JP2013010925A - ポリウレタンエラストマーおよびポリウレタン樹脂組成物 - Google Patents
ポリウレタンエラストマーおよびポリウレタン樹脂組成物 Download PDFInfo
- Publication number
- JP2013010925A JP2013010925A JP2012045420A JP2012045420A JP2013010925A JP 2013010925 A JP2013010925 A JP 2013010925A JP 2012045420 A JP2012045420 A JP 2012045420A JP 2012045420 A JP2012045420 A JP 2012045420A JP 2013010925 A JP2013010925 A JP 2013010925A
- Authority
- JP
- Japan
- Prior art keywords
- active hydrogen
- containing compound
- hydrogen group
- molecular weight
- polyurethane elastomer
- 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
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- 229920003225 polyurethane elastomer Polymers 0.000 title claims abstract description 63
- 229920005749 polyurethane resin Polymers 0.000 title claims abstract description 16
- 239000011342 resin composition Substances 0.000 title claims abstract description 16
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 104
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 104
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 89
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 125000000524 functional group Chemical group 0.000 claims abstract description 32
- 229920000909 polytetrahydrofuran Polymers 0.000 claims abstract description 23
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 6
- 229920005862 polyol Polymers 0.000 description 52
- 150000003077 polyols Chemical class 0.000 description 49
- -1 polytetramethylene Polymers 0.000 description 41
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 25
- 239000012948 isocyanate Substances 0.000 description 24
- 150000002513 isocyanates Chemical group 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 238000004519 manufacturing process Methods 0.000 description 21
- 229920000768 polyamine Polymers 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 239000002245 particle Substances 0.000 description 14
- 239000000178 monomer Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229920002635 polyurethane Polymers 0.000 description 10
- 239000004814 polyurethane Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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- 239000003054 catalyst Substances 0.000 description 9
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- 229920005906 polyester polyol Polymers 0.000 description 9
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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 7
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- 125000003118 aryl group Chemical group 0.000 description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 6
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
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- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
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- 229930195733 hydrocarbon Natural products 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
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- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 3
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
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- 230000000996 additive effect Effects 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 238000012662 bulk polymerization Methods 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
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- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
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Abstract
【解決手段】ポリイソシアネート成分の平均官能基数が2.5未満であるポリイソシアネート成分と、非晶性のポリテトラメチレンエーテルグリコールを含む活性水素基含有化合物成分とを含有するポリウレタン樹脂組成物から、ポリウレタンエラストマーを得る。このようなポリウレタンエラストマーおよびポリウレタン樹脂組成物によれば、低硬度でありながら、耐熱性および機械物性の向上を図ることができる。
【選択図】なし
Description
