JP2012077255A - 水性ポリウレタン樹脂、親水性樹脂およびフィルム - Google Patents
水性ポリウレタン樹脂、親水性樹脂およびフィルム Download PDFInfo
- Publication number
- JP2012077255A JP2012077255A JP2010226173A JP2010226173A JP2012077255A JP 2012077255 A JP2012077255 A JP 2012077255A JP 2010226173 A JP2010226173 A JP 2010226173A JP 2010226173 A JP2010226173 A JP 2010226173A JP 2012077255 A JP2012077255 A JP 2012077255A
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- JP
- Japan
- Prior art keywords
- group
- aqueous
- resin
- polyurethane resin
- isocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 104
- 239000012948 isocyanate Substances 0.000 claims abstract description 90
- 150000002513 isocyanates Chemical group 0.000 claims abstract description 89
- 229920005862 polyol Polymers 0.000 claims abstract description 76
- 150000003077 polyols Chemical class 0.000 claims abstract description 75
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- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 47
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 39
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- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 6
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- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 4
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
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- 238000013329 compounding Methods 0.000 description 4
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- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
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- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 3
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Abstract
【解決手段】芳香環および脂環を含有しないかまたは芳香環または脂環を1つ含有する複数環不含ポリイソシアネートを50質量%以上含有するポリイソシアネート、ポリオキシエチレンポリオール、および、水酸基またはイソシアネート基を分子末端に2つ以上有しポリオキシエチレン基を側鎖に有するポリオキシエチレン側鎖含有活性化合物を反応させて得られるイソシアネート基末端プレポリマーと、水を含む鎖伸長剤とを反応させ、イソシアネート基末端プレポリマーにおけるイソシアネート基の60モル%以上が、水で鎖伸長されている水性ポリウレタン樹脂を得る。
【選択図】なし
Description
ポリオキシエチレン側鎖含有ポリオールの配合割合は、水性ポリウレタン樹脂の原料総量(仕込み総量)に対して、例えば、5〜40質量%である。
