JPWO2012121291A1 - ペンタメチレンジイソシアネート、ペンタメチレンジイソシアネートの製造方法、ポリイソシアネート組成物、ポリウレタン樹脂およびポリウレア樹脂 - Google Patents
ペンタメチレンジイソシアネート、ペンタメチレンジイソシアネートの製造方法、ポリイソシアネート組成物、ポリウレタン樹脂およびポリウレア樹脂 Download PDFInfo
- Publication number
- JPWO2012121291A1 JPWO2012121291A1 JP2013503579A JP2013503579A JPWO2012121291A1 JP WO2012121291 A1 JPWO2012121291 A1 JP WO2012121291A1 JP 2013503579 A JP2013503579 A JP 2013503579A JP 2013503579 A JP2013503579 A JP 2013503579A JP WO2012121291 A1 JPWO2012121291 A1 JP WO2012121291A1
- Authority
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- Japan
- Prior art keywords
- mass
- pentamethylene diisocyanate
- pentamethylenediamine
- group
- acid
- 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
Links
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- 239000000203 mixture Substances 0.000 title claims description 216
- 239000005056 polyisocyanate Substances 0.000 title claims description 190
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- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims abstract description 431
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Abstract
Description
(a)イソシアヌレート基
(b)アロファネート基
(c)ビウレット基
(d)ウレタン基
(e)ウレア基
また、本発明のポリウレタン樹脂は、上記のペンタメチレンジイソシアネート、および/または、上記のポリイソシアネート組成物と、活性水素化合物とを反応させることにより得られることを特徴としている。
上記一般式(3)で示される化合物として、より具体的には、例えば、2−(アミノメチル)−3,4,5,6−テトラヒドロピリジンなどが挙げられる。
(a)イソシアヌレート基
(b)アロファネート基
(c)ビウレット基
(d)ウレタン基
(e)ウレア基
上記(a)の官能基(イソシアヌレート基)を含有するポリイソシアネート組成物は、ペンタメチレンジイソシアネートのトリマー(三量体)であって、例えば、ペンタメチレンジイソシアネートを公知のイソシアヌレート化触媒の存在下において反応させ、三量化することにより、得ることができる。
<ペンタメチレンジアミンの反応収率(単位:mol%)>
L−リシン一塩酸塩(和光純薬工業社製)、および、後述する(ペンタメチレンジアミンの蒸留)で得られた精製ペンタメチレンジアミンを用い、以下のHPLC(高速液体クロマトグラフ)分析条件下で得られたクロマトグラフの面積値から作成した検量線により、ペンタメチレンジアミンの濃度を算出し、L−リシン一塩酸塩およびペンタメチレンジアミンの合計濃度に対するペンタメチレンジアミンの濃度の割合を、ペンタメチレンジアミンの反応収率とした。
カラム温度;40℃
溶離液;0.2mol/L リン酸ナトリウム(pH7.7)+2.3mmol/L 1−オクタンスルホン酸ナトリウム
流量;0.5mL/min
L−リシン一塩酸塩およびペンタメチレンジアミンの検出には、オルトフタルアルデヒドを用いたポストカラム誘導体化法〔J.Chromatogr.,83,353−355(1973)〕を採用した。
<ペンタメチレンジアミンの純度(単位:質量%)>
後述する(ペンタメチレンジアミンの蒸留)で得られた精製ペンタメチレンジアミンを用い、以下のガスクロマトグラフ(GC)分析条件で得られたガスクロマトグラムの面積値から作成した検量線により、ペンタメチレンジアミンの純度を算出した。
カラム;WCOT FUSED SILICA CP−SIL 8CB FOR AMINES(VARIAN社製)
オーブン温度;40℃で3分間保持、40℃から300℃まで、10℃/minで昇温、300℃で11分間保持
注入口温度;250℃
検出器温度;280℃
キャリアガス;ヘリウム
検出法;FID
<抽出率(単位:質量%)>
抽出溶媒によるペンタメチレンジアミンの抽出率を求めるため、上記(ペンタメチレンジアミンの純度)と同様の測定を行い、抽出操作前のペンタメチレンジアミン水溶液中のペンタメチレンジアミン濃度と、抽出操作後の抽出溶媒中のペンタメチレンジアミン濃度とを測定した。
(a)抽出溶媒中のペンタメチレンジアミンの質量=抽出溶媒中のペンタメチレンジアミン濃度×抽出溶媒の質量/100
(b)仕込んだペンタメチレンジアミン水溶液中のペンタメチレンジアミンの質量=抽出操作前のペンタメチレンジアミン水溶液のジアミノペンタン濃度×仕込んだペンタメチレンジアミン水溶液の質量/100
抽出率(質量%)=(a)/(b)×100
<C=N結合を含む環状構造を有した化合物の総含有量(単位:質量%)>
