KR20150132552A - 공중합체 제조 방법 - Google Patents
공중합체 제조 방법 Download PDFInfo
- Publication number
- KR20150132552A KR20150132552A KR1020157030041A KR20157030041A KR20150132552A KR 20150132552 A KR20150132552 A KR 20150132552A KR 1020157030041 A KR1020157030041 A KR 1020157030041A KR 20157030041 A KR20157030041 A KR 20157030041A KR 20150132552 A KR20150132552 A KR 20150132552A
- Authority
- KR
- South Korea
- Prior art keywords
- atoms
- optionally substituted
- copolymer
- cyclic ester
- cyclic
- 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.)
- Withdrawn
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 78
- 238000004519 manufacturing process Methods 0.000 title description 7
- -1 cyclic ester Chemical class 0.000 claims abstract description 91
- 239000003054 catalyst Substances 0.000 claims abstract description 70
- 238000000034 method Methods 0.000 claims abstract description 52
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 45
- 125000004429 atom Chemical group 0.000 claims abstract description 34
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 46
- 150000002596 lactones Chemical group 0.000 claims description 35
- 230000008569 process Effects 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 28
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 25
- 125000003107 substituted aryl group Chemical group 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000007334 copolymerization reaction Methods 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 150000004703 alkoxides Chemical class 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052782 aluminium Inorganic materials 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims description 7
- 150000007942 carboxylates Chemical class 0.000 claims description 7
- 150000007944 thiolates Chemical class 0.000 claims description 7
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 238000001542 size-exclusion chromatography Methods 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 claims description 4
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 4
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 claims description 4
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 4
- 229910052706 scandium Inorganic materials 0.000 claims description 4
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 150000003949 imides Chemical class 0.000 claims description 3
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 3
- 150000002602 lanthanoids Chemical class 0.000 claims description 3
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- WRMFBHHNOHZECA-UHFFFAOYSA-N butan-2-olate Chemical compound CCC(C)[O-] WRMFBHHNOHZECA-UHFFFAOYSA-N 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 125000005374 siloxide group Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 abstract description 27
- 125000001424 substituent group Chemical group 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 description 43
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- 229920005604 random copolymer Polymers 0.000 description 25
- 238000006116 polymerization reaction Methods 0.000 description 21
- 239000003999 initiator Substances 0.000 description 16
- 239000000178 monomer Substances 0.000 description 15
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 10
- 229920001400 block copolymer Polymers 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 238000005809 transesterification reaction Methods 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 230000009257 reactivity Effects 0.000 description 8
