Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
  • C08G59/50—Amines
  • C08G59/5046—Amines heterocyclic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/13—Phenols; Phenolates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/17—Amines; Quaternary ammonium compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/49—Phosphorus-containing compounds
  • C08K5/51—Phosphorus bound to oxygen
  • C08K5/52—Phosphorus bound to oxygen only
  • C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
  • C08K5/526—Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl compounds

Definitions

• the present invention relates to a composition, a resin composition, and a cured product.
• Patent Document 1 Compounds containing a low-molecular amino group and a cyclic ether structure, such as 2,5-bis(aminomethyl)tetrahydrofuran, are widely used as curing agents for thermosetting resins such as epoxy resins, and raw materials for polyamide resins.
• Patent Document 2 low-molecular-weight diamine compounds tend to become discolored due to air oxidation, and have the disadvantage of being discolored during production and continuing to discolor during storage, resulting in restrictions on materials that require transparency. It is known that there are drawbacks (Patent Document 3).
• the present inventor conducted a study and found that, for example, pentaerythritol tetrakis [3-(3,5 -di-tert-butyl-4-hydroxyphenyl)propionate] was blended and heat treated, it turned yellow and it was found that a sufficient antioxidant effect could not be achieved.
• the present invention aims to solve such problems, and provides a composition containing a low molecular weight compound containing an amino group and a cyclic ether structure and an antioxidant, which suppresses yellowing after heat treatment.
• the present invention aims to provide a resin composition and a cured product using the composition, as well as a resin composition and a cured product using the composition.
• the above-mentioned problems can be solved by blending an unhindered phenolic antioxidant into a low-molecular compound containing an amino group and a cyclic ether structure.
• the above problem was solved by the following means.
• ⁇ 1> A composition containing an amino group and a cyclic ether structure, a compound having a molecular weight of 1000 or less, and an unhindered phenolic antioxidant.
• ⁇ 2> The composition according to ⁇ 1>, wherein the compound containing the amino group and a cyclic ether structure and having a molecular weight of 1000 or less is represented by formula (F).
• n1 represents an integer from 0 to 3
• n2 represents an integer from 1 to 4.
• ⁇ 3> The composition according to ⁇ 1> or ⁇ 2>, further comprising a phosphorus antioxidant.
• the mass ratio of the unhindered phenolic antioxidant to the phosphorus antioxidant is 0.6 to 1.4
• ⁇ 5> The composition according to any one of ⁇ 1> to ⁇ 4>, wherein the content of the unhindered phenolic antioxidant is 100 to 5000 ppm by mass.
• ⁇ 6> Furthermore, it contains a phosphorus-based antioxidant, and the mass ratio of the unhindered phenol-based antioxidant to the phosphorus-based antioxidant (unhindered phenol-based antioxidant/phosphorus-based antioxidant) is 0. 6 to 1.4, and the content of the unhindered phenolic antioxidant is 100 to 5000 ppm by mass, the composition according to ⁇ 1>.
• a resin composition comprising the composition according to any one of ⁇ 1> to ⁇ 6> and a thermosetting resin.
• ⁇ 8> The resin composition according to ⁇ 7>, wherein the thermosetting resin contains an epoxy resin.
• ⁇ 9> A cured product of the resin composition according to ⁇ 7> or ⁇ 8>.
• the present invention provides a composition containing a low molecular weight compound containing an amino group and a cyclic ether structure and an antioxidant, which suppresses yellowing after heat treatment, and a resin using the composition. Now we can provide compositions and cured products.
• this embodiment a mode for carrying out the present invention (hereinafter simply referred to as "this embodiment") will be described in detail.
• the present embodiment below is an illustration for explaining the present invention, and the present invention is not limited only to this embodiment.
• " ⁇ " is used to include the numerical values described before and after it as a lower limit value and an upper limit value.
• various physical property values and characteristic values are assumed to be at 23° C. unless otherwise stated.
• the description that does not indicate substituted or unsubstituted includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group).
