JPWO2018092744A1 - 発泡用熱可塑性ポリウレタン樹脂およびその製造方法、ならびに、成形品 - Google Patents
発泡用熱可塑性ポリウレタン樹脂およびその製造方法、ならびに、成形品 Download PDFInfo
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- JPWO2018092744A1 JPWO2018092744A1 JP2018513894A JP2018513894A JPWO2018092744A1 JP WO2018092744 A1 JPWO2018092744 A1 JP WO2018092744A1 JP 2018513894 A JP2018513894 A JP 2018513894A JP 2018513894 A JP2018513894 A JP 2018513894A JP WO2018092744 A1 JPWO2018092744 A1 JP WO2018092744A1
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- Prior art keywords
- foaming
- thermoplastic polyurethane
- polyurethane resin
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- polyol
- Prior art date
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Abstract
Description
,4−ビス(イソシアナトメチル)シクロヘキサン(以下、トランス1,4体とする。)の立体異性体があり、本発明では、1,4−ビス(イソシアナトメチル)シクロヘキサンは、トランス1,4体を、例えば、60モル%以上、好ましくは、70モル%以上、より好ましくは、80モル%以上、さらに好ましくは、85モル%以上、例えば、99モル%以下、好ましくは、96モル%以下、より好ましくは、90モル%以下の割合で、含有している。換言すると、1,4−ビス(イソシアナトメチル)シクロヘキサンは、トランス1,4体およびシス1,4体の総量が100モル%であるため、シス1,4体を、例えば、1モル%以上、好ましくは、4モル%以上、より好ましくは、10モル%以上、例えば、40モル%以下、好ましくは、30モル%以下、より好ましくは、20モル%以下、さらに好ましくは、15モル%以下の割合で、含有している。
<ビス(イソシアナトメチル)シクロヘキサンの製造>
製造例1(1,4−ビス(イソシアナトメチル)シクロヘキサン(1)(以下、1,4−BIC(1)とする。)の製造)
特開2014−55229号公報の製造例6の記載に準拠して、純度99.5%以上のトランス体/シス体比98/2の1,4−ビス(アミノメチル)シクロヘキサンを92%の収率で得た。
13C−NMR測定によるトランス体/シス体比が93/7の1,4−ビス(アミノメチル)シクロヘキサン(三菱瓦斯化学社製)を原料として、特開2014−55229号公報の製造例1の記載に準拠して、385質量部の1,4−BIC(2)を得た。
攪拌機、温度計、還流管、および、窒素導入管を備えた4つ口フラスコに、製造例1で得られた1,4−BIC(1)を200質量部、製造例2で得られた1,4−BIC(2)を800質量部装入し、窒素雰囲気下、室温にて1時間攪拌して、1000質量部の1,4−BIC(3)を得た。
攪拌機、温度計、還流管、および、窒素導入管を備えた4つ口フラスコに、製造例2で得られた1,4−BIC(2)を865質量部、後述の製造例7で得られた1,4−BIC(7)を135質量部装入し、窒素雰囲気下、室温にて1時間攪拌して、1000質量部の1,4−BIC(4)を得た。
攪拌機、温度計、還流管、および、窒素導入管を備えた4つ口フラスコに、製造例2で得られた1,4−BIC(2)を615質量部、後述の製造例7で得られた1,4−BIC(7)を385質量部装入し、窒素雰囲気下、室温にて1時間攪拌して、1000質量部の1,4−BIC(5)を得た。
