JP4775764B2 - 重合性不飽和樹脂用硬化促進剤及び重合性不飽和樹脂組成物 - Google Patents
重合性不飽和樹脂用硬化促進剤及び重合性不飽和樹脂組成物 Download PDFInfo
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- JP4775764B2 JP4775764B2 JP2006176111A JP2006176111A JP4775764B2 JP 4775764 B2 JP4775764 B2 JP 4775764B2 JP 2006176111 A JP2006176111 A JP 2006176111A JP 2006176111 A JP2006176111 A JP 2006176111A JP 4775764 B2 JP4775764 B2 JP 4775764B2
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- Prior art keywords
- polymerizable unsaturated
- acid
- meth
- curing
- unsaturated resin
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- 230000001588 bifunctional effect Effects 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- 229940103091 potassium benzoate Drugs 0.000 description 1
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
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- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
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- 239000004576 sand Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
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Landscapes
- Polymerization Catalysts (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
本発明の他の目的は、そのような硬化促進剤を含有し、外気温度の低い冬季においても短時間で硬化し生産性を高めることのできる重合性不飽和樹脂組成物を提供することにある。
本発明の更に他の目的は、硬化剤とそのような硬化促進剤を用いて重合性不飽和樹脂組成物を硬化させる方法を提供することにある。
更に、本発明は、重合性不飽和樹脂、硬化剤及び硬化促進剤を含有する重合性不飽和樹脂組成物において、硬化促進剤が有機酸コバルトホウ素金属塩である重合性不飽和樹脂組成物を提供する。
更にまた、本発明は、硬化剤と硬化促進剤としての有機酸コバルトホウ素金属塩を用いて、重合性不飽和樹脂組成物を硬化させる方法を提供する。
また、本発明の重合性不飽和樹脂組成物及び該組成物の硬化方法によれば、そのような強い硬化促進性を有する硬化促進剤を使用するため、外気温度の低い冬季においても短時間で組成物を硬化させ生産性を高めることができる。
B(OCoR)3 (1)
(式中、Rは有機酸基を表し、分子中の3つのRは同一でもよく又は異なっていてもよい。)
で表される有機酸金属塩を包含する。
一般式(1)中、有機酸基Rは、例えばプロピオン酸、オクチル酸、ナフテン酸、ネオデカン酸、桐油酸、亜麻仁油酸、大豆油酸、樹脂酸等の有機酸のカルボキシレート基であり、好ましくは炭素原子数3〜12の脂肪族モノカルボン酸のカルボキシレート基であり、より好ましくはオクチル酸、ナフテン酸、ネオデカン酸のカルボキシレート基である。
合成例1(ネオデカン酸コバルトホウ素金属塩の合成)
ネオデカン酸3モル、プロピオン酸3.1モルの混合物に水酸化コバルト3モルを添加し、その後190℃にて反応させ、6モルの水が生成留去するまで加熱を続けた。生成したコバルトのプロピオン酸塩にホウ酸n−ブチル1モルを添加し、220℃まで昇温して、生成留去するプロピオン酸ブチルが3モルになるまで加熱を続けることによって、目的とするネオデカン酸コバルトホウ素金属塩(A1)を得た。得られたネオデカン酸コバルトホウ素金属塩(A1)の水で抽出されるホウ素の含有率(測定方法は、本文中に記載)は0.04重量%であり、コバルト含有率は22重量%であった。
温度計、攪拌機、不活性ガス導入口、及び還流冷却器を備えた2Lの4つ口フラスコにプロピレングリコール353部、イソフタル酸249部、フマル酸348部を仕込み、210℃まで昇温し、エステル化反応を行い、14時間反応後、スチレンモノマー774部、ハイドロキノン0.04部を加え、樹脂分55.0%、酸価17の不飽和ポリエステル樹脂組成物(R1)を得た。