• alkyl group includes not only an alkyl group without a substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
• the weight average molecular weight and number average molecular weight are polystyrene equivalent values measured by GPC (gel permeation chromatography) unless otherwise specified. If the measurement methods, etc. explained in the standards shown in this specification differ from year to year, unless otherwise stated, they shall be based on the standards as of January 1, 2022.
• the composition of this embodiment includes a compound containing an amino group and a cyclic ether structure and having a molecular weight of 1000 or less (herein sometimes referred to as a "low molecular compound containing an amino group and a cyclic ether structure”), It is characterized by containing a non-hindered phenolic antioxidant. With such a configuration, yellowing after heat treatment can be effectively suppressed. In order to prevent oxidation of amine compounds, it has been conventional practice to add antioxidants to amine compounds.
• the composition of this embodiment contains an amino group and a cyclic ether structure and a compound having a molecular weight of 1000 or less (a low molecular compound containing an amino group and a cyclic ether structure).
• the molecular weight of the low molecular weight compound containing an amino group and a cyclic ether structure is preferably 80 or more, more preferably 90 or more, even more preferably 100 or more, and even more preferably 110 or more. is more preferably 120 or more, further preferably 800 or less, more preferably 600 or less, even more preferably 400 or less, even more preferably 300 or less. It is preferably 200 or less, even more preferably 180 or less, and even more preferably 150 or less.
• the low molecular compound containing an amino group and a cyclic ether structure preferably has 1 to 4 amino groups in one molecule, more preferably 2 to 4, and has 2 or 4 amino groups. It is even more preferable to have two.
• the amino group may be bonded directly to the cyclic ether structure or may be bonded via a linking group.
• the amino group is preferably bonded to the cyclic ether structure via a linking group, and the aliphatic hydrocarbon group (preferably carbon number The bonding is more preferably via an alkylene group (preferably an alkylene group having 1 to 5 carbon atoms).
• a group other than the group having an amino group may be bonded to the cyclic ether structure. Examples of groups other than the group having an amino group include a hydroxyl group, an alkyl group (preferably an alkyl group having 1 to 5 carbon atoms), and a halogen atom.
• the cyclic ether structure of the low molecular weight compound containing an amino group and a cyclic ether structure is preferably a 3-membered ring, a 4-membered ring, a 5-membered ring or a 6-membered ring, more preferably a 5-membered ring or a 6-membered ring, and a 5-membered ring. is even more preferable.
• cyclic ether structure possessed by a low molecular compound containing an amino group and a cyclic ether structure include a pyran ring, a furan ring, an oxirane ring, an oxetane ring, a tetrahydropyran ring, and a tetrahydrofuran ring, with a tetrahydrofuran ring being preferred.
• the low molecular weight compound containing an amino group and a cyclic ether structure is preferably represented by formula (F).
• formula (F) n1 represents an integer from 0 to 3
• n2 represents an integer from 1 to 4.
• n1 is preferably an integer of 1 to 3, more preferably 1 or 2, and even more preferably 1.
• n2 is preferably an integer of 2 to 4, more preferably 2 or 4, and even more preferably 2.
• each n1 may be the same or different, but preferably the same.
• the group represented by -((CH 2 ) n1 NH 2 ) n2 is preferably bonded to at least one of the 2-position and the 5-position.
• the compound represented by formula (F) is preferably a compound (H-AMF) represented by formula (F1).
• the composition of this embodiment usually has a low molecular compound containing an amino group and a cyclic ether structure as a main component, and the content thereof is preferably 95% by mass or more, and 98% by mass or more in the composition. It is more preferably at least 99% by mass, even more preferably at least 99% by mass.
• the upper limit of the low molecular weight compound containing an amino group and a cyclic ether structure in the composition of this embodiment is when all components other than the unhindered phenolic antioxidant are low molecular weight compounds containing an amino group and a cyclic ether structure. means.
