Novel compounds

Abstract

To provide a control agent having a melting point lower than that of 1-ethynyl-1-cyclohexanol, for suppressing a hydrosilylation addition reaction of a silicone rubber composition at room temperature.SOLUTION: The control agent contains a compound represented by formula (1) (R is an alkyl group).SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to novel compounds. [Background technology]

[0002] It is known that a platinum catalyst inhibitor such as 1-ethynyl-1-cyclohexanol is used to suppress the hydrosilylation addition reaction of a silicone rubber composition at room temperature. However, because 1-ethynyl-1-cyclohexanol has a melting point of 30 to 33°C, adding and mixing it into a silicone rubber composition requires heating the silicone rubber composition to a temperature above the melting point of 1-ethynyl-1-cyclohexanol, which is a problem.

[0003] In order to solve the above problems, Patent Document 1 below describes a method for producing an addition-curable liquid silicone rubber composition that contains (A) an organopolysiloxane having alkenyl groups bonded to at least two silicon atoms in one molecule, (B) an organohydrogenpolysiloxane having hydrogen atoms bonded to at least two silicon atoms in one molecule, (C) an addition reaction catalyst, and (D) a control agent, in which the control agent is: (a) 1-ethynyl-1-cyclohexanol, and A method for producing an addition-curable liquid silicone rubber composition is disclosed, which is characterized by using a regulator that contains (b) an acetylene alcohol other than the above-mentioned component (a) that has a freezing point or melting point of 15°C or lower, and that causes the crystal precipitation temperature of a premix of components (a) and (b) to be 25°C or lower, and by adding and mixing the premix to a compound that contains at least a portion of the above-mentioned component (A), or at least a portion of component (A) and component (B) and has a temperature of less than 33°C. According to the technology disclosed in Patent Document 1, even when 1-ethynyl-1-cyclohexanol is used as a control agent in a manufacturing site that is in extremely cold conditions, such as below freezing, the control agent does not crystallize and can be reliably dispersed in the silicone rubber composition without the use of a solvent, thereby achieving excellent stability. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2015-108088 Summary of the Invention [Problem to be solved by the invention]

[0005] As described in Patent Document 1, 1-ethynyl-1-cyclohexanol (ECH) has long been known to be an effective retarder; however, its melting point is approximately 31°C, making it a solid at room temperature. From the standpoint of mixing and dispersing with silicone rubber, it is preferable for the retarder to be liquid. Therefore, when using ECH as a retarder, it must be heated and melted before use, or a solvent must be used that is a volatile organic compound (VOC), or an easily mixed inactive ingredient that is not a VOC. In Patent Document 1, acetylene alcohol is an example of such an inactive ingredient. However, the use of such an inactive ingredient increases the number of production steps, resulting in disadvantages in terms of time and economy of productivity. An object of the present invention is to solve the above-mentioned conventional problems and to provide a novel compound that can be used as, for example, a platinum catalyst inhibitor. [Means for solving the problem]

[0006] The present invention provides a compound represented by the following general formula (1):

[0007] [ka]

[0008] (In the general formula (1), R represents an alkyl group having 1 to 4 carbon atoms.)

[0009] The present invention also provides a method for producing a compound represented by general formula (1), comprising a step of reacting 1-ethynyl-1-cyclohexanol with a carboxylic acid anhydride in the presence of a catalyst represented by the following general formula (14):

[0010] [ka] (In the general formula (14), M represents a metal ion, Z represents an anion, and n represents an integer of 1 to 4.)

