JP2024080774A - Foaming composition, method for producing foaming composition, and method for producing foam - Google Patents
Foaming composition, method for producing foaming composition, and method for producing foam Download PDFInfo
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- JP2024080774A JP2024080774A JP2022193994A JP2022193994A JP2024080774A JP 2024080774 A JP2024080774 A JP 2024080774A JP 2022193994 A JP2022193994 A JP 2022193994A JP 2022193994 A JP2022193994 A JP 2022193994A JP 2024080774 A JP2024080774 A JP 2024080774A
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- 239000000203 mixture Substances 0.000 title claims abstract description 107
- 238000005187 foaming Methods 0.000 title claims abstract description 87
- 239000006260 foam Substances 0.000 title claims abstract description 74
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 34
- 229920005989 resin Polymers 0.000 claims abstract description 35
- 239000011347 resin Substances 0.000 claims abstract description 35
- 238000002156 mixing Methods 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims description 114
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims description 34
- 239000004088 foaming agent Substances 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000001118 alkylidene group Chemical group 0.000 claims description 11
- 239000002861 polymer material Substances 0.000 claims description 7
- -1 pyrazolone compound Chemical class 0.000 abstract description 197
- 239000000463 material Substances 0.000 abstract description 11
- 239000004604 Blowing Agent Substances 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 46
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- 244000043261 Hevea brasiliensis Species 0.000 description 15
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- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 4
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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- GVUNLYBSNQOHBD-UHFFFAOYSA-N 3-propyl-1,4-dihydropyrazol-5-one Chemical compound CCCC1=NNC(=O)C1 GVUNLYBSNQOHBD-UHFFFAOYSA-N 0.000 description 3
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- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 description 3
- 235000019399 azodicarbonamide Nutrition 0.000 description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 3
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
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- NBOCQTNZUPTTEI-UHFFFAOYSA-N 4-[4-(hydrazinesulfonyl)phenoxy]benzenesulfonohydrazide Chemical compound C1=CC(S(=O)(=O)NN)=CC=C1OC1=CC=C(S(=O)(=O)NN)C=C1 NBOCQTNZUPTTEI-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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- 125000005110 aryl thio group Chemical group 0.000 description 2
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- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical group CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- 125000001391 thioamide group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- XJUNLJFOHNHSAR-UHFFFAOYSA-J zirconium(4+);dicarbonate Chemical compound [Zr+4].[O-]C([O-])=O.[O-]C([O-])=O XJUNLJFOHNHSAR-UHFFFAOYSA-J 0.000 description 1
Landscapes
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Abstract
【課題】本発明の目的は、優れた発泡倍率と微細なセル径を有する発泡体の製造方法を提供することである。【解決手段】高分子材料（樹脂）と特定のピラゾロン系化合物とを混合して発泡用組成物を得る工程（Ａ）、前記工程（Ａ）で得られた発泡用組成物に、発泡剤を混合し、発泡組成物を得る工程（Ｂ）、並びに前記工程（Ｂ）で得られた発泡組成物を発泡させて発泡体を得る工程（Ｃ）。【選択図】なし[Problem] The object of the present invention is to provide a method for producing a foam having an excellent expansion ratio and a fine cell diameter. [Solution] The method comprises the steps of: (A) mixing a polymeric material (resin) with a specific pyrazolone compound to obtain a foaming composition; (B) mixing a blowing agent with the foaming composition obtained in the step (A) to obtain a foaming composition; and (C) foaming the foaming composition obtained in the step (B) to obtain a foam. [Selected Figure] None
Description
本発明は、発泡用組成物、発泡組成物の製造方法、及び発泡体の製造方法に関する。 The present invention relates to a foaming composition, a method for producing a foaming composition, and a method for producing a foam.
発泡体は、軽量性及び断熱性等に優れていることから、自動車外装・内装部品、家電部品等で広く使用されている。 Because of their lightweight and insulating properties, foams are widely used in automobile exterior and interior parts, home appliance parts, etc.
上記発泡体は、一般的にゴムや樹脂に発泡剤を添加させることで製造することができるが、軽量性、及び断熱性等の発泡体性能の更なる向上に加え、発泡剤の使用量の削減による経済的制約等が求められており、優れた発泡倍率を有する発泡体の需要が高い。 The above foams can generally be produced by adding a foaming agent to rubber or resin, but in addition to further improvements in foam performance such as light weight and insulation, there is a demand for economic constraints such as reducing the amount of foaming agent used, and so there is a high demand for foams with excellent expansion ratios.
また、発泡体の機械強度の観点から、微細な平均セル径を有する発泡体の需要も高い。 In addition, from the perspective of the mechanical strength of the foam, there is a high demand for foams with fine average cell diameters.
特許文献１は、化学発泡剤と特定の平均粒子径を有するマイクロカプセルとを併用する発泡剤を開示している。 Patent Document 1 discloses a foaming agent that uses a chemical foaming agent in combination with microcapsules having a specific average particle size.
特許文献２は、本出願人が提供する技術であり、高分子材料用発泡倍率向上剤を開示している。 Patent Document 2 is a technology provided by the present applicant, and discloses a foaming ratio enhancer for polymeric materials.
本発明の目的は、優れた発泡倍率、及び微細な平均セル径を有する発泡体を得ることができる発泡用組成物を提供することである。 The object of the present invention is to provide a foaming composition capable of producing a foam having an excellent expansion ratio and a fine average cell diameter.
本発明の目的は、優れた発泡倍率、及び微細な平均セル径を有する発泡体を得ることができる発泡組成物の製造方法を提供することである。 The object of the present invention is to provide a method for producing a foaming composition that can produce a foam having an excellent expansion ratio and a fine average cell diameter.
本発明の目的は、優れた発泡倍率、及び微細な平均セル径を有することができる発泡体の製造方法を提供することである。 The object of the present invention is to provide a method for producing a foam that has an excellent expansion ratio and a fine average cell diameter.
本発明者らは、前記課題を解決するために鋭意検討を重ねた結果、以下の工程で製造された発泡体が、優れた発泡倍率、及び微細な平均セル径を有することを見出した。 As a result of extensive research into solving the above problems, the inventors have found that a foam produced by the following process has an excellent expansion ratio and a fine average cell diameter.
（Ａ）高分子材料（樹脂）と特定のピラゾロン系化合物とを混合して発泡用組成物を得る工程、
（Ｂ）前記工程（Ａ）で得られた発泡用組成物に、化学発泡剤を混合し、発泡組成物を得る工程、及び
（Ｃ）前記工程（Ｂ）で得られた発泡組成物を発泡させて発泡体を得る工程。
(A) a step of mixing a polymeric material (resin) with a specific pyrazolone compound to obtain a foaming composition;
(B) a step of mixing a chemical foaming agent with the foaming composition obtained in the step (A) to obtain a foaming composition; and (C) a step of foaming the foaming composition obtained in the step (B) to obtain a foam.
すなわち、本発明は、以下に示す発泡用組成物、発泡組成物の製造方法、及び発泡体の製造方法を提供する。 That is, the present invention provides the following foaming composition, method for producing a foamed composition, and method for producing a foamed product.
項１．
樹脂、並びに
式（１）及び（２）で表される化合物、並びに該化合物の塩から選ばれる少なくとも一種の化合物：
Item 1.
A resin, and at least one compound selected from compounds represented by formulas (1) and (2) and salts of said compounds:
を含む、発泡用組成物（但し、発泡剤を含まない）。
1. A foaming composition comprising, but not including a blowing agent.
項２．
高分子材料、並びに、
式（１）及び（２）で表される化合物、並びに該化合物の塩から選ばれる少なくとも一種の化合物：
Item 2.
Polymer materials, and
At least one compound selected from the compounds represented by formulas (1) and (2) and salts of said compounds:
のみからなる、発泡用組成物。
A foaming composition comprising only the above-mentioned.
項３．
発泡組成物の製造方法であって、
（Ａ）樹脂、並びに、式（１）及び（２）で表される化合物、並びに該化合物の塩から選ばれる少なくとも一種の化合物を混合して、発泡用組成物を得る工程、及び
（Ｂ）前記工程（Ａ）で得られた発泡用組成物に、化学発泡剤を混合し、発泡組成物を得る工程
を含む、製造方法。
Item 3.
A method for producing a foam composition, comprising the steps of:
A production method comprising: (A) a step of mixing a resin and at least one compound selected from the group consisting of compounds represented by formulas (1) and (2) and salts of said compounds to obtain a foaming composition; and (B) a step of mixing a chemical foaming agent with the foaming composition obtained in the step (A) to obtain a foaming composition.
項４．
発泡体の製造方法であって、
請求項３に記載の製造方法に、更に
（Ｃ）前記工程（Ｂ）で得られた発泡組成物を、発泡させて、発泡体を得る工程
を含む、製造方法。
Item 4.
A method for producing a foam, comprising the steps of:
The method according to claim 3 , further comprising: (C) a step of foaming the foam composition obtained in the step (B) to obtain a foam.
項５．
樹脂、並びに、
式（１）及び（２）で表される化合物、並びに該化合物の塩から選ばれる少なくとも一種の化合物：
Item 5.
Resin, as well as
At least one compound selected from the compounds represented by formulas (1) and (2) and salts of said compounds:
を含む組成物（但し、発泡剤を含まない）の、
発泡のための使用。
A composition comprising the steps of:
Use for foaming.
項６．
高分子材料、並びに、
式（１）及び（２）で表される化合物、並びに該化合物の塩から選ばれる少なくとも一種の化合物：
Item 6.
Polymer materials, and
At least one compound selected from the compounds represented by formulas (1) and (2) and salts of said compounds:
のみからなる、組成物の、
発泡のための使用。
A composition consisting essentially of
Use for foaming.
本発明は、優れた発泡倍率、及び微細な平均セル径を有する発泡体を得ることができる発泡用組成物、発泡組成物の製造方法、及び優れた発泡倍率と微細な平均セル径を有することができる発泡体の製造方法を提供することができる。 The present invention provides a foaming composition capable of producing a foam having an excellent expansion ratio and a fine average cell diameter, a method for producing a foaming composition, and a method for producing a foam having an excellent expansion ratio and a fine average cell diameter.
以下に本発明を詳細に説明する。 The present invention is described in detail below.
本発明を表す実施の形態は、発明の趣旨がより良く理解出来る説明であり、特に指定のない限り、発明内容を限定するものではない。 The embodiments of the present invention are intended to provide a better understanding of the spirit of the invention, and unless otherwise specified, do not limit the content of the invention.
本明細書において、「含む」及び「含有」は、「含む（comprise）」、「実質的にのみからなる（consist essentially of）」、及び「のみからなる（consist of）」のいずれも包含する概念である。 In this specification, the terms "comprise" and "contain" are concepts that encompass all of "comprise," "consist essentially of," and "consist of."
本明細書において、数値範囲を「Ａ～Ｂ」で示す場合、数値範囲は「Ａ以上、Ｂ以下」を意味する。 In this specification, when a numerical range is indicated as "A to B," the numerical range means "greater than or equal to A and less than or equal to B."
１．発泡用組成物
本発明の発泡用組成物は、
樹脂、並びに、
式（１）及び（２）で表される化合物、並びに該化合物の塩から選ばれる少なくとも一種の化合物：
1. Foaming Composition The foaming composition of the present invention is
Resin, as well as
At least one compound selected from the compounds represented by formulas (1) and (2) and salts of said compounds:
を含む。
including.
但し、本発明の前記発泡用組成物は、発泡剤を含まない。 However, the foaming composition of the present invention does not contain a foaming agent.
本発明の発泡用組成物を用い、化学発泡剤と組み合わせ、発泡させることにより、優れた発泡倍率、及び微細な平均セル径を有する発泡体を得ることができる。 By using the foaming composition of the present invention and combining it with a chemical foaming agent, it is possible to obtain a foam with an excellent expansion ratio and a fine average cell diameter.
本発明の発泡用組成物は、好ましく発泡のために使用することができる。 The foaming composition of the present invention can be preferably used for foaming.
１－１．樹脂
本発明の発泡用組成物は、樹脂を含む。
1-1. Resin The foaming composition of the present invention contains a resin.
本発明の発泡用組成物に適用することのできる樹脂としては、特に限定はなく、公知の樹脂を広く使用することが可能である。例えば、熱硬化性樹脂と熱可塑性樹脂が挙げられる。 There are no particular limitations on the resins that can be used in the foaming composition of the present invention, and a wide range of known resins can be used. Examples include thermosetting resins and thermoplastic resins.
熱硬化性樹脂としては、ポリウレタン、エポキシ樹脂、フェノール樹脂、メラミン樹脂、尿素樹脂、不飽和ポリエステル樹脂、アルキド樹脂、熱硬化性ポリイミド等が挙げられる。 Thermosetting resins include polyurethane, epoxy resin, phenolic resin, melamine resin, urea resin, unsaturated polyester resin, alkyd resin, thermosetting polyimide, etc.
