JP6519147B2 - 1液湿気硬化性樹脂組成物 - Google Patents
1液湿気硬化性樹脂組成物 Download PDFInfo
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- JP6519147B2 JP6519147B2 JP2014227078A JP2014227078A JP6519147B2 JP 6519147 B2 JP6519147 B2 JP 6519147B2 JP 2014227078 A JP2014227078 A JP 2014227078A JP 2014227078 A JP2014227078 A JP 2014227078A JP 6519147 B2 JP6519147 B2 JP 6519147B2
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
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- 239000010695 polyglycol Substances 0.000 description 1
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- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
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- BPJZKLBPJBMLQG-KWRJMZDGSA-N propanoyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(=O)CC BPJZKLBPJBMLQG-KWRJMZDGSA-N 0.000 description 1
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- 239000002994 raw material Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
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- 230000008961 swelling Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
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- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
1液湿気硬化性樹脂組成物としては、従来、例えば特許文献1に記載のものが提案されている。
本発明の組成物は、アミン化合物と反応する末端イソシアネート基含有ウレタンプレポリマー(A)と、大気中の水分と反応しアミン化合物を生成するイミン化合物(B)と、脂肪酸処理された炭酸カルシウム(C)と、アミノシラン化合物(d1)と3官能以上のポリイソシアネート化合物(d2)とを、反応前における前記ポリイソシアネート(d2)のイソシアネート基(NCO)に対する前記アミノシラン(d1)のイミノ基(NH)の当量比(NH/NCO)が、0.2〜0.8となるように反応させて得られる加水分解性アルコキシ基を含むシラン化合物(D)と、を主成分として含有する1液湿気硬化性樹脂組成物である。
本発明の組成物は、アミン化合物と反応する末端イソシアネート基含有ウレタンプレポリマー(A)(以下では単に「ウレタンプレポリマー(A)」ともいう)を含有する。
本発明の組成物は、大気中の水分と反応しアミン化合物を生成するイミン化合物(B)(以下では単に「イミン化合物(B)」ともいう)を含有する。
イミン化合物(B)は、ウレタンプレポリマー(A)など硬化性樹脂に対して使用できるものであれば特に限定されない。イミン化合物(B)は、潜在性硬化剤として用いられ、ウレタンプレポリマー(A)に対する硬化性、配合してから塗布するまでの作業性、貯蔵安定性に優れる。
本発明の組成物は脂肪酸処理された炭酸カルシウム(C)(以下では「表面処理炭酸カルシウム(C)」ともいう)を含有する。
表面処理炭酸カルシウム(C)は、脂肪酸を含む表面処理剤を用いて炭酸カルシウムを表面処理して得られるものである。ウレタンプレポリマー(A)に表面処理炭酸カルシウム(C)を含めることで、優れた揺変性を付与することができる。表面処理炭酸カルシウム(C)の含有量は、ウレタンプレポリマー(A)100質量部に対して30質量部以上300質量部以下が好ましく、より好ましくは50質量部以上200質量部以下である。表面処理炭酸カルシウム(C)の含有量が、30質量部以上であると、本発明の組成物の粘度は高く作業性に優れる。また、表面処理炭酸カルシウム(C)の含有量が、300質量部以下であると、本発明の組成物の粘度が高くなり過ぎず作業性に優れるからである。
As=Tg/Sw[mg/m2] ・・・(i)
Swは、窒素吸着法によるBET比表面積(m2/g)であり、Tgは、200℃以上500℃以下の表面処理炭酸カルシウム1g当たりの熱減量(mg/g)である。
本発明の組成物は、アミノシラン化合物(d1)と3官能以上のポリイソシアネート化合物(d2)とを、反応前における前記ポリイソシアネート(d2)のイソシアネート基(NCO)に対する前記アミノシラン(d1)のイミノ基(NH)の当量比(NH/NCO)が、0.2〜0.8となるように反応させて得られる加水分解性アルコキシ基を含むシラン化合物(D)(以下では単に「シラン化合物(D)」ともいう)を含有する。
チオホスフェートはイソシアネート基と炭化水素基を介して結合することができる。炭化水素基としては、例えば、脂肪族炭化水素基、脂環式炭化水素基、芳香族炭化水素基(例えば、フェニレン基)、これらの組み合わせが挙げられる。
チオホスフェートとしては、例えば、下記式で表されるものが挙げられる。
S=P−(OR)3
式中、Rはイソシアネート基を有する炭化水素基である。
ポリイソシアネート化合物(d2)は、トリス(イソシアネートフェニル)チオホスフェートを含有するのが好ましく、トリス(p−イソシアネートフェニル)チオホスフェートがより好ましい。
トリス(p−イソシアネートフェニル)チオホスフェートは下記式(4)で表される。
ここで「主成分」とは、本発明の組成物が含有する不揮発分(固形分)の合計量に対する割合(含有率)として50質量%以上であることを意味する。すなわち、本発明の組成物において、ウレタンプレポリマー(A)、イミン化合物(B)、表面処理炭酸カルシウム(C)およびシラン化合物(D)の合計量の、本発明の組成物が含有する全不揮発分(固形分)の合計量に対する割合(含有率)は50質量%以上である。この含有率は55質量%以上であることが好ましく、60質量%以上であることがより好ましく、65質量%以上であることがより好ましく、70質量%以上であることがより好ましく、75質量%以上であることがさらに好ましい。
本発明の組成物は、本発明の目的を損なわない範囲で(具体的には例えば50質量%以下の範囲で)、上述した各成分以外に、必要に応じて、各種の添加剤を含有することができる。添加剤としては、例えば、充填剤、可塑剤、シランカップリング剤、顔料、染料、老化防止剤、酸化防止剤、帯電防止剤、難燃剤、接着性付与剤、安定剤、分散剤、防カビ剤、イミン化合物の開環触媒等が挙げられる。
[ウレタンプレポリマー(A)の合成]
攪拌機、温度計、窒素導入管および加熱・冷却装置の付いた反応容器に、窒素ガス気流下で、ポリオキシプロピレンジオール(旭硝子社製、エクセノール3020、数平均分子量3,200)を220gと、ポリオキシプロピレントリオール(旭硝子社製、エクセノール5030、数平均分子量5,100)を100g仕込み、攪拌しながらヘキサメチレンジイソシアネート(住化バイエルウレタン社製、デスモジュールH、分子量168)を33.5gと、ジブチル錫ジラウレートを0.05g加えた後、加温して70〜80℃で2時間攪拌して反応させた。イソシアネート基含有量が理論値(2.37質量%)以下となった時点で室温まで冷却して反応を終了させ、ウレタンプレポリマー(A)を合成した。
得られたウレタンプレポリマー(A)は、滴定によるイソシアネート基含有量2.15質量%、常温で粘稠な液体であった。
[イミン化合物(B)の合成]
攪拌機、温度計、エステル管および加熱・冷却装置の付いた反応容器に、ジエタノールアミン(分子量105)を435gとトルエンを183g仕込み、攪拌しながらイソブチルアルデヒド(分子量72.1)を328g添加した後、加温して110〜150℃で3時間、副生する水を系外に除去しながら還流脱水反応をおこなった。除去した水の量は74.5gであった。次いで、50〜70hPaに減圧しながら加熱し、トルエンと未反応のイソブチルアルデヒドを除去し、中間の反応生成物である2−イソプロピル−3−(2−ヒドロキシエチル)オキサゾリジンを得た。
