JP6246839B2 - ポリブタジエン変性ポリマーポリオール、ポリブタジエン変性ポリマーポリオールから製造したフォーム、及びそれらの製造方法 - Google Patents
ポリブタジエン変性ポリマーポリオール、ポリブタジエン変性ポリマーポリオールから製造したフォーム、及びそれらの製造方法 Download PDFInfo
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- JP6246839B2 JP6246839B2 JP2015561393A JP2015561393A JP6246839B2 JP 6246839 B2 JP6246839 B2 JP 6246839B2 JP 2015561393 A JP2015561393 A JP 2015561393A JP 2015561393 A JP2015561393 A JP 2015561393A JP 6246839 B2 JP6246839 B2 JP 6246839B2
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- Prior art keywords
- polybutadiene
- polymer polyol
- weight
- modified polymer
- free radical
- Prior art date
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Classifications
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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
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
- C08G18/4845—Polyethers containing oxyethylene units and other oxyalkylene units containing oxypropylene or higher oxyalkylene end groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3275—Hydroxyamines containing two hydroxy groups
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Description
(A)一種以上のベースポリオール、
(B)少なくとも一種の予備成形された安定剤、
(C)一種以上のエチレン系不飽和モノマー、
及び
(D)ポリブタジエンの、
(E)少なくとも一種のフリーラジカル重合触媒、
及び所望により
(F)一種以上の連鎖移動剤
の存在下における、フリーラジカル重合生成物を含んでなり、該ポリブタジエンは、ポリマーポリオール中に、該予備成形された安定剤を通して、及び/又は別個の反応物として、導入され、該ポリブタジエンは、ポリマーポリオール中に、ポリマーポリオール100重量%に対して0.03〜1.0重量%の量で存在する。
(A)一種以上のベースポリオール、
(B)少なくとも一種の予備成形された安定剤、
(C)一種以上のエチレン系不飽和モノマー、
及び
(D)ポリマーポリオール100重量%に対して0.03〜1重量%、好ましくは0.1〜0.5重量%のポリブタジエンの、
(E)少なくとも一種のフリーラジカル重合触媒、
及び所望により
(F)一種以上の連鎖移動剤
の存在下における、フリーラジカル重合生成物を含んでなる。
(A)一種以上のベースポリオール、
(B)予備成形された安定剤100重量%に対して0.5〜13重量%、好ましくは1〜6重量%のポリブタジエンを含んでなる、少なくとも一種の予備成形された安定剤と、
(C)一種以上のエチレン系不飽和モノマーの、
(E)少なくとも一種のフリーラジカル重合触媒、
及び所望により
(F)一種以上の連鎖移動剤
の存在下における、フリーラジカル重合生成物を含んでなる。
本明細書において、下記の用語は以下の意味を有する。
OH=(56.1×1000×f)/mol.wt.