温度計、攪拌機、不活性ガス導入口、及び還流冷却器を備えた2Lの4つ口フラスコに数平均分子量400のPPG1.8モルを仕込み、トリレンジイソシアネート3.6モル(626.4g)加え発熱を抑制しながら80℃で5時間反応した。NCO当量が理論値とほぼ同じ374となり安定した後に40℃迄冷却し、2−ヒドロキシエチルメタクリレート3.7モル(481g)加え、空気雰囲気下90℃で7時間反応させた。NCO%が0.1重量%以下となった後、ハイドロキノン0.067部とターシャルブチルカテコール0.033部、2−ヒドロキシエチルメタクリレート466gを添加し均一に溶解し、アクリルウレタン樹脂組成物(R2)を得た。
温度計、攪拌機、不活性ガス導入口、及び還流冷却器を備えた4つ口フラスコに、ビスフェノールAとエピクロルヒドリンとの反応により得られたエポキシ当量が185の「エピクロン850」〔大日本インキ化学工業社製、エポキシ樹脂〕1850g、メタクリル酸860g、ハイドロキノン1.36g及びトリエチルアミン10.8gを仕込んで120℃まで昇温させ、同温度で10時間反応を続けて、酸価3.5、色数2の液状エポキシメタアクリレートを得た。これを2−ヒドロキシエチルメタクリレート1459gに均一溶解し、エポキシメタアクリレート樹脂組成物(R3)を得た。
合成例1で得られた金属塩、及び「Co−NAPHTHENATE 6%」、「DICNATE 5000」(いずれも大日本インキ化学工業社製、商品名)を用いて、表1に記載の配合比で硬化促進剤を調整した。なお、「Co−NAPHTHENATE 6%」は、ナフテン酸コバルト塩のミネラルスピリット溶液であり、コバルト金属含有量が6%であり、DICNATE 5000は、ネオデカン酸コバルトの無溶液品で、コバルト金属含有量が14%である。
合成例2〜4で得られた樹脂組成物(R1)〜(R3)に、硬化剤のメチルエチルケトンパーオキサイド(日本油脂社製、「パーメックN」)、及び実施例1〜3と比較例1〜2で得られた硬化促進剤を表2に示す割合で混合し、硬化させた。
ゲルタイム経時変化 :条件 25℃、室温静値
ゲルタイム :条件 25℃
Claims (12)
- 有機酸コバルトホウ素金属塩からなることを特徴とする重合性不飽和樹脂用硬化促進剤。
- 前記有機酸コバルトホウ素金属塩が、一般式(1)
B(OCoR)3 (1)
(式中、Rは有機酸基を表し、分子中の3つのRは同一でもよく又は異なっていてもよい。)
で表される有機酸金属塩である、請求項1に記載の重合性不飽和樹脂用硬化促進剤。 - 前記有機酸コバルトホウ素金属塩が、一般式(1)
B(OCoR)3 (1)
(式中、Rは炭素原子数3〜12の脂肪族モノカルボン酸のカルボキシレート基を表し、分子中の3つのRは同一でもよく又は異なっていてもよい。)で表される有機酸金属塩である、請求項1に記載の重合性不飽和樹脂用硬化促進剤。 - 前記有機酸コバルトホウ素金属塩が、一般式(1)
B(OCoR)3 (1)
(式中、Rはプロピオン酸、オクチル酸、ナフテン酸、又はネオデカン酸のカルボキシレート基を表し、分子中の3つのRは同一でもよく又は異なっていてもよい。)で表される有機酸金属塩である、請求項1に記載の重合性不飽和樹脂用硬化促進剤。 - 更に有機酸コバルト金属塩を含有する、請求項1〜4のいずれか1項に記載の重合性不飽和樹脂用硬化促進剤。
- 重合性不飽和樹脂と硬化剤と硬化促進剤を含有する重合性不飽和樹脂組成物において、該硬化促進剤が請求項1〜5のいずれか1項に記載の重合性不飽和樹脂用硬化促進剤であることを特徴とする重合性不飽和樹脂組成物。
- 前記重合性不飽和樹脂が、不飽和ポリエステル、エポキシ(メタ)アクリレート、ウレタン(メタ)アクリレート、不飽和ポリエステル(メタ)アクリレート、及び重合性不飽和基を分子末端に有するマクロモノマーからなる群から選択される少なくとも1種である、請求項6に記載の重合性不飽和樹脂組成物。
- 前記硬化剤が有機過酸化物である、請求項6又は7に記載の重合性不飽和樹脂組成物。
- 硬化剤と硬化促進剤を用いて重合性不飽和樹脂組成物を硬化させる方法において、該硬化促進剤として請求項1〜5のいずれか1項に記載の重合性不飽和樹脂用硬化促進剤を用いることを特徴とする重合性不飽和樹脂組成物の硬化方法。
- 前記重合性不飽和樹脂が、不飽和ポリエステル、エポキシ(メタ)アクリレート、ウレタン(メタ)アクリレート、不飽和ポリエステル(メタ)アクリレート、及び重合性不飽和基を分子末端に有するマクロモノマーからなる群から選ばれた少なくとも1種である、請求項9に記載の重合性不飽和樹脂組成物の硬化方法。
- 前記硬化剤が有機過酸化物である、請求項9又は10に記載の重合性不飽和樹脂組成物の硬化方法。
- 請求項6〜8のいずれか1項に記載の重合性不飽和樹脂組成物の硬化物からなることを特徴とする成型物。
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