TW202222905A - 組成物及使用其之矽氧烷系熱塑性樹脂,及該等之製造方法 - Google Patents
組成物及使用其之矽氧烷系熱塑性樹脂,及該等之製造方法 Download PDFInfo
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- TW202222905A TW202222905A TW110135123A TW110135123A TW202222905A TW 202222905 A TW202222905 A TW 202222905A TW 110135123 A TW110135123 A TW 110135123A TW 110135123 A TW110135123 A TW 110135123A TW 202222905 A TW202222905 A TW 202222905A
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- carbon atoms
- independently
- substituent
- siloxane
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- 239000000203 mixture Substances 0.000 title claims abstract description 31
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- 238000000034 method Methods 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 166
- -1 diol compound Chemical class 0.000 claims abstract description 141
- 125000001424 substituent group Chemical group 0.000 claims abstract description 63
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 53
- 125000003118 aryl group Chemical group 0.000 claims abstract description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 37
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 33
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
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- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 150000007514 bases Chemical class 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 10
- 229910000024 caesium carbonate Inorganic materials 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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- 238000005227 gel permeation chromatography Methods 0.000 description 8
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 8
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- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 7
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- 229920001296 polysiloxane Polymers 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
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- 229910052757 nitrogen Inorganic materials 0.000 description 5
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 4
- 239000004713 Cyclic olefin copolymer Substances 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 150000001339 alkali metal compounds Chemical class 0.000 description 4
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 4
- 238000011088 calibration curve Methods 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
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- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 239000011112 polyethylene naphthalate Substances 0.000 description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 description 2
- ZKBUCVUKEWAMGB-UHFFFAOYSA-N 2-[1-[2-(2-hydroxyethoxy)-6-phenylnaphthalen-1-yl]-6-phenylnaphthalen-2-yl]oxyethanol Chemical group C1(=CC=CC=C1)C=1C=C2C=CC(=C(C2=CC=1)C1=C(C=CC2=CC(=CC=C12)C1=CC=CC=C1)OCCO)OCCO ZKBUCVUKEWAMGB-UHFFFAOYSA-N 0.000 description 2
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
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- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
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- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
