JP6942140B2 - ポリウレタンフォームおよびポリイソシアヌレートフォームのための反応性難燃剤 - Google Patents
ポリウレタンフォームおよびポリイソシアヌレートフォームのための反応性難燃剤 Download PDFInfo
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- JP6942140B2 JP6942140B2 JP2018544768A JP2018544768A JP6942140B2 JP 6942140 B2 JP6942140 B2 JP 6942140B2 JP 2018544768 A JP2018544768 A JP 2018544768A JP 2018544768 A JP2018544768 A JP 2018544768A JP 6942140 B2 JP6942140 B2 JP 6942140B2
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- oxide
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Description
R1、R2、R3、およびR4は、独立して、H、一個から四個の炭素原子を有する直鎖状または分岐鎖状のアルキル基、好ましくはメチルまたはエチル;または塩素から選択され、
ならびにXは、・・・(Z)k−R7または
ならびに、Xが、・・・(Z)k−R7である場合、Zは、−(Y−O)n−であり、この場合、Yは、二個から八個の炭素原子、好ましくは二個から四個の炭素原子を有する直鎖状または分岐鎖状のアルキレン基、より好ましくはエチレン、プロピレン、またはイソプロピレンであり、nは、1から20、好ましくは1から5の整数を表し、
kは、0または1であり得;
R7は、水素、二個から約八個の炭素原子、好ましくは二個から四個の炭素原子を有するヒドロキシ末端の直鎖状または分岐鎖状のアルキレン基から選択され;ならびに
ただし、kがゼロの場合、R7は、当該ヒドロキシ末端の直鎖状または分岐鎖状アルキレン基であり、kが1の場合、R7は水素であり、ならびに、
Xが、
あるいは、R5およびR6は、お互いに結合して、五個から約八個の炭素原子、好ましくは六個の炭素原子を有するシクロアルキル基を形成する]であり;ならびに、式(I−B)は、
R1、R2、R3、およびR4は、独立して、H、一個から四個の炭素原子を有する直鎖状または分岐鎖状のアルキル基、好ましくはメチルまたはエチル;または塩素から選択され、
n1およびn2のそれぞれは、1以上であり、好ましくはn1およびn2のそれぞれは、約1から約5であり、その場合、n1+n2は、3以上、好ましくは約3から約5であり、ならびに、
Z2は、n1+n2の結合価を有する分岐鎖状ポリオールに由来する部分であり、ならびに当該一般式:
この場合、Rは、以下:
式I−A−2は、
HO−(Z)k−R7 (V)
[式中、Z、R7、および当該添え字kは、上記において定義される通りである]の脂肪族ジオールとの当該反応によって調製される。
1.Terate HT5100−Invistaから入手可能な、295mgKOH/gのヒドロキシル値を有する芳香族ポリエステルポリオール。
2.JEFFOL R 425X − Huntsmanから入手可能な、425mgKOH/gのヒドロキシル値を有するポリエーテルポリオール。
Kosa Terate 2541 − Invistaから入手可能な、234mgKOH/gのヒドロキシル値を有する芳香族ポリエステルポリオール。
Polycat77:Air Productsから入手可能なN−[3−(ジメチルアミノ)プロピル]−N,N’,N’−トリメチルプロパン−1,3−ジアミン
DABCO BL−11:N,N,N’,N’−テトラメチル−2,2’−オキシビス(エチルアミン)、Air Productsから入手可能なアミン触媒
DC193:Air Productsから入手可能なシリコーン界面活性剤
Bicat 8210:Shepard Chemicalから入手可能なビスマストリス(2−エチルヘキサノエート)
DMCHA:ジメチルシクロヘキシルアミン
Dabco TMR30:2,4,6−トリス(ジメチルアミノメチル)フェノール、Air Productsから入手可能なアミン触媒
Tegostab B8460:Evonikから入手可能なポリエーテル変性ポリシロキサン界面活性剤
Kosmos 75:Evonikから入手可能なカリウム−2−エチルヘキサノエート触媒
HFC−245fa:Honeywellから入手可能な発泡剤
ペンタン:発泡剤
イソシアネートMDI:Huntsmanから入手可能なポリマー性ジフェニルメタンジイソシアネート
当該難燃性組成物を使用して噴霧配合ウレタンフォームを調製するプロセス
当該フォーム調製のための手順は以下の通りである。
