JP2974076B2 - Method for producing reactive composition containing monomer - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a method for producing a reactive composition containing a reaction product of a hydroxyalkyl vinyl ether and a lactone as a main component and containing a monomer.

[Prior art] Conventionally, hydroxyalkyl vinyl ether is a fluorinated paint resin having a hydroxyl group by radical copolymerization with a fluorine-based ethylene monomer such as chlorotrifluoroethylene together with an alkyl vinyl ether, a fatty acid vinyl ester, an allyl ether monomer and the like. It has attracted attention and has been widely used for ultra-durable paints using a resin or a polyvalent isocyanate compound as a curing agent.

[Problems to be Solved by the Invention] However, even these paints have not always been satisfactory for applications requiring elongation of the coating film.

The present inventors have intensively studied to obtain a compound capable of imparting excellent flexibility to a fluororesin-based paint in order to solve these problems, and as a result, have obtained a hydroxy compound produced by the production method of the present invention. The present inventors have found that a reactive composition containing a monomer obtained by ring-opening addition polymerization of a lactone monomer with an alkyl vinyl ether is extremely effective, and arrived at the present invention.

[Means for Solving the Problems] That is, the present invention relates to the following formula: [Wherein, R ³ and R ⁴ may be the same or different and each represent a hydrogen atom or a methyl group or an ethyl group, and R ³ and R ⁴ bonded to adjacent carbons may be the same or different; Y represents an integer of 3 to 7. A compound represented by the following formula (1) obtained by subjecting a lactone monomer represented by the following to an addition reaction with a hydroxyalkyl vinyl ether: [Wherein, R ¹ and R ² may be the same or different and each represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R ¹ and R ² bonded to adjacent carbons are the same or different. R ³ and R ⁴ may be the same or different, each represents a hydrogen atom or a methyl group or an ethyl group, and R ³ and R ⁴ bonded to adjacent carbons may be the same or different, and x Represents an integer from 1 to 10, and n represents an integer from 1 to 100. When producing a reactive composition containing the lactone monomer, the water content in the lactone monomer is 0.02% by weight or less, and the water content in the hydroxyalkyl vinyl ether is 1.0% by weight or less. Reacting the lactone monomer with a hydroxyalkyl vinyl ether such that the water content in the reactive composition containing the monomer is 1.02% by weight or less; Method. It is.

In the production method of the present invention, specific examples of lactone monomers in a starting material component for producing a reactive composition containing a monomer include butyrolactone, β-methylpropiolactone, ε-caprolactone, 3, There are 3,5-trimethylcaprolactone, 3,5,5-trimethylcaprolactone, β-methyl-δ-valerolactone and the like, and these can be used alone or as a mixture of two or more kinds at any ratio. . Industrially, ε-caprolactone is mainly used, and 3,3,5-trimethylcaprolactone, 3,5,5-trimethylcaprolactone or β-methyl-δ-valerolactone is added at an arbitrary ratio depending on the purpose. Is advantageous.

Ε-caprolactone, 3,3,5-trimethylcaprolactone, and 3,5,5-trimethylcaprolactone used in the present invention are obtained by oxidizing cyclohexanone and 3,3,5-trimethylcyclohexanone by a Bayer-Billiger reaction using a peracid. Can be manufactured.

In particular, 3,3,5-trimethylcaprolactone and 3,5,5
Trimethylcaprolactone can be obtained as a mixture by reacting 3,3,5-trimethylcyclohexanone with a peracid, but the mixture can be separated by a known method such as distillation and used alone or in a mixture. Can also.

