JP6179697B1 - 水性ウレタン樹脂組成物、及び、合成皮革 - Google Patents
水性ウレタン樹脂組成物、及び、合成皮革 Download PDFInfo
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- JP6179697B1 JP6179697B1 JP2017521162A JP2017521162A JP6179697B1 JP 6179697 B1 JP6179697 B1 JP 6179697B1 JP 2017521162 A JP2017521162 A JP 2017521162A JP 2017521162 A JP2017521162 A JP 2017521162A JP 6179697 B1 JP6179697 B1 JP 6179697B1
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- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/12—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins
- D06N3/14—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins with polyurethanes
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
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- C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
- C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
- C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
- C08G18/0866—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being an aqueous medium
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- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
- C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
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- C08G18/2805—Compounds having only one group containing active hydrogen
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- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
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- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
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Abstract
Description
カラム:東ソー株式会社製の下記のカラムを直列に接続して使用した。
「TSKgel G5000」(7.8mmI.D.×30cm)×1本
「TSKgel G4000」(7.8mmI.D.×30cm)×1本
「TSKgel G3000」(7.8mmI.D.×30cm)×1本
「TSKgel G2000」(7.8mmI.D.×30cm)×1本
検出器:RI(示差屈折計)
カラム温度:40℃
溶離液:テトラヒドロフラン(THF)
流速:1.0mL/分
注入量:100μL(試料濃度0.4質量%のテトラヒドロフラン溶液)
標準試料:下記の標準ポリスチレンを用いて検量線を作成した。
東ソー株式会社製「TSKgel 標準ポリスチレン A−500」
東ソー株式会社製「TSKgel 標準ポリスチレン A−1000」
東ソー株式会社製「TSKgel 標準ポリスチレン A−2500」
東ソー株式会社製「TSKgel 標準ポリスチレン A−5000」
東ソー株式会社製「TSKgel 標準ポリスチレン F−1」
東ソー株式会社製「TSKgel 標準ポリスチレン F−2」
東ソー株式会社製「TSKgel 標準ポリスチレン F−4」
東ソー株式会社製「TSKgel 標準ポリスチレン F−10」
東ソー株式会社製「TSKgel 標準ポリスチレン F−20」
東ソー株式会社製「TSKgel 標準ポリスチレン F−40」
東ソー株式会社製「TSKgel 標準ポリスチレン F−80」
東ソー株式会社製「TSKgel 標準ポリスチレン F−128」
東ソー株式会社製「TSKgel 標準ポリスチレン F−288」
東ソー株式会社製「TSKgel 標準ポリスチレン F−550」
