Isoindoline compounds

Abstract

To provide a bio-derived isoindoline compound which can be used as an isoindoline-based yellow pigment and is produced by a safe, clean, green and carbon-neutral approach; and a composition containing the isoindoline compound.SOLUTION: An isoindoline compound contains a radiocarbon atom 14C and has a group represented by formula (A).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to isoindoline compounds, compositions containing the isoindoline compounds, and methods for producing the isoindoline compounds. [Background technology]

[0002] Isoindoline yellow pigments are not as large as azo dimers and have relatively high light and heat fastness even though they do not contain halogens, making them highly promising for many applications, including automotive paints, decorative paints, GI coatings, plastics, inks, and special applications. Commercially available isoindoline-based yellow pigments are produced by coupling specific building blocks to DII (1,3-diiminoisoindoline). Such DII is mainly synthesized using phthalonitrile as a starting material (see, for example, Non-Patent Document 1), but DII synthesized using phthalic anhydride as a starting material (see, for example, Patent Document 1) has also been reported. However, phthalonitrile is toxic to humans and has adverse environmental effects, and is generally only available from petroleum sources. In recent years, from the perspectives of sustainable development, reducing carbon dioxide emissions, and safety, there has been an increasing movement to switch from petroleum-derived raw materials to bio- (biomass)-derived raw materials and to replace harmful chemicals with less toxic ones. Currently produced isoindoline-based yellow pigments are unlikely to meet future environmental demands, and from the standpoints of clean, green, and carbon neutrality, it is desirable to provide bio-derived isoindoline-based yellow pigments. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 7-330729 [Non-patent literature]

[0004] [Non-Patent Document 1] Chem. Lett. 1984 8 1423-1426 Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide a bio-derived isoindoline compound that can be used as an isoindoline-based yellow pigment and that can be obtained through a safe, clean, green, and carbon-neutral approach, and a composition containing the isoindoline compound. [Means for solving the problem]

[0006] As a result of investigations to solve the above-mentioned problems, the present inventors have found that a radioactive carbon atom can be produced by using bio-derived furan and bio-derived maleic anhydride as raw materials, obtaining a DA intermediate by a Diels-Alder (DA) reaction, dehydrating the DA intermediate, aromatizing it, and converting it into an amine with urea. 14 The present inventors have found that bio-derived isoindoline compounds that can be used as isoindoline-based yellow pigments can be obtained by obtaining bio-DII containing C and coupling the bio-DII with building blocks, and have thus completed the present invention.

[0007] That is, the present invention includes the following aspects. [1] Radioactive carbon atoms 14 An isoindoline compound containing C and having a group represented by the following formula (A): [ka] (In the formula (A), R 1 ~R 4 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a phenyl group which may be substituted with an alkyl group. 2 and R 3may be ring-closed to form a 5- to 8-membered ring. 7 ~R 8 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which may be substituted with an alkyl group. * represents a bond. [2] The isoindoline compound according to [1], wherein the isoindoline compound having a group represented by formula (A) is an isoindoline compound represented by the following formula (A-1) or the following formula (A-2): [ka] [ka] (In the formula (A-1) and the formula (A-2), R 1 ~R 4 is the above R 1 ~R 4 It has the same meaning as R 7 ~R 8 is the above R 7 ~R 8 It has the same meaning as R 9 ~R 10 is the R 7 ~R 8 Similarly, each independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which may be substituted with an alkyl group.) [3] The isoindoline compound according to [2], wherein the isoindoline compound represented by the formula (A-1) is an isoindoline compound represented by the following formula (A-1-1), or the isoindoline compound represented by the formula (A-2) is an isoindoline compound represented by the following formula (A-2-1): [ka] [ka] [4] A composition containing an isoindoline compound having a group represented by formula (A) according to [1]. [5] The composition according to [4], which is used as a pigment composition. [6] The composition according to [4], which contains at least two or more isoindoline compounds having a group represented by formula (A). [7] The composition according to [4], containing an isoindoline compound represented by the following formula (A-1) and an isoindoline compound represented by the following formula (A-3): [ka] [ka] (In the formula (A-1) and the formula (A-3), R 1 ~R 4 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a phenyl group which may be substituted with an alkyl group. 2 and R 3 may be ring-closed to form a 5- to 8-membered ring. 7 ~R 10 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which may be substituted with an alkyl group. [8] The composition according to [7], wherein the proportion of the isoindoline compound represented by the formula (A-3) in the composition is 0.5 to 10.0 mass %. [9] The composition according to [7], wherein the isoindoline compound represented by the formula (A-1) is an isoindoline compound represented by the following formula (A-1-1), and the isoindoline compound represented by the formula (A-3) is an isoindoline compound represented by the following formula (A-3-1): [ka] [ka]

[10] Radioactive carbon atoms 14 A method for producing an isoindoline compound containing C and having a group represented by the following formula (A), [ka] (In the formula (A), R 1 ~R 4 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a phenyl group which may be substituted with an alkyl group. 2 and R 3 may be ring-closed to form a 5- to 8-membered ring. 7 ~R 8 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which may be substituted with an alkyl group. * represents a bond. A method for producing an isoindoline compound, comprising reacting a compound represented by the following formula (I-2) with a barbituric acid represented by the following formula (B) in an acid-free solvent or in a solvent containing at least one acid selected from the group consisting of hydrochloric acid, sulfuric acid, methanesulfonic acid, p-toluenesulfonic acid, acetic acid, triflic acid, phosphoric acid, polyphosphoric acid, pyrophosphoric acid, and nitric acid, to obtain an isoindoline compound having a group represented by the formula (A). [ka] (In the formula (I), R 1 ~R 4 is the above R 1 ~R 4 It has the same meaning as [ka] (In the formula (B), R 5 ~R 6 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which may be substituted with an alkyl group.

[11] The compound represented by formula (I-2) A compound represented by the following formula (PA) is obtained from a compound represented by the following formula (DA), [ka] (In the formula (DA), R1 ~R 4 is the above R 1 ~R 4 It has the same meaning as [ka] (In the formula (PA), R 1 ~R 4 is the above R 1 ~R 4 It has the same meaning as The method for producing an isoindoline compound according to

[10] , wherein the isoindoline compound represented by the formula (I-2) is obtained from the compound represented by the formula (PA).

[12] The method for producing an isoindoline compound according to

[10] , wherein the solvent is any one selected from the group consisting of HO, dimethylacetamide (DMA), dimethylformamide (DMF), dimethyl sulfoxide (DMSO), MeOH, EtOH, isopropyl alcohol (IPA), and tBuOH. [Effects of the Invention]

[0008] According to the present invention, it is possible to provide a bio-derived isoindoline compound that can be used as an isoindoline-based yellow pigment and that can be obtained by a safe, clean, green, and carbon-neutral approach, and a composition containing the isoindoline compound. [Brief explanation of the drawings]

[0009] [Figure 1] FIG. 1 is a diagram showing the results of TEM observation of the pigment of Example 1. [Figure 2] FIG. 2 is a diagram showing the results of TEM observation of the pigment of Comparative Example 1. DETAILED DESCRIPTION OF THE INVENTION

[0010] The present invention will be described in detail below. Note that the following explanation of the constituent elements is an example for explaining the present invention, and the present invention is not limited to these contents.

