JP6049148B2 - （ホスホニル）芳香族ジエステルおよび酸のホモポリマーおよびコポリマーの調製 - Google Patents
（ホスホニル）芳香族ジエステルおよび酸のホモポリマーおよびコポリマーの調製 Download PDFInfo
- Publication number
- JP6049148B2 JP6049148B2 JP2014545899A JP2014545899A JP6049148B2 JP 6049148 B2 JP6049148 B2 JP 6049148B2 JP 2014545899 A JP2014545899 A JP 2014545899A JP 2014545899 A JP2014545899 A JP 2014545899A JP 6049148 B2 JP6049148 B2 JP 6049148B2
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- Japan
- Prior art keywords
- dimethyl
- structural formula
- phosphonyl
- methoxy
- phenoxy
- 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.)
- Expired - Fee Related
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- 229920001577 copolymer Polymers 0.000 title claims description 12
- 229920001519 homopolymer Polymers 0.000 title claims description 6
- -1 aromatic diesters Chemical class 0.000 title description 21
- 125000005499 phosphonyl group Chemical group 0.000 title description 11
- 238000002360 preparation method Methods 0.000 title description 7
- 239000002253 acid Substances 0.000 title description 5
- 150000007513 acids Chemical class 0.000 title description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
- 150000001491 aromatic compounds Chemical class 0.000 claims description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims 2
- GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 claims 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 12
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 12
- 229940035437 1,3-propanediol Drugs 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000003063 flame retardant Substances 0.000 description 9
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 9
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- NJLFKVDADYXYFX-UHFFFAOYSA-N dimethyl 5-(dimethylphosphorylmethoxy)benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(OCP(C)(C)=O)=CC(C(=O)OC)=C1 NJLFKVDADYXYFX-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000002411 thermogravimetry Methods 0.000 description 6
- DOSDTCPDBPRFHQ-UHFFFAOYSA-N dimethyl 5-hydroxybenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(O)=CC(C(=O)OC)=C1 DOSDTCPDBPRFHQ-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920013627 Sorona Polymers 0.000 description 3
- VACOMSNNWGXHSF-UHFFFAOYSA-N chloro(dimethylphosphoryl)methane Chemical compound CP(C)(=O)CCl VACOMSNNWGXHSF-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229920001707 polybutylene terephthalate Polymers 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 2
- KEULOYYBYNGHRJ-UHFFFAOYSA-N 5-(dimethylphosphorylmethoxy)benzene-1,3-dicarboxylic acid Chemical compound CP(C)(=O)COC1=CC(C(O)=O)=CC(C(O)=O)=C1 KEULOYYBYNGHRJ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- IGPFFLDNJJJXHV-UHFFFAOYSA-N [chloromethyl(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(CCl)C1=CC=CC=C1 IGPFFLDNJJJXHV-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- YXEDCURRROXRPL-UHFFFAOYSA-K bis[(2-hydroxyacetyl)oxy]stibanyl 2-hydroxyacetate Chemical compound [Sb+3].OCC([O-])=O.OCC([O-])=O.OCC([O-])=O YXEDCURRROXRPL-UHFFFAOYSA-K 0.000 description 2
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229940071125 manganese acetate Drugs 0.000 description 2
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000004122 cyclic group Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- MBAPFXBNYNNIPE-UHFFFAOYSA-N dimethyl 5-(dimethylphosphorylmethoxy)benzene-1,3-dicarboxylate Chemical compound CP(=O)(C)COC=1C=C(C=C(C(=O)OC)C1)C(=O)OC.CP(=O)(C)COC=1C=C(C=C(C(=O)OC)C1)C(=O)OC MBAPFXBNYNNIPE-UHFFFAOYSA-N 0.000 description 1
- KLXIGANBJHKQHL-UHFFFAOYSA-N dimethyl 5-(diphenylphosphorylmethoxy)benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(OCP(=O)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 KLXIGANBJHKQHL-UHFFFAOYSA-N 0.000 description 1
- RQOKIVVUNQCMJS-UHFFFAOYSA-N dimethylphosphorylmethanol Chemical compound CP(C)(=O)CO RQOKIVVUNQCMJS-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000569 multi-angle light scattering Methods 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 239000008096 xylene 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
- C08G63/6924—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6926—Dicarboxylic acids and dihydroxy compounds
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)
- Fireproofing Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/314,616 | 2011-12-08 | ||
| US13/314,616 US8722846B2 (en) | 2011-12-08 | 2011-12-08 | Preparation of homopolymer and copolymers of (phosphonyl)aromatic diesters and acids |
