CA1049030A - Oxaphospholanes-1,2 - Google Patents
Oxaphospholanes-1,2Info
- Publication number
- CA1049030A CA1049030A CA74208588A CA208588A CA1049030A CA 1049030 A CA1049030 A CA 1049030A CA 74208588 A CA74208588 A CA 74208588A CA 208588 A CA208588 A CA 208588A CA 1049030 A CA1049030 A CA 1049030A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- oxaphospholane
- oxo
- methyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- FXPDGSSSQUFIPW-UHFFFAOYSA-N oxaphospholane Chemical class C1COPC1 FXPDGSSSQUFIPW-UHFFFAOYSA-N 0.000 title abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 56
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 150000002576 ketones Chemical class 0.000 claims abstract description 10
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 63
- -1 tetrahydrofurfuryl Chemical group 0.000 claims description 63
- 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 claims description 37
- 229910052708 sodium Inorganic materials 0.000 claims description 37
- 239000011734 sodium Substances 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- WJUVPWDPVNGYNX-UHFFFAOYSA-N 5-diethoxyphosphoryl-2-ethoxy-3,3,5-trimethyl-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound CCOP(=O)(OCC)C1(C)CC(C)(C)P(=O)(OCC)O1 WJUVPWDPVNGYNX-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 claims description 2
- JVSLFVADXKFWJL-UHFFFAOYSA-N 5-dimethoxyphosphoryl-2-methoxy-3,3,5-trimethyl-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound COP(=O)(OC)C1(C)CC(C)(C)P(=O)(OC)O1 JVSLFVADXKFWJL-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 10
- 229920005989 resin Polymers 0.000 abstract description 9
- 239000011347 resin Substances 0.000 abstract description 9
- 229920005830 Polyurethane Foam Polymers 0.000 abstract description 7
- 239000011496 polyurethane foam Substances 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 4
- 229920003023 plastic Polymers 0.000 abstract description 4
- 239000004033 plastic Substances 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000003223 protective agent Substances 0.000 abstract 1
- 238000005979 thermal decomposition reaction Methods 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- 239000003795 chemical substances by application Substances 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 19
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 16
- 229960000583 acetic acid Drugs 0.000 description 16
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 16
- 238000009835 boiling Methods 0.000 description 15
- 239000012362 glacial acetic acid Substances 0.000 description 15
- 239000006260 foam Substances 0.000 description 14
- 229910052698 phosphorus Inorganic materials 0.000 description 12
- 238000004821 distillation Methods 0.000 description 11
- 239000003822 epoxy resin Substances 0.000 description 11
- 125000004437 phosphorous atom Chemical group 0.000 description 11
- 229920000647 polyepoxide Polymers 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000001228 spectrum Methods 0.000 description 11
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 229920002678 cellulose Polymers 0.000 description 7
- 239000001913 cellulose Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920002292 Nylon 6 Polymers 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 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 6
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 6
- 239000000306 component Substances 0.000 description 6