熱可塑性樹脂としては、ポリエチレン、ポリプロピレン、ポリ塩化ビニル、エチレン－酢酸ビニル共重合体、ポリスチレン、ポリ酢酸ビニル、ポリウレタン、ポリテトラフルオロエチレン、アクリロニトリル－ブタジエン－スチレン樹脂、アクリロニトリル－スチレン樹脂、アクリル樹脂、ポリビニルアルコール等が挙げられる。 Thermoplastic resins include polyethylene, polypropylene, polyvinyl chloride, ethylene-vinyl acetate copolymer, polystyrene, polyvinyl acetate, polyurethane, polytetrafluoroethylene, acrylonitrile-butadiene-styrene resin, acrylonitrile-styrene resin, acrylic resin, polyvinyl alcohol, etc.
これらの樹脂の中でも、ポリエチレン、ポリプロピレン、ポリ塩化ビニル、エチレン－酢酸ビニル共重合体、ポリウレタンが好ましく、ポリエチレン、エチレン－酢酸ビニル共重合体がより好ましい。 Among these resins, polyethylene, polypropylene, polyvinyl chloride, ethylene-vinyl acetate copolymer, and polyurethane are preferred, and polyethylene and ethylene-vinyl acetate copolymer are more preferred.
１－２．式（１）及び（２）で表される化合物、並びに該化合物の塩
本発明の発泡用組成物は、式（１）及び（２）で表される化合物、並びに該化合物の塩から選ばれる少なくとも一種の化合物を含む。
1-2. Compounds represented by formulas (1) and (2) and salts of said compounds The foaming composition of the present invention contains at least one compound selected from the compounds represented by formulas (1) and (2) and salts of said compounds.
以下、これらを総称して「ピラゾロン誘導体」ということがある。 Hereinafter, these will be collectively referred to as "pyrazolone derivatives."
本発明の式（１）で表される化合物、及び該化合物の塩は、下記式（１）で表される化合物である。 The compound represented by formula (1) of the present invention and the salt of the compound are compounds represented by the following formula (1).
以下、当該化合物及びその塩を総称して、単に化合物（１）とも記す。 Hereinafter, this compound and its salts will be collectively referred to simply as compound (1).
式（１）中、Ｒ３とＲ４とは互いに結合してアルキリデン基を形成してもよく、Ｒ２、Ｒ３及びＲ４のいずれか２つが互いに結合してアルキレン基を形成してもよい。 In formula (1), R 3 and R 4 may be bonded to each other to form an alkylidene group, or any two of R 2 , R 3 and R 4 may be bonded to each other to form an alkylene group.
式（１）中、これら各基は、それぞれ１個以上の置換基を有していてもよい。 In formula (1), each of these groups may have one or more substituents.
本発明の式（２）で表される化合物、及び該化合物の塩は、下記式（２）で表される化合物である。 The compound represented by formula (2) of the present invention and the salt of the compound are compounds represented by the following formula (2).
以下、当該化合物及びその塩を総称して、単に化合物（２）とも記す。 Hereinafter, this compound and its salts will be collectively referred to simply as compound (2).
式（２）中、これら各基は、それぞれ１個以上の置換基を有していてもよい。 In formula (2), each of these groups may have one or more substituents.
化合物（１）又は（２）において、「アルキル基」としては、特に限定はなく、例えば、直鎖状、分岐鎖状又は環状のアルキル基が挙げられ、具体的には、例えば、メチル、エチル、ｎ－プロピル、イソプロピル、ｎ－ブチル、イソブチル、ｓ－ブチル、ｔ－ブチル等の炭素数１～４の直鎖状又は分岐鎖状のアルキル基、更に、１－エチルプロピル、ｎ－ペンチル、イソペンチル、ネオペンチル、ｎ－ヘキシル、イソヘキシル、３－メチルペンチル、ｎ－ヘプチル、ｎ－オクチル、ｎ－ノニル、ｎ－デシル、ｎ－ウンデシル、ｎ－ドデシル、５－プロピルノニル、ｎ－トリデシル、ｎ－テトラデシル、ｎ－ペンタデシル、ヘキサデシル、ヘプタデシル、オクタデシル等を加えた炭素数５～１８の直鎖状又は分岐鎖状アルキル基；シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチル等の炭素数３～８の環状アルキル基等が挙げられる。 In the compound (1) or (2), the "alkyl group" is not particularly limited, and examples thereof include linear, branched, or cyclic alkyl groups. Specific examples thereof include linear or branched alkyl groups having 1 to 4 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl, linear or branched alkyl groups having 5 to 18 carbon atoms, such as 1-ethylpropyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, 3-methylpentyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, 5-propylnonyl, n-tridecyl, n-tetradecyl, n-pentadecyl, hexadecyl, heptadecyl, and octadecyl, and cyclic alkyl groups having 3 to 8 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.
化合物（１）又は（２）において、「アラルキル基」としては、特に限定はなく、例えば、ベンジル、フェネチル、トリチル、１－ナフチルメチル、２－（１－ナフチル）エチル、２－（２－ナフチル）エチル基等が挙げられる。 In compound (1) or (2), the "aralkyl group" is not particularly limited, and examples thereof include benzyl, phenethyl, trityl, 1-naphthylmethyl, 2-(1-naphthyl)ethyl, and 2-(2-naphthyl)ethyl groups.
化合物（１）又は（２）において、「アリール基」としては、特に限定はなく、例えば、フェニル、ビフェニル、ナフチル、ジヒドロインデニル、９Ｈ－フルオレニル基等が挙げられる。 In compound (1) or (2), the "aryl group" is not particularly limited, and examples thereof include phenyl, biphenyl, naphthyl, dihydroindenyl, and 9H-fluorenyl groups.
化合物（１）又は（２）において、「複素環基」としては、特に限定はなく、例えば、２－ピリジル、３－ピリジル、４－ピリジル、２－ピラジニル、２－ピリミジル、４－ピリミジル、５－ピリミジル、３－ピリダジル、４－ピリダジル、４－（１，２，３－トリアジル）、５－（１，２，３－トリアジル）、２－（１，３，５－トリアジル）、３－（１，２，４－トリアジル）、５－（１，２，４－トリアジル）、６－（１，２，４－トリアジル）、２－キノリル、３－キノリル、４－キノリル、５－キノリル、６－キノリル、７－キノリル、８－キノリル、１－イソキノリル、３－イソキノリル、４－イソキノリル、５－イソキノリル、６－イソキノリル、７－イソキノリル、８－イソキノリル、２－キノキサリル、３－キノキサリル、５－キノキサリル、６－キノキサリル、７－キノキサリル、８－キノキサリル、３－シンノリル、４－シンノリル、５－シンノリル、６－シンノリル、７－シンノリル、８－シンノリル、２－キナゾリル、４－キナゾリル、５－キナゾリル、６－キナゾリル、７－キナゾリル、８－キナゾリル、１－フタラジル、４－フタラジル、５－フタラジル、６－フタラジル、７－フタラジル、８－フタラジル、１－テトラヒドロキノリル、２－テトラヒドロキノリル、３－テトラヒドロキノリル、４－テトラヒドロキノリル、５－テトラヒドロキノリル、６－テトラヒドロキノリル、７－テトラヒドロキノリル、８－テトラヒドロキノリル、１－ピロリル、２－ピロリル、３－ピロリル、２－フリル、３－フリル、２－チエニル、３－チエニル、１－イミダゾリル、２－イミダゾリル、４－イミダゾリル、５－イミダゾリル、１－ピラゾリル、３－ピラゾリル、４－ピラゾリル、５－ピラゾリル、２－オキサゾリル、４－オキサゾリル、５－オキサゾリル、２－チアゾリル、４－チアゾリル、５－チアゾリル、３－イソオキサゾリル、４－イソオキサゾリル、５－イソオキサゾリル、３－イソチアゾリル、４－イソチアゾリル、５－イソチアゾリル、４－（１，２，３－チアジアゾリル）、５－（１，２，３－チアジアゾリル）、３－（１，２，５－チアジアゾリル）、２－（１，３，４－チアジアゾリル）、４－（１，２，３－オキサジアゾリル）、５－（１，２，３－オキサジアゾリル）、３－（１，２，４－オキサジアゾリル）、５－（１，２，４－オキサジアゾリル）、３－（１，２，５－オキサジアゾリル）、２－（１，３，４－オキサジアゾリル）、１－（１，２，３－トリアゾリル）、４－（１，２，３－トリアゾリル）、５－（１，２，３－トリアゾリル）、１－（１，２，４－トリアゾリル）、３－（１，２，４－トリアゾリル）、５－（１，２，４－トリアゾリル）、１－テトラゾリル、５－テトラゾリル、１－インドリル、２－インドリル、３－インドリル、４－インドリル、５－インドリル、６－インドリル、７－インドリル、１－イソインドリル、２－イソインドリル、３－イソインドリル、４－イソインドリル、５－イソインドリル、６－イソインドリル、７－イソインドリル、１－ベンゾイミダゾリル、２－ベンゾイミダゾリル、４－ベンゾイミダゾリル、５－ベンゾイミダゾリル、６－ベンゾイミダゾリル、７－ベンゾイミダゾリル、２－ベンゾフラニル、３－ベンゾフラニル、４－ベンゾフラニル、５－ベンゾフラニル、６－ベンゾフラニル、７－ベンゾフラニル、１－イソベンゾフラニル、３－イソベンゾフラニル、４－イソベンゾフラニル、５－イソベンゾフラニル、６－イソベンゾフラニル、７－イソベンゾフニル、２－ベンゾチエニル、３－ベンゾチエニル、４－ベンゾチエニル、５－ベンゾチエニル、６－ベンゾチエニル、７－ベンゾチエニル、２－ベンゾオキサゾリル、４－ベンゾオキサゾリル、５－ベンゾオキサゾリル、６－ベンゾオキサゾリル、７－ベンゾオキサゾリル、２－ベンゾチアゾリル、４－ベンゾチアゾリル、５－ベンゾチアゾリル、６－ベンゾチアゾリル、７－ベンゾチアゾリル、１－インダゾリル、３－インダゾリル、４－インダゾリル、５－インダゾリル、６－インダゾリル、７－インダゾリル、２－モルホリル、３－モルホリル、４－モルホリル、１－ピペラジル、２－ピペラジル、１－ピペリジル、２－ピペリジル、３－ピペリジル、４－ピペリジル、２－テトラヒドロピラニル、３－テトラヒドロピラニル、４－テトラヒドロピラニル、２－テトラヒドロチオピラニル、３－テトラヒドロチオピラニル、４－テトラヒドロチオピラニル、１－ピロリジル、２－ピロリジル、３－ピロリジル、フラニル、２－テトラヒドロフラニル、３－テトラヒドロフラニル、２－テトラヒドロチエニル、３－テトラヒドロチエニル、５－メチル－３－オキソ－２，３－ジヒドロ－１Ｈ－ピラゾール－４－イル基、モルホリノ基等が挙げられる。 In the compound (1) or (2), the "heterocyclic group" is not particularly limited, and examples thereof include 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrazinyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 3-pyridazyl, 4-pyridazyl, 4-(1,2,3-triazyl), 5-(1,2,3-triazyl), 2-(1,3,5-triazyl), 3-(1,2,4-triazyl), 5-(1,2,4-triazyl), 6-(1,2,4-triazyl), 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, and the like. noryl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalyl, 3-quinoxalyl, 5-quinoxalyl, 6-quinoxalyl, 7-quinoxalyl, 8-quinoxalyl, 3-cinnolyl, 4-cinnolyl, 5-cinnolyl, 6-cinnolyl, 7-cinnolyl, 8-cinnolyl, 2-quinazolyl, 4-quinazolyl, 5-quinazolyl, 6-quinazolyl, 7-quinazolyl, 8-quinazolyl, 1-phthalazyl, 4-phthalazyl, 5-phthalazyl, 6-phthalazyl, 7 -phthalazyl, 8-phthalazyl, 1-tetrahydroquinolyl, 2-tetrahydroquinolyl, 3-tetrahydroquinolyl, 4-tetrahydroquinolyl, 5-tetrahydroquinolyl, 6-tetrahydroquinolyl, 7-tetrahydroquinolyl, 8-tetrahydroquinolyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl , 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 4-(1,2,3-thiadiazolyl), 5-(1,2,3-thiadiazolyl), 3-(1,2,5-thiadiazolyl), 2-(1,3,4-thiadiazolyl), 4-(1,2,3-oxadiazolyl), 5-(1,2,3-oxadiazolyl), 3-(1,2,4-oxadiazolyl), 5-(1,2,4-oxadiazolyl), 3-(1 , 2,5-oxadiazolyl), 2-(1,3,4-oxadiazolyl), 1-(1,2,3-triazolyl), 4-(1,2,3-triazolyl), 5-(1,2,3-triazolyl), 1-(1,2,4-triazolyl), 3-(1,2,4-triazolyl), 5-(1,2,4-triazolyl), 1-tetrazolyl, 5-tetrazolyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 1-benzimidazolyl, 2-benzimidazolyl, 4-benzimidazolyl, 5-benzimidazolyl, 6-benzimidazolyl, 7-benzimidazolyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-benzothienyl, 3-benzothienyl nyl, 4-benzothienyl, 5-benzothienyl, 6-benzothienyl, 7-benzothienyl, 2-benzoxazolyl, 4-benzoxazolyl, 5-benzoxazolyl, 6-benzoxazolyl, 7-benzoxazolyl, 2-benzothiazolyl, 4-benzothiazolyl, 5-benzothiazolyl, 6-benzothiazolyl, 7-benzothiazolyl, 1-indazolyl, 3-indazolyl, 4-indazolyl, 5-indazolyl, 6-indazolyl, 7-indazolyl, 2-morpholyl, 3-morpholyl, 4-morpholyl, 1-piperazyl, 2-piperazyl Examples of the group include 1-piperidyl, 2-piperidyl, 3-piperidyl, 4-piperidyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl, 4-tetrahydrothiopyranyl, 1-pyrrolidyl, 2-pyrrolidyl, 3-pyrrolidyl, furanyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 5-methyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl group, and morpholino group.
