1,1-dicyanoethylene-containing composition

Abstract

Provided is a 1,1-dicyanoethylene-containing composition comprising 1,1-dicyanoethylene and a carbonyl compound (I) represented by the following formula (1), wherein the content of the carbonyl compound (I) is 0.1 to 300,000 mass ppm relative to the 1,1-dicyanoethylene. (Each symbol in formula (1) is as defined in the specification.)

Description

1,1-dicyanoethylene-containing composition

[0001] The present invention relates to a 1,1-dicyanoethylene-containing composition.

[0002] Because 1,1-dicyanoethylene is highly reactive, it is known that its storage stability should be enhanced by using acid stabilizers or the like during storage. For example, Patent Document 1 proposes using benzenesulfonic acid, chlorobenzenesulfonic acid, p-toluenesulfonic acid, etc., as acid stabilizers.

[0003] U.S. Patent No. 2,535,861

[0004] However, the method proposed in Patent Document 1, while sometimes improving storage stability, had the problem that if the acid stabilizer was present in excess relative to 1,1-dicyanoethylene, the storage stability of 1,1-dicyanoethylene would decrease. In addition, the mixture containing 1,1-dicyanoethylene and the acid stabilizer may become discolored.

[0005] The present invention has been made in view of the above circumstances, and aims to provide a 1,1-dicyanoethylene composition that has excellent storage stability and suppressed discoloration.

[0006] As a result of diligent research by the present inventors, it was discovered that by coexisting 1,1-dicyanoethylene with a specific amount of a particular carbonyl compound, the storage stability of 1,1-dicyanoethylene is improved and discoloration caused by 1,1-dicyanoethylene can be suppressed. Based on this finding, further research was conducted to complete the present invention.

[0007] In other words, the present invention is as follows: [1] A 1,1-dicyanoethylene-containing composition comprising a carbonyl compound (I) represented by the following formula (1) and 1,1-dicyanoethylene, wherein the carbonyl compound (I) is contained in an amount of 0.1 to 300,000 ppm by mass relative to the 1,1-dicyanoethylene. (In formula (1), R １ R is an alkyl group having 1 to 25 carbon atoms, or a cycloalkyl group having 3 to 12 carbon atoms. ２(These are alkyl groups having 1 to 25 carbon atoms, cycloalkyl groups having 3 to 12 carbon atoms, aryl groups having 6 to 25 carbon atoms, halogen atoms, or cyano groups.) [2] R １ The 1,1-dicyanoethylene-containing composition described in [1] above, wherein the alkyl group has 1 to 12 carbon atoms. [3] R １ The 1,1-dicyanoethylene-containing composition described in [1] or [2] above, wherein is a methyl group. [4] R ２ The 1,1-dicyanoethylene-containing composition according to any one of [1] to [3] above, wherein is a cyano group. [5] The 1,1-dicyanoethylene-containing composition according to any one of [1] to [4] above, which contains water, wherein the water content is 1 to 1,000 ppm by mass. [6] The 1,1-dicyanoethylene-containing composition according to any one of [1] to [5] above, wherein the 1,1-dicyanoethylene content is 1 to 99.9% by mass. [7] The 1,1-dicyanoethylene-containing composition according to any one of [1] to [6] above, which contains the carbonyl compound (I) in an amount of 0.1 to 1,000 ppm by mass relative to the 1,1-dicyanoethylene. [8] The 1,1-dicyanoethylene-containing composition according to any one of [1] to [7] above, which contains at least one selected from methanesulfonic acid, sulfuric acid, sulfur dioxide, hydrogen chloride, nitric acid, sulfurous acid, p-toluenesulfonic acid, and phosphoric acid.

[0008] According to the present invention, it is possible to provide a 1,1-dicyanoethylene composition that has excellent storage stability and suppressed discoloration.

[0009] The following description is based on an example of an embodiment of the present invention. However, the embodiments shown below are illustrative examples for realizing the technical concept of the present invention, and the present invention is not limited to the following description. In this specification, preferred forms of embodiments are shown, but combinations of two or more individual preferred forms are also preferred forms. If there are several numerical ranges for an item indicated by a numerical range, a preferred form can be obtained by selectively combining the lower and upper limits of those ranges. Also, when a numerical range is described as "XX to YY", it means "XX or more and YY or less".