- 150000002924 oxiranes Chemical class 0.000 description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000002485 combustion reaction Methods 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 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 5
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N 3-Methyl-3-buten-2-one Chemical compound CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 229920002239 polyacrylonitrile Polymers 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000004848 polyfunctional curative Substances 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 230000009183 running Effects 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- BWHOZHOGCMHOBV-UHFFFAOYSA-N Benzalacetone Natural products CC(=O)C=CC1=CC=CC=C1 BWHOZHOGCMHOBV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 3
- UFFAFBPZFGAMJJ-UHFFFAOYSA-N (2-methoxy-4,6-dimethylphenyl)boronic acid Chemical compound COC1=CC(C)=CC(C)=C1B(O)O UFFAFBPZFGAMJJ-UHFFFAOYSA-N 0.000 description 2
- UUKRKWJGNHNTRG-NSCUHMNNSA-N (e)-4-(4-chlorophenyl)but-3-en-2-one Chemical compound CC(=O)\C=C\C1=CC=C(Cl)C=C1 UUKRKWJGNHNTRG-NSCUHMNNSA-N 0.000 description 2
- NMRPZFYCWHAWFP-UHFFFAOYSA-N 5-diethoxyphosphoryl-2-ethoxy-5-methyl-3-(4-methylphenyl)-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound CCOP1(=O)OC(P(=O)(OCC)OCC)(C)CC1C1=CC=C(C)C=C1 NMRPZFYCWHAWFP-UHFFFAOYSA-N 0.000 description 2
- ZYFXKDPHRREMBV-UHFFFAOYSA-N 5-diethoxyphosphoryl-2-methoxy-3,3,5-trimethyl-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound CCOP(=O)(OCC)C1(C)CC(C)(C)P(=O)(OC)O1 ZYFXKDPHRREMBV-UHFFFAOYSA-N 0.000 description 2
- QYMYTEQEHMGWIL-UHFFFAOYSA-N 5-dioctoxyphosphoryl-2-ethoxy-3,3,5-trimethyl-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound CCCCCCCCOP(=O)(OCCCCCCCC)C1(C)CC(C)(C)P(=O)(OCC)O1 QYMYTEQEHMGWIL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- XVXPYZHHKRLFFC-UHFFFAOYSA-N bis(oxolan-2-ylmethyl) hydrogen phosphite Chemical compound C1CCOC1COP(O)OCC1CCCO1 XVXPYZHHKRLFFC-UHFFFAOYSA-N 0.000 description 2
- OXLDKMFHLBAHLV-UHFFFAOYSA-N bis(prop-2-enyl) hydrogen phosphite Chemical compound C=CCOP(O)OCC=C OXLDKMFHLBAHLV-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 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 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 2
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 2
- XMQYIPNJVLNWOE-UHFFFAOYSA-N dioctyl hydrogen phosphite Chemical compound CCCCCCCCOP(O)OCCCCCCCC XMQYIPNJVLNWOE-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- YFVIOSLVIRXREX-UHFFFAOYSA-N oxaphospholan-5-ylphosphonic acid Chemical class OP(O)(=O)C1CCPO1 YFVIOSLVIRXREX-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000000930 thermomechanical effect Effects 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- WRRZKDVBPZBNJN-ONEGZZNKSA-N (e)-4-(4-methoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=C(\C=C\C(C)=O)C=C1 WRRZKDVBPZBNJN-ONEGZZNKSA-N 0.000 description 1
- GBKGJMYPQZODMI-SNAWJCMRSA-N (e)-4-(furan-2-yl)but-3-en-2-one Chemical compound CC(=O)\C=C\C1=CC=CO1 GBKGJMYPQZODMI-SNAWJCMRSA-N 0.000 description 1
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- JTDBMCUIIOOHKX-UHFFFAOYSA-N 2-butoxy-5-dibutoxyphosphoryl-3,3,5-trimethyl-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound CCCCOP(=O)(OCCCC)C1(C)CC(C)(C)P(=O)(OCCCC)O1 JTDBMCUIIOOHKX-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RZBRJTWRZWNSJI-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-diethoxyphosphoryl-2-ethoxy-5-methyl-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound CCOP1(=O)OC(P(=O)(OCC)OCC)(C)CC1C1=CC=C(Cl)C=C1 RZBRJTWRZWNSJI-UHFFFAOYSA-N 0.000 description 1
