JP7184615B2 - ポリウレタン - Google Patents
ポリウレタン Download PDFInfo
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- JP7184615B2 JP7184615B2 JP2018225692A JP2018225692A JP7184615B2 JP 7184615 B2 JP7184615 B2 JP 7184615B2 JP 2018225692 A JP2018225692 A JP 2018225692A JP 2018225692 A JP2018225692 A JP 2018225692A JP 7184615 B2 JP7184615 B2 JP 7184615B2
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
- C08G18/4615—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen
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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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6607—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6611—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6644—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6852—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from hydroxy carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/823—Preparation processes characterised by the catalyst used for the preparation of polylactones or polylactides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/44—Polyester-amides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/05—Alcohols; Metal alcoholates
- C08K5/053—Polyhydroxylic alcohols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/06—Polyurethanes from polyesters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
Description
本発明の他の目的は、耐水性、柔軟性、耐久性、及び耐溶剤性に優れるポリウレタンを提供することにある。
そして、本発明のポリエステルポリオールを原料として得られるポリウレタンは、耐水性、柔軟性、耐久性、及び耐溶剤性を兼ね備える。そのため、各種成形品、繊維、フィルム、シート、樹脂やエラストマーの原料、改質材、塗料、接着剤等に好適に使用することができる。
本発明のポリエステルポリオールは、下記式(1)で表される化合物である。本発明のポリエステルポリオールは、一分子中に少なくとも2つのアミド結合を有することを特徴とする。
上記ポリエステルポリオールは、例えば、1~20ppmのスズ化合物の存在下、下記式(11)で表される化合物を開始剤とし、当該開始剤に環状エステルを開環重合させることにより製造することができる。
本発明のポリウレタンは、上記ポリエステルポリオールとポリイソシアネートとの付加重合物からなるセグメント(1)を有することを特徴とする。
1,6-ヘキサメチレンジアミン116.2gとε-カプロラクトン883.8gを、オクチル酸第一スズ5ppmの存在下、窒素雰囲気下で、5つ口フラスコに仕込んだ後、170℃に昇温し、重合反応を行った。ガスクロマトグラフィーによる分析で、残存するε-カプロラクトン濃度が1.0%未満となっていることを確認してから冷却した。製品として、分子量分布(Mw/Mn)1.1、数平均分子量1000、水酸基価111.2のポリエステルポリオール(1)を得た。
1,6-ヘキサメチレンジアミンを58.1gとε-カプロラクトンを941.9g使用した以外は実施例1と同様に行った。製品として、分子量分布(Mw/Mn)1.1、数平均分子量2000、水酸基価56.9のポリエステルポリオール(2)を得た。
オクチル酸第一スズ5ppmに代えてテトラn-ブトキシチタン10ppmを使用した以外は実施例1と同様に行った。製品として、分子量分布(Mw/Mn)1.2、数平均分子量1000、水酸基価111.7のポリエステルポリオール(3)を得た。
<分子量分布:Mw/Mn>
高速GPC装置を用いて、ポリスチレン標品との比較により数平均分子量(Mn)、重量平均分子量(Mw)を求め、その比を分子量分布の指標とした。
測定条件
測定装置:高速GPC装置「HLC-8220GPC」、東ソー(株)製
移動相:テトラヒドロフラン
フラスコに、ポリオール(A)としてのポリエステルポリオール(1)と、架橋剤(C)としてのトリメチロールプロパンを下記表に記載の割合で仕込み、80℃に加温して混合した。その後、4,4’-ジフェニルメタンジイソシアネートをNCO/OH(モル比)=1.05となる割合で投入し、30秒間混合して混合液を得た。
得られた混合液を注型し、圧縮成形機を用いて120℃で15分間圧縮成形を行った。その後、圧縮成形機から取り出し、120℃で16時間2次硬化を行うことでポリウレタン(1)(=熱硬化性ポリウレタン)を得た。
・硬度:ISO 7619-1に準拠した方法で測定した
・伸び:ISO 34に準拠した方法で測定した
・引張強度:ISO 34に準拠した方法で測定した
・引裂強度:ISO 37に準拠した方法で測定した
・耐溶剤性:ISO 1817に準拠した方法で測定した。詳細には、試験片を室温下にて溶剤に24時間浸漬し、試験前後の試験片の重量変化から耐溶剤性を評価した。
下記表に記載の通りに処方を変更した以外は実施例3と同様にした。
A-1:実施例1で得られたポリエステルポリオール(1)
A-3:比較例1で得られたポリエステルポリオール(3)
A-4:ポリカプロラクトンジオール(数平均分子量1000、水酸基価113.1、Mw/Mn=1.2、PLACCEL 210N、(株)ダイセル製)
A-5:エチレングリコール-アジピン酸縮合系ポリエステルジオール(数平均分子量1000、水酸基価115.5、Mw/Mn=1.5、CMA1024、HUADA CHEM製)
A-6:1,6-ヘキサンジオール-アジピン酸縮合系ポリエステルジオール(数平均分子量1000、水酸基価117.3、Mw/Mn=1.4、CMA1066、HUADA CHEM製)
A-7:ポリカーボネートジオール(数平均分子量1000、水酸基価114.2、Mw/Mn=1.5、Eternacol UH-100、宇部興産(株)製)
A-8: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、水酸基価114.7、Mw/Mn=1.6、PolyTHF、BASF製)
B-1:4,4-ジフェニルメタンジイソシアネート、(Millionate MT、東ソー(株)製)
C-1:トリメチロールプロパン
C-2:ポリカプロラクトントリオール(数平均分子量550、PLACCEL 305、(株)ダイセル製)
Claims (2)
- 下記式(1)で表され、数平均分子量が500~2500、分子量分布が1.2未満であるポリエステルポリオール(I)と、ポリイソシアネートとの付加重合物からなるセグメント(1)と、
イソシアネート基との反応性を有する基を3個以上備える化合物であって前記ポリエステルポリオール以外の化合物(II)と、ポリイソシアネートとの付加重合物からなるセグメント(2)を有し、
前記セグメント(1)を形成するポリエステルポリオール(I)と、前記セグメント(2)を形成する化合物(II)の合計に対する、前記化合物(II)の割合が5~10重量%であるポリウレタン。
- 前記化合物(II)の分子量が100~600である、請求項1に記載のポリウレタン。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2018225692A JP7184615B2 (ja) | 2018-11-30 | 2018-11-30 | ポリウレタン |
CN201980077421.5A CN113166353B (zh) | 2018-11-30 | 2019-11-27 | 聚酯多元醇及聚氨酯 |
US17/298,215 US20220089807A1 (en) | 2018-11-30 | 2019-11-27 | Polyester polyol and polyurethane |
EP19888725.9A EP3889199A4 (en) | 2018-11-30 | 2019-11-27 | POLYESTER POLYOLS AND POLYURETHANE |
PCT/JP2019/046390 WO2020111130A1 (ja) | 2018-11-30 | 2019-11-27 | ポリエステルポリオール、及びポリウレタン |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2018225692A JP7184615B2 (ja) | 2018-11-30 | 2018-11-30 | ポリウレタン |
Publications (2)
Publication Number | Publication Date |
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JP2020084158A JP2020084158A (ja) | 2020-06-04 |
JP7184615B2 true JP7184615B2 (ja) | 2022-12-06 |
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Country Status (5)
Country | Link |
---|---|
US (1) | US20220089807A1 (ja) |
EP (1) | EP3889199A4 (ja) |
JP (1) | JP7184615B2 (ja) |
CN (1) | CN113166353B (ja) |
WO (1) | WO2020111130A1 (ja) |
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2019
- 2019-11-27 US US17/298,215 patent/US20220089807A1/en active Pending
- 2019-11-27 CN CN201980077421.5A patent/CN113166353B/zh active Active
- 2019-11-27 EP EP19888725.9A patent/EP3889199A4/en active Pending
- 2019-11-27 WO PCT/JP2019/046390 patent/WO2020111130A1/ja unknown
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WO2007023655A1 (ja) | 2005-08-24 | 2007-03-01 | Daicel Chemical Industries, Ltd. | ポリエステルポリオール及びポリウレタン系樹脂 |
JP2007262241A (ja) | 2006-03-28 | 2007-10-11 | Daicel Chem Ind Ltd | ポリウレタン系樹脂及びその塗膜 |
JP2011174037A (ja) | 2009-10-30 | 2011-09-08 | Mitsubishi Chemicals Corp | ポリエステルポリオール、それを用いたポリウレタン及びその製造方法、並びにポリウレタン成形体 |
JP2012131838A (ja) | 2010-12-17 | 2012-07-12 | Tosoh Corp | ポリウレタンエラストマー及びその製造法 |
CN105418918A (zh) | 2015-12-07 | 2016-03-23 | 中北大学 | 耐高温聚酰胺及其合成方法 |
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Publication number | Publication date |
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JP2020084158A (ja) | 2020-06-04 |
EP3889199A4 (en) | 2022-08-17 |
WO2020111130A1 (ja) | 2020-06-04 |
CN113166353A (zh) | 2021-07-23 |
US20220089807A1 (en) | 2022-03-24 |
CN113166353B (zh) | 2023-10-20 |
EP3889199A1 (en) | 2021-10-06 |
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