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000012986 chain transfer agent Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 108010031797 Candida antarctica lipase B Proteins 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 108090001060 Lipase Proteins 0.000 description 3
- 239000004367 Lipase Substances 0.000 description 3
- 102000004882 Lipase Human genes 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 235000019421 lipase Nutrition 0.000 description 3
- 150000007931 macrolactones Chemical class 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 239000013110 organic ligand Substances 0.000 description 3
- 239000011574 phosphorus Chemical group 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 241000894007 species Species 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- YKVIWISPFDZYOW-UHFFFAOYSA-N 6-Decanolide Chemical compound CCCCC1CCCCC(=O)O1 YKVIWISPFDZYOW-UHFFFAOYSA-N 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229920005603 alternating copolymer Polymers 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- SPRIOUNJHPCKPV-UHFFFAOYSA-N hydridoaluminium Chemical compound [AlH] SPRIOUNJHPCKPV-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- NVIPUOMWGQAOIT-UHFFFAOYSA-N (E)-7-Hexadecen-16-olide Natural products O=C1CCCCCC=CCCCCCCCCO1 NVIPUOMWGQAOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- AOLNDUQWRUPYGE-UHFFFAOYSA-N 1,4-dioxepan-5-one Chemical compound O=C1CCOCCO1 AOLNDUQWRUPYGE-UHFFFAOYSA-N 0.000 description 1
- QUPWPPWMSDSBKD-UHFFFAOYSA-N 1,6-dioxacycloheptadec-8-en-7-one Chemical compound O=C1OCCCCOCCCCCCCCC=C1 QUPWPPWMSDSBKD-UHFFFAOYSA-N 0.000 description 1
- MZLRFHKWWCSGHB-UHFFFAOYSA-N 1,8-dioxacycloheptadecan-9-one Chemical compound O=C1CCCCCCCCOCCCCCCO1 MZLRFHKWWCSGHB-UHFFFAOYSA-N 0.000 description 1
- QILMAYXCYBTEDM-UHFFFAOYSA-N 1-oxacycloheptadec-10-en-2-one Chemical compound O=C1CCCCCCCC=CCCCCCCO1 QILMAYXCYBTEDM-UHFFFAOYSA-N 0.000 description 1
- ZYXGECMFJMLZNA-UHFFFAOYSA-N 1-oxacyclohexadec-12-en-2-one Chemical compound O=C1CCCCCCCCCC=CCCCO1 ZYXGECMFJMLZNA-UHFFFAOYSA-N 0.000 description 1
- AGZBJJSLDGWKSU-UHFFFAOYSA-N 1-oxacyclohexadec-13-en-2-one Chemical compound O=C1CCCCCCCCCCC=CCCO1 AGZBJJSLDGWKSU-UHFFFAOYSA-N 0.000 description 1
- USYAGNRXEGBFEX-UHFFFAOYSA-N 1-oxacyclopentadec-6-en-2-one Chemical compound O=C1CCCC=CCCCCCCCCO1 USYAGNRXEGBFEX-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- UPVAIJPDWVTFKT-UHFFFAOYSA-N 3,3-dimethyloxolan-2-one Chemical compound CC1(C)CCOC1=O UPVAIJPDWVTFKT-UHFFFAOYSA-N 0.000 description 1
- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 description 1
- MUHFZFOKQDJYON-UHFFFAOYSA-N 3-hexoxycyclotridecan-1-one Chemical compound CCCCCCOC1CCCCCCCCCCC(=O)C1 MUHFZFOKQDJYON-UHFFFAOYSA-N 0.000 description 1
- NYBXFCLDEATPCM-UHFFFAOYSA-N 3-methyloxetan-2-one Chemical compound CC1COC1=O NYBXFCLDEATPCM-UHFFFAOYSA-N 0.000 description 1
- VNXMFQWTDCWMDQ-UHFFFAOYSA-N 5-methyloxepan-2-one Chemical compound CC1CCOC(=O)CC1 VNXMFQWTDCWMDQ-UHFFFAOYSA-N 0.000 description 1
- YZRXRLLRSPQHDK-UHFFFAOYSA-N 6-Hexyltetrahydro-2H-pyran-2-one Chemical compound CCCCCCC1CCCC(=O)O1 YZRXRLLRSPQHDK-UHFFFAOYSA-N 0.000 description 1
