of the rosin derivative obtained in Example 1. FIG. 3 is a ¹ H NMR chart of the rosin derivative obtained in Example 2. 4 is an IR chart of the rosin derivative obtained in Example 2. FIG. FIG. 5 is a ¹ H NMR chart of the rosin derivative obtained in Example 3. 6 is an IR chart of the rosin derivative obtained in Example 3. FIG. FIG. 7 is a ¹ H NMR chart of the rosin derivative obtained in Example 4. FIG. 8 is an IR chart of the rosin derivative obtained in Example 4.

Claims (6)

General formula (1): Ro [—COO—CH (CH ₃ ) —O—R—A] _X (In the formula (1), Ro is tetrahydroabietic acid, dehydroabietic acid, dihydroabietic acid, acrylopimaric acid, and acrylopimaric acid. A cyclic hydrocarbon residue of one kind of resin acid selected from the group consisting of hydrides of the following: R is an alkylene group having 2 to 20 carbon atoms, an oxyalkylene group having 2 to 20 carbon atoms and 6 to 11 carbon atoms A (meth) acryloyl group-containing rosin derivative represented by one selected from the group consisting of the following aromatic groups, A represents a (meth) acryloyl group, and X represents an integer of 1 to 3. The general formula _{(1), Ro [-COO-} CH (CH 3) -O- (C 2 H 4 O) -A] is _X, as claimed in claim 1 (meth) acryloyl group-containing rosin derivative. Hydrogenated rosin or α, β unsaturated carboxylic acid modified rosin and general formula (2): CH ₂ ═CH—O—R—A (wherein R is an alkylene group having 2 to 20 carbon atoms, carbon A (meth) acryloyl group-containing monomolecule represented by the following: one selected from the group consisting of oxyalkylene groups having 2 to 20 carbon atoms and aromatic groups having 6 to 11 carbon atoms, and A represents a (meth) acryloyl group) A (meth) acryloyl group-containing rosin derivative obtained by subjecting a vinyl ether compound to a hemiacetal esterification reaction. The (meth) acryloyl group-containing rosin derivative according to claim 3 , wherein the (meth) acryloyl group-containing vinyl ether compound represented by the general formula (2) is 2- (vinyloxyethoxy) ethyl (meth) acrylate. Hydrogenated rosin or α, β unsaturated carboxylic acid modified rosin and general formula (2): CH ₂ ═CH—O—R—A (wherein R is an alkylene group having 2 to 20 carbon atoms, carbon A (meth) acryloyl group-containing monovinyl ether compound represented by one kind selected from an oxyalkylene group having 2 to 20 carbon atoms and an aromatic group having 6 to 11 carbon atoms, and A represents a (meth) acryloyl group) Is a hemiacetal esterification reaction, and a method for producing a (meth) acryloyl group-containing rosin derivative. The production method of claim 5 , wherein the (meth) acryloyl group-containing vinyl ether compound represented by the general formula (2) is 2- (vinyloxyethoxy) ethyl (meth) acrylate.

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