ポリオキシエチレン側鎖含有ポリイソシアネートの配合割合は、水性ポリウレタン樹脂の原料総量(仕込み総量)に対して、例えば、5〜40質量%である。
温度計、窒素ガス導入管および攪拌機を備えた反応器中で、窒素ガスを導入しながら、ヘキサメチレンジイソシアネート(タケネート700、三井化学社製)627.1部、50℃に加温した数平均分子量1000のメトキシポリエチレングリコール(MPEG−1000、東邦化学社製)372.9部を仕込み、80℃で6時間反応させた。所定のイソシアネート基含有量に到達した後、スミス式薄膜蒸留器にて未反応のヘキサメチレンジイソシアネートを除去し、ポリオキシエチレン鎖含有モノイソシアネートを得た。このポリオキシエチレン鎖含有モノイソシアネートの計算上の数平均分子量は、1168であった。
還流冷却管、窒素導入管、温度計、攪拌機を備えた4つ口フラスコ中に、1,3−(ビスイソシアナトメチル)シクロヘキサン(商品名:タケネート600、三井化学製)93.8部と、数平均分子量1000のポリエチレングリコール(商品名:PEG−1000、東邦化学社製)357.8部と、ポリオキシエチレン側鎖含有ポリオールA38.4部と、アセトニトリル210部とを仕込み、窒素雰囲気下で、反応温度を73〜77℃に調整して、7時間で反応率99%以上まで反応させた。次いで、これを30℃まで冷却し、イソシアネート末端プレポリマーを得た。
下記の表1に示す配合処方に基づいて、実施例1と同様の方法により、水性ポリウレタン樹脂Bの水分散液(実施例2)、水性ポリウレタン樹脂Cの水分散液(実施例3)、水性ポリウレタン樹脂Dの水分散液(実施例4)、水性ポリウレタン樹脂Eの水分散液(実施例5)、水性ポリウレタン樹脂Fの水分散液(実施例6)、水性ポリウレタン樹脂Gの水分散液(比較例1)、水性ポリウレタン樹脂Hの水分散液(比較例2)、および、水性ポリウレタン樹脂Iの水分散液(比較例3)を、それぞれ調製した。
H6XDI:1,3−ビス(イソシアナトメチル)シクロヘキサン、商品名タケネート600、三井化学社製
IPDI:イソホロンジイソシアネート、商品名VESTANAT IPDI エボニック社製
H12MDI:4,4´−メチレンビス(シクロヘキシルイソシアネート)、商品名デスモジュールW、バイエル社製
PEG−1000:数平均分子量1000のポリエチレングリコール、東邦化学社製
POE側鎖ポリオールA:ポリオキシエチレン側鎖含有ポリオールA
トリエチレングリコール:和光純薬社製
エチレンジアミン:和光純薬社製
モノエタノールアミン:和光純薬社製
ジエタノールアミン:和光純薬社製
アミノアルコールEA:N−(2−アミノエチル)エタノールアミン、日本乳化剤社製
合成例1(第2水性ポリウレタン樹脂Aの合成)
還流冷却管、窒素導入管、温度計、攪拌機を備えた4つ口フラスコ中に、4,4’−メチレンビス(シクロヘキシルイソシアネート)(商品名:デスモジュールW、バイエル社製)89.3部と、数平均分子量2000のポリテトラメチレンエーテルグリコール(商品名:PTHF−2000、BASFジャパン社製)234.2部と、ジメチロールヘプタン(商品名:ブチルエチルプロパンジオール、協和発酵ケミカル社製)6.6部と、ジメチロールプロピオン酸(商品名:Bis−MPA、パーストープ社製)11.4部と、アセトニトリル150部とを仕込み、窒素雰囲気下で、反応温度を73〜77℃に調整して、7時間で反応率99%以上まで反応させた。
下記の表2に示す配合処方に基づいて、合成例1と同様の方法により、第2水性ポリウレタン樹脂Bの水分散液(合成例2)、第2水性ポリウレタン樹脂Cの水分散液(合成例3)、第2水性ポリウレタン樹脂Dの水分散液(合成例4)、および、第2水性ポリウレタン樹脂Eの水分散液(合成例5)を、それぞれ調製した。
還流冷却管、窒素導入管、温度計、攪拌機を備えた4つ口フラスコ中に、4,4’−メチレンビス(シクロヘキシルイソシアネート)(商品名:デスモジュールW、バイエル社製)78.5部と、数平均分子量2000のポリテトラメチレンエーテルグリコール(商品名:PTHF−2000、BASFジャパン社製)208.5部と、エチレングリコール4.9部と、ポリオキシエチレン側鎖含有ポリオールA33.1部、アセトニトリル139部とを仕込み、窒素雰囲気下で、反応温度を73〜77℃に調整して、7時間で反応率99%以上まで反応させた。
H12MDI:4,4´−メチレンビス(シクロヘキシルイソシアネート)、商品名デスモジュールW、バイエル社製
PTHF2000:数平均分子量2000のポリテトラメチレンエーテルグリコール、BASFジャパン社製
ジメチロールヘプタン:ブチルエチルプロパンジオール、協和発酵ケミカル社製
ソバモール908:水添ダイマーアルコール(ダイマー酸の還元により得られるダイマー脂肪族アルコール、コグニスジャパン社製
ネオペンチルグリコール:三菱瓦斯化学社製
トリメチロールプロパン:三菱瓦斯化学社製
エチレングリコール:和光純薬社製
2,2−ジメチロールプロピオン酸:Bis−MPA、パーストープ社製
POE側鎖ポリオールA:ポリオキシエチレン側鎖含有ポリオールA
トリエチルアミン:和光純薬社製
イソホロンジアミン:和光純薬社製
1,6−ヘキサメチレンジアミン:HMD(ヘキサメチレンジアミン)、インビスタジャパン社製
調製例2(硬化剤Aの調製)
攪拌機、温度計、還流冷却管を取り付けた4つ口フラスコを窒素置換した後、タケネートD−110N(キシリレンジイソシアネートのトリメチロールプロパンアダクト体、固形分75質量%、三井化学社製)341部と、メチルエチルケトン64.7部とを仕込み、攪拌し、タケネートD−110Nをメチルエチルケトンに溶解させた。
下記の表3に示す配合処方に基づいて、調製例2と同様の方法により、硬化剤B(調製例3)、硬化剤D(調製例5)、硬化剤E(調製例6)および硬化剤F(調製例7)を、固形分40質量%の水分散体としてそれぞれ調製した。
攪拌機、温度計、還流冷却管を取り付けた4つ口フラスコを窒素置換した後、タケネートD−110N(キシリレンジイソシアネートのトリメチロールプロパンアダクト体、固形分75質量%、三井化学社製)293.8部と、ポリエチレングリコールモノメチルエーテル(商品名メトキシPEG−1000、東邦化学社製)56.3部とを仕込み、74℃で3時間反応させた。次いで、メチルエチルケトン76.5部を仕込み、攪拌し、内温を50〜60℃に保ち、攪拌しながら、3,5−ジメチルピラゾール(大塚化学社製)73.4部を1時間かけて添加した。
D−110N:キシリレンジイソシアネートのトリメチロールプロパンアダクト体、固形分75質量%、三井化学社製
D−103H:トリレンジイソシアネートのトリメチロールプロパンアダクト体、固形分75質量%、三井化学社製
D−160N:ヘキサメチレンジイソシアネートのトリメチロールプロパンアダクト体、固形分75質量%、三井化学社製
MEOPEG1000:ポリエチレングリコールモノメチルエーテル、商品名メトキシPEG−1000、分子量1000、東邦化学社製
3,5−ジメチルピラゾール:大塚化学社製
メチルエチルケトオキシム:メチルエチルケトンオキシム、宇部興産社製
エマルゲンA−500:ポリオキシエチレンジスチレン化フェニルエーテル 固形分濃度:100質量%、HLB:18.0、花王社製(なお、実施例では4倍希釈し、25質量%水溶液として用いた。)
ノナール912A:ポリオキシエチレンクミルフェニルエーテル、固形分濃度:100質量%、HLB:14.3、東邦化学工業社製
ルノックス100:アルキルベンゼンスルホン酸ナトリウム、固形分濃度60質量%、東邦化学工業社製(なお、実施例では6倍希釈し、10質量%水溶液として用いた。)
消泡剤:BYK−022、ビックケミー社製
実施例7(親水性樹脂Aの調製)
高速攪拌可能なホモディスパーを備えた容器に、水性ポリウレタン樹脂Aの水分散液(固形分35.1質量%)34部と、第2水性ポリウレタン樹脂Aの水分散液(固形分30.6質量%)の168部を加え、更に、硬化剤Aを、水性ポリウレタン樹脂Aと第2水性ポリウレタン樹脂Aとの総量(水分散液として)に対して2.8質量部の割合で配合し、2000min−1で10分間攪拌混合した。その後、減圧下で脱泡し、親水性樹脂Aの水分散液を得た。
表4〜7に示す配合処方に基づいて、実施例7と同様の方法により、親水性樹脂B〜Yの水分散液を調製した。なお、実施例8〜15、17〜21、23〜27および比較例5においては、水を配合した。また、実施例16および17は硬化剤を配合せず、実施例28は第2水性ポリウレタン樹脂を配合せず、比較例6は水性ポリウレタン樹脂を配合しなかった。
膜の外観
各実施例および各比較例の親水性樹脂の水分散液を、キャスティングして、120℃において2分間、さらに、170℃において2分間硬化させ、膜厚0.04mmの乾燥透明フィルム(実施例7、16は0.02mmの乾燥透明フィルム)を形成した。このフィルムの外観を以下の基準に従って評価した。その結果を表4〜7に示す。
(評価基準)
「○」:平滑で綺麗な膜が得られた
「△」:表面が均一に荒れた膜が得られた
「×」:表面がまだらに荒れた膜が得られた
耐水性
各実施例および各比較例の親水性樹脂の水分散液を、キャスティングして、120℃において2分間、さらに、170℃において2分間硬化させ、膜厚0.04mmの乾燥透明フィルム(実施例7、16は0.02mmの乾燥透明フィルム)を形成した。その後、このフィルムを水に2分間浸漬し、色の変化を目視により観察し、以下の基準に従ってその耐水性を判定した。その結果を表4〜7に示す。
(評価基準)
「○」:透明なまま色が殆ど変化しない