化合物（１）又は（２）において、「アルキレン基」としては、特に限定はなく、例えば、エチレン基、トリメチレン基、テトラメチレン基、ペンタメチレン基、ヘキサメチレン基、ヘプタメチレン基等の炭素数２～７のアルキレン基を挙げることができる。これらアルキレン基は、窒素原子、酸素原子、硫黄原子を含んでいてもよく、フェニレン基を介していてもよい。このようなアルキレン基としては、例えば、－ＣＨ２ＮＨＣＨ２－、－ＣＨ２ＮＨＣＨ２ＣＨ２－、－ＣＨ２ＮＨＮＨＣＨ２－、－ＣＨ２ＣＨ２ＮＨＣＨ２ＣＨ２－、－ＣＨ２ＮＨＮＨＣＨ２ＣＨ２－、－ＣＨ２ＮＨＣＨ２ＮＨＣＨ２－、－ＣＨ２ＣＨ２ＣＨ２ＮＨＣＨ２ＣＨ２ＣＨ２－、－ＣＨ２ＯＣＨ２ＣＨ２－、－ＣＨ２ＣＨ２ＯＣＨ２ＣＨ２－、－ＣＨ２ＳＣＨ２ＣＨ２－、－ＣＨ２ＣＨ２ＳＣＨ２ＣＨ２－、 In compound (1) or (2), the "alkylene group" is not particularly limited and examples thereof include alkylene groups having 2 to 7 carbon atoms, such as an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, a heptamethylene group, etc. These alkylene groups may contain a nitrogen atom, an oxygen atom, or a sulfur atom, and may be connected via a phenylene group. Examples of such alkylene groups include, for example, -CH 2 NHCH 2 -, -CH 2 NHCH 2 CH 2 -, -CH 2 NHNHCH 2 -, -CH 2 CH 2 NHCH 2 CH 2 -, -CH 2 NHNHCH 2 CH 2 -, -CH 2 NHCH 2 NHCH 2 -, -CH 2 CH 2 CH 2 NHCH 2 CH 2 CH 2 -, -CH 2 OCH 2 CH 2 - , -CH 2 CH 2 OCH 2 CH 2 -, -CH 2 SCH 2 CH 2 -, -CH 2 CH 2 SCH 2 CH 2 -,
化合物（１）又は（２）において、「アルキリデン基」としては、炭素数が１～４程度であって、特に限定はなく、例えば、メチリデン、エチリデン、プロピリデン、イソプロピリデン、ブチリデン基等が挙げられる。 In compound (1) or (2), the "alkylidene group" has about 1 to 4 carbon atoms, and is not particularly limited, and examples thereof include methylidene, ethylidene, propylidene, isopropylidene, and butylidene groups.
これらアルキル基、アラルキル基、アリール基、複素環基、及びアルキレン基は、置換可能な任意の位置にそれぞれ１個以上の置換基を有していてもよい。 These alkyl groups, aralkyl groups, aryl groups, heterocyclic groups, and alkylene groups may each have one or more substituents at any position where substitution is possible.
該「置換基」としては、特に限定はなく、例えば、ハロゲン原子、アミノ基、アミノアルキル基、アルコキシカルボニル基、アシル基、アシルオキシ基、アミド基、カルボキシル基、カルボキシアルキル基、ホルミル基、ニトリル基、ニトロ基、アルキル基、ヒドロキシアルキル基、水酸基、アルコキシ基、アリール基、アリールオキシ基、複素環基、チオール基、アルキルチオ基、アリールチオ基等が挙げられる。 The "substituent" is not particularly limited, and examples thereof include halogen atoms, amino groups, aminoalkyl groups, alkoxycarbonyl groups, acyl groups, acyloxy groups, amide groups, carboxyl groups, carboxyalkyl groups, formyl groups, nitrile groups, nitro groups, alkyl groups, hydroxyalkyl groups, hydroxyl groups, alkoxy groups, aryl groups, aryloxy groups, heterocyclic groups, thiol groups, alkylthio groups, and arylthio groups.
該置換基は、好ましくは１～５個、より好ましくは１～３個有していてもよい。 The number of such substituents may be preferably 1 to 5, and more preferably 1 to 3.
化合物（１）又は（２）において、「ハロゲン原子」としては、フッ素原子、塩素原子、臭素原子、及びヨウ素原子が挙げられ、好ましくは塩素原子、臭素原子、及びヨウ素原子である。 In compound (1) or (2), the "halogen atom" includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and is preferably a chlorine atom, a bromine atom, or an iodine atom.
化合物（１）又は（２）において、「アミノ基」としては、－ＮＨ２で表されるアミノ基だけでなく、例えば、メチルアミノ、エチルアミノ、ｎ－プロピルアミノ、イソプロピルアミノ、ｎ－ブチルアミノ、イソブチルアミノ、ｓ－ブチルアミノ、ｔ－ブチルアミノ、１－エチルプロピルアミノ、ｎ－ペンチルアミノ、ネオペンチルアミノ、ｎ－ヘキシルアミノ、イソヘキシルアミノ、３－メチルペンチルアミノ基等の直鎖状又は分岐鎖状の炭素数１～６程度のモノアルキルアミノ基；ジメチルアミノ、エチルメチルアミノ、ジエチルアミノ基等の直鎖状又は分岐鎖状の炭素数１～２程度のアルキル基を２つ有するジアルキルアミノ基等の置換アミノ基も含まれる。 In the compound (1) or (2), the "amino group" includes not only the amino group represented by -NH2 , but also substituted amino groups such as linear or branched monoalkylamino groups having about 1 to 6 carbon atoms, such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, s-butylamino, t-butylamino, 1-ethylpropylamino, n-pentylamino, neopentylamino, n-hexylamino, isohexylamino, and 3-methylpentylamino groups; and linear or branched dialkylamino groups having two alkyl groups having about 1 to 2 carbon atoms, such as dimethylamino, ethylmethylamino, and diethylamino groups.
化合物（１）又は（２）において、「アミノアルキル基」としては、特に限定はなく、例えば、アミノメチル、メチルアミノメチル、エチルアミノメチル、ジメチルアミノメチル、エチルメチルアミノメチル、ジエチルアミノメチル、２－アミノエチル、２－（メチルアミノ）エチル、２－（エチルアミノ）エチル、２－（ジメチルアミノ）エチル、２－（エチルメチルアミノ）エチル、２－（ジエチルアミノ）エチル、３－アミノプロピル、３－（メチルアミノ）プロピル、３－（エチルアミノ）プロピル、３－（ジメチルアミノ）プロピル、３－（エチルメチルアミノ）プロピル、３－（ジエチルアミノ）プロピル基等の炭素数１～７程度のアミノアルキル基、モノアルキル置換アミノアルキル基又はジアルキル置換アミノアルキル基等が挙げられる。 In compound (1) or (2), the "aminoalkyl group" is not particularly limited, and examples thereof include aminoalkyl groups having about 1 to 7 carbon atoms, such as aminomethyl, methylaminomethyl, ethylaminomethyl, dimethylaminomethyl, ethylmethylaminomethyl, diethylaminomethyl, 2-aminoethyl, 2-(methylamino)ethyl, 2-(ethylamino)ethyl, 2-(dimethylamino)ethyl, 2-(ethylmethylamino)ethyl, 2-(diethylamino)ethyl, 3-aminopropyl, 3-(methylamino)propyl, 3-(ethylamino)propyl, 3-(dimethylamino)propyl, 3-(ethylmethylamino)propyl, and 3-(diethylamino)propyl groups, as well as monoalkyl-substituted aminoalkyl groups and dialkyl-substituted aminoalkyl groups.
化合物（１）又は（２）において、「アルコキシカルボニル基」としては、特に限定はなく、例えば、メトキシカルボニル、エトキシカルボニル基等の炭素数１～４の直鎖状又は分岐鎖状アルコキシカルボニル基が挙げられる。 In compound (1) or (2), the "alkoxycarbonyl group" is not particularly limited, and examples thereof include linear or branched alkoxycarbonyl groups having 1 to 4 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl groups.
化合物（１）又は（２）において、「アシル基」としては、特に限定はなく、例えば、アセチル、プロピオニル、ピバロイル基等の炭素数１～４の直鎖状又は分岐鎖状アルキルカルボニル基が挙げられる。 In compound (1) or (2), the "acyl group" is not particularly limited, and examples thereof include linear or branched alkylcarbonyl groups having 1 to 4 carbon atoms, such as acetyl, propionyl, and pivaloyl groups.
化合物（１）又は（２）において、「アシルオキシ基」としては、特に限定はなく、例えば、アセチルオキシ、プロピオニルオキシ、ｎ－ブチリルオキシ基等の炭素数１～４の直鎖状又は分岐鎖状アシルオキシ基等が挙げられる。 In compound (1) or (2), the "acyloxy group" is not particularly limited, and examples thereof include linear or branched acyloxy groups having 1 to 4 carbon atoms, such as acetyloxy, propionyloxy, and n-butyryloxy groups.
化合物（１）又は（２）において、「アミド基」としては、特に限定はなく、例えば、アセトアミド、ベンズアミド基等のカルボン酸アミド基；チオアセトアミド、チオベンズアミド基等のチオアミド基；Ｎ－メチルアセトアミド、Ｎ－ベンジルアセトアミド基等のＮ－置換アミド基；等が挙げられる。 In compound (1) or (2), the "amide group" is not particularly limited, and examples thereof include carboxylic acid amide groups such as acetamide and benzamide groups; thioamide groups such as thioacetamide and thiobenzamide groups; and N-substituted amide groups such as N-methylacetamide and N-benzylacetamide groups.
化合物（１）又は（２）において、「カルボキシアルキル基」としては、特に限定はなく、例えば、カルボキシメチル、カルボキシエチル、カルボキシ－ｎ－プロピル、カルボキシ－ｎ－ブチル、カルボキシ－ｎ－ペンチル、カルボキシ－ｎ－ヘキシル基等のカルボキシアルキル基が挙げられる。 In compound (1) or (2), the "carboxyalkyl group" is not particularly limited, and examples thereof include carboxyalkyl groups such as carboxymethyl, carboxyethyl, carboxy-n-propyl, carboxy-n-butyl, carboxy-n-pentyl, and carboxy-n-hexyl groups.
化合物（１）又は（２）において、「ヒドロキシアルキル基」としては、特に限定はなく、例えば、ヒドロキシメチル、ヒドロキシエチル、ヒドロキシ－ｎ－プロピル、ヒドロキシ－ｎ－ブチル基等のヒドロキシアルキル基が挙げられる。 In compound (1) or (2), the "hydroxyalkyl group" is not particularly limited, and examples thereof include hydroxyalkyl groups such as hydroxymethyl, hydroxyethyl, hydroxy-n-propyl, and hydroxy-n-butyl groups.
化合物（１）又は（２）において、「アルコキシ基」としては、特に限定はなく、例えば、直鎖状、分岐鎖状又は環状のアルコキシ基が挙げられ、具体的には、例えば、メトキシ、エトキシ、ｎ－プロポキシ、イソプロポキシ、ｎ－ブトキシ、ｔ－ブトキシ、ｎ－ペンチルオキシ、ネオペンチルオキシ、ｎ－ヘキシルオキシ基の直鎖状又は分岐鎖状のアルコキシ基；シクロプロピルオキシ、シクロブチルオキシ、シクロペンチルオキシ、シクロヘキシルオキシ、シクロヘプチルオキシ、シクロオクチルオキシ基等の環状アルコキシ基等が挙げられる。 In compound (1) or (2), the "alkoxy group" is not particularly limited, and examples thereof include linear, branched, or cyclic alkoxy groups. Specific examples thereof include linear or branched alkoxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, t-butoxy, n-pentyloxy, neopentyloxy, and n-hexyloxy groups; and cyclic alkoxy groups such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, and cyclooctyloxy groups.
化合物（１）又は（２）において、「アリールオキシ基」としては、特に限定はなく、例えば、フェノキシ、ビフェニルオキシ、ナフトキシ基等が挙げられる。 In compound (1) or (2), the "aryloxy group" is not particularly limited, and examples thereof include phenoxy, biphenyloxy, and naphthoxy groups.