得られた2−イソプロピル−3−(2−ヒドロキシエチル)オキサゾリジン659gに、さらにヘキサメチレンジイソシアネート(分子量168)を348g加え、80℃で8時間反応させた。滴定による実測NCO含有量が0.0質量%となった時点を反応終点とし、分子内にウレタン結合とオキサゾリジン環2個を有するイミン化合物(B)を得た。
得られたイミン化合物(B)は、室温で半透明の液体であった。
[シラン化合物(D1)の合成]
上記式(3)で表される化合物(Silquest A−Link15、Momentive社製)と、HDIイソシアヌレート体(スミジュールN3300、住化バイエルウレタン社製)とを、イミノ基(NH)/イソシアネート基(NCO)=1/2となるように配合して反応させ、シラン化合物(D1)を得た。
このシラン化合物(D1)は、本発明の組成物が含有するシラン化合物(D)に該当する。
[シラン化合物(D2)の合成]
上記式(3)で表される化合物(Silquest A−Link15、Momentive社製)と、HDIビウレット体(官能基数2、スミジュールN3200、住化バイエルウレタン社製)とを、イミノ基(NH)/イソシアネート基(NCO)=1/2となるように配合して反応させ、シラン化合物(D2)を得た。
このシラン化合物(D2)は、本発明の組成物が含有するシラン化合物(D)に該当する。
[シラン化合物(X1)の合成]
上記式(3)で表される化合物(Silquest A−Link15、Momentive社製)と、ヘキサメチレンジイソシアネートとを、イミノ基(NH)/イソシアネート基(NCO)=1/2となるように配合して反応させ、シラン化合物(X1)を得た。
このシラン化合物(X1)は、本発明の組成物が含有するシラン化合物(D)に該当しない。
[シラン化合物(X2)の合成]
上記式(3)で表される化合物(Silquest A−Link15、Momentive社製)と、HDIイソシアヌレート体(スミジュールN3300、住化バイエルウレタン社製)とを、イミノ基(NH)/イソシアネート基(NCO)=1/1となるように配合して反応させ、シラン化合物(D1)を得た。
このシラン化合物(X2)は、本発明の組成物が含有するシラン化合物(D)に該当しない。
攪拌機、窒素導入管および加熱・冷却装置付き混練容器に、窒素ガス気流下で、合成例1で得たウレタンプレポリマー(A)を100g仕込み、攪拌しながら、予めそれぞれ100〜110℃の乾燥機中で乾燥して水分含有量を0.05質量%以下にした重質炭酸カルシウム25gと酸化チタン10gを仕込み、内容物が均一になるまで混合した。次いで、予めジメチルカーボネート5gにヒンダードアミン系光安定剤1.5gとヒンダードフェノール系酸化防止剤1.5gを溶解した溶解液8g、表面処理炭酸カルシウム(C)100g、合成例2で得たイミン化合物(B)8g、希釈用ポリオキシアルキレン系樹脂32g、および有機溶剤(1)18gを仕込み、さらに内容物が均一になるまで混合した。その後、合成例3で得たシラン化合物(D1)10gと、可塑剤10gと、有機溶剤(2)10gとの混合物を加えて、さらに内容物が均一になるまで混合した。
次いで、50〜70hPaで減圧脱泡し、ペーパーカートリッジ容器に充填、密封して、組成物を調製した。
得られた組成物は、室温で硬化する白色ペースト状であった。
実施例1ではシラン化合物(D1)の使用量を10gとしたが、これを3gとすること以外は、すべて実施例1と同様とした操作を行い、組成物を得た。
実施例1ではシラン化合物(D1)を10g用いたが、代わりに合成例4で得たシラン化合物(D2)を3g用いること以外は、すべて実施例1と同様とした操作を行い、組成物を得た。
実施例1ではシラン化合物(D1)を10g用いたが、代わりにHDIイソシアヌレート体(スミジュールN3300、住化バイエルウレタン社製、第1表において「シラン化合物(X3)と記す)を3g用いること以外は、すべて実施例1と同様とした操作を行い、組成物を得た。
実施例1ではシラン化合物(D1)を10g用いたが、これを用いないこと以外は、すべて実施例1と同様とした操作を行い、組成物を得た。
実施例1ではシラン化合物(D1)を10g用いたが、代わりに上記式(3)で表される化合物(Silquest A−Link15、Momentive社製、第1表において「シラン化合物(X4)と記す)を3g用いること以外は、すべて実施例1と同様とした操作を行い、組成物を得た。