[0011] The present invention also provides an addition-curable liquid silicone rubber composition comprising: (A) an organopolysiloxane having alkenyl groups bonded to at least two silicon atoms in one molecule; (B) an organohydrogenpolysiloxane having hydrogen atoms bonded to at least two silicon atoms in one molecule; (C) an addition reaction catalyst; and (D) a retarder, The present invention provides an addition-curable liquid silicone rubber composition, in which the (D) inhibitor contains a compound represented by the general formula (1). [Effects of the Invention]

[0012] The compound of the present invention represented by the general formula (1) can exhibit the same effect as a platinum catalyst inhibitor as that of the prior art. Furthermore, the compound of the present invention represented by the general formula (1) is liquid even at room temperature or low temperatures (e.g., below -14°C), eliminating the need for inactive ingredients such as acetylene alcohol. Therefore, the process of melting by heating or dissolving in a solvent is no longer necessary, thereby shortening productivity and reducing the number of production steps, which is also economically effective. [Brief explanation of the drawings]

[0013] [Figure 1] FIG. 1 shows a TIC obtained by GC / MS analysis of the GC / MS analysis sample obtained in Synthesis Example 2. [Figure 2] FIG. 1 shows the MS spectrum of peak No. 3 of the TIC. [Figure 3]FIG. 1 shows the MS spectrum of peak No. 4 of the TIC. [Figure 4] FIG. 1 shows the MS spectrum of peak No. 9 of the TIC. DETAILED DESCRIPTION OF THE INVENTION

[0014] Hereinafter, an embodiment of the present invention will be described. The compound of the present invention is represented by the following general formula (1).

[0015] [ka]

[0016] (In the general formula (1), R represents an alkyl group having 1 to 4 carbon atoms.)

[0017] Examples of the compound represented by general formula (1) of the present invention include 1-ethynyl-1-cyclohexylpropionate, 1-ethynyl-1-cyclohexyl-n-butyrate, 1-ethynyl-1-cyclohexyl-sec-butyrate, 1-ethynyl-1-cyclohexyl-tert-butyrate, 1-ethynyl-1-cyclohexyl isobutyrate, 1-ethynyl-1-cyclohexyl valerate, 1-ethynyl-1-cyclohexyl isovalerate, and 1-ethynyl-1-cyclohexyl pivalate.

[0018] The compounds of the present invention represented by the general formula (1) are useful as platinum catalyst inhibitors that retard the hydrosilylation addition reaction at room temperature in silicone rubber compositions.

[0019] The compound of the present invention represented by the general formula (1) can be produced by a production method including a step of reacting 1-ethynyl-1-cyclohexanol and a carboxylic acid anhydride in the presence of a catalyst represented by the following general formula (14):

[0020] [ka] (In the general formula (14), M represents a metal ion, Z represents an anion, and n represents an integer of 1 to 4.)

[0021] Examples of the carboxylic acid anhydride include acetic anhydride, propionic anhydride, butanoic anhydride, isobutanoic anhydride, pentanoic anhydride, isopentanoic anhydride, and pivalic anhydride.

[0022] The catalyst represented by the general formula (14) may be, for example, a catalyst in which M is an ion of at least one metal selected from the group consisting of scandium, vanadium, manganese, iron, cobalt, rhodium, nickel, hafnium, cerium, and bismuth, and Z is an ion of a halide ion, an oxide ion, an acetate ion, a sulfate ion, a nitrate ion, a trifluoromethanesulfonate ion (CF3SO3 - ), perfluorooctanesulfonate ion (CF 17 SO3 - ) or acetylacetonate ion (acac).

[0023] The solvent used in the reaction includes acetonitrile, tetrahydrofuran, methylene chloride, and the like.

[0024] The ratio of the raw materials used can be as follows, for example: For 1 mole of 1-ethynyl-1-cyclohexanol, 1 to 3 moles of carboxylic acid anhydride, 0.01 to 0.50 moles of the catalyst represented by the general formula (14).

[0025] The reaction conditions include stirring, atmospheric pressure, a temperature of -20 to 100°C, preferably -20 to 90°C, and a reaction time of 30 minutes to 24 hours, preferably 60 minutes to 20 hours.

