JP4867386B2 - ポリエステルの製造方法 - Google Patents
ポリエステルの製造方法 Download PDFInfo
- Publication number
- JP4867386B2 JP4867386B2 JP2006042474A JP2006042474A JP4867386B2 JP 4867386 B2 JP4867386 B2 JP 4867386B2 JP 2006042474 A JP2006042474 A JP 2006042474A JP 2006042474 A JP2006042474 A JP 2006042474A JP 4867386 B2 JP4867386 B2 JP 4867386B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- polyester
- group
- esterification reaction
- slurry
- 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.)
- Active
Links
- 229920000728 polyester Polymers 0.000 title claims description 252
- 238000004519 manufacturing process Methods 0.000 title claims description 61
- 238000005886 esterification reaction Methods 0.000 claims description 224
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 170
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 162
- 238000006068 polycondensation reaction Methods 0.000 claims description 154
- 238000000034 method Methods 0.000 claims description 141
- 239000002002 slurry Substances 0.000 claims description 137
- 230000032050 esterification Effects 0.000 claims description 35
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 35
- 238000002360 preparation method Methods 0.000 claims description 31
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 15
- 239000007795 chemical reaction product Substances 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 13
- 239000000376 reactant Substances 0.000 claims description 9
- -1 polyethylene terephthalate Polymers 0.000 description 303
- 229910052698 phosphorus Inorganic materials 0.000 description 88
- 239000011574 phosphorus Substances 0.000 description 87
- 229910052782 aluminium Inorganic materials 0.000 description 84
- 230000000694 effects Effects 0.000 description 66
- 239000000126 substance Substances 0.000 description 61
- 150000002430 hydrocarbons Chemical group 0.000 description 59
- 239000003054 catalyst Substances 0.000 description 58
- 125000004432 carbon atom Chemical group C* 0.000 description 57
- 150000001875 compounds Chemical class 0.000 description 56
- 150000003018 phosphorus compounds Chemical class 0.000 description 53
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 50
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 47
- 125000003118 aryl group Chemical group 0.000 description 46
- 125000001424 substituent group Chemical group 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 41
- 239000000243 solution Substances 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 28
- 230000003197 catalytic effect Effects 0.000 description 27
- 125000003827 glycol group Chemical group 0.000 description 27
- 125000000217 alkyl group Chemical group 0.000 description 26
- 239000001257 hydrogen Substances 0.000 description 26
- 229910052739 hydrogen Inorganic materials 0.000 description 26
- 125000003545 alkoxy group Chemical group 0.000 description 25
- 239000002253 acid Substances 0.000 description 24
- 229910052751 metal Inorganic materials 0.000 description 22
- 239000002184 metal Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 20
- 230000001276 controlling effect Effects 0.000 description 19
- 125000001624 naphthyl group Chemical group 0.000 description 19
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 18
- 230000001965 increasing effect Effects 0.000 description 18
- 230000000704 physical effect Effects 0.000 description 18
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 description 17
- 125000002947 alkylene group Chemical group 0.000 description 17
- 238000005259 measurement Methods 0.000 description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 17
- 125000002723 alicyclic group Chemical group 0.000 description 16
- 229920001225 polyester resin Polymers 0.000 description 16
- 239000004645 polyester resin Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 13
- 229910052708 sodium Inorganic materials 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- 238000012546 transfer Methods 0.000 description 13
- WSOJYRTVHMMFST-UHFFFAOYSA-N benzyl(ethoxy)phosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=CC=C1 WSOJYRTVHMMFST-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 241000894007 species Species 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 11
- 150000001340 alkali metals Chemical class 0.000 description 11
- 229940009827 aluminum acetate Drugs 0.000 description 11
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 11
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 11
- 125000005647 linker group Chemical group 0.000 description 11
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 11
- 150000003009 phosphonic acids Chemical class 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 10
- 150000001342 alkaline earth metals Chemical class 0.000 description 10
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 229910052744 lithium Inorganic materials 0.000 description 10
- 239000012528 membrane Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 9
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 229910052749 magnesium Inorganic materials 0.000 description 9
- 239000011777 magnesium Substances 0.000 description 9
- 229920000139 polyethylene terephthalate Polymers 0.000 description 9
- 239000005020 polyethylene terephthalate Substances 0.000 description 9
- 229910052719 titanium Inorganic materials 0.000 description 9
- 239000010936 titanium Substances 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 8
- 230000008901 benefit Effects 0.000 description 8
- 238000007334 copolymerization reaction Methods 0.000 description 8
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 8
- 229910052718 tin Inorganic materials 0.000 description 8
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 7
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229920006267 polyester film Polymers 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229920002799 BoPET Polymers 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 229910052790 beryllium Inorganic materials 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- AIPRAPZUGUTQKX-UHFFFAOYSA-N diethoxyphosphorylmethylbenzene Chemical compound CCOP(=O)(OCC)CC1=CC=CC=C1 AIPRAPZUGUTQKX-UHFFFAOYSA-N 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 229910052712 strontium Inorganic materials 0.000 description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 5
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 5
- MILSYCKGLDDVLM-UHFFFAOYSA-N 2-phenylpropan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 description 5
- 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 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 229910052788 barium Inorganic materials 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 238000011088 calibration curve Methods 0.000 description 5
- 239000013522 chelant Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 5
- UFZOPKFMKMAWLU-UHFFFAOYSA-N ethoxy(methyl)phosphinic acid Chemical compound CCOP(C)(O)=O UFZOPKFMKMAWLU-UHFFFAOYSA-N 0.000 description 5
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 5
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 4
- GJDRKHHGPHLVNI-UHFFFAOYSA-N 2,6-ditert-butyl-4-(diethoxyphosphorylmethyl)phenol Chemical compound CCOP(=O)(OCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GJDRKHHGPHLVNI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001339 alkali metal compounds Chemical class 0.000 description 4
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 4
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000002685 polymerization catalyst Substances 0.000 description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- LUMDPYUBJBEXKD-UHFFFAOYSA-N (3-butylphenyl)methylphosphonic acid Chemical compound CCCCC1=CC=CC(CP(O)(O)=O)=C1 LUMDPYUBJBEXKD-UHFFFAOYSA-N 0.000 description 3
- 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 3
- NYYLZXREFNYPKB-UHFFFAOYSA-N 1-[ethoxy(methyl)phosphoryl]oxyethane Chemical compound CCOP(C)(=O)OCC NYYLZXREFNYPKB-UHFFFAOYSA-N 0.000 description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Natural products CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- OXDOANYFRLHSML-UHFFFAOYSA-N dimethoxyphosphorylbenzene Chemical compound COP(=O)(OC)C1=CC=CC=C1 OXDOANYFRLHSML-UHFFFAOYSA-N 0.000 description 3
- BEQVQKJCLJBTKZ-UHFFFAOYSA-N diphenylphosphinic acid Chemical compound C=1C=CC=CC=1P(=O)(O)C1=CC=CC=C1 BEQVQKJCLJBTKZ-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000011002 quantification Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- OBIWKSIDJBJZSC-UHFFFAOYSA-N (2-hydroxyphenyl)methylphosphonic acid Chemical compound OC1=CC=CC=C1CP(O)(O)=O OBIWKSIDJBJZSC-UHFFFAOYSA-N 0.000 description 2
- WBSRIXCTCFFHEF-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WBSRIXCTCFFHEF-UHFFFAOYSA-N 0.000 description 2
- SDCQMEQCOBYSQI-UHFFFAOYSA-N (3-methyl-5-nitrophenyl)phosphonic acid Chemical compound CC1=CC([N+]([O-])=O)=CC(P(O)(O)=O)=C1 SDCQMEQCOBYSQI-UHFFFAOYSA-N 0.000 description 2
- WZLRATMNLTXDAV-UHFFFAOYSA-N 1-benzofuran-2-ylmethylphosphonic acid Chemical compound C1=CC=C2OC(CP(O)(=O)O)=CC2=C1 WZLRATMNLTXDAV-UHFFFAOYSA-N 0.000 description 2
- HTBJIESBRFWCQY-UHFFFAOYSA-N 1-diethoxyphosphoryl-3-methyl-5-nitrobenzene Chemical compound CCOP(=O)(OCC)C1=CC(C)=CC([N+]([O-])=O)=C1 HTBJIESBRFWCQY-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- SAJFQHPVIYPPEY-UHFFFAOYSA-N 2,6-ditert-butyl-4-(dioctadecoxyphosphorylmethyl)phenol Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SAJFQHPVIYPPEY-UHFFFAOYSA-N 0.000 description 2
- CJBVGVDGFXKBJU-UHFFFAOYSA-N 2,6-ditert-butyl-4-(diphenoxyphosphorylmethyl)phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)=C1 CJBVGVDGFXKBJU-UHFFFAOYSA-N 0.000 description 2
- OXANJCRGVJNHTB-UHFFFAOYSA-N 2-(diethoxyphosphorylmethyl)phenol Chemical compound CCOP(=O)(OCC)CC1=CC=CC=C1O OXANJCRGVJNHTB-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- XBIUWALDKXACEA-UHFFFAOYSA-N 3-[bis(2,4-dioxopentan-3-yl)alumanyl]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)[Al](C(C(C)=O)C(C)=O)C(C(C)=O)C(C)=O XBIUWALDKXACEA-UHFFFAOYSA-N 0.000 description 2
- MORLYCDUFHDZKO-UHFFFAOYSA-N 3-[hydroxy(phenyl)phosphoryl]propanoic acid Chemical compound OC(=O)CCP(O)(=O)C1=CC=CC=C1 MORLYCDUFHDZKO-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- XNDIKJYVRQVEEP-UHFFFAOYSA-N 4-[4-[[ethoxy(hydroxy)phosphoryl]methyl]benzoyl]benzoic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C(=O)C1=CC=C(C(O)=O)C=C1 XNDIKJYVRQVEEP-UHFFFAOYSA-N 0.000 description 2