Specific examples of the hydroxyalkyl vinyl ether as the other compound in the starting material components include hydroxymethyl vinyl ether, 2-hydroxyethyl vinyl ether, 3-hydroxypropyl vinyl ether, 4-hydroxybutyl vinyl ether, 3-hydroxybutyl vinyl ether, 5-hydroxypentyl vinyl ether, 5-hydroxyhexyl vinyl ether, diethylene glycol monovinyl ether, triethylene glycol monovinyl ether, cyclohexane dimethanol monovinyl ether, and a monovinyl ether of an ethylene oxide adduct of bisphenol A,
Monovinyl ethers of ethylene oxide adducts of terephthalic acid, monovinyl ether compounds of dihydric alcohols, 6-hydroxyhexyl vinyl ether and the like can be mentioned.

These hydroxyalkyl vinyl ethers are prepared by a method of adding an alkanediol to acetylene [US Pat. No. 3,429,845 or Ann., Chem., 601, 81 (1956).
And a method of synthesizing a compound by an ether exchange reaction between an alkyl vinyl ether and an alkanediol (see JP-A-1-34211).

One mole of hydroxyalkyl vinyl ether, one of the starting materials used in the present invention, is subjected to a ring-opening addition reaction of 1 to 100 moles, preferably 1 to 12 moles, of a lactone monomer. This ring-opening addition reaction product is a main product in the reactive composition containing the monomer, and is represented by the above formula (1).
When the amount of the lactone monomer is 100 mol or more, the resin becomes too soft, which is not preferable.

The ring-opening addition reaction of the lactone to the hydroxyalkyl vinyl ether is carried out at 0 to 230 ° C, preferably at 50 to 220 ° C. At a temperature lower than 50 ° C, the reaction rate is low.
At a temperature of 0 ° C. or higher, the degree of coloring increases, and a decomposition reaction easily occurs, which is not preferable.

It is preferable to use a catalyst for this reaction. Examples of the catalyst include titanium compounds such as tetrabutyl titanate, tetrapropyl titanate, and tetraethyl titanate; organic tin compounds such as tin octylate, dibutyltin oxide and dibutyltin laurate; and stannous chloride, stannous bromide, and iodide. tin halide with an alkali metal alcoholate of the first tin, butyl lithium, p-toluenesulfonic acid, may be used an alkali or acid catalyst such as sulfuric acid, BF _3.

The amount of the catalyst used is 0.01 to 200 ppm, preferably 0.1 to 50 ppm.
It is.

When a tin-based catalyst is used, a product having a higher molecular weight is obtained than when a titanium-based catalyst is used. In the case of a tin-based catalyst, side reactions such as polymerization and intramolecular cyclization of hydroxyalkyl vinyl ether, or addition and polymerization of a compound represented by the formula (1) occur. Is more preferred.

Further, when the reaction is performed in an air atmosphere, the color tends to be colored. Therefore, the reaction is preferably performed in an inert atmosphere such as nitrogen.

This reaction is preferably performed in the presence of a suitable inhibitor that prevents polymerization of the double bond of the hydroxyalkyl vinyl ether, but may be performed in the absence of the same.

These inhibitors include hydroquinone monomethyl ether, benzoquinone, phenothiazine, methylhydroquinone, 2,5-di-t-butylquinone, hydroquinone, and the like.

The amount of inhibitor used is 1000 ppm or less, preferably 500 pp
m or less.

The reaction may be performed without a solvent, or may be performed in an inert solvent having no active hydrogen such as toluene, xylene, methyl ethyl ketone, and methyl isobutyl ketone.

The use of the solvent is effective in lowering the viscosity of the reaction crude liquid in the system after the completion of the reaction, and facilitates temperature control during the reaction.

Whether or not an inert solvent is used can be arbitrarily selected according to the intended use of the reactive monomer composition produced by the production method of the present invention. That is, it can be used for products that may contain a solvent such as a paint.

Further, as a matter of course, the inert solvent may be added to the crude reaction solution after the completion of the reaction. The amount of inert solvent used is 5 to 80% by weight, preferably 10 to 50% by weight. However,
Solvents having ester bonds are not preferred. This is because a transesterification reaction occurs with the ester group of polycaprolactone during the reaction, and a lactone polymer not bonded to the hydroxyalkyl vinyl ether may be formed.