• the composition of this embodiment may contain only one type of low molecular compound containing an amino group and a cyclic ether structure, and may contain two or more types. When two or more types are included, it is preferable that the total amount falls within the above range. In this embodiment, it is preferable that 99% by mass or more of the low molecular weight compounds containing an amino group and a cyclic ether structure contained in the composition are the same compound.
• the composition of this embodiment contains a less hindered phenolic antioxidant.
• Phenolic antioxidants include, for example, hindered phenolic antioxidants in which hydrogen atoms at both ortho positions of the phenol hydroxyl group are substituted with sterically bulky groups, and hydrogen atoms at one ortho position of the phenol hydroxyl group.
• Semi-hindered phenolic antioxidants in which the atom is substituted with a sterically bulky group and the hydrogen atom at the other ortho position is substituted with a methyl group, and the hydrogen atom at one ortho position of the phenolic hydroxyl group.
• Unhindered phenolic antioxidants are known in which the hydrogen atom is substituted with a sterically bulky group, and the other hydrogen atom at the ortho position is not substituted. In the present embodiment, among these, by using an unhindered phenolic antioxidant, it is possible to effectively suppress an increase in the YI value of a low-molecular compound containing an amino group and a cyclic ether structure.
• the sterically bulky group refers to, for example, a branched alkyl group other than a linear alkyl group or an aromatic ring group.
• tertiary alkyl groups such as t-butyl group, t-pentyl group, t-hexyl group; secondary alkyl groups such as i-propyl group, sec-butyl group, sec-pentyl group; i-butyl group; and branched primary alkyl groups such as i-pentyl group; cycloalkyl groups such as cyclohexyl group and cyclopentyl group; and aromatic ring groups such as phenyl group, benzyl group, and naphthyl group.
• the unhindered phenolic antioxidant is preferably a compound having the following partial structure, more preferably a compound having 2 to 5 of the following partial structures, and a compound having 2 to 4 of the following partial structures. More preferred are compounds having two to three of the following partial structures.
• the wavy line is a bonding site with another part.
• the molecular weight of the unhindered phenol antioxidant is preferably 300 or more, preferably 1000 or less, and more preferably 800 or less.
• unhindered phenolic antioxidants include 4,4'-thiobis(3-methyl-6-t-butyl)phenol (for example, Nocrac 300 manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd.), 1,1,3 -tris-(2-methyl-4-hydroxy-5-t-butylphenyl)butane (e.g. Adeka Stab AO-30 from Adeka), 4,4'-butylidenebis(3-methyl-6-t-butyl)phenol (e.g. Examples include Adeka Stab AO-40) manufactured by Adeka Corporation.
• the content of the unhindered phenolic antioxidant in the composition of the present embodiment is preferably 100 mass ppm or more, more preferably 200 mass ppm or more when the composition is 100 parts by mass. , more preferably 300 mass ppm or more, even more preferably 400 mass ppm or more, even more preferably 600 mass ppm or more, and even more preferably 800 mass ppm or more. By setting it above the lower limit, the YI value of the composition or a cured product using the composition tends to be lower. Further, the content of the unhindered phenolic antioxidant in the composition of the present embodiment is preferably 5000 mass ppm or less, and preferably 4000 mass ppm or less, when the composition is 100 parts by mass.
• the resin composition of this embodiment may contain only one type of unhindered phenolic antioxidant, or may contain two or more types of unhindered phenolic antioxidant. When two or more types are included, it is preferable that the total amount falls within the above range.
• the composition of this embodiment may or may not contain a hindered phenolic antioxidant other than the unhindered phenolic antioxidant.
• the composition of the present embodiment preferably does not substantially contain any hindered phenolic antioxidants other than unhindered phenolic antioxidants. "Substantially free” means that the content of hindered phenolic antioxidants other than unhindered phenolic antioxidants contained in the composition is 10% by mass of the content of unhindered phenolic antioxidants. It is preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 1% by mass or less.
• the composition of this embodiment may contain a phosphorous antioxidant.
• a phosphorous antioxidant By including a phosphorous antioxidant, it is possible to effectively suppress an increase in the YI value of a low-molecular compound containing an amino group and a cyclic ether structure.
