WO2006085485A1 - 開環重合法および開環重合用活性炭触媒 - Google Patents
開環重合法および開環重合用活性炭触媒 Download PDFInfo
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- WO2006085485A1 WO2006085485A1 PCT/JP2006/301853 JP2006301853W WO2006085485A1 WO 2006085485 A1 WO2006085485 A1 WO 2006085485A1 JP 2006301853 W JP2006301853 W JP 2006301853W WO 2006085485 A1 WO2006085485 A1 WO 2006085485A1
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- WIPO (PCT)
- Prior art keywords
- ring
- opening polymerization
- polymerization method
- activated carbon
- compound
- Prior art date
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 112
- 238000000034 method Methods 0.000 title claims abstract description 42
- 239000003054 catalyst Substances 0.000 title claims abstract description 28
- 238000007151 ring opening polymerisation reaction Methods 0.000 title claims description 52
- -1 oxirane compound Chemical class 0.000 claims abstract description 43
- 229920002557 polyglycidol polymer Polymers 0.000 claims abstract description 26
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 10
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims abstract description 9
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 5
- 239000003999 initiator Substances 0.000 claims abstract description 5
- 125000000524 functional group Chemical group 0.000 claims abstract description 4
- 150000001923 cyclic compounds Chemical class 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 238000007142 ring opening reaction Methods 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 abstract description 3
- 150000005215 alkyl ethers Chemical class 0.000 abstract description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 241001550224 Apha Species 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005639 Lauric acid Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 2
- 239000003575 carbonaceous material Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 1
- CEGRHPCDLKAHJD-UHFFFAOYSA-N 1,1,1-propanetricarboxylic acid Chemical compound CCC(C(O)=O)(C(O)=O)C(O)=O CEGRHPCDLKAHJD-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 244000274847 Betula papyrifera Species 0.000 description 1
- 235000009113 Betula papyrifera Nutrition 0.000 description 1
- 235000009109 Betula pendula Nutrition 0.000 description 1
- 235000010928 Betula populifolia Nutrition 0.000 description 1
- 235000002992 Betula pubescens Nutrition 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- VHRXDQDBJHKEJS-UHFFFAOYSA-N oxetane hydrofluoride Chemical compound F.C1COC1 VHRXDQDBJHKEJS-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
Definitions
- the present invention relates to a ring-opening polymerization method using activated carbon as a catalyst and a catalyst for ring-opening polymerization.
- the ring-opening polymerization method is a polymerization method in which polymerization proceeds by ring-opening of a cyclic compound as a monomer to synthesize a polymer.
- a cyclic compound as a monomer to synthesize a polymer.
- nylon, polyester, polyether, polyethyleneimine, polysiloxane and the like are used.
- Various industrially important synthetic polymers are produced by the ring-opening polymerization method.
- the catalyst acts on the cyclic compound and promotes the ring-opening reaction.
- a catalyst for example, a cation-reactive monomer such as cyclic ether, cyclic formal, or cyclic imine, Lewis acid such as BF-0 (C H), SnCl, or A1C1; alkyl chloride, alkyl, etc.
- Alkyl halides such as rubromide
- Super strong acids such as CF SO H
- CF SO R (R is alkyl
- Li, Na, K, RCOONa, RONa, R NLi (R is an alkyl group), etc. are used for key-on reactive monomers such as cyclic siloxanes, ratatas, and acid anhydrides.
- a catalyst in which oxetane fluoride is supported on an alkali metal fluoride support such as activated carbon.
- the active site is an alkali metal fluoride, and activated charcoal is only a carrier (Patent Literature). 1).
- MoCl and WC1 are used for functional monomers.
- Patent Document 1 Japanese Patent Publication No. 1 49340 (see claim 5)
- an object of the present invention is to provide a catalyst that has an excellent catalytic effect, does not cause side reactions, and does not remain in the produced polymer by filtration and does not cause a decrease in safety or performance deterioration. It is an object of the present invention to provide a catalyst for use in a ring-opening polymerization method using benzene and a powerful polymerization method.