In particular, in the present reaction, a titanium-based catalyst is effective, and it is preferable to avoid an ester-based solvent since the titanium-based catalyst easily promotes the transesterification reaction.

In the present invention, the water content in the lactone monomer used is 0.02.
Wt% or less, the water content in the hydroxyalkyl vinyl ether should be 1.0 wt% or less, or the lactone monomer so that the water content in the reactive composition containing the reacted monomer is 1.02 wt% or less. It is essential to react with hydroxyalkyl vinyl ether. The lower the water content in the raw material, the better. However, from the viewpoint of economy, the water content in the lactone monomer is 0.001% to 0.02%.
A weight percent is sufficient. In addition, about 0.001 to 1.0% by weight of water in the hydroxyalkyl vinyl ether is sufficient. If the raw material contains a large amount of water, the lactone monomer is opened to increase the acid value of the product, which adversely affects the product.

That is, it promotes the hydrolysis reaction of the compound represented by the formula (1), which is the main component in the composition produced by the production method of the present invention. On the other hand, when synthesizing a silane coupling agent using a platinum catalyst, the catalyst poisons platinum and causes a decrease in reactivity.

Therefore, when the raw material contains a large amount of water, a product having a low acid value can be obtained by heating under reduced pressure to distill only water before the catalyst is charged and the reaction is started. The lactone may be dehydrated using a dehydrating agent such as molecular sieve.

When the reaction is terminated under the above conditions, an example of a typical ratio of components other than the inert solvent in the reactive composition containing the obtained monomer is as follows.

That is, the lactone monomer is 0.5% by weight or less, the hydroxyalkyl vinyl ether is 50% by weight or less, the by-product is 2% by weight or less, the compound represented by the above formula (1) is 97% by weight or less, and the catalyst is about 200 ppm or less. , And the inhibitor is about
The composition is about 500 ppm or less. For example, when the content of the lactone monomer is desired to be 0.5% by weight or less, a long reaction time may be taken. However, in this case, the content of the by-products increases.

On the other hand, when it is desired that the content of the lactone monomer and the content of the hydroxyalkyl vinyl ether be 5 to 10% by weight, the reaction may be terminated in the middle. In this case, the content of by-products decreases. To end the reaction halfway, specifically, lower the reaction temperature maintained at 70 ° C to 200 ° C to less than 60 ° C, preferably to about room temperature, or add a catalyst masking agent such as a phosphorus-containing compound. Then, the catalyst may be deactivated and the temperature may be lowered.
A composition containing such unreacted components will be in a state similar to a composition containing an inert solvent. The content of the by-products increases when the amount of the catalyst used is large or when the synthesis is performed under the condition of a high reaction temperature. Further, when the polymerization is carried out under the same conditions, it depends on the type of the catalyst.

Specific forms of the by-products include, for example, lactones containing a carboxyl group and a hydroxyl group at a terminal formed by ring-opening polymerization of the lactone monomer due to moisture or the like remaining slightly in the lactone monomer and the hydroxyalkyl vinyl ether. Or a compound produced by a transesterification reaction, as shown by the following formulas (2) and (3), produced by an addition reaction of an intramolecular and intermolecular hydroxyl group to a vinyl group of an initiator by an acid catalyst. Acetal-type compounds In addition, a small amount of a polymer in which a vinyl group portion is polymerized, and a small amount of a side reaction product whose structure is difficult to identify. As for the content of the catalyst, the amount added to the starting material remains almost as it is. If necessary, it can be removed by washing or an adsorbent.

The reactive composition containing a lactone-modified hydroxyalkyl vinyl ether as a main component according to the production method of the present invention can be copolymerized with, for example, polyfluoroolefin to obtain a fluorine-containing copolymer having a hydroxyl group. Further, it can be reacted with a curing agent such as an isocyanate or a melamine resin to obtain a paint having excellent weather resistance and flexibility.