攪拌機、温度計、還流管、および、窒素導入管を備えた4つ口フラスコに、製造例2で得られた1,4−BIC(2)を462質量部、後述の製造例7で得られた1,4−BIC(7)を538質量部装入し、窒素雰囲気下、室温にて1時間攪拌して、1000質量部の1,4−BIC(6)を得た。
13C−NMR測定によるトランス体/シス体比が41/59の1,4−ビス(アミノメチル)シクロヘキサン(東京化成工業社製)を原料として、特開2014−55229号公報の製造例1の記載に準拠して、388質量部の1,4−BIC(7)を得た。
<イソシアネート基末端ポリウレタンプレポリマーの合成>
合成例1〜13
表1に記載した種類および質量割合でポリイソシアネート成分および第1ポリオール成分を、攪拌機、温度計、還流管および窒素導入管を備えた4つ口フラスコに仕込み、窒素雰囲気下、80℃にて1時間攪拌した。その後、合成例1、2、4〜11および13(イソシアネート基末端ポリウレタンプレポリマー(以下、プレポリマーとする。)(a)、(b)、(d)〜(k)および(m))においては、予めジイソノニルアジペート(ジェイ・プラス社製)により4質量%に希釈したオクチル酸スズ(商品名:スタノクト、エーピーアイコーポレーション社製)を、合成例3(プレポリマー(c))においては、予めジイソノニルアジペート(ジェイ・プラス社製、DINA)により4質量%に希釈したオクチル酸ビスマス(商品名:ネオスタンU−600、日東化成社製)を、ポリイソシアネート成分および第1ポリオール成分の総量に対して、触媒量として10ppm(ポリイソシアネート成分および第1ポリオール成分の総量10000質量部に対して、0.10質量部)添加し、合成例12(プレポリマー(l))においては、触媒を添加せずに、80℃の温調下、窒素気流下で攪拌混合しながら、プレポリマー(a)〜(l)を得た。
1,4−BIC:各製造例で製造した1,4−ビス(イソシアナトメチル)シクロヘキサン
1,3−BIC: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)
MDI:ジフェニルメタンジイソシアネート(商品名:コスモネートPH、三井化学SKCポリウレタン社製)
PLACCEL 230N:ポリカプロラクトンジオール(商品名:PLACCEL 230N、水酸基価:37.4mgKOH/g、数平均分子量:3000、ダイセル社製)
PTG3000SN:ポリテトラメチレンエーテルグリコール(商品名:PTG−3000SN、水酸基価:37.5mgKOH/g、数平均分子量:3000、保土ヶ谷化学工業社製)
PEG#4000:ポリエチレングリコール(商品名:PEG#4000、水酸基価:36.9mgKOH/g、数平均分子量:3000、日油社製)
<発泡用熱可塑性ポリウレタン樹脂の製造>
実施例1〜15、33および比較例1〜5
第2ポリオール成分(第1ポリオール成分を配合する場合は、第1ポリオール成分および第2ポリオール成分)中のヒドロキシ基(OH基)に対するプレポリマー中のイソシアネート基(NCO基)の割合(NCO基/OH基、NCOインデックス)が、実施例1〜3、5〜15、33および比較例1〜5(発泡用熱可塑性ポリウレタン樹脂(A)〜(C)および(E)〜(W))においては、1.01となるように、実施例4(発泡用熱可塑性ポリウレタン樹脂(D))においては、1.03となるように、第2ポリオール成分(第1ポリオール成分を配合する場合は、第1ポリオール成分および第2ポリオール成分)をステンレスカップに計量し、80℃に温調した。プレポリマーおよび第2ポリオール成分(第1ポリオール成分を配合する場合は、第1ポリオール成分および第2ポリオール成分)の総量に対して、イルガノックス245(BASF社製、耐熱安定剤)0.3質量%、チヌビン234(BASF社製、紫外線吸収剤)0.25質量%およびアデカスタブLA−72(ADEKA社製、耐光安定剤(HALS))0.15質量%を、ステンレス容器中で80℃に温調したプレポリマー中に添加し、高速ディスパーを使用して、500〜1500rpmの攪拌下、約3分間攪拌混合した。次いで、80℃に温調していた、第2ポリオール成分(第1ポリオール成分を配合する場合は、第1ポリオール成分および第2ポリオール成分)を配合し、高速ディスパーを使用して、500〜1500rpmの攪拌下、約10分間攪拌混合した。