- NVIPUOMWGQAOIT-DUXPYHPUSA-N 7-hexadecen-1,16-olide Chemical compound O=C1CCCCC\C=C\CCCCCCCCO1 NVIPUOMWGQAOIT-DUXPYHPUSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 229910010277 boron hydride Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000010813 internal standard method Methods 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229940089513 pentadecalactone Drugs 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- PYLIDHFYDYRZSC-UHFFFAOYSA-N propan-2-olate;yttrium(3+) Chemical compound [Y+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] PYLIDHFYDYRZSC-UHFFFAOYSA-N 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- 230000007704 transition Effects 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/84—Boron, aluminium, gallium, indium, thallium, rare-earth metals, or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/823—Preparation processes characterised by the catalyst used for the preparation of polylactones or polylactides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13001358.4 | 2013-03-18 | ||
| EP13001358 | 2013-03-18 | ||
| PCT/IB2014/059897 WO2014147546A1 (en) | 2013-03-18 | 2014-03-17 | Process for preparing a copolymer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150132552A true KR20150132552A (ko) | 2015-11-25 |
Family
ID=47901748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020157030041A Withdrawn KR20150132552A (ko) | 2013-03-18 | 2014-03-17 | 공중합체 제조 방법 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9512268B2 (enExample) |
| EP (1) | EP2976375B1 (enExample) |
| JP (1) | JP2016512857A (enExample) |
| KR (1) | KR20150132552A (enExample) |
| CN (1) | CN105143303A (enExample) |
| BR (1) | BR112015019566A2 (enExample) |
| WO (1) | WO2014147546A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3010952A1 (en) | 2013-06-20 | 2016-04-27 | Saudi Basic Industries Corporation | Pe-like polyesters |
| JP6807336B2 (ja) | 2015-05-22 | 2021-01-06 | サビック グローバル テクノロジーズ ベスローテン フェンノートシャップ | 改良された異相ポリプロピレン |
| CN107849321B (zh) | 2015-05-22 | 2020-04-28 | Sabic环球技术有限责任公司 | 聚合物组合物 |
| JP6862358B2 (ja) | 2015-05-22 | 2021-04-21 | サビック グローバル テクノロジーズ ベスローテン フェンノートシャップ | ポリマー組成物 |
| US10144802B2 (en) * | 2016-12-05 | 2018-12-04 | Novomer, Inc. | Beta-propiolactone based copolymers containing biogenic carbon, methods for their production and uses thereof |
| US20220267550A1 (en) | 2019-08-18 | 2022-08-25 | Sabic Global Technologies B.V. | Use of a composition for the manufacture of a foamed article |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2535562A1 (de) | 1975-08-08 | 1977-02-17 | Wolfgang Dr Ast | Ungesaettigte polyester-kautschuk- copolymerisate und verfahren zu ihrer herstellung |
| JP3408347B2 (ja) | 1994-06-08 | 2003-05-19 | 高砂香料工業株式会社 | 光学活性ブロック共重合ポリエステル及びその製造方法 |
| US6262278B1 (en) * | 1995-03-14 | 2001-07-17 | President And Fellows Of Harvard College | Stereoselective ring opening reactions |
| DE69928101T2 (de) | 1998-05-28 | 2006-08-10 | Gunze Limited, Ayabe | Lactid entahltende knochenfixierungsvorrichtung |
| JP4770092B2 (ja) * | 2001-08-24 | 2011-09-07 | 財団法人名古屋産業科学研究所 | ラクトンの開環重合用触媒、ポリエステルの製造方法、及びブロック共重合体の製造方法。 |
| GB0305927D0 (en) | 2003-03-14 | 2003-04-23 | Ic Innovations Ltd | Compound |
| CN1212343C (zh) * | 2003-11-27 | 2005-07-27 | 中国科学院长春应用化学研究所 | 环酯开环聚合催化剂及制备方法 |
| DE102005017049A1 (de) * | 2005-04-12 | 2006-10-19 | Basf Ag | Verfahren zur Herstellung von Polyhydroxyalkanoaten |
| JP2009528435A (ja) | 2006-03-01 | 2009-08-06 | ファイヤーストーン ポリマーズ エルエルシー | 再利用による着色を低減したメタセシス重合体を含有するポリエステル組成物 |
| EP2091995A1 (de) | 2006-11-14 | 2009-08-26 | Basf Se | Hoch- oder hyperverzweigte polyester sowie deren herstellung und verwendung |
| DE102008055870A1 (de) | 2008-10-31 | 2010-05-06 | Gkss-Forschungszentrum Geesthacht Gmbh | Multiphasen Polymernetzwerk mit Triple-Shape-Eigenschaften und Formgedächtniseffekt |