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- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000005265 dialkylamine group Chemical class 0.000 description 2
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- 150000002009 diols Chemical class 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
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- 239000012535 impurity Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229940046892 lead acetate Drugs 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
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- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
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- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
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- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 1
- WLSZYOASAQMMAV-UHFFFAOYSA-N 1,1'-biphenyl biphenylene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C1=CC=C2C3=CC=CC=C3C2=C1 WLSZYOASAQMMAV-UHFFFAOYSA-N 0.000 description 1
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- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
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- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
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- OANQELUUJGCUOQ-UHFFFAOYSA-N hexaphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 OANQELUUJGCUOQ-UHFFFAOYSA-N 0.000 description 1
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- 229910017053 inorganic salt Inorganic materials 0.000 description 1
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- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
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- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
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- 159000000002 lithium salts Chemical class 0.000 description 1
- HGPXWXLYXNVULB-UHFFFAOYSA-M lithium stearate Chemical compound [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
- 239000002370 magnesium bicarbonate Substances 0.000 description 1
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical compound [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical class [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- HTISDHGSRIQJEV-UHFFFAOYSA-N octacyclo[36.4.0.02,7.08,13.014,19.020,25.026,31.032,37]dotetraconta-1(42),2,4,6,8,10,12,14,16,18,20,22,24,26,28,30,32,34,36,38,40-henicosaene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 HTISDHGSRIQJEV-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000005880 oxathiolanyl group Chemical group 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- LYTNHSCLZRMKON-UHFFFAOYSA-L oxygen(2-);zirconium(4+);diacetate Chemical compound [O-2].[Zr+4].CC([O-])=O.CC([O-])=O LYTNHSCLZRMKON-UHFFFAOYSA-L 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000005563 perylenylene group Chemical group 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000000176 sodium gluconate Substances 0.000 description 1
- 235000012207 sodium gluconate Nutrition 0.000 description 1
- 229940005574 sodium gluconate Drugs 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- WJMMDJOFTZAHHS-UHFFFAOYSA-L strontium;carbonic acid;carbonate Chemical compound [Sr+2].OC([O-])=O.OC([O-])=O WJMMDJOFTZAHHS-UHFFFAOYSA-L 0.000 description 1