後述する(2,3,4,5−テトラヒドロピリジン濃度)と(2−(アミノメチル)−3,4,5,6−テトラヒドロピリジン濃度)との合計値により求めた。
<2,3,4,5−テトラヒドロピリジン濃度(単位:質量%)>
後述する(未知物質の構造解析)で得られた、2,3,4,5−テトラヒドロピリジンを用い、(ペンタメチレンジアミンの純度)に記載と同条件の測定により得られたガスクロマトグラムの面積値から作成した検量線により、2,3,4,5−テトラヒドロピリジン濃度を算出した。
<2−(アミノメチル)−3,4,5,6−テトラヒドロピリジン濃度(単位:質量%)>
後述する(未知物質の構造解析)で得られた、2−(アミノメチル)−3,4,5,6−テトラヒドロピリジンを用い、(ペンタメチレンジアミンの純度)に記載と同条件の測定により得られたガスクロマトグラムの面積値から作成した検量線により、2−(アミノメチル)−3,4,5,6−テトラヒドロピリジン濃度を算出した。
<ペンタメチレンジイソシアネートの純度(単位:質量%)>
ペンタメチレンジイソシアネートの純度は、以下[1]、[2]の何れかの方法にて測定した。
[1]後述する実施例1で得られたペンタメチレンジイソシアネート(a)を用い、以下のGC分析条件下で得られたクロマトグラムの面積値から検量線を作成し、ペンタメチレンジイソシアネートの純度を算出した。
カラム;UADX−30(フロンティア・ラボ社製)0.25mmφ×30m、膜厚0.15μm
オーブン温度;50℃で5分間保持、50℃から200℃まで、10℃/minで昇温、200℃から350℃まで、20℃/minで昇温、350℃で7.5分間保持
注入口温度;250℃
検出器温度;250℃
He流量 ; 1.2mL/min
注入モード ; スプリット
検出方法;FID
[2]電位差滴定装置を用いて、JIS K−1556に準拠し、n−ジブチルアミン法により測定したイソシアネート基濃度から、ペンタメチレンジイソシアネートの純度を算出した。
<熱処理におけるペンタメチレンジイソシアネートの収率(単位:質量%)>
熱処理におけるペンタメチレンジイソシアネートの収率は、以下の式により算出した。
(a):熱処理前のペンタメチレンジイソシアネートの質量部
(b):熱処理前のペンタメチレンジイソシアネートの純度
(c):熱処理後のペンタメチレンジイソシアネートの質量部
(d):熱処理後のペンタメチレンジイソシアネートの純度
<加水分解性塩素の濃度(単位:%)>
イソシアネートに含有される加水分解性塩素の濃度(HC)は、JIS K−1556(2000)の附属書3に記載されている加水分解性塩素の試験方法に準拠して測定した。
<式(1)で示される化合物および式(2)で示される化合物の総含有量(単位:ppm>
下記一般式(1)で示される化合物、および、下記一般式(2)で示される化合物の総含有量は、(ペンタメチレンジイソシアネートの純度)の[1]と同条件の測定により得られたガスクロマトグラムの面積値とした。
後述する実施例1で得られたペンタメチレンジイソシアネート(a)を用い、以下のHPLC分析条件下で得られたクロマトグラムの面積値から作成した検量線により、ポリイソシアネート組成物中のペンタメチレンジイソシアネートの濃度を算出した。
1) ポンプ LC−20AT
2) デガッサ DGU−20A3
3) オートサンプラ SIL−20A
4) カラム恒温槽 COT−20A
5) 検出器 SPD−20A
カラム;SHISEIDO SILICA SG−120
カラム温度;40℃
溶離液;n−ヘキサン/メタノール/1,2−ジクロロエタン=90/5/5(体積比)
流量;0.2mL/min
検出方法;UV 225nm
<イソシアネート基の転化率(単位:%)>
イソシアネート基の転化率は、以下のGPC測定条件において得られたクロマトグラムにより、全ピーク面積に対するペンタメチレンジイソシアネートのピークよりも高分子量側にあるピークの面積の割合を、イソシアネート基の転化率とした。
カラム;G1000HXL、G2000HXLおよびG3000HXL(以上、東ソー製商品名)を直列に連結
カラム温度;40℃
溶離液;テトラヒドロフラン
流量;0.8mL/min
検出方法;示差屈折率
標準物質;ポリエチレンオキシド(東ソー社製、商品名:TSK標準ポリエチレンオキシド)
<イソシアネート3量体濃度(単位:質量%)>
上記した(イソシアネート基の転化率)と同様の測定を行い、ペンタメチレンジイソシアネートの3倍の分子量に相当するピーク面積比率を、イソシアネート3量体濃度とした。
<イソシアネート基濃度(単位:質量%)>
ポリイソシアネート組成物のイソシアネート基濃度は、電位差滴定装置を用いて、JIS K−1556に準拠したn−ジブチルアミン法により、測定した。
<粘度(単位:mPa・s)>
東機産業社製のE型粘度計TV−30を用いて、ポリイソシアネート組成物の25℃における粘度を測定した。
<色相(単位:APHA)>
JIS K−0071に準拠した方法により、ポリイソシアネート組成物の色相を測定した。
(ペンタメチレンジアミンの蒸留)
温度計、蒸留塔、冷却管および窒素導入管を備えた4つ口フラスコに、ペンタメチレンジアミン(東京化成社製)を仕込み、塔頂温度が111〜115℃、10KPaの条件下、さらに還流しながら精留し、精製ペンタメチレンジアミンを得た。蒸留精製したペンタメチレンジアミンは、ガスクロマトグラフィーの面積比が100%であった。
(リジン脱炭酸酵素遺伝子(cadA)のクローニング)
Escherichia coli W3110株(ATCC27325)から常法に従い調製したゲノムDNAをPCRの鋳型に用いた。
(形質転換体の作製)
pCADAを用いてEscherichia coli W3110株を通常の方法で形質転換し、得られた形質転換体をW/pCADAと命名した。
