Lactone Compounds

Abstract

To provide a lactone compound having excellent radical trapping performance.SOLUTION: The present invention provides a lactone compound represented by the formula (I) [where A, B, X and Y independently represent an alkyl group or alkoxy group; m1, m2, n1 and n2 independently represent an integer of 0-4; L represents a specific linking group].SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a novel lactone compound. [Background technology]

[0002] 3-Arylbenzofuranone, a type of lactone compound, is known to be suitable as a stabilizer for organic materials susceptible to oxidation, heat or photodecomposition (see, for example, Patent Documents 1 and 2). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 07-233160 [Patent Document 2] Japanese Patent Application Publication No. 07-165745 Summary of the Invention [Problem to be solved by the invention]

[0004] The present inventors have studied the lactone compounds described in Patent Documents 1 and 2 and have found that there is room for improvement in the performance of scavenging radicals (hereinafter abbreviated as "radical scavenging ability").

[0005] Therefore, an object of the present invention is to provide a lactone compound having excellent radical scavenging ability. [Means for solving the problem]

[0006] Means for Solving the Problems The present inventors have conducted extensive research to achieve the above object and have found that a bis-lactone compound having a specific linking group has excellent radical scavenging ability, thereby completing the present invention. That is, the present inventors have found that the above object can be achieved by the following configuration.

[0007] [1] A lactone compound represented by formula (I) described below. [2] The lactone compound according to [1], wherein m1 and m2 in the formula (I) described below both represent 0. [3] The lactone compound according to [1] or [2], wherein n1 and n2 in the formula (I) described below each represent 2. [4] The lactone compound according to [3], represented by formula (I-1) described below. Effect of the Invention

[0008] According to the present invention, a lactone compound having excellent radical scavenging ability can be provided. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0009] The present invention will be described in detail below. The following description of the components may be based on representative embodiments of the present invention, but the present invention is not limited to such embodiments. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits.

[0010] [Lactone compounds] The lactone compound of the present invention is a lactone compound represented by the following formula (I). [ka] Here, in the above formula (I), A, B, X and Y each independently represent an alkyl group or an alkoxy group. m1 represents an integer of 0 to 4, and when m1 is an integer of 2 to 4, the multiple As may be the same or different substituents. m2 represents an integer of 0 to 4, and when m2 is an integer of 2 to 4, the multiple B's may be the same or different substituents. n1 represents an integer of 0 to 4, and when n1 is an integer of 2 to 4, a plurality of Xs may be the same or different substituents, and may be bonded to each other to form a ring. n2 represents an integer of 0 to 4, and when n2 is an integer of 2 to 4, a plurality of Y's may be the same or different substituents, and may be bonded to each other to form a ring. L represents a linking group represented by the following formula (L1) or (L2). [ka] In the above formulas (L1) and (L2), * represents the bonding position to the phenylene group in the above formula (I). In the above formula (L1), R 1 and R 2 each independently represents a hydrogen atom, an alkyl group, or an alkoxy group; n3 represents an integer of 1 to 12; when n3 is an integer of 2 to 12, a plurality of R 1 may be the same or different substituents, and multiple R 2 may be the same or different substituents. In the above formula (L2), R 11 , R 12 , R 13 and R 14 each independently represents a hydrogen atom, an alkyl group, or an alkoxy group.

[0011] A, B, X, Y, m1, m2, n1, n2, and L in the above formula (I) will be explained in detail below.

[0012] In the above formula (I), the alkyl group represented by one embodiment of A and B is, for example, preferably a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms (e.g., a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a cyclohexyl group, etc.), still more preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably a methyl group or an ethyl group. The alkoxy group represented by one embodiment of A and B is, for example, preferably an alkoxy group having 1 to 18 carbon atoms, more preferably an alkoxy group having 1 to 8 carbon atoms (e.g., a methoxy group, an ethoxy group, an n-butoxy group, a methoxyethoxy group, etc.), still more preferably an alkoxy group having 1 to 4 carbon atoms, and particularly preferably a methoxy group or an ethoxy group.