• the phosphorus-based antioxidant is not particularly limited as long as it contains a phosphorus atom.
• Specific examples of phosphorus-based antioxidants include phosphorus oxoacids such as phosphoric acid, phosphonic acid, phosphorous acid, phosphinic acid, and polyphosphoric acid; acidic pyrolines such as sodium acid pyrophosphate, potassium acid pyrophosphate, and calcium acid pyrophosphate. Acid metal salts; Phosphates of Group 1 or Group 2B metals such as potassium phosphate, sodium phosphate, cesium phosphate, zinc phosphate; Examples include phosphate compounds, phosphite compounds, and phosphonite compounds; Particularly preferred are compounds.
• the phosphorus-based antioxidant used in this embodiment preferably has an aromatic ring, more preferably has a di- or triarylphosphite structure, and is even more preferably represented by formula (P).
• Formula (P) (In formula (P), Rp each independently represents an aryl group having 6 to 30 carbon atoms.) Rp may be an aryl group having a substituent, and an aryl group substituted with an alkyl group is preferable.
• the aryl group is preferably a phenyl group.
• the alkyl group as the substituent is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a butyl group, and even more preferably a t-butyl group.
• Examples of the phosphorus antioxidant represented by formula (P) include ADEKA STAB 2112, ADEKA STAB 1178, ADEKA STAB TPP, and the like.
• phosphorus-based antioxidants having a pentaerythritol diphosphite structure can also be preferably used, and the details of these can be exemplified by compounds described in International Publication No. 2013/088796. .
• the content thereof is preferably 100 mass ppm or more, more preferably 300 mass ppm or more, based on 100 parts by mass of the composition. It is more preferably 700 mass ppm or more, and may be 1200 mass ppm or more. By setting it at or above the lower limit, it tends to be possible to more effectively suppress the increase in the YI value of the cured product of the composition or resin composition.
• the upper limit of the content of the phosphorus antioxidant is preferably 5000 mass ppm or less, more preferably 3000 mass ppm or less, and 2500 mass ppm or less based on 100 parts by mass of the composition. It is more preferable that the amount is 1,800 mass ppm or less.
• the composition of this embodiment may contain only one type of phosphorus antioxidant, or may contain two or more types of phosphorus antioxidant. When two or more types are included, it is preferable that the total amount falls within the above range.
• the composition of the present embodiment also has a mass ratio of the unhindered phenolic antioxidant to the phosphorus antioxidant (unhindered phenolic antioxidant/phosphorus antioxidant) of 0.2 or more. It is preferably at least 0.3, more preferably at least 0.4, even more preferably at least 0.6, even more preferably at least 0.8, Further, it is preferably 3.0 or less, more preferably 1.8 or less, even more preferably 1.4 or less, and even more preferably 1.2 or less. By setting the above lower limit or more and below the upper limit, it tends to be possible to more effectively suppress the increase in the YI value of the cured product of the composition or resin composition.
• the total amount of the unhindered phenolic antioxidant and the phosphorus antioxidant is preferably 500 mass ppm or more, and 900 mass ppm or more, based on 100 parts by mass of the composition. It is more preferable that it is, it is still more preferable that it is 1100 mass ppm or more, and it may be 1600 mass ppm or more. By setting it at or above the lower limit, it tends to be possible to more effectively suppress the increase in the YI value of the cured product of the composition or resin composition.
• the upper limit of the content of the phosphorus antioxidant is preferably 3000 mass ppm or less, more preferably 2800 mass ppm or less, and 2400 mass ppm or less, based on 100 parts by mass of the composition. There may be. By setting it below the above-mentioned upper limit, there is a tendency that an increase in the YI value of the cured product of the composition or resin composition can be more effectively suppressed.
• the composition of this embodiment may consist only of a low molecular weight compound containing an amino group and a cyclic ether structure and an unhindered phenol antioxidant, or may contain other components.