フラスコに、L−リシン一塩酸塩(和光純薬製)を、終濃度が45質量%となるように、および、ピリドキサールリン酸(和光純薬製)を、終濃度が0.15mmol/Lとなるように調製した基質溶液120質量部を加えた。次に、上記のW/pCADA菌体破砕液(仕込み乾燥菌体換算重量0.3g)を添加し反応を開始した。反応条件は37℃、200rpmとした。反応液のpHは6mol/Lの塩酸にてpH6に調整した。24時間後のペンタメチレンジアミンの反応収率は99%に達していた。上記の反応24時間後の反応液を、6mol/Lの塩酸にてpH2に調整し、0.6質量部の活性炭(三倉化成社製 粉末活性炭PM−SX)を添加し、25℃で1時間攪拌を行った後、濾紙(ADVANTEC社製 5C)にて濾過を行った。次に、この濾液を水酸化ナトリウムにてpH12に調整し、ペンタメチレンジアミン水溶液(17.0質量%水溶液)を得た。
分液ロートにペンタメチレンジアミン水溶液100質量部とn−ブタノール100質量部とを仕込み、10分間混合し、その後30分間静置した。水層である下層を抜き出し、次いで有機層(ペンタメチレンジアミンを含むn−ブタノール)である上層を抜き出した。抽出率を測定した結果、91.6%であった。次いで、温度計、蒸留塔、冷却管および窒素導入管を備えた4つ口フラスコに有機層の抽出液80質量部を仕込み、オイルバス温度を120℃とし、10kPaの減圧下でn−ブタノールを留去させた。次いで、オイルバス温度を140℃とし、10kPaの減圧下でペンタメチレンジアミンを留去させ、純度99.9質量%のペンタメチレンジアミン(a)を得た。
n−ブタノール100質量部に代えて、イソブタノール100質量部を仕込んだ以外は、上記の製造例1と同様にして溶媒抽出を行った。抽出率を測定した結果、86.0%であった。
次いで、製造例1と同様にして、イソブタノールを留去させ、純度99.8質量%のペンタメチレンジアミン(b)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、調製例2で得られたペンタメチレンジアミン水溶液200質量部を装入し、38kPa、80℃で水を留去させ、19.7質量%のペンタメチレンジアミン水溶液を得た。
分液ロートにペンタメチレンジアミン水溶液100質量部とクロロホルム100質量部とを仕込み、10分間混合し、その後30分間静置した。水層である下層を抜き出し、次いで有機層である上層を抜き出した。抽出率を測定した結果、61.7%であった。次いで、温度計、蒸留塔、冷却管および窒素導入管を備えた4つ口フラスコに有機層の抽出液80質量部を仕込み、オイルバス温度を120℃とし、10kPaの減圧下でクロロホルムを留去させ、ペンタメチレンジアミン(d*)を得た。次いで、オイルバス温度を140℃とし、10kPaの減圧下でペンタメチレンジアミンを留去させ、純度99.2質量%のペンタメチレンジアミン(d)を得た。
固相抽出カートリッジ(VARIAN社製、型式1225−6067)を用いて、ペンタメチレンジアミンに含まれる不純物の分取を行い、GC−MS分析およびNMR分析により構造解析を行った。
2回目;メタノール50mLとクロロホルム450mLの混合溶液
3回目;メタノール100mLとクロロホルム400mLの混合溶液
4回目;メタノール100mLとクロロホルム400mLの混合溶液
5回目;メタノール100mLとクロロホルム400mLの混合溶液
1、2回目の流出液を窒素パージにより溶媒除去し、得られた化合物を、下記GC−MS分析1の条件で測定した。その結果、ペンタメチレンジアミンは検出されず、面積比99%の2,3,4,5−テトラヒドロピリジンが検出された。
<GC−MS分析1>
装置;Q1000GC K9(日本電子社製)
イオン化法;EI
カラム;WCOT FUSED SILICA CP−SIL 8CB FOR AMINES(VARIAN社製)、0.25mmφ×30m
オーブン温度;40℃で3分間保持、40℃から300℃まで、10℃/minで昇温、300℃で11分間保持
注入口温度;250℃
He流量 ; 0.7mL/min
注入モード ; スプリット
<GC−MS分析2>
装置;JMS−T100GC(日本電子製)
イオン化法;FI
カラム;WCOT FUSED SILICA CP−SIL 8CB FOR AMINES(VARIAN製)、0.25mmφ×30m
オーブン温度;40℃で3分間保持、40℃から300℃まで、10℃/minで昇温、300℃で11分間保持
注入口温度;250℃
He流量 ; 0.7mL/min
注入モード ; スプリット
<NMR分析>
装置;核磁気共鳴装置 ECA500(日本電子製)
測定法;1H−NMR、13C−NMR、COSY、HMQC、HMBC
試験例2(不純物濃度の測定)
各製造例により得られたペンタメチレンジアミンに含まれる不純物(2,3,4,5−テトラヒドロピリジン、および、2−(アミノメチル)−3,4,5,6−テトラヒドロピリジン)の濃度を、以下に示す手法により、算出した。
電磁誘導撹拌機、自動圧力調整弁、温度計、窒素導入ライン、ホスゲン導入ライン、凝縮器、原料フィードポンプを備え付けたジャケット付き加圧反応器に、o−ジクロロベンゼン2000質量部を仕込んだ。次いで、ホスゲン2300質量部をホスゲン導入ラインから加え、撹拌を開始した。反応器のジャケットには冷水を通し、内温を約10℃に保った。そこへ、ペンタメチレンジアミン(a)400質量部をo−ジクロロベンゼン2600質量部に溶解した溶液を、フィードポンプにて60分かけてフィードし、30℃以下、常圧下で冷ホスゲン化を開始した。フィード終了後、加圧反応器内は淡褐白色スラリー状液となった。
装置;Q1000GC K9(日本電子社製)
イオン化法;EI
カラム;DB−5MS+DG(アジレント・テクノロジー社製)0.25mmφ×30m、膜厚0.25μm
オーブン温度;40℃で3分間保持、40℃から300℃まで、10℃/minで昇温、300℃で11分間保持
注入口温度;200℃
He流量 ; 0.7mL/min
注入モード ; スプリット