| PCT/US2012/060009 WO2013085619A1 (en) | 2011-12-08 | 2012-10-12 | Preparation of homopolymer and copolymers of (phosphonyl)aromatic diesters and acids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015500370A JP2015500370A (ja) | 2015-01-05 |
| JP2015500370A5 JP2015500370A5 (enExample) | 2015-11-26 |
| JP6049148B2 true JP6049148B2 (ja) | 2016-12-21 |
Family
ID=48572580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014545899A Expired - Fee Related JP6049148B2 (ja) | 2011-12-08 | 2012-10-12 | （ホスホニル）芳香族ジエステルおよび酸のホモポリマーおよびコポリマーの調製 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8722846B2 (enExample) |
| EP (1) | EP2788399B1 (enExample) |
| JP (1) | JP6049148B2 (enExample) |
| KR (1) | KR101922756B1 (enExample) |
| CN (1) | CN103958563B (enExample) |
| AU (1) | AU2012348327B2 (enExample) |
| IN (1) | IN2014DN03466A (enExample) |
| WO (1) | WO2013085619A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8513454B2 (en) * | 2011-12-08 | 2013-08-20 | E I Du Pont De Nemours And Company | Preparation of (phosphonyl) aromatic diesters and acids |
| EP3337844A1 (en) | 2015-08-20 | 2018-06-27 | 3M Innovative Properties Company | Functionalized polyester polymers and film articles |
| CN112480168B (zh) * | 2020-11-26 | 2022-05-31 | 江苏利思德新材料有限公司 | 一种含磷阻燃剂和阻燃高分子材料 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4131594A (en) | 1974-05-25 | 1978-12-26 | Teijin Limited | Fire-resistant thermoplastic polyester resin compositions and process for rendering polyesters fire-resistant |
| US3932566A (en) * | 1974-09-16 | 1976-01-13 | Celanese Corporation | Phosphonate polymers |
| US4157436A (en) * | 1975-10-14 | 1979-06-05 | Toyo Boseki Kabushiki Kaisha | Phosphorus-containing polyesters |
| US4127566A (en) * | 1977-12-22 | 1978-11-28 | Monsanto Company | Process for preparation of flame retardant polyesters |
| JPH0641512B2 (ja) * | 1989-01-18 | 1994-06-01 | 日本エステル株式会社 | 耐炎性ポリエステルの製造法 |
| KR960701122A (ko) | 1993-02-22 | 1996-02-24 | 나가따 마사오 | 난연 폴리에스테르(flame retardant polyester) |
| JP3321233B2 (ja) * | 1993-03-11 | 2002-09-03 | 日本エステル株式会社 | 接着剤用ポリエステル |
| DE4436079A1 (de) * | 1994-10-10 | 1996-04-11 | Hoechst Ag | Verfahren zur Herstellung phosphorhaltiger Dicarbonsäuren |
| JPH11315212A (ja) * | 1998-05-01 | 1999-11-16 | Toray Ind Inc | 難燃性樹脂組成物 |
| EP1153953B1 (en) | 1998-10-23 | 2008-11-05 | Toyo Boseki Kabushiki Kaisha | Polymerization catalyst for polyester production, polyester, and process for producing polyester |
| JP3724622B2 (ja) * | 1999-03-12 | 2005-12-07 | 東洋紡績株式会社 | 抗菌性繊維及びその製造方法 |
| TW593526B (en) * | 2001-09-20 | 2004-06-21 | Wangsuen Su Jen | Phosphorus group containing flame retardant hardener, advanced epoxy resins and cured epoxy resins thereof |
| US8895648B2 (en) | 2009-05-13 | 2014-11-25 | Chemtura Corporation | Phosphorus-containing flame retardants |
| WO2011028778A2 (en) | 2009-09-02 | 2011-03-10 | E. I. Du Pont De Nemours And Company | Polyesters comprising fluorovinylether functionalized aromatic moieties |
| AU2010289572A1 (en) | 2009-09-02 | 2012-03-15 | E. I. Du Pont De Nemours And Company | Fluoroether functionalized aromatic diesters and derivatives thereof |
| CN101805444B (zh) * | 2010-03-16 | 2012-04-25 | 四川大学 | 耐熔滴阻燃聚酯及其纳米复合材料和它们的制备方法 |
| US8513454B2 (en) | 2011-12-08 | 2013-08-20 | E I Du Pont De Nemours And Company | Preparation of (phosphonyl) aromatic diesters and acids |
-
2011
- 2011-12-08 US US13/314,616 patent/US8722846B2/en active Active
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2012
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- 2012-10-12 AU AU2012348327A patent/AU2012348327B2/en not_active Ceased
- 2012-10-12 EP EP12855446.6A patent/EP2788399B1/en not_active Not-in-force
- 2012-10-12 KR KR1020147018474A patent/KR101922756B1/ko not_active Expired - Fee Related
- 2012-10-12 JP JP2014545899A patent/JP6049148B2/ja not_active Expired - Fee Related
- 2012-10-12 CN CN201280058423.8A patent/CN103958563B/zh active Active
- 2012-10-12 IN IN3466DEN2014 patent/IN2014DN03466A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US8722846B2 (en) | 2014-05-13 |
| KR20140109923A (ko) | 2014-09-16 |
| EP2788399A1 (en) | 2014-10-15 |
| WO2013085619A1 (en) | 2013-06-13 |
| CN103958563A (zh) | 2014-07-30 |
| EP2788399B1 (en) | 2016-09-14 |
| KR101922756B1 (ko) | 2018-11-27 |
| AU2012348327B2 (en) | 2016-07-28 |
| JP2015500370A (ja) | 2015-01-05 |
| US20130150548A1 (en) | 2013-06-13 |
| AU2012348327A1 (en) | 2014-05-22 |
| EP2788399A4 (en) | 2015-07-29 |
| IN2014DN03466A (enExample) | 2015-06-05 |
| CN103958563B (zh) | 2015-09-23 |
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