JP6689858B2 - 新規ポリウレタン硬化剤 - Google Patents
新規ポリウレタン硬化剤 Download PDFInfo
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- JP6689858B2 JP6689858B2 JP2017530726A JP2017530726A JP6689858B2 JP 6689858 B2 JP6689858 B2 JP 6689858B2 JP 2017530726 A JP2017530726 A JP 2017530726A JP 2017530726 A JP2017530726 A JP 2017530726A JP 6689858 B2 JP6689858 B2 JP 6689858B2
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- catalyst composition
- tetrakis
- bismuth
- polyol
- flexible
- Prior art date
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000004759 spandex Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Description
本出願は、2015年1月15日に出願された米国仮特許出願第62/102,726号「Novel Polyurethane Curatives(新規ポリウレタン硬化剤)」の優先権を主張し、その全体を参照として本明細書に組み込む。
硬化剤8840の作製
硬化剤8842の作製
硬化剤8842を使用した2成分のPU系のスプレーフォーム製剤
硬化剤8842を使用した2成分のPU系のフォームの反応速度と密度
水(3.5%w/w)
シリコン系界面活性剤(不定量)
BDMAEE(0.12%w/w)
BICAT8842(0.02%w/w)
または、オクタン酸第一スズ(0.02%w/w)
硬化剤8842を使用した2成分のPU系のスラブストックフォームの応用
TDI80‐20 80%w/w
TDI65 20%w/w
ポリエーテルポリオール(OH=28) 90%w/w
高分子ポリオール 10%w/w
水 2.75%w/w
TEDA(DPG中) 0.125%w/w
BDMAEE(DPG中) 0.125%w/w
シリコンコポリマー 2.05%w/w
難燃剤 6.0%w/w
オクタン酸第一スズまたはBiCAT8842 0.16%w/w
硬化剤の劣化加速
(1) リガンドとしての1,1’,1’’,1’’’−(1,2−エタンジイルジニトリロ)テトラキス[2−プロパノール]ネオデカン酸、及びビスマスカルボキシレートを含む、ビスマスベースの触媒。
(2) 前記触媒が、ポリウレタン触媒である、実施態様1に記載の触媒。
(3) 2,2’,2’’,2’’’−(1,2−エタンジイルジニトリロ)テトラキス[エタノール]ネオデカン酸、及びビスマスカルボキシレートを含む、ビスマス触媒。
(4) 前記触媒が、ポリウレタン触媒である、実施態様3に記載の触媒。
(5) 1,1’,1’’,1’’’−(1,2−エタンジイルジニトリロ)テトラキス[2−プロパノール]ネオデカン酸、2,2’,2’’,2’’’−(1,2−エタンジイルジニトリロ)テトラキス[エタノール]ネオデカン酸、及びビスマスカルボキシレート、の混合物を含む、ビスマス触媒。
(7) ポリイソシアネート、ポリオール、およびビスマス触媒の触媒反応により形成される可撓性、準可撓性または剛性ポリウレタンフォーム。
(8) 前記ビスマス触媒が、ビスマスカルボキシレートを有する、1,1’,1’’,1’’’−(1,2−エタンジイルジニトリロ)テトラキス[2−プロパノール]ネオデカン酸、を含む、実施態様7に記載の可撓性、準可撓性または剛性ポリウレタンフォーム。
(9) 前記ビスマス触媒が、ビスマスカルボキシレートを有する2,2’,2’’,2’’’−(1,2−エタンジイルジニトリロ)テトラキス[エタノール]ネオデカン酸、を含む、実施態様7に記載の可撓性、準可撓性または剛性ポリウレタンフォーム。
(10) 反応混合物に用いられる前記ビスマス触媒が、ポリオール100重量部に対して0.05から5重量部の量である、実施態様7に記載の可撓性、準可撓性または剛性ポリウレタンフォーム。