ペンタメチレンジイソシアネート(a)は、式(1)で示される化合物および式(2)で示される化合物の総含有量が25ppmであった。
実施例1と同様の条件および操作にて、純度98.9質量%のペンタメチレンジイソシアネート(b0)を557質量部得た。
実施例1と同様の条件および操作にて、純度98.8質量%のペンタメチレンジイソシアネート(c0)を557質量部得た。
実施例1と同様の条件および操作にて、純度98.7質量%のペンタメチレンジイソシアネート(d0)を558質量部得た。
ペンタメチレンジアミン(a)に代えて、ペンタメチレンジアミン(c)を用いた以外は、実施例1と同様の条件および操作にて、純度98.4質量%のペンタメチレンジイソシアネート(e0)を552質量部得た。
次いで、実施例1と同様の条件および操作にて精留し、純度99.9質量%のペンタメチレンジイソシアネート(e)を得た。ペンタメチレンジイソシアネート(e)は、HCが0.008%、式(1)で示される化合物および式(2)で示される化合物の総含有量が280ppmであった。
実施例1と同様の条件および操作にて、純度98.7質量%のペンタメチレンジイソシアネート(f0)を558質量部得た。
次いで、実施例1と同様の条件および操作にて精留し、純度99.8質量%のペンタメチレンジイソシアネート(f)を得た。ペンタメチレンジイソシアネート(f)は、式(1)で示される化合物および式(2)で示される化合物の総含有量が340ppmであった。
実施例1と同様の条件および操作にて、純度98.6質量%のペンタメチレンジイソシアネート(g0)を559質量部得た。
ペンタメチレンジアミン(a)に代えて、ペンタメチレンジアミン(c)を用いた以外は、実施例1と同様の条件および操作にて、純度98.4質量%のペンタメチレンジイソシアネート(h0)を552質量部得た。
実施例1と同様の条件および操作にて、純度98.7質量%のペンタメチレンジイソシアネート(i0)を558質量部得た。
ペンタメチレンジアミン(a)に代えて、ペンタメチレンジアミン(d)を用いた以外はい、実施例1と同様の条件および操作にて、純度92.1質量%のペンタメチレンジイソシアネート(j0)を561質量部得た。
金属製容器にペンタメチレンジイソシアネート(a)を移し、2,6−ジ(tert−ブチル)−4−メチルフェノール(以後、BHTと略する場合がある)をペンタメチレンジイソシアネート100質量部に対し0.005質量部添加し、窒素パージ後、50℃のオーブン中に14日間静置し、貯蔵安定性試験を実施した。貯蔵安定性試験後のペンタメチレンジイソシアネート(a)の純度は99.8%であった。
金属製容器にペンタメチレンジイソシアネート(b)を移し、2,6−ジ(tert−ブチル)−4−メチルフェノール(以後、BHTと略する場合がある)をペンタメチレンジイソシアネート100質量部に対し0.005質量部添加し、窒素パージ後、50℃のオーブン中に14日間静置し、貯蔵安定性試験を実施した。貯蔵安定性試験後のペンタメチレンジイソシアネート(b)の純度は99.8%であった。
金属製容器にペンタメチレンジイソシアネート(c)を移し、BHTをペンタメチレンジイソシアネート100質量部に対し0.005質量部添加し、窒素パージ後、50℃のオーブン中に14日間静置し、貯蔵安定性試験を実施した。貯蔵安定性試験後のペンタメチレンジイソシアネート(c)の純度は99.8%であった。
金属製容器にペンタメチレンジイソシアネート(d)を移し、BHTをペンタメチレンジイソシアネート100質量部に対し0.005質量部添加し、窒素パージ後、50℃のオーブン中に14日間静置し、貯蔵安定性試験を実施した。貯蔵安定性試験後のペンタメチレンジイソシアネート(d)の純度は99.8%であった。
金属製容器にペンタメチレンジイソシアネート(e)を移し、BHTをペンタメチレンジイソシアネート100質量部に対し0.005質量部添加し、窒素パージ後、50℃のオーブン中に14日間静置し、貯蔵安定性試験を実施した。貯蔵安定性試験後のペンタメチレンジイソシアネート(e)の純度は99.8%であった。
金属製容器にペンタメチレンジイソシアネート(f)を移し、BHTをペンタメチレンジイソシアネート100質量部に対し0.005質量部添加し、窒素パージ後、50℃のオーブン中に14日間静置し、貯蔵安定性試験を実施した。貯蔵安定性試験後のペンタメチレンジイソシアネート(f)の純度は99.6%であった。
金属製容器にペンタメチレンジイソシアネート(g)を移し、BHTをペンタメチレンジイソシアネート100質量部に対し0.005質量部添加し、窒素パージ後、50℃のオーブン中に14日間静置し、貯蔵安定性試験を実施した。貯蔵安定性試験後のペンタメチレンジイソシアネート(g)の純度は99.2%であった。
金属製容器にペンタメチレンジイソシアネート(i)を移し、BHTをペンタメチレンジイソシアネート100質量部に対し0.005質量部添加し、窒素パージ後、50℃のオーブン中に14日間静置し、貯蔵安定性試験を実施した。貯蔵安定性試験後のペンタメチレンジイソシアネート(i)の純度は99.0%であった。
金属製容器にペンタメチレンジイソシアネート(j)を移し、BHTをペンタメチレンジイソシアネート100質量部に対し0.005質量部添加し、窒素パージ後、50℃のオーブン中に14日間静置し、貯蔵安定性試験を実施した。貯蔵安定性試験後のペンタメチレンジイソシアネート(j)の純度は98.4%であった。
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、ペンタメチレンジイソシアネート(a)を500質量部、イソブタノールを19質量部、2,6−ジ(t−ブチル)−4−メチルフェノールを0.3質量部、トリス(トリデシル)ホスファイトを0.3質量部装入し、85℃に昇温し、3時間ウレタン化反応を行った。次いで、アロファネート化触媒としてオクチル酸鉛を0.02質量部添加し、イソシアネート基濃度が計算値に達するまで反応を行った後、o−トルエンスルホンアミドを0.02質量部添加した。得られた反応液を薄膜蒸留装置(真空度0.093KPa、温度150℃)に通液して未反応のペンタメチレンジイソシアネートを除去し、さらに、得られた組成物100質量部に対し、o−トルエンスルホンアミドを0.02質量部添加し、ポリイソシアネート組成物(J)を得た。