- RXSHXLOMRZJCLB-UHFFFAOYSA-L strontium;diacetate Chemical compound [Sr+2].CC([O-])=O.CC([O-])=O RXSHXLOMRZJCLB-UHFFFAOYSA-L 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 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
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- RSNQKPMXXVDJFG-UHFFFAOYSA-N tetrasiloxane Chemical compound [SiH3]O[SiH2]O[SiH2]O[SiH3] RSNQKPMXXVDJFG-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229920006304 triacetate fiber Polymers 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 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
- QZNXARNIBFGRRC-UHFFFAOYSA-N triphenyl-(2,3,4,5-tetrabutylphenyl)azanium borate Chemical compound B([O-])([O-])[O-].C(CCC)C=1C(=C(C(=C(C1)[N+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)CCCC)CCCC)CCCC.C(CCC)C=1C(=C(C(=C(C1)[N+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)CCCC)CCCC)CCCC.C(CCC)C=1C(=C(C(=C(C1)[N+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)CCCC)CCCC)CCCC QZNXARNIBFGRRC-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
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Abstract
Description
本發明係有關於組成物及使用其之矽氧烷系熱塑性樹脂,及該等之製造方法。
以往,含矽氧烷嵌段之二醇化合物,已知作為於構造中包含矽嵌段之各種樹脂原料而為有效,例如可使用於影像複印中之剝離層、光阻材料、聚碳酸酯用塑化劑、粉末表面塗佈系之成分等用途。
於末端具有羥基之含矽氧烷嵌段之二醇化合物,例如,若與聚碳酸酯進行共聚合,則可對聚碳酸酯賦予耐藥品性、低溫衝撃性、耐候性、阻燃性等功能。
作為這種含矽氧烷嵌段之二醇化合物,專利文獻1記載:較佳為以下述式(a)~(c)表示之含矽氧烷嵌段之二醇化合物(羥基芳基末端聚矽氧烷)。
專利文獻1記載:藉由於如上述之含矽氧烷嵌段之二醇化合物添加規定之無機鹽及/或有機鹽,利用無溶劑熔融法製造聚二有機矽氧烷-聚有機嵌段共聚物,而改善所獲得之共聚物的熔融安定性、對於溶劑對水之分解安定性及耐低溫衝擊性。
[先前技術文獻]
[專利文獻]
專利文獻1:日本特表2016-538362號公報
[發明欲解決之課題]
然而,已明暸如上述之專利文獻1所記載的含矽氧烷嵌段之二醇化合物,存在作為原料之矽氧烷化合物與二醇化合物的反應性低,難以於工業上製造的情況。
因此,本發明提供一種工業上容易製造之組成物,其包含:含矽氧烷嵌段之二醇化合物。
[用以解決課題之手段]
本發明人等為了解決上述課題而努力地進行研究。其結果,發現藉由將含矽氧烷嵌段之二醇化合物設為規定的構造,而可解決上述課題,遂完成本發明。亦即,本發明例如為以下所述者。
[1] 一種組成物,其包含:含矽氧烷嵌段之二醇化合物,
前述含矽氧烷嵌段之二醇化合物係以下述式(I)表示,
[式中,
R
1及R
2分別獨立地為可具有取代基之碳數1~20之烷基、可具有取代基之碳數6~30之芳基,
m為1~25之整數,
n為3~200之整數,
X分別獨立地為下述式(I
1)~(I
6):
此時,
A
1及A
2分別獨立地為-(CR
6AR
6B)
q1-或-(O-(CR
6AR
6B)
q2)
q3-,此處,R
6A及R
6B分別獨立地為H或碳數1~6之烷基,q1為0~10之整數,q2為0~10之整數,q3為0~10之整數,
R
3及R
4分別獨立地為鹵素原子、碳數1~20之脂肪族烴基、碳數1~20之烷氧基、碳數3~20之環烷基、碳數6~20之芳香族烴基、碳數7~20之芳烷基、碳數6~20之芳香族烴氧基、碳數3~20之環烷氧基,
p1及p2分別獨立地為0~4之整數,
R
5分別獨立地為H或碳數1~6之烷基,
X
1及X
2分別獨立地為單鍵或下述所表示之基:
此處,R
7及R
8分別獨立地為H、鹵素原子、可具有取代基之碳數1~20之脂肪族烴基、可具有取代基之碳數1~20之烷氧基、可具有取代基之碳數6~20之芳香族烴基,或者R
7及R
8可鍵結而形成碳數3~20之碳環或5~12員的雜環;R
9及R
10分別獨立地為H、碳數1~6之烷基;R
11~R
16分別獨立地為鹵素原子、可具有取代基之碳數1~20之脂肪族烴基、可具有取代基之碳數1~20之烷氧基、可具有取代基之碳數6~12之芳香族烴基;r1為2~20之整數,
X
3分別獨立地為碳數15~32之2價芳香族烴基,
X
4分別獨立地為包含1個以上之烴環或雜環之2價基,此處,包含1個以上之烴環或雜環之2價基可與選自由R
5、R
6A及R
6B所成群組中之至少1個一起鍵結而形成,
X
5分別獨立地為2價飽和雜環基,此處,2價飽和雜環基可與選自由R
5、R
6A及R
6B所成群組中之至少1個一起鍵結而形成,
X
6分別獨立地為可包含氧原子之碳數1~10之伸烷基,
s1及s2分別獨立地為0~10之整數]。
[2] 一種矽氧烷系熱塑性樹脂,其包含:源自上述[1]所記載之含矽氧烷嵌段之二醇化合物的構成單元。
[3] 一種上述[1]所記載之組成物之製造方法,其包含:
使(A)以下述式(1)表示之環狀矽氧烷化合物及/或以下述式(2)表示之直鏈狀矽氧烷化合物、
(B)以下述式(J
1)~(J
6)表示之二醇化合物,與
(C)鹼性化合物觸媒
進行反應的步驟;
[式中,
R
1及R
2分別獨立地為可具有取代基之烷基、可具有取代基之烯基、可具有取代基之芳基,
n為3~30之整數]
[式中,
R
3及R
4分別獨立地為可具有取代基之烷基、可具有取代基之烯基、可具有取代基之芳基,
X分別獨立地為氫原子、羥基、可具有取代基之碳數1~10之烷氧基、可具有取代基之碳數1~10之矽氧烷基、可具有取代基之碳數1~10之烴基、可具有取代基之碳數1~10之含氧原子之基、可具有取代基之碳數1~10之含氮原子之基、可具有取代基之胺基,
m為2~10000之整數]
[式中,A
1及A
2、X
1~X
6、R
3~R
5、p1~p2及s1~s2與上述[1]之定義相同]。