(12) ポリウレタンフォームを製造するためのプロセスであって、該プロセスは、ポリイソシアネートと、ポリオールと、アルカノールアミンリガンドも有するビスマスカルボキシレート触媒との間の反応を含む、前記プロセス。
(13) 前記ビスマス触媒がBiCAT8840またはBiCAT8842であって、ビスマス:アルカノールアミンリガンドの比率が約1:3〜1:5である、実施態様12に記載のプロセス。
(14) 前記ビスマス触媒がBiCAT8840またはBiCAT8842であって、ビスマス:アルカノールアミンリガンドのモル比が約0.1:2.0である、実施態様12に記載のプロセス。
(15) 有機ポリイソシアネートと、ポリエーテルポリオールとポリエステルポリオールから選択されるポリオールとの反応により、ポリウレタンを生成するプロセスであって、
NCO基の水酸基に対する比率が、N,N,N’,N’−テトラキス(2−ヒドロキシプロピル)エチレンジアミンと、N,N,N’,N’−テトラキス(2−ヒドロキシエチル)エチレンジアミンから選択されるアルカノールアミンリガンドを有する、分子中に2から20の炭素原子を有するカルボン酸のビスマス塩の触媒量の存在下で約0.70:1から1.35:1である、前記プロセス。
(17) 前記反応が、反応物質重量基準で約0.01から1.5重量パーセントのビスマス塩存在下で実施される、実施態様15に記載のプロセス。
(18) 前記反応が、反応物質重量基準で約0.01から1.5重量パーセントの、分子中に8個から12個の炭素原子を有するカルボン酸のビスマス塩存在下で実施される、実施態様15に記載のプロセス。
(19) 前記ビスマス塩がBiCAT8840である、実施態様15に記載のプロセス。
(20) 前記ビスマス塩がBiCAT8842である、実施態様15に記載のプロセス。
(22) 前記アルカノールアミンが、N−メチルジエタノールアミン、N−メチルエタノールアミン、ジエタノールアミンジイソプロパノールアミン、N,N−ジエチルエタノールアミン、N,N−ジメチルエタノールアミン、2‐(2‐アミノエトキシ)エタノール、2‐アミノ−2‐メチル−1−プロパノール、1−ジメチルアミノ−2‐プロパノール、2‐(((2‐ジメチルアミノ)エチル)メチルアミン)エタノール、2‐(ブチルアミノ)エタノール、2−(エチルアミノ)エタノール、2‐(メチルアミノ)エタノール、1−アミノ−2−プロパノール、3−アミノ−1−プロパノール、テトラキス(2−ヒドロキシエチル)エチレンジアミン、及びエチレンジニトリロ−テトラ−2−プロパノール、より選択される、実施態様21に記載のポリウレタン触媒。
(23) ポリオールが、ポリエチレングリコール、ポリプロピレングリコール、およびポリブチレンエーテルグリコール、より選択される、実施態様21に記載のポリウレタン触媒。
(24) 前記カルボキシレートが、1個から19個の炭素原子を有し、アルキル基、シクロアルキル基、アリール基、アルカリル基、より選択される、実施態様21に記載のポリウレタン触媒。
(25) 前記ビスマスカルボキシレートが、ネオデカン酸ビスマスである、実施態様21に記載のポリウレタン触媒。
(27) 前記アルカノールアミンが、エチレンジニトリロ‐テトラ‐2‐プロパノールである、実施態様25に記載のポリウレタン触媒。
Claims (21)
- 1,1’,1’’,1’’’−(1,2−エタンジイルジニトリロ)テトラキス[2−プロパノール]ネオデカン酸、ネオデカン酸ビスマス、及びポリオールを含む、ポリウレタンフォーム調製のための製剤用の、触媒組成物であって、
前記ポリオールが、ポリエチレングリコール、ポリプロピレングリコール、およびポリブチレンエーテルグリコール、より選択される、触媒組成物。 - 2,2’,2’’,2’’’−(1,2−エタンジイルジニトリロ)テトラキス[エタノール]ネオデカン酸、ネオデカン酸ビスマス、及びポリオールを含む、ポリウレタンフォーム調製のための製剤用の、触媒組成物であって、