化合物（１）又は（２）において、「アルキルチオ基」としては、特に限定はなく、例えば、メチルチオ基、エチルチオ基、及びｎ－プロピルチオ基等が挙げられる。 In compound (1) or (2), the "alkylthio group" is not particularly limited, and examples thereof include a methylthio group, an ethylthio group, and an n-propylthio group.
化合物（１）又は（２）において、「アリールチオ基」としては、特に限定はなく、例えば、フェニルチオ基、ナフチルチオ基、ビフェニルチオ基等が挙げられる。 In compound (1) or (2), the "arylthio group" is not particularly limited, and examples thereof include a phenylthio group, a naphthylthio group, and a biphenylthio group.
化合物（１）の中でも、Ｒ１が水素原子である化合物が好ましい。 Among the compounds (1), those in which R 1 is a hydrogen atom are preferred.
化合物（１）の中でも、Ｒ２が、水素原子、炭素数１～４の直鎖状若しくは分岐鎖状アルキル基、アラルキル基、アリール基、又は複素環基である化合物が好ましく、水素原子、炭素数１～４の直鎖状若しくは分岐鎖状アルキル基、ベンジル基、フェニル基、ナフチル基、又はフリル基である化合物がより好ましく、水素原子、又は炭素数１～４の直鎖状アルキル基である化合物が更に好ましい。 Among the compounds (1), preferred are compounds in which R 2 is a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, an aralkyl group, an aryl group, or a heterocyclic group, more preferred are compounds in which R 2 is a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, a benzyl group, a phenyl group, a naphthyl group, or a furyl group, and even more preferred are compounds in which R 2 is a hydrogen atom, or a linear alkyl group having 1 to 4 carbon atoms.
化合物（１）の中でも、Ｒ３及びＲ４の少なくとも一方が水素原子である化合物が好ましく、Ｒ３及びＲ４が共に水素原子である化合物がより好ましい。 Among the compounds (1), compounds in which at least one of R 3 and R 4 is a hydrogen atom are preferred, and compounds in which both R 3 and R 4 are hydrogen atoms are more preferred.
化合物（１）の中でも、Ｒ１が水素原子であり、Ｒ２が水素原子、炭素数１～４の直鎖状若しくは分岐鎖状アルキル基、アラルキル基、アリール基、又は複素環基であり、Ｒ３及びＲ４が共に水素原子である化合物、及び、Ｒ１が水素原子であり、Ｒ２が水素原子、炭素数１～４の直鎖状若しくは分岐鎖状アルキル基、アラルキル基、アリール基、又は複素環基であり、Ｒ３とＲ４とが一緒になってアルキリデン基を形成している化合物が更に好ましく、Ｒ１が水素原子であり、Ｒ２が水素原子若しくは炭素数１～４の直鎖状アルキル基であり、Ｒ３及びＲ４が共に水素原子である化合物が特に好ましい。 Among the compounds (1), a compound in which R 1 is a hydrogen atom, R 2 is a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, an aralkyl group, an aryl group, or a heterocyclic group, and R 3 and R 4 are both hydrogen atoms, and a compound in which R 1 is a hydrogen atom, R 2 is a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, an aralkyl group, an aryl group, or a heterocyclic group, and R 3 and R 4 together form an alkylidene group are more preferred, and a compound in which R 1 is a hydrogen atom, R 2 is a hydrogen atom or a linear alkyl group having 1 to 4 carbon atoms, and R 3 and R 4 are both hydrogen atoms are particularly preferred.
化合物（２）の中でも、Ｒ５は水素原子であり、Ｒ６は炭素数１～４の直鎖状若しくは分岐鎖状アルキル基、アラルキル基、又はアリール基であり、Ｒ７及びＲ８は同一又は異なって、水素原子、炭素数１～４の直鎖状若しくは分岐鎖状アルキル基、アラルキル基、アリール基、アミノ基又は複素環基である化合物が好ましい。 Among the compounds (2), a compound in which R5 is a hydrogen atom, R6 is a linear or branched alkyl group having 1 to 4 carbon atoms, an aralkyl group, or an aryl group, and R7 and R8 may be the same or different and are a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, an aralkyl group, an aryl group, an amino group, or a heterocyclic group is preferable.
化合物（２）の中でも、Ｒ６が炭素数１～４の直鎖状アルキル基、アラルキル基、又はアリール基である化合物が好ましく、炭素数１～４の直鎖状アルキル基、又はアリール基である化合物がより好ましい。 Among the compounds (2), compounds in which R 6 is a linear alkyl group having 1 to 4 carbon atoms, an aralkyl group, or an aryl group are preferred, and compounds in which R 6 is a linear alkyl group having 1 to 4 carbon atoms, or an aryl group are more preferred.
化合物（２）の中でも、Ｒ７及びＲ８が同一又は異なって、水素原子、炭素数１～４の直鎖状アルキル基、又はアミノ基である化合物が好ましい。 Among the compounds (2), compounds in which R 7 and R 8 are the same or different and each represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms, or an amino group are preferred.
化合物（２）の中でも、Ｒ５は水素原子であり、Ｒ６が炭素数１～４の直鎖状アルキル基、又はアリール基であり、Ｒ７及びＲ８が同一又は異なって、水素原子、炭素数１～４の直鎖状アルキル基、又はアミノ基である化合物が好ましい。 Among the compounds (2), preferred are those in which R 5 is a hydrogen atom, R 6 is a linear alkyl group having 1 to 4 carbon atoms or an aryl group, and R 7 and R 8 are the same or different and are a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms, or an amino group.
化合物（１）及び化合物（２）の中でも、化合物（１）が特に好ましい。 Among compounds (1) and (2), compound (1) is particularly preferred.
化合物（１）としては、例えば、５－ピラゾロン、３－メチル－５－ピラゾロン、３－（ナフタレン－２－イル）－１Ｈ－ピラゾール－５（４Ｈ）－オン、３－（フラン－２－イル）－１Ｈ－ピラゾール－５（４Ｈ）－オン、３－フェニル－１Ｈ－ピラゾール－５（４Ｈ）－オン、３－プロピル－１Ｈ－ピラゾール－５（４Ｈ）－オン、３－ｔ－ブチル－１Ｈ－ピラゾール－５（４Ｈ）－オン、３－ウンデシル－１Ｈ－ピラゾール－５（４Ｈ）－オン、４－（２－ヒドロキシエチル）－３－メチル－１Ｈ－ピラゾール－５（４Ｈ）－オン、４－ベンジル－３－メチル－１Ｈ－ピラゾール－５（４Ｈ）オン、４，４’－（フェニルメチレン）ビス（５－メチル－１Ｈ－ピラゾール－３（２Ｈ）－オン）、４－［（ジメチルアミノ）メチリデン］－３－メチル－１Ｈ－ピラゾール－５(４Ｈ)－オン、４－メチル－２，３－ジアゾスピロ［４．４］ノン－３エン－１－オン、５－メチル－２－（４－ニトロフェニル）－１Ｈ－ピラゾール－３（２Ｈ）－オン、５－メチル－２－フェニル－２，４－ジヒドロ－３Ｈ－ピラゾール－３－オン、４，５，６，７－テトラヒドロ－２Ｈ－インダゾール－３（３ａＨ）－オン、４－{[４－ジメチルアミノ]フェニル}メチリデン｝－３－メチル－１Ｈ－ピラゾール－５（４Ｈ）－オン、４，４’－（４－ヒドロキシフェニルメチレン）ビス（５－メチル－１Ｈ－ピラゾール－３（２Ｈ）－オン）、１，３－ジフェニル－１Ｈ－ピラゾール－５（４Ｈ）－オン、及び４，４’－（４－ニトロフェニルメチレン）ビス（５－メチル－１Ｈ－ピラゾール－３（２Ｈ）－オン）等が挙げられる。 Examples of compound (1) include 5-pyrazolone, 3-methyl-5-pyrazolone, 3-(naphthalene-2-yl)-1H-pyrazol-5(4H)-one, 3-(furan-2-yl)-1H-pyrazol-5(4H)-one, 3-phenyl-1H-pyrazol-5(4H)-one, 3-propyl-1H-pyrazol-5(4H)-one, 3-t-butyl-1H-pyrazol-5(4H)-one, H)-one, 3-undecyl-1H-pyrazol-5(4H)-one, 4-(2-hydroxyethyl)-3-methyl-1H-pyrazol-5(4H)-one, 4-benzyl-3-methyl-1H-pyrazol-5(4H)-one, 4,4'-(phenylmethylene)bis(5-methyl-1H-pyrazol-3(2H)-one), 4-[(dimethylamino)methylidene]-3-methyl-1H- Pyrazol-5(4H)-one, 4-methyl-2,3-diazospiro[4.4]non-3en-1-one, 5-methyl-2-(4-nitrophenyl)-1H-pyrazol-3(2H)-one, 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, 4,5,6,7-tetrahydro-2H-indazol-3(3aH)-one, 4-{[4-dimethylamino]phenyl}methylidene}-3-methyl-1H-pyrazol-5(4H)-one, 4,4'-(4-hydroxyphenylmethylene)bis(5-methyl-1H-pyrazol-3(2H)-one), 1,3-diphenyl-1H-pyrazol-5(4H)-one, and 4,4'-(4-nitrophenylmethylene)bis(5-methyl-1H-pyrazol-3(2H)-one) are included.
化合物（２）としては、例えば、１，５－ジメチル－２－フェニル－１Ｈ－ピラゾール－３（２Ｈ）－オン、１－フェニル－１Ｈ－ピラゾール－３（２Ｈ）－オン、及び４－アミノ－１，５－ジメチル－２－フェニル－１Ｈ－ピラゾール－３（２Ｈ）－オン等が挙げられる。 Examples of compound (2) include 1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one, 1-phenyl-1H-pyrazol-3(2H)-one, and 4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one.
中でも、好ましい化合物は、５－ピラゾロン、３－メチル－５－ピラゾロン、３－ｔ－ブチル－１Ｈ－ピラゾール－５（４Ｈ）－オン、３－（ナフタレン－２－イル）－１Ｈ－ピラゾール－５（４Ｈ）－オン、３－（フラン－２－イル）－１Ｈ－ピラゾール－５（４Ｈ）－オン、３－フェニル－１Ｈ－ピラゾール－５（４Ｈ）－オン、及び３－プロピル－１Ｈ－ピラゾール－５（４Ｈ）－オンがより好ましい。 Among these, preferred compounds are 5-pyrazolone, 3-methyl-5-pyrazolone, 3-t-butyl-1H-pyrazol-5(4H)-one, 3-(naphthalen-2-yl)-1H-pyrazol-5(4H)-one, 3-(furan-2-yl)-1H-pyrazol-5(4H)-one, 3-phenyl-1H-pyrazol-5(4H)-one, and more preferably 3-propyl-1H-pyrazol-5(4H)-one.
本発明の発泡用組成物に含まれる化合物（１）及び（２）としては、上記した化合物を一種のみ単独で含んでもよいし、二種以上を混合して含んでもよい。 The compounds (1) and (2) contained in the foaming composition of the present invention may contain only one of the above-mentioned compounds alone, or may contain a mixture of two or more of them.
化合物（１）又は（２）の中には、互変異性体を生じるものがある。互変異性化が可能である（例えば、溶液中である）場合に、互変異性体の化学平衡に達し得る。化合物（１）又は（２）は、例えば、式（３）～（９）で表されるような互変異性体として存在することができる。 Some compounds (1) or (2) can occur as tautomers. When tautomerization is possible (e.g., in solution), a chemical equilibrium of the tautomers can be reached. Compounds (1) or (2) can exist as tautomers, for example, as represented by formulas (3)-(9).
前記式（１）において、Ｒ１及びＲ３が水素原子である化合物（化合物（１）－Ａ）には、以下の式（３）～（５）で表される互変異性体が存在する。 In the compound (1) in which R 1 and R 3 are hydrogen atoms (compound (1)-A), there exist tautomers represented by the following formulas (3) to (5).
前記式（１）において、Ｒ３が水素原子である化合物（化合物（１）－Ｂ）には、以下の式（６）～（７）で表される互変異性体が存在する。
In the compound of formula (1) where R 3 is a hydrogen atom (compound (1)-B), there exist tautomers represented by the following formulas (6) and (7).
前記式（１）において、Ｒ１が水素原子である化合物（化合物（１）－Ｃ）には、以下の式（８）で表される互変異性体が存在する。
In the above formula (1), a compound in which R 1 is a hydrogen atom (compound (1)-C) has a tautomer represented by the following formula (8).
前記式（２）において、Ｒ５が水素原子である化合物（化合物（２）－Ａ）には、以下の式（９）で表される互変異性体が存在する。
In the above formula (2), a compound in which R 5 is a hydrogen atom (compound (2)-A) has a tautomer represented by the following formula (9).
式（１）又は（２）で表される化合物の塩としては、特に限定はなく、あらゆる種類の塩が含まれる。このような塩としては、例えば、塩酸塩、硫酸塩、硝酸塩等の無機酸塩;酢酸塩、メタンスルホン酸塩等の有機酸塩；ナトリウム塩、カリウム塩等のアルカリ金属塩；マグネシウム塩、カルシウム塩等のアルカリ土類金属塩；ジメチルアンモニウム、及びトリエチルアンモニウム等のアンモニウム塩等が挙げられる。 The salt of the compound represented by formula (1) or (2) is not particularly limited and includes all kinds of salts. Examples of such salts include inorganic acid salts such as hydrochloride, sulfate, and nitrate; organic acid salts such as acetate and methanesulfonate; alkali metal salts such as sodium salt and potassium salt; alkaline earth metal salts such as magnesium salt and calcium salt; ammonium salts such as dimethylammonium and triethylammonium, etc.