[0010] [1,1-Dicyanoethylene-containing composition] The 1,1-dicyanoethylene-containing composition according to the embodiment of the present invention contains a carbonyl compound (I) represented by formula (1) and 1,1-dicyanoethylene, wherein the carbonyl compound (I) is contained in an amount of 0.1 to 300,000 ppm by mass relative to the 1,1-dicyanoethylene. When storing 1,1-dicyanoethylene, the storage stability can be improved by using an acid stabilizer or the like. However, if the acid stabilizer is present in excess relative to the 1,1-dicyanoethylene, the storage stability may decrease or discoloration may occur. This is presumed to be due to the reaction of the excess acid stabilizer with the cyano group on the 1,1-dicyanoethylene, causing the cyano group to protonate. Thus, when adhesives and the like are manufactured using 1,1-dicyanoethylene with protonated cyano groups, it is presumed that the curing reaction will not proceed and the expected performance cannot be obtained. On the other hand, the 1,1-dicyanoethylene-containing composition according to this embodiment contains a specific amount of a specific carbonyl compound, which not only improves the storage stability of 1,1-dicyanoethylene regardless of the presence or absence of an acid stabilizer, but also suppresses discoloration caused by the cyano group of 1,1-dicyanoethylene.

[0011] <Carbonyl Compound (I)> The carbonyl compound (I) according to this embodiment is represented by the following formula (1).

[0012]

[0013] In formula (1), R １ R is an alkyl group having 1 to 25 carbon atoms, or a cycloalkyl group having 3 to 12 carbon atoms. ２ These are alkyl groups having 1 to 25 carbon atoms, cycloalkyl groups having 3 to 12 carbon atoms, aryl groups having 6 to 25 carbon atoms, halogen atoms, or cyano groups.

[0014] R １ Examples of alkyl groups having 1 to 25 carbon atoms represented by include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, and n-hexyl group.

[0015] R １ Examples of the cycloalkyl group having 3 to 12 carbon atoms represented by R include, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like.

[0016] R １ From the viewpoints of storage stability and suppression of coloring, R is preferably an alkyl group having 1 to 12 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms, more preferably an alkyl group having 1 to 12 carbon atoms, still more preferably an alkyl group having 1 to 6 carbon atoms, even more preferably an alkyl group having 1 to 3 carbon atoms, and even more preferably a methyl group.

[0017] R ２ Examples of the alkyl group having 1 to 25 carbon atoms and the cycloalkyl group having 3 to 12 carbon atoms represented by R are the same as those of R １ and the like.

[0018] R ２ Examples of the aryl group having 6 to 25 carbon atoms represented by R include, for example, phenyl group, tolyl group, xylyl group, naphthyl group, biphenylyl group, terphenylyl group, anthryl group and the like.

[0019] R ２ Examples of the halogen atom represented by R include fluorine atom, chlorine atom, bromine atom, iodine atom and the like.

[0020] R ２ From the viewpoints of storage stability and suppression of coloring, R is preferably an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a halogen atom, and a cyano group, more preferably an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a cyano group, still more preferably a cyano group.

[0021] The carbonyl compound (I) according to the present embodiment is preferably an acetyl cyanide in which R １ is a methyl group and R ２ is a cyano group from the viewpoints of storage stability and suppression of coloring.

[0022] <1,1-dicyanoethylene> 1,1-dicyanoethylene may be produced according to the manufacturing method described in J. Am. Chem. Soc., 1989, 111, 9078-9081 or the manufacturing method described in U.S. Patent No. 2,476,270. The purity of the 1,1-dicyanoethylene used in the 1,1-dicyanoethylene-containing composition according to the embodiment of the present invention is preferably 95% or higher, more preferably 97% or higher, even more preferably 98% or higher, and even more preferably 99% or higher. The purity of 1,1-dicyanoethylene can be determined, for example, by gas chromatography. Furthermore, the produced 1,1-dicyanoethylene may be stored in coexistence with, for example, aromatic solvents such as toluene and xylene; aliphatic solvents such as hexane and heptane; naphthenic solvents such as cyclohexane; ester solvents such as ethyl acetate; and ether solvents such as tetrahydrofuran and diethyl ether until immediately before use.

