JP5832392B2 - ポリウレタンエラストマーの製造方法、ポリウレタンエラストマーおよび成形品 - Google Patents
ポリウレタンエラストマーの製造方法、ポリウレタンエラストマーおよび成形品 Download PDFInfo
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- JP5832392B2 JP5832392B2 JP2012181662A JP2012181662A JP5832392B2 JP 5832392 B2 JP5832392 B2 JP 5832392B2 JP 2012181662 A JP2012181662 A JP 2012181662A JP 2012181662 A JP2012181662 A JP 2012181662A JP 5832392 B2 JP5832392 B2 JP 5832392B2
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- polyol
- polyurethane elastomer
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- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 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
- 239000004065 semiconductor Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 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
- 238000003856 thermoforming Methods 0.000 description 1
- 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 1
- 238000004448 titration Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 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
- 238000012546 transfer Methods 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
Description
<1,4−ビス(イソシアナトメチル)シクロヘキサン(1,4−H6XDI)の製造>
(ポリイソシアネートの加水分解性塩素濃度の測定)
各1,4−ビス(イソシアナトメチル)シクロヘキサンに含有される加水分解性塩素の濃度(以下、HCと略する。)は、JIS K−1556(2000)の附属書3に記載されている加水分解性塩素の試験方法に準拠して測定した。
13C−NMR測定によるトランス/シス比が93/7の1,4−ビス(アミノメチル)シクロヘキサン(三菱瓦斯化学社製)を原料として、冷熱2段ホスゲン化法を加圧下で実施した。
13C−NMR測定によるトランス/シス比が41/59の1,4−ビス(アミノメチル)シクロヘキサン(東京化成工業社製)を原料として、1,4−BIC1と同様の方法にて388質量部の1,4−BIC2を得た。得られた1,4−BIC2のガスクロマトグラフィー測定による純度は99.9%、APHA測定による色相は5、13C−NMR測定によるトランス/シス比は41/59であった。HCは22ppmであった。
攪拌機、温度計、還流管、および、窒素導入管を備えた4つ口フラスコに、製造例1の1,4−BIC1を865質量部、製造例2の1,4−BIC2を135質量部装入し、窒素雰囲気下、室温にて1時間撹拌した。得られた1,4−BIC3のガスクロマトグラフィー測定による純度は99.9%、APHA測定による色相は5、13C−NMR測定によるトランス/シス比は86/14であった。HCは19ppmであった。
<プレポリマー合成工程>
合成例1(プレポリマー(a)の合成)
攪拌機、温度計、還流管および窒素導入管を備えた4つ口フラスコに、PTXG(旭化成せんい社製、商品名:PTXG、数平均分子量1800、テトラヒドロフランとネオペンチルグリコールとを共重合した非晶性ポリテトラメチレンエーテルグリコール)0.518mol、1−オクタデカノール0.058molを装入し、第1ポリオール成分を得た。次いで、1,4−BIC3を1.174mol装入した。窒素雰囲気下、80℃にてイソシアネート基含量が4.47質量%になるまで反応させ、イソシアネート基末端ポリウレタンプレポリマー(以下、プレポリマーと略する。)aを得た。
PTXGを0.659mol、1−オクタデカノールを0.015mol、1,4−BIC3を1.292mol用い、イソシアネート基含量が3.64質量%になるまで反応させた以外は、合成例1と同様の操作にて、プレポリマーbを得た。