[4] 一種矽氧烷系熱塑性樹脂之製造方法,其包含:使上述[1]所記載之組成物與熱塑性樹脂,於觸媒存在下,以160~400℃進行反應的步驟。
[發明的效果]
藉由本發明提供一種工業上容易製造之組成物,其包含:含矽氧烷嵌段之二醇化合物。
以下詳細說明用以實施本發明之形態。
<組成物>
本發明之組成物包含含矽氧烷嵌段之二醇化合物。前述組成物除此之外亦可包含源自環狀矽氧烷化合物、直鏈狀矽氧烷化合物、二醇化合物、鹼性化合物觸媒等原料之雜質、該等之分解物。
[含矽氧烷嵌段之二醇化合物]
含矽氧烷嵌段之二醇化合物係以下述式(I)表示。
式(I)中,X之中與羥基鍵結之碳原子(式(I
1)~(I
6)中的-CHR
5-)為一級碳原子或二級碳原子。藉此,衍生出X之構成單元的二醇化合物、與衍生出矽氧烷嵌段的環狀矽氧烷化合物及/或直鏈狀矽氧烷化合物之反應性變高。其結果,工業上製造以式(I)表示之化合物(即,含矽氧烷嵌段之二醇化合物)變容易。
上述式中,R
1及R
2分別獨立地為可具有取代基之碳數1~20之烷基、可具有取代基之碳數6~30之芳基。
作為前述碳數1~20之烷基,並無特別限制,可列舉甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、正己基、正辛基、正癸基、正十五烷基、正二十烷基等。該等中,碳數1~20之烷基,較佳為碳數1~10之烷基,更佳為碳數1~6之烷基,進而佳為碳數1~4之烷基,特佳為碳數1~2之烷基,最佳為甲基。
作為前述碳數6~30之芳基,並無特別限制,可列舉苯基、茚基、萘基、聯苯基、苊基、茀基、萉基(phenalenyl)、菲基、蒽基、三亞苯基(triphenylenyl)、芘基、䓛基(chrysenyl)、稠四苯基(naphthacenyl)、苝基等。該等中,碳數6~30之芳基,較佳為碳數6~12之芳基,更佳為苯基。
作為前述R
1及R
2之取代基,並無特別限制,可列舉羥基、鹵素原子、胺基、乙烯基、羧基、氰基、(甲基)丙烯醯氧基、縮水甘油氧基、巰基等。另外,本說明書中,「胺基」除未取代之胺基(-NH
2)以外,包含:經1個碳數1~6之烷基取代之單烷基胺基、經2個碳數1~6之烷基取代之二烷基胺基。作為該胺基之具體例,並無特別限制,可列舉胺基(-NH
2);甲基胺基、乙基胺基、正丙基胺基、異丙基胺基、正丁基胺基、異丁基胺基、第三丁基胺基、正戊基胺基、正己基胺基等單烷基胺基;二甲基胺基、二乙基胺基、二(正丙基)胺基、二異丙基胺基、二(正丁基)胺基、二異丁基胺基、二(正戊基)胺基、二(正己基)胺基、乙基甲基胺基、甲基(正丙基)胺基、正丁基甲基胺基、乙基(正丙基)胺基、正丁基乙基胺基等二烷基胺基。該等中,胺基較佳為未取代之胺基(-NH
2)。
m為1~25之整數,較佳為1~20,更佳為3~15。
n為3~200之整數,較佳為3~100,更佳為3~50,進而佳為3~10。
X分別獨立地以下述式(I
1)~(I
6)表示。
即,式(I)中,羥基所鍵結之-CHR
5-為一級碳原子或二級碳原子。
A
1及A
2分別獨立地為-(CR
6AR
6B)
q1-或 -(O-(CR
6AR
6B)
q2)
q3-。
此時,R
6A及R
6B分別獨立地為H或碳數1~6之烷基。
作為前述碳數1~6之烷基,可列舉甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、正己基等。
q1為0~10之整數,較佳為0~5,更佳為0~3。
q2為0~10之整數,較佳為0~5,更佳為0~3。
q3為0~10之整數,較佳為0~5,更佳為0~3。
R
3及R
4分別獨立地為鹵素原子、碳數1~20之脂肪族烴基、碳數1~20之烷氧基、碳數3~20之環烷基、碳數6~20之芳香族烴基、碳數7~20之芳烷基、碳數6~20之芳香族烴氧基、碳數3~20之環烷氧基。
作為鹵素原子,可列舉氟原子、氯原子、溴原子、碘原子等。
碳數1~20之脂肪族烴基即為一價脂肪族烴基,雖並無特別限制,但可列舉碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基。
作為前述碳數1~20之烷基,並無特別限制,可列舉甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、正己基、正辛基、正癸基、正十五烷基、正二十烷基等。該等中,作為碳數1~20之烷基,較佳為碳數1~10之烷基,更佳為碳數1~6之烷基,進而佳為碳數1~4之烷基,特佳為碳數1~2之烷基,最佳為甲基。
作為前述碳數2~20之烯基,並無特別限制,可列舉乙烯基(ethenyl)(乙烯基(vinyl))、1-丙烯基、2-丙烯基(propenyl)(烯丙基(allyl))、異丙烯基、2-丁烯基、3-丁烯基、異丁烯基、戊烯基、己烯基、辛烯基、癸烯基、十五烯基、二十烯基等。該等中,作為碳數2~20之烯基,較佳為碳數2~10之烯基,更佳為碳數2~6之烯基,進而佳為乙烯基(ethenyl)(乙烯基(vinyl))、2-丙烯基(propenyl)(烯丙基(allyl))。
作為前述碳數2~20之炔基,並無特別限制,可列舉乙炔基、1-丙炔基、2-丙炔基、2-丁炔基、3-丁炔基、戊炔基、己炔基、辛炔基、癸炔基、十五炔基、二十炔基等。該等中,作為碳數2~20之炔基,較佳為碳數2~10之炔基,更佳為碳數2~6之炔基,進而佳為碳數2~4之炔基,特佳為碳數2~3之炔基。
碳數1~20之烷氧基即為碳數1~20之直鏈狀或支鏈狀之一價脂肪族烴氧基,雖並無特別限制,但可列舉甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、第三丁氧基、正戊氧基、正己氧基等。該等中,作為碳數1~20之烷氧基,較佳為碳數1~10之烷氧基,更佳為碳數1~6之烷氧基,進而佳為碳數1~4之烷氧基,特佳為碳數1~2之烷氧基,最佳為甲氧基。
碳數3~20之環烷基即為碳數3~20之一價環狀飽和脂肪族烴基,雖並無特別限制,但可列舉環丙基、環丁基、環戊基、環己基、金剛烷基等。該等中,作為碳數3~20之環烷基,較佳為碳數3~10之環烷基。
碳數6~20之芳香族烴基即為碳數6~20之一價芳香族烴基,雖並無特別限制,但可列舉苯基、茚基、萘基、聯苯基、苊基、茀基、萉基(phenalenyl)、菲基、蒽基、三亞苯基(triphenylenyl)、芘基、䓛基(chrysenyl)、稠四苯基、苝基等。該等中,作為碳數6~20之芳香族烴基,較佳為碳數6~12之芳香族烴基,更佳為苯基。
碳數7~20之芳烷基即為經1個芳香族烴基取代之烷基,雖並無特別限制,但可列舉苄基、苯乙基、苯丙基、萘甲基、萘乙基、聯苯基甲基等。該等中,作為碳數7~20之芳烷基,較佳為苄基。
碳數6~20之芳香族烴氧基即為碳數6~20之一價芳香族烴氧基,雖並無特別限制,但可列舉苯氧基、茚氧基、萘氧基、聯苯氧基、苊氧基、茀氧基、萉氧基、菲氧基、蒽氧基、蒽氧基、三亞苯基氧基(triphenylenyloxy)、芘氧基、䓛氧基、稠四苯基氧基(naphthacenyloxy)、苝氧基等。該等中,作為碳數6~20之芳香族烴氧基,較佳為碳數6~12之芳香族烴氧基,更佳為苯氧基。
作為碳數3~20之環烷氧基,並無特別限制,可列舉環丙基氧基、環丁基氧基、環戊基氧基、環己基氧基、金剛烷基氧基、環十二烷基等。該等中,碳數3~20之環烷氧基較佳為碳數3~12之環烷基氧基。
p1及p2分別獨立地為0~4之整數,較佳為0~2,更佳為0~1。
R