| WO2010110460A1 (ja) | 2009-03-27 | 2010-09-30 | 国立大学法人名古屋大学 | ラクチド・ε－カプロラクトン共重合体の製造方法 |
| EP2640766B1 (en) | 2010-11-18 | 2014-12-17 | Saudi Basic Industries Corporation | Process for preparing a polyester |
| CN102617369B (zh) | 2012-02-17 | 2014-10-15 | 华东理工大学 | 类salan单酚类配体金属络合物及其制备方法与应用 |
| US9080012B2 (en) | 2013-07-10 | 2015-07-14 | Xerox Corporation | One-pot, neat ring opening polymerization to prepare resin |
-
2014
- 2014-03-17 CN CN201480016425.XA patent/CN105143303A/zh active Pending
- 2014-03-17 US US14/766,254 patent/US9512268B2/en not_active Expired - Fee Related
- 2014-03-17 EP EP14718751.2A patent/EP2976375B1/en not_active Not-in-force
- 2014-03-17 BR BR112015019566A patent/BR112015019566A2/pt not_active IP Right Cessation
- 2014-03-17 WO PCT/IB2014/059897 patent/WO2014147546A1/en not_active Ceased
- 2014-03-17 KR KR1020157030041A patent/KR20150132552A/ko not_active Withdrawn
- 2014-03-17 JP JP2016503756A patent/JP2016512857A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP2976375B1 (en) | 2017-11-29 |
| WO2014147546A1 (en) | 2014-09-25 |
| US9512268B2 (en) | 2016-12-06 |
| BR112015019566A2 (pt) | 2017-07-18 |
| JP2016512857A (ja) | 2016-05-09 |
| EP2976375A1 (en) | 2016-01-27 |
| CN105143303A (zh) | 2015-12-09 |
| US20150376330A1 (en) | 2015-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20150132552A (ko) | 공중합체 제조 방법 | |
| JP5943491B2 (ja) | ポリエステルを調製するプロセス | |
| US10364319B2 (en) | Ring-opening polymerization methods and recyclable biorenewable polyesters | |
| KR20160040468A (ko) | 폴리에스테르의 제조 방법 | |
| US20160083510A1 (en) | Block copolymer and process for preparing the same | |
| Sanchez-Roa et al. | N-heterocyclic carbene-carbodiimide (NHC-CDI) betaines as Organocatalysts for β-butyrolactone polymerization: synthesis of green PHB plasticizers with tailored molecular weights | |
| Li et al. | Lipase-catalyzed ring-opening copolymerization of ω-pentadecalactone and δ-valerolactone by reactive extrusion | |
| Huang et al. | Access to Polyhydroxyalkanoates with Diverse Syndiotacticity via Polymerization by Spiro‐Salen Complexes and Insights into the Stereocontrol Mechanism | |
| US11613605B2 (en) | Block copolymers of cyclic esters and processes for preparing same | |
| Ulker et al. | Enzymatic synthesis and characterization of biodegradable poly (ω-pentadecalactone-co-ε-caprolactone) copolymers | |
| KR101183225B1 (ko) | 폴리락타이드 수지, 이의 제조 방법 및 이를 포함하는 폴리락타이드 수지 조성물 | |
| Yan et al. | Hydrogen Bonding-Driven Ring-Opening Polymerization of β-Lactones to Polyhydroxyalkanoates Using Aminocyclopropenium Carboxylates | |
| WO2023053128A1 (en) | Group 4 complexes of amine tris(phenolate) ligands, ring-opening polymerization of cyclic esters employing same, and polymers and block co-polymers obtained thereby | |
| JP7772471B2 (ja) | ポリ乳酸重合体の製造方法 | |
| Kashio et al. | Ring-opening polymerization of ɛ-caprolactone by base catalyst for synthesis of grafted polysilsesquioxane | |
| US20170226283A1 (en) | Polyester stereocomplexes, compositions comprising same, and methods of making and using same | |
| Habibzadehbizhani | Indium catalysts supported by pincer ligands as initiators for lactide polymerization | |
| CN120435349A (zh) | 碱金属酚类化合物及其用途 | |
| EP4092067A1 (en) | Process for preparing tailor-made lactide copolymers and lactide copolymers thereby obtained | |
| Xu | Living and immortal polymerization of cyclic esters with a dinuclear indium catalyst |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20151016 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |