JP2020172612A - 硬化性に優れるポリウレタンフォーム製造用のアミン触媒組成物及びそれを用いたポリウレタンフォームの製造方法 - Google Patents
硬化性に優れるポリウレタンフォーム製造用のアミン触媒組成物及びそれを用いたポリウレタンフォームの製造方法 Download PDFInfo
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- JP2020172612A JP2020172612A JP2019076535A JP2019076535A JP2020172612A JP 2020172612 A JP2020172612 A JP 2020172612A JP 2019076535 A JP2019076535 A JP 2019076535A JP 2019076535 A JP2019076535 A JP 2019076535A JP 2020172612 A JP2020172612 A JP 2020172612A
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- polyurethane foam
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 27
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- 238000009835 boiling Methods 0.000 description 1
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- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- DWFKOMDBEKIATP-UHFFFAOYSA-N n'-[2-[2-(dimethylamino)ethyl-methylamino]ethyl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound CN(C)CCN(C)CCN(C)CCN(C)C DWFKOMDBEKIATP-UHFFFAOYSA-N 0.000 description 1
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UIEKYBOPAVTZKW-UHFFFAOYSA-L naphthalene-2-carboxylate;nickel(2+) Chemical compound [Ni+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UIEKYBOPAVTZKW-UHFFFAOYSA-L 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
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- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
[1] 下記一般式(1)で示される第3級アミン化合物(A)、下記一般式(2)で示される第3級アミン化合物(B)及び下記一般式(3)で示される環状アミン化合物(C)を含有するポリウレタンフォーム製造用のアミン触媒組成物。
[2] 上記一般式(1)で表される第3級アミン化合物(A)が、N,N−ジメチルエチレンジアミン、N,N−ジメチルプロパンジアミン、N,N−ジエチルエチレンジアミン、又はN,N−ジエチルプロパンジアミンである[1]に記載のポリウレタンフォーム製造用のアミン触媒組成物。
[3] 上記一般式(2)で表される第3級アミン化合物(B)が、2,2’−イミノビス(N,N−ジメチルエチルアミン)、3,3’−イミノビス(N,N−ジメチルプロピルアミン)、2,2’−イミノビス(N,N−ジエチルエチルアミン)、又は3,3’−イミノビス(N,N−ジエチルプロピルアミン)である[1]又は[2]に記載のポリウレタンフォーム製造用のアミン触媒組成物。
[4] 上記一般式(3)で表される環状アミン化合物(C)が、2−ヒドロキシメチルトリエチレンジアミンである[1]乃至[3]のいずれかに記載のポリウレタンフォーム製造用のアミン触媒組成物。
[5] 第3級アミン化合物(A)、第3級アミン化合物(B)、及び環状アミン化合物(C)の混合比率が、[第3級アミン化合物(A)と(B)の合計含有量]/[環状アミン化合物(C)の含有量]=60/40〜99/1(重量比)の範囲であることを特徴とする[1]乃至[4]のいずれかに記載のポリウレタンフォーム製造用のアミン触媒組成物。
