JP7491949B2 - ポリウレタン樹脂組成物、撥剤、繊維撥水剤および防汚コート剤 - Google Patents
ポリウレタン樹脂組成物、撥剤、繊維撥水剤および防汚コート剤 Download PDFInfo
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- JP7491949B2 JP7491949B2 JP2021567449A JP2021567449A JP7491949B2 JP 7491949 B2 JP7491949 B2 JP 7491949B2 JP 2021567449 A JP2021567449 A JP 2021567449A JP 2021567449 A JP2021567449 A JP 2021567449A JP 7491949 B2 JP7491949 B2 JP 7491949B2
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- active hydrogen
- polyurethane resin
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- 229920005749 polyurethane resin Polymers 0.000 title claims description 67
- 239000011342 resin composition Substances 0.000 title claims description 65
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- -1 hydrogen compound Chemical class 0.000 claims description 93
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- 125000001931 aliphatic group Chemical group 0.000 claims description 74
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- 125000002091 cationic group Chemical group 0.000 claims description 64
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 48
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
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- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 7
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- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
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Classifications
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Description
1.脂肪族ポリイソシアネート誘導体の調製
合成例1(ヘキサメチレンジイソシアネートのイソシアヌレート誘導体)
温度計、攪拌装置、窒素導入管および冷却管が装着された反応器において、窒素雰囲気下、1,6-ヘキサメチレンジイソシアネート(HDI、三井化学社製、商品名:タケネート700)500質量部、2,6-ジ(tert-ブチル)-4-メチルフェノール(別名:ジブチルヒドロキシトルエン、BHT、ヒンダードフェノール系酸化防止剤)0.25質量部、テトラフェニル・ジプロピレングリコール・ジホスファイト(有機亜リン酸エステル、助触媒)0.25質量を混合した後、この混合液に1,3-ブタンジオール10.7質量部を加え、窒素を、その液相に1時間導入した。その後、混合液を80℃に昇温し3時間反応後、60℃に降温した。その後、イソシアヌレート化触媒として、トリメチル-N-2-ヒドロキシプロピルアンモニウム・2-エチルヘキサノエート 0.2質量部加え、1.5時間反応させた。その後、HDI 100質量部に対して、o-トルエンスルホンアミド 0.04質量部を添加した。その後、この反応混合液を、薄膜蒸留装置(温度150℃、真空度93.3Pa)に通液して、残存HDIモノマー量が0.5%以下になるまで蒸留し、脂肪族ポリイソシアネート誘導体(ヘキサメチレンジイソシアネートのイソシアヌレート誘導体)を得た。得られた脂肪族ポリイソシアネート誘導体の、イソシアネート基含有率は20.9%、平均イソシアネート官能基数は3.0であった。