<発泡用熱可塑性ポリウレタン樹脂の評価>
得られた発泡用熱可塑性ポリウレタン樹脂(A)〜(O)および(R)〜(W)について、以下の評価方法により評価した。なお、その結果を表2〜表6に示す。
(ゲルパーミエーションクロマトグラフィー(GPC)による発泡用熱可塑性ポリウレタン樹脂の重量平均分子量測定)
発泡用熱可塑性ポリウレタン50mg(サンプル)を、三角フラスコ中で10mLのN−メチルピロリドン中に浸漬し、100℃に温調し、サンプルが溶解するまでスターラーを用いて攪拌した。その後、この溶液を室温まで冷却した後、0.45μmの濾過フィルターを用いて濾過後、濾液を下記の分析条件でGPC測定した。そして、測定されたクロマトグラムから、クロマトグラムにおけるピークにおいて、ピークの総面積に対する、重量平均分子量が400,000以上となる高分子量成分に相当する面積の割合を算出した。なお、実施例2および比較例1のGPC測定より得られたクロマトグラムを図1に示す。
装置:東ソー HLC−8220GPC
カラム:Shodex KF−805L×2本 + KF−G4A(ガードカラム)
カラム温度:40℃
溶離液:N−メチルピロリドン(臭化リチウム50mM含有)
流量:0.7mL/min
試料濃度:0.5wt%
注入量:100μl
検出器:RI検出器(示差屈折計)
分子量マーカー:ポリスチレン(TSKゲル標準ポリスチレン)
(発泡用熱可塑性ポリウレタン樹脂のハードセグメント濃度)
ハードセグメント(ポリイソシアネート成分と第2ポリオール成分との反応により形成されるハードセグメント)濃度は、各成分の配合割合(仕込)から下記式により算出した。
式:[第2ポリオール成分の質量(g)+(第2ポリオール成分の質量(g)/第2ポリオール成分の平均分子量(g/mol))×ポリイソシアネート成分の平均分子量(g/mol)]÷(第1ポリオール成分の質量(g)+ポリイソシアネート成分(g)+第2ポリオール成分の質量(g))×100
(示差走査熱計(DSC)による発泡用熱可塑性ポリウレタン樹脂の凝集温度測定)
示差走査熱量計(エスアイアイ・ナノテクノロジー社製、商品名:EXSTAR6000 PCステーション、および、DSC220C)を使用して測定した。発泡用熱可塑性ポリウレタン約8mgを、アルミニウム製パンにできるだけ密着可能な形状となるように薄く切断して採取した。このアルミニウム製パンにカバーを被せてクリンプしたものを測定用試料(サンプル)とした。同様にアルミナを採取したものをリファレンス試料とした。サンプルおよびリファレンスをセル内の所定位置にセットした後、流量40NmL/minの窒素気流下、試料を10℃/minの速度で−100℃まで冷却し、同温度で5分間保持後、次いで、10℃/minの速度で270℃まで昇温した。さらに270℃で5分間保持した後、−70℃まで10℃/minの速度で冷却した。この冷却の間に現れる発熱ピークの温度を発泡用熱可塑性ポリウレタン樹脂の凝集温度とした。
(発泡用熱可塑性ポリウレタン樹脂の硬度測定)
実施例1〜15、33および比較例1〜5で得られた発泡用熱可塑性ポリウレタン樹脂のペレットを、それぞれ、射出成型機(型式:NEX−140、日精樹脂工業社製)を使用して、スクリュー回転数80rpm、バレル温度150〜270℃の設定にて、金型温度20℃、射出時間10秒、射出速度60mm/sおよび冷却時間20〜60秒の条件で、シート状に射出成形した。得られた2mm厚みのシートを、80℃のオーブン中で3日間アニール処理をした後、室温23℃、相対湿度55%の恒温恒湿条件下にて、7日間養生し、実施例1〜15、33および比較例1〜5それぞれの発泡用熱可塑性ポリウレタン樹脂のエラストマーシートを得た。
<ポリウレタン発泡成形品の製造>
以下のようにして、実施例1〜15、33および比較例1〜5の発泡用熱可塑性ポリウレタン樹脂からポリウレタン発泡成形品(A)〜(W)を得た。