ペンタメチレンジイソシアネート(a)に代えて、ペンタメチレンジイソシアネート(g)を用い、実施例13と同様の方法にてウレタン化、およびアロファネート化反応を行ったが、イソシアネート基濃度の測定から反応速度が低いことが確認されたため、オクチル酸鉛をさらに0.01質量部加え、ポリイソシアネート組成物(K)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、ペンタメチレンジイソシアネート(a)を500質量部、トリス(トリデシル)ホスファイトを0.2質量部、トリメチルリン酸を8質量部、水を4質量部装入し、130℃に昇温し、イソシアネート基濃度が計算値に達するまで反応を行った。得られた反応液を薄膜蒸留装置(真空度0.093KPa、温度150℃)に通液して未反応のペンタメチレンジイソシアネートを除去し、ポリイソシアネート組成物(L)を得た。
ペンタメチレンジイソシアネート(a)に代えて、ペンタメチレンジイソシアネート(g)を用い、実施例14と同様の方法にて反応を行い、ポリイソシアネート組成物(M)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、実施例1のペンタメチレンジイソシアネート(a)を500質量部、および、低分子量ポリオールとしてトリメチロールプロパン(略号:TMP)40質量部を装入した(当量比(NCO/OH)=5.8)。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に達するまで、83℃で反応させた。
ペンタメチレンジイソシアネート(a)に代えて、ペンタメチレンジイソシアネート(g)を用い、実施例15と同様の方法にて反応を行い、ポリイソシアネート組成物(O)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、ペンタメチレンジイソシアネート(a)を500質量部、2,6−ジ(tert−ブチル)−4−メチルフェノールを0.3質量部、トリス(トリデシル)ホスファイトを0.3質量部、平均分子量400のメトキシポリエチレンエーテルグリコールを105質量部装入し、窒素雰囲気下85℃で3時間反応させた。
ペンタメチレンジイソシアネート(a)に代えて、ペンタメチレンジイソシアネート(g)を用い、実施例16と同様の方法にてトリマー化反応を行ったが、イソシアネート基濃度の測定から反応速度が低いことが確認されたため、N−(2−ヒドロキシプロピル)−N,N,N−トリメチルアンモニウム−2−エチルヘキサノエートを0.2質量部加え、反応を2時間継続し、ポリイソシアネート組成物(Q)を得た。
実施例7で得られたポリイソシアネート組成物(A)と、アクリルポリオール(三井化学社製、商品名:オレスターQ666、以下、Q666と略する。)とを、アクリルポリオール中の水酸基に対するポリイソシアネート組成物中のイソシアネート基の当量比(NCO/OH)が1.0となる割合で配合し、23℃で90秒間攪拌し、反応混合液を得た。次いで、この反応混合液を、JIS G 3303に準拠した標準試験板(種類:電気めっきぶりき、以下、試験板と略する。)に塗布し、その後、80℃で30分、さらに110℃で1時間硬化させ、厚みが約45μmのポリウレタン樹脂(A)を得た。
ポリイソシアネート組成物(A)に代え、実施例11で得られたポリイソシアネート組成物(E)を用いた以外は、実施例17と同様の条件および操作にて、厚みが約45μmのポリウレタン樹脂(B)を得た。
ポリイソシアネート組成物(A)に代え、実施例12で得られたポリイソシアネート組成物(F)を用いた以外は、実施例17と同様の条件および操作にて、厚みが約45μmのポリウレタン樹脂(C)を得た。
アクリルポリオールUQ666に代え、ひまし油を主成分とする植物由来ポリオール(三井化学社製、商品名:タケラックU−27、以下、U−27と略する。)を用いた以外は、実施例17と同様の条件および操作にて、厚みが約45μmのポリウレタン樹脂(D)を得た。
ポリイソシアネート組成物(A)に代え、比較例5で得られたポリイソシアネート組成物(G)を用いた以外は、実施例17と同様の条件および操作にて、厚みが約45μmのポリウレタン樹脂(E)を得た。
ポリイソシアネート組成物(A)に代え、比較例6で得られたポリイソシアネート組成物(H)を用いた以外は、実施例17と同様の条件および操作にて、厚みが約45μmのポリウレタン樹脂(F)を得た。
ポリイソシアネート組成物(A)に代え、比較例7で得られたポリイソシアネート組成物(I)を用いた以外は、実施例17と同様の条件および操作にて、厚みが約45μmのポリウレタン樹脂(G)を得た。
攪拌機、温度計、還流冷却装置、及び窒素導入管を備えた4つ口フラスコに、有機溶剤として酢酸ブチルを100質量部仕込み、窒素置換しながら95℃に加熱昇温した。次いでこの中に、重合可能な単量体として、メチルメタアクリレート34.3部、ブチルアクリレート25.5部、2−ヒドロキシエチルアクリレート10.2部、イソボルニルメタアクリレート30質量部と重合開始剤としてtert−ブチルパーオキシ−2−エチルヘキサノエート(以下、PBOと略記する)0.4質量部の混合液を4時間かけてフィードした。フィード終了より1時間後と2時間後にPBOをそれぞれ0.2質量部添加した。PBOの添加後より2時間反応させポリオールAを得た。