5分別獨立地為H或碳數1~6之烷基。此時,作為前述碳數1~6之烷基,可列舉甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、正己基等。
X
1及X
2分別獨立地為單鍵或下述所表示之基。
上述式中,R
7及R
8分別獨立地為H、鹵素原子、可具有取代基之碳數1~20之脂肪族烴基、可具有取代基之碳數1~20之烷氧基、可具有取代基之碳數6~20之芳香族烴基,或者R
7及R
8可鍵結而形成碳數3~20之碳環或5~12員的雜環。
碳數1~20之脂肪族烴基、碳數1~20之烷氧基、碳數6~20之芳香族烴基係如同上述者。
又,作為前述碳數1~20之脂肪族烴基及碳數1~20之烷氧基可具有之取代基,並無特別限制,可列舉碳數1~6之烷氧基、碳數1~7之醯基、鹵素原子、胺基、硝基、氰基、胺甲醯基等。
另一方面,作為前述碳數6~20之芳香族烴基可具有之取代基,並無特別限制,可列舉碳數1~6之烷基、碳數1~6之烷氧基、碳數1~7之醯基、鹵素原子、胺基、硝基、氰基、胺甲醯基等。
作為R
7及R
8鍵結所形成之碳數3~20之碳環,並無特別限制,可列舉可具有取代基之碳數3~20之環烷基、環烷基與芳香族烴基之縮合環。作為前述縮合環,可列舉苊基、茀基等。
另外,作為前述碳數3~20之碳環可具有之取代基,並無特別限制,可列舉碳數1~6之烷基、碳數1~6之烷氧基、碳數1~7之醯基、鹵素原子、胺基、硝基、氰基、胺甲醯基等。
又,作為R
7及R
8鍵結所形成之5~12員雜環,並無特別限制,可列舉環氧乙烷基(oxiranyl)、氮丙啶基、四氫呋喃基、四氫噻吩基、吡咯啶基、氧硫雜環戊基(oxathiolanyl)、哌啶基,1(3H)-異苯并呋喃基等。
R
9及R
10分別獨立地為H、碳數1~6之烷基。此時,作為前述碳數1~6之烷基,可列舉甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、正己基等。
r1為2~20之整數,較佳為2~10,更佳為2~5。
R
11~R
16分別獨立地為鹵素原子、可具有取代基之碳數1~20之脂肪族烴基、可具有取代基之碳數1~20之烷氧基、可具有取代基之碳數6~12之芳香族烴基,其具體例係與R
7及R
8所記載者相同。
作為衍生出具有式I
1之X的二醇化合物,並無特別限制,可列舉α,ω-雙[3-(鄰羥基苯基)丙基]聚二甲基矽氧烷、9,9-雙[4-(2-羥基乙氧基)苯基]茀(BPEF)、9,9-雙[4-(2-羥基乙氧基)-3-甲基苯基]茀、9,9-雙[4-(2-羥基乙氧基)-3-第三丁基苯基]茀、9,9-雙[4-(2-羥基乙氧基)-3-異丙基苯基]茀、9,9-雙[4-(2-羥基乙氧基)-3-環己基苯基]茀、9,9-雙[4-(2-羥基乙氧基)-3-苯基苯基]茀、2,2-雙(4-(2-羥基乙氧基)苯基)丙烷、4,4-雙(2-羥基乙氧基)聯苯、2,2’(9H-茀-9,9’-二基)雙(乙烷-1-醇)、9H-茀-9,9-二基二甲醇、2,2’-(1,4-伸苯基)雙(乙烷-1-醇)、2,2’-(1,4-伸苯基)雙(甲烷-1-醇)、2,2’-(1,4-伸苯基雙(氧基))雙(乙烷-1-醇)等。該等中,衍生出具有式I
1之X的二醇化合物,較佳為9,9-雙[4-(2-羥基乙氧基)苯基]茀(BPEF)。
一實施形態中,衍生出具有式I
1之X的二醇化合物之構造係如下所示。
作為衍生出具有式I
2之X的二醇化合物,並無特別限制,可列舉9,9-雙[6-(1-羥基甲氧基)萘-2-基]茀、9,9-雙[6-(2-羥基乙氧基)萘-2-基]茀、9,9-雙[6-(3-羥基丙氧基)萘-2-基]茀、9,9-雙[6-(4-羥基丁氧基)萘-2-基]茀、2,2’-雙(2-羥基乙氧基)-6,6’-二苯基-1,1’-聯萘等。該等中,衍生出具有式I
2之X的二醇化合物,較佳為9,9-雙[6-(2-羥基乙氧基)萘-2-基]茀、2,2’-雙(2-羥基乙氧基)-6,6’-二苯基-1,1’-聯萘。
X
3分別獨立地為碳數15~32之2價芳香族烴基。
作為前述碳數15~32之2價芳香族烴基,並無特別限制,可列舉伸熒蒽基(fluoranthrenylene)、伸醋菲烯基(acephenanthrylenylene)、伸醋蒽烯基(aceanthrylenylene)、聯伸三苯基(triphenylene)、伸芘基、伸䓛基(chrysenylene)、伸稠四苯基(naphthacenylene)、伸七曜烯基(pleiadenylene)、伸苉基(picenylene)、伸苝基(perylenylene)、伸聯苯基(biphenylene)、伸五苯基(pentaphenylene)、伸稠五苯基(pentacenylene)、伸四伸苯基(tetraphenylenylene)、六伸苯基(hexaphenylene)、伸稠六苯基(hexacenylene)、伸茹基(rubicenylene)、伸蒄基(coronenylene)、伸聯三萘基(trinaphthylenylene)、七伸苯基(heptaphenylene)、伸稠七苯基(heptacenylene)、伸吡蒽基(pyranthrenylene)、伸莪基(ovalenylene)等二價縮合多環式芳香族烴基;伸三聯苯基(terphenylene)、伸四聯苯基(quarterphenylene)等。
作為衍生出具有式I
3之X的二醇化合物,並無特別限制,可列舉聯萘二醇化合物。具體而言,可列舉2,2’-雙(1-羥基甲氧基)-1,1’-聯萘、2,2’-雙(2-羥基乙氧基)-1,1’-聯萘、2,2’-雙(3-羥基丙氧基)-1,1’-聯萘、2,2’-雙(4-羥基丁氧基)-1,1’-聯萘等。該等中,衍生出具有式I
3之X的二醇化合物,較佳為2,2’-雙(2-羥基乙氧基)-1,1’-聯萘。
X
4分別獨立地為包含1個以上之烴環或雜環之2價基。
作為前述烴環或雜環,並無特別限制,可列舉分別具有1個以上之下述基團的二價基:可具有取代基之碳數6~32之二價芳香族烴基、可具有取代基之碳數3~20之二價環烷基、可具有取代基之碳數6~32之二價芳香族烴基及碳數3~20之二價環烷基。
前述碳數6~32之二價芳香族烴基,只要是以整體而言顯示芳香族性者,亦可為包含選自氧原子、硫原子、氮原子之雜原子者。作為碳數6~32之二價芳香族烴基,並無特別限制,可列舉以下者。
前述碳數3~20之二價環烷基,亦可為包含選自氧原子、硫原子、氮原子之雜原子者。作為碳數3~20之二價環烷基,並無特別限制,可列舉以下者。
作為分別具有1個以上之前述碳數6~32之二價芳香族烴基及碳數3~20之二價環烷基的二價基,並無特別限制,可列舉以下者。
作為分別具有1個以上之碳數6~32之二價芳香族烴基、碳數3~20之二價環烷基、碳數6~32之二價芳香族烴基及碳數3~20之二價環烷基的二價基可具有之取代基,並無特別限制,可列舉碳數1~6之烷基、碳數1~6之烷氧基、碳數1~7之醯基、鹵素原子、胺基、硝基、氰基、胺甲醯基等。
另外,2價飽和雜環基可與選自由R
5、R
6A及R
6B所成群組中之至少1個一起鍵結而形成。例如,作為衍生出具有式I
4之X的二醇化合物之1,4-環己烷二甲醇(CHDM),藉由與R
5、R
6A及R
6B一起鍵結,而使式(I)中的X具有環己烷環。
X
5分別獨立地為2價飽和雜環基。
作為前述2價之飽和雜環基,並無特別限制,可列舉以下者。
另外,2價飽和雜環基可與選自由R
5、R
6A及R
6B所成群組中之至少1個一起鍵結而形成。例如,作為衍生出具有式I
4之X的二醇化合物之2,4-二羥基-1,4-二噁烷,藉由與R
5、R
6A及R
6B一起鍵結,而使式(I)中的X具有環己烷環。
X