「△」:フィルムが青っぽくなり、曇る
「×」:フィルムが濁り、白っぽくなる
透湿性試験(透湿性試験A−1法)
各実施例および各比較例の親水性樹脂の水分散液を、キャスティングして、120℃において2分間、さらに、170℃において2分間硬化させ、膜厚0.02mmの乾燥透明フィルムを形成した。その後、このフィルムを、JIS L1099(2006)A−1法(塩化カルシウム法)に準拠して透湿性を評価した。その結果を表4〜7に示す。
機械強度試験
各実施例および各比較例の親水性樹脂の水分散液を、キャスティングして、120℃において2分間、さらに、170℃において2分間硬化させ、膜厚0.04mmの乾燥透明フィルム(実施例7、16は0.02mmの乾燥透明フィルム)を形成した。その後、このフィルムを1cmの短冊状に切断し、引張速度200mm/分の条件で引張試験し、破断時の応力(破断強度(MPa))、伸び率(破断伸び(%))および100%モジュラス(MPa)を測定した。その結果を表4〜7に示す。
Claims (18)
- 芳香環および脂環を含有しないか、または、芳香環または脂環を1つ含有する複数環不含ポリイソシアネートを、50質量%以上含有するポリイソシアネート、
ポリオキシエチレンポリオール、および、
水酸基またはイソシアネート基を分子末端に2つ以上有し、ポリオキシエチレン基を側鎖に有するポリオキシエチレン側鎖含有活性化合物を、
少なくとも反応させることにより得られるイソシアネート基末端プレポリマーと、
水を含む鎖伸長剤と
の反応により得られる水性ポリウレタン樹脂であって、
イソシアネート基末端プレポリマーにおけるイソシアネート基の60モル%以上が、水で鎖伸長されていることを特徴とする、水性ポリウレタン樹脂。 - 固形分濃度30質量%の水分散液における粘度が、5000mPa・s未満であることを特徴とする、請求項1に記載の水性ポリウレタン樹脂。
- ポリオキシエチレン基が、50〜90質量%含有されていることを特徴とする、請求項1または2に記載の水性ポリウレタン樹脂。
- ポリオキシエチレンポリオールの数平均分子量が、600〜6000であることを特徴とする、請求項1〜3のいずれか一項に記載の水性ポリウレタン樹脂。
- ポリオキシエチレン側鎖含有活性化合物において、ポリオキシエチレン基の数平均分子量が、600〜6000であることを特徴とする、請求項1〜4のいずれか一項に記載の水性ポリウレタン樹脂。
- ポリオキシエチレン側鎖含有活性化合物は、ウレア基、ウレタン基およびアロファネート基から選択される少なくとも1種の化学結合を有していることを特徴とする、請求項1〜5のいずれか一項に記載の水性ポリウレタン樹脂。
- 親水性改質剤であることを特徴とする、請求項1〜6のいずれか一項に記載の水性ポリウレタン樹脂。
- 第1水性樹脂として、請求項1〜7のいずれか一項に記載の水性ポリウレタン樹脂を含有することを特徴とする、親水性樹脂。
- 第2水性樹脂を含有することを特徴とする、請求項8に記載の親水性樹脂。
- 水分散性のイソシアネート硬化剤を含有することを特徴とする、請求項8または9に記載の親水性樹脂。
- 第2水性樹脂は、原料として、ポリエステルポリオール、ポリカーボネートポリオールおよびアルキレン基の炭素数が3〜10のポリオキシアルキレンポリオールからなる群から選択される少なくとも1種の疎水性マクロポリオールを含み、
疎水性マクロポリオールが、第2水性樹脂の原料総量に対して50質量%以上含まれていることを特徴とする、請求項9または10に記載の親水性樹脂。 - 第2水性樹脂は、原料として、さらに、カルボン酸基含有ポリオールを含んでいることを特徴とする、請求項11に記載の親水性樹脂。
- イソシアネート硬化剤が、
イソシアネートがブロック剤によりブロックされているブロックイソシアネートであることを特徴とする、請求項10〜12のいずれか一項に記載の親水性樹脂。 - ブロックイソシアネートが、外部乳化剤により水分散されていることを特徴とする、請求項13に記載の親水性樹脂。
- ブロックイソシアネートにおいて、イソシアネートが、芳香環を1つ含有するポリイソシアネートまたはその変性体であることを特徴とする、請求項13または14に記載の親水性樹脂。
- ブロックイソシアネートにおいて、ブロック剤が、3,5−ジメチルピラゾールであることを特徴とする、請求項13〜15のいずれか一項に記載の親水性樹脂。
- 透湿防水加工のためのコーティング剤であることを特徴とする、請求項8〜16のいずれか一項に記載の親水性樹脂。
- 請求項8〜17のいずれか一項に記載の親水性樹脂から得られることを特徴とする、フィルム。
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