撹拌機、還流冷却管、温度計及び窒素導入管を備えた4ツ口フラスコに、窒素気流下、ポリカーボネートジオール(宇部興産株式会社製「ETERNACOLL UH−200」数平均分子量:2,000、以下「PC−1」と略記する。)500質量部、両末端ジオール型反応性シリコーン(JNC株式会社製「サイラプレーンFM−4425」数平均分子量:10,000、以下「両末端ジオール型Si−1」と略記する。)125質量部、ジメチロールプロピオン酸(以下「DMPA」と略記する。)25質量部、メチルエチルケトン360質量部を加え、均一に混合した後、ジシクロヘキシルメタンジイソシアネート(以下「H12MDI」と略記する。)177質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させることによって、分子末端にイソシアネート基を有するウレタンプレポリマーのメチルエチルケトン溶液を得た。次いで、得られたウレタンプレポリマーのメチルエチルケトン溶液にトリエチルアミン19質量部を加え、前記ウレタンプレポリマー中にカルボキシル基を中和した後、イオン交換水1960質量部を加え、次いで、エチレンジアミン(以下「EDA」と略記する。)14質量部を加え反応させた。反応終了後、メチルエチルケトンを減圧下留去することによって、水性ウレタン樹脂組成物(X−1)(不揮発分;30質量%、酸価;13KOHmg/g)を得た。
撹拌機、還流冷却管、温度計及び窒素還流管を備えた4ツ口フラスコに、窒素気流下、ポリカーボネートジオール(旭化成ケミカルズ株式会社製「DURANOL T5652」、数平均分子量:2,000、以下「PC−2」と略記する。)500質量部、片末端ジオール型反応性シリコーン(信越化学工業株式会社製「X−22−176GX−A」、数平均分子量:14,000、以下「片末端ジオール型Si−1」と略記する。)26質量部、DMPA8質量部、メチルエチルケトン269質量部を加え、均一に混合した後、イソホロンジイソシアネート(以下「IPDI」と略記する。)86質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させることによって、分子末端にイソシアネート基を有するウレタンプレポリマーのメチルエチルケトン溶液を得た。次いで、得られたウレタンプレポリマーのメチルエチルケトン溶液にトリエチルアミン6質量部を加え、前記ウレタンプレポリマー中にカルボキシル基を中和した後、イオン交換水1463質量部を加え、次いで、ピペラジン(以下「PZ」と略記する。)7質量部を加え反応させた。反応終了後、メチルエチルケトンを減圧下留去することによって、水性ウレタン樹脂組成物(X−2)(不揮発分;30質量%、酸価;5KOHmg/g)を得た。
撹拌機、還流冷却管、温度計及び窒素還流管を備えた4ツ口フラスコに、窒素気流下、ポリカーボネートジオール(旭化成ケミカルズ株式会社製「DURANOL T4692、数平均分子量:2,000、以下「PC−3」と略記する。)500質量部、片末端ジオール型反応性シリコーン(JNC株式会社製「サイラプレーン FM−DA21」、数平均分子量:5,000、以下「片末端ジオール型Si−2」と略記する。)88質量部、DMPA26質量部、メチルエチルケトン332質量部を加え、均一に混合した後、H12MDIを145質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させることによって、分子末端にイソシアネート基を有するウレタンプレポリマーのメチルエチルケトン溶液を得た。次いで、得られたウレタンプレポリマーのメチルエチルケトン溶液にトリエチルアミン20質量部を加え、前記ウレタンプレポリマー中にカルボキシル基を中和した後、イオン交換水1808質量部を加え、次いで、イソホロンジアミン(以下「IPDA」と略記する。)16質量部を加え反応させた。反応終了後、メチルエチルケトンを減圧下留去することによって、水性ウレタン樹脂組成物(X−3)(不揮発分;30質量%、酸価;14KOHmg/g)を得た。
撹拌機、還流冷却管、温度計及び窒素還流管を備えた4ツ口フラスコに、窒素気流下、PC−2を500質量部、ポリテトラメチレングリコール(数平均分子量:1,000、以下「PTMF1000」と略記する。)133質量部、片末端ジオール型反応性シリコーン(信越化学工業株式会社製「X−22−176F」、数平均分子量:12,000、以下「片末端ジオール型Si−3」と略記する。)33質量部、DMPA17質量部、メチルエチルケトン385質量部を加え、均一に混合した後、IPDIを86質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させることによって、分子末端にイソシアネート基を有するウレタンプレポリマーのメチルエチルケトン溶液を得た。次いで、得られたウレタンプレポリマーのメチルエチルケトン溶液にトリエチルアミン13質量部を加え、前記ウレタンプレポリマー中にカルボキシル基を中和した後、イオン交換水2098質量部を加え、次いで、EDA15質量部を加え反応させた。反応終了後、メチルエチルケトンを減圧下留去することによって、水性ウレタン樹脂組成物(X−4)(不揮発分;30質量%、酸価;8KOHmg/g)を得た。