[6] [1]乃至[5]のいずれかに記載のポリウレタンフォーム製造用のアミン触媒組成物の存在下で、ポリオール類とポリイソシアネート類とを反応させることを特徴とするポリウレタンフォームの製造方法。
整泡剤: SH190(シリコーン整泡剤、東レ・ダウコーニングシリコーン社製)
金属触媒: スタナスジオクトエート(和光純薬社製)
発泡剤: 水
ポリイソシアネート液: トリレンジイソシアネート(東ソー社製コロネートT−80,NCO含量=48.3%)
Bis DMAPA: 3,3’−イミノビス(N,N−ジメチルプロピルアミン)(Aldrich社製)
DMAPA: N,N−ジメチルプロパンジアミン (東京化成工業社製)
RZETA: 1,4−ジアザビシクロ[2,2,2]オクタン−2−メタノール 33%ジプロピレングリコール溶液(東ソー社製)
TEDA−L33: トリエチレンジアミン 33%ジプロピレングリコール溶液(東ソー社製)
DPA: N−ジメチル−N,N’−ジ(2−ヒドロキシプロピル)プロピレンジアミン(Huntsman社製)。
ポリオール 100重量部、整泡剤 1.0重量部、金属触媒 0.12重量部及び発泡剤(水) 3.5重量部を、秤量し、十分に攪拌混合して原料配合液を調整した。次いで、調整した原料配合液 366.2gを1000mlポリエチレンカップに取り、更に表1及び2に示したアミン化合物の組成物からなる触媒組成物を、ポリオール 100重量部に対して表1及び2に記載の重量部となるように添加して、触媒含有原料配合液を調製し、20℃に温度調整した。なお、前記触媒組成物添加量は、反応性が下記のライズタイムで100±2秒となるように調整したものである。20℃に温度調整したポリイソシアネート液を、イソシアネートインデックス〔ポリイソシアネート液の[イソシアネート基]/触媒含有原料配合液の[OH基](モル比)×100)〕が110となる量だけ、前記の触媒含有原料配合液が入ったポリエチレンカップの中に入れ、次いで、素早く攪拌機にて3500rpmで10秒間攪拌した。混合攪拌した混合液を40℃に温度調節した縦×横が25cm×25cm角のアルミ製モールドに移し、発泡中の反応性を以下に示す方法で測定した。また、フォーム表面の硬化時間を以下に示す方法で測定した。
・クリームタイム: 発泡開始時間、フォームが上昇開始する時間を目視にて測定
・ライズタイム: フォーム高さが最高点に達した時間をレーザー変位計にて測定
[ポリウレタンフォームの表面硬化性]
上記の発泡反応で得られたポリウレタンフォームについて、発泡反応開始から7分後に、モールドから脱型し、直ちに室温23±1℃、湿度50±3%に維持された室内に保管した。発泡反応開始30分後から1分毎に、先端が円錐状になった710gの鉄製の棒を、ポリウレタンフォームへ落下させた。フォーム表面が十分に硬化し、鉄製の棒にフォーム表面の剥離片が付着しなる時点をキュア完了点とした。前記の発泡反応開始時点からキュア完了点までの時間をキュアタイムとした。
Claims (6)
- 下記一般式(1)で示される第3級アミン化合物(A)、下記一般式(2)で示される第3級アミン化合物(B)及び下記一般式(3)で示される環状アミン化合物(C)を含有するポリウレタンフォーム製造用のアミン触媒組成物。
- 上記一般式(1)で表される第3級アミン化合物(A)が、N,N−ジメチルエチレンジアミン、N,N−ジメチルプロパンジアミン、N,N−ジエチルエチレンジアミン、又はN,N−ジエチルプロパンジアミンである請求項1に記載のポリウレタンフォーム製造用のアミン触媒組成物。
- 上記一般式(2)で表される第3級アミン化合物(B)が、2,2’−イミノビス(N,N−ジメチルエチルアミン)、3,3’−イミノビス(N,N−ジメチルプロピルアミン)、2,2’−イミノビス(N,N−ジエチルエチルアミン)、又は3,3’−イミノビス(N,N−ジエチルプロピルアミン)である請求項1又は請求項2に記載のポリウレタンフォーム製造用のアミン触媒組成物。
- 上記一般式(3)で表される環状アミン化合物(C)が、2−ヒドロキシメチルトリエチレンジアミンである請求項1乃至請求項3のいずれかに記載のポリウレタンフォーム製造用のアミン触媒組成物。
- 第3級アミン化合物(A)、第3級アミン化合物(B)、及び環状アミン化合物(C)の混合比率が、[第3級アミン化合物(A)と(B)の合計含有量]/[環状アミン化合物(C)の含有量]=60/40〜99/1(重量比)の範囲であることを特徴とする請求項1乃至請求項4のいずれかに記載のポリウレタンフォーム製造用のアミン触媒組成物。
- 請求項1乃至請求項5のいずれかに記載のポリウレタンフォーム製造用のアミン触媒組成物の存在下で、ポリオール類とポリイソシアネート類とを反応させることを特徴とするポリウレタンフォームの製造方法。
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