[0013] In the above formula (I), m1 and m2 each represent an integer of 0 to 4, preferably an integer of 0 to 2, and more preferably 0, because this makes the molecule rigid and makes it difficult for the compound to bleed when incorporated into a polymer compound.

[0014] In the above formula (I), examples of the alkyl group represented by one embodiment of X and Y include the same as the alkyl group represented by one embodiment of A and B described above. Examples of the alkoxy group represented by an embodiment of X and Y include the same alkoxy groups as those represented by an embodiment of A and B described above. Among these, X and Y are preferably a branched alkyl group, more preferably a branched alkyl group having 3 to 12 carbon atoms, and further preferably a tert-butyl group, a tert-amyl group (1,1-dimethylpropyl group), or a tert-octyl group (1,1,3,3-tetramethylbutyl group). On the other hand, when a plurality of Xs are bonded to each other to form a ring, and when a plurality of Ys are bonded to each other to form a ring, examples of the ring formed include a benzene ring, a naphthalene ring, a cyclohexane ring, etc., and among these, a benzene ring is preferable.

[0015] In the above formula (I), n1 and n2 each represent an integer of 0 to 4, preferably an integer of 1 to 4, and more preferably an integer of 2, because this improves the reactivity for forming a lactone ring containing the substituent X or Y in a synthesis utilizing a reaction between phenol and glyoxylic acid (Friedel-Crafts reaction).

[0016] As described above, L in the above formula (I) represents a linking group represented by the following formula (L1) or (L2). [ka] In the above formulas (L1) and (L2), * represents the bonding position to the phenylene group in the above formula (I). In the above formula (L1), R 1 and R 2 each independently represents a hydrogen atom, an alkyl group, or an alkoxy group; n3 represents an integer of 1 to 12; when n3 is an integer of 2 to 12, a plurality of R 1 may be the same or different substituents, and multiple R 2 may be the same or different substituents. In the above formula (L2), R 11 , R 12 , R 13 and R 14 each independently represents a hydrogen atom, an alkyl group, or an alkoxy group.

[0017] R in the above formula (L1) 1 and R 2 and R in the above formula (L2) 11 , R 12 , R 13 and R 14 Examples of the alkyl group in one embodiment of the above include the same alkyl groups as those in one embodiment of A and B above. Also, R 1 and R 2 , and R 11 , R 12 , R 13 and R 14 Examples of the alkoxy group represented by one embodiment of the formula (I) include the same alkoxy groups as those represented by one embodiment of the formula (A) and (B) described above. In addition, n3 in the above formula (L1) represents an integer of 1 to 12. From the viewpoint of radical scavenging ability, it preferably represents an integer of 1 to 8, more preferably an integer of 1 to 4, and even more preferably 2.

[0018] The lactone compound of the present invention is preferably a lactone compound represented by the following formula (I-1) because the reactivity for forming a lactone ring containing a substituent X or Y is improved in the synthesis utilizing the reaction of phenol with glyoxylic acid (Friedel-Crafts reaction) and the radical scavenging ability is further improved. [ka] Here, in the above formula (I-1), A, B, X, Y, m1, m2 and L are all the same as those explained in the above formula (I).

[0019] In the present invention, L in the above formula (I) or the above formula (I-1) preferably represents a linking group represented by the above formula (L1) because the radical scavenging ability is further improved. 1 and R 2 more preferably, each of n3 in the above formula (L1) represents a hydrogen atom, and further preferably, n3 in the above formula (L1) represents 2.

[0020] Specific examples of the lactone compound represented by the above formula (I) include compounds (1) to (17) represented by the following formulas (1) to (17). [ka] JPEG0007674988000006.jpg9980JPEG0007674988000007.jpg12884JPEG0007674988000008.jpg137100

[0021] [High molecular compound] The lactone compound of the present invention can be used as a stabilizer for polymer compounds. Here, the polymer compound is not particularly limited as long as it is an organic material that is susceptible to oxidation, heat or photolysis, and may be either a water-soluble polymer compound or a water-insoluble polymer compound.