[0011] (Radioactive carbon atoms 14 an isoindoline compound containing C and having a group represented by the following formula (A): The isoindoline compounds of the present invention contain a radioactive carbon atom. 14 Contains C. The isoindoline compound of the present invention has a group represented by the following formula (A).

[0012] [ka]

[0013] In formula (A), R 1 ~R 4 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a phenyl group which may be substituted with an alkyl group. 2 and R 3 may be ring-closed to form a 5- to 8-membered ring. 7 ~R 8 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which may be substituted with an alkyl group. * represents a bond.

[0014] The isoindoline compound of the present invention is a radioactive carbon atom compound represented by the following formula (I-2), which is produced using bio-derived furan and bio-derived maleic anhydride. 14 Since the isoindoline compound of the present invention is produced using a bioisoindoline compound containing C, it contains a bio (biomass) component derived from a biological raw material. The inclusion of a biocomponent in the isoindoline compound of the present invention can be explained by, for example, the presence of a radioactive carbon atom. 14 This can be confirmed by measuring C.

[0015] [ka]

[0016] In the above formula (I-2), R 1 ~R 4is the above R 1 ~R 4 It has the same meaning as:

[0017] For example, compounds and compositions derived from living organisms and those derived from petroleum do not differ in physical properties such as molecular weight, mechanical properties, or thermal properties. To distinguish between them, the biomass ratio is generally used. In this biomass ratio, the carbon in petroleum-derived compounds and compositions has the following characteristics: 14 Since it does not contain C (radioactive carbon 14, half-life 5730 years), 14 By measuring the C concentration using accelerator mass spectrometry, it is possible to determine whether the compounds or compositions produced are petroleum-derived or bio-derived compounds.

[0018] This biomass degree can be measured, for example, by burning a sample to be measured to generate carbon dioxide, which is then purified in a vacuum line and reduced with hydrogen using iron as a catalyst to generate graphite. This graphite was then used in a tandem accelerator-based 14 Attach it to the C-AMS dedicated device (manufactured by NEC) 14 Counting C, 13 The concentration of C ( 13 C / 12 C). 14 The concentration of C ( 14 C / 12 C) is measured, and the carbon content of the sample is compared to the standard modern carbon. 14 It can be determined by calculating the percentage of C concentration. For the measurement, oxalic acid (HOxII) provided by the National Institute of Standards (NIST) can be used as a standard sample.

[0019] One index for evaluating the degree of biomass is, for example, percent modern carbon (pMC). Here, pMC (percent modern carbon) can be calculated by measurement according to ASTM-D6866-18, and is the percentage of standard modern carbon. 14 C concentration in the target 14 It represents the percentage of C concentration. 14If C is not contained, the pMC will be 0%.

[0020] In the above formula (I), R 2 and R 3 As described above, may close a ring to form a 5- to 8-membered ring. The ring structure may be a functional ether, alcohol, or carboxyl functional group. Here, the term "functional functional group" means that the ring structure may have an -OH group, a -COOH group, or an -O- group. For example, the ring structure may be a compound represented by the following formula (v), (vi), or (vii):

[0021] [ka]

[0022] Preferred embodiments of the isoindoline compound having a group represented by formula (A) include, for example, an isoindoline compound represented by the following (A-1) and an isoindoline compound represented by the following (A-2).

[0023] [ka]

[0024] [ka]

[0025] In the above formula (A-1) and the above formula (A-2), R 1 ~R 4 is the above R 1 ~R 4 It has the same meaning as R 7 ~R 8 is the above R 7 ~R 8 It has the same meaning as R 9 ~R 10 is the above R 7 ~R 8Similarly, each independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which may be substituted with an alkyl group.

[0026] The pMC (percent modern carbon) of the isoindoline compound represented by formula (A-1) or the isoindoline compound represented by formula (A-2) is preferably 1% or more, more preferably 50% or more, even more preferably 75% or more, still more preferably 90% or more, and even more preferably 99% or more.

[0027] Furthermore, a preferred embodiment of the isoindoline compound represented by formula (A-1) is, for example, an isoindoline compound represented by the following (A-1-1), and a preferred embodiment of the isoindoline compound represented by formula (A-2) is, for example, an isoindoline compound represented by the following (A-2-1). Note that the isoindoline compound represented by (A-1-1) is a compound known to constitute the pigment Y139, and the isoindoline compound represented by (A-2-1) is a compound known to constitute the pigment Y185.

[0028] [ka]

[0029] [ka]

[0030] The isoindoline compound of the present invention containing a group represented by formula (A), or a composition containing the isoindoline compound, is a compound having a radioactive carbon atom. 14 It is used as an isoindoline-based yellow pigment containing C, i.e., containing biocomponents.

[0031] (Method for producing an isoindoline compound containing a group represented by formula (A)) radioactive carbon atoms 14The isoindoline compound of the present invention containing C, that is, containing a group represented by formula (A) containing a biocomponent, can be obtained by the method described below. The reaction can proceed without an acid with a compound represented by the following formula (I-2), but more preferably, the reaction can be carried out in a solvent containing an acid with a barbituric acid represented by the following formula (B), to obtain an isoindoline compound having a group represented by the above formula (A).

[0032] [ka]

[0033] In the above formula (I-2), R 1 ~R 4 is the above R 1 ~R 4 It has the same meaning as:

[0034] [ka]

[0035] In the above formula (B), R 5 ~R 6 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which may be substituted with an alkyl group.

[0036] A preferred embodiment of the method for producing an isoindoline compound containing a group represented by formula (A) is a production method in which the isoindoline compound is particularly an isoindoline compound represented by formula (A-1). The isoindoline compound represented by formula (A-1) can be obtained by the following method.

[0037] [ka]

[0038] In the above formula (I-2) and the above formula (A-1), R 1 ~R10 is the above R 1 ~R 10 It has the same meaning as:

[0039] <Reaction G> The isoindoline compound represented by formula (A-1) can be obtained by reacting the compound represented by formula (I-2) with the barbituric acid represented by formula (B) in a solvent containing an acid (more specifically, a solvent containing at least one acid selected from the group consisting of hydrochloric acid, sulfuric acid, methanesulfonic acid, p-toluenesulfonic acid, acetic acid, triflic acid, phosphoric acid, polyphosphoric acid, pyrophosphoric acid, and nitric acid) or in a solvent not containing an acid, although the reaction can proceed without an acid.

