JP7364780B2 - 発泡ポリウレタン樹脂組成物および発泡ポリウレタンエラストマー - Google Patents
発泡ポリウレタン樹脂組成物および発泡ポリウレタンエラストマー Download PDFInfo
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- C08G18/163—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
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- C08G18/20—Heterocyclic amines; Salts thereof
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- C08G18/08—Processes
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- 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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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
- C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end groups
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—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
- C08G18/757—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 at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group
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- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/02—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by the reacting monomers or modifying agents during the preparation or modification of macromolecules
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Description
<原料>
A.第1液(イソシアネート基末端プレポリマー)の原料
A-1.ポリイソシアネート原料
(1)1,4-H6XDI
1,4-ビス(イソシアナトメチル)シクロヘキサン、国際公開第2009/51114号の製造例3に従って合成した。純度(ガスクロマトグラフィー測定による。)99.9%、トランス/シス比(モル基準)=86/14
(2)1,3-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
(3)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、KUMHO MITSUI CHEMICALS社製
A-2.プレポリマー用ポリオール
(1)PTG-1000
結晶性ポリテトラメチレンエーテルグリコール、商品名:PTG-1000、数平均分子量:1000、平均水酸基価:112.1mgKOH/g、保土谷化学工業社製
(2)PTG-2000
結晶性ポリテトラメチレンエーテルグリコール、商品名:PTG-2000、数平均分子量:2000、平均水酸基価:56.1mgKOH/g、保土谷化学工業社製
(3)PTG-3000
結晶性ポリテトラメチレンエーテルグリコール、商品名:PTG-3000SN、数平均分子量:3000、平均水酸基価:37.4mgKOH/g、保土谷化学工業社製
(4)PPG DL-4000
ポリオキシプロピレングリコール、商品名:PPG DL-4000、数平均分子量4000、平均水酸基価28.1mgKOH/g、三井化学SKCポリウレタン社製
B.第2液(レジンプレミックス)の原料
B-1.発泡成形用ポリオール(高分子量ポリオール)
(1)PTG-1000
結晶性ポリテトラメチレンエーテルグリコール、商品名:PTG-1000、数平均分子量:1000、平均水酸基価:112.1mgKOH/g、保土谷化学工業社製
(2)PTG-1400
結晶性ポリテトラメチレンエーテルグリコール、商品名:PTMEG-1400、数平均分子量:1400、平均水酸基価:80.1mgKOH/g、KOREAPTG社製
(3)PTG-1500
結晶性ポリテトラメチレンエーテルグリコール、商品名:PTG-1500SN、数平均分子量:1500、平均水酸基価:74.8mgKOH/g、保土谷化学工業社製
(4)ED-28
ポリオキシエチレン末端ポリオキシプロピレングリコール、商品名:ED-28、数平均分子量4000、平均水酸基価28mgKOH/g、三井化学SKCポリウレタン社製(5)ED-56
ポリオキシエチレン末端ポリオキシプロピレングリコール、商品名:ED-56、数平均分子量2000、平均水酸基価56mgKOH/g、三井化学SKCポリウレタン社製(6)EP-950