前記ポリオールが、ポリエチレングリコール、ポリプロピレングリコール、およびポリブチレンエーテルグリコール、より選択される、触媒組成物。 - 1,1’,1’’,1’’’−(1,2−エタンジイルジニトリロ)テトラキス[2−プロパノール]ネオデカン酸、2,2’,2’’,2’’’−(1,2−エタンジイルジニトリロ)テトラキス[エタノール]ネオデカン酸、ネオデカン酸ビスマス、及びポリオールの混合物を含む、ポリウレタンフォーム調製のための製剤用の触媒組成物であって、
前記ポリオールが、ポリエチレングリコール、ポリプロピレングリコール、およびポリブチレンエーテルグリコール、より選択される、触媒組成物。 - 前記製剤はスプレーフォーム製剤である、請求項1〜3のいずれか一項に記載の触媒組成物。
- ポリイソシアネートと、請求項1〜4のいずれか一項に記載の触媒組成物との触媒反応により形成される、可撓性、準可撓性または剛性ポリウレタンフォーム。
- 前記触媒組成物が、ネオデカン酸ビスマスを有する、1,1’,1’’,1’’’−(1,2−エタンジイルジニトリロ)テトラキス[2−プロパノール]ネオデカン酸、を含む、請求項5に記載の可撓性、準可撓性または剛性ポリウレタンフォーム。
- 前記触媒組成物が、ネオデカン酸ビスマスを有する2,2’,2’’,2’’’−(1,2−エタンジイルジニトリロ)テトラキス[エタノール]ネオデカン酸、を含む、請求項5に記載の可撓性、準可撓性または剛性ポリウレタンフォーム。
- 1,1’,1’’,1’’’−(1,2−エタンジイルジニトリロ)テトラキス[2−プロパノール]ネオデカン酸、2,2’,2’’,2’’’−(1,2−エタンジイルジニトリロ)テトラキス[エタノール]ネオデカン酸と、ネオデカン酸ビスマスとの合計量が、ポリオール100重量部に対して0.05から5重量部の量である、請求項5に記載の可撓性、準可撓性または剛性ポリウレタンフォーム。
- ポリウレタンフォームを製造するためのプロセスであって、該プロセスは、ポリイソシアネートと、請求項1〜4のいずれか一項に記載の触媒組成物との間の反応を含む、前記プロセス。
- 前記触媒組成物がBiCAT8840またはBiCAT8842を含み、ビスマス:アルカノールアミンリガンドの比率が1:3〜1:5である、請求項9に記載のプロセス。
- 前記触媒組成物がBiCAT8840またはBiCAT8842を含み、ビスマス:アルカノールアミンリガンドのモル比が0.1:2.0である、請求項9に記載のプロセス。
- 有機ポリイソシアネートと、請求項1〜4のいずれか一項に記載の触媒組成物との反応により、ポリウレタンを生成するプロセスであって、
NCO基の水酸基に対する比率が、N,N,N’,N’−テトラキス(2−ヒドロキシプロピル)エチレンジアミンと、N,N,N’,N’−テトラキス(2−ヒドロキシエチル)エチレンジアミンから選択されるアルカノールアミンリガンドを有する、ネオデカン酸ビスマスの触媒量の存在下で0.70:1から1.35:1である、前記プロセス。 - 前記ポリオールの分子量が1000から10,000である、請求項12に記載のプロセス。
- 前記反応が、反応物質重量基準で0.01から1.5重量パーセントのビスマス塩存在下で実施される、請求項12に記載のプロセス。
- 前記反応が、反応物質重量基準で0.01から1.5重量パーセントの、前記ネオデカン酸ビスマスの存在下で実施される、請求項12に記載のプロセス。
- 前記触媒組成物がBiCAT8840を含む、請求項12に記載のプロセス。
- 前記触媒組成物がBiCAT8842を含む、請求項12に記載のプロセス。
- アルカノールアミンを有するネオデカン酸ビスマスとポリオールの間の反応により生成される、ポリウレタンフォーム調製のための製剤用の触媒組成物であって、
前記ポリオールが、ポリエチレングリコール、ポリプロピレングリコール、およびポリブチレンエーテルグリコール、より選択され、
前記アルカノールアミンが、テトラキス(2−ヒドロキシエチル)エチレンジアミン又はエチレンジニトリロ−テトラ−2−プロパノールである、触媒組成物。 - 前記アルカノールアミンが、テトラキス(2−ヒドロキシエチル)エチレンジアミンである、請求項18に記載の触媒組成物。
- 前記アルカノールアミンが、エチレンジニトリロ−テトラ−2−プロパノールである、請求項18に記載の触媒組成物。
- 前記製剤はスプレーフォーム製剤である、請求項18〜20のいずれか一項に記載の触媒組成物。
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