[0040] The concentration of the acid used in the above reaction G is preferably 0.5 to 30% by mass, more preferably 1 to 10% by mass.

[0041] The solvent used in the reaction of the barbituric acid represented by the formula (B) is preferably any one selected from the group consisting of HO, dimethylacetamide (DMA), dimethylformamide (DMF), dimethyl sulfoxide (DMSO), MeOH, EtOH, isopropyl alcohol (IPA), and tBuOH.

[0042] In the isoindoline compound having a group represented by the above formula (A-1) obtained by reaction G, R 7 and R 8 are R in the above formula (B), respectively. 5 and R 6 corresponds to R 7 R 5 With R 8 R 6 Even if R 7 R 6 With R 8 R 5 Either one is acceptable. 9 and R 10 Similarly, each of R in the above formula (B) 5 and R 6 corresponds to R9 R 5 With R 10 R 6 Even if R 9 R 6 With R 10 R 5 Either one is fine.

[0043] The compound represented by the above formula (I-2) is A compound represented by the following formula (PA) is obtained from a compound represented by the following formula (DA),

[0044] [ka] (In formula (DA), R 1 ~R 4 is the above R 1 ~R 4 It has the same meaning as

[0045] [ka] (In formula (PA), R 1 ~R 4 is the above R 1 ~R 4 It has the same meaning as The isoindoline compound represented by the above formula (I-2) can be obtained from the compound represented by the above formula (PA).

[0046] When obtaining the compound represented by formula (PA) from the compound represented by formula (DA), the reaction can be carried out under acidic conditions. The acidic conditions may be any conditions that allow the reaction to proceed favorably, and may be, for example, formed by using any acid selected from the group consisting of hydrochloric acid, sulfuric acid, methanesulfonic acid, p-toluenesulfonic acid, acetic acid, acetic anhydride, triflic acid, phosphoric acid, phosphoric anhydride, polyphosphoric acid, pyrophosphoric acid, nitric acid, and mixtures of these acids.

[0047] When obtaining the isoindoline compound represented by the formula (I-2) from the compound represented by the formula (PA), the amination reaction is carried out in the presence of molybdenum ammonium as a catalyst and urea or NH3 as an amine source.

[0048] A preferred embodiment of the method for producing the isoindoline compound represented by formula (I-2) is, for example, the production method described below.

[0049] <Method for producing the isoindoline compound represented by (I-2)> The isoindoline compound represented by formula (I-2) can be obtained from the compound represented by formula (DA) via the compound represented by formula (PA) or formula (I-2 nitrate). The specific reaction pathway of this production method is shown below.

[0050] [ka] (R in the formula 1 ~R 4 is the above R 1 ~R 4 It has the same meaning as

[0051] <<Reaction A>> Compound (DA) can be subjected to a ring-opening dehydration reaction to produce compound (PA). Any reaction solvent may be used as long as it allows the reaction to proceed favorably, but water, acetonitrile, toluene, xylene, alkylbenzene, a mixed solvent of these, or no solvent is preferred. The reaction temperature may be any temperature that allows the reaction to proceed favorably, but is preferably 20 to 150° C., more preferably 30 to 120° C., and more preferably 40 to 100° C. The lower limit is preferably 20° C. or higher, preferably 25° C. or higher, preferably 30° C. or higher, preferably 35° C. or higher, and preferably 40° C. or higher. The upper limit is preferably 150° C. or lower, preferably 140° C. or lower, preferably 130° C. or lower, preferably 120° C. or lower, preferably 110° C. or lower, and preferably 100° C. or lower.

[0052] The reaction can be carried out under acidic conditions, which may be any conditions that allow the reaction to proceed favorably, and may be formed by using any acid selected from the group consisting of hydrochloric acid, sulfuric acid, methanesulfonic acid, p-toluenesulfonic acid, acetic acid, acetic anhydride, triflic acid, phosphoric acid, phosphoric anhydride, polyphosphoric acid, pyrophosphoric acid, nitric acid, and mixtures of these acids. Among these, it is preferable to use an acid containing sulfur or phosphorus, because these acids have a δ + and δ - This is because there is a possibility that the arrangement will be as follows.

[0053] [ka] (In formula (p), X represents -OH, -ONa, -OK, or a methyl group; Y represents a sulfur atom or a phosphorus atom; Z represents a hydrogen atom, -COCH3, -COH, or -(PO2) n OH.)

[0054] The amount of the acid is preferably 0.1 to 3000 mol%, preferably 0.5 to 2500 mol%, preferably 1 to 2000 mol%, preferably 5 to 1500 mol%, preferably 10 to 1000 mol%, preferably 20 to 500 mol%, preferably 50 to 500 mol%, preferably 70 to 500 mol%, preferably 100 to 500 mol%, preferably 150 to 500 mol%, preferably 200 to 500 mol%, preferably 250 to 500 mol%, preferably 300 to 500 mol%. The lower limit is preferably 0.1 mol% or more, preferably 0.5 mol% or more, preferably 1 mol% or more, preferably 5 mol% or more, preferably 10 mol%, preferably 20 mol% or more, preferably 50 mol% or more, preferably 70 mol% or more, preferably 100 mol% or more, preferably 150 mol% or more, preferably 200 mol% or more, preferably 250 mol% or more, and preferably 300 mol% or more. The upper limit is preferably 3000 mol% or less, preferably 2500 mol% or less, preferably 2000 mol% or less, preferably 1500 mol% or less, preferably 1000 mol% or less, and preferably 500 mol% or less. These upper and lower limits can be used in any combination.

[0055] <<Reaction C>> As shown in Reaction A above, after reaction under acidic conditions, in Reaction C, amination can be carried out in the presence of ammonium molybdate as a catalyst and urea or NH3 as an amine source. In reaction C, when oxygen atoms in the compound represented by compound (PA) are substituted with nitrogen atoms, there is no need to add any additive if only one or two oxygen atoms are substituted. However, in order to replace all oxygen atoms with nitrogen atoms as in reaction C, it is preferable to add a compound represented by formula (q) below in order to prevent side reactions such as oligomerization and polymerization.

[0056] [ka] (In formula (q), M f+is NH4 + , Li + , Na + , K. + , Mg 2+ , Ca 2+ , or Al 3+ represents.)

[0057] <<Reaction D>> In the above reaction D, the reaction product obtained through reaction C is treated with aqueous ammonia and sodium hydroxide to produce an isoindoline compound represented by formula (I-2).

[0058] When produced by the above production method, a composition containing the compound represented by formula (I-2) is obtained, but it is also possible to isolate only the compound represented by formula (I-2) by purifying it using a known, conventional method.

[0059] The compound represented by the formula (DA) used to produce the isoindoline compound represented by the formula (I-2) above can be obtained by reacting a compound represented by the following formula (FR) with maleic anhydride.