- the first of the present invention is a ring-opening polymerization method in which activated carbon is used as a catalyst in a ring-opening polymerization method in which polymerization proceeds by ring-opening of the cyclic compound (A) as a monomer.
- a polymerization method in which activated carbon is used as a catalyst in a ring-opening polymerization method in which polymerization proceeds by ring-opening of the cyclic compound (A) as a monomer.
- a second aspect of the present invention provides the ring-opening polymerization method according to the first aspect of the present invention, wherein the activated carbon is powdered activated carbon.
- a third aspect of the present invention is the first aspect of the present invention in which the ring-opening polymerization method is ring-opening homopolymerization of the cyclic compound (A) or ring-opening copolymerization of two or more cyclic compounds (A).
- the ring-opening polymerization method described in 2 is provided.
- a fourth aspect of the present invention is the ring-opening according to any one of the first to third aspects of the present invention, wherein the cyclic compound (A) is an oxysilane compound (a) represented by the following general formula (1): A polymerization method is provided.
- R 1 and also H a branched or straight chain alkyl group or aryl group having 1 to 30 carbon atoms; and —CH—M (M is OH, F, Cl, Br, —OR 3 ( R 3 is an Al having 1 to 20 carbon atoms A functional group represented by a kill group, an aryl group or an aryl group)), which may be the same or different. )
- the oxysilane compound (a) is ethylene oxide or propylene oxide.
- Ring-opening polymerization method wherein at least one selected from the group consisting of, butylene oxide, ⁇ -olefin epoxide having 6 to 30 carbon atoms, styrene oxide, glycidol and epichlorohydrin is also selected.
- at least one selected from the group consisting of, butylene oxide, ⁇ -olefin epoxide having 6 to 30 carbon atoms, styrene oxide, glycidol and epichlorohydrin is also selected.
- a sixth aspect of the present invention provides the ring-opening polymerization method according to the fifth aspect of the present invention, wherein the oxsilani compound (a) is glycidol.
- a seventh aspect of the present invention provides the ring-opening polymerization method according to the sixth aspect of the present invention, in which glycidol is reacted using the active hydrogen compound (b) as an initiator.
- An eighth aspect of the present invention provides the ring-opening polymerization method according to the seventh aspect of the present invention, wherein the active hydrogen compound (b) is water or a polyvalent hydroxyl compound, and the product is polyglycidol.
- a ninth aspect of the present invention provides the ring-opening polymerization method according to the seventh aspect of the present invention, wherein the active hydrogen compound (b) is an aliphatic alcohol and the product is a polyglycidol aliphatic alkyl ether.
- a tenth aspect of the present invention provides the ring-opening polymerization method according to the seventh aspect of the present invention, wherein the active hydrogen compound (b) is an aliphatic carboxylic acid and the product is a polyglycidol aliphatic carboxylic acid ester. To do.
- the eleventh aspect of the present invention is (1) comprising only activated carbon.
- a catalyst for ring-opening polymerization is provided.
- a twelfth aspect of the present invention provides the ring-opening polymerization catalyst described in the eleventh aspect of the present invention, which is used for the ring-opening polymerization of an oxsilane compound.
- the activated carbon used has an excellent catalytic effect, does not cause side reactions, and does not remain in the produced polymer by filtration, causing a reduction in safety and performance deterioration.
- An activated carbon used in a ring-opening polymerization method and a vigorous polymerization method using a catalyst that does not have a problem can be provided.
- the cyclic compound (A) which is a monomer is not particularly limited as long as it undergoes ring-opening polymerization in the presence of an activated carbon catalyst.
- Examples of the cyclic compound (A) that can be used in the present invention include oxsilane (a) represented by the following general formula (1).
- R 1 and R 2 are H; a branched or straight chain alkyl group or aryl group having 1 to 30 carbon atoms; and —CH—M (M is OH, F, Cl, Br, —OR 3 (R 3 is an alkyl group having 1 to 20 carbon atoms.