合成例1で得られたポリオールA、および、U−27を、ポリオールA/U−27=78.9/21.1(重量比)の割合で配合した混合ポリオールと、実施例7で得られたポリイソシアネート組成物(A)とを、混合ポリオール中の水酸基に対するポリイソシアネート組成物中のイソシアネート基の当量比(NCO/水酸基)が1.0となる割合で配合し、23℃で90秒間攪拌し、反応混合液を得た。次いで、この反応混合液を、JIS G 3303に準拠した標準試験板(種類:電気めっきぶりき、以下、試験板と略する。)に塗布し、その後、80℃で30分、さらに110℃で1時間硬化させ、厚みが約45μmのポリウレタン樹脂(H)を得た。
主剤としてアルマテックスRE4788(水性アクリルエマルション、固形分濃度44.3質量%、水酸基価86mgKOH/g、三井化学社製)と、水とを、硬化剤添加後における固形分濃度が20質量%となるように配合し、マグネチックスターラーで撹拌しながら、硬化剤として、実施例16で得られたポリイソシアネート組成物(P)を、主剤中の水酸基に対する硬化剤中のイソシアネート基の当量比(NCO/水酸基)が1.0となる割合で配合した。
イソフタル酸339.4質量部、エチレングリコール110.9質量部、ネオペンチルグリコール107.2質量部、1,6−ヘキサンジオール158.1質量部、酢酸亜鉛0.21質量部を仕込み、200〜220℃で6時間エステル化反応を行い、所定量の水の留出後、アジピン酸99.5質量部を加え、更に7時間エステル化反応を行った。その後、徐々に減圧し、133〜266Pa、200〜230℃で4時間エステル交換反応を行い、数平均分子量6,000のポリエステルポリオールを得た。これを酢酸エチル420質量部に溶解し、固形分濃度60%のポリオールBを得た。
イソフタル酸529.4質量部、エチレングリコール128.8質量部、ネオペンチルグリコール302.4質量部を配合して、窒素気流下180〜220℃でエステル化反応を行った。所定量の水を留出後、セバシン酸214.8質量部を加え、180〜220℃でエステル化反応を行い、数平均分子量2500のポリエステルポリオールを得た。この全量を酢酸エチル428.6質量部に溶解し、固形分70%の溶液とした。このポリエステルポリオール643.3質量部に窒素雰囲気下でイソホロンジイソシアネート49.6質量部を加え、77〜80℃で3時間ウレタン化反応を行った。その後、触媒としてオクチル酸第1錫0.10質量部を加え、さらに3時間ウレタン化反応を継続し、数平均分子量10,000のポリウレタンポリオールを得た。これに酢酸エチル307.0質量部を加えて固形分濃度50%のポリオールCを得た。
実施例7で得られたポリイソシアネート組成物(A)を1質量部と、ポリオールBを15質量部で混合し、接着剤を調整した。次いで、接着剤を、それぞれ常温下、バーコーターを用いてナイロンフィルム(15μm厚)上に固形分で3.5g/m2となるように塗布し、溶剤を揮発させた。その後、接着剤塗布面と未延伸ポリエチレンフィルム(40μm厚、片面コロナ処理)のコロナ処理面とを貼り合わせ、40℃で5日間養生して接着剤を硬化させて、2層複合フィルムのポリウレタン樹脂(J)を得た。得られた2層複合フィルムのポリウレタン樹脂(J)の常態接着強度を測定した。次いで、2層複合フィルムのポリウレタン樹脂(J)の端をヒートシールして、130mm×170mmのパウチを作製し、内容物として水/サラダ油=10/1(vol比)の混合物を100ml充填した。次いで充填パウチを100℃×30分間、煮沸滅菌を行った。次いで、内容物を取り出し、煮沸滅殺菌後接着強度を測定した。
実施例7で得られたポリイソシアネート組成物(A)を1質量部と、ポリオールCを20質量部で混合した以外は、実施例23と同様の条件および操作にて、2層複合フィルムのポリウレタン樹脂(K)を得た。実施例23と同様にして、常態接着強度、煮沸殺菌後パウチ外観、煮沸殺菌後接着強度を測定した。
窒素雰囲気下、撹拌翼、温度計および水冷式コンデンサーを装着した反応機に、予め減圧脱水処理した、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(保土ヶ谷化学社製、商品名:バイオPTG2000SN、以下、PTMEGと略する。)126.4質量部と、PTMEG中の水酸基に対するペンタメチレンジイソシアネートのイソシアネート基の当量比(NCO/水酸基)が1.7となるように、実施例1で得られたペンタメチレンジイソシアネート(a)16.6質量部とを仕込み、70℃まで昇温した。
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、予め減圧脱水処理した、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(保土ヶ谷化学社製、商品名:バイオPTG2000SN、バイオマス濃度:95%、以下、PTMEGと略する。)を100質量部と、PTMEG中の水酸基に対するペンタメチレンジイソシアネートのイソシアネート基の当量比(NCO/水酸基)が2.0となるように、実施例1で得られたペンタメチレンジイソシアネート(a)を23.1質量部装入し、窒素雰囲気下、80℃にてイソシアネート基含量が6.8質量%になるまで反応させ、イソシアネート基末端ポリウレタンプレポリマー(以下、プレポリマーと略する。)を得た。
80℃に調整した非晶質ポリテトラメチレンエーテルグリコール(旭化成せんい社製、商品名:PTXG−1800)を95質量部と、特許第3905638公報の実施例2記載の方法により、ホスファゼニウム化合物を触媒として、ジプロピレングリコールにプロピレンオキシドを付加重合した数平均分子量1800(水酸基価31.2mgKOH/g)のポリオキシプロピレングリコールを5質量部に対して、水酸基に対するイソシアネート基の当量比(NCO/水酸基)が0.54となるように、実施例7で得られたポリイソシアネート組成物(A)を10.3質量部、触媒のジラウリン酸ジブチルすず(IV)(和光純薬工業社製)0.01質量部、消泡剤(ビックケミー・ジャパン社製、商品名:BYK−088)を0.005質量部、ステンレス容器に入れ、スリーワンモータ(新東科学社製、商品名:HEIDOM FBL3000)を使用して、700rpmの撹拌下、1分間撹拌混合した。直ちに減圧脱泡を行い、混合液中の泡を取り除いた後、予め離型剤(ミヨシ油脂社製、商品名:ミラックスRS−102)を塗布し、80℃に温調した厚さ2mmのシート、厚さ15mmのブロック、厚さ12.5mm、直径29mmのボタン金型に泡が入らないように注意しながら、混合液を流し込み、80℃にて5時間反応を行い、ポリウレタン樹脂(N)を得た。その後、得られたポリウレタン樹脂(N)を金型から取り外し、23℃、相対湿度55%の室内にて7日間静置した。