[0026] After the reaction is completed, the reaction mixture is concentrated under reduced pressure, and the resulting residue is dissolved in a chlorine-based solvent and washed with an aqueous alkali solution to remove the by-product carboxylic acid corresponding to the carboxylic acid anhydride used. The organic layer is then concentrated, and the target compound represented by the general formula (1) can be obtained.

[0027] The compound of the present invention represented by the general formula (1) is useful as a platinum catalyst inhibitor that retards the hydrosilylation addition reaction at room temperature in a silicone rubber composition, as described above. The silicone rubber composition can contain other components, such as (A) an organopolysiloxane having alkenyl groups bonded to at least two silicon atoms in one molecule, (B) an organohydrogenpolysiloxane having hydrogen atoms bonded to at least two silicon atoms in one molecule, and (C) an addition reaction catalyst, together with the compound represented by the general formula (1).

[0028] The components (A) to (C) will now be described. -(A) Organopolysiloxane- The organopolysiloxane used in the present invention contains at least two alkenyl groups bonded to silicon atoms in each molecule and is preferably a diorganopolysiloxane that is liquid or rubber-like at room temperature (23°C). (A) Organopolysiloxane can be represented by the following average composition formula (2):

[0029] R 3 a SiO (4-a) / 2 (2) (In the formula, R 3 are the same or different unsubstituted or substituted monovalent hydrocarbon groups having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, and a is a positive number ranging from 1.5 to 2.8, preferably 1.8 to 2.5.

[0030] Here, the above R 3Examples of the unsubstituted or substituted monovalent hydrocarbon group include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, cyclohexyl, octyl, nonyl, and decyl; aryl groups such as phenyl, tolyl, xylyl, and naphthyl; aralkyl groups such as benzyl, phenylethyl, and phenylpropyl; alkenyl groups such as vinyl, allyl, propenyl, isopropenyl, butenyl, hexenyl, cyclohexenyl, and octenyl; and groups in which some or all of the hydrogen atoms of these groups have been substituted with halogen atoms such as fluorine, bromine, and chlorine, or with cyano groups, such as chloromethyl, chloropropyl, bromoethyl, trifluoropropyl, and cyanoethyl. 3 In particular, 90 mol % or more of R 1 is an alkyl group, and all R 2 is an alkyl group except for an alkenyl group. 3 is preferably a methyl group. 3 Preferably, two or more of these groups are alkenyl groups (preferably those having 2 to 8 carbon atoms, more preferably those having 2 to 6 carbon atoms, and particularly preferably vinyl groups). The degree of polymerization of (A) organopolysiloxane is, for example, preferably 30 to 10,000, and more preferably 50 to 5,000. Note that this degree of polymerization is the average degree of polymerization measured as a weight average value converted into polystyrene by gel permeation chromatography (GPC) analysis (the same applies hereinafter).

[0031] The structure of this organopolysiloxane is basically such that the main chain contains diorganosiloxane units (R 3 2SiO 2 / 2 ), and both ends of the molecular chain are triorganosiloxy groups (R 33SiO 1 / 2 ), but may also have a partially branched structure, a cyclic structure, etc. (R 3 is as above.)

[0032] -(B) Organohydrogenpolysiloxane- The organohydrogenpolysiloxane (B) used in the present invention is an organohydrogenpolysiloxane containing at least two silicon-bonded hydrogen atoms (SiH groups) per molecule, and acts as a crosslinking agent that cures the composition by a hydrosilylation addition reaction with the alkenyl group-containing organopolysiloxane. It is represented by the following average composition formula (3), and is preferably one having at least two, preferably three or more (usually about 3 to 200), more preferably 3 to 100, and particularly 3 to 50 silicon-bonded hydrogen atoms (SiH groups) per molecule. R 4 b H c SiO (4-b-c) / 2 (3) (In the formula, R 4 is an unsubstituted or substituted monovalent hydrocarbon group having 1 to 10 carbon atoms. b is a positive number that satisfies the range of 0.7 to 2.1, particularly 0.8 to 2.0, c is a positive number that satisfies the range of 0.001 to 1.0, and b+c is a positive number that satisfies the range of 0.8 to 3.0, particularly 1.0 to 2.5.