PTMEG(BASF社製、商品名:polyTHF2000S(数平均分子量2000、テトラヒドロフランからなるポリテトラメチレンエーテルグリコール(結晶性))を0.402mol、1−オクタデカノールを0.059mol、イソブタノール0.018mol、1,4−BIC3を1.367mol用い、イソシアネート基含量が7.16質量%になるまで反応させた以外は、合成例1と同様の操作にて、プレポリマーcを得た。
PEG(三井化学社製、商品名:タケラックU−2024(数平均分子量2000、アジピン酸系ポリエステルポリオール)を0.516mol、1−オクタデカノールを0.053mol、1−ドデカノールを0.016mol、1,4−BIC3を1.371mol用い、イソシアネート基含量が5.23質量%になるまで反応させた以外は、合成例1と同様の操作にて、プレポリマーdを得た。
PTXGを0.501mol、1−ドデカノールを0.083mol、1,4−BIC3を1.275mol用い、イソシアネート基含量が5.27質量%になるまで反応させた以外は、合成例1と同様の操作にて、プレポリマーeを得た。
PTXGを0.553mol、1−オクタデカノールを0.003mol、1,4−BIC3を1.295mol用い、イソシアネート基含量が4.99質量%になるまで反応させた以外は、合成例1と同様の操作にて、プレポリマーfを得た。
PTXGを0.529mol、1−トリアコンタノールを0.037mol、1,4−BIC3を1.288mol用い、イソシアネート基含量が5.10質量%になるまで反応させた以外は、合成例1と同様の操作にて、プレポリマーgを得た。
PTXGを0.503mol、1−オクタデカノールを0.079mol、1,4−BIC3を1.277mol用い、イソシアネート基含量が5.26質量%になるまで反応させた以外は、合成例1と同様の操作にて、プレポリマーhを得た。
PTXGを0.793mol、1−オクタデカノールを0.059mol、1,4−BIC3を1.282mol用い、イソシアネート基含量が2.29質量%になるまで反応させた以外は、合成例1と同様の操作にて、プレポリマーiを得た。
PTXGを0.942mol、1−オクタデカノールを0.058mol、1,4−BIC3を1.174mol用い、イソシアネート基含量が0.88質量%になるまで反応させた以外は、合成例1と同様の操作にて、プレポリマーjを得た。
PTXGを0.814mol、イソブタノールを0.186mol、1,4−BIC3を1.153mol用い、イソシアネート基含量が1.21質量%になるまで反応させた以外は、合成例1と同様の操作にて、プレポリマーkを得た。
PTXGを0.964mol、1−トリアコンタノールを0.036mol、1,4−BIC3を1.177mol用い、イソシアネート基含量が0.83質量%になるまで反応させた以外は、合成例1と同様の操作にて、プレポリマーlを得た。
PTMEGを0.559mol、1,4−BIC3を1.325mol用い、イソシアネート基含量が4.68質量%になるまで反応させた以外は、合成例1と同様の操作にて、プレポリマーmを得た。
PESを0.507mol、1−オクタデカノールを0.093mol、HDIを1.297mol用い、イソシアネート基含量が4.97質量%になるまで反応させた以外は、合成例1と同様の操作にて、プレポリマーnを得た。
1,4−H6XDI:製造例3にて得られた1,4−BIC3
HDI:ヘキサメチレンジイソシアネート
PTXG:旭化成せんい社製、商品名:PTXG(数平均分子量1800、テトラヒドロフランとネオペンチルグリコールとを共重合した非晶性ポリテトラメチレンエーテルグリコール)
PTMEG:BASF社製、商品名:polyTHF2000S(数平均分子量2000、テトラヒドロフランからなるポリテトラメチレンエーテルグリコール(結晶性))
PEG:日油社製(数平均分子量2000、ポリエチレングリコール)
PES:三井化学社製、商品名:タケラックU−2024(数平均分子量2000、アジピン酸系ポリエステルポリオール)
OD:1−オクタデカノール
DO:1−ドデカノール
IBA:イソブタノール
TR:1−トリアコンタノール
<第2ポリオール成分の調製>
調製例1(第2ポリオール成分(a)の調製)
攪拌機、温度計、還流管および窒素導入管を備えた4つ口フラスコに、PTXG0.424mol、1,4−BD(1,4−ブタンジオール(三菱化学株式会社製))0.172mol、さらに耐熱安定剤(商品名:イルガノックス245、BASFジャパン社製)を0.75質量部、触媒としてスタノクト(オクチル酸スズ、エーピーアイ・コーポレーション製、商品名:スタノクト))20ppmを装入し、80℃にて2時間撹拌混合し、第2ポリオール成分aを得た。
PTXG0.325mol、1,4−BD0.289mol、耐熱安定剤を1質量部、触媒としてU−600(オクタン酸ビスマス、日東化成製、商品名:ネオスタンU−600)20ppmを用いた以外は、調製例1と同様の操作にて、第2ポリオール成分(b)を得た。