6分別獨立地為可包含氧原子之碳數1~10之伸烷基。
作為前述可包含氧原子之碳數1~10之伸烷基,並無特別限制,可列舉亞甲基、伸乙基、伸丙基、伸異丙基、伸丁基等伸烷基;氧亞甲基(-CH
2-O-)、氧伸乙基(-CH
2CH
2-O-)、二氧伸乙基(-CH
2CH
2-O-CH
2CH
2-O-)、三氧伸乙基(-CH
2CH
2-O-CH
2CH
2-O-CH
2CH
2-O-)等含氧原子之伸烷基等。
又,s1及s2分別獨立地為0~10之整數,較佳為0~5,更佳為0~3。
作為衍生出具有式I
6之X的二醇化合物,可列舉乙二醇(EG)、1,3-丙二醇(PG)、1,4-丁二醇(BD)、2-丁基-2-乙基-1,3-丙二醇(BEPG)、新戊二醇(NPG)等。
上述含矽氧烷嵌段之二醇化合物,可單獨包含於組成物中,亦可組合2種以上而包含於組成物中。
含矽氧烷嵌段之二醇化合物之重量平均分子量(Mw),較佳為10000~1000000,更佳為30000~800000,進而佳為40000~250000。另外,本說明書中,將「重量平均分子量(Mw)」之值設為採用以實施例的方法所測定之值。
含矽氧烷嵌段之二醇化合物之數平均分子量(Mn),較佳為10000~500000,更佳為20000~300000,進而佳為30000~200000。另外,本說明書中,將「數平均分子量(Mn)」之值設為採用以實施例的方法所測定之值。
含矽氧烷嵌段之二醇化合物之相對於數平均分子量(Mn)之重量平均分子量(Mw)(Mw/Mn),較佳為1~4,更佳為1.05~3,進而佳為1.1~2。
<含矽氧烷嵌段之二醇化合物之製造方法>
依據本發明之一形態,提供上述含矽氧烷嵌段之二醇化合物之製造方法。
含矽氧烷嵌段之二醇化合物之製造方法包含:使(A)環狀矽氧烷化合物及/或直鏈狀矽氧烷化合物、(B)二醇化合物、與(C)鹼性化合物觸媒進行反應的步驟。
[(A)環狀矽氧烷化合物及/或直鏈狀矽氧烷化合物]
環狀矽氧烷化合物係以下述式(1)表示。
式中,R
1及R
2分別獨立地為可具有取代基之烷基、可具有取代基之烯基、可具有取代基之芳基。此時,R
1及R
2較佳為可具有取代基之合計碳數1~20之烷基、合計碳數6~30之芳基。
作為前述可具有取代基之合計碳數1~20之烷基,較佳為合計碳數1~10之烷基,更佳為合計碳數1~6之烷基,進而佳為合計碳數1或2之烷基。
作為前述合計碳數6~30之芳基,較佳為合計碳數6~20之芳基,更佳為合計碳數6~12之芳基,進而佳為合計碳數6~8之芳基。
作為前述取代基,可列舉羥基、鹵素、胺基、乙烯基、羧基、氰基、(甲基)丙烯醯氧基、縮水甘油氧基、巰基等。
作為R
1及R
2之較佳具體例,可列舉甲基、苯基、乙烯基、丙基。
n為3~30之整數,較佳為3~15,更佳為3~10,進而佳為3~8,特佳為3~5。
以式(1)表示之環狀矽氧烷化合物之分子量,較佳為2000以下,更佳為1600以下,進而佳為1200以下,特佳為1000以下。又,以式(1)表示之環狀矽氧烷化合物之分子量,較佳為100以上,更佳為150以上,進而佳為200以上。
作為以式(1)表示之環狀矽氧烷化合物之較佳具體例,可列舉十甲基環五矽氧烷(D5)、八甲基環四矽氧烷(D4)、八苯基環四矽氧烷(OPTS)。
直鏈狀矽氧烷化合物係以下述式(2)表示。
式中,R
3及R
4分別獨立地為鹵素原子、碳數1~20之脂肪族烴基、碳數1~20之烷氧基、碳數3~20之環烷基、碳數6~20之芳香族烴基、碳數7~20之芳烷基、碳數6~20之芳香族烴氧基、碳數3~20之環烷氧基。此時,R
3及R
4較佳為可具有取代基之合計碳數1~20之烷基、合計碳數6~30之芳基。
作為前述可具有取代基之合計碳數1~20之烷基,較佳為合計碳數1~10之烷基,更佳為合計碳數1~8之烷基,進而佳為合計碳數1或2之烷基。
作為前述合計碳數6~30之芳基,較佳為合計碳數6~20之芳基,更佳為合計碳數6~12之芳基,進而佳為合計碳數6~8之芳基。
作為前述取代基,可列舉羥基、鹵素、胺基、乙烯基、羧基、氰基、(甲基)丙烯醯氧基、縮水甘油氧基、巰基等。
作為R
3及R
4之較佳具體例,可列舉甲基、苯基、乙烯基、丙基。
X分別獨立地為氫原子、羥基、可具有取代基之碳數1~10之烷氧基、可具有取代基之碳數1~10之矽氧烷基、可具有取代基之碳數1~10之烴基、可具有取代基之碳數1~10之含氧原子之基、可具有取代基之碳數1~10之含氮原子之基、可具有取代基之胺基。其中,X較佳為羥基、可具有取代基之碳數1~10之矽氧烷基、可具有取代基之碳數1~10之烴基,更佳為羥基、可具有取代基之碳數1~5之矽氧烷基、可具有取代基之碳數1~5之烴基,進而佳為羥基、三甲基矽基氧基、三乙基矽基氧基、第三丁基二甲基矽基氧基、甲基、乙基、丙基、異丙基、丁基、正丁基、第二丁基、第三丁基。
m為2~10000之整數,較佳為10~7000,更佳為100~2000,進而佳為200~500。
以式(2)表示之直鏈狀矽氧烷化合物之分子量,較佳為60000以下,更佳為56000以下,進而佳為50000以下,特佳為45000以下。又,以式(2)表示之直鏈狀矽氧烷化合物之分子量,較佳為1000以上,更佳為5000以上,進而佳為10000以上。
作為以式(2)表示之直鏈狀矽氧烷化合物之較佳具體例,可列舉直鏈狀聚二甲基矽氧烷(直鏈狀PDSM)。
環狀矽氧烷化合物及直鏈狀矽氧烷化合物,可單獨使用,亦可組合2種以上使用。
[(B)二醇化合物]
作為二醇化合物,並無特別限制,可列舉以下述式(J
1)~(J
6)表示之二醇化合物。
上述式中,A
1及A
2、X
1~X
6、R
3~R
5、p1~p2及s1~s2與上述相同。
其中,二醇化合物較佳為9,9-雙[4-(2-羥基乙氧基)苯基]茀(BPEF)、1,4-環己烷二甲醇(CHDM)、乙二醇(EG)、1,3-丙二醇(PG)、1,4-丁二醇(BD)、2-丁基-2-乙基-1,3-丙二醇(BEPG)、新戊二醇(NPG)。
上述二醇化合物可單獨使用,亦可組合2種以上使用。
[(C)鹼性化合物觸媒]
鹼性化合物觸媒具有促進(A)環狀矽氧烷化合物及/或直鏈狀矽氧烷化合物、與(B)二醇化合物進行反應的功能。
作為前述鹼性化合物觸媒,可列舉鹼金屬化合物、鹼土類金屬化合物等。
作為前述鹼金屬化合物,並無特別限制,可列舉氫氧化鋰、氫氧化鈉、氫氧化鉀等鹼金屬氫氧化物;碳酸鈉、碳酸鉀、碳酸銫等鹼金屬碳酸鹽;碳酸氫鈉、碳酸氫鉀、碳酸氫銫等鹼金屬碳酸氫鹽等。
作為前述鹼土類金屬化合物,並無特別限制,可列舉氫氧化鎂、氫氧化鈣等鹼土類金屬氫氧化物;碳酸鎂、碳酸鈣等鹼土類金屬碳酸鹽等。
上述中,鹼性化合物觸媒較佳為鹼金屬碳酸鹽、鹼金屬碳酸氫鹽,更佳為碳酸鈉、碳酸鉀、碳酸銫、碳酸氫鈉、碳酸氫鉀,進而佳為碳酸鉀、碳酸銫,特佳為碳酸銫。另外,上述鹼性化合物觸媒,可單獨使用,亦可組合2種以上使用。
鹼性化合物觸媒之添加量,並無特別限制,相對於二醇化合物較佳設為1.5~100倍莫耳,更佳為2.0~50倍莫耳,進而佳為3.0~30倍莫耳,特佳為4.0~20倍莫耳。
[反應]
反應並無特別限制,較佳為於(C)鹼性化合物觸媒存在下,加熱(A)環狀矽氧烷化合物及/或直鏈狀矽氧烷化合物、以及(B)二醇化合物進行反應。
反應溫度並無特別限制,較佳為30~300℃,更佳為80~250℃,進而佳為100~230℃。
反應環境並無特別限制,較佳為於惰性氣體環境下進行。作為前述惰性氣體,可列舉氮氣、氬氣等。
藉由進行前述反應,可製造包含含矽氧烷嵌段之二醇化合物之組成物。
另外,在藉由反應而獲得之生成物中可含有的副反應物、未反應原料之中,較低沸點的雜質(環狀矽氧烷化合物等)可藉由減壓餾除而適當地去除。