• Other components include modifying components such as plasticizers, reactive or non-reactive diluents, fluidity adjusting components such as thixotropic agents, pigments, tackifiers, etc., anti-cissing agents, flow spreading agents, etc. Examples include antifoaming agents, antifoaming agents, ultraviolet absorbers, light stabilizers, and curing accelerators.
• the composition of this embodiment can be effectively used in various applications where low-molecular amine compounds are used. Specifically, it can be widely used as a curing agent for thermosetting resins, a raw material for polyamide resins and other resins, a raw material for adhesives, and the like. As an example of the use of a curing agent for a thermosetting resin, the composition of this embodiment may be used instead of the curing agent described in International Publication No. 2016/158871 and JP 2012-153857.
• composition of the present embodiment is a composition substantially consisting only of a low molecular compound containing an amino group and a cyclic ether structure and an unhindered phenolic antioxidant.
• substantially means that components other than low molecular weight compounds containing amino groups and cyclic ether structures and unhindered phenolic antioxidants are low molecular weight compounds containing amino groups and cyclic ether structures and unhindered phenolic antioxidants.
• 5% by mass or less of the total amount of the agent preferably 3% by mass or less, more preferably 1% by mass or less, even more preferably 0.1% by mass or less, 0.
• the content is .01% by mass or less, even more preferably that it is 0.001% by mass or less, and it is especially more preferable that it is not actively blended. It is preferable that such a composition consisting essentially of a low molecular weight compound containing an amino group and a cyclic ether structure and an unhindered phenolic antioxidant is sealed in a container as it is. Such a composition is sold, for example, as a reagent for a low-molecular compound containing an amino group and a cyclic ether structure.
• the resin composition of this embodiment includes the composition of this embodiment and a thermosetting resin.
• the thermosetting resin preferably contains one or more selected from the group consisting of epoxy resin, benzoxazine resin, phenol resin, unsaturated polyester resin, maleimide resin, thermosetting polyimide resin, and silicone resin. More preferably, it contains a resin.
• the epoxy resin the description in paragraph 0036 of International Publication No. 2016/158871 can be referred to, and this content is incorporated herein.
• the resin composition of the present embodiment may include modifying components such as fillers and plasticizers, reactive or non-reactive diluents, fluidity adjusting components such as thixotropic agents, pigments, and adhesives.
• Components such as imparting agents and additives such as anti-cissing agents, spreading agents, antifoaming agents, ultraviolet absorbers, light stabilizers, and curing accelerators can be used within the range that does not impair the effects of the present invention.
• the resin composition of this embodiment is, for example, a paint or adhesive for concrete, cement mortar, various metals, leather, glass, rubber, plastic, wood, cloth, paper, etc.; adhesive tape for packaging, adhesive label, frozen food label. , removable labels, POS labels, adhesive wallpapers, adhesives for adhesive flooring; processed papers such as art paper, lightweight coated paper, cast coated paper, coated paperboard, carbonless copiers, impregnated paper; natural fibers, synthetic fibers, It can be used in a wide range of applications, including fiber treatment agents such as binding agents, fraying prevention agents, and processing agents for glass fibers, carbon fibers, and metal fibers; building materials such as sealants, cement admixtures, and waterproofing materials.
• fiber treatment agents such as binding agents, fraying prevention agents, and processing agents for glass fibers, carbon fibers, and metal fibers
• building materials such as sealants, cement admixtures, and waterproofing materials.
• the cured product of this embodiment is a cured product of the resin composition of this embodiment.
• the form of the cured product may be a film, a sheet, or any other form.
• 1,3-BAC 1,3-bis(aminomethyl)cyclohexane, manufactured by Mitsubishi Gas Chemical Co., Ltd.