[0022] Water-soluble polymer compounds are not particularly limited, and known ones can be used.Specific examples include proteins such as gelatin, casein, and albumin, polysaccharides such as starch and dextrin, cellulose and its derivatives (e.g., carboxymethylcellulose, hydroxypropylcellulose, methylcellulose, etc.), alginic acid, carrageenan, guar gum, xanthan gum, fucoidan, chitosan, hyaluronic acid, polyethylene oxide, polyvinyl alcohol, polyvinylpyrrolidone, polyvinyl methyl ether, polyacrylamide, polyethyleneimine, polyallylamine, polyvinylamine, polylysine, polyacrylic acid, and graft polymers thereof.Also, compounds modified by known methods such as succinated gelatin can be used.

[0023] The water-insoluble polymer compound is not particularly limited, and any known homopolymer or copolymer can be used. Examples of homopolymers include polymers of vinyl acetate, vinyl chloride, styrene, methyl acrylate, butyl acrylate, methacrylonitrile, butadiene, isoprene, and the like. Examples of copolymers include ethylene-butadiene copolymers, styrene-butadiene copolymers, styrene-p-methoxystyrene copolymers, styrene-vinyl acetate copolymers, vinyl acetate-vinyl chloride copolymers, vinyl acetate-diethyl maleate copolymers, methyl methacrylate-acrylonitrile copolymers, methyl methacrylate-butadiene copolymers, methyl methacrylate-styrene copolymers, methyl methacrylate-vinyl acetate copolymers, methyl methacrylate-vinylidene chloride copolymers, methyl acrylate-acrylonitrile copolymers, methyl acrylate-butadiene copolymers, methyl acrylate-styrene copolymers, methyl acrylate-vinyl acetate copolymers, acrylic acid-butyl acrylate copolymers, methyl acrylate-vinyl chloride copolymers, butyl acrylate-styrene copolymers, polyesters, polycarbonates, and various urethanes.

[0024] The content of such a polymer compound is not particularly limited, but is preferably 1,000 to 10,000,000 parts by mass, more preferably 100,000 to 10,000,000 parts by mass, and even more preferably 200,000 to 2,000,000 parts by mass, relative to 100 parts by mass of the lactone compound of the present invention described above. The content of the lactone compound of the present invention described above is preferably 0.001 to 10 parts by mass, more preferably 0.001 to 1 part by mass, even more preferably 0.001 to 0.1 part by mass, and particularly preferably 0.005 to 0.05 parts by mass, relative to 100 parts by mass of the polymer compound.

[0025] In addition, when the lactone compound of the present invention is used as a stabilizer, etc., it can be used in combination with a co-stabilizer described in paragraphs

[0180] to

[0212] of Patent Document 1 (JP Patent Publication No. 07-233160) and paragraphs

[0199] to

[0222] of Patent Document 1 (JP Patent Publication No. 2019-014826). EXAMPLES

[0026] The present invention will be described in more detail below with reference to examples. The materials, amounts, ratios, processing contents, processing procedures, etc. shown in the following examples can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the following examples.

[0027] [Example 1] [Synthesis of compound (1)] 21.3 parts by mass of 2,4-di-tert-butylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 10.4 parts by mass of glyoxylic acid monohydrate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 0.051 parts by mass of p-toluenesulfonic acid monohydrate (manufactured by Tokyo Chemical Industry Co., Ltd.), and 40 parts by mass of 1,2-dichloroethane (manufactured by Tokyo Chemical Industry Co., Ltd.) were weighed into a flask. The weighed flask was then placed in an oil bath at 105°C, and heating was continued until the internal temperature reached 86°C by adding 1,2-dichloroethane in an amount equal to the amount of the distillate while distilling off the distillate using a Dean-Stark flask. Next, the oil bath was heated to 120°C, and the mixture was concentrated so that the remaining amount of 1,2-dichloroethane was less than 10 parts by mass. Thereafter, the reaction solution was cooled to room temperature (23°C), and 100 parts by mass of hexane and 100 parts by mass of water were added and stirred. Thereafter, the hexane layer was collected, and 100 parts by mass of saturated saline was added and stirred. Thereafter, the hexane layer was collected, and 1 part by mass of magnesium sulfate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was added and dried for 1 hour. Next, the magnesium sulfate was filtered off, and the hexane layer was concentrated to dryness using an evaporator to obtain 27.0 parts by mass of a brown viscous body (1) containing a compound represented by the following formula (1a). [ka]