撹拌機、還流冷却管、温度計及び窒素還流管を備えた4ツ口フラスコに、窒素気流下、ポリカーボネートジオール(旭化成ケミカルズ株式会社製「DURANOL G3452」、数平均分子量:1,000、以下「PC−4」と略記する。)500質量部、片末端モノオール型反応性シリコーン(JNC株式会社製「サイラプレーンFM−0425」、数平均分子量:10,000、以下「片末端モノオール型Si−1」と略記する。)56質量部、DMPA17質量部、メチルエチルケトン291質量部を加え、均一に混合した後、ヘキサンメチレンジイソシアネート(以下「HDI」と略記する。)86質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させることによって、分子末端にイソシアネート基を有するウレタンプレポリマーのメチルエチルケトン溶液を得た。次いで、得られたウレタンプレポリマーのメチルエチルケトン溶液にトリエチルアミン13質量部を加え、前記ウレタンプレポリマー中にカルボキシル基を中和した後、イオン交換水1586質量部を加え、次いで、IPDA22質量部を加え反応させた。反応終了後、メチルエチルケトンを減圧下留去することによって、水性ウレタン樹脂組成物(X−5)(不揮発分;30質量%、酸価;10KOHmg/g)を得た。
撹拌機、還流冷却管、温度計及び窒素還流管を備えた4ツ口フラスコに、窒素気流下、PC−1を500質量部、両末端ジアミン型反応性シリコーン(JNC株式会社製「サイラプレーンFM−3325」、数平均分子量:10,000、以下「両末端ジアミン型Si−1」と略記する。)125質量部、DMPA25質量部、メチルエチルケトン362質量部を加え、均一に混合した後、H12MDIを165質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させることによって、分子末端にイソシアネート基を有するウレタンプレポリマーのメチルエチルケトン溶液を得た。次いで、得られたウレタンプレポリマーのメチルエチルケトン溶液にトリエチルアミン19質量部を加え、前記ウレタンプレポリマー中にカルボキシル基を中和した後、イオン交換水1972質量部を加え、次いで、IPDAを31質量部を加え反応させた。反応終了後、メチルエチルケトンを減圧下留去することによって、水性ウレタン樹脂組成物(X−6)(不揮発分;30質量%、酸価;12KOHmg/g)を得た。
撹拌機、還流冷却管、温度計及び窒素還流管を備えた4ツ口フラスコに、窒素気流下、ポリテトラメチレングリコール(数平均分子量:2,000、以下「PTMG2000」と略記する。)500質量部、片末端ジオール型Si−2を167質量部、DMPAを23質量部、メチルエチルケトン400質量部を加え、均一に混合した後、IPDIを203質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させることによって、分子末端にイソシアネート基を有するウレタンプレポリマーのメチルエチルケトン溶液を得た。次いで、得られたウレタンプレポリマーのメチルエチルケトン溶液にトリエチルアミン18質量部を加え、前記ウレタンプレポリマー中にカルボキシル基を中和した後、イオン交換水2176質量部を加え、次いで、PZを39質量部加え反応させた。反応終了後、メチルエチルケトンを減圧下留去することによって、水性ウレタン樹脂組成物(X−7)(不揮発分;30質量%、酸価;11KOHmg/g)を得た。
撹拌機、還流冷却管、温度計及び窒素還流管を備えた4ツ口フラスコに、PC−1を500質量部、両末端ジオール型反応性シリコーン(信越化学工業株式会社製「KF−6002、数平均分子量:3,200、以下「両末端ジオール型Si’−1」と略記する。)125質量部、DMPAを25質量部、メチルエチルケトン360質量部を加え、均一に混合した後、H12MDIを177質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させることによって、分子末端にイソシアネート基を有するウレタンプレポリマーのメチルエチルケトン溶液を得た。次いで、得られたウレタンプレポリマーのメチルエチルケトン溶液にトリエチルアミン19質量部を加え、前記ウレタンプレポリマー中にカルボキシル基を中和した後、イオン交換水1986質量部を加え、次いで、EDAを14質量部を加え反応させた。反応終了後、メチルエチルケトンを減圧下留去することによって、水系ポリウレタン樹脂組成物(X’−1)(不揮発分;30質量%、酸価;13KOHmg/g)を得た。
撹拌機、還流冷却管、温度計及び窒素還流管を備えた4ツ口フラスコに、窒素気流下、PC−3を500質量部、片末端ジオール型反応性シリコーン(JNC製「サイラプレーン FM−DA11」、数平均分子量:1,000、以下「片末端ジオール型Si’−1」と略記する。)88質量部、DMPAを26質量部、メチルエチルケトン343質量部を加え、均一に混合した後、H12MDIを167質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させることによって、分子末端にイソシアネート基を有するウレタンプレポリマーのメチルエチルケトン溶液を得た。次いで、得られたウレタンプレポリマーのメチルエチルケトン溶液にトリエチルアミン20質量部を加え、前記ウレタンプレポリマー中にカルボキシル基を中和した後、イオン交換水1865質量部を加え、次いで、IPDAを18質量部を加え反応させた。反応終了後、メチルエチルケトンを減圧下留去することによって、水性ウレタン樹脂組成物(X’−2)(不揮発分;30質量%、酸価;14KOHmg/g)を得た。