[0023] <Other Components> The 1,1-dicyanoethylene-containing composition of this embodiment may contain other components besides carbonyl compound (I) and 1,1-dicyanoethylene. Examples of other components include water, polymerizable monomers other than 1,1-dicyanoethylene, acid stabilizers (Brønsted acid compounds), phenol compounds, organic solvents, acid anhydrides, Lewis acid compounds, thickeners, dehydrating agents, radical polymerization inhibitors, plasticizers, pigments, rubber, organic fillers, inorganic fillers, etc. Other components can be used in amounts that do not impair the effects of the present invention. Acid anhydrides may function as dehydrating agents. Rubber may function as organic fillers. Inorganic fillers may function as thickeners. Among these, water may be included in the composition, from the viewpoint that 1,1-dicyanoethylene is stabilized in the composition by the water in the composition forming an oxonium ion. Furthermore, an acid stabilizer may be included, from the viewpoint of further improving storage stability. The acid stabilizer may include at least one selected from methanesulfonic acid, sulfuric acid, sulfur dioxide, hydrogen chloride, nitric acid, sulfurous acid, p-toluenesulfonic acid, and phosphoric acid.

[0024] Examples of polymerizable monomers other than 1,1-dicyanoethylene include ethylene, propylene, butadiene, isobutylene, isoprene, 1-hexene, 1-octene, vinyl acetate, vinyl propionate, vinyl butyrate, styrene, α-methylstyrene, p-methylstyrene, acrylic acid, methacrylic acid, alkyl acrylates such as butyl acrylate, alkyl methacrylates such as methyl methacrylate and dodecyl methacrylate, acrylonitrile, vinyl chloride, vinylidene chloride, vinylidene fluoride, alkyl 2-cyanoacrylate, alkyl 2-cyanopentadienate, and dialkyl methylidenemalonate. The polymerizable monomer other than 1,1-dicyanoethylene may be one type or multiple types.

[0025] Examples of acid stabilizers include inorganic acids, carboxylic acids, and organic sulfonic acids. Specifically, examples include methanesulfonic acid, sulfuric acid, hydrogen chloride, nitric acid, acetic acid, benzenesulfonic acid, p-toluenesulfonic acid, sulfur dioxide, and phosphorus pentoxide, which react with water to produce compounds that exhibit Brønsted acidity. Among these, methanesulfonic acid, sulfuric acid, sulfur dioxide, hydrogen chloride, nitric acid, sulfurous acid, p-toluenesulfonic acid, and phosphoric acid are preferred. In this embodiment, even when an acid stabilizer is included in the 1,1-dicyanoethylene-containing composition, the reaction between the acid stabilizer and the carbonyl compound (I) improves the storage stability of 1,1-dicyanoethylene and suppresses discoloration.

[0026] Examples of phenol compounds include hydroquinone, p-methylphenol, p-methoxyphenol, and t-butylhydroquinone. Also, 2,6-di-tert-butyl-4-methylphenol, 2,6-di-tert-butylphenol, pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, 2,4-di-tert-butylphenol, 2,2'-methylenebis(4-methyl-6-t-butylphenol), 2,2'-methylenebis-(4- Ethyl-6-t-butylphenol) (Yoshinox 425), 4,4'-butylidenebis-(6-t-butyl-3-methylphenol) (Yoshinox BB), 2,2'-methylenebis[6-tert-butyl-4-methylphenol] (Smirizer MDP-S), 1,1,3-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane (Adekasta AO-30), 4,4'-butylidenebis(6-tert-butyl-m-cresol) (Adekasta) Bu AO-40), Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (Adekastab AO-50), 2,2'-dimethyl-2,2'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)dipropane-1,1'-diyl=bis[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate] (Adekastab AO-80), 1,3,5-trimethyl-2,4,6-tris(3, 5-di-tert-butyl-4-hydroxybenzyl)benzene (Adekastab AO-330), 4,4'-thiobis[3-methyl-6-(tert-butyl)phenol] (Smirizer WX-R), 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol, 2,4,6-tris(3',5'-di-tert-butyl-4'-hydroxybenzyl)mesitylene, 1'-hydroxy[2,2'-ethylidenebis[4,6-bis(1,Examples include specific o-substituted phenol compounds such as 1-dimethylpropyl)benzene]]-1-yl (Smilizer GS), 2-tert-butyl-4-methyl-6-(2-hydroxy-3-tert-butyl-5-methylbenzyl)phenyl acrylate (Smilizer GM), and 2-tert-butyl-6-methyl-4-{3-[(2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosfepin-6-yl)oxy]propyl}phenol (Smilizer GP).