PTMEG0.521mol、1,4−BD0.380mol、耐熱安定剤を0.6質量部、触媒としてスタノクト20ppmを用いた以外は、調製例1と同様の操作にて、第2ポリオール成分(c)を得た。
PEG0.414mol、1,4−BD0.383mol、耐熱安定剤を0.75質量部、スタノクト20ppmを用いた以外は、調製例1と同様の操作にて、第2ポリオール成分(d)を得た。
PTXG0.415mol、1,4−BD0.273mol、耐熱安定剤を0.75質量部、スタノクト20ppmを用いた以外は、調製例1と同様の操作にて、第2ポリオール成分(e)を得た。
PTXG0.444mol、1,4−BD0.292mol、耐熱安定剤を0.75質量部、スタノクト20ppmを用いた以外は、調製例1と同様の操作にて、第2ポリオール成分(f)を得た。
PTXG0.434mol、1,4−BD0.285mol、耐熱安定剤を0.75質量部、スタノクト20ppmを用いた以外は、調製例1と同様の操作にて、第2ポリオール成分(g)を得た。
PTXG0.418mol、1,4−BD0.275mol、耐熱安定剤を0.75質量部、スタノクト20ppmを用いた以外は、調製例1と同様の操作にて、第2ポリオール成分(h)を得た。
PTXG0.149mol、1,4−BD0.279mol、耐熱安定剤を2質量部、スタノクト20ppmを用いた以外は、調製例1と同様の操作にて、第2ポリオール成分(i)を得た。
1,4−BD0.172mol、スタノクト20ppmを用いた以外は、調製例1と同様の操作にて、第2ポリオール成分(j)を得た。
1,4−BD0.151mol、スタノクト20ppmを用いた以外は、調製例1と同様の操作にて、第2ポリオール成分(k)を得た。
1,4−BD0.176mol、耐熱安定剤を0.75質量部、スタノクト20ppmを用いた以外は、調製例1と同様の操作にて、第2ポリオール成分(l)を得た。
PTMEG0.441mol、1,4−BD0.322mol、耐熱安定剤を0.75質量部、スタノクト20ppmを用いた以外は、調製例1と同様の操作にて、第2ポリオール成分(m)を得た。
PES0.400mol、HDA0.294molを用いた以外は、調製例1と同様の操作にて、第2ポリオール成分(n)を得た。
PTXG:旭化成せんい社製、商品名:PTXG(数平均分子量1800、テトラヒドロフランとネオペンチルグリコールとを共重合した非晶性ポリテトラメチレンエーテルグリコール)
PTMEG:BASF社製、商品名:polyTHF2000S(数平均分子量2000、テトラヒドロフランからなるポリテトラメチレンエーテルグリコール(結晶性))
PEG:日油社製(数平均分子量2000、ポリエチレングリコール)
PES:三井化学社製、商品名:タケラックU−2024(数平均分子量2000、アジピン酸系ポリエステルポリオール)
Irg.245:耐熱安定剤(商品名:イルガノックス245、BASFジャパン社製)
スタノクト:オクチル酸スズ、エーピーアイ・コーポレーション製
U−600:オクタン酸ビスマス、日東化成製、商品名:ネオスタンU−600
<ポリウレタンエラストマーの合成>
実施例1(ポリウレタンエラストマー(A)の合成)
予め80℃に調整したプレポリマー(a)600質量部、80℃に温調した第2ポリオール成分(a)400質量部をステンレス容器に入れ、高速ディスパーを使用して、1000rpmの撹拌下、約10分間撹拌混合した。
プレポリマー(b)700質量部、第2ポリオール成分(b)300質量部使用した以外は、実施例1と同様の操作にて、ポリウレタンエラストマー(B)を得た。
プレポリマー(c)500質量部、第2ポリオール成分(c)500質量部使用した以外は、実施例1と同様の操作にて、ポリウレタンエラストマー(C)を得た。
プレポリマー(d)600質量部、第2ポリオール成分(d)400質量部使用した以外は、実施例1と同様の操作にて、ポリウレタンエラストマー(D)を得た。
プレポリマー(e)600質量部、第2ポリオール成分(e)400質量部使用した以外は、実施例1と同様の操作にて、ポリウレタンエラストマー(E)を得た。
プレポリマー(f)600質量部、第2ポリオール成分(f)400質量部使用した以外は、実施例1と同様の操作にて、ポリウレタンエラストマー(F)を得た。
プレポリマー(g)600質量部、第2ポリオール成分(g)400質量部使用した以外は、実施例1と同様の操作にて、ポリウレタンエラストマー(G)を得た。
プレポリマー(h)600質量部、第2ポリオール成分(h)400質量部使用した以外は、実施例1と同様の操作にて、ポリウレタンエラストマー(H)を得た。
プレポリマー(i)800質量部、第2ポリオール成分(i)200質量部使用した以外は、実施例1と同様の操作にて、ポリウレタンエラストマー(I)を得た。