ポリオキシエチレン末端ポリオキシプロピレントリオール、商品名:EP-950、数平均分子量5000、平均水酸基価33.7mgKOH/g、三井化学SKCポリウレタン社製
(7)PTG-L2000
非晶性ポリテトラメチレンエーテルグリコール、商品名:PTG-L-2000、数平均分子量2000、平均水酸基価56.1mgKOH/g、保土谷化学工業社製
B-2.発泡成形用ポリオール(低分子量ポリオール)
(1)1,4-BD
1,4-ブタンジオール、三菱化学社製
B-3.架橋剤
(2)DEOA
ジエタノールアミン、東京化成工業社製
C.発泡剤
(1)水(イオン交換水)
D.触媒
D-1.含窒素有機触媒
(1)DABCO TMR
脂肪族アミン触媒、2-ヒドロキシプロピルトリメチルアンモニウム・オクチル酸塩、Evonik社製
(2)DABCO33LV
脂肪族アミン触媒、トリエチレンジアミン、Evonik社製
(3)NIAX CATALYST A-1
脂肪族アミン触媒、ビス(ジメチルアミノエチル)エーテルの70%ジプロピレングリコール溶液、モメンティブ社製
(4)POLYCAT41
トリアジン触媒、1,3,5―トリス[3―(ジメチルアミノ)プロピル]ヘキサヒドロー
s-トリアジン、エボニック社製
D-2.金属触媒
(1)K-KAT XK-633
亜鉛系金属触媒、KING社製
(2)BiCAT8108
ビスマス系金属触媒、ビスマスネオデカネート(ネオデカン酸ビスマス(III))、シェファードケミカル製
E.安定剤
(1)Irganox245
酸化防止剤、ヒンダードフェノール化合物、商品名:イルガノックス245、BASFジャパン社製
(2)LA-72
耐光安定剤、ヒンダードアミン化合物、商品名:アデカスタブLA-72、ADEKA社製
<実施例および比較例>
1.第1液の調製
各表に示す質量部数で、ポリイソシアネート原料と、プレポリマー用ポリオール(ポリオール原料の一部)とを、撹拌機、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(イソシアネートインデックスNCO/OH=3.71~5.08)、窒素雰囲気下、80℃にて1時間撹拌した。
各表に示す質量部数で、発泡成形用ポリオール(ポリオール原料の残部)と、発泡剤(イオン交換水)と、整泡剤と、含窒素有機触媒と、安定剤(耐光安定剤、酸化防止剤)とを、均一に撹拌混合して、50℃のオーブン中に1時間静置した。
得られた第2液(レジンプレミックス)全量と、80℃に温調した第1液(イソシアネート基末端プレポリマー)100質量部と、各表に示す質量部数の金属触媒(23℃)とを配合し、それらをハンドミキサー(回転数5000rpm)によって10秒間撹拌して、発泡混合物を調製した。
<評価方法>
(1)密度
発泡ポリウレタンエラストマーから測定試料を切り出し、JIS K 7222:2005に従って、測定試料の見かけ密度を測定した。結果を各表に示す。
JIS K 7312-7:1996に従って、発泡ポリウレタンエラストマーのアスカーC硬度を測定した。結果を各表に示す。
(3)引張試験(破断強度、破断伸び)
厚さ10mmの発泡ポリウレタンエラストマーから、JIS-1号ダンベルを用いて測定試料を作製し、JIS K 6400-5:2012に従って、測定試料の破断強度および破断伸びを測定した。結果を各表に示す。
(4)デマッチャ耐屈曲性(耐屈曲き裂性)
発泡ポリウレタンエラストマーから、140mm×25mm×10mmの測定試料を切り出し、JIS K 6260:2010に準拠して、測定試料の耐屈曲性を測定した。結果を各表に示す。なお、10万回の屈曲試験ののち破断していないものは>100(×1000回)以上と表記した。
発泡ポリウレタンエラストマーの耐変色性を、以下の方法で評価した。
Claims (4)
- ポリイソシアネート原料と、ポリオール原料と、水と、触媒とを含む発泡ポリウレタン樹脂組成物であり、
前記ポリイソシアネート原料は、1,4-ビス(イソシアナトメチル)シクロヘキサンを含有し、
前記ポリオール原料は、
結晶性ポリテトラメチレンエーテルグリコールと、
非晶性ポリテトラメチレンエーテルグリコールおよび/またはポリオキシプロピレングリコールと
を含有し、
前記ポリイソシアネート原料の総量に対して、1,4-ビス(イソシアナトメチル)シクロヘキサンの割合が、98質量%以上であり、
前記ポリオール原料の総量に対して、結晶性ポリテトラメチレンエーテルグリコール、非晶性ポリテトラメチレンエーテルグリコールおよびポリオキシプロピレングリコールの合計量が、90質量%以上であり、
結晶性ポリテトラメチレンエーテルグリコール、非晶性ポリテトラメチレンエーテルグリコールおよびポリオキシプロピレングリコールの総量に対して、前記結晶性ポリテトラメチレンエーテルグリコールが、60質量%以上90質量%以下である
ことを特徴とする、発泡ポリウレタン樹脂組成物。 - 前記発泡ポリウレタン樹脂組成物は、
前記ポリイソシアネート原料、および、前記ポリオール原料の一部の反応生成物であるイソシアネート基末端プレポリマーを含む第1液と、
前記ポリオール原料の前記一部に対する残部、前記水および前記触媒を含有する第2液と
を含むことを特徴とする、請求項1に記載の発泡ポリウレタン樹脂組成物。 - 前記触媒が、1,3,5-トリス[3-(ジメチルアミノ)プロピル]ヘキサヒドロ-s-トリアジンを含む
ことを特徴とする、請求項1に記載の発泡ポリウレタン樹脂組成物。 - 請求項1に記載の発泡ポリウレタン樹脂組成物の発泡硬化物を含むことを特徴とする、発泡ポリウレタンエラストマー。
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