[0027] Examples of organic solvents include aromatic solvents such as toluene and xylene; aliphatic solvents such as hexane and heptane; naphthenic solvents such as cyclohexane; ester solvents such as ethyl acetate; and ether solvents such as tetrahydrofuran and diethyl ether.

[0028] <Content of each component> The 1,1-dicyanoethylene-containing composition according to this embodiment contains carbonyl compound (I) in an amount of 0.1 to 300,000 ppm by mass relative to 1,1-dicyanoethylene. In one embodiment of the present invention, from the viewpoint of further improving storage stability and further suppressing discoloration, the 1,1-dicyanoethylene-containing composition preferably contains carbonyl compound (I) in an amount of 0.1 to 200,000 ppm by mass, more preferably 1 to 100,000 ppm by mass, even more preferably 10 to 50,000 ppm by mass, and even more preferably 30 to 30,000 ppm by mass, relative to 1,1-dicyanoethylene. In another aspect of the present invention, from the viewpoint of further improving storage stability and further suppressing discoloration, the 1,1-dicyanoethylene-containing composition preferably contains carbonyl compound (I) in an amount of 0.1 to 10,000 ppm by mass, more preferably 0.1 to 1,000 ppm by mass, even more preferably 0.1 to 100 ppm by mass, and still more preferably 0.1 to 10 ppm by mass, relative to 1,1-dicyanoethylene.

[0029] The content of 1,1-dicyanoethylene in the 1,1-dicyanoethylene-containing composition is preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 5% by mass or more, and even more preferably 7% by mass or more, from the viewpoint of the amount of active ingredients in the composition. There is no particular upper limit on the above monomer, but from the viewpoint of storage stability, it is preferably 99.9% by mass or less, more preferably 99.5% by mass or less, even more preferably 99% by mass or less, even more preferably 50% by mass or less, and even more preferably 40% by mass or less. The content of 1,1-dicyanoethylene in the 1,1-dicyanoethylene-containing composition is preferably 1 to 99.9% by mass, more preferably 3 to 99.5% by mass, even more preferably 5 to 99% by mass, even more preferably 7 to 50% by mass, and even more preferably 7 to 40% by mass.

[0030] When the 1,1-dicyanoethylene-containing composition contains water, the amount of water in the 1,1-dicyanoethylene-containing composition is preferably 1 to 1,000 ppm by mass, more preferably 5 to 500 ppm by mass, even more preferably 10 to 200 ppm by mass, and even more preferably 10 to 110 ppm by mass, from the viewpoint of suppressing the formation of precipitates and suppressing increased viscosity.

[0031] When the 1,1-dicyanoethylene-containing composition contains an acid stabilizer, the content of the acid stabilizer in the 1,1-dicyanoethylene-containing composition is preferably 0.0005% by mass or more, more preferably 0.0009% by mass or more, and even more preferably 0.004% by mass or more, from the viewpoint of further improving the storage stability of the 1,1-dicyanoethylene-containing composition, and preferably 10% by mass or less, more preferably 5% by mass or less, even more preferably 2% by mass or less, and even more preferably 1% by mass or less, from the viewpoint of further suppressing discoloration. That is, the content of the acid stabilizer in the 1,1-dicyanoethylene-containing composition is preferably 0.0005 to 10% by mass, more preferably 0.0009 to 5% by mass, even more preferably 0.004 to 2% by mass, and even more preferably 0.004 to 1% by mass.

[0032] <Method for Producing 1,1-Dicyanoethylene-Containing Composition> There are no particular restrictions on the method for producing the 1,1-dicyanoethylene-containing composition. For example, it can be produced by a method that includes a mixing step of mixing a specific amount of carbonyl compound (I), 1,1-dicyanoethylene, and other components. To prevent the polymerization reaction from proceeding due to moisture, it is preferable to produce the 1,1-dicyanoethylene-containing composition under a dry atmosphere. There are no particular restrictions on the method of mixing each component, and they can be mixed by known methods.