- Preferable oxysilane compound (a) includes a compound in which R 1 and R 2 are PTC in the general formula (1), and R 1 is H and R 2 is a branch having 1 to 30 carbon atoms. Or a straight-chain alkyl group or aryl group, or —CH—M (M is OH, F, Cl, Br, 0 3 is C 1-2.
- alkyl group 0 alkyl group, aryl group or aryl group
- ethylene oxide propylene oxide, butylene oxide, ⁇ -olefin epoxide having 6 to 30 carbon atoms, styrene oxide, glycidol, and epichlorohydrin.
- the ring-opening homopolymerization is a method for ring-opening polymerization of one kind of cyclic compound ( ⁇ ).
- the ring-opening copolymerization is a ring-opening polymerization of two or more kinds of cyclic compounds ( ⁇ ).
- activated carbon used as a catalyst in the present invention those known as conventional porous carbonaceous adsorbents can be used.
- These activated carbons are mainly natural carbon derived from plants such as coal, coatas, pitch, bone charcoal, charcoal, coconut shells, wood, sawdust, and lignin.
- Carbonaceous materials such as quality, natural carbon derived from animals such as bovine bones, organic polymers such as synthetic resin such as phenol cinnamon polyacrylonitrile, and carbonaceous materials such as cocoon are obtained by heat treatment and activated. It is out.
- activated carbon itself may be used!
- activated carbon may be supported on a carrier such as plastic, mineral, ceramics, fiber, etc.
- powdered activated carbon may be granulated using a binder, and mineral or ceramic powder may be used. Powdered activated carbon may also be granulated.
- bone charcoal, charcoal, graphite, carbon black, and the like may contain activated carbon in their structure, these can also be mentioned as partially containing activated carbon in the present invention.
- the activated carbon used in the present invention is not particularly limited as long as the specific surface area is 500 m 2 Zg or more.
- the force is preferably 750 m 2 Zg or more, more preferably 900 m 2 Zg or more, and the upper limit is usually 3000 m 2. It is about Zg.
- the shape of the activated carbon used in the present invention may be any shape such as granular, powder, fibrous, plate-like, Hercam's.
- granular activated carbon Toyo (currently Mitsubishi Chemical) Calgon Co., Ltd. F 400, F300, PCB, BPL, CAL, CPG or APC; Nihon Enviguchi Chemicals Co., Ltd. granular white WH or granular white birch C; Kuraray Examples include Kuraray Coal KW manufactured by Chemical Co., Ltd. and BAC manufactured by Kureha Kagaku Kogyo Co., Ltd.
- the powdered activated carbon include Hakuho A or Hakuho C manufactured by Nippon Environmental Chemicals Co., Ltd.
- fibrous activated carbon examples include FX-300 manufactured by Toho Rayon Co., Ltd .; M-30 manufactured by Osaka Gas Co., Ltd .; KF-1500 manufactured by Toyobo Co., Ltd., etc.
- fibrous activated carbon examples include FX-300 manufactured by Toho Rayon Co., Ltd .; M-30 manufactured by Osaka Gas Co., Ltd .; KF-1500 manufactured by Toyobo Co., Ltd., etc.
- the amount of the activated carbon used is not particularly limited, but is preferably in the range of 0.01 to L0 parts by weight, more preferably 0.1 to 1 parts by weight with respect to 100 parts by weight of the cyclic compound (A). It is.
- the cyclic compound (A) when the cyclic compound (A) has active hydrogen, for example, glycidol, ring-opening homopolymerization using a hydroxyl group of glycidol as an initiator, or other cyclic without active hydrogen. Ring-opening copolymerization with compound (A) is possible.
- active hydrogen compound (b) is used, and the active hydrogen compound (b) is used as an initiator for ring-opening homopolymerization or ring-opening copolymerization with other cyclic compounds (A).
- Active hydrogenation Compound (b) has, for example, one or more hydroxyl group, carboxyl group, amino group and z or thiol group.