- MTMBHYORFSPVAZ-UHFFFAOYSA-N 4-[4-[[ethoxy(hydroxy)phosphoryl]methyl]phenoxy]benzoic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1OC1=CC=C(C(O)=O)C=C1 MTMBHYORFSPVAZ-UHFFFAOYSA-N 0.000 description 2
- PZCXTPUMSALHHO-UHFFFAOYSA-N 4-[4-[[ethoxy(hydroxy)phosphoryl]methyl]phenyl]sulfanylbenzoic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1SC1=CC=C(C(O)=O)C=C1 PZCXTPUMSALHHO-UHFFFAOYSA-N 0.000 description 2
- NWYCCOQDKLJCDB-UHFFFAOYSA-N 4-[[4-[[ethoxy(hydroxy)phosphoryl]methyl]phenyl]methyl]benzoic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1CC1=CC=C(C(O)=O)C=C1 NWYCCOQDKLJCDB-UHFFFAOYSA-N 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- YCYLCVMIVJNHOV-UHFFFAOYSA-N 4-dimethoxyphosphorylphenol Chemical compound COP(=O)(OC)C1=CC=C(O)C=C1 YCYLCVMIVJNHOV-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 2
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- RBUSKRANSOJGID-UHFFFAOYSA-N [4-(4-butylbenzoyl)phenyl]methyl-ethoxyphosphinic acid Chemical compound C1=CC(CCCC)=CC=C1C(=O)C1=CC=C(CP(O)(=O)OCC)C=C1 RBUSKRANSOJGID-UHFFFAOYSA-N 0.000 description 2
- YAVQVNMMBVXEPS-UHFFFAOYSA-N [4-(4-butylphenyl)sulfonylphenyl]methyl-ethoxyphosphinic acid Chemical compound C1=CC(CCCC)=CC=C1S(=O)(=O)C1=CC=C(CP(O)(=O)OCC)C=C1 YAVQVNMMBVXEPS-UHFFFAOYSA-N 0.000 description 2
- MEIKLVLBWBGUPF-UHFFFAOYSA-N [4-[(4-butylphenyl)methyl]phenyl]methyl-ethoxyphosphinic acid Chemical compound C1=CC(CCCC)=CC=C1CC1=CC=C(CP(O)(=O)OCC)C=C1 MEIKLVLBWBGUPF-UHFFFAOYSA-N 0.000 description 2
- YLEKXZFMCOFOCG-UHFFFAOYSA-N [4-[2-(4-butylphenyl)propan-2-yl]phenyl]methyl-ethoxyphosphinic acid Chemical compound C1=CC(CCCC)=CC=C1C(C)(C)C1=CC=C(CP(O)(=O)OCC)C=C1 YLEKXZFMCOFOCG-UHFFFAOYSA-N 0.000 description 2
- JKHZLDHYHLPKOW-UHFFFAOYSA-N [PH2](OC1=CC=C(C=C1)O)=O Chemical compound [PH2](OC1=CC=C(C=C1)O)=O JKHZLDHYHLPKOW-UHFFFAOYSA-N 0.000 description 2
- HPUPGAFDTWIMBR-UHFFFAOYSA-N [methyl(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(C)OC1=CC=CC=C1 HPUPGAFDTWIMBR-UHFFFAOYSA-N 0.000 description 2
- PEGCITODQASXKH-UHFFFAOYSA-N [methyl(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C)C1=CC=CC=C1 PEGCITODQASXKH-UHFFFAOYSA-N 0.000 description 2
- CDOMXXVCZQOOMT-UHFFFAOYSA-N [phenoxy(phenyl)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(C=1C=CC=CC=1)(=O)OC1=CC=CC=C1 CDOMXXVCZQOOMT-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- NLEMQLLVZYBBBF-UHFFFAOYSA-N benzylphosphonic acid;magnesium Chemical compound [Mg].OP(O)(=O)CC1=CC=CC=C1.OP(O)(=O)CC1=CC=CC=C1 NLEMQLLVZYBBBF-UHFFFAOYSA-N 0.000 description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 2
- 229940005991 chloric acid Drugs 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000011437 continuous method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 2
- WCOATMADISNSBV-UHFFFAOYSA-K diacetyloxyalumanyl acetate Chemical compound [Al+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WCOATMADISNSBV-UHFFFAOYSA-K 0.000 description 2
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- VZEGPPPCKHRYGO-UHFFFAOYSA-N diethoxyphosphorylbenzene Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1 VZEGPPPCKHRYGO-UHFFFAOYSA-N 0.000 description 2
- LNHLAKVYPNQLQR-UHFFFAOYSA-L dilithium;1-naphthalen-1-ylpropyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [Li+].[Li+].C1=CC=C2C(C(CC)P([O-])([O-])=O)=CC=CC2=C1 LNHLAKVYPNQLQR-UHFFFAOYSA-L 0.000 description 2
- KJGANGXUPIUXKS-UHFFFAOYSA-J dimagnesium 1-naphthalen-1-ylpropyl-dioxido-oxo-lambda5-phosphane Chemical compound C(C)C(C1=CC=CC2=CC=CC=C12)P([O-])([O-])=O.C(C)C(C1=CC=CC2=CC=CC=C12)P([O-])([O-])=O.[Mg+2].[Mg+2] KJGANGXUPIUXKS-UHFFFAOYSA-J 0.000 description 2
- QLNYTKJCHFEIDA-UHFFFAOYSA-N dimethoxyphosphorylmethylbenzene Chemical compound COP(=O)(OC)CC1=CC=CC=C1 QLNYTKJCHFEIDA-UHFFFAOYSA-N 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000006840 diphenylmethane group Chemical group 0.000 description 2
- CIJWIJSYZZLMGD-UHFFFAOYSA-N diphenylphosphoryloxybenzene Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)OC1=CC=CC=C1 CIJWIJSYZZLMGD-UHFFFAOYSA-N 0.000 description 2
- OJHFUEJZAGFPHM-UHFFFAOYSA-L disodium;1-naphthalen-1-ylpropyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [Na+].[Na+].C1=CC=C2C(C(CC)P([O-])([O-])=O)=CC=CC2=C1 OJHFUEJZAGFPHM-UHFFFAOYSA-L 0.000 description 2
- DGOHHJOTBMONNG-UHFFFAOYSA-L disodium;benzyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [Na+].[Na+].[O-]P([O-])(=O)CC1=CC=CC=C1 DGOHHJOTBMONNG-UHFFFAOYSA-L 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
- 238000004993 emission spectroscopy Methods 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- CWUYZGOAWKLTQW-UHFFFAOYSA-N ethoxy-(3-methyl-5-nitrophenyl)phosphinic acid Chemical compound CCOP(O)(=O)C1=CC(C)=CC([N+]([O-])=O)=C1 CWUYZGOAWKLTQW-UHFFFAOYSA-N 0.000 description 2
- ZFROBPHQQFZCMC-UHFFFAOYSA-N ethoxy-[(2-hydroxyphenyl)methyl]phosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=CC=C1O ZFROBPHQQFZCMC-UHFFFAOYSA-N 0.000 description 2
- TUHQILXYEWBBDR-UHFFFAOYSA-N ethoxy-[(4-hydroxyphenyl)methyl]phosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=C(O)C=C1 TUHQILXYEWBBDR-UHFFFAOYSA-N 0.000 description 2
- MNEMDNZHKRYLQQ-UHFFFAOYSA-N ethoxy-[(4-methoxyphenyl)methyl]phosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=C(OC)C=C1 MNEMDNZHKRYLQQ-UHFFFAOYSA-N 0.000 description 2
- YGMVUOHNJAZZFB-UHFFFAOYSA-N ethoxy-[[4-(4-methoxycarbonylbenzoyl)phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C(=O)C1=CC=C(C(=O)OC)C=C1 YGMVUOHNJAZZFB-UHFFFAOYSA-N 0.000 description 2
- NYHUGRCSYSCKPG-UHFFFAOYSA-N ethoxy-[[4-(4-methoxycarbonylphenyl)sulfanylphenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1SC1=CC=C(C(=O)OC)C=C1 NYHUGRCSYSCKPG-UHFFFAOYSA-N 0.000 description 2
- YQWMWNUUHFQRQV-UHFFFAOYSA-N ethoxy-[[4-[(4-methoxycarbonylphenyl)methyl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1CC1=CC=C(C(=O)OC)C=C1 YQWMWNUUHFQRQV-UHFFFAOYSA-N 0.000 description 2
- SHOZYQJAEDUEFF-UHFFFAOYSA-N ethoxy-[[4-[2-(4-methoxycarbonylphenyl)propan-2-yl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C(C)(C)C1=CC=C(C(=O)OC)C=C1 SHOZYQJAEDUEFF-UHFFFAOYSA-N 0.000 description 2
- JBMQLIQCWRUXLP-UHFFFAOYSA-N ethoxy-[[4-[4-(2-methoxyethoxy)benzoyl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C(=O)C1=CC=C(OCCOC)C=C1 JBMQLIQCWRUXLP-UHFFFAOYSA-N 0.000 description 2
- JBGPDHXMINWQSZ-UHFFFAOYSA-N ethoxy-[[4-[4-(2-methoxyethoxy)phenyl]sulfanylphenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1SC1=CC=C(OCCOC)C=C1 JBGPDHXMINWQSZ-UHFFFAOYSA-N 0.000 description 2
- ZPKQAXYEKHELHM-UHFFFAOYSA-N ethoxy-[[4-[4-(2-methoxyethoxy)phenyl]sulfonylphenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1S(=O)(=O)C1=CC=C(OCCOC)C=C1 ZPKQAXYEKHELHM-UHFFFAOYSA-N 0.000 description 2
- NFOIYFOKCFWXAM-UHFFFAOYSA-N ethoxy-[[4-[[4-(2-methoxyethoxy)phenyl]methyl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1CC1=CC=C(OCCOC)C=C1 NFOIYFOKCFWXAM-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 238000009616 inductively coupled plasma Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- DWHMMGGJCLDORC-UHFFFAOYSA-N methoxy(methyl)phosphinic acid Chemical compound COP(C)(O)=O DWHMMGGJCLDORC-UHFFFAOYSA-N 0.000 description 2
- ZUYQAYFMISSPTF-UHFFFAOYSA-N methoxy-oxo-phenylphosphanium Chemical compound CO[P+](=O)C1=CC=CC=C1 ZUYQAYFMISSPTF-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- LYGCMUNBGIOQAB-UHFFFAOYSA-N naphthalen-1-ylmethylphosphonic acid Chemical compound C1=CC=C2C(CP(O)(=O)O)=CC=CC2=C1 LYGCMUNBGIOQAB-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 150000004028 organic sulfates Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- LEGSDIBWTVJPPR-UHFFFAOYSA-N oxo-phenoxy-phenylphosphanium Chemical compound C=1C=CC=CC=1[P+](=O)OC1=CC=CC=C1 LEGSDIBWTVJPPR-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 229940090668 parachlorophenol Drugs 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 2
- MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical compound OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 230000037048 polymerization activity Effects 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 230000001105 regulatory effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 2
- 239000011800 void material Substances 0.000 description 2
- 238000004876 x-ray fluorescence Methods 0.000 description 2
- UBORTALGZOJIIK-UHFFFAOYSA-N (2-butylphenyl)methyl-methoxyphosphinic acid Chemical compound COP(O)(=O)CC1=C(C=CC=C1)CCCC UBORTALGZOJIIK-UHFFFAOYSA-N 0.000 description 1
- GWJOXCMAHKFACU-UHFFFAOYSA-N (2-butylphenyl)methylphosphonic acid Chemical compound CCCCC1=CC=CC=C1CP(O)(O)=O GWJOXCMAHKFACU-UHFFFAOYSA-N 0.000 description 1
- RYBMGBPJTDMKLQ-UHFFFAOYSA-N (2-methoxycarbonylphenyl)methylphosphonic acid Chemical compound COC(=O)C1=CC=CC=C1CP(O)(O)=O RYBMGBPJTDMKLQ-UHFFFAOYSA-N 0.000 description 1
- NKVDWVIMDKLENB-UHFFFAOYSA-N (2-methyl-4-nitrophenyl)phosphonic acid Chemical compound CC1=CC([N+]([O-])=O)=CC=C1P(O)(O)=O NKVDWVIMDKLENB-UHFFFAOYSA-N 0.000 description 1
- MTNQLAKBYRCDTF-UHFFFAOYSA-N (2-nitrophenyl)phosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1[N+]([O-])=O MTNQLAKBYRCDTF-UHFFFAOYSA-N 0.000 description 1
- YMRVMALXSXGSQN-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl-methoxyphosphinic acid Chemical compound COP(O)(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 YMRVMALXSXGSQN-UHFFFAOYSA-N 0.000 description 1
- YFZSFXHZUQXULO-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl-phenoxyphosphinic acid Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CP(O)(=O)OC=2C=CC=CC=2)=C1 YFZSFXHZUQXULO-UHFFFAOYSA-N 0.000 description 1
- UEKWTSVNJAYRFS-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl-propan-2-yloxyphosphinic acid Chemical compound CC(C)OP(O)(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 UEKWTSVNJAYRFS-UHFFFAOYSA-N 0.000 description 1
- ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical compound CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 1
- CQDOVPVQKPULTJ-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid;magnesium Chemical compound [Mg].CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O CQDOVPVQKPULTJ-UHFFFAOYSA-N 0.000 description 1