[0028] Next, 4.41 parts by mass of ethylene glycol diphenyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.), 15.88 parts by mass of tin(IV) chloride pentahydrate (manufactured by Tokyo Chemical Industry Co., Ltd.), and 81 parts by mass of 1,2-dichloroethane (manufactured by Tokyo Chemical Industry Co., Ltd.) were weighed into the brown viscous body (1) and refluxed for 4 hours using an oil bath at 105°C. Next, 40 parts by mass of 1,2-dichloroethane was distilled off, and the reaction solution was cooled to room temperature (23°C), and 200 parts by mass of ethyl acetate and 200 parts by mass of water were added. Then, the ethyl acetate layer was collected, and 200 parts by mass of saturated saline was added and stirred. Then, the ethyl acetate layer was collected, and separation and purification were repeated using 200 parts by mass of saturated saline until the pH of the saturated saline layer became 6. Then, the ethyl acetate layer was collected, and 1 part by mass of magnesium sulfate was added and dried for 1 hour. Next, the magnesium sulfate was filtered through Celite, and the ethyl acetate layer was concentrated to dryness using an evaporator to obtain 21 parts by mass of a brown viscous material (2). The resulting brown viscous substance (2) was purified by column chromatography to obtain compound (1) represented by the above formula (1). The obtained compound (1) 1 The H-NMR (Nuclear Magnetic Resonance) data and their assignments are shown below. 1HNMR(CDCl3=7.26ppm)δ(ppm)=1.29(18H,s),1.43(18H,S),4.31(4H,s),4.78(2H,s),6.94(4H,d),7.04(2H,s),7.16(4H,d),7.32(2H,s) [ka]

[0029] [Evaluation of radical scavenging ability] Compound (1) was added to polycarbonate resin at a concentration of 150 ppm, and the mixture was dry-mixed for 10 minutes. The mixture was then kneaded at a melt temperature of 260°C using a twin-screw extruder (TEX30α (L / D=42, Φ=30 mm) manufactured by Japan Steel Works, Ltd.) to obtain pellets. The obtained pellets were used to prepare plate-shaped test pieces having a width of 50 mm, a length of 90 mm and a thickness of 1.5 mm, at 290° C. using an injection molding machine (J100EII-P manufactured by Japan Steel Works, Ltd.). Next, the test piece was irradiated with UV (ultraviolet) light, and the amount of radicals generated was quantified by electron spin resonance (ESR). As a result, the increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 0.10×10^3[au].

[0030] [Example 2] The reaction was carried out in the same manner as in Example 1, except that 4.41 parts by mass of ethylene glycol diphenyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 4.98 parts by mass of 1,2-bis(3-methylphenoxy)ethane (manufactured by Sankosha), to obtain the following compound. Next, the amount of radicals generated on the test piece on the plate was quantified in the same manner as in Example 1. The increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 0.15×10^3[au]. [ka]

[0031] [Example 3] The reaction was carried out in the same manner as in Example 1, except that 4.41 parts by mass of ethylene glycol diphenyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 5.64 parts by mass of 1,2-bis(2-methoxyphenoxy)ethane synthesized according to Journal of Molecular Structure, 2019, vol. 1175, pp. 414-427, to obtain the following compound. Next, the amount of radicals generated on the test piece on the plate was quantified in the same manner as in Example 1. The increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 0.15×10^3[au]. [ka]

[0032] [Example 4] The reaction was carried out in the same manner as in Example 1, except that 4.41 parts by mass of ethylene glycol diphenyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 4.12 parts by mass of diphenoxymethane (manufactured by Tokyo Chemical Industry Co., Ltd.), to obtain the following compound. Next, the amount of radicals generated on the test piece on the plate was quantified in the same manner as in Example 1. The increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 0.20×10^3[au]. [ka]

[0033] [Example 5] The reaction was carried out in the same manner as in Example 1, except that 4.41 parts by mass of ethylene glycol diphenyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 4.69 parts by mass of 1,3-diphenoxypropane synthesized according to Journal of Molecular Structure, 2019, vol. 1175, p. 414-427, to obtain the following compound. Next, the amount of radicals generated on the test piece on the plate was quantified in the same manner as in Example 1. The increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 0.20×10^3[au]. [ka]

[0034] [Example 6] The reaction was carried out in the same manner as in Example 1, except that 4.41 parts by mass of ethylene glycol diphenyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 5.56 parts by mass of 1,6-diphenoxyhexane synthesized according to Journal of Molecular Structure, 2019, vol. 1175, pp. 414-427, to obtain the following compound. Next, the amount of radicals generated on the test piece on the plate was quantified in the same manner as in Example 1. The increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 0.25×10^3[au]. [ka]

[0035] [Example 7] The reaction was carried out in the same manner as in Example 1, except that 4.41 parts by mass of ethylene glycol diphenyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 6.72 parts by mass of 1,10-diphenoxydecane synthesized according to Journal of Molecular Structure, 2019, vol. 1175, pp. 414-427, to obtain the following compound. Next, the amount of radicals generated on the test piece on the plate was quantified in the same manner as in Example 1. The increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 0.30×10^3[au]. [ka]

[0036] [Example 8] The reaction was carried out in the same manner as in Example 1, except that 4.41 parts by mass of ethylene glycol diphenyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 4.08 parts by mass of dibenzyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.), to obtain the following compound. Next, the amount of radicals generated on the test piece on the plate was quantified in the same manner as in Example 1. The increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 0.80×10^3[au]. [ka]

[0037] [Example 9] The reaction was carried out in the same manner as in Example 1, except that 21.3 parts by mass of 2,4-di-tert-butylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 17.0 parts by mass of 2-tert-butyl-p-cresol (manufactured by Tokyo Chemical Industry Co., Ltd.), to obtain the following compound. Next, the amount of radicals generated on the test piece on the plate was quantified in the same manner as in Example 1. The increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 0.12×10^3[au]. [ka]

[0038] [Example 10] The reaction was carried out in the same manner as in Example 1, except that 21.3 parts by mass of 2,4-di-tert-butylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 24.2 parts by mass of 2,4-di-tert-amylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.), to obtain the following compound. Next, the amount of radicals generated on the test piece on the plate was quantified in the same manner as in Example 1. The increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 0.10×10^3[au]. [ka]

[0039] [Example 11] The reaction was carried out in the same manner as in Example 1, except that 21.3 parts by mass of 2,4-di-tert-butylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 21.3 parts by mass of 4-(1,1,3,3-tetramethylbutyl)phenol (manufactured by Tokyo Chemical Industry Co., Ltd.), to obtain the following compound. Next, the amount of radicals generated was quantified in the same manner as in Example 1. The increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 0.10×10^3[au]. [ka]

[0040] [Example 12] The reaction was carried out in the same manner as in Example 1, except that 21.3 parts by mass of 2,4-di-tert-butylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 28.5 parts by mass of 4-dodecyl-o-cresol (manufactured by Tokyo Chemical Industry Co., Ltd.), to obtain the following compound. Next, the amount of radicals generated was quantified in the same manner as in Example 1. The increase in ESR signal intensity at B=3400G after irradiation for 1200 seconds was 0.12×10^3[au]. [ka]

[0041] [Example 13] The reaction was carried out in the same manner as in Example 1, except that 21.3 parts by mass of 2,4-di-tert-butylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 14.9 parts by mass of 1-naphthol (manufactured by Tokyo Chemical Industry Co., Ltd.), to obtain the following compound. Next, the amount of radicals generated was quantified in the same manner as in Example 1. The increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 0.22×10^3[au]. [ka]

[0042] [Example 14] A plate-shaped test piece was obtained in the same manner as in Example 1, except that the polycarbonate resin was changed to a polyester resin. Next, the amount of radicals generated was quantified in the same manner as in Example 1. The increase in ESR signal intensity at B=3400G after irradiation for 1200 seconds was 0.07×10^3[au].