[0033] <Applications> The 1,1-dicyanoethylene-containing composition according to this embodiment can be used as an (instant) adhesive. Applications of this adhesive include general household adhesives, medical applications, hemostatic adhesives, lamination, bookbinding, shoe assemblies, automobile parts, air conditioning equipment, components of electrical or electronic devices or other durable consumer goods, assembly of components used in the construction industry (e.g., insulation, thermal and / or acoustic applications), packaging, die bonding applications, wound closure, surgical sutures, medical device applications, and all kinds of labeling, eyelash extension adhesives, and cosmetic adhesives. Instant adhesives containing ethyl 2-cyanoacrylate as the main ingredient are widely known, but ethyl 2-cyanoacrylate has the disadvantage of poor heat resistance and moisture resistance, and therefore such instant adhesives have poor heat resistance and moisture resistance. On the other hand, 1,1-dicyanoethylene has excellent heat resistance and moisture resistance, and adhesives using the 1,1-dicyanoethylene-containing composition according to this embodiment have excellent heat resistance and moisture resistance.

[0034] The 1,1-dicyanoethylene-containing composition according to this embodiment can also be used as a coating material. Applications of such a coating material include film capacitors, insulating layers for EL elements, electrostatic induction conversion elements, sensors (e.g., touch sensors, vibration sensors, biosensors, tire sensors (especially sensors installed on the inner surface of tires)), actuators, touch panels, haptic devices, vibration power generation devices (e.g., vibration power generation floors, vibration power generation tires), speakers, microphones, vibration damping sheets, hollow fiber membranes for water purification, and resist films. An example of a haptic device is a device that provides tactile feedback to the user.

[0035] Hereinafter,although the present invention will be specifically described by way of examples and comparative examples,the present invention is not limited thereto.

[0036] [Measurement and Evaluation] The physical properties of the 1,1-dicyanoethylene-containing composition were measured by the following methods.The results are shown in Tables 1 and 2.

[0037] <Content> The contents of 1,1-dicyanoethylene and carbonyl compound (I) in the 1,1-dicyanoethylene-containing composition were measured using gas chromatography (GC-2014AF / SPL manufactured by Shimadzu Corporation).For 1,1-dicyanoethylene,a calibration curve was prepared using 99% 1,1-dicyanoethylene as a standard with respect to the GC detection area ratio.For carbonyl compound (I),a calibration curve was prepared using acetyl cyanide (manufactured by Sigma-Aldrich Japan LLC,purity 90%) as a standard. - Column: InertCap for Amines (30 m × 0.32 mm) - Column temperature: 0 °C × 1 min → 5 °C / min → 90 °C (no hold) → 50 °C / min → 260 °C × 6 min - Vaporization chamber temperature: 150 °C - Detector temperature: 270 °C - Carrier gas: Helium - Pressure: 97.0 kPa - Total flow rate: 36.5 mL / min - Column flow rate: 3.04 ml / min - Linear velocity: 46.6 cm / sec - Purge flow rate: 3.0 mL / min - Split ratio: 10.0 - Injection volume: 0.5 μl - Solvent used: Methyl acetate - Internal standard substance: Tetradecane

[0038] <Water content> The water content in the 1,1-dicyanoethylene-containing composition was measured by the coulometric titration method of the Karl Fischer titration method in accordance with JIS K0113:2005.

[0039] <Storage stability> (Container made of high-density polyethylene) 1 mL of the 1,1-dicyanoethylene-containing composition obtained in the example was placed in a 10-mL container made of high-density polyethylene,sealed,and allowed to stand at 25 °C for 48 hours,and then visually observed and evaluated according to the following criteria. A: No precipitate can be confirmed. B: If a precipitate can be confirmed. If no precipitate can be confirmed,it can be said that the storage stability is excellent.

[0040] (Glass container) The 1,1-dicyanoethylene-containing composition obtained in the example was placed in a 6 mL glass screw-top bottle, sealed tightly, and left to stand at 25°C for 48 hours. After standing, it was observed visually and evaluated according to the following criteria: A: No precipitate was observed. B: White precipitate was observed on the surface of the container. C: White precipitate was observed on the surface of the container, and white sediment was also observed. Or white sediment was observed. If no precipitate or sediment was observed on the surface of the container, it can be said that the storage stability was excellent.

