JP6838133B2 - 発泡ポリウレタンエラストマー原料、発泡ポリウレタンエラストマーおよび発泡ポリウレタンエラストマーの製造方法 - Google Patents
発泡ポリウレタンエラストマー原料、発泡ポリウレタンエラストマーおよび発泡ポリウレタンエラストマーの製造方法 Download PDFInfo
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- JP6838133B2 JP6838133B2 JP2019501308A JP2019501308A JP6838133B2 JP 6838133 B2 JP6838133 B2 JP 6838133B2 JP 2019501308 A JP2019501308 A JP 2019501308A JP 2019501308 A JP2019501308 A JP 2019501308A JP 6838133 B2 JP6838133 B2 JP 6838133B2
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- polyurethane elastomer
- foamed polyurethane
- mass
- raw material
- polyol
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- 239000002994 raw material Substances 0.000 title claims description 47
- 238000004519 manufacturing process Methods 0.000 title claims description 17
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- 239000011496 polyurethane foam Substances 0.000 title description 6
- 238000000034 method Methods 0.000 title description 5
- 229920001971 elastomer Polymers 0.000 title description 4
- 239000000806 elastomer Substances 0.000 title description 4
- 229920003225 polyurethane elastomer Polymers 0.000 claims description 134
- 229920005862 polyol Polymers 0.000 claims description 104
- -1 alkane polyols Chemical class 0.000 claims description 93
- 150000003077 polyols Chemical class 0.000 claims description 57
- 150000002009 diols Chemical class 0.000 claims description 52
- 239000003054 catalyst Substances 0.000 claims description 51
- 229920001228 polyisocyanate Polymers 0.000 claims description 46
- 239000005056 polyisocyanate Substances 0.000 claims description 46
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 43
- 229920000570 polyether Polymers 0.000 claims description 43
- 229910052751 metal Inorganic materials 0.000 claims description 34
- 239000002184 metal Substances 0.000 claims description 34
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 238000005187 foaming Methods 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 17
- 229910052797 bismuth Inorganic materials 0.000 claims description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 11
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 11
- 229910052725 zinc Inorganic materials 0.000 claims description 11
- 239000011701 zinc Substances 0.000 claims description 11
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 10
- 239000006260 foam Substances 0.000 claims description 9
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 239000006096 absorbing agent Substances 0.000 description 13
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
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- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
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- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002518 antifoaming agent Substances 0.000 description 4
- NSPSPMKCKIPQBH-UHFFFAOYSA-K bismuth;7,7-dimethyloctanoate Chemical compound [Bi+3].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O NSPSPMKCKIPQBH-UHFFFAOYSA-K 0.000 description 4
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- 239000001294 propane Substances 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 2
- 241000288673 Chiroptera Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
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- 238000013329 compounding Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000009408 flooring Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
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- 230000000474 nursing effect Effects 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- KYDGMZSIZYYJJJ-UHFFFAOYSA-L [dimethyl-(2-sulfanylacetyl)oxystannyl] 2-sulfanylacetate Chemical compound C[Sn+2]C.[O-]C(=O)CS.[O-]C(=O)CS KYDGMZSIZYYJJJ-UHFFFAOYSA-L 0.000 description 1
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
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-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/10—Water or water-releasing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
- C08J2375/06—Polyurethanes from polyesters
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Footwear And Its Accessory, Manufacturing Method And Apparatuses (AREA)
Description
1.ポリイソシアネート
(1)1,4-ビス(イソシアナトメチル)シクロヘキサン(1,4−BIC、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−ビス(イソシアナトメチル)シクロヘキサン(1,3−BIC、商品名:タケネート600、三井化学社製)
2.マクロポリオール
2−1.直鎖オキシアルキレン基を有するポリエーテルジオール
(1)PTG−1000(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:111.9mgKOH/g、保土ヶ谷化学工業社製)
(2)PTG−2000(ポリテトラメチレンエーテルグリコール、商品名:PTG−2000SN、数平均分子量:2000、平均水酸基価:56.2mgKOH/g、保土ヶ谷化学工業社製)
(3)PTG−3000(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:38.0mgKOH/g、保土ヶ谷化学工業社製)
(4)ポリプロパンジオール−1000(ポリトリメチレンエーテルグリコール、商品名:PO3GH1000、数平均分子量:1000、平均水酸価:112.1mgKOH/g、Weylchem社製)
(5)ポリプロパンジオール−2400(ポリトリメチレンエーテルグリコール、商品名:PO3GH2400、数平均分子量:2400、平均水酸価:48mgKOH/g、Weylchem社製)
2−2.分岐オキシアルキレン基を有するポリエーテルジオール
(1)PPG#3000(ポリオキシプロピレングリコール、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することにより得た。数平均分子量:3000、平均水酸基価:37.5mgKOH/g)
3.アルカンポリオール
3−1.直鎖アルカンジオール
(1)1,4−ブタンジオール(三菱化学社製)
(2)1,3−プロパンジオール(商品名:SUSTERRAプロパンジオール、デュポン社製)
(3)エチレングコール(和光純薬製)
(4)1,5−ペンタンジオール(宇部興産製)
(5)1,6−ヘキサンジオール(和光純薬製)
3−2.分岐アルカンジオール
(1)1,2−プロパンジオール(和光純薬製)
(2)1,3−ブタンジオール(和光純薬製)
3−3.トリオール
(1)グリセリン(和光純薬製)
(2)TMP(1,1,1−トリス(ヒドロキシメチル)プロパン、和光純薬製)
4.ウレタン化触媒
4−1.有機触媒
(1)アミン触媒(トリエチレンジアミン、商品名:DABCO−CRYSTALLINE、エアプロダクツジャパン社製)
(2)イミダゾール触媒(1,2−ジメチルイミダゾールの65〜75%エチレングリコール溶液、商品名:TOYOCATDM−70、東ソー社製)
4−2.金属触媒
(1)ビスマスネオデカネート(ネオデカン酸ビスマス(III)、商品名:BiCAT8108、シェファードケミカル製)
(2)ビスマスオクトエート(オクチル酸ビスマス(III)、商品名:プキャット25、日本化学産業社製)
(3)亜鉛触媒(商品名:K−KAT XK−633、KING社製)
5.整泡剤
(1)サーフロンAF−5000(AGCセイミケミカル社製)
6.添加剤
(1)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)紫外線吸収剤(ベンゾトリアゾール化合物、商品名:チヌビン571、BASFジャパン社製)
(3)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)
<各実施例および比較例>
1.ポリイソシアネート成分(A)の調製
各表に示す質量部数で、ポリイソシアネートおよびマクロポリオールを、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。
各表に示した質量部数のポリオール成分(B)と、発泡剤(イオン交換水)0.86質量部と、整泡剤0.5質量部と、アミン触媒1.2質量部と、イミダゾール触媒1.0質量部と、酸化防止剤0.5質量部と、紫外線吸収剤0.5質量部と、耐光安定剤0.5質量部とを、均一に攪拌混合して、50℃のオーブン中に1時間静置し、レジンプレミックスを調製した。
(1)外観
各実施例および比較例の発泡ポリウレタンエラストマーを目視により観察し、表面の荒れを判定した。各表中に「OK」と記載されている場合、表面が滑らかであることを示す。
(2)見かけ密度
各実施例および比較例の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 K7222:2005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。
(3)反発弾性
各実施例および比較例の発泡ポリウレタンエラストマーから10cm×10cm×1cmの測定試料を切り出し、JIS K6400−3:2012に従って、測定試料の反発弾性を測定した。結果を各表に示す。
(4)アスカーC硬度
JIS K7312−7:1996に従って、各実施例および比較例の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。
(5)破断強度、破断伸び
各実施例および比較例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 K6400−5:2012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。
(6)圧縮永久歪み
各実施例および比較例の発泡ポリウレタンエラストマーから直径29mmで厚み10mmの円板状の測定試料を切り出し、JIS K6262に従って、50℃×6時間、50%圧縮の条件で、測定試料の圧縮永久歪みを測定した。結果を各表に示す。
(7)耐屈曲き裂性
各実施例および比較例の発泡ポリウレタンエラストマーから、140mm×25mm×6.3mmの測定試料を切り出し、JIS K6260:2010に従って、測定試料の耐屈曲き裂性を測定した。結果を各表に示す。
Claims (11)
- ポリイソシアネート成分(A)とポリオール成分(B)とを含む発泡ポリウレタンエラストマー原料であって、
前記ポリイソシアネート成分(A)は、1,4−ビス(イソシアナトメチル)シクロヘキサン(A1)と、炭素数が3から4である直鎖オキシアルキレン基を主鎖として有するポリエーテルジオール(A2)とのプレポリマーを含み、
前記ポリオール成分(B)は、炭素数が3から4である直鎖オキシアルキレン基を主鎖として有するポリエーテルジオールを90質量%以上含むマクロポリオール(B1)と、炭素数が2から6である直鎖または分岐のアルキレン基を有するアルカンポリオール(B2)とを含み、
前記ポリイソシアネート成分(A)中の前記プレポリマーの割合は、70質量%以上、100質量%以下であり、
前記ポリオール成分(B)中の前記アルカンポリオール(B2)の割合は、20質量%以上、50質量%以下であることを特徴とする、発泡ポリウレタンエラストマー原料。 - 前記アルカンポリオール(B2)の配合部数は、前記マクロポリオール(B1)100質量部に対して、25質量部以上、100質量部以下であることを特徴とする、請求項1に記載の発泡ポリウレタンエラストマー原料。
- 前記マクロポリオール(B1)の数平均分子量は、400以上、10000以下であり、
前記マクロポリオール(B1)は、第1の数平均分子量を有する第1ポリエーテルジオール(B1−1)と、前記第1の数平均分子量との差が1000以上である第2の数平均分子量を有する第2ポリエーテルジオール(B1−2)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エラストマー原料。 - 前記ポリオール成分(B)は、複数種類の前記アルカンポリオール(B2)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エラストマー原料。
- 前記ポリオール成分(B)は、直鎖の前記アルカンポリオール(B2)を含むことを特徴とする、請求項4に記載の発泡ポリウレタンエラストマー原料。
- 複数種類の前記アルカンポリオール(B2)の総量中に、炭素数が4である前記アルカンポリオール(B2)が、45mol%以上、95mol%以下含まれることを特徴とする、請求項4に記載の発泡ポリウレタンエラストマー原料。
- 前記ポリオール成分(B)は、炭素数が3である前記アルカンポリオール(B2)を含むことを特徴とする、請求項4に記載の発泡ポリウレタンエラストマー原料。
- 請求項1に記載の発泡ポリウレタンエラストマー原料の発泡体であることを特徴とする、発泡ポリウレタンエラストマー。
- シューズのミッドソールの材料であることを特徴とする、請求項8に記載の発泡ポリウレタンエラストマー。
- 請求項8に記載の発泡ポリウレタンエラストマーを製造するための発泡ポリウレタンエラストマーの製造方法であって、
請求項1に記載の発泡ポリウレタンエラストマー原料を準備する準備工程と、
前記発泡ポリウレタンエラストマー原料を発泡させる発泡工程と
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の製造方法。 - 前記発泡工程において、ビスマスを含有する金属触媒、および、亜鉛を含有する金属触媒の存在下で、前記発泡ポリウレタンエラストマー原料を発泡させることを特徴とする、
請求項10に記載の発泡ポリウレタンエラストマーの製造方法。
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JP6961837B2 (ja) * | 2018-10-11 | 2021-11-05 | 三井化学株式会社 | 発泡ポリウレタンエラストマー原料、発泡ポリウレタンエラストマー、ミッドソールおよび発泡ポリウレタンエラストマーの製造方法 |
JP7296249B2 (ja) * | 2019-05-16 | 2023-06-22 | 三井化学株式会社 | 熱可塑性ポリウレタン樹脂 |
EP4081566A1 (en) * | 2019-12-24 | 2022-11-02 | Covestro Intellectual Property GmbH & Co. KG | Polyurethane resin composition and polyurethane resin molded product |
WO2021177175A1 (ja) * | 2020-03-05 | 2021-09-10 | 三井化学株式会社 | 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 |
EP4118127A4 (en) * | 2020-03-10 | 2024-04-10 | National Research Council of Canada | POLYURETHANE COMPOSITIONS AND ELASTOMERS MADE THEREFROM |
CN112409557B (zh) * | 2020-11-25 | 2023-06-13 | 天津科技大学 | 一种植物油基聚氨酯薄膜及其制备 |
WO2022230584A1 (ja) * | 2021-04-26 | 2022-11-03 | キヤノン株式会社 | ポリウレタンエラストマー、及びその製造方法 |
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