本発明の発泡用組成物において、上記化合物（１）又は（２）を上記樹脂にあらかじめ混合する事に依り、発泡用組成物より製造された発泡体は、優れた発泡倍率と微細な平均セル径を有する。 In the foaming composition of the present invention, by mixing the compound (1) or (2) with the resin in advance, the foam produced from the foaming composition has an excellent expansion ratio and a fine average cell diameter.
１－３．その他の配合剤
本発明の発泡用組成物には、上記成分以外にも、その目的及び効果を損なわない範囲内で、様々な配合剤を添加しても良い。例えば、カーボンブラック、無機充填剤、老化防止剤、オゾン防止剤、軟化剤、加工助剤、ワックス、オイル、ステアリン酸等の炭素数８～３０の脂肪酸、脂肪酸金属塩、酸化亜鉛(ＺｎＯ)、架橋助剤、架橋剤、顔料、染料、粘着性付与剤、気泡核剤、悪臭吸着剤、紫外線吸収剤、光安定剤、酸化防止剤、遮光剤、金属不活性剤、消光剤、防曇剤、防黴剤、抗菌剤、防臭剤、可塑剤、帯電防止剤、界面活性剤、重合禁止剤、増感剤、硬化促進剤、希釈材、流動性調整剤、レベリング剤、粘着剤、接着剤、滑剤、離型剤、潤滑剤、固体潤滑剤、強化剤、相溶化剤、導電剤、アンチブロッキング剤、アンチトラッキング剤、蓄光剤、難燃剤、分散剤等を、本発明の目的を害しない範囲内で適宜選択して配合することができる。これら配合剤としては、市販品を好適に使用することができる。 無機充填材としては、特に制限はなく、例えば、シリカ；γ－アルミナ、α－アルミナ等のアルミナ（Ａｌ２Ｏ３）；ベーマイト、ダイアスポア等のアルミナ一水和物（Ａｌ２Ｏ３・Ｈ２Ｏ）；ギブサイト、バイヤライト等の水酸化アルミニウム［Ａｌ（ＯＨ）３］；炭酸アルミニウム［Ａｌ２（ＣＯ３）３］、水酸化マグネシウム［Ｍｇ（ＯＨ）２］、酸化マグネシウム（ＭｇＯ）、炭酸マグネシウム（ＭｇＣＯ３）、タルク（３ＭｇＯ・４ＳｉＯ２・Ｈ２Ｏ）、アタパルジャイ（５ＭｇＯ・８ＳｉＯ２・９Ｈ２Ｏ）、チタン白（ＴｉＯ２）、チタン黒（ＴｉＯ２ｎ－１）、酸化カルシウム（ＣａＯ）、水酸化カルシウム［Ｃａ（ＯＨ）２］、酸化アルミニウムマグネシウム（ＭｇＯ・Ａｌ２Ｏ３）、クレー（Ａｌ２Ｏ３・２ＳｉＯ２）、カオリン（Ａｌ２Ｏ３・２ＳｉＯ２・２Ｈ２Ｏ）、パイロフィライト（Ａｌ２Ｏ３・４ＳｉＯ２・Ｈ２Ｏ）、ベントナイト（Ａｌ２Ｏ３・４ＳｉＯ２・２Ｈ２Ｏ）、ケイ酸アルミニウム（Ａｌ２ＳｉＯ５、Ａｌ４・３ＳｉＯ４・５Ｈ２Ｏ等）、ケイ酸マグネシウム（Ｍｇ２ＳｉＯ４、ＭｇＳｉＯ３等）、ケイ酸カルシウム（Ｃａ２・ＳｉＯ４等）、ケイ酸アルミニウムカルシウム（Ａｌ２Ｏ３・ＣａＯ・２ＳｉＯ２等）、ケイ酸マグネシウムカルシウム（ＣａＭｇＳｉＯ４）、炭酸カルシウム（ＣａＣＯ３）、酸化ジルコニウム（ＺｒＯ２）、水酸化ジルコニウム［ＺｒＯ（ＯＨ）２・ｎＨ２Ｏ］、炭酸ジルコニウム［Ｚｒ（ＣＯ３）２］、アクリル酸亜鉛、メタクリル酸亜鉛、各種ゼオライトのように電荷を補正する水素、アルカリ金属又はアルカリ土類金属を含む結晶性アルミノケイ酸塩等が挙げられる。この中でも、炭酸カルシウム、タルク、クレーが好ましい。
1-3. Other Additives In addition to the above-mentioned components, various additives may be added to the foaming composition of the present invention within the limits that do not impair the purpose and effect of the composition. For example, carbon black, inorganic fillers, antioxidants, antiozonants, softeners, processing aids, waxes, oils, fatty acids having 8 to 30 carbon atoms such as stearic acid, fatty acid metal salts, zinc oxide (ZnO), crosslinking aids, crosslinking agents, pigments, dyes, tackifiers, bubble nucleating agents, odor absorbers, ultraviolet absorbers, light stabilizers, antioxidants, light-shielding agents, metal deactivators, quenchers, antifogging agents, antifungal agents, antibacterial agents, deodorants, plasticizers, antistatic agents, surfactants, polymerization inhibitors, sensitizers, curing accelerators, diluents, flow regulators, leveling agents, pressure sensitive adhesives, adhesives, lubricants, release agents, lubricants, solid lubricants, reinforcing agents, compatibilizers, conductive agents, antiblocking agents, antitracking agents, phosphorescent agents, flame retardants, dispersants, etc. may be appropriately selected and blended within a range that does not impair the object of the present invention. Commercially available products may be suitably used as these blending agents. The inorganic filler is not particularly limited, and examples thereof include silica; alumina (Al 2 O 3 ) such as γ-alumina and α-alumina; alumina monohydrate (Al 2 O 3 .H 2 O) such as boehmite and diaspore; aluminum hydroxide [Al(OH) 3 ] such as gibbsite and bayerite; aluminum carbonate [Al 2 (CO 3 ) 3 ], magnesium hydroxide [Mg(OH) 2 ], magnesium oxide (MgO), magnesium carbonate (MgCO 3 ), talc (3MgO.4SiO 2.H 2 O), attapulgite (5MgO.8SiO 2.9H 2 O), titanium white (TiO 2 ), titanium black (TiO 2n-1 ), calcium oxide (CaO), calcium hydroxide [Ca(OH) 2 ], magnesium aluminum oxide (MgO.Al 2 O 3 ), clay (Al 2 O 3.2SiO 2 ), kaolin (Al 2 O 3.2SiO 2.2H 2 O), pyrophyllite (Al 2 O 3.4SiO 2.H 2 O ) , bentonite (Al 2 O 3.4SiO 2.2H 2 O ) , aluminum silicate (Al 2 SiO 5 , Al 4.3SiO 4.5H 2 O, etc.), magnesium silicate (Mg 2 SiO 4 , MgSiO 3 , etc.), calcium silicate (Ca 2.SiO 4 , etc.), aluminum calcium silicate (Al 2 O 3.CaO.2SiO 2 , etc. ) , magnesium calcium silicate (CaMgSiO 4 ), calcium carbonate (CaCO 3 ), zirconium oxide (ZrO 2 ) , zirconium hydroxide [ZrO(OH) 2.nH 2 O], zirconium carbonate [Zr(CO 3 ) 2 ], zinc acrylate, zinc methacrylate, crystalline aluminosilicates containing hydrogen, alkali metals or alkaline earth metals that correct the charge, such as various zeolites, etc. Among these, calcium carbonate, talc and clay are preferred.
２．高分子材料、並びにピラゾロン誘導体のみからなる発泡用組成物
本発明の発泡用組成物は、
高分子材料、並びに、
式（１）及び（２）で表される化合物、並びに該化合物の塩から選ばれる少なくとも一種の化合物（ピラゾロン誘導体）：
2. Polymer material and foaming composition consisting of pyrazolone derivative only The foaming composition of the present invention is
Polymer materials, and
At least one compound (pyrazolone derivative) selected from compounds represented by formulas (1) and (2) and salts of said compounds:
のみからなる組成物を含む。
This includes compositions consisting only of:
本発明の「高分子材料、並びにピラゾロン誘導体のみからなる発泡用組成物」とは、実質的に、高分子材料、並びにピラゾロン誘導体（式（１）及び（２）で表される化合物、並びに該化合物の塩から選ばれる少なくとも一種の化合物）のみを含む組成物であり、本発明の効果を阻害しない程度に、上記１－３に示す、その他の配合剤を含んでいても良い。 The "foaming composition consisting only of a polymeric material and a pyrazolone derivative" of the present invention is a composition that essentially contains only a polymeric material and a pyrazolone derivative (at least one compound selected from the compounds represented by formulas (1) and (2) and salts of said compounds), and may contain other compounding agents as shown in 1-3 above to the extent that the effects of the present invention are not impaired.
本発明の高分子材料、並びにピラゾロン誘導体のみからなる発泡用組成物を用い、化学発泡剤と組み合わせ、発泡させることにより、優れた発泡倍率、及び微細な平均セル径を有する発泡体を得ることができる。 By using a foaming composition consisting only of the polymer material of the present invention and a pyrazolone derivative, in combination with a chemical foaming agent, and foaming, it is possible to obtain a foam having an excellent expansion ratio and a fine average cell diameter.
本発明の発泡用組成物は、好ましく発泡のために使用することができる。 The foaming composition of the present invention can be preferably used for foaming.
２－１．高分子材料
本発明の高分子材料、並びにピラゾロン誘導体のみからなる発泡用組成物は、高分子材料を含む。
2-1. Polymeric Material The polymeric material of the present invention and the foaming composition consisting of only a pyrazolone derivative contain a polymeric material.
高分子材料としては、特に限定はなく、公知の高分子材料を広く使用することが可能である。例えば、ゴム、樹脂、熱硬化性エラストマー、熱可塑性エラストマー等である。 There are no particular limitations on the polymeric material, and a wide range of known polymeric materials can be used. Examples include rubber, resin, thermosetting elastomers, and thermoplastic elastomers.
ゴムとしては、特に制限はなく、例えば、ジエン系ゴム、非ジエン系ゴム、並びにジエン系ゴムと非ジエン系ゴムとの混合物等が挙げられる。 There are no particular limitations on the rubber, and examples include diene rubber, non-diene rubber, and mixtures of diene rubber and non-diene rubber.
ジエン系ゴムとしては、天然ゴム、スチレン－ブタジエン共重合体ゴム（ＳＢＲ）、ブタジエンゴム（ＢＲ）、イソプレンゴム（ＩＲ）、スチレン－イソプレン－ブタジエンゴム（ＳＩＢＲ）、ニトリルゴム（ＮＢＲ）、クロロプレンゴム（ＣＲ）、スチレン－イソプレン-スチレン三元ブロック共重合体（ＳＩＳ）、スチレン－ブタジエン－スチレン三元ブロック共重合体（ＳＢＳ）等、及びこれらの変性ジエン系ゴムが挙げられる。中でも、天然ゴム、ブタジエンゴム、スチレン－ブタジエン共重合体ゴムが好ましい。 Examples of diene rubbers include natural rubber, styrene-butadiene copolymer rubber (SBR), butadiene rubber (BR), isoprene rubber (IR), styrene-isoprene-butadiene rubber (SIBR), nitrile rubber (NBR), chloroprene rubber (CR), styrene-isoprene-styrene ternary block copolymer (SIS), styrene-butadiene-styrene ternary block copolymer (SBS), and modified diene rubbers thereof. Of these, natural rubber, butadiene rubber, and styrene-butadiene copolymer rubber are preferred.
天然ゴムとしては、天然ゴムラテックス、技術的格付けゴム（ＴＳＲ）、スモークドシート（ＲＳＳ）、ガタパーチャ、杜仲由来天然ゴム、グアユール由来天然ゴム、ロシアンタンポポ由来天然ゴムなどが挙げられ、更にこれら天然ゴムを変性した、エポキシ化天然ゴム、メタクリル酸変性天然ゴム、ハロゲン変性天然ゴム、脱蛋白天然ゴム、マレイン酸変性天然ゴム、スルホン酸変性天然ゴム、スチレン変性天然ゴムなどの変性天然ゴムなどを使用することも好ましい。 Examples of natural rubber include natural rubber latex, technically graded rubber (TSR), smoked sheet (RSS), gutta percha, natural rubber derived from Eucommia ulmoides, natural rubber derived from guayule, and natural rubber derived from Russian dandelion. It is also preferable to use modified natural rubbers such as epoxylated natural rubber, methacrylic acid modified natural rubber, halogen modified natural rubber, deproteinized natural rubber, maleic acid modified natural rubber, sulfonic acid modified natural rubber, and styrene modified natural rubber.