On the other hand, a platinum catalyst in the obtained hydroxyl-containing lactone-modified hydroxyalkyl vinyl ether containing 0.1 to 1000 ppm
By adding and reacting with trimethoxysilane, silicon is added to the double bond of the vinyl group to obtain a silane coupling agent. The obtained silane coupling agent has much higher compatibility with resins and shows excellent adhesion as compared with those not modified with lactones.

These compositions are solids or liquids, with the most preferred compositions being liquids.

These compositions contain a compound represented by the above formula (1) as a main component, a lactone of 20% by weight or less, a hydroxyalkyl vinyl ether of 50% by weight or less, a small amount of other reaction products, and a catalyst residue of 2000 ppm or less. , And 500 ppm or less of the inhibitor, and their contents can be controlled in an arbitrary range.

Hereinafter, specific examples of the present invention will be described with reference to examples,
The present invention is not limited by these examples.

Example 1 A flask equipped with a nitrogen inlet tube, a thermometer, a cooler and a stirrer was charged with 110.9 g of 4-hydroxybutyl vinyl ether and ε
327.5 g of caprolactone, 0.2230 g of hydroquinone monomethyl ether as an inhibitor, and 2.20 g of stannous chloride (1% ε-caprolactone solution) as a catalyst were reacted at 115 ° C. for 22 hours while passing air. The conversion of ε-caprolactone was 75%.

Example 2 In a flask equipped with the same apparatus as in Example 1, 50.0 g of 4-hydroxybutyl vinyl ether and ε-caprolactone 1
47.9 g, hydroquinone monomethyl ether 0.0998 g as an inhibitor, and 1.00 g of stannous chloride (1% ε-caprolactone solution) as a catalyst were added at 150 ° C. while passing air.
Allowed to react for hours. The reaction rate of ε-caprolactone is 99.6%
Met.

Example 3 In a flask equipped with the same apparatus as in Example 1, 50.0 g of 4-hydroxybutyl vinyl ether and ε-caprolactone 1
47.4 g, 0.0990 g of hydroquinone monomethyl ether as an inhibitor and 0.2000 g of stannous chloride (1% ε-caprolactone solution) as a catalyst are added at 150 ° C. while passing air.
The reaction was performed for 12 hours.

The conversion of ε-caprolactone was 90%. This was cooled and taken out, and the properties were examined. The results were as follows.

Appearance (APHA) 35 Acid value (mgKOH / g) 0.113 OH value (mgKOH / g) 102.10 Viscosity (cp 45 ° C) 52 H ₂ O (%) 0.086 Example 4 A flask equipped with the same apparatus as in Example 1 4-hydroxybutyl vinyl ether 50.0 g, ε-caprolactone 1
49.2 g, hydroquinone monomethyl ether 0.1000 g as an inhibitor, and 1.00 g of stannous chloride (1% ε-caprolactone solution) as a catalyst were added.
Allowed to react for hours. The reaction rate of ε-caprolactone is 99.7%
Met.

This was cooled, taken out and examined for properties. The results were as follows.

Appearance (APHA) 150 Acid value (mgKOH / g) 0.540 OH value (mgKOH / g) 16.49 Viscosity (cp 45 ° C) 6200 H ₂ O (%) 0.046 Iodine value 9.39 Example 5 Equipped with the same apparatus as in Example 1. 52.1 g of 4-hydroxybutyl vinyl ether, ε-caprolactone 1
53.6 g and stannous chloride (1% ε-caprolactone solution) 0.2230 g as a catalyst were added and reacted at 170 ° C. for 8 hours while passing nitrogen.

The conversion of ε-caprolactone was 99.5%. This was cooled, taken out, and examined for properties. The results were as follows.