[0060] [ka] (In formula (FR), R 1 ~R 4 is the above R 1 ~R 4 It has the same meaning as

[0061] The maleic anhydride is preferably derived from biomass. The compound represented by the above formula (FR) is preferably derived from biomass. It is more preferable that both the maleic anhydride and the compound represented by formula (FR) are derived from biomass.

[0062] The biomass content of the raw materials used in the above manufacturing method is preferably 1% or more, more preferably 50% or more, more preferably 75% or more, more preferably 90% or more, and even more preferably 99% or more. Furthermore, if biomass raw materials are available using the mass balance method or the book and claim method, it is easier to achieve a biomass content of 1% or more up to 100%. This patent covers biomass contents including biomass raw materials using the mass balance method and the book and claim method.

[0063] Biomass-derived maleic anhydride can be obtained by cyclization of maleic acid obtained by oxidizing FF or HMF obtained by the methods described in, for example, Japanese Patent No. 5791838 or Japanese Patent No. 6328990, or by direct oxidation. The biomass-derived compound represented by formula (FR) can be obtained by, for example, performing an appropriate combination of decarbonylation, reduction, dehydration, etc. on FF or HMF obtained by the methods described in the above-mentioned Japanese Patent No. 5791838 or Japanese Patent No. 6328990.

[0064] The specific reaction pathway of the above production method is shown below.

[0065] [ka]

[0066] <<Reaction a>> Compound (DA) can be produced by subjecting compound (FR) and maleic anhydride to a Diels-Alder reaction. The reaction may be carried out in the presence or absence of a reaction solvent. Any reaction solvent may be used as long as it allows the reaction to proceed favorably, but chloroform, dioxane, ethyl acetate, alkylbenzene, toluene, xylene, and diethyl ether are preferred. The reaction temperature may be any temperature that allows the reaction to proceed favorably, but is preferably -10 to 100°C, more preferably 0 to 80°C, even more preferably 10 to 70°C, and particularly preferably 15 to 50°C. The lower limit is preferably -10°C or higher, more preferably 0°C or higher, even more preferably 10°C or higher, and particularly preferably 15°C or higher. The upper limit is preferably 100°C or lower, more preferably 80°C or lower, even more preferably 70°C or lower, and particularly preferably 50°C or lower.

[0067] The reaction pressure may be any pressure that allows the reaction to proceed favorably, but is preferably 0.1 to 5 MPa, more preferably 0.1 to 3 MPa, even more preferably 0.1 to 1 MPa, and particularly preferably 0.1 to 0.5 MPa. The lower limit is preferably 0.1 MPa or more, preferably 0.2 MPa or more, preferably 0.3 MPa or more, and preferably 0.4 MPa or more. The upper limit is preferably 5 MPa or less, preferably 3 MPa or less, preferably 1 MPa or less, preferably 0.9 MPa or less, preferably 0.8 MPa or less, preferably 0.7 MPa or less, preferably 0.6 MPa or less, and preferably 0.5 MPa or less.

[0068] (Composition containing an isoindoline compound) The present invention may be a composition containing the isoindoline compound of the present invention having a group represented by formula (A). The composition is preferably used as a pigment composition, particularly as an isoindoline-based yellow pigment. The composition of the present invention may contain, for example, one or more isoindoline compounds having a group represented by formula (A). A more preferred embodiment of the composition of the present invention is, for example, a composition containing an isoindoline compound represented by the following formula (A-1) and / or an isoindoline compound represented by the following formula (A-3).

[0069] [ka]

[0070] [ka]

[0071] In the above formula (A-1) and the above formula (A-3), R 1 ~R 4 is the above R 1 ~R 4 It has the same meaning as R 7 ~R 10 is the above R 7 ~R 10 It has the same meaning as:

[0072] The proportion of the isoindoline compound represented by the above formula (A-3) in the composition is preferably 0 to 30 mass%, more preferably 0.001 to 15 mass%, more preferably 0.01 to 10 mass%, more preferably 0.1 to 7 mass%, and even more preferably 0.5 to 5.0 mass%.

[0073] As explained above in the section <Method for producing an isoindoline compound represented by (I-2)>, bio-derived furan and bio-derived maleic anhydride are used as raw materials, and a compound represented by the above formula (DA) is obtained by the Diels-Alder (DA) reaction. The compound represented by formula (DA) is then dehydrated, aromatized, and converted to an amine with urea, thereby obtaining a radioactive carbon atom. 14 An isoindoline compound represented by formula (I-2) containing C is produced. In this case, the composition containing the isoindoline compound represented by formula (I-2) may contain the isoindoline compound represented by the following formula (I-1) produced in the production process.

[0074] [ka]

[0075] In the above formula (I-1), R 1 ~R 4 is the above R 1 ~R 4 It has the same meaning as:

[0076] When a composition containing an isoindoline compound represented by formula (I-1) in addition to the isoindoline compound represented by formula (I-2) is reacted with a barbituric acid represented by formula (B) described in the column <Reaction G> above in (Method for producing an isoindoline compound containing a group represented by formula (A)), an isoindoline compound represented by formula (A-3) is also produced in addition to the isoindoline compound represented by formula (A-1). The present invention provides a composition containing an isoindoline compound represented by formula (A-3) in addition to the isoindoline compound represented by formula (A-1). This pigment composition has excellent color strength and exhibits pigment performance equal to or superior to commercially available non-bioisoindoline pigment compositions. This allows the provision of a bioisoindoline-based yellow pigment composition Y139 with excellent color strength.

[0077] A more preferred embodiment of the composition of the present invention is a composition containing an isoindoline compound represented by the following formula (A-1-1) and an isoindoline compound represented by the following formula (A-3-1).

[0078] [ka]

[0079] [ka]

[0080] The proportion of the isoindoline compound represented by the above formula (A-3-1) in the composition is preferably 0 to 30 mass%, more preferably 0.001 to 15 mass%, more preferably 0.01 to 10 mass%, more preferably 0.1 to 7 mass%, and even more preferably 0.5 to 5.0 mass%. The BET value of the composition of the present invention is 20 to 100 m 2 / g is preferred, and 30 to 95m 2 / g is preferred, and 40 to 90m 2 / g is preferred, and 50 to 85m2 / g is preferred. In particular, for ink applications, 20 to 80 is preferred, for paint applications, 40 to 90 is preferred, for resin applications, 50 to 90 is preferred, and for color filters, 50 to 100 is preferred. The BET value can be measured by weighing 0.1 g of pigment into a measurement cell and setting it in a specific surface area meter (Macsorb 1208).