当該ポリオール、水、界面活性剤、難燃剤(以下の当該表において「FR」と略される)、および触媒を秤量し、ミキシングビーカーに入れ、混合して均一な溶液を形成した。この溶液に、HFC−245faを加え、蒸発に対してその重量を維持しながら、さらに混合した後、当該ポリマー性イソシアネートを加えた。当該混合物を、20℃において、5500rpmで3秒間、手短に撹拌し、厚紙のケーキボックスに注ぎ入れた。結果として形成された当該フォームを、室温において少なくとも24時間維持し、次いで、当該ボックスから取り出し、鋸によって試験片へと切断した。次いで、当該試料を、DIN 4102 B2試験手順に従って燃焼性を試験した(15.0cm以下の炎の高さは、当該フォームが当該試験を合格したことを意味する)。表1は、当該フォーム調製のための当該原材料およびパラメータならびに当該試験の当該結果を表す。
当該難燃性組成物を使用して、300%のMDIインデックスを有する硬質ポリイソシアヌレートフォーム(PIR)を調製するプロセス
当該フォーム調製のための手順は以下の通りである。
当該ポリオール、水、界面活性剤、難燃剤、および触媒を秤量し、ミキシングビーカーに入れ、混合して均一な溶液を形成した。この溶液に、ペンタンを加え、さらに撹拌した後、当該ポリマー性イソシアネート。次いで、当該混合物を、20℃において、3500rpmで6秒間撹拌し、厚紙のケーキボックスに注ぎ入れた。結果として形成された当該フォームを、室温において少なくとも24時間維持し、次いで、当該ビーカーから取り出し、鋸によって試験片へと切断した。次いで、当該試料を、DIN 4102 B2試験手順に従って燃焼性を試験した(15.0cm以下の炎の高さは、当該フォームが当該試験を合格したことを意味する)。表2は、当該フォーム調製のための当該原材料およびパラメータならびに当該フォームの試験の当該結果をまとめる。
本発明の当該新規の化合物の当該適用を、軟質ポリウレタンフォーム(適用例3)のための標準的配合における難燃剤としてのそれらの使用によって実証する。当該難燃剤に加えて、当該フォームの当該調製において、当該以下の成分を使用した。
当該ポリオールと、それぞれ調製実施例1および2のヒドロキシル官能性ホスホレン−1−オキシドとを混合することによってフォーム試料を調製した。イソシアネートを除く、水、アミン触媒、シリコーン界面活性剤、およびスズ触媒を含む当該配合の残りの成分を当該ポリオール/ヒドロキシル官能性ホスホレン−1−オキシド混合物に加え、ポリエーテルフォームの場合は2500rpmにおいて30秒、ポリエステルフォームの場合は1000rpmにおいて60秒撹拌した。当該反応混合物を激しく撹拌しながらの当該イソシアネートの添加および組み入れの後すぐに、当該完全な反応混合物を、8×8×5インチ(20×20×20cm)のボックスに注ぎ入れ、十分に発泡させた。次いで、当該ボックスを通気されたドラフトに24時間入れて、室温において硬化させた。当該フォーム試料の上部および底部の0.5インチならびに当該フォームの当該紙の裏打ち側を除去した。次いで、試料を切断し、燃焼性を連邦自動車安全基準No.302(FMVSS 302),California Technical Bulletin 117(CAL 117,2000)により試験し、揮発性については、DIN75201重量測定およびVDA 277により試験した。フォーム試料と色標準との間の当該色差であるデルタEを測定することによって、スコーチを評価した。フォーム試料を180℃のオーブンに、30分間、60分間、90分間、および120分間入れた。次いで、上記の時間間隔においてデルタEを測定した。デルタEの値が高いほど、退色が高いことを意味する。
調製実施例8のヒドロキシル官能性ホスホレン−1−オキシドをベースとする当該難燃性組成物を使用して低密度(0.5lbs/ft3)噴霧配合ポリウレタンフォームを調製するためのプロセス
当該フォーム調製の当該手順は以下の通りである。
当該ポリオール、水、界面活性剤、難燃剤(以下の当該表において「FR」と略される)、および触媒を秤量し、ミキシングビーカーに入れ、混合して均一な溶液を形成した。この溶液に、当該ポリマー性イソシアネートを加えた。当該混合物を、手短に、室温で5500rpmにおいて3秒間撹拌し、1リットルの厚紙のカップに注ぎ入れた。結果として形成された当該フォームを、室温で少なくとも24時間維持し、次いで、当該ボックスから取り出し、鋸で試験片へと切断した。次いで、当該試料をASTM dの酸素指数試験手順に従って燃焼性について試験した。表5は、当該フォーム調製のための当該原材料およびパラメータならびに当該試験の当該結果を表す。
Claims (17)
- 下記の該式(I−A):
R1、R2、R3、およびR4は、独立して、H、一個から四個の炭素原子を有する直鎖状または分岐鎖状のアルキル基、または塩素から選択され;ならびに、
Xは、・・・(Z)k−R7または
Xが、・・・(Z)k−R7である場合、Zは−(Y−O)n−であり、この場合、Yは、二個から八個の炭素原子を有する直鎖状または分岐鎖状のアルキレン基であり、ならびにnは、1から20の整数を表し;