式中、OHは、ポリオールのヒドロキシル価を表し、
fは、ポリオールの官能性、即ち、ポリオールの1分子あたりの水酸基の平均数を表し
及び
mol.wt.は、ポリオールの分子量を表す。
ポリオールA ソルビトールのプロピレンオキシド付加物、16%エチレンオキシドキャップを含み、ヒドロキシル価が28であり、粘度が1700mPa.sである。
ベースポリオールA ソルビトール及びグリセリンのプロピレンオキシド付加物、17%エチレンオキシドキャップを含み、ヒドロキシル価が32であり、粘度が1100mPa.sである。
ベースポリオールB グリセリンのプロピレンオキシド付加物、20%エチレンオキシドキャップを含み、ヒドロキシル価が36であり、粘度が820mPa.sである。
CTA イソプロパノール、連鎖移動剤
SAN スチレン:アクリロニトリル
TMI イソプロペニルジメチルベンジルイソシアネート(不飽和脂肪族イソシアネート)、Cytec IndustriesからTMI(登録商標)として市販
MDI モノマー状MDI、MDIの4,4’−異性体約42重量%、MDIの2,4’−異性体約57重量%を含んでなり、残りがMDIの2,2’−異性体
TBPEH tert−ブチルペルオキシ−2−エチルヘキサノアート
AIBN 2,2’−アゾビスイソブチロニトリル、フリーラジカル重合開始剤、E.I.DuPont de Nemours and Co.からVAZO 64として市販
イソシアネートA トルエンジイソシアネート、2,4−異性体80重量%及び2,6−異性体20重量%を含んでなり、NCO基含有量48.3重量%
ポリオールB グリセリン/ソルビトールから出発したポリエーテルポリオール、プロピレンオキシド約81〜82%及びエチレンオキシド約17〜18%を含み、公称官能性が約3.5及びOH価が約31.5である
触媒A ジプロピレングリコール30重量%中ビス[2−ジメチルアミノエチル]エーテル70重量%、アミン触媒、Momentive Performance MaterialsからNIAX A−1として市販
触媒B ジプロピレングリコール67重量%中ジアザビシクロオクタン33重量%、アミン触媒、Momentive Performance MaterialsからNIAX A−33として市販
界面活性剤A シリコーン界面活性剤、DC 5043として市販
粘度 動的粘度、25℃でmPa.sとして報告
マクロマーA ポリオールA(100g)、TMI(0.5g)、MDI(0.5g)、及びCosCat 83(即ち、ビスマス(III)ネオデカノアート)触媒100ppmを75℃で4時間加熱することにより調製した。
マクロマーB ポリオールA(100g)、TMI(0.5g)、MDI(0.5g)、Ricon 131B(5g)、及びCosCat 83触媒100ppmを75℃で4時間加熱することにより調製した。
予備成形された安定剤は、インペラ及び4枚のバッフルを備えた、連続撹拌タンク反応器(CSTR)(第一段階)及びプラグ−フロー反応器(第二段階)を含んでなる2段階反応システムで調製した。各反応器における滞留時間は、約60分間であった。反応物を、供給タンクから反応基へ、イン−ライン静止ミキサーを通して、次いで供給チューブを通して反応器に連続的にポンプ輸送し、十分に混合した。反応混合物の温度は、120±5℃に制御した。第二段階反応器からの生成物は、各段階の圧力を65psigに制御するように設計された圧力調整器を通して連続的にオーバーフローさせた。次いで、生成物、即ち予備成形された安定剤は、冷却器を通り、収集容器中に送られた。予備成形された安定剤処方物は、表1に示す。
このシリーズの例は、ポリマーポリオールの製造に関する。ポリマーポリオールは、インペラ及び4枚のバッフルを備えた、連続撹拌タンク反応器(CSTR)(第一段階)及びプラグ−フロー反応器(第二段階)を含んでなる2段階反応システムで調製した。各反応器における滞留時間は、約60分間であった。反応物を、供給タンクから、イン−ライン静止ミキサーを通して、次いで供給チューブを通して反応器に連続的にポンプ輸送し、十分に混合した。反応混合物の温度は、115±5℃に制御した。第二段階反応器からの生成物は、各段階の圧力を45psigに制御するように設計された圧力調整器を通して連続的にオーバーフローさせた。次いで、生成物、即ちポリマーポリオールは、冷却器を通り、収集容器中に送られた。粗製物は、真空ストリッピングにかけ、揮発成分を除去した。生成物中の総重合体重量%は、ストリッピング前の粗製ポリマーポリオール中で測定したモノマーの濃度から計算した。