- Examples of the active hydrogen compound (b) include water, diols such as ethylene glycol, propylene glycol, butanediol, neopentyl glycol, and hexanediol; ether diols that are condensates thereof; glycerin and trimethylol. And trifunctional or higher polyhydric hydroxyl group compounds such as ethane, trimethylolpropane, pentaerythritol and dipentaerythritol.
- polyglycidol a product obtained by using glycidol as the cyclic compound (A) and using these compounds as the active hydrogen compound (b) is referred to as polyglycidol.
- the active hydrogen compound (b) may be a monohydroxy compound, preferably an aliphatic, alicyclic or aromatic alcohol having 1 to 30 carbon atoms, more preferably an aliphatic alcohol. It is. Specific examples include lower alcohols having 1 or more carbon atoms and higher alcohols having 10 or more carbon atoms.
- the product is the corresponding alcohol ester of polyglycidol.
- an aliphatic alcohol is used as the active hydrogen compound (b)
- a polyglycidol aliphatic alkyl ether is obtained.
- the active hydrogen compound (b) may be a mono- or polycarboxylate compound.
- lower aliphatic carboxylic acids such as formic acid, acetic acid to decanoic acid, polymerizable unsaturated carboxylic acids such as (meth) acrylic acid, higher aliphatic carboxylic acids such as lauric acid to stearic acid; maleic acid, succinic acid Aliphatic saturated or polymerizable unsaturated dicarboxylic acids such as acids and adipic acids; Alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid; Aromatic dicarboxylic acids such as phthalic acids; Propanetricarboxylic acid, trimellitic acid, aminotriacetic acid And polycarboxylic acids such as butanetetracarboxylic acid, pyromellitic acid, and tetracarboxylic acids such as ethylenediaminetetraacetic acid.
- the product is the corresponding carboxylic acid ester of polyglycidol.
- a polyglycidol aliphatic carboxylic acid ester is obtained.
- the reaction temperature and reaction time of the ring-opening polymerization are not particularly limited, but the reaction temperature is, for example, 100 ° C to 200 ° C, and the reaction time is preferably 1 hour or more, and 5 hours. More preferably, it is the above.
- a cyclic compound as a monomer and activated carbon are included as essential components in the reaction system.
- low molecular weight hydrocarbons for example, carbon Aliphatic hydrocarbons of about 4 to 12
- cycloaliphatic hydrocarbons such as cyclohexane
- aromatic hydrocarbons such as toluene
- chain ethers such as dimethyl ether to ethylene glycol dimethyl ether
- Add a solvent such as ketones such as acetone, methylethylketone, cyclohexanone, amides such as N, N-dimethylformamide, and cyclic ethers such as tetrahydrofuran and dioxane.
- the reaction format may be batch, semi-batch or continuous.
- the reaction apparatus include a stirring tank type, a flow type like a packed tower, and a fluidized bed type.
- a packed tower type reaction apparatus is used, and activated carbon as a catalyst is packed therein to form a catalyst layer, and the cyclic compound compound (A) alone or the cyclic compound (A) and the active hydrogen compound (b)
- a method in which a mixture of the above is passed through the catalyst layer is preferred. According to this method, it is possible to easily reactivate and dry by passing water vapor through the deactivated catalyst layer, which can save the trouble of filtering the catalyst.
- the obtained polyglycidol had hue (APHA) 20, acid value (KOHmgZg) O. 20, moisture (%) 0.22, hydroxyl value (KOHmgZg) 1146, viscosity (mPa.sZ40.C) 8600.
- the obtained polyglycidol had a hue (APHA) of 15, an acid value (KOHmgZg) of 0.06, a water content (%) of 0.21, a hydroxyl value (KOHmgZg) of 948, and a viscosity (mPa'sZ60 ° C) of 7100.
- the obtained polyglycidol lauryl ether has a hue (APHA) of 20, an acid value (KOHmg / g) of 0.45, a water content (%) of 0.013, an OH value (KOHmgZg) of 583.0, and a viscosity (mPa-S, 40 ° C) 15200.