温度計、攪拌装置、窒素導入管および冷却管が装着された反応器において、窒素雰囲気下、1,6-ヘキサメチレンジイソシアネート(HDI、三井化学社製、商品名:タケネート700)500質量部、および、トリメチロールプロパン(略号:TMP)45.8質量部を装入した。窒素雰囲気下、75℃まで昇温し、トリメチロールプロパンが溶解したことを確認した後、イソシアネート基濃度が計算値(未反応のイソシアネート基の理論量)37.9%に達するまで、83℃で反応させた。その後、この反応溶液を55℃まで降温し、混合抽出溶剤(n-ヘキサン/酢酸エチル=90/10(質量比))を350質量部加え、10分間撹拌し、10分間静置した後、抽出溶剤層を除去した。同抽出操作を4回繰り返した。その後、得られた反応液から、減圧下、80℃に加熱して、反応液中に残留する抽出溶剤を除去した。この反応液のイソシアネート基濃度は17.1質量%であった。さらに、酢酸エチルを加え、濃度75%の脂肪族ポリイソシアネート誘導体(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付加体)を含む反応液を得た。得られた脂肪族ポリイソシアネート誘導体の、イソシアネート基含有率は12.8%、平均イソシアネート官能基数は3.3であった。
温度計、攪拌装置、窒素導入管および冷却管が装着された反応器において、窒素雰囲気下、1,6-ヘキサメチレンジイソシアネート(HDI、三井化学社製、商品名:タケネート700)500質量部、イソブチルアルコール24質量部、2,6-ジ(tert-ブチル)-4-メチルフェノール(別名:ジブチルヒドロキシトルエン、BHT、ヒンダードフェノール系酸化防止剤)0.3質量部、トリス(トリデシル)ホスファイト0 .30質量部を挿入し、85℃で3時間ウレタン化反応させた。その後、アロファネート触媒としてトリス(2-エチルヘキサン酸)ビスマス0.02質量部を添加し、イソシアネート基濃度が計算値(46.7%)に達するまで反応させた後、o-トルエンスルホンアミド0.02質量部を添加した。その後、この反応混合液を、薄膜蒸留装置(温度150℃、真空度93.3Pa)に通液して、残存HDIモノマー量が0.5%以下になるまで蒸留した。その後、反応液100質量部に対し、o-トルエンスルホンアミド0.02質量部を添加し、脂肪族ポリイソシアネート誘導体(ヘキサメチレンジイソシアネートのアロファネート誘導体)を得た。得られた脂肪族ポリイソシアネート誘導体の、イソシアネート基含有率は19.3%、平均イソシアネート官能基数は2.1であった。
温度計、攪拌装置、窒素導入管および冷却管が装着された反応器において、窒素雰囲気下、1,6-ヘキサメチレンジイソシアネート(HDI、三井化学社製、商品名:タケネート700)500質量部、トリス(トリデシル)ホスファイト0.3質量部、トリメチルリン酸8質量部、水3.57質量部を装入し、130℃に昇温し、イソシアネート基含有率が44.6%に達するまで反応させた。その後、この反応混合液を、薄膜蒸留装置(温度150℃、真空度93.3Pa)に通液して、残存HDIモノマー量が0.5%以下になるまで蒸留し、脂肪族ポリイソシアネート誘導体(ヘキサメチレンジイソシアネートのビウレット誘導体)を得た。得られた脂肪族ポリイソシアネート誘導体の、イソシアネート基含有率は22.6%であり、平均イソシアネート官能基数は2.8であった。
2.ポリウレタン樹脂組成物および撥水性処理液の調製
実施例1
攪拌機、温度計、冷却器および窒素ガス導入管を備えた反応器に、脂肪族ポリイソシアネート誘導体として、合成例1の脂肪族ポリイソシアネート誘導体100.08g、長鎖活性水素化合物として、カルコール8098(ステアリルアルコール、花王株式会社製)90.03gを混合し、窒素雰囲気化110℃で、イソシアネート基の濃度が3.67%になるまで4時間反応させた。
表1に従って、配合処方を変更した以外は、実施例1と同様にして、ポリウレタン樹脂組成物を含む水分散液、および、撥水性処理液を調製した。
表1に従って、配合処方を変更した以外は、実施例1と同様にして、ポリウレタン樹脂組成物を含む水分散液を製造した。
攪拌機、温度計、冷却器および窒素ガス導入管を備えた反応器に、脂肪族ポリイソシアネート誘導体として、合成例1の脂肪族ポリイソシアネート誘導体79.88g、および、合成例2の脂肪族ポリイソシアネート誘導体27.55g、長鎖活性水素化合物として、カルコール8098(ステアリルアルコール、花王株式会社製)67.37g、オレイルアルコール22.22gを混合し、窒素雰囲気下80℃で、固形分あたりのイソシアネート基の濃度が3.66%になるまで反応させた。
表1に従って、配合処方を変更した以外は、実施例6と同様にして、ポリウレタン樹脂組成物を含む水分散液、および、撥水性処理液を調製した。
攪拌機、温度計、冷却器および窒素ガス導入管を備えた反応器に、合成例1の脂肪族ポリイソシアネート誘導体99.46g、長鎖活性水素化合物として、カルコール8098(ステアリルアルコール、花王株式会社製)89.48gを混合し、窒素雰囲気下110℃で、固形分あたりのイソシアネート基濃度が3.67%になるまで4時間反応させた。
オーバーヘッド撹拌機、熱電対、ディーン・スターク/コンデンサを備えた250mlの四つ口丸底フラスコに、レオドールSP-S30V(ソルビタントリステアレート、花王株式会社製)116.0gと、4-メチル-2-ペンタノン(MIBK)150gを添加した。得られた反応液を1時間還流させ、残留水分を全て除去した。1時間後、反応液を50℃まで冷却し、デスモデュール(DESMODUR)N-100(ヘキサメチレンジイソシアネートのビウレット誘導体、Bayer社製)30gを加え、次いで、触媒を添加して、溶液を80℃まで1時間加熱した。これにより、ソルビタンウレタン/MIBK溶液を調製した。