実施例1ではシラン化合物(D1)を10g用いたが、代わりに合成例6で得たシラン化合物(X2)を3g用いること以外は、すべて実施例1と同様とした操作を行い、組成物を得た。
実施例1ではシラン化合物(D1)を10g用いたが、代わりに合成例5で得たシラン化合物(X1)を3g用いること以外は、すべて実施例1と同様とした操作を行い、組成物を得た。
実施例2ではイミン化合物(B)を8g用いたが、これを用いないこと以外は、すべて実施例2と同様とした操作を行い、組成物を得た。
また、以下に各成分について具体的に記す。
・表面処理炭酸カルシウム(C):カルフォシール15B、丸尾カルシウム社製
・重質炭酸カルシウム:スーパーS、丸尾カルシウム社製
・酸化チタン:R−820、石原産業社製
・ヒンダードアミン系光安定剤:チバ・スベシャルティ・ケミカルズ社製、TINUVIN 765、セバシン酸ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)
・ヒンダードフェノール系酸化防止剤:チバ・スペシャルティ・ケミカルズ社製、IRGANOX 1010、ペンタエリスリトール−テトラキス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]
・ジメチルカーボネート:DMC、三井化学ファイン社製
・希釈用ポリオキシアルキレン系樹脂:サンフレックス GPA3000、三洋化成社製
・有機溶剤(1):エクソールD40、エクソンモービル社製
・可塑剤:DINP、ジェイプラス社製
・有機溶剤(2):ミネラルスピリット、JX日鉱日石エネルギー社製
樹脂組成物表面の硬化時間は、硬化反応開始後に樹脂組成物の表面タックがある時間、即ちタックフリータイムを硬化時間とした。実施例1〜3および比較例1〜6において得られた各々の組成物について、縦10cm×横1cm×高さ1cmのポリエチレン製の枠の中に気泡が入り込まないように流し込み、上端の大気に触れている表面を平らにならした試験体を作成する。この試験体を20℃、55%湿度条件下におき、このときの時間を、硬化時間を測定するための開始時間とする。次に、硬化反応中の試験体について、24時間後に表面をポリエチレン製のフィルムで軽く触れ、試験体がフィルムに付着しなくなっていれば硬化性を○とし、逆に試験体がフィルムに付着すれば硬化性を×とした。
モルタル製の型枠(50mm×50mm×深さ25mm)を23±2℃×50±5%RHの雰囲気内に24時間以上放置する。その後、50mm幅のガムテープ(布製)でモルタル製の型枠の側面を捲いてカバーし、さらに、25mm幅のガムテープ(布製)が型枠の上側へ5〜7mm余るように、側面を捲いてカバーする。次に、モルタル製の型枠の内部へ、エアーを含まないように組成物を充填し、直ちに40℃のオーブンで3日養生する。その後、カッターナイフで切れ目を入れ、硬化した組成物をモルタル製の型枠から手剥離し、それらの界面について目視により観察し、発泡の有無を確認する。そして、泡の数が0〜1個のものを○、2〜3個のものを△、4個以上のものを×と評価した。
日本ゴム協会標準規格(SRIS)0101に準じてアスカーC(ASKER C)硬度を測定した。アスカーC硬度は、得られた各組成物を40℃×95%RHの雰囲気に5日間放置して硬化させた後の硬度を、アスカーC型硬度計(高分子計器社製)を用いて、それぞれ測定した。そして、アスカーC硬度が40以上であれば硬度が高いと判断して○、40未満であれば硬度が高くないとして×と評価した。
Claims (1)
- アミン化合物と反応する末端イソシアネート基含有ウレタンプレポリマー(A)と、
大気中の水分と反応しアミン化合物を生成するオキサゾリジン化合物(B)と、
脂肪酸処理された炭酸カルシウム(C)と、
アミノシラン化合物(d1)と3官能以上のポリイソシアネート化合物(d2)とを、反応前における前記ポリイソシアネート(d2)のイソシアネート基(NCO)に対する前記アミノシラン(d1)のイミノ基(NH)の当量比(NH/NCO)が、0.2〜0.8となるように反応させて得られる加水分解性アルコキシ基を含むシラン化合物(D)と、を主成分として含有し、
前記オキサゾリジン化合物(B)の含有量が、前記ウレタンプレポリマー(A)が有するイソシアネート基の数に対する前記オキサゾリジン化合物(B)から発生し得る活性水素の数の比が0.01以上2.0以下になる量である1液湿気硬化性樹脂組成物。
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