• AO-30 Manufactured by ADEKA, ADEKA STAB, unhindered phenolic antioxidant
• AO-40 Manufactured by ADEKA, ADEKA STAB, unhindered phenolic antioxidant
• AO-50 Manufactured by ADEKA, ADEKA STAB AO-50, hindered phenolic antioxidant
• AO-60 Manufactured by ADEKA, ADEKA STAB AO-60, hindered phenolic antioxidant
• Phosphorous oxidizing agent ADEKA STAB 2112, manufactured by ADEKA
• Example 1 As a diamine, Composition 1 was obtained by blending 1000 parts by mass of the above H-AMF with 1000 mass ppm of unhindered amine antioxidant (A-30) without blending the phosphorous antioxidant. The obtained composition was heated at 160° C. for 30 minutes, and after heating, the composition was cooled to room temperature by air cooling, and the YI value of the composition was measured. The YI value was measured using a spectroscopic haze meter SH-7000 manufactured by Nippon Denshoku Industries Co., Ltd.
• Reference Example 1 a composition containing only H-AMF and not containing a phosphorus antioxidant and a unhindered amine antioxidant
• the YI value was measured.
• the difference ( ⁇ YI) between the YI value of the composition 1 and the composition of Reference Example 1 was -5.3, which was much lower than that of the composition of Reference Example 1.
• Example 2 Composition 2 was obtained in the same manner as in Example 1 except that the content of the unhindered amine antioxidant (A-30) was changed to 1500 ppm by mass. Composition 1 in Example 1 was changed to Composition 2, and the other procedures were the same, and the obtained ⁇ YI value was -4.3, which was a much higher YI value than the composition of Reference Example 1. It got lower.
• Example 3 Composition 3 was obtained in the same manner as in Example 1 except that the content of the unhindered amine antioxidant (A-30) was changed to 2000 ppm by mass. Composition 1 in Example 1 was changed to Composition 3, and the other procedures were the same, and the obtained ⁇ YI value was -2.6, which was a much higher YI value than the composition of Reference Example 1. It got lower.
• Example 4 Composition 4 was obtained in the same manner as in Example 1 except that the type of unhindered amine antioxidant was changed from Adekastab A-30 to Adekastab AO-40. Composition 1 in Example 1 was changed to Composition 4, and the other procedures were carried out in the same manner. The obtained ⁇ YI value was -5.0, which was a much higher YI value than the composition of Reference Example 1. It got lower.
• Example 5 Composition 5 was obtained in the same manner as in Example 4 except that the content of the unhindered amine antioxidant (A-40) was changed to 1500 ppm by mass. Composition 4 in Example 4 was changed to Composition 5, and the other procedures were carried out in the same manner. The obtained ⁇ YI value was -3.5, which was a much higher YI value than the composition of Reference Example 1. It got lower.
• Example 6 In Example 4, the content of the unhindered amine antioxidant (A-40) was changed to 2000 ppm by mass, and the same procedure was repeated to obtain Composition 6. Composition 4 in Example 4 was changed to Composition 6, and the other procedures were carried out in the same manner. The obtained ⁇ YI value was -3.0, which was a much higher YI value than the composition of Reference Example 1. It got lower.
• Example 7 In Composition 1 of Example 1, 500 mass ppm of a phosphorous antioxidant was further added, and the other procedures were the same to obtain Composition 7. Composition 1 in Example 1 was changed to Composition 7, and the other procedures were carried out in the same manner. The obtained ⁇ YI value was -5.7, which was a much higher YI value than the composition of Reference Example 1. It got lower.
• Example 8 In Composition 2 of Example 2, 500 mass ppm of a phosphorous antioxidant was further blended, and the other procedures were the same to obtain Composition 8. Composition 2 in Example 2 was changed to Composition 8, and the other procedures were carried out in the same manner. The obtained ⁇ YI value was -4.9, which was a much higher YI value than the composition of Reference Example 1. It got lower.
• Example 9 In Composition 4 of Example 4, 500 mass ppm of a phosphorous antioxidant was further added, and the other procedures were the same to obtain Composition 9. Composition 4 in Example 4 was changed to Composition 9, and the other procedures were carried out in the same manner. The obtained ⁇ YI value was -5.0, which was a much higher YI value than the composition of Reference Example 1. It got lower.