プレポリマー(j)989質量部、第2ポリオール成分(j)11質量部、耐熱安定剤0.3質量部を使用した以外は、実施例1と同様の操作にて、ポリウレタンエラストマー(J)を得た。
プレポリマー(k)989質量部、第2ポリオール成分(k)11質量部、耐熱安定剤0.3質量部を使用した以外は、実施例1と同様の操作にて、ポリウレタンエラストマー(K)を得た。
プレポリマー(l)989質量部、第2ポリオール成分(l)11質量部を使用した以外は、実施例1と同様の操作にて、ポリウレタンエラストマー(L)を得た。
プレポリマー(m)600質量部、第2ポリオール成分(m)400質量部を使用した以外は、実施例1と同様の操作にて、ポリウレタンエラストマー(M)を得た。
プレポリマー(n)990質量部、第2ポリオール成分(n)10質量部、耐熱安定剤0.3質量部を使用した以外は、実施例1と同様の操作にて、ポリウレタンエラストマー(N)を得た。
Irg.245:耐熱安定剤(商品名:イルガノックス245、BASFジャパン社製)
(評価)
各実施例および各比較例において得られたエラストマーシートおよびフィルムを、下記する方法により評価した。その結果を表3に併せて示す。
<硬度>
射出成形により得られたシートを用いて、JIS K−7311(1995)に準拠し、アスカーゴム硬度計(高分子計器社製、形式A)を用いてA硬度を測定した。
<寸法安定性(寸法変化率)(%)>
射出成形後、室温23℃、相対湿度55%の恒温恒湿条件下にて、7日間養生したシートにある、樹脂の流れ方向に平行な向きに金型に刻印されている10cmの長さのマークを測定し、10cmに対する長さの変化量を下記式により求め、寸法安定性(寸法変化率)(%)とした。
<フィッシュアイ(FE)(単位:個/100cm2)>
押出成形により得られたフィルムを無作為に5箇所抽出し、10×10cm当たりに目視にて観察されるフィッシュアイの量をカウントし、その平均値を算出した。
<全光線透過率(単位:%)>
Haze Meter(日本電色工業製、モデル:NDH 2000)を用いて、フィルム成形後、室温23℃、相対湿度55%の恒温恒湿条件下にて、7日間養生した200μm厚のポリウレタンエラストマーフィルムの全光線透過率(JIS K7105(光源:D65)(2010)に準拠)を測定した。
Claims (9)
- 1,4−ビス(イソシアナトメチル)シクロヘキサンを含むポリイソシアネート成分と、数平均分子量300以上の高分子量ポリオールおよびモノアルコールを含む第1ポリオール成分とを反応させてイソシアネート基末端プレポリマーを合成するプレポリマー合成工程と、
前記イソシアネート基末端プレポリマーと、数平均分子量300以上の高分子量ポリオールおよび鎖伸長剤を含む第2ポリオール成分とを反応させてポリウレタンエラストマーを合成するエラストマー合成工程と
を備え、
前記モノアルコールが、炭素数15〜25のモノアルコールを含有することを特徴とする、ポリウレタンエラストマーの製造方法。 - 前記エラストマー合成工程において、
前記イソシアネート基末端プレポリマーと前記第2ポリオール成分とを、80:20〜40:60の質量比で反応させることを特徴とする、請求項1に記載のポリウレタンエラストマーの製造方法。 - 前記モノアルコールを、前記ポリイソシアネート成分、第1ポリオール成分および第2ポリオール成分の総量に対して、0.05質量%以上1質量%以下の割合で配合することを特徴とする、請求項1または2に記載のポリウレタンエラストマーの製造方法。
- 前記数平均分子量300以上の高分子量ポリオールが、非晶性ポリエーテルグリコールを含有することを特徴とする、請求項1〜3のいずれか一項に記載のポリウレタンエラストマーの製造方法。
- 前記ポリウレタンエラストマーのJIS K7312(1996)に基づく硬度が、50A以上75A以下であることを特徴とする、請求項1〜4のいずれか一項に記載のポリウレタンエラストマーの製造方法。
- 1,4−ビス(イソシアナトメチル)シクロヘキサンを含むポリイソシアネート成分と、数平均分子量300以上の高分子量ポリオールおよびモノアルコールを含む第1ポリオール成分とを反応させてイソシアネート基末端プレポリマーを合成するプレポリマー合成工程と、
前記イソシアネート基末端プレポリマーと、数平均分子量300以上の高分子量ポリオールおよび鎖伸長剤を含む第2ポリオール成分とを反応させてポリウレタンエラストマーを合成するエラストマー合成工程と
を備え、
前記モノアルコールが、炭素数15〜25のモノアルコールを含有するポリウレタンエラストマーの製造方法により得られることを特徴とする、ポリウレタンエラストマー。 - 請求項6に記載のポリウレタンエラストマーが用いられていることを特徴とする、成形品。
- 管として成形されていることを特徴とする、請求項7に記載の成形品。
- 帯として成形されていることを特徴とする、請求項7に記載の成形品。
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