Appearance (APHA) 45 Acid value (mgKOH / g) 0.121 OH value (mgKOH / g) 78.8 Viscosity (cp 45 ° C) 142 H ₂ O (%) 0.02 Iodine value 8.28 Example 6 Equipped with the same apparatus as in Example 1. 50.0 g of 4-hydroxybutyl vinyl ether, ε-caprolactone 1
47.5 g and 1.00 g of stannous chloride (1% ε-caprolactone solution) as a catalyst were added and reacted at 170 ° C. for 3 hours while passing nitrogen.

The conversion of ε-caprolactone was 99.5%. This was cooled, taken out, and examined for properties. The results were as follows.

Appearance (APHA) 65 Acid value (mgKOH / g) 0.61 OH value (mgKOH / g) 34.2 Viscosity (cp 45 ° C) 740 H ₂ O (%) 0.021 Example 7 A flask equipped with the same apparatus as in Example 1 4-hydroxybutyl vinyl ether 50.0 g, ε-caprolactone 1
47.4 g, hydroquinone monomethyl ether 0.0981 g as an inhibitor and 0.1946 g of stannous chloride (1% ε-caprolactone solution) as a catalyst are added at 170 ° C. while passing nitrogen.
The reaction was performed for 19 hours.

 The conversion of ε-caprolactone was 82%.

Example 8 A flask equipped with the same apparatus as in Example 1 was charged with 43.1 g of 4-hydroxybutyl vinyl ether and ε-caprolactone 1
27.0 g and 0.0855 g of stannous chloride (1% ε-caprolactone solution) as a catalyst were added and reacted at 170 ° C. for 5 hours while passing nitrogen.

The reaction rate of ε-caprolactone was 99.3%. This was cooled, taken out, and examined for properties. The results were as follows.

Appearance (APHA) 170 Acid value (mgKOH / g) 0.41 OH value (mgKOH / g) 42.17 Viscosity (cp 45 ° C) 640 H ₂ O (%) 0.053 Example 9 In a flask equipped with the same apparatus as in Example 1, 43.70 g of 4-hydroxybutyl vinyl ether, ε-caprolactone
128.70 g, stannous chloride (1% ε-caprolactone solution) 0.1723 g as a catalyst, and 200 ° C. while passing nitrogen 3
Allowed to react for hours.

The conversion of ε-caprolactone was 99.4%. This was cooled, taken out, and examined for properties. The results were as follows.

Appearance (APHA) 150 Acid value (mgKOH / g) 0.254 OH value (mgKOH / g) 56.71 Viscosity (cp 45 ° C) 300 H ₂ O (%) 0.039 Iodine value 29.59 Example 10 Equipped with the same equipment as in Example 1. In a flask, 39.51 g of 4-hydroxybutyl vinyl ether, ε-caprolactone
116.35 g and 0.1456 g of tetrabutyl titanate (1% heptane solution) as a catalyst were added at 170.degree.
Allowed to react for hours. The reaction rate of ε-caprolactone is 99.4%
Met.

This was cooled, taken out, and examined for properties. The results were as follows.

Appearance (APHA) 70 Acid value (mgKOH / g) 0.126 OH value (mgKOH / g) 107.94 Viscosity (cp 45 ° C) 95 H ₂ O (%) 0.042 Iodine value 40.43 Example 11 Equipped with the same apparatus as in Example 1. 38.64 g of 4-hydroxybutyl vinyl ether, ε-caprolactone
113.80 g, and 0.1561 g of tetrabutyl titanate (1% heptane solution) as a catalyst were added at 150 ° C. while passing nitrogen gas.
Allowed to react for hours.

The conversion of ε-caprolactone was 99.4%. This was cooled, taken out, and examined for properties. The results were as follows.

Appearance (APHA) 65 Acid value (mgKOH / g) 0.080 OH value (mgKOH / g) 109.71 Viscosity (cp 45 ° C) 82 H ₂ O (%) 0.029 Iodine value 41.74 Example 12 Equipped with the same apparatus as in Example 1. 40.25 g of 4-hydroxybutyl vinyl ether, ε-caprolactone
118.55 g, 0.1143 g of tetrabutyl titanate (1% heptane solution) as a catalyst, and 5 ° C. at 170 ° C. while passing nitrogen.
Allowed to react for hours.