- IAPZDDAMFHKHFX-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-dimethoxyphosphoryl-2-methoxy-5-methyl-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound COP1(=O)OC(P(=O)(OC)OC)(C)CC1C1=CC=C(Cl)C=C1 IAPZDDAMFHKHFX-UHFFFAOYSA-N 0.000 description 1
- USXMUOFSQBSHGN-UHFFFAOYSA-N 4-(4-methylphenyl)but-3-en-2-one Chemical compound CC(=O)C=CC1=CC=C(C)C=C1 USXMUOFSQBSHGN-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- NGTGNTLWUWUBMI-UHFFFAOYSA-N 5-bis(phenylmethoxy)phosphoryl-5-methyl-2-phenylmethoxy-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound O1C(C)(P(=O)(OCC=2C=CC=CC=2)OCC=2C=CC=CC=2)CCP1(=O)OCC1=CC=CC=C1 NGTGNTLWUWUBMI-UHFFFAOYSA-N 0.000 description 1
- FEWQTGUATMQCNW-UHFFFAOYSA-N 5-diethoxyphosphoryl-2-ethoxy-3,5-diphenyl-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound CCOP1(=O)OC(P(=O)(OCC)OCC)(C=2C=CC=CC=2)CC1C1=CC=CC=C1 FEWQTGUATMQCNW-UHFFFAOYSA-N 0.000 description 1
- WHQIRRPVXWURRU-UHFFFAOYSA-N 5-diethoxyphosphoryl-2-ethoxy-4,5-dimethyl-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound CCOP(=O)(OCC)C1(C)OP(=O)(OCC)CC1C WHQIRRPVXWURRU-UHFFFAOYSA-N 0.000 description 1
- SYWWCVWRBMCPTO-UHFFFAOYSA-N 5-diethoxyphosphoryl-2-ethoxy-5-methyl-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound CCOP(=O)(OCC)C1(C)CCP(=O)(OCC)O1 SYWWCVWRBMCPTO-UHFFFAOYSA-N 0.000 description 1
- NESZELZIKRVEFU-UHFFFAOYSA-N 5-diethoxyphosphoryl-2-ethoxy-5-methyl-3-phenyl-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound CCOP1(=O)OC(P(=O)(OCC)OCC)(C)CC1C1=CC=CC=C1 NESZELZIKRVEFU-UHFFFAOYSA-N 0.000 description 1
- WTAALVNBFLZCHE-UHFFFAOYSA-N 5-dimethoxyphosphoryl-2-ethoxy-3,3,5-trimethyl-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound CCOP1(=O)OC(C)(P(=O)(OC)OC)CC1(C)C WTAALVNBFLZCHE-UHFFFAOYSA-N 0.000 description 1
- PVNKNIPGSAQUCI-UHFFFAOYSA-N 5-dimethoxyphosphoryl-2-methoxy-3,5-diphenyl-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound COP1(=O)OC(P(=O)(OC)OC)(C=2C=CC=CC=2)CC1C1=CC=CC=C1 PVNKNIPGSAQUCI-UHFFFAOYSA-N 0.000 description 1
- PAKFVOJWCOYJGH-UHFFFAOYSA-N 5-dimethoxyphosphoryl-2-methoxy-5-(4-methylphenyl)-3-phenyl-1,2lambda5-oxaphospholane 2-oxide Chemical compound COP1(=O)OC(P(=O)(OC)OC)(C=2C=CC(C)=CC=2)CC1C1=CC=CC=C1 PAKFVOJWCOYJGH-UHFFFAOYSA-N 0.000 description 1
- WMKMBORGAAHPRQ-UHFFFAOYSA-N 5-dimethoxyphosphoryl-2-methoxy-5-methyl-3-[(4-methylphenyl)methyl]-1,2lambda5-oxaphospholane 2-oxide Chemical compound COP1(=O)OC(P(=O)(OC)OC)(C)CC1CC1=CC=C(C)C=C1 WMKMBORGAAHPRQ-UHFFFAOYSA-N 0.000 description 1
- CHXRFFVTTVSUDD-UHFFFAOYSA-N 5-dipropoxyphosphoryl-2-ethoxy-3,3,5-trimethyl-1,2lambda5-oxaphospholane 2-oxide Chemical compound O=P1(OC(CC1(C)C)(P(=O)(OCCC)OCCC)C)OCC CHXRFFVTTVSUDD-UHFFFAOYSA-N 0.000 description 1
- MYUXBYJZLGLUOJ-UHFFFAOYSA-N 5-dipropoxyphosphoryl-3,3,5-trimethyl-2-propoxy-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound CCCOP(=O)(OCCC)C1(C)CC(C)(C)P(=O)(OCCC)O1 MYUXBYJZLGLUOJ-UHFFFAOYSA-N 0.000 description 1
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- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
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- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
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- XNINJQATBBNSIK-UHFFFAOYSA-N benzyl methyl hydrogen phosphite Chemical compound COP(O)OCC1=CC=CC=C1 XNINJQATBBNSIK-UHFFFAOYSA-N 0.000 description 1
- GGCXLVWDCPTFMN-UHFFFAOYSA-N bis(2-chloroethyl) hydrogen phosphite Chemical compound ClCCOP(O)OCCCl GGCXLVWDCPTFMN-UHFFFAOYSA-N 0.000 description 1