実施例及び比較例で得られた水性ウレタン樹脂組成物を乾燥し、乾燥固化した樹脂粒子の0.05g〜0.5gを、300mL三角フラスコに秤量し、次いで、テトラヒドロフランとイオン交換水との質量割合[テトラヒドロフラン/イオン交換水]が80/20の混合溶媒約80mLを加えそれらの混合液を得た。
次いで、前記混合液にフェノールフタレイン指示薬を混合した後、あらかじめ標定された0.1mol/Lの水酸化カリウム水溶液で滴定し、滴定に用いた水酸化カリウム水溶液の量から下記計算式(1)に従い、水性ウレタン樹脂(A)の酸価(mgKOH/g)を求めた。
計算式 A=(B×f×5.611)/S (1)
式中、Aは樹脂の固形分酸価(mgKOH/g)、Bは滴定に用いた0.1mol/L水酸化カリウム水溶液の量(mL)、fは0.1mol/L水酸化カリウム水溶液のファクター、Sは樹脂粒子の質量(g)、5.611は水酸化カリウムの式量(56.11/10)である。
実施例及び比較例で得られた水性ウレタン樹脂組成物100質量部、水分散性黒色顔料(DIC株式会社製「ダイラックHS−9530」)10質量部、会合型増粘剤(DIC株式会社製「ハイドラン アシスター T10」)1質量部を配合し、離型紙上に乾燥後の膜厚が30μmとなるように塗布し、70℃で2分間乾燥させ、表皮層を得た。
次いで、水性ウレタン接着剤(DIC株式会社製「ハイドランWLA−412」)を100質量部、会合型増粘剤(DIC株式会社製「ハイドラン アシスター T10」)1質量部、ポリイソシアネート架橋剤(DIC株式会社製「ハイドラン アシスター C5」)を9質量部配合し、前記表皮層上に乾燥後の膜厚が50μmとなるように塗布し、70℃で3分間乾燥させた。乾燥後、直ちにT/R起毛布を貼り合せ、120℃で2分間熱処理し、50℃で2日間熟成させてから離型紙を剥離して合成皮革を得た。
得られた合成皮革に対し、平面磨耗試験(JASO−M403−88B法、荷重;1kg、ストローク;140mm)を行い、合成皮革の表面が磨耗し基布が確認できるまでの回数を測定し、以下のように評価した。
「A」;30,000回以上
「B」;10,000回以上30,000回未満
「C」;10,000回未満
得られた合成皮革を70℃、湿度95%の湿熱条件下で5週間養生した後の外観変化を確認し、以下のように評価した。
「A」;外観に変化なし。
「B」;外観に艶の変化が生じた。
「C」;外観に艶の変化が生じ、かつ、べたつきが生じた。
Claims (4)
- ポリオール(a1)と、数平均分子量が4,000以上であり、イソシアネート基と反応する官能基を有する反応性シリコーン(a2)と、ポリイソシアネート(a3)とを必須原料とした反応物であるウレタン樹脂(A)、及び、水性媒体(B)を含有し、乳化剤を含有しないことを特徴とする水性ウレタン樹脂組成物。
- 前記反応性シリコーン(a2)の使用量が、ウレタン樹脂(A)を構成する原料の合計質量中1〜25質量%の範囲である請求項1記載の水性ウレタン樹脂組成物。
- 前記ウレタン樹脂(A)が、酸価が20mgKOH/g以下のアニオン性ウレタン樹脂である請求項1又は2記載の水性ウレタン樹脂組成物。
- 請求項1〜3のいずれか1項記載の水性ウレタン樹脂組成物により形成された表皮層及び/又は表面処理層を有することを特徴とする合成皮革。
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CN112703287A (zh) * | 2018-06-07 | 2021-04-23 | Dic株式会社 | 合成皮革 |
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CN113085314A (zh) * | 2019-12-23 | 2021-07-09 | Dic株式会社 | 合成皮革 |
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CN107531861A (zh) | 2018-01-02 |
TW201807001A (zh) | 2018-03-01 |
EP3444286A1 (en) | 2019-02-20 |
EP3444286B1 (en) | 2023-01-11 |
JPWO2017179291A1 (ja) | 2018-04-19 |
TWI719185B (zh) | 2021-02-21 |
KR20170134574A (ko) | 2017-12-06 |
US20180142409A1 (en) | 2018-05-24 |
KR101966579B1 (ko) | 2019-04-05 |
EP3444286A4 (en) | 2019-12-25 |
WO2017179291A1 (ja) | 2017-10-19 |
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