表4に示すフォームは、ポリオール、界面活性剤、水、触媒、及びジエタノールアミンをフラスコ中で混合し、マスターブレンドを形成することにより、製造した。次いで、望ましい量のポリマーポリオールを、望ましい量のマスターブレンドを含むカップに加えた。カップの内容物を55秒間混合した。イソシアネートインデックス100を与える望ましい量のイソシアネート成分をマスターブレンド及びポリマーポリオール混合物を含むカップに加えた。カップの内容物を5秒間混合し、反応混合物を、150°Fの水ジャケットを備えた型の中に急速に注ぎ込んだ。4.5分後、型からフォームを取り出し、セル開口粉砕装置にかけ、次いで250°Fの加熱炉中に30分間入れて、後硬化させた。温度及び湿度を調整した実験室で24時間エージング後、フォームを物理的特性試験にかけた。
Claims (30)
- ポリブタジエン変性されたポリマーポリオールであって、
(A)一種以上のベースポリオール、
(B)少なくとも一種の予備成形された安定剤、
(C)一種以上のエチレン系不飽和モノマー、
及び
(D)ポリブタジエンの、
(E)少なくとも一種のフリーラジカル重合触媒、
及び所望により
(F)一種以上の連鎖移動剤
の存在下における、フリーラジカル重合生成物を含んでなり、前記ポリブタジエンが、前記ポリマーポリオール中に、前記予備成形された安定剤を通して、及び/又は別個の試薬として、導入され、前記ポリブタジエンが、前記ポリマーポリオール中に、前記ポリマーポリオール100重量%に対して0.03〜1.0重量%の量で存在する、ポリブタジエン変性されたポリマーポリオール。 - 前記ポリブタジエン(D)が、前記ポリマーポリオール100重量%に対して0.1〜0.5重量%の量で前記ポリマーポリオール中に存在する、請求項1に記載のポリブタジエン変性されたポリマーポリオール。
- 前記エチレン系不飽和モノマー(C)が、スチレン及びアクリロニトリルを含んでなる、請求項1に記載のポリブタジエン変性されたポリマーポリオール。
- 前記一種以上のベースポリオール(A)が、約2〜約8の官能性及び約10〜約1000のOH価を有する、少なくとも一種のポリエーテルポリオールを含んでなる、請求項1に記載のポリブタジエン変性されたポリマーポリオール。
- 前記ポリブタジエン(D)が、数平均分子量1000〜10,000を有するポリブタジエンのホモポリマーを含んでなる、請求項1に記載のポリブタジエン変性されたポリマーポリオール。
- スチレン及びアクリロニトリルが、80:20〜20:80の重量比で存在する、請求項3に記載のポリブタジエン変性されたポリマーポリオール。
- 前記ポリマーポリオールの固体含有量が約20重量%〜約75重量%までである、請求項1に記載のポリブタジエン変性されたポリマーポリオール。
- イソプロパノールを含んでなる連鎖移動剤が存在する、請求項1に記載のポリブタジエン変性されたポリマーポリオール。
- 前記フリーラジカル重合触媒(E)が、過酸化物、アゾ化合物、及びそれらの混合物からなる群から選択される、請求項1に記載のポリブタジエン変性されたポリマーポリオール。
- ポリブタジエン変性されたポリマーポリオールであって、
(A)一種以上のベースポリオール、
(B)少なくとも一種の予備成形された安定剤、
(C)一種以上のエチレン系不飽和モノマー、
と
(D)総ポリマーポリオール100重量%に対して0.03〜1重量%のポリブタジエンの、
(E)少なくとも一種のフリーラジカル重合触媒、
及び所望により
(F)一種以上の連鎖移動剤
の存在下における、フリーラジカル重合生成物を含んでなる、ポリブタジエン変性されたポリマーポリオール。 - ポリブタジエン変性されたポリマーポリオールであって、
(A)一種以上のベースポリオール、
(B)予備成形された安定剤100重量%に対して0.5〜13重量%のポリブタジエンを含んでなる、少なくとも一種の予備成形された安定剤と、
(C)一種以上のエチレン系不飽和モノマーの、
(E)少なくとも一種のフリーラジカル重合触媒、
及び所望により
(F)一種以上の連鎖移動剤
の存在下における、フリーラジカル重合生成物を含んでなる、ポリブタジエン変性されたポリマーポリオール。 - 前記予備成形された安定剤中に1〜6重量%ポリブタジエンが存在する、請求項11に記載のポリブタジエン変性されたポリマーポリオール。
- ポリブタジエン変性されたポリマーポリオールの製造方法であって、
(I)(A)一種以上のベースポリオール、
(B)少なくとも一種の予備成形された安定剤、
(C)一種以上のエチレン系不飽和モノマー、
及び
(D)ポリブタジエンを、
(E)少なくとも一種のフリーラジカル重合触媒、
及び所望により
(F)一種以上の連鎖移動剤