- Lauric acid 0.5mol (100.16g) and activated carbon (Nippon Enviguchi Chemicals, Shirasagi A) 3.224g in a 1 liter 4-liter flask equipped with a nitrogen inlet tube, stirrer, condenser, temperature controller and dropping cylinder was heated and heated to 140 ° C. Next, while maintaining the reaction temperature at 140 ° C., 3.0 mol (222.24 g) of glycidol was added dropwise over 5 hours, and the reaction was continued until the oxolan concentration in the system was less than 0.1%. After cooling, the activated carbon was removed from the reaction system by filtration to obtain about 300 g of polyglycidol monolaurate.
- the resulting polyglycidol monolaurate has appearance (APHA) 20, acid value (KOH mg / g) 2.44, moisture (%) 0.049, OH value (KOHmg / g) 598.1, saponification value (KOH mg / g) was 88.8, and the viscosity (mPa ′ S, 40 ° C.) was 14470.
- the resulting polyglycidol monolaurate has an appearance (APHA) of 15, acid value (KOH mg / g) of 0.32, moisture (%) of 0.088, OH value (KOHmgZg) of 639, Keny rating (KOHmg / g ) 61.1, Viscosity (mPa 'S, 40. C) 44000.
- the activated carbon to be used is excellent in catalytic activity, and side reactions are suppressed.
- the catalyst can be easily separated and removed from the target product by filtration, and the force does not cause problems of safety and performance deterioration of the target product unlike conventional catalysts. Therefore, the method of the present invention is extremely excellent as an industrial production method of a ring-opening polymer of a cyclic compound.
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Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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EP06712996A EP1857485B1 (en) | 2005-02-10 | 2006-02-03 | Ring-opening polymerization method using activated carbon as catalyst |
CN2006800033668A CN101111533B (zh) | 2005-02-10 | 2006-02-03 | 开环聚合方法和开环聚合用活性炭催化剂 |
JP2007502584A JP5094383B2 (ja) | 2005-02-10 | 2006-02-03 | 開環重合法および開環重合用活性炭触媒 |
DE602006021286T DE602006021286D1 (de) | 2005-02-10 | 2006-02-03 | Ringöffnungspolymerisation mittels aktivkohle als katalysator |
KR1020077020498A KR101257525B1 (ko) | 2005-02-10 | 2006-02-03 | 개환 중합법 및 개환 중합용 활성탄 촉매 |
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JP2005034764 | 2005-02-10 | ||
JP2005-034764 | 2005-02-10 |
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WO2006085485A1 true WO2006085485A1 (ja) | 2006-08-17 |
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PCT/JP2006/301853 WO2006085485A1 (ja) | 2005-02-10 | 2006-02-03 | 開環重合法および開環重合用活性炭触媒 |
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US (1) | US7851583B2 (ja) |
EP (1) | EP1857485B1 (ja) |
JP (1) | JP5094383B2 (ja) |
KR (1) | KR101257525B1 (ja) |
CN (1) | CN101111533B (ja) |
DE (1) | DE602006021286D1 (ja) |
TW (1) | TWI389933B (ja) |
WO (1) | WO2006085485A1 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2009249500A (ja) * | 2008-04-07 | 2009-10-29 | Hakuto Co Ltd | 重合性高分岐ポリマー及びその製造方法 |
WO2010087395A1 (ja) | 2009-01-29 | 2010-08-05 | 花王株式会社 | ポリグリセリルエーテル誘導体の製造方法 |
JP2011038095A (ja) * | 2009-08-10 | 2011-02-24 | Mitsubishi Chemicals Corp | ポリオキシアルキレングリコールの製造方法 |
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US3250807A (en) * | 1963-08-23 | 1966-05-10 | Du Pont | Dicarboxylic acids of fluorocarbon ethers and fluorides, esters, amides and salts thereof |