<矽氧烷系熱塑性樹脂>
依據本發明之一形態,提供矽氧烷系熱塑性樹脂,其包含:源自上述含矽氧烷嵌段之二醇化合物的構成單元。
作為前述矽氧烷系熱塑性樹脂,並無特別限制,可列舉聚碳酸酯樹脂、聚酯碳酸酯樹脂、聚甲基丙烯酸甲酯(PMMA)等丙烯酸樹脂、聚對苯二甲酸乙二酯(PET)、三乙酸纖維素(TAC)、聚萘二甲酸乙二酯(PEN)、聚醯亞胺(PI)、環烯烴共聚物(COC)、含降莰烯樹脂、聚醚碸、賽璐玢、芳香族聚醯胺等。
一實施形態中,矽氧烷系熱塑性樹脂係使含矽氧烷嵌段之二醇化合物、與前述熱塑性樹脂或其單體進行反應而成之共聚物。
以下,針對矽氧烷系熱塑性樹脂為矽氧烷系聚碳酸酯樹脂的情況進行詳細說明。
矽氧烷系聚碳酸酯樹脂包含:源自含矽氧烷嵌段之二醇化合物的構成單元、與源自碳酸酯化合物的構成單元。
前述碳酸酯化合物,只要是可於矽氧烷系聚碳酸酯樹脂導入聚碳酸酯構成單元之羰基(-CO-基)者,則無特別限制。例如,可列舉碳酸二苯酯、碳酸二苄基酯、碳酸二甲苯基酯、碳酸雙(氯苯基)酯、間甲苯酚基碳酸酯等碳酸二芳酯;碳酸二甲酯、碳酸二乙酯、碳酸二丁酯、碳酸二環己酯等碳酸二烷酯;單芳基單烷基碳酸酯等。
該等碳酸酯化合物,可單獨使用,亦可組合2種以上使用。
矽氧烷系聚碳酸酯樹脂可進而包含其他構成單元。作為該其他構成單元,並無特別限制,可列舉源自芳香族二醇化合物的構成單元、源自二芳氧基矽烷化合物的構成單元等。
矽氧烷系聚碳酸酯樹脂之重量平均分子量,較佳為10000~1000000,更佳為20000~800000,進而佳為30000~700000。
矽氧烷系聚碳酸酯樹脂之源自含矽氧烷嵌段之二醇化合物的構成單元、與源自碳酸酯化合物的構成單元之莫耳比,較佳為0.01:99.99~99.99:0.01,更佳為1:99~99:1,進而佳為10:90~90:10,特佳為30:70~70:30。
上述矽氧烷系熱塑性樹脂,由於包含含矽氧烷嵌段之二醇化合物的構成單元,因此耐藥品性、低溫衝撃性、耐候性、阻燃性等優異。
<矽氧烷系熱塑性樹脂之製造方法>
依據本發明之一形態,提供矽氧烷系熱塑性樹脂之製造方法。前述矽氧烷系熱塑性樹脂之製造方法,包含:使組成物與熱塑性樹脂,於觸媒存在下,以160~400℃進行反應的步驟。
[組成物]
作為組成物,可使用包含上述含矽氧烷嵌段之二醇化合物之組成物。
[熱塑性樹脂]
作為熱塑性樹脂,並無特別限制,可列舉聚碳酸酯樹脂、聚酯碳酸酯樹脂、聚甲基丙烯酸甲酯(PMMA)等丙烯酸樹脂、聚對苯二甲酸乙二酯(PET)、三乙酸纖維素(TAC)、聚萘二甲酸乙二酯(PEN)、聚醯亞胺(PI)、環烯烴共聚物(COC)、含降莰烯樹脂、聚醚碸、賽璐玢、芳香族聚醯胺、該等之單體。
[觸媒]
作為觸媒,並無特別限制,可列舉鹼金屬化合物、鹼土類金屬化合物、含氮化合物、金屬鹽。
作為前述鹼金屬化合物,並無特別限制,可列舉氫氧化鈉、氫氧化鉀、氫氧化銫、氫氧化鋰、碳酸氫鈉、碳酸鈉、碳酸鉀、碳酸銫、碳酸鋰、乙酸鈉、乙酸鉀、乙酸銫、乙酸鋰、硬脂酸鈉、硬脂酸鉀、硬脂酸銫、硬脂酸鋰、硼氫化鈉、苯基化硼鈉、苯甲酸鈉、苯甲酸鉀、苯甲酸銫、苯甲酸鋰、磷酸氫二鈉、磷酸氫二鉀、磷酸氫二鋰、苯基磷酸二鈉、葡萄糖酸鈉、雙酚A之二鈉鹽、二鉀鹽、二銫鹽、二鋰鹽、苯酚之鈉鹽、鉀鹽、銫鹽、鋰鹽等。
作為前述鹼土類金屬化合物,並無特別限制,可列舉氫氧化鎂、氫氧化鈣、氫氧化鍶、氫氧化鋇、碳酸氫鎂、碳酸氫鈣、碳酸氫鍶、碳酸氫鋇、碳酸鎂、碳酸鈣、碳酸鍶、碳酸鋇、乙酸鎂、乙酸鈣、乙酸鍶、乙酸鋇、硬脂酸鎂、硬脂酸鈣、苯甲酸鈣、磷酸苯基鎂等。
作為前述含氮化合物,並無特別限制,可列舉四甲基氫氧化銨、四乙基氫氧化銨、四丙基氫氧化銨、四丁基氫氧化銨、三甲基苄基氫氧化銨等具有烷基及/或芳基之4級氫氧化銨類;三乙基胺、二甲基苄基胺、三苯基胺等3級胺類;二乙基胺、二丁基胺等2級胺類;丙基胺、丁基胺等1級胺類;2-甲基咪唑、2-苯基咪唑、苯并咪唑等咪唑類;氨、四甲基硼氫化銨、四丁基硼氫化銨、四丁基四苯基硼酸銨、四苯基四苯基硼酸銨等鹼或鹼性鹽等。
作為前述金屬鹽,並無特別限制,可列舉乙酸鋅、苯甲酸鋅、2-乙基己酸鋅等鋅鹽;氯化錫(II)、氯化錫(IV)、乙酸錫(II)、乙酸錫(IV)、二丁基二月桂酸錫、二丁基氧化錫、二丁基二甲氧化錫等錫鹽;乙醯丙酮鋯、氧乙酸鋯、四丁氧化鋯等鋯鹽;乙酸鉛(II)、乙酸鉛(IV)等鉛鹽等。
上述觸媒可單獨使用,亦可組合2種以上使用。
[反應]
反應並無特別限制,較佳為使組成物與熱塑性樹脂,於觸媒存在下進行反應。
此時,反應溫度為160~400℃,較佳為200~350℃,更佳為220~320℃,進而佳為240~310℃。
藉由進行前述反應,可製造矽氧烷系熱塑性樹脂。
[實施例]
以下,例舉實施例具體說明本發明,但本發明並不限定於該等。另外,若無特別排除,則「%」為質量基準。
[測定條件]
<聚矽氧烷、環狀矽氧烷之含量>
使用NMR來算出。另外,以下
1H-NMR分析中之化學位移係將作為TMS(四甲基矽烷)之波峰的0ppm設為基準。
以
1H-NMR分別於0.1~1.0ppm、0.079ppm、0.094ppm觀測到相當於聚矽氧烷、作為環狀矽氧烷之十甲基五環矽氧烷(D5)、八甲基四環矽氧烷(D4)之源自Si上之甲基之波峰。將0.079ppm、0.094ppm之波峰面積之和設為環狀矽氧烷含量,將從0.1~1.0ppm之波峰面積減去0.079 ppm、0.094ppm之波峰面積的值設為聚矽氧烷含量,基於該值求出聚矽氧烷生成率、環狀矽氧烷生成率。
<聚苯乙烯換算重量平均分子量(Mw、Mn、Mw/Mn)>
使用GPC(凝膠滲透層析法),將氯仿作為展開溶劑,使用已知分子量(分子量分布=1)之標準聚苯乙烯(Shodex STANDARD,SM-105)而作成檢量線。從所測定之標準聚苯乙烯繪製各波峰之溶出時間與分子量值,進行利用三次式之近似,作成校正曲線。
接著,基於所獲得的校正曲線,從下述式以聚苯乙烯換算值求出重量平均分子量(Mw)。
[計算式]
Mw=Σ(Wi×Mi)/Σ(Wi)
Mn=Σ(Ni×Mi)/Σ(Ni)
上述式中,i表示分割分子量M時之第i個分割點,Wi表示第i個之重量,Mi為第i個之分子量,Ni表示第i個分子數。又,分子量M表示校正曲線之相同溶出時間下以聚苯乙烯換算之分子量值。
另外,Mw/Mn表示分子量分散度。其係判定分子量分布廣或窄之參數,該值越接近1.0則表示分子量分布越窄,若越大則表示分子量分布越廣。
[測定條件]
・裝置:島津製作所股份有限公司製Labsolutions
・管柱:保護管柱(Shodex GPC K-G 4A)×1支,分析管柱(Shodex GPC K-805L)×2支
・溶劑:氯仿(HPLC等級)
・注入量:10μL
・試樣濃度:2000ppm
・溶劑流速:1mL/min
・測定溫度:40℃
・檢測器:RI
<玻璃轉移溫度(Tg)之測定>
作為測定樣品,將5~12mg之試驗片於AI自動取樣器用試樣容器(RDC鋁盤,直徑6.8mm,高度2.5mm之圓柱容器)秤量,將試樣容器之上部藉由AI自動取樣器用罩蓋密封而調製。
測定係使用示差掃描熱量計(DSC)於氮環境下(氮流量:50ml/min)進行,參考單元中使用藍寶石10.0mg作為標準物質。接著,將調整至30℃的測定樣品以20℃/min升溫至280℃後,以20℃/min進行冷卻降溫至30℃。之後,以10℃/min升溫至280℃並進行測定。
測定裝置:示差掃描熱量計(DSC) (製品名「DSC-7020」,日立高新技術科學股份有限公司製(Hitachi High-Tech Science Corporation))