(溶融粘度および流動開始温度の測定)
高化式フローテスター(島津製作所社製、型式:島津フローテスターCFT−500)を用いて、流動開始温度を測定し、その流動開始温度より20℃低い温度を測定開始温度として、荷重を196N、昇温速度を2.5℃/minとして溶融粘度を測定した。なお、測定に用いた発泡用熱可塑性ポリウレタン樹脂は、窒素気流下、80℃で一昼夜乾燥したものを使用した。
発泡用熱可塑性ポリウレタン樹脂(A)〜(O)および(R)〜(W)から、超臨界二酸化炭素を用いた押出発泡法により、ポリウレタン発泡成形品(A)〜(O)および(R)〜(W)を成形した。
発泡用熱可塑性ポリウレタン樹脂(B)から、超臨界二酸化炭素を用いた射出発泡法により、ポリウレタン発泡成形品(P)を成形した。
発泡用熱可塑性ポリウレタン樹脂(B)から、超臨界二酸化炭素を用いたビーズ発泡法により、ポリウレタン発泡体(Q)を成形した。
<ポリウレタン発泡成形品の評価>
得られたポリウレタン発泡成形品(A)〜(W)について、以下の評価方法により評価した。その結果を表2〜6に示す。
(セルの均一性)
得られたポリウレタン発泡成形品のセルの均一性を目視で観察し、以下のように、評価5〜1を設定し、5段階で評価した。
評価5:ほとんどのセルが微細で、セルの大きさはほぼ均一である。
評価4:粗大なセルは少なく、セルの大きさはほぼ均一である。
評価3:粗大なセルは少ないが、セルの大きさはそろっていない。
評価2:粗大なセルが多く、セルの大きさはそろっていない。
評価1:粗大なセルがほとんどであり、その大きさはそろっていない。
(コア密度(単位:kg/m3))
得られたポリウレタン発泡成形品から10cm×10cmのサイズの直方体を切り出して、測定試料を作製した。
(硬度(ASKER C)
得られたポリウレタン発泡成形品を重ねて、厚みを12mmとし、JIS K7312(1996年)の硬さ試験(タイプC)に準拠して、C硬度を測定した。
(反発弾性(単位:%))
得られたポリウレタン発泡成形品から10cm×10cmのサイズの直方体に切り出した後、厚みが12mmになるようにその直方体を重ねて測定試料とした。
(圧縮永久歪(単位:%))
得られたポリウレタン発泡成形品を直径29mmサイズの円柱状に切り出した後、厚みが12mmになるように測定試料を作製した。
(破断強度(単位:MPa))
得られたポリウレタン発泡成形品から、JIS−1号ダンベルを用いて測定試料を作製し、その後、測定試料の破断強度をJIS K6400−5(2012)に従って測定した。
(引裂強度(単位:kN/m))
得られたポリウレタン発泡成形品から、JIS−B型ダンベルを用いて測定試料を作製し、その後、測定試料の引裂強度をJIS K6400−5(2012)のB法に従って測定した。
(初期色相:b*、耐紫外線(UV)変色性:Δb)
ポリウレタン発泡成形品から30mm×40mmのサイズの直方体を切り出して、測定試料を作製し、色差計(東京電色社製、カラーエースMODEL TC−1)を用いて、黄色度b*を測定した。なお、b*は、一般に、ポリウレタンの色相の指標とされる。
プレポリマー:イソシアネート基末端ポリウレタンプレポリマー
1,4−BD:1,4−ブタンジオール(三菱化学社製)
PLACCEL 230N:ポリカプロラクトンポリオール(商品名:PLACCEL 230N、水酸基価:37.4mgKOH/g、数平均分子量:3000、ダイセル社製)
<ポリウレタン発泡成形品の用途>
参考実施例1
発泡用熱可塑性ポリウレタン樹脂(B)を用いて、実施例31と同様にして、射出発泡により密度0.25g/cm3のミッドソール用のポリウレタン発泡成形品に成形した。
発泡用熱可塑性ポリウレタン樹脂(B)を用いて、実施例31と同様にして、射出発泡により密度0.50g/cm3のショックアブソーバー用のポリウレタン発泡成形品に成形した。
発泡用熱可塑性ポリウレタン樹脂(B)を用いて、実施例31と同様にして、射出発泡により密度0.30g/cm3の化学機械研磨(Chemical Mechanical Polishing、CMP)パッド用のポリウレタン発泡成形品に成形した。