- CKVMIRDJDNYTLY-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid;sodium Chemical compound [Na].CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O CKVMIRDJDNYTLY-UHFFFAOYSA-N 0.000 description 1
- YCTVNAQRHYBQKV-UHFFFAOYSA-N (3-methoxy-5-nitrophenyl)phosphonic acid Chemical compound COC1=CC([N+]([O-])=O)=CC(P(O)(O)=O)=C1 YCTVNAQRHYBQKV-UHFFFAOYSA-N 0.000 description 1
- CQTHVIPQUGJODY-UHFFFAOYSA-N (3-methoxycarbonylphenyl)methylphosphonic acid Chemical compound COC(=O)C1=CC=CC(CP(O)(O)=O)=C1 CQTHVIPQUGJODY-UHFFFAOYSA-N 0.000 description 1
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- OXWXINKWKITCIH-UHFFFAOYSA-N (3-nitrophenyl)phosphonic acid Chemical compound OP(O)(=O)C1=CC=CC([N+]([O-])=O)=C1 OXWXINKWKITCIH-UHFFFAOYSA-N 0.000 description 1
- VZQMGOMNLVSUDS-UHFFFAOYSA-N (4-aminophenyl)methyl-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=C(N)C=C1 VZQMGOMNLVSUDS-UHFFFAOYSA-N 0.000 description 1
- OEXKFCJDJPIFQR-UHFFFAOYSA-N (4-aminophenyl)methyl-methoxyphosphinic acid Chemical compound COP(O)(=O)CC1=CC=C(N)C=C1 OEXKFCJDJPIFQR-UHFFFAOYSA-N 0.000 description 1
- NEKHKXMBGWNTOO-UHFFFAOYSA-N (4-aminophenyl)methylphosphonic acid Chemical compound NC1=CC=C(CP(O)(O)=O)C=C1 NEKHKXMBGWNTOO-UHFFFAOYSA-N 0.000 description 1
- RYNIUXUALLJKOL-UHFFFAOYSA-N (4-butylphenyl)methyl-ethoxyphosphinic acid Chemical compound CCCCC1=CC=C(CP(O)(=O)OCC)C=C1 RYNIUXUALLJKOL-UHFFFAOYSA-N 0.000 description 1
- NUBNCLFSFYCBAF-UHFFFAOYSA-N (4-butylphenyl)methylphosphonic acid Chemical compound CCCCC1=CC=C(CP(O)(O)=O)C=C1 NUBNCLFSFYCBAF-UHFFFAOYSA-N 0.000 description 1
- NAOKJQSOWJEJDY-UHFFFAOYSA-N (4-chlorophenyl)methyl-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=C(Cl)C=C1 NAOKJQSOWJEJDY-UHFFFAOYSA-N 0.000 description 1
- LXLJQKUHFUBPAS-UHFFFAOYSA-N (4-chlorophenyl)methyl-phenoxyphosphinic acid Chemical compound C=1C=CC=CC=1OP(=O)(O)CC1=CC=C(Cl)C=C1 LXLJQKUHFUBPAS-UHFFFAOYSA-N 0.000 description 1
- KFNFQPHCXKFJDR-UHFFFAOYSA-N (4-chlorophenyl)methylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=C(Cl)C=C1 KFNFQPHCXKFJDR-UHFFFAOYSA-N 0.000 description 1
- MVCIBABYNNIPFI-UHFFFAOYSA-N (4-chlorophenyl)phosphonic acid Chemical compound OP(O)(=O)C1=CC=C(Cl)C=C1 MVCIBABYNNIPFI-UHFFFAOYSA-N 0.000 description 1
- PVHCWKRXUOYBKN-UHFFFAOYSA-N (4-hydroxyphenyl)-phenylphosphinic acid Chemical compound C1=CC(O)=CC=C1P(O)(=O)C1=CC=CC=C1 PVHCWKRXUOYBKN-UHFFFAOYSA-N 0.000 description 1
- ZHBRSHSRMYZHLS-UHFFFAOYSA-N (4-hydroxyphenyl)methylphosphonic acid Chemical compound OC1=CC=C(CP(O)(O)=O)C=C1 ZHBRSHSRMYZHLS-UHFFFAOYSA-N 0.000 description 1
- YIDVLWDHYNWHMH-UHFFFAOYSA-N (4-hydroxyphenyl)phosphonic acid Chemical compound OC1=CC=C(P(O)(O)=O)C=C1 YIDVLWDHYNWHMH-UHFFFAOYSA-N 0.000 description 1
- UFCVSHWPVFVPBK-UHFFFAOYSA-N (4-methoxycarbonylphenyl)methylphosphonic acid Chemical compound COC(=O)C1=CC=C(CP(O)(O)=O)C=C1 UFCVSHWPVFVPBK-UHFFFAOYSA-N 0.000 description 1
- XUAVFSMXCWTYNM-UHFFFAOYSA-N (4-methoxyphenyl)methylphosphonic acid Chemical compound COC1=CC=C(CP(O)(O)=O)C=C1 XUAVFSMXCWTYNM-UHFFFAOYSA-N 0.000 description 1
- FZNXRFYRXBFQMX-UHFFFAOYSA-N (4-nitrophenyl)methylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=C([N+]([O-])=O)C=C1 FZNXRFYRXBFQMX-UHFFFAOYSA-N 0.000 description 1
- CBWCNKVANCTCAD-UHFFFAOYSA-N (4-nitrophenyl)phosphonic acid Chemical compound OP(O)(=O)C1=CC=C([N+]([O-])=O)C=C1 CBWCNKVANCTCAD-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 1
- CHXUEWZEKNGMPP-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-2-(2-methoxyethoxy)benzene Chemical compound CCOP(=O)(OCC)CC1=CC=CC=C1OCCOC CHXUEWZEKNGMPP-UHFFFAOYSA-N 0.000 description 1
- QEBHHKWNGUKKPT-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-3,5-bis(2-methoxyethoxy)benzene Chemical compound CCOP(=O)(OCC)CC1=CC(OCCOC)=CC(OCCOC)=C1 QEBHHKWNGUKKPT-UHFFFAOYSA-N 0.000 description 1
- KEOFIDPBEODIEY-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-3-(2-methoxyethoxy)benzene Chemical compound CCOP(=O)(OCC)CC1=CC=CC(OCCOC)=C1 KEOFIDPBEODIEY-UHFFFAOYSA-N 0.000 description 1
- KEZJRCWXGNFPCG-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-4-(2-methoxyethoxy)benzene Chemical compound CCOP(=O)(OCC)CC1=CC=C(OCCOC)C=C1 KEZJRCWXGNFPCG-UHFFFAOYSA-N 0.000 description 1
- SWQQSYWJGGTDCJ-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-4-[4-(2-methoxyethoxy)phenyl]benzene Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1C1=CC=C(OCCOC)C=C1 SWQQSYWJGGTDCJ-UHFFFAOYSA-N 0.000 description 1
- NKARVHNAACNYGE-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-4-methoxybenzene Chemical compound CCOP(=O)(OCC)CC1=CC=C(OC)C=C1 NKARVHNAACNYGE-UHFFFAOYSA-N 0.000 description 1
- FORMFFDDQMCTCT-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-4-nitrobenzene Chemical compound CCOP(=O)(OCC)CC1=CC=C([N+]([O-])=O)C=C1 FORMFFDDQMCTCT-UHFFFAOYSA-N 0.000 description 1
- YSLTULGACFDGRF-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-9-(2-methoxyethoxy)anthracene Chemical compound C1=CC=C2C(OCCOC)=C3C(CP(=O)(OCC)OCC)=CC=CC3=CC2=C1 YSLTULGACFDGRF-UHFFFAOYSA-N 0.000 description 1
- WYLUKBADGDKPDF-UHFFFAOYSA-N 1-[ethoxy(methyl)phosphoryl]oxynaphthalene Chemical compound C1=CC=C2C(OP(C)(=O)OCC)=CC=CC2=C1 WYLUKBADGDKPDF-UHFFFAOYSA-N 0.000 description 1
- GJMCVDFIGNBVKX-UHFFFAOYSA-N 1-benzofuran-2-ylmethyl(ethoxy)phosphinic acid Chemical compound C1=CC=C2OC(CP(O)(=O)OCC)=CC2=C1 GJMCVDFIGNBVKX-UHFFFAOYSA-N 0.000 description 1
- ILEBALPDBGGXRL-UHFFFAOYSA-N 1-benzofuran-5-yl(ethoxy)phosphinic acid Chemical compound CCOP(O)(=O)C1=CC=C2OC=CC2=C1 ILEBALPDBGGXRL-UHFFFAOYSA-N 0.000 description 1
- FWUZDBLXDPZORI-UHFFFAOYSA-N 1-benzofuran-5-ylphosphonic acid Chemical compound OP(O)(=O)C1=CC=C2OC=CC2=C1 FWUZDBLXDPZORI-UHFFFAOYSA-N 0.000 description 1
- IHIWKDKBWGHSBI-UHFFFAOYSA-N 1-butyl-2-(diethoxyphosphorylmethyl)benzene Chemical compound CCCCC1=CC=CC=C1CP(=O)(OCC)OCC IHIWKDKBWGHSBI-UHFFFAOYSA-N 0.000 description 1
- DMVPGSWYWMGBOO-UHFFFAOYSA-N 1-butyl-3-(diethoxyphosphorylmethyl)benzene Chemical compound CCCCC1=CC=CC(CP(=O)(OCC)OCC)=C1 DMVPGSWYWMGBOO-UHFFFAOYSA-N 0.000 description 1
- VOPQYFCGOUWFAW-UHFFFAOYSA-N 1-butyl-4-(diethoxyphosphorylmethyl)benzene Chemical compound CCCCC1=CC=C(CP(=O)(OCC)OCC)C=C1 VOPQYFCGOUWFAW-UHFFFAOYSA-N 0.000 description 1
- SXDGJSPEJGSOPD-UHFFFAOYSA-N 1-butyl-4-[4-(diethoxyphosphorylmethyl)phenyl]benzene Chemical compound C1=CC(CCCC)=CC=C1C1=CC=C(CP(=O)(OCC)OCC)C=C1 SXDGJSPEJGSOPD-UHFFFAOYSA-N 0.000 description 1
- BVQPVBZRJSFOEZ-UHFFFAOYSA-N 1-chloro-4-(diethoxyphosphorylmethyl)benzene Chemical compound CCOP(=O)(OCC)CC1=CC=C(Cl)C=C1 BVQPVBZRJSFOEZ-UHFFFAOYSA-N 0.000 description 1
- UMDFLKHMFHZJRR-UHFFFAOYSA-N 1-chloro-4-diethoxyphosphorylbenzene Chemical compound CCOP(=O)(OCC)C1=CC=C(Cl)C=C1 UMDFLKHMFHZJRR-UHFFFAOYSA-N 0.000 description 1
- DSJPQMWLICAABG-UHFFFAOYSA-N 1-diethoxyphosphoryl-2-methyl-4-nitrobenzene Chemical compound CCOP(=O)(OCC)C1=CC=C([N+]([O-])=O)C=C1C DSJPQMWLICAABG-UHFFFAOYSA-N 0.000 description 1
- AYSAUUWVVFICJE-UHFFFAOYSA-N 1-diethoxyphosphoryl-2-nitrobenzene Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1[N+]([O-])=O AYSAUUWVVFICJE-UHFFFAOYSA-N 0.000 description 1
- PYDXLLRJYMIIMA-UHFFFAOYSA-N 1-diethoxyphosphoryl-3-methoxy-5-nitrobenzene Chemical compound CCOP(=O)(OCC)C1=CC(OC)=CC([N+]([O-])=O)=C1 PYDXLLRJYMIIMA-UHFFFAOYSA-N 0.000 description 1
- XULZFYBFQWRFDJ-UHFFFAOYSA-N 1-diethoxyphosphoryl-3-nitrobenzene Chemical compound CCOP(=O)(OCC)C1=CC=CC([N+]([O-])=O)=C1 XULZFYBFQWRFDJ-UHFFFAOYSA-N 0.000 description 1
- AWAKGNAIMIGBNG-UHFFFAOYSA-N 1-diethoxyphosphoryl-4-nitrobenzene Chemical compound CCOP(=O)(OCC)C1=CC=C([N+]([O-])=O)C=C1 AWAKGNAIMIGBNG-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- WJQZZLQMLJPKQH-UHFFFAOYSA-N 2,4-dichloro-6-methylphenol Chemical compound CC1=CC(Cl)=CC(Cl)=C1O WJQZZLQMLJPKQH-UHFFFAOYSA-N 0.000 description 1
- HIOUZOMPJOAAGL-UHFFFAOYSA-N 2,6-ditert-butyl-4-(dibutoxyphosphorylmethyl)phenol Chemical compound CCCCOP(=O)(OCCCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 HIOUZOMPJOAAGL-UHFFFAOYSA-N 0.000 description 1
- OPYDNGQRKKKKNC-UHFFFAOYSA-N 2,6-ditert-butyl-4-[di(propan-2-yloxy)phosphorylmethyl]phenol Chemical compound CC(C)OP(=O)(OC(C)C)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 OPYDNGQRKKKKNC-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- UIOSPCOLCQEPHP-UHFFFAOYSA-N 2-(diethoxyphosphorylmethyl)-1,4-bis(2-methoxyethoxy)benzene Chemical compound CCOP(=O)(OCC)CC1=CC(OCCOC)=CC=C1OCCOC UIOSPCOLCQEPHP-UHFFFAOYSA-N 0.000 description 1
- NUYVYQVDHXHGRT-UHFFFAOYSA-N 2-(diethoxyphosphorylmethyl)-1-benzofuran Chemical compound C1=CC=C2OC(CP(=O)(OCC)OCC)=CC2=C1 NUYVYQVDHXHGRT-UHFFFAOYSA-N 0.000 description 1
- ZZRMXCIHMHVJRW-UHFFFAOYSA-N 2-(diethoxyphosphorylmethyl)benzoic acid Chemical compound CCOP(=O)(OCC)CC1=CC=CC=C1C(O)=O ZZRMXCIHMHVJRW-UHFFFAOYSA-N 0.000 description 1
- DAKLXYIFDSBDCL-UHFFFAOYSA-N 2-(diethoxyphosphorylmethyl)terephthalic acid Chemical compound CCOP(=O)(OCC)CC1=CC(C(O)=O)=CC=C1C(O)=O DAKLXYIFDSBDCL-UHFFFAOYSA-N 0.000 description 1
- CMMZFWKXZFHQDO-UHFFFAOYSA-N 2-(phosphonomethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CP(O)(O)=O CMMZFWKXZFHQDO-UHFFFAOYSA-N 0.000 description 1
- GHFGXWIVJKVROY-UHFFFAOYSA-N 2-(phosphonomethyl)terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(CP(O)(O)=O)=C1 GHFGXWIVJKVROY-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- AUXIOKFDPHBBGN-UHFFFAOYSA-N 2-[2-(diethoxyphosphorylmethyl)phenoxy]ethanol Chemical compound CCOP(=O)(OCC)CC1=CC=CC=C1OCCO AUXIOKFDPHBBGN-UHFFFAOYSA-N 0.000 description 1
- XVJPOHFJILRDBE-UHFFFAOYSA-N 2-[3-(diethoxyphosphorylmethyl)-4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound CCOP(=O)(OCC)CC1=CC(OCCO)=CC=C1OCCO XVJPOHFJILRDBE-UHFFFAOYSA-N 0.000 description 1
- YSSGYGQBZFNQPH-UHFFFAOYSA-N 2-[3-(diethoxyphosphorylmethyl)-5-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound CCOP(=O)(OCC)CC1=CC(OCCO)=CC(OCCO)=C1 YSSGYGQBZFNQPH-UHFFFAOYSA-N 0.000 description 1
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 1
- JVGDVPVEKJSWIO-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)cyclohexyl]ethanol Chemical compound OCCC1CCC(CCO)CC1 JVGDVPVEKJSWIO-UHFFFAOYSA-N 0.000 description 1
- OZAZGORNKCQYAV-UHFFFAOYSA-N 2-[4-(diethoxyphosphorylmethyl)phenoxy]ethanol Chemical compound CCOP(=O)(OCC)CC1=CC=C(OCCO)C=C1 OZAZGORNKCQYAV-UHFFFAOYSA-N 0.000 description 1
