JP2002030129A - 微発泡ポリウレタンエラストマー及びその製造方法 - Google Patents
微発泡ポリウレタンエラストマー及びその製造方法Info
- Publication number
- JP2002030129A JP2002030129A JP2001034209A JP2001034209A JP2002030129A JP 2002030129 A JP2002030129 A JP 2002030129A JP 2001034209 A JP2001034209 A JP 2001034209A JP 2001034209 A JP2001034209 A JP 2001034209A JP 2002030129 A JP2002030129 A JP 2002030129A
- Authority
- JP
- Japan
- Prior art keywords
- polyurethane elastomer
- polyol
- microfoamed
- mass
- polyoxyalkylene polyol
- 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.)
- Pending
Links
- 229920003225 polyurethane elastomer Polymers 0.000 title claims abstract description 138
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 26
- 238000007906 compression Methods 0.000 claims abstract description 25
- 230000006835 compression Effects 0.000 claims abstract description 25
- 229920005862 polyol Polymers 0.000 claims description 249
- 150000003077 polyols Chemical class 0.000 claims description 248
- 150000001875 compounds Chemical class 0.000 claims description 59
- 239000003054 catalyst Substances 0.000 claims description 51
- 239000005056 polyisocyanate Substances 0.000 claims description 42
- 229920001228 polyisocyanate Polymers 0.000 claims description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 33
- 229920005906 polyester polyol Polymers 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 25
- 239000000178 monomer Substances 0.000 claims description 22
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 20
- 238000012644 addition polymerization Methods 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 9
- 239000010419 fine particle Substances 0.000 claims description 8
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 4
- 239000011496 polyurethane foam Substances 0.000 claims description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004815 dispersion polymer Substances 0.000 claims 1
- 230000006872 improvement Effects 0.000 abstract description 5
- 238000004904 shortening Methods 0.000 abstract description 3
- -1 polyoxypropylene Polymers 0.000 description 49
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 40
- 239000000203 mixture Substances 0.000 description 25
- 230000000052 comparative effect Effects 0.000 description 23
- 230000000704 physical effect Effects 0.000 description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- 239000006260 foam Substances 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 229920001451 polypropylene glycol Polymers 0.000 description 15
- 150000005846 sugar alcohols Polymers 0.000 description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 14
- 239000003381 stabilizer Substances 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000004970 Chain extender Substances 0.000 description 11
- 125000002947 alkylene group Chemical group 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
- 125000006353 oxyethylene group Chemical group 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical class CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 229920006311 Urethane elastomer Polymers 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- 230000014509 gene expression Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004604 Blowing Agent Substances 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000000806 elastomer Substances 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000004088 foaming agent Substances 0.000 description 4
- 150000002483 hydrogen compounds Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229920001610 polycaprolactone Polymers 0.000 description 3
- 239000004632 polycaprolactone Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- QCYNHVHWJXDSOW-UHFFFAOYSA-N tetrakis[(tripyrrolidin-1-yl-$l^{5}-phosphanylidene)amino]phosphanium Chemical compound C1CCCN1P(N1CCCC1)(N1CCCC1)=N[P+](N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)N=P(N1CCCC1)(N1CCCC1)N1CCCC1 QCYNHVHWJXDSOW-UHFFFAOYSA-N 0.000 description 1
- GLBZKFGGCHCGAG-UHFFFAOYSA-M tetrakis[[tris(dimethylamino)-$l^{5}-phosphanylidene]amino]phosphanium;hydroxide Chemical compound [OH-].CN(C)P(N(C)C)(N(C)C)=N[P+](N=P(N(C)C)(N(C)C)N(C)C)(N=P(N(C)C)(N(C)C)N(C)C)N=P(N(C)C)(N(C)C)N(C)C GLBZKFGGCHCGAG-UHFFFAOYSA-M 0.000 description 1
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- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Footwear And Its Accessory, Manufacturing Method And Apparatuses (AREA)
- Polyurethanes Or Polyureas (AREA)
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| JP2001034209A JP2002030129A (ja) | 2000-02-17 | 2001-02-09 | 微発泡ポリウレタンエラストマー及びその製造方法 |
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| JP2002030129A true JP2002030129A (ja) | 2002-01-31 |
| JP2002030129A5 JP2002030129A5 (enrdf_load_stackoverflow) | 2008-02-14 |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008026367A1 (fr) * | 2006-08-29 | 2008-03-06 | Unimatec Co., Ltd. | Procédé de production d'élastomère polyuréthanne expansé |
| JP2011503314A (ja) * | 2007-11-14 | 2011-01-27 | ビーエーエスエフ ソシエタス・ヨーロピア | 改良された耐屈曲特性を有する発泡ポリウレタン |
| JP2011207969A (ja) * | 2010-03-29 | 2011-10-20 | Sanyo Chem Ind Ltd | ポリウレタンスラブフォーム用ポリオール組成物 |
| JP2016204403A (ja) * | 2015-04-15 | 2016-12-08 | 三井化学株式会社 | 発泡ポリウレタンエラストマーの製造方法、発泡ポリウレタンエラストマーおよび緩衝材 |
| KR20180026747A (ko) | 2015-08-18 | 2018-03-13 | 미쓰이 가가쿠 가부시키가이샤 | 발포 폴리유레테인 재료, 성형품, 및 발포 폴리유레테인 재료의 제조 방법 |
| US10029528B2 (en) | 2014-03-26 | 2018-07-24 | Sumitomo Riko Company Limited | Urethane bumper spring, and method for producing same |
| WO2020129806A1 (ja) * | 2018-12-21 | 2020-06-25 | 東ソー株式会社 | 軟質ポリウレタンフォーム成型用ポリオール組成物 |
| JP2020128519A (ja) * | 2018-12-21 | 2020-08-27 | 東ソー株式会社 | 軟質ポリウレタンフォーム成型用ポリオール組成物 |
| JP2021038299A (ja) * | 2019-09-02 | 2021-03-11 | 東ソー株式会社 | ポリウレタンインテグラルスキンフォーム用組成物、ポリウレタンインテグラルスキンフォーム、およびその製造方法 |
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| JPH0347202A (ja) * | 1989-04-11 | 1991-02-28 | Asahi Glass Co Ltd | ポリウレタン系樹脂製靴底，およびその製造方法 |
| JPH03121116A (ja) * | 1989-10-03 | 1991-05-23 | Toyo Tire & Rubber Co Ltd | 靴底用ポリウレタン組成物 |
| JPH08166695A (ja) * | 1994-12-13 | 1996-06-25 | Bridgestone Corp | 現像部材 |
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008056730A (ja) * | 2006-08-29 | 2008-03-13 | Yunimatekku Kk | 発泡ポリウレタンエラストマーの製造方法 |
| KR101465486B1 (ko) * | 2006-08-29 | 2014-11-26 | 에누오케 가부시키가이샤 | 발포 폴리우레탄 엘라스토머의 제조 방법 |
| WO2008026367A1 (fr) * | 2006-08-29 | 2008-03-06 | Unimatec Co., Ltd. | Procédé de production d'élastomère polyuréthanne expansé |
| JP2011503314A (ja) * | 2007-11-14 | 2011-01-27 | ビーエーエスエフ ソシエタス・ヨーロピア | 改良された耐屈曲特性を有する発泡ポリウレタン |
| JP2011207969A (ja) * | 2010-03-29 | 2011-10-20 | Sanyo Chem Ind Ltd | ポリウレタンスラブフォーム用ポリオール組成物 |
| US10029528B2 (en) | 2014-03-26 | 2018-07-24 | Sumitomo Riko Company Limited | Urethane bumper spring, and method for producing same |
| JP2016204403A (ja) * | 2015-04-15 | 2016-12-08 | 三井化学株式会社 | 発泡ポリウレタンエラストマーの製造方法、発泡ポリウレタンエラストマーおよび緩衝材 |
| KR20180026747A (ko) | 2015-08-18 | 2018-03-13 | 미쓰이 가가쿠 가부시키가이샤 | 발포 폴리유레테인 재료, 성형품, 및 발포 폴리유레테인 재료의 제조 방법 |
| US10513575B2 (en) | 2015-08-18 | 2019-12-24 | Mitsui Chemicals, Inc. | Foam polyurethane material, molded article, and method for producing foam polyurethane material |
| WO2020129806A1 (ja) * | 2018-12-21 | 2020-06-25 | 東ソー株式会社 | 軟質ポリウレタンフォーム成型用ポリオール組成物 |
| JP2020128519A (ja) * | 2018-12-21 | 2020-08-27 | 東ソー株式会社 | 軟質ポリウレタンフォーム成型用ポリオール組成物 |
| JP7443696B2 (ja) | 2018-12-21 | 2024-03-06 | 東ソー株式会社 | 軟質ポリウレタンフォーム成型用ポリオール組成物 |
| JP2021038299A (ja) * | 2019-09-02 | 2021-03-11 | 東ソー株式会社 | ポリウレタンインテグラルスキンフォーム用組成物、ポリウレタンインテグラルスキンフォーム、およびその製造方法 |
| JP7470889B2 (ja) | 2019-09-02 | 2024-04-19 | 東ソー株式会社 | ポリウレタンインテグラルスキンフォーム用組成物、ポリウレタンインテグラルスキンフォーム、およびその製造方法 |
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