攪拌機、温度計、冷却器および窒素ガス導入管を備えた反応器に、合成例1の脂肪族ポリイソシアネート誘導体141.09g、カチオン性活性水素化合物として、N-メチルジエタノールアミン13.94g、溶剤として、メチルエチルケトン 85.71gを混合し、窒素雰囲気化60℃で2時間、その後、70℃に昇温し、固形分あたりのイソシアネート基濃度が12.7%になるまで反応させた。
3.評価
a)平均イソシアネート官能基数
各合成例の脂肪族ポリイソシアネート誘導体の平均イソシアネート官能基数は、脂肪族ポリイソシアネート誘導体のイソシアネート基濃度A、固形分濃度B、および、以下の装置および条件にて測定されるゲルパーミエーションクロマトグラフィーの数平均分子量Cから、下記式(1)により算出した。
(式中、Aは、脂肪族ポリイソシアネート誘導体のイソシアネート基濃度を示し、Bは、固形分濃度を示し、Cは、数平均分子量を示す。)
また、脂肪族ポリイソシアネート誘導体を、2種併用する実施例6~実施例9の平均イソシアネート官能基数は、脂肪族ポリイソシアネート誘導体の重量比とその平均イソシアネート官能基数により算出した。その結果を表1に示す。
(数平均分子量の測定条件)
装置:HLC-8220GPC(東ソー製)
カラム:TSKgelG1000HXL、TSKgelG2000HXL、およびTSKgelG3000HXL(東ソー製)を直列に連結した
検出器:示差屈折率計
注入量:100μL
溶離液:テトラヒドロフラン
流量:0.8mL/min
温度:40℃
検量線:106~22450の範囲の標準ポリエチレンオキシド(東ソー製、商品名:TSK標準ポリエチレンオキシド)
b)撥水性および洗濯耐久性
(処理布の準備)
各実施例および各比較例の撥水性処理液に、試験用綿布(カナキン3号)を1回含浸した後、この試験用綿布を1回絞り(ピックアップ100%)、その後、110℃で2分乾燥した。
(洗濯前撥水性)
各実施例および各比較例の処理布(170℃2分)および処理布(170℃10分)に、スポイトで水滴を10滴落とし、その水滴が、処理布に染み込まないで残っていた水滴の数を、計測した。
(洗濯後撥水性)
各実施例および各比較例の処理布(170℃2分)および処理布(170℃10分)を、以下の条件で洗濯した後(5回または10回洗濯した後)、スポイトで水滴を10滴落とし、その水滴が、処理布に染み込まないで残っていた水滴の数を、計測した。なお、計測は、スポイトで水滴を10滴落とした後から、15分経過後と、30分経過後または90分経過後とに実施した。その結果を表2に示す。
洗濯:東芝 AW-F42S(パルセーター式洗濯機)標準モード
洗剤:洗濯用合成洗剤 ボールド フレッシュピュアクリーン(プロクター・アンド・ギャンブル・ジャパン株式会社製)記載の濃度(水45Lに対して洗剤約43g)
乾燥:東芝 ED-50(タンブラー式乾燥機) 標準モード
(撥水性および洗濯耐久性の評価)
各実施例および各比較例について、以下の基準に基づいて、撥水性を評価した。その結果を表2に示す。
〇:処理布(170℃10分)に関して、洗濯前撥水性評価(15分経過後)および洗濯前撥水性評価(30分経過後)における水滴の数が、ともに、10である。
△:処理布(170℃10分)に関して、洗濯前撥水性評価(15分経過後)および洗濯前撥水性評価(30分経過後)のうち、少なくとも一方おける水滴の数が、1以上10未満である。
×:処理布(170℃10分)に関して、洗濯前撥水性評価(15分経過後)および洗濯前撥水性評価(30分経過後)のうち、少なくとも一方における水滴の数が、0である。
〇:処理布(170℃10分)に関して、洗濯後撥水性評価(10回洗濯後、15分経過後)および洗濯後撥水性評価(10回洗濯後、30分経過後)における水滴の数が、ともに、10である。
△:処理布(170℃10分)に関して、洗濯後撥水性評価(10回洗濯後、15分経過後)および洗濯後撥水性評価(10回洗濯後、30分経過後))のうち、少なくとも一方における水滴の数が、1以上10未満である。
×:処理布(170℃10分)に関して、洗濯後撥水性評価(10回洗濯後、15分経過後)および洗濯後撥水性評価(10回洗濯後、30分経過後))のうち、少なくとも一方における水滴の数が、0である。
(防汚性)
実施例2の撥水性処理液を、以下の条件で各基材(ガラス、ボンデ鋼板、アクリル(白)およびPETフィルム)に塗布し塗膜を作成した。
炭化水素基の濃度が、30%以上85%以下である実施例1~実施例11は、炭化水素基の濃度が、30%未満である比較例1よりも、撥水性および洗濯耐久性に優れる。
Claims (6)
- 平均イソシアネート基数2以上の脂肪族ポリイソシアネート誘導体と、
炭素数12以上30以下の炭化水素基および1つの水酸基を併有する長鎖活性水素化合物と、
活性水素基およびカチオン性基を併有するカチオン性活性水素化合物と、
カチオン性基と塩を形成する酸化合物との反応生成物を含み、
前記脂肪族ポリイソシアネート誘導体は、ヘキサメチレンジイソシアネートのイソシアヌレート誘導体またはペンタメチレンジイソシアネートのイソシアヌレート誘導体を含み、
前記カチオン性活性水素化合物は、N-メチルジエタノールアミン、N-エチルジエタノールアミン、N-プロピルジエタノールアミン、N-ブチルジエタノールアミン、および、N-メチルジプロパノールアミンからなる群より選択される少なくとも1つであり、