[0043] [Example 15] A plate-shaped test piece was obtained in the same manner as in Example H, except that under the conditions of Example 1, UV-008 (manufactured by Fujifilm Corporation) was further added at a concentration of 150 ppm relative to the polyester resin. Next, the amount of radicals generated was quantified in the same manner as in Example 9. The increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 0.05×10^3[au].

[0044] [Comparative Example 1] The amount of radicals generated was quantified in the same manner as in Example 1, except that compound (1) was not added. As a result, the increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 1.50×10^3[au].

[0045] [Comparative Example 2] The amount of radicals generated was quantified in the same manner as in Example 1, except that 150 ppm of a compound (H1) represented by the following formula (H1) was used instead of 150 ppm of the compound (1). As a result, the increase in ESR signal intensity at B=3400G after 1200 seconds of irradiation was 1.20×10^3[au]. [ka]

[0046] From the results shown in Examples 1 to 15 and Comparative Examples 1 and 2, when the lactone compound represented by the above formula (I) was used, the increase in ESR signal intensity was less than half compared to when no lactone compound was used or when a lactone compound not corresponding to the above formula (I) was used, and therefore it was found that the compound represented by the above formula (I) is a compound with excellent radical scavenging ability. In particular, when a compound in which L in the above formula (I) is represented by L1 is used, the increase in ESR signal intensity is one-tenth or less compared to when no lactone compound is used or when a lactone compound not corresponding to the above formula (I) is used, and therefore it was found to be a compound with superior radical scavenging ability.

Claims

1. A lactone compound represented by the following formula (I): 【Chemistry 1】 Here, in the formula (I), A, B, X and Y each independently represent an alkyl group or an alkoxy group. m1 represents an integer of 0 to 4, and when m1 is an integer of 2 to 4, the multiple As may be the same or different substituents. m2 represents an integer of 0 to 4, and when m2 is an integer of 2 to 4, the multiple B's may be the same or different substituents. n1 represents an integer of 0 to 4. When n1 is an integer of 2 to 4, the multiple Xs may be the same or different substituents, and may be bonded to each other to form a ring. n2 represents an integer of 0 to 4. When n2 is an integer of 2 to 4, the multiple Ys may be the same or different substituents, and may be bonded to each other to form a ring. L represents a linking group represented by the following formula (L1) or (L2). 【Chemistry 2】 In the formulae (L1) and (L2), * represents the bonding position to the phenylene group in the formula (I). In the formula (L1), R １ and R ２ each independently represents a hydrogen atom, an alkyl group, or an alkoxy group; n3 represents an integer of 1 to 12; when n3 is an integer of 2 to 12, a plurality of R １ may be the same or different substituents, and multiple R ２ may be the same or different substituents. In the formula (L2), R １１ , R １２ , R １３ and R １４ each independently represents a hydrogen atom, an alkyl group, or an alkoxy group.

2. The lactone compound according to claim 1 , wherein m1 and m2 in formula (I) each represent 0.

3. The lactone compound according to claim 1 or 2, wherein n1 and n2 in the formula (I) each represent 2.

4. The lactone compound according to claim 3, represented by the following formula (I-1): 【Chemistry 3】 Here, in the formula (I-1), A, B, X and Y each independently represent an alkyl group or an alkoxy group. m1 represents an integer of 0 to 4, and when m1 is an integer of 2 to 4, the multiple As may be the same or different substituents. m2 represents an integer of 0 to 4, and when m2 is an integer of 2 to 4, the multiple B's may be the same or different substituents. L represents a linking group represented by the following formula (L1) or (L2). 【Chemistry 4】 In the formulae (L1) and (L2), * represents the bonding position to the phenylene group in the formula (I). In the formula (L1), R １ and R ２ each independently represents a hydrogen atom, an alkyl group, or an alkoxy group; n3 represents an integer of 1 to 12; when n3 is an integer of 2 to 12, a plurality of R １ may be the same or different substituents, and multiple R ２ may be the same or different substituents. In the formula (L2), R １１ , R １２ , R １３ and R １４ each independently represents a hydrogen atom, an alkyl group, or an alkoxy group.

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