- JNCADEXFDKTYRO-UHFFFAOYSA-N 2-[4-[4-(diethoxyphosphorylmethyl)phenyl]phenoxy]ethanol Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1C1=CC=C(OCCO)C=C1 JNCADEXFDKTYRO-UHFFFAOYSA-N 0.000 description 1
- LLSLRCCISINSMU-UHFFFAOYSA-N 2-[[ethoxy(hydroxy)phosphoryl]methyl]benzoic acid Chemical compound CCOP(O)(=O)CC1=CC=CC=C1C(O)=O LLSLRCCISINSMU-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 1
- MMINFSMURORWKH-UHFFFAOYSA-N 3,6-dioxabicyclo[6.2.2]dodeca-1(10),8,11-triene-2,7-dione Chemical group O=C1OCCOC(=O)C2=CC=C1C=C2 MMINFSMURORWKH-UHFFFAOYSA-N 0.000 description 1
- GYJREHMTTLYKRJ-UHFFFAOYSA-N 3-(2-fluorophenyl)-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C=1C=CC=CC=1COC(=O)NC(C(=O)O)CC1=CC=CC=C1F GYJREHMTTLYKRJ-UHFFFAOYSA-N 0.000 description 1
- FZKURNSIBVVIEU-UHFFFAOYSA-N 3-(diethoxyphosphorylmethyl)benzoic acid Chemical compound CCOP(=O)(OCC)CC1=CC=CC(C(O)=O)=C1 FZKURNSIBVVIEU-UHFFFAOYSA-N 0.000 description 1
- QIDFDDOEXSPDGN-UHFFFAOYSA-N 3-(phosphonomethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(CP(O)(O)=O)=C1 QIDFDDOEXSPDGN-UHFFFAOYSA-N 0.000 description 1
- WKRIXJWFPCEODF-UHFFFAOYSA-N 3-[[ethoxy(hydroxy)phosphoryl]methyl]benzoic acid Chemical compound CCOP(O)(=O)CC1=CC=CC(C(O)=O)=C1 WKRIXJWFPCEODF-UHFFFAOYSA-N 0.000 description 1
- QXFUBAAEKCHBQY-UHFFFAOYSA-N 3-[hydroxy(methyl)phosphoryl]propanoic acid Chemical compound CP(O)(=O)CCC(O)=O QXFUBAAEKCHBQY-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- QLIQIXIBZLTPGQ-UHFFFAOYSA-N 4-(2-hydroxyethoxy)benzoic acid Chemical compound OCCOC1=CC=C(C(O)=O)C=C1 QLIQIXIBZLTPGQ-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
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- ZVAYUUUQOCPZCZ-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)aniline Chemical compound CCOP(=O)(OCC)CC1=CC=C(N)C=C1 ZVAYUUUQOCPZCZ-UHFFFAOYSA-N 0.000 description 1
- BYKRBDLOUKSWNM-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)benzoic acid Chemical compound CCOP(=O)(OCC)CC1=CC=C(C(O)=O)C=C1 BYKRBDLOUKSWNM-UHFFFAOYSA-N 0.000 description 1
- RNIILMHZBDEEDW-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)phenol Chemical compound CCOP(=O)(OCC)CC1=CC=C(O)C=C1 RNIILMHZBDEEDW-UHFFFAOYSA-N 0.000 description 1
- OXYRLNBFAYYOPG-UHFFFAOYSA-N 4-(phosphonomethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CP(O)(O)=O)C=C1 OXYRLNBFAYYOPG-UHFFFAOYSA-N 0.000 description 1
- ONPFYQQKCRYEFY-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-methylphosphoryl]phenol Chemical compound C=1C=C(O)C=CC=1P(=O)(C)C1=CC=C(O)C=C1 ONPFYQQKCRYEFY-UHFFFAOYSA-N 0.000 description 1
- LXAYMDJRNVVCGG-UHFFFAOYSA-N 4-[2-[4-(diethoxyphosphorylmethyl)phenyl]propan-2-yl]phenol Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1C(C)(C)C1=CC=C(O)C=C1 LXAYMDJRNVVCGG-UHFFFAOYSA-N 0.000 description 1
- LIGJJZIFUIICQF-UHFFFAOYSA-N 4-[2-[4-(phosphonomethyl)phenyl]propan-2-yl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(C)(C)C1=CC=C(CP(O)(O)=O)C=C1 LIGJJZIFUIICQF-UHFFFAOYSA-N 0.000 description 1
- PEPQHAIJJABWGM-UHFFFAOYSA-N 4-[2-[4-[[ethoxy(hydroxy)phosphoryl]methyl]phenyl]propan-2-yl]benzoic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C(C)(C)C1=CC=C(C(O)=O)C=C1 PEPQHAIJJABWGM-UHFFFAOYSA-N 0.000 description 1
- VKPUGPALTSAXHT-UHFFFAOYSA-N 4-[4-(diethoxyphosphorylmethyl)phenoxy]phenol Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1OC1=CC=C(O)C=C1 VKPUGPALTSAXHT-UHFFFAOYSA-N 0.000 description 1
- YSULCZRUTURPLE-UHFFFAOYSA-N 4-[4-(diethoxyphosphorylmethyl)phenyl]phenol Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1C1=CC=C(O)C=C1 YSULCZRUTURPLE-UHFFFAOYSA-N 0.000 description 1
- RBFWQHJVKQLRTC-UHFFFAOYSA-N 4-[4-(diethoxyphosphorylmethyl)phenyl]sulfanylphenol Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1SC1=CC=C(O)C=C1 RBFWQHJVKQLRTC-UHFFFAOYSA-N 0.000 description 1
- RHSHJFYIYLGDAV-UHFFFAOYSA-N 4-[4-(diethoxyphosphorylmethyl)phenyl]sulfonylphenol Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 RHSHJFYIYLGDAV-UHFFFAOYSA-N 0.000 description 1
- MKMHBKOLMAXVLJ-UHFFFAOYSA-N 4-[4-(phosphonomethyl)benzoyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=C(CP(O)(O)=O)C=C1 MKMHBKOLMAXVLJ-UHFFFAOYSA-N 0.000 description 1
- UWMNLNRBXRWJOG-UHFFFAOYSA-N 4-[4-(phosphonomethyl)phenoxy]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(CP(O)(O)=O)C=C1 UWMNLNRBXRWJOG-UHFFFAOYSA-N 0.000 description 1
- QECRHEYLYVSPNL-UHFFFAOYSA-N 4-[4-(phosphonomethyl)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(CP(O)(O)=O)C=C1 QECRHEYLYVSPNL-UHFFFAOYSA-N 0.000 description 1
- VSOPCXLKSHTBOT-UHFFFAOYSA-N 4-[4-(phosphonomethyl)phenyl]sulfanylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1SC1=CC=C(CP(O)(O)=O)C=C1 VSOPCXLKSHTBOT-UHFFFAOYSA-N 0.000 description 1
- AUYNLXPKSYVGTL-UHFFFAOYSA-N 4-[4-(phosphonomethyl)phenyl]sulfonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(CP(O)(O)=O)C=C1 AUYNLXPKSYVGTL-UHFFFAOYSA-N 0.000 description 1
- NNWLDISWQQOREO-UHFFFAOYSA-N 4-[4-[[ethoxy(hydroxy)phosphoryl]methyl]phenyl]benzoic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C1=CC=C(C(O)=O)C=C1 NNWLDISWQQOREO-UHFFFAOYSA-N 0.000 description 1
- XVKPLYDKLPGUIL-UHFFFAOYSA-N 4-[4-[[ethoxy(hydroxy)phosphoryl]methyl]phenyl]sulfonylbenzoic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 XVKPLYDKLPGUIL-UHFFFAOYSA-N 0.000 description 1
- HMFJRHXHKOGIOD-UHFFFAOYSA-N 4-[[4-(diethoxyphosphorylmethyl)phenyl]methyl]phenol Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1CC1=CC=C(O)C=C1 HMFJRHXHKOGIOD-UHFFFAOYSA-N 0.000 description 1
- QCVGLWFGUFILNH-UHFFFAOYSA-N 4-[[4-(phosphonomethyl)phenyl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C(CP(O)(O)=O)C=C1 QCVGLWFGUFILNH-UHFFFAOYSA-N 0.000 description 1
- OMTGMXIILUYECO-UHFFFAOYSA-N 4-[[ethoxy(hydroxy)phosphoryl]methyl]benzoic acid Chemical compound CCOP(O)(=O)CC1=CC=C(C(O)=O)C=C1 OMTGMXIILUYECO-UHFFFAOYSA-N 0.000 description 1
- ARNMLISJGAUXFO-UHFFFAOYSA-N 4-[methoxy(phenyl)phosphoryl]phenol Chemical compound C=1C=C(O)C=CC=1P(=O)(OC)C1=CC=CC=C1 ARNMLISJGAUXFO-UHFFFAOYSA-N 0.000 description 1
- LMBQOLBVWODAFG-UHFFFAOYSA-N 4-bis(4-hydroxyphenyl)phosphorylphenol Chemical compound C1=CC(O)=CC=C1P(=O)(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 LMBQOLBVWODAFG-UHFFFAOYSA-N 0.000 description 1
- RKDQFNLPHKSPGL-UHFFFAOYSA-N 4-diethoxyphosphorylphenol Chemical compound CCOP(=O)(OCC)C1=CC=C(O)C=C1 RKDQFNLPHKSPGL-UHFFFAOYSA-N 0.000 description 1
- AQPFPXSCYLHYDX-UHFFFAOYSA-N 4-diphenoxyphosphorylphenol Chemical compound C1=CC(O)=CC=C1P(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 AQPFPXSCYLHYDX-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical group C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 1
- NJCWEPQCBHYSKZ-UHFFFAOYSA-N 5-(diethoxyphosphorylmethyl)benzene-1,3-dicarboxylic acid Chemical compound CCOP(=O)(OCC)CC1=CC(C(O)=O)=CC(C(O)=O)=C1 NJCWEPQCBHYSKZ-UHFFFAOYSA-N 0.000 description 1
- ATEDZEYFTCGZFE-UHFFFAOYSA-N 5-(phosphonomethyl)benzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(CP(O)(O)=O)=CC(C(O)=O)=C1 ATEDZEYFTCGZFE-UHFFFAOYSA-N 0.000 description 1
- AKCJZTBVYGOSBP-UHFFFAOYSA-N 5-[[ethoxy(hydroxy)phosphoryl]methyl]benzene-1,3-dicarboxylic acid Chemical compound CCOP(O)(=O)CC1=CC(C(O)=O)=CC(C(O)=O)=C1 AKCJZTBVYGOSBP-UHFFFAOYSA-N 0.000 description 1
- GXLGISXFYKHELQ-UHFFFAOYSA-N 5-diethoxyphosphoryl-1-benzofuran Chemical compound CCOP(=O)(OCC)C1=CC=C2OC=CC2=C1 GXLGISXFYKHELQ-UHFFFAOYSA-N 0.000 description 1
- ZUGAOYSWHHGDJY-UHFFFAOYSA-K 5-hydroxy-2,8,9-trioxa-1-aluminabicyclo[3.3.2]decane-3,7,10-trione Chemical compound [Al+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O ZUGAOYSWHHGDJY-UHFFFAOYSA-K 0.000 description 1
- XIWJFDQMTPICJF-UHFFFAOYSA-N 5-phenylnonan-5-ylphosphonic acid Chemical compound CCCCC(CCCC)(P(O)(O)=O)C1=CC=CC=C1 XIWJFDQMTPICJF-UHFFFAOYSA-N 0.000 description 1
- KCLPHLKDXLHASP-UHFFFAOYSA-N 9-(diethoxyphosphorylmethyl)anthracene Chemical compound C1=CC=C2C(CP(=O)(OCC)OCC)=C(C=CC=C3)C3=CC2=C1 KCLPHLKDXLHASP-UHFFFAOYSA-N 0.000 description 1
- MKGUMBVZDGBTNO-UHFFFAOYSA-N 9-[ethoxy(methyl)phosphoryl]oxyanthracene Chemical compound C1=CC=C2C(OP(C)(=O)OCC)=C(C=CC=C3)C3=CC2=C1 MKGUMBVZDGBTNO-UHFFFAOYSA-N 0.000 description 1
- DEVXQDKRGJCZMV-UHFFFAOYSA-K Aluminum acetoacetate Chemical compound [Al+3].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O.CC(=O)CC([O-])=O DEVXQDKRGJCZMV-UHFFFAOYSA-K 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- YTQQKAMNMZFWHW-UHFFFAOYSA-J C(C)(C)(C)C=1C=C(C(P([O-])([O-])=O)O)C=C(C1CC)C(C)(C)C.C(C)(C)(C)C=1C=C(C(P([O-])([O-])=O)O)C=C(C1CC)C(C)(C)C.[Mn+4] Chemical compound C(C)(C)(C)C=1C=C(C(P([O-])([O-])=O)O)C=C(C1CC)C(C)(C)C.C(C)(C)(C)C=1C=C(C(P([O-])([O-])=O)O)C=C(C1CC)C(C)(C)C.[Mn+4] YTQQKAMNMZFWHW-UHFFFAOYSA-J 0.000 description 1
- YOVOSLAKHAETMW-UHFFFAOYSA-J C(C)(C)(C)C=1C=C(CP([O-])([O-])=O)C=C(C1O)C(C)(C)C.C(C)(C)(C)C=1C=C(CP([O-])([O-])=O)C=C(C1O)C(C)(C)C.[Ni+4] Chemical compound C(C)(C)(C)C=1C=C(CP([O-])([O-])=O)C=C(C1O)C(C)(C)C.C(C)(C)(C)C=1C=C(CP([O-])([O-])=O)C=C(C1O)C(C)(C)C.[Ni+4] YOVOSLAKHAETMW-UHFFFAOYSA-J 0.000 description 1
- FUXCAOCCVREQNI-UHFFFAOYSA-J C(C)(C)(C)C=1C=C(CP([O-])([O-])=O)C=C(C1O)C(C)(C)C.C(C)(C)(C)C=1C=C(CP([O-])([O-])=O)C=C(C1O)C(C)(C)C.[Zn+2].C(C)(C)(C)C=1C=C(CP(O)(O)=O)C=C(C1O)C(C)(C)C.C(C)(C)(C)C=1C=C(CP(O)(O)=O)C=C(C1O)C(C)(C)C.[Cu+2] Chemical compound C(C)(C)(C)C=1C=C(CP([O-])([O-])=O)C=C(C1O)C(C)(C)C.C(C)(C)(C)C=1C=C(CP([O-])([O-])=O)C=C(C1O)C(C)(C)C.[Zn+2].C(C)(C)(C)C=1C=C(CP(O)(O)=O)C=C(C1O)C(C)(C)C.C(C)(C)(C)C=1C=C(CP(O)(O)=O)C=C(C1O)C(C)(C)C.[Cu+2] FUXCAOCCVREQNI-UHFFFAOYSA-J 0.000 description 1
- YMUSQAKJFULFGU-UHFFFAOYSA-L C(C)C(C1=CC=C(C=C1)O)P([O-])([O-])=O.[Na+].[Na+] Chemical compound C(C)C(C1=CC=C(C=C1)O)P([O-])([O-])=O.[Na+].[Na+] YMUSQAKJFULFGU-UHFFFAOYSA-L 0.000 description 1
- FBMKNVMYQRUVAC-UHFFFAOYSA-J C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.[Mg+2].[Mg+2] Chemical compound C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.[Mg+2].[Mg+2] FBMKNVMYQRUVAC-UHFFFAOYSA-J 0.000 description 1
- UJUSCKYTJJMZHV-UHFFFAOYSA-J C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.[Mn+4] Chemical compound C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.[Mn+4] UJUSCKYTJJMZHV-UHFFFAOYSA-J 0.000 description 1
