JP2018505246A - 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
- Publication number
- JP2018505246A JP2018505246A JP2017530726A JP2017530726A JP2018505246A JP 2018505246 A JP2018505246 A JP 2018505246A JP 2017530726 A JP2017530726 A JP 2017530726A JP 2017530726 A JP2017530726 A JP 2017530726A JP 2018505246 A JP2018505246 A JP 2018505246A
- Authority
- JP
- Japan
- Prior art keywords
- bismuth
- catalyst
- polyurethane
- polyol
- tetrakis
- 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.)
- Granted
Links
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- 229920002635 polyurethane Polymers 0.000 title claims abstract description 48
- 239000003795 chemical substances by application Substances 0.000 title abstract description 23
- 229910052797 bismuth Inorganic materials 0.000 claims abstract description 66
- -1 bismuth carboxylates Chemical class 0.000 claims abstract description 39
- 150000003077 polyols Chemical class 0.000 claims abstract description 35
- 229920005862 polyol Polymers 0.000 claims abstract description 34
- 239000003446 ligand Substances 0.000 claims abstract description 19
- NSPSPMKCKIPQBH-UHFFFAOYSA-K bismuth;7,7-dimethyloctanoate Chemical compound [Bi+3].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O NSPSPMKCKIPQBH-UHFFFAOYSA-K 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims description 97
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 31
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- 150000001621 bismuth Chemical class 0.000 claims description 10
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 9
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- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- QPSMHALKTWHJNP-UHFFFAOYSA-N 2-[2-[bis(2-hydroxyethyl)amino]ethyl-(2-hydroxyethyl)amino]ethanol 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O.OCCN(CCO)CCN(CCO)CCO QPSMHALKTWHJNP-UHFFFAOYSA-N 0.000 claims description 5
- MQUOZMRDWUIJKO-UHFFFAOYSA-N C(CCCCCC(C)(C)C)(=O)O.C(CN(CC(C)O)CC(C)O)N(CC(C)O)CC(C)O Chemical compound C(CCCCCC(C)(C)C)(=O)O.C(CN(CC(C)O)CC(C)O)N(CC(C)O)CC(C)O MQUOZMRDWUIJKO-UHFFFAOYSA-N 0.000 claims description 5
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- 125000000217 alkyl group Chemical group 0.000 claims description 4
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 claims description 3
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 3
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 2
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- UAAOUMOKBUUQEB-UHFFFAOYSA-N C(CCCCCC(C)(C)C)(=O)O.C(C)O.C(C)O.C(C)O.C(C)O Chemical compound C(CCCCCC(C)(C)C)(=O)O.C(C)O.C(C)O.C(C)O.C(C)O UAAOUMOKBUUQEB-UHFFFAOYSA-N 0.000 claims 2
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- DLPQTXRSAXAVGX-UHFFFAOYSA-N C(CCCCCC(C)(C)C)(=O)O.CC(C)O.CC(C)O.CC(C)O.CC(C)O Chemical compound C(CCCCCC(C)(C)C)(=O)O.CC(C)O.CC(C)O.CC(C)O.CC(C)O DLPQTXRSAXAVGX-UHFFFAOYSA-N 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 abstract description 13
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- 238000004519 manufacturing process Methods 0.000 abstract description 4
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- 239000002904 solvent Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 15
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 14
- 239000006260 foam Substances 0.000 description 13
- 239000000806 elastomer Substances 0.000 description 12
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- 238000009472 formulation Methods 0.000 description 9
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000000576 coating method Methods 0.000 description 6
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- 125000002947 alkylene group Chemical group 0.000 description 4
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- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 2
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000616 occupational exposure limit Toxicity 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- BWOROQSFKKODDR-UHFFFAOYSA-N oxobismuth;hydrochloride Chemical compound Cl.[Bi]=O BWOROQSFKKODDR-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 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
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000004759 spandex Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 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
- 238000012546 transfer Methods 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- VNTDZUDTQCZFKN-UHFFFAOYSA-L zinc 2,2-dimethyloctanoate Chemical compound [Zn++].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O VNTDZUDTQCZFKN-UHFFFAOYSA-L 0.000 description 1
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Abstract
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 (27)
- 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。
- 前記触媒が、ポリウレタン触媒である、請求項1に記載の触媒。
- 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。
- 前記触媒が、ポリウレタン触媒である、請求項3に記載の触媒。
- 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。
- 前記触媒がポリウレタン触媒である、請求項5に記載の触媒。
- 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。
- 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、請求項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。
- 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、請求項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。
- 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、請求項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。
- 前記カルボキシレートがC4〜15脂肪族カルボン酸に由来する、請求項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。
- 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。
- 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、請求項12に記載のプロセス。
- 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、請求項12に記載のプロセス。
- 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。 - 前記ポリオールの分子量が約1000から10,000である、請求項15に記載のプロセス。
- 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、請求項15に記載のプロセス。
- 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、請求項15に記載のプロセス。
- 前記ビスマス塩がBiCAT8840である、請求項15に記載のプロセス。
- 前記ビスマス塩がBiCAT8842である、請求項15に記載のプロセス。
- アルカノールアミンを有するビスマスカルボキシレートとポリオールの間の反応により生成される、ポリウレタン触媒。
- 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、請求項21に記載のポリウレタン触媒。
- 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、請求項21に記載のポリウレタン触媒。
- 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、請求項21に記載のポリウレタン触媒。
- 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、請求項21に記載のポリウレタン触媒。
- 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25に記載のポリウレタン触媒。
- 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25に記載のポリウレタン触媒。
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