[實施例1]
將十甲基環五矽氧烷(D5) 3.708g (10mmol,Si莫耳量:50mmol)、新戊二醇(NPG) 0.052g (0.5mmol)、及作為觸媒之碳酸銫(Ca
2CeO
3) 3.2582mg (10μmol)於氮環境下進行取代並以150℃加熱。藉由於150℃下攪拌2小時,而獲得無色油狀之包含含矽氧烷嵌段之二醇化合物(聚矽氧烷化合物)之組成物。
[實施例2]
將十甲基環五矽氧烷(D5) 37.05g (100mmol,Si莫耳量:500mmol)、2-丁基-2-乙基-1,3-丙二醇(BEPG) 3.205g (20mmol)、及作為觸媒之碳酸銫(Ca
2CeO
3) 1.3mg (4μmol)於氮環境下進行取代並以200℃加熱。於200℃下攪拌1小時後,冷卻至室溫並添加乙酸17.5mg (0.29mmol)。藉由於減壓下(2hPa)以80℃加熱2小時,餾除大部分環狀矽氧烷的同時,製造包含含矽氧烷嵌段之二醇化合物(聚矽氧烷化合物)之組成物。
[實施例3~17、比較例1~4]
除了將原料、反應溫度、反應時間變更為表1所記載者以外,與實施例1同樣地進行。
另外,表1中的簡稱係如下所述者。
(A)矽氧烷化合物
D5:十甲基環五矽氧烷
D4:八甲基環四矽氧烷
OPTS:八苯基環四矽氧烷
直鏈狀PDSM:直鏈狀聚二甲基矽氧烷
(B)二醇化合物
NPG:新戊二醇
BEPG:2-丁基-2-乙基-1,3-丙二醇
EG:乙二醇
PG:1,3-丙二醇
BD:1,4-丁二醇
CHDM:1,4-環己烷二甲醇
BPEF:9,9-雙[4-(2-羥基乙氧基)苯基]茀
BPA:雙酚A
HQ:氫醌
AD:1.3-金剛烷二醇
PHEP:2-(4-羥基苯基)乙醇
(C)鹼性化合物觸媒
Cs
2CO
3:碳酸銫
K
2CO
3:碳酸鉀
將於實施例1~17、比較例1~4所獲得的組成物以
1H-NMR及GPC進行分析。將所獲得的結果示於下述表2。
從表2的結果得知:實施例1~17可合適地製造含矽氧烷嵌段之二醇化合物。
另外,若對比使用1級醇作為(B)二醇化合物之實施例1、10~15,與使用2級醇作為(B)二醇化合物之實施例17,則可得知實施例1、10~15能夠以高產率製造含矽氧烷嵌段之二醇化合物。
[實施例a]
使用於實施例2製造之組成物(經餾除大部分環狀矽氧烷)與聚碳酸酯化合物來製造聚碳酸酯共聚物。
具體而言,將於實施例2製造之組成物2.00g、與聚碳酸酯20.01g(分子量=Mw18,783,Mn10,227,饋入碳酸銫作為觸媒,相對於雙酚A之莫耳數包含0.167μmol,Tg=122℃),於減壓下(2hPa)以230℃進行加熱。藉由於230℃下攪拌2小時,而獲得白色之矽氧烷嵌段共聚合聚碳酸酯。
使用GPC測定矽氧烷嵌段共聚合聚碳酸酯之Mw、Mn的結果為Mw44,619,Mn25,003。
[實施例b]
使用於實施例2製造之組成物與聚碳酸酯化合物來製造聚碳酸酯共聚物。
將聚碳酸酯20.00g(分子量=Mw18,783,Mn10,227,饋入碳酸銫作為觸媒,相對於雙酚A之莫耳數包含0.167μmol,Tg=122℃),於氮環境下以240℃進行加熱並使其熔融。該聚碳酸酯熔融後,以滴液漏斗滴入於實施例2製造之組成物10.00g。於240℃下緩緩地減壓,到達2hPa後升溫至260℃,藉由攪拌1小時,而獲得白色之矽氧烷嵌段共聚合聚碳酸酯。
使用GPC測定矽氧烷嵌段共聚合聚碳酸酯之Mw、Mn的結果為Mw101,401,Mn57,702。
[實施例c]
使用於實施例2製造之組成物與聚碳酸酯化合物來製造聚碳酸酯共聚物。
具體而言,將於實施例2製造之組成物2.50g、與聚碳酸酯10.00g(分子量=Mw18,783,Mn10,227,饋入碳酸銫作為觸媒,相對於雙酚A之莫耳數包含0.167μmol,Tg=122℃),於減壓下(2hPa)以260℃進行加熱。藉由於260℃下攪拌1小時20分鐘,而獲得白色且粉狀之矽氧烷嵌段共聚合聚碳酸酯。
使用GPC測定矽氧烷嵌段共聚合聚碳酸酯之Mw、Mn的結果為Mw356,597,Mn79,718。又,Tg為140℃。
Claims (4)
- 一種組成物,其包含:含矽氧烷嵌段之二醇化合物, 前述含矽氧烷嵌段之二醇化合物係以下述式(I)表示, [式中, R 1及R 2分別獨立地為可具有取代基之碳數1~20之烷基、可具有取代基之碳數6~30之芳基, m為1~25之整數, n為3~200之整數, X分別獨立地為下述式(I 1)~(I 6): , 此時, A 1及A 2分別獨立地為-(CR 6AR 6B) q1-或 -(O-(CR 6AR 6B) q2) q3-,此處,R 6A及R 6B分別獨立地為H或碳數1~6之烷基,q1為0~10之整數,q2為0~10之整數,q3為0~10之整數, R 3及R 4分別獨立地為鹵素原子、碳數1~20之脂肪族烴基、碳數1~20之烷氧基、碳數3~20之環烷基、碳數6~20之芳香族烴基、碳數7~20之芳烷基、碳數6~20之芳香族烴氧基、碳數3~20之環烷氧基, p1及p2分別獨立地為0~4之整數, R 5分別獨立地為H或碳數1~6之烷基, X 1及X 2分別獨立地為單鍵或下述所表示之基: , 此處,R 7及R 8分別獨立地為H、鹵素原子、可具有取代基之碳數1~20之脂肪族烴基、可具有取代基之碳數1~20之烷氧基、可具有取代基之碳數6~20之芳香族烴基,或者R 7及R 8可鍵結而形成碳數3~20之碳環或5~12員的雜環;R 9及R 10分別獨立地為H、碳數1~6之烷基;R 11~R 16分別獨立地為鹵素原子、可具有取代基之碳數1~20之脂肪族烴基、可具有取代基之碳數1~20之烷氧基、可具有取代基之碳數6~12之芳香族烴基;r1為2~20之整數, X 3分別獨立地為碳數15~32之2價芳香族烴基, X 4分別獨立地為包含1個以上之烴環或雜環之2價基,此處,包含1個以上之烴環或雜環之2價基可與選自由R 5、R 6A及R 6B所成群組中之至少1個一起鍵結而形成, X 5分別獨立地為2價飽和雜環基,此處,2價飽和雜環基可與選自由R 5、R 6A及R 6B所成群組中之至少1個一起鍵結而形成, X 6分別獨立地為可包含氧原子之碳數1~10之伸烷基, s1及s2分別獨立地為0~10之整數]。
- 一種矽氧烷系熱塑性樹脂,其包含:源自如請求項1之含矽氧烷嵌段之二醇化合物的構成單元。
- 一種如請求項1之組成物之製造方法,其包含: 使(A)以下述式(1)表示之環狀矽氧烷化合物及/或以下述式(2)表示之直鏈狀矽氧烷化合物、 (B)以下述式(J 1)~(J 6)表示之二醇化合物,與 (C)鹼性化合物觸媒 進行反應的步驟; [式中, R 1及R 2分別獨立地為可具有取代基之烷基、可具有取代基之烯基、可具有取代基之芳基, n為3~30之整數] [式中, R 3及R 4分別獨立地為可具有取代基之烷基、可具有取代基之烯基、可具有取代基之芳基, X分別獨立地為氫原子、羥基、可具有取代基之碳數1~10之烷氧基、可具有取代基之碳數1~10之矽氧烷基、可具有取代基之碳數1~10之烴基、可具有取代基之碳數1~10之含氧原子之基、可具有取代基之碳數1~10之含氮原子之基、可具有取代基之胺基, m為2~10000之整數] [式中,A 1及A 2、X 1~X 6、R 3~R 5、p1~p2及s1~s2與請求項1之定義相同]。
- 一種矽氧烷系熱塑性樹脂之製造方法,其包含:使如請求項1之組成物與熱塑性樹脂,於觸媒存在下,以160~400℃進行反應的步驟。
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