水酸基に対するイソシアネート基の当量比(イソシアネート基/水酸基)が0.54とし、ポリイソシアネート組成物(A)に代え、タケネートD−170N(三井化学社製)を12.2質量部用いた以外は、実施例27と同様の条件および操作にて、ポリウレタン樹脂(O)を得た。その後、得られたポリウレタン樹脂(O)を金型から取り外し、23℃、相対湿度55%の室内にて7日間静置した。
各実施例および各比較例で得られたポリウレタン樹脂(以下、塗膜と略する。)のマルテンス硬さ、破断強度、耐溶剤性、表面状態、ゲル分率、接着強度、煮沸殺菌後パウチ外観、100%変形応力、破断強度2、破断伸度、繰返し伸長変形後の残留歪、硬度、破断強度3、破断伸度2、圧縮永久歪、軟化温度、タック性を、以下の方法で測定した。その結果を表5〜11に示す。
<マルテンス硬さ(単位:N/mm2)>
試験板に密着した状態の塗膜を、超微小硬度計(島津製作所社製、DUH−211)を用いて、圧子の種類:Triangular115、試験モード:負荷−除荷試験、試験力:10.00mN、負荷速度3.0mN/sec、負荷保持時間:10secの条件にてマルテンス硬さ(HMT115)を測定した。
<破断強度(TS)(単位:MPa)>
塗膜を、幅1cm、長さ10cmのサイズにダンベルで打ち抜いた。次いで、この試験サンプルに対して、引張圧縮試験機(インテスコ社製、Model205N)を用いて、23℃、相対湿度55%の雰囲気下、引張速度10mm/min、チャック間距離50mmの条件で引張試験した。これにより、破断強度(TS)を測定した。
<耐溶剤性(単位:回)>
試験液を充分に含浸させた綿棒を、試験板に密着した塗膜上に置き、一定荷重がかかるようにして約1cmの距離を往復させた。この作業を繰返し、塗膜に損傷が観察されたら時点で試験を終了させた。往復を1回とし、塗膜に損傷が観察されるまでの回数を耐溶剤性とした。試験液は、酢酸エチル、メチルエチルケトンとした。
<表面状態>
ポリウレタン樹脂を75℃の温水に含浸し、1日後、7日後の表面状態を以下の基準で評価した。
○:変化が観察されたなった。
△:わずかに白かすることが確認された。
×:著しく白かすることが確認された。
<ゲル分率(単位:質量%)>
ゲル分率は以下の式により算出した。
<接着強度(単位:N/15mm)>
複合フィルムから、長さ100mm×幅15mmの試験片を切り出し、引張試験機(インテスコ社製、Model201B)を用いて、23℃、相対湿度55%の雰囲気下、剥離速度300mm/minの条件でT型剥離試験を実施し、接着強度を測定した。
<煮沸殺菌後パウチ外観>
煮沸滅菌後パウチ外観を以下の基準で評価した。
○:変化が観察されなかった。
×:変化が確認された。
<100%変形応力(単位:MPa)>
ポリウレタン樹脂を、幅1cm、長さ10cmのサイズにダンベルで打ち抜いた。次いで、この試験サンプルに対して、引張試験機(インテスコ社製、Model205N)を用いて、23℃、相対湿度55%の雰囲気下、引張速度300mm/min、チャック間距離30mmの条件で引張試験した。100%変形時、すなわちチャック間距離が60mmの時の応力を100%変形応力とした。
<破断強度2(単位:MPa)>
100%変形応力と同様の条件にて引張試験し、破断強度2を測定した。
<破断伸度(単位:%)>
100%変形応力と同様の条件にて引張試験し、破断伸度を測定した。
<繰返し伸長変形後の残留歪(単位:%)>
ポリウレタン樹脂を、幅1cm、長さ10cmのサイズにダンベルで打ち抜いた。次いで、引張圧縮試験機(島津製作所製、AG−X)を用いて、23℃、相対湿度55%の雰囲気下、引張試験を行なった。より具体的には、引張方向に30mmの試料長(L1)であるフィルムを、引張速度500mm/minで300%まで伸長する操作を5回繰り返した。
<破断強度3(単位:MPa)>
シート金型で得られたポリウレタン樹脂を、JIS−3号ダンベルにて打ち抜いた。次いで、引張試験機(エー・アンド・デイ社製、モデル:RTG−1310)を用いて、23℃、相対湿度55%の雰囲気下、引張速度500mm/min、チャック間距離20mmの条件で引張試験した。これにより、破断強度3を測定した。
<破断伸度2(単位:%)>
破断強度3と同様の条件にて引張試験し、破断伸度2を測定した。
<硬度(単位:C)>
ブロック金型で得られたポリウレタン樹脂を用い、JIS K7312に準じてタイプC硬さ試験を測定した。
<平行光線透過率(単位:%>
シート金型で得られたポリウレタン樹脂を用い、JIS K7105に準じて、Haze Meter(日本電色工業製、モデル:NDH 2000、光源:D65)により、平行光線透過率を測定した。
<ヘイズ(単位:%)>
シート金型で得られたポリウレタン樹脂を用い、平行光線透過率と同様の条件にて、ヘイズを測定した。
<引裂強度(単位:kN/m)>
シート金型で得られたポリウレタン樹脂を、JIS−B型ダンベルにて打ち抜いた。次いで、破断強度3と同様の条件にて引張試験し、引裂強度を測定した。
<圧縮永久歪(単位:%)>
ボタン金型で得られたポリウレタン樹脂を用い、JIS K6262に準じ、測定温度23℃、および70℃、相対湿度55%の雰囲気下において、圧縮する割合を25%、保持時間を22時間の条件にて測定した。