前記反応生成物は、第2中間反応生成物および前記酸化合物のみの反応生成物であり、
前記第2中間反応生成物は、第1中間反応生成物および前記カチオン性活性水素化合物のみからなる反応生成物であり、
前記第1中間反応生成物は、前記脂肪族ポリイソシアネート誘導体および前記長鎖活性水素化合物のみからなる反応生成物であり、
前記炭化水素基の濃度が、30%以上85%以下であり、
前記長鎖活性水素化合物が、直鎖状飽和炭化水素基含有アルコールを含むことを特徴とする、ポリウレタン樹脂組成物。 - 前記カチオン性活性水素化合物において、
前記カチオン性基が、3級アミノ基であり、
前記活性水素基が、水酸基であり、
前記カチオン性活性水素化合物は、1分子あたり2つ以上の水酸基を有することを特徴とする、請求項1に記載のポリウレタン樹脂組成物。 - 前記酸化合物が、有機酸を含むことを特徴とする、請求項1に記載のポリウレタン樹脂組成物。
- 請求項1に記載のポリウレタン樹脂組成物を含むことを特徴とする、撥剤。
- 請求項1に記載のポリウレタン樹脂組成物を含むことを特徴とする、繊維撥水剤。
- 請求項1に記載のポリウレタン樹脂組成物を含むことを特徴とする、防汚コート剤。
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EP1496073A1 (de) * | 2003-07-08 | 2005-01-12 | Ciba Spezialitätenchemie Pfersee GmbH | Extender für die Behandlung von Fasermaterialien |
JP4994116B2 (ja) * | 2007-05-25 | 2012-08-08 | 三井化学株式会社 | 水性ウレタン樹脂 |
JP5368525B2 (ja) * | 2011-09-29 | 2013-12-18 | 三井化学株式会社 | アロファネート基含有ポリイソシアネート、ならびにウレタンプレポリマー、ポリウレタン樹脂組成物およびその用途 |
CA2916047C (en) * | 2013-06-27 | 2020-11-17 | Asahi Kasei Chemicals Corporation | Polyisocyanate composition and method of manufacturing the same, blocked polyisocyanate composition and method of manufacturing the same, resin composition, curable resin composition and hardened material |
JP6386086B2 (ja) * | 2014-12-15 | 2018-09-05 | 三井化学株式会社 | 自己修復性ポリウレタン樹脂原料、自己修復性ポリウレタン樹脂、自己修復性コーティング材料、自己修復性エラストマー材料、自己修復性ポリウレタン樹脂原料の製造方法、および、自己修復性ポリウレタン樹脂の製造方法 |
JP6741442B2 (ja) * | 2016-02-29 | 2020-08-19 | 日華化学株式会社 | 撥水助剤、非フッ素系撥水剤組成物、及び撥水性繊維製品の製造方法 |
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WO2006038466A1 (ja) | 2004-10-05 | 2006-04-13 | Adeka Corporation | 水分散型ポリウレタン組成物 |
JP2009203316A (ja) | 2008-02-27 | 2009-09-10 | Adeka Corp | 水系ポリウレタン樹脂組成物及びそれを塗布してなる被塗物 |
JP2016524628A (ja) | 2013-03-29 | 2016-08-18 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | 非フッ素化ウレタン系コーティング |
JP2017160354A (ja) | 2016-03-10 | 2017-09-14 | 株式会社Adeka | 水系ポリウレタン樹脂組成物、及び該組成物を用いてなる塗料 |
JP2019173185A (ja) | 2018-03-27 | 2019-10-10 | 松本油脂製薬株式会社 | 繊維用撥水剤組成物及びその利用 |
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WO2021132170A1 (ja) | 2021-07-01 |
TW202134306A (zh) | 2021-09-16 |
US20230053165A1 (en) | 2023-02-16 |
CN114829435A (zh) | 2022-07-29 |
CN114829435B (zh) | 2024-07-02 |
KR20220127231A (ko) | 2022-09-19 |
EP4083146A1 (en) | 2022-11-02 |
JPWO2021132170A1 (ja) | 2021-07-01 |
EP4083146A4 (en) | 2024-01-24 |
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