- MQJGEEYGIJXZKJ-UHFFFAOYSA-J C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.[Sr+2].[Sr+2] Chemical compound C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.[Sr+2].[Sr+2] MQJGEEYGIJXZKJ-UHFFFAOYSA-J 0.000 description 1
- NAFWZRNYFPCBND-UHFFFAOYSA-L C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.[Na+].[Na+] Chemical compound C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.[Na+].[Na+] NAFWZRNYFPCBND-UHFFFAOYSA-L 0.000 description 1
- MNZWSZVSSLNRSU-UHFFFAOYSA-J C(C)C1=C(C=CC=C1)P([O-])([O-])=O.C(C)C1=C(C=CC=C1)P([O-])([O-])=O.[Zn+2].[Zn+2] Chemical compound C(C)C1=C(C=CC=C1)P([O-])([O-])=O.C(C)C1=C(C=CC=C1)P([O-])([O-])=O.[Zn+2].[Zn+2] MNZWSZVSSLNRSU-UHFFFAOYSA-J 0.000 description 1
- IKPNDJCWNOBSPH-UHFFFAOYSA-N C(C)OP(O)(=O)C(C1=CC=CC=C1)OCCO Chemical compound C(C)OP(O)(=O)C(C1=CC=CC=C1)OCCO IKPNDJCWNOBSPH-UHFFFAOYSA-N 0.000 description 1
- FXLDBAMZDKSISF-UHFFFAOYSA-N C(C)OP(O)(=O)CC1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C(=O)O.C(CCC)C1=CC=C(C=C1)C(C1=CC=C(CP(O)(O)=O)C=C1)(C)C Chemical compound C(C)OP(O)(=O)CC1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C(=O)O.C(CCC)C1=CC=C(C=C1)C(C1=CC=C(CP(O)(O)=O)C=C1)(C)C FXLDBAMZDKSISF-UHFFFAOYSA-N 0.000 description 1
- YNPIYYAFFIRMAQ-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCC(C1=CC=C(C=C1)O)P(=O)(O)O Chemical compound CCCCCCCCCCCCCCCCCCC(C1=CC=C(C=C1)O)P(=O)(O)O YNPIYYAFFIRMAQ-UHFFFAOYSA-N 0.000 description 1
- OJIGNQVRMPTBOJ-UHFFFAOYSA-N COC(=O)C(C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C34)P(O)(O)=O Chemical compound COC(=O)C(C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C34)P(O)(O)=O OJIGNQVRMPTBOJ-UHFFFAOYSA-N 0.000 description 1
- GJDJBZOHMBAZRR-UHFFFAOYSA-N COCCOC1(CP(O)(O)=O)CC=CC=C1.C(C)OP(O)(=O)CC1=C(C=CC=C1)OCCOC Chemical compound COCCOC1(CP(O)(O)=O)CC=CC=C1.C(C)OP(O)(=O)CC1=C(C=CC=C1)OCCOC GJDJBZOHMBAZRR-UHFFFAOYSA-N 0.000 description 1
- MGXKMKSFEFYEHL-UHFFFAOYSA-N COCCOC=1C=C(CP(O)(O)=O)C=CC1.C(C)OP(O)(=O)CC1=CC(=CC=C1)OCCOC Chemical compound COCCOC=1C=C(CP(O)(O)=O)C=CC1.C(C)OP(O)(=O)CC1=CC(=CC=C1)OCCOC MGXKMKSFEFYEHL-UHFFFAOYSA-N 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
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- RWGYKCFHWQAGSE-UHFFFAOYSA-N OC1=CC=C(C=C1)P(OC)=O Chemical compound OC1=CC=C(C=C1)P(OC)=O RWGYKCFHWQAGSE-UHFFFAOYSA-N 0.000 description 1
- BVVPKZPSWGYDCX-UHFFFAOYSA-N OC1=CC=C(C=C1)P(OC1=CC=CC=C1)=O Chemical compound OC1=CC=C(C=C1)P(OC1=CC=CC=C1)=O BVVPKZPSWGYDCX-UHFFFAOYSA-N 0.000 description 1
- WNLALASIJZQWSD-UHFFFAOYSA-N Oc1ccc(cc1)P(O)=O Chemical compound Oc1ccc(cc1)P(O)=O WNLALASIJZQWSD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- 241001483078 Phyto Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- DGVJTZKFAMINOJ-UHFFFAOYSA-N [2,5-bis(2-hydroxyethoxy)phenyl]methylphosphonic acid Chemical compound OCCOC1=CC=C(OCCO)C(CP(O)(O)=O)=C1 DGVJTZKFAMINOJ-UHFFFAOYSA-N 0.000 description 1
- VVQRMZDFDGXVTD-UHFFFAOYSA-N [2,5-bis(2-methoxyethoxy)phenyl]methyl-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)CC1=CC(OCCOC)=CC=C1OCCOC VVQRMZDFDGXVTD-UHFFFAOYSA-N 0.000 description 1
- PAWMKKBCUFAOAB-UHFFFAOYSA-N [2,5-bis(methoxycarbonyl)phenyl]methylphosphonic acid Chemical compound COC(=O)C1=CC=C(C(=O)OC)C(CP(O)(O)=O)=C1 PAWMKKBCUFAOAB-UHFFFAOYSA-N 0.000 description 1
- ZZFVDRJALPBENE-UHFFFAOYSA-N [2-(2-hydroxyethoxy)phenyl]methylphosphonic acid Chemical compound OCCOC1=CC=CC=C1CP(O)(O)=O ZZFVDRJALPBENE-UHFFFAOYSA-N 0.000 description 1
- XDODWINGEHBYRT-UHFFFAOYSA-N [2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCCC1CO XDODWINGEHBYRT-UHFFFAOYSA-N 0.000 description 1
- LRYRDMCHBWXZPD-UHFFFAOYSA-N [3,5-bis(2-hydroxyethoxy)phenyl]methyl-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)CC1=CC(OCCO)=CC(OCCO)=C1 LRYRDMCHBWXZPD-UHFFFAOYSA-N 0.000 description 1
- CWKTZLMYVMVWNK-UHFFFAOYSA-N [3,5-bis(2-hydroxyethoxy)phenyl]methylphosphonic acid Chemical compound OCCOC1=CC(CP(O)(O)=O)=CC(OCCO)=C1 CWKTZLMYVMVWNK-UHFFFAOYSA-N 0.000 description 1
- XQGSPVWQGYJGCK-UHFFFAOYSA-N [3,5-bis(2-methoxyethoxy)phenyl]methyl-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)CC1=CC(OCCOC)=CC(OCCOC)=C1 XQGSPVWQGYJGCK-UHFFFAOYSA-N 0.000 description 1
- AXSZVDWWNMYXPF-UHFFFAOYSA-N [3,5-bis(methoxycarbonyl)phenyl]methyl-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)CC1=CC(C(=O)OC)=CC(C(=O)OC)=C1 AXSZVDWWNMYXPF-UHFFFAOYSA-N 0.000 description 1
- CRQLTWJGLOOBGZ-UHFFFAOYSA-N [3,5-bis(methoxycarbonyl)phenyl]methylphosphonic acid Chemical compound COC(=O)C1=CC(CP(O)(O)=O)=CC(C(=O)OC)=C1 CRQLTWJGLOOBGZ-UHFFFAOYSA-N 0.000 description 1
- OONJCUWQVDSVDW-UHFFFAOYSA-N [3-(2-hydroxyethoxy)phenyl]methylphosphonic acid Chemical compound OCCOC1=CC=CC(CP(O)(O)=O)=C1 OONJCUWQVDSVDW-UHFFFAOYSA-N 0.000 description 1
- PBVFRAVUEQPXKP-UHFFFAOYSA-N [4-(2-hydroxyethoxy)phenyl]methylphosphonic acid Chemical compound OCCOC1=CC=C(CP(O)(O)=O)C=C1 PBVFRAVUEQPXKP-UHFFFAOYSA-N 0.000 description 1
- CFLYWUGDDDZDAX-UHFFFAOYSA-N [4-(4-butylbenzoyl)phenyl]methylphosphonic acid Chemical compound C1=CC(CCCC)=CC=C1C(=O)C1=CC=C(CP(O)(O)=O)C=C1 CFLYWUGDDDZDAX-UHFFFAOYSA-N 0.000 description 1
- GJWROPMTYZAMQJ-UHFFFAOYSA-N [4-(4-butylphenoxy)phenyl]methyl-ethoxyphosphinic acid Chemical compound C1=CC(CCCC)=CC=C1OC1=CC=C(CP(O)(=O)OCC)C=C1 GJWROPMTYZAMQJ-UHFFFAOYSA-N 0.000 description 1
- YBARJFGTNBQZBT-UHFFFAOYSA-N [4-(4-butylphenoxy)phenyl]methylphosphonic acid Chemical compound C1=CC(CCCC)=CC=C1OC1=CC=C(CP(O)(O)=O)C=C1 YBARJFGTNBQZBT-UHFFFAOYSA-N 0.000 description 1
- AGIZTRQGZHREEA-UHFFFAOYSA-N [4-(4-butylphenyl)phenyl]methyl-ethoxyphosphinic acid Chemical compound C1=CC(CCCC)=CC=C1C1=CC=C(CP(O)(=O)OCC)C=C1 AGIZTRQGZHREEA-UHFFFAOYSA-N 0.000 description 1
- MQXDROLASVWDEB-UHFFFAOYSA-N [4-(4-butylphenyl)phenyl]methylphosphonic acid Chemical compound C1=CC(CCCC)=CC=C1C1=CC=C(CP(O)(O)=O)C=C1 MQXDROLASVWDEB-UHFFFAOYSA-N 0.000 description 1
- ARAIHHQXLPAAHL-UHFFFAOYSA-N [4-(4-butylphenyl)sulfanylphenyl]methyl-ethoxyphosphinic acid Chemical compound C1=CC(CCCC)=CC=C1SC1=CC=C(CP(O)(=O)OCC)C=C1 ARAIHHQXLPAAHL-UHFFFAOYSA-N 0.000 description 1
- BLGLOVJEABVIKC-UHFFFAOYSA-N [4-(4-butylphenyl)sulfanylphenyl]methylphosphonic acid Chemical compound C1=CC(CCCC)=CC=C1SC1=CC=C(CP(O)(O)=O)C=C1 BLGLOVJEABVIKC-UHFFFAOYSA-N 0.000 description 1
- OZYUZJAJEYRGBX-UHFFFAOYSA-N [4-(4-butylphenyl)sulfonylphenyl]methylphosphonic acid Chemical compound C1=CC(CCCC)=CC=C1S(=O)(=O)C1=CC=C(CP(O)(O)=O)C=C1 OZYUZJAJEYRGBX-UHFFFAOYSA-N 0.000 description 1
- MLYKEIYNIWNWJM-UHFFFAOYSA-N [4-(4-hydroxybenzoyl)phenyl]methylphosphonic acid Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(CP(O)(O)=O)C=C1 MLYKEIYNIWNWJM-UHFFFAOYSA-N 0.000 description 1
- WHEYJCCLEOXKPY-UHFFFAOYSA-N [4-(4-hydroxyphenoxy)phenyl]methylphosphonic acid Chemical compound C1=CC(O)=CC=C1OC1=CC=C(CP(O)(O)=O)C=C1 WHEYJCCLEOXKPY-UHFFFAOYSA-N 0.000 description 1
- QGEFPGZTXPWQCP-UHFFFAOYSA-N [4-(4-hydroxyphenyl)phenyl]methylphosphonic acid Chemical compound C1=CC(O)=CC=C1C1=CC=C(CP(O)(O)=O)C=C1 QGEFPGZTXPWQCP-UHFFFAOYSA-N 0.000 description 1
- FWMLPPUJWNDCPY-UHFFFAOYSA-N [4-(4-hydroxyphenyl)sulfanylphenyl]methylphosphonic acid Chemical compound C1=CC(O)=CC=C1SC1=CC=C(CP(O)(O)=O)C=C1 FWMLPPUJWNDCPY-UHFFFAOYSA-N 0.000 description 1
- WMNUQJCXYDWZRZ-UHFFFAOYSA-N [4-(4-hydroxyphenyl)sulfonylphenyl]methylphosphonic acid Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(CP(O)(O)=O)C=C1 WMNUQJCXYDWZRZ-UHFFFAOYSA-N 0.000 description 1
- PXFITAKFWOHXRL-UHFFFAOYSA-N [4-(4-methoxycarbonylbenzoyl)phenyl]methylphosphonic acid Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)C1=CC=C(CP(O)(O)=O)C=C1 PXFITAKFWOHXRL-UHFFFAOYSA-N 0.000 description 1
- GAKNJTRWBBPCAY-UHFFFAOYSA-N [4-(4-methoxycarbonylphenoxy)phenyl]methylphosphonic acid Chemical compound C1=CC(C(=O)OC)=CC=C1OC1=CC=C(CP(O)(O)=O)C=C1 GAKNJTRWBBPCAY-UHFFFAOYSA-N 0.000 description 1
- WOZMHEBJSGSTGC-UHFFFAOYSA-N [4-(4-methoxycarbonylphenyl)phenyl]methylphosphonic acid Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(CP(O)(O)=O)C=C1 WOZMHEBJSGSTGC-UHFFFAOYSA-N 0.000 description 1
- HNFSHKZAYWNAAX-UHFFFAOYSA-N [4-(4-methoxycarbonylphenyl)sulfanylphenyl]methylphosphonic acid Chemical compound C1=CC(C(=O)OC)=CC=C1SC1=CC=C(CP(O)(O)=O)C=C1 HNFSHKZAYWNAAX-UHFFFAOYSA-N 0.000 description 1
- FJWVQSIWXQSLLE-UHFFFAOYSA-N [4-(4-methoxycarbonylphenyl)sulfonylphenyl]methylphosphonic acid Chemical compound C1=CC(C(=O)OC)=CC=C1S(=O)(=O)C1=CC=C(CP(O)(O)=O)C=C1 FJWVQSIWXQSLLE-UHFFFAOYSA-N 0.000 description 1
- RRPBUIADMSIWBG-UHFFFAOYSA-N [4-(diethoxyphosphorylmethyl)phenyl]-(4-hydroxyphenyl)methanone Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1C(=O)C1=CC=C(O)C=C1 RRPBUIADMSIWBG-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- RRGHHJWVXRWLFR-UHFFFAOYSA-N [4-[(4-butylphenyl)methyl]phenyl]methylphosphonic acid Chemical compound C1=CC(CCCC)=CC=C1CC1=CC=C(CP(O)(O)=O)C=C1 RRGHHJWVXRWLFR-UHFFFAOYSA-N 0.000 description 1
- XENOTFCRGMWRRW-UHFFFAOYSA-N [4-[(4-hydroxyphenyl)methyl]phenyl]methylphosphonic acid Chemical compound C1=CC(O)=CC=C1CC1=CC=C(CP(O)(O)=O)C=C1 XENOTFCRGMWRRW-UHFFFAOYSA-N 0.000 description 1
- PLKWXDQPMWTNEM-UHFFFAOYSA-N [4-[(4-methoxycarbonylphenyl)methyl]phenyl]methylphosphonic acid Chemical compound C1=CC(C(=O)OC)=CC=C1CC1=CC=C(CP(O)(O)=O)C=C1 PLKWXDQPMWTNEM-UHFFFAOYSA-N 0.000 description 1
- FBCNWKJOAIGTOT-UHFFFAOYSA-N [4-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]methylphosphonic acid Chemical compound C=1C=C(CP(O)(O)=O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 FBCNWKJOAIGTOT-UHFFFAOYSA-N 0.000 description 1
- PJMVWJVUCREVLB-UHFFFAOYSA-N [4-[2-[4-(2-methoxyethoxy)phenyl]propan-2-yl]phenyl]methylphosphonic acid Chemical group C1=CC(OCCOC)=CC=C1C(C)(C)C1=CC=C(CP(O)(O)=O)C=C1 PJMVWJVUCREVLB-UHFFFAOYSA-N 0.000 description 1
- OIURSBJBBQMZAC-UHFFFAOYSA-N [4-[4-(2-hydroxyethoxy)phenyl]phenyl]methylphosphonic acid Chemical compound C1=CC(OCCO)=CC=C1C1=CC=C(CP(O)(O)=O)C=C1 OIURSBJBBQMZAC-UHFFFAOYSA-N 0.000 description 1
- XSVKKSQIBPFUBU-UHFFFAOYSA-N [4-[4-(2-methoxyethoxy)benzoyl]phenyl]methylphosphonic acid Chemical compound C1=CC(OCCOC)=CC=C1C(=O)C1=CC=C(CP(O)(O)=O)C=C1 XSVKKSQIBPFUBU-UHFFFAOYSA-N 0.000 description 1
- SAXCUODBBAHJNC-UHFFFAOYSA-N [4-[4-(2-methoxyethoxy)phenoxy]phenyl]methylphosphonic acid Chemical compound C1=CC(OCCOC)=CC=C1OC1=CC=C(CP(O)(O)=O)C=C1 SAXCUODBBAHJNC-UHFFFAOYSA-N 0.000 description 1