の存在下で、フリーラジカル重合させることを含んでなり、
前記ポリブタジエンが、ポリマーポリオール中に、前記予備成形された安定剤を通して、及び/又は別個の反応物として、導入され、前記ポリブタジエンが、前記ポリマーポリオール中に、ポリマーポリオール100重量%に対して0.03〜1.0重量%の量で存在する、方法。 - 前記ポリブタジエン(D)が、前記ポリマーポリオール100重量%に対して0.1〜0.5重量%の量で前記ポリマーポリオール中に存在する、請求項13に記載の方法。
- 前記エチレン系不飽和モノマー(C)が、スチレン及びアクリロニトリルを含んでなる、請求項13に記載の方法。
- 前記一種以上のベースポリオール(A)が、約2〜約8の官能性及び約10〜約1000のOH価を有する、少なくとも一種のポリエーテルポリオールを含んでなる、請求項13に記載の方法。
- 前記ポリブタジエン(D)が、数平均分子量1000〜10,000を有するポリブタジエンのホモポリマーを含んでなる、請求項13に記載の方法。
- スチレン及びアクリロニトリルが、80:20〜20:80の重量比で存在する、請求項15に記載の方法。
- 前記ポリマーポリオールの固体含有量が約20重量%〜約75重量%までである、請求項13に記載の方法。
- イソプロパノールを含んでなる連鎖移動剤が存在する、請求項13に記載の方法。
- 前記フリーラジカル重合触媒(E)が、過酸化物、アゾ化合物、及びそれらの混合物からなる群から選択される、請求項13に記載の方法。
- ポリマーポリオールの製造方法であって、
(I)(A)一種以上のベースポリオール、
(B)少なくとも一種の予備成形された安定剤、
(C)一種以上のエチレン系不飽和モノマーと、
(D)総PMPO生成物の重量に対して0.03〜1重量%のポリブタジエンを、
(E)少なくとも一種のフリーラジカル重合触媒、
及び所望により
(F)一種以上の連鎖移動剤
の存在下で、フリーラジカル重合させること
を含んでなる、ポリマーポリオールの製造方法。 - ポリブタジエン変性されたポリマーポリオールの製造方法であって、
(I)(A)一種以上のベースポリオール、
(B)予備成形された安定剤100重量%に対して0.5〜13重量%のポリブタジエンを含んでなる、少なくとも一種の予備成形された安定剤と、
(C)一種以上のエチレン系不飽和モノマーを、
(E)少なくとも一種のフリーラジカル重合触媒、
及び所望により
(F)一種以上の連鎖移動剤
の存在下でフリーラジカル重合させること
を含んでなる、ポリブタジエン変性されたポリマーポリオールの製造方法。 - 前記予備成形された安定剤中に1〜6重量%ポリブタジエンが存在する、請求項23に記載の方法。
- フォームであって、
(1)ポリイソシアネート成分と、
(2)請求項1に記載のポリブタジエン変性されたポリマーポリオールを含んでなるイソシアネートと反応性がある成分の、
(3)一種以上の触媒、
(4)一種以上の発泡剤、
及び
(5)一種以上の界面活性剤
の存在下における反応生成物を含んでなる、フォーム。 - ポリウレタンフォームであって、
(1)ポリイソシアネート成分と、
(2)請求項10に記載のポリブタジエン変性されたポリマーポリオールを含んでなるイソシアネートと反応性がある成分の、
(3)一種以上の触媒、
(4)一種以上の発泡剤、
及び
(5)一種以上の界面活性剤
の存在下における反応生成物を含んでなる、ポリウレタンフォーム。 - ポリウレタンフォームであって、
(1)ポリイソシアネート成分と、
(2)請求項11に記載のポリブタジエン変性されたポリマーポリオールを含んでなるイソシアネートと反応性がある成分の、
(3)一種以上の触媒、
(4)一種以上の発泡剤、
及び
(5)一種以上の界面活性剤
の存在下における反応生成物を含んでなる、ポリウレタンフォーム。 - ポリウレタンフォームの製造方法であって、
(1)ポリイソシアネート成分と、
(2)請求項1に記載のポリブタジエン変性されたポリマーポリオールを含んでなるイソシアネートと反応性がある成分を、
(3)一種以上の触媒、
(4)一種以上の発泡剤、
及び
(5)一種以上の界面活性剤
の存在下で反応させることを含んでなる、ポリウレタンフォームの製造方法。 - ポリウレタンフォームの製造方法であって、
(1)ポリイソシアネート成分と、
(2)請求項10に記載のポリブタジエン変性されたポリマーポリオールを含んでなるイソシアネートと反応性がある成分を、
(3)一種以上の触媒、
(4)一種以上の発泡剤、
及び
(5)一種以上の界面活性剤
の存在下で反応させることを含んでなる、ポリウレタンフォームの製造方法。 - ポリウレタンフォームの製造方法であって、