JP2002030144A (ja) * | 2000-07-14 | 2002-01-31 | Nof Corp | ポリエーテル化合物の製造方法 |
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US3370056A (en) | 1963-04-04 | 1968-02-20 | Takeda Chemical Industries Ltd | Production of polyoxyalkylene ethers |
GB1038365A (en) * | 1963-05-16 | 1966-08-10 | Du Pont | Novel perfluoroolefin epoxide polyethers |
NL8104025A (nl) * | 1981-08-29 | 1983-03-16 | Stamicarbon | Werkwijze voor de bereiding van ethercarboxylaten. |
JPS60136536A (ja) * | 1983-12-26 | 1985-07-20 | Daikin Ind Ltd | 2,2,3−トリフルオロプロピオニルフルオライドの製法 |
US4769184A (en) * | 1987-09-08 | 1988-09-06 | Nippon Mektron Limited | Process for producing carbonyl fluoride compound |
US5010187A (en) * | 1988-11-18 | 1991-04-23 | Dow Chemical Company | Production of polyether polyols with reduced unsaturation |
US5952457A (en) * | 1995-09-12 | 1999-09-14 | Mitsui Chemicals, Inc. | Polymerization catalyst for alkylene oxide compound and production process of poly(alkylene oxide) |
US5798412A (en) * | 1997-07-16 | 1998-08-25 | Huntsman Petrochemical Corporation | Alkylene glycol production using carbon catalysts |
IT1301999B1 (it) * | 1998-08-05 | 2000-07-20 | Enichem Spa | Catalizzatore, processo per la produzione di acqua ossigenata esuo impiego in processi di ossidazione. |
JP5036989B2 (ja) * | 2005-09-01 | 2012-09-26 | 株式会社ダイセル | ポリグリセリンおよびその製造方法 |
-
2006
- 2006-02-03 WO PCT/JP2006/301853 patent/WO2006085485A1/ja active Application Filing
- 2006-02-03 DE DE602006021286T patent/DE602006021286D1/de active Active
- 2006-02-03 EP EP06712996A patent/EP1857485B1/en not_active Not-in-force
- 2006-02-03 KR KR1020077020498A patent/KR101257525B1/ko not_active IP Right Cessation
- 2006-02-03 JP JP2007502584A patent/JP5094383B2/ja active Active
- 2006-02-03 CN CN2006800033668A patent/CN101111533B/zh not_active Expired - Fee Related
- 2006-02-03 US US11/795,803 patent/US7851583B2/en not_active Expired - Fee Related
- 2006-02-09 TW TW095104301A patent/TWI389933B/zh not_active IP Right Cessation
Patent Citations (2)
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US3250807A (en) * | 1963-08-23 | 1966-05-10 | Du Pont | Dicarboxylic acids of fluorocarbon ethers and fluorides, esters, amides and salts thereof |
JP2002030144A (ja) * | 2000-07-14 | 2002-01-31 | Nof Corp | ポリエーテル化合物の製造方法 |
Non-Patent Citations (1)
Title |
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See also references of EP1857485A4 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009249500A (ja) * | 2008-04-07 | 2009-10-29 | Hakuto Co Ltd | 重合性高分岐ポリマー及びその製造方法 |
WO2010087395A1 (ja) | 2009-01-29 | 2010-08-05 | 花王株式会社 | ポリグリセリルエーテル誘導体の製造方法 |
JP2011038095A (ja) * | 2009-08-10 | 2011-02-24 | Mitsubishi Chemicals Corp | ポリオキシアルキレングリコールの製造方法 |
Also Published As
Publication number | Publication date |
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KR20070108395A (ko) | 2007-11-09 |
EP1857485A4 (en) | 2008-12-31 |
JPWO2006085485A1 (ja) | 2008-06-26 |
US7851583B2 (en) | 2010-12-14 |
CN101111533A (zh) | 2008-01-23 |
TWI389933B (zh) | 2013-03-21 |
EP1857485B1 (en) | 2011-04-13 |
KR101257525B1 (ko) | 2013-04-23 |
DE602006021286D1 (de) | 2011-05-26 |
US20080161533A1 (en) | 2008-07-03 |
JP5094383B2 (ja) | 2012-12-12 |
CN101111533B (zh) | 2011-02-09 |
EP1857485A1 (en) | 2007-11-21 |
TW200635981A (en) | 2006-10-16 |
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