[0033] where R 4 As the alkenyl group-containing organopolysiloxane, R 3 Although the same groups as those mentioned above can be mentioned, those having no aliphatic unsaturated bond, such as alkenyl groups, are preferred.

[0034] The silicon-bonded hydrogen atoms may be bonded to silicon atoms at the ends of the molecular chain, or to silicon atoms in the middle of the molecular chain (non-ends of the molecular chain), or to both.

[0035] The molecular structure of this organohydrogenpolysiloxane may be linear, cyclic, branched, or a three-dimensional network structure, but the number of silicon atoms in one molecule (or degree of polymerization) is preferably 2 to 1,000, preferably 3 to 500, more preferably 3 to 300, and particularly preferably about 4 to 150.

[0036] Examples of the organohydrogenpolysiloxane include tris(dimethylhydrogensiloxy)methylsilane, tris(dimethylhydrogensiloxy)phenylsilane, 1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethylcyclotetrasiloxane, methylhydrogencyclopolysiloxane, methylhydrogensiloxane-dimethylsiloxane cyclic copolymer, methylhydrogenpolysiloxane capped at both ends with trimethylsiloxy groups, and dimethylsiloxane-methylhydrogen polysiloxane capped at both ends with trimethylsiloxy groups. Phenylsiloxane copolymer, dimethylpolysiloxane end-blocked with dimethylhydrogensiloxy groups, methylhydrogenpolysiloxane end-blocked with dimethylhydrogensiloxy groups, dimethylsiloxane-methylhydrogensiloxane copolymer end-blocked with dimethylhydrogensiloxy groups, methylhydrogensiloxane-diphenylsiloxane copolymer end-blocked with trimethylsiloxy groups, methylhydrogensiloxane-diphenylsiloxane-dimethylsiloxane copolymer end-blocked with trimethylsiloxy groups, (CH3)2HSiO 1 / 2 Units and SiO 4 / 2 A copolymer consisting of (CH3)2HSiO units 1 / 2 Units and SiO 4 / 2 Units and (C6H5)SiO 3 / 2 and copolymers consisting of these exemplified compounds in which some or all of the methyl groups have been substituted with other alkyl groups such as ethyl groups and propyl groups, aryl groups such as phenyl groups, halogen-substituted alkyl groups such as 3,3,3-trifluoropropyl groups, etc.

[0037] The amount of this organohydrogenpolysiloxane to be added is, for example, 0.1 to 50 parts by mass, and more preferably 0.1 to 30 parts by mass, per 100 parts by mass of the organopolysiloxane (A).

[0038] -(C) Addition reaction catalyst (curing catalyst)- The addition reaction catalyst used in the present invention is a catalyst for promoting the hydrosilylation addition reaction between alkenyl groups bonded to silicon atoms in the organopolysiloxane and SiH groups in the organohydrogenpolysiloxane. Examples of this addition reaction catalyst include platinum-based catalysts such as platinum black, platinic chloride, chloroplatinic acid, reaction products of chloroplatinic acid with monohydric alcohols, complexes of chloroplatinic acid with olefins, and platinum group metal-based catalysts such as platinum bisacetoacetate, palladium-based catalysts, and rhodium-based catalysts.

[0039] The amount of this addition reaction catalyst to be added can be a catalytic amount, but it is usually preferred to add about 0.5 to 1,000 ppm, and especially about 1 to 500 ppm, of platinum group metal relative to the total mass of the organopolysiloxane components.