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- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- SBOHMURKJVRVGE-UHFFFAOYSA-N cyclohexyl propan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC1CCCCC1 SBOHMURKJVRVGE-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 1
- HEGXHCKAUFQNPC-UHFFFAOYSA-N dicyclohexyl hydrogen phosphite Chemical compound C1CCCCC1OP(O)OC1CCCCC1 HEGXHCKAUFQNPC-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- RQKYHDHLEMEVDR-UHFFFAOYSA-N oxo-bis(phenylmethoxy)phosphanium Chemical compound C=1C=CC=CC=1CO[P+](=O)OCC1=CC=CC=C1 RQKYHDHLEMEVDR-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
- C08K5/5373—Esters of phosphonic acids containing heterocyclic rings not representing cyclic esters of phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
- C08K5/5357—Esters of phosphonic acids cyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1289073 | 1973-09-07 | ||
| CH698174 | 1974-05-21 | ||
| CH1046574 | 1974-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1049030A true CA1049030A (fr) | 1979-02-20 |
Family
ID=27175658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA74208588A Expired CA1049030A (fr) | 1973-09-07 | 1974-09-05 | Oxaphospholanes-1,2 |
Country Status (15)
| Country | Link |
|---|---|
| JP (2) | JPS5055641A (fr) |
| AR (1) | AR203399A1 (fr) |
| AU (1) | AU7271274A (fr) |
| BR (1) | BR7407457D0 (fr) |
| CA (1) | CA1049030A (fr) |
| DE (1) | DE2441998A1 (fr) |
| DK (1) | DK439274A (fr) |
| ES (1) | ES429804A1 (fr) |
| FR (1) | FR2257600B1 (fr) |
| GB (1) | GB1443114A (fr) |
| IE (1) | IE39888B1 (fr) |
| IL (1) | IL45509A (fr) |
| IT (1) | IT1021153B (fr) |
| LU (1) | LU70856A1 (fr) |
| NL (1) | NL7411754A (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4042649A (en) * | 1975-09-18 | 1977-08-16 | Ciba-Geigy Corporation | 1,2-Oxaphospholanes |
| US6353080B1 (en) | 1997-06-26 | 2002-03-05 | The Dow Chemical Company | Flame retardant epoxy resin composition |
| CN116987262A (zh) * | 2022-04-26 | 2023-11-03 | 中国科学院化学研究所 | 一种尼龙、含该尼龙的抗熔滴阻燃材料及制备方法 |
-
1974
- 1974-08-16 DK DK439274A patent/DK439274A/da unknown
- 1974-08-21 IL IL45509A patent/IL45509A/en unknown
- 1974-08-27 AU AU72712/74A patent/AU7271274A/en not_active Expired
- 1974-09-02 DE DE2441998A patent/DE2441998A1/de active Pending
- 1974-09-04 NL NL7411754A patent/NL7411754A/xx unknown
- 1974-09-05 JP JP49102456A patent/JPS5055641A/ja active Pending
- 1974-09-05 LU LU70856A patent/LU70856A1/xx unknown
- 1974-09-05 GB GB3881074A patent/GB1443114A/en not_active Expired
- 1974-09-05 IE IE1846/74A patent/IE39888B1/xx unknown
- 1974-09-05 AR AR255476A patent/AR203399A1/es active
- 1974-09-05 CA CA74208588A patent/CA1049030A/fr not_active Expired
- 1974-09-06 BR BR7457/74A patent/BR7407457D0/pt unknown
- 1974-09-06 FR FR7430276A patent/FR2257600B1/fr not_active Expired
- 1974-09-06 IT IT27030/74A patent/IT1021153B/it active
- 1974-09-06 ES ES429804A patent/ES429804A1/es not_active Expired
- 1974-12-07 JP JP49141065A patent/JPS50126665A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1443114A (en) | 1976-07-21 |
| DK439274A (fr) | 1975-05-05 |
| FR2257600B1 (fr) | 1976-10-22 |
| ES429804A1 (es) | 1976-10-01 |
| BR7407457D0 (pt) | 1975-07-08 |
| IE39888B1 (en) | 1979-01-17 |
| IL45509A0 (en) | 1974-11-29 |
| DE2441998A1 (de) | 1975-03-13 |
| AR203399A1 (es) | 1975-09-08 |
| IT1021153B (it) | 1978-01-30 |
| FR2257600A1 (fr) | 1975-08-08 |
| IL45509A (en) | 1977-02-28 |
| JPS5055641A (fr) | 1975-05-15 |
| LU70856A1 (fr) | 1975-06-11 |
| AU7271274A (en) | 1976-06-17 |
| NL7411754A (nl) | 1975-03-11 |
| JPS50126665A (fr) | 1975-10-04 |
| IE39888L (en) | 1975-03-07 |
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