(1)ポリイソシアネート成分と、
(2)請求項11に記載のポリブタジエン変性されたポリマーポリオールを含んでなるイソシアネートと反応性がある成分を、
(3)一種以上の触媒、
(4)一種以上の発泡剤、
及び
(5)一種以上の界面活性剤
の存在下で反応させることを含んでなる、ポリウレタンフォームの製造方法。
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US13/790,249 | 2013-03-08 | ||
PCT/US2014/018505 WO2014137678A1 (en) | 2013-03-08 | 2014-02-26 | Polybutadiene modified polymer polyols, foams prepared from polybutadiene modified polymer polyols, and processes for the production thereof |
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US (1) | US9163099B2 (ja) |
EP (3) | EP2964689B1 (ja) |
JP (1) | JP6246839B2 (ja) |
KR (1) | KR20150126925A (ja) |
CN (1) | CN105008430B (ja) |
BR (1) | BR112015021989A2 (ja) |
CA (1) | CA2903913A1 (ja) |
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-
2013
- 2013-03-08 US US13/790,249 patent/US9163099B2/en active Active
-
2014
- 2014-02-26 JP JP2015561393A patent/JP6246839B2/ja not_active Expired - Fee Related
- 2014-02-26 KR KR1020157027890A patent/KR20150126925A/ko not_active Application Discontinuation
- 2014-02-26 CA CA2903913A patent/CA2903913A1/en not_active Abandoned
- 2014-02-26 EP EP14759944.3A patent/EP2964689B1/en active Active
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- 2014-02-26 WO PCT/US2014/018505 patent/WO2014137678A1/en active Application Filing
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Also Published As
Publication number | Publication date |
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JP2016510825A (ja) | 2016-04-11 |
US20140256839A1 (en) | 2014-09-11 |
MX2015011761A (es) | 2016-01-15 |
EP2964689A1 (en) | 2016-01-13 |
EP2964689A4 (en) | 2016-10-26 |
EP2964689B1 (en) | 2017-11-08 |
WO2014137678A1 (en) | 2014-09-12 |
CN105008430A (zh) | 2015-10-28 |
US9163099B2 (en) | 2015-10-20 |
BR112015021989A2 (pt) | 2017-12-19 |
EP3284769A1 (en) | 2018-02-21 |
KR20150126925A (ko) | 2015-11-13 |
CN105008430B (zh) | 2017-08-08 |
CA2903913A1 (en) | 2014-09-12 |
EP3284768A1 (en) | 2018-02-21 |
MX345758B (es) | 2017-02-15 |
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