変性ジエン系ゴムには、主鎖変性、片末端変性、両末端変性などの変性手法によるジエン系ゴムが包含される。ここで、変性ジエン系ゴムの変性官能基としては、エポキシ基、アミノ基、アルコキシシリル基、水酸基などの各種官能基が挙げられ、これら官能基は１種又は２種以上が変性ジエン系ゴムに含まれていてもよい。 Modified diene rubbers include diene rubbers modified by methods such as main chain modification, one-end modification, and both-end modification. Here, modified functional groups of modified diene rubbers include various functional groups such as epoxy groups, amino groups, alkoxysilyl groups, and hydroxyl groups, and one or more of these functional groups may be contained in the modified diene rubber.
ジエン系ゴムの製造方法は、特に制限はなく、乳化重合、溶液重合、ラジカル重合、アニオン重合、カチオン重合などが挙げられる。また、合成ジエン系ゴムのガラス転移点も、特に制限はない。 There are no particular limitations on the manufacturing method of diene rubber, and examples include emulsion polymerization, solution polymerization, radical polymerization, anionic polymerization, and cationic polymerization. There are also no particular limitations on the glass transition point of synthetic diene rubber.
非ジエン系ゴムとしては、ブチルゴム、エチレン－プロピレンゴム（ＥＰＭ）、エチレン－プロピレン－ジエン三元共重合体ゴム（ＥＰＤＭ）、ウレタンゴム（Ｕ）、六フッ化プロピレン‐フッ化ビニリデン共重合体（ＦＫＭ）、テトラフルオロエチレン‐プロピレン共重合体（ＦＥＰＭ）、テトラフルオロエチレン‐パーフルオロビニルエーテル共重合体（ＦＦＫＭ）、メチルシリコーンゴム（ＭＱ）、ビニル・メチルシリコーンゴム（ＶＭＱ）、フェニル・メチルシリコーンゴム（ＰＭＱ）、アクリルゴム（ＡＣＭ）、多硫化ゴム（Ｔ）、エピクロルヒドリンゴム（ＣＯ，ＥＣＯ）等、及びこれらの変性非ジエン系ゴムが挙げられる。中でも、ブチルゴム、エチレン－プロピレン－ジエン三元共重合体ゴム（ＥＰＤＭ）が好ましい。 Examples of non-diene rubbers include butyl rubber, ethylene-propylene rubber (EPM), ethylene-propylene-diene terpolymer rubber (EPDM), urethane rubber (U), hexafluoropropylene-vinylidene fluoride copolymer (FKM), tetrafluoroethylene-propylene copolymer (FEPM), tetrafluoroethylene-perfluorovinyl ether copolymer (FFKM), methyl silicone rubber (MQ), vinyl-methyl silicone rubber (VMQ), phenyl-methyl silicone rubber (PMQ), acrylic rubber (ACM), polysulfide rubber (T), epichlorohydrin rubber (CO, ECO), and modified non-diene rubbers thereof. Among these, butyl rubber and ethylene-propylene-diene terpolymer rubber (EPDM) are preferred.
変性非ジエン系ゴムには、主鎖変性、片末端変性、両末端変性などの変性手法による非ジエン系ゴムが包含される。ここで、変性非ジエン系ゴムの変性官能基としては、エポキシ基、アミノ基、アルコキシシリル基、水酸基などの各種官能基が挙げられ、これら官能基は１種又は２種以上が変性合成非ジエン系ゴムに含まれていてもよい。 Modified non-diene rubbers include non-diene rubbers modified by methods such as main chain modification, one-end modification, and both-end modification. Here, modified functional groups of modified non-diene rubbers include various functional groups such as epoxy groups, amino groups, alkoxysilyl groups, and hydroxyl groups, and one or more of these functional groups may be contained in the modified synthetic non-diene rubber.
非ジエン系ゴムの製造方法は、特に制限はなく、乳化重合、溶液重合、ラジカル重合、アニオン重合、カチオン重合などが挙げられる。また、合成非ジエン系ゴムのガラス転移点においても、特に制限はない。 There are no particular limitations on the method for producing non-diene rubber, and examples include emulsion polymerization, solution polymerization, radical polymerization, anionic polymerization, and cationic polymerization. There are also no particular limitations on the glass transition point of synthetic non-diene rubber.
また、天然ゴム及びジエン系ゴムの二重結合部のシス／トランス／ビニルの比率については、特に制限はなく、いずれの比率においても好適に用いることができる。また、ジエン系ゴムの数平均分子量および分子量分布についても、特に制限はなく、数平均分子量５００～３００００００、分子量分布１．５～１５が好ましい。非ジエン系ゴムとしては、公知のものを広く使用することができる。 There are no particular restrictions on the cis/trans/vinyl ratio of the double bonds of the natural rubber and diene rubber, and any ratio can be used suitably. There are no particular restrictions on the number average molecular weight and molecular weight distribution of the diene rubber, and a number average molecular weight of 500 to 3,000,000 and a molecular weight distribution of 1.5 to 15 are preferred. A wide range of known non-diene rubbers can be used.
ゴムは、１種単独で又は２種以上を混合（ブレンド）して用いることができる。 The rubber can be used alone or in a mixture (blend) of two or more types.
ゴムの中でも、エチレン－プロピレン－ジエン三元共重合体ゴム（ＥＰＤＭ）、イソプレンゴム（ＩＲ）、ブチルゴム（ＩＩＲ）、を使用することが好ましい。 Among rubbers, it is preferable to use ethylene-propylene-diene terpolymer rubber (EPDM), isoprene rubber (IR), and butyl rubber (IIR).
樹脂としては、特に限定はなく、公知の樹脂を広く使用することが可能である。例えば、上記１－１に示す、樹脂が挙げられる。 There are no particular limitations on the resin, and a wide range of known resins can be used. Examples include the resins shown in 1-1 above.
中でも、ポリエチレン、ポリプロピレン、ポリ塩化ビニル、エチレン－酢酸ビニル共重合体、ポリウレタンが好ましく、ポリエチレン、エチレン－酢酸ビニル共重合体がより好ましい。 Among these, polyethylene, polypropylene, polyvinyl chloride, ethylene-vinyl acetate copolymer, and polyurethane are preferred, and polyethylene and ethylene-vinyl acetate copolymer are more preferred.
熱硬化性エラストマーとしては、特に限定はなく、公知の熱硬化性エラストマーを広く使用することが可能である。例えば、フェノール系エラストマー、ウレア系エラストマー、メラミン系エラストマー、エポキシ系エラストマーおよびエステル系エラストマー等が挙げられる。 There are no particular limitations on the thermosetting elastomer, and a wide variety of known thermosetting elastomers can be used. Examples include phenol-based elastomers, urea-based elastomers, melamine-based elastomers, epoxy-based elastomers, and ester-based elastomers.
熱可塑性エラストマーとしては、特に限定はなく、公知の熱可塑性エラストマーを広く使用することが可能である。例えば、エチレン－メチルアクリレート共重合体、スチレン系エラストマー、ウレタン系エラストマーおよびポリオレフィン系エラストマー等
が挙げられる。
The thermoplastic elastomer is not particularly limited, and a wide variety of known thermoplastic elastomers can be used, such as ethylene-methyl acrylate copolymers, styrene-based elastomers, urethane-based elastomers, and polyolefin-based elastomers.
２－２．ピラゾロン誘導体
本発明の高分子材料、並びにピラゾロン誘導体のみからなる発泡用組成物は、上記１－２に示す、ピラゾロン誘導体を含む。
2-2. Pyrazolone Derivatives The polymer material of the present invention and the foaming composition consisting of only a pyrazolone derivative contain the pyrazolone derivative shown in 1-2 above.
中でも、好ましいピラゾロン誘導体は、５－ピラゾロン、３－メチル－５－ピラゾロン、３－ｔ－ブチル－１Ｈ－ピラゾール－５（４Ｈ）－オン、３－（ナフタレン－２－イル）－１Ｈ－ピラゾール－５（４Ｈ）－オン、３－（フラン－２－イル）－１Ｈ－ピラゾール－５（４Ｈ）－オン、３－フェニル－１Ｈ－ピラゾール－５（４Ｈ）－オン、及び３－プロピル－１Ｈ－ピラゾール－５（４Ｈ）－オンがより好ましい。 Among these, preferred pyrazolone derivatives are 5-pyrazolone, 3-methyl-5-pyrazolone, 3-t-butyl-1H-pyrazol-5(4H)-one, 3-(naphthalen-2-yl)-1H-pyrazol-5(4H)-one, 3-(furan-2-yl)-1H-pyrazol-5(4H)-one, 3-phenyl-1H-pyrazol-5(4H)-one, and more preferably 3-propyl-1H-pyrazol-5(4H)-one.
３．発泡組成物の製造方法
発泡組成物は、上記発泡用組成物に、発泡剤を混合した組成物を示す。
3. Method for Producing Foaming Composition The foaming composition refers to a composition obtained by mixing the foaming composition described above with a foaming agent.
本発明の発泡組成物の製造方法は、
（Ａ）樹脂、並びに、式（１）及び（２）で表される化合物、並びに該化合物の塩から選ばれる少なくとも一種の化合物を混合して、発泡用組成物を得る工程、並びに、
（Ｂ）前記工程（Ａ）で得られた発泡用組成物に、化学発泡剤を混合し、発泡組成物を得る工程
を含む。
The method for producing the foam composition of the present invention comprises the steps of:
(A) a step of mixing a resin and at least one compound selected from the compounds represented by formulas (1) and (2) and salts of said compounds to obtain a foaming composition; and
(B) A step of mixing a chemical foaming agent with the foaming composition obtained in the step (A) to obtain a foaming composition.
本発明の製造方法で得られた発泡組成物を用い、発泡させることにより、優れた発泡倍率、及び微細な平均セル径を有する発泡体を得ることができる。 By foaming the foam composition obtained by the manufacturing method of the present invention, a foam having an excellent expansion ratio and a fine average cell diameter can be obtained.
３－１．工程（Ａ）
工程（Ａ）は、樹脂、並びに、式（１）及び（２）で表される化合物、並びに該化合物の塩から選ばれる少なくとも一種の化合物とを混合して、発泡用組成物を得る工程である。
3-1. Step (A)
Step (A) is a step of mixing a resin with at least one compound selected from the compounds represented by formulas (1) and (2) and salts of said compounds to obtain a foaming composition. be.
樹脂としては、上記１－１に示す、樹脂を用いることができる。 The resins shown in 1-1 above can be used.
工程（Ａ）の樹脂とピラゾロン誘導体とを混合する工程において、化学発泡剤を含まないことで、最終的に優れた発泡倍率と微細な平均セル径を有する発泡体を得ることができる。 By not including a chemical foaming agent in the step (A) of mixing the resin and pyrazolone derivative, it is possible to obtain a foam with an excellent expansion ratio and a fine average cell diameter.
工程（Ａ）における混合方法としては、公知の方法で混合することができる。混合は、例えば、回転ボールミル、振動ボールミル、遊星ミル、ペイントシェーカー、ロッキングミル、ロッキングミキサー、ビーズミル、撹拌機等を用いて、湿式及び乾式のどちらでも行うことができる。 The mixing method in step (A) can be a known method. Mixing can be performed in either a wet or dry manner using, for example, a rotary ball mill, a vibrating ball mill, a planetary mill, a paint shaker, a rocking mill, a rocking mixer, a bead mill, or a stirrer.
工程（Ａ）では、更に必要に応じて、上記１－３に示す、その他の配合剤等を配合することができる。 In step (A), other compounding agents such as those shown in 1-3 above can be further compounded as necessary.
３－２．工程（Ｂ）
工程（Ｂ）は、上記工程（Ａ）で得られた発泡用組成物に、化学発泡剤を混合し、発泡組成物を得る工程である。
3-2. Step (B)
The step (B) is a step of mixing a chemical foaming agent with the foaming composition obtained in the step (A) to obtain a foaming composition.
工程（Ｂ）で得られる発泡組成物を発泡させて得られる発泡体は、優れた発泡倍率と微細な平均セル径を有する。 The foam obtained by foaming the foam composition obtained in step (B) has an excellent expansion ratio and a fine average cell diameter.
工程（Ｂ）における混合方法としては、公知の方法で混合することができ、上記工程（Ａ）における混合方法と同様である。 The mixing method in step (B) can be a known method, and is the same as the mixing method in step (A) above.
また、工程（Ａ）で混合した樹脂を、更に工程（Ｂ）でも追加して混合してもよい。 The resin mixed in step (A) may also be further mixed in step (B).
工程（Ｂ）で混合することができる樹脂は、工程（Ａ）の発泡用組成物に適用した樹脂と同じ樹脂でもよいし、異なる樹脂でもよく、特に限定はない。上記１－１に示す、樹脂を混合することができる。 The resin that can be mixed in step (B) may be the same resin as that applied to the foaming composition in step (A) or a different resin, and is not particularly limited. The resins shown in 1-1 above can be mixed.
工程（Ｂ）では、更に必要に応じて、上記１－３に示す、その他の配合剤等を配合することができる。 In step (B), other compounding agents such as those shown in 1-3 above can be further compounded as necessary.