[0040] An organic peroxide curing agent may also be used. Any organic peroxide curing agent may be used as long as it is used as a catalyst to promote the crosslinking reaction of component (A), and conventionally known organic peroxide curing agents can be used. Examples include, but are not limited to, benzoyl peroxide, 2,4-dichlorobenzoyl peroxide, p-methylbenzoyl peroxide, o-methylbenzoyl peroxide, 2,4-dicumyl peroxide, 2,5-dimethyl-bis(2,5-t-butylperoxy)hexane, di-t-butyl peroxide, t-butyl perbenzoate, and 1,1-bis(t-butylperoxycarboxy)hexane. The amount of the organic peroxide curing agent added is a catalytic amount, which may be selected appropriately depending on the curing rate. It is typically in the range of 0.1 to 10 parts by weight, preferably 0.2 to 2 parts by weight, per 100 parts by weight of component (A).

[0041] The silicone rubber composition of the present invention may contain any additive components commonly used in silicone rubber compositions, as needed. Examples of such additive components include fine silica particles such as fumed silica, precipitated silica, fused silica, calcined silica, spherical silica prepared by the sol-gel method, crystalline silica (quartz powder), and diatomaceous earth; fillers such as calcium carbonate, clay, diatomaceous earth, and titanium dioxide; hydrosilylation reaction inhibitors; colorants; and carbon black.

[0042] The amount of the compound represented by the general formula (1) of the present invention to be added is not particularly specified as long as it is the amount necessary to control the silicone rubber composition, but is usually 0.001 to 1.0 part by mass, more preferably 0.01 to 0.1 part by mass, per 100 parts by mass of silicone rubber (total of components (A) and (B) below).

[0043] In the present invention, when preparing the silicone rubber composition, (A) the organopolysiloxane, (B) the organohydrogenpolysiloxane, (C) the addition reaction catalyst, (D) the inhibitor consisting of the compound of the present invention represented by general formula (1) above, and other additives may all be simultaneously mixed at room temperature using equipment such as a planetary mixer or kneader. However, in the case of a liquid silicone rubber composition, a two-component composition may be prepared in advance, in which a catalyst-containing compound A (containing an organopolysiloxane and an addition reaction catalyst) and a crosslinking agent-containing compound B (containing an organopolysiloxane, reinforcing silica, an organohydrogenpolysiloxane, and the compound of the present invention represented by general formula (1) above) are generally prepared, and compound A and compound B are mixed immediately before use.

[0044] The silicone rubber composition thus obtained has excellent flame retardancy and electrical conductivity, and also has thixotropy, making it excellent in moldability. Therefore, it can be molded into the required application by various molding methods that are usually used to mold liquid silicone rubber compositions, such as cast molding, LIM injection molding, mold pressure molding, knife (blade) coating, and screen printing, and the molding conditions can be any known conditions and are not particularly limited.

[0045] The silicone rubber composition obtained by the present invention can be suitably used for structural components used in image-forming devices for business machines, adhesives, image-forming components, coating components for automobile airbags, and optical materials for LEDs. In particular, because of its excellent water vapor barrier properties, it is also useful as a sealant for photovoltaic power generation devices. [Example]

[0046] The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples.

[0047] Synthesis Example 1 of 1-ethynyl-1-cyclohexyl isobutyrate A 100 ml three-neck flask was charged with 30 g of tetrahydrofuran and 2 g of 1-ethynyl-1-cyclohexanol under a nitrogen stream and stirred. Subsequently, 3 g of isobutanoic anhydride and 0.5 g of bismuth(III) trifluoromethanesulfonate were added sequentially, and the mixture was stirred at 25°C for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue (3.6 g) was dissolved in a chlorine-based solvent for washing. The solution was washed twice with an alkaline aqueous solution, and the organic layer was concentrated to obtain 2.3 g of crude product.