還流冷却管、窒素導入管、温度計、攪拌機を備えた4つ口フラスコ中に、ポリプロピレングリコール(開始剤:ジプロピレングリコール、数平均分子量2000)82.6質量部、および、4,4’−ジフェニルメタンジイソシアネート17.4質量部を加えて、80℃で反応させることにより、イソシアネート基末端プレポリマーを得た。
還流冷却管、窒素導入管、温度計、攪拌機を備えた4つ口フラスコ中に、ポリテトラメチレンエーテルグリコール(数平均分子量1000)15質量部、ポリテトラメチレンエーテルグリコール(数平均分子量2000)70質量部、および、2,4−トリレンジイソシアネートと2,6−トリレンジイソシアネートとの混合物(それぞれ質量比で80/20)15質量部を加えて、80℃で反応させることにより、イソシアネート基末端プレポリマーを得た。
還流冷却管、窒素導入管、温度計、攪拌機を備えた4つ口フラスコ中に、ポリテトラメチレンエーテルグリコール(数平均分子量1000)60質量部、および、4,4’−ジフェニルメタンジイソシアネート40質量部を加えて、90℃で反応させることにより、イソシアネート基末端プレポリマーを得た。
ヘキサメチレンジイソシアネートのアロファネート変性体(D−178NL 三井化学社製)を用意し、これを、ポリイソシアネート成分4とした。なお、イソシアネート基の含有量(イソシアネート基含量、NCO%)は、19質量%、平均官能基数は、2.3であった。
1,6−ヘキサメチレンジイソシアネートの3量体(D−170HN 三井化学社製(ヘキサメチレンジイソシアネートとイソブチルアルコールとのウレタン化反応物を少量含有))を用意し、これを、ポリイソシアネート成分5とした。なお、イソシアネート基の含有量(イソシアネート基含量、NCO%)は、23質量%、平均官能基数は、3であった。
1,6−ヘキサメチレンジイソシアネートの3量体(コロネートHX 日本ポリウレタン工業社製(ヘキサメチレンジイソシアネートと、ブタンジオールおよび数平均分子量2000の高分子量ポリオールとのウレタン化反応物を少量含有))を用意し、これを、ポリイソシアネート成分6とした。なお、イソシアネート基の含有量(イソシアネート基含量、NCO%)は、21質量%、平均官能基数は、3であった。
還流冷却管、窒素導入管、温度計、攪拌機を備えた4つ口フラスコ中に、ポリテトラメチレンエーテルグリコール(数平均分子量1500)85.3質量部、および、2,4−トリレンジイソシアネート14.7質量部を加えて、80℃で反応させることにより、イソシアネート基末端プレポリマーを得た。
表1〜表3に示す配合処方で、ポリイソシアネート成分と活性水素基含有化合物成分と触媒とを、50℃にて、活性水素基含有化合物成分中の活性水素基に対するポリイソシアネート成分中のイソシアネート基の当量比(NCO/活性水素基)が、それぞれ、表1〜3に示す値となる割合で投入し、混合しながら減圧下にて脱泡した。
<ショアA硬度>
JIS K7312(1996)の「熱硬化性ポリウレタンエラストマー成形物の物理試験方法」の7項の「硬さ試験」の記載およびJIS K6253(2006)「加硫ゴム及び熱可塑性ゴム−硬さの求め方」の6項の「デュロメーター硬さ試験」の試験タイプAの記載に準拠して測定した。その結果を表1〜表3に示す。
<アスカーC硬度>
JIS K7312(1996)付属書2に記載の「スプリング硬さ試験タイプC試験方法」の記載に準拠して測定した。その結果を表1〜表3に示す。
<引裂強さ>
JIS K7312(1996)の6項の「引裂試験」に準拠し、6.3項の「試験片」に記載の(B)切込みなしアングル形試験片を用いて、各実施例および各比較例で得られたポリウレタンエラストマーの引裂強さ(破断時引裂き応力)を測定した。その結果を表1〜表3に示す。
<反発弾性>
JIS K7312(1996)の10項の「反発弾性試験」に準拠し、14.3項の「試験片」に記載の直円柱形試験片を用いて測定し、10.5項の「計算」の記載に準拠して、各実施例および各比較例で得られたポリウレタンエラストマーの反発弾性を算出した。その結果を表1〜表3に示す。
<耐熱性>
各実施例および各比較例で得られたポリウレタンエラストマーを、120℃の熱風乾燥機中で1日間(24時間)加熱し、その溶融の有無について観測した。その結果を、表1〜表3に示す。
◎:溶融せず(100体積%残存)。
○:20体積%溶融。
×:100体積%溶融(残存せず)。
ポリイソシアネート成分1:製造例1のイソシアネート基末端プレポリマー(平均官能基数2、NCO%=2.3%)
ポリイソシアネート成分2:製造例2のイソシアネート基末端プレポリマー(平均官能基数2、NCO%=2.8%)
ポリイソシアネート成分3:製造例3のイソシアネート基末端プレポリマー(平均官能基数2、NCO%=8.0%)
ポリイソシアネート成分4:製造例4のイソシアネート基末端プレポリマー(平均官能基数2.3、NCO%=19%)
ポリイソシアネート成分5:製造例5のイソシアネート基末端プレポリマー(平均官能基数3、NCO%=23%)
ポリイソシアネート成分6:製造例6のイソシアネート基末端プレポリマー(平均官能基数3、NCO%=21%)
ポリイソシアネート成分7:製造例7のイソシアネート基末端プレポリマー(平均官能基数2、NCO%=2.85%)
PTXG1000:非晶性ポリテトラメチレンエーテルグリコール(平均分子量1000、旭化成せんい社製)
PTXG1800:非晶性ポリテトラメチレンエーテルグリコール(平均分子量1800、旭化成せんい社製)
PTG−L1000:非晶性ポリテトラメチレンエーテルグリコール(平均分子量1000、保土谷化学工業社製)
PTG−L3500:非晶性ポリテトラメチレンエーテルグリコール(平均分子量3500、保土谷化学工業社製)
EP−3043:ペンタエリスリトールのアルキレンオキサイド付加ポリエ−テルポリオール(平均分子量5000、三井化学社製)
TIPA:トリイソプロパノールアミン
TMP:トリメチロールプロパン
1,4BG:1,4−ブチレングリコール
F−65DE:中空粒子(マツモトマイクロスフェアーF−65DE、既膨張ドライタイプ、平均粒子径90〜130μm、松本製薬工業社製)
スタノクト:オクチル酸錫(API社製)
Claims (6)
- ポリイソシアネート成分と、活性水素基含有化合物成分との反応により得られるポリウレタンエラストマーであって、
前記ポリイソシアネート成分の平均官能基数が2.5未満であり、
前記活性水素基含有化合物成分が、非晶性のポリテトラメチレンエーテルグリコールを含むことを特徴とする、ポリウレタンエラストマー。 - 前記活性水素基含有化合物成分が、低分子量活性水素基含有化合物と、高分子量活性水素基含有化合物とを含有し、
前記低分子量活性水素基含有化合物の平均官能基数が、2を超過し、6以下であり、
前記高分子量活性水素基含有化合物が、非晶性のポリテトラメチレンエーテルグリコール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エラストマー。 - 前記低分子量活性水素基含有化合物成分が、トリイソプロパノールアミンを含有することを特徴とする、請求項2に記載のポリウレタンエラストマー。
- JIS K7312(1996)に基づくショアA硬度が、10A以上であり、かつ、
JIS K7312(1996)に基づく引裂強さが、7N/mm以上であることを特徴とする、請求項1〜3のいずれか一項に記載のポリウレタンエラストマー。 - JIS K7312(1996)に基づくショアA硬度が、10A未満であり、かつ、
JIS K7312(1996)に基づく引裂強さが、5N/mm以上であることを特徴とする、請求項1〜3のいずれか一項に記載のポリウレタンエラストマー。 - ポリイソシアネート成分と、活性水素基含有化合物成分とを含有するポリウレタン樹脂組成物であって、
前記ポリイソシアネート成分の平均官能基数が2.5未満であり、
前記活性水素基含有化合物成分が、非晶性のポリテトラメチレンエーテルグリ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。
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JP2016204466A (ja) * | 2015-04-17 | 2016-12-08 | 東ソー株式会社 | ウレタンプレポリマーおよびそれを用いた2液型ウレタン粘着剤 |
CN114375355A (zh) * | 2019-09-25 | 2022-04-19 | 陶氏环球技术有限责任公司 | 非溶剂2k聚氨酯人造皮革组合物、用其制备的人造皮革及其制备方法 |
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