The reaction rate of ε-caprolactone was 99.6%. This was cooled, taken out, and examined for properties. The results were as follows.

Appearance (APHA) 90 Acid value (mgKOH / g) 0.110 OH value (mgKOH / g) 104.38 Viscosity (cp 45 ° C) 105 H ₂ O (%) 0.026 Example 13 A flask equipped with the same apparatus as in Example 1 39.40 g of 4-hydroxybutyl vinyl ether, ε-caprolactone
116.65 g, and 0.1602 g of tetrabutyl titanate (1% heptane solution) as a catalyst were added at 130 ° C. while passing nitrogen gas.
Allowed to react for hours.

The conversion of ε-caprolactone was 99.1%. This was cooled, taken out, and examined for properties. The results were as follows.

Appearance (APHA) 70 Acid value (mgKOH / g) 0.11 OH value (mgKOH / g) 113.6 Viscosity (cp 45 ° C) 71 H ₂ O (%) 0.064 Example 14 A flask equipped with the same apparatus as in Example 1 4-hydroxybutyl vinyl ether 600.0 g, ε-caprolactone
589.6 g and 1.2970 g of tetrabutyl titanate (1% heptane solution) as a catalyst were added and reacted at 150 ° C. for 10 hours while passing nitrogen.

The product of this reaction contained 0.8% by weight of ε-caprolactone, 15.5% by weight of 4-hydroxybutyl vinyl ether and 10.7 ppm of catalyst.

This was cooled to room temperature, taken out and examined for properties,
It was as follows.

Appearance (APHA) 55 Acid value (mgKOH / g) 0.118 OH value (mgKOH / g) 222.43 Viscosity (cp 45 ° C) 50 H ₂ O (%) 0.042 Example 15 A flask equipped with the same apparatus as in Example 1 300.0 g of 4-hydroxybutyl vinyl ether, ε-caprolactone
1473.9g, 1.8219g of tetrabutyl titanate (1% heptane solution) as a catalyst and 9 at 160 ° C while passing nitrogen.
Allowed to react for hours.

The product of this reaction contained 0.3% by weight of ε-caprolactone, 1.5% by weight of 4-hydroxybutyl vinyl ether and 10.1 ppm of catalyst.

This was cooled to room temperature, taken out and examined for properties. The results were as follows.

Appearance (APHA) 90 Acid value (mgKOH / g) 0.111 OH value (mgKOH / g) 78.15 Viscosity (cp 45 ° C) 186 H ₂ O (%) 0.022 Example 16 A flask equipped with the same apparatus as in Example 1 58.0 g of 4-hydroxybutyl vinyl ether, ε-caprolactone 2
28.0 g and 3,3,5-trimethylcaprolactone and 3,5,5
57.0 g of a mixture with trimethylcaprolactone, 0.34 of tetrabutyl titanate (1% heptane solution) as catalyst
3 g was added and reacted at 160 ° C. for 15 hours while passing nitrogen.

0.3% by weight of ε-caprolactone, 7.6% by weight of a mixture of trimethylcaprolactone,
-Contains 1.8% by weight of hydroxybutyl vinyl ether and 10 ppm of catalyst.

This was cooled to room temperature, taken out and examined for properties. The results were as follows.

Appearance (APHA) 90 Acid value (mgKOH / g) 0.32 OH value (mgKOH / g) 75.13 Viscosity (cp 45 ° C) 170 H ₂ O (%) 0.081 Example 17 A flask equipped with the same apparatus as in Example 1 50.5 g of 4-hydroxybutyl vinyl ether, ε-caprolactone 1
98.5 g and β-methyl-δ-valerolactone 49.6 g, tetrabutyl titanate (1% heptane solution) as a catalyst
0.2986 g was added and reacted at 160 ° C. for 15 hours while passing nitrogen.