３－３．化学発泡剤
化学発泡剤としては、特に限定はなく、公知の化学発泡剤を広く使用することが可能である。例えば、アゾジカルボンアミド、Ｎ，Ｎ’－ジニトロソペンタンメチレンテトラミン、ｐ，ｐ’－オキシビスベンゼンスルホニルヒドラジド、パラトルエンスルホニルヒドラジド、ｐ－トルエンスルホニルセミカルバジド、ジアゾアミノベンゼン、ヒドラゾジカルボンアミド、バリウムアゾジカルボキシレート、アゾビスイソブチロニトリル、クエン酸モノナトリウムなど有機酸及びそれらの金属塩等の有機系化学発泡剤及び、重曹、炭酸水素アンモニウム、炭酸ナトリウム、炭酸アンモニウム、酢酸アルミニウム、亜硝酸アンモニウム、ホウ化水素ナトリウム等の無機系化学発泡剤が挙げられる。
3-3. Chemical Foaming Agent There is no particular limitation on the chemical foaming agent, and a wide variety of known chemical foaming agents can be used. Examples of the chemical foaming agent include organic chemical foaming agents such as azodicarbonamide, N,N'-dinitrosopentanmethylenetetramine, p,p'-oxybisbenzenesulfonylhydrazide, paratoluenesulfonylhydrazide, p-toluenesulfonylsemicarbazide, diazoaminobenzene, hydrazodicarbonamide, barium azodicarboxylate, azobisisobutyronitrile, monosodium citrate, and other organic acids and metal salts thereof, and inorganic chemical foaming agents such as sodium bicarbonate, ammonium hydrogen carbonate, sodium carbonate, ammonium carbonate, aluminum acetate, ammonium nitrite, and sodium borohydride.
上記化学発泡剤は、１種単独で、又は２種以上を混合（ブレンド）して用いることができる。 The above chemical foaming agents can be used alone or in a mixture (blend) of two or more.
上記化学発泡剤の中でも、アゾジカルボンアミド、ｐ，ｐ’－オキシビスベンゼンスルホニルヒドラジド、Ｎ，Ｎ’－ジニトロソペンタンメチレンテトラミン、又は重曹が好ましい。 Among the above chemical foaming agents, azodicarbonamide, p,p'-oxybisbenzenesulfonylhydrazide, N,N'-dinitrosopentanemethylenetetramine, or sodium bicarbonate are preferred.
３－４．配合割合
工程（Ａ）、及び（Ｂ）で使用する樹脂の全量を１００質量部とした場合、発泡組成物中のピラゾロン誘導体の配合量は、好ましくは、０．１質量部～３０質量部であり、より好ましくは、０．３質量部～１０質量部である。
3-4. Blending ratio When the total amount of the resins used in steps (A) and (B) is 100 parts by mass, the blending amount of the pyrazolone derivative in the foaming composition is preferably 0.1 to 30 parts by mass, more preferably 0.3 to 10 parts by mass.
工程（Ａ）、及び（Ｂ）で使用する樹脂の全量を１００質量部とした場合、発泡組成物中の化学発泡剤の配合量は、好ましくは、０．１質量部～８０質量部であり、より好ましくは、０．３質量部～５０質量部である。 When the total amount of the resins used in steps (A) and (B) is 100 parts by mass, the amount of the chemical foaming agent in the foaming composition is preferably 0.1 parts by mass to 80 parts by mass, and more preferably 0.3 parts by mass to 50 parts by mass.
４．発泡体の製造方法
本発明の発泡体の製造方法は、
（Ｃ）上記工程（Ｂ）で得られた発泡組成物を発泡させる工程
を含む。
4. Method for Producing Foam The method for producing a foam of the present invention comprises the steps of:
(C) A step of foaming the foam composition obtained in the above step (B).
上記工程（Ｂ）で得られた発泡組成物を発泡させる方法としては、公知の方法で発泡させることができ、例えば、発泡組成物を加熱して、発泡を行うことにより、製造することができる。 The foam composition obtained in step (B) can be foamed by a known method, for example, by heating the foam composition to foam it.
加熱温度は、発泡組成物に含まれる化学発泡剤が分解する温度以上であればよく、好ましくは、５０℃～３００℃程度であり、より好ましくは、８０℃～２５０℃程度であり、更に好ましくは、１００℃～２００℃程度である。 The heating temperature should be equal to or higher than the temperature at which the chemical foaming agent contained in the foaming composition decomposes, and is preferably about 50°C to 300°C, more preferably about 80°C to 250°C, and even more preferably about 100°C to 200°C.
加熱時間は、好ましくは、５秒間～２４時間程度であり、より好ましくは、１０秒～１２時間であり、更に好ましくは、２分間～３時間程度である。 The heating time is preferably about 5 seconds to about 24 hours, more preferably about 10 seconds to about 12 hours, and even more preferably about 2 minutes to about 3 hours.
以下、実施例に基づき、本発明の実施形態をより具体的に説明する。 Hereinafter, the embodiment of the present invention will be described in more detail based on the examples.
本発明がこれらに限定されるものではない。 The present invention is not limited to these.
（１）実施例１～１１、及び比較例１～６
（１－１）発泡体の製造
下記表１の工程Ａに記載の各成分をその割合（質量部）でミキシングロールにて、１２０℃で、表１の「工程Ａでの混合時間」に記載の時間で、混合し、本発明の発泡用組成物を得た。
(1) Examples 1 to 11 and Comparative Examples 1 to 6
(1-1) Production of Foam The components shown in step A of Table 1 below were mixed in the ratio (parts by mass) using a mixing roll at 120° C. for the time shown in “Mixing time in step A” of Table 1 to obtain a foaming composition of the present invention.
得られた発泡用組成物に、表１の工程Ｂに記載の各成分をその割合（質量部）で投入し、ミキシングロールにて、１２０℃で混合し、発泡組成物を得た。 The components listed in step B of Table 1 were added to the obtained foaming composition in the proportions (parts by mass) shown, and mixed at 120°C using a mixing roll to obtain a foaming composition.
得られた発泡組成物を１１０℃に加熱したプレス機にて、縦１６０ｍｍ、横１６０ｍｍ、厚み３ｍｍの金型を用いて、発泡前のシートを作成した。発泡前シートを２２０℃のギヤオーブンで加熱する事で発泡体を製造した。 The obtained foam composition was pressed in a press heated to 110°C using a mold measuring 160 mm in length, 160 mm in width, and 3 mm in thickness to create a pre-foamed sheet. The pre-foamed sheet was heated in a gear oven at 220°C to produce a foam.
比較例１～３、及び５（表２）は、ピラゾロン誘導体を添加しない以外は、各実施例と同じ配合内容で、上記製造方法で製造した発泡体である。 Comparative Examples 1 to 3 and 5 (Table 2) are foams produced by the above-mentioned production method with the same composition as each Example, except that no pyrazolone derivative was added.
比較例４及び６（表２）は、ピラゾロン誘導体を工程Ｂに加えること以外は、各実施例と同じ配合内容で、上記製造方法で製造した発泡体である。 Comparative Examples 4 and 6 (Table 2) are foams produced by the above-mentioned production method with the same composition as each Example, except that a pyrazolone derivative was added in step B.
（１－２）発泡倍率指数
発泡倍率は電子比重計（ＡＬＦＡ ＭＩＲＡＧＥ製ＭＤＳ－３００）を用いて発泡成形前後の比重を測定し、発泡倍率を算出した。
(1-2) Expansion Ratio Index The expansion ratio was calculated by measuring the specific gravity before and after expansion molding using an electronic specific gravity meter (MDS-300 manufactured by ALFA MIRAGE).
比較例の発泡体を作製し、その発泡倍率を１００とした指数で表し、下記式に基づいて、実施例、及び比較例の発泡体の発泡倍率指数を算出した。 A comparative example foam was produced, and its expansion ratio was expressed as an index with 100 as the expansion ratio. The expansion ratio index of the examples and comparative examples foam was calculated based on the following formula.
発泡倍率指数の値が大きい程、発泡倍率が大きく、発泡体として優れている。 The higher the value of the expansion ratio index, the higher the expansion ratio and the better the foam.
式：発泡倍率
＝発泡成形前の比重／発泡成形後の比重×１００
式：実施例１～３の発泡倍率指数
＝（実施例１～３の発泡倍率）×１００／（比較例１の発泡倍率）
式：実施例４～７の発泡倍率指数
＝（実施例４～７の発泡倍率）×１００／（比較例２の発泡倍率）
式：実施例８～９の発泡倍率指数
＝（実施例８～９の発泡倍率）×１００／（比較例３の発泡倍率）
式：比較例４の発泡倍率指数
＝（比較例４の発泡倍率）×１００／（比較例３の発泡倍率）
式：実施例１０～１１の発泡倍率指数
＝（実施例１０～１１の発泡倍率）×１００／（比較例５の発泡倍率）
式：比較例６の発泡倍率指数
＝（比較例６の発泡倍率）×１００／（比較例５の発泡倍率）
Formula: Expansion ratio = specific gravity before foam molding/specific gravity after foam molding x 100
Formula: Expansion Ratio Index of Examples 1 to 3 = (Expansion Ratio of Examples 1 to 3) x 100 / (Expansion Ratio of Comparative Example 1)
Formula: Expansion Ratio Index of Examples 4 to 7 = (Expansion Ratio of Examples 4 to 7) x 100 / (Expansion Ratio of Comparative Example 2)
Formula: Expansion Ratio Index of Examples 8 to 9 = (Expansion Ratio of Examples 8 to 9) x 100 / (Expansion Ratio of Comparative Example 3)
Formula: Expansion Ratio Index of Comparative Example 4 = (Expansion Ratio of Comparative Example 4) x 100 / (Expansion Ratio of Comparative Example 3)
Formula: Expansion Ratio Index of Examples 10 to 11 = (Expansion Ratio of Examples 10 to 11) x 100 / (Expansion Ratio of Comparative Example 5)
Formula: Expansion Ratio Index of Comparative Example 6 = (Expansion Ratio of Comparative Example 6) x 100 / (Expansion Ratio of Comparative Example 5)
（１－３）平均セル径指数
平均セル径はＡＳＴＭ Ｄ２８４２－６９に準拠し、算出した。
(1-3) Average Cell Size Index The average cell size was calculated in accordance with ASTM D2842-69.
比較例の発泡体を作製し、その平均セル径を１００とした指数で表し、下記式に基づいて、実施例、及び比較例の発泡体の平均セル径指数を算出した。 A comparative foam was produced, and its average cell diameter was expressed as an index of 100. The average cell diameter index of the foams of the examples and comparative examples was calculated based on the following formula.
平均セル径指数の値が小さい程、平均セル径が小さく、発泡体として優れている。 The smaller the average cell size index value, the smaller the average cell size and the better the foam.
式：実施例１～３の平均セル径指数
＝（実施例１～３の平均セル径）×１００／（比較例１の平均セル径）
式：実施例４～７の平均セル径指数
＝（実施例４～７の平均セル径）×１００／（比較例２の平均セル径）
式：実施例８～９の平均セル径指数
＝（実施例８～９の平均セル径）×１００／（比較例３の平均セル径）
式：比較例４の平均セル径指数
＝（比較例４の平均セル径）×１００／（比較例３の平均セル径）
式：実施例１０～１１の平均セル径指数
＝（実施例１０～１１の平均セル径）×１００／（比較例５の平均セル径）
式：比較例６の平均セル径指数
＝（比較例６の平均セル径）×１００／（比較例５の平均セル径）
Formula: Average cell size index of Examples 1 to 3 = (average cell size of Examples 1 to 3) x 100 / (average cell size of Comparative Example 1)
Formula: Average cell size index of Examples 4 to 7 = (average cell size of Examples 4 to 7) x 100 / (average cell size of Comparative Example 2)
Formula: Average cell size index of Examples 8 to 9 = (average cell size of Examples 8 to 9) x 100 / (average cell size of Comparative Example 3)
Formula: Average cell size index of Comparative Example 4 = (average cell size of Comparative Example 4) x 100 / (average cell size of Comparative Example 3)
Formula: Average cell size index of Examples 10 to 11 = (average cell size of Examples 10 to 11) x 100 / (average cell size of Comparative Example 5)
Formula: Average cell size index of Comparative Example 6 = (average cell size of Comparative Example 6) x 100 / (average cell size of Comparative Example 5)
（２）実施例１２～１４、及び比較例７～８
（２－１）発泡体の製造
下記表３の工程Ａに記載の各成分をその割合（質量部）でミキシングロールにて、１２０℃で、表３の「工程Ａでの混合時間」に記載の時間で、混合し、本発明の発泡用組成物を得た。
(2) Examples 12 to 14 and Comparative Examples 7 to 8
(2-1) Production of Foam The components shown in step A of Table 3 below were mixed in the ratio (parts by mass) using a mixing roll at 120° C. for the time shown in “Mixing time in step A” of Table 3 to obtain a foaming composition of the present invention.
得られた発泡用組成物に、表３の工程Ｂに記載の各成分をその割合（質量部）で投入し、ミキシングロールにて、１２０℃で混合し、発泡組成物を得た。 The components listed in step B of Table 3 were added to the obtained foaming composition in the proportions (parts by mass) shown, and mixed at 120°C using a mixing roll to obtain a foaming composition.
得られた発泡組成物を１６０℃に加熱したプレス機にて、発泡体を製造した。 The resulting foam composition was heated to 160°C in a press to produce a foam.
比較例７～８（表３）は、ピラゾロン誘導体を添加しない以外は、各実施例と同じ配合内容で、上記製造方法で製造した発泡体である。 Comparative Examples 7 to 8 (Table 3) are foams produced using the above manufacturing method with the same formulation as each Example, except that no pyrazolone derivative was added.
（２－２）発泡倍率指数
発泡倍率は電子比重計（ＡＬＦＡ ＭＩＲＡＧＥ製ＭＤＳ－３００）を用いて発泡成形前後の比重を測定し、発泡倍率を算出した。
(2-2) Expansion Ratio Index The expansion ratio was calculated by measuring the specific gravity before and after expansion molding using an electronic specific gravity meter (MDS-300 manufactured by ALFA MIRAGE).
比較例の発泡体を作製し、その発泡倍率を１００とした指数で表し、下記式に基づいて、実施例の発泡体の発泡倍率指数を算出した。 A foam of the comparative example was produced, and its expansion ratio was expressed as an index with 100 as the expansion ratio, and the expansion ratio index of the foam of the example was calculated based on the following formula.
発泡倍率指数の値が大きい程、発泡倍率が大きく、発泡体として優れている。 The higher the value of the expansion ratio index, the higher the expansion ratio and the better the foam.
式：実施例１２～１３の発泡倍率指数
＝（実施例１２～１３の発泡倍率）×１００／（比較例７の発泡倍率）
式：実施例１４の発泡倍率指数
＝（実施例１４の発泡倍率）×１００／（比較例８の発泡倍率）
Formula: Expansion Ratio Index of Examples 12 to 13 = (Expansion Ratio of Examples 12 to 13) x 100 / (Expansion Ratio of Comparative Example 7)
Formula: Expansion Ratio Index of Example 14 = (Expansion Ratio of Example 14) x 100 / (Expansion Ratio of Comparative Example 8)
（３）実施例１５～１６、及び比較例９～１０
（３－１）実施例１５、及び１６の発泡体の製造
下記表５の工程Ａに記載の各成分をその割合（質量部）で投入し、バンバリーミキサーにて、１１０℃で混合し、表５の工程Ａに記載の各成分の混合物を得た。
(3) Examples 15 to 16 and Comparative Examples 9 to 10
(3-1) Production of foams of Examples 15 and 16 Each component shown in step A of Table 5 below was added in the corresponding ratio (parts by mass) and mixed at 110°C in a Banbury mixer to obtain a mixture of each component shown in step A of Table 5.
得られた表５の工程Ａに記載の各成分の混合物に、表５の工程Ｂに記載の各成分をその割合（質量部）で投入し、ミキシングロールにて、４０℃で混合し、発泡組成物を得た。 The components listed in step B of Table 5 were added to the mixture of components listed in step A of Table 5 in the proportions (parts by mass) listed in step B of Table 5, and mixed at 40°C using a mixing roll to obtain a foaming composition.
表５の「発泡用組成物１」は、下記表４に記載の各成分をその割合（質量部）でミキシングロールにて、１２０℃で、５分間混合してできた、本発明の発泡用組成物である。 "Foaming composition 1" in Table 5 is a foaming composition of the present invention obtained by mixing the components shown in Table 4 below in the ratio (parts by mass) at 120°C for 5 minutes on a mixing roll.
発泡組成物を２２０℃のギヤオーブンで加熱する事で発泡体を製造した。 The foam was produced by heating the foam composition in a gear oven at 220°C.
比較例９（表５）は、発泡用組成物１を添加しない以外は、実施例１５、及び１６と同じ配合内容で、上記製造方法で製造した発泡体である。 Comparative Example 9 (Table 5) is a foam produced by the above-mentioned production method with the same composition as in Examples 15 and 16, except that foaming composition 1 was not added.
比較例１０（表５）は、発泡用組成物１を添加しない代わりに、ピラゾロン誘導体を工程Ｂに加えること以外は、実施例１５、及び１６と同じ配合内容で、上記製造方法製造した発泡体である。 Comparative Example 10 (Table 5) is a foam produced by the above-mentioned production method with the same composition as in Examples 15 and 16, except that instead of adding foaming composition 1, a pyrazolone derivative was added in step B.
（３－２）発泡倍率指数
発泡倍率は電子比重計（ＡＬＦＡ ＭＩＲＡＧＥ製ＭＤＳ－３００）を用いて発泡成形前後の比重を測定し、発泡倍率を算出した。
(3-2) Expansion Ratio Index The expansion ratio was calculated by measuring the specific gravity before and after expansion molding using an electronic specific gravity meter (MDS-300 manufactured by ALFA MIRAGE).
比較例の発泡体を作製し、その発泡倍率を１００とした指数で表し、下記式に基づいて、実施例の発泡体の発泡倍率指数を算出した。 A foam of the comparative example was produced, and its expansion ratio was expressed as an index with 100 as the expansion ratio, and the expansion ratio index of the foam of the example was calculated based on the following formula.
発泡倍率指数の値が大きい程、発泡倍率が大きく、発泡体として優れている。 The higher the value of the expansion ratio index, the higher the expansion ratio and the better the foam.
式：発泡倍率
＝発泡成形前の比重／発泡成形後の比重×１００
式：実施例１５～１６の発泡倍率指数
＝（実施例１５～１６の発泡倍率）×１００／（比較例９の発泡倍率）
式：比較例１０の発泡倍率指数
＝（比較例１０の発泡倍率）×１００／（比較例９の発泡倍率）
Formula: Expansion ratio = specific gravity before foam molding/specific gravity after foam molding x 100
Formula: Expansion Ratio Index of Examples 15 to 16 = (Expansion Ratio of Examples 15 to 16) x 100 / (Expansion Ratio of Comparative Example 9)
Formula: Expansion Ratio Index of Comparative Example 10 = (Expansion Ratio of Comparative Example 10) x 100 / (Expansion Ratio of Comparative Example 9)
（３－３）平均セル径指数
平均セル径はＡＳＴＭ Ｄ２８４２－６９に準拠し、算出した。
(3-3) Average Cell Size Index The average cell size was calculated in accordance with ASTM D2842-69.
比較例の発泡体を作製し、その平均セル径を１００とした指数で表し、下記式に基づいて、実施例、及び比較例の発泡体の平均セル径指数を算出した。 A comparative foam was produced, and its average cell diameter was expressed as an index of 100. The average cell diameter index of the foams of the examples and comparative examples was calculated based on the following formula.
平均セル径指数の値が小さい程、平均セル径が小さく、発泡体として優れている。 The smaller the average cell size index value, the smaller the average cell size and the better the foam.
式：実施例１５～１６の平均セル径指数
＝（実施例１５～１６の平均セル径）×１００／（比較例９の平均セル径）
式：比較例１０の平均セル径指数
＝（比較例１０の平均セル径）×１００／（比較例９の平均セル径）
Formula: Average cell size index of Examples 15 to 16 = (average cell size of Examples 15 to 16) x 100 / (average cell size of Comparative Example 9)
Formula: Average cell size index of Comparative Example 10 = (average cell size of Comparative Example 10) x 100 / (average cell size of Comparative Example 9)
各成分の詳細
※１：低密度ポリエチレン、ＭＦＲ値 １．９
※２：低密度ポリエチレン、ＭＦＲ値 ３．７
※３：ピラゾロン誘導体、３－メチル－５－ピラゾロン
※４：アゾジカルボンアミド
※５：重曹
※６：ジクミルパーオキサイド、日本油脂社製
※７：東ソー社製、ウルトラセン６３０
※８：Ｎ,Ｎ’－ジニトロソペンタメチレンテトラミン
※９：尿素
※１０：エチレン-プロピレン-ジエン-三元共重合体、住友化学社製、エスプレン５０ ５Ａ
※１１：旭カーボン社製、＃５０
※１２：出光昭和シェル社製、ダイアナプロセスオイルＰＷ－９０
※１３：大内新興化学社製、ノクセラーＭ
※１４：大内新興化学社製、ノクセラーＢＺ－Ｐ
※１５：大内新興化学社製、ノクセラーＴＥＴ－Ｇ
※１６：大内新興化学社製、ノクセラーＴＲＡ
Details of each component *1: Low density polyethylene, MFR value 1.9
*2: Low density polyethylene, MFR value 3.7
*3: Pyrazolone derivative, 3-methyl-5-pyrazolone *4: Azodicarbonamide *5: Sodium bicarbonate *6: Dicumyl peroxide, manufactured by Nippon Oil & Fats Co., Ltd. *7: Ultrathene 630, manufactured by Tosoh Corporation
*8: N,N'-dinitrosopentamethylenetetramine *9: Urea *10: Ethylene-propylene-diene-terpolymer, manufactured by Sumitomo Chemical Co., Ltd., Esprene 50 5A
*11: Asahi Carbon Co., Ltd., #50
*12: Diana Process Oil PW-90, manufactured by Idemitsu Showa Shell Co., Ltd.
*13: Noccela M, manufactured by Ouchi Shinko Chemical Co., Ltd.
*14: Noccela BZ-P, manufactured by Ouchi Shinko Chemical Co., Ltd.
*15: Noccela TET-G, manufactured by Ouchi Shinko Chemical Co., Ltd.
*16: Noccela TRA, manufactured by Ouchi Shinko Chemical Co., Ltd.
本発明の製造方法で製造された発泡体は、優れた発泡倍率と微細なセル径を有する。 The foam produced by the method of the present invention has an excellent expansion ratio and fine cell diameter.
本発明の発泡体の製造方法は、以下の工程（Ａ）～（Ｃ）を含む。 The method for producing a foam of the present invention includes the following steps (A) to (C).
（Ａ）高分子材料（樹脂）と特定のピラゾロン系化合物とを混合して発泡用組成物を得る工程。 (A) A process for obtaining a foaming composition by mixing a polymeric material (resin) with a specific pyrazolone compound.
（Ｂ）前記工程（Ａ）で得られた発泡用組成物に、発泡剤を混合し、発泡組成物を得る工程。 (B) A process for mixing a foaming agent with the foaming composition obtained in the process (A) to obtain a foaming composition.
（Ｃ）前記工程（Ｂ）で得られた発泡組成物を発泡させて発泡体を得る工程。 (C) A process for foaming the foam composition obtained in the process (B) to obtain a foam.
本発明は、優れた発泡倍率、及び微細なセル径を有する発泡体の製造方法を提供することができる。 The present invention provides a method for producing a foam with an excellent expansion ratio and fine cell diameter.
Claims (4)
式（１）及び（２）で表される化合物、並びに該化合物の塩から選ばれる少なくとも一種の化合物：
を含む、発泡用組成物（但し、発泡剤を含まない）。 A resin, and at least one compound selected from compounds represented by formulas (1) and (2) and salts of said compounds:
1. A foaming composition comprising the steps of:
式（１）及び（２）で表される化合物、並びに該化合物の塩から選ばれる少なくとも一種の化合物：
のみからなる、発泡用組成物。 Polymer materials, and
At least one compound selected from the compounds represented by formulas (1) and (2) and salts of said compounds:
A foaming composition comprising only the above-mentioned.
（Ａ）樹脂、並びに、式（１）及び（２）で表される化合物、並びに該化合物の塩から選ばれる少なくとも一種の化合物を混合して、発泡用組成物を得る工程、及び
（Ｂ）前記工程（Ａ）で得られた発泡用組成物に、化学発泡剤を混合し、発泡組成物を得る工程
を含む、製造方法。 A method for producing a foam composition, comprising the steps of:
A production method comprising: (A) a step of mixing a resin and at least one compound selected from the group consisting of compounds represented by formulas (1) and (2) and salts of said compounds to obtain a foaming composition; and (B) a step of mixing a chemical foaming agent with the foaming composition obtained in the step (A) to obtain a foaming composition.
請求項３に記載の製造方法に、更に
（Ｃ）前記工程（Ｂ）で得られた発泡組成物を、発泡させて、発泡体を得る工程
を含む、製造方法。 A method for producing a foam, comprising the steps of:
The method according to claim 3 , further comprising: (C) a step of foaming the foam composition obtained in the step (B) to obtain a foam.
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|---|---|---|---|
| JP2022193994A JP2024080774A (en) | 2022-12-05 | 2022-12-05 | Foaming composition, method for producing foaming composition, and method for producing foam |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022193994A JP2024080774A (en) | 2022-12-05 | 2022-12-05 | Foaming composition, method for producing foaming composition, and method for producing foam |
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| Publication Number | Publication Date |
|---|---|
| JP2024080774A true JP2024080774A (en) | 2024-06-17 |
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ID=91483264
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022193994A Pending JP2024080774A (en) | 2022-12-05 | 2022-12-05 | Foaming composition, method for producing foaming composition, and method for producing foam |
Country Status (1)
| Country | Link |
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2022
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