[0048] Synthesis Example 2 of 1-ethynyl-1-cyclohexyl isobutyrate A 100 ml three-neck flask was charged with 20 g of tetrahydrofuran and 0.5 g of bismuth(III) trifluoromethanesulfonate under a nitrogen stream, stirred, and cooled with water. A mixture of 2 g of 1-ethynyl-1-cyclohexanol, 3 g of isobutanoic anhydride, and 20 g of tetrahydrofuran was then added dropwise, followed by stirring at 10°C for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue (5 g) was dissolved in 60 g of a chlorinated solvent for washing. This was then washed with an alkaline aqueous solution. After confirming the disappearance of the isobutyric acid peak by GC, the organic layer was concentrated to yield 2-4 g of crude product. This was then distilled (47°C, 60 Pa) to yield 2-4 g of a colorless, transparent liquid (89.7%).

[0049] The colorless, transparent liquid obtained in Synthesis Example 2 was subjected to the following GC / MS analysis under the following analysis conditions. GC / MS conditions: Device name: Shimadzu QP-2010Plus Column: InertCAP 5MS (φ0.25 μm, length 40 m) GC oven temperature: 40°C (3.0 min) to 310°C (15 min), 10°C / min Injection mode: Split Split ratio: 1 / 50 Sample: 0.2 ml of the colorless transparent liquid was mixed with 0.2 ml of chloroform to prepare a sample for GC / MS analysis.

[0050] The TIC obtained by the GC / MS analysis is shown in FIG. The MS spectrum of the TIC peak No. 3 is shown in FIG. The MS spectrum of peak No. 4 of the TIC is shown in FIG. The MS spectrum of No. 9, which is the main peak of the TIC, is shown in FIG.

[0051] A library search of the MS spectrum of peak No. 3 in Figure 2 detected the presence of 1-cyclohexene and 1-ethynyl compounds (fragment numbers 91 and 106). A library search of the MS spectrum of peak No. 4 in Figure 3 detected isobutyric acid anhydride (fragment numbers 43 and 71). In Figure 4, the m / z: 194 of Peak No. 9 is the M + (molecular ion peak).

[0052] [ka]

[0053] Considering the fragment of m / z: 194 of peak No. 9 in Figure 4, fragment numbers 43 and 71 are isobutyric acid anhydride produced by cleavage of 1-ethynyl-1-cyclohexyl isobutyrate as shown above (fragment numbers 43 and 71: see Figure 3). Considering the fragment of m / z:194 of peak No. 9 in Figure 4, the fragment ions 91 and 106 are 1-ethynyl-1-cyclohexene produced by the cleavage of 1-ethynyl-1-cyclohexyl isobutyrate. (91 and 106: see Figure 2) From the above, the presence of 1-ethynyl-1-cyclohexyl isobutyrate was confirmed in the GC / MS analysis sample.

[0054] Next, a silicone rubber composition was prepared. 100 parts of dimethylpolysiloxane (degree of polymerization 350) with both ends blocked with dimethylvinylsiloxy groups, and a BET specific surface area of ​​110 m 2 Hydrophobically treated fumed silica (R-972, manufactured by Nippon Aerosil Co., Ltd.) with a viscosity of 1000 ppm / g was placed in a planetary mixer according to the formulation (parts by mass) shown in Table 1 below, and after stirring at room temperature (23°C) for 30 minutes, the mixture was mixed and heat-treated at a high temperature of 150°C for 4 hours to produce silicone bases S1 to S3, each with a viscosity at 23°C of 50 to 1,200 Pa s, as shown in the table below. The silicone bases S1 to S3 above were stored in a constant temperature bath at 23°C for 24 hours, and the following blending was carried out while the silicone base was cooled to 23°C. All raw materials (platinum catalyst, oils, control agents) were also adjusted to 23°C before blending, and the mixer's mechanical, kettle, and blending atmosphere temperatures were also all kept at 23°C.