[0041] <Coloring> After placing 1 mL of the 1,1-dicyanoethylene-containing composition obtained in the example into a 10 mL container made of high-density polyethylene, the color was observed visually and evaluated according to the following criteria. Subsequently, 97% sulfuric acid (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. (purity: 96-98%)) was added in an amount equal to 1% by mass relative to the composition, and the color of the mixture (1,1-dicyanoethylene-containing composition) was observed visually and evaluated according to the following criteria. A: Colorless B: Pale yellow C: Yellow Note that "yellow" means that the color was darker than "pale yellow".

[0042] [Production Example 1: Production of 1,1-dicyanoethylene] 1,1-dicyanoethylene: 1,1,3,3-tetracyanopropane (yield 73% by mass) was synthesized from malononitrile using the production method described in J. Am. Chem. Soc., 1989, 111, 9078-9081. The obtained crystalline 1,1,3,3-tetracyanopropane was mixed with phosphorus pentoxide and decomposed by heating at 180°C to obtain a crude product of 1,1-dicyanoethylene (yield 60% by mass). The obtained crude product was purified by vacuum distillation (480 Pa) to obtain 1,1-dicyanoethylene with a purity of 99% by mass.

[0043] [Example 1] 50 g of the obtained 1,1-dicyanoethylene was mixed with 1.39 mg of acetylcyanide (carbonyl compound (I), manufactured by Sigma-Aldrich Japan LLC, 90% purity) to obtain a mixture containing 25 ppm by mass of acetylcyanide (carbonyl compound (I)) relative to 1,1-dicyanoethylene. 3 g of this mixture was mixed with 97 g of toluene and 1 mg of water to prepare a 1,1-dicyanoethylene composition.

[0044] [Examples 2-28 and Comparative Examples 1-4] 1,1-dicyanoethylene compositions were prepared in the same manner as in Example 1, except that the amounts of 1,1-dicyanoethylene, acetylcyanide, and toluene were changed to achieve the content shown in Table 1.

[0045]

[0046]

[0047] Tables 1 and 2 show that the 1,1-dicyanoethylene-containing compositions of Examples 1 to 28 exhibited superior storage stability and suppressed discoloration compared to the 1,1-dicyanoethylene-containing compositions of Comparative Examples 1 to 4.

Claims

1. A 1,1-dicyanoethylene-containing composition comprising a carbonyl compound (I) represented by the following formula (1) and 1,1-dicyanoethylene, wherein the carbonyl compound (I) is contained in an amount of 0.1 to 300,000 ppm by mass relative to the 1,1-dicyanoethylene. (In formula (1), R １ R is an alkyl group having 1 to 25 carbon atoms, or a cycloalkyl group having 3 to 12 carbon atoms. ２ (These are alkyl groups having 1 to 25 carbon atoms, cycloalkyl groups having 3 to 12 carbon atoms, aryl groups having 6 to 25 carbon atoms, halogen atoms, or cyano groups.) 2. R １ The 1,1-dicyanoethylene-containing composition according to claim 1, wherein is an alkyl group having 1 to 12 carbon atoms.

3. R １ The 1,1-dicyanoethylene-containing composition according to claim 1, wherein is a methyl group.

4. R ２ The 1,1-dicyanoethylene-containing composition according to claims 1 to 3, wherein is a cyano group.

5. A 1,1-dicyanoethylene-containing composition according to claims 1 to 3, wherein the water content is 1 to 1,000 ppm by mass.

6. The 1,1-dicyanoethylene-containing composition according to claims 1 to 3, wherein the content of 1,1-dicyanoethylene is 1 to 99.9% by mass.

7. The 1,1-dicyanoethylene-containing composition according to claims 1 to 3, wherein the carbonyl compound (I) is contained in an amount of 0.1 to 1,000 ppm by mass relative to the 1,1-dicyanoethylene.

8. A 1,1-dicyanoethylene-containing composition according to claims 1 to 3, comprising at least one selected from methanesulfonic acid, sulfuric acid, sulfur dioxide, hydrogen chloride, nitric acid, sulfurous acid, p-toluenesulfonic acid, and phosphoric acid.

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