[0081] (Application of the isoindoline compound of the present invention) A radioactive carbon atom having a group represented by formula (A) obtained by the above method. 14 The isoindoline compound of the present invention containing C and a composition containing the isoindoline compound constitute isoindoline-based yellow pigments such as Y139 and Y185. The isoindoline compound of the present invention contains carbon derived from biomass and contributes to reducing the environmental load by being carbon neutral. Furthermore, since the isoindoline compound of the present invention is obtained by the above production method, the number and positions of various types of functional groups can be controlled by changing the type of furan or by changing to another type of diene. The isoindoline compound of the present invention and the isoindoline-based yellow pigment comprising a composition containing the isoindoline compound can be used as a coloring composition, a molding composition, or the like. Furthermore, the isoindoline compound of the present invention and the isoindoline-based yellow pigment comprising a composition containing the isoindoline compound are mixed with other resins, rubbers, additives, solvents, pigments, dyes, etc., as necessary, and prepared for use as coating materials for cosmetics, pharmaceuticals, or agricultural chemicals, or as printing markers, stationery, writing implements, printing inks, inkjet inks, metal inks, paints, plastic colorants, toners (color toners), color filters, etc.

[0082] <Coloring composition> The coloring composition preferably contains an isoindoline-based yellow pigment composition comprising the isoindoline compound of the present invention or a composition containing the isoindoline compound, and a dispersion medium.

[0083] <<Dispersion medium>> Examples of the dispersion medium include resins and solvents. Examples of the resin include resin-type dispersants and binder resins. Examples of the solvent include water and organic solvents. If necessary, a low-molecular-weight dispersant such as a surfactant can be used.

[0084] Examples of types of resins in resin-type dispersants include styrene-(meth)acrylic acid copolymers, (meth)acrylic acid-(meth)acrylic acid alkyl ester copolymers, styrene-(meth)acrylic acid-(meth)acrylic acid alkyl ester copolymers, styrene-α-methylstyrene-(meth)acrylic acid copolymers, styrene-α-methylstyrene-(meth)acrylic acid-(meth)acrylic acid alkyl ester copolymers, poly(meth)acrylic acid, vinylnaphthalene-(meth)acrylic acid copolymers, styrene-maleic acid copolymers, maleic acid-maleic anhydride copolymers, α-olefin-maleic acid (anhydride) copolymers, α-olefin-maleic acid (anhydride)-polyalkylene glycol allyl ether copolymer vinylnaphthalene-maleic acid copolymers, polyester-modified (meth)acrylic acid polymers, and salts thereof. The form of the resin in the resin-type dispersant may be, for example, a water-soluble resin or an emulsion (water-insoluble resin).

[0085] The binder resin may be, for example, a polyolefin resin, a polyester resin, a styrene copolymer, an acrylic resin, or a modified resin thereof. Specific examples include polyolefin resins such as polyethylenes (e.g., high-density polyethylene (HDPE), linear low-density polyethylene (L-LDPE), and low-density polyethylene (LDPE)) and polypropylene; polyester resins (e.g., polyethylene terephthalate); and styrene copolymers (e.g., styrene-p-chlorostyrene copolymer, styrene-vinyltoluene copolymer, styrene-vinylnaphthalene copolymer, styrene-acrylic acid ester copolymer, styrene-methacrylic acid ester copolymer, styrene-α-chloromethyl methacrylate copolymer, styrene-acrylonitrile copolymer, styrene-vinyl methyl ether copolymer, styrene-vinyl ethyl ether copolymer, styrene-vinyl methyl ketone copolymer, styrene-butadiene copolymer, styrene-isoprene copolymer, and styrene-acrylonitrile-indene copolymer. acrylic resins such as acrylic resins and methacrylic resins; polyvinyl chloride, phenolic resins, naturally modified phenolic resins, natural resin-modified maleic acid resins, polyvinyl acetate, silicone resins, polyurethane resins, ethylene-vinyl acetate copolymer resins, vinyl acetate resins, nitrocellulose resins, polyamide resins, epoxy resins, xylene resins, polyvinyl butyral resins, polyvinyl acetal resins, cellulose ester resins, alkyd resins, rosin resins, ketone resins, cyclized rubbers, chlorinated polyolefin resins, terpene resins, coumarone-indene resins, alkyd resins, amino resins, petroleum resins, and modified resins thereof.

[0086] Organic solvents can be classified into water-soluble solvents and water-insoluble solvents. Examples of water-soluble solvents include ethanol, n-propanol, isopropanol, isobutanol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, and glycerin. Examples of water-insoluble solvents include toluene, xylene, butyl acetate, methyl acetate, methyl ethyl ketone, methyl isobutyl ketone, butyl alcohol, and aliphatic hydrocarbons.

[0087] Each material constituting the coloring composition can be used alone or in combination of two or more kinds.

[0088] <Molding composition> The molding composition contains a coloring composition (pigment composition, resin). The molding composition preferably contains a thermoplastic resin in the resin. The molding composition containing a thermoplastic resin is preferably melted and kneaded, and molded into a desired shape to produce a molded product.

[0089] Examples of thermoplastic resins include homopolymers or copolymers using ethylene, propylene, butylene, styrene, or the like as monomer components. More specifically, examples include polyethylenes such as high-density polyethylene (HDPE), linear low-density polyethylene (L-LDPE), and low-density polyethylene (LDPE), as well as polyolefin resins such as polypropylene and polybutylene. Specific examples of other useful resins include polyester resins such as polyethylene terephthalate, polyamide resins such as nylon 6 and nylon 66, polystyrene resins, and thermoplastic ionomer resins. Among these, polyolefin resins and polyester resins are preferred. The number-average molecular weight of the thermoplastic resin is preferably greater than 30,000 and not greater than 200,000.

[0090] The molding composition may contain wax. Waxes are made of low-molecular-weight polyolefins. These are polymers of olefin monomers such as ethylene, propylene, and butylene, and may be block or random copolymers or terpolymers. Specifically, they are polymers of α-olefins such as low-density polyethylene (LDPE), high-density polyethylene (HDPE), and polypropylene (PP). The number average molecular weight of the wax is preferably 1,000 to 30,000, more preferably 2,000 to 25,000. Within this range, the wax migrates appropriately to the surface of the molded article, resulting in an excellent balance between sliding properties and bleed-out suppression. The melting point of the wax is preferably 60 to 150° C., more preferably 70 to 140° C. If the melting point is within this range, the processability when melt-kneading the thermoplastic resin and wax will be good.

[0091] The molding composition may contain other additives, which are materials commonly used in the technical field of molded articles, such as antioxidants, light stabilizers, dispersants, metal soaps, antistatic agents, flame retardants, lubricants, fillers, and colorants other than the isoindoline compound of the present invention.

[0092] The molding composition can be produced, for example, as a masterbatch containing a high concentration of the isoindoline compound. The masterbatch is preferably prepared by, for example, melt-kneading a thermoplastic resin and a pigment composition, and then molding the mixture into any desired shape for easy use in the next step. The masterbatch is then melt-kneaded with a diluting resin (e.g., the thermoplastic resin used in the masterbatch) to form a molded product of the desired shape. Examples of the masterbatch shape include pellets, powder, and plates. To prevent aggregation of the pigment composition, it is preferable to first melt-knead the pigment composition and wax to produce a dispersion, and then melt-knead this dispersion with the thermoplastic resin to produce the masterbatch. The device used for the dispersion is preferably, for example, a blend mixer or a three-roll mill.