[0055] [Table 1]

[0056] Liquid A and liquid B were mixed in the formulation (parts by mass) shown in Table 2 below, and various physical properties were examined. The results are shown in Table 2. The notes in Table 2 are as follows: *1 The silicone base S1 created above *2 The silicone base S2 created above *3 The silicone-based S3 *4 Addition reaction catalyst (platinum catalyst) *5 H siloxane (dimethylsiloxane-methylhydrogensiloxane copolymer with both ends of the molecular chain blocked with dimethylhydrogensiloxy groups) *6 Control agent A (1-ethynyl-1-cyclohexanol, melting point = 30-33°C) *7 Control agent B (3-methyl-1-butyn-3-ol, melting point = 3°C) *8 Regulator C (1-ethynyl-1-cyclohexyl isobutyrate of the present invention prepared in Synthesis Example 2 above, melting point = -30°C) *9 Crystallization temperature of inhibitor (℃) = The temperature at which crystallization begins when the inhibitor is premixed and the temperature is lowered from 40℃ at a rate of 0.5℃ per hour. *10 Viscosity (Pa s) = Viscosity at a shear rate of 0.9 (1 / s) measured by a shear viscosity measuring device. Using a ThermoFisher Scientific HAAKE MARS 40 / 60 rheometer, cone plate: 20 mm, angle 2°, gap setting: 0.105 mm (volume 0.08 ml), held at 23°C for 30 seconds, and then measured at a shear rate increase rate of 0.001 (1 / s) → 20 (1 / s) / 300 seconds, the shear viscosity at 0.9 (1 / s) was recorded. *11 Mixing start temperature (℃) = temperature of the mixture when the control agent is added *12 Mixing end temperature (℃) = Temperature at the end after mixing for 30 minutes with a planetary mixer *13 Curing speed T10(sec)=10% curing time *14 Curing speed T90(sec)=90% curing time *15 Usable time (tack-free time) *16 Hardness (Durometer A) *17 Dispersibility = The dispersibility of the composition raw materials was evaluated visually.

[0057] [Table 2]

[0058] As can be seen from the results in Table 2, Examples 1 to 6, which correspond to the working examples of the present invention, have a pot life of over 24 hours and are easy to handle. Furthermore, the curing speed T10 tends to be long and the T90 tends to be short, so the torque is low in the early stages of vulcanization and gradually increases sharply, which has the advantage of completing vulcanization in a short time while avoiding a situation where vulcanization progresses while the rubber is being distributed throughout the mold.

Claims

1. A compound represented by the following general formula (1): 【Chemistry 1】 (In the general formula (1), R represents an alkyl group having 1 to 4 carbon atoms.)

2. A method for producing the compound according to claim 1, comprising a step of reacting 1-ethynyl-1-cyclohexanol with a carboxylic acid anhydride in the presence of a catalyst represented by the following general formula (14): 【Chemistry 2】 (In the general formula (14), M represents a metal ion, Z represents an anion, and n represents an integer of 1 to 4.)

3. An addition-curable liquid silicone rubber composition comprising: (A) an organopolysiloxane having alkenyl groups bonded to at least two silicon atoms in one molecule; (B) an organohydrogenpolysiloxane having hydrogen atoms bonded to at least two silicon atoms in one molecule; (C) an addition reaction catalyst; and (D) a regulator; 2. An addition-curable liquid silicone rubber composition, wherein the control agent (D) is the compound according to claim 1.

4. A structural member used in an image forming device for business machines, comprising a cured product of the addition-curable liquid silicone rubber composition of claim 3.

5. An adhesive comprising a cured product of the addition-curable liquid silicone rubber composition according to claim 3.

6. An image-forming member comprising a cured product of the addition-curable liquid silicone rubber composition according to claim 3.

7. 4. A coating member for an automobile airbag, comprising a cured product of the addition-curable liquid silicone rubber composition according to claim 3.

8. An optical material for LEDs, comprising a cured product of the addition-curable liquid silicone rubber composition according to claim 3.

9. A sealing material for a photovoltaic power generation device, comprising a cured product of the addition-curable liquid silicone rubber composition according to claim 3.

Images