- WYIPRDBFIYYCSU-UHFFFAOYSA-N [4-[4-(2-methoxyethoxy)phenyl]sulfanylphenyl]methylphosphonic acid Chemical compound C1=CC(OCCOC)=CC=C1SC1=CC=C(CP(O)(O)=O)C=C1 WYIPRDBFIYYCSU-UHFFFAOYSA-N 0.000 description 1
- ZOFVENAWSNYRPM-UHFFFAOYSA-N [4-[4-(hydroxymethoxy)benzoyl]phenyl]methylphosphonic acid Chemical compound C1=CC(OCO)=CC=C1C(=O)C1=CC=C(CP(O)(O)=O)C=C1 ZOFVENAWSNYRPM-UHFFFAOYSA-N 0.000 description 1
- WVGQJZNHJOITBE-UHFFFAOYSA-N [4-[4-(hydroxymethoxy)phenoxy]phenyl]methylphosphonic acid Chemical compound C1=CC(OCO)=CC=C1OC1=CC=C(CP(O)(O)=O)C=C1 WVGQJZNHJOITBE-UHFFFAOYSA-N 0.000 description 1
- XYZCSHGEWDNHTE-UHFFFAOYSA-N [4-[4-(hydroxymethoxy)phenyl]sulfanylphenyl]methylphosphonic acid Chemical compound C1=CC(OCO)=CC=C1SC1=CC=C(CP(O)(O)=O)C=C1 XYZCSHGEWDNHTE-UHFFFAOYSA-N 0.000 description 1
- FPIZQGYAASBQJA-UHFFFAOYSA-N [4-[4-(hydroxymethoxy)phenyl]sulfonylphenyl]methylphosphonic acid Chemical compound C1=CC(OCO)=CC=C1S(=O)(=O)C1=CC=C(CP(O)(O)=O)C=C1 FPIZQGYAASBQJA-UHFFFAOYSA-N 0.000 description 1
- ZSVHWCWEUOIYOX-UHFFFAOYSA-N [4-[[4-(hydroxymethoxy)phenyl]methyl]phenyl]methylphosphonic acid Chemical compound C1=CC(OCO)=CC=C1CC1=CC=C(CP(O)(O)=O)C=C1 ZSVHWCWEUOIYOX-UHFFFAOYSA-N 0.000 description 1
- CFRBDLDYWUNBNF-UHFFFAOYSA-N [9-(2-hydroxyethoxy)anthracen-1-yl]methylphosphonic acid Chemical compound C1=CC(CP(O)(O)=O)=C2C(OCCO)=C(C=CC=C3)C3=CC2=C1 CFRBDLDYWUNBNF-UHFFFAOYSA-N 0.000 description 1
- CIFBVGOLNHOUFR-UHFFFAOYSA-N [9-(2-methoxyethoxy)anthracen-1-yl]methylphosphonic acid Chemical compound C1=CC(CP(O)(O)=O)=C2C(OCCOC)=C(C=CC=C3)C3=CC2=C1 CIFBVGOLNHOUFR-UHFFFAOYSA-N 0.000 description 1
- NCPIYHBOLXSJJR-UHFFFAOYSA-H [Al+3].[Al+3].[O-]P([O-])=O.[O-]P([O-])=O.[O-]P([O-])=O Chemical compound [Al+3].[Al+3].[O-]P([O-])=O.[O-]P([O-])=O.[O-]P([O-])=O NCPIYHBOLXSJJR-UHFFFAOYSA-H 0.000 description 1
- UKQZIZWJJVPSNV-UHFFFAOYSA-J [Mg+2].[Mg+2].CCC(P([O-])([O-])=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1.CCC(P([O-])([O-])=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 Chemical compound [Mg+2].[Mg+2].CCC(P([O-])([O-])=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1.CCC(P([O-])([O-])=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 UKQZIZWJJVPSNV-UHFFFAOYSA-J 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- BHUMZHDFNOXAMC-UHFFFAOYSA-N [methoxy(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(OC)C1=CC=CC=C1 BHUMZHDFNOXAMC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 102000011759 adducin Human genes 0.000 description 1
- 108010076723 adducin Proteins 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- MJWPFSQVORELDX-UHFFFAOYSA-K aluminium formate Chemical compound [Al+3].[O-]C=O.[O-]C=O.[O-]C=O MJWPFSQVORELDX-UHFFFAOYSA-K 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940118662 aluminum carbonate Drugs 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- GGWQIZGNRUCMAP-UHFFFAOYSA-K aluminum;2,2,2-trichloroacetate Chemical compound [Al+3].[O-]C(=O)C(Cl)(Cl)Cl.[O-]C(=O)C(Cl)(Cl)Cl.[O-]C(=O)C(Cl)(Cl)Cl GGWQIZGNRUCMAP-UHFFFAOYSA-K 0.000 description 1
- GQSZLMMXKNYCTP-UHFFFAOYSA-K aluminum;2-carboxyphenolate Chemical compound [Al+3].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O GQSZLMMXKNYCTP-UHFFFAOYSA-K 0.000 description 1
- KLMDYFUUSKOJAX-UHFFFAOYSA-K aluminum;acetate;dihydroxide Chemical compound CC(=O)O[Al](O)O KLMDYFUUSKOJAX-UHFFFAOYSA-K 0.000 description 1
- HQQUTGFAWJNQIP-UHFFFAOYSA-K aluminum;diacetate;hydroxide Chemical compound CC(=O)O[Al](O)OC(C)=O HQQUTGFAWJNQIP-UHFFFAOYSA-K 0.000 description 1
- KMJRBSYFFVNPPK-UHFFFAOYSA-K aluminum;dodecanoate Chemical compound [Al+3].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O KMJRBSYFFVNPPK-UHFFFAOYSA-K 0.000 description 1
- YNCDEEFMDXHURQ-UHFFFAOYSA-N aluminum;ethyl 3-oxobutanoate Chemical compound [Al].CCOC(=O)CC(C)=O YNCDEEFMDXHURQ-UHFFFAOYSA-N 0.000 description 1
- LIQDVINWFSWENU-UHFFFAOYSA-K aluminum;prop-2-enoate Chemical compound [Al+3].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C LIQDVINWFSWENU-UHFFFAOYSA-K 0.000 description 1
- DMGNPLVEZUUCBT-UHFFFAOYSA-K aluminum;propanoate Chemical compound [Al+3].CCC([O-])=O.CCC([O-])=O.CCC([O-])=O DMGNPLVEZUUCBT-UHFFFAOYSA-K 0.000 description 1
- CSJKPFQJIDMSGF-UHFFFAOYSA-K aluminum;tribenzoate Chemical compound [Al+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 CSJKPFQJIDMSGF-UHFFFAOYSA-K 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- IWQBBAGODHIDOD-UHFFFAOYSA-N anthracen-9-ylmethyl(ethoxy)phosphinic acid Chemical compound C1=CC=C2C(CP(O)(=O)OCC)=C(C=CC=C3)C3=CC2=C1 IWQBBAGODHIDOD-UHFFFAOYSA-N 0.000 description 1
- ZDXDKCJCSZZBDU-UHFFFAOYSA-N anthracen-9-ylmethylphosphonic acid Chemical compound C1=CC=C2C(CP(O)(=O)O)=C(C=CC=C3)C3=CC2=C1 ZDXDKCJCSZZBDU-UHFFFAOYSA-N 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- FNGGVJIEWDRLFV-UHFFFAOYSA-N anthracene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=CC3=C(C(O)=O)C(C(=O)O)=CC=C3C=C21 FNGGVJIEWDRLFV-UHFFFAOYSA-N 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- ZCLVNIZJEKLGFA-UHFFFAOYSA-H bis(4,5-dioxo-1,3,2-dioxalumolan-2-yl) oxalate Chemical compound [Al+3].[Al+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O ZCLVNIZJEKLGFA-UHFFFAOYSA-H 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- SJEZDMHBMZPMME-UHFFFAOYSA-L calcium;(3,5-ditert-butyl-4-hydroxyphenyl)methyl-ethoxyphosphinate Chemical compound [Ca+2].CCOP([O-])(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1.CCOP([O-])(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SJEZDMHBMZPMME-UHFFFAOYSA-L 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical group 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical compound OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MJUJXFBTEFXVKU-UHFFFAOYSA-N diethyl phosphonate Chemical compound CCOP(=O)OCC MJUJXFBTEFXVKU-UHFFFAOYSA-N 0.000 description 1
- PAGBSTCJQYFPLU-UHFFFAOYSA-L dilithium 2,6-ditert-butyl-4-(1-phosphonatopropyl)phenol Chemical compound C(C)C(C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)P([O-])([O-])=O.[Li+].[Li+] PAGBSTCJQYFPLU-UHFFFAOYSA-L 0.000 description 1
- KWZDEJROQPGVCA-UHFFFAOYSA-L dilithium 2,6-ditert-butyl-4-(phosphonatomethyl)phenol Chemical compound C(C)(C)(C)C=1C=C(CP([O-])([O-])=O)C=C(C=1O)C(C)(C)C.[Li+].[Li+] KWZDEJROQPGVCA-UHFFFAOYSA-L 0.000 description 1
- IEEVPULXESHFOP-UHFFFAOYSA-L dilithium dioxido-oxo-(1-phenylpropyl)-lambda5-phosphane Chemical compound C(C)C(C1=CC=CC=C1)P([O-])([O-])=O.[Li+].[Li+] IEEVPULXESHFOP-UHFFFAOYSA-L 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- MPJWUHTTWDIHSG-UHFFFAOYSA-N dimethyl 2-(diethoxyphosphorylmethyl)benzene-1,4-dicarboxylate Chemical compound CCOP(=O)(OCC)CC1=CC(C(=O)OC)=CC=C1C(=O)OC MPJWUHTTWDIHSG-UHFFFAOYSA-N 0.000 description 1
- IEIQALPPNHUYOE-UHFFFAOYSA-N dimethyl 5-(diethoxyphosphorylmethyl)benzene-1,3-dicarboxylate Chemical compound CCOP(=O)(OCC)CC1=CC(C(=O)OC)=CC(C(=O)OC)=C1 IEIQALPPNHUYOE-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- GQDMYDOOJSEVTE-UHFFFAOYSA-L dipotassium;2,6-ditert-butyl-4-(1-phosphonatopropyl)phenol Chemical compound [K+].[K+].CCC(P([O-])([O-])=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GQDMYDOOJSEVTE-UHFFFAOYSA-L 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- GGTJZPPHIMQXDL-UHFFFAOYSA-L disodium 2,6-ditert-butyl-4-(1-phosphonatopropyl)phenol Chemical compound C(C)C(C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)P([O-])([O-])=O.[Na+].[Na+] GGTJZPPHIMQXDL-UHFFFAOYSA-L 0.000 description 1
- VJOHORKTVYHDPP-UHFFFAOYSA-L disodium 4-(1-phosphonatoethyl)aniline Chemical compound CC(C1=CC=C(C=C1)N)P([O-])([O-])=O.[Na+].[Na+] VJOHORKTVYHDPP-UHFFFAOYSA-L 0.000 description 1
- JOQAMSDLZYQHMX-UHFFFAOYSA-L disodium;dioxido-oxo-phenyl-$l^{5}-phosphane Chemical compound [Na+].[Na+].[O-]P([O-])(=O)C1=CC=CC=C1 JOQAMSDLZYQHMX-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- UMWAPNRTJHWNEY-UHFFFAOYSA-N ethoxy(naphthalen-1-ylmethyl)phosphinic acid Chemical compound C1=CC=C2C(CP(O)(=O)OCC)=CC=CC2=C1 UMWAPNRTJHWNEY-UHFFFAOYSA-N 0.000 description 1
- IZLBLQZBOSEKCC-UHFFFAOYSA-N ethoxy(naphthalen-2-ylmethyl)phosphinic acid Chemical compound C1=CC=CC2=CC(CP(O)(=O)OCC)=CC=C21 IZLBLQZBOSEKCC-UHFFFAOYSA-N 0.000 description 1
- CIPINZYLNJJJOZ-UHFFFAOYSA-N ethoxy-(2-methyl-4-nitrophenyl)phosphinic acid Chemical compound CCOP(O)(=O)C1=CC=C([N+]([O-])=O)C=C1C CIPINZYLNJJJOZ-UHFFFAOYSA-N 0.000 description 1
- CQURPOCUZFPNQS-UHFFFAOYSA-N ethoxy-(2-nitrophenyl)phosphinic acid Chemical compound CCOP(O)(=O)C1=CC=CC=C1[N+]([O-])=O CQURPOCUZFPNQS-UHFFFAOYSA-N 0.000 description 1
- RWZULQFTFLWFPB-UHFFFAOYSA-N ethoxy-(3-methoxy-5-nitrophenyl)phosphinic acid Chemical compound CCOP(O)(=O)C1=CC(OC)=CC([N+]([O-])=O)=C1 RWZULQFTFLWFPB-UHFFFAOYSA-N 0.000 description 1
- FJMJEDWMEBBWND-UHFFFAOYSA-N ethoxy-(3-nitrophenyl)phosphinic acid Chemical compound CCOP(O)(=O)C1=CC=CC([N+]([O-])=O)=C1 FJMJEDWMEBBWND-UHFFFAOYSA-N 0.000 description 1
- HXOZGFLNQDJKJU-UHFFFAOYSA-N ethoxy-(4-nitrophenyl)phosphinic acid Chemical compound CCOP(O)(=O)C1=CC=C([N+]([O-])=O)C=C1 HXOZGFLNQDJKJU-UHFFFAOYSA-N 0.000 description 1
- TVRHYZDYCVPYOU-UHFFFAOYSA-N ethoxy-[(2-methoxycarbonylphenyl)methyl]phosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=CC=C1C(=O)OC TVRHYZDYCVPYOU-UHFFFAOYSA-N 0.000 description 1
- WEVOGHTXPNJKBH-UHFFFAOYSA-N ethoxy-[(2-methylphenyl)methyl]phosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=CC=C1C WEVOGHTXPNJKBH-UHFFFAOYSA-N 0.000 description 1
- WTMQQSQJVRHJHI-UHFFFAOYSA-N ethoxy-[(3-methoxycarbonylphenyl)methyl]phosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=CC(C(=O)OC)=C1 WTMQQSQJVRHJHI-UHFFFAOYSA-N 0.000 description 1
- MBQUKBUOPJYRBY-UHFFFAOYSA-N ethoxy-[(4-methoxycarbonylphenyl)methyl]phosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=C(C(=O)OC)C=C1 MBQUKBUOPJYRBY-UHFFFAOYSA-N 0.000 description 1
- CCSDDMRYRITCDV-UHFFFAOYSA-N ethoxy-[(4-nitrophenyl)methyl]phosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=C([N+]([O-])=O)C=C1 CCSDDMRYRITCDV-UHFFFAOYSA-N 0.000 description 1
- LVTQAMZTACTALM-UHFFFAOYSA-N ethoxy-[[2-(2-hydroxyethoxy)phenyl]methyl]phosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=CC=C1OCCO LVTQAMZTACTALM-UHFFFAOYSA-N 0.000 description 1
- WOZJBTFQYATSJA-UHFFFAOYSA-N ethoxy-[[3-(2-hydroxyethoxy)phenyl]methyl]phosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=CC(OCCO)=C1 WOZJBTFQYATSJA-UHFFFAOYSA-N 0.000 description 1