0.8% by weight of ε-caprolactone, 6.6% by weight of β-methyl-δ-valerolactone,
1.6% by weight of hydroxybutyl vinyl ether and catalyst 1
0 ppm was contained.

This was cooled to room temperature, taken out and examined for properties. The results were as follows.

Appearance (APHA) 100 Acid value (mgKOH / g) 0.15 OH value (mgKOH / g) 78.53 Viscosity (cp 45 ° C) 160 H ₂ O (%) 0.026 Example 18 A flask equipped with the same apparatus as in Example 1 72.0 g of 6-hydroxyhexyl vinyl ether, 171.0 g of ε-caprolactone, and 0.243 g of tetrabutyl titanate (1% heptane solution) as a catalyst were charged at 170 ° C. while passing nitrogen.
Allowed to react for hours.

0.3% by weight of ε-caprolactone and 3.8% by weight of 6-hydroxyhexyl vinyl ether were contained in the product of this reaction.
And 10 ppm of catalyst.

This was cooled to room temperature, taken out and examined for properties. The results were as follows.

Appearance (APHA) 70 Acid value (mgKOH / g) 0.11 OH value (mgKOH / g) 113.45 Viscosity (cp 45 ° C) 90 H ₂ O (%) 0.031 Synthesis conditions from Example 1 to Example 18 and obtained Table 1 shows the mixing ratio of each component in the synthesized product.

Claims (8)

(57) [Claims] 1. The following formula [Wherein, R ³ and R ⁴ may be the same or different and each represent a hydrogen atom or a methyl group or an ethyl group, and R ³ and R ⁴ bonded to adjacent carbons may be the same or different; Y represents an integer of 3 to 7. A compound represented by the following formula (1) obtained by subjecting a lactone monomer represented by the following to an addition reaction with a hydroxyalkyl vinyl ether: [Wherein, R ¹ and R ² may be the same or different and each represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R ¹ and R ² bonded to adjacent carbons are the same or different. R ³ and R ⁴ may be the same or different, each represents a hydrogen atom or a methyl group or an ethyl group, and R ³ and R ⁴ bonded to adjacent carbons may be the same or different, and x Represents an integer from 1 to 10, and n represents an integer from 1 to 100. When producing a reactive composition containing the lactone monomer, the water content in the lactone monomer is 0.02% by weight or less, and the water content in the hydroxyalkyl vinyl ether is 1.0% by weight or less. The water content in the reactive composition containing the monomer is calculated from the ratio of reacting when a lactone monomer having a water content of 0.02% by weight and a hydroxyalkyl vinyl ether having a water content of 1.0% by weight are used. A method for producing a reactive composition containing a monomer, comprising reacting the lactone monomer with a hydroxyalkyl vinyl ether so as to have a water content or less. " 2. The process according to claim 1, wherein the lactone monomer is ε-caprolactone. 3. The method of claim 1, wherein the lactone monomer is a mixture of 3,3,5-trimethylcaprolactone and 3,5,5-trimethylcaprolactone. 4. The method for producing a reactive composition containing a monomer according to claim 1, wherein the lactone monomer is a mixture of ε-caprolactone and β-methyl-δ-valerolactone. 5. The method according to claim 5, wherein the hydroxyalkyl vinyl ether is 4-
The method for producing a reactive composition containing the monomer according to claim 1, which is hydroxybutyl vinyl ether. 6. 70 ° C. to 200 ° C. in the presence of about 200 ppm or less of a catalyst.
The method for producing a reactive composition containing the monomer according to claim 1, wherein the reaction is carried out at a temperature of: 7. A lactone monomer comprising ε-caprolactone,
The method for producing a reactive composition containing a monomer according to claim 1, which is a mixture of 3,3,5-trimethylcaprolactone, 3,5,5-trimethylcaprolactone, and β-methyl-δ-valerolactone. 8. The method for producing a reactive composition containing a monomer according to claim 1, wherein a titanium-based catalyst is used.