[0093] The molding composition can be used for, for example, plastic molded articles, sheets, films, and the like.

[0094] <Toner> The toner contains a coloring composition (pigment composition, resin). The resin in the toner is called a binder resin, and is preferably a thermoplastic resin. The toner may be a dry toner or a wet toner. For example, a dry toner can be produced by melting and kneading the pigment composition and binder resin, cooling the mixture, and then pulverizing and classifying the mixture. This is followed by a post-processing step in which additives are blended and mixed.

[0095] Examples of binder resins include styrene-p-chlorostyrene copolymers, styrene-vinyltoluene copolymers, styrene-vinylnaphthalene copolymers, styrene-(meth)acrylate copolymers, styrene-α-chloromethyl methacrylate copolymers, styrene-acrylonitrile copolymers, styrene-vinyl methyl ether copolymers, styrene-vinyl ethyl ether copolymers, styrene-vinyl methyl ketone copolymers, styrene-butadiene copolymers, styrene-isoprene copolymers, styrene-acrylonitrile-indene copolymers, polyvinyl chloride, phenolic resins, naturally modified phenolic resins, naturally resin-modified maleic acid resins, (meth)acrylic resins, polyvinyl acetate, silicone resins, polyester resins, polyurethanes, polyamide resins, furan resins, epoxy resins, xylene resins, polyvinyl butyral, terpene resins, coumarone-indene resins, and petroleum-based resins.

[0096] Among these, polyester resins and styrene copolymers are preferred, and polyester resins are more preferred. The pigment composition has particularly excellent compatibility with polyester resins, allowing the isoindoline compound to be uniformly and finely dispersed in the toner, thereby producing a high-quality toner.

[0097] The weight average molecular weight (Mw) of the polyester resin is preferably 5,000 or more, more preferably 10,000 to 1,000,000, and even more preferably 20,000 to 100,000. When a polyester resin with an appropriate Mw is used, a toner having good offset resistance and low-temperature fixability can be obtained. The acid value of the polyester resin is preferably 10 to 60 mgKOH / g, more preferably 15 to 55 mgKOH / g. When a polyester resin with an appropriate acid value is used, the release agent is easily prevented from being released, and a decrease in image density in a high-humidity environment is unlikely to occur.

[0098] The toner may further contain a charge control agent. The use of a charge control agent makes it easier to obtain a toner with a stable charge amount. The charge control agent may be selected appropriately from positive and negative charge control agents.

[0099] The toner may contain a release agent, such as hydrocarbon waxes such as polypropylene wax, polyethylene wax, and Fischer-Tropsch wax, synthetic ester waxes, and natural ester waxes such as carnauba wax and rice wax.

[0100] If necessary, lubricants, fluidizing agents, abrasives, conductivity-imparting agents, image peeling prevention agents, etc. may be added to the toner.

[0101] The toner can be used as a one-component developer or a two-component developer. The two-component developer can further contain a carrier. Examples of the carrier include magnetic powders such as iron powder, ferrite powder, and nickel powder, as well as those whose surfaces are coated with resin, etc. Examples of the resin that coats the carrier surface include styrene-(meth)acrylic acid ester copolymers, (meth)acrylic acid ester copolymers, fluorine-containing resins, silicone-containing resins, polyamide resins, ionomer resins, and polyphenylene sulfide resins.

[0102] <Paint> The paint contains a coloring composition (pigment composition, resin, solvent). Examples of the resin include thermosetting resins and thermoplastic resins. The thermosetting resin preferably has a glass transition temperature of 10°C or higher. Examples of the thermosetting resin include acrylic resin, polyester, and polyurethane. The thermosetting resin preferably has a functional group that can react with a curing agent. Examples of the functional group include a carboxyl group and a hydroxyl group. Examples of the curing agent include an isocyanate curing agent, an epoxy curing agent, an aziridine curing agent, and an amine curing agent. The thermoplastic resin is preferably a resin having a glass transition temperature of 30°C or higher. Examples of the thermoplastic resin include nitrocellulose and polyester. The thermosetting resin and the thermoplastic resin can be used in combination.

[0103] Among the solvents, examples of water-insoluble solvents include toluene, xylene, butyl acetate, methyl acetate, methyl ethyl ketone, methyl isobutyl ketone, butyl alcohol, and aliphatic hydrocarbons. Among solvents, examples of water-soluble solvents include water, monohydric alcohols, dihydric alcohols, and glycols. Examples of water-soluble solvents include ethanol, n-propanol, isopropanol, isobutanol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, and glycerin. Also included are water-dilutable monoethers derived from polyhydric alcohols. Specific examples include methoxypropanol and methoxybutanol. Also included are water-dilutable glycol ethers such as butyl glycol and butyl diglycol. When a paint contains water as a solvent, it is called an aqueous paint.

[0104] The coating material may further contain known additives.

[0105] Examples of uses of the paint include paint for metals and paint for plastics.

[0106] <Printing ink> Printing ink contains a coloring composition (pigment composition, resin, solvent). Printing ink is ink other than inkjet ink, and examples include offset printing ink, flexographic printing ink, gravure printing ink, silk screen printing ink, and color filter ink. When the solvent contains water, it is called aqueous printing ink.

[0107] Examples of the resin include rosin resin, rosin-modified phenolic resin, polyurethane, nitrocellulose, acrylic resin, styrene-acrylic resin, and petroleum resin.

[0108] Examples of the water-insoluble solvents include toluene, xylene, butyl acetate, methyl acetate, methyl ethyl ketone, methyl isobutyl ketone, butyl alcohol, and aliphatic hydrocarbons.

[0109] Examples of water-soluble solvents include ethanol, n-propanol, isopropanol, isobutanol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, and glycerin. Other examples include water-dilutable monoethers derived from polyhydric alcohols, such as methoxypropanol and methoxybutanol. Other examples include water-dilutable glycol ethers such as butyl glycol and butyl diglycol.

[0110] The printing ink may further contain a lustrous material. The lustrous material is a particle having an average thickness of 0.5 to 10 μm and an average particle diameter of 5 to 50 μm, and examples thereof include metal flakes, mica, and coated glass flakes. Examples of metal flakes include aluminum flakes and gold powder. Examples of mica include ordinary mica and coated mica. Examples of coated glass flakes include glass flakes coated with a metal oxide such as titanium oxide.

[0111] The printing ink may further contain known additives.

[0112] <Inkjet ink> Inkjet inks contain a pigment composition and a resin, and preferably further contain a solvent. Inkjet inks can be broadly classified into (solvent-based) inkjet inks, aqueous inkjet inks, and solvent-free inkjet inks depending on whether or not they contain a solvent and the type of solvent. The following description will focus on aqueous inkjet inks.