kは、0または1であり得;
R7は、水素、二個から八個の炭素原子を有するヒドロキシ末端の直鎖状または分岐鎖状のアルキレン基から選択され、
ただし、kがゼロの場合、R7は、当該ヒドロキシ末端の直鎖状または分岐鎖状アルキレン基であり、kが1の場合、R7は水素であり、ならびにXが、
- 下記の該式(I−B):
R1、R2、R3、およびR4は、独立して、H、一個から四個の炭素原子を有する直鎖状または分岐鎖状のアルキル基、または塩素から選択され;
n1およびn2のそれぞれは、1以上の整数であり、その場合、n1+n2は、3以上であり、ならびに
Z2は、n1+n2の結合価を有する分岐鎖状ポリオールに由来する部分であり、ならびに当該一般式:
この場合、Rは、以下:
この場合、各R8は、独立して、Hであるか、または一個から四個の炭素原子のアルキルであり、xは、≧1であり、yは、2または3であり;zは、2から5の整数であり;ならびに、m≧1である]の、少なくとも1つのリン含有基を有する、多価アルコールの該部分的リン酸化によるリン含有ポリオール反応生成物を含む硬質または半硬質ポリウレタンまたはポリイソシアヌレート。 - 前記ポリイソシアヌレートが、フォーム、コーティング剤、接着剤、およびエラストマーのうちの任意の一つである、請求項1に記載の硬質または半硬質ポリイソシアヌレート。
- さらに、少なくとも1種のハロゲン化または非ハロゲン化難燃剤を含む、請求項1に記載の硬質または半硬質ポリウレタンまたはポリイソシアヌレート。
- 前記ハロゲン化難燃剤が、臭素化ビスフェノールA化合物、臭素化ビスフェノールS化合物、臭素化ビスフェノールF化合物、臭素化ビスフェノールAカーボネートオリゴマー、臭素化ビスフェノールAエポキシ樹脂、エンドキャップされた臭素化ビスフェノールAエポキシ樹脂、脂肪族臭素化アルコールおよびグリコール、ジブロモネオペンチルグリコール、臭素化フタレートおよびテトラブロモフタレートジオール、臭素化ホスフェート、臭素化フェノール、臭素化フタル酸、およびそれらの組み合わせからなる該群より選択される臭素化難燃剤である、請求項6に記載の硬質または半硬質ポリウレタンまたはポリイソシアヌレート。
- 模造木材、断熱材、梱包材、履物、ガスケット、粘弾性フォーム、スピーカー用のエアフィルターおよび装飾的表面仕上げ材、および積層機械で作製されたフォームシートからなる群より選択される物品であって、請求項1に記載の硬質または半硬質ポリウレタンまたはポリイソシアヌレートを含む、物品。
- 前記断熱材は、シート被覆、成形、および噴霧技術によって適用されたタンクおよびパイプ用断熱材、冷蔵庫用断熱材、冷凍庫用断熱材、湯沸かし器用断熱材、屋根用パネル断熱材、壁用パネル断熱材、天井用断熱材、床用断熱材、ならびに窓およびドア用断熱材から選択される、請求項10に記載の物品。
- 前記断熱材が前記屋根用パネル断熱材である請求項11に記載の物品を含む屋根構造体。
- 前記断熱材が前記壁用パネル断熱材である請求項11に記載の物品を含む壁構造体。
- ポリオールと、ポリイソシアネートと、下記の該式(I−A):
R1、R2、R3、およびR4は、独立して、H、一個から四個の炭素原子を有する直鎖状または分岐鎖状のアルキル基、または塩素から選択され;ならびにXは、・・・(Z)k−R7または
Xが、・・・(Z)k−R7である場合、Zは−(Y−O)n−であり、この場合、Yは、二個から八個の炭素原子を有する直鎖状または分岐鎖状のアルキレン基であり、ならびにnは、1から20の整数を表し;
kは、0または1であり得;
R7は、水素、二個から八個の炭素原子を有するヒドロキシ末端の直鎖状または分岐鎖状のアルキレン基から選択され、
ただし、kがゼロの場合、R7は、当該ヒドロキシ末端の直鎖状または分岐鎖状アルキレン基であり、kが1の場合、R7は水素であり、ならびに
Xが、
- ポリオールと、ポリイソシアネートと、下記の該式(I−B):
R1、R2、R3、およびR4は、独立して、H、一個から四個の炭素原子を有する直鎖状または分岐鎖状のアルキル基、または塩素から選択され;n1およびn2のそれぞれは、1以上の整数であり、その場合、n1+n2は、3以上であり、ならびに、Z2は、n1+n2の結合価を有する分岐鎖状ポリオールに由来する部分であり、ならびに当該一般式:
この場合、Rは、以下:
この場合、各R8は、独立して、Hであるか、または一個から四個の炭素原子のアルキルであり、xは、≧1であり、yは、2または3であり;zは、2から5の整数であり;ならびに、m≧1である]の、少なくとも1つのリン含有基を有する、多価アルコールの該部分的リン酸化によるリン含有ポリオール反応生成物とによる該反応生成物を含む硬質または半硬質ポリウレタンフォームまたはポリイソシアヌレートフォーム。
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