- HPAIGDGLZZBWJQ-UHFFFAOYSA-N ethoxy-[[4-(2-hydroxyethoxy)phenyl]methyl]phosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=C(OCCO)C=C1 HPAIGDGLZZBWJQ-UHFFFAOYSA-N 0.000 description 1
- SIYSVFKKVSIOQZ-UHFFFAOYSA-N ethoxy-[[4-(2-methoxyethoxy)phenyl]methyl]phosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=C(OCCOC)C=C1 SIYSVFKKVSIOQZ-UHFFFAOYSA-N 0.000 description 1
- LVSWDUMBWWVXCH-UHFFFAOYSA-N ethoxy-[[4-(4-hydroxybenzoyl)phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C(=O)C1=CC=C(O)C=C1 LVSWDUMBWWVXCH-UHFFFAOYSA-N 0.000 description 1
- UDHWTYVEJMMAQR-UHFFFAOYSA-N ethoxy-[[4-(4-hydroxyphenoxy)phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1OC1=CC=C(O)C=C1 UDHWTYVEJMMAQR-UHFFFAOYSA-N 0.000 description 1
- IDFUAGRPKNBVPL-UHFFFAOYSA-N ethoxy-[[4-(4-hydroxyphenyl)phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C1=CC=C(O)C=C1 IDFUAGRPKNBVPL-UHFFFAOYSA-N 0.000 description 1
- LYZFZPXSNKLASB-UHFFFAOYSA-N ethoxy-[[4-(4-hydroxyphenyl)sulfanylphenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1SC1=CC=C(O)C=C1 LYZFZPXSNKLASB-UHFFFAOYSA-N 0.000 description 1
- DLTKNJVGDIZIIZ-UHFFFAOYSA-N ethoxy-[[4-(4-hydroxyphenyl)sulfonylphenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 DLTKNJVGDIZIIZ-UHFFFAOYSA-N 0.000 description 1
- QHWHXDMPZGGCAJ-UHFFFAOYSA-N ethoxy-[[4-(4-methoxycarbonylphenoxy)phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1OC1=CC=C(C(=O)OC)C=C1 QHWHXDMPZGGCAJ-UHFFFAOYSA-N 0.000 description 1
- LFGLBHSTDLLHEK-UHFFFAOYSA-N ethoxy-[[4-(4-methoxycarbonylphenyl)sulfonylphenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1S(=O)(=O)C1=CC=C(C(=O)OC)C=C1 LFGLBHSTDLLHEK-UHFFFAOYSA-N 0.000 description 1
- HLCNJXVKCYOOAD-UHFFFAOYSA-N ethoxy-[[4-[(4-hydroxyphenyl)methyl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1CC1=CC=C(O)C=C1 HLCNJXVKCYOOAD-UHFFFAOYSA-N 0.000 description 1
- LHTODJVKYKVTDU-UHFFFAOYSA-N ethoxy-[[4-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C(C)(C)C1=CC=C(O)C=C1 LHTODJVKYKVTDU-UHFFFAOYSA-N 0.000 description 1
- ROZGWFKVQCLLLP-UHFFFAOYSA-N ethoxy-[[4-[2-[4-(2-hydroxyethoxy)phenyl]propan-2-yl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C(C)(C)C1=CC=C(OCCO)C=C1 ROZGWFKVQCLLLP-UHFFFAOYSA-N 0.000 description 1
- VFOIFWXGCHIMQG-UHFFFAOYSA-N ethoxy-[[4-[2-[4-(2-methoxyethoxy)phenyl]propan-2-yl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C(C)(C)C1=CC=C(OCCOC)C=C1 VFOIFWXGCHIMQG-UHFFFAOYSA-N 0.000 description 1
- QCNFQQUNSYKAGL-UHFFFAOYSA-N ethoxy-[[4-[2-[4-(hydroxymethoxy)phenyl]propan-2-yl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C(C)(C)C1=CC=C(OCO)C=C1 QCNFQQUNSYKAGL-UHFFFAOYSA-N 0.000 description 1
- BWAOSFAKBKDBOC-UHFFFAOYSA-N ethoxy-[[4-[4-(2-hydroxyethoxy)benzoyl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C(=O)C1=CC=C(OCCO)C=C1 BWAOSFAKBKDBOC-UHFFFAOYSA-N 0.000 description 1
- XYIDYIDCHFBVSJ-UHFFFAOYSA-N ethoxy-[[4-[4-(2-hydroxyethoxy)phenoxy]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1OC1=CC=C(OCCO)C=C1 XYIDYIDCHFBVSJ-UHFFFAOYSA-N 0.000 description 1
- OYEAQRWCZQUIBL-UHFFFAOYSA-N ethoxy-[[4-[4-(2-hydroxyethoxy)phenyl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C1=CC=C(OCCO)C=C1 OYEAQRWCZQUIBL-UHFFFAOYSA-N 0.000 description 1
- UAPDCVCWIMGKTG-UHFFFAOYSA-N ethoxy-[[4-[4-(2-hydroxyethoxy)phenyl]sulfanylphenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1SC1=CC=C(OCCO)C=C1 UAPDCVCWIMGKTG-UHFFFAOYSA-N 0.000 description 1
- RSIHFOQEVRHDKI-UHFFFAOYSA-N ethoxy-[[4-[4-(2-methoxyethoxy)phenoxy]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1OC1=CC=C(OCCOC)C=C1 RSIHFOQEVRHDKI-UHFFFAOYSA-N 0.000 description 1
- YFYQZSGNWNJEQC-UHFFFAOYSA-N ethoxy-[[4-[4-(2-methoxyethoxy)phenyl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C1=CC=C(OCCOC)C=C1 YFYQZSGNWNJEQC-UHFFFAOYSA-N 0.000 description 1
- XXENDFLKGZMDBM-UHFFFAOYSA-N ethoxy-[[4-[4-(hydroxymethoxy)benzoyl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C(=O)C1=CC=C(OCO)C=C1 XXENDFLKGZMDBM-UHFFFAOYSA-N 0.000 description 1
- JDCOQJXVBRYYHQ-UHFFFAOYSA-N ethoxy-[[4-[4-(hydroxymethoxy)phenoxy]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1OC1=CC=C(OCO)C=C1 JDCOQJXVBRYYHQ-UHFFFAOYSA-N 0.000 description 1
- KJFUDJKHDUZFMR-UHFFFAOYSA-N ethoxy-[[4-[4-(hydroxymethoxy)phenyl]sulfanylphenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1SC1=CC=C(OCO)C=C1 KJFUDJKHDUZFMR-UHFFFAOYSA-N 0.000 description 1
- CDPWICUCBGRQPF-UHFFFAOYSA-N ethoxy-[[4-[4-(hydroxymethoxy)phenyl]sulfonylphenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1S(=O)(=O)C1=CC=C(OCO)C=C1 CDPWICUCBGRQPF-UHFFFAOYSA-N 0.000 description 1
- MJLBMZLYJGRBHA-UHFFFAOYSA-N ethoxy-[[4-[[4-(2-hydroxyethoxy)phenyl]methyl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1CC1=CC=C(OCCO)C=C1 MJLBMZLYJGRBHA-UHFFFAOYSA-N 0.000 description 1
- CPOIBAYCHWYIFK-UHFFFAOYSA-N ethoxy-[[4-[[4-(hydroxymethoxy)phenyl]methyl]phenyl]methyl]phosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1CC1=CC=C(OCO)C=C1 CPOIBAYCHWYIFK-UHFFFAOYSA-N 0.000 description 1
- NTMZYORBLLMVGP-UHFFFAOYSA-N ethoxy-[[9-(2-hydroxyethoxy)anthracen-1-yl]methyl]phosphinic acid Chemical compound C1=CC=C2C(OCCO)=C3C(CP(O)(=O)OCC)=CC=CC3=CC2=C1 NTMZYORBLLMVGP-UHFFFAOYSA-N 0.000 description 1
- KKABPCHNGKEZJY-UHFFFAOYSA-N ethoxy-[[9-(2-methoxyethoxy)anthracen-1-yl]methyl]phosphinic acid Chemical compound C1=CC=C2C(OCCOC)=C3C(CP(O)(=O)OCC)=CC=CC3=CC2=C1 KKABPCHNGKEZJY-UHFFFAOYSA-N 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- VUERQRKTYBIULR-UHFFFAOYSA-N fosetyl Chemical compound CCOP(O)=O VUERQRKTYBIULR-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002291 germanium compounds Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 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 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- KYEFPKZGBZCJTB-UHFFFAOYSA-N methoxy-[[3-(2-methoxyethoxy)phenyl]methyl]phosphinic acid Chemical compound COP(O)(=O)CC1=CC(=CC=C1)OCCOC KYEFPKZGBZCJTB-UHFFFAOYSA-N 0.000 description 1
- YAXYIMRYSXZDLX-UHFFFAOYSA-N methyl 2-(diethoxyphosphorylmethyl)benzoate Chemical compound CCOP(=O)(OCC)CC1=CC=CC=C1C(=O)OC YAXYIMRYSXZDLX-UHFFFAOYSA-N 0.000 description 1
- OYDOFGBVULDGDS-UHFFFAOYSA-N methyl 3-(diethoxyphosphorylmethyl)benzoate Chemical compound CCOP(=O)(OCC)CC1=CC=CC(C(=O)OC)=C1 OYDOFGBVULDGDS-UHFFFAOYSA-N 0.000 description 1
- YTYPSGYDIRZUOQ-UHFFFAOYSA-N methyl 4-(diethoxyphosphorylmethyl)benzoate Chemical compound CCOP(=O)(OCC)CC1=CC=C(C(=O)OC)C=C1 YTYPSGYDIRZUOQ-UHFFFAOYSA-N 0.000 description 1
- YVRQWULFGBYQIJ-UHFFFAOYSA-N methyl 4-[4-(diethoxyphosphorylmethyl)phenyl]benzoate Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1C1=CC=C(C(=O)OC)C=C1 YVRQWULFGBYQIJ-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- BCDIWLCKOCHCIH-UHFFFAOYSA-N methylphosphinic acid Chemical compound CP(O)=O BCDIWLCKOCHCIH-UHFFFAOYSA-N 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- HELZKSLXGDCKJK-UHFFFAOYSA-N naphthalen-2-ylmethylphosphonic acid Chemical compound C1=CC=CC2=CC(CP(O)(=O)O)=CC=C21 HELZKSLXGDCKJK-UHFFFAOYSA-N 0.000 description 1
- CHDRADPXNRULGA-UHFFFAOYSA-N naphthalene-1,3-dicarboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC(C(O)=O)=C21 CHDRADPXNRULGA-UHFFFAOYSA-N 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 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 description 1
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 description 1
- 238000001320 near-infrared absorption spectroscopy Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- RJQRCOMHVBLQIH-UHFFFAOYSA-N pentane-1-sulfonic acid Chemical compound CCCCCS(O)(=O)=O RJQRCOMHVBLQIH-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 238000004448 titration Methods 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
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Description
本発明者等は、最終エステル化反応槽出口のポリエステルオリゴマーのカルボキシル末端基濃度の変動を抑制する方法について鋭意検討し、該最終エステル化反応槽出口のポリエステルオリゴマーのカルボキシル末端基濃度の変動は、第1エステル化反応槽出口のポリエステルオリゴマーのカルボキシル末端基濃度によりほぼ支配されることおよび該第1エステル化反応槽出口のポリエステルオリゴマーのカルボキシル末端基濃度は、第1エステル化反応槽へ供給されるスラリーにより持ち込まれる熱量の変動により第1エステル化反応槽の温度制御が過応答することにより第1エステル化反応槽温度変動が増大することにより引き起こされており、該過応答は第1エステル化反応槽内に滞留している反応物温度と第1エステル化反応槽に供給されるスラリー温度との温度差とスラリー流量およびスラリー比熱より求められる該第1エステル化反応槽に供給されるスラリーの単位時間当たりの熱量を一定にするという極めて単純な方法で抑制することができことを見出して本発明を完成した。すなわち、該方法により第1エステル化反応槽出口のポリエステルオリゴマーのカルボキシル末端基濃度の変動が抑制でき、結果として後続の重縮合反応やポリエステル品質に対して大きな影響を及ぼす最終エステル化反応槽出口のポリエステルオリゴマーのカルボキシル末端基濃度変動が抑制されることに立脚している。当然のことであるが、第1エステル化反応槽以降のエステル化反応条件により最終エステル化反応槽出口のポリエステルオリゴマーのカルボキシル末端基濃度が変化するので、該反応条件は一定範囲に制御する必要があるが、該制御は従来公知の方法を適用し制御するレベルで、本発明方法で得られる高度なカルボキシル末端基濃度の制御が可能となる。
該アルミニウム系重縮合としては、アルミニウム化合物からなる群より選ばれる少なくとも一種と、リン化合物からなる群より選ばれる少なくとも一種からなる重縮合触媒系が好ましい。
芳香環構造に結合した置換基は、C1〜C10のアルキル基、カルボキシルおよびカルボキシルエステル基、アルキレングリコールおよびモノアルコキシアルキレングリコールなどが挙げられる。異物低減効果の点でより好ましくは、カルボキシルおよびカルボキシルエステル基、アルキレングリコールおよびモノアルコキシアルキレングリコールである。その理由は不明であるが、ポリエステルおよび触媒の媒体であるアルキレングリコールとの相溶性が改善されることによると推測している。
リン化合物は次のようなものである。
[ポリエステルに不溶なアルミニウム系異物評価法]
溶融重縮合上がりのポリエステルペレット30gおよびパラクロロフェノール/テトラクロロエタン(3/1:重量比)混合溶液300mlを攪拌機付き丸底フラスコに投入し、該ペレットを混合溶液に100〜105℃、2時間で攪拌・溶解する。該溶液を室温になるまで放冷し、直径47mm/孔径1.0μmのポリテトラフルオロエチレン製のメンブレンフィルター(Advantec社製PTFEメンブレンフィルター、品名:T100A047A)を用い、全量を0.15MPaの加圧下で異物を濾別する。有効濾過直径は37.5mmとした。濾過終了後、引き続き300mlのクロロホルムを用い洗浄し、次いで、30℃で一昼夜減圧乾燥する。該メンブレンフィルターの濾過面を走査型蛍光X線分析装置(RIGAKU社製、ZSX100e、Rh管球4.0kW)でアルミニウム原子量を定量した。定量はメンブレンフィルターの中心部直径30mmの部分について行う。なお、該蛍光X線分析法の検量線はアルミニウム原子含有量が既知のポリエチレンテレフタレート樹脂を用いて求め、見掛けのアルミニウム原子量をppmで表示する。測定はX線出力50kV−70mAで分光結晶としてペンタエリスリトール、検出器としてPC(プロポーショナルカウンター)を用い、PHA(波高分析器)100−300の条件でアルミニウム−Kα線強度を測定することにより実施する。検量線用ポリエチレンテレフタレート樹脂中のアルミニウム原子量は、高周波誘導結合プラズマ発光分析法で定量する。
形成されて、該ボイドにより光の散乱が起こり成型体の透明性が低下することが原因となっていると推定している。
200rpmで攪拌した室温の純水1500mlにアルミニウム化合物30gを添加し、室温で6時間攪拌を続ける。引き続き液温を95℃に加温し、同温度で更に3時間攪拌を続行しアルミニウム化合物を溶解さる。得られた溶液を室温になるまで放冷し、孔径0.2μmのセルロースアセテート製のメンブレンフィルター(Advantec社製セルロースアセテートタイプメンブレンフィルター、品名:C020A047A)で濾過し、50mlの純水で洗浄する。得られた不溶分を濾過したフィルターを60℃の真空乾燥器で12時間乾燥し不溶分重量(W)を求める。アルミニウム化合物の水に対する不溶分量は下記式で算出する。アルミニウム化合物が水溶液の場合は、水溶液の一部を採取し、該水溶液を蒸発乾固することにより水溶液中の固形分を測定し、該固形分をアルミニウム化合物重量として水溶液中のアルミニウム化合物濃度を求め、水溶液中のアルミニウム化合物量が30gとなる量の水溶液を濾過することにより求める。該水溶液の場合は、水溶液中のアルミニウム化合物濃度が2質量%より濃い場合は、2質量%になるように純水を加えアルミニウム希釈して濾過を行った。該希釈は上記の固形アルミニウム化合物の溶解と同じ条件で行う。なお、上記操作はクリーンベンチ中で実施する。
[一軸延伸フィルムのヘイズ値]