[0113] The resin used in aqueous inkjet ink is important for ensuring the ink adheres well to the substrate. Examples of resin types include acrylic resins, styrene-acrylic resins, polyester resins, polyamide resins, and polyurethane resins. Resin forms include water-soluble resins and emulsion particles. Among these, emulsion particles are preferred. Emulsion particles include single-component particles and core-shell particles, and any type can be selected and used. The use of emulsion particles facilitates the reduction of the viscosity of aqueous inkjet inks, making it easy to obtain recorded materials with excellent water resistance. The acidic functional groups of the resin can be neutralized, if necessary, with a pH adjuster such as ammonia, various amines, or various inorganic alkalis.

[0114] Examples of solvents include water-insoluble solvents, water, and water-soluble solvents. Examples of water-soluble solvents include glycol ethers and diols. These solvents penetrate substrates very quickly, even into low-absorbency or non-absorbent substrates such as coated paper, art paper, vinyl chloride sheets, films, and fabrics. This allows for fast drying during printing, resulting in accurate printing. Furthermore, due to their high boiling points, they also function as wetting agents.

[0115] The water-soluble solvent is important for preventing drying and solidification at the nozzle portion of the printer head of the aqueous inkjet ink and for achieving ink ejection stability. Examples of the water-soluble solvent include ethylene glycol, diethylene glycol, propylene glycol, triethylene glycol, polyethylene glycol, glycerin, tetraethylene glycol, dipropylene glycol, ketone alcohol, diethylene glycol monobutyl ether, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, 1,2-hexanediol, N-methyl-2-pyrrolidone, substituted pyrrolidone, 2,4,6-hexanetriol, tetrafurfuryl alcohol, and 4-methoxy-4-methylpentanone.

[0116] The inkjet ink may further contain additives such as a drying accelerator, a penetrant, a preservative, a chelating agent, and a pH adjuster.

[0117] Inkjet ink is prepared by blending and mixing the various materials. Mixing can be performed using a blade stirrer, various dispersers, emulsifiers, etc. The order in which the materials are added and the mixing method are optional.

[0118] After mixing, the inkjet ink is preferably filtered or centrifuged to remove coarse particles, which improves the ejection properties from the inkjet printer. Filtration and centrifugation can be performed by known methods. Inkjet ink can be used in various inkjet systems, including, for example, charge control systems, continuous jet systems such as spray systems, piezo systems, thermal systems, and electrostatic suction systems. [Example]

[0119] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In the following examples, "%" in the compositions means "% by mass."

[0120] (Synthesis Example 1) Synthesis of DA intermediate In a nitrogen atmosphere, 12 g of biomass-derived maleic anhydride was dissolved in diethyl ether (250 mL) in a reactor equipped with a stirrer, and 10 g of biomass-derived furan was added. The mixture was reacted at room temperature and 0.25 MPa for 24 hours. The white crude product was then filtered and dried in vacuo to obtain 20 g of a DA intermediate.

[0121] (Synthesis Example 1) Bio DII 14 g of acetic anhydride was added to 74 g of methanesulfonic acid, and 5 g of the DA intermediate was slowly added while cooling in an ice bath. The reaction mixture was stirred at room temperature for 2 hours and then heated at 80 °C for 4 hours. The reaction mixture was extracted with toluene (3 × 50 mL). The combined toluene was washed with brine and sodium bicarbonate and evaporated under reduced pressure. The resulting white powder was mixed with 13 g of urea, 6 g of ammonium nitrate, and 0.03 g of molybdenum in 10 mL of alkylbenzene. The reaction mixture was heated at 165 °C for 5 hours, after which the alkylbenzene was removed by distillation under reduced pressure. 30 mL of methanol was added, and the mixture was distilled for 15 minutes. The mixture was then cooled to room temperature and filtered. The resulting solid was dispersed in 10 mL of water, and 3 g of aqueous ammonia and 4.4 mL of 25% caustic soda were added. The solution was cooled in an ice bath, and the precipitated solid was filtered and washed with water. The resulting solid was dried under reduced pressure to identify radiocarbon C. 14 2.9 g of a compound containing the following in its molecule was obtained.

[0122] (Example 1) Synthesis of isoindoline compounds In a reaction vessel equipped with a condenser, 1.2 g of Bio-DII obtained in Synthesis Example 1, 2.7 g of barbituric acid, 19 mL of water, and 1 mL of 5% by mass acetic acid were added and heated to 90°C with stirring. After stirring for 1.5 hours, the mixture was cooled to room temperature, and the crude product was filtered off and washed with water, IPA, and water in that order. The resulting solid was then dried in an oven to obtain radiocarbon C. 14 2.7 g of an isoindoline compound containing the following in its molecule was obtained.

[0123] (Comparative Example 1) Commercially available Y139 (Fanchon Yellow 279-5139) (manufactured by Sun Chemical Co.) was purchased and used.

[0124] (mass spectrometry) The pigment compositions containing the isoindoline compounds obtained in Example 1 and Comparative Example 1 were subjected to mass spectrometry. For the analysis, 5 mg of the obtained pigment compositions were dissolved in THF and subjected to FD-MS JMS-T100GC (manufactured by JEOL). The results are shown in the table below.

[0125] [Table 1]

[0126] The results in Table 1 above show that the pigment composition of Example 1 contains 96.6% of the compound represented by formula (A-1-1) above and 3.0% of the compound represented by formula (A-3-1) above.

[0127] (TEM observation) The pigment compositions containing the isoindoline compounds obtained in Example 1 and Comparative Example 1 were observed by TEM to confirm the state of the particles. The results of TEM observation of Example 1 are shown in FIG. 1, and the results of TEM observation of Comparative Example 1 are shown in FIG. The specific surface area (BET value) of Example 1 is 74 m 2 / g, and the BET value of Comparative Example 1 was 18m 2 / g.

[0128] (Accelerator mass spectrometry (AMS method)) Tandem accelerator-based 14 Using a dedicated C-AMS device (manufactured by NEC), 14 Counting C, 13 C concentration ( 13 C / 12 C). 14 C concentration ( 14 C / 12 C) was measured. For the measurements, oxalic acid (HOxII) provided by the National Institute of Standards (NIST) was used as the standard sample. Measurements of this standard sample and a background sample were also carried out simultaneously. pMC (percent Modern Carbon) is the ratio of sample carbon to standard modern carbon. 14 C concentration ratio. The results of the AMS analysis of Example 1 and Comparative Example 1 are shown in Table 2 below.

[0129] [Table 2]

[0130] (plate ink test) Using each of the pigment compositions of Example 1 and Comparative Example 1, 1 part of the pigment composition and 4 parts of MG63 varnish were mixed in a Huber Marler, and 10 times the amount of FG79 white was added. The resulting ink was spread on paper and measured using a spectrophotometer (Datacolor 650). * a * b * C * h * The value and color intensity were measured. * a * b * C * h * The difference between the values ​​of Example 1 and Comparative Example 1 (Example 1 - Comparative Example 1) is shown in Table 3 below.