<軟化温度(単位:℃)>
シート金型で得られたポリウレタン樹脂を、幅5mm、長さ10cmのサイズにダンベルで打ち抜いた。次いで、動的粘弾性装置(ティー・エイ・インスツルメント社製、モデル:RSA−III)を用いて、窒素雰囲気下、引張モード(Auto Tension、Auto Strain制御)、測定温度−100から200℃、昇温速度3℃/min、周波数10Hzの条件で測定し、高温側の貯蔵弾性率の平坦領域と流動領域の接線が交差する温度を軟化温度とした。
<タック性>
シート金型で得られたポリウレタン樹脂を5cm角に切り出し、PP板上に並べて、23℃、相対湿度55%の室内にて1日静置した。次いで、PP板を逆さまに反転し、1分以内の落下の有無を観察し、タック性として評価した。
○:1分以内に落下した。
×:1分以内に落下しない。
実施例1記載のペンタメチレンジイソシアネート(a)と、製造例1記載のペンタメチレンジアミン(a)とを用いて、特開2008−56790号公報記載の真空処理装置により、蒸着重合反応を行った。透明導電膜(ITO)付きガラス基板(コーニング社製、商品名:イーグルXG)を基板として、20℃に調整した。一方、ペンタメチレンジアミン(a)を20℃、ペンタメチレンジイソシアネート(a)を70℃とし、各々20Paに制御して、同時に蒸発させた。このとき、ペンタメチレンジアミン(a)とペンタメチレンジイソシアネート(a)の化学量論比が1:1となるようにそれぞれを供給した。このときの装置のチャンバー内の温度は20℃に制御した。
ペンタメチレンジイソシアネート(a)に代えて、比較例4記載のペンタメチレンジイソシアネート(j)を用いた以外は、実施例28と同様の方法により、ポリウレア樹脂を得た。このポリウレア樹脂の圧電d定数d33は最大で20×10−12C/Nであった。
Claims (9)
- 生化学的手法により、ペンタメチレンジアミンまたはその塩の水溶液を得て、
前記水溶液から、ペンタメチレンジアミンまたはその塩を抽出し、
抽出された前記ペンタメチレンジアミンまたはその塩をホスゲン化することによりペンタメチレンジイソシアネートを得て、
前記ペンタメチレンジイソシアネートを、不活性ガスの存在下において、180℃〜245℃で加熱し、その後、蒸留精製する
ことにより得られることを特徴とする、請求項1に記載のペンタメチレンジイソシアネート。 - 前記ペンタメチレンジイソシアネートを、リン含有化合物の存在下において加熱することを特徴とする、請求項2に記載のペンタメチレンジイソシアネート。
- 下記一般式(1)で示される化合物、および、下記一般式(2)で示される化合物の総含有量が、5〜400ppmであるペンタメチレンジイソシアネートの製造方法であって、
生化学的手法により、ペンタメチレンジアミンまたはその塩の水溶液を得る工程、
前記水溶液から、ペンタメチレンジアミンまたはその塩を抽出する工程、
抽出された前記ペンタメチレンジアミンまたはその塩をホスゲン化することによりペンタメチレンジイソシアネートを得る工程、および、
前記ペンタメチレンジイソシアネートを、不活性ガスの存在下において、180℃〜245℃で加熱し、その後、蒸留精製する工程
を備えることを特徴とする、ペンタメチレンジイソシアネートの製造方法。
- 前記ペンタメチレンジイソシアネートを、リン含有化合物の存在下において加熱することを特徴とする、請求項4に記載のペンタメチレンジイソシアネートの製造方法。
- 前記活性水素化合物が植物由来であることを特徴とする、請求項7に記載のポリウレタン樹脂。
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Also Published As
Publication number | Publication date |
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EP2684867B1 (en) | 2019-01-02 |
EP2684867A1 (en) | 2014-01-15 |
US9376404B2 (en) | 2016-06-28 |
EP3486230A1 (en) | 2019-05-22 |
EP2684867A4 (en) | 2014-09-24 |
MY163292A (en) | 2017-09-15 |
KR101604961B1 (ko) | 2016-03-18 |
US9371413B2 (en) | 2016-06-21 |
TWI560173B (ja) | 2016-12-01 |
JP5849088B2 (ja) | 2016-01-27 |
BR112013023020A2 (pt) | 2017-06-13 |
WO2012121291A1 (ja) | 2012-09-13 |
US20160083503A1 (en) | 2016-03-24 |
ES2714299T3 (es) | 2019-05-28 |
HK1186171A1 (zh) | 2014-03-07 |
PT2684867T (pt) | 2019-02-07 |
US9234069B2 (en) | 2016-01-12 |
CN103347852A (zh) | 2013-10-09 |
US20130338330A1 (en) | 2013-12-19 |
KR20130127504A (ko) | 2013-11-22 |
KR20150038648A (ko) | 2015-04-08 |
TW201302680A (zh) | 2013-01-16 |
KR101544296B1 (ko) | 2015-08-13 |
CN103347852B (zh) | 2016-04-13 |
US20160090368A1 (en) | 2016-03-31 |
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