発泡用熱可塑性ポリウレタン樹脂(B)を用いて、実施例31と同様にして、射出発泡により密度0.15g/cm3の自動車内装部材用のポリウレタン発泡成形品に成形した。この発泡成形品を、直径50mmの円状(厚み3mm)に打ち抜き、23℃のオレイン酸へ7日間浸漬し、体積変化率(((V1(浸漬後の体積)−V0(浸漬前の体積))/V0)×100(%))を算出した結果、7%であった。
Claims (10)
- ビス(イソシアナトメチル)シクロヘキサンを含むポリイソシアネート成分と、ポリオール成分との反応生成物である発泡用熱可塑性ポリウレタン樹脂であって、
前記発泡用熱可塑性ポリウレタン樹脂をゲルパーミエーションクロマトグラフィーにより測定して得られるクロマトグラムのピークにおいて、重量平均分子量400,000以上の高分子量成分の面積が、前記ピークの総面積に対して、25%以上60%以下であることを特徴とする、発泡用熱可塑性ポリウレタン樹脂。 - 前記発泡用熱可塑性ポリウレタン樹脂の、示差走査熱量計により測定した凝集温度が、90℃以上180℃以下であることを特徴とする、請求項1に記載の発泡用熱可塑性ポリウレタン樹脂。
- 前記ビス(イソシアナトメチル)シクロヘキサンが、1,4−ビス(イソシアナトメチル)シクロヘキサンであることを特徴とする、請求項1に記載の発泡用熱可塑性ポリウレタン樹脂。
- 前記1,4−ビス(イソシアナトメチル)シクロヘキサンが、70モル%以上96モル%以下の割合でトランス体を含有することを特徴とする、請求項3に記載の発泡用熱可塑性ポリウレタン樹脂。
- ビス(イソシアナトメチル)シクロヘキサンを含むポリイソシアネート成分と、ポリオール成分とを反応させて一次生成物を得る反応工程と、
前記一次生成物を、50℃以上100℃以下で、3日以上10日以下、熱処理する熱処理工程と
を備えることを特徴とする、発泡用熱可塑性ポリウレタン樹脂の製造方法。 - 請求項1に記載の発泡用熱可塑性ポリウレタン樹脂を含むことを特徴とする、成形品。
- ミッドソールであることを特徴とする、請求項6に記載の成形品。
- ショックアブソーバーであることを特徴とする、請求項6に記載の成形品。
- 化学機械研磨パッドであることを特徴とする、請求項6に記載の成形品。
- 自動車内装部材であることを特徴とする、請求項6に記載の成形品。
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- 2017-11-14 WO PCT/JP2017/040836 patent/WO2018092744A1/ja unknown
- 2017-11-14 CN CN201780027713.9A patent/CN109071766B/zh active Active
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TWI738922B (zh) | 2021-09-11 |
EP3543273A4 (en) | 2020-06-03 |
KR102021270B1 (ko) | 2019-09-11 |
TW201829523A (zh) | 2018-08-16 |
JP6338809B1 (ja) | 2018-06-06 |
ES2907349T3 (es) | 2022-04-22 |
US20190211136A1 (en) | 2019-07-11 |
CN109071766B (zh) | 2019-09-27 |
US10633483B2 (en) | 2020-04-28 |
EP3543273B1 (en) | 2022-01-26 |
CN109071766A (zh) | 2018-12-21 |
EP3543273A1 (en) | 2019-09-25 |
KR20190041018A (ko) | 2019-04-19 |
WO2018092744A1 (ja) | 2018-05-24 |
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