[0131] [Table 3] The color strength of the pigment composition of Example 1 was 100, and that of the pigment composition of Comparative Example 1 was 66. It was found that the color strength of the offset ink of the pigment composition of Y139 of the present invention was 34% higher than that of the commercially available pigment composition of Y139.

[0132] [1] radioactive carbon atoms 14 An isoindoline compound containing C and having a group represented by the following formula (A): [ka] (In the formula (A), R 1 ~R 4 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a phenyl group which may be substituted with an alkyl group. 2 and R 3 may be ring-closed to form a 5- to 8-membered ring. 7 ~R 8 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which may be substituted with an alkyl group. * represents a bond. [2] The isoindoline compound according to [1], wherein the isoindoline compound having a group represented by formula (A) is an isoindoline compound represented by the following formula (A-1) or the following formula (A-2): [ka] [ka] (In the formula (A-1) and the formula (A-2), R 1 ~R 4 is the above R 1 ~R 4 It has the same meaning as R 7 ~R 8 is the above R 7 ~R 8 It has the same meaning as R 9 ~R 10 is the R 7 ~R 8 Similarly, each independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which may be substituted with an alkyl group.) [3] The isoindoline compound according to [2], wherein the isoindoline compound represented by the formula (A-1) is an isoindoline compound represented by the following formula (A-1-1), or the isoindoline compound represented by the formula (A-2) is an isoindoline compound represented by the following formula (A-2-1): [ka] [ka] [4] A composition containing an isoindoline compound having a group represented by formula (A) described in [1]. [5] The composition according to [4], which is used as a pigment composition. [6] The composition according to [4], which contains at least two or more isoindoline compounds having a group represented by the formula (A). [7] The composition according to [4], which contains an isoindoline compound represented by the following formula (A-1) and an isoindoline compound represented by the following formula (A-3): [ka] [ka] (In the formula (A-1) and the formula (A-3), R 1 ~R 4 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a phenyl group which may be substituted with an alkyl group. 2 and R 3 may be ring-closed to form a 5- to 8-membered ring. 7 ~R 10 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which may be substituted with an alkyl group. [8] The composition according to [7], wherein the proportion of the isoindoline compound represented by the formula (A-3) in the composition is 0.5 to 10.0 mass %. [9] The composition according to [7], wherein the isoindoline compound represented by formula (A-1) is an isoindoline compound represented by formula (A-1-1) below, and the isoindoline compound represented by formula (A-3) is an isoindoline compound represented by formula (A-3-1) below. [ka] [ka]

[10] radioactive carbon atoms 14 A method for producing an isoindoline compound containing C and having a group represented by the following formula (A), [ka] (In the formula (A), R 1 ~R 4 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a phenyl group which may be substituted with an alkyl group. 2 and R 3 may be ring-closed to form a 5- to 8-membered ring. 7 ~R 8 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which may be substituted with an alkyl group. * represents a bond. A method for producing an isoindoline compound, comprising reacting a compound represented by the following formula (I-2) with a barbituric acid represented by the following formula (B) in an acid-free solvent or in a solvent containing at least one acid selected from the group consisting of hydrochloric acid, sulfuric acid, methanesulfonic acid, p-toluenesulfonic acid, acetic acid, triflic acid, phosphoric acid, polyphosphoric acid, pyrophosphoric acid, and nitric acid, to obtain an isoindoline compound having a group represented by the formula (A). [ka] (In the formula (I), R 1 ~R 4 is the above R 1 ~R 4 It has the same meaning as [ka] (In the formula (B), R 5 ~R 6 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which may be substituted with an alkyl group.

[11] The compound represented by the formula (I-2) is A compound represented by the following formula (PA) is obtained from a compound represented by the following formula (DA), [ka] (In the formula (DA), R 1 ~R4 is the above R 1 ~R 4 It has the same meaning as [ka] (In the formula (PA), R 1 ~R 4 is the above R 1 ~R 4 It has the same meaning as The method for producing an isoindoline compound according to

[10] , wherein the isoindoline compound represented by the formula (I-2) is obtained from the compound represented by the formula (PA).

[12] The method for producing an isoindoline compound according to

[10] , wherein the solvent is any one selected from the group consisting of HO, dimethylacetamide (DMA), dimethylformamide (DMF), dimethyl sulfoxide (DMSO), MeOH, EtOH, isopropyl alcohol (IPA), and tBuOH.

Claims

1. radioactive carbon atoms １４ an isoindoline compound represented by at least one of the following formulas (A-1) and (A-2), which contains C and has a pMC (percent modern carbon) of 1% or more; and １４ A method for producing a composition containing an isoindoline compound represented by the following formula (A-3) containing C, a step of producing the isoindoline compound represented by the formula (A-1) and the isoindoline compound represented by the formula (A-3) using a compound represented by the following formula (I-2) containing a radioactive carbon atom 14 C; A method for producing a composition, comprising: a step of producing the compound represented by formula (I-2) using raw materials in which at least one of furan and maleic anhydride is bio-derived. 【Chemistry 1】 【Chemistry 2】 【Transformation 3】 (In the formula (A-1), the formula (A-2) and the formula (A-3), R １ ~R ４ are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a phenyl group which may be substituted with an alkyl group. ２ and R ３ may close a ring to form a 5- to 8-membered ring. ７ ~R １０ are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which may be substituted with an alkyl group. 【Chemistry 4】 (In the formula (I), R １ ~R ４ is the R １ ~R ４ It has the same meaning as

2. In the reaction pathway for producing the compound represented by formula (I-2) from the furan and maleic anhydride via the compound represented by formula (DA) below and the compound represented by formula (PA) below, ammonium molybdate, urea or NH ３ and adding a compound represented by the following formula (q): 【Transformation 5】 (In the formula (DA), R １ ~R ４ is the R １ ~R ４ It has the same meaning as 【Transformation 6】 (In the formula (PA), R １ ~R ４ is the R １ ~R ４ It has the same meaning as 【Transformation 7】 (In formula (q), M ｆ＋ is NH ４ ＋ , Li ＋ , Na ＋ , K. ＋ , Mg ２＋ , Ca ２＋ , or Al ３＋ Represents.)

3. The method for producing a composition according to claim 1, wherein the proportion of the isoindoline compound represented by formula (A-3) in the composition is 0.5 to 10.0 mass%.

4. The method for producing a composition according to claim 1, wherein the isoindoline compound represented by formula (A-1) is an isoindoline compound represented by formula (A-1-1) below, and the isoindoline compound represented by formula (A-3) is an isoindoline compound represented by formula (A-3-1) below. 【Transformation 8】 【Chemistry 9】

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