• Example 10 In Composition 5 of Example 5, 500 mass ppm of a phosphorous antioxidant was further blended, and the other procedures were carried out in the same manner to obtain Composition 10. Composition 5 in Example 5 was changed to Composition 10, and the other procedures were carried out in the same manner. The obtained ⁇ YI value was -5.5, which was a much higher YI value than the composition of Reference Example 1. It got lower.
• Example 11 In Example 1, the content of the unhindered amine antioxidant (A-30) was changed to 500 mass ppm, and 1000 mass ppm of phosphorus antioxidant was added, and the other procedures were repeated in the same manner to prepare a composition. I got 11. Composition 1 in Example 1 was changed to Composition 11, and the other procedures were carried out in the same manner. The obtained ⁇ YI value was -5.2, and the YI value was much higher than that of the composition of Reference Example 1. It got lower.
• A-30 unhindered amine antioxidant
• Example 12 Composition 12 was obtained in the same manner as in Example 1, except that 1000 mass ppm of a phosphorous antioxidant was added. Composition 1 in Example 1 was changed to Composition 12, and the other procedures were the same, and the obtained ⁇ YI value was -7.4, which was a much higher YI value than the composition of Reference Example 1. It got lower.
• Example 13 In Composition 4 of Example 4, the content of the unhindered amine antioxidant (A-40) was changed to 500 mass ppm, and 1000 mass ppm of phosphorus antioxidant was added, but the other procedures were the same. As a result, Composition 13 was obtained. Composition 4 in Example 4 was changed to Composition 13, and the other procedures were carried out in the same manner. The obtained ⁇ YI value was -6.3, which was a much higher YI value than the composition of Reference Example 1. It got lower.
• A-40 unhindered amine antioxidant
• Example 14 In Composition 4 of Example 4, the content of the phosphorous antioxidant was further changed to 1000 mass ppm, and the other procedures were carried out in the same manner to obtain Composition 14. Composition 4 in Example 4 was changed to Composition 14, and the other procedures were carried out in the same manner. The obtained ⁇ YI value was -7.6, which was a much higher YI value than the composition of Reference Example 1. It got lower.
• Example 15 Composition 15 was obtained in the same manner as in Example 11 except that the content of the phosphorus antioxidant was changed to 1500 ppm by mass. Composition 14 in Example 11 was changed to Composition 15, and the other procedures were carried out in the same manner. The obtained ⁇ YI value was -6.2, which was a much higher YI value than the composition of Reference Example 1. It got lower.
• Example 16 Composition 16 was obtained in the same manner as in Example 13 except that the content of the phosphorus antioxidant was changed to 1500 ppm by mass. Composition 13 in Example 13 was changed to Composition 16, and the other procedures were carried out in the same manner. The obtained ⁇ YI value was -6.5, which was a much higher YI value than the composition of Reference Example 1. It got lower.
• Comparative example 1 Comparative composition 1 was obtained by blending unhindered amine antioxidant (A-30, 2000 mass ppm) with 100 parts by mass of the above 1,3-BAC as a diamine without blending a phosphorus antioxidant. . The obtained comparative composition 1 was heated at 160° C. for 30 minutes, and the YI value after heating was measured. Furthermore, the composition of Reference Example 2 (a composition containing only 1,3-BAC and not containing a phosphorus antioxidant and a unhindered amine antioxidant) was similarly heated at 160°C for 30 minutes. The subsequent YI value was measured. The difference ( ⁇ YI) between the YI value of Comparative Composition 1 and the composition of Reference Example 2 was 1.9, and the YI value was higher than that of the composition of Reference Example 2.
• Comparative example 2 In Comparative Example 1, Comparative Composition 2 was obtained by replacing the unhindered amine antioxidant (A-30, 2000 mass ppm) with the unhindered amine antioxidant (A-40, 2000 mass ppm). Comparative composition 1 in Comparative Example 1 was changed to Comparative Composition 2, and the other procedures were carried out in the same manner. The obtained ⁇ YI value was 4.8, and the YI value was significantly higher than that of the composition of Reference Example 2. It has become expensive.

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