ポリエステル樹脂を真空下、130℃で12時間乾燥し、ヒートプレス法で1000±100μmのシートを作成する。ヒートプレス温度、圧力および時間はそれぞれ320℃、100kg/cm2Gおよび3秒とする。プレス後シートは水中に投入し急冷却する。得られたシートをバッチ式延伸機(T.M.LONG CO.,INC製、FILM STRETCHER)で3.5倍に一軸延伸し300±20μmの一軸延伸フィルムを得る。延伸温度はブロー温度95℃/プレート温度100℃とする。また、延伸速度は1.5万%/分で行う。得られた一軸延伸フィルムのヘイズをJIS−K7136に準拠し、ヘイズメータ(日本電色工業社製、300A)を用いて測定する。なお、測定は5回行い、その平均値を求める。ヘイズ値はフィルム厚み300μmの換算値で表示する。一軸延伸フィルムのヘイズ値は0.5%以下がより好ましい。ヘイズ値が0.6%を超えた場合は、フィルムやボトル等の延伸を伴う成型により成型された成型体について高度に透明性の高い成型体が得られないので好ましくない。
[二軸延伸フィルムの微弱白濁感]
また、二軸延伸フィルムにした場合、約9.4mmの厚みになるように多数枚のフィルムを重ね合わせて(フィルム厚み188μmの場合で50枚重ね)、蛍光灯下で垂直に対して45度の角度で肉眼観察した時に評価される極めて微妙な白濁感が見られなくなるという効果が発現される。該白濁感は極めて僅かな光学特性差であり従来公知のヘイズ値等では差別化できない特性である。従って、汎用の光学用途の使用に関しては問題にならない特性であるが、高度な光学特性を要求される用途においては問題になる可能性のある特性値として注目される。以下本特性値を微弱白濁感と称する。
試料を0.200g精秤したのち、フェノール/テトラクロロエタン(重量比6/4)50mlに溶解する。この溶液を40mlウベローデ粘度管に取り、30℃の恒温槽中で落下秒数を計測して極限粘度(IV)を算出した。なお、式(1)中におけるTは試料溶液の落下秒数(秒)、T0は溶媒の落下秒数(秒)、Cは試料溶液濃度(g/dl)を示す。
該測定は3回行いその平均値を用いた。
オリゴマーを乾燥に呈すことなくハンディーミル(粉砕器)にて粉砕した。試料1.00gを精秤し、ピリジン20mlを加えた。沸石を数粒加え、15分間煮沸還流し溶解させた。煮沸還流後直ちに、10mlの純水を添加し、室温まで放冷した。フェノールフタレインを指示薬としてN/10−NaOHで滴定した。試料を入れずにブランクも同じ作業を行う。なお、オリゴマーがピリジンに溶解しない場合は、ベンジルアルコール中で行った。下記式に従って、AVo(eq/ton)を算出する。
AVo=(A−B)×0.1×f×1000/W
(A=滴定数(ml),B=ブランクの滴定数(ml),f=N/10−NaOHのファクター,W=試料の重さ(g))
該定量を3回測定してその平均値を用いた。
試料9mgを試料管に入れ、CDCl3+HFIP−d2(1+1)0.3mlを加えて溶解。CDCl3 0.3mlwokuwae,saranipirizin−d5 30maikurolを添加して、よく混ぜたのち、遠心分離を行い、可溶分のH-NMRスペクトルを500MHzの装置を用いて測定した。
試料15mgをヘキサフルオロイソプロパノール(HFIP)/CDCl3=1/1混合溶媒0.13mlに溶解し、CDCl3 0.52mlで希釈し、さらに0.2Mトリエチルアミン溶液(HFIP/CDCl3 1/9)を22μl添加した溶液を用いて、500MHzのH−NMR測定をして定量した。該測定は3回行いその平均値を用いた。
溶融重縮合上がりのポリエステルペレット30gおよびパラクロロフェノール/テトラクロロエタン(3/1:重量比)混合溶液300mlを攪拌機付き丸底フラスコに投入し、該ペレットを混合溶液に100〜105℃、2時間で攪拌・溶解した。該溶液を室温になるまで放冷し、直径47mm/孔径1.0μmのポリテトラフルオロエチレン製のメンブレンフィルター(Advantec社製PTFEメンブレンフィルター、品名:T100A047A)を用い、全量を0.15MPaの加圧下で異物を濾別した。有効濾過直径は37.5mmとした。濾過終了後、引き続き300mlのクロロホルムを用い洗浄し、次いで、30℃で一昼夜減圧乾燥した。該メンブレンフィルターの濾過面を走査型蛍光X線分析装置(RIGAKU社製、ZSX100e、Rhライン球4.0kW)でアルミニウム原子量を定量した。定量はメンブレンフィルターの中心部直径30mmの部分について行った。なお、該蛍光X線分析法の検量線はアルミニウム原子含有量が既知のポリエチレンテレフタレート樹脂を用いて求め、見掛けのアルミニウム原子量をppmで表示した。測定はX線出力50kV−70mAで分光結晶としてペンタエリスリトール、検出器としてPC(プロポーショナルカウンター)を用い、PHA(波高分析器)100−300の条件でAl−Kα線強度を測定することにより実施した。検量線用PET樹脂中のアルミニウム原子量は、高周波誘導結合プラズマ発光分析法で定量した。
ポリエステル樹脂を真空下、130℃で12時間乾燥し、ヒートプレス法で1000±100μmのシートを作成した。ヒートプレス温度、圧力および時間はそれぞれ320℃、100kg/cm2Gおよび3秒とした。プレス後シートは水中に投入し急冷却した。得られたシートをバッチ式延伸機(T.M.LONG CO.,INC製、FILM STRETCHER)で3.5倍に一軸延伸し300±20μmの一軸延伸フィルムを得た。延伸温度はブロー温度95℃/プレート温度100℃とした。また、延伸速度は1.5万%/分で行った。得られた一軸延伸フィルムのヘイズをJIS−K7136に準拠し、ヘイズメータ(日本電色工業社製、300A)を用いて測定した。ヘイズ値はフィルム厚み300μmの換算値で表示した。なお、測定は5回行ってその平均値を求めた。
二軸延伸ポリエステルフィルムを複数枚重ね合わせて約9.4mmの厚み(フィルム厚み188μmの場合で50枚重ね)とし、蛍光灯下で垂直に対して45度の角度で肉眼観察した時の白濁感を観察して以下の基準で判定した。
〇 :白濁感がない
△ :極わずかな白濁感がある
× :白濁感がある
××:白濁感が強い
(1)重縮合触媒溶液の調製
(リン化合物のエチレングリコール溶液の調製)
窒素導入管、冷却管を備えたフラスコに、常温常圧下、エチレングリコール2.0リットルを加えた後、窒素雰囲気下200rpmで攪拌しながら、リン化合物として(化39)で表されるIrganox1222(チバ・スペシャルティーケミカルズ社製)の200gを加えた。さらに2.0リットルのエチレングリコールを追加した後、ジャケット温度の設定を196℃に変更して昇温し、内温が185℃以上になった時点から60分間還流下で攪拌した。その後加熱を止め、直ちに溶液を熱源から取り去り、窒素雰囲気下を保ったまま、30分以内に120℃以下まで冷却した。得られた溶液中のIrganox1222のモル分率は40%、Irganox1222から構造変化した化合物のモル分率は60%であった。
冷却管を備えたフラスコに、常温常圧下、純水5.0リットルを加えた後、200rpmで攪拌しながら、塩基性酢酸アルミニウム200gを純水とのスラリーとして加えた。さらに全体として10.0リットルとなるよう純水を追加して常温常圧で12時間攪拌した。その後、ジャケット温度の設定を100.5℃に変更して昇温し、内温が95℃以上になった時点から3時間還流下で攪拌した。攪拌を止め、室温まで放冷し水溶液を得た。
上記方法で得たアルミニウム化合物水溶液に等容量のエチレングリコールを加え、室温で30分間攪拌した後、内温80〜90℃にコントロールし、徐々に減圧して、到達27hPaとして、数時間攪拌しながら系から水を留去し、20g/lのアルミニウム化合物のエチレングリコール溶液を得た。得られたアルミニウム溶液の27Al−NMRスペクトルのピーク積分値比は2.2であった。
3基の連続エステル化反応槽および3基の重縮合反応槽よりなり、かつ第3エステル化反応槽から第1重縮合反応槽への移送ラインに高速攪拌器を有したインラインミキサーが設置された連続式ポリエステル製造装置に高純度テレフタル酸1質量部に対してエチレングリコール0.75質量部とをスラリー調製槽に連続的に供給し、第1エステル化槽が反応温度250℃、110kPa、第2エステル化反応槽が260℃、105kPa、第3エステル化反応槽が260℃、105kPaとして、第2エステル化反応槽にエチレングルコール0.025質量部を連続的に投入しポリエステルオリゴマーを得た。上記方法において第1エステル化反応槽に供給するスラリー供給量の変動をロータリーピストン流量計を用いて送液ポンプの回転数を変えて設定値の±2.0%以内になるように制御した上で、第1エステル化反応槽内に滞留している反応物温度と第1エステル化反応槽に供給されるスラリー温度を計測してこれらの温度差とスラリー流量およびスラリー比熱より算出される該スラリーにより持ち込まれる単位時間当りの熱量が一定になるようにスラリー温度を制御することにより行った。該スラリー温度の制御はスラリー調製槽内のスラリー温度と該調製槽に供給するグリコール温度を連続的に監視しながら、フィードバック回路により連続的にグリコール添加温度を熱交換器を用いて変更することとスラリー調製槽に温度調整機能を付加してスラリー温度調整精度を上げる方法で実施した。上記方法で算出した第1エステル化反応槽に供給するスラリーの単位時間当たりの熱量変動は±1.7%であった。なお、第1エステル化反応槽に供給するスラリー温度は90℃を中心値として温度制御をした。また、熱量計算の単位時間は1時間当たりで算出した。なお、反応槽内に滞留する反応物温度は、反応槽の底部の缶壁より300mm内部に入った位置で測定した。また、エチレングリコール及びテレフタル酸をモル比は、±0.25%以内に制御した。該モル比の調整は、近赤外線分光光度計を用いてスラリーのテレフタル酸量を計測して、スラリー調製槽に供給するエチレングリコール量を調整することにより行った。また、第1エステル化反応槽の温度および圧力変動は±1.3%以内に制御した。また、第1エステル化反応槽の液面レベルの変動は±0.2%以内であった。第1エステル化反応槽出口のオリゴマーのAVoは平均値で2200eq/tonであった。また、第3エステル化反応槽出口のオリゴマーのAVoおよびOHVoはそれぞれ平均値で800eq/tonおよび985eq/tonであり、AV%は44.8モル%であった。該オリゴマーを3基の反応槽よりなる連続重縮合装置に連続的に移送すると共に、該移送ラインに設置されたインラインミキサーに上記方法で調製したアルミニウム化合物のエチレングリコール溶液およびリン化合物のエチレングリコール溶液をそれぞれポリエステル中の酸成分に対してアルミニウム原子およびリン原子として0.015モル%および0.036モル%となるように攪拌式のミキサーで攪拌しながら連続的に添加し、初期重縮合反応槽が265℃、9kPa、中期重縮合反応槽が265〜268℃、0.7kPa、最終重縮合反応槽が273℃、13.3Paで重縮合しIV0.620のPETを得た。得られたPETの特性値を表1に示す。なお、上記攪拌式ミキサー出口のアルミニウム化合物溶液とリン化合物溶液との混合液のNMRスペクトルにはアルミニウム化合物のエチレングリコール溶液と混合する前のリン化合物のエチレングリコール溶液のスペクトルには存在しない5〜24ppmの範囲にブロードなピーク(配位ピークと称する)が観察された。該配位ピークの積分値はアルミニウム化合物のエチレングリコール溶液と混合する前のリン化合物のエチレングリコール溶液のNMRスペクトルに存在する25〜27ppm付近に観察される水酸基が結合したリン原子のNMRスペクトルピークの積分値に対して45%であった。
上記方法で得られたポリエステル樹脂を135℃、133Paで6時間減圧乾燥し、押出機に供給して約280℃でシート状に溶融押出し、表面温度20℃に保った金属ロール上で急冷固化し、厚さ1400μmのキャストフィルムを得た。この際、溶融PETの異物除去用濾材として濾過可能な粒子サイズが10μm(初期濾過効率95%)のステンレススチール製焼結濾材を用いて精密濾過を行った。このキャストフィルムを、加熱したロール群および赤外線ヒーターで100℃に加熱し、その後周速差のあるロール群で長手方向に3.5倍延伸して一軸配向PETフィルムを得た。
塗布液は以下の方法で調製した。
なお、表1に示した値は、12時間毎にサンプリングした50個のサンプル(25日分)の評価結果である。また、ポリエステルオリゴマーのカルボキシル末端基の変動幅は、50個のサンプルの最大値、最小値および平均値より下記式(1)で求めた。
標準偏差(s)={(測定値―平均値)2の和/サンプル数(50)}1/2・・(2)
実施例1の方法において、スラリー温度およびスラリー熱量制御を取り止める以外は、実施例1と同様の方法でポリエステルを得た。第1エステル化反応槽に供給されるスラリーの単位時間当たりの熱量の変動は±5.2%であった。結果を表1に示す。
実施例1の方法において、スラリー調製時のスラリーの単位時間当たりの熱量が一定になる制御を止め、単に、スラリー調製槽内温度と該調製槽に供給するグリコール温度を連続的に監視しながら、フィードバック回路により連続的にグリコール添加温度を熱交換器を用いて変更しスラリー調製槽内のスラリー温度が一定になるように調整するのみに変更する以外は、実施例1と同様の方法でポリエステルを得た。第1エステル化反応槽に供給されるスラリーの単位時間当たりの熱量変動は±3.6%であった。結果を表1に示す。
本比較例におけるポリエステルオリゴマーのカルボキシル末端基濃度の変動は大きかった。そのために、得られるポリエステル樹脂およびフィルムの透明性が劣っていた。例えば、二軸延伸PETフィルムにおいて、微弱白濁感が多発した。
実施例1の方法において、第1エステル化反応槽に供給するスラリー流量の変動幅を設定値±1.0%に向上するように変更する以外は、実施例1同様の方法でポリエステルを得た。第1エステル化反応槽に供給するスラリーの単位時間当たりの熱量変動は±0.9%に向上した。結果を表1に示す。
実施例1の方法において、スラリー調製槽からエステル化反応槽への移送ラインの途中に攪拌機および温度調整機能を有したスラリー貯留槽を設けて、該スラリー貯留槽においてもスラリーの温度制御を行いスラリー温度の調整精度を上げるように変更する以外は、実施例1同様の方法でポリエステルを得た。第1エステル化反応槽に供給するスラリーの単位時間当たりの熱量変動は±0.5%に向上した。結果を表1に示す。
従って、産業界に寄与することが大である。
Claims (9)
- ジカルボン酸とグリコールとからなるスラリーをスラリー調製槽で調製して該スラリーをエステル化反応槽に連続的に供給し、複数のエステル化反応槽を用いてエステル化反応を行い引き続き重縮合を行うことによりポリエステルを連続的に製造する方法において、第1エステル化反応槽内に滞留している反応物温度と第1エステル化反応槽に供給されるスラリー温度との温度差とスラリー流量およびスラリー比熱より求められる該第1エステル化反応槽に供給されるスラリーの単位時間当たりの熱量を設定値の±2.0%以内になるように制御することを特徴とするポリエステルの製造方法。
- 上記第1エステル化反応槽に供給されるスラリーの単位時間当たりの熱量制御をスラリー温度制御により行うことを特徴とする請求項1に記載のポリエステルの製造方法。
- 第1エステル化反応槽内に滞留する反応物の温度および第1エステル化反応槽内に滞留する反応物の液面レベルをそれぞれ設定値の±2.0%以内および±0.2%以内になるように同時に制御することを特徴とする請求項1または2に記載のポリエステルの製造方法。
- 第1エステル化反応槽圧力を設定値の±4%以内になるように制御することを特徴とする請求項1〜3のいずれかに記載のポリエステルの製造方法。
- 第1エステル化反応槽出口のポリエステルオリゴマーのカルボキシル末端基濃度を設定値の±10%以内に制御することを特徴とする請求項1〜4のいずれかに記載のポリエステルの製造方法。
- 最終エステル化反応槽出口のポリエステルオリゴマーのカルボキシル末端基濃度の変動が設定値±6%以内であることを特徴とする請求項1〜5のいずれかに記載のポリエステルの製造方法。
- 第1エステル化反応槽出口のポリエステルオリゴマーのカルボキシル末端基濃度の設定値が1400〜3700eq/tonであることを特徴とする請求項1〜6のいずれかに記載のポリエステルの製造方法。
- 最終エステル化反応槽出口のポリエステルオリゴマーのカルボキシル末端基濃度の設定値が500〜900eq/tonであることを特徴とする請求項1〜7のいずれかに記載のポリエステルの製造方法。
- 最終エステル化反応槽出口のポリエステルオリゴマーの全末端基濃度に対するカルボキシル末端基濃度の割合が35超〜49%であることを特徴とする請求項1〜8のいずれかに記載のポリエステルの製造方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006042474A JP4867386B2 (ja) | 2006-02-20 | 2006-02-20 | ポリエステルの製造方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006042474A JP4867386B2 (ja) | 2006-02-20 | 2006-02-20 | ポリエステルの製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007217637A JP2007217637A (ja) | 2007-08-30 |
JP4867386B2 true JP4867386B2 (ja) | 2012-02-01 |
Family
ID=38495255
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006042474A Active JP4867386B2 (ja) | 2006-02-20 | 2006-02-20 | ポリエステルの製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP4867386B2 (ja) |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3681244B2 (ja) * | 1996-12-17 | 2005-08-10 | 日本エステル株式会社 | ポリエステルの連続製造法 |
JP3690768B2 (ja) * | 1997-03-10 | 2005-08-31 | 日本エステル株式会社 | ポリエステルの連続製造方法 |
JPH11106498A (ja) * | 1997-10-06 | 1999-04-20 | Nippon Ester Co Ltd | ポリエステルの連続製造方法 |
JP2001329058A (ja) * | 2000-05-19 | 2001-11-27 | Toray Ind Inc | ポリエステルの製造方法 |
JP2005187555A (ja) * | 2003-12-25 | 2005-07-14 | Toyobo Co Ltd | ポリエステルならびにポリエステルの製造方法 |
JP2005187666A (ja) * | 2003-12-25 | 2005-07-14 | Toyobo Co Ltd | ポリエステルの製造方法 |
-
2006
- 2006-02-20 JP JP2006042474A patent/JP4867386B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
JP2007217637A (ja) | 2007-08-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR20080048025A (ko) | 폴리에스테르, 폴리에스테르의 제조방법, 및 폴리에스테르성형체 | |
JP2008030370A (ja) | 積層ポリエステルフィルム | |
JPWO2005075539A1 (ja) | ポリエステル重合触媒およびこれを用いて製造されたポリエステル並びにポリエステルの製造方法 | |
KR101018219B1 (ko) | 폴리에스테르의 제조방법 및 이를 이용하여 제조된폴리에스테르 및 폴리에스테르 성형체 | |
KR20030094236A (ko) | 폴리에스테르 중합촉매, 폴리에스테르 및 폴리에스테르의제조방법 | |
JP2005187556A (ja) | ポリエステルならびにポリエステルの製造方法 | |
JP4857625B2 (ja) | ポリエステルの製造方法 | |
JP4867386B2 (ja) | ポリエステルの製造方法 | |
JP2006282801A (ja) | ポリエステルフィルム製造方法 | |
JP2006282800A (ja) | ポリエステルフィルム | |
JP4983080B2 (ja) | ポリエステルの製造方法 | |
JP2007211045A (ja) | ポリエステルの製造方法 | |
JP2007009154A (ja) | ポリエステルの製造方法 | |
JP2007211046A (ja) | ポリエステルの製造方法 | |
JP2007308554A (ja) | ポリエステルの製造方法 | |
JP2007131743A (ja) | ポリエステルの製造方法 | |
JP2007217635A (ja) | ポリエステルの製造方法 | |
JP2007217634A (ja) | ポリエステルの製造方法 | |
JP2007211047A (ja) | ポリエステルの製造方法 | |
JP2007009153A (ja) | ポリエステルの製造方法 | |
JP2008266360A (ja) | ポリエステル重合触媒およびこれを用いて製造されたポリエステル並びにポリエステルの製造方法 | |
JP5076437B2 (ja) | ポリエステルの製造方法 | |
JP2007217636A (ja) | ポリエステルの製造方法 | |
JP2006282799A (ja) | ポリエステル及びポリエスル成形体 | |
JP5181409B2 (ja) | ポリエステル重合触媒およびこれを用いて製造されたポリエステル並びにポリエステルの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20090216 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20100701 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20111018 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20111031 |
|
R151 | Written notification of patent or utility model registration |
Ref document number: 4867386 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R151 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20141125 Year of fee payment: 3 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
R371 | Transfer withdrawn |
Free format text: JAPANESE INTERMEDIATE CODE: R371 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |