JP6038775B2 - 再生可能資源含有量を有する熱成形フォーム製造に適したポリオール - Google Patents
再生可能資源含有量を有する熱成形フォーム製造に適したポリオール Download PDFInfo
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Description
Q(NCO)n
〔式中、nは2〜5、好ましくは2〜3の数であり、Qは、2〜18個、好ましくは6〜10個の炭素原子を含有する脂肪族炭化水素基、4〜15個、好ましくは5〜10個の炭素原子を含有する脂環式炭化水素基、8〜15個、好ましくは8〜13個の炭素原子を含有する芳香脂肪族炭化水素基、6〜15個、好ましくは6〜13個の炭素原子を含有する芳香族炭化水素基である〕
により示されるイソシアネートが挙げられる。
触媒としてKOHを用いて製造された11%エチレンオキシド(混合ブロック中に添加された5%および末端キャップとして添加された6%)の合計を有する、グリセリンで開始された56ヒドロキシル価ポリエーテル。
触媒としてKOHを用いて製造された末端キャップとして添加された17.5%エチレンオキシドの合計を有するグリセリンおよびソルビトール(72/28重量%)で共開始された31.5ヒドロキシル価ポリエーテル
36ヒドロキシル価グリセリン系ポリエーテル中に分散した43%ポリ(アクリロニトリル/スチレン)(37/63重量%)を含有する20ヒドロキシル価ポリマーポリオール
POおよびEOで活性化前に、スターターとされたヒドロキシル化大豆油(BioBased TechnologiesによるArgol 4.0)を100ppmリン酸と共に加えたスターター/触媒混合物を得、90/10のPO/EO比にて3.5%のEOを添加し、次いで25/75のPO/EO比にて25%のEOを添加し、アルコキシル化した;OH価=56.7、全EO含有量=28.5%、第1級ヒドロキシル=31.3%。
90/10のPO/EO比にて5.6%のEOを添加し、次いで35/65のPO/EO比にて15%のEOを添加し、アルコキシル化した;OH価=56.1、全EO含有量=20.6%、第1級ヒドロキシル=33%。
ヒマシ油について開始処理を行い、90/10のPO/EO比にて4.1%のEOを添加し、次いで35/65のPO/EO比にて25%のEOを添加し、アルコキシル化した;OH価=55.9、全EO含有量=29.1%、第1級ヒドロキシル=35.8%。
ヒマシ油について開始処理を行い、90/10のPO/EO比にて5.5%のEOを添加し、次いで25/75のPO/EO比にて20%のEOを添加し、アルコキシル化した;OH価=56.7、全EO含有量=25.5%、第1級ヒドロキシル=37.3%。
POおよびEOで活性化前に、スターターとされたヒマシ油およびヒドロキシル化大豆油(BioBased TechnologiesによるArgol 4.0)を100ppmリン酸と共に加えたスターター/触媒混合物を得、90/10のPO/EO比にて4.2%のEOを添加し、次いで25/75のPO/EO比にて25%のEOを添加し、アルコキシル化した;OH価=55.9、全EO含有量=29.2%、第1級ヒドロキシル=38.3%。
ヒマシ油について開始処理を行い、90/10のPO/EO比にて5.1%のEOを添加し、次いで20/80のPO/EO比にて25%のEOを添加し、アルコキシル化した;OH価=54.8、全EO含有量=30.1%、第1級ヒドロキシル=45.8%。
ヒマシ油について開始処理を行い、90/10のPO/EO比にて5.4%のEOを添加し、次いで15/85のPO/EO比にて25%のEOを添加し、アルコキシル化した;OH価=56.8、全EO含有量=30.4%、第1級ヒドロキシル=47.8%。
ヒマシ油について開始処理を行い、90/10のPO/EO比にて6.2%のEOを添加し、次いで15/85のPO/EO比にて30%のEOを添加し、アルコキシル化した;OH価=56.1、全EO含有量=36.2%、第1級ヒドロキシル=52.6%。
柔軟ポリウレタンフォームは、表1に示すポリオールの100重量部(pbw)、3.50pbwの蒸留水、1.0pbwのEvonikから名称B−4900として市販のシリコーン界面活性剤、0.10pbwの名称Dabco T−9としてAir Productsから市販のオクタン酸錫触媒、0.15pbwのMomentive Performance Materialsから名称Niax A−1として市販のアミン触媒およびBayer MaterialScienceからMondur TD−80として市販のトルエンジイソシアネートを、100のNCO/OH指数を得るために必要な量で用いて擬似熱硬化成形法により製造した。
柔軟ポリウレタンフォームは、表2に示す45重量部(pbw)のポリオールCおよび55pbwのポリオールBまたは他のポリオールおよび/または2種の組み合わせ、2.25pbwの蒸留水、0.5pbwのAir Productsから名称DC−5164として市販のシリコーン界面活性剤、0.30pbwのMomentive Performance Materialsから名称Niax A−33として市販のアミン触媒、0.10pbwのMomentive Performance Materialsから名称Niax A−1として市販のアミン触媒、およびBayer MaterialScienceからMondur TD−80として市販のトルエンジイソシアネートを、100のNCO/OH指数を得るために必要な量で用いて標準高復元力(HR)「低温」成形法により製造した。フォーム形成性混合物を、15×15×4インチアルミニウム金型中へ65.6℃にて導入し、反応混合物を、該金型中で5.0分間発泡させた。成形フォームを金型から取出し、物理特性をASTM 標準手順により試験する前に7日間硬化させた。該フォームの物理特性もまた表2に示す。
Claims (7)
- 成形ポリウレタンフォームの製造方法であって、
a)(i)少なくとも1つのポリイソシアネートを含むポリイソシアネート成分と、
(ii)iia)ヒドロキシル官能性基を含有する植物油をDMC触媒と組み合わせて混合物を形成する工程、
iib)エチレンオキシドおよび/またはプロピレンオキシドおよび必要に応じて1以上の他のアルコキシドを、iia)からの混合物へ添加してDMC触媒を活性化する工程、iic)エチレンオキシド、プロピレンオキシドおよび必要に応じて1以上の他のアルコキシドを、iib)からの活性化DMC触媒を含有する混合物へ、ポリオール中のエチレンオキシドの百分率と製造されたポリオール中の第1級ヒドロキシル基の百分率とを足した合計が50〜77%であり、第1級ヒドロキシル基の百分率が少なくとも30%であるが50%未満であるような量で添加する工程
を含むアルコキシル化法により製造された再生可能資源に基づくポリオールを含むポリオール成分、および
(iii)発泡剤
とを組み合わせてポリウレタン形成性混合物を形成する工程、
b)ポリウレタン形成性混合物を金型中へ導入する工程、
c)金型を少なくとも94℃へ加熱する工程、
d)ポリウレタン形成性混合物を反応させてポリウレタンフォームを形成する工程、
e)冷却し、およびポリウレタンフォームを金型から取り出す工程、および
f)必要に応じて、ポリウレタンフォームを加熱炉中で硬化する工程
を含んでなる、製造方法。 - 製造された再生可能資源に基づくポリオール中のエチレンオキシドの量は、20重量%および30重量%の間である、請求項1に記載の方法。
- エチレンオキシドを、ポリオール中の第1級ヒドロキシル基の百分率が45%未満であるような量で添加する、請求項2に記載の方法。
- ヒドロキシ官能性基を含有する植物油を、大豆油、ヒマワリ油、キャノーラ油、亜麻仁油、綿実油、キリ油、パーム油、ケシ油、トウモロコシ油およびピーナッツ油から選択される少なくとも1つの油から誘導する、請求項1に記載の方法。
- 植物油はヒマシ油である、請求項1に記載の方法。
- 植物油は、重量による少なくとも50%ヒマシ油および他のヒドロキシ官能性基を含有する植物油を含むブレンドである、請求項1に記載の方法。
- ポリオール成分は、少なくとも30重量%の再生可能資源に基づくポリオールを含んでなる、請求項1に記載の方法。
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US32726210P | 2010-04-23 | 2010-04-23 | |
US61/327,262 | 2010-04-23 | ||
PCT/US2011/000685 WO2011133208A2 (en) | 2010-04-23 | 2011-04-15 | Polyols suitable for hot molded foam production with high renewable resource content |
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JP6038775B2 true JP6038775B2 (ja) | 2016-12-07 |
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US (1) | US10323212B2 (ja) |
EP (1) | EP2560944A4 (ja) |
JP (1) | JP6038775B2 (ja) |
KR (1) | KR20130091631A (ja) |
CN (1) | CN102858732B (ja) |
BR (1) | BR112012027070A2 (ja) |
CA (1) | CA2796656C (ja) |
MX (1) | MX2012012117A (ja) |
SG (2) | SG10201503146WA (ja) |
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US8598248B2 (en) * | 2010-07-16 | 2013-12-03 | Bayer Materialscience Llc | Flexible polyurethane foams made from alkoxylated natural oil |
CN102532457B (zh) * | 2012-02-09 | 2013-10-02 | 中国农业大学 | 一种利用玉米芯和工业辣椒废渣合成可降解聚氨酯的方法 |
JP2014125516A (ja) * | 2012-12-26 | 2014-07-07 | Kao Corp | 硬質ポリウレタンフォーム製造用ポリオール混合物 |
US10000601B2 (en) | 2014-03-27 | 2018-06-19 | Trent University | Metathesized triacylglycerol polyols for use in polyurethane applications and their related properties |
WO2015143563A1 (en) * | 2014-03-27 | 2015-10-01 | Trent University | Certain metathesized natural oil triacylglycerol polyols for use in polyurethane applications and their related physical properties |
WO2016119049A1 (en) * | 2015-01-26 | 2016-08-04 | Trent University | Methods of making triacylglycerol polyols from fractions of metathesized natural oils and uses thereof |
US9777245B2 (en) | 2015-01-30 | 2017-10-03 | Trent University | Methods of fractionating metathesized triacylglycerol polyols and uses thereof |
CA2986015A1 (en) * | 2015-05-15 | 2016-11-24 | Stepan Company | Ethoxylated vegetable oils in low density spray foam formulations |
CN106748767B (zh) * | 2015-11-19 | 2020-03-17 | 中国石油化工股份有限公司 | 一种低羟值植物油基多元醇及其制备方法 |
CN108003323B (zh) * | 2017-11-20 | 2021-01-15 | 万华化学(北京)有限公司 | 一种减震吸能聚氨酯材料及其制备方法 |
CN109134841A (zh) * | 2018-07-18 | 2019-01-04 | 江苏理工学院 | 一种高活性植物多元醇的制备方法 |
US11912814B2 (en) * | 2018-12-14 | 2024-02-27 | Nanjing Tech University | Preparation method of flexible polyurethane foam |
US11920017B2 (en) * | 2018-12-14 | 2024-03-05 | Nanjing Tech University | Preparation method of polyurethane foam |
US11613604B2 (en) | 2021-06-28 | 2023-03-28 | Covestro Llc | Isocyanate-reactive compositions, polyurethane foams formed therefrom, multi-layer composite articles that include such foams, and methods for their preparation |
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TW307778B (ja) * | 1992-10-28 | 1997-06-11 | Takeda Pharm Industry Co Ltd | |
JPH09124766A (ja) * | 1995-10-27 | 1997-05-13 | Asahi Glass Co Ltd | 軟質ポリウレタンフォームの製造方法 |
DE19903274A1 (de) * | 1999-01-28 | 2000-08-03 | Basf Ag | Verfahren zur Herstellung von Polyetherpolyolen |
DE19928156A1 (de) * | 1999-06-19 | 2000-12-28 | Bayer Ag | Aus Polyetherpolyolen hergestellte Polyurethan-Weichschäume |
DE10240186A1 (de) * | 2002-08-28 | 2004-03-11 | Basf Ag | Verfahren zur Herstellung von emissionsarmen Polyurethan-Weichschaumstoffen |
US20060073321A1 (en) * | 2004-10-01 | 2006-04-06 | Kaushiva Bryan D | Molded flexible polyurethane foams with reduced flammability and superior durability |
US20060229375A1 (en) * | 2005-04-06 | 2006-10-12 | Yu-Ling Hsiao | Polyurethane foams made with alkoxylated vegetable oil hydroxylate |
DE102005041142A1 (de) | 2005-08-30 | 2007-03-01 | Basf Ag | Verfahren zur Herstellung von Polyetheralkoholen |
DE102005056432A1 (de) | 2005-11-26 | 2007-05-31 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyolen auf Basis natürlicher Öle |
US20070238798A1 (en) * | 2006-04-05 | 2007-10-11 | Mcdaniel Kenneth G | Flexible polyurethane foams made from vegetable oil alkoxylated via DMC-catalysis |
WO2008075725A1 (ja) * | 2006-12-19 | 2008-06-26 | Asahi Glass Company, Limited | 軟質ポリウレタンフォームの製造方法 |
MX2012012596A (es) | 2010-04-30 | 2013-05-06 | Basf Se | Polioles de polieter, proceso para preparar polioles de polieter y su uso para producir poliuretanos. |
US9115246B2 (en) * | 2010-04-30 | 2015-08-25 | Basf Se | Polyether polyols, process for preparing polyether polyols and their use for producing polyurethanes |
US8598248B2 (en) | 2010-07-16 | 2013-12-03 | Bayer Materialscience Llc | Flexible polyurethane foams made from alkoxylated natural oil |
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2011
- 2011-04-15 KR KR1020127027437A patent/KR20130091631A/ko not_active Application Discontinuation
- 2011-04-15 SG SG10201503146WA patent/SG10201503146WA/en unknown
- 2011-04-15 WO PCT/US2011/000685 patent/WO2011133208A2/en active Application Filing
- 2011-04-15 EP EP20110772349 patent/EP2560944A4/en not_active Withdrawn
- 2011-04-15 US US13/641,890 patent/US10323212B2/en not_active Expired - Fee Related
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WO2011133208A3 (en) | 2012-02-23 |
CA2796656C (en) | 2018-07-03 |
US20130210951A1 (en) | 2013-08-15 |
EP2560944A2 (en) | 2013-02-27 |
BR112012027070A2 (pt) | 2016-07-26 |
WO2011133208A2 (en) | 2011-10-27 |
EP2560944A4 (en) | 2014-03-26 |
SG10201503146WA (en) | 2015-06-29 |
KR20130091631A (ko) | 2013-08-19 |
CN102858732B (zh) | 2015-11-25 |
CN102858732A (zh) | 2013-01-02 |
MX2012012117A (es) | 2012-12-17 |
JP2013530263A (ja) | 2013-07-25 |
CA2796656A1 (en) | 2011-10-27 |
SG184309A1 (en) | 2012-11-29 |
US10323212B2 (en) | 2019-06-18 |
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